Sissy Blowjob Stories

38,451 results
Orientation
Length
Source
Infinite Scroll

The Alpha Who Made Me a Sissy Ch. 01

by HB77 on Jul 31, 2019
Transgender & Crossdressers

So there I was again on all fours in his bed. My peach coloured thong panties pulled to the side, and my daddy behind me with one hand on my hip and the other Gripped onto the back of my red corset. Chad relentlessly filling my ass pussy with his gorgeous rock hard 8" as I moaned "oh daddy, oh daddy don't ever stop fucking me, I love you" over and over in my...

My First Time as a Sissy Ch. 02

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

This story is about my journey to being fucked as a sissy for the first time. Part One should be read first. ***** When Raoul left after I had given him the first blowjob I had ever given I was feeling confused. I knew that I had enjoyed it but, didn't know how I felt about having to do it again as he had promised I would have to. I guess I wasn't going to...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

Correspondence Ch 1.01

by jimmysub on Sep 17, 2017
Loving Wives

July 15,2001 Dear Jimmy: Lauren mentioned to me that you were feeling cranky and unappreciated by us. I am writing this note to express my respect and appreciation for you. She pointed out that your tolerance for being teased seems to vary. When I tease you it is in good clean fun. We might like to see you blush, but there is humor in your brining us coff...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Mamma Mia - En Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"Ah chico, I think you already know the answer. It's making you into exactly the lover I want," Mia said as she brought a hand over to rub her cuddling stepson's chest. "It's making you into a woman like me." All the changes he'd experienced over the past weeks suddenly clicked in Tommy's head. The swelling and tenderness in his chest. The slight widening o...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Brandi's Turn Pt. 02

by 9volt on Mar 3, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** So we woke up with my sister looking, mouth agape, at my husband in his torn panties, garter belt stockings and bra and me with a 6-inch strapon cock jutting from my otherwise naked body. There wasn't even a blanket handy to pull over ourselves. There was a pretty awkward silence...

A Night at the Club Pt. 01

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Dani nervously looked at his reflection in his trusty compact mirror. He was sitting in the passenger seat of Keyshawn's black Escalade, about to enter one of the most exclusive clubs in the city. His mascara made his naturally thick eyelashes flutter attractively, his eyeliner perfectly framed his blue eyes, and his Candy Apple lipstick was flawlessly appli...