“Of COURSE I’m Gonna Sleep With My Boss!”

Firstly, “mad props” to Boinkology.com and Haoneg.com for linking to us. We appreciate it. Today’s entry is the first in a two-part series about the former exploits of “Georgiana.” She is now in a long-term domestic partnership, and the semi-respectable mother of a toddler, but in former years she enjoyed a wild single life in New York City. She once showed me a pair of black, suede, thigh-high, high heeled boots she had, which she described as “the literal wages of sin” and a souvenir from a time when she was sleeping with a much older, richer man. I had never hear the full story behind the boots, but I felt it might be of interest to our readers, so I phoned her up to get it.

The backstory: Georgiana was in her 20′s and working in New York for a fashion company that produced “the dowdiest, most anti-aphrodisiac clothes you’ve ever seen.” She had just suffered through a bad breakup with her boyfriend, “Fitzwilliam,” who was 20 years older than her. It seems that one of Fitzwilliam’s big issues had always been a jealous fear that she would sleep with her boss, “Rochester”; “rumor had it he was hung like a bull.” (The boss, 10 years older than her, was married but had also been fucking one of her co-workers.) As so often happens after a relationship ends, she lost a lot of weight and started dressing better. Our story begins one morning when she walked into the office wearing a tight-fitting black miniskirt suit, black stockings and black high-heeled ankle boots. The boss was “totally blown away.” He commented on it, and she said “you know, what I really need with this is a pair of thigh-high boots.” He said “Let’s go out to dinner. I’ll buy you the boots.”

That evening, they bought the boots on a shoe store on 8th Street in the Village, and she wore them to the restaurant. While all this was going on, she was keeping in mind how jealous Fitzwilliam had always been, and said to herself, “of course I’m gonna sleep with my boss!” Because she was still in the throes of heartbreak, though, she spent the dinner getting herself all liquored up to nerve herself up for the encounter to come. Then they went back to his apartment. (He lived with his wife in Long Island, but kept a pied-a-terre in Manhattan.)

About their night of passion, Georgiana says “you know, it’s one of those ones I’ve always regretted.” Why? It’s obvious: If you’re going to fuck someone who’s really good in bed, “you need to be in a state where you can really enjoy it.” Instead, she was all messed up and filled with conflicting emotions. She gives Rochester a score of 9.8 for technical merit, but it was wasted on her.

I don’t want you to think, however, that this story ends on a depressing note, like that pig-roast thing did. No, indeed: “I would say I used those boots on the next three boyfriends to good effect.” Because her usual policy was to “screw on the first date, if possible” (that way you can tell if the guy is worth bothering with — we endorse this policy), she could just bring out the boots if it was taking too long. Apparently it worked, and furthermore, “if you’re wearing hooker boots and the guy won’t fuck you, you really are wasting your time.”

Wool crepe suit jacket

CTGML tip of the day: Buy a regular skirt suit, then get it hemmed so it’s really short.

Via Spiga ankle boot

Christian Louboutin black suede boot

Another option here; bargains don’t seem to be available, so get your own rich older man.