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

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

Dropping the L-bomb

Dear Mistress,

One of my most trusted male advisers assured me that I, as a woman, should never say "I love you" first, and surely not within the first few months of a relationship.

I've been with my man for just a couple of months but find myself falling quickly into what feels a heck of a lot like love — trust him like no other, never felt this way before, yadda, yadda, yadda. The past few women he's been with have done him very wrong, and there was a moment at the beginning of our relationship when he got squirrelly about getting involved with someone again. The squirrelly phase has since passed, but I completely understand his anxiety about women and wonder if he'll be slow to drop the proverbial "L-bomb" before he's confident that I feel the same. Thus, should I say it first?

Signed,
L-Bomb Scare

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Dear L-Bomb,

The beginning of a relationship is equal parts thrilling and terrifying — and the "I love you" dance is all part of the ride. It would be much easier if we never had to be the one to say "I love you" first, but then we'd never know what it's like to take a chance, put our hearts on the line and declare our true feelings.

That said, getting an "I love you"' too soon is akin to having the proverbial cigarette before fucking instead of afterward -- it's unearned and far less satisfying. Besides, it's only been a couple months — you still have much to discover about one another, including about a million of his annoying habits that might make the idea of saying "I love you" lose its luster.

As for women in hetero relationships not saying "I love you" first — that's crap. All feminist posturing aside, this archaic way of thinking is also offensive to men. If we say that men must have control over the word "love," we're also saying that they are unable to accept love that is offered to them. Men deserve a little more credit than that, don't you think?

Saying "I love you" should feel effortless. If you're having anxiety about the potential outcomes, why not let yourself off the hook for a while. Take a deep breath, let it out and relax. Enjoy your new boyfriend and the love you're feeling. I guarantee, you'll know when the moment's right to drop the "L-bomb" — if he doesn't drop it first.

Preparing the bomb shelter,
MM

Effeminate Mystique

Dear Mistress,

I was friendly with this guy for over a year. I always thought he was really hot, but I assumed he was gay because he's on the effeminate side, and I witnessed him drunkenly kissing boys at bars. However, in November, he corrected me and told me that he was "definitely straight." As soon as he said that, I asked him out. We've been "dating" ever since, hanging out a couple times per week and having sex every two weeks or so — not exactly a whirlwind romance, but our connection is too compelling to let him go.

He says he has a hard time thinking of me as more than a good friend, but he still allows me to plan — and pay for — elaborate dates. Then he dropped a bomb on me last week: He told me he has a crush on another girl and asked me for advice. Oh, and by the way, he's still making out with men on occasion. I'm a 36-year-old woman — aren't I too old for this bullshit?

Also, I feel like I should have my sexuality figured out by now, but I'm constantly confusing myself. I've had sex with a number of gay men, and I've also tried dating women. I find that I'm only attracted to feminine women and effeminate men — what is my deal?

Please help,
Fractured Attraction

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Dear Fractured,

Girlfriend, whether or not your boyfriend is gay is the least of your worries.

Let's review: He makes out with other people, he doesn't pay for dates, he only sexes you every two weeks, and he's asking you for advice about other women. How much more time are you willing to waste on this guy?  

As for your "deal" — comedian and queer icon Margaret Cho said in the latest edition of Original Plumbing Magazine that "I'm really attracted to masculinity whether it's in a female-bodied person or a male-bodied person. To me, masculinity is sexually arousing, that's what I'm oriented to..." Have you considered that you might be like Cho, only attracted to femininity? Forget about being attracted to a gender and go with whatever turns you on. Dump your waffling, freeloading boyfriend for a feminine person — male, female or transgender — who can love you back.

Femininely yours,
MM

Bet on Wet

Dear Mistress,

Why is it that some women get really wet during sex and others do not? I've been with women who get so wet, it's almost intimidating; however, some of my partners remain mostly dry and make me wonder if they're even interested in me.

What's the deal with wetness, and how can I maneuver wet and dry without making my partner feel awkward?

Signed,
Weathering the Tide

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Dear Weathering,

Simply put, every vagina is different. It's nearly impossible to gauge a woman's level of arousal by wetness alone, so it's better to take it as it comes (so to speak).

Vaginal wetness can be dictated by a number of factors, including menstrual cycle and medications. I'm no pharmacist, but I've had friends complain that various medications, especially antidepressants and antihistamines, can cause vaginal dryness.

