Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

Controlling Sissy Janice Pt. 02

by sissy_janice on Jul 6, 2020
Fetish

Lilly instructed me to go upstairs and strip, and to remove my wig. "I have to get some bags out of my car. I want you naked and in the shower when I come back." I did as I was told. I was in a bit of a fog. I was now going beyond what I'd ever contemplated. Even if I'd worked up the courage to tell Lilly the truth, the most I'd have hoped for was the occas...

Dressing Room Punishment

by bluesbirds on Jun 1, 2020
Transgender & Crossdressers

I immediately knew I wanted the plain black sweater on the closest rack to the left. It was cut off at the belly button, but it looked warm and cozy. It clung tightly to the mannequin, the breasts noticeably perky under the fuzzy fabric and highlighting the curves inward to the hips. Tight sleeves came down about halfway to the elbow. It wasn't particularly...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...

His Sissy Bitch Ch. 05

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I'm scared to death. Feel apprehension, I've never been 'outted' before, never been out in public dressed fem. He will not be dissuaded, told me I had to do it. As I sit and try to concentrate on work I can see him across the hall in his office. See the people he meets with, know he could out me to them if he liked, and I know tonight I may be seen by any on...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Neighbourhood Terror to Sissy Pt. 09

by Fibaro on May 27, 2019
Transgender & Crossdressers

While Mark was going through his night time ritual and sleeping Lisa was at CC's getting licked to orgasm after orgasm by Stephanie. The more she learned about sissies the more she knew it was what she had always wanted. She had never been with a such a pretty girly girl like Stephanie, and definitely never with anyone who was that good with a tongue. The th...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Sammi's Place in College

by Sissy_Sammi_ on Dec 17, 2017
Transsexuals & Crossdressers

Sammi was up at seven AM, as usual, fully dressed and dolled up and tidying up the suite. Something had broken in her brain at this point, she had been re-wired. Her life had taken some drastic turns, and who she was and what drove her had been completely replaced by something new. Sam, in the past, had been at the helm and would occasionally allow Sammi he...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...