Sissy Wife Gay Stories

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Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Faye's Official CHYOA Story Contest 2025

by Spindizzy on Apr 29, 2025

Hey there, sexy readers, it's me again, Faye, your faithful flirty filthy CHYOA librarian. Gosh, it's been simply ages since we've had a chance to chat, but I've been so busy filing away all your delightfully dirty stories I've hardly had a moment to relax. What I really need is a little me time. A chance to unwind with my favourite toys and the highest qual...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Becoming Her Bitch

by HerLittlePiggy on Sep 13, 2017
BDSM

"Take it like a man you sissy bitch," Jennifer said as she thrust her big strap on into my ass. "Yes mistress," I groaned as the long life like dick pounded my prostate. "I'm not your fucking mistress you sissy pig," my wife yelled as she slapped my ass hard leaving it stinging and red. "A mistress wouldn't have her cock inside your sissy ass. From now on...

This Cock Tastes Like My Wife Ch. 04

by Turned on Sep 17, 2017
BDSM

This is part 6 and 7 of the series. Parts 1-3 were contained in chapter one. Part 4 in chapter 2. Part 5 in chapter 3. Part 6 – The Battle Against Reality "Honey? Honey? Are you awake?" I cracked my eyes slightly, but pretended to still be asleep. DD was wearing red thong panties and a matching bra, checking herself in the mirror atop the dresser. She...

Lingerie Does Make the Man

by lingerielover on Sep 12, 2017
Fetish

What do you think you are doing? She asked, and I knew I was caught and I was going to have to pay for my indiscretions. I didn't know what was going to happen, but I knew it wasn't going to be good. I guess I should start from the start of the day. I got up early like I always do and was just waiting for everyone to leave the house for the day. The kids wo...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...

Sissy Surprise

by silkstockingslover on Jul 18, 2018
Interracial Love

Editor's note: this story contains scenes of gay male sexual content. Summary: Wife discovers her husband is a slut for BBC and... Note 1: This is a NUDE DAY 2018 Contest Story. Note 2: Thanks to Tex Beethoven, and MesaMan for editing this story. - SISSY SURPRISE My husband hadn't been the same since he returned from a six-month military tour. There w...

Alone with a Sissy

by JRussell on Sep 16, 2017
Fetish

Home alone with the wife conveniently out of town for the next four days, Mark wanted badly - badly - to act on his urges to be intimate with a man, to hug, kiss, touch, rub, stroke, suck, the whole progression of lovemaking. He was starting from scratch, as his gay friends also were his wife's friends and he didn't want to take a chance that a careless word...