In my 20s, I was a handsome young guy with a proportionate, fit build. I had a great ass, a lot of people said, and because I was a runner, I had great legs, well-developed thighs and calves. I lived in Chicago and for about 7 months a year would run about 20 miles a week along the lake shore, among other things. But I was self-conscious and unaware of how I presented, both good and bad. Going to a gay bar was an excruciating experience for me; I didn’t know how to flirt and had “flirting blindness”, I could never tell when someone was flirting with me. I was unapproachable for a number of reasons, certainly with poor social skills but also because of my relatively good looks, a factor I was kind of unaware of in the sense that they weren’t any kind of valuable currency to me. At least not one I knew how to use. My sexual experiences were sporadic, confusing and often disappointing.
For a time, I worked as an event planner/supervisor for a very high end, boutique catering company, sort of the Glorious Foods of the Midwest. I interacted with all the clients and was very well liked. (Managed the staff as well, which used to come from one of the modelling agencies, probably Elite, so we staffed our events with a lot of hot young men, both blonde and brunette, and gawd they we’re stupid but damn they were gorgeous. Even amongst them, there was a pecking order. I certainly wasn’t in their league, understandably. And this was in the late ‘80s/early ‘90s, when plastic surgery and cosmetic procedures weren’t at all rampant. There was just good genes and more natural standards of beauty.)
Anyway, my boss - a talented chef and former male model himself, who thought highly of me - asked me to work a solo gig, not something we did very often, but a prominent gay lawyer in town with a big firm wanted someone to staff a BBQ/pool party he was throwing for the junior partners in his firm or something like that. Apparently it was an annual thing. It was about 10 -12 people, I would just serve drinks, put out some prepared food and clean up, etc. for a few hours and be paid cash. On a Sunday, late afternoon, on Chicago’s Gold Coast.
It was a really nice property and all the guys were pretty attractive, hot young gay lawyers. The host, who I’d met at a few events, was older and had a reputation. The guys were all really nice to me and one guy, probably of Mediterranean descent with gorgeous blue eyes and thick hair that covered his muscular legs and chest, was likely hitting on me as he kept coming to talk to me in the kitchen, etc. Stupid me.
As things wound down, it was really just a cocktail party, I made sure to have just about everything done so I could leave after the last guest - I didn’t want to be left alone with the host for too long, etc. But it didn’t matter because as it turned out, he wasn’t going to let me get away. As I tried to wrap things up and get paid, he insisted that I come down to the pool and have a drink with him. He was older but he took care of himself, he wasn’t particularly handsome at that age but he wasn’t a troll or anything, and he carried himself with an unyielding authority you’d expect from a high-powered lawyer. He spoke very firmly and insisted upon things. I made us drinks and went down to the pool with him, unaware that I had any other option.
Almost as soon as we sat side by side on some outdoor, rod iron love seat, he put his hand on the back of my neck and forced his tongue down my throat. I remember the stiffness of his moustache, still the only man I’ve ever been kissed by with a moustache or even facial hair. He quickly suggested that we go upstairs to his bedroom and at that point I was resigned to the fact this was happening and decided to just proceed without delay. Within minutes we were on his bed, making out, completely naked. It was a very “man and his boy” dynamic with him restraining me and trying to take charge, even though I was a fully grown, fit man.
(cont.)
