Fucking a school teacher silly while her best friend watched. Or: mountain vacation sex [MF] [F]

This was years ago, but always fresh in my mind. Shelly (32) was a middle school English teacher. Shoulder-length, straight, chestnut brown hair, rich brown eyes, olive skin with a tan, 5’5” and a set of DD’s that we’re her favorite feature (they were spectacular). Shelly and I (23 at the time) for about 4 months has one of those hit, passionate, raw relationships that they write about in coming of age novels. I, feeling like a king for being the young guy who landed the smokin’ hot older girl, her with a confidence boost for landing the younger guy, turned that summer upside down.

Shelly was living in Florida with a long-time boyfriend. After breaking up, she moved up to the coastal town I lived in to stay with her friend, who happened to be my best friend. We met casually at a bar one night when my band was playing; I thought she was gorgeous and loved her body, we chatted for a bit but that was that. I never really thought anything else about it until I saw her again at a 4th of July party. My friends and I went down to a party on the harbor and she met up with my best friend and joined us. We said hello but never really separated again for the rest of the night. Conversation was natural and fun, we set a date for later in the week.

First time anal [MF] (long)

Suzy and I dated for several years. But I don’t really understand why. The relationship was a mess. She was fun, loved life and travel, loved trying new foods, really, on paper the kind of girl I’d go for.

From a distance you’d think she was the nicest girl you’ve ever met, because that’s the side she let others see. But she was also a narcissistic, hot headed, lunatic control freak. I was really only semi attracted to her: blond hair, A-cups, small ass, amazing muscular legs, girl-next-door-lower-end-of-pretty-face, her legs are what she had going for her physically. Sex was mediocre, bordering on inexperienced. She didn’t know what to do with her body and just sort of moved around in bed like a sack of concrete. BUT, it was adventurous sex. Which may be why I put up with her controlling rage and narcissism. If I ever wanted sex, all I had to do was initiate in some way, it didn’t matter where it was. She was down for it. Like in her parents driveway (that happened) or a hotel balcony (happened too) the middle of the back yard (yup) standing in front of the window at night with the lights on in our downtown condo overlooking one of the heavy foot traffic street in our town (no joke).

[FFM] unexpected threesome (long)

The scene:

The bar is packed, I’ve just finished a 4 song guest appearance in the band’s set; I’m sitting at a round table in the corner with some old friends enjoying a few drinks. Having moved three hours away from my hometown a year ago I don’t see them very often. It’s great to catch up the couple times a year that I am able to get down here.

It’s around 11 o’clock, we’re laughing conversation is flowing, the band has people happy, the bar has people drunk, my friends are starting to one by one call it a night. I’m starting to get the same idea as my drink is running down, my buddy Jonathan and a female friend of his are the last two at the table with me. I’m looking around for our server to tab out when I see Maggie walk in.

Stories of Maggie [MF] (long) Vol. 1

The story of Maggie is wide spanning with lots of great material to write about. If anyone enjoys I’ll write of our notable encounters in future posts.

Some backstory: I’ve known Maggie for 20 years. We were together for the first 5 of those years and remained number one on each other’s booty call speed dial up/fuck buddies list for another year and a half or so after that. The greatest sexual stories of my life were with Her.

The good: Maggie was the embodiment of perfection as far as my radar goes. She was (is) funny, loved to have fun, loved to travel, incredibly career driven (almost to a fault), VERY intelligent, spoke 3 languages (Spanish, English, french), she was a pistol, would never hesitate to snap you back in line, and was/is off the charts sexy.

Descriptors (me): I stand 6’ even, dark hair, olive complexion, slim, fit but not muscular or hard bodied but not at all lanky. I’m a grower not a show-er, certainly not in the 7” reddit army of delusion. Average length, 5-5.5” but 6“ girth. I’m 60/40 ass/boob man (respectively) in sexual preference and have a foot/toe fetish and prefer short women and small feet. I can’t be with someone with ugly feet, yes I realize the scale of vanity there. I love beautiful toes and a high arch. I love to give foot massages and get rock hard in doing so. I love sucking on toes, foot jobs, cumming on toes.