Take the Initiative

He never initiates.

Mind you, he's always courteous and responsive when I send an email. And he's very timely. But I don't think it would ever occur to him to send the initial message.

I'm speaking of the Nerd.

We lost touch for a bit. The email I had for him kept kicking back as undeliverable. But I found another way - got an updated address, and we have occasionally have found some time that works for us both.  ......and he's always receptive of coming by.

Part of me thinks he thinks he isn't worthy..........then he totally is.  I mean, you remember his member, right?

And he's totally cute in that nerdy kind of way.  But eye contact is a rare thing. Conversation can be a little stilted, but truth be told, I'm not looking to exchange thoughts on world or local views.

He was over recently, shy and reserved as usual. We chit-chatted a bit before he reached out to touch my crotch. Usually, I greet him fully clothed and we take it from there. This time, I was in the midst of changing from work when he showed......so I was in my boxer briefs and t-shirt.

Now, he does reach for my cock. And he will hold it, but he's never stroked it and certainly never sucked it. I'd say I think he's totally gay, but maybe he is bi or something. Or just a total top  - shy and non-aggressive as he might be.

I will say, he usually reaches for my dick, but only on the way to elsewhere.

The many likes feeling my legs, my taint and my hole. And I like him touching them.

Often there is our version of foreplay. Some talk, though not as dirty as I'd prefer, but I try to not shock him with filth. I don't know he would be offended or could keep up - I just assume he would and can't. But I've been wrong before.

I wasn't fully prepared for anything other than oral.  I wanted to be.  Fuck, I wanted to be. But I wasn't. I think when we are all in the heat of the moment, we've taken that risk (if we give it any thought at all), but this was not that day.

Still, his working of my nipples had me thinking differently. And unexpectedly he leaned down and took the left one in his mouth.  This was new.  18 months into playing on and off and we hit something new. The joke was, he is no novice to this.  He was an expert at it. I think he was trying to get me to just bend over,  no questions asked. The sensation made question it all.

Had he just been assertive and bent me over, I'd have gone with it.  But he didn't.

As he had done in the past, he brought up the possibility of watching someone fuck me or me sucking someone else. As it turns out, I might have someone in mind who'd be into it.  This excited him to a point I had never seen.

Reserved as he is, he did a second thing we've never done. He kissed me.  Wild. Passionate. Not shy or hesitant the way you might expect.  It went on for a few minutes.

I had his cock in my hand and noticed he had discharged something more than precum but less than cum.  I licked the stringy contents from my fingers and he went for the kiss again, with his semi-jizz still on my tongue - not ingested..........yet.  Another surprise.

He was so excited, and I know him well enough, that I had to go to my knees. He was too on his way to getting off that fucking would be out of the question - or only be partially inserted until he shot. So a blowjob was the way to go.

It did not take me long to have him on edge.  I miscalculated the edging process. The confidence I had to take him to, but not over, the brink was flawed. I would have buried his cock deeper into my throat had I known he was there. As it was, the head and 1-2" was in my mouth.

That mouth started filling with cum.  He was gripping the bottom of his shirt, partially to keep a good view of what was going on down there and partially for something to hold onto during orgasm.

The man trembled during and after quite a bit. I must have stayed on it for a good two minutes after capturing his entire load and all the stray remnants.

He claimed to have jacked off the day before, wanting to give it to me, but that he had not seen me.

There it is with the initiation part. Had he just sent a message, I'd have known he was interested and had a week's worth of scum in his nuts. But for only having a 24 hour load, it was nicely sized.

Next time though - no matter what - I think he needs to fuck me with that big cock.