Shemale First Time Stories

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Infinite Scroll

Becoming Her Wife Ch. 09

by Scribler on Sep 25, 2017
Fetish

When the alarm sounded my eyes open in a flash to stare at it. It was nine thirty in the morning. I had to get up for my diving lessons. I tried to move my hand to silence the alarm, but they were still chained behind my back. I still had the penis gag in and my cock was still being restrained by the chastity belt. On top of all this I had to pee really...

The Fucking Machine Party

by mindventure on Sep 13, 2017
Exhibitionist & Voyeur

Author's note: This is the fourth story in the 'Audrey Chronicles.' As before, they are loosely coupled so it's not necessary to read them all if you don't want to spend the time. However, the ladies' sophisticated sex toys have some interesting qualities and it might be a little difficult to understand all of this story without reading at least a portion o...

Kim Lazenby's Resumé

by PrimalRoots on Sep 12, 2017
Group Sex

(All characters sexually active in this story are at or above the age of eighteen. All characters are purely fictional. Check out my profile!) I like to think of myself as a master of exploitation. Others will call me a bitch, a whore, or just plain evil. But my interference in the affairs of others is minimal; its victims further extend the problems I ca...

Erin Goes Anal

by Mike Franklin on Sep 11, 2017
Anal

My name is Erin, and I'm going to tell you about my first anal experience – well, actually my first four anal experiences! It happened last year after had just turned 18 and was a junior in high school and dating a guy named Kevin. It all started on the bus rides home from our volleyball games. We girls would get to talking and eventually the conversation w...

Kasey's Confession Ch. 07

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Whatever Derek had given me, it lowered my inhibitions and made me very eager to give into my fantasies. The voice inside that told me to run from the situation was getting fainter and while I was somewhat panicked by Mr. Smith's stated intention to "break" me, a larger part of me was intrigued. It wasn't like I hadn't been with men before and it wasn't like...

Pimped Out in Vegas

by dysfunctionaldreams on Sep 12, 2017
Transsexuals & Crossdressers

I had flown out to Vegas for business and was staying at one of the hotels just off the strip, The Hilton. My business ended by 6pm every night, so I had some down time. The first night, I just stayed in and got used to the change in time zones. The second night though, I decided to get a little dressed up. I had brought a couple pairs of panties and a bra...

First Taste of Longtime Desire

by DirtyInnocence on Sep 13, 2017
Erotic Couplings

This is only my second erotic work, so any constructive feedback will be greatly appreciated! *** "My first impression?" Juliet smiled to herself as she thought about the first time she had laid eyes on Matthew. Her smile grew a little wider, and she hoped her mischievous thoughts weren't visible from her face alone. She remembered seeing him looking at he...

Ramu On A School Trip

by sahebji on Sep 1, 2017
Group Sex

Dear readers, remember I had promised to ask Ramu for more tales from his erotic life. The other day when Ramu visited me we sat sipping a drink and chatting. I asked him that he should tell me some more stories. He laughed and replied that there is nothing more to tell. I did not believe him and persisted. 'You are a principal of a school and there are many...

Shopping in the Big Apple Ch. 01

by Gentandhisbootslut on Sep 16, 2017
Mature

David's Narrative. So we are on a shopping trip to the big apple. You've had a great day, bought a new pair of black thigh highs, with a 4" killer heel on. I buy you a gorgeous black leather halterneck mini dress, not to short but very, very sexy. Both purchases are in the softest leather you can imagine. We return to the hotel and get our key from the desk...

The Shieldmaiden and Swordbearer Ch. 02

by Tara_Neale on Sep 14, 2017
NonHuman

Tara ached all over. Her head throbbed so badly that she could not force her eyes open even though she had been awake for some time. She was cold, icy cold but she did not have the energy to pull the duvet higher. She was drained. It had been getting worse lately. The price she paid for using her gifts. For healing others. What had she been thinking yest...