Husband Crossdressing Stories

106,581 results
Orientation
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Infinite Scroll

Marriage Transformation Ch. 09

by jealouscuck on Feb 6, 2018
Fetish

Once Elizabeth had experienced Dan's big cock, Chris watched for any apparent changes in her attitude toward him. A few nights after the big event, Elizabeth came out of the bedroom dressed exactly as she had been for Dan. Chris looked at her and wondered what was about to happen. She approached him and began kissing him. She took his pants down and sucked...

Feminine Fate Fulfilled

by mattpantyhose on Jun 15, 2020
Transsexual

Like all of my other stories this one had been already published on Literotica. You can find it here: https://www.literotica.com/s/feminine-fate-fulfilled__ For whatever reason Chyoa doesn't include Crossdressing in the category of Transsexual and doesn't have a separate category for that theme. This story does not include any transsexuals, but I considered...

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Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

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:...

Sarah has a Crossdressing Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before e...

Aileen Ch. 01

by TiffyKitty93 on Sep 19, 2017
Transsexuals & Crossdressers

~The following is just a fantasy. Any actual names or likenesses to real persons or events in entirely unintentional and coincidental.~ Rain. Oh how I hate the rain. Only bad things have ever happened to me in the rain. Two years ago, when I was sixteen, My parents argued and decided to get divorced in the middle of a rain storm. However what happened in...

Head Shrinking - Big, or Little?

by justincbenedict on Dec 9, 2019
BDSM

India smiled at the young couple. She loved seeing clients in this office. It seemed so cozy and the clients could cuddle while talking to her... It was a great couch. Reed looked a bit tense, but it had been months since he'd been out of his thing...of course when India thought of her husband and how long he had been in a tube, it didn't really give her mu...

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

Crossdressing For My Boyfriend

by dmk241 on Sep 12, 2017
Transsexuals & Crossdressers

My name is Chris and I'm a 25 year old, white, bisexual male. I stand 5'9" and weigh 135 pounds with light brown hair and brown eyes. I've always had somewhat of a feminine body and I've always enjoyed being a "bottom" when with other men. I met my boyfriend Mark about a year ago at a bar. The minute that I saw him, I knew I had to have his cock inside of m...