Back Seat Wonders

Is there a new normal about what is appropriate in the backseat of a car? (By ‘appropriate,’ please consider the loosest form of the adjective.)

I am familiar with some back seat action, which first transpired in my youthful days growing up in suburban Los Angeles, where who and what you drove were everything. However, since turning 29, the backseat of a car has become quite the playground. I didn’t go rogue overnight though. It was a slow evolution:

2001: First kiss in my boyfriend’s car parked in front of Barnes and Nobles in sunny Calabasas, California—so wholesome 

2002: Boyfriend and I engage in heavy petting whilst stationed in front of the local park—keeping it classy

2006-2008: General making out with a couple different guys in a couple different NYC taxis—oh so saucy

2009: Light groping in London minicabs with select British gentlemen—ever so slightly cheeky

2011: The first back-seat-straddle transpires. Out of nowhere, I surprisingly jump on my cab companion and give him a preview of what will soon transpire—risqué minx move (so I thought at the time)

2012: I back-seat-straddle nearly every man with whom I have a romantic rendezvous—bow chica wow wowwww

Then 2013 happened.

The night started out as typically as could be. I met a Princeton alum at an Apollo Circle Metropolitan Museum Soiree; we continued the evening over a dimly lit dinner at Rosemary’s. Soon after dinner, we went to an even darker wine bar tucked away in a West Village corner. Next, we shared a cab and started making out. Yadda, yadda, yadda–so far, so standard.

But then, I pulled back for just a little breather (Upper West Side was quite the trek from West 4th Street), and suddenly without hesitation he picked up my legs, parted them, and went down on my town as we drove uptown.

I pressed one foot against the roof of the car, thinking WHAT WAS HAPPENING?? Is the cab driver watching us?  Am I wearing my go-to flesh-toned spanx?? Can people see us from outside? Why is this so natural to him—has he done this before? Does everyone do this?? Is my leg blocking the cabbie’s view from the rear view mirror? I am definitely not wearing a seatbelt—what if we get pulled over? Am I going to get a ticket?!

nyctaxiI thought my experience was clearly an anomaly – I mean cab hanky-panky wasn’t even featured on HBO’s Girls, my current sexual barometer for what the cool kids are doing these days, so evidently this was special stuff. Then just a few months later, in a different car with a different man, I found we were somewhat rounding third base, within literally just moments of getting in the taxi. Again—WHAT WAS HAPPENING??

All these years, had I just been missing out on these racy rides, or was this a new move men have begun to exhibit? Plus, others must routinely go all the way in the back of these shared vehicles, meaning I might consider dousing the back seat with hand sanitizer before next sitting down. Regardless of what is customary, the next time I enter into a taxicab with the man of the hour, I know to sit back, enjoy the ride, and most importantly– tip well!

Choke me maybe

I have heard a thing or two about men and women who enjoy a good sex choke. But I always thought chokers and chokees were sexual deviants, the types who frequent the underground clubs teeming with leather whips and ball gags you always see as crime scenes in Law and Order: SVU.

But I learned this week, far from any sex club or asphyxia-nados, that was not the case.

C (C for Choker) and I first met when we were both in grad school at Harvard and have been friends for a few years now. We had a budding rapport, but he had a girlfriend so nothing ever ensued. Although one summer’s eve, we shared this magical moment where after hours, we somehow discovered a hidden elevator in Grand Central Terminal that led us to an amazing private view of the mural of stars, where we talked until sunrise, when the next morning’s construction crew kicked us out. We lost touch over the last year. Suddenly, last week, two days before he was set to move to Chicago, C texted.

We started the unassuming Wednesday night at a Stanford (his alma mater) open bar in the East Village, and after more vino on my Tribeca rooftop on the perfect August evening, C finally made his move. As he first kissed me, he softly whispered that he had wanted to do this since our time at Grand Central. Our connection started off so romantic and tender—as though this was a night two years in the making.

Fast forward 40 minutes (I think? I lost track of time…), and somehow he is grabbing me by my hair and choking me.

