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Sasha: Dispatch from a sex work conference in Las Vegas

LAS VEGAS, NEVADA -- Holy fuck, is it ever hot in Las Vegas in July.

Like you-could-fry-an-egg-between-your-tits hot. But it's a dry heat, as everyone says. It's dry, and for some reason that does make it somewhat more bearable -- on the hair anyway. God, my hair looked good in Vegas.

I'm not going to lie to you -- I did not want to leave Toronto. My life exploded about two hours before I had to be at the airport, and since I'd spent the past year with my life exploded while on planes, in airports and faraway places (I am now an expert at bawling my face off in foreign cities), I was kind of flipping out. Being triggered, as the womenfolk say. But I got on the damn plane. Because, come hell or high lesbian drama, I had to get to a hooker convention in Sin City.

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Sasha: Perfect sex and conscientious letter writing

Dear Sasha,

I am a 31-year-old straight male, fairly experienced with long-term relationships but much more experienced being single. Single guy wants threesome -- like what guy doesn't?

I've had a few experiences but definitely want more. Relationship threesomes are always awkward, and she never really wants to "share" her boy friend, no matter what she says beforehand. I'm single and looking for that perfect threesome I had once before when I was single, but I don't know where to start looking. I can't go to a bar and approach some cute girl, saying, "Hey, I'm looking to have a threesome with you and another girl."

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Sasha: The nature of (young) things

Dear Sasha,

I am a middle-aged, divorced environment writer with an affectionate eye on a much younger woman.

My friends consider me polite, outspokenly critical and a fit, reasonably good-looking man. My potential love interest, who is unattached, appreciates and even sought my mature attention to her singular life and talents as yoga teacher and videographer.

We met in a coffee shop, and superficially we have much in common. Acting, instinctively, I crave caring and sharing, and even intimacy, were her mood ever to become affirmative. I cannot yet intuit whether or not to pursue closeness with this tantalizing creature across a complex age gap.

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Ms. Communicate: How to meet single progressives

Editor's Note: This column is the second of a two-part investigation on dating for progressives. Read the first part here.

1. Online

Yes, many cool lefties are meeting online. It's not just for "losers" anymore. My own past few significant relationships of two years or longer in duration (as well as other less-significant relationships) were all from various online dating sites. The easy part is that you can already know a bit about the person beforehand, and have a sense of areas in which you will find common ground, if they answered the questions on favourite music genre and movies, etc.

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Sasha: No time for a relationship? Try a love doll

Dear Sasha,

I was wondering if you have any information on sex dolls. I am a person with no time at all for a serious relationship. I want to know about the sensation. I mean, how different could it be? We're talking like, a $200 doll. I need to know if it's a good buy.

Mr. Need To Know

I'm going to suggest you visit jackinworld.com, which offers intriguing tips on a variety of masturbation techniques and has message boards where you can ask others about their experiences with sex dolls and/or genital stimulators/simulators.

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Sasha: How to stand bi your friends

Dear Sasha,

What do most of the women you know think about bisexual/gay males? Are they turned on by the thought of watching a man fellating another man, or revolted? Would they like to part of a three-way where the men have contact with one another? You know how most males would love to see two women having sex with each other? I'm wondering if women feel the same about seeing two males together sexually.

Alex

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Sasha: Dating impossible men, planning a foursome and finding an orgasm

Dear Sasha,

I'm in love with impossible people. I always find myself chasing the people who aren't interested. I've missed a lot of good relationships and hurt a lot of really good people because of this.

I had a girlfriend who was really loving to me, but I lost interest and started obsessing over a guy who was clearly unavailable. It destroyed her, not only because I wanted to be with a man (how could she compete with that?), but also because I started to be a real bitch to her. Nothing she did was ever good enough, and eventually I dumped her. I really broke her heart.

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Sasha: How to get your guy into erotic massage

I've run out of arguments to convince my boyfriend to accompany me for an erotic massage.

I went out of my way last year to search out a nice salon where girls without fake boobs seem to have fun working together and feel like friends. I found a gem. It isn't at all easy to find a girl willing to give another girl an erotic massage. I liked the experience so much that I've asked my boyfriend to join me next time.

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Sasha: Safety and the sexual fetish

Dear Sasha,

I have the unfortunate enjoyment of a very painful fetish. I enjoy being kicked/kneed/otherwise struck in the groin by women whom I find attractive. I don't mean CBT, with its overly gentle flicks and pokes. I mean doubled over or down on my knees and/or making funny noises because some hot thang let loose on my manhood.

If she does it in the new shoes we picked out together, all the better.

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| June 9, 2010
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