1. We have been casually seeing each other for a few months. Once or twice a week that is. I made sure she was given every chance to be the one who initiated the conversation and suggested we meet. Which, in my not so humble opinion, is the reason why it has taken so long to get to this point.
2. Tonight should be the night. I had my lawyers contact her lawyers a few days ago, to present her with the contract. She had some minor remarks that my legal team tweaked into something acceptable, and got her legal team to agree on, and the contract was signed earlier today. A scanned copy just arrived in my email. I could barely contain myself, when I read it.
3. Tonight will be the night! I have studied up on the signs of females being uncomfortable. I aced the test on line. There is: blushing, giggling, gesturing, saying "no", saying "we shouldn't", saying "maybe not" saying "I don't know", saying "yes,.. but" saying "yes" but not meaning it, not saying anything but thinking "no", swatting my hand with her hand, kicking me in the chin, rolling her eyes, giving me a bj reluctantly, asking me if we could stop, I know it ALL. There is nothing she can surprise me with.
4. But a certain level of nervousness did set in, I have to admit. Should I record the whole thing, in case she changes her mind post-action? But wouldn't that make me a creep? I mean I would tell her first of course. But what if she then says my request to record our physical encounter made her feel she was obligated to say yes? Better not risk it. Ok it is settled. No recording.
5. I took one last call from my lawyer. He advised me again that having a sexual relationship is considered a high-risk activity and that I should re-think it. And if I am still convinced I want to proceed, I want to make sure I have my sexual liability insurance in good standing. Check! Yes I do! The show must go… into making. After all, whats the worst that could really happen, right?
6. I thought about many of my friends, who have given up on trying to pursue real-life sex and just played more video games and jerked off to more porn. I would consider this lifestyle also, but having watched porn almost every day since I was seven made me somewhat immune to it now. Unless it was something really creepy like they fuck without a legal contract in place. But that stuff is hard to get with all the monitoring in place! I felt like only a real life sexual experience could help me deal with my erectile dysfunction. I hoped.
7. There were stories about guys turning gay just because dealing with men turned out to be much easier and less risky. I tried. I really did. But being gay is just not my forte. Cocks do not appeal to me, even though I have one. Weird, I know. No thank you, I will stick to the warm and silky vaginas. That is, if I muster up my courage to go through with tonight.
8. The safest practice out there is doing it with a bunch of lawyers present. But then it's usually at least 4 people standing around, while you try to have sex. Plus they also take notes. I would just lose my hard-on because I'd wonder what their notes say. No, lawyers are good to prep the paperwork but when there is time for the real actions, they should stay away, like the roaches they are.
9. I thought about 10-15 years ago, when everything was easier. You could ask a girl out, you could initiate a kiss, you could even suggest you go home and fuck. Hell I could even put her in handcuffs and spank her without being afraid of being dragged the next day, week, month or a decade. But those times are long gone, brother. Long gone.
10. She just got here. My phone alerted me. I gave our contract one last quick glance. Yes, I understand that she has the right to stop blowing me mid-way and just walk out. Yes I understand I cannot even mention the words "blue balls" or "bitch, finish what you started". And if I think it, I must not show it on my face. I am also aware that should she start blushing, giggling, gesturing, saying "no", saying "we shouldn't, saying "maybe not" saying "I don't know", saying "yes but" saying "yes" but not meaning it, not saying anything but thinking "no", swatting my hand with her hand, kicking me in the chin, rolling her eyes, giving me a bj reluctantly, asking me if we could stop I must seize my action immediately, and call my lawyer. Man, this date is going to be really expensive, if it gets out of hand. But then again, better safe than sorry, right?