Sissy Plug Stories

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Infinite Scroll

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

Covid 19 - Pete Turned into Charleigh Pt. 03

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes." Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certa...

My New Friend Amy Ch. 03

by DRobbie06 on Dec 23, 2019
Fetish

As I drove home that evening I had the replay of the days events running on a loop in my mind. I can't believe I paraded around in panties at lingerie store in front of strange women at the instruction of my new mistress. Hell, I signed a contract to obey her no matter what she says! Then I begged to jack off in front of her. I'm even a panty wearing sissy n...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Covid 19 - Pete Turned into Charleigh Pt. 04

by His_fag_wife on Jul 27, 2020
Transgender & Crossdressers

Red unlocked the locks, unclasped the clasps on the box and then popped the lids back on the two bottles of poppers, but popped them in place for later. After this first session being so much of a hit, she thought Charleigh might be in the box for some time, every day for the coming weeks, if the lockdown remained in place for that long. At least then the du...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

Mistress Patty Ch. 02

by timeagain93 on Sep 17, 2017
BDSM

Mistress Patty was brushing her teeth in the motel bathroom; she paused to spit and continued talking. "Y'should see what my sister does to her husband! You're getting off light, believe me!" I could only nod. I was blindfolded, butt plug in my mouth, hands cuffed behind my back on the toilet. She uncuffed me and removed the plug. When the motel door slamm...