Whether the forecast is flooding or drought, you should always be prepared for the weather. Unfortunately, women are taught to be self-conscious about their bodies and can therefore be uncomfortable with their own vaginal wetness (or lack thereof). If your partner is super-wet, tell her how much you love being able to feel her arousal. By the same token, if your partner is on the drier side, be sure to keep a water-based lube handy to maximize enjoyment. Have fun with it — lube isn't a punishment, it's a slippery good time for all parties involved.

Meet you at the wet bar,
MM

Pervy Payback

Dear Mistress,

I'm a guy in my early thirties, and I've been seeing a woman for a few months. She has completely blown my mind wide open about sex. Until her, I'd always had "pleasant" sex with my girlfriends. Now I never know what to expect. She recently fulfilled a long-time fantasy of mine by meeting me for a drink at a bar on Church Street wearing nothing but a garter belt, stockings and high heels underneath an overcoat. Needless to say, it was hot!

So, what's the problem? I feel like she's doing all the work, and I'm just going along for the ride. I try to think of things that I could do to excite her as much as she excites me, but I find myself doubting my abilities. I worry my ideas will fall flat, and I'll look like an ass. How can I repay her for all the unbelievable sex she's given me?

Signed,
Indebted

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Dear Indebted,

Stop living like you're in debt and begin living like a rich man, because you've certainly hit the jackpot with this partner.

While it's admirable that you want to reciprocate the naughty gifts your girlfriend is masterfully giving, you can't let your penchant for payback paralyze you and make you doubt your abilities. Remember, there's nothing more unattractive than low self-esteem.

In all likelihood, your girl is enjoying every sinful second of your love affair just as much as you are. Your encouragement and willingness to bend to her every whim must be a turn-on for her, or else she wouldn't keep dreaming up dirty deeds to share with you.

That said, you always want to be an equal partner in your relationship. The best way to know if you're living up to your partner's expectations is simply to ask. Tell her how enamored you are of her overactive erotic imagination and ask her if you can contribute further. She sounds like an über-confident woman — I'm sure she'll let you know if it's time to pay the piper.

Imaginatively yours,
MM

Casual Jealousy?

Dear Mistress,

I'm a thirtysomething woman living in Montpelier. I've been sleeping with this guy on and off for over a year — no strings attached. Ultimately, I'm just not interested in him in that way, plus he's made it clear he's not into a relationship with me.

I'm writing to you because he's now interested in this girl I know. I hate to admit it, but I'm finding myself a little jealous. What's more is that this girl and I have a good mutual friend in common, and we've recently been invited to the same small social gatherings — she nearly ended up at my house last week with our mutual friend, and that would have made me really uncomfortable.

I have two questions. First, is it normal for me to be jealous, even though I don't want a relationship with this guy? Second, how do I deal with this impending "friendship" with this girl, if we keep ending up at the same places?

Signed,
Strings Attached

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Dear Strings,

Having casual sex in a small city like Montpelier is vastly more complicated than getting it on in a larger town. In a rural state like Vermont, you may be able to keep your emotions in check for a "no-strings-attached" affair, but you'll most likely still have to navigate seeing your ex-lovers in social situations — and that includes watching them move on to new relationships.

When you have a year-long relationship with someone, whether it is purely physical or not, you develop feelings; it's natural. Don't be too worried about your jealousy — just keep it in check. If you truly do not want a relationship with this guy, stop wasting your time worrying about whom he's seeing — channel that energy into worrying about your own life.

As for the girl, know your boundaries. You don't have to be B.F.F with her just because you have a mutual friend. Be classy and polite in public, but stop short of divulging your innermost secrets. Believe it or not, it is possible to keep acquaintances at arm's length — even in Vermont.

Casually,
MM

Madonna vs. Whore

Dear Mistress,

I'm a single woman in my thirties who understands her sexual needs and is not afraid to fulfill them. I've been single for a while, and I date quite a bit.

Recently I was having a "fling" with this guy. He made it very clear he did not want more, and I was fine with that. When we took a short break, I had a "fling" with another guy. Later, I started things up with the first guy again, and it ended shortly thereafter.

I recently found out that these two guys know each other and that they somehow figured out that I had "flung" with both of them. Now I'm the "bad girl." Neither one of them wanted a relationship with me — so why am I in the wrong?

