Free Shemale Stories

Anal Queen

Amanda fell to her knees in the darkened theater and slowly unzipped my pants. My cock throbbed. As she pulled down my underwear, I felt my manhood spring forth. Amanda took the whole sausage into her warm, soft mouth. I could barely see her face in the darkness, but I could feel her between my l... read more

shemale lover November 24, 2012 66%

First Time: How I Love Cock

The first time I ever sucked a dick was when I was around 12 years old. I was at a sleep over with a friend. We were camped out in his backyard in a tent and he started things out tentatively by asking about my luck with the ladies, which was non-existent. Then he suggested that since neither of us ... read more

wickeddogg December 11, 2019 83%

Ellen's Candy

Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... read more

shemale lover April 2, 2012 100%

Being Curious Has Big Rewards

I was brought up believing that men were not supposed to have sex together. The thought of this taboo type of sex was always made me curious. When I was 18 or 19, I visited an adult book store, just because I was horny and wanted to get a magazine that showed people getting fucked so I would have... read more

shemale lover April 26, 2012 100%

The Bet

I've always been quite the ladies man. Eversince high school I've always had all the pussy I could ever want. Given a little time I could fuck any girl I wanted. Until I met Irene. Irene was a tall brunette, long legs, full figure, and the most gorgeous eyes you ever saw. I met her at a social di... read more

shemale lover May 9, 2012 100%

Betrayed Chapter 1

She's having an affair. I couldn't ignore it any longer; the evidence was right there on my monitor that Wednesday afternoon. I had felt so... tawdry – a word I had thought I would never use – hiring the detective to follow her, follow up on my suspicions. It was as though I was betrayin... read more

shemale lover May 28, 2012 100%

Fantasy Cum to Life

Ryan and Alyssa were in the midst of wild make – out session on his living room couch. She was leaning over him, one hand on his chest, the other behind his head; both of his hands we placed firmly on her ass. Ryan actually had the conscious thought that he had probably not kissed anyone this ... read more

shemale lover May 30, 2012 100%

The Intimate Dinner Party

Susan and I were filled with anticipation as we arrived at Victoria’s house. We had been invited to what the written invite referred to as a “Sexy and Intimate Dinner Party”. Victoria was renowned for her unusual, and always different, dinner and cocktail parties. She certainly ... read more

shemale lover June 8, 2012 87%

Ellen's Candy

Sometimes I get in the mood to suck a dick but I’ve never considered myself gay. I’m @ the very least bisexual but I don’t like to limit myself to that either because I think it restricts my sexuality. I get turned on watching all types of sexual situations that you could think of;... read more

shemale lover June 23, 2012 100%

Nightclub Cum Slut

After splitting with my first boyfriend I went through a period of time I call my slut phase. I explored my sexuality in a massive way and did as much cock ass and pussy as I could. I thought that after I had been in a few relationships that my slut phase was over. I still had the odd one night stan... read more

shemale lover January 10, 2013 73%

Three In A Day

Clara felf especially slutty today. She briefly gazed at her long legs shimmered in the smooth, silky black stockings, and black patent leather pumps as she pressed the gas pedal of her car. Her olive skin and black wig were set off by the brightest shade of red lipstick she could find. Driving d... read more

iluvgurls November 12, 2018 80%

SUMMER VACATION by Spanky de Bautumn

In our house, it was a well-known secret that my mother kept her change in the top drawer of her dresser. The same drawer she kept her slips, chemises, panties, and all other satin, nylon, or lacy ladies undergarments. During the summer, my brother and I would run to that wondrous drawer when... read more

SpankydeBautumn January 22, 2021 84%

Alex and Jon

Alex was not beautiful, but had a sexy attractiveness that most could not help but take a second look. This was the case with Jon as he searched adult Friend-Finder ads for someone that would satisfy his desires and dreams of a companion. Alex, a transgendered Filipina girl, had the bronze skin colo... read more

Jon Paul September 21, 2022 88%

Darren's Girl?

I'm Darren. I live in downtown Memphis. I head the IT Department in one of the corporate buildings on Second St. I don't consider myself to be the most attractive guy in the world but I don't have any trouble with the ladies. You know, I work out four times a week and run everyday but Sunday. I'm ve... read more

shemale lover July 20, 2012 90%

50 Shades of A Bookseller

So, I finally got a "proper" job and managed to move out of my parent's house. It was a damn good job too, as my crossdressing was becoming increasingly difficult to keep secret. Numerous times my Mum would try to talk to me through my bedroom door, whilst also slowly creeping it open to ... read more

shemale lover August 14, 2012 85%

Why I’ll Never Go Sharking Again Chapter 3

If you've been following along, you'll know what I went through yesterday. A few days ago, I was a normal college student. Actually, a few days ago, I was a normal HETEROSEXUAL college student, but now I'm not sure what to make of myself. I share an apartment with my friend Jason and we're not gay, ... read more

shemale lover November 4, 2012 92%

Angel & Two More Men

The sex on Friday night and Saturday with Bob Marley Cliff was the best Angel had experienced up until that date, but it was only one of many fabulous carnal adventures in her life. Because of her beauty, her sexual prowess and her reputation as a woman who was free and open with her charms, she had... read more

shemale lover November 29, 2012 100%

Angel Chapter 10

The sex on Friday night and Saturday with Bob Marley Cliff was the best Angel had experienced up until that date, but it was only one of many fabulous carnal adventures in her life. Because of her beauty, her sexual prowess and her reputation as a woman who was free and open with her charms, she had... read more

shemale lover December 2, 2012 100%

My Girlfriend's Mother Has a Secret

A young man, 18, is caught spying on his girlfriends mother in her bedroom, and is taught a hard lesson. Characters: Tim, 18, Student; Susan, Tim's Girlfriend; and Julie, 44, Susan's Mother ;-). Julie sat at her dressing table, preparing for bed; she brushed her long dark, which was one of the pr... read more

shemale lover February 27, 2015 98%

Interracial Sissy Story

(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences... read more

shemale lover May 1, 2015 93%