Shemales Porn Stories
Page 80

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: 1655  |  
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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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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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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: 2750  |  
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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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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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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 7 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1126  |  
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CD Maid Fantasy

Nervously, I knelt on the ground, and wait for Mistress to return. The whole day, I had spent cleaning her house, wearing my maid outfit, always making sure that everything on it was in order. It was difficult to keep the white stockings and gloves clean, but I had managed to do so, all while in 5" black heels, a lace-like maid outfit, and of course, a plug, collar, and cage to keep me from playing early. So I had finished my tasks, re applied my make-up, combed my short black, hair and had been on my knees for almost an hour: all as instructed. As it drew closer and closer to seven o'clock, I... Continue»
Posted by RosalynLee3 1 month ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 937  |  
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Flowers For Pansy

Daffodils were Pansy's favorite. To this day she is still a silly little flower gurl wanting, waiting, craving for another man to bring a fresh bouquet. But today was not an ordinary day. With the vacuum grinding and sucking and growling the knock on the door was just slightly audible. The little sissy . . . excuse me, pansy (she just loved being called a pansy) flamboyantly sashayed her way with little itty bitty tiny steps. She swung the door open and presented a lush bright smile. "Yessss?" She said with a lisp.

"Flowers for pansy." The delivery boy read off his note.

Pansy gasped wit... Continue»
Posted by amberfemxd 1 year ago  |  Categories: Anal, Shemales  |  Views: 430  |  
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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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Paying for my own birthday present!

My wife told me that she'd arranged for us to spend a weekend in London, see a show and do a bit of shopping for my Birthday.

Great I thought.

We got to London, from Wales, early evening on the Friday. Checked into a quite nice hotel in the west end and headed up to our room. When we got up there, my wife headed for the bathroom and told me to come with her. Knowing what to expect, I stripped off and laid in the bath. She climbed in, pulled up her skirt, moved her g-string to one side and pissed straight into my mouth. We'd been in the car for about 5 hours, so what I got was stale and b... Continue»
Posted by garyw 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 2034  |  
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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: 993  |  
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Trapped and Trained Sissy Ch. 05

Trapped and Trained Ch. 05
There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session.

I looked down at myself and shivered as I saw the short edge of my form fitting black dress riding up to where I could already see the tip of my black chastity belt peaking out from underneath. That belt had been absolute hell for me the past 36 hours or so. It... Continue»
Posted by hpm12 8 months ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1006  |  
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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: 2574  |  
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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: 1668  |  
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Impregnated by tentacles

I had just finished a session up at the gym and began walking back to my car. It was dark out and the large car park was empty, nobody could see me. I was wearing just a tight grey leotard. Like this…

My big bulging cock showing clearly up my stomach, small wet patch from a little pre cum, my tits free, no bra, nipples erect from the cold, wobbling as I walked, along with my ass and thighs.

As I got to my car I got in and got myself comfortable, suddenly I was locked in my own car, from under my seat crawled fle... Continue»
Posted by shemalecharlotte 7 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 3634  |  
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Delilah and the Deep Blue Sea. (Part One.)



This story has taken me forty years to tell and I only finally relate it now in the firm conviction that nobody will believe a single word of it. In many respects that doesn’t concern me. I have other motives than those of persuading the reader of the veracity of my tale. I write it more to exorcise a ghost that has haunted me for most of my adult life and will doubtless continue to do so for the rest of my days. It is a story, the memory of which, has been my constant companion these past forty years and has dominated my life in the sense that everything I am today has been shaped by tho... Continue»
Posted by Mikebasil 2 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  Views: 1537  |  
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