I have had my hair pulled before, but his roughhousing was certainly level 2—and I liked it. The choking was more of an introductory move, as I could see he was tepid and wanted to gauge my reaction. I didn’t even realize it was happening at first. I thought, does he realize that’s my throat, and I use it for breathing?? Quickly, I understood his maneuver was no accident.

CH2I always thought that anything out of the sexual ‘norm’ a la choking was only de rigeur for freaks. Or at least for two strangers passing in the night—no feelings required. But at that moment, it was part of the racy repertoire between C and me, who have had somewhat of a history. I also thought it was surprising that C employed this tactic on me—was I somehow subconsciously emitting that I hate oxygen?! I’m pretty sure it was clear that I did not think air was overrated.

In the end, we had pleasant time, he moved to Chicago, and we set a date for a fall rendezvous. Who knows how part deux will transpire. I realized, I never know what anyone has up their sleeves, and it’s not necessarily just about me or what I project. But I know not to over analyze—just breathe in (or gasp?) and enjoy!

Look into my eyes

In the past when I hooked up with someone I loved (or liked-plus), sometimes it was tender and romantic, teeming with whispers of sweet nothings, and almost always replete with eye contact, where we gazed into each other’s souls.

Well, with a rando I have found it’s more of a get it in, get it done, slap an ass-cheek and call it a night.


When presenting at a work meeting or just ordering the two-cheeseburger meal from McDonalds (this happened last night– don’t judge me), I found that making eye contact is irrefutably one of the best ways to connect with others. So naturally, I tried to apply the same theory to the boudoir to build a rapport with my audience of one. Granted our between the sheets bond will last anywhere from three to seventeen minutes, but still, a connection is a connection. So I was slightly surprised the first time I hooked up with someone and we didn’t lock eyes for the entirety of the deed. (Also, I obviously am only discussing the bedroom moments where eye contact is actually feasible. If at some point, he isn’t staring at the back of my head or some other non-face body part, we probably just aren’t doing it right.)

Now clearly, even I am not naive enough to think that ‘like-plus’ sex would be similar to that with someone I have known for two hours or two weeks. When I first boned with minimal eye contact, I wasn’t hurt, just slightly taken aback. Listen, I don’t need my soul peered into during every romp but I assumed a little looky-loo was common courtesy. I make eye-contact with the stranger I’m sharing the 6 train with, so if it’s you I’m sharing a bed with, I expect the same. But what do I know—clearly I am a novice in this casual sex game, so I can take a hint. The next time, I will be ready.

Fast forward a few weeks (Okay, maybe a little longer. Being slutty takes time!). I’m ready to get down with a different dude. Now, I know the drill. I’m ready for a gaze and close: look at each other for a few minutes so as not to seem disrespectful, then avert my eyes and let it be. So that’s precisely what I did. But as I broke eye contact, I saw him still looking at me—really looking at me. What’s this now?? This chap wants to stare at my face the entire time! Just when I thought I had learned some sex etiquette, I realized– I knew nothing.

I’m not a (total) bozo; I get that not all eye contact equates to deep, meaningful sex. Some men just like to stare. Perhaps those particular menfolk are more eager to please so watch for cues for direction, or they are happy making me happy and watch for hints of success so they can pat themselves on the back– look ma, no hands! Then there are those boys who don’t like to look for whatever reasons. Either way—I discovered that, even though it’s the same act over and over, there are no protocols in sex. Anything that seems standard, is not. So play by ear, and look on! (or don’t!)

Am I Secret-ing Sex?

Today, it went down. I thought it was just a myth– an urban legend stemming from Sex and the City. Or at least something that materializes for an elite few. But, no. On this unassuming Sunday morning, it became true:

I was asked out at the gym.

It was an especially rare day, as I was bereft of all Lululemon and makeup. (I wear foundation to pick up packages from my doorman—sad truth). I left the encounter feeling dazed and confused – how was this happening!?  I remember wishing that my Tom Ford oversized sunnies were even more gargantuan so as to mask the beads of sweat pouring from what seemed like every pore on my face. Does this man only possess three of five senses? Clearly, if he could see or smell me, he would have assuredly run the other way.

