Free Shemale Stories

The Greatest Lie Part 13

Does Life Imitate Art? I love technology, in spite of the stereotype about girls. Although I was a guy, at least outwardly, until a year ago, I think I was always inwardly a girl. According to the stereotype, we girls are supposed to be indifferent to anything more technical than the designer cov... read more

shemale lover January 20, 2012 0%

Annoying Roommate

My name is Mike I'm 24 years old right out of college entering the workforce as a entry level pharmacist. I'm about 6'2 about 180 but being so busy studying for the past few years my body is a bit soft. I always have been bad with women, I'm what you call the typical nerd/geek/loser. I live in a sma... read more

shemale lover December 15, 2012 100%

Lindsay: One of us

The first cock I ever sucked belonged to a girl named Lindsay. It was my senior year of college and I’d been accepted to an internship at a large radio station in Boston. My enthusiasm for the internship diminished considerably when I realized all I would be doing was monitoring the station&rs... read more

shemale lover February 15, 2012 100%

An Arse To Die For

I'd arrived in Honolulu in the early evening from Sydney and got a cab straight to my brother-in-law's apartment on Kuhio, which he'd lent me for a fortnight while he was up in Europe on business. It's in an ideal situation, a couple of blocks back from all the hotels and Waikiki Beach. I slept l... read more

shemale lover November 10, 2012 83%

Mandy Awakens Dave's Desires

We had been flirting across the bar for several weeks at this point. She was just so easy to talk to. Although she wasn't stunningly beautiful, she was quite attractive. Mandy is about 5'2" or so, 110 pounds. She has a light complexion to go with her strawberry blond hair, which she wear... read more

shemale lover January 10, 2012 80%

Lady Denisa's Gang Banged

The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... read more

shemale lover November 22, 2011 0%

7/11

His name was jason. he was just a workin class guy, not much in the way of looks, slightly longer hair than normal, somewhat athletic, and gifted with a 11 inch penis and good sized testicles.he would go out after work and survey the bars and theaters, goin to concerts or events and haveing fun. the... read more

shemale lover December 10, 2011 100%

A Perfect Pandemic: A Transsexual Transition in a Troubled Time

A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... read more

the greatest liar November 16, 2021 100%

Big Dick Alessia Visits Dallas

Alessia Hung Mature MILF travels to visit a Big Dicked Man and his Sexy Household If you like Transexuals, big cocks, bondage, BBWs, big clits, deep throat, fisting, 69, ass fucking, sounding, piercing, cum swallowing and big loads this story is for you. If not don't bother reading. If you fav... read more

darrell April 20, 2022 100%

Darla's Diary: Slutfest 1993

Vacation Day One At last!! Another fantastic two weeks of freedom...the freedom to do as I pleased and dress as I pleased because it was my VACATION TIME!!! This year was better than other years because it was the first time my wife and I had two weeks vacation each. Just like she does every othe... read more

shemale lover July 14, 2012 100%

Thai Holiday

On Friday afternoon I had the car go around to collect Krissy at her office, then my wife, Mei, from home, and then me at my office. The girls were both wearing light, summer dresses and looked beautiful! Unfortunately as I was coming from the office I was wearing a Suit (But as usual with Black Lac... read more

shemale lover February 5, 2012 0%

Career Shift

Receptions are not my favourite things in the world to attend. I don't mingle and 'rub elbows' like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one ... read more

shemale lover March 6, 2012 80%

Duel With the Devil, Chapter 20 of The Greatest Liar

Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... read more

the greatest liar July 19, 2023 33%

I will go back there!

Gotta thank our reader Amanda for this lovely ladyboy sex story. As an openly gay women I had heard so much about Katoeys in Thailand and that they were affectionate and prepared to do most things. I have to go to Bangkok on a marketing junket so decide to test the waters. The first bar I walked ... read more

shemale lover February 11, 2015 90%

TG girlfriend is my new neighbor

With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... read more

Jon Paul January 17, 2022 100%

TG Neighbor

With Christmas and New Year’s over, the weather here in Florida has become cooler, 45 degrees last night and it will be in the mid-sixties for the rest of the week. We live in a sub-division right off the waterway, very private. My neighbor usually comes down around Christmas and stays until tax ti... read more

Jon Paul April 22, 2022 100%

Bagging a Bitch with Balls

Watching porn has given me a lot of ideas concerning what to do in bed--and elsewhere. Some of the guys and sluts in X-rated videos do it outdoors--in the woods, a park, poolside, or in a parked car. Some chicks flash their dicks--yeah, I watch shemale movies sometimes, too--in public places, and so... read more

shemale lover September 27, 2011 100%

The Greatest Lie Part 4

Don’t get me wrong, I don’t hate being around people. Actually, I hate being alone: it brings out the weird self-critic inside me. But god, do I hate crowds. Fall registration brought mobs to the campus. The half-empty dormitory that I had shared with a few Asian engineering students was... read more

shemale lover January 19, 2012 100%

Backsliding: Tim's Story

Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... read more

shemale lover February 9, 2012 75%

Lana: Second Encounter

Well, you may remember the satisfaction I felt at the end of my first encounter with Lana. I had not really expected to find a CD with whom I felt so comfortable. Usually, I had left my experiences with some discomfort about the surroundings or the person I had been with. Not in this case, she was... read more

shemale lover November 11, 2011 66%