Mr. Midnight

Dear Mistress,

I'm just going to come out and say it. I hate New Year's Eve. People put all this pressure on themselves to make it the best night of the year when, in reality, it's just like any other night. Oh, except that it costs double the amount of money to go out to eat, all the bars are packed with drunken douchebags, and you can't get a cab — not to mention it's almost always the coldest night of the year.

I know, I know. I should just quit my whining and stay home, right? Well, I can't. You see, my girlfriend LOVES New Year's Eve. She wants to go out on the town and live it up, and she expects me to enthusiastically do the same.

Normally I'm all about making her happy, but the thought of going downtown on New Year's Eve drives me crazy. Is there any help for me, or am I doomed to a night of socializing with drunken assholes in the freezing cold?

Signed,
Mr. Midnight

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Dear Mr. Midnight,

One thing's for sure — with an attitude like that, you're destined to have a rotten time, no matter what you do.

Call me superstitious, but I believe New Year's Eve is a foreshadowing of the year to come. If you spend the night being a negative influence on yourself and everyone around you, you'll be doomed to spend the rest of 2010 in the doldrums. However, if you can get over yourself and go with the flow on NYE, you'll spend the rest of the year welcoming happiness and unexpected good times.

That said, you seem certain your girlfriend has her heart set on going out. But maybe she just wants the night to be a special one that involves your showing a little effort. Have you considered asking her to co-host your own New Year's bash and inviting all your friends? Or you could suggest staying in, making a romantic dinner and watching the ball drop over Times Square (followed by your own fireworks in the bedroom).

Tread lightly. If she balks at your suggestions, let it go, and get ready to have a good time on the town — cabs or no cabs.

Happy New Year,
MM

Cheetah Woods

I was asked twice yesterday why I haven't commented on the Tiger Woods scandal. Frankly, the topic bores me — and pisses me off. Men who have money and power cheat on their wives. Okay, not all of them — but for those who do, why do we give them so much attention? People are up in arms because Tiger Woods was supposed to be this shining example for monogamy and fatherhood. Please. The media painted him with a hero's stroke, and now they'll burn him at the putter just as easily. I'm a pretty open-minded person, with a lot of patience for people who have commitment and/or relationship issues — but I have absolutely no tolerance for cheating.

Alas, I realize some of you readers might be curious about Tiger's indiscretions. To quench your desire for details, here's Gawker's "The Tiger Woods Saga: A Definitive Timeline."

Spork! An Erotic Love Story

Last weekend, I popped some popcorn and invited some of my favorite gays over to watch the 2009 version of Star Trek. Starring hotties like Chris Pine, Zachary Quinto, Karl Urban and Eric Bana, it's pretty much every gay geek's wet dream. Or, it would be, if all the male characters would stop chasing after chicks and start beaming into each others' beds.

Apparently my friends and I are not the only ones who think Kirk and Spock should screw at warp speed. A friend sent me this YouTube video called Spork! An Erotic Love Story. The words are taken from Alan Dean Foster's "Star Trek" audiobook (read by Zachary Quinto) and spliced together to describe a very hot encounter between the two main characters.

Enjoy! But, be careful, this clip is definitely not safe for work.

To tell, or not to tell...

Dear Mistress,

I have been with my boyfriend for several years, and we're incredibly happy. My boyfriend works at a small company, and he's in charge of training new hires. Well, the guy they just hired happens to be the guy I lost my virginity to in college. My boyfriend will be working with him, one on one, for the next month.

We all went to the same college, so I think my boyfriend knows I at least dated this guy, and I may have even told him about losing my virginity to him — but, honest to God, I can't remember.

The company holiday party is next week, and we'll all be there! I am freaking out. Should I remind my boyfriend that I once dated him? What if he then asks about the extent of our relationship? I just want to make the proper and mature decision, so I don't hurt my boyfriend's feelings.

Signed,
Cherry

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Dear Cherry,

Don't freak out. Think this through logically: Most couples, at one time or another, swap stories about losing their virginity. Either you have already told him your story and don't remember, or it will come up at some point in the future. And, now that this guy has reappeared in your life, you must acknowledge it. Remain calm. As with any touchy situation, if you treat this like a big deal, you're more likely to get a dramatic response from your guy.

Don't waste any more time before the holiday party. Ask how your guy's day at work was, and then ask him if he remembers that you and his new trainee dated in college. From there, I would let him guide the conversation. If he wants more details, he'll ask. If he doesn't care to know the extent of your sexual relationship, don't force it on him.

Some people might say you shouldn't tell your boyfriend, but remember — if you don't have a relationship built on trust and honesty, what do you really have?

Honestly,
MM

Stocking Stuffers

If you're looking to give a gift that's more naughty than nice this year, check out my picks for insertable toys. You can stuff them in stockings -- or anyplace else you desire. Obviously, the links below may not be suitable for viewing at work.

Leo
A fairly standard silicone dildo, measuring 7-1/8 inches long by 1-1/2 inches wide. Leo also suctions to smooth surfaces, and you can upgrade to the vibrating Leo kit for that extra holiday buzz.

Babeland.com says, "It could be its perfect size—just a tiny bit bigger than most, or the pleasing shape—realistic but not too realistic."

MM says, "As far as an everyday dildo goes, the Leo is perfect -- no bells and whistles, just a well-made, perfectly-shaped insertable to please most any user. Plus, it can be worn with a harness for some added fun."

Tristan Plug
A highly-rated butt plug, the Tristan is named after its creator, Tristan Taormino -- the queen of ass play. This silicone plug measures 3-1/4 inches in length by 1-1/2 inches in width.

