Hello, people. I am Sahil. I am currently living in Mumbai in a shared apartment with my roommate Raj. We both doing our engineering from different colleges in Mumbai. This story is based on my and my roommate’s real life experience. Which is how I am engaged in a sexual relationship with Raj. Let us start with the introduction. Introduction: Sahil The author of the story. I am 24 years old. Since I was at 14 I have a very strange fantasy of Crossdressing as a beautiful girl. Whenever I was alone at my home, I used to wear my sister’s lingerie, clothes. I am not much-socialized person hence I was not attending functions of relatives and rather preferring to stay at home alone. Those are my golden days to explore my fantasies of cross-dressing. I used to wear my sister’s bra, panty, pantyhose, saree etc. I also wear makeup and put long hair wig. I have learned to wear sarees from the Youtube videos and makeups. Those days I wore it whole day and night pretending to be a beautiful girl in the house. When I got the admission in one of college in Mumbai, I was shifted here with Raj as a roommate. As I was shifted Mumbai, now I have no privilege to use my sister’s clothes. Hence, initially, I have purchased my own bra, panties etc from the online sellers. Gradually I have purchased my own set of ladies’ items like hair wig, lipstick, bangles, saree, nighty etc. I use the same to become a girl in my apartment whenever Raj is not at home or whenever he is visiting his Hometown. Raj doesn’t know about all stuff I have since I moved in. Raj: Raj is 26 and living in Mumbai since a year ago when I moved in. He has an athlete and strong body. He is kind of Intimidating. The only habit Raj has is he is a bit alcoholic. He has a group of college friends who are rich and having late night parties. Raj also involved in this group and become alcoholic. But Raj could not be able to handle alcohol much and ended up throwing up it usually. Also since this much consumption of alcohol daily basis, he would not be able to remember anything on next day that what was happened last night or where was he or where were they go for such parties. He came home late in the same situation and after having some dramatic conversation with me slept the whole night and forgot everything in the morning even the talk we had. The other reason why he becomes so much alcoholic was his bad break up with his girlfriend. Sometimes, after coming home he tends to imagine me as a girlfriend and starts arguing with me about his issues with her. Many times, in the frustration he even hit me also. Main Part of the story: I was always fascinated about reading crossdressing stories at such time and read the experience of the people involved in such fantasies. Apart from the fantasy of being a beautiful girl, I also have other fantasy of being a slave to other person and completely obey their orders. I like to be the cross-dresser for such person and give up my control to him. It is fascinating to allow him to use me as his sex slave and give me all the pain he wants. Once, when Raj is gone with his group for the whole day I have a chance to become a girl for a whole day and explore my feminine side. I can be like a girl and do the normal stuff a girl can do for the whole day. Hence, I was going to prepare for such time. That day I had taken a hot bath and remove my body hair even on the genital area. After such removal, my whole body become smooth like a girl. I have started with the clothes which I have bought and wear all those clothes one by one. Firstly, I put my bra and panty. The silk of the bra and panty made excited. Then I put on blouse and saree and become a beautiful girl. Then I did my makeup and put my long hair wig. The smell of the hair made me crazy. My dick becomes rock-hard with its smell. I also wore lipstick, the red one to suite it with my other ornaments. I had spent my entire evening in my feminine avatar. On that day, I have done the stuff like cleaning house, making dinner for myself etc. which usually girls are doing. I then had my dinner watching Saas-Bahu serials. At the time around 9:30 p.m. I became exhausted with the weight of that Saree and other ornaments, hence I decided to put on my Sexy nighty which I have purchased from online. It feels like I was some kind of whore who came to that apartment to please the man. As Raj never ever came before 1 o’clock as per his regular schedule, I have plenty of time to remain in my feminine avatar. At around 10:15 p.m., when I was watching the TV, someone has entered the apartment keys and suddenly enters in the room. He was Raj. I was terrified and I was not even being able to think what was going on. Raj came in the room in his usual situation, totally drunk, having no idea whether it is his apartment or someone else. But that day, he had seen me in my nighty half naked as the night was covering only up to my hips. I was totally in the shock. Raj was staring at me like a wild animal who has not eaten for like a month and searching for the meat desperately. I was so much ashamed in front of him and feel shy. I was about to cry and suddenly he said: “Nisha, you are back?”