Dear Sashas, To tell you how it started would take a book, so I’ll tell you up front that a man in my building pays me to “rent” my chocolate brown, knee high riding boots a couple of nights a week. I don’t know when he returns them, but they are always 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 to let him “look after them” while I wear them. I’m not sure what he means by “looking after,” though I can imagine. My question is how can I be assured that I’m not getting into dangerous territory here and that he’s as harmless and submissive as he seems?
-Hate to Lose the Rent
Dear Hate,
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: highly fetishized footwear, a nine to fiver 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 negotiating involving limits and safety, and I won’t lie to you, you are entering terrain that may be more work than you’re ready for. Slaves can be kittle-cattle, often trying, as evidenced by his escalating demands, to push for a more personal exchange.
Can you trust him to behave acceptably if you fulfil this latest one? 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’re 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? What would be a deal breaker?
Most people who do jobs that are considered risky (babysitting, mountain climbing, to name two others) make sure that someone has their coordinates before they set out. I suggest you do what many working girls do and leave your cell phone number and a time to call, when you will be sure to answer, with a trusted friend.
Dear Sasha, I’ve been seeing my girlfriend for a few months and recently she asked if I’d be interested in some anal play—my receiving it from her. I said I’d give it a shot and I’ve found myself enjoying it. But shortly afterwards, she started making little comments—”jokes,” she calls them—here and there that she’s turned me gay etc.
I laughed it off at first but she keeps going on and on about it, even making suggestive remarks about it in front of our friends. As a result, I got really annoyed with her and told her off. She then started calling me homophobic and said that she didn’t think I was, “that kind of guy.” The whole thing has upset me because I don’t think that’s fair at all. Are my actions wrong?
-Anal Banal
Dear Anal,
Hand this newspaper to your girlfriend right now. Girlfriend, we do not ask our new boyfriend to try ass play, have him graciously agree, and subsequently enjoy it, then make homophobic remarks by implying that anal sex is the exclusive province of gay men (and that moreover being gay is something worth being teased about), then call him a homophobe himself when he gets ticked off.
Look, I know you’re doing it because you think you’re such a renegade for fucking your boyfriend’s ass and you’re trying to find some way of working it into casual conversation but just stop it, will you? Everyone is doing anal now, it’s no big deal. Go get yourself a tranny boyfriend if you want something to wow your friends.
Got any questions for Sasha? E-MAIL: POULEDELUXE@YAHOO.COM
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