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

Straight-O Student

Dear Mistress,

I'm a twentysomething girl, and I've been with my boyfriend for a little less than a year. We're having some difficulties. Mainly, the problem is my inability to orgasm regularly. I really like being with him, and I know it disappoints him not to "please me." I have had orgasms with him, but it has only happened when I've "assisted" him. I guess I don't do it on a regular basis because it makes me feel self-conscious to touch myself in front of him.

He recently suggested that I try masturbating more on my own, thinking it might help me orgasm more with him. I'm upset by his suggestion because I feel like he's giving me homework to do in order to have sex with him. What do you think, MM? Am I overreacting? How do I fix this?

Signed,
Touchy Subject

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Dear Touchy Subject,

I recently had the pleasure of listening to Kelly Arbor, a sex educator from Babeland, give a talk on gender and sexual pleasure. During his talk, he suggested that we must spend time masturbating to learn how our bodies like to be touched. Arbor says expecting our partners to know how to touch us when we don't know how to touch ourselves is "a lot to put on someone." I have to agree.

Your boyfriend has made an excellent suggestion. The more comfortable you are with your body, the better you'll be able to coach him on giving you an orgasm. His "homework" isn't meant to penalize you; it's meant to help you and strengthen your relationship.

The even better news is, you already know how to have an orgasm with him. Touching yourself during sex with a partner is not weird — many people do it, and most partners find it hot to watch.

In the end, it's all about being intimate with your partner and sharing the ultimate of pleasures; exchanging "homework" assignments and discussing your bodies without fear will only create a stronger bond between you. So put on your schoolgirl uniform and crack the books.

Studiously yours,
MM

Kissed Off

Dear Mistress,

I've been in a relationship with my girlfriend for a year. We are monogamous, and presumably most of our other lesbian friends are, too. However, when our group goes out on the town and the tequila shots start flowing, it generally turns into a no-holds-barred make-out fest. Our friends are all very flirty, and they view
French kissing as other people view handshakes — no big deal.

When my girlfriend and I first discussed our friends' loose lips, she was adamantly opposed to us making out with other people, saying it felt like cheating. I was sort of disappointed, because I think making out is harmless fun. So you can imagine my surprise when we were out last Saturday, and I turned around and saw her kissing a girl on her hockey team. At first I was excited and encouraged it, but then I got kind of pissed when we got home. Shouldn't we have talked about this again first?

Signed,
Lip Locked

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Dear Lip Locked,

You're right — if you and your girl previously decided not to participate in your friends' kissing circles, she should have initiated a talk with you before locking lips with her teammate.

However, you're now in a classic "don't cut your nose off to spite your face" situation. If you want to be able to slide lips with your friends on the dance floor, do not overreact to your partner's infraction. Approach her calmly and let her know how you're feeling about what happened. Explain to her that while you're willing — and even a little excited — to discuss kissing outside your relationship, you wish she had thought to run it by you beforehand.

If you decide to open your mouths to others, be sure to set parameters you're both comfortable with. Do both of you need to be present, or can this extracurricular kissing happen on a solo night out? Can you only make out with friends, or are strangers fair game? If jealousy issues come up, how will you deal with them?

And one more thing: Though kissing is relatively safe, it's not 100 percent benign. Be sure the girls you're smooching are worth the risks of mononucleosis, herpes and swine flu.

Kissed off,
MM

Roommates to Mates?

Dear Mistress,

I recently broke up with my boyfriend, and I have a dilemma. I've been roommates with Joe (not his real name) for a few months, and he's a great guy. Whenever we’re home, we laugh and talk a lot. We went to a friend’s party together and had a great time, but I can’t tell if he is interested in me. Considering my recent state of singleness, I'm hesitant to get involved with Joe, because I don’t want to transfer any residual feelings I have for my ex onto him.

To remove temptation, I set Joe up with a friend of mine. I’ve heard they are having fun, and now I am envious that my friend gets to enjoy Joe’s romantic interest. My questions are: Has roommate-turned-cuddle-buddy ever produced a noncomplex relationship that didn’t end badly? Should I have bit the bullet and told Joe about my interest in him and not introduced him to my friend? Can I still tell him, even though he’s gone on dates with my friend?

