Shemales Porn Stories
Page 59

His teacher, The transsexual

A really nice story from another web page! Enjoy

Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't accept excuses.

Greg had only started his last year of high school here after his eighteenth birthday a few months ago. He was worried about the impressions he was making. He got to the door of his health class and checked his watch apprehensive... Continue»
Posted by Ankakalle 2 years ago  |  Categories: Shemales  |  Views: 1563  |  
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Why I miss my ex

Why I Miss My Ex
I feel obligated to say that I am not a passable crossdresser, not even close. Even without my beard, I’m very masculine, large framed, and I have a very deep voice. All of these things aside, I love to dress up in sexy lingerie, panties, dresses, bras etc. While I’m dressed, I love to be verbally humiliated, although, I don’t think being called names like “sissy” or “fag” or “cuckold” is actually humiliating. For me, it’s a huge turn on, and I love to think about sucking cock while I’m being humiliated.
It’s quite a long story about how I got my ex-wife to play with ... Continue»
Posted by pbg732 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 890  |  
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How I Became Vanessa Chapter 3

Hello dear readers,

I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life.

*

At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all the things that happened at July's, blushing as Jeff was watching me with desire.

Elena hadn't changed her sexy outfit and her beautiful face leaned towards Jeff's crotch uncovering his 10 inch cock which was even thicker than John's. She started to suck it hungrily, encouraging me to join her whi... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  Views: 909  |  
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Delilah and the Deep Blue Sea. (Part Two)



When I awoke the next morning I was alone. I rose up from my bed amidst the ruins of the villa and peered around cautiously. There was no sign of her. Carefully I tip-toed out from the ruins and conducted a quick scan of the surroundings. The little olive grove was quite deserted other than the small creatures with which I shared the island. These seemed busy at this early hour. There was a little dark grey bird singing from the scrub at the edge of the olive grove. It had a musical voice I found quite soothing. I was to become familiar with that little bird and the mate he found to build ... Continue»
Posted by Mikebasil 2 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 1005  |  
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Used Like A BBC Whore

About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night.

He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would notice them watching me. When I would walk by they never said anything but one of the guys always smiled at me.

While one night I got a phone call and he said his name was Rick and he lived down the hall from me. He told me what he looked like and then I realized it was the young black guy that... Continue»
Posted by sissy_gurl 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 2858  |  
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The Making of A Sissy-Part One

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father. Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind. Jane’s girls took special delight in dressing their sissy b*****r and loved to take him out to the mall and such places, dressed in pink frilly skirts, where he learned to be humiliated. He was shown to the packs of small... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1712  |  
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THE DARK BACKWARDS CONTINUES !

I jerked off several times while watching the SULKA video. At this point I wanted more. I returned the videocassette to the video store and made my way towards the darkness that was the ADULT section. I opened the door and there were several people in the room. My excitement turned to fear. Fear of being in a room of strangers looking for porn. My hands shook a little as I tried to hide my shame. I nervously looked around the room to find a spot where I could sheild my face.

I wanted the room to myself. I waited and pretended to be interested in the straight porn. I must have been in th... Continue»
Posted by bryanferryfan 1 year ago  |  Categories: Shemales  |  Views: 879  |  
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Being a shemale's toy can be fun

Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my needs this week end.'

Sensing desperation, I gave my demands 'reward me up front in large bills in an envelop that I will address and drop into the post office before we do any thing, you will give me your car keys before we enter any building, and I have the last word as to what I will and ... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1392  |  
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Dirty Tranny gang bang

Deep breath Charlotte, step into the night air and strut your stuff girl.

This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glitter in the light reflected from the street lamps.

It is not quite 8 pm as I walk the short distance from my hotel to the pre-arranged meeting place just outside the pub near Tower Bridge.

Two men walk past; mid thirties and well dressed, they have both been looking at me for some time,... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1175  |  
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roadside ass-istance...part 1

as i was driving home, thinking about malcolm, i saw a car on the side of the road, ahead of me. as i got closer, i saw a very cute black woman standing by the side of the road, looking very irritated. i slowed down & pulled off the road behind her car, then got out & asked her if i could help. she asked if i could give her a ride, because she couldn't get a tow truck 2 come out 4 at least an hour. i told her 2 hop in & she gave me her home address, saying that she would just call the towing company when she got there. as we cruised along & chatted, she told me that her name was angela & that... Continue»
Posted by tight_virginal_ass 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 2185  |  
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A Halloween Hoodie story

*crossdress story*
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excitement that spurred me on.

