How I Became A Sissy Roommate free porn video

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Hi this is Jeet from Mumbai. It was the end of my 12th boards and I had gotten admission in an engineering college in Pune. It was always my fantasy to be a sissy slut for a guy and so I began to find people online who were looking for roommates on planet Romeo a gay social website. I found a guy named Paras who had a flat in Pune which was near my college and he wanted a roommate to split the rent. He was a 23 year old dominant top and wanted a bottom as a roommate. We discussed the rent and he asked me about my stats and told me to send naked pics to which he approved. He sent his pics too n I was looking at a dark 6 foot tall guy with a nice build and a nice thick 7 inches cock, whereas I was an average built fair guy with a 4 inches sissy cock. So the day arrived and I reached Pune. I was given instructions on how to reach and he had told me to call him as soon as I reached his building.

I reached and gave him a call. He told me to come on the 4th floor and he opened the door. He welcomed me in and gave me place to keep my bags. Then we talked about the things that we had discussed on the internet. He told me to get naked and I obeyed. I had shaved my face clean and my hair was long enough. He told me to turn around and he saw that I had hair on my chest arms and legs. He instructed me to go to the bathroom and he made me sit in the bathtub. He used a razor to shave all my body hair, it was very awkward for me but he finished in a few minutes and now I was completely hairless and smooth.

Now came the part where he told me I was to be his sissy slut and dress as a girl full time and behave as a girl too. This was a dream come true for me and so I agreed instantly. He took me out and made sit in front of the mirror. He brought in a few bags saying these were the clothes I was supposed to wear when I was at home and I wasn’t allowed to dress like a guy at home. He brought a small chastity device and locked my sissy cock into it and said I would be given the key to it only at the end of the day I won’t be allowed to cum till then. Now my cock was in bondage and I couldn’t masturbate so I would remain excited for a long time. He gave me pink stockings a lacy pink bra and thong panties to wear. Upon that I was given a short black skirt and a tight white top which showed the shape of my boobs and nice cleavage since I was wearing a push up bra. He gave me a makeup kit and tied my hair into two tight high ponies. I looked like a complete sissy girl. I couldn’t believe myself. It was a dream come true.

Now he told me to get up and took me in the hall and made me ramp walk for him, do a little dance steps. I could see his cock bulging in his pants and I wanted it badly. He got up and held me tightly and started kissing on my lips and fondling my breasts. He kept on kissing me deep with his tongue and I was in ecstasy. He removed my top and my skirt. My cock was trying to get hard but it couldn’t due to the chastity device. He removed his shirt and told me to get on my knees. I did so obediently. He brought forth his crotch and said you know what to do slut. Like a hungry slut I pulled his pants down and his 7 inch throbbing cock came right on my face it was nice and hot and oozing pre-cum.

I slowly licked the tip to taste the pre-cum it was nice and salty and I finished licking it off, then I took his warm cock in my mouth and started sucking it slowly. I used my tongue from the inside to lick the tip which made him crazy. I sucked like a pro and he was enjoying it. Then he told me to stop and he suddenly held the two ponies he has tied on my head and thrust his cock in my mouth deep. He held them tightly and started fucking my face. I made gagging noises as his cock went deep in my throat and it turned him on even more. This went on for a good 10 minutes and then finally without any warning he shot his warm load in my mouth in short but huge bursts. I could taste his warm salty cum and I drank it all.

He was exhausted and sat on the sofa. He told me to spread my ass in front of him and then he started applying Vaseline on my asshole. I had never been fucked in my ass so when he put his finger in I felt a sharp pain and flinched. He told me to stand steady and slowly he started fingering my ass with two fingers then three then 4 and I was in heaven. His cock was up and ready by then so he took me to the bedroom he had the mirror in front of the bed he told me kneel in front of the mirror so that I could see myself and he came from behind. I could see he was going to fuck me in doggy style. With one quick blow he was in me and I screamed he held me back and his cock was in my ass.

My ass got adjusted to his cock and then he started thrusting his cock slowly in my ass. I started liking the feeling and I saw in the mirror, I was like a girl in two ponies and a dark guy was fucking me in the ass it was a dream come true. He fucked me for a nice long 20 minutes and when he was about to cum he removed his cock from my ass and blew his cum all over my face. The hot cum on my face felt awesome and I licked it all off. When we were done he removed my chastity lock and my cock was rock hard the moment it was released. He held it and squeezed it hard and that was all it took me to cum and I blew a huge load which he told me to lick and finish.

So this was the first day with my roommate. Stay tuned for more adventures where I was introduced to BDSM how I was fucked by two guys and how I went out as a girl with my roommate. To contact me mail me at I am situated in Mumbai.

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Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

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