Pantyboy Stories

87 results
Orientation
Length
Source
Infinite Scroll

The Pantysissy Diaries Ch. 02

by JPantyboyVSL on Jun 5, 2018
Transsexuals & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2. *** The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get...

More Panties For Him in Vegas

by jennycnnn on Sep 11, 2017
Fetish

Sunday morning came sooner than I hoped it would but nonetheless it was here. It was around 8 am and I had ordered breakfast in bed to be delivered at 9:30. I rolled over and saw Steve still sleeping soundly facing away from me. He was still in his new sheer black babydoll and tanga panties that I had given him last night as a gift for a wonderful orgasm. If...

Secrets of The New World Order Ch. 04

by bjmichaels on Sep 14, 2017
Sci-Fi & Fantasy

"Judith, you're awfully quiet tonight... is something wrong?" asked Mary. I heard her voice, but not the words. I was holding up a cute bra and panty set pretending to be admiring the sexy lingerie, when in reality my mind was a million - miles away. "I'm sorry - what did you say?" I asked my friend. "Sweetie, you've been distracted all night...your eyes...

Finally Wearing His Panties Again

by jennycnnn on Sep 26, 2017
Fetish

For the past sixteen months, my sex life has been scaled back to what I would call "ordinary." My husband and I moved to Hong Kong with our children for a temporary assignment with his company that ended just two weeks ago. We decided before we left home that it would be best to leave our fetishes behind because we would be closely "supervised" by our host c...

The Descent

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence....

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)...

Secrets of The New World Order Ch. 06

by bjmichaels on Sep 16, 2017
Sci-Fi & Fantasy

Your child's eighteenth birthday marks a significant rite of passage every mother faces with ambivalent feelings...soon, the child will be out of the house on their own, meeting new challenges every day, and all you can do now is hope you've prepared them for the highs and lows the real world will throw at them. In my case, it meant I had just one child rem...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Spanked by His Neighbor Ch. 02

by rickiee_2002 on Sep 13, 2017
BDSM

I was sitting at home, contemplating what had just happened to me. My ass was stinging and I was excited. I really wanted to just go upstairs and masturbate and was about to when the telephone rang. The caller ID let me see it was Alayne. My heart began to beat hard in my chest ... and had feelings of sexual excitement as well as fear. "Hello" I said into t...

Panties for the Ladies Ch. 1

by megan on Sep 25, 2017
Fetish

I had just graduated from high school and woke up the morning after our big party. Before I went downstairs I slipped off my panties and put on a pair of boxers. Mom was already up and in the kitchen pouring a cup of coffee as I went downstairs. "Good morning, sleepy head," she said to me. "Hi, Mom," I answered. Mom was wearing a long sheer gown. Her bre...