Boipussy Stories

101 results
Orientation
Length
Source
Infinite Scroll

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

The Classmate Ch. 03

by EricSilence on Sep 14, 2017
Transsexuals & Crossdressers

Oh, Victoria. I couldn't explain to you what was going on in my head if I tried. One minute, I'm a straight, horny, pussy-loving male, and the next I'm guzzling cum from the cock of the most beautiful girl in school. Then, I spend the next six weeks obsessing over her, obsessing over my own tangled sexuality, and when I finally see her, ready to confront my...

In My Bedroom...

by Lea1234 on Sep 12, 2017
Transsexuals & Crossdressers

Daddy walks in to my room and lays down in bed, right behind me. He starts caressing my stocking covered legs...daddy likes it when I lay in bed in my sexy lingerie. I'm wearing a white garter belt, white stockings and silky white panties. Daddy caresses my sissy bum as he starts kissing my neck and my upper back. I push back my lil sissy butt against his wa...

A Glorious Adventure

by Bobbirox2 on Oct 5, 2020
Transgender & Crossdressers

It was an unusually warm Thanksgiving evening in upstate NY, and I was called out to make an emergency run for my delivery job. I should have checked the weather better before leaving the house to make the run, as my route usually takes me about 4 hours each way with me expecting to get home by around 9AM if everything went well and I didn't stop anywhere ot...

COVID-19 - Campus Closed

by puzziboi on May 12, 2020
Transgender & Crossdressers

"Momma, they're shutting down the campus on Friday," lamented the college junior. "I figured they would. I've been on the phone with Aunt Nettie. You can stay with her for the time being since she's close." "Doesn't she already have a ton of people living with her." "Patrick..I mean, Prisha," she swallowed hard. "There's just not a lot of options right no...

Maid The Wrong Bet...

by Lea1234 on Sep 25, 2017
Transsexuals & Crossdressers

Part 1 Around the end of my last high school year, my curiosity for crossdressing had just emerged, but I didn't explore the fantasies too much as I thought it was just a phase. The following fantasy is something I have dreamed about for years... A friend of mine, Peter, was into the same video games as I was, and we made a bet on who would win the next ga...

The Making of a TLB Pt. 03

by TheMarlboroMan on Sep 23, 2019
Transgender & Crossdressers

I suggest you read parts one and two to pick up a man's journey to womanhood caused by the woman he loves, his wife. Some of the items used may not be available in the market today. Rest assured they will be. The key to any conversion is the manipulation of one's mind. What the wife fails to remember is that each one of us has freedom of thought. I got up e...

A BDSM Sissy finds Daddy Ch. 01

by Secret_sissy712 on Jul 13, 2020
Transgender & Crossdressers

As I walked back to my van after finishing up the apartment complex two men pulled up in a van and park a few spaces away. As I open my door and I take my tool belt off my shirt rides up just enough for them to get a sneak peak at the red satin thong panties popping out the top of my jeans. The fact that they do is no mistake. I wear them high and the jeans...

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...