Sissy Whore Stories

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His First Taste of the Real Thing

by 2easy2 on Sep 19, 2017
Fetish

My girlfriend, Angie, has been dressing me in women's lingerie and pegging me with her strap on dildo for a couple years now. It started with an occasional pair of satin panties and quickly moved to sexy little nighties, stockings and painted toenails. As bad as I hate to admit it, I absolutely love it. It's all I think about anymore. I love the submissive...

Sharing

by thetoy on Sep 12, 2017
Fetish

My wife and I over the years had developed a relationship between Domina and submissive sissy that was utterly grounded in love. Indeed, that was the only thing that had allowed us to go as deeply into the perverse and bizarre as we had. She had a marvelous ability to anticipate just what I would be able to stretch to reach. I trusted her absolutely and deli...

Mike the Gang Bang Bitch

by sissyneko on Mar 17, 2020
Transgender & Crossdressers

Standing in the bathroom wearing just his little pink bikini panties and stockings, Mikes gaze was transfixed. Not on the panties, the usual draw of his lust, or even his white thigh high stockings with their little pink bows at the top. None of that drew his attention, it was the bathroom itself, it was run down, dingy and in the worse part of town. But non...

Megan's Bitch

by magicrub on Sep 14, 2017
Fetish

"Why are your clothes still on?" demanded Megan as she smacked her bitch across the face. "I'm sorry Mistress..." bitch replied before being sharply smacked again. "I did not give you permission to speak bitch!" replied Megan. "Besides, a Mistress does not have a cock like this one! Does she slut?" "No Mistr..err Master?" replied the bitch, starring at t...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...

Miss Guided Pt. 02

by MissMarianne on Mar 26, 2019
Transgender & Crossdressers

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, f...

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Master Gene's Email Response

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Back at home that night I kept thinking of what had transpired that morning with Master Gene while still wearing my cum stained panties as Master had told me I could only remove them to shower. Otherwise the pink thong panties that had been soaked in cum would remain on at all times until I was told I could switch to other panties of mine. Was this a sign Ma...

Mr Derrek

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

The room is filled with the sounds of sex emanating from the wide screen tv. On screen a sylph of a gurl is on display all fours on a small low table surrounded by a sea of men in various stages of undress. The slim smooth skinned gurl is dressed in a short flared skirt that frames her sweet ass beautifully in layers of ruffles and lace with her pretty match...