A Hooker With a Heart of Gold
By: William, Dollar Bill
Tags: Drugs, Inspiration, Sex, Culture, Life

A Hooker With a Heart of Gold

Her generosity knew no bounds

photo by William Mersey (of the actual girl)

Skylar might have been my favorite escort of all time. The reasons are many. First, using the aliases of April, Jamie, Lisa and many others, Skylar advertised literally everywhere an escort could…figuring that whenever she turned on her phone, said phone would ring with a customer on the line within 30 seconds. And when you’re the guy selling the ads (which I was but no longer am), that translates into more commissions for you! So I was in love right away!

Next…she had big, natural tits which I’m sure the customers enjoyed. But that didn’t matter to me. We weren’t “friends” like that! Still, her Pike’s peaks did work on my behalf as lots of guys went to see her and thus, Skylar always had the ad money when I arrived.

Not only that, she was always extremely generous. Fifty and hundred dollar tips on top of all her ad purchases were the rule rather than the exception. Girls rarely tipped back when I sold them media ads. Skylar was the exception.

Here’s a perfect example of her generosity: One time, I arrived at her place of business wearing some worn out sneakers — and the girls started snapping on me for my ragged footwear. I explained that I’d been shopping for a new pair, but hadn’t yet found a style that appealed to me. So while I’m bull shitting with the other girls, Skylar disappears and within a few minutes, Summer (her BFF) gets a quick phone call and then signs off to say “Billy! What size shoe do you wear?” And after I answer, she adds “don’t go anywhere. Skylar will be right back and she wants to talk to you about something.”

Guess what! Ten minutes later, Skylar arrives with not one — but two pairs of new Nikes!

Skylar and I had one crucial trait that bonded us. We both liked our sex playmates to be of the ghetto black variety. Hers were men…and mine women (just to clarify)…but we were both lily whites who craved dark black lovers. That didn’t mean she held her boys in high esteem (as she often referred to them as n…..s)…it just meant that black dick turned her on!

Once Skylar introduced me to her new boyfriend…this short and not-very attractive black guy named Stan. So after he departed I asked, “am I missing something here?” And she answered “yeah! He’s got the biggest dick I’ve ever seen! He also can’t last more than 15 seconds! But we’re working on that!” Two weeks later he was gone. She got tired of his 50 yard dash and moved on to the next scrub. What are ya gonna do?

Unfortunately, her predilection for black thugs was Skylar’s downfall. A few boyfriends later, she hooked up with a pot dealer who was flying kilos of product from Mexico to her address on the Upper West Side of Manhattan. One day, a dog sniffed the stash at Kennedy Airport and she became part of a huge bust (and I’m not talkin’ her tits here)!

For months, I heard all about the court case and all the money it was taking to defend herself. The last time I saw her, the jury had found her guilty…but the judge set aside their verdict because he felt she’d been found culpable unjustly — and probably because she was a big-breasted white girl fucking a nasty black scrub.

She wasn’t worried but then? Nothing. Skylar completely disappeared from the face of the earth. I figured the worst assuming that maybe the judge didn’t set aside the verdict and she’d been incarcerated after all. Well…maybe 7 years later (which was a couple of months ago), I googled her name in an idle moment to see if I could find anything about her. And in a NY Post article written a few years back, she was named as one of New York’s most infamous fugitives — thought to be somewhere around the New York/Canadian border!

My second favorite Skylar story revolves around a car she bought. Upon seeing the ride, I admonished her on the cost of parking and maintaining a vehicle in New York City.

And she responded “no problem on the maintenance front. Whenever the car breaks down, I just blow the mechanic at the dealership and he fixes me up free!”

Gotta love that girl. I hope she blew somebody to secure her freedom. That would end the story perfectly.

P.S. Five years later, I found Skylar on Facebook and gave her a call. After a few years as a fugitive, she negotiated a deal and surrendered to the feds. Three years in a cushy federal prison was her punishment. She is now a professional dog walker in Brooklyn, New York. And guess what! After we reconnected and she found out I was being prosecuted by the federal government, what do you think was the first question Skylar asked? Yup! “Do you need any money?”