Shemales Porn Stories
Page 14

First time

Continuing with my life stories, this recounts my very first man.

I was still a teenager and still at school. Those were mere technicalities and certainly had no bearing on my libido and overwhelming desire to experience a man for the first time.

I had heard through various sources and local papers that there was an increasing issue with gay men cruising in a certain park in my town. I had to find out more. One day I told my parents that I was staying late at school to catch up on some homework. This gave me the opportunity to check this park out, plan my strategy and eye the talent t... Continue»
Posted by TerriSlut 1 year ago  |  Categories: Anal, Shemales  |  
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Getting back at the bully

Hi, my name's Rose Marie, and though you may have already guessed, I'm a hermaphrodite. Don't let that fool you though; I'm not some wimpy little girl. I'll admit I can get a little rough, but I can be laid back too. I just turned 17, and just like a lot of other people, the good 'ol hormones are ragin, but I do a lot better job of hiding them from most people, when I want to that is....

I'll be a junior in high school this year, I’ve had a mostly quiet summer. I have dark red hair, I put some white streaks in it with one of those hair styling kits, I’m not trying to be the center of attent... Continue»
Posted by wheels1825 3 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  
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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the room. Like I said there were lots of beautiful ladys there but one caught my eye. She was not too ta... Continue»
Posted by wildbill975 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Morning Surprise

Not my story

I walked into the hotel bar after the closing reception of my week- long conference ended and she was sitting there. Absolutely gorgeous. Blonde, about 30, maybe 5' 4", probably 110# and a 34C. I was stunned, but with nothing to lose I wandered up and took the chair next to her. She acknowledged me as I ordered a drink. We chatted and I noticed she turned towards me opening her legs slightly. Her body language told me I had made a good decision to sit by her.

We enjoyed several drinks as our inhibitions dropped. We chatted and laughed. I realized it was time to make my move,... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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What Happens In Vegas! (copy, I wish i was able to

Hi there! I'm Ann. I would like to share a true lifestyle story with you that has been permanently embedded in my memory and makes me cum every time I think of it!
Let me begin by giving you a bit of background about my husband, (Tony), and my swinging history. Tony and I are a happily married couple living in Las Vegas and have been in the lifestyle for over 15 years now. We have certainly enjoyed our adventures over the years and have brought every fantasy we have had to reality. Living in Las Vegas, we enjoy the fact that we have a constant source of play mates in the large number of tour... Continue»
Posted by pervert76 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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glory hole dressing

I had the night off and decided to go down the block (WeHo) to a local book/video store. I got dressed into my sexiest short skirt and slinkey top (with my latex boobs) wig,makeup and "cleaned up" below.

I walked the the store and a few jaws dropped as I slowley looked around. I picked out a small butt plug ,some lube and went to the counter and paid for my items...and asked for 5 dollars in quarters,winked at the cashier then strutted off to a booth in the back.

At first I just wanted to watch some movies,but I got so hot I placed a drop of lube on the plug and eased it in slow...POP...... Continue»
Posted by sodeep2 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Moms friend Vanessa


My mom had a best friend named Vanessa. She was more like an aunt

and always was around. She had big tits, a thin waist, a fat ass,

and nice big legs. She would always wear short skirts or short

summer dresses that showed her wonderful legs. One time my mother

was at work and Vanessa was watching me until she got home. I was about

8 at the time watching tv in my spiderman underwear laying on the floor.

Vanessa was sitting on the sofa reading a magazine. She crossed her legs

just as I had looked up. What I saw made me very curious to say the least.

I saw what look... Continue»
Posted by moms_sissy 2 years ago  |  Categories: Mature, Shemales, Taboo  |  
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The Fam...CH 1

Key Players;

Father - Dave

Mother - Brenda

Male sibling- Stevie

Female sibling - Alicia

Neighbor mother - Lakeysha "candy"

Neighbor twins - Keke & Tricia






"Fuck daddy...that was fucking hot" Stevie said while scooping up his f@+=€r's cum from the side of his face with his finger. Stevie was kneeling by the side of the bed with Dave's quickly deflating 9 inch black cock only inches from his face. Stevie is a young tw€|>e year old b•y that has recently been diagnosed with gender identity disorder. He is the youngest product of an interracial marriage between Da... Continue»
Posted by TS_LoverBoy 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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My Crossdressing Teen Neighbor

There is a duplex across the street, the kind with an ill arranged addition that sprouts out of the top and basically looks like shit. It's a slum lord house, geared toward your average broke ass people. You'd think I was complaining, but I am actually quite glad such a place is right in plain view.
There is a young couple that lives there, hipster punk types. The dude is nice enough but a little awkward, but the blonde chick is a little flat chested blonde hottie with piercings and pastel highlights and a plus size ass. Needless to say I'd like to breed her good. Someone looks to ha... Continue»
Posted by cumquarts 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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FIRST TIME WHORIN'

FIRST TIME WHORIN'

I was just 18 when I went out whorin' for the first time. It was something I had an overwhelming urge to do after fantasising it countless times. I had been painting up and dressing since I was 13 and my 18 month older b*****r had been fucking me regularly since I was seven until he went away in the Army when I was 16, plus I had been shoving all types of objects in my pussy almost daily. My desire to have my pussy ravaged was insatiable. I used cucumbers and even a slender long Japanese eggplant about two inches in diameter, fantasizing it was a BBC. I reveled as I watc... Continue»
Posted by tvsllutmichelle 10 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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A Slut Is Born

There I was, one week before the end of high school. Going to college in the fall. Nice car, good f****y, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat?

