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Last summer I was visiting Kolkata and after a hard day’s work I needed some alcohol to relieve tensions.I ended up going over to the night club at the same hotel where I was staying. Entered the bar late on a weekday and found that there were very few people there. I sat down and asked for some whiskey. Whiskey always seem to help get me fucked up and that’s all I wanted to be right now. Too much seem to be on my mind as I stared off into space. I had only downed two shots. The bartender asked if something was wrong and I didn’t say a word. I heard the door open then close but didn’t turn my head to see what had walked in until she sat down next to me. I looked her over and she was absolutely gorgeous. Probably about five foot eight, athletic, long smooth legs embraced by black leather boots, dark hair, sexy lips, great breast, and an amazing ass. The skirt was tight and I was quick to notice the shape of her ass pressed against it. I just thought to myself “God damn what a piece of ass.”

I had planned on getting to my room at 1am but this woman had kept me here. I saw her looking through her purse for something, I was assuming was a lighter since an unlit cigarette was resting between her glossy lips. Reaching into my pocket I pulled out my lighter. I leaned towards her, lighting it for her. She thanked me as the smoke smoothly flowed out of her half open mouth. I started a conversation with her and got to know her name finally. She was Lipika and she told me that I was in for a shock.After what appeared to be hours I did convince her to come over to my room. I was surprised that such a beautiful girl would want anything to do with me. She had told me she finds it hard to find men that accept her for how she is which I never understood until she took off her clothes. What a shock it was though I of course didn’t mind.

Lipika put her cigarette out in an empty bowl on the table before telling me to strip. Doing as I was told, I dropped my pants and removed my underwear, then my shirt. I was erect and standing at 6 inches. Lipika stood up removing her shirt and skirt. “Close your eyes,” she quietly said to me. I closed my eyes as I waited patiently, wondering what was to come. She grabfloor my hand and put it down her panties. I felt around and found a dick. This beautiful girl had a big cock and I loved it. Opening my eyes I smiled at her, which she smiled back as I rubfloor her dick, causing her to become hard.Turning away from me, she removed her panties. As her front came back into view I saw a large, almost 9″ long, thick, smooth cock. She had shaved her pubic region and her balls. Pushing on the top of my head she told me to get down on my knees and suck her dick like a good boy. I dropped to my knees. I wrapped my fingers around her balls, squeezing them tightly in my hand. Running my tongue along her balls make her moan lightly. I took her nuts in my mouth, sucking on them as my tongue poked her sack. She brought her hand down to her dick and pulled her balls away. I looked up at her as she shoved her long dick in my mouth. I hungrily sucked at it, coating it with my saliva. She thrusted a little as I licked her smooth nine inches of meat.

Before long I felt her cock grow inside my wet mouth as her semen rushed out onto my tongue. She forced me to eat it all. I swallowed it. She replied, “Good boy, now you get a treat.” I was relieved now thinking I was going to get off. Standing up, I waited for her to drop to her knees. She looked at me like I was fucking crazy as she threw me on the ground. I put my hands on the couch to help myself up. As I started to stand up I felt something enter my anal entry.She thrusted her cock in fast and hard with no mercy. I have never had a cock in my ass so her huge cock was tearing my ass apart. I was trying to hold in the screams but they escaped. Grabbing my hair and pulling it, she rammed all nine inches inside my ass. I could feel her penis poking my inside walls. My ass was too tight for her and she didn’t seem to care. The more I tried rejecting it the more she pushed in me.

“Congratulations”, said Lipika, “You are the first guy to take all of my cock without breaking down and crying.”I was in such pain. Lipika then pulled slowly back out of me about half way and turned me around making me lie down on the floor and face her and pushed slowly back into me again. She did this over and over until she was pulling out to the head of her cock and plunging all the way back into me. I was starting to get used to the size of her cock and the feeling of my insides moving around to accommodate her. The pain was down to a dull throb and as I watched her fuck me I was once again struck by the fact that a beautiful woman was on top of me thrusting her big dick into me. Without being told to, I reached my hands up to her breasts and began to rub them through the fabric of her dress while I gently pinched her nipples. This brought more moans of pleasure and Lipika increased the tempo of her thrusts into me. I hooked my feet just below her firm bottom and began to pull her into me. This really set her on fire and she began to pound me into the floor. After a few minutes of pounding she pushed up off of my chest and quickly reached down and pulled the rest of her dress over her head and threw it to the floor.

