Me: Are you still with your girlfriend by the way?
Kyle: Kind of. She moved. Things are holding on by a thread that’s about as thin as my one remaining moral fiber.
Me: Wow. That’s one fucking thin thread.
Kyle: Thanks.

I’ve been in those shoes before and I can’t empathize enough. I told him that the situation reminded me of my favorite song off John Mayer’s third album “Continuum” (which, on the whole, is amazing):

It’s not a silly little moment
It’s not the storm before the calm
This is the deep and dyin breath of
this love we’ve been workin on
Can’t seem to hold you like I want to
so I can feel you in my arms
Nobody’s gonna come and save you
we pulled too many false alarms

We’re goin down and you can see it too
We’re goin down and you know that we’re doomed
my dear, we’re slow dancing in a burnin room

I was the one you always dreamed of
you were the one i tried to draw
how dare you say it’s nothin to me
baby, you’re the only light I ever saw

I make the most of all the sadness
you’ll be a bitch because you can
you try to hit me just to hurt me
so you leave me feelin dirty cuz you can’t understand

We’re goin down and you can see it too
We’re goin down and you know that we’re doomed
my dear, we’re slow dancing in a burnin room

My roommates told me the entire time that they couldn’t believe how irresponsible I was.

“It’s just wrong,” one of them said. But it was hard to fully believe them because they disapprove of so many things in my life that reproach is more obligation on their part than actual expectation for me to change. Half the time, I operate thinking that my friends are secretly intrigued by my willingness to do what others wouldn’t dare. This case was no different. Taking risks and acting irrationally was as exciting for me as it was for the onlookers. At the very least, they had something to get indignant about. But this time, I wasn’t the only one affected by my rash decisions.

“Are you in love?”
“I don’t know. Maybe that means no.”
“Do you say it to her?”
“Do I say it? Yes I do … but I know that most of the time I feel emotionally blank.”

At least he didn’t love her, I rationalized. Which, in the end, was just a rationalization, because even if he couldn’t bring himself to call it love, he certainly cared. Yet we still slept together.

Maybe I wasn’t so bothered by my actions because I strongly believe that life is karmic. Payback’s a bitch and sooner or later, I was going to get mine. Just not in the immediate future. And hey, that was fine by me.

Then two months later, in a hotel room in the middle of Manhattan, karma paid me a visit in the most unexpected manner. My friend’s boyfriend propositioned me. Suddenly, the concept of being the other woman fully hit me.

The last time Kyle suggested that we get together, I told him I had a boyfriend, which was not exactly the truth but was the easiest explanation I could muster up at the time. I didn’t want him to feel rejected, because I wasn’t rejecting him so much as I was rejecting the circumstances. The funny thing is that I genuinely enjoyed his company, his not-so-moral viewpoint on life, his atypical approach to romance, and yes, even the way he talked about his girlfriend. Save for the sex, he was I’d look for in a male friend, and whether hooking up was part of the equation or not, I wanted him to be in my life.

My vow to discontinue the sexual nature of our relationship was spurred by the events in New York that weekend when I realized that I didn’t know how to break the news of her boyfriend to my friend, that it was a heartbreaking and difficult situation with no easy resolution, that I would be culpable were Kyle’s girlfriend ever to be placed in her position. And at the time, I thought that was the extent of my punishment for my moral infraction: seeing the look on my friend’s face when she realized what her boyfriend had done.

Today, I realized that New York was just the precursor, a set-up in so many ways that it is incredible to examine that weekend in retrospect. I guess cosmic forces are not so kind and karma not so forgiving after all. I have classically catastrophic relationships, but being told that I am the accidental “other woman” today really takes the cake.

And yet, I think I’m getting off pretty easy for messing around with someone else’s guy. I think we’re both getting off pretty easy because he’s still got the girl and I’ve got … well, the dignity of not being called out for what I am. Still, I refuse to regret anything I do in life, and no matter what any of my friends or roommates say, I would not never take back the decisions I made regarding Kyle. There are a lot of reasons for that, not least of which my sanity which he played a role in preserving. At the time we intially met, he served a really important purpose, a purpose that my friends don’t quite understand, a purpose I don’t even think he’s aware of.

