Sissy Lesbian Stories

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Infinite Scroll

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

The New Neighbors (Black Femdom)

by Dunn81 on Aug 12, 2019
BDSM

Hi my name is Julia i'm 42 years old and i'm with my daughter Sofia who's 20. I'm a pretty fit girl who are vegan. I Lost my husband 5 years ago and since that i never dated anyone. I'm a 5'2 brunette with medium size boobs and a medium sized ass too. I weighted around 130 pounds. My Daughter is 5'5 big boobs and small ass. She trained at the gym a lot since...

One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

Once Upon a Laundry Ch. 02

by thekestrelkid on Aug 7, 2018
Transsexuals & Crossdressers

At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt a...

Sarah Visits Chicago

by SarahCD on Sep 19, 2017
Transsexuals & Crossdressers

I was on a business trip to Chicago and I was staying at a nice downtown hotel. I decided to go out for the evening dressed as Sarah. Well, what did I have to lose? No one knew me there and I would never see anyone that I met again. I put on blue lace panties and a matching bra. It was a warm summer evening and so just I wore an ankle length blue strappy su...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

Sissy Pantyhose Twins Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Twice The Fun... Part One... My Slut had received her orders in the envelope which was always left on the kitchen counter before I left for work. She was to perform whatever was mentioned in this envelope, each day, without question -- either during the day if so asked, or to be ready for me when I get home. Whether it was a new outfit, a specific outfit,...

OMG My Daddy’s a Sissy (Prequel)

by fittexanman on Aug 22, 2018
Fetish

All characters are purely fictional and of legal age (over 18). * I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn't take us long to realize that we weren't like the others at this school. As it was located in the Southern part of the country, our co...

Suspected Affair - Confirmed

by 69Jance on Jun 1, 2020
Transgender & Crossdressers

Second Part of Suspected Affair After confirming my suspicions, I was looking forward to seeing what was next with a hot wife and a pair of handsome twins. Actually though, from what Maxwell said, they all were looking forward to bringing me out of the proverbial closet and see what is next for their new sissy. Maxwell had said "We should go meet Heather a...