Shemales Porn Stories
Page 6

Shopping with my s****r - Part 2

Continued...

We drove along chatting freely, laughing when we saw guys checking out the two hot babes in the car next to them. Jane told me what purchases she planned for me, practically a whole new wardrobe I thought to myself, but hey who am I to complain. Jane pulled up in a quiet corner of the carpark and leant over and kissed me gently on the lips, her tongue probing mine. "Come on Dannii, lets go shop!" she giggles.

I climbed out of the car as ladylike as I possibly could, feeling the fresh air up my skirt and flow over my balls felt amazing, a nervous excitement building in... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 6112  |  
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My First Time

when i was 18 i first started to dress up when my mom was out and i loved it. well this is a story of my first time and i would like to share it with everyone. me and my mom live alone and she used to always bring guys back to the house and i used to always hear them having sex and it really turned me on so i tried to peek into the doorway each time and one time a guy left is underwear in the hallway so i picked them up and smelt them and it made me really horny. however this guy turned out to be my moms boyfriend so he came to our house on a daily basis but one time when my mom was out and i ... Continue»
Posted by MegCD 4 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 6081  |  
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My First Time

It must have been 4 years ago.
I was alone and curious, and had been for a while now. I had plenty of girlfriends and knew I was not gay. I just never had feelings for guys, only women. But sex..... sex is sex I thought.
Looking at pictures, watching videos, toying with myself while dressing up in panties and other girly things, had kept me amused up until now. But my desires had grown too strong.

I had frequented a few chat sites, getting into kinky conversations with guys, loving the way they all hit on me and tried to seduce me. It drove me wild and gave me more confidence all the whil... Continue»
Posted by MissieUK 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 6029  |  
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Tranny teacher

Hi Al, how is your house sitting summer going ? Pretty good Tim a little boring but the beach is nice. By the way, I didn't mean to but I saw you last night through my window... you were wearing woman's underwear. OH I hope I didn't disturb you Al. Actually I was totally turned on, especially when you pulled out your hard cock.

Really, if you like I can arrange for a private show ... interested ? I don't know I have never seen a man up close before. Ah.. well if you pretend I'm a lady I can walk you through some fun. So you will put on your stockings and the silky things. OH yes and a wig ... Continue»
Posted by TenderLoins 11 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6008  |  
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The Neighbor...

My next door neighbor had never shown any interest in me before. He was married and straight, as far as I could tell.
One night, however, there was a knock at my door. I looked through the peephole and saw my neighbor standing there. He was tall and stocky, with a beer gut that I found sexy.
I answered, not knowing what to expect.
"Hi. I'm sorry to bother you so late." He said.
"Its ok. Is there something wrong?"
"Look, I don't really know how to do this... so I'm just going to be blunt. I know that your gay. My wife and I have seen several different men coming and going at all... Continue»
Posted by bttmblw 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  Views: 6006  |  
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Weekend with my s****r - part 1

Continued from sunbathing with my s****r.

The week went so slowly, my mind always wandering back to our day together....stroking my cock endlessly replaying each and every kiss, touch and stroke. We stuck to our agreement of not talking about it when anyone else was in the house, not touching or staring was the hardest part, the sexual tension between us was incredible, I can't believe our parents didn't sense anything. We did leave bedroom and bathroom doors open just enough it was safe. Each morning when Jane left for work she'd leave some underwear on her bed for me.....twice it was e... Continue»
Posted by ukdan78 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5958  |  
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Car Bonnet Cockriding Whore

Hi Guys,




This true story dates back about 4 1/2 months now, and takes place outdoors, well over a car bonnet to be exact.


I had been chatting to this lovely guy called Dave, we had been chatting on a different site and arranged for him to come over from where he lived to where I live in Droitwich. Well I had been getting my self ready most of the evening showering, shaving my self totally smooth including my pussy, made a real effort to look hot with my makup and clothes. The usual things, stockings suspenders, 1/4 cup bra with matching thong, and high heels, a loose fitting top ... Continue»
Posted by donnamarie09 4 months ago  |  Categories: Anal, Shemales  |  Views: 5953  |  
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A Friend's Treat

had recently split with my wife and was feeling very down.

I was invited to spend a few days with my old friend Dave and his wife Tracey.

The first night I was there Tracey turned to Dave and said that we needed a boys' night out and why not go to his club. Dave agreed it was a good idea and within minutes Tracey was dropping us outside what appeared too be a Georgian townhouse.

I hadn’t known that Dave was in a club and was surprised to find he was a member of one. He had refused to reveal what type of club we were going to.

The door opened as we approached and a dinner suited do... Continue»
Posted by maninnylons 9 months ago  |  Categories: Gay Male, Shemales  |  Views: 5972  |  
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Oh My, You Have a Cock...

