Shemales Porn Stories
Page 80

first time with both

I was young and I had a girlfriend who I confided a dark secret with, which I had never felt comfortable to tell anyone. She asked what I wanted to tell her and the suspense in the air as I told her was quite thick.
"I've always felt like a woman trapped in my body." I casually said.
"Why did you never tell me?"
"you are the first person I have trusted to tell."
She looked at me for a while, but then told me it was cool, and that I really had the body to pull it off. I was so relieved. She brought me sexy lingerie to try on and it fit, except for in the bust. I didn't care though I even s... Continue»
Posted by Lauren_lee 2 years ago  |  Categories: First Time, Group Sex, Shemales  |  Views: 2709  |  
94%
  |  7

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 neck, drawing him close. They kissed, tongues ... Continue»
Posted by adel5000 3 years ago  |  Categories: Anal, Shemales  |  Views: 913  |  
94%
  |  6

My very first experience with my classmate (episod

He was amused by the sight...of me in lingerie..standing on the porch,it was obvious he was in a shock (or state of extacy?) and couldn't take his sparkling blue eyes off my firm body inside the dress...he closed the door behind,like he was worrying if someone could see us ..I don't know why but i felt the tears running down my cheeks as a result of this emotional discharge and hugged him,saying ''I was scared to death..of losing you...I thought you would never talk to me again''...Maybe i was being hysterical but i really wasn't thinking healthy at that moment..a typical girl:) I started to ... Continue»
Posted by Slave4str8twinks 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1410  |  
94%
  |  5

A cum slut is born

There's little doubt about what turns me on most -- just check out my favorite videos and photos. Cum, Cum, and more cum. I'm a late bloomer as far as discovering my kinky side. After a long, dull marriage consisting of vanilla sex, I got divorced a few years back and decided to explore some fantasies. I love porn, and I've always been somewhat envious of the chicks in the xxx vids, they always seemed like they were having tons of fun getting their cunts, mouths and asses filled with hot cum. Multiple cum shots really turned me on. But I'd always identified as heterosexual -- so how could it b... Continue»
Posted by jizzlover123 2 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 3568  |  
94%
  |  20

I CAUGHT YOU, SO NOW WHAT!

YES, MOST OF US , YET NOT ALL OF US, HAVE BEEN COUAGHT BY SOMEONE ELSE, WHOMEVER THAT MIGHT HAVE BENN WHILE WE WERE MASTURBATING, EITHER OUR COCK OR PUSSY, AND OUR REATION IF CAUGHTCAN BE SO DIFFERENT! YES, I WAS CAUGHT JACKING OFF MY SHEMALE COCK ONCE AND ONLY ONE, BUT THAT WAS ENOUGH OF AN EMBARRESMENT IN ITSELF, SO I TAKE MORE CAUTION WHEN I MASTURBATE NOW, YET IIT DID OCCUR! AND NOT BY A STRANGER, BUT BY THE STEPDAD OF ONE OF MY GIRLFRIENDS, WHOSE HOUSE WE WERE HAVING A sl**pOVER WITH, I WAS ABOUT 18 AT THE TIME, READY TO GRAD HIGH SCHOOL, AND GAVE NO THOUGHT TO EVEN EVER BEING CAUGHT MAST... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 2138  |  
94%
  |  13

First Times a Charm... My 1st love.

It was late August 2002. I was 21, and looking for a room to rent getting out of Baltimore to broaden my horizons. I wanted to start fresh with maybe some new friends, and seek new ambitions. My folks had split up, after a nasty divorce, so I had to get my head clear. I was an only c***d, and was very close to them except now I seemed to be estranged to the both of them. So, after picking up the Sun paper, I browsed the "shared housing" section. I called, and talked to a few people. Some for one reason or another didn't really fit my fancy. One woman I talked to had a whole laundry lis... Continue»
Posted by gurlinpumps 1 month ago  |  Categories: First Time, Mature, Shemales  |  Views: 3310  |  
94%
  |  6

Pia's T-girl adventure

I met Pia a couple of years ago when I was out with friends at a transgendered night club in London. Originally she was born in Finland but she has lived in London now for several years. Her looks are typically Scandinavian with platinum blonde hair and a beautiful, friendly smile. Although I had never had sex with her or seen her naked, I could tell that she has a lovely, shapely body. After chatting with her I discovered that she is bisexual and really only interested in meeting other woman or couples after enduring, what she calls, too much ‘vanilla sex’ with straight men. I also discovered... Continue»
Posted by lightwave40 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1606  |  
94%
  |  7

Made my hubby crossdress and get fucked by bbc!

