Shemales Porn Stories
Page 113

Tranny and Me Meet The MILF

This past Friday morning my phone rang. It was Chandra my tranny friend who I met and fucked some weeks ago. She told me that she had nothing to do this weekend and that her roommate was out of town and she was alone. I told her that if she wanted to get out of the city that she could spend the weekend at my place. She said that was a great idea and that she would be over in a few hours. When Chandra got to my place she was horney as hell. She dropped her overnight bag, dropped to her knees and opened my pants. She pulled out my cock and began to suck it really good. She was licking my balls, ... Continue»
Posted by adw276 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1784  |  
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Deep sexual fantasy part 1

Let me start off saying that i am a spiritual person, deeply believe in god and TRY to follow his way (which is hard being the sexual person that i am)....but i feel like this is a good way to air out my sexual desires.


Imma start off my talking about my sexual experience.

I first lost my virginity at the age of 13 when i first entered high school. The girl that i fucked was 17 years old, at first i didn't find sex to be as great is people say it is(we probably didn't do it to the fullest idk) but at the age of 17 i started have sex again. The reason behind that i was a athlete in my ... Continue»
Posted by Caribbean_Freak20 3 years ago  |  Categories: First Time, Mature, Shemales  |  Views: 766  |  
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Halloween Disguise: pre-story by DanaWu

an original story by me. its not true more of a fantasy...

this story starts october 14th. first of all i am a 23 year old boy, i just moved to a different state to go to college, i dont have many friends and have only been her a couple of months.

today was like any other day, had to wake up early and go to work for a couple hours before school. julia, one of the first people i met here, approached me today and told me about an "awesome" party tons of the students have every halloween. she tells me about the last years party and some of the crazy things people dressed up as. she mentions... Continue»
Posted by DanaWu 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1411  |  
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A Great night in by myself

I love dressing up in women's cloths they feel so smooth and sexy against my skin. A backless pinstripe lycra dress shows off my shoulders and back stretched tight over my peachy round buttocks. A little pair of white lace boxers underneath just visible as the skirt rides my thighs when I admire myself in the mirror.

I then peel down my knickers a little and run my hands over my bare ass. Next I lube up a finger and slide it between my cheeks, teasing my tight little hole. One finger slips into my bum soon followed by a second and a third mmmmm I'm really hard now and stroke my... Continue»
Posted by lovinanalxxx 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 454  |  
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Shemales- The Martini affair - Part 3 - finale

I could not stop thrusting back with my ass on her face as her tongue went crazy over my anal clit and tight bud. But I could not take it for long as I fell to the floor turning around to face her on my back. As if knowing what I had in my mind, she looked into my eyes and slowly took my cock throat deep in her mouth. Just as she did that I pulled her ankles and she knew what I wanted.

So very gently she moved her hips towards me and came over me with her glistening throbbing precum weeping cock right above my eyes. I took a moment to take in and enjoy that beautiful view. Then grabbing bot... Continue»
Posted by socuri 3 years ago  |  Categories: Shemales  |  Views: 449  |  
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Willows transformation 2

"Now the preliminaries are over, and it's time for the entertainment part of our evening!"

That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation.

Fern had found a magazine I'd left on the bedroom floor, showing a transvestite being tortured and humiliated by a couple. Although she had always known I liked to crossdress, she had never paid any attention to that side of me. Now she had ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 561  |  
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Julie's Journal - Day Two Continued:- Arrivin

Day Two continued: - The flight was smooth, being honest journal I slept all the way. I think it was the exertions of the previous night. That’s assuming it wasn’t a dream and if it was, well I would love for it to happen real. Must have been a dream though as Gina always seems to go with guys.

Landing at the airport and going through customs would have been okay except we were routinely stopped at the customs bar and told we were to be searched. I admit I was really terrified; these big coloured guys at customs seemed to be nodding to each other and smiling. We were all taken ... Continue»
Posted by Cybertease 3 years ago  |  Categories: Interracial Sex, Shemales, Voyeur  |  Views: 513  |  
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I posted a craigslist ad.

