Free Shemale Stories

After Church

I was just horny. All of the time. I just wanted to fuck someone in the worst way. 18 years old, never had a date. Too skinny, too weird. I wore my hair long, not a very hairy body, not very athletic. Just a skinny kid who didn't get any attention. Lot of church girls in the bible belt but they were... read more

shemale lover August 19, 2012 100%

Meeting Hynden Walch

Two months had passed since I had fucked Grey deLisle and now I was going to another convention, where Tara Strong, another hot girl I had stuck my she-dick into, wanted to introduce me to somebody else, and we both knew that the sole purpose of the meeting was so that I would end up having sex with... read more

shemale lover September 26, 2012 50%

The Coach's Chance Encounter

Eddy McCants rolled the rack of basketballs back into the athletic storage room at Liddell County High School. After coaching the varsity boys to the final four in the state tournament last season, he had a good feeling that his team would make it at least as far this time around because he had thre... read more

shemale lover October 26, 2012 100%

The Meeting

He could not believe that he was finally going to see her after all these years. Since his divorce, she had been all he could think of. He fantasized every day how it would be to see her again, make love to her again, and now the day had finally arrived. He could barely sit still. He had decided... read more

shemale lover December 21, 2012 100%

Letter To Max, My Online Friend

You remember that time I'd landed in LA and found my way to your house? Ha! The look on your face. I wasn't sure at first if you'd be angry with me, which would have been understandable, given that I'd sprung out your PC and onto your front garden. It was worth though wasn't it, lovely Max? I wa... read more

shemale lover January 10, 2013 100%

The Dinner Party

The clock above the kitchen sink read 7:48 when I heard the metallic snap of Aya's key unlocking the front door. I opened the oven door and was rewarded with a blast of steam that smelled like a lazy August afternoon, all rich garden spices and earthy head. Inside was a boxy cookie sheet covered in ... read more

shemale lover January 11, 2013 91%

The Mind Flip

IT was a weekend like any other, in the city in the north of England. Rain poured in sheets down the basement windows of the flat I shared with my friend Joe, breaking up the shapes of the buildings on the opposite side of the road like a kaleidoscope, and I sat indoors, slouched in front of the com... read more

shemale lover January 17, 2013 100%

Intro to a Dream Made Real

Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much a... read more

shemale lover January 22, 2013 75%

Riding Home With Strangers

The music was running, the booze was flowing through my veins and I was not ready to leave just yet. My ride had to leave early, because my driver's hours were up, and I didn't want to force him. I didn't think I would be having so much fun before I came here. I met a group down here who li... read more

shemale lover January 30, 2013 96%

How I Met Alyssa

I groaned as the sun was shining onto my face. I turned around so I could get some more sleep, but I saw it was 9:22 am and I decided it was time to get up. I got out of bed and went to the bathroom of my little apartment to freshen up a bit. I looked at myself in the mirror and saw a 20 year o... read more

shemale lover February 12, 2013 97%

Pygmalion

Some of the coed students in Professor Higgins' Sculpture 101 class regard him as a sexist or, as Amanda Blake describes him, as if she were living back in the sixties, "a male sexist pig." He does have an eye for the ladies, I'll grant you that (he's ogled me enough times!), but what man ... read more

shemale lover February 22, 2013 100%

A "Girl" for Kelly

Kelly was sort of a loner throughout her life. She had very few friends throughout high school and college, and if she weren't around them, she would spend her time alone. Her love life was just the same. She did have a few boyfriends, and only ever managed to get one to have sex with her. It wasn't... read more

shemale lover March 27, 2013 100%

This that go Bump in the Night

It was the ideal time. My wife was away for the weekend and a long weekend at that. So on the way home from work, I stocked up. Some pantyhose, lips gloss, stockings and fake nails. I raced home, turned off the phone and ran a warm bath. Soon I was soaking in the bath with candles and light music. A... read more

shemale lover March 28, 2013 77%

Penitentiary Pussy-Butt Boy

Hi: My name is Bobbie. Would you like me to tell you how I became a Penitentiary Pussy-Butt-Boy? Well, it all started with a robbery gone wrong. I wasn’t even in the bank when the guard got shot and I still got almost as much time as the others. So, not long after the trial I was sent to the sta... read more

NaughtyBobbie April 11, 2014 94%

Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river. It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site. I had been chattin... read more

shemale lover December 3, 2014 90%

My first big cock

So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective. I tried an online dating site ... read more

Cbosh40s March 31, 2015 91%

THE WEATHERGIRL BY B-MAN

PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... read more

bennyx709 July 29, 2015 85%

The Masseuse

I book a massage at an upscale private place in downtown Toronto. I arrive and the masseuse looks gorgeous, dressed casually, in a tank top and short cut off jean shorts. Her breasts barely being restrained under the bra-less top. Her stomach exposed, flat, toned, with hips exposed just above her ti... read more

Basil5503 September 18, 2016 94%

Third times the charm!

After my first 2 times with a ts it basically just became an urge that I had to have a need I had to satisfy! Just like regular sex the more I thought about it the more I wanted it. I finally asked Liz if she knew anymore from around where we were. Luckily for me she did and set me up with her frie... read more

Duke04 April 4, 2017 89%

My Vancouver get a way....

I was in a different city, where no one knows me, free. My boi hole started to tingle as soon as I realized I could finally prowl the gay scene of a big city, with two and a half days of zero commitments I had little time to waste. I went to the hotel room in Abbotsford and showered, shaved and trie... read more

badbadboi667 December 14, 2020 91%