Free Shemale Stories

From accidental trans porn addiction to a cum filled booty

One night when I was around 30 or so I was watching some porn, nothing unusual for a guy like me, aka a sex addict. Sex addiction is great if you’re Tiger Woods and swimming in poon, but for guys like me - regular, awkward, slightly handsome in a very boyish way, weirdos — it’s not that fun. We... read more

CDJaneBooty April 1, 2022 100%

Mutually Assured Attraction Part 1

Max's life sucks. His job is leading nowhere and women avoid him like the plague. On most weekends his free-time is spent drunk in bars, hitting on women that don't want his attention and ultimately passing out in some back-alley. To make matters worse, his hairline has all but receded off the back ... read more

shemale lover September 15, 2011 50%

The Tranny Trucker

A gust of freezing wind blasted across my face. I succumbed to worries of frostbite as I walked aimlessly along the side of the highway.\r\n\r\nThe wind of passing trucks nearly knocked me off my feet. This must have been dangerous. It\'s something I should have considered.\r\n\r\nMy parents separat... read more

shemale lover July 19, 2013 93%

Anna, Ted & She Male (Carley)

Returning from Anna's class reunion, both Ted and Anna were pleased with their adventures. Anna was able to again experience something really hard and full between her legs and Ted was able to again perform as he did a couple of years ago after being turned on seeing his loving wife with two other m... read more

shemale lover December 13, 2012 100%

First Time I Experienced Eating a Tgirl Out

So this is likely going to seem tabboo for some and if this is not your thing, I respect that but everyone is different. Eating pussy came natural to me like it does for most guys once they start having sex with girls. Other than one time 69ing with a female and having what I would call "incidental ... read more

AllenB October 21, 2022 100%

My step mom turned me into a sissy slut for dad

When I was in High school I would spend the summers with my dad and step mom. She was so hot and always dressed sexy, They were always very playful about sex, not like my mom and step dad. I loved the atmosphere. During the week they would work all day and I would have the place to myself. I would ... read more

shemale lover February 20, 2012 90%

Becoming Alanna Part 3

We went up stairs to the kitchen and she had me start to help her ice down beer and get bottles of booze out and open. There was a large bar but I noticed not much in the way of food. I helped tidy and set up cups and get ice and then with a sudden shock to my heart the doorbell rang. As it did I ca... read more

shemale lover August 7, 2012 66%

You've Got Mail Mom (male)

You decide to take the bull by the horns. One Friday evening, as you're helping your mom clean up after dinner, you tell her, "Mom, there's something we need to discuss." "What is it, Jamie?" Erin asks. She puts a bowl in the dishwasher as she speaks. "Let's finish up here and go talk in the l... read more

CHARMINN October 9, 2023 80%

My sex education from my hot aunt

My story was inspired by a recent discovery of a clip of Miriam Rivera. Since see the remarkable resemblance to my aunt I am constantly jerking off fantasizing about it. Let start with the true part of the unique experience going through puberty relating to my aunt and the latter part is fantasy I ... read more

Pabloduro April 24, 2024 100%

Medicine of Magic

“I can’t believe that you don’t like women, my woman said to me. I had just kissed her passionately and slid my hands to cup her firm buttocks, my lips now moving across her throat. I murmured against the sweetness of her neck, “I didn’t say that I don’t like w... read more

shemale lover December 2, 2011 100%

High Rent Tranny Whore

It's morning already and I wish I could just sleep but Maria has a client coming in at 10:00AM and Jasmine is here already to wake me up. Jas is great and has a huge cup of French Vanilla Coffee for me. "Wake up Barbie, Maria will need the lounge to dress and get ready for her session".... read more

shemale lover December 3, 2011 100%

Candy Pink

Life pretty much sucked. I was the son of Ralph and Cindy Cassella. They named me Ralph Junior and my dad was thrilled to have a son he could raise to live out his past glory. My dad wasn't a bad guy and never abused me but I knew he was disappointed. He worked as a contractor in the present but he ... read more

shemale lover December 8, 2011 75%

Fellatio in pantyhose fantasy fulfilled

As those of you who have read my stories know, I love pantyhose. I'm also quite heterosexual in that I'm extremely turned on by femininity; thus the pantyhose fetish. I have no desire to "be" a female as I love my big penis and I love the way it feels in pantyhose. I also love shooting spe... read more

shemale lover January 23, 2012 50%

LADY SUKI

It was my best friend who dragged to this little club downtown promising something I had never seen before. It turned out to be a little strip club. We found a seat right in front of the stage and we watched strippers of various shapes, sizes, and ages perform with a bored mechincalness. "And ... read more

bigtranslover December 13, 2013 87%

Shemale

My whole world changed when Brant came into the scene. I was all set to take over from father in the Jann Troika, something I’d been trained for since birth, and doing anything else just never entered my mind. Then I met Brant Tor, a Killian soldier. I’d met Killians before, and like ... read more

shemale lover September 22, 2011 0%

What If My Mom Part 2

Peggy and Me We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute" Just as Mom left Peggy rolled onto her side facing... read more

shemale lover June 23, 2012 100%

Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one ni... read more

shemale lover April 5, 2014 90%

Miko and Mali; Thailand's finest teen sisters

Last August my friends and I went on a “lads holiday” to the beautiful country of Thailand. We had booked a fortnight, which was to consist of five nights in a city hotel in Bangkok, and the remainder in a stunning 5* resort in Phuket. It was my first time in the country, my friends hav... read more

shemale lover June 25, 2014 86%

Seven Minutes in Heaven

This is purely a work of fiction about two 18/19 year olds... It is the summer before our first year of college and we are home alone at his house. My mom works from home, but his place will be empty until his sister gets home from her summer internship. We have been playing truth or dare since... read more

shemale lover September 20, 2011 100%

Date With A Mistress

It was a sultry afternoon and I was sitting in my study remembering the events of the past weekend. Never before had I thought that I would endever to fulfill my fantasies until I met Angela. Friday Night: It was late in the afternoon when I decided to check the adds on my computer. I was look... read more

shemale lover November 4, 2011 90%