Shemales Porn Stories
Page 79

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 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1977  |  
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A Girl Too Remember (part 2)

It’s only been 3 months since I found out Snow is a hermaphrodite. Things haven’t changed between us much. We are slowly getting closer. Not sure if it’s possible for me to want her even more. School however has gradually gotten worse. Apparently there was a girl that wanted to date Snow and now she has a grudge against me. She didn’t care that I was with Snow, she just wanted me out of the way.

Her name was Carla. She’s from Puerto Rico. She’s beautiful with long black hair. I think her bust was an E. She sounds like the kind of girl all the guys would kill for. The thing that kept them al... Continue»
Posted by nightheart13 5 months ago  |  Categories: Voyeur, Shemales  |  Views: 2141  |  
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Her first shemale

It was no secret to me that my girl was bi; we had talked about it and I encouraged her to express and explore her bi side. When I managed to get us a date with a hot girl, I decided to keep it a secret.
I took my girl to a nice dinner, and while being seated our date for the night showed up and introduced herself- her name was Ann. We had a nice dinner, and on our way back I asked the girls to sit on the back seat. Ann was not shy, and neither was my girl, so before I knew it Ann had her hand up my girl’s skirt and they were kissing hard. By the time we got home, my girl was already wet and... Continue»
Posted by angelslover 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 2130  |  
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Encounter In The Park

It was near the end of my junior year in high school and my parents ere in the midst of their big divorce drama so I was spending most of my time at my best friend Kelly's. It was just Kelly and her Mother because her dad left the picture several years earlier. Kelly’s mom was a great surrogate mother because she knew what I was all about and accepted me with no reservations. Kelly was well on her way to becoming a hardcore lesbian so her mom really enjoyed doing girlie things with me. We used shop for clothes together and she taught me the proper way to apply my make-up and style my hair. ... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2815  |  
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Would I be happy if I could remember...

My story began a few years ago when I was in college. My roommate decided
to let his girl move in with us and although it is annoying working my
schedule around their love life, she was very hot and I didn't mind the
occasional show when she would run from her shower to their bedroom. I have
to admit. My roomie was a lucky man. That girl had to have the nicest
breast on campus and an ass to die for.

Eventually as most love stories go, things fell apart
between them she had somehow talked my roommate into moving out. I should
have known she wore the pants in that relationship. How do... Continue»
Posted by urgonnaputthatwhere 1 year ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2098  |  
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Something in my drink, the captive part 2

So there I lay face down in the floor, hands bound a ball gag in my mouth and cum dripping from my mouth and ass, those tranny bitches really did a number on me, and left me like this in the floor in a dark room, exhausted and still confused from the mickey in my drink I feel asl**p.

I did manage to get some good sl**p, and I awoke to Tara giving me a sponge bath, my hands still bound, and a collar around my neck chained to the rails behind me, I was still a captive with no options. Tara was being much more gentle to me this morning, even feeding me breakfast, brushing my teeth, and puttin... Continue»
Posted by smonkeys32 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 2771  |  
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The GloryHole [true story]

one evening,I was feeling realy horny,so I got dressed to go to the local adult x store.wearing nothing than a strapless black lace corset,no panties,short mini skirt,and a pair of thigh high boots.and went with a short blonde wig.well walking thru the door,I turn to the left wear the door stood to the rooms,I could tell it was crowded,and there were alot of guys either standing around,or walking.well I found myself a cubicle,and went inside,slip a few bucks in to turn on video.a few seconds later I had a big cock sliding thru the hole as I reach down to pull it in my mouth licking it,and st... Continue»
Posted by blonde68 2 years ago  |  Categories: Shemales  |  Views: 1882  |  
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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: 1770  |  
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The Blind Date Night Part 1

The date was arranged by a good friend of mine, she said she'd shown my picture to Warren and he kept pestering her to arrange a meeting. I finally agreed to meet him with no strings attached or promises. I had no idea what to expect or how far things might go but I always like to be prepared. I showered, shaved my legs and any other area that needed attention, shampooed my hair and perfumed and powdered my body. I decided to wear black thigh hi stockings, a black push-up bra and the cutest tiniest string bikini panty. The panty was black with a touch of lime green lacy trim. The lime green st... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  Views: 702  |  
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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 2 years 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: 563  |  
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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: 650  |  
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roxanna's gyrl script

so... there's lots of stuff we have to go through to bring out our gyrl... hair removal, voice training, early clown makeup nightmares (mine still make me shudder...) & all other kinds of stuff... but amongst all the options out there i really love hypnosis...

the key to hypnosis is to relax... not relax till you fall asl**p but to just relax so that you're brain isn't thinking about anything else but one thing... the hypnosis script... ideally, you'd be in a state of relaxation that's exactly the place smack dab in the middle of being awake & falling asl**p WHILE AT THE SAME TIME... concen... Continue»
Posted by roxxanna 1 year ago  |  Categories: Shemales  |  Views: 448  |  
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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: 1654  |  
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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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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 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1848  |  
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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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Passionate Sex with a Beautiful Shemale

Passionate Sex with a Beautiful Shemale


a man and his shemale lover get down to business
Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.

“Mmm,” she moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in goosebumps.

She turned to face him, wrapping her arms around his n... Continue»
Posted by adel5000 3 years ago  |  Categories: Shemales  |  Views: 618  |  
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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 11 months ago  |  Categories: Shemales  |  Views: 2720  |  
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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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