Sissy Cocksucker Stories

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Infinite Scroll

A Friend Catches Me Ch. 03

by PinkPanties4me on Dec 2, 2019
Transgender & Crossdressers

Sorry it took so long to continue my story...For those of you just finding this, please read my first two sections, A friend catches me 1 and 2. *** Karen looked at me and said," I have had an idea for a while, so now is as good a time as any!" She took out her cellphone and made a call. "Hello Roberto, no I don't need to make an appointment to get my hai...

First Time Sissy at the Gloryhole

by Stephen_Heathcote on Sep 16, 2017
Transsexuals & Crossdressers

Once I realized that I liked to wear panties, I wanted to be seen in them. But I didn't want to be seen by anyone that I knew. That would be too embarrassing. I drove to the next city over and walked around with the satiny fabric caressing my cock beneath my clothes. I had dinner. I shopped. It was fun having a secret, but the excitement wore off quickly. I...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Kasey's Confession Ch. 19

by KaseyLegs on Sep 13, 2017
Transsexuals & Crossdressers

I woke up very early in the morning, having fallen asleep in my bathtub. The water had turned ice cold, which along with the discomfort of having my head planted in the corner of the tiled wall, had jolted me into an early awakening. Tuesday was Lisa's funeral, and I had the day off for it. In the morning, after getting some more sleep back in my bed, I wou...

One Step Too Far

by SatinDreamGirl on Sep 16, 2017
Fetish

The clock on the bedside table clicked loudly in the otherwise quiet room. A soft buzz of cicadas outside drifted in through the small gap in the raised window. The room seemed to glow with pink from the afternoon sun. The room hadn't changed much since Rachel had begun her fashion phase in high school. Her closet (and the closet of the guest room) were stu...

In the Club

by girlygay on Sep 23, 2019
Transgender & Crossdressers

No longer virginal, now degraded. That is my life as Dave's sissy whore Chandra. With my girlfriend Nikki and her boytoy Adam, we descended into our city's LGBT club scene with a fervor. Dave and Adam were only too happy to share their girls with their friends, and Nikki and I adored the attention, the sex, and the feeling of being desired by so many men. O...

Jack and Jill Pt. 01: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

Dinner was almost ready when the doorbell rang. He turned down the stove and went to answer the door. She was taller than he expected, broader too, but she was undeniably a very attractive black woman. 'Hi,' she smiled 'You must be Jack, I'm Jean, it's nice to finally meet you.' Jean was Jill's colleague from work, he had heard about her many times over t...

Girl's Night Pt. 11

by DifferentBreed on Sep 14, 2017
Fetish

The applause from the gallery died as abruptly as it started and Fisher looked to Sophie, searching her face for an indication of what she was feeling. He stood, hand in hand with Eve, growing increasingly uneasy with her silence. "Mistress?" he finally managed to blurt, "What do I do now?" "Now?" Sophie said, "now, you get to cum. Aren't you excited Candi...

Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...