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Story tag results for sissy

Found 31 result(s)

Dommy Mommies and Chastity Belts!

-       Dommy Mommies and Chastity Belts!               TJ Ryder          The 15th Annual DommyMommy Ball!     Briarcliff Academy      Jan 15  7 PM *************************************    Terrence/Te...

By: tjr | Category: Incest | Score: 3| Added: 19 Mar 2009

Miss Teresa's Beauty School

- I wrote this story as a narrative and I made it into a 45 minute audio story. The Interview: Come in, I've been expecting you. I had a long talk with your boss the other day and it seems that you h...

By: Teresab | Category: Crossdressing | Score: 4.8| Added: 01 Jul 2009

Fulfilling A Girl's Male Fantasy Part 2

- Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relations...

By: starbelliedboy | Category: Crossdressing | Score: 4.8| Added: 31 Aug 2009

My Girlfriend Made Me a Sissy

- This is my first attempt at a story so any feedback would be greatly appreciated. Feel free to email me about anything: feedback requests or just to chat. When I was 16, in spite of my shyness and n...

By: libertina | Category: Bisexual | Score: 4.9| Added: 08 Sep 2009

My Girlfriend Made Me A Sissy 2

- My Girlfriend Made Me A Sissy - 2 Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy -------------------...

By: libertina | Category: Bisexual | Score: 4.8| Added: 09 Sep 2009

My Girlfriend Made Me A Sissy - Part 3

- Here's the 3rd part of my story, I hope I didn't make you guys wait too long. Hope you enjoy, its best read one handed ;-) My Girlfriend Made Me a Sissy - Part 3 -------------------------...

By: libertina | Category: Bisexual | Score: 4.9| Added: 20 Sep 2009

Working It

- I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago...

By: Teresab | Category: Crossdressing | Score: 4.5| Added: 26 Oct 2009

Webmeets Diary Ch. 03

- Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out...

By: starbelliedboy | Category: Crossdressing | Score: 4.4| Added: 09 Jan 2010

I become my wife's girlfriend. The beginning.

- My name is Tony and I'm a regular straight guy. This is the story about my life as the part of lesbian couple, and yes, I'm aware of weirdness of this statement. During the first period of our relati...

By: thony777 | Category: Crossdressing | Score: 4.7| Added: 20 Mar 2011

Mike's new girlfriend

- It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock sta...

By: nicole77 | Category: Crossdressing | Score: 4.8| Added: 17 Apr 2012

Mike's new girlfriend - part 2

- The following Monday couldn’t come round soon enough. It had been a long, difficult and very confusing seven days at home, with my wife, Amy. I had been so distant and argumentative with her and I cou...

By: nicole77 | Category: Crossdressing | Score: 4.7| Added: 09 May 2012

The Awakening of Susi

- Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I...

By: susi_swallows | Category: Crossdressing | Score: 4.8| Added: 05 Dec 2012

Busted by my Sister

- I had the rarest of rarities - an afternoon home, alone. I could hardly believe my luck. My sister, Teresa, was out with her boyfriend, or at the mall or...who really cared, she was out. Mom and Dad h...

By: pantywriter | Category: Incest | Score: 4.8| Added: 02 Jan 2013

The Perfect Choice

- Andrew had moved in with Hannah a few short months ago and so far everything was going just the way she wanted. She was an endless tease; wearing short skirts and dresses when they were out during th...

By: libertina | Category: Crossdressing | Score: 4.8| Added: 05 Jan 2013

Sissy at the Bookstore

- I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decid...

By: jessicahahn | Category: Crossdressing | Score: 4.7| Added: 29 Jan 2013

sissyboy jake is harshly used - part 1

- sissyboy jake is harshly used - part 1 It's two o'clock in the morning. The story I have to tell you started at noon yesterday and ended just after midnight. Twelve hours. The most incredibly inte...

By: culotte_de_dentelle | Category: BDSM | Score: 4.9| Added: 06 Jun 2013

My New Sissy Life

- I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted onl...

