Sissy Lesbian Stories

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A Husband Named Cathy Ch. 02

by cathynylons on Sep 18, 2017
Transsexuals & Crossdressers

When Toni had finished inserting my butt plug she turned to me and said, "There, now you'll see how much more feminine you walk. We will be going out later this afternoon so I think now would be a good time for you to go to your room and think about your behavior yesterday." I went to my room and sat at the vanity and began applying my eyeliner, eye shadow...

Sissy Crissi Ch. 02

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2 -- Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and man...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Graduate Studies to Gay Pt. 02

by jamtby on Apr 9, 2019
Transgender & Crossdressers

After the night at James' apartment the previous quarter, I had tried to put all that out of my mind and concentrate on school and be normal. I did see James once on campus and he asked how I was doing. He hoped I had gotten a good grade on that paper I was writing when I met him at Jimmie's that fateful Friday night. He also said that if I wanted to earn so...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Our Sissy Slave Ch. 02

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that....

Life With Miss Ida Ch. 02

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

When I woke the next day, Saturday – late as it was due to the long evening earlier – I started playing everything over in my mind again and kept coming up with the same result – there was nothing that suggested to me that Ida would not welcome Georgia into this relationship – she never once turned me off, nor seemed turned off by how I was dressed. She didn...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 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 dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...

Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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