Virginity for Valentine’s Day // Reigniting The High Of Love // Lesbian Cuckolding

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Ms. M.,

I’m still a virgin. I’ve been dating the same guy for seven months and he is a virgin too. My mom always told me having sex before marriage was okay as long as I love the person. We say I love you, but I don’t really know if I truly love him. I plan on moving across the country for college next year and he plans on staying here to work at his family’s business. I’ve decided I don’t want to go off to college still a virgin. Most of my friends have already had sex and I always feel like I’m missing out on something when they talk about it. I think I want to give my boyfriend my virginity for Valentine’s Day. Is there anything I should know first to prepare? Do you have any pointers or tips for first timers?


What an exciting idea, Ready! One thing is for sure, Valentine’s Day, 2013 will always be a benchmark in your book!

While parents and older generations like to put the idea in our heads that sex is only deemed acceptable if you love someone (or the more antiquated view—only if you’re married), it’s simply not true. Sex and love are two different things, even though they go quite nicely when paired together. You can be madly in love with someone, and still fantasize about, or be driven to have sex with someone else. This is completely human. This is completely normal. The key is to always be honest with yourself, your partner(s), and not hurt people along the way.

Sex is perfectly acceptable when you desire to have it, if you’re safe and responsible, and if you’re with someone who is respectful of you, your body, your needs, and your pleasure.

But I would advise you be respectful of your own pleasure first. Can you orgasm when you masturbate? The first step to loving yourself is to give yourself a little lovin’. You won’t have an orgasm with a guy if you can’t give one to yourself. Your orgasm is not some gift he gives to you; it’s the gift you give to yourself, and he gets the honor of being present and a part of it when you do. Next, to prove he is respectful of your body and your pleasure, have him get you off with his hands or his mouth before you let him go inside of you. If all women made this a golden rule, the world would be a much better and happier place. Why risk STDs or pregnancy if you’re not even going to orgasm?

Oh wait, you’re curious. You said it yourself, you don’t want to go off to college a virgin and you feel like you’re missing out on something. And you know what? That’s really effing cool of you. In all honesty, I don’t think most girls loose their virginity to cum. I think most of them hope it will make a guy like them more or commit more. You, however, with your perfectly healthy curiosity are in the best possible scenario—in control and aware of what you want and why you want it, which doesn’t involve using sex to manipulate your boyfriend or the relationship.

You should know it’s not going to be fireworks and orgasmic explosions your first time. The best part of it will probably be the foreplay and kissing before penetration, then the cuddling after you’re done. My first time was awkward, I bled, and it hurt. It hurt really badly. But I did it again the next day, and the next day. It’s kind of like learning how to ride a bike or water ski. You have to practice, and it might hurt the first few times, but you have to keep going. Loosing your virginity may seem like an event, but remember, this is only the beginning to the process of your sexuality. It’s like opening a door to a magical land that has yet to be discovered and explored. You must keep exploring.

Make sure you both know how to use a condom properly—from how you open the wrapper, to how you put it on him. They are only effective if they are used the right way. If I were you, I’d go with a lubricated condom, and have some water-based lube nearby. Sliquid is a great brand, and the one I would recommend.

Don’t worry about whether or not he thinks your thighs are fat or if he sees that pimple on your bum or what he thinks of how your pussy looks. He’s going to be so excited that his rocket ship penis is about to blast off into your supernatural slit of galactic outer space, he’s not going to pay attention to whatever it is about your body that makes you insecure. We all have something we’re insecure about—even him—so brush that dirt off your shoulder.

Be sure you’re relaxed and in a safe comfortable environment. Don’t just go for it. Take your time. Spend a long time kissing and working your way up to that moment. Giggle along the way—it builds intimacy and comfort. When you do finally go for it, breathe deep. Don’t clinch. Let go. Relax.

And remember, sex is like Chinese food: you can have it once and it’s God-awful horrible and you think you never want to have it again. But don’t let it turn you off forever. Be open to trying it again with someone new, somewhere new, because I promise you there’s an infinite amount of variation out there in this world and you’re sure to find at least one where you can’t seem to get enough.

Love Always,

Ms. M.


Dear Ms. M.,

I’ve been married for six years to the same man. We’re happy and active in our sex life. But lately it feels kind of boring, like we’re in a rut. The sex is great but also routine. I think we’re too accustomed to each other. I was wondering, can you suggest anything we can do in our sex life or otherwise, that might give us that feeling of being newly in love again? I miss that.



