Shemales Porn Stories
Page 15

Shemale before emails

1996, Old enough to get the fuck out if the sl**py little Scottish village I was brought up in and take part in the clubscene born in 88. Myself and 3 friends had boarded a flight to Ibiza.we hit it hard the first night and the second. On the third I flaked out in the hotel as my mates headed bk to San Antonio for more treats, lights and beats. They were all arrested for swimming in the fountains on the main drag. When. Police arrived one of them got a lucky punch on the polis man's jaw. Then they were beaten into a meat wagon,had their passports stolen, all their £ lost or stolen in the proce... Continue»
Posted by cockaine666xxx 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
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A cumslut gets fed - Apr 2017.

Well it's been a few months and I haven't gotten much action. I guess I've been too distracted. Regardless, I was horny as all hell last month and decided to check out the talent online - by which I mean Craigslist.

I wasn't too impressed by the options, but I did find one ad that caught my attention. "I come to you, and you cum in me," it read. The poster's name was Taylor. Though I usually go for TG women who are in transition with long hair and big boobs, I would characterize her as more cross-dresser and/or sissie type. That's labeling of course, and something I try not to get to... Continue»
Posted by Quadrilateralus 5 months ago  |  Categories: Anal, Shemales  |  
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REPLACING MOMMY

Laying on my belly dressed in her favorite Victoria Secret naughties I have on her red high heels and her long chestnut brown wig and makeup I look over into the mirror and I see her he always called me her clone I looked like her was built like her and everything hell I even had her personality so when she died in that accident I was not really surprised when he turned to me for comfort and now for sex pumped up full of female hormones my body feels different my hips are wider and my lips fuller heck I even have tits now thank god we moved away and I quit school or this would be a ... Continue»
Posted by laceysgirl 5 months ago  |  Categories: First Time, Shemales  |  
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Halloween party II

Laying on Steve, I looked around and noticed no one was paying any attention to us. Listening to music and talking to each other. Steve said, why don't you take off the sheet, I said I only had underwear on. Really, he whispered. He ran his hand down he slipped it under the sheet. He rubbed across my crotch and up to the waistband of my underwear. Putting my hand on his to stop him he said relax, no body is watching. Taking a deep breath and a big drink of the beer, I said ok and moved my hand. He pushed his hand under them and found my dick. Mmm very nice, he said. Thanks I told him. He ru... Continue»
Posted by 1120scott 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My first gay expierence

During this time in my life I was searching for a trans girl. I just went to through a breakup with a female and wanted something different. I was 28 at the time and had only been with women. I think my attraction came in high school when I used to masturbate side by side with this cute little Asian boy. He was in the band and I played football. Plus, I had a girlfriend so it was sort of my little guilty pleasure, and extremely secret. I was young so being popular actually mattered and I'm sure jerking off with the gay band nerd would've destroyed my reputation. Since, I've grown up, an... Continue»
Posted by shooterdude33 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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latent trav since 15

Hello Lovely tv's tg's, cd's and all gender neutral folks out there.
Let me tell you my story about how I've come to love gender neutral people with a preference for femininity.
As of the age, what I can remember of it, of 5, I loved women, and at that age more specifically, my mom, in pantyhose. Yes it's true, at the age of 5 I got turned on by my moms black shiny pantyhose, and what was so funny, at the age of 5, there's no taboos, you just shout out loud what you like. Obviously at a certain age, I stopped getting horny of my moms pantyhose. But I kept getting horny of older then me women... Continue»
Posted by tsjarli 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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My Tgirl lover

This is my first attempt at writing one off these stories so if you like it than please let me know and I'll look into writing another one also any feedback would be welcome
My names Phil, I'm 28 and I currently live with my girlfriend with whom I've been dating for several years. Up until moving in together the sex between us was pretty good, we would do some BDSM on each other as well as having sex outdoors but unfortunately as soon as we moved in together back in mid 2016 the sex all but dried up to the point that we were only having sex on an average of once every six weeks and it was al... Continue»
Posted by Maillihp 5 months ago  |  Categories: First Time, Hardcore, Shemales  |  
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Continued Sissy Date

