Boy Toy Troubles

20th Century Fox

“Dear Ms. Mix and Bitch,

I’m a 20-year-old guy who has just started dating a 35-year-old, newly divorced woman. She’s the best thing to ever happen to me. I really like her a lot. We have only dated for a few weeks, but we haven’t slept together yet. While I have slept with plenty of girls, she would be my first real woman, ya know? And it scares the shit out of me. I know to college girls, I’m great in bed, but I don’t know if I will measure up to her. Before she was married, she told me she had a lot of boyfriends. I can sense she’d getting restless with me – and if I keep her waiting much longer, both of us will explode. But if I suck at it, I’m afraid she’ll bolt.  Can you offer any sex tips? I would figure since you have a husband and kids, that you two are probably close in age.



Dear Jake,

So you’ve fallen for a cougar and you’re wondering if you can claw with the best of them. I wish more guys would ask older women this question. Would save lots of time and aggravation.

Before I get into the sex advice, let me just say this: be careful. Dating anyone fresh off of a painful divorce may result in suffering from the rebound effect. If you were just in it for a good time, then fine. However, you saying she’s the best thing to ever happen to you says to me you’ve fallen hard. Don’t get me wrong…love is amazing at any age. However, being in my thirties myself, I find it difficult to see how a 35-year-old can take someone your age anymore seriously than a recuperative roll in the hay. But hey, I may be wrong. Older guys are constantly falling for women much younger than themselves, and doing just fine. What’s good for the goose, right?

O.k., that out of the way, I have a three-tiered approach for pleasing a woman in bed:

(1) Do your homework

Order some books online on pleasing women in bed, or go down to a sex positive shop (if you were in San Fran, I’d send you to – in places like this, you could go right up to the counter, share your dilemma, and they’d hook you up) – watch some porn directed by women. I personally learned some of my best moves from good ol’ classic porn (my husband is VERY grateful I did). Peruse through the Jenna Jameson cannon for some pointers (literally).

(2) Worship, Worship, Worship Her

There’s nothing more alluring for a woman than a man that is totally into her body in bed. And not just her breasts or the parts you like. Everything, everywhere. Rub, kiss, or lick the small of her back or the inside of her thighs. Tell her she’s the most beautiful, sexy woman you’ve ever seen. And last, and CERTAINLY, not least….savor going down on her. When I was single, if I was dating a guy that either didn’t give head or felt he was just rushing through it, I’d dumped his sorry ass fast.  Trust me, we can tell if you’re just phoning it in. Conversely, I have stayed with certain men longer than I would have intended because they were so orally gifted.

Also, DON’T keep asking her what she wants you to do to her in bed – once or twice, fine. But over and over again, then we end up feeling like a traffic cop – and that’s no fun, my friend. Instead, learn the cues she’s giving you physically. Does she moan a little louder when you hit a particular sweet spot? Or does she tense up and try to wiggle away a bit? Everyone is different and what turned on one woman may make another one cringe. So pay attention.

(3) Be Confident

Nothing serves as a better afrodiasiac for a woman than a confident (not cocky) man. If you don’t feel as such, fake it ’til you make it, young stud. Remember, she likes you. Enjoy that!

 Good luck, young stud. You are experiencing the stuff that writes great memoirs.

Boy Toy Mix

1. “Hungry Like the Wolf,” Duran Duran [Rio]

2. “Like a Virgin,” Madonna [Like a Virgin]

3. “Brick House,” Commodores [Commodores]

4. “Southern Girl,” Incubus [A Crow Left of the Murder]

5. “Dreamgirl,” Dave Matthews Band [Stand Up]

6, “I Wanna Roo You (Scottish Derivative),” Van Morrison [Van Morrison – Live from San Francisco]

7. “Beautiful Man,” Lori McKenna [The Kitchen Tapes]

8. “Only You,” Joshua Radin [We Were Here]

9. “Just Like Heaven,” The Cure [Kiss Me, Kiss Me, Kiss Me]



4 responses to “Boy Toy Troubles

  1. I have actual relevant input for this conversation (as opposed to my other comments recently). I’m 24 and my girlfriend is 37. It has worked for near 3 years thus far because:
    a) She’s slightly immature and if you met her you totally would not peg her for 37 (maybe 28-32 but not 37).
    b) I have the heart of an 80 year old man … get off my lawn you damn kids!
    c) I took the time to explore all the ways to get her to orgasm again and again and again and again. Then, I learned the sheer joy of watching her turn into a screaming, panting, writhing, sweaty ball of girlfriend.
    d) I make constant references to how I can’t believe anything could be older than 30 and look at her as though she must be the most ancient person on the face of the planet. That does wonders for the ol’ self-esteem that does.
    e) We share the same completely inappropriate sense of humor.
    f) She accepts my dorky pursuits as part of who I am and not something to be changed.

    So, it can work. It doesn’t have to be like that crappy Uma Thurman movie that came out last year (or the year before or whenever it came out).

  2. I saw that film, and thought it was bogus – although she’s a yummy treat to savor on screen.

    Sounds like YOU could’ve written this column 🙂 I am sure Jake appreciates your point of view.

  3. Yes, I’m a lucky, lucky man. And I do worship every part of you – especially that hot mouth of yours…


    Your Husband

  4. Blushing and smirking at the same time…

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