Dear Donna,

Love and sex! Two different things, but great when they go together—kind of like strawberries and champagne. I was recently on a Real Love panel with the ever-so-brilliant, Dr. Helen Fisher. I’ve followed her work for years, as she studies the science of romantic love and the brain in love. So when I finally met her, I was more than excited to introduce her to Mr. M. and credit her for teaching me what I know about keeping that spark alive. I was thrilled to confess that I have used her scientifically proven trick to boost that being-in-love feeling: novelty. Doing something completely new, thrilling, and risky together boosts dopamine in the brain. And dopamine is the chemical that gives you the feeling of being high on love.

A couple of years ago, Mr. M. and I were on an evening flight on a mostly empty small plane. There weren’t people sitting around us, so when the flight attendants were required to be seated for landing, I went down on him right there in the seat. No blanket over my head, just me giving him head. He finished just as the wheels touched down.

Another time, we were walking from our apartment to Grand Central Market to do some shopping. I grinned, grabbed his hand, and told him to follow me as I took him on a little surprise detour. We walked into what was then, the Helmsley Hotel on 42nd Street, past the front desk agents and onto the elevator. We got off on a random floor, walked into a stairwell, and had sex. Then there was the time we made love on the twirly stairs inside the lighthouse on Isla Mujeres overlooking the ancient Mayan ruins. Once he went down on me atop Mont Royal—I was wearing a skirt with no panties and thankfully, it was summer in Montreal and not too cold. There was a pebbly beach in Sitges, Spain and a sandy beach on an early spring morning in Amagansett. Another time we rode our bikes out into a field of blooming yellow flowers in Bath Spa, England, then rolled around making love in them. There was the roof of his parents’ house … lots of roofs actually. I can’t even get started on the numerous bars, clubs, and restaurants where we’ve frolicked … oh, and once in a library. At home, there is not one inch of surface area that hasn’t seen us naked. We especially like the kitchen, though I’d advise never messing around after chopping hot peppers. Johnny Cash’s Ring of Fire ain’t got nothin’ on a body part that’s encountered the fiery juice of a jalapeño.

I would hope all couples incorporate such spontaneity into their sex lives because it also boosts the dopamine, which boosts that feeling of being in love. Lingerie and candles are fine and sexy, but they’re not going to give you or your partner as big of a thrill as doing something novel or even risky together. If my experiences are a little too dangerous for you, then try something like renting a limo and taking a romping ride around town. Or check out day use hotels, get a room for the day, invite him over, and surprise him with a role-play scenario. Try to make part of the routine to never have sex the same way twice in a row.

It’s important to remember though, novelty doesn’t always have to be sexual. You could go on a hot air balloon ride, sky diving, bungee jumping, or just do something new and out of your element together.

Happy Valentine’s Day,

Ms. M.


Help Ms. M.,

I am worried. I have this fantasy about my girlfriend that plagues me. I am a thirty-three year old lesbian living with my girlfriend nine years my junior. Like me, she has always been aware of her sexuality. But unlike me she has slept with a man. Actually, he was the last person she slept with before we got together.

They both worked at the same spot bartending and the hours were gruesome. At four in the morning after doing shots and drinking on the job she would usually go sleep at his place because it was two blocks away versus her commute home which was over an hour. They would continue the party at his, and inevitably wound up sleeping together. This went on for nine months. She practically lived with him. It all ended when he confessed he was in love with her. She told him it wouldn’t ever work because she couldn’t love him the same way he loved her.

I knew her and went to the bar where she worked with him for months before she and I got together. We were friends. We always had chemistry. When we finally got together, the sex was explosive. I’ve never experienced anything that comes close. A few months in we bought a strap-on and I began fucking her with it. When I do she cums harder and more intensely than any other way we have sex. It turns me on so much I usually orgasm from watching and feeling her orgasm.

