Crossdressing In Pantyhose Stories

360,254 results
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Infinite Scroll

You Knew

by TwistedPanties on Mar 18, 2020
Transgender & Crossdressers

You had willingly searched and jerked off to sissy porn for years. You regularly read Literotica fiction and would love to stroke yourself for hours. It was not uncommon for you to chat or flirt with other bloggers or online friends. You sought out a deeper role. The hypnosis of online flirts and short sissy skirts led to cravings, stronger and stronger with...

Pretty Chris-tine Ch. 03

by jealouscuck on Sep 26, 2017
Fetish

After I had learned to openly share all my fears and inhibitions with my wife, Sharon, we really began to enjoy our sex life even more. In the last chapter, I told about how she encouraged me to dress up "pretty" for her. This was not our entire role playing event, but rather a very titillating one we both enjoyed. And now, I totally enjoyed our evenings and...

What is Going On?

by dontholdyourbreath on Sep 13, 2017
Transsexuals & Crossdressers

This story is dedicated to Ms. Karen-Anne Brown and all the amazing Nifty transgender writers who wrote mind control stories back in the 90's. I grew up reading Nifty stories and always loved the mind control category so I felt compelled to try my hand at it. I hope I did all the great writers who have come before me a little justice. Please also check out m...

Pretty in Pink Ch. 04

by jealouscuck on Sep 25, 2017
Fetish

Having a lifelong fetish for sexy lingerie was exciting, but my concern was having someone catch me wearing. After my wife, Jessica found out about my stash of women's clothing, I thought my marriage might be over. Her eventual understanding, learning and acceptance of my little kink was a life changer for our marriage and my peace of mind. When in fact she...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

How Marissa Became a Woman

by CDSean on Sep 19, 2017
Transsexuals & Crossdressers

This is a work of pure fiction. It deals with adult subject matter including crossdressing, and consensual male on male sex. If any of this offends you, please stop reading now. This is my first story for others so any feedback would be appreciated. ***** Henry and Lisa have been married for many years. During that, time both of them made many little pe...

Staying Together

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"I'm not sure further sessions will be of much use to either of you. After seeing both of you twice of week for two months, neither of you is any closer to resolving your concerns than we were when you first came to me." Dr. Nelson was good. She had the ability to examine a problem, bound it, and then dissect it into smaller pieces. She'd done that with bot...

Initial Crossdressing Adventures

by vjak19 on Sep 19, 2017
Transsexuals & Crossdressers

Since the first article I wrote described the last time that I dressed as a woman was generally well received, I have decided to share some more of my story. To do that I will start the journey at the beginning and travel through to some of the first times that I ventured out into public dressed as a woman. For those that did not read my initial offering le...

Pillow Talk Ch. 02

by MicheleNylons on Sep 10, 2018
Transsexuals & Crossdressers

Chapter Two -- Tranny 101 Michelle Clooney sat in a booth in a rundown coffee shop near Times Square. The grimy window provided views of go-go bars, sex shops, peep shows and adult theatres, the iconic square had not improved any since it's setting for Midnight Cowboy a few years earlier. Michelle was dressed in red spandex hotpants, a long sleeved purple...

One for the Team Ch. 03

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter Three - Maid Service October 1984 Charles reported to Robert's dormitory room as directed the next morning straight after breakfast. During breakfast service William Larkin was upbeat and caromed around Charles like an excited puppy under his feet. "So we're hanging around with the upper housemen now that we're a top rugby player?" he teased. "If...