Straight man is turned into a submissive sissy Part 2

178 Min Read

I had to earn this load.

My throat was open, and my ability to breathe was sporadic, and I think I was taking all but the last inch, when he finally announced, “Get ready.”

I was more than ready, and I kept sucking until he shot his load in my mouth. I milked his amazing cock for every drop of his cum… then continued just cleaning it up, not stopping until he eventually pulled out.

He said, “Thanks, man.”

“No, thank you,” I responded.

My jaw was sore and I waggled it around, figuring I was done. I was standing up to go when a voice ordered, “Over here, cock sucker.”

I looked over and saw another flaccid black cock.

A smaller one.

I figured, Why not? One more for the road.

As I approached, the man surprised me by asking, “What’s your name, sissy?”

No reason not to tell him, so I replied in my unmistakably masculine voice, “I’m Kendra, Sir.”

“Well Kendra, it’s nice to meet you. Will you please suck my cock?”

“Yes Sir, I’ll be glad to,” warming to his mix of humiliation and courtesy. I went over to it and took it into my mouth… getting it hard quickly.

“That’s it, cock sucker,” he encouraged me. “You’re a natural, Kendra.”

Once he was hard I bobbed hungrily, wanting both to deep throat this six-inch cock… same size as mine… and to get him off quickly.

After a couple minutes of deep throat sucking, he ordered, “Kendra, jerk me off. I want to shoot all over your slutty face.”

“Yes, Sir,” I agreed, a facial something that did intrigue me.

“Beg for my cum, Kendra-faggot,” he ordered.

“Yes Sir, please come on me. Shoot your load all over my sissy face. Coat my face with your cum,” I begged him, just as his cock exploded a massive load all over my face. The first rope hit me right in an open eye. A second rope followed, landing on my nose and cheek as I closed my eyes before two more ropes splattered my open mouth and chin.

“Thank you, Sir,” I said. Between his courtesy and praise on the one hand, and his calling me humiliating names on the other, this man had kept my emotions swirling from warmth and gratitude, to the degradation I welcomed as a dirty slut.

“You’re welcome, bitch,” he said brusquely, before his cock disappeared.

My head still spinning from this chaotic treatment, I stood up and hurried out of the room before any more cocks showed up. I mean I kind of wanted more, but my jaw was sore, and my knees were aching. I briefly contemplated next time bringing along a cushion to kneel on, but that idea died a quick death when I pictured how it would look as I carried it in and out through the store.

I walked back into the store and saw Jeremy, a student in my Advanced English class, manning the till. I turned my face away and scurried out, praying he didn’t recognize me.

Praying my wig and uncharacteristic outfit concealed my identity.

I got into my car and drove away, not looking at myself until I reached a red light.

My face was coated.

I looked like a cheap slut.

Fortunately however, completely unrecognizable.

I drove home, removing the wig when I got close. Happily, I didn’t need to leave the car until I was in the garage with the door closed.

I went into the house and directly up to the washroom, where I saw my eye was red and bloodshot.


And I have to go out tonight!

I took another shower as I replayed the crazy four black cocks I’d sucked.

I felt dirty.

I felt guilty.

I felt hungry for more.


That night, I went to the party.

I drank.

I chatted with Paige on Facetime.

At midnight I didn’t kiss anyone, but I did receive a text.

Your New Year’s Resolution is to become a complete sissy. Say it.

I shook my head in… I don’t know… Dismay? Self-loathing? Acceptance? Gratitude? Even exhilaration? I decided all of those terms applied as I whispered happily to myself, “My New Year’s Resolution is to become a complete sissy.”

DAY 8: Tuesday the 1st

A New Year.


Day 8.

Last night I’d made a resolution that I hoped to keep.

A resolution I was scared to keep.

Paige would arrive home in a few days.

How was I going to explain any of this?

To Paige or to anyone?

That problem was for another day.

Today I was curious what would come next.

Today I was to go to my parents’.

Shit… in an hour.

I’d slept until one in the afternoon.

And I was still kind of hung over.

I went to the box and opened the Day 8 gift.

It was another butt plug.

This one had a pocket-sized remote control.

I read the note.


Your training is getting close to the end.

Did you enjoy sucking cock yesterday?

Are you craving cock right now?

Are you craving cum right now?

Don’t worry, we both know the answer.

Today, you will wear your new butt plug in your cunt from the moment you finish reading these instructions (unless you haven’t yet showered) until you go to bed. You will, every hour, set the vibrations as follows:

Hour 1: 1 minute on level 1.

Hour 2: 2 minutes on level 1.

Hour 3: 3 minutes on level 2.

Hour 4: 4 minutes on level 2.

Hour 5: 5 minutes on level 3.

Hour 6: 6 minutes on level 3.

Hour 7: 7 minutes on level 4.

Hour 8: 8 minutes on level 4.

Hour 9: 9 minutes on level 5.

Hour 10: 10 minutes on level 6.

During the first nine hours you must experience the vibrations for exactly the number of minutes specified. The tenth hour, you may go longer if you wish.

But of course, you may not come.

PS: Each hour should start at the same minute.

Mistress M

This was going to be hard… pun intended.

I would be at my parents’ for the next few hours.

Inwardly thanking my Mistress for her latitude I showered, dried myself off, lubed up the plug, and slowly slid it inside me. Even though it was longer than my other plugs, it was a little thinner than the dildo I’d used the other day, so I experienced only a slight burn.

I donned panties and pantyhose, jeans and a dress shirt.

I looked at the clock.

1: 25.

I started the stopwatch on my phone and turned the vibe plug to 1.

Ooooooh, my!

What a strange, pleasurable feeling!

No wonder girls love their vibes!


The minute passed far too quickly.

But when my phone dinged, I obeyed and shut it off.

I made the salad I always did for family dinners (I make an amazing Greek salad in case you care) and headed over.

I arrived at 2:20, 5 minutes before my next scheduled vibrating session.

I remained in my car for a few minutes, feeling compelled to obey the letter of the law… or I guess I mean of my instructions.

At 2:25 I turned on the remote and sat there enjoying the gentle buzz.

Fuck, I can’t believe how nice this feels! My cock is getting hard in seconds!

Two minutes flew by, and I shut it off and headed inside… impressed with how naturally I was learning to walk with a toy in my cunt.

As usual, the next couple of hours were frantic.

People coming in.

Mom completing her preparations for the meal with help from her sister Mabel.

Dad watching football.

It was easy to sneak into the washroom at 3:25 and enjoy three minutes of vibrations, now with a pattern that briefly doubled in intensity every few seconds.

I was a minute late at 4:25 because I was out front helping grandma bring in the desserts from her car (her lefsa is the ultimate treat… I’m partly Norwegian in case you care). I hurried back outside once I’d set down my first load of dessert trays, so I could do my four minutes. This session seemed super long, because I was outside and people were waiting inside… and just as the fourth minute began, a car pulled up.

I allowed the pleasure to continue as my auntie and uncle got out of their car. My uncle Harold was old school, so my Aunt Rosemary waited patiently while he walked around the car to open the door and assist her in rising. Such a gracious couple!

I waved to them using that as an excuse to delay before grabbing the final tray from grandma’s car, with ten seconds left.

I lingered for the last pleasurable seconds before reaching in my pocket to shut it off just as Aunt Rosemary called out, “Happy New Year, Kenny.”

“You too, auntie,” I replied, as I walked into the house with my pussy simmering down, but my hard-on wanting more.

I’d just finished dinner when hour five came around.

I excused myself to the bathroom again, and discovered level three was faster, and it featured three quick, intense vibrations every few seconds. Most bathrooms can be embarrassingly effective sound chambers, but fortunately my… my cunt plug?… was quite silent.

At 6:25 as we watched television and sat on couches and easy chairs while eating dessert, I decided to turn on my plug while I was in a room with other people. I was sitting in a chair by myself, and the television was loud, because my father has hearing problems.

I’m not going to lie: it was exhilarating to enjoy six minutes of secretive pleasurable vibrations while we all watched TV. I even answered a question more or less intelligibly while I indulged myself.

I was in the kitchen, my pussy still feeling the after pleasure of the six minutes when Mom asked, once we were alone, “Are you wearing pantyhose, Ken?”

I froze.

“I can see the top of them,” she explained.

“Oh,” was all I could say.

Mom added, as she tucked the back of my shirt in for me, “It’s no big deal, sweetie. I love wearing them, too.”

I turned around and told her defensively, “I don’t normally wear them.”

“I’m happy whether you do or don’t. No judging,” she shrugged and then added, “I mean, you used to wear mine all the time.”

“You knew?” I gasped.

“You used to leave some interesting stains in my panties and pantyhose,” she smiled, just as Aunt Rosemary walked in.

“What are you two talking about?” she asked.

“The past,” Mom answered smoothly.

I was mortified, but also relieved that Mom knew I used not only to use, but even to ejaculate in her panties and pantyhose, and she seemed okay with it. If she could keep my secret for this many years, I had no worries about her opinion of me and her discretion at this late date.

I wished our conversation could have gone further, but we were never alone again for the rest of the night.

At 7:25 I did seven minutes on level four. This one gave me a wide variety of fast and then slow vibrations… never predictable… creating a variety of pleasures. Fuck, each hour enhanced the pleasure. And God, did I want to come.

I headed out at precisely 8:20, giving myself enough time to drive to a 7-11. I turned on the vibrations for eight minutes in the parking lot. God, I needed to get fucked! I wish I had permission to fuck myself with that dildo again.

Maybe I could?

No, bad idea: it was okay to fuck myself, but not to come. That would be too frustrating.

Although I was supposed to continue on with this vibrating pleasure stick for ten straight hours.

I’m not sure my ass (my pussy) would ever be the same after the dildo before and now the amazing teasing pleasure of my vibrating plug.

After my eight minutes, I went into the 7-11 and got a slurpee, not worrying about the caffeine, figuring I needed to remain awake for two more hours at least.

I got home, got undressed, just remaining in my panties and pantyhose, and logged online.

I was scrolling through Tumblr browsing through sissy gifs for a few minutes before I spied a link for hypno sissy videos.

I’d seen that before, but had never clicked on it.

Figuring why not, I clicked on it.

I then spent more than two hours immersed in a whole new world. A world that seemed like a natural extension of the past eight days.

I watched a few videos:

-girls sucking cocks, while I could hear soft but still audible words repeated over and over: “You’re a cock sucker.”

-girls sucking black cocks (scenes changing every few seconds) as a different and sultry voice called me (well, whomever was watching) a variety of names belittling my manhood compared to superior BBC.

-shemales getting fucked (shemales are damn hot) by a variety of cocks.

-white girls getting ass fucked in rapid succession by BBC (following each five-second scene, a word flashed on the screen: faggot, cock sucker, bimbo, slut, etc.)

-girls bouncing forward and back, taking two cocks at once (the sultry voice was back, this time periodically purring different phrases: “Your cunt loves cock… Your tummy loves cum… Dirty sissies are good sissies… Girl cunts produce beautiful babies, but sissy cunts produce only something too filthy to mention…” and on and on.

As I continued watching these vids, I did hour nine. The vibrations were now more intense and more varied. I was never fucking hornier in my life!

Then as hour ten hit, I turned on level six and could do nothing but moan, it was so intense. Fast hard vibrations that literally had my body trembling.

I watched another captivating hypno sissy video that focused on BBC.

Then Paige called.

Fuck! I still had five minutes left in my ten-minute minimum.

“Hi, honey,” I greeted, after putting the laptop on mute.

“Miss me?” she asked.

“You’re gone?” I asked with my usual sarcastic wit.

“Asshole,” she teased.

And it’s really full at the moment, I thought to myself as it vibrated like crazy. “I miss you too.”

“Only a few more days,” she said.

“It’s been forever,” I said.

“Yeah, I mean, I haven’t seen you since last year,” she joked, something I would usually say.

“That’s my joke,” I protested.

“Clearly we’ve been dating too long,” she teased. “You’ve corrupted my wit.”

“An eternity,” I said.

“So… what have you been up to?”

“Watching a lot of porn,” I admitted truthfully.

“I bet.”

“You?” I asked.

“Sightseeing every day,” she said, before adding, “I’ve finally concluded you can see too many castles.”

“I bet,” I said, trying to pay attention to the love of my life while I watched big black cocks destroying white girls’ asses.

“You seem distracted,” she observed.

“Just tired,” I lied, “doing New Year’s Day with the family was great, but I was there for hours.” I was feeling good about my dissimilation until I let out a soft moan as the toy soared into an intense vibration pattern.

“Did you just moan?”

“No, but I did just yawn,” I said.

“Bullshit. You’re watching porn,” she caught on.

“I plead the Fifth,” I admitted.

“I’m stuck in a hotel room with my Mom, and you get to watch porn,” she sighed, the only girl I’d ever dated that liked watching porn. When we watched it together, it often led to some great sex.


“I’m hiding out in the bathroom, so for now I can say whatever I want. What kind of porn are you watching?” she asked.

“BBC porn,” I admitted, skirting the hypno sissy part.

“I do enjoy the feel of a nice big black cock,” she teased, reminding me of her last boyfriend.

I thought to myself, Me too, but only said, “I know, I know.”

“Anal?” she asked.

“Yes, please,” I joked.

“The scene, asshole.”

“Of course it is,” I revealed.

“You and your fascination with anal sex,” she said.

“Hey, blame Deadpool,” I protested.

“You know I still have my strap-on from my college days,” she revealed.

“You do, do you?” I leered with my voice. She had been rather frank about her college days which besides her black boyfriend, had included a few lesbian encounters.

“I figured maybe we could have a threesome one day,” she continued driving me crazy.

“I love you,” I said.

“You know, I think I’ll buy us a new strap-on,” she said. “I mean we’ll be in Amsterdam tomorrow. Where better to find a sex toy?”

“Make sure it’s big and black,” I joked, although I wasn’t really joking at all.

“You keep talking like that, and I’m going to come home and fuck the living shit out of you,” she said sexily.

“Don’t promise anything you can’t back up,” I said, hinting I was okay with it… which I was.

