Sissy Boyfriend Stories

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The Perfect Age Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It wasn't long after I became his lover that he had me seeing other men. The first time was at a party he took me to several months after I started seeing him. He had me go down on a friend of his while he watched. Assured me all was okay, it would be 'safe'. 'Just do it, you'll do that for me, baby, right?'...I did. I actually enjoyed it. I found out early...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Sarah was Made into a Sissy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

It was Saturday morning and I decided to get my laundry done before going out for lunch. I took my stuff down stairs to the basement laundry room, loaded a washer and started the cycle. I was about to go back up to my place and wait for my things when I noticed a basket of laundry on the table. I went over and found a mix of girls and guys stuff, I guessed t...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

His Sissy Bitch Ch. 06

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tuc...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Jade in Control

by Slutboy88 on Oct 26, 2020
Fetish

I woke up still lay on the floor with my hands tied behind my back. I could still taste my own cum in my mouth after Jade had made me eat it from her pussy the night before and my ass hole was throbbing from the brutal fucking she had given me with her strap on the night before. My mouth was dry and I felt disgusting. I desperately wanted Jade to untie me so...