Lipika repositioned herself without pulling out of me, so that she was in a sitting position on the floor and I was sitting on her lap impaled on her huge cock. I was trying to move up and down on her some, but she was so big that I couldn’t really get much movement going. With me still in her lap she sat up to the corner of the bed and put her feet on the floor. I still had my legs around her as she grabbed me at the waist and began to raise me up and down on her cock. The look on her face told me she was in complete control and that everything she was doing was for her pleasure only. She stayed in that position for a few minutes then stood up with my legs still wrapped around her.She was so beautiful, and yet so strong!She asked me to hold her around her neck. She grabbed my ass cheeks strongly pressing me stongly on her lap and started to fuck me wildly. I lowered my lips on to hers and she started to kiss me like an animal, sucking my lips and tongue and biting me savagely, and at the same time holding me up in the air and pumping my virgin ass with her strong meat.

Lipika then dropped back on the bed and reached up to pull me to her chest. She started to thrust into me again with her arms wrapped strongly around my waist. She pulled my mouth to hers, forced her Tongue into me as far as it would go, and started to cum deep in my ass. As soon as she started to orgasm I joined her with one of my own. I could feel her cumming endlessly and she must have filled up my bowel with a cup full for her cum. When we were finished cuming I lay there on top of her and we kissed while she made small slow thrusts into me to keep herself hard. After a short time Lipika whispered in my ear, “Do you want to be my fuck buddy for life?, I can make you sit on my lap for the rest of our life and fuck you again and again till I make you pregnant”. “Pregnant…?”, I shuddered, “How is that possible?, I am a man…”. “Leave that to me”, she smiled.I lay there on top of Lipika, feeling her cock slowly moving inside of me and asked myself if I wanted her to keep going. I knew I wasn’t going to be able to sit down no matter what happened next. Lipika was so soft and beautiful yet hard and sexy at the same time. I had never felt so content as I did right now with her inside me as my head rose and fell with her breasts as she breathed. I felt warm and protected in her arms. I had always thought that was how a woman was supposed to feel after sex, and yet I liked feeling that way in her arms. As I was thinking, Lipika started to move her cock a little faster and farther with each thrust.

She said, “I’m almost to the point of no return, if I get anymore turned on we’re going to keep going whether you want to or not.” As she said this, her hands moved down onto my hips and she started to pump into me again in earnest. “Never mind, it seems that my cock has decided for you.” she said in a low voice.She started to pump my ass again with deep thrusts and pulled my face on to hers locking our mouths in a wild kiss. We held each other as my ass was getting filled with her cum again, and I thought to myself, “Wow!!! What a great beginning to a great relationship”.The story will continue with my further experiences with Lipika and her other friends. Shemale lovers can mail me at Dominant females, shemales, cross dressers are also welcome to write to me.

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“Curious? Bi?” Well, yes, but only with a shemale. Beyond that I’m a firmly planted heterosexual.For many years I longed to have sex with a shemale but never did anything about it. (I’m not much of an initiator).The community I live in has lots of shemale beauts; maybe that started my interest. One such ravishing creature has a gallery close to my office, and I fantasize every time I see her in the coffee shop. She also has an eye popping diamond on her ring finger.Once in a while I’d visit...

2 years ago
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MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few...

4 years ago
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Young shemale with mature woman

High speed internet has arrived at our cottage, fibre-optics! We own almost 500 acres with a very large pond, nice home with a pool in its backyard. Pond has a lovely beach but is a serious walk from our house/cottage, roughly 20 minutes via a trail through the woods. Seclusion is paramount, peace and quiet, love it!! We've decided to try living at our cottage and have a grown daughter with her husband and k**s live at our house. I went on an extended trip to Europe for business. Wife loved...

3 years ago
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Shemale Ne Mummy Ko Choda

Hi friends yeh story meri, meri mummy aur shemale ke beech hai. Is story mein btaunga kaise shemale ko maine choda aur phir kaise shemale ne meri mummy ki chudai ki. Meri mummy jinka figure 34-30-36, bank mein job karti hai. Unka divorce hue 6 saal ho gaye hai. Mummy job ke karan kafi fit hai. Yeh incident 3 mahine pahle ka hai. Main aise hi net surffing kar raha tha.Tabhi ek din maine shemale wali video dekhi.Woh mujhe kafi achi lagi. Us mein shemale gand marwata hai aur marta bhi hai. Mujhe...

3 years ago
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Mommys Christmas Shemale for David

She had to make it good. It couldn't be just another gift wrapped cologne set, or a gift card to Ulta. She wanted this Christmas to celebrate her newfound lust with her k**s. She wanted David and Dana's presents to be fun, kinky and perverted. That's why, after a few weeks of thinking about it and a little searching, she had finally found David's gift.David had very open tastes. He was very in touch with his sexuality; he knew what he liked, and he was willing to explore new things to keep...

