Simon/Joy: March Madness!

Things are going well for me. I'm making tons of money, keeping busy, and having tons of sex. Sometimes I feel guilty about it, like I shouldn't like having a guy stick his prick in me, but I'm stuck in Joy's body wired to like having my pussy poked so why fight it? You gotta live your life, it's no different from playing with myself except at its best it's like 1000x hotter (at its worst it's a pretty big disappointment but I just don't call those guys again.)

So yeah, I get laid like two or three times a week, whenever I'm feeling it. It's nice just to be able to text a guy and be like "Hey come over" without having to specify what it's for, but he knows. It's all very casual, I make that clear up front.

Except things have gotten complicated lately.

I went out on a date with Stretch. I was putting vibes out at work just to see if I could add one of those guys to my regular rotation, and Stretch finally picked up on it. I know he's been nursing a crush on me since at least Christmas. Except I have a rule never to ask a guy out, that's beneath me. If they want me they have to come get me.

It took him a while to pick up on that, though. He gets really flustered when I'm around, which is... cute. And I remember when I first had that thought - "That guy's cute." That's different from knowing a man is attractive and feeling he'd be a suitable sex partner. That's when I knew things were getting a bit weird.

I got scared and almost called it off but that's not my style. I went along with pleasuring myself when I wanted to try that, and I went along with exploring with Joey and all those other guys, and that worked out great. So I figured why pussy out now? I look like a chick, obviously I have some of the tastes of a chick. If I'm gonna like guys, so be it. Life is too short to deny yourself anything.

So we went out and it was... nice. Different from having a quick drink as a preliminary for sex, with a muscle-bound dude who is going to be fun in bed. We had to make conversation, share stories, be a bit more open... and to be honest that is not my strong suit. I think I excel at hookups because it's a transaction, like sales. This is true when I'm a guy, too - I've dated and hooked up a lot but I'm not really a "meet the parents" kind of guy (I've already met his parents! How messed up!) And as a chick I've gravitated more toward guys who remind me of me, alphas, go-getters and takers, and Stretch is... even though we work in the same biz, he's more soft and sensitive (kind of like a woman??) We're very different, and it was awkward, but he appeals to me, sooo...

We've been out a few times this month, when schedules permit, but I haven't fucked him yet. It feels weird to broach the subject, like I shouldn't be giving it away with him even though I have no problem doing that with other guys. I'm still not sure if I like the idea of committing to just one guy and if I do if it should be him, but I'm, I dunno, open minded I guess about it. I still have all summer since I booked my return trip to the Inn for August.

It's weird. Suddenly I feel weird talking about it. This is different.

PS!! He does not know about my other hook-ups except I have told him we are not exclusive. The rest is my business and my business only. He seems okay with it, albeit reluctantly.