Gay Lingerie Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about crossdressing men wearing and having sex in lingerie listed by date.

8.9
31 Votes

Earning Power

Story by Petr-Johan

25 Sep 2020 1771 Readers comments 25 Min Read

Two factory workers find that their boyfriends, bored at home, have taken a fancy to ladies lingerie. Their money is stolen which forces all four of them into a line of work that none of them had ever done before but desperation for funds is very motivating.

Topics: Anal Sex, Crossdressing, Prostitution, Incest, Oral & Blowjobs, Sex, Lingerie, Boyfriends, Body Modification, Fucking, Porn

7.0
54 Votes

A Harmless White Nylon Thong

Story by nylonlingerie

3 Aug 2020 21508 Readers comments 4 Min Read

I received a small parcel through the post, not ordered anything from any mail order, so I carefully opened it..

Topics: Crossdressing, Dildo, Transformation, Underwear, Lingerie

9.3
114 Votes

Fighter Pilot's Pussy

Story by Clark Wayne

4 Apr 2020 11089 Readers comments 24 Min Read

Bi fighter pilot comes home to find his fighter pilot fuck-buddy waiting for him in sexy lingerie.

Topics: Anal Sex, Muscle, Crossdressing, Straight Men, Humiliation, Bisexual, Power Bottom, Master & Slave, Lingerie, Married, Fucking

7.9
51 Votes

Gary: The Cock Hungry, Cum Guzzling, Sissy Faggot

Story by cock whore kimmy

27 Feb 2020 6999 Readers comments 25 Min Read

Kim comes home early from work and hears a whore getting fucked in her bedroom. She can only assume her BF Gary is in there cheating on her. So she slips in to catch him in the act, but what she finds in nothing like what she thought. She finds Gary all alone, lying on the bed. He’s wearing some of her sluttiest clothing, and trashiest lingerie. And he’s fucking himself with her favorite ...

Topics: Sex, Lingerie

8.7
102 Votes

Broken

Story by Clark Wayne

17 Feb 2020 11246 Readers comments 6 Min Read

Straight man is attracted to an alpha. He becomes the alpha's toy. He tries to rebel but his new Alpha has decided to fix his attitude and humiliate him. If the closeted straight guy wants to get fucked, he'll have to wear some panties to show his devotion.

Topics: Anal Sex, Muscle, Crossdressing, Straight Men, Humiliation, Bisexual, Master & Slave, Lingerie, Fucking

8.2
54 Votes

The Victoria's Secret Male Model

Story by A. Williams

6 Aug 2015 2996 Readers comments 4 Min Read

NO MAN had ever modeled for Victoria's Secret in woman's lingerie and he believed he should be the first. Really...see what happens between the male model and the male photographer...

Topics: Relationship, Lingerie

7.5
12 Votes

Used and Abused

Story by Flyman

19 Nov 2013 4248 Readers comments 16 Min Read

A few minutes later I stood in front of the mirrored wall looking at a man dressed totally as a cheap whore with red lingerie and with bright red lipstick on. I had on a long blond wig and felt very slutty. This was my first time in adult women's clothes and it brought back memories of the times my mother dressed me as a girl when I was a little Tot.

Topics: Piss, Fisting, Sloppy Hole, Slut, Blond, Lingerie

7.9
10 Votes

I was shopping for a girl

Story by craig

22 Jun 2012 2104 Readers comments 6 Min Read

How I came to be feminized and how I learned to like getting made up and shopping for my lingerie, and other female attire, I was good at being their sexy girl.

Topics: First Time, Lingerie, Feminization

8.8
10 Votes

Sales Figures

Story by edknipe

26 Nov 2008 1208 Readers comments 15 Min Read

"It is a sound business plan" moaned Chris as he rechecked the figures before him "We're in the middle of a 90% gay owner area and a men's lingerie shop should be booming."

Topics: Relationship, Gloryhole, Lingerie