Ain't sayin' she's a gold-digger

Recession romance, bondage bonding and addressing one's ass

Q

I’m a 28-year-old straight girl who’s dated quite a bit but hasn’t ever found the love of her life. Lately, with all the economic bad news, I’ve been seriously considering focusing on finding a guy who’s rich (if they even exist anymore) and latching on for dear life. I’m really not a superficial person, and of course I would have to be attracted to the guy in some ways, and he’d have to be kind and affectionate and trustworthy, but he’s also going to have to have a whole bunch of money. The reason I’m writing to you is because I feel like you’re smarter than I am and will be able to see the major flaws in this plan. I’ve thought through the whole thing and realize that I might be throwing away some fairy-tale relationship for financial security and the ability to live in a nice home and have as many kids as I want, and I think I’m okay with that. What do you think?

A

I think the biggest flaw in that plan is that there’s no way in hell you’re ever going to follow through on it. To be a serious gold digger you’ve got to be seriously committed to looking for dollar signs and nothing else. Not dollar signs and kindness, or dollar signs and trustworthiness, just dollar signs. You’ve already blown it by requiring that the guy of your fiscal dreams have a bunch of the “fairy-tale” qualities you’ve always expected your husband would have. Basically, I think you’re just disappointed and frustrated with dating. You probably had high hopes for the last guy you dated, and when that didn’t work out, you said, “Screw it, just get me a big, beer-bellied baron of Wall Street and let’s call it a day.” This too shall pass. Although it’s true that the dating process can be especially hard on those who are sensitive and romantic and idealistic, it’s also a fact that those kinds of folks can’t just suddenly retrofit their hearts to accept money as a replacement for true love. Trust me, you’ll eventually work it out. And I can tell just from the few sentences you wrote to me that you’re the type of person who’d be much happier if she were living paycheck to paycheck with a guy who touches her in some deep way, than living high on the hog with some dude you simply tolerate because he’s financially hung.

Q

I’m a 19-year-old guy who’s already pretty deep into the bondage scene. I’m not sure where this came from, but I love being dominated by a woman. Just last night, this girl I’ve been seeing strapped me to a table and then fucked me with a strap-on. Hot, hot, hot. The sex part I’ve got down cold, but it’s the time after sex I have an issue with. I’m just not into the cuddling thing. In fact, since I like my women to be strong and domineering, it’s kind of a turnoff to suddenly have them be all needy and clingy. So I’m confused about what I could do after sex that wouldn’t seem too cold but that didn’t involve a lot of hugging and heartfelt conversations. Any ideas?

A

So far I’ve heard about the things that you have done to you sexually, but I haven’t heard a thing about what you do to the women you’re with. As my mother used to tell me: Just because you’ve been table-fucked to orgasm doesn’t mean the sex is automatically over. If you’re not into cuddling, then the least you could do is take that strap-on out of your ass, bring the woman over to a bed and do whatever it is she orders you to do with your tongue, hands or whatnot. Now I know you’re only 19, but if I were you, I’d start working on those intimacy issues. At your age it’s still permissible to be all about the sex, but the day will soon be coming when being that emotionally unavailable will make you an extremely unattractive mate. I get that you like your women to be domineering during sex, but you can’t expect them to be completely emotionless sexual automatons. And cuddling does not necessarily equal clingy. You’ve just had an extremely intimate encounter on the kitchen table; frankly, I think a little huggy time would make a nice counterpart to that. And by the way, why is it okay for you to be so needy sexually (“Tie me up, fuck me, treat me like your slave”), but when a woman wants something from you it suddenly becomes a turnoff? I don’t mean to get on your case, but instead of trying to figure out ways to avoid those intimate postcoital moments, I think you should be pushing yourself to expand your emotional horizons.

Q

I’m a 33-year-old gay guy who was sexually molested as a child. Consequently, my ass is completely clamped shut. The only time I’ve ever had a dick up there is when some guy I picked up turned out to have the smallest pencil dick I’ve ever seen, so I figured I may as well put it to some decent use. But even then I had trouble getting it in, and wasn’t all that into the experience once I managed it. The thing is, I’m sick of being so one-dimensional and I’d love to see what all the fuss is about regarding getting plowed by nice, big cock. Believe me, I’ve tried. I’ve tried it using lots of lube, I’ve put myself in charge of inserting the dick into my ass, I even tried doing it after smoking pot, but no go. I’m now contemplating using muscle relaxers, but I’m not even sure if that will work. Is there anything I can do to unclamp my ass?

A

I’m not a big believer in using drugs to help you do something that ought to happen naturally, and, of course, it goes without saying that you should be seeking professional help to cope with your heartbreaking history of abuse. Given your past, though, anal sex may just not be your thing. It takes trust and a level of relaxation that might not be possible for you anymore. That being said, I think you should go with your pencil-dick instincts and buy a finger-size dildo and practice on yourself. Lube up well, take things slowly and work your way into feeling comfortable with a foreign object in your ass. If you have success, you can keep increasing the size of the dildo until you feel like you’re ready for the real thing. The next time you try it with another human being, make sure you pick someone who’s willing to be patient and work with you until you feel receptive enough to make it happen. There are plenty of anal sex resources out there—both online and in bookstores—that you should read to get as many tips as possible on how to relax your sphincter muscles (deep breathing, pushing down with the muscles, etc.). At this point, the very act of trying to make it happen is likely leading to self-defeat. Just chill out. In the scheme of things, if you don’t get to have a big dick in your ass, you won’t really be missing out on a key part of life. I definitely encourage you to keep trying, but just give yourself a break and let it happen naturally. Maybe your ass is trying to tell you that for you, this is not going to be all it’s cracked up to be. And I don’t know about you, but I always find it helpful to listen to my ass.

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Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com. Check out "Sex on the Street" with Jamie Bufalino at timeoutnewyork.com/video.