Ainsley: Out Of Bounds

Nobody told me going on my first first date in three years would be this nerve-wracking!

OK that's a lie, everybody told me that. My friends, kind of my roommate, musicians, those reality TV ladies who've had enough of their exes' bullcrap but also haven't had enough of Netflix's bullcrap. And even kind of me, but the last time I'd just gotten over a breakup was... I don't even wanna think about it! So, it turns out it's just another one of those things you have to learn firsthand no matter how many times people try to warn you.

Tinder hasn't gotten any better since I was fresh out of college, that's for sure. But it's not like I had high expectations in the first place? I'd just like to know at what age I'll see fewer pics of guys holding up a fish than of them. I don't know. Golfing? From what I hear at work there's a point when a set of golf clubs magically zaps into a man's bedroom and he starts having opinions about who's going to win The Masters.

You know it had to be a dog pic that got me. Yeah yeah, I'm so predictable, I get it!!! But what am I supposed to do, just turn down the chance to meet an adorable Dachshund? Hey guys-- bigger isn't always better when it comes to dogs! It leans in to the whole inoffensively cute vibe the guy -- Erik -- had that let me feel comfortable enough to roll the dice. Don't want to get back into dating on a bad note, after all.

We met up outside the restaurant he picked and that's when it hit me how I hadn't really had a one-on-one conversation with a man in. Well over a year, I think? Not counting work stuff.

But dinner went really well actually, and not just the surprisingly great Korean/Mexican fusion food! I would've been happy to let him do most of the talking, just to put the pressure off since I'm still a little nervous about everything. Instead he seemed really interested in my hobbies instead of just wanting to go on all evening about the rock climbing gym he's at half the time. Not that I have a ton of interesting hobbies right now, lol. But it was a good excuse as any to bring up SugarBunny and the dog talk carried us the rest of the way through dinner.

Erik's a busy guy, and before we met up he told me about another hobby of his and invited me to come with. Contra dancing. Really?? I didn't know anything about it but I figured the average age would be like, 50 so it seemed pretty harmless and I said yes. I can handle a little dancing, right? It won't be a nightclub this time, I should be able to have fun somewhere like that.

My first impression was the crowd was actually pretty young, so I was wrong about that! Maybe I'm not as in touch as I like to think. Dinner ran kinda late so we got there with only a couple minutes left of everyone standing around and Erik giving me a rapidfire explanation of how to contradance before the music started and everyone paired up. There was some kind of emcee on stage saying random phrases that correspond to dance moves but I had no idea what any of them went, so I just kind of let Erik guide me through whatever we had to do and tried to follow along. Then before I know it everyone switched partners and I stood there staring around at the crowd of strangers before this other guy made eye contact and came up before I could say anything. He tried twirling me around but before I could even think about where to put my feet everyone switched partners again, this girl with a pixie cut looked at me, and the same thing happened again! Finally it was back to Erik, where I hoped I'd get at least a couple minutes to catch myself.

But I didn't get any better. Erik kept telling me to just relax, try not to move so stiffly, and I wasn't able to make myself do it. The others who wanted to dance with me seemed just as unimpressed. It's like, no matter what I tried, I was always out of step with everyone else. We lasted fifteen minutes before Erik took me aside and asked if I was having a good time. I think Mel would have a good time at a place like this. Sara would act all embarrassed about going somewhere this wholesome and have some choice words, but she'd find a way to have fun with it anyway. And Ainsley... Ainsley...

Okay, look. I know that I owe any of you readers who may happen to be concerned a real explanation for what's going on with me. I'm going to say it up front: I know I'm not Ainsley, I don't believe I'm Ainsley, I didn't wake up one morning so unable to cope with the reality of the Inn and my own body's uncertain status that I convinced myself I'm someone else. Regardless of what anyone else does, I'm going to Old Orchard Beach when the reservation receipt says I am.

But if everyone kept telling you there's something wrong with you, whether they know the truth or not, and you start to believe it, and you kind of always did. And there was a hole in the world, one whose shape you suddenly fit, one you become immersed in every hour of your life for months, and you can tell how badly everyone around you wishes it were never there, and what left it behind had a better life than you... Wouldn't you eventually want to fill it? Just to see what it's like? Would it really be so horrible to try more than just the minimum of what the world expects?

That's what I realized, lying in my bed late one night. I hated the idea of giving in to the shit Sara and Marvin keep throwing at me, and a lot of Ainsley's choices weren't exactly ones I'd make on my own-- but I knew what those choices are! I had a guidebook, embedded into this entire life, for what's expected of the person shaped like Ainsley Thomas.

So I followed it-- more than the amount I'd been that's just enough to keep her from losing her job or (more of) her social life. I didn't wake up the next morning thinking I'm Ainsley, but I kept telling myself I did. I went to the gym, immersed myself in her interests, made small talk, annoyed my roommate, cooed at dogs, and generally tried to act like a happier person. And, to my shock, it sort of worked? Maybe it's the forced optimism but I think people have been nicer to me since I started doing this. The air of confused concern surrounding I used to get from Ainsley's circle lessened, even if it didn't go away. And over time, I got these moments where I could just, stop thinking about it and coast off the inertia of my own Ainsley impression. Like I've previously said, the important thing is keeping myself too busy and immersed to run out of momentum.

It essentially became a game where I'd ask myself how far I could take this. That's probably how I managed to talk myself into getting on Tinder, the prospect of which would've caused the me of even two months ago to spontaneously combust. Even still, I didn't intend taking it any further than going on one date and saying whatever I needed to to end things after that. I'd assumed that a random Tinder guy would give me plenty of reasons to regardless. But no, somehow my date turned out to know how to treat a lady.

That's a lot of what I thought in the back of my mind as I ran down my standard Ainsley small-talk script at Erik, being treated that way. How big his arms are compared to mine, getting the door opened for me, they way his speech was weird combination of respectful and slightly patronizing. He kept looking at me. Obviously I've experienced all this one way or another just by existing in public but that was always in situations where I could just leave or, at worst, zone out. But there, we both signed up for it, and I, Ainsley Thomas want to be treated that way on a date, I reminded myself. It's normal. Maybe I actually did kind of like parts of it once the sense of danger wore off a bit, but it's hard to tell whether I've Pavloved myself at this point. Or it was the novelty. I don't know.

The point is, I'd mentally prepared myself for my date to be the one to ruin it, but no, I had to ruin it when I finally hit the limit of my Ainsley persona. I just can't bring myself to dance. It's more funny than sad, compared to the nightclub from the bachelorette party. Clubs like that are high-pressure environments full of stressors that would've set me on edge even if I didn't have Ainsley's relationship with her best friend on the line. But I still can't find it in me to move freely in an all-ages group dance in a brightly lit gym? Come on. It makes it feel unreachable, that sense of fluidity and gracefulness (or enthusiasm, if the first two aren't great) all the women Ainsley's age I meet seem to have. Not that I could dance as a guy either but at least then it felt like there's lower expectations. Everyone at the contra dance could tell, they looked concerned, they were right to be!

I held off Erik's requests that we could seriously just chill out by the side and talk if I wasn't having any fun for about ten more minutes of dancing before I caved. But it felt like there wasn't anything to discuss. The momentum left broken and how un-Ainsley I really am returning in full force. Soon enough I left, telling him I'd had a good time (not completely a lie) and I'd talk to him later. We haven't spoken since, and now I don't know who I'm going to be in three days, in a different sense from how I don't know who I'm going to be in three months.

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