How Low Can You Go?

OK...had some fun in the great indoors tonite. Jake, a cute guy from work and I struck up a friendly conversation via text message today. Now, I am notoriously poor at returning texts. It's not intentional, I just get immersed into whatever I'm doing and texting slips my mind. Apparently the same goes for phone calls.

Well, Jake and I started at about 2pm yesterday. We joked a bit about various topics. We eventually got to my homosexual experiences, if such a laughable record could be called experience. He told me that I could ask anything I wanted to know about. So I asked. The conversation turned out to be enlightening. We discussed everything from bottoming, oral sex, identifying and responding to flirting, and a few things in between. In the midst of the conversation we drifted to why he doesn't top. He said because he's too large and it hurts people. Naturally my mind spun with the possibilities, and naturally not having a bevy of experience with dick, I wanted to see his. So, for about three hours we teased each other about one sending a picture to the other. I initially decided to go safe, and took a pic of my lower body, with my hand grabbing my junk. He countered with a picture of his lower abs.

I have mentioned that I am an "in the moment" guy. The less time to think I have, the more "fun" I am according to sources. I got swept up in the moment and finally I acquiesced, praying that this would not come back to haunt me, went to the bathroom, snapped some shots in the mirror. I started with some pubeage [sic] and just a peek of shaft and then took four more progressively lower pictures, each showing more than the previous.

In my mind I tried to think of all the ways that this could spin out of control and take a giant bite out of my rear. A few minutes later I receive a picture from Jake similar to mine. For the time, being "in the moment" was paying off. I decided that I like this game; enough in fact, to raise the stakes. I message a little dare about upping the ante and sent a second picture. Though I am a shy person, and I detest that I let my physique fall into disrepair, curiosity and my tendency to be bold "in the moment" pushed me. I had to wait a little longer, but sure enough was more of Jake's dong. ***Since it has been so long since I posted, Jake would be cute, out gay guy that works with me. Everyone loves him. Cool dude.***

Being horny, and having the breadth of my same sex experience happen at a club nearly a year ago, I was hype. My pictures came out decent. I was actually laughing because it looked like I had plenty of dick. DOES NOT seem that way in person, but I guess I should ask someone to look around there and give me there opinion ;).but back to the story....2am... Low wasn't low enough. I sent my third picture. I guess I was all in, but I still couldn't reveal the full monty just yet. The fourth picture was me in all my humble glory, but I needed to know if he would go for it. I had ran out of penis at that point anyway.

My hopes were dashed however. I did not receive a third picture from him. He fell ASLEEP!!!!! To be fair he had driven a few hundred miles on a road trip for the weekend and it was nearly 4am at this point. I vow compensatory actions, but let him sleep. I'm gonna ask to touch it or something freaky....damn I just planned ahead. Whatever I ask for, I won't plan it. I'll wait and play it by ear, see what I come up with...any suggestions?

Also, I asked Jake how to approach and/or tell if a guy is interested. He gave me some very concrete tips. If there is something that any veterans or just plain lucky mofos want to add, I welcome it.