Transsexuals & Crossdressers Stories

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Nikki 02: The Friend

by JacksonMarks on May 11, 2020
Transgender & Crossdressers

Note from the author: This is the second part of the Nikki series. The first was Nikki - The Friend of a Friend. ***** Nikki led me upstairs. She held my hand the entire way. I could still taste her cum in my mouth and I was excited to find out what she had in mind. We got to Nikki's bedroom. Stopping at the foot of her bed. Turning round she looked me in...

Strawberry Milk Pt. 01

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I was in my last year of college and frankly broke and depressed and pissed off at life. Debt sucked and despite my ever so awesome computer degree that big tech job never came. And broke means no dating. No dating means no girlfriend. And the cycle spun on like that through my last year of college until desperate I found a private ad for a developing na...

The new Secretary Ch. 02

by 13feathers on Apr 13, 2020
Transgender & Crossdressers

The next morning Melody woke, only to find she was still very securely and effectively tied up. To her right, a Television programme on bondage was on, and Melody gave it her full attention. She found herself agreeing with the contents, how delicious and sexy it was for a woman to lose control of her movement, the thrill of being helplessly bound in latex or...

From Business Owner to Prostitute

by Kellycumslut on Dec 2, 2019
Transgender & Crossdressers

How things have changed. From respected business owner to insatiable street prostitute. For a long time I ran a very successful business in London employing 14 staff and loving my work. I worked six days a week and on Sunday I did the paperwork, wages and stock checks. I had no time for social life, I was working for a successful future and in the evenings...

Taking the Lad out of Alladin Ch. 08

by CaseyHeart on Oct 21, 2019
Transgender & Crossdressers

"Oh for fuck's sake Alain! Come on!" I grimaced, and pulled my boobs apart to stare down at my dick. The head was sticking out of my panties and I think it winked back at me. That's panties, plural, by the way. The top pair was bright red, and Jasmine had me in three pairs of tight panties. She was trying to teach me how to tuck my dick back, but the treac...

The Package - The Magic Deepens

by TransFormationTypewriter on Jul 29, 2019
Transgender & Crossdressers

Josephine drops the bag off her shoulder and stares, as if in a trance, at the hand furiously rubbing up and down Amy's new cock. Her reason for visiting becoming more and more vague in the back of her mind as she stares at the deliciously naughty scene in front of her; Amy, her friend since university, who has never owned a penis before now but suddenly now...

My Sissy Boss

by newbie88 on Sep 24, 2019
Transgender & Crossdressers

I knew this is why you'd hired me. I knew it from the start but had wanted to be sure before I actioned any of the dirty thoughts that filled my head on a daily basis. I had watched you watch me, had seen the desire in your eyes. I knew you wanted me, knew what you wanted and I could not wait to give it to you. I chose my outfit carefully that day. A loose...

Home Alone Ch. 02

by Hickorydickorydock on Nov 18, 2019
Transgender & Crossdressers

The Next Day: My head was pounding and my eyes felt sealed shut. I pride them open to see the cold light of the beginning of a gloomy day streaming through the living room windows. I'd fallen asleep on the couch. A sharp pain was coming from my left arm, the side I was lying on. As I looked down I saw the wine bottle from last night tucked underneath, cutti...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

Shemale in Porn Theatre

by Subman666 on Apr 14, 2020
Transgender & Crossdressers

This action begins with my weekly trip to the local porn shop, made up of the typical video booths as well as four open rooms with big TVs showing various movies. It's afternoon when I enter, and I immediately walk into the video viewing area, a dark open room with straight porn continuously running. The place is set up like a big square track, so as I walk...