It happened: The First Night with Mr. IT Pilot

Following the episode of me walking out of the IT Pilot's apartment, I decided to invite him over to my apartment for a sleepover. I felt like maybe I should give it one last shot, to see if I meant anything to him.

I guess I misinformed about wanting to be coddled- I WANT THAT. My self esteem is shot, and has been for a while. I know it's really unattractive not to be confident, and I really wish I was, so I really don't mind at all when he asks me what I'm thinking. I like it. I just don't know how to process what I'm thinking and say them correctly and not scare him off. So yes, I had told him to bring clothes, (he responded with "lol.... ok") but honestly at the moment I texted him the invitation, I wasn't feeling it. It just feels like a hookup, and I knew eventually, he'd just end up walking away. They always do. They realize it takes too much to make me happy, and that I require too much attention; I admit, it's overwhelming. I didn't want to have sex with him right away because I didn't know how he would take it; I didn't know what he would think of me, and since he'd told me he'd dated and spent so much money on his last "date" over the last 6 months, I FIGURED he'd be ok to wait.... idk... maybe 2 weeks or something.

It was all moot at that point. MOOT I tell yah, MOOOOOOT.Things just got totally twisted..... this is what happens when you're a girl.....


So he came up to my apartment after work, took in the surroundings, we talked for a bit, and he set me out at arms' length and said "So listen..... I'm sorry about the other night. I realize I shouldn't have done that so.... I was wrong, and you were right" I was like, Wow. This is EXACTLY what I needed him to do- apologize. 

We had a geeky date. REALLY geeky. We went out to dinner at one of my favorite restaurants, and talked, then he got this bright idea that he wanted to play board games..... ?...... I was like...hmmm okay..... maybe when I was 16, but alright, let's give it a shot. We went to Target to the game section and picked up a game of Jenga and some beer. We came back to my place, and we played a couple of games, which I lost at terribly because I was getting tipsy already. We watched TV, and started making out..... and then I straddled him and asked him what he was thinking.... etc etc.

I wanted him to tell me what he really wanted to do, but he wouldn't say it. So at one point he asked me what I was thinking and I just flat out said it "I want to [BLEEP] you. Well... more like, I want you to [BLEEP] me."

So we both jumped up from the floor and went into the bedroom...

We went into the bedroom and got into bed and as he was trying to take off my bra, I tried to help him. I didn't even get to put both hands behind me when he says "No, I got this" and unstrapped with ONE HAND. I was like "????Zomg!!"

We got completely naked and he took out the condoms from his bag (because he had brought a bag with his extra clothes for the next day- just like he'd been told to. Though I personally didn't expect him to bring a bag- just a shirt...)

Anyway, we started going at it, and Mr. IT Pilot did the job exceptionally well. He didn't come as fast as I anticipated, after being abstinent for 9 months. He went for a good.... 15 minutes, and gave me three orgasms during the first round- I was mouth agape. I was like.... Holy Crap!! Either he's really good, or I haven't had good sex in a while.......

He came and collapsed onto me, and just rested. We had some pillow talk, and then I asked him about the text that had left me confused for the entire afternoon (i.e. "I'll think about it") He said he normally says he needs to think about things before saying anything else, so that he doesn't say something wrong. He said he didn't mean to leave me in the dark.

Anyway, we got settled for bed, again, and went for a repeat. This time, I lost track of how many orgasms I had. He ended up spending the night, and we both left for work together the next morning.

Once at work, I had a great attitude, and I got called out for it, so I was like.. Ok.. relax, I need to play it cool and get this grin off my face. Later on in the morning, I get this text from him saying "Can't stop thinking about you."

And later on: "Can I add you on Facebook? ;)"

HOLY SHIT!