The thing is, now I can’t stop thinking about seeing a man fucking her. I have never in my life been attracted to a man and I don’t have any desire to have sex with one. But I can’t help but fantasize about a man fucking her from behind while she’s going down on me, feeling her face fuck me with each one of his hard thrusts. I wonder what she would taste like with a man’s juices inside and outside of her. I fantasize about eating a man’s cum off of her. I think about walking in on her and catching her fucking a man behind my back. These thoughts make me cum harder and more intensely than anything I’ve ever experienced. They are my go to thoughts when I masturbate and always when we’re fucking. The thing is, I’m not sure if I want to try this in real life. Part of me is scared she might like being with a man so much she will leave me, even though we have a great relationship and we’re madly in love. I’ve only shared this with my best guy friend who laughed and told me I was a cuckold. He said I should tell my girlfriend, but I am afraid she will feel degraded or actually want to try this, and I don’t know if I’m ready or if I could handle that. I definitely don’t want to ruin our relationship. Is there a science behind cuckolding? Do you think I’m a cuckold? Should I tell my girlfriend about my fantasies? Do you think we should try them? Is something wrong with me? I am tormented holding all of this inside.

My Dear,

I am so sorry to hear of your torment. You’ll be relieved to know nothing is wrong with you. You’re absolutely fine! Everyone who has a healthy imagination has fantasies, even the non-sexual kind. So stop beating yourself up and stop being so hard on yourself.

As far as cuckolding, yes there are quite a few theories behind it which extend far beyond cuckolding being just another category of videos on a porn site. The cuckold is so turned on and titillated from seeing his hot wife getting railed by a stud, or super stud (typically with a much bigger cock), that the cuckold’s feelings of jealousy dissolve. Some theories suggest there is a sperm-competition drive: seeing his hot wife being pleasured by the stud with a bigger longer-lasting cock makes the cuckold’s balls more productive thereby granting the cuckold a stronger orgasm. Another theory is that the cuckold has a subconscious desire to submit to a bigger cock, and therefore in his mind, the way to do that is to give his hot wife to the stud with the bigger cock. And then there’s the whole delving into matriarchal societies in relation to cuckolding but I’m not going to go into all of that here.

Because Darling, I actually don’t think you’re a cuckold. I think what’s really happening here, from your email and all the background information you’ve given me, is that you’ve fetishized your girlfriend’s past. You’ve sexually processed what she went through, but you haven’t processed it emotionally. Maybe that’s because it’s difficult for you to fully understand why she would ever sleep with a man if she’s a lesbian. And I bet that scares you a little. And that’s why it also turns you on. In the field of fantasy research, it is commonly known that what scares us a little is often the precipice of what turns us on the most.

I’ll tell you about something I went through when I was much much younger, in my early 20s. I was dating an older guy who was a big shot hedge funder. They’re a dime a dozen in Manhattan, especially when you’re a barely 21 hottie. We had great sex, albeit, it usually involved a lot of alcohol and cocaine. One day he was really high and looking through folders on his computer searching for old pictures to share with me. He mistakenly opened one called TR-Investments, which from the name, I assumed involved his work. WRONG! It was his stash of tranny porn—an entire folder devoted to nothing but movie clips of trannies he had downloaded from the internet. And instantly, I became insecure. I was threatened. I wondered if he was gay. I wondered if he needed something sexually I could never give him.

Add time, more alcohol, and more cocaine, and the next thing I know, I’m watching tranny porn left and right—with him and on my own.

We broke up. I still watched tranny porn. I even had sex with a stunningly gorgeous one I had befriended, who was fully functional and had great tits. (Gay men, I know you’re judging me right now—you always do.) I lived out the fantasy, but it wasn’t as exciting as I had built it up in my mind to be. I too, had sexually processed something I couldn’t understand, which manifested itself into a fantasy. And when I tried that fantasy in real life, it wasn’t all that. I haven’t looked at tranny porn in years. It does nothing for me now.

I happen to think fantasies are much healthier if they go through phases, if you explore them, because when you evolve, so do they. Being stuck on the same fantasy your entire life can’t be healthy … or satisfying.

Should you tell your girlfriend? Absolutely. Keeping your fantasies locked in and all to yourself is not fully sharing who you are with your partner. It’s a recipe for torment, because while you’re having sex, your mind is playing a movie of something else to get you off, and you’re not being fully present in the moment, fully enjoying your lover. That’s not fair to either of you!

How and when you tell her is the important part. For example, I wouldn’t blurt out, “I want to see a big cock pumping you from behind,” during sex. But what you can tell her, perhaps over dinner or whilst snuggling together on the couch, is that feeling her cum when you’re using the strap-on makes you more turned on and excited than anything you’ve ever experienced. And so you wonder if she ever misses being with a man. See where the conversation goes from there. If she says no, I suppose that’s good for you, and if she says yes, I suppose that’s good for your fantasy. Either way, having this conversation is going to be a catalyst for your relationship to grow, whether that growth is sexually, emotionally, or intimately.

