Shemales Porn Stories
Page 60

Crossdress fuck

One day while at university I went to the toilet. There was some one in the next cubicle. I could see a shadow under the partition. It was moving back and fort very fast. Was he wanking? I started to feel horny thinking about it. As a cross-dresser i was wearing a satin night-dress under my clothes. I decided to get brave. I stood on the toilet and looked over the thin wall. Oh god ya, he was masturbating hard. I pleasured my self as I witness something new & exiting. Then I let out an unexpected moan. He quickly turned to his left to find me staring at his dick. I jumped off the toilet, tuck... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2113  |  
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My trip to Mistress Cindy’s House – Pa

Cindy and I had worked together for years. We had been peers for several years and became good friends, then I became Her manager. Our friendship continued but many coworkers were certain we were having an affair. We weren’t having an affair, but ate lunch together nearly every day and shared the most intimate parts of our lives with each other. She was and still is my best friend and the only one I have ever felt comfortable sharing every detail of my life with. One day we happened to be talking about role playing and I told Her I had always fantasized about Her being Dominant and making... Continue»
Posted by wannabesubformt 1 year ago  |  Categories: Fetish, Shemales  |  Views: 2198  |  
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Moms Trannie

It was Saturday night and my friends had told me about a new club. It was about an hour out of here and had an older crowd. This sparked my interest some what having a fondness for older women.

I walked into the place and looked around, not much going on so I wandered over to the bar and ordered up a beer. A little while later the crowd picked up and things started to get moving.

The women were defineatly older here, I asked a few to dance and had a few takers but couldn't seem to lock in with them.

While I was dancing I must have missed the two that came in, a blonde and brunette wit... Continue»
Posted by frswriter 1 year ago  |  Categories: Shemales  |  Views: 4533  |  
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BIRTHDAY

I had just got home from work , and what to my wondering surprise my gf is naked and waiting for me on my lazy boy , with her legs spread , playing with her pussy.

ON the couch are 3 shemales also naked and playing with there cocks , how she did this i have no idea , but its been my fantasy to have a shemale and my gf in a sexual frenzy ,now i had this and plus two more , wow what a girl.

IM licking my lips as i watch all 4 of them playing , my gf tells me she has run a bath for me and has nikki one of the shemales lead me upstairs to get washed and relaxed , and says we will be waiting... Continue»
Posted by cocklover47 3 years ago  |  Categories: Shemales  |  Views: 1271  |  
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Got Caught

2 weeks ago i found myself alone as the wife had taken the k**s away for the weekend i felt the need to play. I went to work and finished early and raced home feeling very naughty indeed. I got in and ran a bath and had a nice long soak indeed and thought about what i would do and where i might get some fun at such short notice?

I got out my gear and put on a black basque with fake 40c inserts, lacy see thru black panties, black lacy top stockings, black strappy heels, skirt, top. I put on my wig and did the make up as best i could being a novice and looked into the mirror and got extremly... Continue»
Posted by abicd 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3146  |  
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the train ride




The Train Ride

Has anyone taken a night train following a major event in an
Asian country? I have. If you think trains are crowded during
peak hours in New York, you must experience riding trains in
Asian countries. Then you may ask what is common between a
crowded train in Asia and a can of sardine.

The idea to see the festival was planted in our minds by George,
who was our bartender at the hotel. He stated that the Kandy
parade was a once in lifetime experience, two days before we were
to head back to Oslo. After hearing what we were about to miss,
we made plans to hit... Continue»
Posted by pcarter 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1662  |  
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Caught again

So I’m finding it hard to get privacy to dress up of late. So I decide to go down the country and rent out a holiday home for a weekend. I brought all my gear including make-up,and wig. When i arrived at the holiday park I entered the reception area. Behind the counter was a pretty women named Jill. I introduced myself and filled out the required forms.

“You be staying in trailer 9, my husband will show the way……Mike!!!!. She yelled.

Mike walked in to room, introduced him self and took my bags. Little did he know one bag was full of lingerie and dildos. Mike was medium build and around ... Continue»
Posted by monkeynuts0 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1793  |  
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Painted Toes in Private Gym Showers

I'm soo thankful to have feminine feet and legs. My cock is around 6 and a half inches and I have a cute boi-pussy that is tight, but can take a sizeable dick. I would also like to point out that I have enemas on a regular basis so my butt is pretty clean. That part is true and the only part of this story is me at the locker room showers with my painted toes.
In the gym that I go to there are three individual showers. The way the showers themselves are set up to where you push the first curtain aside and there is a little area to change and a small bench to put your bag or sit on while your c... Continue»
Posted by sissyjulie 2 years ago  |  Categories: Fetish, Shemales  |  Views: 1378  |  
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Working Away From Home

Im an engineer by trade and my job sometimes takes me to different parts of the country, customers want me to design a specific peice of machinery for them.

I had an appointment with a firm just on the outskirts of Manchester, my company had booked me into a nice hotel for 3 nights whilst i was up there.

After my first days work i went back to my hotel and had a shower, got dressed and set out to find a nice restuarant for my evening meal, the consierge had suggested i went a particular restuarant that he new and gave me directions.

I got there it seemed very nice sat down at a table ... Continue»
Posted by BAZSEX 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 2098  |  
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my first tranny (pt. 1)

you always remember your first time.


