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.

The beauty of lingerie

By Thatslife 23 Feb 2024

This is a true story that started my passion for lingerie, it also involved the two women in my family. I was given the opportunity to touch their lingerie while they wore it. I was hooked then

8.0 (22) 2454 4 Min Comments

Laundry will never be the same

By Ky 3 Jan 2024

Growing up laundry was one of our chores my brother and I had to rotate weekly between our sisters. We jokingly dared each other to try on our sisters clothes but had no idea what start between us

7.0 (15) 3933 3 Min Comments

A Lesson in Humility

By Victor 10 Dec 2023

Turner is an alpha male who hooks up with Beau, a cocky, closeted frat boy who turns out to be an experienced power bottom. Turner has rules and Beau breaks an important rule. His punishment is a lesson in humility and emasculation.

9.3 (127) 7907 25 Min Comments

Why Him, of All People (ch. 4)

By I. Dusk 27 Nov 2023

“I hope you like red stockings. I’ve been hard the whole night because I wore them under the pants.” I turned to him and watched him with hunger. I took a step toward him. “A-a-a, big guy! Not here! We are still not finished.” He grinned at me flirtatiously. I growled and turned back to wipe the glasses.

9.5 (10) 1968 13 Min Comments

Nasty Time in BDSM

By BillyBoy 19 Nov 2023

A Domme transvestite seduces me then introduces me to a few of her other slave fuck buddies. i'm the meat in this crazy sandwich!

8.8 (32) 4830 11 Min Comments

Coercion (ch. 3)

By Tommy 16 Nov 2023

My adventures and awakening continue and I knew Mr. Waxman had some plans that I was looking forward too.

9.4 (29) 2931 14 Min Comments

Living my sub fantasies (ch. 2)

By Italiansub 1 Nov 2023

Chapter 2 of my submission to Josh. In this chapter Josh has an exciting surprise for me and decides that i should be in chastity for a longer period of time.

9.4 (33) 7380 13 Min Comments

Mandeleter

By BillyBoy 8 Sep 2023

a man seduces me into being his bitch.

9.4 (31) 5672 21 Min Comments

Turning Chase (ch. 4)

By Chase Huxley 4 Sep 2023

Chase Huxley is a star athlete on his wrestling and rugby teams. He's always been a nice, wholesome person, but his older stepbrother Brad is in the process of turning him into a complete cock slut this summer.

9.4 (199) 21997 31 Min Comments

Turning Chase (ch. 3)

By Chase Huxley 31 Aug 2023

Chase Huxley is a star athlete on his wrestling and rugby teams. He's always been a nice, wholesome person, but his older stepbrother Brad has plans to turn him into a complete cock slut by the end of the summer. In this chapter, Brad's plan to pop his little stepbro's anal cherry finally gets put into motion.

9.4 (247) 26481 23 Min Comments

Why Him, of All People (ch. 3)

By I. Dusk 26 Aug 2023

I heard his chuckle and looked at him. "What's so funny?" "You are, Sam. I can't figure you out." "Trust me, me neither. I am one smart person, but for some reason, when you are near, I start babbling like a moron. Like now, for example. Damn it." He was grinning like a mischievous little brat. Great.

9.4 (19) 1657 15 Min Comments

Trailer trash cumdump

By Alleykat 19 Aug 2023

How I became white trash for rednecks at the trailer park

8.5 (144) 26329 3 Min Comments

Why Him, of All People (ch. 2)

By I. Dusk 9 Aug 2023

“Do you want me to quit?” “No. Do you want to quit?” “No.” “Good. I think you looked good behind that bar.” He smirked and raised his eyebrow. Idiot! “I mean, you were good at bartending.” I don’t know why this is happening?! I can usually form two basic sentences without rambling like a fool. So why do I suddenly get so nervous when he is near?

9.4 (34) 2092 12 Min Comments

Frat Initiation

By Victor 2 Aug 2023

The president of the frat is slowly manipulating his freshman pledge, a masculine, cocky, gorgeous muscleboy to his will during hell week when all the pledges have to dress up like French maids and serve their future frat brothers at a party. The new pledge realizes he liked it a little too much.

9.2 (171) 18695 28 Min Comments

First or was panties

By Alleykat 24 Jul 2023

I kept staring at those sexy panties in the adult bookstore

9.4 (89) 10248 5 Min Comments

Crossing the line (ch. 2)

By lickme 14 Jul 2023

A hetero guy starts to enjoy his feminine side and begins to learn how to satisfy his cravings

9.1 (15) 3492 3 Min Comments

Bobby's Pink Panties

By luvaslip 6 Jul 2023

Bobby has been hiding a big secret and he meets a stranger who helps him fulfill that secret and more.