Before James arrived, I checked myself in the mirror; to make sure I looked great for him. My girlfriend Ann taught me well how to apply my shade and I styled my hair long and curly, so it just d****d over my shoulders, my short grey dress stretched tightly over my chubby frame and looked great against my light chocolate skin tone. I painted my toes so when they poked out the 3-inch mule they would be very pleasing. A little lip gloss and finally a dab of my favorite perfume behind each ear. After a few more poses I asked myself “Does this dress my butt look big?” then chuckled to myself remem... Continue»
Posted by MatureBrownMan 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Veronica

I met Veronica whilst on holiday in the USA. I found myself in Houston Texas lost with nowhere to stay and got chatting to this beautiful angel. She told me her name her voice was so sexy and her eyes just melted my heart. She invited me for a drink but I told her I was a bit lost and looking for some place to stay to my surprise she said you can sl**p at my place if you like and sort yourself out in the morning. The smile on her face was so inviting she was dressed in such tight fitting clothes showing of her curves but I thought to myself ahh she is just being friendly and I gladly accepted... Continue»
Posted by yesyesyesplease 5 months ago  |  Categories: Anal, First Time, Shemales  |  
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Sissy Lucy meets her daddy

I’m in my late 20’s and manage a local restaurant/bar. I am 5ft 8 and slim with quite feminine features. To most people I’m just Tom, a regular guy who has occasional girlfriends, likes a beer and watching the football. To my closest friends I’m Lucy, a sissy slut who loves cock.
Recently I’d found a ‘daddy’ online. He was an older more experienced man. We started off chatting and I sent him some naughty photos and video clips of Lucy playing.
As we talked I revealed that I like to be dominated, told what to wear and how to act, made to be naughty and told how to fuck myself. Daddy slipped... Continue»
Posted by emilykingx 5 months ago  |  Categories: Gay Male, Shemales  |  
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Awakening My Trans Nature, My Second Experience Of

Previously I had described about getting the panties and starting in a small way anal play. Well a month later I was asked to change rooms for redecoration. The new room was at the back and had a bay window which when you looked out there were flats and balconies. You could see the occupants getting on with their lives and, as it was summer, sunbathing sometimes. One night I had stripped naked, totally shaved myself which always felt great and put the panties on. It must have been about 11ish and was admiring myself in the mirror, my thin hairless body and long legs, really it was quite girly.... Continue»
Posted by SapphireSomeday 5 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
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ARE YOU FULL YET?

"Are you full yet?" That is the questions he always asks me as I lay there across his knee with the nozzle of the enema bag shoved deep inside me...I will answer "No Sir not yet!" As he squirts his ice cold urine into my colon it has to be ice cold so I can feel it rise up inside of me and I do inch by frigid in it creeps up my intestines and I cramp a little from the cold see he saves his pee all day long and stores it in the fridge and then every morning he feeds it into my ass he enjoys doing this to me and I must let him I am his sub you see and do everything he wants...Finally I ... Continue»
Posted by laceysgirl 5 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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A Kitty's Revenge

Like many people, I was bullied in school. I was small, slender and effeminate and, as a result, was often called gay, queer, fag and sissy by school bullies. The fact that what they said was sort of true just made it closer to the bone and more painful to hear. Like many teenage boys, I was going through something of an identity crisis surrounding my body and my blossoming sexuality. The feelings that I had always had as a c***d that me being a boy wasn't quite right were now increasingly pronounced. Of course, under the circumstances, this just made me more embarrassed and insecure; I was so... Continue»
Posted by CumLovingKitty 5 months ago  |  Categories: Hardcore, Shemales  |  
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How to make a vacation fun. Pt3

This is the end of the vacation series. It contains Femboy, Oral, Anal, and Older/Younger. Done in FP PoV