Once upon a time, when I first signed up for Equinox, this man was assigned to me as my trainer (think abs of steel). It was only a few months ago when he was grabbing my belly fat to calculate my body mass index. In what world could that have been foreplay?? I have always been baffled by how a man who exercises such discipline could find an indulgent mac-and-cheese loving woman attractive. The fact that I tend to ponder such enigmas over cupcakes probably does not help my search for the truth…


As I bite into said red-velvet delicacy, I wonder: Why have I recently been asked out with such a higher frequency than is standard for me? (One caveat: My normal is essentially zero, so there is only upside). We have all heard the countless clichés about the power of positive thinking. Once, while lamenting over the dearth of decent graduate school boys at Harvard, my classmate mentioned the cult classic, The Secret, which posits that the law of attraction determines our personal lives through the process of “like attracts like.” Her friend Secret-ed that a boy would ask her out, and literally within the week he brought her flowers! (Anyone who has gone to graduate school can understand exactly what a rarity that is.)

Is the Secret legit? I don’t know. However, I do know these days– I like sex, and sex seems to like me.

I have always loved boys, yet that alone clearly has not been sufficient enough to attract a lasting mate. (See blog title). But lately, something has been different. Yes, the ostensible change is that I have set my inner whore free. Does that solely warrant why my adventures have been kicked up a notch?

Perhaps my recent love of sex willed the universe to make Trainer strike up a longer conversation with me and eventually ask me on a date. Or, possibly I am just happier in general from all my past romps and the positive repercussions, i.e. not having a stick up my ass constantly, and thus I was more willing to partake in the aforementioned banter. Or, maybe all sluts experience a comparable hot-streak and to me it’s just a novelty.

Despite his rock hard body, I politely declined the date with Trainer. I was not interested and I didn’t want to have to avoid the gym for any other reason aside from my pure laziness. At the end of the day, it doesn’t matter if like attracts like or if ho-ing it up gets the job done—sexcapades will come!

Pretty please, with a cherry on top?

All you have to do is ask.

I essentially paid $200k for a Wharton education to learn the pivotal business negotiation tactic above. But I have recently found that the tenet holds true for sex as well. Until recently, I thought the hard to get card was the best one to play (at least whilst sober), and I still accept that it is human nature to want what you cannot have. However, I have also witnessed that people want what is simple, and right in front of them. To get it, you simply have to ask nicely.

I try to be easy breezy, but I end up mostly feigning it. Add just plain easy to that outlook, and you most certainly end the night with a romp. Case in point: this past week I reconnected with an old high school friend. He has reached out to me over the last 10+ years (clue 1 he wants to bone) although we have probably only seen each other twice since graduation. We met for drinks in a dark West Village wine bistro (clue 2: a dimly lit bar = ideal pre-bone setting) on a Thursday evening (clue 3: no one really bones for the first time during the first half of the week). Based on my Nancy Drew-like sleuthing skills, I naturally assumed that based on his behavior pattern and the fact that he possesses a penis, he clearly wants to get it in.

So, I askcheese-charcuterie-boarded him, in between bites of charcuterie, and in the easiest of breeziest ways, “Do you want to have sex with me?”

There was a look of shock cum excitement cum shock again before he answered. He rambled on about how he just wanted to catch up and how he even mentally told himself not to hit on me tonight. Ultimately, I have never seen a man pay the check so quickly.

Would I ever have been that direct pre-age 29? Absolutely not. All I sought from my old pal in that moment was a little action between the sheets. There were no games, no dalliances, and no mysteries– he knew exactly what I wanted. I got exactly what I asked for, and eleven years later– so did he. It was honest, mature, and very, very fun. (PS- he is ALSO a lawyer—that’s four in a row now! Separate blog post idea: On Boning Barristers?)

It has been written that nice girls don’t ask, but smart women do. Although that advice was given to those who desire to climb the corporate ladder, I have discovered that the same applies if you just want to climb up on a man. Yes, this behavior will probably not lead towards a long-lasting and loving relationship (can someone say snoozefest??). But at 29—I get it. I’m in this for the same reason this bozo on top of me is. And I am going to enjoy it for what it is. So I have learned—ask and I shall receive!

