Castrated Sissy Boys Stories

65,188 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Zamindars Pt. 02: Thakur & Champa

by prithvik1947 on Jun 18, 2019
Group Sex

In Zamindars Part 1, I had described the situation that I witnessed on arriving at my friend Vivek's estate. His father, Subhash (The Thakur) was openly having a sexual relationship with Champa who was 20 years younger to him and the wife of his driver. Part 2 is more about what I saw between Subhash uncle & Champa. Champa was sitting in uncle's lap while h...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

For Marion's Pleasure Ch. 03

by MarionsPuppy on Dec 3, 2017
Fetish

"Crawl over to us puppy. As you can see, your Master is having a post-coitus snooze. He has fucked me wonderfully as usual, as you never could, and his ejaculation is starting to ooze from Mummy's cunt lips. I need you to be a good clean up boy and swallow all his jism before it drips onto the sofa. That's it pet, long slow licks from my ass all the way up t...

Zamindars Pt. 03: Unbridled lust

by prithvik1947 on Jul 16, 2019
Group Sex

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** In 'Zamindars Pt 2" I had described the shameless and lusty fuck session between my friend's father - The Thakur - and his young maid and fuck toy Champa. It was now almost 3am in the morning. Uncle emptied himself inside Champa's cunt right there in the living room on th...

From Husband to Castrated Sissy

by meeah on Sep 25, 2017
Transsexuals & Crossdressers

"Oh my god!" My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?" "Kelli what the fuck's going on here?!" At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...

Feminizing First Step Ch. 07

by antares34 on Aug 24, 2020
Transgender & Crossdressers

I was meeting my internet "daddy" for the first time today. His last text message to me had been very clear: tie myself to the motel bed and wait for him to arrive. I stared at the antique bed with its black metal frame and headboard, wondering to myself if this was such a good idea. This rundown motel had been hard enough to find. I had never been to this...

Helen, my Wife and Cuckoldress

by siscuc on Sep 12, 2017
Fetish

She stood before me, eyeing me up and down shaking her head. "So this is what really turns you on, hey?" she said mockingly as she slowly ran her fingernails over my cock through the lacy panties she had told me to wear. "Look at you getting all excited but your dicky is so small it can't even escape from those panties!" She laughed as she turned on her heel...