Free Shemale Stories

She-Male Pimp Daddy

I’ve been working the streets for a long time and I know all the ends and outs of the flesh market. I have six she-males that work for me and I get 50% of everything they make plus all the sex I want, any time I want it. I make them work seven days a week rain or shine. I buy their clothes an... read more

shemale lover July 18, 2013 90%

My way to shemale sex

It all started with porn. 10 years ago, i was watching porn on my bed, jerking off watching a girl sucking a big cock. I looked at my cock and started wondering what that beautiful peace of meat tasted like. After a few moments of hesitation, my curiosity took over and i put my back against the wall... read more

andre_xp_8 July 24, 2018 87%

Caught Before My Brother and Friends Could Use Me.

Caught Before My Brother and Friends Could Use Me. By TVTrinity As a boy, I was fascinated by the petite little girl I saw in the mirror when crossdressed. When I got caught dressing by my uncle. I experienced the effect it had on men firsthand. He looked at me the way a man looks at a girl. I... read more

Tvtrinity April 7, 2021 92%

Outdoor Tranny Sluts Lust

I wake up really early one morning with my cock throbbing hard under the sheets. I got a white camisole on. Out of bed i go with a desire to vouyer and masturbate somewhere around my home. I'm home alone so i head out to my garden with my cock bouncing up, down & dripping cum. It's about 5am... read more

Tracy Bel February 14, 2023 80%

A Grand Awakening

By the time I completed my military service and returned home for civilian life, most of my friends from high school had completed university degrees and had relocated to other cities for lucrative career opportunities. I was absolutely delighted when I went to a popular disco club and found one of ... read more

DRILLMASTER October 25, 2023 100%

My first ass fuck! From Anita

Hi! My name is Anita, I live my life always wearing lace and satin. I have always loved the way those materials feel against my soft skin. I have long red hair and bright green eyes. My friends used to call me Charles but about 12 years ago I had this epiphany of feeling that being a woman was just ... read more

shemale lover May 23, 2014 94%

From Gloryhole Peegasm to Shemale

I was in a porn video booth. I young guy stepped into the next one. I was already jerking my small dick, but he didn't even pull his pants down. He asked me if I wanted my dick sucked. Actually I think he said something like, "hey, let me suck your dick." Recently I had let some weird, ... read more

shemale lover August 18, 2011 38%

First Time With Shemale

For as long as I can remember, I've preferred my chicks with dicks. There's something about a sexy babe with perfect makeup and hair and a cock that just turns me on. Maybe that makes me a pervert - I don't care! I remember I was just out of high school, 18, the first time I made it with a tranny. S... read more

shemale lover August 26, 2011 100%

The Ultimate Cock Ball Torture

I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... read more

shemale lover November 12, 2011 60%

She took her licks getting there,now she loves to do the licking

I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale than a... read more

shemale lover November 15, 2011 100%

My shemale GF Part 3

Christy and I are on the couch, we had just woke up, I have a butt plug in and slept with it in cause she was going to fuck me today. She has a Pink G-string on and a Pink bra with her G-string pushed to the side for her cock. Me I'm wearing Metal Mulisha boxers and a Tyler, the creator T-shirt on, ... read more

shemale lover July 9, 2012 33%

Blushing Bride Chapter 4

Chapter Four: The Hen Party I've already told you all about the night a couple of days before my wedding, the night of my stag party, the night where I got to live out all my fantasies and play the blushing bride, dressing in my soon to be wife Gina's gorgeous white wedding dress and lingerie and... read more

shemale lover July 21, 2012 100%

Cow Girl`s got something hard in her jeans

Last Friday night me and the guys from work stopped to have a couple of beers. which of course turned out to be a whole lot more. boy was i going to be in trouble when i got home. but when i got home it was all quite, too quite. then i saw the note. "You son of a bitch you knew we had that dinn... read more

shemale lover July 21, 2012 100%

A Warrior's Tail

It was Limdour's first time in the aspect shrines and he was nervous. He was here to finally become the warrior he promised his father he would be on his death bed. He walked through the hall, It's huge walls swallowed the sound of his footsteps as he tried to decide which warrior aspect he would... read more

shemale lover July 23, 2012 66%

In Love with a Shemale

I was out one night in a busy club and I couldn't help to notice this one girl staring at me constantly. She was incredible wearing a tight little skirt showing off her long legs with an amazing smile and a very cute face. I planned my move and went to the bar when she did and she started talki... read more

curiousshemalelover November 29, 2014 94%

Born to suck

I’m a straight guy who watches to much porn and when I hit my thirty’s regular porn was getting boring. while searching the web I stumbled across some tranny porn, now I always loved blowjob porn it was my favourite but now watching a big dicked tranny getting her cock sucked is my favourite and I ... read more

Beesknees March 2, 2018 100%

Trance club

It was the worst day in my life. My girlfriend Ally and I had been quarreling and rowing for several weeks, we were on the verge of breaking up. I just wanted her to be happy. I lived my life for her. I guess I stood no chance to make her smile at me again. We broke up. Ally said everything was chan... read more

shemale lover May 25, 2014 80%

A night to remember

Josie wasn't a girl a man would turn his head for if he saw her on the streets. She was a small, petite girl, her breasts barely an B cup. She was wearing her light brown hair in an inconspicuous short cut and the thick glasses she needed for being able to see anything in her surrounding, didn'... read more

shemale lover December 11, 2011 100%

Black Mafia - 1975

Bucky Collins downed the last of his whiskey and collected his chips to cash in. His cousin, Don Lee, who served as his driver and bodyguard escorted the Black Mafia attorney-slash-lieutenant to front door. His leisure trip to the Big Apple had been fruitful. Tonight, his winnings totaled $2,300.00.... read more

shemale lover July 1, 2012 50%

1st time with Thai shemale

So after months of crosssdressing , camming and phone sex i finally decided to have a meet. I found a lovely Thai shemale on birchplace and went to see her in London. She was gorgeous and put me at ease straight away. After a few minutes of massage she started licking and sucking my nipples, then as... read more

Nutcracker29 April 9, 2013 100%