Ménage à Trois

I knew I officially graduated from Sex 1.0, when I was invited into a threesome. To someone whose sexual proficiency is still under construction, it’s quite high praise. Why, thank you kind sir, for believing I posses the adroitness to execute on such an advanced encounter!

Spoiler Alert: This story does NOT end with my participating in a threesome. I am not interested. I think women are beautiful, and their bodies are seductive, but the thought of doing ANYTHING with lady parts—no thank you. And, no way could I be with two men. I am still discovering what to do with just one dude in my bed—two requires a dexterity I have yet to acquire.

I was first asked to participate in a three way in 2011 at Beach Week in Miami in business school. Wharton’s Beach Week is a slutfest in absolute form and I’m thankful that my burgeoning sexuality was still under wraps then, as I would have surely not survived the week (or grad school) without at least one STD or pregnancy scare. Anyway, a classmate asked my hottie BFF and I to head back to his room at the W to get down and dirty. I’m pretty sure that in my near blackout phase, I accepted his advances. But my wise friend knew that’s not how I roll, so the situation quickly dissipated.

More recently, after closing down the open bar at an evening in the garden at Central Park’s Conservancy, a super-cute NYC bestie and I headed for dinner at Del Monico’s in Midtown. We ate at the bar, and a dapper gentleman sat next to me. I flashed him my freshly Crest-whitestripped smile and learned he was an investment banker from San Francisco here on business. A very handsome investment banker, at that. Somehow over a couple glasses of sauvignon blanc, both Bestie and I showed the Banker some lust worthy lingerie pictures of us on our iPhones (I just happened to take them earlier that week as I was waiting for the cable guy—thanks Time Warner for showing up late). After that, I can’t really fault the Banker for thinking he may actually have a chance to fulfill his girl-on-girl-on-him fantasy. He gave it a good effort, but after all that flirtation, the three of us went home alone. (life is hard).


After both of these indecent proposals, I felt a sense of pride. Especially after the request from a stranger; clearly my first impression was provocative enough to elicit such an illicit pitch. Look at me world—I’m so fun! And I have come a long way. But then I realized, I really was just riding on the sexy coattails of my pretty pals. And you know what, there is no shame in that! Just the requests alone built my sexual self-esteem: these men didn’t think I was boring in bed. I’m still working my way up the boning learning curve—but I’ve made good progress!

Am I good in bed?

Malcom Gladwell of Tipping Point and Outliers fame, asserts that to attain expertise in any area, one needs 10,000 hours of practice. Well, by that measurement, I should be the worst lay in Manhattan. Yet, I have been told, more than once, that I can throw it down (I was shocked too!).

Given my obvious lack of practice, I used to feel incredibly insecure about my sexual prowess. I’d usually allay any trepidation by downing extra dirty Grey Goose martinis pre-act. But let’s be real—blackout sex is bad sex. In fact, one winter night after four said martinis at Hakassan, I tried to be bold and really sass it up whilst on top. The only thing that got banged that evening was my head against the bedroom wall, mid thrust. Note to self: concussed sex is also bad sex.

Initially, I thought that the men who complimented my boudoir abilities, were just sweet talkers. But upon closer examination, maybe, just maybe, they were on to something. So what helped my bedroom transformation? First, I love what I do (the who I do seems to be less important). Just like a fat kid loves cake, I LOVE boys. I always want to get down. Now, I give into those desires with more frequency. Clearly not every time is a home run, but I adore it nonetheless! Plus, I believe in positive reinforcement. I will tell the lucky lad I am with, exactly what I enjoy about his penis. I never lie (though sometimes I embellish via moan-volume), but he will know if he is succeeding in the sack. And he will be rewarded. Besides, what fellow doesn’t take pleasure in a compliment to his manhood?!

Second, I’m confident. And I faked it until I made it. I’m no Melissa McCarthy, but I consume cheeseburgers and fries on the regs. (I’m not going to lie, I had Haagen-Dazs for breakfast.) We all have body issues, but boys aren’t thinking about my cellulite when inside me. So why should I? Go ahead– keep the lights on. And after, pass the pizza!

Third, I’m open-minded. This took work, but I’m a quick study (thanks MIT).  Simple acts used to repulse me, and I have literally smacked away body parts if they approached the no-fly zone circa two inches from my mouth. But I have since learned to lower my gag reflex, and more generally my inhibitions.


