Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

Hit The Right Spot

by Gregory_Andrews on Sep 14, 2017
Fetish

My name is Jack, and man I have a wild story! Let me give you a brief back story before I begin to take you down my latest sexual journey. My girlfriend Kelly, well more like long distance girlfriend because I recently had to move due to my job changing location. See, we never lived together and she let me fuck basically any girl I wanted. She usually got al...

Schoolgirl Homework Ch. 02

by Templar_Writer on Apr 10, 2019
First Time

All characters in this story are eighteen years or older. So, having more than two hundred followers feels like a bit of a milestone, meaning I am considering having a Q & A. If I get at least ten good questions I will post it. ***** After another week of experimenting and even twice more with Neville, during which she even noted Neville had started to im...

Sailing Away Ch. 04

by Jasmyn_White on Jan 22, 2020
Fetish

Chapter 4 - the strapon When I got back, Lacy was done reading. This was evident by her wearing the red feeldoe in her favorite Aslan leather harness, stroking it, and watching the door for me to come in. "How's Captain Brian?" she asked. I told her how our conversation went. She seemed pleased at the idea, but wanted to know more. "Take off your cloth...

Pegging With Lisa

by slutfreya on Sep 25, 2017
BDSM

Lisa and I have been swinging for a number of years and have always been pretty open with each other sexually. She is a beautiful, 42 year old bi, blonde standing 5'7" and a trim but shapely 135lbs. Her shaven pussy is absolutely sweet and she will squirt, usually when with other women or new male lovers. I'm Al, your average guy, 48, 6', 235lbs (working on...

Undercover Mistress Pt. 03

by nexomorph on Nov 26, 2019
BDSM

I was feminized, depraved, used, abused, and happy. I felt her kiss on my cum stained lips. Her tongue penetrated my mouth playing with mine in a whirlwind. Aury was one hell of an MILF, with a dark side, and I was a goodfella with a submissive tendency. A perfect match for a hard and deep play. Aury laughed upon me, lifted me up and kissed me once more. Sh...

Mr. Asshole, My Submissive Super

by Goddess_Meanie on Mar 7, 2018
BDSM

Let Me tell you about me. I mean, what I want you to know. I really do enjoy the life I live, I wouldn't trade it for the world. It wasn't always good though. All my experiences have brought me to where I am today. I like to think I'm a great judge when it comes to people. I can spot a weak man a mile away and once i have them in my grasp I do what I want wi...

Seductress & Daemon: Sissy Pt. 01

by SeducedKnight on Sep 15, 2017
BDSM

After Eating out my Seductress for the last hour, we hear a knock at the hotel room door. "Go open it." I go to the door dressed only in my rubber wrist and ankle bands with heels and a pink crotchless panty, I have a plug in my ass and a cold metal cage on my cock. I open the door wide in my full nakedness to reveal a prettily dressed sissy outside. "...

My Wife Caught Me Cross Dressing Pt. 03

by RhondaParker54 on Feb 12, 2019
Transgender & Crossdressers

The next morning they all woke late, well 10 am, but as it was a Saturday, it didn't matter. After the usual morning greetings of quick cuddles and kisses and was quickly agreed breakfast was top of the agenda, being in their lingerie didn't bother anyone except Jane who slipped her discarded panties back on and put her breasts back into her corset. As had b...

Valerie Finds Her Man

by escriterra on Sep 25, 2017
Fetish

Valerie Nicholls had found her motivation to work out regularly. His name was Connor, and he owned the gym that was incongruously tucked away behind an upscale European furniture store in what most people probably assumed was an area of tony shops and places where you paid four dollars for a small pastry that was wrapped up for you to take away in a small bo...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...