Gay Lingerie Stories

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Adventures with Dolores

by beaverjoe on Sep 25, 2017
Mature

I've had a huge crush on one of my coworkers for the past few years. Her name is Dolores. She is 49 and a mother of three so she definitely qualifies as a MILF. Dolores is a little over five feet tall and is very slim with short brown hair. Her breasts are very small, my guess would be 34A, maybe B. My favorite part of her body is definitely her ass. It also...

A Happy Couple

by seeshyotama on Sep 13, 2017
Fetish

All characters in this story are older than 18 when they perform these sexual acts. Also there is a 99.9% gay male in female lingerie, a female penetrating a 99.9% gay male with a strapless dildo, impregnation, a marriage proposal, and two happy people in a monogamous relationship. If you don't like any of what you just read then I don't think this story is...

Club Inzest 12

by BrettJ on Sep 26, 2017
Novels and Novellas

Chapter 12: Wedding Bells by Micaela Reynolds as told to BrettJ © 2009 We were all having a late lunch one afternoon and Christina ran into the room, squealing and nearly hysterical. Neither her mother nor I could understand a single word she was saying, she was crying and emotional. Chris, who can normally understand his twin in the oddest of situations...

Eric's Dreams Pt. 03

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

Eric kept thinking about his sex problem. He was a crossdresser. But most gay men didn't like that. The sex, yes, but not the crossdressing. Gay men, at least most gay men, had no interest in lipstick and lingerie, and the thrill of passing as a woman. They wanted to fuck and be fucked by men. They wanted to have their cocks sucked by men. And they wanted to...

Exploring My Feelings Ch. 01

by dave1967fun on Jun 19, 2018
Transsexuals & Crossdressers

I was in my second year of college when I first realized that I was curious about men. Ok, so let me go back a bit. I have always been a man's man, and played sports in High School, including football, baseball, etc. But one night when I was in 12th grade (18 yo) and I was staying overnight at a friends house. They had me stay in his sisters room. She was a...

Kayla Caught Me Ch. 01

by lulu_dools on May 1, 2018
Transsexuals & Crossdressers

Hello there. Let me tell you what happens when you get caught... You see I am a cross dresser when I get time and have lots and lots of clothes and lingerie to play with. I keep all my female stuff in the computer room where no one ever gets to go. I am 40 years old with long curly brown hair and brown eyes. I weigh about 80kgs and am 5ft 8inches tall. I l...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Making a Woman of Him Ch. 01

by ElRoylk on Sep 15, 2017
Fetish

"Who's he?" Millard pointed to the slight figured guy passing hors d'oeuvres through the crowded party room. "Chester," John responded, screwing up his face. "He's kind of queer." "I'll say. Isn't it a little late to be rushing?" "Oh, he isn't rushing," John paused to take a swig from his beer. "No...Chester was accepted last fall. He just dresses that...

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...

Working Relationship

by Jonnyflies on Aug 31, 2017
Fetish

Sarah had been working as P.A for David, a junior partner at the legal firm, for over a year. She was happy in her work and they got on well together. From her first day Sarah had felt a 'connection' to him and this empathy seemed to show in the work that they were involved in. She could tell that he liked her, he was kind and considerate, and she seemed to...