1. I'm a 57-year-old guy, married but separated, in reasonable shape. I usually masturbate at night as a “sleeping pill.” Over the past few years, it's gotten more difficult to orgasm. I get hard, I vary my technique, but I just can't come. Sometimes I'm up for hours jerking it before trying to fall asleep. Toys like sleeves sometimes help, but they're messy since they need lube, so that's not my first choice. Any magic suggestions for things to try?

Fire on all cylinders — use sleeves and lube (keep a small stack of hand towels on your nightstand), put clothespins on your tits (whether they’re wired or not), get a powerful vibrator with a sleeve attachment, slip a plug in your ass (flared base!), read some erotica and/or watch some porn. Past a certain age, you may need to really crank things up to meet your production goals.

2. Best lube for anal sex?

Adrenochrome when available...

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