Transgender Stories

GayDemon's porn library, in this story category you can find gay erotic stories involving transgender sex, MTF & FTM.

8.7
12 Votes

TG Gangbang (ch. 2)

Story by gary_4_u

7 Apr 2022 1686 Readers comments 6 Min Read

When at the club I I had to remain silent unless asked a direct question or told to speak. Almost always Kelli or one of our friends would take me up on stage and we would put on a sex show of some kind. But always with me getting fucked at both ends.

Topics: Anal Sex, Group Sex, Transgender, Oral & Blowjobs

8.1
7 Votes

Gunpoint (ch. 3)

Story by Tom C

20 Mar 2022 713 Readers comments 11 Min Read

“Gunpoint” is a story told in three parts of the abduction of a young trans woman, Lucy, and her foster siblings. The kidnapper’s boss has sex with Lucy, an inexperienced lover, and she develops feelings for him. Even so, Lucy realizes she must act to help her siblings.

Topics: Anal Sex, Dildo, Transgender, Alpha Male, Sissy, Deep Throat, Boss

9.4
17 Votes

Stories of a Bi Bottom slut (ch. 11)

Story by Tucsondude85716again

28 Feb 2022 6668 Readers comments 18 Min Read

More loads in my ass, lots of fun freaky party and play activity along the way.

Topics: Poppers, Rimming, Transgender, Creampie, Drugs, Breeding, Felching, Bareback, Gangbang, Penis Pump, Orgy

8.9
434 Votes

Oliver's Story

Story by Caliban

23 Feb 2022 5049 Readers comments 18 Min Read

A transgender love story... (updated version)

Topics: Crossdressing, Romance, Transgender, Straight Sex

9.0
19 Votes

Henry and Kennedy

Story by Randy Rogue

14 Feb 2022 2276 Readers comments 9 Min Read

What truly is gay? If a trans girl fucks a guy, is that gay. A slight off-kilter take on a cuckolding story.

Topics: Anal Sex, Rimming, Transgender, Oral & Blowjobs, Cuckold, Redhead, Deep Throat

7.3
28 Votes

The Naive Sailor

Story by Habu

12 Feb 2022 2313 Readers comments 3 Min Read

Young freighter sailor Cory learns the ropes in Bangkok.

Topics: Asian Men, DP, Voyeurism, Threesome, Transgender, Interracial

9.2
18 Votes

Alessia Travestita Hung Trans meets Big Dick in Vegas

Story by Stan

29 Dec 2021 2648 Readers comments 13 Min Read

Alessia Travestita (Real Porn Star Ashemale, Pornhub and Hamster) meets a big dicked man in Vegas for sex and fun. They are both smoothly shaven, big cocks, very oral and insatiable sex drive. Alessia gave me her background she is on Flkr I saw her immense thick cock. She requested some of the acts in the plot. I created Robert and the setting.

Topics: Anal Sex, Bondage, Big Dick, Transgender, Feet, Daddy, Cum, FanFiction, Shaved, Mature Men

9.1
7 Votes

Two hung Amazons meet Two sexy Ladyboys

Story by Stan

28 Dec 2021 1899 Readers comments 48 Min Read

Two BBW hung Amazons meet for BDSM extreme fetish sex with two petite sexy Ladyboys for an afternoon of hedonistic sex. The story ends up in a twisted erotic four-some.

Topics: Big Dick, Fisting, Transgender, Feet, Creampie, Sounding, BDSM, Deep Throat, Sixty Nine, Throat Fucking

8.2
26 Votes

I knew she was a trans

Story by BillyBoy

17 Dec 2021 2972 Readers comments 3 Min Read

She works in advertising. She is HOT! I waited for a long time to even say hello. I've never been with a trans girl. Does she still have a dick? I don't know. But I want to find out!

Topics: Transgender, Oral & Blowjobs, Hookups & Dates

9.3
166 Votes

Tranny at the bar

Story by djfmonkey

8 Nov 2021 7853 Readers comments 9 Min Read

The best looking girl in the bar was a guy and I love her.

Topics: Crossdressing, Transgender, Boypussy, Oral & Blowjobs, Shaved, Sixty Nine

8.9
40 Votes

Seduced by the 'girl next door'

Story by BillyBoy

29 Oct 2021 3761 Readers comments 6 Min Read

I know she is a trans or whatever. But she is so nice. I finally agree to stop over for a drink and some pie. Later she had me sucking her straw and eating her ass like a pie.

