Sissy Fag Stories

7,843 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...

Generation Z

by contactsteph77 on Apr 3, 2019
Transgender & Crossdressers

1 - James the scavenger James was born into a new world. One of the last people ever to be born. When he was just four weeks old, a virus began to spread across the USA. It was an illness that only seemed to be contracted by females of sexual maturity. Initially the survival rate was around eighty-five to ninety percent. It didn't take long before the ai...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Controlling Sissy Janice Pt. 02

by sissy_janice on Jul 6, 2020
Fetish

Lilly instructed me to go upstairs and strip, and to remove my wig. "I have to get some bags out of my car. I want you naked and in the shower when I come back." I did as I was told. I was in a bit of a fog. I was now going beyond what I'd ever contemplated. Even if I'd worked up the courage to tell Lilly the truth, the most I'd have hoped for was the occas...

Christine Cuckolds her Husband

by dreamweaver5539 on Sep 13, 2017
Interracial Love

My Daughter-in-Law Christine, married to my step-son John, as I have mentioned in previous journal entries, is a truly stunning lady. In her early 30's, she is a slender and gorgeous blonde whose appearance simply overwhelms most men on the sight of her. Long of legs with dainty thighs, her breasts are well developed, a comfortable 36C I would guess. With lo...

Susan

by FredTR on Apr 17, 2019
Transgender & Crossdressers

It's important to understand that even though I had sucked cock before, it had been many years ago. A few times experimenting when I was younger, over a decade ago, was all I had done. And now... well, I'm getting ahead of myself. Justine (my wife) and I had been married for almost 12 years. We were both in out late 30s, closing fast on 40. We had one son t...

My Dom's Decisions

by davesubboi on Oct 12, 2017
BDSM

The thought of being submissive and letting another superior being guide, direct and change me has become one of my driving desires. Over the past 15 years I have realized I am much better at pleasing others and have determined based on numerous online doms/master/mentors that I really should not care about my own pleasure if I can serve another and give the...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Dress Up For The Girls Next Door Ch. 02

by JackorJill on Jul 15, 2020
Transgender & Crossdressers

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot. “I have a few cold beers in the fridge,” she cooed. “Why don’t you take a b...

Mistress Aimz

by hyperpress on Aug 17, 2017
Fetish

Mistress ordered me into my chastity device. I complied. "you may not cum this week," she told me. I didn't. I was good. I used depilatory cream and removed all my leg, clit and pussy hair for mistress. It was Friday. She told me to take off my chastity and jack off into a glass. She said I could cum as much as I want Friday and Saturday, but to cum in th...