Finally convinced me husband to stop watching me take big cocks and to put on a pair of heels and to get fucked while its my turn to watch him!

ive always loved being a cuckold wife, meeting new people, having fun wherever it happens to be at, it really improved our marriage, finally i took it to the next step.

i spend alot of time at nights checking out mostly pics on xhamster and few videos. ive always been turned on by crossdressers, cumshots, and a few others fetishes im into. this time i finally got to see a live crossdresser fucked, my cuckold husband!

so we arranged to meet a f... Continue»
Posted by discreet4rmlanc 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 5833  |  
94%
  |  20

A Very Good Night

I sat on the edge of the bed waiting for his text. He told me he would let me know when he pulled into the parking lot so I could be ready. He wanted it to be completely anonymous. The room was mostly dark and I was to be blindfolded and on all fours, ass up and at the edge of the bed ready to be fucked. I LOVE anonymous sex. Sex clubs, video stores, cruising spots. The act of taking an unknown cock in my hungry cunt had my heart racing. I had no idea how old he is, age, or his race. All I knew about him as that he loved to fuck tranny pussy and fill it with cum.

My phone went off and I ope... Continue»
Posted by kbking70 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1795  |  
94%
  |  8

Back Seat Booty

“My head hurts,” Charmaine Epps informed her date. “I think I’m ready to go home.”
“Yeah. That’s cool,” Steve Parker replied trying to hide his disappointment.

The six-foot-four-inch, two-hundred-fifteen-pound athletically built man had been enjoying the holiday party thrown by Charmaine’s employer. She was a former beauty queen with honey colored skin. This was the fourth date in as many weeks and the divorced mother of two was completely up front with him about her ‘three month monogamy’ rule. It was her philosophy to only give up the pussy after three months in a committed exclusive rel... Continue»
Posted by faggyboi 9 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 3474  |  
94%
  |  4

SUCKING COCK

The first time I sucked cock, I knew I was was addicted. I grasped his semi-hard cock in my hand. So hot and velvety soft skin. I could feel his heartbeat with my fingertips. I leaned in and giddy with excitement, I placed my tougne on the tip of his cock. The taste was like a d**g, my pulsed raced and I had to get it into my mouth. To feel his reaction, the way his cock got instantly completely hard. I knew instantly that I owned him, if only as long as I was sucking his cock, He was mine. The way his head seemed to fit on my toungr like it was always meant yo be there. I wanted to see how m... Continue»
Posted by jennifersusan 3 years ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 3375  |  
94%
  |  16

Cum hungry paper boy sissy

Cum hungry paper boy sissy



When I was thirteen our next door neighbor Pat offered me a summer job
helping him deliver papers and magazines. I quickly said yes and my
foster parents agreed. I liked Pat a lot as he always patted my ass when
Vance and Liz were doing something when he came over for dinner as he
smiled and winked. I loved the way it felt and smiled back as my cock got
hard.

I was light build and kept my long blonde hair in a pony tail and always
wore cut off jean shorts. I had also been jerking off and eating my
creamy delicious cum loads for over a year as I loved... Continue»
Posted by jayymie 2 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 6235  |  
94%
  |  4

Quick Fuck

I was working the counter at the burger joint, as i asked the next customer for their order I was startled to her a distant but familiar voice. 'I don't think what I want is on the menu.' I looked up with a jolt and standing dare as sex as she/he wants to be is, blonde hair blues eyes, Bambi,'

I looked frantically around my fellow co-workers were busy in the back and no other customers were at the register. I whispered quietly 'Bambi, I need this job, what ever you want, I get off at four meet me across the street.' 'Silly boy,' Bambi started, 'I want a burger and fries.' I placed her/h... Continue»
Posted by d4david 2 years ago  |  Categories: Shemales  |  Views: 1938  |  
94%
  |  4

June 3rd 2011, Dream Come True!

