Gay Sissy Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressed and made into girls and sissification listed by date.

8.7
New

Chrisy - The Sissy Slave

Story by Slutty Whore

4 May 2024 2478 Readers comments 5 Min Read

See how two horny ass adults convert a straight boy into a submissive sissy slave that becomes a horniest slut

Topics: Crossdressing, Sissy, Master & Slave, Age Difference, Domination, Cum Eating

9.0
New

Lord Laywood Gets Pimped Out (ch. 4)

Story by EasyWhenDrunk

2 May 2024 1960 Readers comments 5 Min Read

The men from the local tavern have Lord Eden Laywood right where they want him... drunk in the bathroom with his legs spread open. Now they get to take their time and do whatever they want with the slutty prince. He's powerless to stop them.

Topics: Group Sex, Slut, Sissy, Breeding, Verbal, Rape, Degradation, Fucking

9.2
New

Straight Arab Roommate

Story by employee007

21 Apr 2024 4765 Readers comments 20 Min Read

A medical student's world is turned upside down when he is paired with his new roommate, an Arab exchange student.

Topics: Arab, Straight Men, College, Sissy, Sweat, Roommate, Feminization

9.1
6 Votes

Stacey's First Love

Story by luvaslip

14 Apr 2024 731 Readers comments 16 Min Read

Stacey remembers her first love and more

Topics: Crossdressing, Sissy, Oral & Blowjobs, Fucking

9.2
42 Votes

Lord Laywood Gets Pimped Out (ch. 2)

Story by EasyWhenDrunk

13 Apr 2024 2937 Readers comments 4 Min Read

A servant finds our prince passed out on his bed. He can't resist what comes next, but... neither can Eden Laywood, the slutty prince.

Topics: Sissy, Breeding, Fantasy, Verbal, Rape, Anonymous

9.1
47 Votes

Lord Laywood Gets Pimped Out

Story by EasyWhenDrunk

12 Apr 2024 4063 Readers comments 3 Min Read

Eden Laywood's father pimps him out to strangers to fund his estate. The only thing his father doesn't know...he's a slut and needs cock bad.

Topics: Forced, Sissy, Fantasy, Verbal, Fucking

7.1
9 Votes

Gay or Not Gay?

Story by BillyBoy

27 Mar 2024 1745 Readers comments 6 Min Read

How did I know? I wasn't just walking into a gay porn club and waving a rainbow flag. I needed to be persuaded, seduced or pushed a little bit, so I could say, I'm not gay, they made me gay!

Topics: Rough Sex, Bondage, Sissy

5.7
26 Votes

How to become a good cocksucker

Story by Gayguy69

9 Mar 2024 1759 Readers comments 1 Min Read

Billy was a sissy of a boy always playing with his sisters dolls and wishing he was a girl

Topics: Public Sex, Bathroom, Sissy, Twink, Oral & Blowjobs

9.3
14 Votes

Mr Tippet's young lover (ch. 3)

Story by Okamaguy

18 Feb 2024 1661 Readers comments 6 Min Read

Schoolmaster Tippet dresses me as his sissy student and gives me a lesson

Topics: Crossdressing, College, Sissy, Teacher, Age Difference

9.2
7 Votes

Coercion (ch. 8)

Story by Tommy

11 Jan 2024 1251 Readers comments 8 Min Read

My adventures into sexual awareness was becoming complicated and more fun and I love the fun and sexual adventures, the complicated would change me.

Topics: Crossdressing, Sissy, Twink, Domination, Mature Men

7.7
11 Votes

Got my wish (ch. 2)

Story by Luvonstkylip

18 Dec 2023 2383 Readers comments 2 Min Read

This is the other part of " Got my wish".. My crossdressing encounter that I had one night when I was spun!!!

