Wednesday, July 6, 2011

Opportunity knocks

Just had a chat with a guy on grindr. He basically gave me an open invitation to come over any day of the week for a blow job. He happens to be on my way to work in the morning, which makes this a dream opportunity. I have his phone number. All I have to do is call.

This guy is older than I am, in his forties, and he is also married.  Clearly he has had more experience than I have, or doesn't struggle with the same shyness. He knew exactly what to say to make me feel comfortable. Didn't pressure me, but was very direct. He promised discretion and convenience.

I know, without a doubt, that I will eventually have sex with a man.  Probably sooner rather than later. But how I go about it is still to be determined. Is this guy the right one, the one with whom I should jump into the deep end? What are the warning signs to look for when hooking up with a complete stranger? Am I ready for this?


  1. Only you can answer your last question. If you're feeling "good" about a guy and you're ready to take the plunge, meet him somewhere in public so you can talk. That may provide the information, the level of comfort your'e looking for b4 u take the next step.

  2. God, I wish I'd had something like this when I was going through what you're experiencing. You have no idea how lucky you are to have all this advice and council. Take it all with a grain of salt. Everyone has their opinion and they all want to tell you what you should do or not do. What do you want out of this encounter? Where do you see it going? Where do you see yourself in a year, in five years? Still married? With a man? At some point Jay, you're going to need to confront the fact that you made a commitment to your wife and how does all this fit into that and are you still able to fulfill that commitment? I know Will was a huge buzz kill, but there is an element of truth there that will need to be addressed at some point. It took me 20 years to get there. Some of us are more dense than others. LOL. You are taking responsiblity for your actions and that is good. Good luck, buddy.


  3. I suggest you read my blog, and use the archive thingy on the right hand side, to read from the beginning.

    I was so scared and nervous the first time! When I was actually getting out of my car, and going to this dudes door, I felt like I was in some kind of dream.

    Of course I've calmed down since then.

    After that first one, I told myself with the experience under my belt, there was no need to do any more.

    Oh how fucking wrong I was!

    I was hooked. HARD! (pun intended.)

    I don't regret it now at all. I have so much more confidence.

    I'm not saying the random or anonymous hookup is for everyone, but for me, it's done wonders to my self esteem and my sense of adventure and even my outlook on life, strangers I meet, and everyday living.

    Did I forget to mention, it's totally fucking fun?

    You can find my blog by clicking my photo icon. Yes, that's really me.

  4. Sounds good. Meet him for coffee at Starbucks and have a nice chat. If your ready, you will know. If not, just cost you a cup of java.

  5. Aside from feeling comfortable, rugbysex, or dealing with those serious issues, miracleman, what should I look out for? I am such a virgin when it comes to this, and I'm worried that I am literally going to walk into a trap while missing the obviously warning signs.
    Jack, I started at the beginning of your blog this morning. Great stuff! That's what I am talking about. What are the practical things I need to do, so that if I do decide to go through with this, I stay protected, safe? What are the obvious warning signs of danger?

  6. My first time was with a guy I met via a personal advert, and after much nervousness, a few emails and a phone chat we arranged to meet at a hotel. I got there first and got really nervous while I awaited his arrival. I even nearly walked away from it after having second thoughts. After we met we had a drink first, then eased into the physical by having a shower together - a real ice breaker. Being naked together let me feel ralaxed and I just reached out and held a cock for the first time ever. Soon I was on my knees sucking him, and the rest was just an amazing blur of pleasure. The first step is the hardest because I had to overcome all the negative emotions and doubts, but once I experienced it I felt likie I was being released and reborn. It was the sexiest, most erotic night of my life, ever. Yes, I was hooked as well. I'm very, very glad I had the guts to try. The worst that could happen is you decide it's not for you, so what's to lose?