Wearing Lingerie Stories

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CD Asst. Secy. Ch. 03: Request & More

by cdtycoon on Jun 2, 2020
Transgender & Crossdressers

LAJJIKA'S REQUEST The next day, I was the first to wake at 5:00 a.m. and saw that both were still sleeping with their towels loosened and displaced. So I cover them again with quilt and went to collect our clothes wearing my towel at chest level. On returning, I started wearing back clothes, first I wore stockings followed by panties, bra with pads & ball...

Weekend Games Ch. 02

by SissyAndi on Sep 16, 2017
Transsexuals & Crossdressers

I relived the things that had happened between Tammy and myself over and over. I was not sure how Tammy would act around me after what we had done that first weekend but when I picked her up for work the next Wednesday she didn't mention it and acted like nothing had happened. The week dragged on and I would begin to think it was all part of my active imag...

Caught in Ex-GF's Underwear Pt. 01

by HiddenThoughtz on Oct 6, 2020
Transgender & Crossdressers

Hello everyone...welcome to my crazy kinky life lol. This origin story takes place right before my 21st birthday. This all started when I finished my junior year at college. School had ended and I was taking summer classes so my workload senior year would be easier and I could enjoy my last semester. My two roommates had gone back home to work for the summe...

Caught by Tricia

by CorsetCutie69 on Sep 16, 2017
Transsexuals & Crossdressers

My life changed dramatically shortly after my wife of 23 years passed away last year. My wife knew of my cross-dressing and even supported it. She even started encouraging it after our son moved out to attend college. We had many girls' nights – both of us in lingerie watching movies and enjoying each other. She was diagnosed with breast cancer and kept it f...

Panty Consequences No. 01

by PantiesAndPies on Sep 11, 2017
Fetish

This series of stories are all standalone so can be read in any order. They are about my favourite fantasy -- my first time wearing, or first time caught wearing panties. Obviously then they include lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men. If this may offend you I suggest you stop now ... otherwis...

Caught For the Last Time Ch. 01

by TGJamie on Sep 12, 2017
Transsexuals & Crossdressers

I should have known something was up. When I arrived home, I was greeted with a big hug and a long, passionate kiss as I walked in the door. This was not quite the usual greeting, but it was a nice change. Then she slowly slid her hand down the back of my pants, pushed me back and yelled..."What are you wearing??" That day, like many others, I had slipped...

Whispers

by lovinlife0828 on Sep 15, 2017
Illustrated

Note: This is a story that another reader asked me to write. They gave me a brief outline and I went from there. I have added a few drawings that I did. If you are a reader who gets offended when the wife has sex with someone else, please stop now. This story is not for you. I hope that you enjoy this little sexcapade. * Allow me to introduce myself. My n...

Promotional Photos

by photoscribe on Dec 19, 2018
Illustrated

I was recently promoted and put in charge of developing the marketing materials for a new product. I have been involved in putting together other projects but this was the first where I was one responsible. At the recommendation of our Art department I contacted a local photographer before heading to the train and home. While on the train I checked and saw...

Christy's Fantasy Come True Ch. 06

by curious_cd on Sep 19, 2017
Transsexuals & Crossdressers

The alarm went off and Christy rolled over and hit the off button. The clock face was starting back at her flashing 8:00. Since it was Friday she had slept in a bit. Jim had gotten up early and left for work after spending the night. They had gotten into a minor argument last night but came to an accord and made up with some hot sex throughout the house. J...

Growing Up Male & Becoming a Girl

by TammyPanty on Mar 26, 2019
Transgender & Crossdressers

My sister is four years older than me, and since our father left the family when I was very young, I have really never known of a household that wasn't dominated by women. Growing up in the late 50's and early 60's, female lingerie was extremely feminine. Most every female wore a bra and full cut panties under a half or full slip every day. Garter belts and...