BONUS NUMBER 42: 201 THINGS EVERY GAY MAN SHOULD KNOW ABOUT SEX
(Did You Sleep With the Models?)
Back in March, in my Second Letter to Subscribers, I wrote:
“Expect to see on here a little book I completed in 1999 titled 201 Things Every Gay Man Should Know About Sex. As subscribers, you’ll be able to read all 201 of them — and add your own.
I continued, “Here’s No. 8 as an hors d’oeuvre: Kiss him as though you were still in high school, and he were the cutest guy in your class.”
And No. 104: “Underwear is important. You'll project a sexier image in sexy underwear. Choose your style and colors as you would choose jeans or a swimsuit, for, like those items, your underwear will be noticed. And when the time comes to take it off, don't rush. Make this revelation last, although not so long that your partner wants to fast-forward.”
Here’s more good advice, a graffito I once saw on a restroom wall:
Never believe anyone who says,
The check is in the mail.
Go straight ahead, you can't miss it.
I won't cum in your mouth.
My agent and my editor at the time thought this not quite the proper tome to follow All About “All About Eve,” which was published in 2000. Perhaps they were right. Times are different now. I’ve also escaped the grip of governessy agents and the small town mentality of what-will-people-think editors. That unpublished book is now a Substack exclusive.
Reading through these lascivious suggestions, I recalled Zsa Zsa Gabor's famous bon mot, uttered around the time of her ninth wedding: "I don't know anything about sex. I was always married."
I might say that I don't know anything about sex because I was always editing Mandate, Honcho, and Playguy. In truth, I could not possibly have engaged in, or even sampled, every erotic practice spotlighted among these 201 tips. A number of friends contributed, some of whom learned about sex while married. Think of the tips, suggestions, notions, and cautions as the gay male equivalent of Martha Stewart's exhortations on home décor and culinary excellence.
Need I add that in 1999 there was no Grindr, Squirt, OnlyFans, nor social media as we know them today, and cell phones were barely on the horizon. There was not much ink (meaning tattoos), only occasional piercings, and lots of eye contact rather than phone gazing. I’ve updated a bit, but I leave it to one of you, on Tik Tok or Instagram, to think up 201 Things Every Millennial LGBTQ+ Should Know About…Whatever.
I hope some of these 201 items will make you laugh in addition to prodding the libido. As you read, just imagine how furious puritans of all kinds and religious fundamentalists will be if they sneak into Substack. And pity them for what they're missing.
The first 50 are free to everyone. After that, for subscribers. Watch for the remaining 151 sex tips in a few days.
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1. Try to make your adult orgasms as erotic and satisfying as your first jack-off or an early wet dream.
2. You'll meet more sex partners at the gym than in most bars.
3. Wink at a man. It's dynamite communication.
4. Take off all your clothes except the white athletic socks. They enhance your nakedness.
5. What ever happened to showing box? Try wearing jeans with no underwear and see what happens. This was big in the ‘70s and ‘80s. If you haven't tried it since then, do it again. If you've never done it, what are you waiting for?
6. Manscaping is the "in" thing. Whether or not you go full body depends on various factors. But at least clip your pubic hair to make your dick more prominent. Unless you want your crotch mistaken for a robin’s nest.
7. Call him "Buddy." It conveys genuine warmth.
8. Kiss him as though you were still in high school, and he were the cutest guy in your class.
9. Nostalgic for the 1950s? Try necking with a man in a parked car. Will you go all the way?
10. If you indulge in cock worship, you're following one of mankind's earliest forms of reverence. It dates to the start of recorded history, and probably eons earlier.
11. P.S. Cock worship doesn't mean you have to give up your religion.
12. True or false: I'm a cock-watcher.
13. If size is important to you, don't settle for less than seven. Or one that looks and feels like seven, or eight, or nine…But know that inflation exists here, as in the economy.
14. On the other hand, if size doesn't matter, don't pretend it does. Five-and-a-half rock hard is better than nine limp.
15. Don't get hung up on size.
16. A man who asks that trite question, "What's your sign?" is often trite in bed.
17. Turn off the TV while you're having sex. Off means picture and sound. And your cell phone should be left in the car.
18. Only a bumpkin refers to "French" and "Greek" when he means "suck" and "fuck."
19. Keep a small jar of your semen in the fridge. Before going out, dab a few drops behind each ear and let it dry. You'll attract more men this way than with any product of Calvin Klein's.