“Trust me,” she continued. “When I put on a cock, I become a different person.”

“That I want to see,” I said, imagining her pegging me.

“Clearly we both need to get laid,” she appraised.

“Agreed,” I said.

“I need to get in there,” I overheard her Mom saying.

“I was about to suggest some phone sex, but alas, I have to go,” she sighed.

“I’ll just go and use a vibe in my ass then,” I said. I really said that? That was way too honest!

“You better not,” she forbade me, before adding, “that ass is mine.”

“Mmmmmm,” I mmmed noncommittally.

“Although unfortunately we won’t be arriving back until Sunday the sixth, instead of this Saturday like we’d planned. So… you and I will have to put off any ass-claiming until then.”

“That is a shame: I really miss you,” I replied. I realized that her delay also meant that I’d now complete my 12-day training the day before she got home.

“I miss you too. Love you,” she said.

“Love you too,” I returned.

I hung up, turned up the volume and watched the rest of the scene.

I then sighed… knowing I wasn’t allowed to come… so I shut off the laptop and the toy.

I went into the bathroom to take out the plug and clean it, suddenly feeling empty as I got ready for bed, replaying that Mom knew about my hosiery wearing perversion.


DAY 9: Wednesday the 2nd

Two-thirds done.

Only four days left.

What could be left?

Only one way to find out.

I went downstairs and opened Box 9.

This one was also empty except for a note.

I read the note.

Cock Sucking Kendra

On your phone, in your apps, is an app called SCORE. Your account is already created with the username SISSYCUMBUCKET and your password is BIMBOBITCH.

You will need to answer the questions yourself, but once you finish, you can get all the cock you want.

You must take at least three loads today, but if you want, you can take as many more as you wish.

PS: If you feel ambitious and are craving some BBC, go to the top floor of the engineering building at the college and you may never leave.

PPS: You may suck as many cocks as you wish: 3, 5, 50, but you may not take anything up your cunt.

Mistress M

Of course, the first thing I did was find the app and log in… not really concerned how it got on my phone in the first place.

Questions popped up.

Yes __X__ No _____ 1. Do you suck cock?
A few days ago the answer would have been no… but now it was a definite YES!

Yes __X__ No _____ 2. Do you swallow?
Again… a recent YES, and the question had me craving another load in my mouth.

Yes _____ No __X__ 3. Are you a bottom?
I hadn’t done that yet… but I had come from a vibrating dildo in my ass, and was curious. That said, I answered with my truth of the moment.

Yes __X__ No _____ 4. Are you submissive?
Based on the first eight days, that had to be a big YES!

Yes _____ No __X__ 5. Do you want to top?
I wanted to suck cock.

I maybe wanted to be fucked.I had NO interest in getting sucked by a guy or fucking a guy. Those were things I could do with Paige… and thus would definitely be cheating.

Yes __X__ No _____ 6. Do you like wearing panties?

Yes _____ No __X__ 7. Do you define yourself as straight?
I honestly wasn’t sure… but at the moment the answer seemed to be not any more.

Yes __X__ No _____ 8. Are you willing to take a facial?
Already had and would do so again, given the opportunity.

Yes _____ No __X___ 9. Would you allow a man to give you a massage?

Yes __X__ No _____ 10. Are you willing to have sex in a public washroom?
At the moment I would suck a cock almost anywhere… I was craving cum!

Yes __X__ No _____ 11. Are you willing to have sex with any age from 18-90?
Although 90 seemed rather extreme, I wasn’t fussy about who the cock was attached to. What I wanted wasn’t a very high bar: just a cock with a load in its balls.

I then was transitioned to a new page.

Please choose the one of the following that describes you best:
All were animated gif pictures with brief summaries:

A man on his knees sucking cock
You are available to suck cock anytime, anyplace.

A man in a dress on his knees sucking cock
You’ll dress up (panties, pantyhose, heels) to look like the sissy you are.

A man in a dress on all fours bouncing back on a cock
You have two holes available for use.

A close-up of a cock fucking a mouth
You are generously offering your cock for oral.

A close up of a cock fucking an ass
You are generously offering your cock to an eager bottom.

Two guys in a 69
You can top or bottom depending on the needs of the other.

A guy with cocks in both holes as he rides back and forth
Simply put, you are a cock slut willing to serve cock with both your holes. The more the merrier.

Well, I was getting off on being sissified, so I chose SISSY COCK SUCKER.

I was taken to yet another page.

A new checklist was displayed:

You are:


I clicked on white, and the picture of the cock sucker in a dress went a shade whiter.

Another question popped up:

You are:

Skinny (slightly underweight)
Jock (tall and built)
Muscle man (works out, linebacker type)
Chubby (slightly overweight)
Average (the proper weight for your height)

Out of the five the jock fit me best, so I chose that.

A moment later a map popped up of the area around my home with some dots scattered here and there: three REDS, four BLUES, 1 PURPLE and 1 PINK.

I checked the meanings of the colours and learned that:

RED was a top looking for a cock sucker

BLUE was a cock sucker looking for a cock

GREEN was a switch (meaning they could suck or be sucked)

PURPLE was a top looking for a bottom to fuck

PINK was a bottom looking for a cock to fuck his ass

I noticed that a RED was right near my house, as a matter of fact, right next door! Although I wanted to suck cock, I sure didn’t want to do it so close to home.

Suddenly the doorbell rang.


I was wearing only panties and pantyhose.

I ran upstairs and grabbed a robe… considered removing my panties and pantyhose, but felt that would be disobedient.

Instead, I covered up with some pajamas and socks as the doorbell rang again.

I went back down and answered the door.

It was my neighbour’s son Bill.

“Hey, Bill,” I greeted.

“May I come in?” he asked.

“Sure,” I said, although this was weird. Bill wasn’t someone just to come over. Sure, I hung out with his dad sometimes, but Bill had never been in my house in the two years we’ve been neighbours. He was a first-year college student who attended a college in the city.

He walked in and once I closed the door asked, throwing me for a loop, “Where’s your sissy attire, cock sucker?”

“Excuse me?” I goggled, astonished at the question.

He pulled out his phone and showed me the app… the one I had just activated. “It says here you’re a sissy cock sucker. See that blue dot on your house? The one labeled Sissycumbucket?”

“T-t-that must be a mistake,” I stammered, mortified.

“No mistake,” he said. “The app brought me right here.”

I was speechless.

He asked, “Where’s your hot girlfriend?”

“Europe,” I answered.

“Perfect,” he said. “So judging by your confusion, you must have just gotten the app.”

Figuring I was already busted since playing dumb hadn’t worked, I nodded, “Yeah, but it’s not what you think.”

“No, I’m sure it’s exactly what I think. Get your phone,” he said. “I’ll show you how to hide your location. Otherwise people like me are going to just come over unannounced, expecting a blow job.”

“Oh, God,” I moaned, and hurried to grab my phone.

I returned and handed it to him. He showed me how to hide my location and did it for me.

“Thanks,” I said.

“So now you can repay me,” he said.

“Bill, this is weird,” I said, although I couldn’t deny I was craving cock and cum.

“Think of it this way,” he said. “You will always have a cock next door whenever you get a craving.”

“It’s just….”

“And I can generate a few loads a day, so I’m almost always fully loaded,” he added… and oddly that appealed to me. A cock close by. A load I could extract whenever I got the craving.

“I don’t usually do this,” I said, which was true.

He shrugged, “So do you get all sissied up when you go out, or just panties?”

I don’t know why I answered, “Panties and pantyhose usually.”

“I love pantyhose,” he said. “Not enough women wear them anymore.”

“I love them too,” I agreed, liking having a guy to talk with about my weird fetish.

“Go put some on,” he ordered.

Figuring fuck it and craving a cock in my mouth, I admitted, “I’m wearing them right now.”

“You really are a little sissy slut,” he said, looking amused. “Show me.”

“Okay,” I said, feeling partly ashamed, partly excited.

I dropped my robe, pulled down my pajama bottoms and removed my socks.

“Wow, you really are a little sissy,” he mused, “so cute,” looking at me in just my panties and pantyhose.

“Please don’t tell anyone,” I said, shame coursing through me as he looked at me the way I often looked at sexy women.

“If you’re a good sissy cock sucker,” he said, as he guided me to my knees, “this can be our secret arrangement.”

“Okay,” I said, feeling a little embarrassed.

“Let’s go into the living room,” he suggested.


He went to the couch, pulled down his pants and underwear and sat down.

“Get me the TV remote, sissy,” he ordered.

I did, burning in shame at being told what to do by this teenager… although, like the sissy I was becoming, I glanced at his cock, which although it was flaccid, looked to be a decent size.

I handed him the remote and he sat down, turned on the television, started watching sports updates and prompted me, “Sissy, it’s not going to suck itself.”

“Sorry,” I apologized, as I moved to him, lowered myself before him and reached for his flaccid cock.

“Show me what you got,” he said.

I warned him for some reason, “I’ve only sucked a few cocks so far.”

“Well then, you can practice on mine,” he offered agreeably, before adding, “although with the cock app, I imagine you can now get as much cock as you like.”

“I can’t believe such a thing exists,” I said.

“Yeah, it’s quite the app,” he said. “I’ve had guys of all ages come and suck me pretty much anywhere.”

“Anywhere?” I asked.

“At my house, in my car, in a bathroom, at school, and so forth,” he said. “My favourite is always in a roomy mini-van, by some dad who has kids.”

“Crazy,” I said, as I imagined there were others around like me.

“Oh yeah, I’ve had guys my age, guys your age, guys clearly in mid-life crisis mode and even some grandpas,” he said.

“Wow!” as I tried to imagine all different types of men sucking cock in secret.

“Yeah, most are married, it seems,” he said, as I stroked his cock. He instructed, “Get sucking, I have to meet my girlfriend in an hour.”

“Okay,” I said, thinking how strange it was that I was engaged to a beautiful woman and he had a girlfriend he was going to see soon, and yet here I was taking his cock in my mouth.

Weird, even.

“Oh yeah,” he groaned, “get it nice and hard with that cock sucking mouth of yours.”

I couldn’t explain it, but I’d already found that as soon as a cock was in front of me or in my mouth, the dirty talk really enhanced the entire experience.

The shame faded instantly.

I didn’t care that he knew who I was.

I didn’t care that my secret could possibly be outed.

I just wanted his cock.

I just wanted his cum.

I just wanted to be a good cock sucker.

No, a great cock sucker.

His cock hardened in my mouth as I swirled my tongue around and used excess saliva to create more lubrication.

Once it was hard, I began bobbing on his six and a half inch (give or take) cock.

God, it felt so natural.

“Oh yeah,” he groaned, as he watched sports updates, which only enhanced my humiliating excitement.

So for a few minutes… I sucked.

This position with him sitting, was very different from the four glory hole cocks where they were all standing.

I had to lean forward and bob down, which was more challenging for me, and more difficult to get into a consistent rhythm.

I never tried to take it all in, being worried I might gag.

Instead, I just bobbed on four or five inches of it.

Suddenly he ordered, “Crawl onto the couch.”

I did.

“Lay down on your stomach and suck me,” he ordered, “but keep your legs bent up.”

I didn’t understand what he wanted at first, but eventually my mouth was back on his cock, my ass raised and my feet sticking up in the air.

As I resumed sucking, I realized if he was like me, he wanted to look at my nylon legs and feet.

He chuckled, as his hand went to my pantyhose clad ass, “Completely shaved, I see.”

More humiliation even as my hard cock flinched into the couch as a guy was caressing my ass.

“You’re going to be a great sissy,” he moaned, squeezing my ass.

My cheeks burned in shame… even as my cock raged.

My lust for cum overcame the humiliation.

A couple minutes later he warned, “I’m going to come soon.”

Wanting the load in my mouth, I bobbed faster and received the warm load that, to my surprise, didn’t explode into my mouth, but oozed.

I kept sucking as he came and came.

I had to work hard to swallow it all in this awkward position.

Once we were finished, I sat back up and he said, “You’re pretty good.”

“Thanks,” I replied awkwardly.

“I’m going to finish watching the highlights,” he said, his cock still hard.

“Um, okay,” I said, this encounter so much more awkward now that the sex was done. “I’m going to shower.”

“Sure,” he said absently, as he watched my TV.

I went to shower, my head spinning and wondering about the consequences of this new… new relationship?

I got dressed… fresh panties and blue pantyhose… jeans and a t-shirt and returned downstairs. I was expecting him to be gone.

He wasn’t.

He said, looking down at my feet, “I see you’re ready for your day.”

“Yeah,” I said, not sure what else to say.

“Want a second load?” he asked, his cock still out.

Fuck! This was weird.

Yet I did.

I nodded, “Sure.”

“Then take off your jeans,” he ordered.

“Okay,” I said.

Once off, he said, “Come and use your nylon feet to get me hard.”

“Okay,” I said, thinking that was something I wished would happen to me. I hadn’t ever asked Paige to do it for me, but I was pretty sure she would.

I sat on the end of the couch and moved my feet to his semi-erect cock, as he watched Kelly and Ryan.

God, this was weird.

I moved my feet up and down as it slowly hardened.

Once it was hard, he squeezed my feet together and told me, “Now jerk me off with your feet.”

“Okay,” I said, doing as he expected… which was more challenging than one would think. I had to bend my legs a certain way which was awkward and made me look like a frog, and which kind of burned my thighs after a couple minutes.

“That’s nice,” he said, not looking at my face at all, but at my nylon-clad feet pumping his dick.

After only a couple of minutes I said, “Sorry, I’m getting a bit of a cramp.”

He stood up and ordered, “Knees, sissy.”

“Yes, Sir,” I said, to a guy almost ten years younger than I.

“Sir,” he chuckled as I was now before him. “I like that.”

More shame.

Yet, more hunger as his delicious cock (yes, I called it delicious) was now cantilevered right before me and I was in my more comfortable sissy cock sucking position.

“Open wide,” he ordered, as he slid his cock in my mouth.

As soon as my lips were wrapped around this hard, teen cock, my brain shifted directly into submissive sissy mode as I began bobbing… in this position more easily able to take it all in.

