August 2009

JAG Man and I had a wonderful date at The W Hotel’s bar and restaurant, but the elation turned to deflation when his little head took control of his big head. I’m way too old and comfortable in my own skin to tolerate a guy trying to make me feel bad about waiting to have sex. JAG Man told me three days after I met him that he wasn’t sure what he was looking for out of a relationship. I was equally clear with him that I wanted to take my time and get to know him gradually before adding sex into the mix.

After everything went down (pun intended), JAG Man apologized, said that it would never happen again, and that he wanted to continue dating me. I figured that he would try to make it up to me that weekend, but that never happened. For the next ten days, JAG Man sent me lots of e-mails and a few text messages.

Did he call me on the phone? Nope.

Did he ask me out again? Nah.

Ten days seemed liked an eternity because he worked right next door to my place! Next door!

As we were texting back and forth, I made a reference to the fact that I had gotten some new boy shorts. (Yes, I can play dirty.)

JAG Man: You better watch it or I’ll get in my car and drive over there.

Me: What’s stopping you?

We played that game for a little bit and then he called me. I told him that I didn’t want to keep putting the brakes on the physical side of things, but that I wasn’t about to put out for a guy who didn’t have much time to spend with me. (If you’ve read my blog before, you know I’m not a prude. But, I had told myself that I wasn’t going to have sex again unless I was in a relationship and I was sticking to that.)

I did clarify, though, that I was hoping things would progress gradually.

“It’s not my intention to stay at 2nd base indefinitely!” I explained with a laugh. “I’m open to doing a little more than last time when we see each other next.”

“What would more consist of?” JAG Man wondered.

“Hands…no oral,” I said. “Would that work for you?”

He paused before saying, “I’ll be there in 20 minutes.”

I had wondered if he planned on spending the night at my place since it was already after midnight and he had to be at work by 8:30am. But, I realized that wasn’t part of his plan when he arrived at my door without any bags.

We had a drink on the balcony, and then headed to the bedroom. JAG Man is a great kisser so it felt right to have his lips back on my mine. Everything happened naturally, and we lost our clothes pretty quickly. I placed my hand on his cock, and he put his two fingers on top of my pussy. I exhaled when I realized that he knew what he was doing, as he easily found my clit and then my G-spot. I smiled to myself since a guy who can make me cum with just his hands on the first try is clearly no novice. (You would hope that would be the case with all guys in their 30s that I meet, but I’m sad to say that it’s not.)

JAG Man removed his hand from my pussy, and I focused on his cock until he came. When he was finished, he got up to go the bathroom. When he walked back into the bedroom, he found me still lying there with my finger on my clit.

I looked up at him coyly and said, “I’m not done.”

JAG Man got back into bed, leaned over and kissed me. He then took one of my tits in his mouth and put his fingers back on my clit. In less than five minutes, he got me off one more time…then a…

Wait a minute…why did he take his hand away? I was just saying, “Right there.” Put your hand back. Put. Your. Hand. Back!

I thought that to myself, but didn’t say anything out loud. He kissed me once on the lips, and asked me,

“How many times did you cum?”

“2 ½.”

I waited to see what JAG Man would do. Would he realize that I wasn’t done or not? Who responds to a question about orgasms with a half of anything? He would get it, right?

Umm…nope! JAG Man got out of bed and started putting on his clothes.

“So…you’re leaving?” I inquired with some confusion.

“Yeah. I have to get up early tomorrow.”

“Okay. Well, you could’ve spent the night if you had wanted.”

“Well, I always sleep better in my own bed. You don’t need to let me out, though. Go to sleep,” he told me.

“Umm…I’m not finished so I can let you out. I’m going to get off one more time before I crash,” I explained.

I wondered what he would do, and watched as he didn’t deviate from his plan for a second. I walked him to the door, gave him a kiss goodbye, went back to bed and broke out my favorite toy.

I was glad that I had seen JAG Man that night. But, I sure as hell wasn’t thinking about him when I got off that last time. JAG Man had a chance to win some points, but instead, he left me wanting more.

And not in the good way!

This week’s posts: What happened next with JAG Man and how I met Buckeyes Boy :).

Next week’s posts: Back to 2005 and Philly Matt.