Free Shemale Stories

He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of ... read more

shemale lover June 15, 2014 89%

TV television

My girlfriend Gloria and I had just moved into an apartment together, having gone out for six months or so, before making the committment. We moved in furniture from each of our apartments, after deciding what would go best in the new place. With the exception of a television, we really had everythi... read more

shemale lover December 11, 2011 100%

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%

White TV + Black Gangsta - 1st Date

I was having another somewhat boring evening alone. My name is Jill (when I put on women's clothes, that is) I was sitting at my computer, checking out the chat rooms on AOL. Just moments before, I had shed my male persona and taken a long hot bath, followed by a sensuous body shave that had left me... read more

shemale lover November 19, 2012 100%

First time in Bangkok

If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floo... read more

shemale lover January 13, 2015 81%

Growing up CD Part 2

After we left Max, Peter and I fought over who would get to take the magazine home. We decided to tear out some pages so we could have some each. We agreed to catch up the next day and go to his house as his parent were going away for the week. That night after dinner I told mum (dad had left ... read more

shemale lover December 10, 2011 50%

Lana: First Encounter

Well, I occasionally surf Craigslist in the Casual Encounters section clicking on the t4m button. More often than not I see the regular posts. No one over 35, big cock, muscular a +, face pic a must, no cock pic, 420 friendly, you must host, etc, etc. I wonder, ‘what are these people thinking?... read more

shemale lover November 11, 2011 100%

Slaves Wanted

Right, if you're reading this, then you are probably already interested in being a good little slave slut. Now I'm going to take you one step further. I'm recruiting slaves now; I don't care if you're a man, woman, cd, tv or shemale, I need you to submit yourself to me. . .now. Here is what yo... read more

shemale lover January 30, 2012 100%

A New Dawn Chapter 5

Tom's life was going well. He had a job he enjoyed, and apartment he was comfortable in and he had Dawn. He watched her in the mirror from the bed they shared as she applied her make up and smiled. Yep, things were pretty good. Dawn saw him watching her and grinned. "What are you smiling abo... read more

shemale lover March 31, 2012 100%

But it's just two guys right?

CD's and TV's are not really chicks they are guys and they have guy sex drives! Unlike many online Cyber Queens as I call them. Years ago I did do some cross dressing. Unlike those AOL and Yahoo frauds I really did dress up and unlike them despite digital cameras being new things and ve... read more

Jennifer4u727 November 3, 2016 100%

Cross-dresser Drinks Cum

Nikki looked up at me with her big, brown eyes as her head bobbed on my cock. Nothing was quite so sweet as one of her blow jobs. She had this way of dragging her tongue along the underside of my cock that made me want to cum in seconds. I always tried to hold it, but Nikki wouldn't let me. When she... read more

shemale lover March 29, 2012 100%

Pippa's Story

I was just entering my prearranged destination. It was 11 pm and just before I paid the admittance fee, I stopped to look at myself in the mirrored walls. Reflected before me was a sexy, if a little sluttish looking woman in her thirties. The only discrepancy being that I was actually a 37-year-o... read more

shemale lover April 4, 2012 100%

A New Life Part 3

I have now lived with Mistress Sara and Master Tom for over two years. They are great Masters to serve. We have interacted with other "families" and I have found them less then satisfactory compared to my own. Mistress Sara is a lovely woman, beyond words lovely. She is extremely strict an... read more

shemale lover April 13, 2012 100%

In Hose and Heels for Daddy

It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and... read more

shemale lover September 30, 2012 90%

TV Times

One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said "Hi" and we got to talking. He was married guy named Mike and he had a very understanding wife who allowed him to meet men and a... read more

bigtranslover December 9, 2013 85%

My shemale GF Part 4

I am now pretty much living at Christys place along with Ashley. So Ive reverted back to my 13 year old self of having wet dreams, and its really annoying especially waking up with a puddle in the bed. Chrisy went shopping, while i was just chilling and smoking weed with Ashley. Christy walks in and... read more

shemale lover July 19, 2012 100%

Amazon TV

Colin O'Bannon stood at the cross walk waiting for the light to change. Colin was a large powerfully built man in his prime. He was dressed in his favorite leisure outfit, jeans, T-shirt, boat shoes and a ball cap. His broad shoulders and slim waist turned many female heads. He felt a tug at his sle... read more

shemale lover October 25, 2012 100%

Barbie Jo Adventures Part 5

Friday Night I've gone all week as Joe; no one at work has said anything to me about Monday morning. So I assume I got away without being exposed as a cross dresser. I was working late all week and finally Friday is here. I am so horny and anxious to become Barbie Jo. Hopefully someone will call,... read more

shemale lover February 18, 2012 100%

Darla's Video Delight

The day had gone well so far with my girlfriend of the time having just left the night before, going out of state for two weeks visiting relatives. It was Saturday so I didn’t have to work, I had completed my chores... shopping, cleaning the apartment and doing laundry and had spent the aftern... read more

shemale lover July 14, 2012 100%

First Sexual Crossdress Experience

How my secretary found out I'm a bi TV and how me and my TV friend educate her into some of the more zany aspects of TV sex. *** As I laid back against the wall of the toilet with my nylon-clad thighs spread wide and my erect cock jutting up lewdly from between them, the wooden door in front o... read more

shemale lover September 27, 2012 40%