“Fuck, I may have to bring you along to poker night,” he said.

My eyes went wide. “Huh?”

“Yeah, there are six to eight of us, and you would be under the table, crawling from cock to cock,” he said.

Oddly, the idea of being under a table serving cock after cock was appealing.

“Although Ben would likely insist on eventually pounding that ass of yours,” he added.

I kept sucking, listening to this crazy future possibility.

“Ever been ass fucked?” he asked, pulling out.

“No, Sir,” I answered, looking up at him.

“Do you want to be?” he asked, as he traced my lips with his cock.

“I’m not sure,” I admitted.

“Cock suckers almost always end up as bottoms too,” he said, as he slid back into my mouth and began deeply fucking my face.

I focused on breathing through my nose.

“Oh yeah, next poker night is next Tuesday when school is back on,” he continued. “I think you’ll indeed be our table cock sucker, would you like that?”

He pulled out and in my hunger for cock, in my submissive sissy persona, I responded without thinking of consequences, “Yes, Sir, I would love that.”

“I knew you would,” he chuckled, as he resumed face fucking me… just as deeply but now more aggressively.

A couple minutes of deep thrusts, and balls bouncing off my chin, he deposited a second load in my mouth… this one oozing smoothly down my throat in this preferred sissy position.

Once done, he said, “I’ll be in touch.”

“Okay,” I said, the taste and feel of his cum still lingering in my mouth.

“I think we’ll dress you all up for that night,” he said.

“Okay,” I said, the idea of being fully dressed as a female a little appealing, and not only to hide my identity.

“Later, cock sucker,” he said, tucking his cock away.

“Bye,” I said.

Once he was gone, I shook my head even as my phone made a unique sound.

I went to it and saw a message from the app: Hungry, cock sucker?

I responded, again letting my hunger for cock and cum override anything else: Yes, Sir.

I put my jeans back on as the text responded: Last stall. Casey’s restaurant. Ten minutes.

That was only a five-minute drive.

I responded: Yes, Sir.

One last response: Be on your knees and ready! I’m in a hurry.

I responded back: Yes, Sir.

I put on my shoes and drove to the restaurant. It was an old school burger place.

I got there a little early, noticed the place was pretty empty (I was arriving a little early for lunch) and went directly to the washroom.

I went into the last stall and stood there waiting.

Fuck, this was weird.

I was waiting in a bathroom stall so I could suck a cock. A stranger’s cock.

I heard the outer door open and hurriedly got down on my knees, facing my door.

Fuck, was I a sissy.

The sound of footsteps came towards me.

The stall door opened and a large man… in priest attire… walked in. He latched the door, undid his belt, pushed down his pants and underwear and said, “Get sucking, sinner.”

I was flabbergasted.

Priests don’t have sex.

I stared at his smallish, but thick cock.

“Now, sinner,” he demanded.

“Yes, Sir,” I replied as I took his flaccid cock in my mouth.

“Such a dirty sinner,” he sneered, as I got his cock nice and hard, still in shock that I was sucking the cock of a priest. Not only that, but one who appeared to despise me for doing so, even though this was his own request.

Once he was hard, I began bobbing on his cock, which was under five inches and therefore one I could easily deep throat.

“Take it all, you demon sucker,” he said, which only added to the weird surreal encounter. If I was a demon sucker, what was he? Certainly not any kind of saint.

Yet I just focused on sucking his short, fat cock.

Over the next couple of minutes, he said a few more things including, “I need to save you, sinner,” and “Suck it Devil’s child,” and “You’re a dirty dick sinner.”

Soon afterwards, “Sinners like you must be baptised pure,” he groaned as I bobbed on his cock, sensing he was close.

He then pulled out and declared, as he jerked his cock off, “I’ll baptise you with God’s cum.”

I closed my eyes, having learned my lesson from the glory hole cum shot to the eye, and waited.

“I’m your saviour,” he claimed loudly, as he grunted, and I felt his warm cum splattering my forehead.

The entire load seemed to have hit just my forehead, and then I could feel it dripping down my face.

“Saved,” he pronounced a moment later, as his cum slithered down across my eyes and nose.

“Thank you,” I replied absurdly.

“You’re welcome, son, you’re forgiven,” he absolved me, seeming to believe he really had saved me in this most unorthodox way, and weirdly forgiven me for the sin of getting him off!

I heard his zipper, and then the outer door opening and closing.

I scooped cum off my left eyelid and reached for the toilet paper.

I closed the stall door he’d uncaringly left open, and wiped the cum off my face.

Fuck, that was weird.

Yet it had turned me on.

I cleaned my face with toilet paper as best I could before leaving the stall and walking over to the mirror. I wiped the rest of the cum off me: I’d missed some on my cheek, forehead and hair.

I then washed my face, examined my hair thoroughly and headed out.

Figuring I was already in the restaurant and kind of hungry (as I realized I hadn’t eaten anything yet today except for three loads of cum which were satisfying, but not filling), I ordered a burger and fries and a chocolate shake.I sat down and waited, gazing at the app. There were a couple dozen coloured dots all over the place.


I ate my lunch and was just finishing when I heard the unique beep (I needed to change that sound). I looked around as I heard the same beep coming from a couple of other places.

I tapped on the blinking red light. I was surprised and disappointed to see it was already taken.

I looked up and saw a guy hurrying out of the restaurant. Was he a cock sucker? Was he rushing off to take my load?

Then I realized how pathetic I was to be dismayed at someone else getting ‘my’ load first.

I examined the app and saw more blues than anything else, which also disappointed me. That meant there was noticeable competition for cock… something that had never occurred to me as being an issue.

I finished eating and headed out… unsure where to go.

If today was my cock sucking day, I felt compelled to suck as many cocks as possible. I had only sucked two cocks… taken three loads… thus I needed at least one more to fulfill the bare minimum of Mistress M’s expectations.

I decided to drive downtown, where I saw a large amount of reds. Makes sense… it’s full of office buildings.

I parked, and my phone buzzed before I even got out of my car. I urgently clicked on it and responded I was available.

A moment later I parked near the address, which was on the top floor of a downtown building.

I walked the single block, went into the building that I saw housed only law offices, and rode up the elevator, my mouth watering.

I walked out of the elevator and was startled to find myself instantly face to face with a secretary/receptionist.

The beautiful brunette asked coldly, “May I help you?”


“Um, I, um…” I began.

“Are you Mr. Dawson’s cock sucker?” she asked, rather matter-of-factly.

My face burned the darkest shade of red ever, I imagine. I whispered, shame coursing through me at admitting to her I was here to suck cock, “Yes.”

“You may go right in,” she said, pointing to a door. Her words and actions were professionally courteous, but her demeanor was anything but. This woman was making it painfully obvious that she didn’t approve of me at all.

“Thank you,” I whispered sheepishly, walking past her, wondering how the conversation would have continued if I hadn’t been Mr. Dawson’s cock sucker, but a client.

I entered the room and saw a large man sitting at his desk. He ordered me, barely looking up, “Crawl under my desk.”

“Yes, Sir,” I nodded, realizing he would have to move his chair back to allow this, as the front of the desk was solid oak.

As usual, shame and lust coursed through me as I obeyed.

He rolled his chair back, stood up and pulled down his pants as I crawled under the desk into a surprisingly roomy space.

He sat back down and slowly rolled his chair forward and told me, “Turn your phone off.”

“Yes, Sir,” I obeyed, pulling out my phone and switching it onto silent.

He then instructed, “Take your time under there for the next while.”

“Okay,” I said absurdly, as I got onto my knees and crawled between his large legs. It was a little dark, but when I saw his dick, I gasped. It was huge, and completely flaccid.

“And be completely silent,” he added. “I’ll be on a skype meeting for a bit, and then hosting an actual meeting.”

“Okay,” I repeated, as my humiliation increased. I was now no more than a dirty little secret.

Nevertheless, I leaned close and took his fat head into my mouth.

I swirled my tongue around just his cock head, figuring I would obey him and take my time.

It was a couple of minutes in, his cock semi-erect, when he spoke. “Good afternoon, Jody.”

A female voice responded from his computer, “Hey, Jerry.”

And for twenty minutes he and Jody chatted about some Asian merger while I sucked his cock. I got it hard. I bobbed slowly. I took it out of my mouth and licked it up and down. I took it back into my mouth.

Once he logged off he said, “Nice job, cock sucker. Now suck on my balls until my next appointment arrives.”

“Yes, Sir,” I agreed obediently, as he slid down a bit and I cupped his big balls in my hand. I’d never sucked balls before obviously, nor had I ever had my own balls sucked… so I had no idea what I was doing.

I sucked his bag into my mouth and searched around for a testicle. Finding one, I sucked it into my mouth and swirled it around. It felt weird.

After a minute or so, I did the same thing to the other ball, although that one was harder to find.

The door opened and the secretary’s voice said, “Mr. Pender is here.”

“Great, send him in,” Mr. Dawson replied.

“Back to sucking,” he ordered me in a soft voice.

I slid my tongue back up his cock and took it back into my mouth… curious how long I had been down here already and how much longer I was expected to remain.

And for twenty minutes, I slowly bobbed.

I tuned out the conversation after a few minutes, and simply focused on sucking.

To my surprise, he uneventfully shot his load in my mouth in mid-conversation.

I swallowed it all and kept sucking… for only a few more minutes, before the meeting ended.

Once we were alone again, he rolled out and said, “Thanks, cock sucker.”

“Thanks, Sir,” I responded, crawling out, my knees sore.

As I stood up he asked, “Do you need validated parking?”

“No,” I said.


“Okay,” he said, resuming his work.

I walked out and the secretary glared at me with a look of extreme judgement, as I walked past her and waited for the elevator.

It took forever to arrive.

Once I was on it, I checked and saw I had missed a call from Paige.


I called her back, but it went to her machine.

I sighed.

I got into my car and began driving home, but when I was about ten minutes away, I got another text: Looking for a cock sucker now! You available?

The missed call from Paige should have been a warning not to sink too deep, yet I was already responding to the text: Yes!

He responded back: 4214 41st Street. There are two of us.


The idea excited me.

I responded: On my way!

I used my GPS and saw I was only three minutes away.

Three minutes later, I parked a few doors down.

I walked up to the house and was surprised when a woman in her forties answered my knock. She smiled teasingly, “Hi, cock sucker.”

“Hi,” I said, now having been called a cock sucker by two women today.

“Come on in,” she said, dressed casually in a knee-length loose skirt and a t-shirt.

“Thanks,” I said, following her in.

“Take your shoes off,” she ordered.

I did… my nylon clad toes now in plain view, although she didn’t seem to notice.

I followed her into a living room where two guys, both about my age, were watching television.

“Hey, man,” one called out.

“Hey,” I said back.

“Do you mind if my wife watches?”

“No, that’s okay,” I said, shocked a wife would want to watch.

“Great,” he said, as both guys stood up and pulled down their pants and underwear.

I was happy when they remained standing, as I wordlessly went to them and dropped to my knees.

Both cocks were a decent size.

Six inches.

I took one in my hand and the other in my mouth.

“That’s it, cock sucker,” the wife approved. “Suck that cock.”

The husband told me, “She really enjoys watching me get blown by another guy.”

“No, I love watching faggots sucking cock,” she corrected, as I tried to multi-task.

“She can also be a bit foul-mouthed,” he added, as I began bobbing on his hard cock.

“My turn,” the other guy said, so I moved to the other cock and sucked it while stroking the first one.

“What a cock whore,” the woman derided me but in a friendly way (completely opposite to the stone-faced secretary), which I couldn’t argue, since I was serving two cocks while a woman watched me, and my focus was strictly on the cocks.

After a minute, I returned to the first cock and she asked, “What do you do for a living, cock sucker?”

“I’m a teacher,” I answered, before taking cock number one back into my mouth and not even thinking of lying.

“Of course you are,” she chuckled harshly.

When I switched back to cock two, she asked, “Married, cock sucker?”

“Engaged,” I answered.

“They’re all married or engaged,” she observed, amused, as I deep throated cock two.

“I prefer married cock suckers,” the guy I was bobbing on said.

“Yeah, they’re always better cock suckers,” the first guy added.

When I switched back to cock one, the wife asked, “How long you been a cock sucker?”

“Just a couple of days,” I answered, before deep throating cock one.

“Wow,” the husband groaned. “Then you’re a natural.”

“Hey, he’s wearing pantyhose,” she scoffed, finally noticing my stocking feet.

“No way,” the other guy said.

“He’s a sissy cock sucker,” the husband pointed out.

“Take off your pants, sissy,” the woman ordered.

I took cock one out of my mouth, stood up and with very little shame after the experiences I’d had so far today, pulled my pants down and off.

“Pink panties, too,” she observed, as I returned to my submissive position on the floor and took cock two back in my mouth.

“He’s quite the cock sucker,” the husband said, as I stroked his cock while sucking the other.

“Maybe you two can spit-roast him.” The wife suggested. “Obviously he’s a complete sissy fuck slut.”

Her nasty words turned me on, but I wasn’t sure I was ready for a cock in the ass… although I was intrigued about what the difference would be from the dildo or vibrating cock that had already been in my cunt.

“What do you think, sissy?” the husband asked.

“Maybe another time,” I answered, as I moved to his cock. “Today I’m just a cock sucking cum bucket.”

“And a faggot,” the wife added.

“Not exactly: I’m a cock sucking sissy,” I corrected her, before taking cock one back in my mouth.

And for a few minutes I went back and forth from cock to cock… until cock two said, “I’m going to come soon.”

“Both of you give our sissy your loads all over her face,” the wife ordered with a moan, as I glanced back and saw she was fucking herself with something. I couldn’t see the action or what she was using because of her skirt; I wasn’t complaining though: I was already occupied, in both senses of the word.

“Sounds good,” guy two said, as he began jerking off in front of me… the husband followed suit and I was now facing two loaded pistols getting ready to shoot.

I opened my mouth, extended my tongue and watched, in complete lust for cock. I could have closed my eyes to avoid another cum shot in the eye, but instead I wanted to watch these cannons blast.

