Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

The Office Ch. 03

by EasilyConfused on Oct 12, 2017
Transsexuals & Crossdressers

Tom awoke with a start. His right hand instinctively fumbled to switch off the alarm clock, but as his hand found the device he realised that his actions did not make the ringing sound stop. His foggy mind could not resolve his confusion instantly but he eventually became aware that the ringing was coming from his front doorbell. Tom shifted from the bed and...

Larry's New Bitch

by sissyneko on Sep 15, 2017
Transsexuals & Crossdressers

I hit a bit of writers block so I grabbed an old half completed story and started back on it. This is the result. I am not the greatest at transcribing the stories as the flow from my mind. While I have given this piece a once over, I am sure that I missed something. If I did I am sorry and I hope that it doesn't pull you out of the story to much. *********...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

Sissy Boy Secretary Ch. 08

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine knew that it was now time to implement her plan to bury her nearest competitor, Bill Andrews... You see Elaine's secretary arranged through the secretarial pool to make sure Tammy, the daughter from next door, got the job as Bill's secretary... As you already know Elaine has used Tammy's information to her advantage and now it seems that Bill was at h...

My First Session with Her

by humbleslave on Sep 17, 2017
BDSM

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider my...

Mum & Sister Dress Him Up

by Quietoldie on Sep 14, 2017
Transsexuals & Crossdressers

"This is my rented flat you know Michelle. It's not fair you being like this with me. I've always been good to you haven't I?" Peter says. He often seems to get into situations like this. He was never very good about sticking up for himself. Now his girlfriend is chucking him out just because she found him dressing up in her things. "I just don't want to l...

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...