Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Made to Obey Ch. 02

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Reprise: I had been watching shemale porn when alone in my Sister-in-law's house. Tempted into wearing some of her underwear whilst masturbating, my wife (Ruth), sister-in-law (Esther) and their mother (Donna) came home much earlier than expected and caught me in the act. * I scampered up the stairs, still dressed in the suspender-belt, stockings and panti...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

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...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

In For a Penny... Ch. 02

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: Thank you for all the positive feedback and encouragement to write Part Two. I apologize for taking so long. However, I didn't want to submit a story that contained any clichés, so I had to take my time to think through how this next installment was going to play out. Let me know how I did. This chapter picks up immediately after Part One. I...