It was the husband who came first, with a massive wad hitting me directly between my eyes… thankfully.

I closed them and felt the warm cream coating my face.

“Oh fuck,” the other guy grunted and just as one finished unloading all over me, the second one began firing his load, hitting me directly in my open mouth.

“Yes!” the woman screamed from behind me as she sounded like she was coming from watching me get two facials… weird.

The next few ropes hit my cheek and chin before guy two shoved his cock back into my mouth and I resumed sucking… swallowing everything that had landed in my mouth, and retrieving any late swimmers.

When he pulled out they both sat down, their cocks still out, and I stood up, feeling completely drenched with cum (I would learn later that a mere two loads wasn’t getting drenched, but that lesson wasn’t yet).

She said, “Come here, faggot.”

I obeyed.

“Suck my dildo clean,” she ordered.

Oddly, this seemed more like cheating than sucking two cocks and taking facials. I said, “Sorry, sissies only suck real cocks.”

She stood up and shoved the dildo into my mouth, “Nope. Sissies suck any cock.”

I gagged as she shoved it deep into my mouth and I could taste her cunt juices.

She pulled it out and ordered, “Don’t move.”

I wasn’t sure what she had in mind, but she returned a moment later, typing into her phone. She handed it to me, “Enter your cell.”

“Okay,” I agreed nervously, and saw she had named me SISSY COCKSUCKER. I couldn’t argue with that.

I handed it back to her and she ordered, “Pose for the camera.”

“Please, no, don…” I began, but was interrupted.

“Now, slut!” she demanded harshly.

I looked into the camera and she took a couple pics of me.

She then showed me one. “I’ll send you one for yourself.”

“Thanks,” I said, surprised that there was less cum showing than I had assumed… although I was no doubt wearing cum.

“We’ll be in contact when we need a sissy cock sucker or perhaps a maid for my girls’ night,” she said.

“She’d be perfect to test your toys on when you have your next sex party,” the husband suggested.

“So true,” she nodded, as I stood there, not knowing what to say; at this point I had no idea what I would be willing to do as soon as tomorrow, let alone several days from now. After a moment she waved me off, “You may go.”

“Thanks,” I said.

“For what?” she asked.

“For allowing me to be a slut for your husband and friend,” I replied, sounding so pathetic.

“You’re welcome,” she laughed, before dialing her phone and bragging to someone, “You won’t believe what we just did!”

“Thanks, guys,” I said to the two guys and headed out.

I was walking back to my car when a girl jogged past me. I kept my head down and I don’t think she saw my cum-coated face.

In my car, I used a wet nap from the glove compartment to get the cum off before driving home.

Fuck, I was pathetic.

Yet, God was I hard.

That said, I decided I’d had enough cock for one day, and logged out of the app. I considered deleting it completely, but I didn’t.

I ate dinner.

I went out to meet some friends for pool.

Then it was ten at night, I was driving home when I remembered Mistress M’s PS. There was a bathroom in the engineering building where I could get some black cock.

On such a wild day where I had sucked a fair amount of cock… been outed by a neighbour… been baptised and forgiven… and had kind of reverse cuckolded a stranger with her husband… I hadn’t had a single black cock.

So I drove to the college, assuming there wouldn’t be anyone there at this time of night.

I’d let fate decide whether I sucked another cock tonight.

I arrived and walked up to the top floor. I took a deep breath… excited in hopes of finding a black cock to suck, but assuming the bathroom would be empty.

It was 11 o’clock during the Christmas break. Almost everyone would be home with their families.

I opened the door and gasped.

It wasn’t an orgy… but it was still wild.

A white older man was on his knees servicing two black cocks in front of the urinals, and a college-age white guy was bent over the counter getting hammered by a large black man.

“Come on in,” offered one of the guys getting serviced by the old guy.

I walked in…. my cock instantly hard, and my only thought was of black cock.

“Cock sucker or bottom?” the guy asked.

“Cock sucker,” I identified myself, no shame in my tone, as he turned towards me to reveal his massive, black, fat cock.

“Fuck, pound my asshole with your big black cock,” the college boy begged in a tone that sounded so lustfully desperate.

“First time here?” asked my greeter.

“Is it obvious?” I asked, my head going back and forth from his massive cock to the rough sodomy occurring a few feet away.

“Your yoyo head movements say so,” he said.

“God, I love your big cock in my asshole,” the bottom whimpered, as he looked to be in complete sexual euphoria… a look I’d never seen on any woman I was with.

“Want some chocolate?”

“Yes,” I answered, my head still moving back and forth.

“Well, get over here,” the guy said, wagging his hard cock at me.

I walked the few steps, looked at the older dude sucking the other cock, as I lowered myself before the massive member.

“That’s Professor George,” the guy explained.

“Oh,” I said, that meaning nothing to me other than he was a Professor.

“Tell me what you are,” the fat black guy demanded, as he stopped fucking the desperate dude.

“Your white fuck toy,” the dude declared.

My black guy slid his cock in my mouth as he said, “And that bottom is a minister’s son.”

Wow, I thought to myself as my mouth was spread wide by the big, fat, black cock.

“What do you worship?” the fat guy asked his bottom, as I began bobbing on the biggest cock I’d sucked yet.

“Black dick,” the bottom declared.

God, I wanted to watch him get fucked… it sounded so amazing.

It was so hot.

And oddly, it didn’t seem gay at all.

“Who’s your God?” the fat guy asked as he resumed fucking him, based on their loud, guttural sounds.

“Black cock and cum,” the dude whimpered loudly.

“Focus on my cock, cock sucker,” my black guy said, “unless you want to be the next one bending over.”

Not ready for that, although the idea was getting more and more enticing, I focused on his cock, just as the guy standing beside me grunted and said, “Swallow it all, Professor.”

I bobbed.

Every few bobs I tried to take a little more in my mouth.

I heard the door open.

I had no idea whether someone was coming or going and I didn’t care. At the moment I had only one task: to worship this black cock and extract his chocolate cream.

A minute later the door opened again.

“I’m going to come in your ass, faggot,” the top guy said.

“Do it. Fill my ass with your cum,” the bottom dude pleaded.

“That will be you one day,” my guy told me as I was now taking over half his cock in my mouth.

The idea made my cock flinch in my pants.

God, part of me did want to get fucked.


That said, I didn’t think some massive black cock should be my first. Eventually though: I needed to keep preparing my pussy for such cocks.

“You’d like that, wouldn’t you?” my guy asked, as I began to bob faster.

“One day,” I admitted, “maybe even soon,” ever so briefly taking his cock out of my mouth to respond.

“Yes!” the bottom dude screamed as I assume he was filled with cum.

“White boys only have two purposes,” my guy continued not unkindly, but as a man of the world explaining things to a novice, as he grabbed my head and began face fucking me. “To suck cock and to get fucked.”

“And to bring us their white sluts,” some new guy added.

“Well, of course, and that,” my guy chuckled, making his cock vibrate in my mouth slightly.

Paige had had a black boyfriend, and I now remembered her saying he was bigger than me… but she never said how big.

I focused again on breathing through my nose, as my guy pumped his monster in and out of my mouth, although never trying to shove all ten-ish inches in me.

He pulled out a minute later and in seconds splattered my face with his cum… as I closed my eyes just in time to avoid another eye reddening.

As soon as he was done, another guy, don’t ask me who, shoved his cock in my mouth and I mindlessly began bobbing.

“Let’s give the first timer a black cum baptism,” one guy said.

“Text bukkake,” someone else said.

Bukkake? Oh my God!

How many guys are going to show up?

How many cocks will I be expected to suck?

How many loads will splatter my face?

Even as I asked myself these questions, while bobbing on cock two, I hoped: a lot, a lot and another lot.

And that’s how I ended up sucking nine black cocks in the next thirty minutes.

That’s how I took nine more loads on my face… and in my hair and on my clothes.

Most of the cocks I never even saw.

I didn’t see any of the guys’ faces.I just sucked whatever was shoved in my mouth… and I jerked off whatever was placed in my hands.

I became a complete, bimbo, cock-sucking, cum-craving slut.

I was a sissy.

I was a cock sucker.

Maybe I was even a faggot.

I just wanted cock.

I just wanted cum.

I just wanted to please.

Every cock.

Every load.

“Thanks faggot,” someone said, when I finally had an empty mouth for more than a few seconds.

“Thank you,” I replied, as I scooped some of the cum from my cheek and put it in my mouth.

So good.

“Eat it all, cock sucker,” someone else urged me.

And I obeyed, scooping cum off my face for a couple of minutes as I ate a mixture of many guys’ loads.

So fucking good.

“Oh, God,” a voice whimpered.

I scooped the cum from my eyes and finally opened them.

The bathroom was almost empty.

No one was in view. Just two pairs of legs in a stall.

I stood up and walked over to a mirror.

My hair was coated in cum.

My shirt had white stains all over it.

I listened briefly, “So big,” some guy, most likely white, moaned.

Fuck, I was going to have to try a cock in my cunt, and soon.

I listened a little longer as the guy began moaning like a bitch in heat, before I walked out and headed straight to my car.

It wasn’t until I turned the car on that I learned I’d been in there for over an hour.


I really was a sissy.

I saw a black man walk into the building and was tempted to get back out and follow him in… but I resisted.


DAY 10: Thursday the 3rd

I woke up the next morning, actually it was 12:30 in the afternoon, following my marathon suck fest at the college, and I replayed yesterday.


I was a massive cock slut yesterday.

Just thinking about it made my cock hard.

So I headed downstairs for Day 10, a little sad there were only three days left.

I went downstairs and eagerly opened Box 10.

It contained a fleshlight and lube.

I read the note:


I bet you sucked more than three.

I bet you ended up in the black bathroom.

I bet you are craving cock and cum right now.

Yes, yes and yes, I thought to myself.

Today no sucking cock.


Today you will practice self-control.

You will watch porn and use the fleshlight.

You will bring yourself to the brink of coming… and then stop.

Wait for an hour and do it again.

You will do this at least six times today.

This is called edging, and it’s an important part of being a sissy… Self cock control.

Mistress M

I took the fleshlight and lube and went upstairs and turned on a hot lesbian scene with Whitney White and Penny Pax called ‘The Sex Addict’ (it seemed appropriate).

I lubed up my cock, slid it inside the fake pussy and slowly masturbated.

I wasn’t even five minutes into the video when I was close to coming.

So I stopped, barely in time.


I won’t bore you with the details, but I repeated this three more times that afternoon, my cock aching, and was making supper when Bill showed up.


He asked, “Hungry?”

I replied, “Not today.”

He laughed, “It was a rhetorical question, cock sucker.”

“Bill, I can’t,” I objected.

“You can and you will,” he insisted, as he saw today’s note on the table and picked it up.

“Bill, no,” I panicked.

But he read it.

“What is this?” he asked.

I sighed. I then explained everything, leaving out a lot of the details, like how many cocks I’d emptied yesterday.

“No way,” he said.

“So you see, I can’t suck you today,” I insisted.

“Okay, I’ll respect that,” he finally agreed as he pulled his pants down. “But you can still jerk me off.”


“Yeah, I’m horny and I can still give you a nice facial.”

“Okay,” I said, arguing to myself that I would be obeying Mistress M and still be getting the thrill of a load on my face.

I dropped before him and jerked him off.

Not going to lie… as soon as I was on my knees, I wanted that sucker in my mouth.

I imagine like a dieting fat woman with a cake a few inches in front of her.

Thankfully, he didn’t last long before he came on my face.

Once done, he said, “I’m gone for the weekend, but when I get back I’ll be texting you and I expect you to be ready to suck my dick.”

“I will,” I nodded, as I felt his warm cum cooling on my face.

He walked out, and I went and washed up.

That night I marked papers and edged myself twice more to the point my dick was aching… and for the first time ever, I had blue balls.

It sucked.

But I sensed this training would be rewarded tomorrow.

Or at least I hoped so.

DAY 11: Friday the 4th

When I awakened in the morning, I found a text on my phone from Paige: Here’s a little something I picked up for us in Amsterdam.

She’d attached a photo of herself, naked except for a large, black strap-on. She was holding a ruler next to it, demonstrating it was a hearty 10-incher.

I immediately texted her back. WOW! I can hardly wait for my stud of a fiancée to get home.

I headed downstairs, still a little raw down below, and realized someone had to have taken the picture of Paige with the strap-on.

Who could have taken it?

I went back upstairs and texted, dying to know: Who took the picture?

I stared at the screen for a minute or two waiting for a response, alas didn’t get one, and headed back downstairs on my original mission.

To open Box 11.

When I did, I was slightly disappointed.

It was empty again, except for a note.


Today you will be rewarded for yesterday’s obedience.

You will go to Diva’s Salon at 1PM. You will be occupied there for a least couple of hours… perhaps much longer.


Mistress M

What else could be done to me at a salon?

I’d already had a complete body Brazilian. I didn’t think I needed a perm.

I arrived on time and headed inside. Except for my panties and pantyhose, I was wearing ordinary guy clothing.

After establishing I was the Kendra Winston they were expecting, I was taken right back to a room, where I was left by myself after being told to remove my shoes and socks.

I did, and then assumed my pantyhose would be an issue, so I removed my jeans and pantyhose and then put my jeans back on, stashing the pantyhose in my knapsack.

Shortly afterwards someone led me to a larger room containing several stations, most of them occupied by women.

I was then given a manicure and pedicure.

I’d always assumed these were just for girls, but the pretty woman who did both for me explained that twenty percent of her clientele was men. And once they’d had one, they usually came back.

I could see why.

It was relaxing.

Especially the pedicure.

The hot water.

The massage.

The pumicing away of dry skin, especially from my heels.

The feet in a cozy warm bag.

It was weird, sure.

But man, was it relaxing.

They then trimmed and filed my nails.

Then… the first surprise… they painted my toenails.


I thought about questioning it, but I didn’t. I assumed this was what was already paid for. What Mistress M had instructed them to do.

This was going to be even tougher to explain than the Brazilian.

