Straight man is turned into a submissive sissy

literotica
literotica
132 Min Read

DAY 1: Tuesday the 25th

It was Christmas morning when I heard a knock at my door, which was, of course, very odd at ten AM.

At noon I would be heading over to my family’s for Christmas, and I seldom had unexpected visitors.

Still in my robe, I went to the door and was surprised to see a man standing there, holding a large box.

“Are you Ken Winston?”

“Yes,” I replied, perplexed at his presence.

“This is for you,” he told me, handing me the box.

“It is?”

“Yes,” he nodded, as I took it.

“Who’s it from?” I asked. There was no writing such as my, or a sender’s name or address on the outside of the box at all. Just shiny green wrapping paper and a big red bow.

“I have no idea,” he said, as he turned to walk away.

“How did you get the box?” I asked, this all seeming rather weird. He was dressed in regular winter clothing, no UPS uniform or anything. I had no recollection of ever seeing his face before.

“It was delivered to me to deliver to you,” he answered unhelpfully.

“Okay,” I said, finding this encounter very strange. I remained on my doorstep watching him walk back to the sidewalk, wondering whether he might climb into a van with some company’s logo on it. But he didn’t even get into a car; he just turned left at the sidewalk, then left again at the corner three houses down, and disappeared.

I took the large box into the house and into the kitchen. Curious, I opened it, where I found a collection of smaller boxes, and a pink envelope on the top saying in big bold letters: READ ME FIRST.

I opened the envelope.

Unfolded a letter.

It was addressed to me.

Dear Ken,

Merry Christmas!

You have been gifted with a very special, rare, 12 Days of Sissy-mas.

I goggled. Sissy-mas? What the fuck is that?

Okay, truth be told, I knew what a sissy was. I’d become a little intrigued and perhaps even slightly obsessed by sissy Tumblr pictures and gifs, as they recalled an obsession with nylons I’d had when I was a teenager.

I continued reading, both intrigued and baffled.

You will OPEN each box on the date indicated.

You will NOT open any of them early.

You will OBEY each instruction given without hesitation.

Do this, and you will find the sexual bliss that has eluded you for all these years.

What?

Obey?

Sexual bliss? I have a live-in fiancée, and she’s great.

What the fuck?

Yet I also noticed the all-caps words… similar to the Tumblr gifs that so intrigued me.

You may be experiencing ‘what the Hell?’ at this moment.

I understand.

But it is my job to guide you through a 12-day journey that will culminate in a full discovery of who you really are, and all you are meant to be.

This was like the most fucked up fortune cookie ever.

Yet I was undeniably curious.

If you are wondering who sent this to you, I am someone who cares about you. And you are fortunate, as only ten of these box collections are given out each Christmas.

Only ten!

You are one of ten recipients in the entire world… yes, the world… to be presented with this intimate exploration of who you are and who you NEED to become!

This just kept getting stranger and stranger.

I’m one of ten in the world?

Exploration?

Who could possibly have sent me this?

The main thing I couldn’t get past was the sissy reference.

I mean, I used to get off on wearing my Mom’s panties and pantyhose to masturbate in back when I was in high school, but I’d refrained from doing anything like that ever since.

Oddly, the next few paragraphs added some clarity, even as they raised more questions.

In the past, gender roles were very clear: the man worked, the wife stayed home. But recently changes… from the feminist movement, to the cost of living, to redefinitions of common sense, have reshaped how society is run, and perceptions of stereotypical gender roles have evolved with them.

Calling a guy a sissy used to be the ultimate insult. It meant you were weak, pathetic, small-dicked, and an utter failure in fulfilling the responsibility of a man to be a provider and the head of the household. Of course even back then it was all a façade. Women have always ruled the home and have worn the pants, metaphorically speaking. Yet the perceptions we usually feel compelled to avow in public have remained decades behind what are becoming ever more common attitudes and practices in private.

Now however, with the growth of the #metoo movement, mixed with the power of the Internet, much of society at long last is changing openly. An increasing number of people are making lifestyle choices that they never before felt permitted to make.

Even as larger numbers of women are exploring their same-gender sexuality, so are men. The number of men who consider themselves straight, yet who nevertheless suck cock, has skyrocketed. (And I know that you, KEN, have in the past considered doing this.)

Shit, although this had never been a serious consideration of mine, I would be lying if I told myself the idea hadn’t popped into my head on occasion. As I’d been scrolling through Tumblr gifs, or while I was watching porn and saw a girl sucking a big cock, I would sometimes wonder what her experience would be like. Then I would come, and afterwards be mortified by the ‘gay’ thoughts in my head.

I didn’t find men attractive.

I wasn’t gay.

I had a fiancée, and she was amazing. Our sex life was pretty good, although right now Paige was gone until January 5th (the last day of the 12 Days), spending Christmas travelling with her Mom (her dad long out of the picture… a story that perhaps one day I would learn more about) in western Europe.

The idea and even the practice of transitioning from a man to a woman, or from a woman to a man, has also increased in frequency, as has the acceptance in wider society of this self-realisation. Although many judgemental people are still critical of transsexuals, that number is dropping with every year that passes.

Yet what is happening more commonly now, is not so much the full transitioning to another gender (although that also is increasing), but rather the exploration of simply appearing and behaving as the gender a person wasn’t born into.

In men this is often known as feminization or sissification, where a man gradually emerges as being more of a female in mind and spirit, although not in body. It is typically a systematic process of psychological change and self-emasculation, wherein a man learns to appear, to himself and to others, more like a woman. Sometimes he (or psychologically she) goes no further than simply wearing girls’ undergarments (panties, bras and pantyhose), but may progress to more obvious cross dressing (the above in addition to heels, dresses, and wigs). Sometimes the person will progress to taking on roles that are typically perceived as feminine (sitting cross-legged, walking sultrily), sometimes even to a full feminine exterior (make-up, nail polish on toes and fingers, shaved legs) and sometimes he (she on the inside) will serve as a sexual being for another man (sucking cock or taking it up her cunt. (A sissy doesn’t typically have an asshole, at least not during sex.)

Why was this collection of boxes and this dissertation being sent to me?

And from whom?

I paused and took everything out of the box and found twelve smaller boxes of widely varying sizes. Each of these boxes was pink, with a red lid and a white ribbon. Each had a white linen card attached to the ribbon, displaying a conspicuous number: one for each day of the 12 Days of Christmas.

I sighed.

Did someone know about my online searches? I had read it was too easy to hack into someone’s laptop computer.

Equal portions of curiosity and frustration swarmed through me: I was intrigued by this letter and yet terrified that someone had discovered that I frequently checked out sissy gifs.

Understand that there is a major difference between a transgender transformation (which means physically changing genders) and becoming a sissy (where a man willingly allows his psychological masculinity to be compromised and perhaps even obliterated).

Also understand that unlike becoming transgender (which includes hormone treatments and surgery, and which is permanent), it is possible for a sissy to revert back to being a man, although that seldom happens. Once a sissy discovers her true self and allows herself to explore her true nature, she seldom wishes to go back. She will have discovered pure pleasure and fulfillment in the role of a submissive… a role that paradoxically is often even more fulfilling when it’s humiliating.

And Ken, someone who cares about you has discovered that deep down behind your professional high school teacher persona, behind your outer manhood and even athleticism, is a deeply hidden secret: YOU’RE A SISSY!

Fuck!

Who would possibly think this?

Who would send me this?

So… are you ready to begin your journey?

Kendra?!

Kendra?

What the fuck?

This is humiliating!

And that’s when I noticed my cock was hard.

Don’t deny it, you’d rather be a girl.

Wouldn’t you, Kendra?

Maybe? I didn’t know what I wanted.

Sure, I’d been intrigued by the sissy Tumblr gifs and captions, but I was also intrigued by incest videos (although I would never do that except in fantasy… I thought my mother was really hot), cuckold videos where a guy (often black) with a huge cock fucks someone’s wife or girlfriend (also something I would never want to witness for real), and lately I’d developed a little interest in the idea of being pegged. I’d even joked about it with Paige after we watched Deadpool 2. She’d laughed at my joke, even saying maybe she should buy us a strap-on… but that was it.

Which was the point… fantasy is fun… as a fantasy.

If you are ready, go ahead and open the Day 1 box. Once you do, you will obey without hesitation every order I will give you for almost two weeks.

Do as I say, and I will lead you to understanding who you really are and to accepting your true purpose in life… being a sissy.

Mistress M

Mistress M?

I wasn’t convinced I wanted to commit to twelve days of obedience to a complete stranger, but I had to admit I was curious.

So I picked up Box 1, which was larger than most of the others, and opened it.

Inside, I found a half dozen pairs of pink panties and a half dozen pairs of pantyhose in a variety of colours. There was also a note printed on a card.

DAY 1:

Starting today, beneath your clothing you will always wear pink panties, plus any colour of pantyhose you wish.

Go to your room right away and put on both.

Remember, you are to obey all my orders without hesitation.

Do not open Day 2 until tomorrow.

Mistress M

PS: Going forward, you’re not allowed to have an orgasm except when you receive permission from either me or another woman.

I’d like to say I ignored the order.

I’d like to say I threw the box and the collection of lingerie in the garbage.

Of course, then I wouldn’t have a story to tell.

Also, I wouldn’t have embarked on my journey and while it may not be obvious yet, that would have been a personal tragedy.

No, I did exactly as I was instructed to do… with a hard-on and excitement.

I went upstairs to Paige’s and my bedroom, opened my robe, stripped off my boxers, and slipped the pink panties on… God, they were so much softer and silkier than any male underwear. I would be lying if I said I didn’t love the feel of them, as well as the way my hard cock felt as they slid snugly into place over it.

I then put on the pantyhose, oddly excited. It took a bit of time to get them on and to smooth the wrinkles out, but once they were in place, I noticed they felt expensive. They were glossy, which I found hot on women. They were sheer silk. They were the sandalfoot variety that displayed the entire toe, unlike the less sexy kind with a reinforced toe.

I was looking into my girlfriend’s full-length mirror and tracing my hands up and down my legs, savouring the soft sensations on my hands, when my phone rang. It was my mother.

I walked over to my dresser to answer it, feeling oddly sexy and comfortable sauntering across the floor in the sheer hosiery. “Hi, Mom, Merry Christmas.”

