Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

You Never Know

by Shady_Lady on Sep 16, 2017
Letters & Transcripts

Note from the Authoress: For any one who has read the Julie Journals they will know I always mention that my stories are a mixture of fact and fantasy. The content of this story is pure fantasy but the characters are fact. For that reason I have not included this as part of the Julie Journals. It is dedicated to a woman who I know and love very dearly. * *...

Getting Kinky with Sarah Pt. 02

by Anoneemuss on Feb 12, 2019
Erotic Couplings

Friday night and I'd come home from work absolutely exhausted. It had been a difficult couple of weeks and I was glad it was a bank holiday weekend. Sarah was home first and a glass of wine was poured for me almost as soon as I'd got through the door. "Here you go, babe, this will make you feel better." I took a swig and kissed her on the lips. "Thanks, I...

My Strapon Fantasy

by libertinaXx on Sep 19, 2017
Transsexuals & Crossdressers

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that...

The Gynarchic Alliance Ch. 05

by gynarchite on Dec 8, 2017
Sci-Fi & Fantasy

Chapter 5 - A trip to the countryside After a few weeks of increasing domestic harmony, Ava organised a trip to the countryside for some friends and her lover. Ava awoke to the dutiful licking of her slave, and had her first orgasm of the day. "Good boy. Now stand Alexi. Go downstairs and fix me breakfast. Bring breakfast up to me." Alexi hurried downstai...

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...

HSPL - Trip to the Sorority

by sissydn on Aug 7, 2019
Transgender & Crossdressers

"After being left on the road by Meghan and Sophie, princess was caught by Cindy and her companions. Zoe, apparently the leader in the group, had informed sissy that she could get back to Sophie and Meghan if she pledged the sorority and joined with honor. If she chooses not to pledge, they would drive her to the other end of town and leave her there in her...

Mistress J's Stepmother!

by Bi_Siamese on Sep 17, 2017
BDSM

(I met Judi when she was twenty five years old and I was twenty. Judi of at the time was a hot 5ft. 4in. tall blue eyed curvaceous blonde with 36C breasts with suckable nipples. Getting her sex education traveling back and forth to New York City on weekends I knew there was a lot that she could teach me sexually and also there were things she really didn't w...

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...

Chastised, Feminized, Sodomized

by Stefani on Sep 25, 2017
BDSM

My name is Kim Lee. I am half Korean and half Chinese. My first name got me teased quite a bit when I was in school. Nor did it help that I am a bit small and slender. Consequently I grew up rather shy and reserved. I never really had many girlfriends, as most women that I ever met seemed to prefer bigger, more macho guys. So I was not prepared at all when I...

The Professors' Dildos

by Boxlicker101 on Jun 16, 2020
Toys & Masturbation

CAUTION: This tale is about two women fucking a man in the ass with dildos, and has an interracial aspect. All the participants are willing and all are over 18, and they all enjoy themselves, but if these kinds of subjects bother you, you probably shouldn't read this story. * On the first day of the fall semester, Professor Patricia "Dixie" Dugan eagerly...