. Nisha was ex- girlfriend. Looking at me in a sexy nighty and hallucinating about his girlfriend, he seems happy and trying to hug me and kiss me. “Nisha, I love you. I can’t believe you back. Please don’t leave me. I so sorry. Please don’t leave me” he said. I was in a shock and bit of confused on the situation. He continuously trying to kiss me but I resisted and push him back. I said, “I am not Nisha, please leave me.” But my efforts were meaningless. He was a quite huge and three times stronger than me. I could not be able to defend myself. He forcefully kissed my lips. In the situation where there was a smooth skin girl in a sexy nighty showing her assets can’t be resisted by a sober person also and yet he was totally drunk. He throws me towards the wall and again forcefully trying to bite my lips and inserting his tongue in my mouth. I can smell the alcohol through his mouth. He has held my hands with a great grip behind my back so that I can’t move. One can imagine the situation where the love of their life come back to them and they don’t want to lose them again. Those feel of Raj has trapped me in his arms. I was terrified with the gesture of Raj and his continuous mouth fucking with his lips. Then he started to remove my panty or else I could say almost tore it. Sensing the situation, I had made my strong defense to push him away and made myself free from his arms. I punched him in his face and ran to my room as fast as I could. He fell down on the chair beside him and might be lost his conscious, though not because of my smooth handed punch but because of the alcohol. Next morning, I was not in a situation to confront him or tell him about my whole cross-dressing fantasy. I was in the room the whole day thinking about the humiliation I was gone through. Of course, I have a fantasy of being control by the other person in bed in with my crossdressing but that night is a horrifying experience for me. I have not plan to face him for next few days but suddenly my door knocked by him asking me to come out to talk with him. I was afraid to face him that I have to. I open the door and came outside. My eyes not even looking to him in the feel of ashamed of myself. I was about to say him sorry and suddenly he said he has some assignment to do with their college friends and for that he has to go out of town for 2 days. Listening to this I was confused why he was acting like this like nothing happened. He said, “Are you Okay, Sahil??” I said “Yeah, everything is fine. You go. Don’t worry”. He then leaves with his bags probably his clothes in it. I was shocked and confused. But then I realized that he never remembered whatever happened last night because of his drinking habits. Now I felt relaxed. He didn’t remember the last night. Next two days, I was thinking about the night. His forceful kisses on my lips and that biting on my lips. His tongue in my mouth. I was thinking the whole time about his domination upon me and to do all the things he wanted to with his girlfriend. Truly the whole experience is terrifying but this is the same fantasy I was a dream about since I was 14. Maybe the situation made me not to do such things and defend myself from his strong grip. I was a dream about it all day or night. It also made me excited and I couldn’t resist myself to masturbate. I had convinced myself to confront him and tell him about my fantasies and persuade him to treat me like his sex slave, a whore. The tremendous power and his passionate kisses made me think like a whore and give up the control to Raj. After two days, he came back to home from his trip. But I was afraid of him and decided not to tell anything. Maybe this could be a bit of an awkward situation for both of us. Hence, I decided not to tell anything to him about that night. As far as I don’t want to think about to the situation the more I end up thinking that night of that passionate kisses. Then the terrific idea born in my mind. I made a plan to do all the thing I was fantasizing about all this year. Raj has the habit of not remembering anything happened last night because of his drinking problem. I made a plan to take advantage of his habit. I planned that whenever he came back home next time late in the evening totally drunk situation I would recreate the same situation as of that night and again he will think about his girlfriend and try to overpower upon me. Then I can satisfy all my fantasies as I want and next day he will not remember anything about that night. I can make him hit me, love me or even fuck me as hard as he wants. Later that evening he was going out with his college friends for drinks. That evening I have decided to prepare myself for the exciting night I am going to have with Raj. I was preparing to be like his girlfriend which was not that difficult as anyways he will be going to think me as his girlfriend, Nisha. I decided to attached my penis and my balls to my stomach so that his not going to find out any loopholes in his imaginary girlfriend he will about to fuck later in that night. I had also made some soft boobs with cotton and attached it to my chest to fake it like real boobs. I had attached my long hair wig to my original hair with pins so that even the force of him will not make it lose and pulling of my hair by him make the real effects on my head. I wore the one of my other sexy nighty which I like the most and wear it only on special occasions of happiness. This one is the sluttiest one. Then I slip over my black pantyhose which my legs even sexier than ever. I was desperately waiting for the Raj to come home and made me his slave. I was looking a complete whore in that nighty. The thoughts running through my mind like what if someone else came instead of Raj. Obviously, no one could leave the hot meat in front of him. Even a sober man also take my full advantage in that situation. The time is passed and then he came back to home. I was hiding behind my room door to make sure that the person is Raj only. So that if anyone else was there then I can save myself from any other issues. The door opens and there he was. Here was Raj in his usual condition, totally drunk. I came