8 years ago I began crossdressing again and playing with toys. After playing one day while watching videos online I decided I wanted to take the next step and be with a man again. My holes craved it but the butterflies in my stomach had stopped me before. Afraid they would do it again this time I got dressed as slutty as possible and put up an ad on craigslist with a photo of me dressed and spitroasting myself with toys. Pic required I put in the posting. I was amazed at the responses and how many people couldn't read or just saw the photo and replied without reading. I didn't think it w... Continue»
Posted by bibottomboi 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1107  |  
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A Wonderful Ordeal Part 2

Saturday Morning Sometime before dawn

I must have fallen asl**p. My wrists where no longer tied to the bed post but they were still tied together and I was still on the floor. My legs were no longer tied. Don was pushing me with his foot and ordering me to wake up. "Who said you could go to sl**p?", Don asked.

"I'm sorry. I must have....", before I could finish my sentence I was slapped across the face.

"Who do you think you are speaking to like that?"

"Stop it. That hurt.", I was slapped again.

"Did that one hurt too? You better learn to speak to me correctly slut. Assum... Continue»
Posted by celeste_tv_2000 3 years ago  |  Categories: BDSM, Shemales  |  Views: 647  |  
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A Wonderful Ordeal

Part 1

Don and I had met on the internet in a chat room. Over the course of a month we had gotten to know each other and had shared our fantasies. Don was very dom and enjoyed the fact that I was very sub. I had shared with Don one of my favorite fantasies in which I'm a*****ed and f***ed into sexual servitude.

Don was a cross country trucker and came through my city very often. We had talked about meeting and living out our fantasy. He was married but was interested in being with a sub TV. He made arrangements for a long stay over in my city so that we could be together for the we... Continue»
Posted by celeste_tv_2000 3 years ago  |  Categories: BDSM, Shemales  |  Views: 914  |  
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some of first from my session with my Mistress

Lisa Ann (16.07.2011 4:38:41): message her and ask if you can be friends
Lisa Ann (16.07.2011 4:39:03): most people sent me a message after adding me
alexxxai (16.07.2011 4:39:15): so Miss what you think about girl who i send?
Lisa Ann (16.07.2011 4:39:26): she looks like your type
alexxxai (16.07.2011 4:39:33): oh yes...
Lisa Ann (16.07.2011 4:39:42): send her a message
Lisa Ann (16.07.2011 4:39:51): ask her to be friends
alexxxai (16.07.2011 4:39:52): and i am sure she is good girl for us..
Lisa Ann (16.07.2011 4:40:09): no doubt
alexxxai (16.07.2011 4:42:00): if you liked it, pleas... Continue»
Posted by alex_in_lingerie 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 269  |  
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the great plan

sorry guys but this aint much of a storey after it happens im gunna write about it. But remember in my first post when i told you guys about how me and my wife met and how she doesnt let me fuck her. well my friend broke up with his gf and my wife says shes going to fuck him (its ok with us because all mine and her friends get regular checks and we fuck togrether and things because were all good friends). But the problem is since my friend had a girlfriend he aint been fucked by her and he doesnt even know shes a shemale. she thinks shes going to get him by suprise... But i told my friend and ... Continue»
Posted by xxjamiexx 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 624  |  
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How I became a GURL -- Part III -- Fulfilling the

Now that I was fully versed in being a gurl, I needed to know if I could turn a man on in person, not just looking through a glory hole. I wanted to have a man treat me totally like a woman, take me to a hotel and make love to me, completely as a woman.

But where to find the guy?

The answer was a chat line. I got an account as a girl -- I signed on as Jennifer, explained what I was and what I was looking for. As you can tell my voice is very fem (listen to my voice into or watch my vid it you don't believe me, giggle) and it was pretty easy to turn guys on and grab their attention.

... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Shemales  |  Views: 825  |  
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I am a slut.....20

I am a slut.....20


This is the continuing story of my transformation from somewhat man to woman....my feminine journey. Enjoy :)


Having staightened ourselves back up, reapplied our makeup and done a line of magic dust, Gloria and I were off with Derek to meet his client and wife....and their friends on their boat. The ride down to the marina was not too bad, just long enough for Gloria and Derek to get aquainted and for Gloria to ask Derek what seemed like a million questions. But after all, she was a woman.

"Who are these people? How do you know them? Is this okay to do? How did... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 939  |  
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Casual Love Affair....(Ts Love Pt.1)

As I go about my day, Clients coming in and out. Tips and winking eyes from women who assume themselves to cougars, I take my break and make my way from the spa to get some lunch and non-aroma therapy scented air. Sitting at my usual table at my usual cafe near the beach, I sit and think about how most guys would to be in position. Massaging nearly nude and for the most part, beautiful women and getting paid to do so. But i find myself needing....more. That's when you walk in. Tall, curvy, sun kissed skin, and a smile that could cause the blind to become aroused. I try not to stare, but the vi... Continue»
Posted by atneverson 3 years ago  |  Categories: Shemales, Taboo  |  Views: 356  |  
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How I became a GURL part II

So I'm in college now, I've learned to love and use porn in all its forms, I've learned to be a great cock sucker and to have my ass fucked. I've learned to tie myself up -- as best as possible -- to pee all over myself to get that humiliating feeling. I'd spread the porn mags all over the floor and spend the entire night playing, trying to shoot my cum onto a photo of a cock so that I could lick it up.

The feeling of release whenever I gave in to all of those instincts was fantastic!

I loved cock! But I was a horny 20 something and still chasing pussy. Eventually the girlfriends star... Continue»
Posted by jenn1 3 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  Views: 887  |  
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Chatroom tricks 3

For those of you first reading this let me fill you in on a Friday that that opened my eyes. I am a 26-year-old normal guy who had for sometime been flirting and playing with an older woman named Mary via an Internet chat room. She was about 41 a firm fit body and gorgeous red hair, perfect, better than that she didn’t live too far away. Our chats didn’t really get too kinky so when she asked us to meet I agreed, as you would.

Well I went to meet her one Friday dinnertime for an afternoon of passionate sex, only things changed, I was tricked. Somehow I found myself dressed as a sissy, thong... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2220  |  
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Willows transformation 1


Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, at best, 5 inches. My touch, or my tongue, on her clit seemed to be much better received than my cock inside her.

I've always been a cross dresser. I can remember being in first grade and wearing my older s****r's clothes and pretending I was on a date with a boy. Before we married I told Fern about this. She treated it as something that would go away once ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2080  |  
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The Martini affair - Part 2

She picked up two glasses of the cocktail she had just made, and walked up to me. She, now just in her red panties which was already stained by the drops of her seeping precum. As she walked towards me my eyes were just stuck on that patch and the outline of that strong piece of meat beneath that. "Here" she said bending down revealing her big round tits cleavage, extending the cocktail to me. she sat next to me and said. "Oh I remember you saying you were a different kind of a girl, what did you mean"? She was smiling wickedly as I bend down my head, blushing not knowing what to tell her. She... Continue»
Posted by socuri 3 years ago  |  Categories: Shemales  |  Views: 487  |  
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I am such a slut.......18

"Hi Derek. I was just thinking about you. I haven't heard from you for a teeny bit" I replied. It was so nice to hear his voice on the phone and the sound of it caused me to stir within. Something about him, about what he did to me, about what he made me do, just had me.....and I think that he knew that.

"Baby, I have a favor to ask. It would mean the world to me if you would do it. And I would be there with you, okay?" he said, and my mind raced at what the favor might be. "I have this client and his wife....and they have a friend or two. I told them about you and showed them some of our ... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 1302  |  
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