Terror To Sissy Stories

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Humiliated by Wonder Woman

by littleerection on Sep 17, 2017
BDSM

So it's a nice day today. I decide to go outside to get some fresh air and go for a walk. I wanna soak in the early spring cool breeze. I find myself going through the woods. Eventually I end up near the end and I see her past the trees standing alone on the cliff: The one and only Wonder Woman, looking out over the town! I couldn't believe my eyes! I've alw...

Tranny G, Gang Bang Queen, 5

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I apologize - I had no idea I would continue to write about Chris and Tranny G or I would have numbered the stories. These two beloved people are so rooted in my life and there is so much to share. I never imagined I would share these stories with anyone. Since my husband and I became swingers, I had no idea what my interests would be, I just simply plunged...

A Missy Affair

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I knew I was being careful. I thought I was being clever. But I never thought I could be caught in such incriminating circumstances by of all people my sister-in-laws husbands parents. I was playing the good brother-in-law by doing a bunch of minor home reno's for my wife's sister and her husband. To my delight they trusted me implicitly and left me alone in...

The 70's Weren't All Care Free

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

It was the 70's. Young, carefree, long-haired hippie, away from home, traveling around the country - having a ball. A couple guys I met and I decided to go for some beers. The local Y was in a sleazy part of town. So we ended up a pretty seedy bar which was hosting a rather bizarre strip show. At another table was an older guy that had been at the Y that aft...

If Women Ruled The World Ch. 02

by chronoxxx on Sep 15, 2017
Fetish

I arrived at the bottom of the stairs of Sulihall College of Etiquette for the final time with my luggage, ready to meet my new Mistress. Nothing seemed real as I headed for the reception desk where 3 Ladies stood talking to each other, their towering high heeled silhouettes casting a shadow from the bright, unknown world outside. My mind was in a fug when I...

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...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

Tales of Sub Asian Sissy Ch. 02

by subASIANsissyJADE on Apr 9, 2019
Transgender & Crossdressers

Once the door closed and I heard the deadbolt latch, I panicked. How on earth could I walk to my car in my current state! I stood there, my heart racing, in my black fishnet thigh highs, no panties, a glass butt plug with a big pink fluffy tail firmly lodged in my tight asspussy, my black lace bra, and my face and chin and neck covered in drying cum. I des...

The Farm Ch. 02

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Trembling with fear I squat naked on the floor where the man who dragged me down the hall has dropped the lead attached to the collar about my neck. Starting with fright at his every sudden movement I watch him sort through piles of clothing sniffing back cum scented tears. Eventually he holds up a pair of girls panties that he inspects closely. With a sat...

The Visitor Ch. 06

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

The shower when it came on surprised me, he had the shower head in his hand and played the spray up and down over my body, I blinked, recoiling in my shock and looked up at him, the shower gel squirted at me. "I like a clean sissy" I just hated that alien electronic voice so much, but I knelt there in front of him only too glad to be rid of the smell of hi...