Lastly, it doesn’t hurt that I have a deep-seated desire to please men (thanks, daddy issues) and that I’m quite bendy (thanks, yoga). Of course, not everyone will find my techniques tantalizing, but that’s perfectly acceptable. I still face hookup-anxiety today, but I believe in my own craft now. And that will make for better sex for both my partner du jour and for me!

It’s okay to like it rough

I love rough sex—and that is perfectly acceptable.

I always thought it was imperative to be hard to get, classy, and sweet. I used to adhere to those mantras (well, not when I was bumping and grinding at Marquee in 2006.  And 2007. OK, and 2008). But then I realized a truth:  life is short—bone. And bone how you want to!

Now, let’s call a spade a spade– I am in no way kinky or experienced enough, really more of the latter, to like it truly rough a la whips and chains (I might be amenable to a light slap across the face, however). I’m talking about enjoying diet rough sex: a little hair-pulling, booty-smacking, sex-bruising, and the like.

I LOVE a good sex bruise. I got my first contusion of the sort in San Francisco, earlier this year. Unless you cbruiseount a hickey I got circa 2001 from my high school boyfriend. My poor Indian mother thought I was getting in fights at school. Sorry Mommy, I’m not a bully, just a ho.

We will call him the Doctor. (He’s currently doing his MD/MBA at Stanford—undoubtedly one of the smartest smartypants I know.) We dated briefly in college and have kept in touch over the last ten or so years. By kept in touch, I mean hooked up. I was staying at the Ritz Carlton for work; perhaps it was the fact that we were in a luxe hotel overlooking the stunning SF skyline that made the Doctor act on his naughty impulses. If not the view of the city, perhaps it was the view of my ass as I greeted him dressed solely in my garter (have I mentioned I LOVE dressing up??). The hookup was a delight—tender, rough, and fun, all rolled up into one act. The cherry on top of this sultry sundae? I had a souvenir from our dirty deed! Every time I looked down (at my arm, neck, inner thigh…) I was greeted with a pleasant reminder of what once transpired.

I recently came back from a trip to see a separate boy in London (I’m so busy), and my only keepsake from the weekend romp was a giant sex shiner on my left arm. You would think I would be embarrassed of looking reminiscent of an abuse victim (a video chat with Mom led her to invoke God for help if I was secretly getting battered). But no—I freaking LOVE the bruise. It is perfect for show and tell. How was my trip, you ask? Well take a look at this baby!

I was taught to be virtuous and pure, and my (crazy) parents essentially ingrained in my head that sex is for sluts and I should do math instead of boys. But you know what—be authentic! Love sex! Love it rough! Or don’t! Just be me. I can still be classy and sophisticated (after all, I wear pearls) and like to get down and dirty. Ludacris said it best: be a “Lady in the streets, freak in the sheets.” Luda—you get me. So at the end of the day, I know what I have to do—keep it real!

Snoozefest sex

Silent sex is boring sex.

Let’s be real– I am a girl and I LOVE talking. When I am with a man, all I want him to do is verbalize what he feels, what he believes, what he ate for dinner, what he thinks of my shoes, what he worries about at work, what kind of laundry detergent he uses. EVERYTHING. (I get it, I’m a crazy girl.) And for me, communication is just as important in the sack.

Until recently, I had never hooked up without a little chit-chat. Now, I probably indulge in a little more dirty talk than is commonplace amongst my over-educated and under-sexed peer group, but I don’t always require raunchy communiqué during the act (but I do love it!). But, I need SOMETHING to work with. A simple “give it to me baby” or even “do you like it like that” would suffice.

The other night, I thought there might have been a silent film playing during sex—because I could hear it.

We will call him Pepe. Pepe and I have known each other for about eight years.  We had been hooking up for about that time, on and off, vast majority off. Yet, we never sealed the deal. In the years past, no number of dinners at fancy restaurants, drinks at trendy bars, or even a brief Italian and Swiss holiday, could get me to take off the chastity belt. Suddenly, this year, Pepe casually mentioned I looked pretty at a recent Garden Party, and I basically threw my panties in his face.

