Gay Crossdressing Stories

GayDemon's gay porn library: in this story category you can find erotic stories with crossdressers and crossdressings.

7.0
54 Votes

A Harmless White Nylon Thong

Story by nylonlingerie

3 Aug 2020 21511 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

9.1
114 Votes

A Sissy Life

Story by Faedirk

7 Jul 2020 25822 Readers comments 13 Min Read

Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.

Topics: Crossdressing, Bondage, Sissy, Face Fuck, Master & Slave, Domination

8.2
20 Votes

Meetup Gone Crazy

Story by Luke Holton

16 Jun 2020 4951 Readers comments 10 Min Read

After I met a guy at his hotel, him and his team tie me to a bed and chloroform me. Read to find out what happens next

Topics: Crossdressing, Bondage, Abduction, Drugs, Sex

9.4
21 Votes

Failed Connections

Story by Habu

12 Jun 2020 2595 Readers comments 41 Min Read

It's all about the pro soccer player's need in fetish play in Denver and Chicago.

Topics: Crossdressing, Sportsmen, Sex, Small Cock, Age Difference, Fucking

9.8
14 Votes

my life (ch. 17)

Story by bijim

10 Jun 2020 2421 Readers comments 9 Min Read

a club dancing and developing a crush on a guy

Topics: Anal Sex, Crossdressing, Romance, Oral & Blowjobs, Love

9.0
38 Votes

Gay sex change?

Story by Rubbertransformation

31 May 2020 7257 Readers comments 5 Min Read

I love taking cock but often wonder what it would be like to have a pussy instead!

Topics: Crossdressing, Dildo, Pantyhose, Piercing, Transformation

8.0
5 Votes

Turn About is Fair Play

Story by Mikal

30 May 2020 483 Readers comments 6 Min Read

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

9.2
11 Votes

Sweet Chrissi (ch. 5)

Story by Mikal

29 May 2020 2337 Readers comments 3 Min Read

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

9.6
23 Votes

Muscleboy Double-Teamed in the Gym Shower (ch. 3)

Story by GameBoy94

9 May 2020 6178 Readers comments 21 Min Read

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

9.1
75 Votes

Crossdressing faggot meets a brutish construction worker

Story by Alex Walker

8 May 2020 12409 Readers comments 6 Min Read

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

7.4
16 Votes

I Love Being a Faggot

Story by cock whore kimmy

5 May 2020 6276 Readers comments 7 Min Read

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

8.9
16 Votes

Caesars Bitch (ch. 2)

Story by Mikal

29 Apr 2020 2730 Readers comments 6 Min Read

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

8.8
33 Votes

Living my dream (ch. 2)

Story by SissyBoi

16 Apr 2020 7584 Readers comments 8 Min Read

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

8.5
39 Votes

Sacked Quarterback

Story by Cracker

7 Apr 2020 4292 Readers comments 9 Min Read

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

8.4
19 Votes

Sissy Transformation

Story by Mikal

5 Apr 2020 5814 Readers comments 4 Min Read

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

8.4
12 Votes

The end of a perfect night out as a sexy woman

Story by Bob Long

1 Mar 2020 3229 Readers comments 11 Min Read

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

7.9
51 Votes

Gary: The Cock Hungry, Cum Guzzling, Sissy Faggot

Story by cock whore kimmy

27 Feb 2020 7005 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

9.0
33 Votes

A Sexual Progression

Story by Alaina

19 Feb 2020 17417 Readers comments 118 Min Read

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

7.8
30 Votes

Before she turned me out

Story by Bob Long

10 Feb 2020 7606 Readers comments 49 Min Read

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

7.8
4 Votes

How I got started (ch. 2)

Story by Bob Long

4 Feb 2020 1884 Readers comments 22 Min Read

This is a continuation of my glorious introduction to crossdressing and sex

Topics: Crossdressing, Rimming

7.3
40 Votes

Parking lot blowjob

Story by Bob Long

1 Feb 2020 9051 Readers comments 24 Min Read

This is the story of how my ex girlfriend, made it her mission to get me to suck a guys cock

Topics: Black Men, Anal Sex, Crossdressing, Handjob, Rimming, Spanking, Role Play, Oral & Blowjobs, Cuckold

8.4
48 Votes

The Art of the Sissygasm

Story by cock whore kimmy

26 Jan 2020 9013 Readers comments 3 Min Read

Little CD fuckdoll has his first sissygasm and his life changed forever!

Topics: Anal Sex, Crossdressing, Big Dick, Sissy, Oral & Blowjobs

8.6
78 Votes

Caught crossdressing

Story by SandyCD

6 Jan 2020 12149 Readers comments 12 Min Read

Caught by daughter with me dressed as woman

Topics: Black Men, Crossdressing, Dildo, Spanking, Sissy

7.7
15 Votes

Big Sissy

Story by Nils Huim

28 Dec 2019 9705 Readers comments 10 Min Read

A gay sissy bottom receives a surprise birthday gift

Topics: Anal Sex, Crossdressing, Hairy men, Sissy

7.8
69 Votes

A Sissy’s Dream Comes True! Again and again!!

Story by FishnetSissy

21 Dec 2019 31982 Readers comments 28 Min Read

2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!

Topics: Anal Sex, Crossdressing, Dildo, Big Dick, Gloryhole, Sissy, Oral & Blowjobs, Small Cock, Blond

7.7
21 Votes

Starbucks

Story by Nils Huim

16 Dec 2019 1566 Readers comments 10 Min Read

Two ex-cons have anal & oral sex and then plot (?) a robbery

Topics: Muscle, Crossdressing, Sissy

8.7
16 Votes

Un-Expected Threesome

Story by Kristen Kross

7 Dec 2019 2599 Readers comments 24 Min Read

CD, girl, and a stranger meet in a motel room

Topics: Anal Sex, Crossdressing, Big Dick, Threesome, Transgender, Sissy, Hotels, Oral & Blowjobs