Sissy Butt Plug Stories

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Orientation
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Infinite Scroll

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Aunt Pamela and Leslie Ch. 02

by fantaseeboy on Jun 25, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** The days passed incredibly slowly after my meeting with Aunt Pamela. She dominated my dreams and fantasies. She often crossed my mind while in class and I would wind up with an erection and squirming in my seat with the memory of the spanking she'd given me and the reward I'd earn...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...

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...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Chrissy the Sissy

by Ide32 on Sep 14, 2017
Transsexuals & Crossdressers

Part 1 The Bank Job Chris or Chrissy as he calls himself has the job of his dreams, he works at a sperm bank for futas. His job is to dispose of samples that are non-viable, low sperm count etc. All day long he dreams about the creamy, yummy cum from futas waiting for him to dispose of it. While he is supposed to put it down the sink, he has a preferred met...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...