Topics: Rimming, Neighbour, Transgender, Seduction, Oral & Blowjobs, Submission

8.0
19 Votes

A weird twist I'll never forget

Story by BillyBoy

11 Oct 2021 5129 Readers comments 4 Min Read

A therapist suggests a strange clinic for me for the weekend. Somehow I get transfered into a womans body for two days. I guess you need to be carefull who you tell your fantasies to. Even your therapist!

Topics: Hypnotized, Sci-Fi, Transformation, Fucking

8.8
21 Votes

I'm a gay sissy transgender fuck toy

Story by BillyBoy

9 Oct 2021 2902 Readers comments 7 Min Read

When I came back from California, changed into a Caitlyn, I was surprised how many of my old schoolmates and teachers were trying to get in touch.

Topics: Crossdressing, Transgender

9.1
42 Votes

Kennedy

Story by Randy Rogue

6 Oct 2021 2680 Readers comments 12 Min Read

Typical Boy meets girl story. But the girl isn't your typical girl.

Topics: Anal Sex, Public Sex, Rimming, Transgender, Ass to Mouth

7.7
16 Votes

i guess you could say she seduced me

Story by BillyBoy

29 Sep 2021 2865 Readers comments 4 Min Read

I met her at the hotel bar. There was a crossdressing convention there that weekend. I didn't know it. But I found out soon enough.

Topics: Crossdressing, Transgender, Seduction, Oral & Blowjobs

9.2
40 Votes

Vicki

Story by Aiden

19 Aug 2021 2380 Readers comments 12 Min Read

She was smoking hot and he had no clue what he was in for. He certainly never expected this. Will he ever see the world the same?

Topics: First Time, Transgender

9.3
138 Votes

The Gym

Story by Caliban

30 Jul 2021 6564 Readers comments 10 Min Read

Have you ever imagined what sex would feel like as a woman?

Topics: Transgender, Sex

9.5
19 Votes

Entrapment

Story by Habu

5 Jul 2021 3409 Readers comments 34 Min Read

Trans rent-boy engaged in political entrapment sting.

Topics: Anal Sex, DP, Rough Sex, Prostitution, Transgender, Hotels, Age Difference, Rentboy

9.2
57 Votes

Jay's Action Night

Story by Simon Peter

8 Oct 2020 3845 Readers comments 16 Min Read

Jay walked into the crowded club with some kind of action on his mind. The music was loud, the clientele was rowdy, the bar was piled with bodies shouting for drinks, the whole atmosphere was intoxicating. Jay thought that this was going to be a hot action night as he pushed and elbowed his way to the bar.

Topics: Public Sex, Straight Men, Transgender, Sex, Straight to Gay, Fucking

8.7
13 Votes

susan new beginnings (ch. 3)

Story by bijim

5 Aug 2020 445 Readers comments 5 Min Read

Susan and Sally become victims of t girls who think they were responsible for there dismissal

Topics: Anal Sex, Bondage, Transgender, Revenge

9.5
18 Votes

my life (ch. 18)

Story by bijim

19 Jun 2020 2273 Readers comments 8 Min Read

the end of my training being turned loose in the world as a transsexual submissive slut

Topics: Anal Sex, Crossdressing, DP, Transgender, Milking

8.5
28 Votes

Luk in a Lincoln

Story by Habu

31 Dec 2019 1532 Readers comments 9 Min Read

T-Girl Luk does New Year's Eve party parking lot valets.

Topics: Transgender

9.0
479 Votes

His Special Something

Story by rae121452

2 May 2019 9356 Readers comments 33 Min Read

What would cause an otherwise str8 guy become obsessed with the security guard?

Topics: Anal Sex, Big Dick, Transgender, Oral & Blowjobs

9.1
198 Votes

Transman

Story by Caliban

30 Apr 2019 4612 Readers comments 13 Min Read

Can a man be a real woman...

Topics: Transgender, Oral & Blowjobs

7.5
68 Votes

Becoming a Girl

Story by Shy Stuart

22 Apr 2019 11635 Readers comments 8 Min Read

Growing up I knew I was different to other boys. At puberty a hormone imbalance caused my breasts to grow. By the time I was 20 I was on hormones and hungry for a man.

Topics: Transgender, Bisexual