To tell you how it started would take a book, but a man in my apartment building pays me to “rent” my chocolate-brown, knee-high riding boots a couple of nights a week. They are always just outside my door when I leave for work in the morning — and clean! Last spring he “rented” them and looked after them for the summer months, returning them as soon as the weather made them fashionable again. This week he offered to up the “rent” if I would consider coming to his apartment once or twice a week and let him look after them while I was wearing them. I’m not sure what he means by “looking after” them, though I can imagine. My question is how can I be assured that I am not getting into dangerous territory here and that he is as harmless and submissive as he seems? HATE TO LOSE THE RENT

It actually should take a book, because this is just the type of story you’d want to submit to an erotica collection. It’s got all the themes in place: fetishized footwear, a 9-to-5er with a wild streak and a mysterious man brave enough to risk troubling a female neighbour for more than just a cup of sugar. Giddy-up.

Many women who work in the sex trade will relate to the internal negotiation involving limits and safety. You’re entering terrain that may be more work than you’re ready for. A slave can be kittle-­cattle, often trying to push for a more personal exchange. Can you trust him to behave acceptably if you fulfill this latest request?

You managed to negotiate the initial arrangement, so what do your instincts tell you? You already trust him enough to let him [insert appropriate verb here] your boots. He also knows exactly where you live and you seem fine with that, too. If you are interested in pursuing this more intimately, it’s up to you to articulate your boundaries by literally writing up a contract. What will you tolerate? How long and where would the exchange take place and what would your fee be?

Most people who do risky jobs (babysitting or mountain climbing, to name two others) make sure someone has their coordinates before they set out. I suggest you do what many working girls do: leave your cell number with a trusted friend, along with a time to call when you will be sure to answer.

ORGASM CHASM
I’ve been in a relationship with a woman for about three months. The first few times we had sex she came from a combination of vaginal penetration and my fingers working her clit. She told me that it was the first time she’d ever come during sex without using her vibrator. What she has used to masturbate since she was a teenager is a large back massager which could lift asphalt if you attached a drill bit to it.

I’m OK with her using it while we fuck if it helps her get off. But is it physiology that makes some women need a dose of heavy-duty direct stimulation in order to orgasm? Is it possible to desensitize the clit through too much use of something like an industrial vibrator? Could it be emotional/psychological issues too? Are there prospects for her finding other ways to achieve the same level of pleasure? She says that oral sex doesn’t get her off — a tragedy for me because I love it — and she’s not all that into foreplay. I’m trying to understand and she’s not always very communicative.
PLEASE DON’T USE MY NAME

Yep, this orgasm thing turns out to be a bit of a pig-fuck, eh? Let’s start with some anecdotal evidence — my own. Despite the fact that I have thrashed away at my vulva with the tool shed–worthy Magic Wand for a decade, once my second Wand cacked out a few months ago, I was inspired to expand my bedside selection and I am now on great terms with a couple of smaller, rechargeable vibrators.

It doesn’t hurt that I get free sex toys — not an option for most women who grow to trust one and generally buy the same again because they know it will get them to an elusive place. The vibrator, regardless of its size and power, is very important to me as it’s an ally in both generating physical excitement and distracting from the things that hinder pleasure during intercourse. (Does my ass look like a giant, churning vat of cottage cheese? When will my tits finally get saggy enough to hit me in the face?) For some women, this reassuring friend will be a pillow or some fingers or an asphalt lifter.

Orgasm itself is an elaborate combination of factors — including age, physiology and cerebral input — and science writer Mary Roach’s new book, Bonk: the Curious Coupling of Science and Sex, confirms this. As Roach astutely notes, “A conclusion you will encounter many times in the course of these pages is that the sexual anatomy and response of the human female are as uniform and predictable as the weather.”

Many of the scientists Roach interviews still marvel at the intricate diversity of orgasm, and many spend years simply debunking outrageous myths from more morally restrictive times. Every chapter holds its fascinations and Roach is exceptionally funny — though if you are easily distracted you may get trampled under her gabby, incessant footnotes. But Chapter 11, “The Immaculate Orgasm” — where Roach visits Marcalee Sipski, an expert on sexuality among people with spinal-cord injuries and diseases — will be of particular interest to you. If a woman with no sensation from the waist down can come, just what the hell is an orgasm and where does it come from? Read Bonk and, while you’re at it, get a copy for your girlfriend, too.