I am sad to find that the old double standard still exists. I did not lead anyone on, nor did I make any vows of exclusivity; thus their problem with me must have more to do with me being a sexually confident female who can separate love and sex. Why is it that "boys will be boys," but girls need to be prudes, virgins or whores?

Can you help us open-minded ladies open the minds of these supposedly open-minded men?

Signed,
Jezebel

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Dear Jezebel,

What we've got here is a classic example of the Madonna/whore dichotomy wherein a woman must either be wholesome, and therefore "good," or sexy, and therefore "bad" — leaving no room for her to be both the Madonna and the whore.

Men like the ones you "flung" with buy into these female archetypes, displaying signs of a Madonna/whore complex. Meaning that they will happily have sex with the "whore" behind closed doors but will only allow themselves to love, marry and have children with the virginal Madonna.

It's high time that sexually confident women got their due; just because a woman knows what she likes sexually and goes after it in the short term does not make her an unfit partner in the long term. Further, men should stop punishing themselves by not giving the "whore" a chance if, in fact, she's what they most desire. 

Jezebel, stay strong. Eventually the right person will come along who honors both the "virgin" and the "whore" in you — or, at least, that's what I keep telling myself.

Whorishly yours,
MM

Engaging Conversation

Dear Mistress,

I'm a woman in my mid-twenties, and I'll be a college graduate in a few months. I have two questions. Is there a deadline in a relationship to move on to the next level? (Like, for example, is five years too long to wait for a relationship to progress?) Secondly, I am in a committed relationship, and I am waiting for my partner to propose. Should I just take matters into my own hands and propose to my partner myself?

Signed,
Anonymous

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Dear Anonymous,

It's amazing that, even after all the gender-role smashing we've done, the most independent of women still get caught up in the engagement game — some to the point of mania. Anticipating a proposal can turn an otherwise smart, confident woman into a self-conscious pile of passive mush.

While there's nothing wrong with your proposing to your partner, be sure you're not acting out of a desperate need for validation in your relationship. Furthermore, forget the Hollywood notion of the surprise proposal on bended knee — it just doesn't work that way for most couples.

Generally, couples communicate about their hopes and goals surrounding marriage and family. Have you talked with your partner about the future? If you can muster up the courage to propose, why not dial it back a notch and simply say, "I love you and want to spend the rest of my life with you, and I need to know whether or not we're on the same page." Start there and see what happens. If you're both in love and intend to stick by each other, who really gives a care about a ring?

Engagingly,
MM

Cyber Brush-off?

Dear Mistress,

I hit the bars last weekend and met this girl. We hung out for the better part of the night, drinking and playing pool. When she and her friends were leaving, I asked for her number. She ended up writing down her email address. WTF? I swear I didn't do anything to deserve it. I was a total gentleman and didn't even spill any beer on my shirt. I thought she was into me, so what's with the cyber brush-off?

Signed,
Cyber Crushed

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Dear Cyber Crushed,

Stop being such a neophyte. We live in a world where the phone is just one of many ways to communicate with a possible mate. Whether she asked you to call, text, Facebook, Twitter or IM her, it sounds like she wanted to get to know you better, and you're blowing it by letting so much time go by.

If you could put your ego aside for a moment, you might see that this girl was actually trying to be smart. In this day and age, a girl can't be too careful — an email address is far less personal than a phone number. Or she could have a limited phone plan and doesn't want to use up her minutes on a guy who could turn out to be a dud.

Write her an email. Be charming and witty, and ask her out. Oh, and be sure to spell check — I knew a woman who used to give out her email address to weed out all the dummies.

TTYL,
MM

Toying with Valentine's Day

Dear Mistress,

I need some advice right away. Last weekend, my girlfriend was hosting a get-together for some of her girlfriends. I was in the kitchen getting a snack before returning to my man lair to watch the game, when I overheard them talking about sex toys. A roomful of women talking about sex toys — every guy's wet dream, right? Well, from the tone of my girlfriend's voice, I got the impression that she'd be into having a toy.

I am flabbergasted and don't want to miss out on this opportunity — I just never thought she'd go for something like that. I can't stop thinking about her and a sex toy. Valentine's Day is quickly approaching. Should I buy her something?

Signed,
Dude in Toyland

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Dear Dude in Toyland,

As exciting as it may seem to surprise your lady with a sex toy on Valentine's Day, you're likely to receive a better reaction from her if you discuss it beforehand and make an educated purchase — especially if you're planning to forgo the roses and chocolates.

