Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

Instructional Jerkoff Sissy

by dirtywordygirl on Aug 19, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

Julie and the Cherry Patch Ranch

by SissyJane on Sep 16, 2017
Transsexuals & Crossdressers

It took a lot of research and careful arrangement of my travel plans. But I was successful. I'd found a feminization fantasy business outside of Las Vegas that I could visit before my conference began. The Cherry Patch was just what I was looking for. A call ahead confirmed that I could get just what I wanted. I ended up packing two extra suitcases with alm...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

Slave Ch. 04

by slaveheathen on Sep 25, 2017
Fetish

Note: Yup. Fetish story. Don't like it, don't read it. Comments and constructive criticism are welcome. On with the depravity... I slept late the next day, oddly enough. Couldn't have had anything to do with being utterly exhausted. Oh, wait. Yeah, it did. I was ready to crash after the shower, but Mistress Kay made me eat her pussy for an hour before sh...

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...

Slave Ch. 01

by slaveheathen on Sep 25, 2017
Fetish

My name is slave. Of course, that's not my real name, but for the story I plan to tell, it will do. For the record, I'm a bisexual submissive male. There are few who know this fact. Common enough story there, I suppose. Truth is, my family and friends could never accept my lifestyle, so that part of myself stays safely locked away. But behind closed doors....

Becoming Her Whore

by ecdilettante on Sep 19, 2017
BDSM

Last time we parted, you told me that you were going to fuck me when we next met. You loved the fact that I've never been taken with a strapon and you promised to be gentle, in the beginning. It sent a shiver of excitement and fear through me, which made you smile. I can imagine heading to your small apartment, anxious and excited. I haven't cum for days a...

Confession Pt. 05

by holukukkar on Jul 17, 2019
Transgender & Crossdressers

After I finished doing my nail makeup Mistress comes to me and notices the work I have done and she was very happy with that and then she told me that she has chosen a shade of matte red lipstick. Me:- Can I see that shade mistress? Mistress:- Yes, it's a bright red shade. Wait let me show you. Me:- okay mistress. Mistress:- Here we go. Me:- (After seei...