I sat in my apartment on my couch trying to make sense of what I was doing. Only months earlier I had been snooping around a male-for-male message board out of pure curiosity when he started the conversation.
His name was Todd. He began pleasantly and we developed a rapport about sports and other mundane things. I wasn't looking for a hook up, and was on my defensive, but the conversations melted away my misgivings. Weeks followed and I looked forward to hearing from him. There was nothing sexual about the exchanges per se, but every once in a while there would be a little innuendo thrown in as a tension breaker. These exchanges being via internet, I would respond in kind, and there was nothing that felt inappropriate about them.
Finally, with the Super Bowl approaching he suggested we make a bet. He was thinking Patriots, I was thinking St. Louis. I couldn't in good conscience agree to New England as I was a staunch Dolphins fan.
"You're pretty sure of yourself, aren't you?" he said.
"Pretty sure the Patriots lose, yes," I said in response.
"Ok," he said. "Let's make this interesting."
Thinking he meant money, I said, "I'm listening."
"Ok. You're a good bit younger than I am, so I'd feel bad about taking your money. How about the loser has to do something for winner?"
"Like what?"
"Ok, I've got it. The winner gets a blowjob."
I was without words. I mean, I knew there was a little vague sexual tension around, but this was way more out front than I was ready for. I was a straight guy, yes curious perhaps, but definitely not experienced or experimental.
"Cat got your tongue?" he said. "Or are you suddenly less confident in your football knowledge?"
The grade school-like challenge was enough to make me speak before thinking it through. Plus, this was over the internet, and I never had to actually meet the guy if I wasn't comfortable.
"Ok," I said. "It's a deal. The winner gets a blowjob."
The next week was filled with trash talking on both sides. We'd never exchanged photos, but I knew that he was a psychologist, a bit out of shape, and had a way with words. Through conversation, I also found that he dabbled in hypnosis. He told me it helped people with phobias or even mild addictions overcome their issues. I told him that as a cyclist I'd been having a bit of performance anxiety before races and he suggested we try it sometime. It seems like a good icebreaker, but I put a pin in it for some other time.
The game came and went. I lost to a last second field goal by Adam Vinateri, in what would be the start of New England's dynasty. Roundly beaten, I kicked around the idea of just ceasing all communications with Todd, but remained intrigued about what he'd mentioned regarding hypnosis. The thought of having to give a blowjob was plenty disturbing, though. I'd never had any interested in other guys, save for the curiosities of my classmates in the locker rooms. Never sexual in nature, only comparison and contrast. I could certainly appreciate a well built guy and could say if one was more attractive than another, but I'd never thought of a sexual encounter with one.
I expressed my nerves with Todd, and he responded by saying that it was just kind of a joke. He didn't want give one either. I was relieved, but it was enough to spark curiosity. After the change in plans, we continued to talk as before. Sexual innuendo continued as well. In the middle of a conversation he might spout off with, "Yeah, well you still should giving me a blowjob." It was met with laughter, but also kept the tension there, just under the surface.
I was a rabid internet porn junkie and used them to masturbate frequently. As I wondered what a blowjob would be like, I began to pay more and more attention to the male actors in the pornos; the size of their dicks, how they came, and what the women did to them. I was increasingly interested in blowjob videos rather than straight-up sex. It became such that just watching another guy cum was enough to get me hard as a rock.
One day Todd suggested we try a little hypnosis to see how susceptible I was. I wasn't sure about it, but finally agreed to meet up at my apartment the next day and give it a shot. So here I was, waiting for this stranger I'd met online. A man who I'd at one time agreed to give a blowjob.
The knock at the door startled me. I didn't know what to expect, and had I expected anything, he wouldn't have been it.