The place all couples should strive for is a place where you can openly and honestly share your fantasies, and even talk them out during sex. Does it mean you’ll try it in real life? Not necessarily. And if you do, it might not turn out to be as exciting in real life as you’ve built it up to be in your mind.

Mr. M. and I tell each other everything. We talk out our fantasies during sex. But it takes two truly secure people in a secure relationship to do this. Being open and honest is a constant test of how strong you are together. And you know what? Sometimes I tell him things or show him porn clips he is so not into and he just shakes his head and laughs. And that’s okay. No two people are the same. No two people like all the same food or all the same music, and therefore, no two people are going to be 100% into the same fantasies 100% of the time. It amazes me how many people profess their unconditional love and acceptance of one another, but then their actions don’t align. Use laughter and acceptance as building blocks, not judgement and definitely not mockery.

It’s helpful if you have a close group of friends to tell things to as well. The more fearlessly authentic you can be with others, the more you finely tune yourself, and the more you let go of shame and accept yourself. Fine self-tuning is a constant process. You don’t just tune a guitar once, and expect it to stay that way forever. Working to keep it in tune while you play is key to making beautiful music, and working to keep yourself constantly in tune is the key to making a beautiful satisfying sexual evolution.

So tune away. Practice having more real conversations with your guy best friend—he sounds good for you. Laugh, especially at yourself. And talk to your girlfriend already! Stop holding this stuff inside that’s tormenting you. If you don’t accept your authentic self, who will?

Love Always,

Ms. M.


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Link Roundup: You’re A Slut

Valentine’s Day at the Museum of Sex was a packed house, sexual enhancement vitamins and aphrodisiac cocktails, but the mood in the rest of New York City has been decidedly more dour.

Perhaps the combination of late-stage winter and a depressing holiday in (as they tend to be), New York had this Valentine’s Day message for its single ladies: It’s your fault.

First, The Village Voice lays out a multi-page treatise on “the plight of the single lady,” and TV writer Tracy McMillan takes it home with the only six reasons you  possibly still be single:

  1. You’re a bitch.
  2. You’re shallow.
  3. You’re a slut.
  4. You’re a liar.
  5. You’re selfish.
  6. You’re not good enough.

The New York Times takes a softer approach to #3 in Why Monogamy Matters, citing research that finds “a significant correlation between sexual restraint and emotional well-being, between monogamy and happiness – and between promiscuity and depression.”

Even Senate Majority Leader Harry Read is on the offensive against sluttiness, asserting that prostitution is bad for Nevada’s economy: “Nevada needs to be known as the first place for innovation and investment—not as the last place where prostitution is still legal.”

Doesn’t he mean the first? In fact, Slate argues that illegal prostitution dwarfs what is “really a very small industry” whose scattering of rural brothels employs some 1,000 people and mostly services truckers.

Where have all the prostitutes gone?

Now that Craigslist Adult Services has been shut down, Wired’s timely How tech tools transformed New York’s sex trade gives statistical credence to the obvious: You don’t get to 500 million friends without a few prostitutes.

In fact, researcher Sudhir Venkatesh reckons Facebook is set to overtake the lead in the “online recruitment space.” 83% of the sex workers he surveyed had Facebook profiles. And… 500 million other people.

The NY Daily News found at least one escort with some sense of decorum: “It’s a place for teenagers to socialize… not a place for some dumb ass to find a piece of ass.”


Need A Condom? There’s An App For That!

Now this is cool.

Leave it to New York’s health department to launch a free condom locator app on the eve of Valentine’s Day.

The NYC Condom Finder, as they call it, is “a free smartphone application designed to locate the five nearest New York City venues that distribute free NYC Condoms.”

The iconic NYC condom was also announced on Valentine’s Day, four years ago in 2007.

Which is also Mayor Bloomberg’s birthday. (Coincidence?)

Wonder what would happen if the health department gave their app data to the DataMine? Bet we’d see some more colorful entries in next year’s NYC BigApps competition….

And all in good fun.

Huffington Post writes:

“We want New York City to be the safest city in the world to have sex,” said the city’s Assistant Health Commissioner Dr. Monica Sweeney. “A lot of people come here for that, so we want them to practice safer sex.”

Download it (free of course) in the iTunes or Android store.