Free Shemale Stories

Crossdresser Lovemaking

Oh Daddy, I'm your little princess! Your wife is out taking your kids to a sleep-over at a friend's house across town and we're in your bedroom. I long for you to see me with bursting lust, and I take off my coat to reveal myself wearing a white tutu with bra, panties, stockings and h... read more

CD Lilee May 20, 2014 80%

Anal Therapy

My new psychiatrist wasn't at all what I expected. When I saw her name in the phone book, I pictured a dowdy old lady wearing a long, gray skirt and flat-soled shoes. What else could Dr. Edith Doss look like? I got my answer when a tall, leggy redhead stepped into the waiting room. A tight, black... read more

shemale lover November 24, 2012 78%

New Girl in Town

Margo sat next to me in the coffee shop late that Saturday afternoon. His real name was Mark, but he was one of the loveliest Drag Queens in New York City. I had been dressing secretly at home in my mother’s and sister’s clothes for just over three years, but at 18 years old, I had never... read more

shemale lover June 4, 2019 94%

A Shemale Vacation Part 2

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragem... read more

shemale lover September 5, 2011 100%

Tara's Adventures

Part 1 I had met them on line. Marla 1st then her owner Mistress Olivia. We chatted for well over a year and had met for drinks. They knew of my submissive fem side and we had planned meetings on several occasions but things always developed that upset them. Then a period of time developed whe... read more

shemale lover August 11, 2012 0%

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%

Caught and Submission Chapter 3

It was several weeks after being made to service all of our friends through a glory hole at a party. Alex kept me busy sucking his cock whenever he wanted it, usually it was early in the morning before he left for class. Alex would wake me up by placing his hard cock on my face, I was resigned to my... read more

shemale lover June 5, 2012 100%

Barbie Jo Adventures Part 3

Saturday Afternoon The sound is ringing in my ears as I drag myself out of a deep sleep. I look over at my clock and realize it's not the right time for my alarm. As I come more to life, I pick up my phone. "Hey gorgeous, how you feeling?" Booms a voice through the receiver, making my h... read more

shemale lover February 18, 2012 100%

Becoming wife of competitor feminized by secretary

I am Siddharth Mittal, running my own Company with USD 100 Million of Business. Everything is going on well and I am excelling in my business. I have a secretary named Sonia. She is a smart and beautiful girl with 36-32-36 size. She knows how to get her work done. She wears simple clothes and is dec... read more

shemale lover May 17, 2012 40%

Chrissie and the Professor

Possibly the after hours engagement with an English Literature professor at college may have been the thing that convinced me that older men might be more to my liking. It was during my Junior year at the university when we were discussing the poetry of Arthur Rimbaud, the French poet, that I beca... read more

shemale lover July 25, 2012 100%

First Cross-dressings Loosing Anal Virginity

It happened after a month of me blowing that guy twice...I mean I was so damn excited and was craving for his cock....I was blowing him every weekend in his car after the school...his cock was almost 7 inches and was so thick and that I like so so much the gagging he was giving everytime, that chock... read more

Trapbomb1 July 29, 2022 100%

1st time anal

JOURNAL ENTRY 2 MIN READ My 1st anal As with most of adventures in the early days its starts with fun night at the bars. Getting a good buzz on and putting an ad on Craigslist. (Rip🙁). I was especially worked up and really wanted some cock. I had been having some fun over the last Few months since... read more

Rachelcdfun May 8, 2024 100%

You Just Never Know... ya know?

I was out on the road, On my way to Montreal at the end of my stint behind the wheel. I pulled into a roadside rest area, or lay-by... or in this case a 'pickle park', a cruising area for local and tranient gay and bi-men looking for a quick NSA hook-up. Hell, so was I. I was all nice and clean f... read more

shemale lover October 3, 2014 75%

Hits, Misses: G

Ok, what follows are some accounts of hookups and almost hookups I've had with transwomen in the late 2000s, early 2010s. Some I think about a lot. Others I've forgotten completely and am attempting to interrogate my memories. Things have changed a lot in the culture, mostly for the better. Visibili... read more

bybaking February 6, 2024 100%

Jacqui

John and his wife had gone to a party at the home of Barbara, one of their friends. Barbara was tall and statuesque. A very striking divorcee who gave every indication of being eager for sexual activity. John had met her before his marriage at a time when his finance was living in another city.... read more

shemale lover November 5, 2011 80%

Flowers in the Heart

Chapter 1 "Hey Scott, Fauna kind of likes you," Jenna said, snickering. "Hey Jenna, it hard to hear yourself over that echo?" Scott said as he caught the football, and then heaved it back to Ronnie. "Huh?" Jenna asked, puzzled. "Yeah, your head up your ... read more

shemale lover November 11, 2012 75%

How My Wife Became a Swinger

Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin. For the fi... read more

Loveto October 12, 2011 100%

Neighborhood Restaurant Surprise - Kimi

I - The Meeting In the neighborhood restaurant I frequented weeknights after work, I had developed a friendly relationship with several of the college kids who worked as servers. Always having been attracted to the most feminine and petite of girls, dark, almond shaped eyes being a super plus, I ... read more

shemale lover April 11, 2012 100%

My first shemale sex

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our ... read more

shemale lover August 14, 2013 90%

MY FIRST SEX WITH SHEMALE

This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous durin... read more

shemale lover December 1, 2013 88%