Crossdressing Twink Asstr Stories

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Sex Stories on the Internet

by H. Jekyll on Sep 16, 2017
Reviews & Essays

Sex Stories on the Internet: The First Twenty or so Years H. Jekyll February 2, 2008 One might wonder how sex stories grew so quickly on the Internet. Not sex, per se, pictures or videos of amazing acts, but stories, which take enormous time to write and edit, and time to read. And that pay so poorly -- for the most part not at all. Free sex stories have...

Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

How Nathan became Natalie Ch. 03

by saintlycd on Dec 31, 2017
Transsexuals & Crossdressers

Friday came and after classes and eating a light meal it was a little after five in the evening when I paid for and checked in the room where I was going to meet Kevin. I gave myself plenty of time to get ready for him. I had decided besides wearing Jennifer's dress I would go even further and try my hand at completely dressing as a girl. I purchased some...

Ragdoll

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'd always assumed I was 100%, no exceptions, one-track-minded Gay; as gay as the day is long. Pretty damn gay. Really, nothing's happened that should technically directly challenge that, there was still plenty of cock involved... but I can't deny the fact I was attracted to some very feminine features. It's not even like he (or rather she) was crossdressing...

Cocksucker: Cum Bucket

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Shemale and others gangbang straight crossdressing anal virgin. You do not need to read the first parts to enjoy this story of a straight man's hotel orgy of gay submission. In case you are curious how this straight married man got into this predicament, here is a brief summary of the first three chapters of "Cocksucker": Chris, a married straig...

The Basement Ch. 02

by FiveDots on Dec 24, 2019
Transgender & Crossdressers

I received a text the next evening. 'Hey dude, come down here and check this out.' Not yet ready to confront him with a revenge plan but not willing to ignore him either, I traveled down the stairs to the basement. My roommate had used the threat of exposing my questionable internet history to coerce me into letting him shrink me temporarily to pleasure him...

W32.GIBE.B@MM: Sexist Male Chauvinist Ch. 01

by HungryGuy on Aug 30, 2017
Erotic Couplings

Foreword: I wrote some of my past stories by request of my fans. In a way, I could also say that this story was written by request. However, it would probably be more accurate to say that this story was provoked than requested. Part 1 of this story is true. Some militant feminist recently started sending me flame mail accusing me of hating women because I...

Literotica: Feedback and Conduct

by TwistedPlayr on Sep 16, 2017
Reviews & Essays

***I hope that I do not offend any of the readers on Literotica who take the time to vote and leave feedback on the stories they read, be they named or anonymous.*** I have been writing for over ten years, and posting to Literotica for almost two. Before I posted my stories to Literotica, I posted them to ASSTR (Newsgroup erotica repository). Throughout all...

Hungry For Vixen

by HungryGuy on Sep 2, 2017
Erotic Couplings

AUTHORS NOTES: This is essentially a true story of how Vixen and I hooked up for a few hours of casual sex after she asked me to run her personal ad on my ASSTR site. Some details have been made up or exaggerated for the sake of the story, some of the awkward and clumsy things have been deleted that occur when two people who just met for the first time have...