Butt Plug Gay Stories

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Sissy Dust Pt. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18 years of age. ***** I'm not a genius or anything but I did get a decent job out of university with my bachelors of chem and started working in a cosmetics company. No not the testing division but in formulations. And it's a boring job really past the actual chem coolness of seeing reactions happen in new things and the way thin...

The Bisexual Boyfriend Dilemma

by Happiestplace on Sep 13, 2017
Anal

I learned fairly early on in our relationship that my boyfriend is bisexual. It's a source of curiosity for me, and apprehension. I'm intrigued by what he's done, with whom, when and where. I also am scared that I, with my large, soft breasts and tight, shaved pussy,am not what he really wants. The problem, of course, is that I love him. Mike, he tells me,...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

The Path to Happiness

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

Author's note, none of the characters are below the age of consent. *** Here I was staring into a full-length mirror, seeing myself glowing in my wedding dress. At 44 years old I never thought the day would come when I would be a blushing bride. As I stared my mind wonders back to my childhood. I was born a boy, Brian Cole. From an early age I knew I was d...

The Making of an Angel Pt. 03

by AngelLawrence on Jul 31, 2019
Transgender & Crossdressers

The making of an Angel part 3. All persons are over the age of 18. *** On the drive home a myriad of thoughts were tumbling through my mind. I'm not gay but I could smell the stranger's cum on my breath and feel my panties teasing my puckered tight little hole. I was aware of my suspender clasps digging into my thighs and the feeling of the sheer nylons o...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

The Poker Party Ch. 06

by tv46 on Sep 26, 2017
Group Sex

"I think I need another beer," Debbie said, intrigued and titillated by Lucy's proposition. The more she thought about it, the more attractive the idea seemed, particularly after she watched Lucy take Jeremy in the ass. "Good idea," Lucy said, "I could use something to eat. How about a pizza?" "Okay, make mine Hawaiian." Lucy headed to the kitchen to grab...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

Magic Dress - Felicity Pt. 02

by SlightlyRude on Apr 9, 2019
Transgender & Crossdressers

CHAPTER 3 One day, rummaging around in the study she came across my butt plugs. "Are these what I think they are?" I said they were. "And how often do you use them?" I said not since she found out about Felicity. "And how do you feel when you use them? Are there any men in particular you think of?" I said I didn't think of men at all, it just seemed nice to...