What Separates Men From Boys

The following is an excerpt from a text conversation I had earlier with a guy I was seeing for a few weeks. The back story: he's great on paper -- smart, funny, has a great job, owns a car. In practice however, he's rather timid, somewhat shy, and incredibly awkward, which I found endearing... until I didn't. He has a big dick, he lasts a long time, and he knows how to use it and his fingers, but not once in the handful of times we had sex did he so much as attempt to take his mouth anywhere below my chest. He also nearly cried when there was a little blood on the condom once. Definitely wasn't going to work.

Last night he started asking me for dating/girl advice, as when I broke it off with him I told him "I think that you're perfect for someone, it's just not me," and as all nice guys do, he wanted to stay friends. He's tried a bit of online dating that's led to nothing, and he doesn't really know how to approach women IRL, but he says that with his new great job, he's finding himself wanting to settle down more and more, (keep in mind, still lives with his parents. Settle in the basement? I don't know.) He's also decided that he wants to date older women. Right.

I gave him some tips, and then went to meet my friend for a few drinks. He texted me more while out, and eventually I felt that this was the appropriate response:

Me: Alright, I'm going to give you the best advice you'll ever get: IF you are going to try dating older women you're going to need to get over your fear of blood, and you're going to need to start going down on them - and I mean that honestly for your own advancement, and in no way as an insult.
Me: Not necessarily at the same time.
Him: I had 2 gut-wrenching experiences in that department, so I'm not sure
Me: In which department?
Him: Going down...
Me: So? You think your spunk tastes like jolly ranchers or something?
Him: I don't know.
Me: Well, it doesn't.
Him: Okay
Me: It separates the men from the boys. And women want men. Otherwise you may as well stick to dating teenagers.

Drunken Encounters: Part 2...The Time I Was Sober

My goal was to have sex with Mr. T within a week of our first encounter but due to a bad cold and severely sore throat, no thanks to Old Guy, I had to postpone until last night.

I went over to his place and brought a couple of beers with me to break any potential tension. He seemed impressed by this and we drank them while watching Iron Chef.

He was sweet, he liked my dress and when Iron Chef was over and I was choosing a movie for us to watch he commented on how he liked that I hadn't stopped smiling since I got there. He said it was contagious and made him happy.

We talked about work and tattoos (he has many) and his mom and he seemed kind of nervous because he kept getting a stutter. He would talk about stuff we should do in the future, like dates and stuff. He also invited me to join his birthday festivities tonight.

We started to watch Austin Powers and I slid in next to him so we could cuddle a bit and after a while he started tickling me and he managed to get my dress up to grope my ass. Then he mumbled something about being quick because his roommate was going to come home from band practice soon. So I suggested we go to his room.

He refused to turn the damn light on because it was so messy, or something, and I knocked some shit off his book shelf because I walked right into it. We made out which turned into vigorous dry humping which turned into me going down on him. Which turned into sex.

He didn't once touch my vag, which I find baffling. He didn't want me to make any noise (which I found VERY hard!) just in case his roommate came home and heard. And when Mr. T came, I didn't even notice. He was soooo quiet and I had to ask him if he did or not and he said "yeah...It's your fault!" (a joke?) and then passed me my dress and bra. Actually he first suggested HE wear my dress, something he had mentioned twice already the first time was when he told me he liked it and the second time was when Britney spears came on TV and he said he wanted to make a music video dressed in her bikini and my dress...

Then we got dressed right away and as we were leaving his room I could swear that he tiptoed out to the living room tentatively just in case his roommate came home and he hadn't heard. So weird.

Then we resumed watching the movie. I sat right next to him but this time there was no cuddling. Soon his roommate DID come home, with some other dudes in tow and they did a drug deal. As soon as the guys walked in Mr. T turned into a bit of a bro. He was louder and showy and the stutter and nervousness were gone.

Soon the guys left, but the roommate stayed and it felt kind of awkward. I left right away because he was tired and had to work at 7am.

The goodbye was kind of awkward. He hugged me and kind of gave me a peck on the neck/shoulder and told me to text him.

I am not going to put much time into puzzling about this one. He was doing really well at the begining but the sex was disappointing. I'll see how it goes. No one is being written off just yet.

In other news, I plan on fucking Old Guy again this week. Fingers crossed!