Of course i was scared of seeing someone i knew, like a neighbour or a friend, but it was about 22:00ish, so i figured it was dark enough and late enough to avoid those kinds of people.

It was a lovely feeling as i stepped outside, the wind rushing... Continue»
Posted by KitsuneTV 4 years ago  |  Categories: Shemales  |  Views: 584  |  
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Becoming Aphrodite Ch 01

My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettable and even the famous porn star I mentioned could not compete with her.

We got married very young and we were very happy for many years but Jennifer was slowly changing, discovering parts of her which could not be ignored any more. In fact, she did not have enough sexual experience before getting marr... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1645  |  
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The wonderful feeling of a sissy penetration by yo

Nothing like that initial penetration is soo wonderful however there is so much more for me. just knowing that i intend to give myself to him submitting to his Big Hard Man Cock is a turn on. He wants me ready for him so he can show me his love and make me his girl.

The act of preparation, the douching and initial lubing, knowing I'm going be taking a real man cock inside me builds on the sexual emotion and makes me feel so submissive and feminine.

laying there in my nighty and panties and assuming the position he desires, normally face down, pussy up, legs together, wiggling my botto... Continue»
Posted by sissygirl 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 781  |  
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My highschool girlfriend 2

It had been a week and me and my girlfriend had not done anything else, but ofcourse we talked about it. Her mostly, saying "I was so sure you were so strait, im so happy your okay with my cock" all I would say was "I was so sure I was strait too, but being with you, just changed that I guess but I love it, you make me hornier than a girl with a vagina ever could." She also brought up another point, that the anal can go both ways, and ask if she could be on top next time. I was kinda scared it would hurt, but thought it may be fun, and told her that and she said she would make it painless, by ... Continue»
Posted by suckmedry69 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1737  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 1 year ago  |  Categories: Mature, Shemales  |  Views: 1338  |  
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Shemale Whore and Arab Pimp

HERMAPHRODITE WHORE

It had been over a year since Johnny threw that tantrum that
ruined me and got him excommunicated from mom.

Holding me down when mom walked through the door with
her friends, colleagues, whatever and they all gasped and
screamed as my big b*****r finished doing me.
We had ample warning, we could have all vanished when
we heard them at the door.
Bobby ran away and got dressed. The chickenshit
denied any knowledge of the event.
Smart but chickenshit.

Mom severed all ties between me and our doctor's
little perv ring, so I had no more money coming in.
I di
... Continue»
Posted by Utubeslut 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 881  |  
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She wanted to Watch!

Everyone knows I'm bi and a Transvestite. I don't dress as much as I wish but I do go out two or three times a week. When I'm not dressed up I tend to hang at a straight redneck bar thats about two blocks from my house. They all know both mark and Kristy there and most are nice to me and respect me because of the respect I give to them.

Well yesterday I was in after work for a couple beers and Cindy the bartender and Lisa wanted me to do some drinks with them. Orange Crushes, wow I didn't want to get d***k cause I had plans for Kristy to go out clubbing. But after encou... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1168  |  
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My First Gangbang

For as long as I can remember, I have always enjoyed wearing women's clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too ;-)

As you may imagine, I became VERY popular! Pretty soon, there wasn't a sl**pover in the neighborhood that I wasn't invited to ;-)

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my... Continue»
Posted by cdsexslut 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 4396  |  
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banged in panties

The day was 10/4/2012 and normally I only wear panties inside never on the outside, but I was feeling kinda kinky. So after doing my running around I decided to stop at a local adult porn store with the booths and private rooms. At the same time I was texting with a friend from here thats crazy about me in my panties. I told him that I was wearing my panties being that I thought we were gonna hook up, but due to scheduling we weren't able to, so he asked me to take a pic with my phone and send it to him, now I wasn't home so I didn't think that i would be able to pull it off, suddenly this nic... Continue»
Posted by frkinatl 2 years ago  |  Categories: Shemales  |  Views: 2437  |  
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The Developing of Emma Part Four

Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. Elaine was right, Emma was beginning to enjoy the plug and as she tried to rub her confined cock, she imagined the plug to be Kurt’s cock; how she wanted to cum! The blue pill she had been given would keep her little cock hard in the cage and make her yearn to orgasm. This would make her extra obedient a... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 832  |  
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