Author: gontish-goat

I (26m) have been in my current job for about a year. My boss (44f) is bit of the intimidator, a mother of three in her forties, no nonsense tolerated and highly competent. She dresses conservatively and somewhat severely, but I’ve always thought she looked good and perhaps had a little more going on than meets the eye…

Last Friday we were talking about work and family in a leisurely end-of-week way. It was an unusually warm day for October and the heat was running in our building super unnecessarily and her office was also getting a lot of afternoon sun.

After about thirty minutes my boss took off her turtle neck sweater. I certainly don’t blame her given how hot it was, but what she had on beneath was more revealing than I’d expected — a black tank top of sorts — not skimpy but also far from conservative — with normal straps and nice material, showing deep cleavage, far larger breasts than I would’ve anticipated, and a sprinkling of freckles. Read more »

I’ve always been a boob guy, but one who — not that anyone cares — never had much luck with any of bustier women I’ve had a chance with. There have been near misses over the years, but I’ve almost never experienced “more than a handful”, as my gfs and hook-ups have been on the trim, petite side of things…

The one *very* memorable exception happened when I was 22 and at a Phish show in Tennessee. Lol. It was early fall and my friends and I were stoned and drunk and goofing around and vibing, like you do. We looked every bit the part with our shaggy hair, flip flops, and Dead paraphernalia, etc.

The couple immediately to my right in the crowd was less obviously part of the scene. Maybe they were fans of the opener, idk. They were both wearing jean jackets and cut off shorts and had a good bit of visible tattoo work. They were also older than us, I’d guess both early/mid 30s. The woman was dirty blond, while the guy looked like an ex-rocker with long brown hair and a mustache. Being the 22 year old horndog that I was, it didn’t take me long to notice the woman’s deep cleavage, which was later revealed more fully when she took off her jacket. She was wearing a dark green tank top that was intended to show some skin, and it was clear that she was working with — well, let’s just say, a lot —“More like soccer balls than grapefruits”, was the way my dopey 22 year old self thought. Read more »