Bisexual Crossdresser Fucked By Drunken Roommate free porn video

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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

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Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

3 years ago
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Sarahs New Roommate

Sarah's New Roommate By Bill Hart "You're very beautiful." Mike pulled the young girl he'd just met in the bar to him again and kissed her. "But I'll bet you already knew that," he smiled, even as Sarah blushed. "How could you not know how beautiful you are, Sarah Jennings?" Sarah continued blushing. No one other than her grandfather had ever called her beautiful before. She wasn't entirely certain why she'd gone to the bar; she wasn't altogether sure why she'd brought Mike home...

2 years ago
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The new situation with a dominant roommate

So if you read my last story then you know the situation...if not a quick summary would be that I have a female roommate who turned out to be very dominant and has joined me and my girlfriend in our sex life.Ok now the new dynamic of the relationship is that me and my girlfriend are still together and everything is normal, except that sometimes my roommate would join us in bed or act in a dominant way with me every now and then, overall its a really good situation although I'm sure it's going...

1 year ago
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crossdresser violation

My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite. Like most...

2 years ago
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CD crossdresser daughterrsquos bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

3 years ago
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Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Crossdressing
1 year ago
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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

1 year ago
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My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

3 years ago
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Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

2 years ago
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Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing
2 years ago
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  • 11
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Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing
2 years ago
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  • 19
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Finding a Roommate

The year after I finished college, I took a job as a junior management trainee in a stock market firm. I hated everything about the job, but it paid my share of the rent while I got my screwed up brain together. One Saturday, a female showed at our door, asking if we would consider a girl for the roommate opening we had posted. She looked presentable, and I invited her in to meet Sean, my one remaining roommate. The lease was in my name, and it wasn't a good time of the year for finding...

1 year ago
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Alice and My Roommate

Alice and I were rolling around in the sheets of my dorm room. She and I had vibrators inside us and we were holding onto each other’s toy – pushing it in and out of soaked swollen pussy. Anyone who has ever felt the odd sensation of something so desired, so thought about, so hoped for, finally complete – anyone who has felt that, could know what I was feeling. My virginity was gone. I felt like a bird released from her cage, and I lavished everything on Alice. I wanted to give everything to...

2 years ago
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Alice and My Roommate

Alice and I were rolling around in the sheets of my dorm room. She and I had vibrators inside us and we were holding onto each other's toy – pushing it in and out of soaked swollen pussy. Anyone who has ever felt the odd sensation of something so desired, so thought about, so hoped for, finally complete – anyone who has felt that, could know what I was feeling. My virginity was gone. I felt like a bird released from her cage, and I lavished everything on Alice. I wanted to give everything to...

Lesbian
1 year ago
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Caught getting fucked from my roommate

Caught getting fucked from by roommate!Ok for those who haven't read my previous stories some quick background info:I live with 2 roommates a guy "Sam" and a girl "Nicky"I have a girlfriend "Sue" who doesn't live with me but is always around. Recently me and my girlfriend started trying out new things in bed which led me to become a bottom for Sam and Nicky became my mistress, also Sam sleeps with my girlfriend from time to time with me sometimes watching.It's a pretty long story but it was the...

3 years ago
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Bisexual Black Fatherhood

There is much to be said about one’s origins, that’s for sure. My name is Solomon Rashid Joseph. I was born in the City of Detroit, Michigan, to a Haitian-American mother and Lebanese immigrant father. My father, Rashid Ahmed, met my mother, Nicolette Joseph, while attending Wayne State University in the 1980s. Unfortunately, as luck would have it, he died while visiting his parents in Beirut, three months before my birth. My mother married a guy named Harold Jacobson three years later, and...

3 years ago
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Drunken Milf Teacher

Peter O’Malley was sulking in the dimly lit parking lot. The loud music blasting from the club continued to remind him of the fun he could be having if only…. “What a stupid law,” he fumed. “I can vote. I can be drafted into the army. But at 18 I can’t go into a place where they serve alcohol. What’s so special about being 21? What a stupid, fuckin’ law!” Peter had tried using his fake id, but the bouncer at the door spotted it right away....

1 year ago
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Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

3 years ago
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  • 14
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Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

3 years ago
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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

3 years ago
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olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

2 years ago
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Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest
1 year ago
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CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

3 years ago
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AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male
3 years ago
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  • 31
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Bisexual Fantasy Fulfilled

Not my Story, but a great read.Bisexual Fantasy Fulfilled # 1 (mmf)bisexual – mmf – threesome - creampie – clean upIntroductionMy wife Lisa and I have been happily married for 14 years, and I still think she's the hottest woman in the world. She's a petite, fiery red-head with a beautiful round face and a little button nose. Making love with Lisa is one of my greatest pleasures in life. She is absolutely fantastic in bed. I love the feel of her ample breasts, and the firm roundness of her...

2 years ago
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My New Roommate

About six months after my divorce, I decided to accept the company’s long-standing offer and transfer to New York. Being a small-town guy from the Midwest, I was a little intimidated about moving to such a big city, but I felt like the change would do me good. Most of my friends had been my ex-wife’s friends first, so I was beginning to feel isolated. If some woman had come along in those six months to pique my interest, I might have stayed longer to see if the relationship might go somewhere,...

Gay Male
3 years ago
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  • 21
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Charlenes Roommate

Charlene was dressed like a high-school girl, and a prudish one at that - white blouse buttoned up to her neck and tucked into a pleated gray skirt that came down almost to her knees. Not that the skirt length made much difference with her legs being totally covered by white stockings.Tommy wasn’t even sure he wanted to admit knowing her. And such a shame too, he thought. Charlene was a pretty girl – not too short and not too tall, petite, but shapely, blond hair to her shoulders, blue eyes and...

College Sex
4 years ago
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Charlenes Roommate

Charlene was dressed like a high-school girl, and a prudish one at that - white blouse buttoned up to her neck and tucked into a pleated gray skirt that came down almost to her knees. Not that the skirt length made much difference with her legs being totally covered by white stockings.Tommy wasn’t even sure he wanted to admit knowing her. And such a shame too, he thought. Charlene was a pretty girl – not too short and not too tall, petite, but shapely, blond hair to her shoulders, blue eyes and...

College Sex
2 years ago
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  • 14
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Bisexual The Life of Stefano

Stefano Jenkins comes home. He’s a twenty-year-old black guy who attends the nearby state college. This buff stud has caramel-colored skin, curly black hair and golden brown eyes. He’s the stuff dreams are made of and he’s really popular with the girls. The fact that he’s also the star of the men’s basketball team also had something to do with it. Stefano wants to become a police officer someday, like his father before him. What Stefano doesn’t know is the fact that someone was waiting for him...

1 year ago
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Watched by My Roommate

My wife and I had been dating for about three months when I got a new roommate. Jason was decidedly gay, though he did a good job of covering it up. As far as roommates goes, he wasn't a bad one at all. Most weekends he was gone and didn't come back until late Sunday evening, so on those weekends that Laura and I were strapped for cash and couldn't afford a hotel off base, it was nice to know that we had some privacy in my room. Because it was a training command, having a guest of the opposite...

Bisexual
2 years ago
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  • 15
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Naughty Drunken Uncle Fucked Me 7

Depending on your age some of you might recall the era of computers being introduced to home and that dreaded dial up tone of the internet. Our computer was initially kept in my parents bedroom but I would sneak in and use it whenever I could. On one such occasion I found my dad's email account had been left open and being the nosy parker that I am, of course I snooped through his emails. There were a string of emails between him and Jim but what really piqued my attention was they were about...

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