Shemales Porn Stories
Page 6

Brandi the Shemale Cums After MNF

So, I come home from watching Monday Night Football with some guys at the local pub. I turn on the TV and some infomercial for an exercise machine comes on. The model working the machine has a great body and seeing her workout is really working me up. My cock even gets a bit hard.
Feeling a bit on the adventurous side, I open the phonebook and look for an e****t service that has shemales. I find one. Just talking to the dispatcher and describing what I want makes my cock hard again.
The hour I have to wait for her to arrive is excruciating. I’m so horny that I decide to prep myself by jerkin... Continue»
Posted by madnessx 2 years ago  |  Categories: Shemales  |  Views: 867  |  
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Honolulu surprise

I haven’t written a story in a while because I moved from Asia to the US and have been busy with work.

Back in Honolulu, I used to fuck plenty of women as I was young, tan, blond, and in super shape with Triathlons. Mostly I would try to close the deal really quickly after I met someone, just going with “Hey you wanna go fuck?” question after a few minutes of chit chat. You would really be surprised how often this technique worked. I got slapped a few times and a few “fuck you’s”, but really it worked more often than not. Actually, looking back it is only logical I would continue to use thi... Continue»
Posted by mahuluvr 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 892  |  
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My Feminization of the day

Ever love the feeling of a woman cummin on you? Well I felt that this evening after I picked up a random woman off the street who asked to be drive home. When we reached the house she asked me to come in. I did and she actually blindfolded me into here bedroom where she tied me up on her bed. I didn't need that but I just played along with it begging to be let go. Of course she didn't let me go. Then she started to tear off my clothing and found me wearing a bra and panty. Then she said,"Well aren't you dressed up nice?" she pulled on my panties and let go juggling my balls around. She laughed... Continue»
Posted by SissySlut9084 2 years ago  |  Categories: BDSM, Shemales  |  Views: 616  |  
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Back Seat Backdoor part 2

After our back seat get together, I was hoping that I would get chance to play with my big black stud in a more comfortable roomy spot. We chatted off and on flirting and teasing each other for a couple of weeks, and everytime I talked to him, my ass would quiver just thinking about how good that huge cock felt. One Saturday afternoon I got a message from him telling me to meet him that he was at a friends apartment and if I wanted to come over and play, he would love to. "have" me. I couldnt turn him down, and I got in the shower, shaved everywhere and made sure I was clean as a whistle. I sl... Continue»
Posted by LRock4fun 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 841  |  
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A Sissy's Long Night Pt.1

We were to meet at a hotel, the seedy kind where nobody respectable would go. I was to meet him in his room, just down the hall from mine. I was very nervous. This was my first time meeting someone like this. Usually, I knew the person before hand, and always met at private parties where other people were around in case something went weird.

No, this time, we met online, chatted, exchanged pictures and then arranged to meet. I changed out of my jeans and workshirt. My clothes laid out on the bed, my make up already set up, wig on its holder. I took my time with the make up, I keep it... Continue»
Posted by sissystephanie2008 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 278  |  
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A Sissy's Long Night Pt.1

We were to meet at a hotel, the seedy kind where nobody respectable would go. I was to meet him in his room, just down the hall from mine. I was very nervous. This was my first time meeting someone like this. Usually, I knew the person before hand, and always met at private parties where other people were around in case something went weird.

No, this time, we met online, chatted, exchanged pictures and then arranged to meet. I changed out of my jeans and workshirt. My clothes laid out on the bed, my make up already set up, wig on its holder. I took my time with the make up, I keep it... Continue»
Posted by sissystephanie2008 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 710  |  
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diffrent, part 2

rosa was hearing things now. she was in the cell her new owner had put her in, a dark, damp, dungeon, and could see almost nothing. tied to the wall, a 10 inch dildo stuffed into her anus, a 9 inch in her mouth, and a chastity device on her newly aquired penis, nipple clamp on her tits, and every once in a while, water dripping on her head, she wanted nothing more than to die. she felt younger, though. like she was in someone elses' skin. scary, yes, but invigorating, it was. she listened for the sounds of her new owner. what had the man said about a "procedure"? it didnt matter. suddenly, foo... Continue»
Posted by mj2397 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 393  |  
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A Certain Perception (c) 2004 by Cherysse St. Clai

A Certain Perception
(c) 2004 by Cherysse St. Claire

Kyra was not the girl of my dreams. I never DARED dream a woman that good would just walk into my life. She was smart, sassy, vivacious, intuitive, resourceful, and a real 'people person'. We met in an Internet chat room called "Working Girls". We're not talking about the kind you find in corporate offices or retail stores. C'mon, be honest; what guy hasn't fantasized about being with a woman like that? The room was filled with the usual posers and wannabes. Every girl was a drop-dead-gorgeous slut who would bang a guy on the hood of ... Continue»
Posted by slim_krak 2 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 722  |  
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fgjghjfgjfg

My mouth was super dry
can i feel your, luscious, lips locking with mine
sweetylittle smooth pussy was saturated with her moisture
u separate my pussy lips and drove ur tongue in
plese held my breasts against ur mouth and starting sucking on them
shall i softly, caressing ur breasts.
laying on the bed, hands in her pants,
i also rarely wore a bra
stuffed her fingers into her pussy
She never wore underwear
pulling her pants off or by sticking my cock in her hand/mouth
three fingers stuffed into her pussy with one hand and was rubbing her clit with the other
walked over to me,... Continue»
Posted by kelly_hot 2 years ago  |  Categories: Sex Humor, Shemales  |  Views: 296  |  
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CD meeting

