Smoking And Crossdressing Stories

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In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Smoking With Friends Ch. 01

by jjww100 on Sep 16, 2017
Transsexuals & Crossdressers

The phone on my nightstand rang and I groaned as I grabbed it and looked at who was calling. It was Benny and I answered it. "Hello". "Yo Justin, I got $250 worth a weed! You need to come pick us up so we can smoke it!" "Just Wait. Who are you with?" "I'm chilling at McDonald's with Matt and Vic." "Okay, I'll be there in twenty minutes." I hung up, qui...

By the Grace of Guile

by komrad1156 on Sep 14, 2017
Transsexuals & Crossdressers

*Author's note: Several years ago, I read an interesting book by author Loyal Rue, a professor of Religion and Philosophy at Luther College, called By the Grace of Guile. An excerpt from one review says this: "For people who are troubled by a world increasingly filled with the sweet-talking duplicity of politicians, preachers, advertisers, and sundry huckste...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

Blackmail

by thosearemysecret on Mar 15, 2013
Miscellaneous

To the average person, your life is fairly mundane. You have a steady job, a decent home in a lovely suburb, a fairly attractive wife (although her age is starting show), and a daughter about to head off to college. Some would probably say that you're fairly ordinary. Many might even say behind your back "Boy, John Doe is boring." It wouldn't surpr...

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Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Story Tags

by Literotica on Sep 18, 2017
How To

You've written your story, edited it within an inch of its life, and are all ready to show it to the world. You open a submission page and – what's this? Story Tags? What the bleep is a Story Tag? The larger any archive grows, the more important organization becomes. Separating stories into our current categories helps connect readers with stories they'll e...

Latex School Girl

by latexcd69 on Sep 25, 2017
Transsexuals & Crossdressers

Not many people knew about my crossdressing. My mind would fill with worries about what everyone would think. I did tell two of my friends, David and Nick. They were experimenting with bisexuality and very open minded. Somehow I knew they would be more understanding, and they were. The three of us lived in a small house for the price of an apartment. It see...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...