Friday June 3rd, 2011, I went out to a local bar. Not crossdressed, just the man in me. I am normal on the outside, beer drinker, hell raiser, party kinda of guy. So anyways, im sittin at the bar with my buddy sam, drinking coors light and shots of cuervo. well sam had to cut out early cause his wife was getting bitchy, so he left and i stayed and got d***k. at the other end of the bar i was eyeing this gorgous red head, id say, 5'3, slim body nice tits, drinkin beer, which is a turn on for me when women drink beer!! And she noticed i was lookin at her. So i got up with my beer and went outsid... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  Views: 844  |  
94%
  |  5

The "Ball" Game

Dad and myself had not had any "Barb" time in quite awhile. We never played when mom was around and needed some time together. A "boys" trip to KC would be just what we needed!

Soon as dad got home from work we headed for KC. He had put my stuff in the trunk and when got a ways from home he got it out. I jumped in the back seat to see what he had brought along for me to wear(he always chose my attire for me). Several very pretty dresses and a couple skirts, one was very short, and some blouses. An eight garter waist cincher and the most beautiful FF nylons! Black, coffee, suntan, all with s... Continue»
Posted by Barb51 2 years ago  |  Categories: Anal, Mature, Shemales  |  Views: 1204  |  
94%
  |  10

tranvestite in trouble part 2

How could i have been so stupid?

Here i was, trapped by a guy twice my size and weight, dressed as a sexy secretary, just as he'd asked me, kneeling on this filthy floor, with his solid 8" cock buried deep in my mouth, gagging me.

Andrew was clearly loving acting out his scenario, with his submissive tranny slut, his eyes were bulging from his head. his hips were pumping, back and forth, litterally fucking my mouth, fucking my face.

i could taste the pre cum oozing from him, so much, i'd had to swallow loads, but i could feel it running down my chin, onto my chest. Still.....he couldn... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 773  |  
94%
  |  6

THE DUNGON!

I walked into the Dungon wearing a black leather bustier that revield my breasts,black leather thigh high boots, and carring a riding crop, my slave was laying on the table tied naked and in the spread eagle posistion facing up, her breasts were ample and niplles semi erect, her shaved pussy very inviting, in her mouth a red gagball,she looked scared, her eyes wide open as she wreathed and wiggled unable to escape, she had disobeyed her mistress and she knew it was time for her punnishment,i walked slowly to her, bent down and looked into her eyes, they were filled with terror for she did not ... Continue»
Posted by kendracd 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 442  |  
94%
  |  1

The Bondage Whore, Chapter 8

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 8 - The Regulars

One of Rachel's most sadistic regular customers was a man she nicknamed "Saddam". Saddam was, Rachel estimated, an arab man in his forties that without a doubt, got off on making Rachel suffer. Saddam tended to visit on slow nights, when Jimmy and Joe would allow him maximum time with Rachel, which meant he was a Sunday night regular.

On this particularly slow Sunday night, locked in position, anticipating another unwanted visit from Saddam, Rachel remembered back to his very first visit: on that ... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 832  |  
94%
  |  8

came to play

I spent my c***dhood at my grandmas house while I was growing up, there was several k**s in the neighborhood... I basically grew up in the ghetto side of town. I knew more black people than white. I went to a school where there was always atleast a fight a day, so I kept to myself for the most part.. when I was 17 I was asked to stay late after school in hopes to help ms. Joliet my favorite teacher clean her room and set up for the next day, atleast that's what I was told. My final class of the day is gym so I was going to shower before I went to joliet's room, when I stepped out of the showe... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 2905  |  
94%
  |  5

My first stranger.

I practiced dressing hundreds of times before I went out in public. I went out in public dozens of times before I tried to pick up someone. I wasn't attracted to gay men - I liked men who appreciated me for my feminine side, so because of that I only wanted to be with a straight guy. Obviously this proves difficult, since straight guys don't want their girl to have a cock. I have found that usually they are so turned on by the time they find you have a cock that they don't care.

This is the first time that happened to me.

I finally decided I was ready to try to pick up on a guy.
... Continue»
Posted by hotchickinchitown 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1963  |  
94%
  |  6