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Crossdressed with Office Colleagues – Hot Crossdressing Sex Story

13 Min Read

Once I was returing from office, I missed my cab. It was raining heavily and I was completely wet. Finally I found an auto and reached home. To my dismay, no one was in the flat and I didn’t have key. I called my room mate and he said he had gone to a party and will return after 12 midnight.I looked at my watch and it was 6 in the evening. I was feeling cold because all my clothes were wet and it was winter too.
Thus, I called my office colleague Annu. She stayed in the same society. I went to her home.
She used to stay alone in a flat. She has wheatish complexion, her age is 25. Her figure is 34 30 34.
She invited me inside and gave me a towel. I wiped my hands, my face and my hair. She told me that I should change clothes otherwise I will catch cold. She went in her bedroom to look for some clothes.
She came back and said that she has kept some clothes in the washroom and I should get freshen up and change clothes.
I agreed.
I went inside and was surprised to see what kind of clothes she kept.
She called from the other room “sorry, I don’t have any male clothes, you can wear my clothes. Its just a matter of few hours.”
I was overwhelmed and said “no problem dear.”
I removed all my clothes.
Then I wore a white panty she had kept for me. It had pink flowers design all over it. I wore the panty. It was very soft and it gave me a hard on.
I thought it would have been so nice if Annu had kept a bra too, however, there was no bra.
She had kept a blue color salwar kameez. Actually it was a Punjabi dress. I wore the Patiala salwar and tied the knot.
Then I slipped my arms in the blue kameez. It was a bit tight for me which made me look hot if I had boobs.
It was deep neck and had a zip at the back. I was dressed in Annu’s clothes and then I realized that I wanted to wear her clothes and I wanted to get dress up like her in the past, and today my dream came true.
I stepped out of the washroom. Annu saw me and she smiled blushingly.
She asked me to sit down.
She told me that if I had long hair and I applied some make up then I would look like a complete girl.
I said that is not possible. But then I said that I would like to try. She said that she doesn’t have a wig.
But she took me to her dressing room, she made me sit at the dressing table. She started applying lipstick on my lips and foundation cream on my face.
She covered my head with a dupatta which hid my short hair. Then she said “look” and started smiling “now you look like a woman.”
I said “no, not yet, I don’t have breasts.”
She said “oh, but what can you do about that.”
I said “I can”
She said “how?”
I stood up, unzipped the back of the kameez and removed it. Then I said “give me a bra”
She was surprised to hear that. She went to her wardrobe and came out with a pink padded bra. I took the bra from her and started wearing it. She helped me by hooking the bra from behind.
Then I said “I need two blouses”
She gave me two. I placed the blouse in the cups of the bra to make fake boobs.
She was surprised and said “wow! I never thought that, do you like to wear these clothes? Have you worn them before?”
I said yes while I started wearing the blue kameez again, she zipped the kameez from the back. Now I looked like a complete woman.
She said “whose clothes do you wear?”
I said said “when I was a child, I used to wear mom’s clothes. When I became an adult, my fondness for cross-dressing increased and I started wearing all types of clothes. Whenever I got a chance, no matter whose clothes it maybe, but I would wear them.”
She said “how are you feeling now?”
I said “a complete woman. I just wish if I had a boyfriend or a husband whenever I am dressed.”
She smiled and said “what do u want now?”
I gathered courage and said “I want to get fucked.”
She said “ok, there is a guy coming to fix internet connection, maybe we can trap him”
I was so happy and at the same time I was nervous. I said “ok, but why will he get attracted to me and not you?”
Annu said “because he is a friend of mine and he is gay.”
Annu took out her cellphone from her bag and called the guy and said that she has a surprise for him. After 15 minutes the door bell rang. A tall guy of height 6 feet stood at the door, his built was good, he was a bit dark and he wore a white ashirt and denims.
She called her inside, he too was completely drenched. Just then I entered the room and he was completely surprised to see me.
Annu said to him “Meet him, he is a friend of mine and likes to dress up as a woman. A perfect match for you.”
He shook hands with me. His grip was tight, I blushed. He said “Hi, my name is Ajay. You are very beautiful.”
I said “Thanks, my name is ***** but I liked to be called as Rani when I am dressed up.”
Annu said “OK Ajay and Rani, both of you sit here and chat while I make tea.”
We sat on the sofa. He sat very close to me. He said “So, u like cross dressing, then you must be gay”
I said “Just when I am dressed, I feel like a woman and I enjoy the company of a decent man.”
He came very close to me and placed his arm over my shoulders. I blushed.
Annu entered and kept the tray of tea on the table.
She said “Both of you are quite close now, I can see. Why don’t you two become partners?”
Anyways, Annu was wearing a silky brown skirt and a black top.
I said “Annu, I would like to dress up as you all the time and I want Ajay to be with me whenever I dress up.”
Annu smiled. Ajay said “Annu, I am completely wet.”
Just then I placed my hand on Ajay’s face and started kissing him, I was sucking his lips and his mouth. He started kissing me back and pressed my fake boobs.
Just then Annu said “Maybe you want to use my bedroom if you want.”
We came to her bedroom, Ajay hugged me titely and started kissing my neck and my shoulders.
Annu sat on the sofa in her bedroom and was looking at us.
Ajay removed his shirt and took me in his arms. I completely gave in to him. He removed his jeans. I could see his hard on clearly from over his jockey underwear.
I pushed him on the bed and came over him. He laid on the bed and I started removing his underwear. WOW! He has a 8 inch long cock.
I took his cock in my hand. It was very warm. I started shaking it. He was moaning “ahh.. suck it Rani”
I kept my lips on the tip of his hard dick. I tasted his precum.
Then I started inserting it in my mouth.
I completely took it in my mouth and started sucking it and rubbed his balls with my hand. He said “Ohh Rani, I wana fuck you bitch.”
He started fucking my mouth.
Then I came over the bed, untied my salwar and removed it. He started pressing my ass from over my panty. He came behind me, made me sit like a bitch, lowered my panty and started rubbing my asshole from the tip of his penis.
I moaned and when I opened my eyes I saw Annu had removed her pink panty from under her skirt and was rubbing her pussy while she enjoyed our session.
Ajay started pushing his rock hard dick inside my asshole.
I felt pain as well as pleasure.
He held me from behind and started pushing his cock in and out of my ass.
Slowly he was gaining speed. He started fucking me madly. I was moaning in pleasure.
He fucked me said “I want to cum, I cant control” and just then he exploded his streams of sperms in my asshole.
Now he was completely exhausted.
I was feeling great, my penis had also become rock hard and I also wanted to take out all my sperms.
I noticed Annu was rubbing her pussy very fast now and had eyes close.
I went to her, grabbed her thighs and started pushing my hard dick inside her pussy. She hesitated but gave in to the heat of the moment.
I raised her top and started pressing both her boobs and also started fucking her madly. I couldn’t control myself and I was fucking her like a Rocky(D). Just then she reached her orgasm and was moaning madly but still I didn’t stop. I fucked her for 5 more minutes and took out all my sperms in her pussy.
Then Annu and me came to the bed.
She removed all her clothes.
Three of us again had sex. Ajay was fucking me while Annu sucked my dick.
I hope you liked the story.

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