Tuesday, January 08, 2019

Tyler/Valerie: Bad timing

I didn't go out and make plans for New Year's Eve but being that I have found myself in the body of a 25-year-old something was bound to happen. A few days before the 31st Maddie and Charlie persuaded me not to get in the way of holding a party at our loft. Not that I could have stopped them but they wanted my blessing and,if possible my participation (read: cooking, house-mom duty.) I said sure, but I needed help with something.

I needed sex.

Okay maybe it's an exaggeration to say I needed it but it was definitely a strong urge. After my meetup with "Cyn" I counted backwards and realized how long it had been since my ill-conceived tumble with Ryan and decided it was time to get back out there... at least for a night.

I was actually a little confused by my sudden need. I've gone long stretches as a woman without sex before - my whole time as Lauren, months as Judith, nearly my whole first year as Valerie. Maybe my desire to abstractly get laid by a man, without having one in mind, was a sign that I'm truly female, and hetero to boot... or maybe it actually makes me a guy who possesses a vagina and is attracted to men. How should I know.

The pursuit of sex has of course changed since I was fully male. Now all I have to do is stand still and - sorry to sound conceited but it's true - someone will want to sleep with me. The problem is it's easy to turn down these offers because, well, men are men. It's easy to find flaws and assume you'll find a better one eventually. Hence you find yourself six months down the road growing cobwebs between your legs. (Kidding, I dust regularly.) Anyway, to that point, I haven't met a good man in a long time. Technically ever, when you consider Ryan was a cad, Rafe was anti-commitment, and Josh impregnated another woman.

And sure, maybe my standards are high, but I deserve to be wowed. I'm a catch. (I've decided that most men would never admit it, but they'd prefer a woman with a man's brain.)

So I must really have wanted it, to want it in spite of all the potential for disappointment, frustration, and the host of other reasons women can be deterred from casual sex. My sudden needs were really eroding my commitment to my standards. But it was only going to be one night.

My ultimatum to Maddie: find me a guy I might potentially want to sleep with or I'll invite Rafe.

She brought me a guy named Erik, a friend of her boyfriend's. His online presence showed he was a clean cut, harmless type. Didn't exactly light my fire, but no red flags. I agreed to meet him. If he could string a few sentences together he would have a very good night.

The party was... what it was. I looked good. I curled my hair into nice wide ringlets and wore a low-cut clingy dress that shows off my assets but still looks appropriate for a house party,(assisted by an insane date night bra I have never worn before that felt like scaffolding) and tights. I busied myself hostessing since, at my age, getting hammered with twentysomethings is something I have reservations about. I did drink a bit to make sure I had the necessary courage. Erik seemed unaware he was there to be my plaything and kept his distance at first, but there was little else for him to do since Maddie had brought all the same people they usually hang out with, and Charlie had brought all her gay friends, which I think a made a vanilla guy like Erik feel a little out of place.

Eventually, Maddie said to him, why don't you keep Val company in the kitchen? He made some feeble attempts to help with what I was doing but I indicated it wasn't necessary and worked to break the ice. He was a little shy, which was simultaneously cute and irritating. He said he liked to travel, and had been through Europe, which I know is a cliche but at least gave us something to discuss. I had another glass of wine and started closing the physical gap by touching his arm. He responded by going right for the kiss. Points for enthusiasm. I told him he could meet me in my room. It was only 10.

I went to the bathroom. I had started feeling strange an hour or so before but hadn't had a chance to investigate because I was busy and it didn't feel urgent. But once I got in there I pulled down my panties and found, yes, my period had showed up a few days early. That kind of explained the horniness, actually. One of these days I will get truly

I hissed a "Damnit!" and threw my underwear in a nearby hamper. I groaned in frustration. As a man I had had period sex within a committed relationship many times but you can't spring that on a guy you just met. Plus I now felt dreadfully unsexy.

I put in a tampon and went to my room, where he was sitting on my bed, as casually as a guy who thinks he might get laid.

"Hey," I somberly informed him, "So... this is awkward but I just got my period. We can, uh, still do some stuff, and I'll understand if sex is off the table."

He looked at me for a few moments, clearly weighing his options. I seemed to be the only single straight girl at the party, thus his only real opportunity to get laid - which I vividly recall 25-year-old guys being wired to pursue at any cost. Still, you can always count on the male discomfort with menstruation to ruin a party.

He shrugged, "Lets, uh, see where it goes." That was very polite.

We made out for a while. It was fun, but the creeping sense it was not going to culminate in anything spectacular for me kind of flattened the experience. I took my top off and let him plsy with my tits (god, they all love my tits. They can take em!) And presumptuously unzipped his jeans, I guess just to see how I might react.

Oh what the hell. It was almost midnight on New Years. I wrapped my hand around his johnson and began to play gently (what do you know, I know my way around one of those things.) I could hear music in the other room. I decided if he could go the length of a song without ejaculating or doing that awful thing where he pushes my head towards it, I would give him oral.

He made it.

I'd never done it before. On the one hand it seems like something you should keep for someone you really like, but on the other it was like something you can do when sex is off the table and you don't want to ruin the moment. An investment, kind of. At first I felt silly. Like I had lost my last shred of manhood and put myself in a position of pleasuring a guy without getting anything back. As if this was the moment there was truly no going back, like I haven't decided that dozens of times in the past year - I'm a woman, and sometimes women do this. the fact that I didn't hesitate probably shows you where I'm at.

But I had a lot of time to think while I was down there. Was it pleasurable for me at all? Was it anything close to what I'd hoped for? No to both. But undignified? Not that either. There was no shame to what I was doing, because we were both consenting adults and I wanted somebody to have a good time. But even after that, I still really needed sex.

"Hey," I said, "If I get you a condom, would you consider it?"

His grunting stopped and he paused to think. "Can we... do anal?"

"Uh... no." I sighed, and finished him roughly with my hand. Here's a kleenex, see ya. In hindsight - not that I would consider it, but I could have let him down gently.

I rejoined the party and kept my distance. He wasn't so bad, the whole experience just soured my night. Maddie was oblivious, but Charlie was amused. We ended up talking for a few hours as the party wound down.

She laughed when I told her he had balked at the offer of period sex.

"I've never had that problem," she said with a wink.

"Don't rub it in..." oh, poor choice of words. We laughed.

The new year began. The search continues. And my thumb hovers over Rafe's name in my contacts. He's not good for me in the long term, but he knows his way around...

-Valerie/Tyler

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