Penis Shrinking Chastity Stories

87,310 results
Orientation
Length
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Infinite Scroll

Lonely Man Becomes a Sissy

by rebeldoll on Sep 12, 2017
Transsexuals & Crossdressers

I am a 28-year-old male. I'm single and live alone. I work days and usually sit at home at nights and watch movies, and talk online. I do small buying and selling on Ebay for extra cash that I stash away for a rainy day. So most of my time is spent online. I use to be into rock music a lot and have had long hair since I was a teenager. I some how lucked out...

The Office Boy Ch. 04

by Aussie Worm on Sep 25, 2017
BDSM

Here I was, back in the city, well an hours drive away in the suburbs, I had managed to find a small two bedroom house to rent for a while until I get things sorted out. I had managed to buy the basics, a little furniture, television, computer and other things, but in reality I had accomplished next to nothing in the two months since I had be asked to leave...

A Valentines Gift for My Lady

by sissymissyct on Sep 1, 2017
Fetish

Her long flowing chestnut brown hair mixed with my long brown hair as we passionately embraced on the king-size four poster bed. I would catch a glimpse or two as I peered up between kisses. Mostly I saw her bright red lips as they neared my pink painted lips. She nibbled gently on my soft lips before driving her tongue into my mouth. Kissing me deeply as th...

White Boi Learns his Place Ch. 03

by sissyashley4bbc on Jul 10, 2018
Transsexuals & Crossdressers

After the group decided we should go to our pool, Emily came up to me and told me she had a bathing suit I could borrow. Daddy told me to go get changed with her, and the guys would start making drinks and rolling joints to take outside. I guess he didn't need to change really, all he has on was athletic shorts that would dry quickly. I followed Emily upst...

A Strapon Tale Pt. 01

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex and chastity play. Alex (29) and I (36) had been seeing each other for about a year now. During our first date I immediately sensed that she had kinky potential. There was simply something about her looks and attitud...

My Secret Revealed Ch. 03

by jealouscuck on Mar 28, 2018
Transsexuals & Crossdressers

I was wondering what Karen had in store for me. When I got up the next morning, showered and shaved, I had little time to wait. She was holding her tiny g-string that she had worn the day before. A certain twinkle in her eye told me that something else was about to happen. "Honey," she said, "Like I told you last night, even with your smaller than average c...

Erin Ch. 03: Male Chastity

by Graves94 on Sep 24, 2019
Fetish

[ Note: This is the third in a multi-part story series. Each installment can stand alone, but to start at the beginning, read: Erin Ch. 1 – Female led Relationship. Followed by: Erin Ch. 2 - Female Led Marriage JQGraves ] ******** Erin and I celebrated our second anniversary enjoying the outdoor attractions where we live. We spent the day riding the gond...

Being a Wife to My Wife

by TammyPanty on Mar 19, 2018
Transsexuals & Crossdressers

My wife and I have been married for over seventeen years. The circumstances under which we live evolved over the first six years of our marriage to a point that makes me so comfortable in my role as the feminine half of our relationship I will forever be grateful I found the woman I did who allows me to fulfill myself as the pretty girl I am. Growing up as...

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...

Letter From Scranton

by justincbenedict on Sep 14, 2020
BDSM

Dear Shoeblossom I had a sister, Huxley, ("Hubert and Huxley, so cute") and we lived at home during our university years, as Pop was bursar at the local college, so we went for free. Huxley had a best friend, Tamsin, who was cute but chubby, and I teased her about it, and one day Tam pulled my pants down when no one was around, and gave me a spanking--me,...