“Hi, honey,” she replied. “Merry Christmas to you, too.”

“How’s the cooking going?” I asked. Mom cooked a full Christmas feast every year for over twenty of us.

“It smells amazing,” she answered.

Playfully, I sniffed audibly. “Yeah, it really does.”

“Silly! When are you coming over?”

“In an hour.”

“When you stop at 7-11 will you grab a couple gallons of milk?” she asked.

“What makes you think I’m stopping at 7-11?” I questioned with a smirk.

“You always arrive with a slurpee.”

“You know me so well,” I laughed, my major addictions being porn and slurpees.

“See you soon,” Mom said.

I hung up and couldn’t help but picture my pretty Mom walking around in her nylon-clad feet all day. Although I didn’t imagine it ever happening in real life, in the past few years I had spent many hours staring at Mom’s stocking-clad feet, and then later jerking off, thinking of her and them. No doubt my nylon fetish is because of her. Not only did she wear them while she worked as a financial analyst, but also at home. She wore them every day, seven days a week, and always under a dress or skirt. Truthfully, I had never seen her in slacks or jeans. Not once. And as I mentioned before, as a teenager I used to wear her panties and pantyhose on occasion.

I put on a pair of jeans and socks, I sure didn’t want to show anyone I was wearing pantyhose (there were no shoes allowed in Mom’s house (yes, my Dad lived there, but it was Mom’s house) … ever). I put on a dress shirt I could tuck in, and then after I finished getting ready, I loaded some presents into my car and headed out of the garage.

I stopped at 7-11 and got my usual slurpee (Coke in case you care) and milk (1% in case you care) and continued on to Mom’s.

I won’t bore you with the day. It was fun, but typical. I felt slightly excited to be wearing panties and pantyhose. I had a hard-on for much of the day because of that, as well as from watching Mom and my Aunt Rosemary both pacing around on nylon-clad feet. And I couldn’t ever get my mind completely off the obvious questions: who sent me the box? And why?

I got a new iPad and a few gift cards, and once I got home I called Paige, as we’d planned earlier. I didn’t think it could possibly be she who’d sent the box… it wasn’t at all like her. She was, in truth, a rather shy girl, although she could get pretty spontaneous and kinky when in the mood and nobody but the two of us were around.

She asked how my day had been, what I got for Christmas and so forth. I asked the same, but neither of us said anything to hint she had anything to do with the mystery box. I was certain she would have nothing to hint at, and I sure wasn’t going to ask her… who knows how she would react.

After hanging up, I still wracked my brain with the obvious questions: WHO? WHY? WHO? WHO? WHO?

Of course, I had no leads at all… I couldn’t think of a single person who would send me such a present, especially via such a generic yet anonymous courier.

No one knew of my crossdressing past, or of my more than slight curiosity with sissy gifs. I’d never shared this secret with a single person… ever.

This, of course, led me to wanting to go online and scroll through Tumblr, which had a wide variety of accounts I followed focusing on incest, cuckolding, interracial and, of course, sissies.

I couldn’t help wondering over and over, Who the fuck is Mistress M? Is she someone I know, or someone hired to train me?

Train me! What a weird concept, but from some erotica I’d read, that seemed to be what Mistress M intended. I also puzzled over her prohibition to come. I felt some perverse compulsion to obey.

Why? I had no idea.

My cock had been raging all day.

My balls had been boiling all day.

Yet I used all my willpower and resisted, instead deciding to end my Christmas Day with the best Christmas movie of all time, Die Hard (yes, it’s a Christmas movie).

DAY 2: Wednesday the 26th

I woke up still in my (my?) panties and pantyhose. I know that’s pathetic, but now that I was wearing them for the first time in several years, I didn’t want to take them off, and since there was no way Mom would catch me like there had been a risk of in the past, I figured why not).

Curious to know what was in the Day 2 box, I traipsed downstairs in just my robe, panties and pantyhose, not even pausing for coffee, and went directly to the box. I opened the box… this one very small and light as a feather… and saw it contained only a printed letter on a sheet of perfume-scented stationery.

Kendra

How was Day 1?

Did you get excited putting the sexy panties on?

Did you rub your hands up and down your legs once the nylons were on?

Did you admire yourself in the mirror?

Did you feel sexy?

Were you horny all day?

Was your cock dying for release?

Did you obey me and not come?

Of course those are rhetorical questions, since I already know the answer to each of them is a resounding Yes; because you’re a good girl, Kendra. Aren’t you? Say it! Say out loud that you’re a good girl, Kendra!

How could she know I’d done all that? How did she know I felt like that?

As I pondered, I heard myself say out loud, “I’m a good girl.”

As I spoke the required phrase, I felt two things in rapid succession: exhilaration, then humiliation.

Why did saying it feel good?

Why did wearing these sexy lace panties and the sheer hosiery make me feel good? Sexy? Worse yet, natural? Why did feeling humiliated turn me on?

Good girl. With true obedience will come true self-discovery. With true self-discovery will come a realization of your true purpose in this world.True purpose?

Being a cross dresser?

A sissy?

Those are roles I should aspire to?

Her words were strange, borderline preposterous even, and yet as I recalled the many Tumblr gifs I had scrolled through during the past few months, I knew exactly where she was coming from… but online these were just silly fantasies… ways to get off… almost always followed by shame that they’d turned me on in the first place. Yet the cycle always continued as I returned to Tumblr a few days later and repeated the excitement, followed by the shame.

Today like every day from now on, you will wear a pair of panties and pantyhose, except when you undress at Claire’s Salon.

Claire’s Salon?

That was the ritziest salon in the city.

It was for women. It was a place Paige had said she dreamed of going. It was also the place I’d purchased a gift card for her for Christmas, that ironically, she would receive when she returned home. She would receive a three-hour diva experience that had set me back 400 bucks.

You have an appointment there today at 1PM under the name Kendra Winston. It is prepaid.

You’re likely wondering why you’re going there. It’s a surprise, but is also an important step in your journey.

Remember, no coming!!!

Mistress M

What could she possibly expect me to have done there?

I couldn’t fathom.

Although I sensed it would be something humiliating.

I ate breakfast, showered, put on a fresh pair of panties and pantyhose, got dressed (no socks this time, figuring I wouldn’t be walking around without shoes anywhere, and headed out, as I wanted to do some post-Christmas Day shopping (so much is on sale the day after Christmas).

I bought a new 4K blu ray machine, since I’d bought a 4K TV on Black Friday (70 inches… size sometimes does matter… LOL) and then I’d learned you needed a 4K blu ray player to watch the 4K movies I had purchased (Both John Wick movies, The Spy Who Dumped Me, Justice League, and Mamma Mia (that last one for my girlfriend, I promise… okay, I’m not going to lie, I loved it too)). I also picked up the Harry Potter and Mission Impossible 4K box sets, and the just-released Venom (which I hadn’t yet seen).

I also went jeans shopping and felt oddly liberated as I tried them on in the change room. Each time I took off a pair of jeans, I admired my legs in the mirror. God, I loved the look and feel of nylons… even on myself.

I bought a couple pair of jeans, had a quick lunch (Subway, honey roasted chicken on honey oat if you care), and headed to Claire’s, even though I was pretty sure I didn’t want to, it would no doubt be almost fatally embarrassing. I knew that the more I obeyed Mistress M’s instructions, the deeper I would fall into this sissy transformation someone had orchestrated for me, and had even paid for. And even as I complied with everything, I still questioned whether this was a direction I wished to travel. I wasn’t leaning strongly one way or the other, but I still kept going forward, which I guess said something all by itself.

Sure, I had liked the first task, gotten excited even, but there were ten more to go after today’s ominous one. An even more ominous thought was that I could only fathom they would become ever more daunting and humiliating as the days progressed.

Yet my cock was hard.

Ultimately I felt compelled to obey.

No matter how much I wanted to deny it, I was enjoying this so far, and I wanted to continue. If things got too weird, I could always walk away. I think.

I reached the salon, walked just inside the door and froze.

Three feet inside the entrance was a prominent sign: No shoes past this point.

Shit!

I looked at the mostly high heels that had been placed on shoe racks along the left-hand wall.

I sighed.

I considered turning around to leave, and yet not seriously. No one was going to pay much attention to me, and the odds of my knowing anyone here was close to zero.

I placed my out of place runners on a rack and walked further inside.

Embarrassment hit me: five women were all seated, waiting their turn in the lobby.

They all looked up at me. Scary!

I went to the front desk and whispered, feeling five sets of eyes staring at me from behind (no idea if they really were, but in my head they definitely were), “One o’clock appointment for Kendra.”

“Pardon?” the drop dead gorgeous blonde-haired, blue-eyed teen asked, far from whispering.

I leaned in and whispered again, “Appointment for Kendra.”

“Oh,” she said, studying me for a moment and then looking down at her computer. After a moment, “I see. Please take a seat.”

“Thank you,” I replied, feeling my cheeks almost bursting into flame. I scuttled over to an open seat and sat down, where I noticed a couple of my quintet of new companions gazing directly at my feet.

I kept my head down for a couple of minutes, unable to look anyone in the eyes, until my new name was called out almost immediately even though these (other?) ladies had gotten here first, only adding to the humiliation of the moment, “Kendra.”

I never even glanced at the faces of the seated women as I got up and followed a short, slender Asian woman, again feeling their stares stabbing into my back.

Once we’d arrived in a room, the woman instructed me, “Get undressed and lie on your back beneath the blanket.”

“Yes, ma’am,” I responded, realizing how subservient my response was.

“Your pantyhose and panties as well,” she added, before walking out.

My jeans are still on! How could she know I’m wearing panties?

My question unanswered, I got naked and climbed under the thin blanket, feeling massive trepidation for whatever was coming.

A minute later there was a businesslike knock at the door and the same woman’s voice, “Ready?”

“Yes,” I responded.

She walked back in, grabbed something from a table and walked over to me. She lifted the blanket off my left leg, and wordlessly began smearing sticky goo all over it. My eyes went wide as I realized she was about to wax my legs.

Oh, fuck!

Yet, I didn’t stop her. I lay there in shocked awe as she coated my (thankfully not too hairy) leg.

