Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

Spanking Night Ch. 05

by Angelscuck on Sep 14, 2017
BDSM

I took out the scissors and cut my beard and mustache as close as I could then used the electric clippers. After that I finished shaving my beard and mustache off with shaving cream and lather. I looked strange without a beard, younger; my face had a feminine look to it. I had not seem my upper lip and chin for at least twenty years. I did the same process t...

The Capture of Sweet Pussy Ch. 03

by SirStroker88 on Sep 17, 2017
BDSM

Chapter 3 – Donna's Story 'Damn Sid, you're right, she is a beautiful sight." Donna was looking down at Pam Martini, the bitch she knew from the office. What she saw now was a frightened young lady on all fours wearing nothing but a collar and a blindfold. She was leashed to a whipping post and quietly sobbing to herself. Donna knelt and stroked Pam Sweet...

No More Secrets

by Gemsissy on Sep 12, 2017
Transsexuals & Crossdressers

I couldn't wait to get home from work. My wife said she had something special ready for me. A month ago, she'd found out about all my sissy fantasies when I forgot to clear my search histories. Instead of divorcing me, she did more research and decided to embrace me as a sissy. Now every time I get home, I strip off my suit down to my panties, thigh highs, a...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Neighbourhood Terror to Sissy Pt. 04

by Fibaro on Mar 25, 2019
Transgender & Crossdressers

The next morning Mark was woken up by a loud mechanical voice. "Wakey wakey sissy, time to start your day, and what better way to start it than with another wank." Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more. Since this had started he had spent countle...

Steve's First Adventure Pt. 02

by gbr2004 on Mar 26, 2019
Fetish

Total fantasy. Do not read if not into gay sex, domination and forced fem. ***** After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He...

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

Cuckold Hypno Assignment

by DivinaTellsAll on Jan 1, 2019
BDSM

My name is Divina. I serve Goddess K. and Madam Vega. I am on a journey to become their perfect sissy girl, and a cuckold slave to Goddess K (who is my wife). The following is a true story of an assignment given to me by Madame Vega, and carried out with Goddess K. Assignment: Watch cuckold hypnosis video pornography, with my chastity cage locked and and...

A Cuckold, Two Blondes, and BBC

by geronimo_appleby on Apr 3, 2019
Novels and Novellas

Okay, a word of warning from the off -- if you're going to be offended by a white cuck husband whose wife gives herself to a group of black men, don't read this piece. If a scene that features black men impregnating white women turns you into a seething ball of outrage, don't read this piece. If you're going to get all snarled up with hate at descriptions of...