Sex With the Expert: Condom Correction + Orgy Guesting

Sex With the Expert: Condom Correction + Orgy Guesting

Why you should care

Because sexy is as sexy does. When it’s done right.

Talking Tricks

EUGENE, SIR: In college a friend, who always had nice stuff, told me how she could afford it. After getting sick of asking her parents for money she actually figured out that men would go on dates with her for cash. She had sex with them if she wanted to, if she didn’t she didn’t, but at the end of the evening she came home with a bag full of cash. It seemed easy enough to me and I started doing it too. None of that is the problem. The problem is do I have a responsibility to tell the people I’m dating that this used to be my job? I am disease-free but outside of that should I say something? It’s not something I am ashamed of and it seems I should be able to talk about it, like most people talk about past jobs, right? — Happy Having Hooked

Dear Xaviera: Well, there’s the way things should be and the way that things are. On Planet Eugene, this information about you having been a ho would be rather ho-hum. It’d be like “it’s raining today” or “I like eggs” or “I screwed 1000 men for cash” and each would have equal weight and be of equal interest. On Planet Eugene. Why here? Because here I’m fully cognizant of the fact that what we do for a job is only one aspect of what we do as a person and is a singular dimension of that which is multidimensional. Namely: you. Or me. Or anyone, really.

However in the real world you have to deal with real people. These are the self-same real people who will feel in the face of this, inadequate. They will find images of you having sex with others intruding when you’re having sex with them. They will wonder when they’re screwing you if this is what it was like when you were working and how they matched up. They will, in essence, lose their minds.

There’s also the possibility that they are not this way and this represents a wholly attractive kink for them. These types are both off center of how YOU really understood what you did but if you had to place a bet for future success I’d bet on the latter and not the former.

Why/how? Because for the latter there’s nothing fundamentally wrong with what you did for a job. For the former? It’ll seem like there was nothing fundamentally right about what you did for a job.

Condominium

EUGENE, SIR: I’m having sex with men in their 20s. They know all about HIV and AIDS and I have to fight to get them to wear condoms? In 2014? What the hell? I know the claim is that it minimizes sensation but so does death. What are they thinking? — Rubber Hitting the Road

Dear Safety First: I’m going to do what no one has done here in just about forever: tell the truth about condoms. Men who complain about sensation are lying. But they’re lying for one very specific reason considering all of the reasons that people lie. Here, very specifically, because they are attempting to conceal a fault. The fault very simply being that the time when condoms matter the most, first time encounters, early stage encounters, most men are fraught with a whole passel of difficult things to deal with up to and including premature ejaculation, failure to get and/or sustain an erection, not doing it well or often enough, not being able to get their partner off, getting back to their wives or husbands or whatever. It’s a symphony of cacaphony and through it all and the tension of not just being adequate but GREAT? Having to smoothly deal with a condom right before you’re about to go on stage, so to speak.

Yup, it’s hard to be a man.

I mean it should say it all that men would rather RISK DEATH than to deal with the penis destroying power of a condom halt. Other advice columnists will advise you to make it part of sex play, to make putting on a condom, sexy. Not bad advice but really it will not quiet down the symphony and the reality of it is the only thing that will? Practice. Which means that men for whom it’s no problem are probably the men who should most be using one.

So consider yourself lucky. Unless you want to have a relationship with one of these Lotharios. Then consider yourself unlucky. Unless you’re only there for the sex in which case? Yes: back to lucky!

Orgy Planning

EUGENE, SIR: We want to have one. Hints on how to do so? — no name

Dear Caligula: Having never had one I can only guess on the basis of the ones I’ve been to. But the first thing to do is to make sure you have the space. A private space. Music. Candles or something other than super bright harsh lighting. Incense because people stink and the more people there are the more they stink. That gets you 20 percent there. The other 80 percent? Your guest list. Too many voyeurs and you got nothing. Too many first time couples and you will have tears and fist fights. No, it’s got to be a mix of something old, something new and a great enough mix of types and personalities to power this kind of party.

It also helps to have some sort of ice-breaking arena: a dance floor, a hot tub, a pool, or drinks. And I don’t know what town you’re in but everything is online now and I’m quite sure unless you live in a prison you can find likeminded folks who don’t live in your neighborhood if that’s of interest to you. Security is also a concern if you’re dealing with strangers but you can minimize problems via a cool locale. With visible sight lines and again: guest list.

There are plenty of other pitfalls – no one showing up, people showing up and leaving too early leaving the party under-attended, too many guys and not enough women – but you can’t really go into this any other way than hoping for the best. Good luck.

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OZYWildcard

Square pegs. Round holes.