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.
“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.”
Topics: Anal Sex, Rimming, Romance, First Time, Feet, Age Difference, Lingerie, Boss, Bartender
My wife catches me in her underwear. She tells her friends. One of her friends husband call me. Then it begins.
Topics: Crossdressing, Sissy, Oral & Blowjobs, Lingerie
In the beginning my 2 older sisters teased and taunted me. At the same time, mom's and their girly underwear was everywhere.
Topics: Crossdressing, Bondage, First Time, Lingerie, Panties
The two football players score a hook up with one of Toby's fuck buddies.
Topics: Crossdressing, Rough Sex, Threesome, Coach, Age Difference, Lingerie, Footballer, Panties, Fucking, CNC
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
Topics: Anal Sex, Crossdressing, Bondage, Rimming, Daddy, Sissy, Domination, Lingerie
Aged but horny dominanca and submission lover
Topics: Daddy, Bisexual, Sissy, Nipple Play, Lingerie
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.
Topics: Crossdressing, Sex, Lingerie
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
Topics: Slut, Sissy, Cum Dump, Age Difference, Gangbang, Lingerie, Panties
After some naughty moment at the restaurant, Aaron meet his Daddy
Topics: Chastity, Big Dick, Fisting, Group Sex, Doctor, Daddy, Creampie, Incest, Bareback, Exhibitionism, Dad & Son, DILF, Lingerie, Mature Men
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.
Topics: Anal Sex, Crossdressing, First Time, Lingerie, Panties
Two teen football studs have a secret. Both dated a girl who introduced them to butt play. She eventually adds in panties to the mix. When the guys find out about each other, they explore their new kink together.
Topics: Anal Sex, Crossdressing, Bisexual, Ass Play, Lingerie, Footballer, Panties, Fucking, CNC
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.
Topics: Anal Sex, Crossdressing, Public Sex, Outdoor, Sissy, Bareback, Oral & Blowjobs, Age Difference, Domination, Young Top, Lingerie
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.
Topics: Anal Sex, Crossdressing, Public Sex, Bareback, Age Difference, Domination, Young Top, Lingerie
College athlete wears lingerie for two bodybuilders from his gym.
Topics: Muscle, Crossdressing, Threesome, Sissy, Underwear, Domination, Lingerie, Kissing, Panties, Fucking, Bodybuilder
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.
Topics: Anal Sex, Public Sex, Rimming, Bathroom, Cum Dump, Verbal, Co-worker, BDSM, Blindfold, Lingerie
I cruise for the first time and learn what that involves .
Topics: Crossdressing, Cruising, Sissy, Exhibitionism, Lingerie, Panties
A custodian at high school who had made a pass at me was remembered as being the only person I was sure was homosexual and as my crossdressing urges grew stronger he became the focus of a plan to act them out . What follows is true .
Topics: Crossdressing, Underwear, Lingerie, Panties
I’ve never thought about of gay sex in my life so far. But one night it changed. As usual boring weekend, I was scrolling through some porn and all of a sudden, some hypno sissy gay porn videos kinda got my attention.
Topics: Crossdressing, Sex, Lingerie
When Blair had agreed to a second date, all I could think about was how to get inside his pants. Turned out to be harder than I thought.
Topics: Transgender, Cum, Co-worker, Hookups & Dates, Deep Throat, Lingerie
Our character discover the pleasure of being filled by hot brothers
Topics: Chastity, Big Dick, Fisting, Group Sex, Humiliation, Doctor, Creampie, Incest, Bareback, Dad & Son, DILF, Lingerie, Nudity, Mature Men
After discovering anal pleasure a straight jock go to his morning classes and it turns sexual.
Topics: Public Sex, Chastity, Rimming, Group Sex, College, Incest, Bullies, Teacher, Dad & Son, Domination, Lingerie, Orgy, Mature Men
A str8 athlete buy with his friends a thong as a joke but this will turn his world upside down.
Topics: Muscle, Big Dick, College, Incest, Breeding, Sportsmen, Dad & Son, Big Ass, Jockstraps, Lingerie
After discovering his father is Robert Durham slave and moved to their house, Josh realizes he has more in common with his father. A story full of cum, thongs and other streched holes.
Topics: Dildo, Big Dick, Humiliation, Alpha Male, Bullies, Dad & Son, Big Balls, Submission, Ass Play, Lingerie, Body Modification
Daddy has fun surprises in store for his boy princess as they mix business and pleasure in Palm Springs
Topics: Anal Sex, Crossdressing, Daddy, Boypussy, Lingerie
Tall, massively muscular Brodin is a no nonsense bottom with many fuck buddies. One night a married fuck buddy asks him to slip on a pair of panties. To Brodin's surprise, he likes it and so starts a new kink for the big, broad bodybuilder.
Topics: Muscle, Crossdressing, Role Play, Lingerie, Married, Bodybuilder
Because he can't pay up his debt, a father decides to turn his whole family into slut slave for his boss family
Topics: Chastity, Rimming, Slut, Incest, Bullies, Dad & Son, Domination, Lingerie, Mature Men
My hot DILF CEO is an alpha with a soft side when we're alone. The older muscle stud wants nothing more than my younger, muscular body to dominate him and make him my bitch.
Topics: Crossdressing, Threesome, Sex, Age Difference, Domination, DILF, Lingerie, Boss, Kissing, Fucking
Bodybuilder Rick help sell posing clothes to wrestling team members and their Coach
Topics: Anal Sex, Muscle, Group Sex, Boypussy, Exhibitionism, Oral & Blowjobs, Lingerie, Bodybuilder
Bodybuilder Rick entertains his new friends bachelor party and gives all the muscle studs a present
Topics: Anal Sex, Muscle, Group Sex, Daddy, Boypussy, Lingerie, Bodybuilder
this is a gay site, right? well, fuck me running. I got a good one!
Topics: Crossdressing, Bisexual, Lingerie, Witch, Panties