I started writing an essay about Kyle in January, left it unfinished in February, and I am only now revisiting it. It is in revising the sentences of my old prose that I have begun to distinguish him from the guy that came before and after him. I have always managed to fall for fuck buddies and I consider it no small miracle that I never fell for Kyle. I think I know why: I idolize boyfriends, but Kyle was never the ideal man and I knew that better than anyone else. The sex was controversial yet never too memorable. It was our conversations I recall most vividly, because he was the only person in my life at the time who understood what it meant to not be perfect and understood that imperfection didn’t mean being a bad person. Flawed as he was, he was inherently good.

Since he cheated on his girlfriend, all my friends naturally said he’s an asshole, but I heard the way he talked about her and his family and his goals and his life. He’s not perfect but he’s not a bad person and he wasn’t looking to hurt anyone any more than I was. I never wanted him for myself and sex barely had anything to do with why we dragged on as long as we did. Now that karma’s already come around twice, I truly hope third time’s not the charm because I don’t think I could forgive myself if I broke them up, if I ever had to explain to her what happened the way I had to explain myself earlier this morning to someone who didn’t have a clue. I don’t regret anything with Kyle but personal responsibility is a difficult burden. What I wish I had known from the very beginning was that karma could only be so retributive, that conscience was what would really continue to haunt me.

Me: “You are the most likable asshole ever.”
Kyle: “Thanks. But to be honest, most people think I’m a sweetheart.”
Me: “Well, you may lack a moral compass, but you also have a charm about you that’s your saving grace. You just happen to be a lucky guy who rarely gets called out.”
Kyle: “Well, I appreciate it. Thank you.”
Me: “Honey, that was no compliment.”
Kyle: “Yes, it was.”
Me: “Maybe for someone with low standards for themselves.”
Kyle: “Nice to meet you.”

Single ain’t so bad on Valentine’s. In the past 24 hours, I’ve traded “I love you’s” with Summer Guy, walked out of a lecture to talk to Sam, and exchanged greetings with a New Yorker I plan on seeing this weekend. I met two boys for the first time (separately, both for coffee), received messages from readers (thanks!), and also managed to piss off Peter via text message. No small feat considering the wonderful timing.

I think it’s fantastic that every guy who remotely gives a shit about me is currently at least 200 miles from Boston.

It’s been a quiet day. Save for my meeting at the Agassiz (I’m producing a show there, can you believe it?) I didn’t do anything terribly productive. I’m sure the weather’s to blame. For dinner, Nate (see left, in better weather) and I went to Tanjore where I ordered Aloo Mutter and lamented my lack of flowers. But what’s really sad is my lack of sex.

I haven’t had sex in a week and a half. I expect to break out into a rash at any second. I suppose I could make a phone call to a local hookup if I really wanted to (and trust me, Valentine’s is the day to do it) but I’m utterly disappointed with the hos in this area code. Then again, pretty much every guy on my current roster — Bostonian or not — has some major failing (be it commitmentphobia or Republicanism).

Just about the only person who doesn’t continually frustrate me is Kyle and that’s probably because my expectations for him are exceedingly low. I was telling my roommates last night that Kyle’s unabashed sleaziness is infinitely better than the shit I encounter from guys like Mark who disappear and reappear at whim or guys like Summer Guy who admit they love me in the same breath they deny our romantic possibility. Kyle may be no saint but at least I know exactly what to expect — nothing.

I think the real cause of my frustrations is the fact that I’ve been playing around with the same five guys since mid November/early December. Like my black leather boots, they’re a season old. But unlike my boots, they don’t complement me better as the winter goes on. If anything, things have stagnated. And by “things,” I mean everything — sex, relationships, conversations, etc. It is February 15 and it might as well be 2006 again. I’m just bored and not even in a self-indulgent, “I have a short attention span, so interest me” kind of way. I’m bored from desperately wanting passion and ending up with excuses about distance and lack of time and youth and bullshit.

I’m tired of bullshit.

Maggie, JB, and I discussed the boundaries of monogamy last night. Both vehemently disagreed that a sexually open relationship could work. But honestly, I see such a clear separation between my physical and emotional needs. The latter can easily be fulfilled at long-distance. The former — though something I’m certainly willing to compromise — obviously necessitates regular interaction. Though I’m quite fond of Summer Guy, I don’t particularly care if he dates or sleeps with other women. It doesn’t make me love him less. The one thing we’re missing is a relationship label, and even then, I can’t tell you if that would dramatically alter the way we relate to one another or my feelings toward physical intimacy with other people. Sex doesn’t mean a damn thing.