I remember my first blow job from an ex. (believe me, thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.

her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was. I was looking in the e****t section of one of those paper you get at a porn shop. I always want... Continue»
Posted by radec_24 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2661  |  
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My Great Adventure

One morning after dressing in s*s’s clothes and she is a hot one.....black fish net stockings and 5” patenet leather pumps and corsets to die for and a pair of padded inserts to enhance her already endowed breasts, I needed some excitement besides the usual pulling of the wang and using my soft foamy dildo,
So I saw that she left the keys to her car and with mum and dad off on holiday...and s*s gone with her boyfriend, I stayed dressed in her clothes and added a yellow slicker and a bonnet to hide the hot cum fcuk me clothes and started up the Audi and off I went to the next town and though i... Continue»
Posted by mia1 3 years ago  |  Categories: Shemales  |  Views: 2279  |  
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My First Time with a Shemale

I had watched porn for a long time, graduating from straight porn to videos of shemales, falling in love with TS stars such as Leilani, Julie Bond, and the gorgeous hermaphrodite Dane Harlowe. However, as much as I fantasized about being with a shemale or cross-dresser, I never thought it would happen.

Then one night when I was living in Indianapolis, after being out drinking and dancing, I stopped at the local adult video store. I had parked near a white van and, as I was drinking some more of the six-pack that I had in my car, I saw that there was a woman in the driver’s seat of the white... Continue»
Posted by TSfanxxx 1 year ago  |  Categories: First Time, Shemales  |  Views: 2410  |  
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My frist time wearing sexy lingerie. Part 2

I could not wait to get home from school the next day after wearing my moms sexy panties the night before.

No one was home so i could have fun.

As soon as i got into my room i took off all my clothes and went into my moms bed room to see what I could put on.

With my mom working at Macy's in the lingerie department she had bought some sexy lingerie there.

I was looking thru her sexy panties and than I found a pink baby doll.

I rember see the girls wearing sexy lingerie like this in the pictures that my uncle had so I put it on.

As I put the baby doll top it made me feel so sex... Continue»
Posted by suecd58 1 year ago  |  Categories: Shemales  |  Views: 1691  |  
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How i became a sissy fuckslave pt1

How i became a sissy fuckslave.

It all started after a series of failed relationships led me alone.Having always been a closet crossdresser, i started dressing more and more often and posting pics and vids of me on a website called xhamster.In time, i started posting vids of me toying my sissy ass, and also gradually building up my fem wardrobe.

After several months and many pics and vids, i met a man who offered to train me online.This was mustually pleasurable to both of us and as time went by he started having me cam for him.Toying my ass while he watched always turned me on, and he ... Continue»
Posted by analsubbieinmissouri 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 3019  |  
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Flirting at the mall.......are you sure about that

Before I begin my story let me say that the next time you're at the mall be very observant because there are more of us t-gurls out there than you might think. Since I am one I know what to look for and can pick them out.......so, ask yourself sometime........is that hottie I'm watching for the next few moments a female or a t-gurl??? Wink wink.

OK, so, at the mall. Shopping for shoes......everybody does it including us "gurls". The real trick to "doing the mall thing" for t-gurls is to totally blend in and be just like the women that are there. They dress down and go totally casual for ... Continue»
Posted by tgurlusa 3 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2565  |  
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How I Became Vanessa Chapter 1

PART I:

I was a man before becoming Vanessa, and my name was Mike. I was heterosexual and I was going out with my first "serious" girl friend for two years when all this started. I was still living with my mother who had been divorced for a decade before getting remarried. Her new husband moved to our place with a beautiful daughter named Elena who was only 18. I was a handsome 22 year old blond boy, quite feminine in my features and certainly very shy with girls because of this very reason. My girlfriend, July, was actually my first one, and she did the first step towards me. I was not rea... Continue»
Posted by slutyvanessa 1 year ago  |  Categories: Shemales  |  Views: 566  |  
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The Developing of Emma part Three

She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence.

“Hello again ‘Emma’; that’s a very pretty name you’ve chosen for yourself, we shall soon have you worthy of being Emma, and you’ll soon know your place amongst men, and women.” The woman was sat with her legs crossed in a throne-like chair, no store clothes now, she wore a one-piece black leather bodice which accentuated her mature curves exquisitely, and black seamed panti... Continue»
Posted by midsummerman 1 year ago  |  Categories: Anal, BDSM, Shemales  |  Views: 530  |  
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When I Still Dressed Chaper II

We layed on her carpet fro a few more menutes than i started to suck her cock again going down here shaft to her balls back to her very beautiful ass hole. I was so hot from just cumming in mouth the was very horny and her cock started to get hard all over again she starts to moan over my ass hole side do you want to fuck my ass i said hell yes. So i raise up her ankles to her head which really opesn up her ass and slip right in she very hot and she looks so sexy. I get a rythm going in and out in and out she goes you feel just right now fuck me harder and harder i didn't ne any more erging i... Continue»
Posted by rafael0058 3 years ago  |  Categories: Anal, Shemales  |  Views: 421  |  
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A Soul touching story from my Beautiful Master, De

I come home, I'm wearing the suit you like me in, you always get so aroused seeing me in this suit, it's power, the lines, the way it d****s my masculine physique, it just speaks to the man I am and the man you love.

I'm tired, but you've been home all day, waiting for me, dressing up sexy, trying on different lingerie, you can't wait to see me. I perk up, my lovely sissy needs some attention. So I relax on the sofa, instructing you to crawl to me, your soft smooth ass cheeks rising and falling as you approach me like a lioness. I unzip, unfold my cock, and let you go to work on me, you nee... Continue»
Posted by Hotassboi 1 year ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 447  |  
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Xdresser Housewife Roxys daily chores while wife i

Well i must be the luckiest guy in the world ,my wife earns all the money so I stay at home to do all the house work and cooking .Now I've always wondered what it would be like to be a girl because women to me are so powerful when they are hot and sexy ,a women can get what she wants when she wants without even speaking as long as she has a sexy pair of platform heels on with a tight micro mini and a great set of tits that's enough to get anything from anyone ,if that isn't power what is ?
So this brings me to what I've been doing at home while my wife is at work .It all started one day when ... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 765  |  
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