out of my room and run to him. I said “Raj, are you okay?? Don’t worry Baby I am here. I am not going anywhere. I never left you again.” And I hugged him as if I was Nisha. He holds me and starts crying seeing his girlfriend is back. He started kissing me more passionately than before on that day. And the night begins as I was fantasizing about. He started kissing my lips and biting my lips. He has put his tongue deep inside my mouth. I was also passionately kissing him. While kissing, he has both his hand on my butt and started squeezing them. It was one of my excited movement where he uses his strong hands on my hand. This makes me hornier and I was started kissing him more passionately like I was going to fucked by him last time. He then started using his hands on my fake boobs. He crushing them like hell. It was fake but I have to make them real so I started moaning with his each crushing like they were my real boobs. He was now kissing my neck and my stomach area above my nighty. It feels so good when he kissing my neck and throwing his warm breath on my sensitive area. I was moaning in the pleasure. He was so much drunk that he was not in the mood of more foreplay. Hence, he stopped and started again kissing me while holding my hands with his great force behind my back. His domination just killing me in the pleasure. He wants to fuck me as soon as possible and as hard as he can. He took me to the bed and throw me on the bed like I am some animal. He then started undressing. He was completely naked and I can see his penis hanging out there. It was 8” inches long in very thick. It was solid hard which about to fuck my ass. He then came to me on the bed and pull my hair towards him. He pushed his penis into my mouth and start trying to deep fucking it. I was in a hell as this was my first time I was giving blowjob to someone. Certainly, I didn’t see this one is coming. He pushed harder it in my mouth. It was good but very stinking because of the entire day’s smell of his pissing. I was choked to death by him. He was using his all power to push it hard. I was also enjoying my first blowjob. After some time, the smell of the piss and the sperm makes me hornier. This was gone about 15-20 minutes when he finally cum into my mouth. I enjoying each drop of it and swallow it. After my mouth fuck, it was the time to intense intercourse. As he was thinking me as if his girlfriend I told him to fuck me today in the asshole as I was on my period and also not to touch my pussy. He totally bought my made up the story. He has now turned me around and asks me to lay on my back. I asked him to punish me for whatever I did to him by spanking me harder on my butt. He also agreed and take his belt and start hitting me on my butt. He spanked me harder and harder relieving his frustration. Each stroke made me cry. I was screaming in pain. It was my fantasy to serve my master in whatever way he wants and feel the pain he wants to give me. This pain gives me pleasure. Hence, with each stroke of hell, I was feeling the pain and enjoying the pleasure from it. Those were about 30 strokes. Finally, he stopped and started licking my asshole. He was playing with his tongue on my asshole. This feels like heaven when he was licking my ass. I enjoyed the entire movement and wished it to never end. Now the real session was about to start. Raj has big and thick 8’ inches penis. I was known that my tiny asshole would never bear the pain of the drunken man’s penis. I lubricated by an asshole and his penis with the lubricant. I had also bought a penis ring from the online seller. This can be placed around a penis, usually at the base, primarily to slow the flow of blood and thus maintaining an erection for a much longer period of time. This will slow down the erection of Raj. I place it in the right area as describe in the manual. The real fucking was started. He has placed his penis in the opening of the hole and started stroking into my ass in one go. This man was totally drunk and not in a sense of what was hurtful to the other person. He started pushing it so harder into my ass that I almost screamed. The pain was hell. He has grabbed me in such a way that I could not be able to move. He pushed it harder. When I resisted in the pain he holds my hands behind my back. Now I was not even protesting the pain. I was screaming in the pain. After some time, this pain becomes bearable and I feel some sort of pleasure. I was moaning in the pain and enjoying each stroke into my ass. My ass was on fire but the same is giving me the excellent pleasure I never had in my life. Because of the penis ring, the fucking session was a bit longer than I was expected. The drunken man making my life fucking miserable with each stroke. Finally, he cum into my asshole. With the last stroke, he fell upon me and I was carrying his entire weight on me. He probably slept after the exhausted session. I have enjoyed it thoroughly as I was the only one who was in his sense while such incredible movement. I was started cleaning the mess around it and put him to his bed properly so that in the morning he cannot realize that something has happened that night. I took my clothes and move to my room and then I take a hot shower thinking about the sex. In the morning, as usual, Raj didn’t remember anything. I was also acted like nothing ever happened. Then after occasionally I enjoying being Nisha, Raj’s girlfriends. This was my first bisexual experience with Raj. Thank you, guys, for reading my story. If you enjoyed it please give your comments. You can mail me on my email id [email protected].
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