Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

The Awakening of a Sissy Pt. 08

by sissyjolie4u on Mar 30, 2020
Transgender & Crossdressers

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

Humiliated Stable Sissy

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

After a long week at work, I was looking forward to a quiet weekend of relaxing in front of the TV with a beer, but my fairy godmother had other ideas. "Good morning sissy," came her stern voice as soon as I woke up Saturday morning. I whimpered, immediately knowing I was in for a humiliating weekend. She frowned, not pleased with my whimpering. She's an ol...

Humiliated Sissy Husband Ch. 04

by rik581 on Oct 9, 2017
Transsexuals & Crossdressers

"A Second Helping" "Come along now Max, the guys will be here soon. You still have chores to do first before we are ready," Tonya called out from the open motel room door. The door was wide open as she waited for Max to get out of the car and come in. She had parked in front of the room but across the parking lot. It would be a good 50' walk for him in 6"...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

Ashley Gets a Real Fucking

by Equinox31 on Sep 13, 2017
First Time

*This story is fictional. Don't read if things such as cuckolding, and male on males offends you* * This is the story of how a college girlfriend turned her wimp boyfriend into a cuckold. Mike and Ashley started dating when we were both 16 and they were now 21 but went to different colleges. All of Mike's friends would tell him to watch out, and that she m...

The Babysitter Takes Over Ch. 02

by sissysherry2 on Mar 20, 2018
BDSM

Chapter 2: The party "Ok bitch, I'm going to invite my friends over tonight for a party. I'm going to text them an invite and I want you to do it. Now go over there and start talking. And you better make it good or I'll post the pictures on my Facebook page." I went over to the corner and started talking while Teri got her phone out again and pointed it at...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...