Sissy Pimp Stories

9,288 results
Orientation
Length
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Infinite Scroll

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

Kim Meets Master Jim

by Master Jim on Sep 16, 2017
Transsexuals & Crossdressers

Their first encounter had been well planned. Since Kim and her master had already corresponded via email for some time and even chatted on the phone, they knew they were ready for the real thing at last. Master Jim had booked the hotel room, stocked it with liquor, then went to the spacious lobby. He sat down and nonchalantly set the room key on the adjoini...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

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...

Chronicles of Heather Maureen Ch. 10

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Showered and with my hair still wet I slipped on a pair of panties and thought over the last while as I fixed and ate breakfast. I needed to control my actions more somehow. I couldn't go on being the wanton sissy slut every night the way I had been and I certainly couldn't go on having unprotected sex all the time! I just didn't know how. I'd start out wit...

Opening Him Up Ch. 03

by humbleboy on Sep 12, 2017
BDSM

Amy laid down next to Tim exhausted. “Tim, now I want you to suck on ALL that cum you just shot in my pussy.” Tim without a word placed his mouth on her trimmed pussy and began to suck and lick her hot organ. “That's good. You love this pussy, don't you?” Amy had always liked the way her husband eat her out, but now it was the power trip getting her off. “D...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....