It was a regular Friday night no different from others I'd experienced before. I was lonely having broken up with my girlfriend earlier that week. What a bitch! I needed to find me a sweet woman capable of matching my libido. My last lady was all about the lights off, missionary position sex, come to think about it I don't think I ever got a good look at her naked. Those are six months I guess I will never get back. As I sat alone in my bachelor apartment, clean for a guy, but still not the greatest place to bring a chick home to, I started feeling sorry for myself. I had a feeling it was goin... Continue»
Posted by Asmarani 29 days ago  |  Categories: Anal, Shemales  |  Views: 5899  |  
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Paying Mommy’s Mortgage

As long as I can remember I have had a penchant for wearing nylons and lingerie: pantyhose; stockings; silk, satin or nylon panties (not those horrible cotton things or G-strings that are like candyfloss in your arse crack -- I mean, full cut panties, cami-knickers, or boy leg panties); garter-belts; slips -- both half and full; basques and corsets.............I can go on but you get the picture.

I also have a fetish for high heel shoes: sandals, pumps, courts, stiletto heels, kitten heels, stacked heels, Cuban heels, platforms, open-toe, "Pilipino bar girl fuck-me shoes"; you name the hig... Continue»
Posted by sparkyking 11 months ago  |  Categories: Anal, Shemales, Taboo  |  Views: 5850  |  
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Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 5835  |  
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The special overnight bag

I did not want to have another boaring sales trip,so I packed up my special overnight bag for this trip. All the items a gurl would need to have a special trip. Inside were a few skirts some stockings and two wigs ( I can never decide)a few items so I could get clean and my laptop and camera.
After my sales meeting I went back to the hotel,took a long bath,cleaned myself and shaved everything smooth. Put on my make up ( this time I got my eyes perfect !) put on my stockings slinkey red skirt and this time I opted for the long black wig.

I felt so slutty walking down to the bar in the hotel... Continue»
Posted by sodeep2 9 months ago  |  Categories: Anal, Shemales  |  Views: 5811  |  
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The heavy girl in the bar.

This is one of those stories from my past that I wouldn't consider rather astounding except for how it ends. It was a monday about 2 years ago. I was recently single and pretty horny so I figured my best bet aside from dating websites would be to go out to a bar and find a girl to hookup with. I hopped from bar to bar in town and everything was pretty empty with mostly men. I got to the last bar I would visit for the night, it was a bit more upscale than usual but there were a few women there. I flirted with them but they turned around at the bar and started ignoring me as if I didn't exist wh... Continue»
Posted by experiencedjojo 2 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5808  |  
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MY GAY PRISON SISSY ****


I'm sure many of you have seen a number of movies or television programs based on prison life behind bars. Having recently spent some 29 months in an undisclosed New England State Pen, I'll now share with you first hand, some of the wildest and most unbelievable sexual experiences one could ever imagine.

While still on parole now, I will change my name here and not mention the state facility involved. Other than to substitute a few names for some of the real ones involved, all of what I'm disclosing here actually happened between late July of 2007 and Dec. of 2009. My work... Continue»
Posted by cddixie 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5789  |  
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Leila Has a Big Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by drew1207 7 months ago  |  Categories: Fetish, Sex Humor, Shemales  |  Views: 5759  |  
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Deer Hunting with Daddy

Every year, a group of my f****y members, mostly uncles and male cousins, all pack up our gear and head into the mountains every fall for the yearly deer hunt. I had been going since I was 5. All the younger cousins slept inside an uncle's trailer, while the adult's and older cousins slept outside in a tent. This tent was huge and was intended to hold up to 10 people.

One year, when I was 8, I was having trouble sl**ping. I left the trailer and went to the "grownup" tent. As I got closer, I could hear strange noises...grunting and moaning noises ;-) I quietly unzipped the tent, but only en... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 5755  |  
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My shemale mother!!!!!!!!

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is....


I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I am not sure of the reasons but I do know that my mother is an average looking woman with nice looks and a not so fantastic body. Her pear shaped figure is a norm for any woman with Indian origin and what I do know best is her mammary g... Continue»
Posted by yarracuda 3 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 5743  |  
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Becoming a Sissy Cocksucker (true story)

I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl.

I always loved watching porn where a guy is sucked off by a
woman. I started to realize, what turned me on the most about it was watching his cock when it orgasmed! I LOVED watching the cum shoot out and on to her face and in her mouth! I used to watch it (and still do) dressed in panties. Well, fantasy eventually took over, I wo... Continue»
Posted by vickiebicd 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5720  |  
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The Day Lana Turned Me Into Her Daughter!

When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if ... Continue»
Posted by lovetopleaseu 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5713  |  
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My sexy wife has a secret

My wife, what can I say she is tall and leggy with thick, natural wavey orange red head with beautiful porceline skin and just enough freckles to tell you she is a ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen.
From the time we started dating my friends all expressed their envy at me landing such a smoking hot piece of ass. She is a freelance writer for fashion magazines and on-line blogs so she is pretty dressed up where ever she goes.
I got home one Friday evening from an afternoon shift. I knew she was home because ... Continue»
Posted by triphammer73 8 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 5708  |  
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