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February 20, 2011
Posted at 8:47 am

The date, was great! The long version follows :)

I had a really fun evening. I was nervous as hell but the tennis pulled a lot of the nervous energy out of me. He's handsome, athletic, well read, smart, charming, has manners. And yes…very sexy. My friend Sunny (hi sis) asked me to say what I wore, so…

For tennis, I wore a traditional white pleated skirt and a torso-hugging white sleeveless athletic top and while all the girls are wearing what they call "boy shorts" underneath, I wore white rayon panties. And I knew full well that when I bent over to pick up the ball, he could see the dark crease of my behind. Yes, I was trying to be sexy, OK?

He was already waiting for me at his club. He was a gentleman and only hit second serves at me, so I had my chances. He was competitor enough to play through and while the play was spirited, I was no match for him. Didn't matter. The tennis was fun, we had some good rallies and I'm glad he didn't lose on purpose. There was a very positive vibe.

We showered and changed at the club. I wore a cute black mini skirt with a snug, red sleeveless top and comfortable flats, in case we went for a walk. We took his car.

His choice for a sushi restaurant was first rate. I had a little sake but stayed totally sober. The conversation flowed very easily.

On to the art show. Walking around, we had a chance to continue talking and I was feeling comfortable and relaxed.

But I know what you're waiting for. Did I have sex with him? Well, yes, sort of. A little. Jesus. I feel like I'm some fucking junior high school girl.

We got back to his club and he pulled in next to where I'd left my car and it was dark and we'd really enjoyed one another's company and he put his arm around me and moved in for a kiss. FUCK, I was nervous! But I kissed him back and it felt really nice and it was OK, so I kissed him again and we did tongues in mouths and on necks and I liked it and his hands started roving and I let him, and my hands started roving and we touched one another in places and all of a sudden I'm feeling very embarrassed telling you this and I don't need to explain every detail but we didn't have intercourse and I didn't blow him or give him a hand job and I didn't let him put his hand inside my panties and it all felt really good and we're going out again next week.

Had we gone any further it would have crossed my comfort line and I'm fine with where we stopped and I'm sure he jerked off when he got home because he had a very manly boner in his pants and yes, I felt it, OK? Yes. LOL.

He insisted I call him when I got home and I waited till I got into bed and while I was talking to him I masturbated, except I felt a little shy about telling him what I was doing. Me? Shy? WTF?

The bottom line here is that at least as far as it went, I was able to get past my issues, plus I enjoyed the company of a boy my age. I'd say it was pretty good evening.

And last, I really appreciate all the emails of advice and support. You're the sweetest collection of pervs in the world.