Once done, she pressed some strips of something onto my legs and warned me, “This may hurt…” she took hold of one of the long strips and yanked it completely off in an instant before finishing, as I screamed, “…a lot.”

I peered up at her in terror as she smiled with a hint of sadism and yanked off the second one while I was still sobbing in pain from the first.

A few more painful yanks… if I hadn’t looked I would have thought she’d pulled off all my skin… and she said routinely, “First leg is done.”

“Holy fuck,” I groaned far from routinely, wondering if this was the pain women always endured when they waxed their legs. (I’ve since learned that the first time is usually the worst.)

“Just relax,” she encouraged me, as she uncovered my second leg.

I chuckled weakly, “Relaxing is the one thing I won’t be doing.”

The pain returned a few minutes later, just as bad.

She then surprised me as she pulled the blanket completely off my naked body and ordered, “Spread your legs.”

“Excuse me?” I asked, having heard her but not believing what I’d heard.

“Time to shave your private area,” she explained.

“Really?” I asked.

“That’s what was paid for,” she told me.

Then for twenty plus minutes, shaving being a lot less painful, every hair in my crotch area was removed. I desperately tried not to get an erection… thankfully I succeeded, even though she cupped my balls many times and casually moved my cock around whenever it was in the way.

She then ordered, “Roll onto your stomach.”

“What’s left?” I asked, then realized I shouldn’t have.

“Your buttocks, of course,” she answered, as I obediently rolled into place.

“Oh,” was all I said, as she spent the next while getting rid of all the hair not only on my ass, but even between my ass cheeks… easily the most macho-crushing moment so far.

She then did my back, rolled me back over to gain access to my front, and did my chest, which was already almost hairless, something I’d always been embarrassed about until now. She also shaved my arms and my pits.

She then announced, “Done.”

“Thank you,” I replied, it seeming the right thing to say.

“You’re welcome,’ she said, handing me a bag. “Use the lotion on all your depilated areas for the next few days, and you should take a long soak tonight with the salts I’ve provided.”

“Okay,” I said, accepting the bag.

“You may feel itchy or get rashes if you don’t take care of your skin, especially your delicate areas,” she explained.

“Yes, ma’am,” I nodded, feeling she was speaking to me as if I were female.

“You may get dressed,” she said, and walked out.

Standing up, I turned slowly around in place, studying myself in the mirror. I was completely hairless except for my head.

It made my six-inch dick look way bigger.

Although the procedure had seemed rather emasculating, the truth was, it actually made me look better: my cock looked bigger, I looked better. Truth be told, I kind of looked like one of the porn stars I watched, who were always shaved down below.

I put my panties (were they mine?) and the pantyhose back on, surprised so sexy I felt with the smoothness of my legs. I finished getting dressed and walked out, feeling a little itchy and sore as I did.

I went to the front desk to pay. The blonde reminded me, “It’s already paid for.”

“Oh, okay,” I nodded, walking to the entrance and putting my shoes back on.

I drove home via McDonalds (getting a quarter pounder without cheese meal in case you care).

I ate dinner at the kitchen table.

I watched some television.

I resisted scratching my itchy skin, as my crotch area especially was begging for attention.

I took a lengthy bath with the unique bath ball that had been given me, feeling somewhat decadent, kind of like Julia Roberts in ‘Pretty Woman’.

I couldn’t deny that I felt very much like a woman.

After the bath, I applied the salon’s lotion as my skin, especially my legs, was noticeably redder than usual.

I then called Paige, telling her about the shopping part of my day, not the rest… although at some point soon after she returned, she would discover what I had done and require an explanation… I mean hairlessness wasn’t something I could hide from someone I shared a bed with.

I would need some time to figure out how to explain why I’d decided to get a complete body wax.

Fuck!

DAY 3: Thursday the 27th

I woke up and applied the lotion again, as my legs looked redder than they had yesterday.

My balls were itchier.

Thankfully the lotion really helped.

Then, wearing only my pink panties, my lavender pantyhose and my robe which I left hanging open, I headed down to the kitchen and to the box, and opened Day 3 with the odd excitement I used to feel when I was a kid on Christmas morning.

Unfortunately as you get older, opening presents gets less and less exciting, as they are usually gift cards, or exactly what you’d asked for. Thus, not many surprises. But these pink gift boxes were intriguing.

This one contained a shot glass.

Weird.

I read the note:

Kendra

Do you feel the changes inside you?

The excitement of wearing panties?

The sexy feeling of wearing pantyhose?

The unnatural sensations of being hairless?

The femininity of it all?

Yes, I could feel changes like these ones inside me, although I couldn’t explain them.

I enjoyed wearing panties.

I did indeed feel sexy in the sheer pantyhose.

I wasn’t sure I felt natural, but looking in the mirror last night (putting my… yes, definitely my panties and pantyhose back on after the lengthy bath because I wanted to sleep in them… which in retrospect is definitely rather sissy-like), my legs looked sexier and more feminine without the hair.

You’re probably wondering about the purpose of the shot glass.

Yep!

Today you get to come.

Awesome!

Into the shot glass.

Then you’ll chug it.

Oh God!

I know you’ve been wondering for a while what cum tastes like.

So today you’ll find out.

Go to Tumblr (I know you love the site) and look up ‘You May be A Sissy if…’ and scroll through them all.

How could she possibly know that about me?

Who the fuck orchestrated all this?

Why am I already fucking hard?

Then you may come.

Then you will drink it down.

Enjoy your treat.

Mistress M

Fuck!

Yet I’d be lying if I pretended I hadn’t pondered what cum tastes like… and pondered it a lot.

More than once I had considered eating my own jism, especially when I was hard as hell and scrolling through Tumblr gifs.

Yet as soon as I came, that curiosity always faded.

So, after a morning of grading papers, I turned on the television, I had six episodes of Manifest to catch up on, flipped open my laptop and found the sissy page she referred to.

My cock got rock hard just from the first picture: a hot blonde slamming her strap-on into another hot blonde with her legs spread and obviously in the midst of an orgasm, with the caption: IF YOU WANT TO BE THE ONE WITH YOUR LEGS OPEN INSTEAD OF THE ONE DOING THE FUCKING… YOU MAY BE A SISSY.

Truthfully, I could imagine myself being either. The idea of being pegged was another fantasy that had been awakened in the past few months.

It first popped into my head watching Deadpool, and then heated up some more when I saw it on a variety of Tumblr gifs.

The next one was a brunette sucking and stroking a hard cock with the words: IF YOU’RE CHECKING OUT THE COCK INSTEAD OF THE HOT GIRL WITH THE BIG TITS… YOU MAY BE A SISSY.

Damn it! I sighed. I realized I was indeed staring at that big cock sliding in and out of the girl’s mouth in this brief gif, and I hadn’t noticed those massive bouncing tits at all.

That was followed by another gif of a pretty brunette slowly sucking a big cock deep into her mouth with the words: IF YOUR FIRST THOUGHT IS ‘I THINK I COULD DO THAT’… YOU MAY BE A SISSY.

I guess I wasn’t too far gone, because it wasn’t until after I’d read the caption that I wondered … Could I do that? Could I take a cock that long all the way into my mouth? This hot girl made it look so easy… so natural.

I probably should have stopped scrolling down, as I could feel myself getting drawn in like I always did… but like always, I kept scrolling so I could take in each gif.

I’m not sure whether I actually did open my mouth, but I was in awe of a massive load spewing out of a white cock as two cute redheads stroked it together while attempting to catch at least their share of his load with the words: IF YOU OPENED YOUR MOUTH TO CATCH THAT ROPE OF CUM… YOU MAY BE A SISSY.

Again, I wasn’t sure if I had… but I was undeniably captivated by the image of all that cum shooting out of a cock. And because it was a gif, it continued shooting over and over and over…

The next one made me think of today’s note from Mistress M and my task, as I watched a hot blonde in glasses (looking nerdy hot) wiping cum off her face and into her mouth while licking her lips seductively, and the words: IF YOU’VE EATEN YOUR OWN CUM AND LIKED IT… YOU MAY BE A SISSY.

I felt a chill go up my spine at this reminder of today’s task.

And no, I hadn’t done it before.

Yet I knew I’d be doing it soon… I’d be eating my own cum whenever this load burning in my balls finally erupted… although I wanted to hold out as long as I could.

The next one wasn’t a gif, but a picture of a brunette in a dress and her feet in nylons with the words: IF YOUR NAME IS UNISEX SUCH AS PAT OR CHRIS… YOU MAY BE A SISSY. EVEN YOUR PARENTS WEREN’T SURE HOW YOU’D TURN OUT.

Until Christmas Day, I’d never once pondered that my name could easily be turned into a feminine one. Yet for three days now, a stranger (or maybe someone close) had been calling me Kendra.

And right now, the name I wanted to be called was Kendra instead of Ken.

Next was a hot black and white gif of a girl with her hands bound behind her back, on her knees, sucking a cock, as a guy held her head and used her roughly. The caption was: IF YOU WONDER WHAT IT WOULD BE LIKE TO BE USED LIKE HER… YOU MAY BE A SISSY.

FUCK!

I’d been thinking exactly that… minus the being bound part, as I hated being confined in any fashion.

But the rest… the idea of just being taken and used… was strangely hot… and I considered how hot it would be to make this fantasy into a reality.

The idea of sucking a cock was hot, but the idea of the reality was scary, if that makes sense.

The next one had apparently been borrowed from the blacked site (which was a hot interracial site of white girls being used by black men… although the scripts were terrible) of two blonde girls sucking two black cocks with the caption: IF YOU CAN’T DECIDE WHICH COCK IS JUICIER… YOU MAY BE A SISSY.

I looked at each cock: one was thick and straight like a rocket; the other was thick and curved.

Each was indeed captivating, and each made my mouth water.

Equally hot was each girl with a juicy cock in her mouth and her eyes looking up at the dominant black man.

The next one was also hot. A normal looking blonde was in awe of a huge black cock as she stroked it, seeming to say ‘Oh my God’ in complete awe of its majestic beauty before sucking it as if it was the last cock on earth with the caption: IF HERS IS ALSO YOUR OWN FIRST REACTION TO THIS DICK… YOU MAY BE A SISSY. AND IT IS, ISN’T IT, SISSY?

