Free Shemale Stories

I meet my new Mistress for the first time

I was feeling excited about and looking forward to Friday night. The reason for this was that I intended to dress up as my alter ego, Tania Harvey, and to go for a night out to a club nearby that is popular with TG’s, TV’s and other like minded people. I took a lot of care and attention over the way... read more

Tania Harvey June 26, 2017 68%

My fist time

Hey i was out on a night in manchaster, meet up with a grill as i thought we had a few drink at the bar, She kissed my Nibley on my both lip as as said let go her place .. We got to her place she pushed me to thrpe bed opened my my buttons started to suck my cock licking up and down , im l... read more

Newbe2 June 29, 2017 34%

Cara's First Time

Cara's First Time This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in... read more

Emma W July 5, 2017 78%

First Time With A Man

Just a true story, first of a few telling how I got where I am: First Time With A Man: Ok, pretty tame but here goes... One night when I was about 14 or so a strange thing happened. I ran out of smokes... that's not weird but if you're a smoker you know it sucks. So I walked up to... read more

lilslutmouth July 7, 2017 65%

She came inside of me

In my city there are several transsexual brothers where there are usually a good amount of attractive girls working. It had been quite a while since I've visited one but on a hot sunday night I decided to pay one of them a visit. Even though I had been here before I was nervous, the place is... read more

Gracemel121 July 18, 2017 83%

Anally destroyed by a Peruvian goddess

Browsing around the Transsexual escort ads here in town I found a new girl, something else than the typical manly faces with heavily photoshopped pictures. A Peruvian girl named Isabella had just arrived in town and was open for business. She has a few retouched pictures but also some natural selfie... read more

Gracemel121 August 7, 2017 70%

erste mal

Ich muss, bevor ich meine Geschichte erzähl, klar stellen, dass ich bi bin aber an einem Mann eigentlich nur den Schwanz geil finde. Ok, also ich ging mal wieder seit langem Samstag Abends aus. Zwar alleine aber ich erhoffte mir vielleicht eine hübsche Frau tu treffen. Also ging ich in meine Stammkn... read more

sam2121 August 7, 2017 67%

My first time with a shemale

This first time I saw a she-male in my live was in Germany Hamburg at the Reeperbahn. I was in a tranny show where I realised I got horney seeing those women do there acts. After there show I went to talk to the ladies. Nothing went feather then some kisses and that there dicks are full operational.... read more

shmlover832220 August 28, 2017 67%

story of Jojo

Some find it confusing of who i am or what i am, including me. i found some kind of definition: femboy A young boy who presents extensive feminine mannerisms and actions often blurring the line between a boy and a girl. Can be confused with a cross dresser, but it usually refers to boys at v... read more

jojo58654 September 12, 2017 55%

Manual Sissificar a tu Novio

MANUAL DE LA ESPOSA Y NOVIA PARA SISSIFICAR A SU HOMBRE, DESCUBRIRLE SU LADO SUMISO Y CONVERTIRLO EN CORNUDO Y MARICÓN por MARINATVFEM Todo el proceso es una batalla psicológica que tienes que ganar siempre. Mantén la calma y no levantes sospechas. Entrénalo día a día con humillaciones continua... read more

Marinatvfem September 25, 2017 58%

SEGUNDO ORAL QUE HIZE

Antes de empezar, quiero aclarar que soy un hombre y en el momento que viví lo que aquí cuento, yo tenía 16 años. Todo comenzó un jueves a las 7:00 pm. Yo estaba en la casa de una amiga que había conocido unos meses antes en un centro comercial, me gane la confianza de ella porque decía que hablar ... read more

jessyca_nal October 2, 2017 33%

Hago otro oral

Antes de empezar, quiero aclarar que soy un hombre y en el momento que viví lo que aquí cuento, yo tenía 16 años. Todo comenzó un jueves a las 7:00 pm. Yo estaba en la casa de una amiga que había conocido unos meses antes en un centro comercial, me gane la confianza de ella porque decía que hablar ... read more

jessyca_nal October 3, 2017 60%

Ann and I

Last night I had an awesome experience. I was down in Fort Worth to meet a tranny I had been talking to on squirt. I got off work early, took a shower and shaved my cock and balls and dressed in jeans and a t-shirt and headed down to Club Changes to meet her at four. The bar was pretty empty, Thu... read more

Giantsquid October 13, 2017 80%

CÓMO SER UNA BUENA SISSY MARICA

CÓMO SER UNA BUENA SISSY  VARIOS COMPORTAMIENTOS: Pasiva, sumisa, perezosa, dominada, obediente, frágil, vulnerable, indefensa, mansa, cariñosa, dulce, encantadora, cálida, blanda, bella, sexy, afeminada, suave, amable, dócil, respetuosa, delicada, débil.  EROTISMO CON LA LENCERÍA: Después cogí... read more

Marinatvfem October 16, 2017 71%

My first encounter

This story details my first encounter with a stranger I met over the internet. I was 25 and reall getting into being a girl, I dressed all the time, and dreamed of sucking a cock dressed as who I really wanted to be. So I took a plunge in meeting someone for a quick bj in the area. I sent him some p... read more

Robyn Peirce October 19, 2017 65%

Garage fun

It was the beginning of the third hour of her time in his garage. Bound to the work table that was the perfect size and height for her head to be over one end and her ass the other just perfect for a cock to enter either entrance. The only way she knew how long she had actually been there was by ... read more

davisdan64 November 2, 2017 80%

Big Changes

Big Changes Jess was getting tired of hearing about all the female problems his sisters or his girlfriend were having. It seemed all they talked about was their sore breasts or their cramps or their bloating. At times he would just tell them to keep their problems to themselves, that he ... read more

PattiCake December 5, 2017 77%

Louise's Bedroom

The dark and humid night consumed the street surroundings, the rain pattered softly against the car window as Scott pulled outside Louise’s house. Louise had never agreed to let Scott visit before and he knew that this would be the only opportunity to make a good impression and be with her in the fu... read more

Master VeeJay December 12, 2017 76%

The first day of a sissy bitch

She's preparing to become a sissy slut First long and extensive showering then a total shave and she started to turn into the femme of a sissy slut. Naked in front of the mirror, she applied the foundation and spread it evenly across all areas of her face and neck. Next she slipped into her b... read more

sqimyetxräa52 December 19, 2017 60%

First time in Key West

I've always been fascinated by shemales.  Aside from having an overall appreciation for how the male member in general functions and, when properly stimulated, pulses and pumps...cum spewing from the tip.  I've watched any number of webcam shows where guys jerk off.  And yeah, I've wa... read more

peepholeman January 4, 2018 87%