Free Shemale Stories

Turn Back Time

If I could turn back time to when I was younger and prettier, I would have loved to make this fantasy cum true. I'd get my long hair styled; my fingernails and toenails painted bright red, and put on a very skimpy stripper outfit with g-string, heels, and mesh dress. I'd walk out on stage in a ro... read more

shemale lover November 14, 2011 100%

Caught by my wife

I was stuck, I couldn't move, literally in headlights... I dress up okay? you caught me, I guess your the master now... I used to control my wives life and for good reason I pleased her, and she pleased me the best she could... well now that's changed.. she came home from work early last Tuesday and... read more

shemale lover December 7, 2011 71%

The best sister ever Part 3

As always yes my sister is a shemale and yes this is all true every word of it. So since we have formed our new relationship we have been fucking not stop for about 4 years now so im 14 and my sister is 16 years old. I have now a thick 6" hard cock and my sister has a huge 7 1/2" cock a... read more

shemale lover December 27, 2011 66%

True story tv first dogging

I am a mature TV living in the north of the UK. I have been dressing since I was 7 and having nylon led sexual fun since my early teens. The result today I have a very large wardrobe of clothes and shoes, am 100% smooth apart from a landing strip and have manicured nails and shaped eyebrows and with... read more

shemale lover January 8, 2012 100%

TS Prostitute Urge

After college I began to explore the world. To that point I was the average male that happened to get a lot of tail. My sexual exploits with women were something I was proud of and always gave me a sense of being a real man. After years of watching straight porn and imagining myself in every possibl... read more

shemale lover January 27, 2012 100%

Dead Ends

* * * My job is simple: I'm a masseuse (code word for prostitute). It used to be fun, too, but, after a while--well, let's just say the thrill is gone. I mean, how many cocks can a girl suck or fuck until the novelty's worn off? (In my case, I reckon the number at about 3,000.) So, I don... read more

shemale lover January 27, 2012 50%

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%

A Future Society

Anna was lined up with the other girls beside her, the heat from the electric torches on the wall stinging her bare backside. Her long blonde hair stretched down to the top of her ass, shielding her back from the heat, but she often wondered during line ups whether or not a bulb would burst and send... read more

shemale lover March 5, 2012 100%

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%

A Glory Hole for Tranny G

I am reveling in what a difference almost a year has made. I remember meeting Chris online, exchanging a few funny e-mails, two days after my birthday. No more and no less, just a person somewhere who I had no idea what he was like or looked like, but someone who made me laugh with our e-mails each ... read more

shemale lover March 7, 2012 85%

A Job in the Theatre Chapter 10

She found Ted and Sarah sipping drinks. Paula walked over and retrieved her cute ruffled panties and then proceeded over to Ted, took his drink and put it on the table and looked at Sarah, "Excuse us. We have some unfinished business." She took Ted into her bedroom and closed the door. ... read more

shemale lover March 13, 2012 100%

Memoranda From Mr. P

Mr. Reddie used to call me Petro, as a short familiar name; his sly friendly way of reminding the two of us of my thick lengthy cock. Mr. Reddie maintained, when it was hard and erect, my cock looked and felt as lovely as Italian marble, hence the contraction of the Italian for stone: Petro. Whi... read more

ColonelSaint March 19, 2012 75%

Three for Fun

I was on my way home from the bar one night when I noticed a group of ladies standing on the corner talking. As I approached one yelled, “hey sexy looking for the time of your life?” I stop for a minute and stare at the three beauties in front of me. “Well the time of my life does ... read more

shemale lover March 26, 2012 95%

A good laugh turns into a new experience

I have a friend that works in theater and makeup, one night he got tickets to a "trans" ball and invited me to go with some friends as a joke. So I figure, throw on a skirt, toss some apples in a bra throw on a wig and go party. I show up at my buddy's house around 8. I figure we're gonna ... read more

shemale lover April 2, 2012 0%

Eric...a Part 2

I was well into my first semester of college. The University I chose was close enough to drive to, but my parents thought it would be a good idea to for me to live on campus. I didn't mind, and actually wanted some freedom. I lived in a single dorm unit and was not having a difficult time of transit... read more

shemale lover April 18, 2012 50%

Threeway Heaven

Times were tough and I took a job as a bouncer in clubs on weekends. It was a pretty boring job most nights, and frustrating having to deal with drunks all the time, so my boss sent me out to a gay club for a change of pace. Also, I was one of his few workers who wasn't homophobic, and therefore les... read more

shemale lover May 10, 2012 100%

Life's a Beach

Turn right at the light. Jen said. Tom turned to look at his girlfriend as he obeyed. Her long brown hair was up in a ponytail, exposing her elegant neck. She flashed him her radiant smile and winked at him with her beautiful green eyes. She wore very short shorts that showed off her long tan leg... read more

shemale lover May 10, 2012 100%

Transsexual Cheerleader

Transsexual Cheerleader Marcus, the football team quarterback, was well known at the university as the "most datable on campus", and he had had his share of women. From the nice virginly freshman, to the hottest senior whores. It was no wonder that he was so popular. 6'4, 240 pounds of pur... read more

shemale lover May 13, 2012 85%

The Making of A Sissy Part 4

After an exhausting evening Bella was made to wait at the door and humbly kiss the guests as they left; some of the males groping her pretty arse as they departed. She was glad of the alcohol she had been treated to as this masked from her the ugliness of some of the brutes she had been forced to en... read more

shemale lover May 24, 2012 85%

Relic fort

So i pull up it is raining and i had packed my nice latex skirt and top so i decided to check things out. out of the car i go heading to the woods which i was told i would find the over grown play fort. sure enough there it was, i hiked around for a few minutes all the while noticing more and more g... read more

shemale lover May 26, 2012 66%