Permanent Sissy Chastity Stories

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Orientation
Length
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The Beauty Therapists and the CD Ch. 03

by satinpaul on Sep 15, 2017
Transsexuals & Crossdressers

The 3 women all go back to the bathroom and close the door, I sit on the bed waiting, anticipating them coming out to then get dressed in their maid outfits, after 10 minutes they come out wearing jeans and t shirts, I'm so frustrated and disappointed. I ask what's going on and Lucy's says they have to go, something has come up (not just my cock then) and...

The Hot Blonde Neighbour Ch. 03

by InvisibleCocks on Sep 19, 2017
Exhibitionist & Voyeur

For a long time I just stood there, transfixed, enjoying the fresh memories of the amazing fuck I'd just had. For a day or so I pretended to be studying, but actually I was daydreaming, about her perfect breasts, the taste of her pussy and the amazing sensations she gave me. I was also starting to realize that she was as much of a bitch as she was beautiful....

Girls in Real Estate

by JackorJill on Sep 12, 2017
Transsexuals & Crossdressers

You have to love the ladies who work real estate for a living. They work hard, you know it is, visiting those beautiful houses on the shore, having a few cocktails for lunch. All kidding aside, working weekends gets old and these ladies do whatever it takes to make a deal happen. I found out first hand how much they work firsthand. My work truck had blown a...

Birthday Wishes Ch. 01

by b_wishing on Sep 16, 2017
Transsexuals & Crossdressers

Everyone in this story is above the age of 18 and no one was harmed in the writing of this story. Look for me on Yahoo messenger as b_wishing for some kinky play like this story. Please like my story too. KISS KISS When I walked in the house I felt like this was my hideaway. Always so relaxed is the way Uncle Woody and Aunt Sandy's house is in the winte...

A New Person

by Reecer on Aug 18, 2017
Fetish

I thought stuff like this didn’t really happen. But I guess it does. I had been married for 7 years, and our sex life sucked. I guess it might have just been the seven year bitch, but we didn’t seem to agree on anything anymore. We only had sex on nights when she was horny, which actually was more often than one might expect. If I would go down on her that w...

House Bitch 01: Panty Slut

by gomez8 on Sep 13, 2017
Fetish

"Suck it, bitch! Suck it, you cunt!" Mistress was in fine form. She and Bec had just had a tussle. It had ended predictably, erotically. Mistress J had forced Bec to surrender and was now enjoying her well-earned delights with a 7-inch black strap-on. Bec's eyes were moist, her skin flushed from the contest, she glowed with heat and energy, and shined as she...

Time for a Kit Kat Ch. 03

by cashcrunch on Sep 17, 2017
Fetish

While kneeling there, before Kat's naked 20-year old body, memories of the summer of 2000 were flooding through Evan's head. Kat's older sister Sharon had been his lover the summer before he headed up to the big city to make a name for himself in corporate finance. Now, Kat had just caught him masturbating while reliving some of their torrid affairs. Worse s...

Alabama Nan: Good Time Granny

by SubLadyD on Sep 16, 2017
Transsexuals & Crossdressers

My first full year of college was over with and I found myself driving to my grandparents for the summer. The 'conversation' I had a day earlier with my folks was fresh in my mind... reminding me why I was making this drive. I could still hear my mother's condescending voice, "Nathan... NO your name is NOT Nancy! Your name YOUNG MAN is Nathan. I didn't car...

Winter Night

by rockhardy on Sep 16, 2017
Romance

The snow squeaks under my shoes as I step along the sidewalk leading to your door. I'm careful not to slip. My breath billows gray smoke in the night air. I check to make sure that I haven't forgotten my bag of goodies. It is too cold to come back to the car. Yes, all there, I assure myself. The bag is heavier than one would suspect. The contents swing with...

Caught Exploring

by SuprHap11 on Sep 12, 2017
Transsexuals & Crossdressers

I open the hotel room door and look around the room. The front room has a couch and table and the back room has two beds. A window in the front room looks out on the walkway and then past to the open atrium. I close the door and walk to the bedroom with my bag. I think again about the chat from last week and how exciting it was. I took the plunge and finall...