Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

Boy with the Butt Pt. 03

by HornetNest471 on Jan 28, 2020
Fetish

*Knock! Knock!* I can't stand my fucking mom. Was it too much to yell at my girlfriend and kick her out of the house when she found us? My answer would lean towards yes. Did she take it a little too far when spanked and verbally degraded me? Definitely. But now, even she might be doing too much. The door in front of me swung open slowly as the head of a...

Strapon Dream Cum True

by AfroerotiK on Sep 13, 2017
Fetish

Edward sat at his computer screen, staring at his monitor until his eyes started to close from exhaustion. Every once in a while, he would get so horny, so desperate to experience his fantasy he would stay up all night just stroking himself and looking at porn, desperate to feel . . . it. He had pretty much resigned himself to the fact that he was never goi...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

I Want to Peg You

by pwlrstr on Sep 25, 2017
Fetish

I slip my hand around your waist and pull you into me, into a tight embrace. I'm wearing four inch heels, but you still stand a couple of inches taller than me, looking down into my gaze, an excited sparkle in your eyes. You run your hands through my hair, pushing it away from my face so you can see me better before coming in for a kiss. My hands run from yo...

The Gynarchic Alliance Ch. 07

by gynarchite on Dec 16, 2017
Sci-Fi & Fantasy

Chapter 7 - An intimate day with friends Lonna had been happy subwife to Ava for two months now and was looking forward to another weekend with Ava and Alexi. After the first month of enforced nudity, Ava had granted Lonna occasional permission to wear clothes. Today, Lonna wore one of her growing collection of short PVC dresses, which showed her shaved sex...

Saturday Night Slut Pt. 03

by Sweetlittlefreak7 on Aug 26, 2019
Group Sex

Hey again everyone! This is Part 3 of my ongoing story of Erika submitting to her Mistress Kaylee, in which Erika is finally used by the party goers. You can read this part without having read the others and still basically know what's going on, but what fun is that? :) I'm still deciding where to go from here with this and also not sure what people think of...

Your Waitresses

by weluvhose on Sep 15, 2017
Transsexuals & Crossdressers

We have not submitted anything for almost a year as daily life as certainly been in the way for ALL of us. My wife and I decided this one would be a slight change to the previous submissions. It is all fantasy but we both would enjoy bringing this one to "true" life if ever possible. Enjoy and we always welcome any comments!...

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Play As I Say

by mobyCock on Sep 12, 2017
Group Sex

It was one of those afternoons after it had rained in the morning where it was unpleasantly muggy. Even inside, even without having looked out the window, you can feel a sense of lethargy in the air that just discourages consideration of heading out, especially if you've been inside most of the day. It's hard to meander around a one bedroom apartment, but I...

The Gynarchic Alliance Ch. 04

by gynarchite on Dec 4, 2017
Sci-Fi & Fantasy

Chapter 4 - Bought Ava led Alex out of the processing building, leading him by his leash. Alex crawled on all fours, impeded by the humbler around his balls. His tail stuck up from his behind, wagging as he moved forward. His new mistress led him to her personal vehicle, and had him crawl up into a caged off area in the back. Slave males who stood upright w...