Bossom Buddies Stories

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My First Shemale Ch. 01

by Richard Norman on Sep 16, 2017
Transsexuals & Crossdressers

We were in a strip joint in Juarez, across the bridge from El Paso. I was sitting with my buddies from Fort Bliss, doing what GI's do in Juarez: eat hot food, get laid in whore houses, and bitch about the Army over beers. We went to strip clubs and got shit-faced before buying pussy. It helps to be high when you shop for whores. The MC introduced the next s...

Monday Night Football

by Just_Another_Joe on Nov 8, 2017
Erotic Couplings

This story is completely factual. Since it happened over 3 decades ago, some of the details are a little hazy, but the overall "thing" itself is still crystal clear in recollection. November, 1980. I was 22 years old, living in an apartment with a couple buddies in my hometown. I would be moving to Texas in 4 months, but didn't know it at the time. What I...

Ms. Dollie's Living Fantasies Ch. 14

by LIVINRFANTASIES on Sep 13, 2017
Exhibitionist & Voyeur

Friends, Foreplay, and a few Yesterdays 'Don't wait until tomorrow.' We told our fuck buddies I've had way more than enough sex and it was starting to be more work than fun. It's good to not be on a schedule and good to be down to only one sex buddy at a time. It's also good to be only getting fucked once or twice a day with several days just staying home...

Amanda's Night of Fucking

by evil evil man on Sep 13, 2017
Erotic Couplings

Amanda paid the cover for the nightclub and went in. She could feel the bouncer checking out her ass as she walked by him. This is the hottest club in town and is known for always having hot guys and loose women. The guy to girl ratio is against her in a place like this but she's never had any trouble meeting men here. Her body attracts guys like a moth to a...

The Bet

by Penny_Tralia on Aug 30, 2017
Group Sex

My husband and I like to bet. Last week I lost my first bet to him and his prize? That I would have to do anything sexual that he wanted me to. Sounded pretty innocent to me, after all he and I had done just about everything imaginable, but what he had in store for I would never have even thought of. He let me know ahead of time that I would have to pay up o...

Her Ass is Used by Friends

by Alex_likes_Butts on Sep 12, 2017
BDSM

I wrapped the strapping tape one last time around the wrists of my girlfriend Ashley. I had secured both of her hands above her head to the stair railing in our hallway. Ashley had a gleam in her eye as I playfully slapped her tight little jean-clad butt. My sexy 32-year-old girlfriend had taken me up on a dare. With a naughty little grin, I gently wrapped...

Just My Imagination

by cuckytoher on Sep 14, 2017
Loving Wives

Was it just my imagination when I would see my wife chatting with the landscaper that she would rub his bicep and laugh in a way that was more than customer and client? Was it my imagination that my wife upon my arrival at home if she was on the phone would chuckle in that high lilting voice that was a different tone than she spoke with her girlfriends? Was...

Trained to Perform

by steve w on Sep 1, 2017
Group Sex

“She’s perfect, man. Where do ya find them?” He smirked. Where indeed? Where do you go to find a young girl, willing to become a submissive little slut at your beck and call? To be honest, he wasn’t quite sure. This new girl, Kelly, was a long way from being his first. He was thirty two now – old enough to know better, young enough to get off on it – and Ke...

Stewardess Strips at a Machine Shop

by StewardessMasturbationFantasy on Dec 9, 2019
Exhibitionist & Voyeur

I am a US Airline flight attendant but what you wouldn't know from your flight with me is that I am an addicted exhibitionist. My husband understands this and has supported my exhibitionist fantasies that I sometimes act out on layovers. But he really surprised me one time by arranging a party with his friend who owns a machine shop just north of the San...

Hotel Bar Pick-Up

by greivous on Sep 18, 2017
Anal

My two buddies and I had been on a week-long fishing trip and we were staying at a hotel close to the airport for one night ahead of our flight home in the morning. It had been a great week, lots of fishing, whiskey, and bullshit - but no pussy, so I was ready to go if the opportunity presented itself. We checked in, got clean, and met up at the hotel bar...