Gay Crossdressing Stories

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Infinite Scroll

After the Ball

by TinyBeth on Sep 12, 2017
BDSM

Author's note: This is a sequel to my Halloween contest entry story "Laine Goes to the Ball." While it is not necessary to read that story to read this one, it may increase your enjoyment of this story to read the earlier introduction to Laine and Xanna. Thank you to everyone that enjoyed the original and encouraged me to write the follow-up. I hope everyone...

Brazilian Discovery Ch. 01

by dan57 on Sep 15, 2017
Transsexuals & Crossdressers

by Dan57 with characters from Jill York Joan arrives in Brazil The plot from Susan and John series : Mr Gupta, the wealthy businessman had built his empire from scrap, starting from a small greengrocer shop in B'ham. He had slowly bought similar shops throughout England, federating them in a company that was powerful enough to build its brand new supermark...

Sally's Ch. 01

by seat542 on Sep 25, 2017
Fetish

This is the first part of a series, thus Part I (duh). As with most of my stories I take time to build a setting. Please stick with it. Part II is in the works, but I'd like to know if there is any thing in particular the readers are interested in. This story involves a bit of cross dressing, a start of Sapphic love, the sharing of cum, and golden showers....

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

Hollyquirk Studios: Week 00

by deathlynx on Sep 12, 2017
Chain Stories

Hollyquirk Studios: Week 0 (Pre-production) Maxwell McGrath looked around his new office with pride. Although most of the pre-production legwork was already done, the studio had only finally gotten around to giving him an office to work out of. Although they claimed they had been waiting for the space to become available, Max suspected it had more to do wit...

L-O-L-A

by Bully_Hayes on Sep 13, 2017
Transsexuals & Crossdressers

We had been dating for; let's see, about two months when I found out the truth. Sure I was shocked at first, but it wasn't something I had to get used to. It was something that just WAS. Let's go back to the beginning. I was 45 years old and recently divorced. Lost really, in a sea of confusion about where my life went from here. I never thought I would be...

Fred

by Stephan on Sep 13, 2017
Group Sex

It was the first time I called another man because I needed his cock! I was in the apartment of Connie, one of the women I service as the "Private Dick" in my apartment complex, and she wasn't alone. It seemed I interrupted a unplanned get-together when I showed up at her door with the tax papers I had prepared for her. Present were Peggy and Mary, two other...

Shannon

by ishouldbeworking on Sep 1, 2017
Group Sex

"My wife would kill me if she knew we were doing this." I smiled. "Yeah, she probably would." Shannon replied as she nibbled on my left earlobe while massaging my aching cock and heavy balls through my khakis. "Of course, it would be completely worth it." I said as lifted her off of the floor by her ass, kissing her passionately as she wrapped her legs aro...

Between The Lines Ch. 03

by mitchfren on Sep 14, 2017
Loving Wives

5. The hardest part about starting a new relationship is learning how to fart silently again. Okay, maybe it's not THE toughest thing, but it's a tough one; when you've spent years' staying on your own, in the cheapest hotels, having to think about things like that comes as a shock to the system. Then, add the fact that you're not entirely sure what kind o...

Endurance Predator

by DragonCobolt on Sep 14, 2017
NonHuman

Tax woke with a rumbling belly, sixteen inches of hard cock, and a serious need to fly. These three things were all somewhat related, but Tax had never been a strong believer in doing things before he absolutely needed to do them. He knew that several of his nestmates saw that as being lazy. He saw it as being frugal. They darted about the mountain peaks, sw...