The Tomboy, or my relationship bootcamp.

I recently shared a photo essay with you where I featured a series of black&white images of past partners and their lovely bums. For fun, I later added a wee poll to collect your thoughts on which images you liked the most. Most of you responded (with an honourable mention for Shayne and the Grrl) to the Tomboy.

Her name is Reese. A soldier in her mid30s, she was the first playmate to message me through (wait for it...) a dating site. I was still in post-Grrl angst at the time, and apart from a five-star-hotel two-night stand with a computer technician from Vancouver, she was the first woman I had sex with since that breakup. It was therapy.

She was literally hanging in a tree when I picked her up on our first date. Clad in jeans and a diving Tshirt, she made no bones about the fact that she was a casual presence, and if I expected heels and garters, I'd be sorely disappointed. Little did she know that most of my women friends were of the punk, dyke, bohemian variety, so we got along just fine. In fact, we were inseparable for the next four days.

Like the Grrl (and me), the Tomboy was polyamorous. Unlike the Grrl however, she was very physically active in a wide variety of esoteric sports, possessed the energy of a caffeinated dynamo, and had the build befitting her training as an infantrywoman.

Among my favourite memories of her include the time we went to the annual carnival. As we stood before a game of shoot-the-pop-cans-with-the-pellet-gun, Tomboy ignored the sexist tauntings of the hawker. "Give it a try... if you can, little lady." A crack markswoman, Tomboy readjusted the sights on her popgun and downed can after can after can after can to the hawker's silent disappointment. She got the giant green froggie.

I wish I could say that sex with the Tomboy was as great. Sadly, for me, her repetoire was severely limited. While she felt comfortable enough to expand her horizons with me, including her first anal experience (which she was amazed by but never quite got over her anxiety to try again), there was a laundry list of activities she simply had a boundary over. Further, her sexual energy worried me, as sometimes she seemed to behave as though she were used to only being sexual with men who didn't give a crap about her at all.

"Ok, I came, I'm done," she said from under me during one night. I had been fucking her as she lay on her stomach, her legs pressed together so that her cute ass was high and tight against my pelvis. "You can finish now," she added, and turned her head to the side as if to wait for me to do just that.

I was so shocked that I almost got up and left the bed. I did stop, actually, but I didn't leave. It was one of the unsexiest things I had ever heard, and it prompted some deep conversations later. With the Tomboy, her zeal for sex never quite seemed reconciled to her distant, aloof energy during it. In a few months, I grew tired of feeling unfulfilled by my partner. While the Tomboy was gradually making "improvements" (in my view), that didn't stop me from playing the poly card and eventually begin seeing someone else as well.

Stef, about whom I'll write in the future, was sexually the complete opposite to the Tomboy. What frustrated me then was that while the Tomboy seemed to have her life together except for the sexual compatibility, Stef was very sexually compatible but had no life. It was a very annoying dynamic for me at the time.

Eventually, exit Stef. I started to withdraw from Tomboy. Codependence. High maintenance. Distant, fragmented sex. The writing was on the wall. I would soon discover Shayne through the same dating site, and I would learn what loving happiness would feel like again.

But not before one sexual evening with Tomboy that actually does stand out in my memory. A friend, fellow soldier, and fuckbuddy of hers, Ethan, was visiting. Tomboy was torn because Ethan had expressed interest in some play, but it was a night she and I had reserved for ourselves. When I casually suggested that Ethan could "join us if you desired it," the look on Tomboy's face was precious.

It hadn't been since days (and nights) with Diva that I had been in a male-male-female threesome. Gentleman that I am, I yielded a lot to the guest as Ethan and Tomboy coiled on her large bed. A well-built guy with short dark hair, Tomboy was bobbing her head on his long cock (something she learned to enjoy after all while we were together) as I took her from behind. Ethan and I traded places every so often, and she squealed with squeezed-shut eyes as he slid his dick into her. The highlight of that evening for Tomboy was when Ethan revealed his bisexuality to me, and I indulged in a very very rare escapade of sucking cock myself. (Surprise!) Taking his girth in my fist, Tomboy was gasping as she jilled herself, wide-eyed and open-mouthed, her hand a blur between her thighs, as she became totally engrossed in watching me blow him for a while.

(Oh, get over yourselves, guys.)

If dating the Tomboy was a rebound for me, somehow I managed to keep my heart on the steady. The disparity between our emotions become more and more apparent, with me never quite going past the friendship, friend-with-benefits stage, despite dating her for almost a year, and Tomboy secretly hoping for a matrimonial proposal.

The bottom line was that, over time, I saw how there simply was no daily-life compatibility for us. Had the sex been great, had she not possessed certain elements that estranged me, maybe I could have considered things longer. But in the end, I simply had to accept that as far as primary partnership was concerned, there wasn't a future. I learned a lot about what I did, and didn't want, by dating her. That's not entirely a bad thing.

I tried to wean her gently. Soon, the poly card came into play on her end, and she met an unemployed yoga instructor who caught her fancy. Once she started beaming with new-relationship-energy again, I made the break. She didn't take it well. Her LiveJournal became interesting. But time has passed since then, and we remain friends. She's good people; she's just too whacked for me as more than a friend.

The irony in submitting this post about her right now is that not long after I strike the key, I'll be biking down to her regiment's mess hall to have a few beers with her, her still-unemployed yoga instructor, and other buds of ours. I haven't been there in months. It'll amuse me to enjoy my pint in the knowledge that I've shared about her here.

She does have a cute butt though, no?

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