PuckerUp.com says, "Thanks to the long neck, the bulbous head, and the two concave cut-outs off the base, it slides easily in past the sphincter muscles and fits nicely between your cheeks!"

MM says, "Tristan Taormino is the ass master, and you should accept no substitutes. You might even pick up a copy of her book, The Ultimate Guide to Anal Sex for Women (my personal ass bible).

njoy Pure Wand
This unconventional toy is made of medical-grade stainless steel and curves for max pleasure. It measures 11 inches in length (curved) by 1-1/2 wide at the most bulbous end.

PinkCherry.com says, "This deliciously curved tool doubles as a prostate massager and a G-spot stimulator, and it's a star at both."

MM says, "The sexiest part of using the Pure Wand is removing it from the body. The once ice-cold steel feels almost hot to the touch, warmed to the temperature inside the body — the heat combined with the weight of the toy is a sensation-slut's wet dream." (Read the full review here.)

Happy gift giving,
MM

Stick It

Dear Mistress,

I am a gay man, and I really like it up the butt. For the first twenty-eight years of my life, my sexual encounters have been few and far between, and I have never been in a relationship.

I recently became involved in a monogamous relationship with a really nice guy. He seems too good to be true, and the sex is so hot. His penis is definitely above average, and we have sex multiple times per week. Recently, one of my girlfriends scared me by saying that as I get older, I'm doomed to suffer anal incontinence, rectal cancer and/or having my rectum turning inside out from all this anal sex. I don't want to believe her, but I would like to know the ramifications of getting rammed in the anal orifice so frequently?

Sincerely,
Mr. Stick It In

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Dear Mr. Stick It In,

The good news is you've found a good guy with an ample member willing to satiate your appetite for up-the-bum delights. The bad news is, you have a majorly misinformed friend.

According to Tristan Taormino — creator of Tristan Taormino's Expert Guide to Anal Sex (Vivid/Smart Ass Productions, 2007) and author of The Ultimate Guide to Anal Sex for Women (Cleis Press, 1997/2006) — when done slowly and with plenty of lube, anal sex is just as safe as any other kind of penetration. Taormino goes further to say that anal sex can actually be good for your butt. She says, "The more you practice controlling and relaxing your sphincter muscles, the more you are exercising and toning them (just like any other muscle) as well as increasing blood flow to the area, all of which can improve the health of your ass."

Other reputable sources site that, although rare, anal incontinence can occur after prolonged injury to the internal sphincter — meaning that insertion would have to be perpetually forceful, without regard for the receiving partner's comfort level.

Thus, as long as you're listening to your body, taking it slowly and using lots of lubrication, you're cleared for as much ramming as your ass can handle.

Ms. Stick It In,
MM

Offline Endeavors

Dear Mistress,

I'm a single woman living in Montpelier, where everyone is either married or undatable. As such, I've all but given up on eyeing people in the bars or striking up conversations in the local bookstore; it's a fruitless effort.

However, I've recently seen a guy around town who I recognize from his profile on an online dating site. I'm not a paid member, so I can't contact him via the site. I'm wondering if it would be weird and/or stalker-like for me to approach him in public and say, "Hello. I've seen you online and like your profile"?

Signed,
Offline

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Dear Offline,

Living in a small rural state like Vermont, finding a mate can be an arduous task. Single, eligible people can seem few and far between — plus, you're severely screwed if you're not into composting, snowboarding or hiking Camel's Hump every weekend. To successfully date in the 802, you must treat it as a no-holds-barred cage match, making connections wherever you can — including approaching your mystery man on the streets of Montpelier. If he's posting photos of himself online and proclaiming to the world that he's single and ready to mingle, he shouldn't be surprised or offended if someone approaches him face to face.

But, before your motherboard interfaces with his hard drive, take a fresh look at his profile. Check to see he's been active on the site within the past month — you don't want to be referencing a profile he hasn't updated since 2006. Also, be sure you fit the description of the mate he's looking for — you don't want to waste his time or yours.

And, I hate to point out the obvious, but if you're having a hard time meeting people around town but finding attractive singles online, shouldn't you consider posting your own profile?

Yours in rural dating,
MM

Unrequited Love

Dear Mistress,

I've been seeing my girlfriend for six months, and I'm really into her. Here's the one problem. She dated a guy prior to me, and because we have so many mutual friends, we see him all over town. The way she tells it, their relationship was casual until she started having real feelings for him. She told him she was falling for him, and he ditched her.

I don't really consider myself a jealous guy, but this situation feels different. They didn't have a relationship that had a beginning, middle and end. If that were the case, I would feel better, like they had some sort of resolution. In this case, she fell in love with him, he rejected her, and then she started going out with me. I can feel the tension when they're in the room together. I don't want to be a jealous prick, but I have a bad feeling about this. How do I resolve this once and for all?

Signed,
Runner Up

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Dear Runner Up,

While unrequited love is a special brand of heartache, it's no more (or less) upsetting than any other type. Your girl may not have had a "beginning, middle and end" with this other guy, but you have to look at the bright side — their relationship never got off the ground.

It sounds like you've discussed her past relationship. But have you expressed your concern that she might still have feelings for him? If you can address the issue calmly and lovingly, ask her about the "tension" you detect when you run into her ex-lover. Let her know that you don't wish to be jealous — you just want to know where you stand.

Remember, she's with you — not him. In the end, you'll have to trust that she's a mature adult, capable of navigating her feelings and making good choices. If you can't find that trust within yourself, your insecurities will be more likely to bring an end to your relationship than her unrequited heart.

Requiting,
MM