By: jennaryder13 | Category: Crossdressing | Score: 4.5| Added: 12 Jun 2013

Sissyboy Jake Is Harshly Used - Part 2

- I lay on the thin blue pad, exhausted and somewhat dazed. As I said, I was very new at this and didn't expect such harsh treatment so quickly. My bottom was sore and I actually thought I felt my insid...

By: culotte_de_dentelle | Category: BDSM | Score: 4.7| Added: 25 Jun 2013

An Uneven Romance - Part Two

- “Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night befo...

By: libertina | Category: Crossdressing | Score: 4.8| Added: 18 Jul 2013

Sissyboy's Punishment

- Mistress was very angry and Sissyboy knew it. He had never crossed her to this extent. She had spent a year grooming him, training him, allowing his fantasy to come true, and allowing him the privileg...

By: poizenivy | Category: Taboo | Added: 28 Jul 2013

A Moment Of Madness

- Alan Jones is in the bedroom wearing his school-uniform. A tight gym-slip hugs a crisp white blouse. Navy blue cotton panties keep his privates well protected. White knee-high socks and black Mary-Jan...

By: HayleyHollyGrace | Category: Fetish | Score: 3.5| Added: 09 Sep 2013

Kinky Regression Ch 2

- “I thinks it’s time to take Holly Grace into the office.” Helen returns Lowri to her normal body. Hayley has Alan in her arms, cuddling him tightly against her breasts. Becky passes the sissy’s belo...

By: HayleyHollyGrace | Category: Fetish | Score: 0| Added: 10 Sep 2013

A Moment Of Madness CH 2

- After more than twenty minutes of inhaling Belinda’s snotty hanky it is removed by the owner and placed back into her hand-bag. Louise spits on a wet-wipe, cleaning his mouth like she would do to a li...

By: HayleyHollyGrace | Category: Fetish | Score: 4.3| Added: 11 Sep 2013

Country Cuckold 2

- When I got home from spending the day working down the road to install the new back deck, I was not expecting what I got. Frankly, I was expecting nothing more than to grab a tall glass of ice water, ...

By: pantywriter | Category: Cuckold | Score: 4.8| Added: 25 Sep 2013

Rick Becomes Rikki, Chapter One

- Rick tried hard to assume the masculine role when he first got married to Sally, but from the day that Sally caught him wearing her panties the jig was up. All her suspicions were confirmed: Rick was ...

By: Janno36 | Category: Cuckold | Score: 4.6| Added: 12 Nov 2013

Feminizing Henry, Part II

- When Henry Fitzwinkle's wife Sally found him wearing her panties she lost all respect for him as a man, but he became more interesting to her as an experiment. Her mother, a dominant woman named Edwin...

By: Janno36 | Category: Crossdressing | Score: 4.5| Added: 26 Nov 2013

Feminizing Henry Part IV

- Well, dears, it was a very embarrassed Henrietta Fitzwinkle who felt a bulge in his panties when he had to welcome his old boss Joe Dugan at the door of his apartment, knowing that Joe could see he wa...

By: Janno36 | Category: Cuckold | Score: 4.3| Added: 10 Jan 2014

Christina and Cheryl

- Christina and I had been dating for nearly two years. Within six months into our relationship, I confessed that I enjoyed dressing in women's clothing. She'd been more than accepting and encouraged me...

By: cheryl_lover | Category: Crossdressing | Score: 4.8| Added: 10 Jan 2014

Happy to be used

- I cannot see or hear. I'm relying on my Daddy to lead me where he wants me. I can feel the tiled floor beneath me as he pulls me, my nipples sore from the chain. He stops and positions me, pushing o...

By: excaliburofthelake | Category: Fetish | Score: 4.5| Added: 13 Feb 2014

Free Clothes

- I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for...

By: PlayfulAshley | Category: Crossdressing | Score: 5| Added: 07 Mar 2014

Night at the Video Store, Part 2

- There were some strong, black street toughs in the SUV, but they got quiet when they saw me step off the curb into the parking lot. My nipples began to get hard under my little black micro mini dress ...

By: jerrixdresser | Category: Crossdressing | Score: 1| Added: 15 Mar 2014