Free Shemale Stories

Cutting Ms Betty's Lawn

My mother had suggested I might consider cutting Ms Betty's lawn as none of the other boys in the neighborhood would. All the other mothers hated Ms Betty and wouldn't allow their sons to associate with her. She was one of my mom's friends and I thought nothing of it, so I agreed to do it every week. It seemed Saturday mornings would be best, so I put her in my schedule and planned on the following Saturday to the first. I was doing a great job with my lawn cutting service, picking up new clients from word of mouth after I did a lawn or two, but my schedule was becoming full.... read more

buttguy January 16, 2018 69%

Carla goes out

As a cross dresser who loves to dress as a dirty slutty girl I was sat at home thinking about what it would feel like to go out dreesed in public. I had often thought about it but never had the courage to do so. I was so fucking horny and wished I had a reason to go out and do something rather than sit at home alone. I thought about the times when I took my Dog for walks on summer evenings and we would walk in the woods and fields for hours at a time. I no longer had my dog sadly so didn’t get out much anymore. It got me thinking though, about what I came across whilst out walking with my Do... read more

Carla Kitten January 16, 2018 50%

First time pretty

This story might not be intresting to anyone, because its true, simple, and not some fancy fantasy. So it was the first time that i dressed in female clothes. I was alone at my home, though I had no idea when someone could come back. I was already shaved on all my body, because its much more comfortable and looks better. First of all I put on stockings, and when I did, it felt really good and warm, I thought its a pity that I don't get to wear it all the time. Unfortunately as I didn't know how much time do I have I didn't put on make-up, instead I took venetian mask (small p... read more

Gwella January 16, 2018 50%

Night With Shana

This meeting took place in Los Angeles, CA. I’m sure many of you are into shemale porn movies and will know who Shana is. For those of you who don’t know her, she is a gorgeous white shemale with long brown/blondish hair, big tits ( think there is some silicone in there — but who cares), lovely, long legs and a nice thick eight-incher. This encounter is true and happened about 4 years ago before she “became a star”. Well anyway I was on a business trip to LA and was horny to have my ass fucked by some hot TS. I checked out some shemale escort sites (the on... read more

shemale lover January 14, 2018 80%

My first taste of tranny cock.

So got my first taste of tyranny cock over the holidays. My wife found a sexy tgirl on Craigslist something we have wanted to do for awhile now. It was so great she was super sexy blonde huge tuts and a fat 9 inch cock that she used on both of us. Best time of my life she fucked me while my wife sucked me and rode my cock. Then fucked my wife while I fucked the sexy smooth shemale the we both stuck our cocks in my wife it was so fucking hot our cocks rubbing together in her pussy. Then to top it off we both shot our loads in my wife then my wife looked at my and said lick it all out of my hole... read more

Trannylover6983 January 4, 2018 70%

Tranny swinging

Chapter 1. My wife Claire rang the doorbell and we both looked at each other, our hearts were racing, what was going to happen when entered these strangers home. The reason for our trepidation and standing in front of this alien door was that we had answered an add on a swingers site after we had discussed that our sex lives were flagging and after entering all the usual data we had spiced up our sexual preferences. We had both put down bisexual and I had ticked the box for crossdressing and transsexual interaction. The invitation we got back stunned us at first, it had requested that both ... read more

Amy4u January 4, 2018 37%

Ejaculation of a person

When you want to fire up to a full reservoir, urgent flood, the whole mind only thought I need to be fuck, need to be ejaculation to ejaculation, need to be fuck orgasm.But that long time can not find, that root can put my When the entire rectory filled the eldest brother, I even thought of madness commute station during work hours, take off underwear, lifted skirts, shouting at passengers to kill me. In order to avoid their own crazy, only to use the old drama code again, masturbation to vent.Use a huge root massage stick hard into the anal, slowly pumping inserted, and the other hand pinch ... read more

gangbang hole January 4, 2018 20%

My Dream pt 3

Our first invitation arrived at the end of September. Sydney spotted it first and tossed it into the trash with out looking at it. She didn't tell me what it was and I didn't bother asking. The next invitation arrived two weeks later. This one Sydney opened and after reading it she passed it to me. It was a formal invitation addressed to the both of us from one of the female teachers at the school. The teacher was a fellow math department teacher that I had talked to on several occasions. She was very sweet, small with small breast and a very cute face. She was a little older then... read more

Sydney Sun Min January 4, 2018 94%

Dressing with my cousin

My First Time When I was about 16, I would spend my Summer vacations, from school, at my Uncles’ house. My cousin and I would sleep in one bedroom, with two beds. He was three years older then me and always knew what we could do, to have fun. I looked up to him and wanted to be like him. We had no secrets between us and we shared everything. One afternoon I came home early, from a friends’ house and found my cousin standing in front of a full length mirror, dressed in a blond wig, black nylons, yellow panties, bra and a yellow summer dress. I could see he was stroking himself under th... read more

Topazsteve January 4, 2018 77%

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 watched my share of shemale videos.  Interesting how you could be with a woman and yet be with a cock at the same time.  Very interesting.  .....  So, the foundation was set. I went fishing in the Florida keys for a few days and someone I knew there said I should checkout Key West since I hadn'... read more

peepholeman January 4, 2018 92%


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