Not for nothing, but if my penchant for documenting sordid tales ranging from throat-chopping Jim Jones fans to penetrating low self esteem having women in the hallowed halls of church buildings suddenly falls on deaf ears - I think I'm going to take up my real calling, and that's exclusively being a gigolo to older women.("Cougars" to be exact). Granted, my germaphobia may be a problem, something about weekly AIDS tests and a guy wearing three condoms and a doctors mask while very cautiously thrusting on top of you sort of takes the romance out of it, but I guess I'll have to cross that bridge when I get to it. That being said, the first time I actually considered receiving payment for my sexual services from women 10+ years my senior came last month when I ran into a woman who 18 years ago unknowingly turned me into the deviant scribe that you all know today. Her name is Sherry. See, Sherry was a friend of my parents who lived with us during my senior year of High School, and despite the fact that she was 28 and I was 17 years old at the time - she took it upon herself to rock my world like cooked cocaine abusing globe salesmen.(Sidebar: To this day my mother has no idea of what transpired between Sherry and I, solely for Sherry's safety. This may be the only time I'm thankful that mother finds reading my blog to be beneath her.)
Even though Sherry violated me in the best ways imaginable(Most of the daydreams that I've had since 1991 have been about some deviant "moment" that we shared), I always wanted to tell her how much she ruined me for every woman that would come after her. Even though being a selfish lover is ingrained into my DNA, I just had a glory-hole installed in my bedroom for Christs sake - having my every sexual desire granted by a grown woman while under the watchful eye of my Michael Jordan posters didn't help matters either. Little did I know that I'd actually have a chance to air said grievance directly to the source, recently we both met up for drinks after not seeing each other for nearly two decades.(She was in town to visit her son, she lives in Nova Scotia) As we drank and nervously chatted as if we were complete strangers, I noticed that she hadn't changed very much. Sure she was older, scattered grey reminders of that fact represented themselves throughout her flowing mane, but in a sexy "Mrs. Robinson" sort of way though. Her attire had gone from skirts that only gynecologists would approve of to very hip business outfits, something you'd imagine Diane Keaton wearing in one of her latter day movies that I've desperately tried to avoid. I also remember a time when everything that escaped her mandible was nothing but rhetorical flourishes involving profanity and sexual innuendo, but that particular night she only waxed poetic about her grandchild and some overpriced wine that I'd never heard of.
Even though I'm the type of asshole who carries condoms around with me on a daily basis "just in case", I was damn near positive that nothing of interest was going to go down after I dropped her off at the hotel she was staying at. I mean, the mere fact that we never discussed our time together signaled she was uncomfortable with it, and even though she was as beautiful as ever I discovered a prejudice against older women that I never knew existed.(Later I figured out that it had something to do with her uttering the word "grandchild", definitely a penis shrinker.) But because I'm single and ship barnacle had started growing on my genitalia, I immediately accepted her offer to go back to her room for a "nightcap". As much as I'd like to go into explicit detail about the events following an impromptu kiss that she sprung on me at her hotel door, I'll respect her wishes and file it into my mental rolodex for strictly masturbatory use at a later date. But I will say this, despite the fact that I've told every white woman ever interested in me that I affectionately refer to my favorite appendage as a "Black myth ruiner" - that particular night, unbelievably, I was rather pleased with my bedroom performance. So much so that when she said something to the effect of "You really know how to treat an old lady right!!", I quickly responded, - "Just be lucky that you don't have any false teeth readily available, because I'd proceed to spike them shits and do an 80's era endzone dance in front of the bed right about now!"
In the morning, after having breakfast and finally talking about how she turned me out like a reversible jacket, we began to wrap things up. After she hugged me and said "Lets not wait until 17 years to do this again", I unfortunately responded with "Don't worry, I don't plan to have my penis in the same zip-code as a 62 year old, sex with you at that point would be like fucking the skin creases on a Bulldog!" She gave me comically bewildered look, as if she was thinking, "Jesus, you really are a fucking dickhead!" - then we proceeded to part ways. But as I drove home, barely being able to piece together the sex in any coherent fashion - I came to the conclusion that I didn't really have sex with her, as beautiful as she was, but I just had sex with the image of her that had haunted me all these years. The woman who was under me, being subjected to me uttering Hip Hop quotables mid-coitus, was merely an afterthought - not for nothing, but I'd imagine that a lot of older ladies out there wouldn't mind their younger suitors getting off to younger versions of themselves. That's where the gigolo idea comes in. I mean, if the women in my employ would give me some old pictures of themselves beforehand for me to study, I'm sure that I could look past the liver spots, Great Depression stories, and ritualistic "Matlock" watching and proceed to do Business. Pelvically that is. Sounds like a lucrative business plan to me.