Shemales Porn Stories
Page 75

FoxxiRoxxi xdresser slut fucked by BBC

Well this has been a fantasy I have had for a long long time .I'm a married man with a f****y and love fucking my wife she has a shaved pussy and a few sex toys so our sex life is good. However I have been xdressing on and off for about 12 years now and I really love it . I really love the feeling I get when I get all dressed up .I could easily have a sex change if I didn't love my f****y so every now and then I get a hotel room and spend the afternoon getting my outfits ready and my wigs brushed for my night as a girl .I get so horny dressing up in sexy fetish outfits and tight short skirts ,... Continue»
Posted by foxxiroxxi 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1019  |  
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Jenny, Melissa and Me

I’m watching you on the screen, Jenny, as you pull down your pretty nylon panties with the floral prints and spread your legs. Your brunette hair hangs down around your lovely eighteen year old face, smiling as your labia open wide and you begin to rub your clitoris, all the while smiling, and gazing at me with yearning through your computer camera.
In front of my camera, so you can see me, I put on a pair of sexy pink panties over yellow nylon stockings and a pink garter belt. I put my hand under a sheer negligee and stroke my shaved cock and silky smooth shaved balls for you to see. I... Continue»
Posted by pantyboykristin 1 year ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 567  |  
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Fun With Frilly Socks and Mary Jane Shoes

As I walked into the bathroom to take my evening shower I noticed that my
daughter's cute pink mary jane shoes and a pair of her white frilly socks
were laying on the small dressing bench. The socks had each been
separately placed just inside each shoe's opening with great care,
certainly not the usual way she would have normally removed and discarded
them by flipping the shoes off in 2 different directions and then pulling
off the socks, turning them inside out and balling them up. No....this
seemed as if tender loving care had been given to the delicate items. So
unlike my daughter.
... Continue»
Posted by ankletsguy 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 658  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1658  |  
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A video shoot - Part 2 of 2

Now there are even more guys on set. About half seem to be jacking off. I ask John what he has up his sleeve and what he needs me for.

It a Bukkake film. Damn, I get to see Tina covered in cum. My cock twitches at the thought. John tells me he needs a fluffer. I don't quite understand. After all Tina is just damn hot. Who would need a fluffer to cum on her? John says Tina is too girly. WTF? He says well some of the guys are gay and are having a hard time getting up. No pun intended. I now get what is happening. I protest weakly. But I am almost in pain from being horny as hell.... Continue»
Posted by nobodywashere 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1691  |  
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SissyRayG at the Roadside Reststop......


Last year I was traveling by car on business between Saskatoon and Regina, Canada. I was looking for a roadside rest area to use the washroom. I had all my sexy lingerie with me and hadn't had a chance to wear it for days as had been way to busy at work.

I saw the roadside rest area I was looking for and pulled off the road and stopped near the rest rooms. There were four stalls in the men’s and three urinals. It was one of my favourite places to dress and attempt to seduce guys. I got out of my car with my backpack full of satin lingerie and high heels and went into the stall in the... Continue»
Posted by SissyRayG 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1966  |  
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The visit

It started out simply enough, I was visiting my s****r and
her husband for the week. They both work so I had the run of
her house and I took advantage of the opportunity to sl**p
in on my vacation. I woke late and assumed everyone had gone
for work. I took a nice long relaxing shower, s*s’s bathroom
was warm and cozy so I took my time.

When I went to put my towel in the hamper I noticed a very slinky
teddy and panty set on top. I had never thought of my s****r
wearing anything like that so I picked it up and looked it
over . It was pink silk and trimmed in lace. It felt so soft,
I ... Continue»
Posted by pandys 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2736  |  
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caught my son crossdressing



I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make-up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching him put on mascara, blush and lipstick. He was completely mesmerized by his own ladylike reflection, completely entranced by the girl in the mirror. He did a very good job with his make-up; clearly he had done this many times before.

Of course, Jamie was very upset and embarrassed when I announc... Continue»
Posted by momandboys 8 months ago  |  Categories: Shemales  |  Views: 2690  |  
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SISSY DANI PART 2

CHAPTER 2

Some six months after Mistress Jennifer first imposed the "sissy
Dani" persona on me through post-hypnotic suggestion, our lives
had settled into a routine. Most of the week was quite
normal--only Jennifer's insistence that I wear a corset and
baby-dolls to bed indicated the hold she had over me. Naturally,
I complied, since she could always threaten to permanently impose
"sissy Dani" on my mind. Weekends, however, were generally spent
in my transformed bondage. Perhaps a description of one such
period will demonstrate the nature of our relationship.

I arrived home fr... Continue»
Posted by alexwd0 3 years ago  |  Categories: Fetish, Shemales  |  Views: 618  |  
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A TGIRL FANTASY

For some time I've had a FANTASY of meeting up with a hot chick and bringing her home to have sex. After relaxing with a bottle of wine and getting aquainted we make our way to the bedroom. Turning the lights down low we beging undressing each other slowly as our passions rise. I lift her slinky dress over her head, she unfastens my pants letting the fall to the floor. I playfully touch her breasts covered by a lacy bra watching her nipples grow hard as she slips her hand inside my boxers. My cock begins to throb growing harder as she fondles me. I unsnap her bra and pull the straps off her sh... Continue»
Posted by querico44 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3010  |  
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How i became a sissy fuckslave pt2

Sometime later, i'm not really how much later since i seem to have dozed off, Sir came back in and woke me up by swatting my ass hard"Wake up slut".

