Sissy Hubby Stories

14,453 results
Orientation
Length
Source
Infinite Scroll

Mrs. Claus's Predicament

by tcs1963 on Jan 7, 2019
BDSM

Wrote this story right before Christmas, Edited and proofread by my friend, TakeMeDown... ***** It was Christmas time again, and everyone was very joyful at the North Pole. Toys were being made on every table, hot chocolate was brewing and smiles abound. It was a beautiful holiday scene, with the exception of Dear old St. Nick being mysteriously absent....

A Whore Wife's Story Ch. 03

by Anal Slave on Aug 30, 2017
Fetish

Well, let me start off by saying that I have a very kinky wife and that we have had many sexual adventures so far in life. This story is going to be a little different, because I am going to let my wife tell you about her sexual likes and pleasures. So sit back and pull your cock out and shoot a big load of cum for my wife. And if your really horny lift you...

My Sissy Wife Pt. 01

by IcelandSpar on Feb 11, 2019
Transgender & Crossdressers

I beep my car and ring the bell, holding the flowers I've just picked up on my way. Roses or lilies, I wondered, before settling on a combination of both. The door opens, and there you are, with your smile that cheers me up. We kiss there on the threshold, a peck that turns into a short kiss, then a longer one. You take the flowers from me, "aww, thank you,...

You Can Always Say No Ch. 02

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We had had 'The Talk' in the afterglow of that first evening of sex in our newly-revised relationship, less than a month before we exchanged vows. There is nothing more abjectly terrifying – for either person – than laying bare your soul at such an intimate level. He admitted his wants, needs, and desires; I reciprocated. He did, indeed, have a 'sissy' strea...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

Birth of a New Sissy Ch. 03

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male & male to female sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I...

The Sexy Cuckold Couple Pt. 10

by cuckcpl4play on Sep 19, 2017
Fetish

After the crazy collaring weekend, our home life shifted slightly back to some form of normalcy. Master would send us occasional texts, orders, etc., but overall there was nothing significant that was transpiring and in fact Miss Jenny seemed sad that more activity was not taking place. At work it was a bit of a different story...Master was his typical domin...

Lou Ciphers Tale

by sissymissyct on Nov 25, 2017
Fetish

Jane worked for a company on the floor above mine. I was a marketing rep and she held a similar position at her company but she was involved in the medical field I dealt with pretty boring consumer products. We had met on the elevator a few times before we finally went for lunch together and then on a few dates. We were both single. Well she was widowed an...

Mr. BBC is Totally Bisexual

by Samuelx on Mar 7, 2018
Transsexuals & Crossdressers

The Glebe area of Ottawa, Ontario, is usually a quiet and upscale neighborhood, but tonight at the Hiller townhouse, things were getting loud and steamy. Mark Dixon had Donna Hiller on all fours, face down and ass up, in the Hiller living room. The big and tall, burly young black man pulled on the curvy redhead's long hair and smacked her big white ass while...

Wife Humiliates, Hubby's Turned On Ch. 02

by Quietoldie on Mar 17, 2020
Transgender & Crossdressers

Bernie (formerly Bernard) That night after Carol had told me she was going to look for another man to inseminate her Carol took me by the hand to our bedroom and dressed me in the loose bra and panties along with the nightie she normally wears to sleep in. "You can wear them from now on sweetie, I've decided to sleep naked in future. You don't mind, do you...