It was mid-morning and a CD friend was passing through, I got a text asking if I wanted my cock sucking, well I don't need asking twice lol. I told Jo that I wouldn't be able to dress up, she said that was no problem. We were to meet in a layby on the A30 just up from Chiverton Cross, at the time there were roadworks taking place so the traffic was not moving very fast. As I drove to meet Jo my heart was racing and I was trembling with excitement and fear, this was to be the first time I had met with a crossdressser. I pulled up in front of her crewcab pickup she was using to do a delivery.... Continue»
Posted by KirstyNylonlover 2 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 957  |  
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Abigail's First Time

This is the story of the first time I dressed for a man. I had been with men before, but had never been with one as a girl. I would say 95% of it is true. I tried to keep it as close to the truth as possible. I will say that the acts described actually happened, and we really did go four times. I leave you to decide which parts you think are the false ones.

I checked my hair and makeup in the mirror for what seemed like the millionth time. Nerves I guess. Tonight was the first time I was going to meet a man while dressed and acting as a girl.

I adjusted my dress, a dark blue bodyc... Continue»
Posted by cdboy22 2 years ago  |  Categories: Shemales  |  Views: 498  |  
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Panties For ME

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. I'd just broken up with a girlfriend and I'd decided I'd finally give in to my urges and try the sissy thing for a few months.

After many advances, I ended up going with someone a little older and little less hot than the others because he had the ingenuity to ask what my fantasy was and actually asked m... Continue»
Posted by rikkk72 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 769  |  
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Night out

My wife knew that I liked to dress and would often help me. Usually it just consisted of dressing up and watching TV or maybe having hot sex. Once she had me dress and took me for a drive to the park where she made me walk around and pose for pictures. She’d also take me to the local thrift stores where we’d buy new things for Michelle. In bed we’d often talk about me dressing up and going someplace in public like a club or show. It seemed to make us both hot and the sex we had afterwards was fantastic.
One weekend we had to go to Providence for a friends wedding. My wife told me she w... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1175  |  
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first time cumming

When I was 12 I began secretly stealing my s****rs pills and clothing and make up, I was dressed up as a girl when I was younger and enjoyed the feeling so growing up I have always had a time to connect with my femme side, when I started stealing her clothes and make up I would look up videos online to see where all the make up went and what was good colors for my complexion, I've always been pretty skinny but the last year I let myself go and put on a few extra pounds and began to fill in the bras and panties a lot better than usual. After noticing how great it felt I began to diet again but ... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 602  |  
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Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift sto... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 2696  |  
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My Sissy Fantsy pt 001

Chapter 1

I reach the campsite just as the sun is going down and the clear sky is bright orange as if in memory to the beautifully warm day it has been. The campsite is popular yet set on secluded farmland and as the season is just over it is practically deserted. The whole camp is surrounded by woodland and a stream lined with more trees cuts through the campsite, dividing it into unequal sections. Walking through the larger first section I can see only ten other pitches occupied by either tents or caravans and I hurry past them. Crossing the rickety bridge I enter the second smaller secti... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 695  |  
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My sissy Fantasy pt 003

We come to another set of double doors, though these are glass paned in Victorian iron work painted white, as is the wall which it I set in. But due to the humidity all the glass is misted, including the dome and I can’t see where they lead outside. Jake opens one of the doors and we step into the rain that has subsided only a little to find myself standing in front of a large infinity pool that seems to drop off the rear edge of the building into that amazing view of the valley. Either side of the pool is a large patio that must run the entire wide of the house before simply dropping away to ... Continue»
Posted by monalottanow 2 years ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 273  |  
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From Andy to Amy


Story codes: CD TV mf voy mast nosex

If you are looking for serious one handed reading, then you are in the wrong place. I hpe you like this. It's the stopry of a young man's first venture into cross dressing. Any similarity to me is entirely coincidental!

Title: Andy to Amy

"Why are you staring at my knickers?"

I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - ... Continue»
Posted by justpeekinout 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1191  |  
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More of my Sweet

I was really becoming attached to this person. From the waist up a she, from the waist down completely a man. In the past, I had given thought to the attraction I often felt toward men, but I would never have taken it any further than the dark corners of the peep shows. I would never have openly dated another guy. It was always completely sexual. I enjoy sex, always have since an early age, and always will till I hit my grave.

Now, along comes this person that is satisfing both sides of my sexual desires. Someone who wanted to be with me and it was confusing to say the least. After ... Continue»
Posted by milkmanj 2 years ago  |  Categories: Fetish, Shemales  |  Views: 516  |  
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my new flat (part 2)

After putting the phone down i started to panic a little , i had just accepted a date from a guy who i had just met a couple of hours before, and whats more he did not know i was not a real girl, what the hell was i going to do, could i bluff my way through this.
Mark was his name he was a nice looking guy i would say he was about 30 at the most quite tall with dark hair and we did seem to get on well when we chatted so i decided i would keep the date i had made with him for that night , my plan was also to tell him i was not a real girl and hope for the best.
Mark was due to pick me up at 8... Continue»
Posted by julieanneff 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1473  |  
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