Anal Virginity Stories

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I Like Big Butts

by Paul44 on Sep 16, 2017
Anal

I love a good looking ass, not one of those things that are skeletal or without any flesh but something with curves and enough flesh to grab hold of as you push your cock deep into a steaming bowel as she cums with the pleasure and screams with happiness. To take a woman's anal virginity is something that is unimaginable, to seduce her and make her give you...

Erica, Virgin No Longer

by Tomhansom on Jul 15, 2020
Anal

This story is another in a series of (mostly) true stories about my wife, Erica. Please enjoy! Fast forward from our honeymoon. We are now married, I am on active duty, and we are at our first duty station in North Carolina. Having dated all through college, living together was not much of a challenge. We loved exploring our new "home" state and living toge...

Nightshift at Judy's Ch. 2

by Dancing Sprite on Sep 12, 2017
Anal

The day after Wendy had lost her anal virginity to Dave, her co- worker at Judy's SuperBurgers, while they were working the nightshift, she showed up for work in high spirits, wearing a miniskirt that covered less than a third of her thighs and no panties. Her tank top hugged her bra-less breasts tightly and her long, reddish-blond hair flowed freely over he...

Strapon Sex For Black Couples

by Samuelx on Sep 1, 2017
Group Sex

My name is Donar Jean-Baptiste and I'm a six-foot-tall, very voluptuous and sexy young black woman with dark brown skin, light brown eyes and long black hair. I've also got a big, round ghetto booty. Along with my large, perky breasts, it's one of many parts of me that drive men wild and make women green with envy. Yeah, I am fine-looking and I know it. I li...

Innocence Lost Ch. 25

by bradley_stoke on Sep 16, 2017
Novels and Novellas

In Which Innocence is matched with virginity, a career in giving pleasure to unknown benefactors is reviewed and Leon's own artistic vocation is revealed. It took quite a lot of persuading and rather a lot of money, but eventually Innocence agreed to make a Virginity Loss film (or Bleeding Fanny Film as they were less subtly known). It wasn't that Innocence...

Aileen Lost Her Virginity Ch. 02: Aileen Got DP'ed

by phallicdesire on Sep 12, 2017
Group Sex

"Why do you think you can fuck my sister?!" I looked up in horror to see Brandon staring us in this position. "Relax, B. She's just your step sister. Besides, I was just doing a favour to her. Did you know she was a virgin?" Keith answered while still having his cock inside my pussy. "I know that, dude. She's hot, and I actually intended to take her virg...

My Shemale

by 1zapatoapestoso on Sep 12, 2017
Transsexuals & Crossdressers

I was a young buck about 23 yrs. old and was touring South America. My friend and I were out and about the city of Rio de Janiero, Brazil. We had been drinking all afternoon long and were feeling pretty happy when the evening rolled in. We were hoping to find some local girls to have some fun. When this lovely lady approached us and started talking. My fr...

The Lady of Winterfell Ch. 07

by MTL17 on Jul 30, 2019
Celebrities & Fan Fiction

Disclaimer: I do not own Game of Thrones. I do not make any money from the writing of this story. ***** Daenerys blinked a few times in disbelief and then asked, "What?" Arya smirked and then cheerfully recapped, "I single-handedly killed Cersei, won you the Throne. Then, out of gratitude, you offered me anything I wanted. I'm here to collect." There wa...

Taken... & Pleasured at Nudist Resort

by MrsJ on Sep 13, 2017
First Time

This is a sequel to 'Taken...on a 7 Night, 8 Lays Cruise' * * * * * The card that arrived in my mail had a picture on the cover – a full arse-on shot of three young ladies standing in line, bending over, completely naked. Exposing everything. I immediately recognised them! The caption read: 'Just a cheeky question for you...' Inside it simply read: 'Wo...

That time I lost my virginity

by malcolmsu on Jul 15, 2020
Anal

For the avoidance of doubt, the following is a true story that describes the occasion when I lost my anal virginity - I was well into my twenties and the young masseuse I guess was about 20 or 21 years old. I was chatting online to someone the other day sharing experiences of losing our virginities. It was obvious, after a little while though, that we were...