Sissy Surgery Stories

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The Path to Happiness Pt. 09

by brendachaplin2000 on Sep 28, 2020
Transgender & Crossdressers

A couple of months passed since my weekend away on the film shoot. I wish I could say Chris and I become an item, but sadly I discovered he was already in a relationship with a girl and she was expecting his baby. My life already had too many complications without becoming the "other woman". On a positive note David had started a relationship with Adam, and...

From John to Jenny

by GaysonPerry on Apr 20, 2020
Transgender & Crossdressers

John put on the little black dress and became a she, her little clitty slipped out from beneath the red lace panties and she fondled the outside of the lacing. With this, she felt sexy: combined with the 'fuck me' pumps and a red bra she was about ready to be a sissy, except there was nobody around except her and her toys. All that ruined the illusion was...

Cheap Sissy Whore To Call Girl

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

I looked at the throbbing red cock within inches of my face, split seconds before I was to be showered with thick musty spunk on the back alley streets while I thought back to what had happened 24 hours ago when I was a normal 22 year old male living a normal heterosexual life. It all started when my girl friend of the time, Doreen, had filmed us having sex...

Breeding Natalia

by sweetsatine on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Nathaniel Geller had been a young, up-and-coming salesman at MedZ who'd shown great potential. In just a few years, he made his way from ambitious college graduate to savvy junior manager. Risky ventures that others were skeptical of luckily always seemed to turn out succes...

Doctors Orders 2nd Appointment

by Misslexia on Sep 13, 2017
Fetish

The instructions in Dr. Jones' letter were clear, if a little puzzling and I followed them exactly. At a quarter past seven the next morning I rang the bell on the surgery door. Margaret let me in. "Morning Chrissie," she greeted me. "Dr. Jones is in room 3 waiting for you, go right in." I went in. Dr Susan Jones was waiting. She looked stunning again. Her...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

Dear Diary

by MissYellowPanties on Mar 26, 2019
Transgender & Crossdressers

Dear Diary. I never really like my job, the best I could manage was feigned enthusiasm in front of my supervisors, but it paid well, and so far I had been able to spoof my way through 3 years of regular paychecks with minimal effort. Cube life sucked the life out of you, but computer programing wasn't really difficult and at least it paid far better than m...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

Abducted For the Better

by BluntSlut on Sep 16, 2017
Transsexuals & Crossdressers

I woke up blind folded to hear many different voices in the room I was in. I did not know where I was and I was blindfolded. I tried to move but it felt like my body was numbed. I must have been drugged because the last thing I remembered was raving at the bar with a group bad bitches. "Where was I, Why was I here, and who are all these people" I thought in...