Lust Online

Dear Mistress,

Sexually frustrated, thirtysomething female here who needs some help getting laid. Yeah, I said it; I need to get laid. I'm creeping up on nine months with no action, and I'm over it!

My friends and I were talking about using the Internet to find hookups. Some of them were totally freaked out by meeting strangers online — yet they have no problem having a one-night stand with a guy they just meet in a bar. I knew a girl after college who used to hook up from Craigslist all the time. What do you think? Can you share some "best practices" when it comes to hooking up online?

Signed,
Have Wi-Fi, Will Travel

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Dear HWWT,

While I appreciate your sexual frustration, are you sure you want to go digging through the online dirt to find your next fuck buddy? The Internet is crawling with shut-ins and idiots, and it takes a lot of work to weed out the undesirables. Plus, hooking up with strangers — whether on the Internet or at the local pub — can be extremely dangerous. Haven't you heard of the Craigslist Killer?

Despite the risks, horny web users hook up all the time on Internet sites like Craigslist and Seven Days' own Hot to Trot. If you decide to try it, write a compelling ad that outlines your desires and describes your likes and dislikes — best to be straight up and honest. Since women are the minority on hook-up sites, your ad is guaranteed to garner much attention — which also means you hold all the cards. Keep yourself safe by not posting a photo with your ad. If you strike up an email conversation with a strong candidate, you may decide to send him a photo — but you're not obliged. If you decide to meet someone offline, demand it be in a public place, and I highly recommend bringing a friend along for the initial meeting. At the very least, tell someone where you're going and whom you're meeting, and agree on a time to check in during the evening.

When looking to get laid, it's always best to find partners organically through friend or community connections. However, that's not always easy, so we turn to the World Wide Web for help. More and more, using the Internet to hook up is becoming socially acceptable, but you still have to be careful. Remember, you can always trust your gut — if something feels off, move along.

Cybersitting,
MM

Gee, Whiz

Dear Mistress,

I've always wondered what it would be like to have a partner ask me to do something sexually that I'm not comfortable with. I wondered how I would react, what I would say, and whether or not I would ultimately push myself to try something new. Of course, being a relatively "vanilla" girl who has always been with relatively "vanilla" guys, I've never had to really worry about it.

However, my boyfriend of nine months recently told me that he fantasizes about me urinating on him. I did my best not to react poorly, but I was shocked. I told him I would think about it, but it's been about two weeks, and neither of us has brought it up again. Things have definitely felt strained — like a big, yellow elephant is in the room.

Can you help me understand why he'd want me to pee on him? Also, if I were going to try it, where would I even begin? I just don't see how it could not be totally awkward!

Signed,
G. Whiz

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Dear G. Whiz,

Kudos to you for not totally closing the lid on your boyfriend's toilet fantasies. As with any fetish, the best place to start is with a conversation. Your guy could be turned on by water sports because of an event in his childhood, or because he likes the idea of being overpowered by a woman brandishing a golden stream of dominance. The only way to know for sure is to ask him.

After your talk, determine how you feel. Remember, you are not obligated to do anything that makes you uncomfortable. If golden showers aren't your thing, that's OK — he'll just have to keep his piss play in fantasy, not reality.

On the other hand, if you decide you'd like to follow the yellow brick road, take it slow and have fun. Invite him for some naughty time in the shower, preferably on a full bladder. After you're both sufficiently turned on, tell him you'd like to try some target practice. The first time might feel awkward and strange, but he'll be grateful you're even trying it. And, you never know, you might enjoy yourself.

Off to see the Whizard,
MM

Going the Distance

Dear Mistress,

My fiancé will be leaving for a month-long class in June. He'll be on the West Coast, and I will be here in Vermont. I'm not worried about our relationship, as it's only a month — but I am going to miss being intimate with him! We have sex just about every day, and I've become accustomed to starting my day with a huge orgasm.

I'm trying to be supportive of his decision to take off for a month and not be too selfish about not getting my orgasms, but I'm wondering if you have any tips for keeping our sex life fresh while we're apart.

Signed,
Long-Distance Diva

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Dear Diva,

Kudos to you for keeping the home fires burning while your fiancé’s away.

First and foremost, make sure you have a good cellphone plan, because you're going to want to reach out and touch someone. Your man can still help you orgasm every morning — you're just going to have to learn how to masturbate and hold a phone at the same time. That or invest in a Bluetooth. If you're more visual, Skype sex is the way to go.

Of course, technology can get boring, so try going old school. Send him some steamy, hand-written love letters describing what you plan to do to him when he returns home. Not a pro with prose? Pick up an erotica book, underline your favorite pervy passages and pop it in the mail — he'll love receiving a care package from home, especially if you include a pair of your panties or a spritz of your perfume.

Above all, remember to be patient. Even the best-laid plans can get derailed by life's everyday nuisances. Remember, it's just a month — so treat this as a fun, experimental time in your relationship, not a burdensome arrangement.

Going the distance,
MM

Just (Don't) Do it

After his lurid fall from grace, Tiger Woods returns to the golf course today to compete in the Masters. As you might recall from the one billion news reports on the subject, Woods took a hiatus from the links after a dozen or so mistresses came forward and confessed affairs with the married superstar. 

To launch his return to the sport, Nike -- one of the only sponsors to stick by Woods -- released a 30-second spot featuring the voice of Woods' deceased father giving him a fatherly talking to. He says, "Tiger, I am more prone to be inquisitive, to promote discussion. I want to find out what your thinking was. I want to find out what your feelings are. And did you learn anything."

For his part, Woods stares into the camera and tries to look appropriately apologetic, but he mostly comes off looking creepy. He's supposed to be thinking "remorse" — but I think he's probably thinking "boobs."

Lord of the Rings

Dear Mistress,

Never in my life did I think I'd be asking anyone about this, but I'm writing to get some information on cock rings. I've been dating my girlfriend for almost a year, and we're very open about sex. Last week, she mentioned that her ex-boyfriend would often wear a cock ring. I played it off like I knew what it was, but, truth be told, I have no idea.

I've never considered using a cock ring, nor do I really have any idea why a woman might like her man to wear one. I guess I always thought it was a gay thing, but now I feel ignorant and, frankly, a little embarrassed to ask her directly. Can you give me an education in cock rings so I will have the confidence to talk with her about it?

Signed,
Out of the Loop

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Dear Out of the Loop,

Many men — both gay and straight — use cock rings to enhance sexual pleasure. Cock rings are most often made of leather, silicone, rubber or metal and are placed around a flaccid penis and/or scrotum. When the penis becomes engorged, the cock ring tightens, restricting blood flow and intensifying the erection. Some men report that they last longer with a cock ring; however, other men say the sensation of the tight ring prompts them to ejaculate more quickly.

If you decide to try a cock ring, be sure to buy the real thing. Some men have suffered serious consequences from using makeshift cock rings (like a metal washer from the hardware store). Without a quick-release mechanism, cock rings can restrict blood flow too long, leading to priapism, penile gangrene and amputation — ouch. In general, cock rings shouldn't be worn for longer than 20 minutes, and you should remove it immediately if your member becomes cold or numb.

If you want to impress your girlfriend with your knowledge of cock rings, ask her if she's ever tried one with a vibrator attached, designed to stimulate her clitoris (or anus) during intercourse. She won't think you're ignorant — she'll think you're the king of the cock rings.

In the Loop,
MM