Sir unlocked my cuffs, and my ankle restraints and said"Down the hall, second door on the right is the bathroom, go there, remove the corset, catsuit, boots and hood, remove the plug and clean it and yourself up.When your done I want you to put the corset on, and hood as well as the boots and then go to the room across from the bathroom.Don't worry about cinching up the corset, I'll do that when you get in the room.If you have to pee, your to... Continue»
Posted by analsubbieinmissouri 2 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1849  |  
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First Time pt 3 by trans_love (Fiction)

Introduction: This is a true story that happened to me when I was a young "woman"

Here's another. Again, I was 13 at the time, I was 5' 2" , 105 lbs, long brown hair, green eyes, ass to die for, I stole my grandma's estrogen pills and started growing boobies, I was now a full b cup.

A couple weeks went by and I only seen my younger black guy a few times. He let me suck his big cock but that was it. One day he told me he met someone else and to not come around any more. As I turned the corner and was heading home his dad, James, pulled up along side me in his car. He said, "Jessica, why d... Continue»
Posted by 1superhornyguy 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1126  |  
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Sucking my own shemale cock!

It is nice to be flexible, as i am lucky to be, being now a personal trainer and formerly a gymnast, so i can bend at the waist with no problem. Recently, i saw a vid where a guy bent and sucked his own cock and came in his mouth, so hot! Well, why not try it, so i did. Went to bed , jacked my 7 inch shemale cock really good, got it hard, then bent over and did it! I first got my mushroom head in my mouth, so i sucked it for the longest time, felt so fucking good, then wa able to get about 4 inches of my cock in my mouth, sucked for a few minutes. then i felt the urge to cum and i let it go, s... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 3026  |  
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Weekend Office Sex

So I am the low man on the scale at work. My job is with the City I work in dispatch and am one of the people responsible for getting road crews, hydro and sewer crews out to fix problems wherever they occur. My boss is a very attractive woman named Jamie. She stands about 152 centimeters and dark chestnut hair that is short at the back but gets long at the front. It matches her deep espresso eyes. She dressed very professionally at work ankle length skirts, blouses and blazers that type of thing. She has perky c cup breasts that when she trots or runs through the office they have a nice... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1867  |  
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Who's watching Me?

It's cold out now and now my favorite time of year. Warmer weather means I get to wear short skirts and midriff length tshirts or halters. I love to wear thigh high stockings and garters along with a thong and go to my local park where
guy cruise for sex on the downlow. Yea I'm a transvestite and I look pretty hot sometimes, but also have clothes for all occations.
This afternoon after getting off work around 2:30 I quickly pulled into a quite spot a few miles from the park and got out my bag. I had as normal worn my thong and size 6 lowrise stretch jeans to work, I love the ... Continue»
Posted by kristygurl 3 years ago  |  Categories: Shemales  |  Views: 994  |  
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First Time Shemale Encounter

Lets start off by saying this a very true story, one that i love to re-live over and over. lets begin

I was in el paso, texas..my girlfriend at the hotel. Something in me decided to go to the strip club. So i did. After a few dances, i decided to leave. I had always heard in mexico it was very easy to find shemales. So i decided to go over the boarder to the very dangerous city of Juarez. After i was in mexico i grabbed a beer and started walking. Within 15 min i noticed these beautiful women all standing outside of an apartment building. I walked over and proceded inside. Not kno... Continue»
Posted by iLoveShemales12 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2585  |  
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When I realized I was Bye and gay

I was a late bloomer I got married had k**s bought a home had all the things to make a happy home but I was restless

i needed something else. I was going out with other women about once a week and it was fun and sometimes very hot i even had a few three somes but I always felt I needed something more. One night when I was driving home there was this girl standing a crosswalk waitting for a taxi she was very hot so I put down the passanger window and offered her a lift she got into my car, the signal changed and as we drove on she told where she wanted to go, I said thats a different type o... Continue»
Posted by rafael0058 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2427  |  
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Learning how to deep throat...

I was working the drive through window at the burger late one Friday night, this somewhat diminutive husky voice placed an order. My cock instantly begin to twitch as I heard the voice. I took the order and instructed the customer to pull up to the first window. As the car approached I observed that the driver was a shemale in full dress with a split up her right thigh to the waist.

I was so absorbed by the sight of that yellow thigh and leg that I fumbled through the rest of the proceeding. The driver looked up at me and whispered 'you'd do better if you looked at my face instead of my... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1667  |  
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Living with Mother ….. continued

Living with Mother was always interesting, especially because she loved to see me dressed as a girl/woman. For almost 4 years, weekends would always be special time, whether Mother, my s****r and I were at home together or whether I was there with either of them. The dressing was just what I did, evenings were always rather easy but the weekends much more intense.

A typical weekend would start Friday evening when I returned home from school, straight into the bath, made myself as clean as possible and then into the clothes I had laid out before I went to school that morning. Nothing too ... Continue»
Posted by antoniaf 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1771  |  
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Teen pussy of 18 years in bathroom stall masturbat

Certain noises merge from a closed bathroom stall door which you well know are only from a girl pleasing herself, so it was no surprise to myself, a shemale, who uses the girls room very discreetly, to hear such moaning 2 days ago in the bathroom stall of a store in the local mall. And since i jack my cock off in those stalls also and spurt my jizz, it is always a thrill to hear another girl moaning, even so slightly, with pleasure as she fingers her wet pussy. Thus, i literally stood next to the door and wham, it was not locked, guess she wanted to be watched, so i went in and she just smiled... Continue»
Posted by cumsquirter 2 years ago  |  Categories: Shemales  |  Views: 2090  |  
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