Transsexuals & Crossdressers Stories

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How I Got My Sissy Name

by allourdesires on Jun 5, 2019
Transgender & Crossdressers

The thing was that He had presented me with the earrings, on my birthday, in front of my wife and innocently enough I had accepted them with embarrassingly gushing sissy enthusiasm, being my first pair that weren't clip-on. The very next day she dragged me along to the local mall, where all of my friends and neighbours shopped, to get my ears pierced at a ce...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...

Trapped! Ch. 04

by EffieMeow on Jun 24, 2019
Transgender & Crossdressers

"hey, what r u doing tomorrow?" My phone vibrated and made a meowing notification sound as I received another text from Damian. We had been steadily exchanging texts all week since our steamy encounter on the weekend. Our conversations ranged from innocuous questions about each other's hobbies to borderline sexting. I had not. Often I would get a text wh...

Locked Out

by kristycross on Jun 18, 2019
Transgender & Crossdressers

I've been at my new job for about 6 months. It's a new/old job as I had been the Building Chief for 4 years ten years earlier when it was Occupied by the Social Security Administration. I left before they moved out and worked for a few more years until I retired at 55. Getting called back was un-expected but the Building was Empty now and privately owned. It...

Gym Surprise

by standingstones on Jul 6, 2020
Transgender & Crossdressers

I had been going to a certain gym for a couple of years. This place had a lack of weights and machines. I asked the manager if they were ever going to upgrade the place. He said they didn't have any money for new equipment. I soon found a new gym to attend. I really liked this new place. There were serious bodybuilders working out there. I soon found out I w...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

My Trans Friend Ch. 02

by Indianaboy6555 on Sep 24, 2019
Transgender & Crossdressers

This one is short and sweet, but is still one of my favorite experiences. My trans friend Maddie and I been messaging back and forth as usual, and finally one day she told me she wanted to come down to visit. I of course agreed in a heartbeat. I was incredibly horny (as usual), and my Dom side was out in full force. I made sure to tell her that; I wanted h...

Meadows

by Dar_Jisbo on Sep 23, 2019
Transgender & Crossdressers

Thank the deity of your choice for Moore's Law. By 2030, computers were bumping up against the speed-of-light limit, but thanks to technological breakthroughs making the circuits smaller, as well as advancements in parallel processing, Moore's Law continued to hold. And by 2035, we'd reached "the singularity", where computers (androids, actually) could des...

Truth or Fantasy 08: Golfing Gurl

by 1sfshermale on Sep 24, 2019
Transgender & Crossdressers

We were on the 12th fairway and again, I had out driven my playing companions by about 15 yards. We were playing from the same tees. I was, for the first time ever, playing golf as a woman. Wearing a short black skirt and wind jacket. The morning clouds finally broke and the sun decided to stay out. The sun was warm. I took off my wind jacket to reveal by y...

Jessica Ch. 01

by jac0879 on Mar 18, 2020
Transgender & Crossdressers

It was a familiar ritual by now. I plugged the drain of the tub and turned on the faucet to draw a hot bath. It was really a pain keeping my body hair tamed, it grew in dark and quickly but I was determined. As the water ascended in the basin, I stripped my clothes, stood in front of the sink and grabbed a razor. I quickly dispensed of every last trace of st...