Crossdressing School Stories

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From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Cindy's Panties

by secretanon on Sep 13, 2017
Fetish

I am around 24 years old and I have always enjoyed wearing panties. I think the feminine feeling of it all really turns me on. At a young age, I discovered masturbation from cumming on my mothers panties after deciding to be bold and try one out from curiosity. I was never able to fufil my love for panties, being in a house full of males, so I never had a si...

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

The Futa next door

by Abusedbyfuta on Jan 11, 2019
BDSM

You have lived in the same l cul de sacyour entire life. It's not a bad place to life, very much a part of suburban America. It's just not very exciting. You live in a large White House that looks the same as all the others on the street, probably a ploy by the developer to keep costs down. Every day you see the same boring neighbors, have the same boring ro...

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Mistress Mariegolds Academy

by Heinrich12345 on Dec 25, 2019
Transsexual

The Academy was founded and is still leadet by Maria Mariegold. With a lot of hard work and pasion she managed to make the Acadamy to one of the most prestigious schools in the whole Empire. Today some of the most influential Families send their kids to this fecilety to become influential Futanari or a great cocksucer for some high class Futanari. Over the l...

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Sarah has a Crossdressing Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before e...