Topics: Anal Sex, Crossdressing, Sissy

9.1
76 Votes

Turned Out

Story by Zac Smith

1 Dec 2023 11596 Readers comments 11 Min Read

How I was turned out in prison

Topics: Anal Sex, Straight Men, Big Dick, Shower, Prison, Transgender, Sissy, Bareback, True Story, Fucking

9.0
14 Votes

Gay Catfight for an Alpha

Story by Derick Gold

23 Nov 2023 2017 Readers comments 8 Min Read

Husband vs Boyfriend for their MAN excerpt from the hot new book NASTY NEIGHBOR

Topics: Wrestling, Alpha Male, Sissy, Twink

8.2
36 Votes

wife mademe a pathetic sissy cocksucking slave

Story by BillyBoy

13 Sep 2023 5967 Readers comments 9 Min Read

my new wife wasn't what she seemed. she turned me into a sissy, then a strap-on fuck toy, then brought in men to fuck her while i watched, then men to fuck me while she watched. It's a long story, but I'm caught up here forever now.

Topics: Bondage, Sissy, Straight Sex, Domination, Pegging

8.6
13 Votes

Sissy's Bizarre Adventure (ch. 3)

Story by Dray Sandrix

4 Sep 2023 2402 Readers comments 8 Min Read

In this chapter, Diana, the newly initiated sissy slave, and her Master, Alex, embark on an electrifying adventure into the unknown. At a BDSM party filled with secrecy and desire, Diana's deepest fantasies are unveiled. Blindfolded and surrounded by eager participants, she embraces her role as "Diana, the Wonder Whore," seeking anonymous encounters that will test her limits and desires.

Topics: Anal Sex, Chastity, Bondage, Slut, Sissy, Master & Slave, BDSM, Blindfold

8.2
85 Votes

Trailer trash cumdump

Story by Alleykat

19 Aug 2023 15770 Readers comments 3 Min Read

How I became white trash for rednecks at the trailer park

Topics: Crossdressing, Forced, Sissy, Cum Dump, Redneck, Lingerie, Panties

9.2
133 Votes

Frat Initiation

Story by Victor

2 Aug 2023 12540 Readers comments 27 Min Read

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.

Topics: Muscle, Crossdressing, College, Sissy, Hazing, Domination, Lingerie, Illustrated, Straight to Gay, CNC

8.6
38 Votes

The taste of cock

Story by BillyBoy

2 Aug 2023 4207 Readers comments 7 Min Read

He told me I was his little slut. Even though I am a middle age guy. But it made me feel so kinky and slutty. I did whatever he told me to get more of it.

Topics: Sissy, Role Play, Oral & Blowjobs, Age Difference, Domination

9.6
60 Votes

Crush on Coach (ch. 2)

Story by Victor

26 Jun 2023 5526 Readers comments 11 Min Read

Drew is a friend of Colt's from chapter one. Drew is the last guy you would think likes to be treated like a bitch. He's a good ole' boy, redneck, drinks beer, drives a truck and keeps his body in top shape. Like Colt, this uber masculine guy with the muscular body loves to wear lingerie when with an another man.

Topics: Muscle, Poppers, Group Sex, Coach, Sissy, Submission, Lingerie, CNC

8.7
15 Votes

Sissy's Bizarre Adventure (ch. 2)

Story by Dray Sandrix

14 Jun 2023 3005 Readers comments 3 Min Read

Sissy's Bizarre Adventure: A captivating tale of submission, desires, and sexual liberation as Dray embraces his inner sissy and dives into the world of BDSM, exploring the boundaries of pleasure, pain, and domination.

Topics: Anal Sex, Crossdressing, Chastity, Slut, Sissy, Submission, BDSM, Blindfold

8.5
15 Votes

Sissy's Bizarre Adventure

Story by Dray Sandrix

13 Jun 2023 3813 Readers comments 5 Min Read

"Sissy's Bizarre Adventure: A captivating tale of submission, desires, and sexual liberation as Dray embraces his inner sissy and dives into the world of BDSM, exploring the boundaries of pleasure, pain, and domination."

Topics: Anal Sex, Chastity, Bondage, Slut, Sissy, Oral & Blowjobs, Submission, BDSM, Blindfold

8.5
55 Votes

Caught by Aunt's Boyfriend

Story by Katie Femboy

5 Jun 2023 8468 Readers comments 3 Min Read

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

Topics: Crossdressing, Uncle, Sissy, Lingerie

9.0
19 Votes

Secret Kisses

Story by luvaslip

5 Jun 2023 1853 Readers comments 5 Min Read

Lance meets the owner of a vacant and haunted house. A romance begins to grow as trust is beginning to be realized and cocks meet and a Virgin pussy is offered.

Topics: Sissy, Virgin