Halloween Crossdressing Stories

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Master's Degree in Crossdressing Ch. 01

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

This series is the follow up to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making confessions to the public for the first time, my wife has generally been aware o...

Good Little Bitch Pt. 01

by Baron_Cumhausen on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1: Halloween "Seriously!" my girlfriend Claire declared, "Nothing faggy or anything like that, just yoga outfits and a little makeup, y'all will be so cute!" It was Halloween night in Austin, always a major event down on Sixth Street with ten thousand people bar hopping and mingling in the street even when it fell on a weeknight. Today was Friday...

Halloween Crossing

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

It all started off so innocently... My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeous, but recently our sex life has become a bit humdrum and mund...

A Halloween to Remember Ch. 02

by jealouscuck on May 7, 2019
Fetish

The morning after the Halloween party, we woke up as usual. I felt a little different under the covers until I remembered what had happened after we made love the night before. We had showered and then I picked out two pair of sexy panties. One for Jeff and one for me. I looked over at him as he started waking up. Jeff had been at home from work for a while...

Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

Summer to Remember Ch. 02

by SummerDreams on Jun 4, 2018
Transsexuals & Crossdressers

When I arrived back on campus in September, I still had these constant, lingering thoughts of being Alexa. Maybe lingering was not the best word. Crossdressing was in my mind even worse than before. It was all I thought about. Everywhere I looked I saw young female classmates sporting their best new clothes for their first week back on campus. It was a da...

The Basement Ch. 02

by FiveDots on Dec 24, 2019
Transgender & Crossdressers

I received a text the next evening. 'Hey dude, come down here and check this out.' Not yet ready to confront him with a revenge plan but not willing to ignore him either, I traveled down the stairs to the basement. My roommate had used the threat of exposing my questionable internet history to coerce me into letting him shrink me temporarily to pleasure him...

Caught Ch. 01

by Love2BeALady on Sep 11, 2017
Transsexuals & Crossdressers

This is my first story and I apologize about any errors. My girlfriend and I had been living together for over a year. She moved into my house that I had custom built about three years ago. I had always been into crossdressing since I was a kid. So when I had my house built, I had a secret room created for my crazy kinky side. None of my girlfriends had ev...

Pantyboy Graduates to Crossdressing

by laceypantyboy on Oct 8, 2018
Transgender & Crossdressers Stories

Pantyboy graduates to public cross-dressing. Hello. Let me just say at the outset that I am not gay. I am a hetero man who really likes panties, stockings and pantyhose. I had been wearing them under my boy clothes for years. Some of my girlfriends were disgusted, some were OK with it while not being turned on by it, and a few of my girlfriends did (and do)...