It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me... Continue»
Posted by MacDaddy714 3 years ago  |  Categories: Anal, Shemales  |  
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my transsexual girlfriend

.........I used to date a transsexual woman named lexxi for about a year. I loved her cock so much it was amazing. It was 9 inches with a 6 inch girth and mine was 8 inches five and a half inch girth. (we measured both of our cocks together). Every morning she would wake up with a pulsating hard dick and i would suck it relgiously. She would wear boxer briefs to sl**p and sometimes she wouldn't shower if she had a long day, so she still had a slight musk between her thigh and balls. She was a manager at a transgender strip club so i would meet tons of beautiful girls that worked there. one day... Continue»
Posted by michneo 1 year ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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White Sissies on Black Dicks

Sunni inhaled the marijuana, held it in for a few moments, and then released a puff of smoke in the air. The effeminate white man with a platinum blonde Mohawk pressed the number two button on his phone to listen to the message. He heard a deep-voiced Black man say he needed his dick sucked and would love to fuck some ass. Sunni replied saying they should do a live conference. Moments later they were connected.

“Hello,” said the baritone.
“Hi there,” beamed Sunni. “How are you?”
“I’m good. You sound happy as shit.”
“Of course. I’m talking to you.”
“That’s wassup,” he laughed. “You said ... Continue»
Posted by faggyboi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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My Bi-Sexual Junior Year

In 1983, my roommate during my junior year in college was gay. Ronnie had come out to me and a few of our friends at the beginning of the year. At first, it was a bit awkward, partially because I was afraid what people would think about me. Although I had one day of torrid gay sex while in high school, I was straight. Girls turned me on. I loved watching them on campus. Guys did nothing for me.
Ronny would tell me how I’d be shocked if I knew who was gay. He claimed a number of guys that I knew were still closeted. I guessed correctly on a few of them and was way off on others. Ronny... Continue»
Posted by StanStutz 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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Santa Baby

Santa Baby

Nikkie Silk

It was the last Friday night before Christmas, and the pub was packed
with office workers intent on celebrating the Christmas spirit by
getting as d***k as they could manage. Slade were belting out ‘Merry
Xmas Everybody’ over the speakers and the whole pub was raucously
joining in with the chorus. People were kissing under pieces of plastic
mistletoe and more than one office romance would begin, and probably
end, that evening.

The group that had grabbed a table to the side of the bar were typical
of the customers in the pub. Working at one of the companie... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: Shemales  |  
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The Triple X cocktail - Wife Shares Shemale With H

"Where are you?" Tara asked in a high pitched voice as if she was either excited or freaked out. "I'm at the boutique" I replied. "Ok I am coming by, something very important. I am so freaked out now and I will tell you all about it when I meet you. Will be there in half an hour see you." She hung up.

The phone call made me really nervous.I had reasons to get nervous if not get a nervous break down. Tara and her husband owns a few restaurants in different cities across the States. I have known Tara since 6 months now since she busted me from one of the restrooms of her restaurants. Well wh... Continue»
Posted by Copious 4 years ago  |  Categories: Group Sex, Lesbian Sex, Shemales  |  
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Drama queen

The Drama Queen

My name is Christopher Robin; I did get a lot of ribbing about it. A well known did not do me any favours; it was friday last working day of the month also start of half term. I was just looking at my payslip. I had enough for my expenses plus a little left over for some luxuries. I tried to be careful with money although being an only offspring of my deceased parents. They were killed by a d***k driver going through a red light at speed. I had a substantive payout from his insurance company, and he would not need insurance for a very long time with prison term of 2 life sen... Continue»
Posted by hottvcarole 1 year ago  |  Categories: Group Sex, Shemales  |  
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My girlie fantasy part 1

On a Halloween night I dress up in my sexy devil costume with my wig & some makeup & go to a local bar sitting alone. A guy ends up sitting next to me & flirts a little before I ask if he wants to go to the restroom with me to which he eagerly agrees. After getting in a stall we makeout for a little as he fondles my small breasts before I go down on my knees & pull his average size snake out & get to work. Shortly after starting he rewards me with my first taste & runs out embarrassed at how quick he finished leaving me wanting more. I sit back down at the bar & eventually another guy takes a ... Continue»
Posted by multiplierx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My Life as a Shemale Part1

In this story, many will find what happened to me socially unacceptable. But since this has happened to me, I get to tell it and if you like, listen.

I was very young when I found myself on the streets and it seems long ago that some things I do not remember but its the important stuff that I do. And yes, like so many other stories start, here is how I looked. 4 foot nothing, skinny, long blond hair and even then had more angelic features then not. I do believe that now, that I was a woman even then but as nature would have it she would have a sense of humor and endowed me with a large peni... Continue»
Posted by gigi750 1 year ago  |  Categories: Hardcore, Shemales, Taboo  |  
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My First Tranny

Cheryl had really opened my desires to fuck. She was, and is totally uninhibited, and a total sex machine, doing whatever she desires at the moment. When I felt my cock enter her throat the first time, and felt her tongue slide up my cock to the balls, and she sucked the cum right out like my urethra was a straw, I knew I had a keeper. I was hoping I was able to satisfy her, and hoping she would keep me around, this was really the best sex ever. I would get no argument from my wife, she was getting all the cock, and later I would discover she was getting pussy also, she had the best of it ... Continue»
Posted by fishkiller 2 months ago  |  Categories: Fetish, Mature, Shemales  |  
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