20. Tattoos on a dick is gilding the willie.
21. Watching someone else have sex, on screen or in the flesh, is a good way to learn technique. Voyeurs often make good lovers.
22. Usher pets out of the bedroom before you start. Even exhibitionists dislike being stared at by that kind of voyeur. Especially if the voyeur barks, or scratches, or wants to join in.
23. What would you do if a 46-year-old man and his 24-year-old son propositioned you for a three-way? Would both men turn you on equally, or would you find the dad hotter? Or the son? Your answer to this question tells a lot about your sexual make-up.
24. Experiment. As Cole Porter said,
“The apple on the top of the tree
Is never too high to achieve
So take an example from Eve
Experiment…”
25. Smile at a man you want to go to bed with. This is so rare in gay life that you'll melt his heart. Assuming he has one.
26. Compliment your sex partner on his prowess, performance, size, or anything else that turns you on. In giving him a better opinion of himself, you'll ensure that he has a good opinion of you.
27. If you invite a man to your place for dinner, have sex first. The way to a man's hard-on is seldom through his taste buds.
28. Have sex again after the meal. Remember to blow out the dinner candles before you...blow him.
29. Next time you're bored at work, think about the moment just before orgasm: the clutching, thrusting, jerking, gasping, moaning, biting.
30. Try to please and excite the man you're with as much as you want him to stimulate and satisfy you. Make sex last on and on.
31. Conversely, a sudden swift and selfish quickie can be loads of fun for giver and receiver.
32. It's gauche to ask a man if he wants to "fool around" when what you mean is "suck and fuck." Don't be coy; your sex life is not a sit-com.
33. Take a second look at someone you don't consider attractive. Be flexible and broad-minded as you look for his sexy side. Try to put him at ease; make him smile. Imagine him turning you on in the most erotic ways. Now take a third look. Since you're only looking, you're not obligated. If he takes a second look at you, invite him to join you for a drink, a pizza, a movie, or a "date." He'll know what you mean.
34. Don't tell a super-hung man how much size matters to you if you don't know what to do when you get it.
35. Dating can build up tension and lead to hotter sex because of fantasies about the eventual orgasm. Incidentally, what is the definition of a date? A very clever man said recently, "If food is involved, it's a date. Otherwise, it's sex."
36. Keep your bed linens fresh. Lovers don't relish cracker crumbs, lint balls, pet fur, or stains on the sheets.
37. After sex, always supply a clean, attractive bath towel, not a forlorn little rag that belongs by the kitchen sink. Offer him other bath accessories he might need: washcloth, soap, shampoo, moisturizer. Make yourself scarce while he freshens up.
38. Ask a man you haven't yet been to bed with to complete this sentence: "An orgasm a day...."
39. Avoid references to Tantric Sex and the Kama Sutra unless you, or your partner, come from Asia.
40. How many men have you had sex with? Make a list. Write their names, dimensions, and sexual turn-ons. Rate them on a scale of 1-10 based on performance, the number of times you did it with each one, and whether you'd like to see him again. If you're so unwise as to post this on social media, you'll probably be sued. Or shot.
41. Be masculine, be aggressive. Don't act declawed, no matter what you might have heard from certain feminists, male or female. No one is turned on by a wimp. If you feel guilty for having balls, change your attitude. Or your gender.
42. True or false: Your most priceless possession is your dick.
43. Some masseurs will give you a massage. Period. Others will jerk you off or not jerk you off, suck your dick, let you suck them, give you a bath, wrap you in hot towels, take their clothes off, keep their clothes on, do a strip-tease, or some combination of the above. Find out his specialty when you book the massage. And remember, a "rub" is not the same as a therapeutic massage. Don’t confuse escort with chiroprator.
44. Make noise when you fuck. It enlivens your own pleasure and flatters your partner. Quiet enjoyment is for the library and the cinema.
45. It's polite to be rude in the bedroom.
46. A man on the street is worth two in the bar. That's because men are sexier in a real-life context than in contrived settings where they project a false image through posing.
47. Next time you see a hard dick, ask yourself whether that's what gay pride is about.
48. Be phallocentric. Celebrate phallocentricity. (Then turn these admonitions into bumper stickers, but for safety reasons, only when driving in San Francisco and perhaps in Provincetown.)
49. Try to understand yourself, who you are and what is important to you. This will help you to better understand your sexual make-up, which in turn will attract men who want what you have to offer.
50. Tell a man how nice looking he is. Even if he seems slightly uncomfortable, he'll remember your compliment and savor it.