Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Becoming a CockWhore

by BiSwingCock on Feb 25, 2019
Group Sex

I'm a cockwhore. That's what I wanted to say when the president of my office machine company handed me the Salesperson of the Year trophy in front of hundreds of my colleagues at the annual convention and said, "Ken, tell us a little about how you pulled this off." Well, the only thing I had successfully pulled off was my pants. Or more specifically, the...

The Visit

by PeterShore on Sep 24, 2019
BDSM

As soon as he had put the envelope down onto the small dressing table she ordered, "Take off your clothes now, and be quick!" As he started to undress she gave him drawstring bag and told him to put his clothes in it. She said that she was going to take his clothes and he would only get them back when she was ready. He quickly took off his clothes, stuffed...

Victoria Pt. 02

by mothman34 on Oct 16, 2018
Transgender & Crossdressers

"Well, good morning stud," Victoria said, smiling, greeting me at the door, "How are you this morning??" "Better than ever thanks to you," I replied, "yesterday was awesome, I can't tell you how much I enjoyed being with you. That was the most amazing experience of my life." "I'm glad you enjoyed it honey," she said, stretching up to kiss me on cheek, "Tha...

Andrea Pegs for Revenge

by sulkingfairy on Oct 16, 2018
Anal

DEPICTED CHARACTERS ARE 18+ Andrea hated Roman. She hated him. She'd hated him since senior year. He'd started as a sort of long term substitute in the second semester, after Professor Marty had her twins, after Andrea had turned 18 and made a pledge to conquer every man she wanted to, now that she could. That pledge got boring rapidly, upon her realizing...

Jaime and Mike Pt. 03

by LadyMelodyDarkheart on Nov 27, 2018
Transgender & Crossdressers

The wedding date was set. We decided since we met near Halloween, we would get married on it. It had been mid July when I asked Jaime to marry me, and we had lots of planning to do, plus get the restaurant open. We divided up the tasks, I would do most of the restaurant work and she would plan the wedding. Of course Jaime had input in what she would need for...

Pegging You-We Both Cum

by TrotskysGirl on Oct 9, 2018
Fetish

I definitely noticed your affectionate mood when I got home tonight. You've been reaching out for more hugs and kisses than usual. I ask you curiously what was up, and you give a mischievous little grin. "I just missed you today," you purr, planting kisses on my cheek as you wrap your arms around me from behind. Hmmm...you want something...that is obvious!...

A Long Cool Woman in a Black Skirt

by DreadWriter6969 on Mar 26, 2019
Transgender & Crossdressers

I first saw her in the lobby of the hotel in which I was staying for my conference. I'm the national sales manager for a large manufacturing company. We hold a national sales meeting every year to which all of the regional managers are gathered for education on new products, sales techniques, etc. She was a tall woman, actually taller than I, but I noticed...

Wife Controls My First Bi Experience

by Judge60 on Mar 26, 2019
Fetish

First, let me thank "HeyAll" who functioned as my "volunteer editor" on this story. His assistance was invaluable to the process and to the content itself. I thank you, sir! BACKGROUND: Approximately two weeks ago I placed a notice in the Literotica Personals. My "Profile" read as follows: "Introduction I am a 65-year-old man and have been straight my en...

Royal Rumble Of Sex

by sixgun8 on Mar 30, 2020
Group Sex

I wish that this story was true... But it's just a fantasy at this point. I'm not a great writer, but I'll do my best here and hope that the story gets y'all attention. * This scenario is to be called the Royal Rumble. I've always wanted to see my wife in a gang bang, but I don't want her to be overwhelmed with too many things happening to her at one time....

Bill Meets Jessica Ch. 06

by lateknew on Mar 18, 2020
Fetish

After the initial mind control Jessica put me through, she further convinced or coerced me to move in. Most of my stuff ended in a warehouse excepting for some of my clothing. She is taking me deeper into submission, I'm losing the knowledge of who I am or was, her obsessive control over me makes me dependent of her and a willing subject to her whim. My like...