Gay Lingerie Stories

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It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

The Night of My Life

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I live in England, and am leaving school this year, and am 18 years old. We've adopted the American tradition of prom, where guys get tuxedos and girls get dresses, and they all go to a party and dance with each other. The prom was in July, and when my story began it was May. People were beginning to ask people to go with them to prom. A few people had girl...

Mommy's Boy?

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

"Hi honey, how was your day?" My mom called out her usual question as I came in through the side door, and tried to quit sniffling. In vain -- I still had the hiccups from my recent crying jag, and my nose was running. I'm sure my face was red too. "F-fine," I hiccuped. Obviously, it hadn't been fine. "Oh, hon, did those boys tease you again? They're so ru...

Three's a Circle, Not a Triangle Ch. 10

by SusanJillParker on Sep 25, 2017
Fetish

Susan has a panty, bra, and shoe fetish and so doesn't William and Liz too. After weeks of giving William and his wife, Liz, the same sexy, striptease show of her stripping herself naked and parading around her room naked before getting in bed to masturbate herself, the next night, Susan gave them a much different show but one as equally erotic. Instead of...

Fifi La Femme: A Pansy at Last Ch. 02

by pris69696 on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2- Missing Big Frank Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me to marry him; to be his gay wi...

Was He Becoming A Cross Dresser Ch. 04

by Alpha2Bravo on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 4 NEEDED MORE I was at a point of no return.... I was spending money like crazy. I didn't care, every chance I had I would run to my computer and go back to the site I had bought most of my cloth and lingerie and searched frantically for a wig. Once I typed in the word "WIG" there were hundreds of sellers. I looked at hundreds and hundreds of wigs t...

Blackmailed Pt. 06

by cdsissybambi69 on Sep 18, 2017
Transsexuals & Crossdressers

I woke up once again, right next to Hannah in my bra and panties to the sobering thought that I had to be a boy tomorrow. The thought killed me. I didn't want to go back to being a nobody after the amazing time that I had this past weekend. I was the center of attention as Bambi, everyone wanted to get to know me, well fuck me, but same thing. I sat up from...

Jackie Pt. 02

by Scribler on Sep 12, 2017
Transsexuals & Crossdressers

Chapter Six Angie woke me at five in the morning. Normally I didn't get up for work until six so I could be at the office by eight. This morning I had to go home and get dressed for work, as I didn't bring anything with me on Saturday. After getting out of the shower Angie handed me a pair of white panties and said. "Will you please wear these today? I wa...

Cuckold: Mia and Greg's Story

by glmike523 on Sep 17, 2017
Fetish

For the last 5 years Greg has been a cuckold husband. It all started one evening when he and his wife Mia decided to relive the spark they once had by going to a darkened parking lot and to have sex in their car. Mia is a very attractive woman and Greg is a handsome man. Greg looks a lot younger than his 42 years but if there is any downside to Greg it is h...

Cinderella - a BDSM Retelling

by MistressMoira on Sep 25, 2017
BDSM

Once upon a time there lived a kinky girl, a very kinky girl indeed, named, well never mind her real name, her chosen nick for play was "Cinderella", for reasons which will become apparent later. Cinderella lived in a polyamorous family with an assortment of bdsm proclivities with her "Daddy" (a switch - top to Cinderella and bottom to his Domme to whom he...