What A Dilemma

It sounds like you are both on the rebound. As long as you are both aware of that, and willing to accept that, then all is fine. However, if either of you might start getting emotionally attached, then don't go down this path.

There is a saying: "Don't sh#($t in your own back yard." What that is about is in life there are people that you need to support you in times of problems. If this guy is in that category, then don't mix it up with romance/sex when you know later on you'll most likely break up and never want to see each other again. A few good orgasmic releases pale in comparison to an additional friend who will be there for you when you need him.

In many ways I'm shy too -- maybe not as bad as when I was younger. That is why it was EASIER for me to have anonymous sex. I would never have the courage to talk to a friend about needing to get off with his help -- especially, if I had already confided in him about my frustrations in my love life. It was always much easier to just meet a stranger, and just get off.
 
My advice is to talk to him. Tell him how you feel and ask him how he feels. Tell him what you've told us and see how your conversation goes. Hopefully you'll both want the same thing and fireworks will fly tonight. :)
 
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