Transgender Stories

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

Taking Him Deep For Movie Night

By Stephanie 27 May 2022

When I had invited him over for movie night, I had hoped it would get physical, but didn't know it would end with my first deepthroat experience.

8.5 (22) 3045 6 Min Comments

My Camping Trip Gets Wet

By Stephanie 25 Apr 2022

When my boyfriend invited me to a weekend camping trip, it wasn't just the tent poles I was fantasizing about pounding into the ground. Alone in the forest, and with a rainstorm lingering on the horizon, I have a feeling that things are about to get really wet between Charlie and me.

8.6 (29) 3599 11 Min Comments

TG Gangbang (ch. 2)

By gary_4_u 7 Apr 2022

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.

8.6 (14) 2128 7 Min Comments

Gunpoint (ch. 3)

By Tom C 20 Mar 2022

“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.

8.1 (7) 846 12 Min Comments

Stories of a Bi Bottom slut (ch. 11)

By Tucsondude85716again 28 Feb 2022

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

9.5 (26) 8317 19 Min Comments

Oliver's Story

By Caliban 23 Feb 2022

A transgender love story... (updated version)

8.9 (434) 5350 19 Min Comments

Henry and Kennedy

By Randy Rogue 14 Feb 2022

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

9.0 (20) 2568 9 Min Comments

The Naive Sailor

By Habu 12 Feb 2022

Young freighter sailor Cory learns the ropes in Bangkok.

7.3 (29) 2632 3 Min Comments

The Struggles of Becoming a Woman

By Getoutofmymind 11 Jan 2022

When becoming a woman things, in the beginning, are extremely difficult! Chapter 1.

9.5 (18) 2238 27 Min Comments

Alessia Travestita Hung Trans meets Big Dick in Vegas

By Stan 29 Dec 2021

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.

9.1 (20) 2861 14 Min Comments

Two hung Amazons meet Two sexy Ladyboys

By Stan 28 Dec 2021

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.

9.2 (8) 2566 50 Min Comments

I knew she was a trans

By BillyBoy 17 Dec 2021

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!

8.3 (28) 3481 3 Min Comments

Tranny at the bar

By djfmonkey 8 Nov 2021

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

9.3 (172) 9713 10 Min Comments

Seduced by the 'girl next door'

By BillyBoy 29 Oct 2021

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.

8.8 (42) 5270 6 Min Comments

A weird twist I'll never forget

By BillyBoy 11 Oct 2021

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!

7.9 (22) 5504 4 Min Comments

I'm a gay sissy transgender fuck toy

By BillyBoy 9 Oct 2021

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.

8.3 (23) 3775 7 Min Comments

Kennedy

By Randy Rogue 6 Oct 2021

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

9.2 (46) 3091 13 Min Comments

i guess you could say she seduced me

By BillyBoy 29 Sep 2021

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.

7.9 (18) 3170 4 Min Comments

Vicki

By Aiden 19 Aug 2021

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?

9.3 (47) 2765 12 Min Comments

Brian takes the pill for male to female tranformation (ch. 3)

By Desertbiguy 7 Aug 2021

Briana just had sex with the second guy on her list who had bullied her in HS. But she has a crush on them. Her fantasy dream team of fuckers.

8.8 (27) 3788 8 Min Comments

The Gym

By Caliban 30 Jul 2021

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

9.3 (138) 6952 10 Min Comments

Entrapment

By Habu 5 Jul 2021

Trans rent-boy engaged in political entrapment sting.

9.6 (20) 3868 36 Min Comments

Jay's Action Night

By Simon Peter 8 Oct 2020

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.

9.2 (61) 4402 16 Min Comments

susan new beginnings (ch. 3)

By bijim 5 Aug 2020

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

8.7 (13) 508 6 Min Comments

my life (ch. 18)

By bijim 19 Jun 2020

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

9.5 (20) 2629 9 Min Comments

Luk in a Lincoln

By Habu 31 Dec 2019

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

8.5 (28) 1596 10 Min Comments

I'll Show You Mine

By Naughtygaywriter 3 May 2019

Two men, one has a secret about what lies underneath his clothes.

9.2 (87) 6650 16 Min Comments

His Special Something

By rae121452 2 May 2019

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

9.0 (489) 9731 35 Min Comments

Transman

By Caliban 30 Apr 2019

Can a man be a real woman...

9.1 (199) 5519 13 Min Comments

Becoming a Girl

By Shy Stuart 22 Apr 2019

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.

7.5 (71) 13558 8 Min Comments