I’m not sure I was that excited, but I was in awe of the huge cock… I mean I realized I’d just called it majestic. And that did indeed seem the exact right word… majestic.

I kept scrolling… each entry making my cock throb… the next one was a cute girl with a ponytail in the midst of receiving a massive facial with a big smile on her face, with the caption: IF YOU’D RATHER BE THE GIRL ON HER KNEES THAN THE MAN STANDING OVER HER… YOU MAY BE A SISSY.

And although I liked the idea of being either… I had to admit that at the moment I preferred being the girl.

The next one made me smile and laugh, even as I agreed with it. Two redheads (God are redheads hot) sharing only a single black cock. One girl had it in her mouth, while the other looked on in jealous hunger with the caption: IF YOU’RE AS JEALOUS AS THE GIRL WITHOUT THE BLACK COCK IN HER MOUTH… YOU MAY BE A SISSY.

And indeed, I did feel envious… I wanted to try a cock in my mouth… and in a perfect world it would be a big, black cock.

Fuck, do I need a cock in my mouth.

I needed to try it.

I knew that until I did, I’d be obsessed with curiosity.

The next one also made me smile, as I looked down at what I was wearing.

Panties.

Pantyhose.

As well as my robe, but that was just hanging open, leaving my girly attire fully visible.

The picture was a cute girl in a blue baby doll nightie and beige pantyhose, posing with the caption: IF YOU’VE EVER WORN PANTYHOSE… YOU MAY BE A SISSY.I admired my nylon-clad legs and smirked.

If that meant you were a sissy, then I was definitely a sissy.

I scrolled through more and more of them until I couldn’t last another moment. I pulled my cock out, stroked it for no more than a dozen seconds, and spewed right into the shot glass. Before I even had time to think, I raised the glass and downed the cum before licking the glass clean.

It was warmer than I imagined… it had never occurred to me what temperature it might be.

It was gooey and slightly salty as it slid down my throat.

And as soon as I was done… my question was, What would it taste like shooting right out of a cock?

Fuck!

I really was losing it.

DAY 4: Friday the 28th

Just like the past couple of days, I went straight downstairs and opened the next box, this time nude except for my panties and pantyhose.

This time I found a pair of 5-inch open-toed heels.

Red.

I bet you’re craving cum.

Yep!

Today whenever you’re at home, you’re to wear the heels. A minimum of four hours today. Practice walking in them. Watch the YouTube clip called: “How to Walk in Heels | Step By Step ★ Glam.com”.

Also, I expect you to scroll through Tumblr (for at least an hour) by searching ‘Sissy Rulebook’. You will save your favourite 12 rules into a file called ‘Sissy Training’ and then email them to me at MistressM@sissified.com.

As usual, no coming.

Mistress M

Curious and still wearing the panties and pantyhose from last night, since sleeping in the hosiery felt, as I mentioned before, comforting and sensual and natural, I slipped into the heels.

And would have fallen on my face if it weren’t for the kitchen table.

How the fuck can women even walk in these with their feet at such an extreme angle?

How do they balance themselves, especially if they have big tits?

I took them off and carried them upstairs to my room. I grabbed my laptop, got onto the bed, put the heels back on, and searched for the Sissy Rulebook.

I then spent a couple of hours scrolling through the impressive account, always being a fan of lists.

I won’t quote every number, just the ones I saved and sent to my mystery Mistress (I have a Mistress? Still a rather surreal concept).

#3 A sissy loves cum (a cute brunette on her knees with her tongue extended and full of cum).

I’m not going to lie… the idea of being on my knees in front of a big cock and tasting cum was becoming more and more intriguing… especially after tasting my own yesterday. Before these 12 days began, it had been simply a curiosity and nothing more… nothing I would ever seriously try… yet.

#4 A sissy loves cock (a close-up of a chubby blonde with a fat cock stretching her mouth).

I have a decent cock. Six inches. Yet I’d be lying if I said I wasn’t intrigued by bigger cocks… thicker cocks. I couldn’t explain it, but it’s probably very much like women who want bigger tits or a tighter ass or whatever they think they don’t have.

#5 A sissy takes it in the ass (a big tittied brunette in thigh highs pounding another girl in the ass with a strap-on).

It was weird how these photos and gifs worked. They used women to enhance the imagery, yet slyly manipulated men into imagining we were the ones on our knees sucking cock, or this time taking it in the ass.

Not going to lie… the idea of taking it in the ass hadn’t ever turned me on before. Yet for the first time I was curious. The girl seemed to be enjoying it… and I know that men can achieve prostate orgasms…. Yet taking it in the ass is definitely gay. Although… Would that be true if it was from a woman wearing a strap-on? Would Paige wear a strap-on for me? Would Paige fuck me? We’d joked about it a bit, but would I want that for real? Fuck, I’m only five rules in, and already I’m wishing for things I haven’t ever seriously considered before.

#8 A sissy dresses like a slut (a hot redhead dressed in a schoolgirl uniform posing commando on her hands and knees, her butt closest to the camera and looking back over her shoulder as if she’s begging for a big hard cock in one of her holes… whichever hole you like).

I’d kind of cross dressed before… I was doing so now… but only in panties and pantyhose. I hadn’t ever considered wearing a completely feminine outfit… although as I lay on my bed in panties, stockings and heels, I realized the only additional garment I needed was a dress. Deciding why not, I got up, almost killed myself again in my heels, and cautiously staggered over to Paige’s closet. I looked through her dresses and chose a black one that I recalled her saying was too big for her.

I pulled it on over my head and looked in the mirror.

A wig and some fake tits, and I could perhaps pass as a girl.

Fuck! What am I thinking?

It was one thing to wear panties and pantyhose, but to become completely feminized was a whole new concept.

I shook my head, but oddly I kept the dress on as I returned to the bed, stumbling once, and resumed scrolling through Tumblr.

#10 A sissy loves facials (a pigtailed blonde coated in at least two loads of cum).

I’d only ever given one facial, and I’d felt guilty afterwards because I felt it was too demeaning for the recipient. Even though she’d begged for it. On the other hand I’m not going to lie, a girl with cum on her face looks pretty hot. I hadn’t ever considered being on the receiving end of one, but now I wondered what it would feel like… oddly, during these first few days, the demeaning humiliation I’d often felt was a strange turn-on I couldn’t explain.

#14 A sissy is a pro cocksucker (a blonde with a big cock in her mouth bobbing furiously as if her life depended on it).

I laughed. If you aspired to being a sissy, you’d better be a cock sucker. It made me wonder what abilities qualified a sissy as a pro cock sucker.

Deep throating?

Not gagging?

Speed?

Passion?

Eagerness?

Swallowing?

I also wondered as the gif replayed over and over, what it would be like to have one in my mouth. This blonde made it look appealing as fuck.

#16 A sissy belongs on her knees (a blonde on her knees smiling with a big black cock right in front of her face).

This one seemed logical, and it seemed to be one of the fundamental truths portrayed in these photos and moving vignettes. The sissy was always either on her (his?) knees sucking, or on all fours getting fucked.

The natural submissive hierarchy intrigued me. Being on your knees looking up at a man was the ultimate declaration of knowing your place.

#18 Sissies swallow (a gif of a cock spewing endlessly into a wide-open mouth).

This one also seemed logical. If you were going to do all the work, you may as well get the reward. Did I just call cum a reward? Fuck!

#20 A sissy will fuck anywhere (a blonde kneeling on a city sidewalk with a cock in her mouth while other people walk by, some of them aghast).

This was the first one that made me really wonder. Would a true sissy really fuck and suck anywhere? I would think a sissy would want to keep this side of her (him?) a secret. I mean it’s one thing to fantasize about this stuff, but another to do it. Equally, it’s one thing to suck a cock, and a completely other thing to do it in public. Would a sissy’s lust for cock and cum override dignity and propriety? If so, shit was that scary.

#23 Cum is your reward (a close-up of a smiling brunette with a nice creamy load all over her face as she scoops it off her chin and eats it).

Did I just call that cum nice and creamy?

Cum as a reward… ha! I just called it that.

God, I can’t help but admit I crave sucking a cock… tasting cum.

#25 You prefer BIG BLACK DICK (a hot redhead on her knees with a thick, black cock in her hand with a look of both shock and lust).

Although race didn’t completely factor into my growing curiosity about sucking a cock, I would be lying if I denied the idea of a black cock certainly enhanced the imagery, and also my stimulation.

#26 Sissies love garters and stockings (a girl in a black garter and stockings giving a foot job to a nice hard cock).

I had never worn a garter before, but I did love stockings, so I was certain that this too, was true.

The idea of a nylon foot job was also rather intriguing. I bet it would feel really nice. Getting one I mean… not giving one.

#27: Sissies love a good gloryhole (a chubby redhead sucking a cock through a glory hole).

I had never been to one. Truth be told, I imagined they were mostly a fairy tale. The idea of getting a blow job from an anonymous person was rather intriguing. As my desire to suck grew, I wondered if there were any glory holes in my town.

Curious, I opened another tab and searched for them.

I gasped.

There were five of them within just an hour’s drive.

One of them was only ten minutes away at an adult store I’d once been to for a bachelor party gift.

Tempting… very tempting.

#28: A sissy loves the taste of her own cum (a close-up of a girl pouring cum into her mouth from a cup).

After yesterday, this was hard to argue against.

#33: Sissies love heels (an otherwise naked girl posing in red high heels and tan pantyhose).

I wasn’t sure I loved heels… so far I was finding them quite awkward. Yet visually, they did help to enhance the ensemble I was wearing. Awkwardness aside, I thought I looked great in them.

Fuck, did I just describe my clothes as an ensemble?

#48: Sissies don’t decide things. Sissies do as they’re told (a girl on her knees begging for cock).

It was weird. Truth was, this entire variety of kink seemed fucked up. Truth was, I was only going along with this indoctrination (for want of a better word) just out of curiosity (which I realize was tough to prove when I took in my hairless body). Yet, here I was on Day Three, doing very little thinking and doing exactly what I was told, without even someone around to enforce the requirements placed upon me.

Maybe deep down I’m a sissy, or at least a sissy wannabe.

Fuck!