8.8 (72) 7578 5 Min Comments

Crossing the line

By lickme 3 Jul 2023

A hetero guy who is gradually groomed to be a feminized cock loving whore

8.2 (47) 5746 2 Min Comments

Playdate with Daddy

By BillyBoy 26 Jun 2023

call me daddy. yes Sir. oh, sorry, yes daddy

8.6 (28) 7756 8 Min Comments

Caught by Aunt's Boyfriend

By Katie Femboy 5 Jun 2023

Stayed at my Aunts house most weekends, thought the house was empty and got caught in her lingerie by her boyfriend. He ran out quite fast but ended up sending me a drunken text message

8.5 (61) 10902 3 Min Comments

Prom Dress Contest for The Boys

By BillyBoy 22 Apr 2023

Having all the sissy's in town show up wasn't as hard as I thought

5.8 (10) 2865 8 Min Comments

Bras, Bros and Blowjobs

By BillyBoy 21 Apr 2023

my study buddy caught me playing in my sisters underwear

7.5 (25) 7645 5 Min Comments

Married to the Game

By Phaggotry 13 Apr 2023

A closeted ex-con biker queer marries a heterosexual woman to the lustful amusement of the colorful cocks they have in common.

8.9 (21) 2869 11 Min Comments

Why Him, of All People

By I. Dusk 4 Apr 2023

“Hi, daddy.” “Hi… please don’t call me daddy.” I was nervous as it was. He was eyeing me shamelessly, and I felt extremely uncomfortable. Nevertheless, I let him pull me in. Checking anxiously if anyone was out there seeing us. “And how would you like me to call you?” “I am Sam. What is your name?” “You can call me boy.”

9.4 (40) 4984 10 Min Comments

A simple mistake

By BillyBoy 20 Mar 2023

My wife catches me in her underwear. She tells her friends. One of her friends husband call me. Then it begins.

6.7 (51) 8770 2 Min Comments

my sissy encounter turns into a bondage fuck-fest

By BillyBoy 27 Feb 2023

Greg searches for submissive sissy type guys on the dating sites. He messages me, seduces me, dresses me in silk and lace, and begins playing in some light bondage. Then he introduces me to his Dom daddy, Bob

8.8 (31) 7773 5 Min Comments

I'm aged but still horny

By Italian sub Cindy 21 Feb 2023

Aged but horny dominanca and submission lover

6.8 (12) 2158 5 Min Comments

Sexy CD's first gay encounter (ch. 2)

By fanny 6 Feb 2023

After our first encounter, he was getting hungry again for some of my ass. After a month, I saw some new packages was sent to me. As I opened them, noticed there are some new sexy lingeries and dresses with panties.

7.9 (15) 1941 2 Min Comments

Neighborhood faggot boy (ch. 3)

By Alleykat 29 Jan 2023

I used to be just an innocent Kidd now I’m a Heather 4 my daddy n his friends. And they know where I live

9.1 (57) 11833 3 Min Comments

The Magical Thong (ch. 4)

By Oliver Andrews 21 Jan 2023

After some naughty moment at the restaurant, Aaron meet his Daddy

8.3 (23) 8449 11 Min Comments

He Wanted Sex In Lingerie

By Jjj1975x 5 Jan 2023

I am a married man who met a guy at a party. The guy wanted to have sex with me in lingerie. That is, he wanted me to wear lingerie. I didn’t think I would like it. But it was amazing.

8.9 (37) 7414 15 Min Comments

Walking the dog leads to more (ch. 2)

By Frankfurt Chronicler 12 Dec 2022

We almost get away with it, but Lars' friends find us and want a piece of the action. This is another long read, but with a ton of sex.

9.3 (21) 2936 22 Min Comments

Walking the dog leads to more

By Frankfurt Chronicler 10 Dec 2022

A mature sissy encounters a young top and his friends in the woods while walking the dog. This is a longer read and my first story, so I'm grateful for any feedback.

9.2 (35) 3735 18 Min Comments

Bodybuilder's Bitch

By Victor 26 Nov 2022

College athlete wears lingerie for two bodybuilders from his gym.

9.3 (119) 16251 10 Min Comments

Own-Me! (ch. 2)

By I. Dusk 24 Nov 2022

N: There is a restroom next to the stairwell. It's usually empty in the morning. What time are you usually in the office? O: 9 o'clock, Sir N: Be there at 7:30, cum-dump N: I will breed that pussy tomorrow, and you will keep it there until 6, when I will fill you again.

9.4 (64) 5490 12 Min Comments