Shemale Sex Stories – Page 5 – Transsexuals Sex Stories

A Night With A Craigslist Transsexual

Credit https://www.gaydemon.com/ markerss

I had always fantasized about being with a transsexual, but never had the guts to pursue it. I had responded to several Craigslist ads to meet trannys, but after only few messages, I usually became overly nervous and I never went through with it. However, there was one Craigslist ad that simply said, “Satisfaction Guaranteed.” The photos she posted were great and she even had her own web site. She looked to have a pretty face, a nice body, and great boobs, and so, I decided to try to contact her. Just like all the other, I became nervous after hitting the send button, but when she finally responded back, she seemed to be personable in her message back.

A Hot Hookup

Credit https://www.gaydemon.com/ cdluvstosuck

I am a 40-something cd who gets off dressing up really slutty. I love wearing nylons or hose, heels, short skirts, bras, panties, wigs, make-up, and painted nails. I love to have my body shaved smooth because it makes me feel soft and fem. When I am all made up all I want to do is please a man. I suck dick, rim ass, swallow cum, and I love to bend over and take it deep in my tight ass.

A Girl Called Eddie

Credit https://www.gaydemon.com/ Pat Sizer

Carrie had always treated me like her little sister, even though we were only third cousins. Though she was only two years older than I was and not of exceptional physical stature, I had allowed her to dominate me for as long as I could remember. Not that she was exceptionally cruel or abusive in any way. It was just that she seemed to realize I was different, long before I myself knew. I could never remember her treating me like a boy. By the time I reached my teens, I was wearing her clothes at any available opportunity, with her permission and no small measure of encouragement. In our secret world, we talked about boys, makeup and fashion, just like two real girls.

2 Girls Out For A Night On The Town

Credit https://www.gaydemon.com/ Pat Sizer

Some of my best friends are transvestites. I met them at a nightclub in L.A. It was pretty famous back in the day. They had a drag and dinner show. Some very talented people worked there.

Some actually lived their lives as women, but a lot didn’t.

I used to hang around with Daniel. He was a very attractive man who also did a great Dionne Warwick. He also did the grand finale of the show – the woman to man transformation. I always loved that part – where he cleans off his makeup, takes off his wig, and becomes a very very handsome young latin man. It always brought down the house.

The investigation P.2

Credit https://www.self-help-sexuality.com/ Hottvcarole

This is pure fiction and resemblance to any persons is coincidental. But if you fit the role feel free to fantasize.

Part 2

The next morning Carole woke showered and dressed in her stockings, suspender belt, lacy bra, with matching panties with her white lacy waist slip as the final item of her lingerie, then her flowing flowered dress. She applied her makeup and brushed her hair. She slipped on her 3 inch court shoes 👠. Picking up her handbag with the paper work she had to follow up on from the investigation. She left her flat and drove into town, parking in the multi story car park. She made her way to the shopping precinct. The lingerie shop she was looking for was just around the corner.

The investigation P.1

Credit https://www.self-help-sexuality.com/ Hottvcarole

This is pure fiction and resemblance to any persons is coincidental. But if you fit the role feel free to fantasize.

“Hello, Carl and Carole investigating agency, how can I help you”? I said.

“Oh hello, I think I need your help. I suspect my future wife is keeping a secret from me, and I wonder if you could check her out, she may really love me but she may just be after my money.” The caller inquired.

Co-worker surprise P.2

Credit https://www.self-help-sexuality.com/ Kerris

I was totally confused and oddly a little angry for some reason, perhaps I was feeling deceived, but then Lexy broke my train of confusion by scooping me into her arms and holding me tight against her, her manly appendage swinging between my thighs and my Vag.

I tried to speak but the words would not come, my throat was dry and tight my breathing ragged and shallow. Lexy’s kisses melted me, so lightly did they land on my lips, then her tongue flickered and probed my mouth, I responded in spite of my confusion, I simply lost myself to the situation.

Co-worker surprise P.1

Credit https://www.self-help-sexuality.com/ Kerris

I really loved my new job in the County Library, I worked with a girl name Alexandra, or Lexy as liked to be called, she was a bit older than me, attractive, nice figure, terrific rack and shapely legs topped off with a nice rounded booty, leading me to believe she had to be a real heart breaker with the guys.

We got on very well and worked together for about three years before I suddenly began to realise that I was strongly attracted to her in a strange way. I’m by no means inclined to being Lesbian or Bi-sexual but the raw fact was that there seemed to be some sort of magnetism or chemistry flowing between us.

Vanessa and the workmen

Credit https://www.self-help-sexuality.com/ Vanessa Luv

The three workmen were slaving away in the back garden, in the hot sun. Vanessa watched them from the upstairs bedroom window, getting more excited by the second. Under her robe she was wearing a beautiful red basque with a red g-string, black stockings and five inch heels. This was topped off with the tiniest lycra red halterneck dress which barely concealed her ass or bulge.

A Surprising Night P.2

Credit https://www.self-help-sexuality.com/ Peter

I went to wipe her thick sticky spunk from my face but she stopped me!

”Leave it!” She firmly pushed my hands down. ”Makes you look like a real whore! ‘Hahaha’ kind of pretty but used!”

I was made to follow the down the dirt track, away from the road and further into the trees. A clearing opened out, well frequented by the look of it, and in the centre was a fallen dead tree, it’s thick trunk about three feet from the ground and covered with an old piece of carpet or rough blanket. The scudding clouds had disappeared and the pale moon lit the whole scene very well. I was hobbling, my jeans and underwear still around my ankles.