Gay Crossdresser Stories

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.

The beauty of lingerie

By Thatslife 23 Feb 2024

This is a true story that started my passion for lingerie, it also involved the two women in my family. I was given the opportunity to touch their lingerie while they wore it. I was hooked then

8.0 (22) 2576 4 Min Comments

The Walk Of Shame

By NeedyScorpio 22 Feb 2024

I was used by two older men after working hard on their property.

8.9 (56) 12345 26 Min Comments

Coercion (ch. 15)

By Tommy 19 Feb 2024

My weekend with David, Roy and Terry I hope was beneficial for all of us, it seems that what has awakened in me this past summer would hopefully turn into life’s lessons.

9.3 (5) 670 9 Min Comments

Mr Tippet's young lover (ch. 3)

By Okamaguy 18 Feb 2024

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

9.5 (19) 3055 7 Min Comments

Spring Break (ch. 3)

By 243907 8 Feb 2024

fucking, group sex, cross-, dressing, domination

8.6 (14) 2489 6 Min Comments

Is it just me? (ch. 3)

By Luvonstkylip 5 Feb 2024

My journey continues as I begin to realize how much I don't understand about myself and where my heart is.

8.5 (2) 886 5 Min Comments

Coercion (ch. 14)

By Tommy 31 Jan 2024

My plan was to share some exciting sexual deviant playtime, but also have some protection and control.

8.8 (6) 743 14 Min Comments

Coercion (ch. 13)

By Tommy 26 Jan 2024

I was happy with myself and the plan I put together for my fun filled Friday with the adults, putting the plan together was also fun with John and Cory.

9.1 (6) 1242 10 Min Comments

Coercion (ch. 12)

By Tommy 23 Jan 2024

Friday was coming quickly and while I was looking forward to this, I wanted to assure for security.

9.7 (4) 674 13 Min Comments

Coercion (ch. 11)

By Tommy 18 Jan 2024

My encounter’s and planning for others to be happy was making me happy as I planned how I was going to visit Roy.

9.7 (4) 694 10 Min Comments

Coercion (ch. 10)

By Tommy 15 Jan 2024

I was looking at how much control I could take of what has become all consuming of my sexual activity and thought at what cost would it take to achieve this as I went to find Cory.

9.8 (7) 1047 6 Min Comments

Coercion (ch. 9)

By Tommy 14 Jan 2024

I am enjoying my new found friends and thinking I may have been wrong about John and enjoyed being his submissive fuck toy as I helped Cory get his boy pussy ready for what was to come next.

9.5 (7) 930 12 Min Comments

His wife missed out this time, or did she?

By deansaz 14 Jan 2024

He and I had sexually shared his wife for a long night, but this time....she didn't show and he had some kinky needs......

8.7 (25) 3173 3 Min Comments

Coercion (ch. 8)

By Tommy 11 Jan 2024

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

9.2 (9) 1722 8 Min Comments

Tip Your Bartender (ch. 2)

By MaskedMan 7 Jan 2024

With connections from the previous party, my summer continues to be filled with new experiences as I get topped for the first time. Based on actual events.

9.4 (39) 2946 19 Min Comments

Coercion (ch. 7)

By Tommy 5 Jan 2024

Two boys exploring, experiencing, experimenting with their sexuality and enjoying it all is it came knowing now that I did have the power to play however I wanted.

8.9 (10) 1078 9 Min Comments

Laundry will never be the same

By Ky 3 Jan 2024

Growing up laundry was one of our chores my brother and I had to rotate weekly between our sisters. We jokingly dared each other to try on our sisters clothes but had no idea what start between us

7.0 (15) 4007 3 Min Comments

Long trips aren't always bad

By Luvonstkylip 3 Jan 2024

A short fantasy of something I've imagined while lying in bed.

8.7 (7) 2128 4 Min Comments

Coercion (ch. 5)

By Tommy 28 Dec 2023

My awakening feels wonderful and I’m now not sure who seduced who with my sisters boyfriend, but adding another new lover felt good.

9.5 (16) 1936 6 Min Comments

Got my wish (ch. 2)

By Luvonstkylip 18 Dec 2023

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

8.0 (19) 3294 2 Min Comments

Got my wish

By Luvonstkylip 17 Dec 2023

A secret dream of a closet crossdresser while spun

8.3 (19) 2316 2 Min Comments

Weekend with a Dom Master fuck buddy

By BillyBoy 12 Dec 2023

i finally joined Grinder and a guy liked my fetish and kinky desires. He fucked me like a whore.

8.2 (17) 4166 6 Min Comments

Femboy chronicles (ch. 10)

By Johndoe 7 Dec 2023

The rest of the evening goes a bit uneventful other than the casual ass grab from Chris and asking me get him this or that and basically being his bitch.

9.5 (11) 3612 7 Min Comments

Steve

By WoodyTyrone 4 Dec 2023

Sex with my friend's dad

8.7 (50) 5464 6 Min Comments

Coercion (ch. 4)

By Tommy 28 Nov 2023

My eyes wide open as my adult mentor’s use me as a toy, but teaching me, or as I let them think.

9.6 (22) 2122 8 Min Comments

Loving my high heels

By Prettyboy 18 Nov 2023

Jackie is a bottom boy who loves wearing his St. Laurent Jonny boots with 3" heels. Rod eyes Jackie and his boots. Intrigued by Jackie, his leather jeans and boots Rod decides to hit on Jackie.

8.7 (24) 1294 3 Min Comments

Coercion (ch. 3)

By Tommy 16 Nov 2023

My adventures and awakening continue and I knew Mr. Waxman had some plans that I was looking forward too.

9.3 (30) 2981 14 Min Comments

Femboy chronicles (ch. 9)

By Johndoe 15 Nov 2023

Caly is in for a rough session after giving Chris a tough time, hope you like it!

8.9 (14) 4401 9 Min Comments

House help is my Master now (ch. 6)

By Slutty Whore 9 Nov 2023

It has been over a week since we are married and I am becoming more of a slave each and every day. My master make sure that I get more humiliated every single day because I am his slave and he decides what should be done with me.

7.3 (15) 3650 4 Min Comments

My Wife's New Tool

By Disbtm 31 Oct 2023

A very perverted, and sexually craved husband and wife wake to find she has grown a beautiful cock. They're not sure how, but they will have fun while it's here, and very hard. A fantasy I dreamed about over and over when I was married. Why can't she have a cock?

9.2 (39) 5464 7 Min Comments

Femboy chronicles (ch. 6)

By Johndoe 17 Oct 2023

Caly is starting to gain a bit of confidence. How will she react to Chris’s attempts to push her limits!?

9.4 (13) 3044 11 Min Comments

Guises

By Habu 17 Oct 2023

Costumes, disguises, and hidden identities in Germany, Italy

9.5 (15) 2002 21 Min Comments

My neighbor

By Eric 14 Oct 2023

My neighbor, didn't see this happening

8.2 (62) 10821 4 Min Comments

Going to my prom

By BillyBoy 12 Oct 2023

Yeah, I'm too old, but I wanted to go to a real prom dressed like a girl anyway.

7.9 (16) 3678 8 Min Comments

Femboy chronicles

By Johndoe 27 Sep 2023

Hi! Thanks for stopping by, first time writer. Feedback is always welcomed, I love more of a slow burn huge build up story. Hoping to make this a series it takes off

8.4 (20) 7646 4 Min Comments