Milton Sissy Kilt Story Stories

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Letter From Montgomery County

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, Loving your "Taped Confessions" series. I am known as the Bitch of Bethesda, for I've really trained a lot of hopeful couples in the femdom life, all over Maryland, D.C. and Northern Virginia. Enjoy! Rhyce, torturer of Chevy Chase Crybabies... "So how goes it with Milton? Did you up the ante like you said you would?" "Jesus, Vermillion,...

She Wears The Trousers

by Quietoldie on Sep 19, 2017
Transsexuals & Crossdressers

I knew that Wendy was a strong willed, ambitious woman when we met. She had been active in a left wing feminist group at University and had landed a good job with prospects after leaving. In contrast I am not a high achiever and dropped out of Uni after a couple of years. Since then I have had a number of low paid jobs and am presently unemployed. To be hone...

Jake Lied on his Resume

by Bobdog82 on May 15, 2019
Exhibitionist & Voyeur

There was this old, but well kept, building at the end of the block. Built back in the 1890's, brick building including the corner, windows and balconies wrapping around and continuing on down to the edge of the next building. It's a beautiful building. It was for sale for the longest time, till just recently. A corporation bought it, one of their companies...

Service, Cock Sucking Panty Ass

by Bluzworld on Sep 16, 2017
Transsexuals & Crossdressers

I consider myself a normal red blooded man who enjoys being with a woman but I have a secret. I love wearing panties and I love being spanked in them. My Lover Blue has yet to experience that with me and I'm excited to find out just how she reacts to our next date. My other secret is that I've always wanted to suck a cock, I know it seems odd since I also en...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Constrained in Corsetry

by susanxdresser on Sep 16, 2017
Transsexuals & Crossdressers

Although I am not into serious bondage I love the erotic pleasures of wearing corsetry and other tight feminine garments next to my skin. When wearing suspenders and stockings I love the erotic sensation from the tightness of the top of my stockings gripping my thighs and the suspenders brushing against my thighs as I walk, as I envisage my suspender belt an...

Trust Ch. 03

by kellyhockey on Sep 16, 2017
Loving Wives

Chapter 3: The Accident Mike went to work on Monday. Around 9:30 am Mike got a call from Jamie. Mike's voice mail system recorded the whole call. "Hey dick head. I am going to fuck your wife tonight. That's right Marine boy. I am going to butt fuck and then cum in her mouth." Jamie went on for about twenty minutes when Mike figured out where he may be call...

Returning Home Ch. 02

by DG Hear on Sep 13, 2017
Romance

Authors note: I've been getting a lot of comments asking about ‘Techsan'. He passed away last month, I think due to intestinal problems. I don't know any more than that. He will be missed by many of us. Again thank you to Mistress Lynn and LadyCibelle for making my story more readable. You may want to read chapter 1 first if you haven't done so already. C...

My Father, The Maid Ch. 03

by SissyOona on Dec 12, 2018
Transgender & Crossdressers

A Case Of The Mondays By Sissy Oona. Sleep came easy that night, I was frankly a bit worn out from the amazing sex we'd had. I was awoken by the door to the room opening and the click of heels on the wood floor. I cleared my weary eyes to see my father entering the room carrying the breakfast tray I had become accustomed to seeing in the morning. Noticing...

Nerds of Hollyweather Ch. 03

by eeric on Sep 16, 2017
Interracial Love

This story is a part of the Blackedmerica series, which is set in an alternate history. ***** Chapter 3 Up on the second floor, in Milton Hobson's science class, Scott Olson finished up his presentation on early 20th-century flight in front of the class. "So if it hadn't been for the Wright brothers..." Scott showed an old photograph of the two black...