2 years ago
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Would love a shemale like this

****d (sort of) by a Shemale!I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable...

3 years ago
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My Sister8217s A Shemale

We are a family of four. Me, my parents and my sister. I am 23 years and my sister is 18 years old. She is very beautiful, fair and very sweet looking with small perky boobs and a very petite slender body. I, on the other, am a regular gym goer and have a very good physique, but the thing with me was that I was gay and loved gay and shemale sex. I have done gay sex a couple of times but have never been with a shemale. I always knew there was something different about my sister as I often...

Gay Male
3 years ago
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A Shemale Fantasy and my Wife Part 2

About an hour later my phone vibrated once again. It was from Carol. This time she had send me a picture of a shemale. The text read "do you think she's hot?" I responded with a YES! And I meant it. This shemale had beautiful big tits and a pretty big dick. In fact it may have been a bit bigger then mine. This was really starting to get interesting, just like Carol had promised. She was texting me dirty pictures and being really naughty. I loved it. I wanted to be naughty just...

4 years ago
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A Shemale Fantasy and my Wife Part 2

Introduction: I didnt know what I was in for. But what a ride I arrived at work, walked into my office and settled in for the day. Just as I was checking emails on my computer my phone vibrated. I took a look. It was a text from Carol. In closed was a picture of her laying in bed totally nude with her legs spread. The text read, my tight wet pussy is waiting for you. I instantly got horny. I would never dreamed Carol would send me a picture like that. I texted back I cant wait to stick my dick...

4 years ago
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A Shemale Fantasy and my wife Part 4

A few hours later I was woken up by Carol. "Wake up baby this day is just getting started" she said. My eyes opened and I was like a kid on Christmas morning. I couldn't wait to see and "feel" what she had in store for me next. Carol instructed me to shower get dressed and leave the house for a few hours. My next surprise needed some set up. I did ask she told me. Before I left Carol came up to me grabbed my dick, kissed me and said "get ready for some fun". Having no...

3 years ago
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A Shemale Fantasy and my wife Part 4

Introduction: The Conclusion Basking in the glow of what just happened, I put my head back and just passed out from total bliss. I didnt know what else Carol had in store, but I knew I wanted to be well rested. A few hours later I was woken up by Carol. Wake up baby this day is just getting started she said. My eyes opened and I was like a kid on Christmas morning. I couldnt wait to see and feel what she had in store for me next. Carol instructed me to shower get dressed and leave the house...

2 years ago
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Shemale Stewardess Seduction

Please note that this story is not written by me! It was stored in my computer for a long time now and decided to share it with you. The author's name as well as the site I found the story are not known... My introduction into the sultry, steamy world of shemales came (and I mean came!) at 35,000 feet, on a plane flight to the Northwest. I had been working myself to the bone, staying until ten or eleven at night, coming back in at six o'clock in the morning, and I guess the stress...

2 years ago
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Beautiful Shemale Sex Fantasy 8211 Part 1

Hello people, Leviathan here with my first story. To describe me, I am an average looking guy with a pint of femme body and many have said I have a great ass. Jumping into the story, this is purely a work of fiction. I request you all forgive me for grammatical and spelling errors. I made up a story by mixing a few of my fantasies and pint of my imagination, and a lot of horniness! It was around 8 pm. I set off for a 16-hour long journey to native, my train just arrived. After a fuss, I managed...

Gay Male
1 year ago
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Sweet Julie Birth of a Shemale

Sweet Julie Birth of a Shemale by Mistress Tawny Suede Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions centre stage, holding hands as the curtain rose one more time. They...

1 year ago
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My Vivid Memory of Sex with a Shemale Free Sex Stories and Adult Erotica Stories

I am a lonely man in his forties. I love to travel, dine and explore new places by myself. But I often wish for a partner. I got divorced early, so the little chance of being with someone was also ruined in my memory. So, each morning I would go to work, do my mundane bank job and visit my nearest LGBT bar. I am sharing my memory of sex with a Shemale and how I found pleasure in it. I am not gay or have any element of pride in me but what really fascinates me is Shemales. I believe they have...

Shemale
2 years ago
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shemale fantasy ive read before and dream

I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon. I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.Her hair was dirty blond...

3 years ago
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A Shemale Vacation

A Shemale Vacation - Part One by Richard-to-Rachel I was eighteen, na?ve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was still a virgin and I was pretty determined that that...

1 year ago
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Making a porn flick and then sex with a shemale

I had met Josie at a bar and she had no qualms in letting me know that she was a shemale. We both were drunk and horny, so she let me feel her up. I had had gay encounters and considered myself bisexual, so I wasn’t afraid of touching another penis. It made me hard. I was too drunk for sex so I shared my contact information with her and when we met, there was a porn flick made on my camera while having sex with a shemale. Josie had arrived at my apartment on Saturday and we were having a few...

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