Once done, the manicure followed, although thankfully they didn’t paint my nails.

I was thankful for only a couple of minutes however, before they glued on fake ones, also red.

It hurt.

All of this was done without a word, although I did get a few peculiar looks from the other female clients. (Yes, I do realize that phrasing implied that I too was female.)

Once that was done, the woman ordered me to follow her and she took me into a room that seemed to be a photo shoot area.


The woman instructed me, “Wait here. Amanda will be right with you.”

“Okay,” I said, wondering what was about to happen.

Of course, it should have been obvious.

Amanda walked in, a large but pretty woman, and said, “Welcome, darling.”

“Thank you,” I said.

“Ready for your photo shoot?” she asked.

“I had no idea I was doing one,” I admitted.

“Well, that’s why you’re here, silly,” she laughed in a boisterous way that made the room echo.

“So it seems,” I said awkwardly.

“You’re cute,” she said, as she did a complete 360 around me that took at least a couple of minutes. She then ordered, “I think I have the perfect outfit to start for you.”

“Okay,” I agreed with trepidation.

“Follow me,” she ordered.

I did, into a room that was deceptively large, filled with many racks of clothing, for both men and women.

She said, before disappearing into the abundance of clothes, “Please remove your shirt and jeans.”

“Um, okay,” I said, this feeling very weird.

I was soon standing in a room wearing only my pink panties, my dick awkwardly hard, for a couple of minutes before she returned.

She looked at me and smiled again, “Cute, very cute.”

My face burned with shame at being seen in no more than pink panties. At least I wasn’t wearing my pantyhose.

“Okay, first let’s get you some titties,” she said.

“Titties?” I asked, as she studied my flat chest.

“Want big ones?” she asked, before laughing, “of course you do, they always do.”

She went to a dresser and pulled out what looked like two breasts and returned. “Completely shaved chest, good. Trust me, you don’t want any hair when these girls come off.”

“Good to know,” I joked awkwardly.

She then grabbed the breasts and held them to my chest. She adjusted their placement for a good couple of minutes before ordering me, “Hold them right there please, and don’t move them at all.”

“Yes, ma’am,” I obeyed, looking down and thinking Man, am I stacked. Then shaking my head slightly at my silly thought.

She grabbed an eyeliner pencil and returned to draw a circle around each breast.

She grabbed a spray can, shook it, and sprayed the back of the breast (I would later learn they’re called ‘breast forms’ in case you were wondering… I mean if you’re still reading this story, you may be a sissy too, and will want to experience this for yourself).

She then placed each breast directly in the drawn circle.

To my surprise, after about thirty seconds she removed them.

She then added something else I would later learn was called Skin Tac both to the back of the breast and to my chest. She said, “Now we wait five minutes.”

“Oh, okay,” I said, still finding it weird to be here with her in my panties only.

She walked back over to the dresser and returned with a pair of mocha stockings and a garter-belt. “Here, put these on.”

“Okay,” I said, completely overwhelmed by what was happening.

I put the garter on and then the stockings. As I did, she came over and helped with the clasps saying, “No dear, the suspenders go beneath your panties.”

Once on, she came over and pressed the breasts back on me, after positioning each one carefully.

She backed away and studied the effect. “Perfect,” she said. I wished there was a mirror for me to look at myself.

She grabbed a pink bra and fastened it on me.

“Very pretty,” she nodded, as she brought me a dress. A gold dress.

She draped it over my head and zipped me up.

She walked away and returned to place a curly blonde wig on me.

She then had me sit down on a short stool and brought me a pair of silver five-inch heels. “Put these on.”

I did.

“Are you ready for me?” a pretty Asian girl asked as she came in.

“Perfect timing,” the woman said. “Doll her up.”

“Yes, ma’am,” the girl nodded. She walked over to me and for twenty minutes or so, she did my make-up. My eyes, my cheeks, my lips.

“Amazing,” Amanda approved, coming back in.

“Thank you, ma’am,” the girl said, standing up and leaving.

“All right,” the woman smiled, “now let’s take some photos.”

“Okay,” I said, speaking for the first time in an eternity.

I followed her out and saw there’d been a backdrop set up since I was last out there.

“All right,” she said. “We’ll take some simple ones first.”

“Okay,” I said, walking to the backdrop, which looked like it was a red carpet for the Oscars.

“Start at the end and strut towards me,” she ordered.

I obeyed, trying to draw out my most feminine walk.

“Nice, good, good,” she said approvingly, snapping picture after picture.

“Now pose,” she instructed.

I did… really getting into it. I posed in a variety of positions, all while imagining I was a beautiful female celebrity.

She took tons of pictures.

“You’re a natural sissy,” she complimented, using that term for the first time.

Feeling so free and wild, I joked, “You should see me with a cock.”

“I could make that happen,” she replied without missing a beat.

“You could?” I asked, as she nodded and handed me an envelope.

I opened it. It was from Mistress M.


Enjoying yourself? Of course you are.

The PG photo shoot is done.

If you don’t want to do any more, you may call it a day.

On the other hand, if you feel adventurous and really want to explore your inner sissy slut, just tell Amanda, and she will do a much wilder photo shoot with a live model or two.

Be warned: there will be photos taken and you will almost certainly have a cock or two in both of your holes.

But this is up to you.

PS: The photos will be yours to keep and won’t be used anywhere else (unless you give permission, as these photo shoots can be sold for a couple thousand dollars; ten grand if you’re willing to have it all filmed and posted online)… although I will also receive copies, as will your benefactor.

Mistress M

PS: If you agree to this additional shoot, you may come.

Holy fuck.

My cock is hard as fuck.

I have permission to come.

I can suck cock.

I can get fucked by a real cock.

I can become a full-blown sissy.

I realized my initial thoughts were all about the sissy side… and almost nothing about the risk.

“So?” Amanda asked. “Are we done here or no?”

“I don’t know. How would it work?” I asked.

“I’d give you a few choices of stories and actors, you would make your choices and then act it out,” she said. “I would take photos and if you wish, it could also be filmed.”

“Wow!” I said.

“It’s a once in a lifetime opportunity,” she said. “Should I show you the options?”

“Please,” I said; it was at least worth seeing them.

She handed me a thin binder and said, “I’ll be back in five minutes.”

“Okay,” I said, as I opened the binder.

SCENE 1: Gloryhole Surprise

You go to the washroom, sit down like a good girl and are surprised a minute later when a nice cock pops through a hole you hadn’t noticed. You, of course, become intrigued, stroking it first. Then sucking it. Climactic cum shot is either:

a. He warns he is close, and you jerk him off and take a nice facial.

b. He comes into the stall, fucks your mouth and coats your face with his load.

Oh my!


It was intriguing, but truth be told, I’d already done that.

SCENE 2: Step-dad’s Dick

You come home late from a party dressed in drag. You wake up your step-dad and he tells you angrily if you want to dress like a slut, he will use you like a slut.

Note: this one includes simulated rape and will have you roughly face fucked and thoroughly ass fucked.

Cum shot can be on face, on ass, or in ass.


The idea of just being taken was kind of hot.

Plus, it would get me past the insecurity of taking a real cock in the ass.

At the moment, this was exactly what I wanted: to suck a cock and to get fucked like a slut.

Before making this choice (if I was going to make a choice… although let’s be real, was there ever really a question about it?) I figured I should check out all the scenarios.

SCENE 3: Black Attack

You’re a teacher in your classroom. Two black students come in and are upset with their grades, calling you a racist. You defend your grading practices, but offer them a chance to improve their grades by doing some extra-credit work. The students decide to improve their grades by spit-roasting you.

Of course you protest, but once they show you the size and majestic beauty of their black cocks, you give in.

Cum shot options:

a. Double facial.

b. One facial one in ass.

c. One facial one on ass.

d. Two loads in ass.

Holy shit.

This was one of my actual fantasies that I jerked off to, on occasion.

To be seduced and taken at school.

Blackmailed or bullied into sucking cock… it didn’t necessarily have to be black cock, but that added detail did indeed enhance the fantasy.

This one was the sure-fire winner.

Yet I kept flipping through.


You arrive home and your sister’s boyfriend is there. Since you’re in drag he sees that you’re a sissy and decides since your sister is on her period, he should use you. He dresses you up in your sister’s cheerleading outfit before using you for his own pleasure.

Variation: Sister is involved in making you a slut.

Cum shot: Face, asshole, or if using the variation, sharing a facial with your sister or even licking the cum off her ass, pussy or face.

Again, this was hot, but not as hot as scene three.


You walk in to see your wife getting fucked by a younger woman with a strap-on. The girl takes control and forces you onto the bed where she takes turns using both of you.

Cum shot: if you cum, you do it on your belly and they feed it to you with their fingers.

That would be an amazing fantasy come true if I walked in on that situation with Paige.


Your wife is working late and you go to drop off supper for her, but you walk in on her getting fucked by her boss. She demands you come over and watch. The boss fucks your face and your ass while your wife watches, and you are humiliated. It ends with your wife catching the cum and sharing it with you via snowball.

Variation: This could be done with an interracial slant if you wish.

Again, this was quite hot. Although the idea of tasting another woman seemed like cheating.

Now I know this is all cheating.

Yet, in my pathetic sissy mind, everything I was doing was something I couldn’t do to Paige, so I rationalized it wasn’t cheating.

Again, I know… pathetic.

But at the moment I was being led by submissive lust, not common sense.


You’re cross-dressed and in the girls’ washroom fixing your hair when a very pretty girl walks in. She too is checking her make-up in the mirror and notices you staring at her. She confronts you, pushes you down to your knees and surprises you with her cock and ends up using both your holes for her personal pleasure.Cum shot options: She, not you, decides where to shoot her load.

Damn it.

Now there were two scenes I was dying to do.

Well, in truth I’d love to do all seven.

But a shemale was the ultimate attraction.

I could admire her feminine beauty and still enjoy her masculine cock.


I was re-reading scenes three and seven when Amanda returned.

She asked, “Make a decision?”

“It’s hard,” I said.

“I bet it is,” she mused, peering down at my crotch.

I laughed, “Well, that too.”

“Which ones are you most intrigued by?” she asked.

“Just the first seven,” I joked… well, kind of joked.

“One scene is paid for already,” she said. “Any extra ones you want to create will come out of your own pocket.”

“Wait a minute. Isn’t this prostitution?” I asked.

“No, because we’re filming it. If call girls always brought a cameraman and some lighting along, maybe they and their clients could avoid any legal difficulties.”

“Interesting thought. How much?” I heard myself asking.

“Seven hundred for a one-actor scene,” she said, “plus two hundred more per extra.”

“That’s not bad,” I said, thinking that over time I could enjoy doing a few of these.

“It’s very reasonable,” she said, before adding, “and any scene is free if you’re willing for us to post the pictures online, and if you allow the video to go online, you can walk away with ten grand in your pocket.”

“Wow!” I said. “Well, let’s start with just one and go from there.”

“Which one?” she asked.

“I can’t decide between scenes three and seven,” I admitted.

“Two very different scenes.”

“I know.”

“If you want to do the shemale scene, we can do it in the outfit you’re currently wearing and begin in a few minutes,” she said. “The classroom scene would have to be tomorrow or another day.”

“Well, shemale scene it is then,” I said, deciding I was definitely doing one now.

“Great,” she smiled. “You have only two model choices who are available right away for this one.”


She grabbed another binder and handed it to me. “Only Zoey and Channa are available now. Angela or Kim could be later tonight, and Winnie is out of town for a few days.”

“Oh, okay,” I said. I looked in the folder to see three pictures of each girl: One fully clothed, another showing her topless, and the last one a close-up of her cock.

Angela was a blonde beauty with an average sized cock and big tits.

Channa looked Filipino with small tits and a seven-inch cock.

Kim was Asian, very elegant and pretty, with small tits and a small cock.

Winnie was a brunette who looked a lot like Angelina Jolie, with huge tits and a massive (frighteningly big) cock.

Zoey was a gorgeous redhead with big firm tits and a nice eight-inch cock.

It was a no brainer.

“I choose Zoey.”

“She’s very aggressive,” Amanda warned.

“Good,” I said.

“Okay. Wait here,” she said. “Someone will come and get you in a few minutes.”


Then I waited.

Was I really doing this?

Of course I was.

It was then I realized I still had no idea what I looked like.

I looked around and saw there was a bathroom near the hallway entrance. I walked into it and looked in the mirror.


If it weren’t for my Adam’s apple, there would be no evidence I was a guy.

I looked… hot!


My chest was voluptuous.

My make-up feminine.


I wished there was a full-length mirror, so I could enjoy the entire package.

I stared at myself for several minutes, in awe of the transformation.

“Kendra,” a voice called out, drawing me out of my daze.

I walked out and froze.

It was Amy.

A student of mine. She was an excellent student, was always courteous and well-spoken, diminutive, very pretty, and seemed to be well-liked. I was amazed to find such a sweet apple-faced girl working here.


“Follow me, please,” she invited, not appearing to recognize me.

I didn’t speak, I just followed her, keeping my head down.

We walked out of the room, down the hallway away from the street entrance, down a flight of stairs (as I learned this place was massive) and to one of eight rooms (I assumed each of them was for one of the seven scenes… I wondered what the eighth was for).

“Go into room three,” Amy instructed.

I nodded, avoiding eye contact as she added sweetly, “Have fun.”

She trotted back up the stairs as I walked into the room, my cheeks burning, but with a slight relief that I didn’t think she’d recognized me.

I entered a bathroom setting, an elegant one.

A nice long mirror with a sink and wide counter. Three stalls with the doors closed. A couch which would ordinarily seem out of place, but in this upscale setting, it worked.

Amanda was already there with a camera, with another girl, in her twenties, with a video camera on a tripod, who asked, “Do you want a video?”

“Sure,” I nodded, figuring it was only for me.

“We don’t script the scenes, we just go with the flow,” she explained.

“Okay,” I nodded.

Amanda handed me a lipstick and directed me, “Go over to the mirror and reapply your make-up and so forth until Zoey comes in.”

“Okay,” I agreed.