The sex was fine. But it was QUIET. One of my favorite things about sex (besides that I am having sex!) is that it keeps me present. That’s probably why I love communicating with men—I am so genuinely interested in what comes out of their (bozo) mouths that I don’t think about anything else in that moment. Throughout my daily routine, I am incessantly ruminating—either about my career, my family, or the latest drama on Real Housewives (Did Vicki really have a threesome??). But during sex, all I can think about is how much I love this penis inside me (or my mouth) right now.

quiet zone

However with Pepe, the silence was almost deafening. I remember thinking hmm, maybe I should breathe heavier?? Or let out a slight moan? Would that make it better?He’s giving it a good effort, I don’t want to make him feel bad. And I think I am liking it? What color should I get for my next manicure? Oh wait, let me arch my back– that might help.

We only did it that one time, but Pepe and I are still friendly. We even carpooled to the Hamptons a few days later. But the experience made me realize how much I love a good tête-à-tête. Maybe because Pepe and I never had that much to say to each other outside the boudoir, we had the same issue when finally inside it. So note to self—gab on!

My first one night stand

I always thought you need to really feel connected to someone to truly enjoy sex. I presumed chemistry was a rarity in this world, shared only with a select few.

Then I boned a rando, and I freaking loved it.

Going from only sleeping with (two) boyfriends, to a one night stand was quite the leap for me. In my rager-filled youth, I rarely had the urge to do anything more than make out with a stranger. A little spit-swapping and feeling up on the dance floor used to hit the spot and then I’d usually just peace out and spend the night with my true love–pizza. But suddenly, a new curiosity emerged: what would sex with a stranger be like?


I assumed it would be awkward, gross, painful, brief– standard fare. No, thank you. I don’t know if I hit the one night stand jackpot but my experience was nothing like that.

Let’s call him The Greek. He was a handsome lawyer with luscious locks and Clark Kent eyeglasses, who I met at a cocktail party for the Apollo Circle at the Met (the only way I was convinced to become a pricey patron of the arts, was the guarantee of countless open bars). Over cocktails, we chatted about the Punk to Couture exhibit and eventually migrated to the Four Seasons with a group of our friends to keep it classy. I don’t know when I decided that he was the Chosen One, but I could feel myself not being able to resist the temptation to finally discover what this whole hit it and quit it behavior was all about.

I suggested we leave our nice friends and head to our respective homes. “We can share a cab and make out a little if you want,” I nonchalantly suggested as if carpooling and french kissing were natural partners. The Greek was amenable.

We hopped in the (not long enough) ride from midtown to SoHo, and I straddled him. Oh yes, I love a good makeout slash straddle session in a taxi. It’s surprising, sexy, and pressing my butt against the backseat TV is better than watching it. When we first got in the cab, I told the driver we were making two stops, going to my Tribeca apartment second. (I’m SO hard to get). But as I ran my hands through that beautiful head of hair, it was at that moment I decided– this is it, we are going all the way.

All of a sudden, I had a thought– is this safe?? Wholly unfamiliar with all one-night-stand protocol, I pulled back from our liplock and asked The Greek two pivotal questions:

1. Are you going to serial kill me?

2. Do you have STDs?

After I felt comfortable I was going to emerge from this undertaking alive and disease free, I was ready to get down to business. And down to business we got. The night was just SO FUN. I remember falling asleep that night and thinking OH MY GOD- WHY HAVEN’T I BEEN BONING RANDOS ALL MY LIFE??? I suddenly understood why everyone was so slutty.

Then the morning came. We parted ways, and like the little bozo I am, I thought this clearly wasn’t a one night stand. I mean who wouldn’t want to have sex like that OVER and OVER again?? I patiently waited for him to text or call me. (And, maybe we will fall in love??) All day at work, I was beaming with the joy of just indulging in the most ravishing and unexpected night I had encountered in a long time.

Well, he never called. But the best part of having a one night stand for the first time at age 29, is that it is OKAY. I wasn’t devastated, I wasn’t appalled. I was zen. I still loved the sex we had. I would have happily re-boned, but alas, this was a lesson. Good sex is out there, not just with people I love. What a twist!!