I am almost convinced that Sam is this happy medium between all the madness. He’s not in Boston, but close enough for visits. The distance makes him attentive in a conveniently non-intrusive way. He’s older (which I prefer) but a student (which is easy to relate to). Sex is great, even orgasmic. And the big one: he’s emotionally available — almost unbelievably so. Just about his only flaw is his fiscal conservatism, and I’m sure I can fix that with time.

So why am I second-guessing his motives all the time? Probably because I’m more used to 20-something boys than I am 20-something men.

We’ll see what the four-day trip away brings. New York tomorrow night. Philly this weekend if I’m feeling spontaneous. See you Monday, Harvard.

I answered the door in a t-shirt and boyshorts. “Hey,” I said to my curly-haired visitor.

He glanced up and shook his head at my (lack of) attire before managing a “hi” with a smirk. It was 3 a.m. and there were no pretensions about why he was here.

Shortly after I ensured that he came with an alibi and condoms, we were wrangling each other’s shirts off, eager to finish the long cocktease I started the last time he landed late in my lap.

And then his phone rang. With mouth pressed against the back of his neck, I whispered, “Answer it.”

He glanced at the name and tossed the phone to the side, atop the small pile of clothing we had made. “Sorry,” he muttered. Within seconds, we were back at it. Grabbing, squeezing, breathing hard against each other.

I got on top and straddled him, half-playfully, half-aggressively. As I ran my fingers over his upper body, his torso twisted to follow the touch of my hand. Each graze of my mouth against his lower stomach elicited a gasp. I dipped my head and pulled down his jeans. He was wearing black boxer briefs, his erection perfectly outlined against the fabric. I turned my head to wrap my lips around his girth, the cotton acting as the only barrier between him and my mouth.

“Oh god,” he whispered as I followed the length of his cock with my lips.. He was running his hands through my hair now, guiding me down. But I resisted the more he pushed. This is fun, I decided as I thumbed the tip of his erection. I was ready to finally deliver on my tease when his phone went off for the second time, emitting a low buzz as it vibrated over my carpet.

“Well?” I asked expectantly.

“I’m so sorry,” he said, before reaching over to flip it open and answer.

It was his friend (the one he ditched to rendezvous with me) inquiring about his whereabouts at a most inopportune time. He responded tersely and vaguely, as I stayed quiet and impatiently rubbed his shoulders.

“I’m sorry,” he said again when he hung up. I responded by tugging at his boxer briefs and revealing his cock inch by beautiful inch. I didn’t know where to start so I decided to aim low and work my way up. I flicked my tongue against the soft flesh at the base and moved my mouth up his shaft, leaving a trail of wetness behind. He was breathing hard now, grunting softly until I finally closed my lips over the head of his cock, inciting a low and hard groan.

He let out another one — more annoyed than turned on — when his phone rang again for the third unwelcome time. The caller was persistent. “What the fuck?” he answered after letting it ring a few more times.

While he talked to his pal, I had no intention of stopping the action on our end. I lowered my mouth over his cock and slid my lips over his shaft easily.

“Oh my god …” he groaned into the receiver. I was bobbing my head up and down while stroking his base with one hand. He lowered his eyes to look at me. “Fuck …” he said, still speaking into the phone. As I sped up my rhythm, he flipped the device shut — his friend still on the line — and watched me working his cock with my mouth. “Oh yeah, just like that,” he whispered. I sucked him off for a few more minutes before pushing him back on my bed and handing him a condom. I wanted to get fucked doggy style. In minutes, he had me on my knees.

- - -

As I straddled him in the afterglow of our encounter, I asked him what he wanted to be called on my blog if he ever warranted a mention. This was the first time I offered such a courtesy to anyone — close friends included, much less casual hookups. My hands tapping on his chest playfully, I waited expectantly for an answer. I already had a name in mind regardless but I was curious to hear what he’d say.

“Kyle,” he finally said after a few seconds of thought.

“What?” I almost fell off my bed from shock. “That’s exactly what I was thinking … did I already tell you?”

“No,” he replied casually. “I just thought it was a good, simple name.”

“That is so weird,” I said.

I shook my head. I could hardly believe it. But then again, Kyle left me bewildered with just about everything.

[For the rest of the Kyle series: Part I, Part II, Part III, and Part IV]