Mom and Jack were back by the time I got back to our camp, and from the looks of things it seemed Brad was still asl**p in our tent. What a lazy ass! Jack was in the process of hauling the canoes down to the lake, and not wanting to just stand around watching like mom was doing, I went to help him out. Mom was quick to take note of the attire I’d chosen to wear today, but other than a quick flicker of worry crossing her expression, she showed no other signs that she cared one w... Continue»
Posted by Wolfshed66 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Sissy Gives First Blowjob

I finally decided to take my crossdressing to the next level. I have been dressing for a while now at home, playing with my toys and I felt like it was time to make a move. I made a Squirt ad about meeting a guy for drinks and fun then posted it. After filtering through the responses, I found the man I would service for the first time. He read my response back to him, and said he wanted to meet ASAP. I left the computer to go get myself ready. I did my makeup with blushed cheeks, dark brown eye shadow, pink lips with lip gloss and my nails in a bright girly pink. I had a long black hair piece ... Continue»
Posted by MatureBrownMan 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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My satin shemale evening ... part two

The night before had been amazing... i had been lured in by a sexy passable shemale and used... it was great.
I could still feel the red marks on my ass from where she had been spanking me the night before....
It was fairly early when I awoke.. hands still bound behind my back, wig and make up still on, dressed in a tight silky fish tail dress that had been torn open from behind in the heat of the moment.
I looked around and saw her there. Leaning on the door starting at me. A loose short black dressing gown completing her curves so well. She spoke...
^how you feeling this morning my lit... Continue»
Posted by satindresser 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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amatuer crossdressing prostitute

So it started out by just a regular day. Work was really becoming a drag, and it was only 11:00 am, and my mind started wandering about what I was going to do when work was over for the day. I stopped at the mall on my lunch break and when I was done at the food court I decided to stroll through Dillard’s on the way back to the parking lot. I couldn’t help but pass through their lingerie section and noticed the cutest little bra and panty set. It was kind of a purplish flower ensemble that I pictured would look good underneath my black mini skirt. I hadn’t dressed in quite some time, so yeah ... Continue»
Posted by stormietv 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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The body Builder

So it was Saturday morning and I had been texting this dude for about a week, getting to know each other and expressing our sexual desires. This guy was straight and was so curious to find out what its like with a DQueen, I told him that It takes a real Man to bring out Cleopatra. I asked him If he was really sure he wanted to be seduced by a Goddess and taste the sex poison from my tongue. We chatted for a while before he told me that he was involved with someone and their sex life was kinda rusty. Being the snoopy Queen i am, I stalked his girlfriend on facebook, and omg she is hot i feel li... Continue»
Posted by Cleopatra69 5 months ago  |  Categories: First Time, Hardcore, Shemales  |  
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How to make a vacation fun. Pt2

Story contains, Femboy, Oral, Interracial, Old/Young. Written in FP PoV

That first day of vacation went by way better than I had expected it to go. Right away I’d gotten a wonderful facial and a decent mouthful of cum from my favorite guy in the whole world. Plus, not an hour after that, I’d been able to bring my step dad to orgasm simply from fondling his boner right through his khakis, which was something I was still trying to figure out how I’d managed to pull off. I mean, did I really turn the guy on that much for him to get off on something as simple as a groping? I had no ans... Continue»
Posted by Wolfshed66 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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My First shemale Mag , and a little More

It was late afternoon when I ventured into the local public toilets , I had been a few times and had been reading the graffiti for ages , so was already excited to be going back.
I went in and checked out the first couple of cubicles and read a few new additions and was already hard and turned on , there is just something so primitive and seedy about wanking in the toilets reading dirty messages , wonderful.

I moved into the third cubicle and discovered a carrier bag stuffed behind the toilet , it was quite full , on top there was a typical porn mag of the time , a fiesta or playboy , it w... Continue»
Posted by jakuk 5 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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