This should have scared me, but with my cock hard and my legs swathed in silk, I resumed scrolling through pictures and gifs that drew me deeper into a place I wasn’t sure I wanted to go… yet was also not sure I could resist.

#50: Sissies love to be degraded (a girl getting slapped in the face by a big, fat cock).

I couldn’t deny it. The degradation thing was turning me on.

I couldn’t explain it. I mean, I’d always seen myself as a man’s man: I worked out, I played sports, etc. Yet cross dressing, getting shaved and even waxed, plus this endless fantasizing about sucking cock, had awakened a side of me I hadn’t known existed. A side of me that wanted to please; one that was very drawn to the idea of being a sissy, a cock sucker.

#51: Big black cock is a delicacy and should be treated as such (a MILF stroking a massive big, black cock with an undeniable look of lust).

The term ‘delicacy’ should have been absurd, yet it seemed appropriate as I stared at the tantalizing cock.

Did I just call it tantalizing?

Fuck!

Yet I couldn’t deny it, there was something particularly appealing about a black cock. Maybe it was the colour. Maybe it was the taboo racial aspect. Maybe it was the myth about all blacks having cocks like stallions. Maybe it was the growing tide of interracial porn.

Likely it was all the above.

But God, the idea of sucking a black cock was all I could think about. I also felt a bit inferior as I stared at this massive cock, knowing Paige’s last boyfriend had been a black basketball player. Did he have a massive cock? Was his bigger than mine?

Fuck!

#63: You’re not a person, you’re just a sissy fuck toy (a girl on all fours taking a cock in both her mouth and her pussy, bouncing back and forth like a manic rocking Rocky(H)).

It’s weird… really weird… that my physical response to that statement was my cock flinching in my panties (equally weird that I could even accurately speak of ‘my panties’).

Yet the idea of my being a fuck toy for two cocks (not two men, men didn’t turn me on, but hard cocks were just so visually appealing) was stirring inside me.

God, when I’m horny, my mind goes places I never thought it would before this entire adventure began:

Crossdressing.

Sucking cock.

Even taking it in the ass.

Fuck!

#76: Sissies love bukkake (a girl with a few loads dribbling down all over her face).

Again, the idea of a facial was hot… the idea of cock after cock spewing on my face was captivatingly intriguing.

Fuck!

#116: Sissies don’t fuck women, women fuck sissies (a gif of a hot woman wearing a strap-on continuously fucking a guy in the ass).

Fuck, that’s hot!

Although the idea of a guy fucking me was somewhat intriguing, the truth was, it scared me and seemed very gay (somehow sucking a cock didn’t… not that I’m making any sense).

On the other hand, the idea of a woman fucking me with a strap-on seemed hot as fuck. I mean if Deadpool can take it in the ass, I sure as hell could (I know I’ve already said that earlier, but it seemed like a fair rationale).

Again, I wondered whether Paige would don a strap-on for me.

Would she be willing to fuck me hard like this woman was doing to her guy?

Fuck!

#143: No cock is too big for a sissy like you (a huge cock spreading a cheerleader’s ass).

Since the idea of sucking a cock was growing in me, and since the idea of being sodomized was lingering, the issue of size was becoming pertinent.

Too long would make me gag.

Too thick would tear my ass apart. Why am I even going there? Fuck!

Yet I would be lying if I pretended I wasn’t fascinated by big cocks. I mean truthfully, I was fascinated by all cocks, but long cocks and thick dicks really drew me in.

Just like girls with average sized breasts (as I have an average sized tool), you always want what you don’t have.

#164 A sissy must be a perfect submissive. On her knees with her mouth open is not only where she belongs, it’s where she lives (a girl in a nurse’s outfit on her knees with a nice cock in her mouth).

I realized the themes were beginning to get repetitive, as if repeated concepts could condition me properly. As I stared at the cock and not at the girl, I began to think that idea may be true, including in my own case.

#173 A sissy must learn not just to love cock, but to worship cock (a redhead kneeling on a bed stroking two black men with large chocolate cocks).

I just called a cock chocolate. As in something delicious and habit-forming,

I wonder what it would feel like to be stroking those massive BBC’s.

I wonder what it would be like to suck one.

I wonder what it would be like to have one in my ass.

I wonder what it would be like to have one pummelling me in each end.

Fuck!

#181 Sissies have no need to worry their pretty little heads with big words or complex thoughts. Sissies are blissfully dumb. All they think about is cock (A blonde-haired girl moving back and forth from one big cock to another).

I couldn’t fathom this one. I was an academic. Yet even so, I could still tell I was being manipulated by the pictures, the gifs and the words. Even analyzing the logic of how it worked didn’t diminish its effect on me.

I wasn’t being brainwashed per se… but I could feel the psychological seeds being planted and taking root.

#183 A sissy is always on her knees ready and waiting before his cock even comes out (a gif, one of the best ever, of a short blonde on her knees literally bouncing up and down with excitement as a sitting man fishes out his cock).

I wonder what I would feel if this fantasy became real.

What if I were on my knees in front of a cock?

What would I feel?

Hunger?

Eagerness?

Lust?

Fuck!

#198 Don’t think of begging on your knees as being degrading (a brunette in stockings on her knees in front of a black man with a cock so huge that I imagine almost any woman would beg to have it).

I imagine if you’d made the commitment to lower yourself before a cock… begging would be the natural next step.

#201 Before you pleasure a man’s cock, take a moment to admire its beautiful size and shape. Take it all in with your eyes before you take it all into your mouth (a woman on her knees, a constant in these pictures and gifs, staring at a cock with lustful admiration).

This was how it started for me.

I started noticing the different cocks.

Different lengths.

Different shapes.

Different girths.

Different colours.

I hadn’t realized I was doing it, but for the past few months I’d been admiring cocks, and not just since Christmas.

#227 When you wear a butt plug, don’t think of it as a toy. Think of it as a place holder for the next big cock you’ll have the pleasure of being filled up with. Let this surrogate cock motivate you to find a man who will replace it with his living cock (a young-looking girl with a ponytail lifting up her short skirt to display a plug in her ass)

This one really amused me.

I couldn’t explain it.

But the words, although ludicrous, made perfect sense to me.

By now I desperately needed to come.

So I tried to calm myself down, feeling compelled to obey my Mistress and to refrain from coming.

I decided to send the pictures and gifs I’d chosen so far to Mistress M. To my surprise, I counted 29 pictures that I’d saved, more than double the required number.

I shrugged, zipped all the pictures and sent them off with a brief note:

Sorry, I couldn’t limit them to 12.

Kendra

I sent it and then shook my head at signing it Kendra without even a thought.

Wanting a break from my raging rod, I found the YouTube clip about high heels and pressed Play.

The clip began with a very attractive and personable black lady introducing herself and then saying, “I’m here to show you the right way to strut your stuff in heels.”

I was hoping simply not to die in heels.

The lady suggested beginning with wedge heels for super stability… a style which I didn’t have.

She followed with chunky heels… which I also didn’t have. Mine were stilettos.

She called the stiletto the mother of all heels… and I had to agree with her.

Mine had platforms at the front below my toes, just like in the video. She stressed that these give you the ultimate effect, and they’re easy to walk in so long as you properly concentrate your weight on your heels or your toes in varying conditions.Ultimate effect… perhaps.

Easy to walk in… God, no.

Finally, her detailed advice:

1. When walking, place your heels first: as this stabilises your feet and gives you more balance.

2. Don’t walk toes first: it looks and feels awkward and clunky.

3. Walk by placing one foot directly in front of the other: this is a great way to establish your signature walk.

4. When going upstairs, place your toes first.

5. When going downstairs, plant your entire foot simultaneously, and be sure to use the rail.

I’m not going to lie… at first the video didn’t help me much at all.

Then I focused on how she was walking and tried to emulate it.

After a few minutes, a few stumbles and a fall, I was getting comfortable with my strut… I began to try walking sexily, as if I were on a runway.

I resisted going to online porn anymore… knowing I couldn’t come without permission… so instead, I remained dressed as a girl and headed downstairs to grade papers.

It wasn’t easy, as my cock begged for attention.

But I resisted like a good girl.

DAY 5: Saturday the 29th

I slept in until almost 11AM, God, I love the holidays.

I had plans for the day: I was meeting a couple of buddies to watch basketball at my friend Derek’s house.

I considered cancelling, but I really needed to get out of the house.

I had to get away from Tumblr.

Yet first, I had to check out today’s task.

I opened the box and found two butt plugs and a tube of anal lube.

Today’s task seemed obvious.

I was expected to explore anal with myself.

I read the note.

Kendra

Today we’ll stretch your boundaries, and I mean that both psychologically and physically.

I expect you to wear the smaller butt plug in your cunt for four hours, and then to replace it with the larger one for the remainder of the day.

Of course… no coming. As a matter of fact, today you’re not allowed to touch your dick at all, except judiciously whenever you pee.

Mistress M

No doubt anal sex had been intriguing me, especially yesterday.

What it would feel like to get ass fucked? Or in sissy language, to have my pussy pounded?

Yet like everything else, fantasy and reality were two different things.

I had breakfast, showered, and then examined the butt plugs more closely. The first was pretty small… the second a reasonable size… neither was massive, thank God.

I had to leave in twenty minutes and wouldn’t be back for at least six hours, as we were watching a double header.

Feeling compelled to obey, I took the lube, coated the small plug, bent over, and gently pushed.

Nothing.

A little firmer push, and after a bit more resistance it slipped inside.

I moaned.

I’d expected a sharp pain… but all I felt was a slight awkward discomfort.

I put on my panties and pantyhose, which I assumed and hoped would keep the plug in place, added a pair of socks and jeans and a dress shirt that I tucked in to avoid any chance of the top of my pantyhose being seen.

Usually I wore my Celtics jersey to watch basketball games, so this departure would be noticed and I’d be called on it… but it was the only way to make sure if I bent over or something, the top of the pantyhose wasn’t accidentally seen by anyone.

I walked around a bit, getting used to having something lodged in my ass that I intended to be there, and was surprised by how quickly I got accustomed to it.

I stuck the second plug and the lube in a knapsack and headed out, not sure how I would change plugs in four hours, but deciding I could figure that out later.

I sat down in my car and groaned as the plug was pushed deeper inside me… reaching new depths and providing me a bit more discomfort than before.

