Monday, January 27, 2025

Daryl/Zee: New Year's Resolution/Confession

Just gonna say it:  I slept with the guy everyone warned me about, on purpose, in spite of or maybe even because of everyone warning me about him. 

I was in a bit of a funk at the end of the year; i didn't really have enough time off accrued to take any sort of Christmas vacation, but work slowed to a crawl because everyone else was making plans around the holidays.  I've made some friends in Boston, but nobody else who was also at loose ends, and I kept finding excuses not to put up a tree or decorate the apartment.  Which is fine until you wake up on the 25th with nothing to do and seriously think about calling your ex to see what he's up to. 

I didn't, but the next week was even slower, so as I sipped my hot chocolate as I wandered around the city's First Night event, I made an actual resolution:  I was not going to be J.T.'s stupid ex who constantly thought about how she gave up her entire life for a man any more.  I was gonna aggressively move on.  I actually said this aloud right before the fireworks started going off; if anyone around me had been paying attention, it would have been so cool. 

Then, a day and a half later, it was First Thursday at The Changeling.  There actually weren't many of us there, and a couple left when the infamous Lenny showed up, and by the end of the night, it was just us. 

It's been a couple months since I've posted, but Lenny stayed at the Inn a few summers ago, got turned into a black woman, but things lined up so he could go back to his real life in just a few weeks.  Since then, he's really had a thing for other Inn people, especially women who used to be men, and hooks up with a lot of them, but it never lasts and often ends badly.  Most of the sizable Boston contingent of transformees at least have a second-hand story.  I was warned.  But, as the saying goes, I wasn't looking for Mr. Right, but Mr. Right Now. 

I was a bit surprised when I actually met him; from the way everyone talked, I was expecting a twenty-something horndog who had either convinced himself that his experience had set the course of his life or learned how to work a very specific new fetish.  Instead, he's forty-ish, balding a little though in decent shape, and using reading glasses.  It's kind of cute, not in an "I'm attracted to him" way, but small and non-threatening.  Even having been warned, it made me underestimate how good his game is.  He maintains eye contact, even though I've taken off my blazer and the turtleneck underneath it's a bit tight, compliments my hair on a way that indicates he knows that it can be a bit of a challenge without underlining it, and waitress for me to bring up sports and other male-coded things without looking relieved afterward. It's better than most people who sit down next to me at a bar manage. 

Long story short, we wind up at his house.  He complains a bit about wearing a condom, but does.  The gossip about his dick isn't exaggerating, and, yeah, he absolutely comes across as someone with first-hand experience in having a clitoris; he finds my g-spot quick! He doesn't fumble around squeezing my breasts like stress balls or putting his dick anywhere i wouldn't want it.  And while it's been a while for me, I do know how to keep him hard so we can go for a long time.

Eventually, we've both climaxed and are lying on top of the sheets, sweaty, naked, and panting in a good way.  He turns and looks at me with a smile.  "That was amazing!  You were meant to be a woman, don't you think?"

I laughed a bit.  "I don't know about that.  You ask me a year ago, and I'm sure I was meant to be one specific man's, uh, life partner."  I tripped a bit there; "girlfriend" seemed insufficient, but i can't say I'd had a lot of specific fantasies of being J.T.'s wife, even by the time I got ready to propose.  "I'm kind of not doing 'meant to be' right now."  The spell broken a bit, I started picking up my clothes and getting dressed.  "Well, aside from being meant to be at work tomorrow, if you know what I mean."

I called a rideshare, got back home, and got three terrible hours of sleep, but there was barely anyone in the office to notice.  Around 11:30am, I got the first text, asking if I wanted to do something more like an actual date the next night.  I was in a call, so I ignored it, and worked through lunch.  By 3pm, there were five messages, not angry or indignant or anything, but it seemed like a lot.  I feel like I would have given a woman I liked a little space, but I was kind of worried about asking anyone if this was a red flag, because the people who wouldn't find a woman in her thirties asking this weird would be all "girl, you slept with Lenny?"

I was bored enough binging the latest season of Lioness (there are like fifteen minutes of characters you actually care about in an hour of that show) to text back, and, yeah, we wound up arranging dinner and a movie the next night.

Based on the movie and restaurant he booked, it was going to be pretty casual, so I showed up in jeans, sneakers, and a hoodie.  Nothing torn up or anything - all Christmas-gift-card-new, in fact - but he raised his eyebrows. 

I tried to be playful.  "What, not what you expect from someone 'meant to be a woman'?  You didn't get to experience wearing skirts in the winter!"

He laughed, but it kind of got weird really fast, and at the end of the movie, we went for drinks, and he pointed out a couple of girls who were more dolled up for their Saturday night and said I'd look good in that or whatever, and by the end, I kind of wasn't in the mood.  I said so, he got kind of pissy about it, but ultimately I just went home.

Anyway, I actually had a busy week at work after that - quarterly planning stuff, and really wasn't looking to go out so much as go home at the end of the day, but he's kept texting me.  Even wanted to know if I was doing anything special for Martin Luther King Day, and, geez, white guys, do not ask your Black friends that.  Especially not if you're looking for a date or fun times; I actually had some 23-year-old ask at work if there were remembrances or events scheduled, and could kind of respect someone not knowing and wanting to know what kind of holiday it was for other people.  I said it wasn't exactly a day where I went to church, but I was kind of new in town and didn't know what was planned myself, and should find out for next year.

Which isn't the point so much that it was a sort of clarifying moment for how presumptuous Lenny could be and how actually dating him was going to be all sorts of uncomfortable even if he did have a certain understanding of my life that 98% of the folks I might meet didn't.  So I finally told him that this wasn't going to happen, but I was grateful for that one night.

It hasn't stopped him from texting me yet, so that's going to be a bit of a thing for a while.  But I don't regret the hook-up; I kind of needed a rebound to prove to myself that I am in fact a heterosexual girl who enjoys that rather than a guy who has spent years as various women because the girl I fell for turned out to be something else.  And also that, while I kind of hope I'll find someone I can share my whole real history with, that may not be an entirely unmixed blessing!

-Zee

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