Awaiting your sage advice,
Close to Home

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Dear Close to Home,

Does Joe know he's living in a post-breakup crazy house? You say you like him, yet you set him up with your friend. You say you're ready to start dating again, yet you're concerned about residual feelings for your ex. It's perfectly natural to act irrationally after a breakup — but you're bringing it a little too close to home.

I suspect you're crushing on your roommate to occupy your time and make you feel less lonely. Furthermore, you most likely set him up with your friend so you could go on crushing without having to make any moves. Let it go. Leave the drama alone and take the time you need to get over your boyfriend.

However, if your home fires continue to burn for Joe, you'll have to move out and then let your feelings be known. Trust me — "roommates-turned-cuddle-buddies" usually turn into "roommates-turned-enemies."

Room for Mates,
MM

Waiting Game

Dear Mistress,

I'm a guy. I like sex (perhaps even more than the average guy). So here's my question: While I can't envision being happy in a long-term relationship without a healthy diet of good sex, I've found that leaping into sexual activity too early in a relationship can — if the sex is really good — put one or both people into a state of blissful desire that can make everything seem exceptionally swell, even if other forms of compatibility may be lacking.

At the same time, dating too long without makin' some moves can have its own drawbacks — you might become very fond of someone, only to find out you're not cut out for bliss in bed.

I'm at a point in life where I want a lasting relationship, but I don't want to wait too long to have sex with a potential partner. Where's the happy medium?

Signed,
First Date Mate

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Dear Mate,

While it's important to know whether you're compatible when it comes to communication, values and goals, it's also important to know if you click in the bedroom. Couples "come together" there to reconnect in the most intimate of ways — and the chemistry has to exist.

That said, if you're looking for a lasting relationship, you would be wise to keep it in your pants for at least a few fact-finding dates. (Forget movies or loud bars where you can't get to know each other in a meaningful way.) If you're still craving her after a number of dates, you're cleared to move it to the bedroom — that is, if she's willing to go with you.

And just because you're not having sex doesn't mean you can't discover clues to your potential chemistry. Kissing, if given the chance, is an incredibly erotic and telling way to explore each other intimately without doing the deed. If your tongues are compatible, chances are your naughty bits will be, too.

Patiently,
MM

Action!

Dear Mistress,

My boyfriend really wants to videotape us having sex, and I'm warming up to the idea, but I'm still nervous. I'm not worried about the video falling into the wrong hands, as we would record it onto my camera, and I would have total control. I'm more worried about what will happen if I'm horrified at the sight of myself having sex. I think we can all agree that things wiggle and jiggle during the act. What if I'm so turned off by myself that I never want to have sex again? (OK, that's a little dramatic, but you know what I'm saying.) Couldn't he have thought of this idea during the summer, when I at least had a tan?

Mistress, you must have some tips on how a girl can look her best on camera. Help!

Thanks,
Camera Shy

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Dear Camera Shy,

Kudos to you for being willing to step outside your comfort zone and try something new. Seeing yourself in all of your boot-knockin' glory can be a daunting thought, but you have to think of yourself as a leading lady — you're hot, no matter what wiggles and jiggles.

Your on-screen debut doesn't have to be under fluorescent lights through a wide-angle lens. Dim the lighting and consider some creative camera positions. Instead of a full-body shot, set up the camera to capture your face and chest while your guy takes you from behind. If you're still feeling shy, add a sassy piece of lingerie to flatter your shape and make you feel more confident.

To get more ideas, check out some amateur porn online — couples all over the world are revolutionizing porn in their own bedrooms, and you can benefit from their expertise. If you can relax and have fun with this project, you'll give new meaning to the command "Action!"

Ready for my close-up,
MM

I Vant To Suck Your Venis

The world has gone Vampire crazy. With Twilight and "True Blood" clogging up our pop culture veins, we're ready to bleed for Edward and Vampire Bill -- and some of us like that idea.

Fleshjack (makers of Fleshlight) came up with a positively spooky way to capitalize on our fang fantasies with Count Cockula -- a soft, fleshy canal with an opening shaped like Brad Pitt's pretty mouth in Interview with a Vampire. Here's what Fleshjack has to say:

Polish up your stake and drive it into this soft, vampire mouth for an orgasm that will wake the living dead. Packing the same punch as the original Fleshjacks but housed in a compact soda can and featuring the exclusive Vampire Fang inner canal texture not found on any other Fleshjack product.

If you've ever wanted a lap dance at Fangtasia, this just might be the product for you.

Happy Halloweenie,
MM