16 Votes
my life (ch. 15)
more abuse from bill a double penetration surprise and falling for a milking machine
Topics: Anal Sex, Crossdressing, DP, Bisexual, Milking, Master & Slave
GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressing up as women and gay sex with transvestites and crossdressers listed by date.
more abuse from bill a double penetration surprise and falling for a milking machine
Topics: Anal Sex, Crossdressing, DP, Bisexual, Milking, Master & Slave
Turn About is Fair Play is a Caesars Bitch Sweet Chrissi cross over both are Detroiters and Jay Jay is mentioned in my 1st Sweet Chrissi as JJ. Anyway Caesar takes his cross dressing sissy boyfriend Jay Jay out they meet Chrissi and things get real naughty.
Topics: Anal Sex, Crossdressing, Dildo, Relationship, Sissy, Boyfriends
Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.
Topics: Anal Sex, Crossdressing, Big Dick, Romance, Sissy
"'Good boy!' He did some blow. 'Want some?' 'Yes sir, please.' He spread two lines on his fat dick that I had just been sucking on. I put my face down and snorted it off him. "Thank you, sir." I was buzzed and horned to take his prize tool up my ass."
Topics: Anal Sex, Crossdressing, Brothers, Uncle, Slut, Incest, Alpha Male, Oral & Blowjobs, Master & Slave, Domination, Submission
Stan has some downers and uppers.
Topics: Crossdressing, Straight Men, Bisexual, Military, Oral & Blowjobs, Marine
"I sat at the kitchen table not believing what my shaking father was trying to explain to me. The only way out was for one of us kids to become a sex worker and work the debt off. I did what I was supposed to do and said yes." More from Timothy.
Topics: Anal Sex, Crossdressing, First Time, Daddy, Incest, Twink, Oral & Blowjobs, Master & Slave, Domination, Submission
we meet the owners and get acquainted to these remarkable people
Topics: Crossdressing, Bisexual, Oral & Blowjobs
The second part of Jake the muscleboy's steamy molestation on a late-night train car.
Topics: Muscle, Crossdressing, Handjob, Group Sex, Forced, Daddy, Edging, Coercion, Master & Slave, Domination, Gangbang, Nipple Play, Control, Cum Control
A crossdressing fag makes a mistake that catches the attention of a burly construction worker and is invited over for some fun.
Topics: Crossdressing, Hairy men, Construction Worker, Daddy, Sissy, Breeding, Bear, Armpits, Master & Slave, Domination
Jake the muscleboy finds himself longing for another encounter like the one he previously had in the gym shower. He also starts wearing tight girly clothes underneath his regular attire to prepare for such an encounter. Little does he know that his deepest, most perverted fantasies are about to come true (again).
Topics: Crossdressing, Public Sex, Bondage, Handjob, Daddy, Edging, Coercion, Gym, Master & Slave, Domination, Nipple Play, Control, Cum Control
A story about being abducted and fucked by demons.
Topics: Anal Sex, Crossdressing, Abduction, Sissy, Face Fuck, Demons
Gary is a cross dressing sissy faggot, and his love of hot, thick, juicy, stud cock has turned him into the biggest little faggot sissy whore! He’s not happy until he’s left cock drunk, with his face covered in cum, and his little asshole is sore and gaping! What a little slut!
Topics: Crossdressing, Dildo, Masturbation, Bisexual, Sissy, Drunk
This is a new installment of Caesars Bitch. In this tale Caesar has been with Jay jay for a time and is starting off on his first romance and is cementing his relationship. Yes there is abusive language but we are all grown ups so if you can't handle it move on.
Topics: Piss, Anal Sex, Crossdressing, Romance, Sissy, Oral & Blowjobs, Sex
Caesars Bitch is combination of a Cross Dressing & Sissy and First timer story. While I normally tell a story from the bottoms prospective I'm trying to expand my creative horizons and telling a good portion of this kinky tale from the Top Caesars prospective. it is also my sincere hope that you enjoy this tale and tell me what you think in the comments box.
Topics: Anal Sex, Crossdressing, Romance, Oral & Blowjobs
A short story about a fem boy.
Topics: Crossdressing, Rimming, Big Dick, Sissy, Oral & Blowjobs
Cute 18 yo femboy crossdresser meets a real man who gives his little boypussy a proper stretching and makes him his bitch
Topics: Anal Sex, Crossdressing, Big Dick, Sloppy Hole, Alpha Male, Sissy, Cum Dump, Big Balls, Oral & Blowjobs, Femboy
While this story fits in the Crossdressing/Sissy catigory it is also a BDSM story. In Sweet Crhissi Chapter 4 Naughty Sissy's get Punished Chrissi is caught in bed with another man by his boyfriend Steve and there is Hell to pay.
Topics: Crossdressing, Spanking, Relationship, Sissy, SM, Oral & Blowjobs, Boyfriends
A macho star quarterback goes from a chick fucker to a cross dressing chick-with-a-dick who gets fucked.
Topics: Black Men, Latin Men, Anal Sex, Crossdressing, Dildo, Oral & Blowjobs
Hi everyone I'm sure many of you are at home board and horny right now. Well I hope I can help relieve some of you with this story about a closeted sissy who meets a mistress that helps him find his true sissy self after he gets in debt to her.
Topics: Piss, Anal Sex, Crossdressing, Sissy, BDSM
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
Sex-charged shenanigans, a touch of danger, an unexpected arrival - open young Hiram's eyes to more of the Farm's horizon than he has glimpsed thus far. Can he keep pace? What will he feel (with his hands) for the very first time? Where does his curiosity lead him this time?
Topics: Crossdressing, Spanking, Locker Room, Transgender
This was the last but ultimately the best part of evening when my girlfriend took me out to a gay club, dressed as a woman just to test the water and to assure me that I not only very passable but also pretty damn hot. I got way much more than I imagined
Topics: Anal Sex, Crossdressing
Abused, rejected little boys journey to a manipulative, desirable and successful woman
Topics: Black Men, Anal Sex, Crossdressing, Dildo, Big Dick, Group Sex, Transgender, Sissy, Oral & Blowjobs, Feminization
Bored and in need of some dick Chrissi gets a surprise visit from a fellow sissy boy friend Daisy and it leads to a three way.
Topics: Black Men, Anal Sex, Crossdressing, Enema, Sissy
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
My girlfriend who fostered my obsession with crossdressing and living as a woman, trained and made me into one hell of a beautiful woman who eventually sucked a mans cock and loved it
Topics: Anal Sex, Crossdressing, Transgender, Oral & Blowjobs
Our continuing story of the greatest time of my life exploring and fulfilling my deep seated desire to be a woman through crossdressing and learning about my sexuality with the best teacher in the world my mom
Topics: Crossdressing, Incest, Oral & Blowjobs
This is a continuation of my glorious introduction to crossdressing and sex
Topics: Crossdressing, Rimming
He could still feel Ezekiel's mouth on his, and on his neck. He could still feel Ezekiel's chest and stomach against his back, Ezekiel in him, and through him, his penis, swelling and pumping in his mouth, the warm touch of the palm of his hand.
Topics: Crossdressing, Relationship, Bisexual
Sex helps sell expensive San Francisco condos.
Topics: Anal Sex, Crossdressing