“Great,” she said, before she banged on the door I’d walked through a couple minutes earlier and called out, “One minute.”

This was really happening.

“Action,” she instructed me.

I looked into the mirror, pulled out my lipstick and reapplied.

God, was I nervous.

Although as mentioned before, I thought I looked pretty hot.

I was just running out of things to do when Zoey waltzed in as if she owned the place. Dressed in a fire red gown. She swanked up to the mirror beside me and stood there admiring herself.

I stared at her. Partly because that was the plot, and partly because she was fucking hot as hell.

She looked at me and asked, her tone harsh, as I stared at her huge tits and her hard nipples poking out against the dress (obviously she wasn’t wearing a bra), “What the fuck are you looking at?”

“N-n-nothing,” I stammered

“You’re calling my tits nothing?” she demanded, turning to me.

“N-n-no,” I stammered again, this feeling very real.

“You’re the bitch who bumped into me during the catwalk aren’t you?” she accused, glaring at me with venom in her eyes.

“Yes, I’m so sorry,” I apologized abjectly, playing along.

“Oh, you’ll be sorry all right,” she growled, as she pushed me roughly to my knees.

“W-w-what are you doing?” I worried, trying to play the role of a shocked woman.

“Teaching you a fucking lesson,” she answered, raising her dress to reveal a cock underneath it.

“Y-y-you have a penis?” I quivered nervously.

“It’s called a cock, Missy,” she corrected, wrapping her hand around it. “It’s a big cock, and you know what it needs right now?”

“No, I…” I tried to get up.

“Sit back down, bitch,” she roared, roughly shoving me back into place, “It needs a slut mouth to get it hard and ready for that cunt of yours.”

“Please, no,” I said, before she shoved her cock into my open mouth.

God this is so hot!

I swirled my tongue around her head in both fear and aroused eagerness to please as she moaned, “That’s it, slut, get it nice and hard.”

I kept using my tongue and my left hand as it hardened in my mouth.

Fuck, there was nothing better than the feeling of a cock hardening in my mouth (the vibrating butt plug being a close second).

Once it was hard, I began sucking energetically.

“That’s it, get it nice and wet for that cunt of yours,” she said. “I’m going to fuck the hell out of you.”

I bobbed faster, showing her I couldn’t wait for that… which was true… although I was also still quite nervous. Her cock was longer than my largest plug, and a similar size to the dildo so it wouldn’t rip me apart… but a real cock seemed a whole new level of submissive debauchery.

“My balls too, cock sucker,” she ordered.

I took her cock out of my mouth and slithered my tongue down her hard shaft and across her hairless balls.

I had no idea what I was doing, since Mr. Dawson at his desk hadn’t given me any feedback, but I sucked her ball bag into my mouth and just as before, found one round ball.

I sucked it into my mouth and swirled it around gently.

I found the other ball and replicated the ball pleasing.

“Now stand up and bend over,” she ordered.

I stood up, braced my hands on the counter for balance, and watched nervously as she stalked behind me.

“Cut,” Amanda called out. “Lube her up.”

The camera girl hurried over, raised my dress, pulled down my panties, lubed my asshole, finger fucked me for a couple minutes, wiggling three fingers inside (is this what really happened in porn? That would explain a lot) and then pulled out. She pulled my panties back on and returned to her tripod, cleaning her fingers with a wipe.

“All right, and… Action,” Amanda ordered.

Zoey lifted my dress up past my waist and scoffed, “Fucking panties. Do sluts wear fucking panties?”

“No, ma’am,” I apologized, as she roughly yanked them down to my knees.

“You’re a dumb fucking slut,” she said, slapping my ass smartly. She wasn’t holding back, that hurt!

It was so humiliating.

So, of course, my cock was rock hard.

I weakly apologized, “Sorry,” as I prepared to feel her cock fill my virgin hole.

She grabbed my hips, positioned her cock and slid easily in. “Fuck, only a slut is ever this wet.”

“Oh God,” I whimpered as she filled me.

She then fucked me for several minutes like I was a cheap slut made only to be used… which I was discovering might actually be my sexual calling.

It was the ultimate humiliating sexual high.

I normally loved being the one doing the fucking… but that was nothing compared to my being the receiver instead of the giver.

This is who I was.

A sissy for cock.

A bimbo for cock.

A fuck toy for cock.

And I loved it.

Each deep thrust sent intense waves of pleasure through me as I discovered how responsive my cunt was (truth be told, I was learning I had a very sensitive prostate).

I could feel every movement…. every twitch… every thrust.

It was like I was made to be fucked. I knew without a doubt I was a sissy. I knew vaginal sex alone would never again be enough for me.

Each nasty name she called me triggered increased mental euphoria because of the knowledge I was completely at her whim.

I was her bitch.

Her slut.

Her whore.

Her bimbo.

Her cum bucket.

The entire time my moans were feminine as I became my true self… as my body gave itself fully into acceptance of my sissy-hood.

I begged for more, this pleasure more intense than anything I’d ever experienced, “Oh please Miss, fuck me harder. Use me as your slut!”

I had never felt so good, and I knew I was going to come once again without having my cock touched. There was no way in hell I’d be able to control myself.

The fucking lasted only a few minutes before I could sense she was going to come… and that I might too.

“I’m going to come in your cunt,” Zoey declared, as her deep thrusts continued.

“Yes please. Fill my cunt with your cum,” I begged, as I felt my own balls boiling like the room was a hundred degrees. I was dying to know what it felt like to have cum spewed inside my no longer virgin cunt.

“Take it all, slut,” Zoey ordered, and I felt her cock twitching as she tensed up.

I could feel her cock starting to pulse in my cunt, and then a lightness and warmth as she came inside me.

This triggered my own orgasm, as I screamed, “OH, GOD!!” reaching a powerful anal orgasm and spewing my load everywhere as my cock swayed every which way from the deep, hard fucking.

I went lightheaded and almost fainted as cum spewed into me while more of it spewed out of me, and I wondered if maybe I wasn’t completely gay.

I mean I loved cock.

In my mouth.

In my cunt.

I loved cum.

Down my throat.

On my face.

In my cunt.

She kept fucking me throughout our simultaneous orgasms.

When she pulled out, she pulled up my panties and said, “You can keep my cum in your cunt as a reminder of who just bred you.”

“Yes, ma’am, thank you, ma’am,” I murmured weakly, completely spent.

She spun me around, pushed me back to my knees and shoved her cock in my mouth.

“Clean me up, whore,” she ordered, yet one more delectable humiliation as I sucked her cock that had just been in my dirty fuck hole for several minutes.

I bobbed for a couple of minutes before she pulled out, pushed me onto the floor and said, “Thanks, slut.”

As she strutted away, I said dazedly, “No, thank you.”

A moment later Amanda said, “Cut.”

“Holy fuck, that was amazing,” the other girl said.

“Did you get him coming all over the place?” Amanda asked.

“I sure did!” the girl exulted.

“This will be a huge seller,” Amanda said.

“I’ve never seen anyone come just from getting ass fucked,” the girl said.

“Me neither,” Amanda said, as she snapped her fingers and the girl immediately dropped before her, under her dress and began licking.

I stared in awe at my first live lesbian show… until I realized the girl was bobbing. I looked more closely and realized Amanda too had a cock… and (how did I miss this until now?) also an Adam’s apple.

Amanda said, “Come back tomorrow. We’ll do the black cock scene for free.”

I asked, “Really?”

“Oh yes,” she said. “You’re a natural.”

“A natural?”

“Natural porn slut,” she elaborated.

“This video is just for me, right?” I asked, no longer so sure.

“We can chat about that tomorrow,” she put me off. “This could be a huge scene.”

“Really?” I asked, more flattered than worried for some reason.

“A sissy who comes without having his cock touched is like a needle in a haystack,” she said.

“Oh,” I said.

“We may be able to turn this into a full feature movie,” she continued.

“I already have a career,” I pointed out.

“You may need to change careers,” she refuted, as she grunted and came in the girl’s mouth.

I got up and said, “I can’t believe I just did that.”

“I can’t believe how raw and real it was,” she replied.

“It was my first anal except for a dildo,” I pointed out.

“Fuck off,” she gasped.

“Seriously,” I said.

“Well, that in itself will double the popularity,” she said, as she added, “Susan, get this to editing.”

“On the double,” Susan agreed, getting off her knees and grabbing the camcorder.

“You won’t release it without my consent, will you?” I asked.

“Of course not,” Amanda said, but in a tone that told me it would be released with or without my consent. “Keep the dress and lingerie, and you can give me a call in the morning.”

I took the card she handed me, and she left.

I stood there for a full minute in a complete daze.

I had officially fallen in deep.

A minute later the door opened, and my student Amy beckoned, “Please come with me.”

I followed her up the stairs and back to the original room.

“That was such a hot scene,” she gushed as we reached the changing room.

My eyes went wide.

I stammered, “Y-y-you saw it?”

“Of course. It was streamed live into our office,” she explained cheerfully.

“Oh God!”

“Yup. That’s what you screamed when you came,” she said. “Without your cock even being touched!”

I kept avoiding eye contact with her but learned it was futile as she added, “It was the hottest scene I’ve ever seen, Mr. Winston… sorry, Ms. Winston.”


I pleaded, “Please don’t tell anyone, Amy.”

“Of course not,” she said. “What happens here, stays here.”

“Thank you,” I said.

“But I have to tell you since we still are here,” she said, “you dress up as one hot girl.”

“Thanks,” I replied awkwardly.

“And since I know a secret about you…” she offered, lifting up her skirt and revealing a rather large cock where her cunt should have been.

“Oh my,” I gasped, staring at my student’s hard cock. Is she hard because of me? She did call me hot.

“If you ever need a cock to serve at school, just let me know,” she smiled, “I wouldn’t mind having a third teacher pet.”

“Third?” I asked, shocked just as much by the big appendage between her legs as by the implication she was fucking two of my colleagues.

“Yep,” she smiled, as she put her cock away.

“Who?” I asked, curious.

“I don’t fuck and tell,” she said. “But one is male and the other is female.”

“Wow,” was all I could say as I began mentally going through all my colleagues.

“See you at school on Monday,” she farewelled.

“See you, Amy,” I said, as she walked out, and my secret sissy life was now even less secret.

I found my clothes, changed out of the dress, laboriously ripped the tits off my chest, but kept the garter and stockings on, put on my jeans and shirt, put the dress in a bag and headed home… my head spinning… what had I just done?

What could possibly be next?

Could I stop this downward fall?

Did I even want to?


Back in my car, I saw I’d missed a few text messages from Paige.

What are you doing today?

I went lingerie shopping with Mom today. You won’t believe what she bought me.

I’m learning a lot about my mother I DID NOT know.

Off to bed… a picture for you to jerk off to.

It was a picture of her wearing the same strap-on as before, but now she was also in black thigh highs and boots and a black leather bra. The makeup on her face looked completely Goth. She looked like a formidable Mistress.


Did her Mom take the earlier photo?

This photo too?

Her mother looked exactly like Paige, just in her late forties. She was a very flirty woman who touched my arm often, dressed like she was in her twenties (she dated guys in their twenties, some of them younger than me) and even had grabbed my ass twice (both times while drunk). She even joked once that if she’d met me before Paige had, she would have been “all over that” (while she pointed directly to my crotch).

So in retrospect it was obvious her mother must have been the one who took the pictures.


Nothing in my life made sense anymore.

And now that my Pandora’s Box was blown wide open, there was no going back.

The question wasn’t whether I was going to tell Paige at some point… the question was how the hell I could do it without her blowing up in my face.

I texted her back: I can’t believe your mom took that picture. What did you tell her? Does she know you are going to pound my pussy when you get home?

I pressed send and then noticed I’d called my ass a pussy.


I sent another text: Oh, my God why did I just write that? See you soon.

Since it was late on the other side of the pond, she was clearly asleep, I didn’t expect a response.

That night I tossed and turned for a while, worried what she would think of my response.

Day 12: Saturday the 5th

Tomorrow there would be no box.

Tomorrow Paige would arrive back home.

Tomorrow if my world didn’t crash and burn, everything might return to normal.

Although… what would normal now mean?

Could I go back to before these watershed days?

Could I quit sucking cock cold turkey?

After yesterday, could I resist my cravings for a cock in my ass?

Could I become straight again?

Did I want to?

Could I?

Was I going to make that second movie today?

I had just gone two whole days without a black cock.

That seemed like a long time.

Shaking my head at my dependence on these 12 days, I went downstairs to open my final box, which was larger than any of the others.

It included: a strap-on cock with a harness; a white garter-belt and matching stockings; a new butt plug; a white bra; a white thong; another pair of tits and the accessories needed to glue them in place; a red sweater; a green and red plaid skirt; a blonde wig; and finally a pair of five-inch stiletto red heels.I grabbed the last note:


Although today is the last day… it really isn’t. In truth, today is the beginning of stage two.

Stage two?

Today you begin the rest of your life.

What is she talking about?

Ready to find out who your benefactor is?

God, yes!

Ready to accept your place in the world as a cock sucking, cunt taking, sissy?


Follow each instruction in order and don’t skip ahead.

1. Take a shower and return naked to the box.

I quickly obeyed, resisting my urge to read the rest of the letter and rushing through a shower.

I wanted this final day to be special, and to last as long as possible.

I returned and read the next item.

2. Put on the garter-belt and stockings.

I obeyed, putting the garter on first, and then sliding the stockings on. Clasping the stockings to the clasps unassisted was more difficult than I thought, especially the back clasps.

So this task took me a good ten minutes to accomplish.

Like the other stockings, these were sheer silk and so fucking soft.

3. Put your tits on and then the bra (there are instructions in the box if you don’t recall the exact procedure from yesterday).

I did recall yesterday, and did it the exact same way. It took me another thirty minutes to get them right, including going up to the washroom to use the mirror.

These tits were even bigger than the ones yesterday.

Today I was really stacked.

The bra made my big boobs look like they were home-grown.

4. Put the new plug in that cunt of yours.

I grabbed some lube and without much effort (after my anal/pussy training and yesterday’s reaming) slid it inside me.