I drove over to Derek’s.

Once I arrived, I was a little more careful when I sat down, and found that every time I moved, I could feel the plug shifting around inside me.

It felt weird, but good.

I took a razzing for the dress shirt, but I told the guys my jersey was dirty since Paige was gone, and I sure as fuck didn’t know how to do my own laundry (which wasn’t true, I did most of the laundry for both Paige and me, and I’d need to do some tomorrow).

We chatted like we usually did and once the first game was over… the 76ers beating the Raptors in overtime, I suggested we order pizza.

They agreed, and I offered to pick it up.

They said we should just have it delivered like we always do, but I argued that I needed to hit the bank, so I’d go pick it up.

They shrugged, figuring whatever.

I went out, drove to the pizza place, and went into the washroom with the knapsack containing the larger butt plug and lube.

I went into a stall, pulled down my pants, pantyhose and panties (the ultimate three P’s…LOL), and pulled out the plug (two more P’s).

The extraction made a little popping sound.

I wiped the plug off with toilet paper after dipping it in the toilet (I know: a little gross, but the better of two options, if you catch my drift) and stored it in the bag.

I was lubing up the larger butt plug just as someone entered the bathroom.

I tried to be quiet as I bent over and inserted the longer and wider butt plug into my cunt. (Yes, I was choosing to call it a cunt, but that raised a conundrum: if it was going into my cunt, then it couldn’t be called a butt plug, could it? But if it wasn’t a butt plug, what should it be called? I didn’t think it qualified as a dildo. Enquiring minds want to know!)

Like the first one, my cunt resisted the invasion, but with a little extra oomph I was again full, and I let out a gasp, as this time there was a sharp pain.

I leaned against the stall door and got used to having the bigger toy inside me.

After a minute, I pulled up all three layers and stood up. Fuck, this was bigger.

I walked out, a little bowlegged as I tried to get used to my new passenger.

I went to the till, got my pizza and carried it out to the car.

I sat down gingerly, but the plug still forced itself deeper into me.

“Fuck,” I groaned to myself at the discomfort… then noticed my cock was hard.

I drove back to Derek’s and walked into his house, desperately trying to get used to the awkwardness before encountering the guys.

I set the box in the kitchen and called out, “Pizza’s here.”

They came in and grabbed slices and beer, and we all trooped out to watch the Celtics game.

I sat down slowly and very gingerly, and luckily the game was already on so no one was paying attention to me, and I ate my pizza and watched the game… trying not to shift around at all.

After a while I got used to it being inside me, which freed me up to change positions very cautiously on occasion. I felt a little slutty, knowing I was dressed in feminine undergarments beneath my clothes while sitting here with my best friends… and well… either I had a plug in my ass, or a toy in my cunt.

I did jump up once when Irving swished a three pointer with four seconds left to tie the game (unfortunately we lost with one second left, in case you care).

I made it through but headed home right after the game, wanting to get away without getting caught by my buds. During the afternoon I’d downed only one beer (a Budweiser, if you care).

I made it through the rest of the day, ending it with something having been in my cunt for ten hours… finally taking it out so I could, you know, go to the washroom and then to bed.

As I drifted off, my pussy felt a little empty and I wondered what it would be like to have something more active going in and out of my pussy.

Perhaps Paige pounding me with a strap-on.

Perhaps a black man reaming me with his massive cock.

Fuck!

Day 6: Sunday the 30th

I got up, showered first and then feeling kinky, inserted the bigger toy (not calling it a plug) into me, before climbing into fresh panties and pantyhose. I then put on another of Paige’s dresses and the red heels (although they didn’t match the outfit), grabbed the laundry (I was now wearing my last pair of panties and pantyhose) and went down to the basement to toss my undies into the washer. For the first time in my life, I used the delicate cycle for my own clothes.

I then went and opened Day 6… realizing I was reaching the halfway mark of this surreal twelve days.

When I opened the box I found a red vibrator and a black dildo.

Oddly, this time there wasn’t a note.

I was rather disappointed.

I looked at the vibrator and turned it on, discovering it already had batteries.

Was Mistress M expecting me to fuck myself with it?

I assumed so.

First though, I did what I did every Sunday morning… I called Mom.

We chatted for an hour… like we always did.

Although this was the first time I’d spoken to her while dressed as a woman.

I got off the phone, made grilled cheese and had lunch (I feel pretty confident you needed to know how much I love grilled cheese).

I went up to my bedroom, grabbed my laptop, and the phone rang.

It was a blocked number but I picked up anyway. Could it be…?

I answered, “Hello?”

“Cheers, Kendra,” the sultriest English voice in history greeted me.

“W-w-who is this?” I stammered, even though such a greeting could only come from Mistress M.

“You know who I am, you silly girl,” she responded, her accent so alluring.

“Mistress M?”

“Of course,” she said.

“How did you get my number?” I asked, wanting to learn more about her.

“If I can get your address, how hard do you think it is to get your phone number?” she answered, giving me absolutely no intel.

“Fair enough,” I said, feeling overwhelmed. Even over the phone, I felt awed by her presence.

“Are the heels on?”

“Yes, I assumed you would expect me to wear them,” I replied, sounding so pathetically submissive.

“Are you used to them yet?”

“Getting there,” I said, before joking, “you could have sent me a pair of wedges to start with.”

“No need: I knew you would be a quick study.”

“Thanks, but I still feel weird in them,” I responded, for some reason wanting this conversation to continue for as long as possible: partly to learn more about her, and partly because her voice was so fucking sultry and hot.

“Practice makes perfect,” she dismissed my concern.

“Okay.”

“29 pictures and gifs?”

“Yeah, I guess I got carried away,” I admitted.

“No worries. You may already be in the advanced stages,” she said.

“Of what?” I asked.

“Sissification,” she said, her tone implying the answer was obvious.

“Who set this up?” I asked, that being the question I wanted answered more than any other.

“I’m sure your benefactor will inform you when he or she sees fit,” she said, before adding, “just be assured it’s someone who cares, and is doing this for you!”

“For me?”

“Before Christmas, were you at all curious about sucking cock?” she asked, the word ‘cock’ sounding so hot with that English accent, almost as if it were spelled ‘kawk’.

“A little.”

“Be honest,” she pressed, “only a little?”

“Well it was becoming more intriguing even before Christmas,” I admitted.

“Good. And now?”

“Now it’s all I can think about,” I admitted to this enchanting stranger.

“Good girl,” she purred, making my cock flinch.

“And do you want a kawk invading that virgin pussy of yours?” she continued, my cock once again flinching in my panties.

“Maybe,” I answered timidly.

“Don’t ever answer me with a maybe,” she scolded. “It’s a yes or no question, Kendra.”

“Yes, then,” I responded too quickly.

“Then maybe you need a nice spit-roast.”

“That would be crazy,” I said, having recently imagined taking a cock in both holes almost nonstop.

“It’s what all good sissies crave,” she explained.

“I guess,” I said.

“Ready for today’s training?”

“Yes.”

“Yes, what?” she prompted.

“Yes, Mistress,” I caught on, addressing her as ‘Mistress’ for the first time.

“Good girl. Go to your laptop, search for ‘Rulestobecomeasissy’ on Tumblr, and find the list of positions,” she instructed.

“Okay,” I said, going back to my bed and finding the account. The first was a gif of a brunette on her knees, in a short, very short skirt, sucking just the head of a cock between her lips, looking up at the man whose face was outside the picture, with the words flashing: SISSY POSITION 1: ON YOUR KNEES: the most natural position for a sissy.

“Found it,” I said.

“Good girl,” she approved. “Now get the vibrator and dildo I so generously left for you.”

“They’re down in the kitchen,” I said.

“Go get them,” she ordered.

“Yes, Mistress,” I agreed.

“Good girl.”

I put the phone down, went to the stairs, and walked carefully down in my heels. Step by step, planting both my heel and toes simultaneously and bracing myself on the rail almost desperately, still not doing too well on the stairs with heels.

But once I left the stairway I was able to actually saunter into the kitchen, flaunting my new feminine persona even though I had no observers, placing each new step directly in front of the prior one.

I grabbed the vibrator and dildo and returned up the stairs, toes first, again relying heavily on the rail for balance.

Back in the room, I grabbed the phone and reported, “I’m back.”

“Get into the same position as the gif,” she ordered.

I knelt.

“Copy it as best you can, using the vibrator as the cock,” she ordered.

“Yes, Mistress,” I said, as I held the vibrator in front of me with my right hand while taking just the head into my mouth, pretending I was looking up into the face of a woman standing before me with her strap-on in my mouth.

After twenty seconds or so, she said, “Move to sissy position two.”

I did.

It said; ASS UP: Your most natural cunt fucking position. It was a woman on a bed lying on her stomach with her ass rearing up and a black man slamming into her from behind.

“Get into that position and position the vibe near your pantyhose clad cunt,” she ordered.

“Yes, Mistress,” I responded, getting into the position.

“Turn on the vibrator and place it at your cunt, Kendra.”

I turned it on and it started buzzing.

“Put your phone on speaker and set it down near your face.”

I did.

“Now press the vibrator against your cunt more firmly and hold it there.”

I did. The vibrations tickled, making the plug still in my cunt also vibrate, and I tried to press it directly against it, but that was awkward. It did make me curious what this would feel like without the panties, pantyhose and toy cushioning the contact.

I’d almost forgotten I was on the phone because of being so lost in these unique pleasure sensations when the sexy voice told me, “Switch to position three.”

“Yes, Mistress,” I repeated, completely drawn in by her voice, and compelled to obey without hesitation.

This position was demonstrated by a skinny girl sitting on a couch leaning against the backrest, with a guy standing above her, his hands resting on both sides of her head as he face fucked her with the caption: Lean back and get face fucked.

I got into position leaning back against the head of my bed and said, “In a similar position, Mistress.”

“Use the vibrator and face fuck yourself, my slut,” she ordered.

“Yes, Mistress,” I obeyed, a chill going up my spine as I heard myself called a ‘slut’ for the first time.

I pumped the vibe into my mouth; it was still buzzing.

“Don’t hold back as you fuck yourself,” she encouraged me.

I obeyed and got more vigorous, but I gagged when I pushed it in too deep.

