Playboys
By Victor 17 Nov 2025
A frat initiation goes sideways for one straight frat boy. Forced to waitress an alumni party while scantily dressed, brings a realization that he may be repressing his true sexual nature.
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.
Rocky Horror
By Victor 14 Nov 2025
Straight, frat boy Colt has never been to the Rocky Horror Picture Show, but his buddies assure him that it's perfectly normal to wear costume lingerie. When he catches the eye of an alpha Marine, he starts to wonder if he actually likes that attention he's getting dressed in slutty lingerie.
Used the wrong medication
By Frank Chainges 7 Oct 2025
Needed to enlarge my manhood and bought some meds off the internet.. results were NOT what I expected
Didn’t know it was a gay bar (ch. 3)
By Alleykat 27 Sep 2025
Drugs blackmail sissyboi
Didn’t know it was a gay bar (ch. 2)
By Alleykat 25 Sep 2025
True story how I went from a straight kid into a sissyboi in a weekend
I Love Wearing Laced Panties
By Prettyboy 9 Sep 2025
Jackie got hard the first time she put on white laced panties and came in them. He partner Jeff is turned by Jackie wearing her laced panties and her pretty pink Nike boots. They enjoy sex with the white lace and pink boots and finish with Jeff pissing on Jackie's laced ass.
Whispers by the Waves (ch. 4)
By gorillaz1993 14 Aug 2025
Their final morning together in the cabin, Alex decides to thank Marcus in his own way...
Whispers by the Waves (ch. 2)
By gorillaz1993 12 Aug 2025
Alex untied it curiously, lifting the lid to reveal black fishnet stockings and a pair of matching black lacy panties, the delicate fabric intricate and sheer. His eyes widened, a flare of nerves twisting in his stomach...
I took 'her' to the prom
By BillyBoy 11 Aug 2025
A new younger friend said he always wanted to go to pram as a girl. I agreed and set it up
Living my sub fantasies (ch. 5)
By Italiansub 2 Jul 2025
Josh, Nathan and Mark team up to abuse my boy pussy, flooding me with cum. Josh makes me downside to a smaller pink cage and turns my hole in a proper pussy.
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Jock Princess
By Victor 28 Jun 2025
My son's jock best friend wants to be daddy's side pussy.
Muscle Boy Girlfriends
By Victor 21 Jun 2025
Two football teammates at odds with each other find out they have some things in common: Muscle, domination, lingerie.
Fan Meet and Greet
By Victor 18 Jun 2025
true story of me relenting to meet with a fan, a big, muscled, closeted, college athlete who was too perfect to pass up.
Gym Bag
By Victor 7 Jun 2025
For extra income, two college jocks whore themselves out to men who like other masculine men in lingerie. One of them meets a man who thinks he's met the man of his dreams.
I'm no longer the man in charge
By BillyBoy 6 Jun 2025
A normal guy gives in to his wife's requests to dress in her lingerie, giving him the best sex ever, but it's all a lie
Sissy for old Men
By Cherrypie 23 Apr 2025
Cute young sissy discovers her need for cock..Old mens cock
My full time journey
By Jester4fun 18 Apr 2025
The story of how and why I went full time feminine
Interracial Couple Roleplay
By Alamander 7 Apr 2025
Carlos and TK meet up in a love hotel to role-play as strangers.
Six Month Anniversary
By Victor 23 Mar 2025
Two formally straight men have been dating for 6 months.For their anniversary, alpha Jenner comes home to find his boyfriend waiting for him dressed up sexy and pretty for him. He's gonna make sure Jenner knows he's the man of the house.
The Mastery of Table-Turning (ch. 28)
By Rawley Myers 13 Feb 2025
Can one imagine anything more blood-curdlingly horrendous to contemplate than for a thirty-year-old man having to stand - in nylon stockings, suspenders and high heels, dressed in a tiny pair of frilly lace knickers, clearly on view and openly revealing his rampantly aroused manhood.
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The Mastery of Table-Turning (ch. 27)
By Rawley Myers 12 Feb 2025
As I was told to stand up, a woman’s black lace suspender belt was produced and fitted round my waist. Elastic straps with satin ribbons hung down at both the front and back of each thigh with the little rubber button clasp.
My first time with Terrell (ch. 2)
By pawb bunny 7 Dec 2024
The days following
My Halloween crossdressing story
By BillyBoy 19 Nov 2024
I knew I shouldn't, but I dressed in women's clothes again this Halloween. It turned out much different from last year, but the final results were the same. A cock in my mouth and another one in my, you know where.
My first time with Terrell
By pawb bunny 14 Oct 2024
White 18 year olds first time having sex and its with a sexy 26 year old black man
CD Hotel sex
By Jester4fun 3 Oct 2024
Sissy CD takes dick in hotel
Lisboa Surprise
By Frankfurt Chronicler 2 Aug 2024
Man's long weekend in Lisbon gets off to a hot start when he hooks up with a mature man into light domination and lingerie.
My Day with Sir
By boi 31 Jul 2024
boi has the day of his dreams with his Sir/Daddy. This came about as a result of a prompt from the guy I’m currently talking to. Let me know your thoughts and let me know if you want this to become a series.
Can I go back to my favourite club? (ch. 3)
By Frankfurt Chronicler 18 Jul 2024
The concluding chapter of the narrator's unexpected sexual adventure at his favourite club while the band plays.
Can I go back to my favourite club? (ch. 2)
By Frankfurt Chronicler 17 Jul 2024
Our narrator's adventure at his favourite club continues with an unexpected sexual encounter while the band plays.
Jocks and Panties
By Victor 17 Jul 2024
Branson is a big, muscular, athletic jock who can't understand his need to be treated like an another man's bitch.
Can I go back to my favourite club?
By Frankfurt Chronicler 16 Jul 2024
Our narrator has an unexpected sexual encounter with two men at the club while the band plays, losing his cherry and his pants in the same evening.
Wearing my wife's thongs
By Viki 15 Apr 2024
Just a short story - I sent him pictures of me in my wife's thong. He liked them, especially how my ass looked in them.
We met for a beer
By BillyBoy 22 Mar 2024
I wore lingerie under my slack and polo. He liked that a lot
Lost Bet
By Victor 8 Mar 2024
Straight acting Chris lost a bet and his punishment was to be a cage dancer for 1 hour at a gay club, but he had to do it dressed like a slut. Colin and Kevin are straight, best friends, and roommates. They venture to the same club that night for a celebration. When Colin sees Chris dancing in a cage, something stirs inside of him and all he wants now is Chris.
The beauty of lingerie (ch. 2)
By Thatslife 25 Feb 2024
Following on from my first introduction to lace, in particular panties by my mother. I was now very interesting in exploring what other types of lingerie effected my cock and level of horniness. My search took me to the contents of my mother's underwear drawers.