Shemales Porn Stories
Page 5

The "Ball" Game 2

I awoke the next morning to dad's cock fucking me from behind. He held me tight as he pumped my ass gently. He gave me a sweet kiss and said he needed to use the bathroom and I was to accompany him there. He told me to step into the shower and he followed. I braced my hands against the wall and he entered me from behind again telling me he was going to "douche" my sweet pussy. I felt a warm sensation flowing into me and knew he was pissing in me! OH it felt so nice, like hot cum exploding in me only it lasted much longer! It started to leak out of me and down my nylon covered legs. I was SOOO ... Continue»
Posted by Barb51 4 years ago  |  Categories: Anal, Mature, Shemales  |  
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my best friend

when i began dressing as Ana i had three sexual experiences one with girls and two with boys.. this is the experience i had with my second boyfriend his name was Connor and he was this cute shorter boy with longish brown hair and he was so cute. anyways when we first met i could tell he knew somehow i was a boy but he still loved me and kept trying to be my boyfriend. one night we were in a movie and he began feeling me up.. i let him do what he wanted while we made out because he never grabbed for my crotch that was until now.. he grabbed my cock but he didn't pause or was surprised , but i w... Continue»
Posted by drewcd 4 years ago  |  Categories: First Time, Shemales  |  
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me and connor at the movies

me and Connor loved to fuck around in public clearly from our first time.. but this time we were bold and wanted to be noticed... we walked into the theater and as soon as the lights went down we snuck up to he front just in front of the screen... and we layed down and started to 69 while the movie was starting... nobody could see us and Connor was especially excited and i had something special for him.. i grabbed his cock and said "shove it in me sweety i want to feel your cum deep in me"... he his cock deep in me and i felt his balls slapping my ass... i was trying to hold in my moans and sc... Continue»
Posted by drewcd 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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My Boi Trish

This is a true story about a young lover whom I will call "Trish".

I attended a Halloween party several years ago. There I saw a cute boy who worked in the same retail store I did. He was all hussied up like a gypsy (still think of him whenever I hear that song by Fleetwood Mac). He had a very smooth, lean body and I think his ethnicity was middle-eastern. Nice almond skin and jet black, shaggy hair, very thick. Anyway, he kept giving me the eye all through the night until I finally walked over and said hello. We chatted about work and other things, etc. until he finally pretended to drop o... Continue»
Posted by RazedGlory68 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Changling

A Fantasie




‘My goodness!’ she exclaimed, ‘It appears that you've had an accident, youngster. You'd better come home with me so that we can make you presentable. It's quite safe, 'cos I live in the big house in the woods on the other side of the hill behind the toilets. Come along, now,’ and taking Colin's hand she led the surprised and unresisting boy through the copse.

Of course he had seen the house before. It was something that he had known about all his life; at various stages he was afraid of it, curious about it and – recently – ignored it. It could be best defined as an Edw... Continue»
Posted by kimii1234 4 years ago  |  Categories: Shemales  |  
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Groundhog Day - from sissifyourself blog

The alarm went off at 6 AM, like it always did. I stirred groggily and
looked over at my fiancée Leah. She looked so scrumptious lying there
that I had half a mind to blow off work and make passionate love to her,
but instead I gave her a little shake on the shoulder. She moaned that
she was awake, and she padded off to the shower. Only having one
bathroom in the apartment meant I was shaving while she was showering. It
was hard to see in the steamed-up mirror, and sure enough, I nicked
myself.


We didn't talk much at breakfast. She had a big presentation she was
making today, so s... Continue»
Posted by slim_krak 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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me and connor at the beach

well Connor always liked to parade me around and i loved it we would always be down by the beach together because he lived neat it one special night we decided we would have sex in as many places as we could all in public we went walking down the beach and he layed out a towel for us to lay on and as the sun went down Connor was sucking on my cock and nipples then he fucked me so gently it was amazing and everyone was staring at us but i loved it... Connor loved me to fuck him as well and i was a little taller then him but he was so cute to me i would love to embarrass him too but he wouldn't ... Continue»
Posted by drewcd 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Cruzin the Ave

About 4pm 1/31/12

On a whim I decided to go out cruzin and found a nice one. I headed west down the Ave and just started up the hill by Auto Zone and Apple Wholesale.
When one fine BSW was heading back east. Mind you I prefer W but this one was a hottie with a killer butt. Decent handfuls for tits too.
She flashed me a what the fuck do you need look and blew me a kiss. I was hooked. I knew I needed to jump this quick. I spun around and stalked her
back down to the Apple Market watching her get looks the whole way. I pulled into the lot and waited on the end for her to cross in front of... Continue»
Posted by shemalefckn 4 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
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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 4 years ago  |  Categories: Shemales  |  
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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 4 years ago  |  Categories: BDSM, Shemales  |  
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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 4 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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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 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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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 4 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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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 4 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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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 4 years ago  |  Categories: Sex Humor, Shemales  |  
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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 4 years ago  |  Categories: Fetish, Mature, Shemales  |  
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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 4 years ago  |  Categories: Shemales  |  
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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 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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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 4 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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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 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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