She revealed herself as being skilled in interpreting my sounds when she told me to “Breathe through your nose.”

I took her advice as I focused on breathing and sucking at the same time. Sure enough, I stopped gagging.

“Good girl,” she purred.

After a couple more minutes she announced, “Final position. Get the dildo.”

“Okay,” I said, and grabbed it off the bed.

“Suction it to the wall,” she ordered.

“Okay,” I repeated, as I looked at the butt end of the dildo and realized it did have a suction cup.

I found an open space on the wall and placed it at the right height for my pussy, as it seemed pretty clear what was coming next. “Done.”

“Lube it up,” she continued.

“Yes, Mistress,” I said, oddly excited that I was about to fuck myself.

“Ready to have that cunt of yours fucked?” she asked.

“Yes, Mistress,” I responded, indeed ready to do just that.

“Good girl,” she purred, as I lavishly lubed the dildo.

“What are you wearing right now?”

“Panties, pantyhose, heels, a dress, and I have the larger butt plug lodged in my ass.”

“Oh my,” she chuckled, clearly amused. “I never even told you to wear a dress: you get extra credit for that. You really are a sissy already.”

“Thank you, Mistress,” I responded absurdly.

“Now that I know what we’re working with, pull down your panties and pantyhose, but only to your knees, and remove the plug from your arse,” she ordered.

“Yes, Mistress,” I said, the word ‘arse’ sounding so nasty.

“You should probably remove your heels too,” she added, as I pulled the plug out. “Once you begin enjoying yourself, it would be a shame if you lost your balance.”

“Yes, Mistress, thank you,” I acknowledged, the anticipation of fucking myself growing in intensity.

“Now get on all fours, feet not knees, and slowly back up to the wall,” she instructed, before adding, “this cock is a little bigger than the plug for that virgin fuck hole of yours.”

God was this degrading.

But as I slowly backed up on all fours like a bitch Rocky(D), my cock was completely hard, and I was completely and willingly subject to her every whim.

“Yes, Mistress,” I repeated, as if those were the only words I knew.

“You’re such a good girl,” she said. “You’re going to be a great sissy slut.”

“I hope so,” I responded, as the tip of the dildo poked into my slightly gaped hole. God was I thankful I’d been wearing a plug for a while to prepare me for this. And, although this entire experience was baffling, and was crushing my masculinity, I really did long for what was about to come.

I was ready to be fucked.

I was ready to become a submissive sissy for real.

“It’s time, Kendra. Press your cunt against your wall-kawk hard enough for it to penetrate.”

I took a deep breath and leaned back, the cock going more easily into me than either plug had done earlier. I moaned as I self-penetrated. “Oh God!”

“That’s it, let the kawk slide gradually into its natural home,” she coaxed, her sultry voice making this seem so natural… like it wasn’t at all weird I was dressed as a girl, on all fours, with a dildo sliding ever deeper into my ‘arse’.

“Feels good,” I reported, which was true, even though it was spreading my virgin pussy wide, and therefore causing me some discomfort and pain.

“Oh, wait until that cunt of yours experiences a real throbbing kawk slamming into it,” she foreshadowed as she made it clear in a single sentence that there was much more in store for me… although with six more days to come (or not to come, depending) I guess that shouldn’t have come as a surprise.

If I were a real man, or at least a stereotypical one, this would have scared me… and yet it didn’t. If I were a real man, I wouldn’t be on my knees with a dildo inside me. If I were a common man, I wouldn’t be dressed as a woman.

So my next words came as little surprise: I’d already given in completely to this sultry stranger, and I said exactly what I felt at the moment: “I can’t wait.”

“Kendra, you may be the most natural sissy I’ve ever trained,” she said; I was unsure whether it was a compliment, or a statement of how pathetic I was.Because of her warm, encouraging tone of voice I took it as a compliment, as the dildo went deeper inside me, causing a crazy mixture of adrenaline rush and increasing inner burn. “Thank you, Mistress.”

“You’re welcome, slut,” she responded, another of her constant reminders of what I was becoming.

After another minute, it was all in. I declared with some pride, even as the burning sensation increased from the dildo reaching new depths, “All in, Mistress.”

“Good girl. How does it feel?”

“Full. Some pain, but good,” I answered, trying to report my feelings as accurately as possible, feeling she was worthy of my complete trust. I’d sometimes read stories about inconsiderate Dommes, and those weren’t her: even though we hadn’t met face to face (that I knew of), I knew that my Mistress had my back. (Or in this instance, my backside, LOL.)

“All as expected,” she said. “Now slowly fuck yourself like the bimbo slut you are. Not too vigorously at first.”

“Yes, Mistress,” I obeyed, as I began doing just that. It’s a surreally strange experience when it isn’t your own cock doing the fucking, as my body moved in opposite ways from when I was with a woman.

As I slowly moved back and forth the pain began to fade, and an undeniable pleasure began to increase, as my rock-hard cock swayed back and forth beneath me. “Oh, God,” I moaned, wanting my Mistress to know I was beginning to enjoy the sodomy.

“Good girl,” she purred. “Is your kawk hard?”

“Very,” I moaned, as I began going faster.

“Very soon we’ll learn if you’re a complete sissy,” she predicted.

“How?” I asked, wanting to be one.

“If you come just from getting fucked and without your kawk being touched, that’s a sissy orgasm,” she explained. “So while you fuck yourself, keep both hands on the floor.”

“Oh,” I said, as I felt my balls boiling, and wondered if I might indeed come just as she described.

“You’re going faster now, aren’t you?” she asked. “Just because you want to, yes?”

“Yes,” I admitted.

“You really are an advanced sissy,” she praised me.

“Thank you,” I moaned, as I fucked myself.

“Tell me how it feels to have your pussy stuffed,” she ordered.

“So good,” I moaned.

“You can do better than that, sissy,” she scolded, “talk to me,” her tone shifting to slightly annoyed.

“Sorry,” I apologized as I rephrased, “I love having my slutty cunt filled with a big fat cock.”

“Better,” she approved. After a moment, she ordered, “Tell me what you are.”

“I’m a slut for big fat cock,” I declared with a moan as her questions and my humiliating answers added to the euphoria building inside me.

“Would you rather have a kawk in that cunt of yours, or have your dick in a pussy?”

That was a tough question. The answer should have been obvious. I mean, any man would prefer their dick in a pussy, wouldn’t they? Yet, at the moment I wasn’t a man, I was a sissy; and the answer for a sissy was equally simple. I replied, giving the answer I felt was truest at the moment, “I’d rather have a cock in my cunt.”

“Good answer, sissy,” she approved. “You are already understanding who you really are.”

I was really fucking myself now, my desire to be a complete sissy consuming me, as well as feeling an indescribable pleasure that was creating pulsations throughout my very core… my cock felt ready to burst without even being touched. Was such a thing even possible?

Wanting her to know I was indeed accepting this part of my inner being, I admitted, “Yes Mistress, I’m a submissive sissy for cock.” I then added, following two deep thrusts, “For any cock.”

“You have my permission to come if you’re able,” she offered, seeming to be impressed by my declaration, “but only if you can do so without touching your dick.”

“Thank you, Mistress,” I moaned, moving much faster now, taking the entire cock in my wanton cunt, desperate to come, wanting nothing more than to experience my first sissy orgasm.

“I can tell that you’re close, sissy,” she told me.

(Her accurate appraisal likely came from hearing my whimpers, which were a blend of masculine and feminine. In essence I felt I was manifesting a third gender that didn’t appear to have a name. ‘Neutral’ wouldn’t work, since my mental and emotional state had nothing to do with the absence of sex. ‘Pansexual’ was too broad a term. ‘Asexual’ would be wrong, since I could never reproduce through mitosis like an amoeba. ‘Shemale’ referred to someone manifesting two physical genders; Perhaps ‘intersex’? Although that term had slightly different connotations from what I was experiencing: I had no desire to become an actual woman; my goal, as I was coming to understand it, was to become more like a woman, a goal which appeared to be perfectly within my reach (with sufficient help and guidance), without requiring any hormonal treatments or surgery. I could tell I was becoming less of a real man, but I wasn’t becoming a true woman, I was heading somewhere in-between. So I guess the perfect term for my mental and emotional state right now was ‘sissy’: and long-term, I was well on the way to becoming a bonafide sissy. But back to the action: I was about to come.)

“Yes, Mistress, I’ve never felt like this before,” I admitted, which was again the truth. This was a completely different experience from being the one doing the fucking (although in essence I was still doing the fucking, but I think you get my drift).

“Your mind and soul are transitioning from your wrongfully born manhood to your natural inner feminine side, that has until recently been locked away dying to get out,” she explained, which would have seemed absurd a week ago, and yet now it could explain so many of my new and confusing feelings. And it also could explain so many of my confusing desires in the past: to wear panties and pantyhose or scroll through Tumblr sissy gifs, and so forth.

“I can feel that,” I admitted, as if even my body were transitioning into an entire new molecular structure: one that was neither masculine or feminine, and yet both at the same time… a hybrid that didn’t really make sense on a strictly physical level,, and yet which went a long way towards explaining my feelings at the moment.

“Oh yes,” she moaned, which made me wonder if she was pleasuring herself while she instructed me in doing so. “Man is becoming woman. Straight is becoming not bi, but bent. Ken is becoming Kendra.”

Her words made complete sense to me, for I could feel my pleasure driving my transition as it consumed me and my balls boiled. “Yes, I’m truly becoming Kendra,” I declared.

“Kendra the sissy,” she added.

“Yes, Kendra the sissy for cock,” I agreed, totally caught up in this transformative experience.

“For any cock,” she embellished.

“Yes indeed, for any cock,” I moaned, wondering if a real cock would feel even better than this inside me… I imagined it would. The pulsations alone of a cock should enhance the pleasure tenfold, I bet.

“Cock sucking isn’t something you do, a cock sucker is who you are,” she continued.

“Yes Mistress, I’m a cum hungry cock sucker,” I agreed, adding, “taking every load in my mouth or on my face.”

“Now come for your Mistress,” she ordered. “Show me how special a sissy you are, Kendra.”

“Oh yes, Mistress,” I moaned, going as fast as I humanly could… taking every last inch inside my slut cunt with each and every thrust, “I want to be a good sissy for you!”