God, it felt good to have something inside me again, like coming home.

So natural.

Now I just needed something in my other fuck hole.

Fuck! I just referred to my mouth as a fuck hole!

5. Put your thong on (it should help keep your toy in place).

I put the thong on. It felt a lot weirder than panties, as the string went right up my crack.

6. Put on the sweater and skirt.

I did.

7. Put the heels on.

I did.

8. Put the wig on.

I did.

9. Text the word READY to the number on the bottom of this paper and wait.

I went to grab my phone and saw that Paige had texted me. I’m definitely going to fuck that pussy of yours. Yes, Mom took the photos and yes, she knows why I bought it. PS: She even gave me some tips on buying the perfect one for you (apparently she has pegged many guys in the past few years… go figure). She also explained it is a great way to balance the power hierarchy of the bedroom.



A second text from Paige: No shame, Ken. I love you unconditionally and look forward to exploring our sexual identities together.

God, I love her.

Maybe she would be able to understand all I’ve been through while she was gone.

Maybe she could accept I was a cross dresser… a cock sucker… a bottom….

God, I hoped so.

I texted back: I love you too Paige, and am looking forward to doing EVERYTHING with you!

I returned to the box, found the number and texted it, assuming it would go to Mistress M.

I received a response: Be there in a few minutes.


I texted back: Okay.

I finished reading the letter.

10. OBEY every command given you today without hesitation.

11. Stay home and wait… your benefactor will be over sometime today.

Mistress M

Was my benefactor coming over to fuck me?

My hard cock hoped so.

Yet, I wasn’t sure I wanted to get fucked by anyone other than Paige.


God, I wished she was here right now, as I began feeling that somehow she was going to be okay with all this. ‘Unconditionally’ was a pretty powerful word.

A few minutes later, the doorbell rang.

I walked over to it… in my heels, which I was pretty good in at the moment, and opened the door (wishing I had a peephole).

It was a young woman.

“Cute,” she smiled, as she breezed inside right past me.

“Thanks,” I said, as I closed the door.

“I’m here to do your makeup,” she informed me, gazing around to take in her surroundings.

“Oh, okay,” I said, as if that was obvious.

“Sit down over there,” she pointed at the kitchen table.

“Okay,” I nodded.

She then spent fifteen minutes doing my face and styling my wig. As she did, I thought how easy it was to be a man. No period of course, but also no lengthy morning war paint ritual and no shaving your body.

When done, she stood up without a word and left.


Obviously, she wasn’t Mistress M.

I then got a phone call.

From a number I didn’t recognize.

I answered it. “Hello!”

“Kendra?” a feminine voice asked.

“Yes,” I said.

“It’s Amanda. I found three black actors for your scene,” she said.

“Oh,” I said.

“But unfortunately we can’t film until tomorrow,” she added.

“Oh, okay,” I said, relieved, as Mistress M’s instructions had been for me to wait here until further notice.

“Be here at eleven in the morning.” she said.

“Sure,” I agreed, knowing that Paige’s flight was arriving at two. I could have one more wild adventure… day 13… before picking her up at the airport.

“Great,” she said, before adding, shocking me, “your first video has already garnered over 7,000 previews, 673 paid downloads and twenty-four comments.”

“It’s online?” I demanded.

“Yeah, it was way too good not to release,” she said. “I’ll text you the web address, and tomorrow while you’re here we can discuss what we’ll need to pay you going forward. We don’t want to lose a talent like yours, so a mere ten grand per shoot is history. Maybe you’ll do better if we give you a percentage rather than a flat fee, but we can fine tune that as we go along. We’ll also need to take some time to come up with a sexy name for you, unless you’re happy to use Kendra.”

“Okay, let’s talk,” I agreed, realizing there was nothing I could do to turn back time, and Amanda appeared eager to keep me happy long-term.

“See you tomorrow,” she said.

“Okay,” I repeated, in a sort of daze.

I received the website by text a moment later. I went upstairs to my computer, clicked on it and saw my scene was featured on the main page. I didn’t watch the preview… I wasn’t sure I wanted to.

I did read the comments, though:

-One hot sissy.

-God, I want that to happen to me.

-Best scene yet.

-That sissy is fucking hot.

-What a hot sissy. No one could fake those moans or that cum shot.

-I hope there are more scenes with this slut.

-Amazing believable scene. Hot shemale, hot sissy.

-Her cock sucking needs work, but wow can she take a cock and man, coming from getting fucked was so HOT!

-*****5 Stars*****

-I came twice.

-Best scene ever. I hope there is a sequel.

-Loved it. Only complaint… it is too short.

-Only a real sissy comes from getting fucked! I want to be a real sissy too.

-Love the nylons.

-God, I want that shemale cock.

-Please make more raw scenes like this.

-Best sissy on the site. I came when she came.

-Hot! Hot! Hot!

-That bitch is sexy as fuck.

-My cunt was on fire watching that scene.


-Oh my GOD!!!

-That is a real sex scene. Sissy clearly loves cock.

-Best video website there is and this the best scene.

Wow! All were positive.

I was perceived as hot.

They wanted more.


Curious, now I watched the preview.

It was only thirty seconds long and showed me looking in the mirror, me on my knees, me sucking cock, me bent over, a close up of my orgasm face (which was so mortifying to see) and me ready for a facial.

It was hot and yet so disturbing.

I went back downstairs and poured myself some water, and the toy in my cunt suddenly began vibrating.

“Oooooooh,” I moaned, from the instant pleasure. As I held the fridge door open, I wondered how the fuck the toy could just start buzzing by itself.

A moment later it stopped.

What the fuck?

I closed the fridge and downed the glass of water.

I started upstairs to watch the clip again… wanting to make sure I couldn’t be identified (I was already pretty sure I couldn’t), when the buzzing started up again, stronger than before.

I stopped walking and just allowed the pleasure to cascade through me.

Then I heard the front door opening.

What the fuck? I know I locked that!

The buzzing stopped again as I went back downstairs to the door, doing pretty well even on stairs by now in my five-inch heels, and froze as I saw the front door closed and my mother standing in my front entranceway.

“Hi, Kendra,” she said with a delighted smile, looking me over and not at all surprised by my completely feminine makeover.

“M-M-Mom?” I stammered in shock at hearing her call me ‘Kendra’.

“You look very pretty,” she said. “I love how you look.”

“Pretty,” I repeated in a complete daze as I tried to process my Mom being here.

“You actually look a lot like me,” she said, walking over to me after slipping out of her heels, which made me robotically glance down to her nylon-clad feet and red painted toenails.

“I do?” I asked, completely overwhelmed.

Now standing directly in front of me, she said, “If I didn’t know it was you, I’d never guess who it was.”

“Really?” I asked, struggling to process at least some of what was happening.

“Yeah, I thought the same thing yesterday,” she said, walking around me. “But face to face is even better.”

“Say what? Yesterday?”

“Your shemale video,” she tossed off as if it should be obvious, and now bending over behind me, as she lifted up my skirt. “Even your ass in this skirt looks feminine and hot.”

“You saw the video?” I asked, mortified by her words and also that my Mom was checking out my ass.

“Yeah, it was pretty hot,” she said, before adding, “and I see you’re just like your father.”

“I am?” I asked, every one of my responses being almost monosyllabic and a question, and every vague answer from Mom only creating more questions.

“Yeah, he too comes from being pegged without having his dick touched,” Mom revealed, as she moved a finger to my butt hole and tapped on the toy in my ass just as it started buzzing again.

“You peg Dad?” I moaned, again the question seeming already to have been answered.

“All the time,” she bragged, as she allowed my skirt to fall back into place.

“Wow!” I said, my body trembling both because of my cunt plug’s activity and from all these surprises.

Even though it should have been obvious based on all that was happening, I asked, the toy in my ass distracting me with its varied vibrations, “W-w-what are you doing here?”

“I’m your benefactor,” she revealed, sauntering back around to face me.

“Y-y-you?” I stammered again, like I suddenly had a stutter I couldn’t control, as I helplessly glanced again at her feet. “You’re Mistress M?”

“No,” she said shaking her head. “She’s an online Mistress who lives in London.”

“Explains the accent,” I mused, my brain unable to process as fast as the reveals kept coming.

“Yeah, she has a sexy voice,” Mom said, as the buzzing stopped again.

“Why?” I asked, wondering why she would do this to me. Or for me, as the note had told me on the first Day.

“Well, I’ve always wanted a daughter,” she said, my being an only child.

“Oh,” I said. I mean what else could I say?

“And since you liked wearing my clothes as a teenager and since you enjoy sissy porn,” she explained, “I figured it was the perfect Christmas gift.”

“For me?” I asked, unable to utter more than a couple of words at a time.

“Honestly, no,” she said.

“No?” I questioned, now even more confused.

“It was partly for you, but just as much if not more so, it was for your darling Paige,” she listed, “Besides, I didn’t want to do it at all without getting her approval up front.” Just as she finished speaking, the vibrations started up again. I looked at both her hands and didn’t see a remote, which only added to the multitude of questions I didn’t have answers for.

“What? Why?” I moaned, somehow even more confused after her answer.

“Well, I wanted to help you discover your true self,” she said.

“My true self?” I questioned.

“Your sissy self,” she clarified patiently. “I realize this is difficult to absorb all at once, but you can stop worrying. Your situation is far better than you can imagine.”


“I thought it was important to give Paige the gift of having her own sissy just like the one I had,” she added, taking my hand.

I didn’t say anything, although a moan escaped my lips as the vibrations inside me sped up.

She led me into the living room, where the next surprise hit me like a ton of bricks.

“Hi, honey,” Paige greeted, naked except for a pair of black thigh highs, a black leather bra with nipple cut-outs, and a strap-on cock… the ten-inch monster from the picture. God, did she look hot, but also rather frightening.

“Paige?” I gasped and moaned at the same time. “But you said you were arriving tomorrow!”

“I lied, darling. I hope you don’t mind, but I couldn’t resist the chance to see the look you have on your face right now. You’re gorgeous, astonished, busted, forgiven and horny all at once! You, my dear sissy, are a perfect storm, and I wouldn’t have missed this for the world!”

“Merry Christmas, slut,” Mom interrupted us, as she walked over and kissed Paige.

On the lips.

For a good, long minute.

While they fondled each other’s breasts.

When Mom broke the kiss, Paige responded to Mom’s earlier greeting, adding yet another shock in a compounding domino of shocks, “Thank you, Mistress; and a Merry Christmas to you, too.”

My eyes went wide. I stammered, “M-M-Mistress?”

“Sure,” Mom nodded, as she unclasped Paige’s bra. “You do know that I knew Paige before you met her?”

“You did?” I asked, this getting weirder and weirder.

“Yes, she was a temporary secretary for me for a few weeks,” Mom continued, as she snapped her fingers and gently guided Paige to the floor.

I stared in awe as Paige stuck her head willingly under Mom’s dress.

“She became my submissive pet,” Mom explained, before adding, “and she still is.”

I was speechless.




Yet horny as fuck.

“She’s an excellent pussy pleaser,” Mom continued.

Finally I said, “I don’t even know what to say.”

“You can say thank you for my setting you two up in the first place,” she offered.

“You set us up?” I asked, as she moaned, and I moaned.

“Yes, I made sure she went into Kennedy’s Coffee shop while you were there, pointed you out through the window, and I had her walk into you, knowing you would think it was your fault, and then I encouraged her to seduce you,” she explained.

I was again speechless.

Mom set us up?

That day I thought fate had brought us together, it was Mom?

Nothing I thought I knew was real anymore.

I was flabbergasted.



“I didn’t know you two would find love,” she added. “I just thought you might be a good match. At the time I had no plans to turn you into a sissy.”

“Wow!” I said finally.

“But then a couple months ago Paige found your sissy porn searches and rushed into my house, all upset,” she continued as my fiancée licked my mother’s pussy… although I couldn’t see her doing it because of Mom’s dress.

“I consoled her until she stopped crying at first, then I fucked her for the first time since I set you two up, and soon afterwards came up with this plan. First of course, I had to explain to her who you really were, deep down,” she finished.

“How could you know I was a sissy deep down?” I asked, not disagreeing with her, but wanting to know. Needing to know. Trying to understand my own confusing, evolving sexuality.

“You showed all the signs: you’re just like your father,” she answered. “Plus, whether you’ve ever noticed it or not, you’ve always displayed a lot of feminine characteristics and mannerisms.”

“I never noticed,” I said, “except for my liking panties and pantyhose.”

“I always knew about that of course, the amount of times I found dried cum on my panties and pantyhose was too many to count,” she said, moaning softly.

“Sorry about that,” I chuckled awkwardly.

“Don’t be. I’m sorry I didn’t do this sooner.”


“It’s obvious you’re a woman living in a man’s body.”

“Can’t I be both?” I asked, not wanting to be restricted to one or the other.

“Of course,” she nodded. “I don’t mean to belittle your masculine traits. I mean, your cock is bigger than most sissies have.”

“Thanks,” I said, finding it weird to hear my mother praising my dick size.

“I’m serious, if you had a small dick, we would cage it,” she said. “You know, like putting a tiny cock in a cage because it’s useless except as a curiosity to look at.”

“Oh,” I said.

“Give me a moment, your sexy little cunt licker is really working Mommy’s pussy,” Mom moaned, as she rested her hand on the arm of the sofa and closed her eyes.

I was watching my fiancée lick my Mom, and Mom seemed about to show me her cum face. Never thought I’d ever see that!


“That’s it, eat my cunt you eager little slut,” Mom moaned. “Show your sissy-man your secret side before she shows you hers.”

I noticed the pronoun change.

“Come closer and watch, Kendra,” Mom ordered.


“Don’t think I don’t know about your Mommy fantasies,” she said, raising her dress to reveal she was wearing crotchless pantyhose and my fiancée’s face was buried in her wet, swollen pussy.

Feeling slightly brave, I said, as I stepped over to her and lowered myself to get an up close and personal look at this surreal sex act between two women I loved and lusted after, “I don’t think you could possibly know about all the fantasies I have about you.”