When the moment's right, talk with her about adding a toy to the mix and observe her response. Keep in mind that she and her girlfriends may have been discussing the use of toys for masturbation, not necessarily using them with significant others. (By the way, either scenario is a win for you — women who masturbate more often have a better sense of how to get off with a partner.) If she's open to the idea, suggest that you browse some toys online together. Sex toys come in all different shapes, sizes and functions, and it's important to know what your girlfriend likes. Does she prefer clitoral or vaginal stimulation? Does she want a high-powered vibrator or a classic insertable with no batteries required? The bonus here is that the mere act of browsing toys online could lead to a hot round of pre-Valentine's Day lovin'.

And, please, don't skimp on your first purchase. You wouldn't buy your girlfriend gas-station roses on Valentine's Day, so don't buy her a cheap toy, either.

Toying with you,
MM

Cheaters Never Prosper

Dear Mistress,

My heart is torn. My ex-girlfriend now lives 1000 miles away, but she is still in love with me, and I love her, too. Our relationship ended in July after she cheated on me in a pretty bad way. However, we've stayed in touch, and she very much wants to get back together with me. She says she's ready to change her ways and promises to be a paragon of virtue. I'm afraid to go there because I got burned last time, and I don't want to ask her to commit because I don't think she can. Also, I've been having fun on the side myself. We're basically in an open relationship at this point, but it's a gray area that I don't enjoy.

Do I hold off until August when we'll be in the same place for a while, or do I jump into a situation that I'm not 100 percent comfortable with? I'm a relationship kind of guy, but this girl is testing my ability to forgive.

Signed,
Any Middle Ground?

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Dear Any Middle Ground,

There's no way around it: Cheating sucks. She betrayed your trust and is now testing your ability to be a forgiving partner by crawling back with promises of change and virtue — pretty rotten, if you ask me. While it's possible for couples to work through infidelity, it takes copious communication, intimacy and dedicated time — things you cannot access with 1000 miles between you. Plus, if your gut is telling you she's still not ready to commit, why would you put yourself in harm's way again?

Take the next six months to focus on yourself, and suggest she do the same. You say you're having fun on the side, and you owe it to yourself to explore new relationships unencumbered by a long-distance cheating ex-lover. If, after you've spent some quality time apart, you're still in love with her, give it a go when you're in the same zip code. Until then, let her be a paragon of virtue for someone else — you've got better things to do.

Paragon of whoop-ass,
MM

Oral Woes

Dear Mistress,

I've been dating a girl for about two years. She's amazing, and I love her very much. We're both really into sex, but here's my quandary: I rarely get off when she gives me oral. It's not that she's unwilling to try, or that she's a prude; I'm pretty sure she'd do whatever I asked of her. I think the problem is a mental block on my part. My thinking goes: "I'm getting head, and I'm about to get sex! Great!" So I stay the course until we end up having sex. Problem is, the few times we can't have sex, and she wants to get me off from oral, she can't. When she asks me how it feels, I say, "Great!" Let's face it: Oral feels good. There isn't much she could be doing differently, but it's really starting to bother her that she can't get me off when doing oral.

What can I do to get rid of this mental block?

Signed,
Orgasmorator

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Dear Orgasmorator,

Well-intentioned guys often train themselves to hold back during foreplay to ensure a rousing round of intercourse. However, this type of behavior puts too much focus on the old "in-and-out" and doesn't leave enough room for all the other pleasurable ways to orgasm. Believe it or not, heterosexual sex doesn't always have to climax with intercourse.

Conduct an experiment with your girlfriend. Choose a night when you'll have ample time and make intercourse off limits. If you're accustomed to lying back while your partner gives you oral, try taking a more active role. Some men report that they can't climax unless they're in control of the motion, so try some new positions where you can simulate thrusting (both of you lying on your sides or her lying on her back with you above her). Just remember — this is a two-way experiment. Whatever oral attention she pays you, you'll need to return blow for blow (so to speak).

Getting you off will make your partner feel like an oral aficionado and boost her sexual confidence. However, if oral still doesn't give you the "Big O," don't sweat it. You and your partner have something special — you're both into giving each other pleasure. So who really cares how you get off? 

Blown Away,
MM

P.S. If you haven't already entered for your chance to win a copy of Best Sex Writing 2010, click here to enter. I'm accepting entries through Monday.

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

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

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