“Good sissy perhaps, but are you a complete sissy?” she pressed, continuing to demean me, as if knowing that by enhancing my humiliation she also enhanced my lust, and her repeatedly calling me a sissy would indeed help to turn me into a sissy (and even a complete sissy)… which at the moment seemed to be an accurate theory, as with every passing moment I became more like the person she said I was.

“Yes, I’m a complete sissy,” I agreed again, not really knowing everything a complete sissy might even do (was I already doing it?), but I was so eager to please my Mistress, and I was getting so desperate to come (I’d never needed to come more fervently than I did at this moment) as I threw myself back on the cock over and over as fast as I could, taking it as deep as I could, feeling my balls getting so close to exploding.

“You’re a two-hole fuck slut for any man,” my Mistress continued her litany.

“Yes, I’m a complete whore for anyone’s cock,” I agreed, before adding, “especially some huge black cocks.”

“Every sissy eventually wants to be used by black kawk,” she chuckled, amused.

“I’d love to have a big black cock right now,” I said, wishing there was one right here for me to suck, and maybe even to fuck.

“Tomorrow,” she promised, making my eyes go wide in astonishment, but I set even that revelation aside for now with my orgasm so fucking close. “Now come, you kawk sucking… cunt taking… SISSY!”

“Fuck!” I screamed, as my cock erupted from the big black cock in my cunt right now, plus my excitement about the prospect of experiencing a big black cock in some fashion tomorrow, and I spewed my load all over the floor.

“Good girl, very good girl,” she purred, as my body trembled in release. “That’s how to come for your Mistress!”

“I am coming for you,” I told her weakly, as cum kept shooting out of me and my entire body shook like Paige’s did when she came… fuck, I was becoming more like a girl: this orgasm was way more intense, and substantially longer, than any I’d ever had before. EVER!!!

“Such a good sissy,” she purred.

“Thank you, Mistress,” I murmured weakly, my entire body now usurped of energy.

“Now don’t waste that cum,” she added briskly. “Lick it all up.”

“Yes, Mistress,” I obeyed, as I mindlessly kneeled down, the dildo sliding out of me, then turned around and licked the cum off the laminate floor like a cat licking up milk.

“Good girl,” she repeated. “Have a good rest of the day, Kendra. Do whatever you like except come. Tomorrow you begin your advanced training.”

“Thank you, Mistress,” I said again, as I heard the phone click and she was gone.

I finished off all the cum, stood up, pulled up my panties and pantyhose, and even though it was still early afternoon I went to the bed… onto which I collapsed, and fell into a deep, satisfied sleep a few minutes later.

DAY 7: Monday the 31st

New Year’s Eve.

I would be spending the evening with a bunch of friends, as Paige wouldn’t return home until Saturday (the twelfth and final day of my sissy training).

I recalled Mistress M promising I would suck someone’s cock today… his black cock.

Did I really want that?

When I was horny, I definitely did.

When not… like now… I wasn’t so sure.

Like I said, fantasy and reality are two very different things… although the line between them had been blurring considerably during the past week.

I headed downstairs, opened the Day 7 box and found inside a red lipstick, a blonde wig, a black dress, and black heels.

I read the note.

Kendra

We are into the action stage now.

Today you will suck your first living cock.

Today you will swallow your first load directly from the source.

Today you might take your first facial.

At 1PM I will text you the address for a gloryhole.

You will go there.

You will suck at least one cock.

You may choose to suck more, if you wish.

You will swallow the first load.

Of course, you will wear your new dress and heels, and I suggest a pair of black pantyhose. You will finish off the ensemble with the wig and some lipstick. I know you’re not experienced with lipstick, but try to apply it as tastefully as you can. You don’t want to look like a slut after all, even though you’ll be acting like one, lol.

Mistress M

Once again, I was torn.

I could already feel my mouth watering.

Yet everything I’d done up to now wasn’t cheating. Wasn’t gay.

Taking a toy in your ass didn’t make you gay.

Sucking a real cock was both cheating and gay.

Yet, although I’d like to say I fought long and hard over what to do, an hour later I was all dressed up and watching a YouTube video on how to apply lipstick properly.

Panties were on.

Pantyhose were on.

Black dress was on.

Black heels were on.

Lipstick was on.

Wig was on and brushed as attractively as I could manage.

I looked in the mirror.

And I had to admit, I looked kind of hot.

I then shook my head because I’d just seen myself as hot.

I waited impatiently for the text.

When it came, I gasped.

It was in the south district.

The black district.

A district that was adjacent to the one where I taught. A district that even had a few students going to our school (usually the academically advanced ones, as we were a better funded school, or because they were the athletes we wanted).

Again, a mixture of excitement (as promised, my first cock would likely be black) and trepidation (this wasn’t an area of town you trespassed into alone, although at one in the afternoon it should be okay).

I went into the garage, removed the wig in case any neighbors saw me, and drove… finding that driving in heels was harder than walking in heels.

I arrived at the location a few minutes early, and received a text.

You’re early!

I responded back: How do you know that?

She responded: GPS tracker.

I texted back, as I put my wig on: Oh.

She responded: Go to room three. Your first cock is already waiting.

I responded, adjusting the wig: It is? (Notice we didn’t refer to the person, but only to his appendage).

She responded: I made sure your first was one you wanted.

She added: BIG!

She texted again: BLACK!

I responded, finally satisfied with my wig: Thanks!

She replied: Of course! Have fun! Stay as long as you like.

Likely I’ll just stay for one.

That’s what they all say, but we’ll see. Now go and become an official cock sucker!

I replied, as I got out of my car: Right away, Mistress.

I sauntered in, using my sultry feminine walk, trying to look as sexy and girly as possible, but was happy to see the adult store was relatively empty.

I walked to the back, keeping my head down as I passed two black men both in their forties, I estimated.

I found some video rooms and went into room three.

Closed the door.

Saw there was a television playing porn. A stool. A hole in each of two walls… likely accessing rooms two and four.

A moment later a black cock, semi-erect, popped into my room.

This was really happening.

I walked over to it wordlessly.

I moved the stool away.

I knelt like a good sissy.

I took it in my hands.

Somebody groaned, whoever was attached to the other end of my new paramour.

I stroked it.

I stared at it in awe.

I opened my mouth and took it in.

It felt… so… natural. As if this is what had been missing from my life until now.

It felt… so… surreal. I was finally making a fantasy I’d never fathomed becoming a reality, become a reality.

It was… so… stimulating. Feeling this cock hardening in my mouth was the most magical thing ever.

I bobbed slowly, taking in only two inches of the eight-inch shaft (give or take), really worried I might gag if I tried taking it all in too soon, and figuring baby suck steps were necessary. (Baby suck steps…. Hehehe did I just make up a new term for rookie cock suckers? Hey, I was now officially a cock sucker. Hey, why was that so exciting?)

Once it was completely hard, I began bobbing a little faster, taking a little more into my mouth every few bobs.

I wasn’t sure how I was doing, but hearing soft groans made me feel I was doing okay at the very least.

It also made me want to get him off… to taste his cum. I realized I couldn’t completely depersonalize this cock, there was a living, breathing, person here, who was getting horny and excited because of what I was doing… not just to his cock… but to him.

“Faster, cock sucker,” a deep voice, a young voice, ordered me.

I obeyed, bobbing faster… wanting to be a good cock sucker, a good sissy.

I sucked for two, perhaps three minutes, his moans getting louder. I was getting about five inches in before he warned, “Get ready, cock sucker.”

I kept bobbing, and was rewarded… and yes, it tasted and felt like a reward… with a sudden gush of cum squirting into my mouth and gliding smoothly down my throat.

Rope after rope was deposited into me… which made me feel so good… which feeling I realized only enhanced the fact I was becoming a sissy.

When he was done, he pulled out and walked away.

He said nothing.

I sat there on my heels… and waited. Mistress M was right: I wanted another cock. I needed another cock.

I waited another minute before I heard a voice from behind me. “Come suck me, faggot.”

“Yes, Sir,” I responded, as I crawled, literally crawled, the few feet to the other wall and another black cock, even though being called a ‘faggot’ made me cringe. It was such a derogatory term.

It was completely flaccid, so I took the entire sausage right in my mouth.

I wanted to feel it going from flaccid to hard.

I wanted to be the one who made that happen.

I swirled my tongue around his cock.

I felt it harden in my mouth.

I felt a rush.

Once hard the guy said, “Now get sucking, faggot. I don’t have all day.”

I smirked as I thought, I do.

I then began bobbing.

This black cock was smaller, seven inches, but so thick now that it was hard, it spread my mouth considerably.

“Take it all, faggot,” he demanded,

I took a deep breath and took it all… my nose actually touching his groin.

I held myself in place for a moment until I gagged and backed off.

“Get that fucking mouth back on my dick,” the guy demanded.

“Sorry, Sir,” I apologized, loving to be told what to do.

“You will be,” he threatened.

I resumed sucking his cock, focusing on breathing through my nose, glad I’d practiced doing this with the vibrator yesterday, and taking as much of his cock in as possible.

I wanted to be a good cock sucker.

I wanted to be able to deep throat.

I bobbed for two or three minutes before he grunted and without any other warning, spewed his salty seed into my mouth.

Fuck, I loved the thrill of having a cock shooting in my mouth.

Fuck, I already loved the taste of cum.

Fuck, I wanted more.

When he pulled out, I said, “Thanks.”

He chuckled but didn’t say anything.

“Over here,” a new voice summoned from behind me.

I turned around and a massive black cock, already erect, was calling to my mouth.

I scurried over and took it in my hands as I said, “Your cock is huge, Sir.”

“I know,” he said, likely hearing that a lot.

“Fucking huge,” I repeated, it was easily ten inches long and almost that in diameter, before I took it in my mouth.

The owner of this massive cock was a man of few words as he allowed me to worship his cock for several minutes.

No name calling.

No humiliation.

Just the odd moan or two.

I knew I’d never be able to take all ten inches in my mouth, but I wanted to take as much of it as I possibly could.

For over ten minutes, I sucked.

During that time I got almost eight inches of it in my mouth.

After ten minutes my jaw began to get sore, yet no way was I going to stop sucking.

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