Sissy Pills Stories

15,811 results
Orientation
Length
Source
Infinite Scroll

Quenching Thirst Ch. 03

by PutItInMyMouth420 on Sep 25, 2018
Transsexuals & Crossdressers

Warning. This story is extremely dirty and graphic. Please read chapters 1 and 2 first. *** I went back to the shower after mr. Warden had owned me. I knew that at this point I would be changed forever. For sure I no longer identified as straight. I knew no matter what happened I love cock too now. That was the most humiliating, embarrassing experience of...

Beauty and the Bully

by xaitonnar22 on Sep 13, 2017
Transsexuals & Crossdressers

The sun was high in the sky, yet a cool breeze blew over the busy metropolitan city of Kingston, California. The students at the local high school, Kingston High, were outside enjoying their half hour of lunch under the warmth of the sun high overhead. Jason Lane darted nervously between the buildings on his way to his next class. Most of the other student...

Creating Ginger Ch. 04

by Ms_Allison on Jun 8, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...

The Landlady Pt. 01

by Manndee on Apr 3, 2018
Transsexuals & Crossdressers

I had been lodging at the address for 7 months now. When I first saw the advert, it made me smile because the lady advertising the room seemed to be so eager to have a lodger. You could see it in her photo. It was not my first choice when I looked through the properties that were available online, but it was the cheapest, and funnily enough, it looked the ni...

My Son In My Clothes Ch. 01

by LeggyVicky on Sep 14, 2017
Transsexuals & Crossdressers

I'll never forget the day it started, the day we caught him. My husband Nick and I had gone out with friends for our anniversary. We intended staying the night at a hotel, but my husband was on pills so he couldn't drink, and we decided to drive home. I pushed open the bedroom door and the giggling and smiles changed to gasps and shocked looks. Staring bac...

Cuckold Chronicles: Paul

by deltonaman2man on Sep 13, 2017
BDSM

Friday night is my night out with the guys. I go to a friends house and we have a small neighborly poker game. My wife likes the time alone, so she stays home and does whatever it is that she does. I don't get out much since my heart attack ( at the tender age of 48). I'm in my mid 50's now and we have been together for over 20 years. We are still very much...

Ms. Margo

by lyzunchik on Apr 3, 2019
BDSM

This is a partially true story, with some embellishments and enhancements out of my own fantasy. I'll allow you, dear readers, to wonder what is true, and what is contrived, where truth ends and fantasy begins. Enjoy. ;) Mistress Margo was waiting for me in the reception hall of Saint Petersburg Airport. I had been there a couple of times before, but this t...

From Husband to Castrated Sissy

by meeah on Sep 25, 2017
Transsexuals & Crossdressers

"Oh my god!" My wife looked up over the muscular shoulder of the huge black guy nailing her on our bed. Her long tanned legs wrapped around v-shaped torso. "Hi honey. What are you doing home early?" "Kelli what the fuck's going on here?!" At that, the black guy turned and shot me a nasty glance. "What's it look like we doing, genius? I'm dicking your old...

Just the Way You Are

by Sandwiches_Are_Good_Too on Sep 16, 2017
Transsexuals & Crossdressers

"No! You are not taking my babies from me!" "This isn't about you! Its about providing my sons with the best home environment, and that's not with the woman who may be high as a kite at any given moment!" "If you had paid an ounce of attention to anything that was going on in your 'home environment,' you would have noticed that I've been clean for twelve...

Angel Learns My Secret Ch. 02

by Angelscuck on Sep 16, 2017
Loving Wives

I couldn't believe my ears. After telling me she would not cuckold me, my lovely wife was dressed to kill and about to go out on a date. "But you said you would not fuck other men, it was just a fantasy!" I exclaimed. I said I would not fuck other men, nothing was said about dating them. Dan is an old friend of mine. He loves opera and is taking me to see t...