“Perhaps not, but for starters, you want to have Mommy suck your cock, you want to come all over Mommy’s face, you want to fuck Mommy’s cunt and pound Mommy’s asshole,” she listed. She then added, moaning, as she grabbed Paige’s head and held her deep in her cunt, “And of course you want a nylon foot job.”

“Don’t forget eating your cunt and getting pounded by your strap-on,” I added.

“How could I?” Mom laughed and moaned simultaneously as she turned her attention to Paige, “That’s it sweetie, suck on my clit, get Mommy off.”

Paige’s head was quivering with intensity, as was her tongue, as she ate Mom’s pussy like it was her final meal. God was it hot!

“Oh yes, fuck yes, eat my cunt, fuck, yes, you dirty fucking slut,” Mom babbled as she came all over Paige’s face.

When Mom let go of Paige’s head, Paige turned to me and shoved my face into Mom’s flooding pussy.

“Eat your Mommy’s cunt, baby,” Paige ordered me, holding my head as I did what any guy would do with his face shoved against a wet, leaking pussy regardless of whose it was… I got straight to work licking and swallowing.”Oh, you dirty slut,” Mom scolded playfully, although I wasn’t sure whether she was calling Paige or me the slut… perhaps both of us.

I lapped up her tasty cum as one longstanding crazy fantasy unexpectedly became a reality.

It only lasted a minute before Mom pushed me away and asked, “Like your present, Paige?”

Paige looked me up and down, smiled radiantly and gushed, “She’s perfect. She’s gorgeous. And she’s mine!”

I felt myself blushing all the way down to my chest as Paige praised my beauty with a heart-wrenching mixture of admiration and love.

She leaned in and kissed me. Both of our lips tasted like my mother’s pussy.

I kissed her back… love conquering all.

“Well, Kendra’s little cunt is likely dying to get filled,” Mom correctly surmised, breaking the intimate moment.

“Shit, I left her toy on high for all this time!” Paige gasped and laughed.

“It’s been driving me crazy,” I pointed out, feeling so beautiful as Paige gazed at me adoringly.

“Oh, I plan on driving you crazy a lot,” Paige said, as she stood up and slid her monster cock in my mouth.

“She’s had a lot of practice in sucking cock while you were gone,” Mom told her.

“I can’t wait to see him suck a real one,” Paige said, as I bobbed on her fake one.

“He’ll be doing the black students shoot tomorrow,” Mom revealed.

“Mmmmmm,” Paige moaned. “Maybe it’ll have to be adapted to include an additional slut.”

“I’m sure that can be arranged,” Mom approved.

“Ready to get fucked, baby?” Paige asked.

“Please call me Kendra when I’m all dolled up like this,” I requested, as she pulled the cock out of my mouth and I shifted mental gears to become Kendra inside and out.

“Gladly. Do you want to be fucked, Kendra my sexy slut?” Paige rephrased as she strolled behind me cock first, and I lowered myself to all fours.

“Yes, Mistress,” I said, wanting her to have all the power.

“She’s already completely trained,” Mom told Paige, as she sat down on the sofa to watch.

“Yes, Mommy had me trained into a submissive sissy for you, Mistress,” I simpered, as Paige pulled my thong down and off.

“Crazy,” Paige said, seemingly as stunned as I was by this whole transformation of her fiancé as she pulled out the toy, still vibrating.

I moaned.

“Fuck is she gaped,” Paige gasped, as she surprised me by not immediately sliding her cock inside me, but instead kneeling down and tonguing me.

I moaned again, her tongue swirling around and even probing a little way into my pussy feeling amazingly pleasant.

“Eat that pussy, you filthy slut,” Mom cheered her on.

After a minute while I closed my eyes and did nothing but enjoy the wet tongue licking and probing into my gaped cunt, Paige leaned up and asked, “Ready for your first experience with my big cock, my personal slut?”

“Yes, fuck me with your massive cock,” I begged, looking back at her over my shoulder.

“I’ve been looking forward to this all week,” she said, as she slid her cock inside me.

“Me too,” I moaned, as my cunt was filled again.

“Take it all, Kendra,” Mom ordered.

“Yes, fill my cunt and fuck me hard,” I begged, wanting to take all ten inches…wanting to be her complete slut… wanting to show off my submissive slut persona to my mother as well.

“Such a good slut,” Paige growled, as she placed her hands on my hips and began fucking me.

“Harder, Mistress,” I begged.

“Make her your slut,” Mom encouraged.

“Yes, yes, pleeeease make me your slut, Mistress,” I squealed, as I closed my eyes and allowed the pleasure to consume me for the next few minutes… Paige sliding seven or eight inches in and out of me.

My cock flew around every which way, as hard as a rock.

My body burned with an unimaginable lust.

My pussy tingled with pleasure I hadn’t known existed before these 12 Days.

My lips moaned with sounds that weren’t manly and yet not completely feminine.

My balls boiled, ready to erupt.

“Bounce back and fuck yourself,” Paige ordered me aggressively. “Take all ten inches, and come like the sissy slut you are!”

“Oh yes!” I moaned in complete rapture, as I obeyed her and bounced back hard, taking all ten inches with one giant backwards bounce. Then I screamed, as an intense pain mixed with an equally intense euphoria swept through me as I impaled myself.

“Such a complete slut,” Mom praised me, “you make your Mommy proud,” as I became a complete bimbo bitch whose only purpose was to come for my Mistresses.

“Oh God, this is soooo good!” I moaned, as I furiously fucked myself.

“Come for me, Kendra,” Paige ordered. “Come for your Mistress.”

“Yes, I’m so close,” I moaned, knowing I was now this close to another non-contact orgasm.

“Come for Mommy,” Mom bellowed loudly, which was the final straw as I grunted and shot my load all over the carpet.

“Such a good girl,” Mom purred, as I collapsed forward, all the energy usurped from me.

Paige followed me down and resumed pounding me throughout my orgasm as I closed my eyes again and just enjoyed an orgasm that went on and on.

A minute later, maybe two, Mom ordered, “Come ride my cock, Paige-slut.”

I opened my eyes to see my Mom was now completely naked except for her crotchless pantyhose and her own strap-on. Even in her late forties, she hadn’t lost her figure at all, and I couldn’t help but stare. And she’s already promised I’ll be getting some more of that!

Paige pulled out of me, walked over to Mom, and lowered herself on the cock.

I stared as Paige put her feet on either side of Mom’s legs and began riding the cock… her strap-on still in place and bobbing up and down in the air.

“So, baby,” Mom said, leaning sideways to look at me still lying on the floor. “Did you like your twelve days?” As she asked, she was pinching one of her nipples, preening under my hungry gaze.

“It was the most life-changing twelve days of my life,” I answered.

“Is that a yes?” she smiled, licking her lips with a sultry smile.

“That’s yes times infinity,” I replied, watching Paige’s tight butt riding up and down on my Mom’s cock.

“Good,” Mom said. “Because there’s no going back.”

“What do you mean?” I asked, Mom’s generous tits bouncing around freely as Paige really rode that cock.

“Once a man becomes a sissy, once a man becomes a cock sucker, once a man takes a cock in her ass, she can never return to the old normal,” she explained.

“I wouldn’t want to anyway,” I said, loving the new me.

The pretty me.

The feminine me.

The slutty me.

No way could I go back to my old normal… my new normal was far more preferable.

“I knew you wouldn’t,” Mom said. “Like I always say, once you discover your true self, there’s no going back.”

“Plus, I love my new sissy,” Paige chipped in, rubbing her clit furiously while bouncing on the cock like it was a cock trampoline.

“And I love being your sissy slut,” I said, thrilled to be watching her enjoying such pleasure.

“And you’re mine too, daughter,” Mom added to me.

“Yes, Mistress Mommy,” I agreed. “I’m your submissive sissy slut too.”

“And mine too,” a new voice spoke up from behind me.

Now what? On a day like today, it’s got to be something else good!

“Hi, Mom,” Paige greeted, not slowing down her riding and pussy rubbing… her orgasm clearly close.

“Hi, slut,” Paige’s Mom greeted her.

“I guess I should add that I had my own 12 days of Christmas,” Paige shared just before she exploded and fell forward on top of my Mom, coming and kissing her passionately.

“It was 12 days of Incest-mas,” Mrs. Danson clarified, as she too got undressed.

I watched Paige’s older twin pull off her dress to reveal she had a cock… a real cock… a big cock!

“Mommy made me into her submissive slut for the entire trip,” Paige crooned, still shaking with pleasure.

“No way,” I said.

“She fucked me at least once in every country we were in,” Paige continued, rolling off the cock and collapsing beside my Mom, “including making me blow her on the plane, finger fucking me on a double decker bus in London, pouring wine in my cunt and allowing three women we’d just met to drink from it during a wine tour, making me wear a load of her cum all over my face in the Louvre, drilling my ass in a Vatican bathroom, and sharing me in a wild shemale and lesbian orgy in Amsterdam.”

“Wow!” I said, this equally as shocking as everything else I had learned and done in the last 12 Days.

“Shit, Kendra is prettier than I am,” Mrs. Danson said, looking down at me, her cock dangling.

“Thanks, Mrs. Danson, but I’m not so sure about that; you’re a doll,” I returned the compliment sincerely, staring at her cock as she looked me up and down and it grew, proving the sincerity of her admiration.

“Hungry?” she asked, leering at me hotly and now stroking her full erection.

“Starving,” I said, as she slid into my open mouth and I started sucking my fiancée’s Mom’s cock. As I did, I wondered if this was actually her biological Mom. Did she transition sometime after Paige was born? Was she actually Paige’s biological Dad who’d taken hormones after she was born? Given the family resemblance, it was impossible that one of these possibilities wasn’t true. I couldn’t wait to learn the whole story, but right now there was something even more urgent on my plate… or on my palate.

“Suck Mommy’s cock, Kendra,” Paige cooed, encouraging me.

I already was.

So I bobbed on her seven-inch cock, wanting to ingest my first load of the day.

“Good girl,” Mrs. Danson moaned. “I haven’t come since I fucked your fiancée’s ass on the flight home.”

“I came twice from that,” Paige added.

Fuck, this was weird.

Yet it was my new normal.

A new normal I wouldn’t change for anything.

A few minutes later, Mrs. Danson grunted and spewed her load into my mouth. She then joked, “Now I’ve come into the mouths of everyone here.”

“I guess this as good a time as any to tell Kendra that her father and I are getting a divorce,” my Mom revealed.

When Mrs. Danson pulled out, freeing my mouth, I blurted, “What?”

“We’d been drifting apart, but we stayed together for you,” she said. “But the truth is, I’ve been in love with Maggie for years. And he’s found a nice macho man to serve. We never cheated on each other, but we had a long heart to heart a while ago and agreed to open up our marriage until we found a good time to sever it.”

“I love you too, Sarah,” Maggie said, as she walked over to my Mom, pulled her up from the couch and squeezed her lovely breasts as she kissed her.

Paige and I both looked at them, stunned.

When they stopped kissing, Mom looked at Paige and me and said, “Why don’t you two go out for dinner or something? Your mothers are going to use your bedroom for the next several hours.”

“Holy shit,” Paige said.

“Shoo,” Mrs. Danson ordered playfully, taking my Mom’s hand and leading her up the stairs towards our bedroom. They both had really nice asses, and I looked forward to getting more closely acquainted with them both sometime soon.

Paige removed her strap-on and said, “I could use a bite to eat.”

“Should I change?” I asked.

“God, no,” she refused. “I love the new you.”

“And I love you,” I said, as I kissed her.

“I love you more than anything… both of you, Ken and Kendra,” she told me, when she broke the kiss.

I smiled, “I also love getting fucked by you.”

“And I love fucking your tight twat,” she said, as she grabbed her dress (and nothing else) from the couch.

“Where to?” I asked.

“Someplace nice,” she said, “I want to show off my new girlfriend.”

“Sophia’s Place?” I asked, it being a nice restaurant a twenty-minute drive away.

“Sure, and for dessert we can go to that glory hole you frequented last week… your Mom was giving me daily reports… and we can share some chocolate cream,” she said, taking my hand.

“The perfect date,” I laughed, thinking how crazy these Twelve Days had been, and how today wasn’t the end… but only the beginning.


December 2018

I’m not going to lie, this story took on a life of its own. It was originally supposed to be a Christmas contest story, but it took 3-plus weeks of writing and rewriting to craft the 12 days.

I love this character.

And if you want to read more, this may only be the beginning of their journey. Here are some potential future plots, and I’m also open to suggestions. These will, of course, be much shorter pieces, focusing on one main sex scene (perhaps two) and hopefully will build on the couple’s blossoming sexual awakening.

“Sissified: A Romantic Slut Night

A romantic supper filled with conversation about what might happen next in their relationship. Followed by a shared chocolate dessert or two at the black cock gloryhole.

“Sissified”: Blacked Teacher Bang

They film the planned scene, with a special guest appearance by Paige (maybe).

“Sissified”: Classroom She-Cock

With Paige’s permission and perhaps even her participation, Kendra’s shemale student helps him to satisfy his cock cravings at school.

“Sissified”: Cucked by Blacks

While Kendra takes charge to serve (up his fiancée), protect and direct traffic, Paige’s BBC gangbang fantasy comes true.

“Sissified”: Family Affair

Kendra and Paige are used by their mothers.

“Sissified”: Mommy’s Sissy

Kendra is used by his mother and her friends at a special party.

“Sissified”: Fuck Toy

Kendra is a FUCK TOY DEMO MODEL at a girls’ sex toy party.

“Sissified”: Poke-Her Night

Kendra serves as a slut for the night for eight men (Bill’s friends).

“Sissified”: Porn Star

Kendra leaves teaching to become a full-time porn star.

“Sissified”: Sissy Bonding

Kendra and his sissy Dad are dishonoured guests at an otherwise all-black frat party.

“Sissified”: The Wedding

Before, during and after adventures for the couple, their Moms, and perhaps select wedding guests watching or participating.

“Sissified”: XXX Honeymoon

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