An Interesting Past Ten Days

I’ve been a little busy for the past ten days… and it hasn’t been all work… Jack is definitely not being a dull boy!
Ten days ago (or so), it was my birthday! I’m now the ripe ol’ age of 33! To celebrate the day, I decided to call up an old buddy to go to a bar in Arlington to have some drinks and play some poker (yes, I’m becoming addicted — at least it’s free)!
So, I grab a beer, grab a chair and go at it. I play decently, but not nearly as well as I did the week before at TT Reynolds, when I won the whole thing. So, after about and hour and a half, I’m out of the tournament. My friend and I head to the bar to continue having some drinks (and to wait for the second tournament to begin).
Well, while we’re waiting, our waitress from the poker area asks us if we’d like something else to drink. I coyly bring up the fact that it’s my birthday (in hopes of getting a free drink), and she replies “What do you want? A hug?”
“Well, OK, if you’re passing them out, I’ll take one!” So, I got my hug and then my friend convinced her to get me a free drink anyway. So, she buys me a shot of Jaegermeister. Let me repeat… SHE BOUGHT IT FOR ME! It wasn’t a comp from the bar, she purchased it, gave it to me, and watched me drink it. And from then on, I begin to notice her smiling my direction, and start thinking that she may be flirting with me… Hmmmmmm!?!?
So, the second tournament begins, and an hour and fourty-five minutes later, I’m out again. And instead of leaving, I, under the influence of some alcohol, think that maybe I should check out the waitress and see where it might go.
So, when the poker tournament made it to the final table, I was standing there watching, and my waitress comes up to me and asks me what I was still doing there. “I want to see what happens!” She asks if I watch the poker games on TV, and I tell her that I do.
And then she asks me what I do (what my job is). Honestly, I answer her that I run the dining and catering services for a private high school.
“Which school” she asks.
“Episcopal High School” I answer.
“I don’t know that school. Our school doesn’t play them.” And at that very instant, I have 2 thoughts enter my head at the exact same time: one, she’s a teacher; or two, oh no!! And then she unloads the fact that she’s only 18. AAAAAAAGGGGHHHHHHH!
I respond something like “and I was just trying to figure out how to get your number, and you’re 18!?! I so had guessed that you were 22 or 23!” And immediately, I begin trying to figure out how to get out of the situation without her thinking that it had anything to do with her being only 18. She has to get someone else a drink, and I sneak away.
18!?! Sorry, can’t do that. I have 18 year old girls at the school where I work — it just wouldn’t be right. I’m still “surprised” by her little revelation!
So…
That following Saturday (almost a week ago), I’ve still got the poker itch in me, and drive all the way down to Woodbridge to a bar called Brittany’s. I have a beer or two, and make it to the final two tables (still not doing as well as I did the first night) before losing. And while waiting for the 10:00 tournament to begin, I start to watch the final table from the first tournament.
And I don’t notice it, but a girl comes up beside me and starts watching the final table too. And then she begins to ask me questions about poker, and I explain it to her as best I can.
And when the 10:00 game begins, she asks if she can sit with me and watch me play. OK, no problem! And while we’re playing, she peaks to see my whole cards. And then she asks other poker-related questions. Every now and then, she’d bring up some other topic, but it wouldn’t get too far because we were playing poker.
Well, we finally get to the point where we’re down to the final two tables again, and another older lady joins the table. She introduces herself, and it was at that time, I learned my “new friend’s” name — Melissa. She also finds out my name — Brian. The game (and I’m not talking poker) had changed just a little bit.
Well, I get knocked out of the game just shy of making the final table — again — I’m really needing more practice before the regionals on June 18! So, as usual, I start watching the final table. And Melissa is right there watching too. And when the final game ended, I took a seat at a nearby table, and Melissa joined me.
And the conversation went something like this:
Me: “What are you going to do now?”
Melissa: “Well, either I can go home all by myself, or I can go to your place.”
Just the kind of answer I was looking for. I followed her to her place to drop her car off, picked her up, and came back to my place. She doesn’t even know my last name, we’ve had next to no conversations (unless it was about poker), and she’s going to go home with me? OK!
Well, in the car, we got to do some other talking. And here’s part of where I’m not sure about Melissa. Some of the conversation seemed quite simplistic. She’s a year older than I am (“twenty and fourteen”, she said), and she starts asking me what my favorite color was and my favorite foods and what kind of music I listened to. I was kind of puzzled by all of that.
Her voice also has the sound as if she may be (or have been) deaf or partially deaf. But I didn’t see any hearing aid, and when I’d talk to her in the bar, she could understand me — and we all know how hard that can be in a bar.
But she has the body type that I really like: thin, petite, long legs, small boobs, and a nice ass. Who would I have been to complain?
And when we got to my place, we both sat down on the couch…
… and … (if you’re easily offended, don’t click on the extended entry link below — and
Mom, you’re not allowed to read below!)

… and we talked and talked and talked.
Yeah, I know part of being a guy is making the first move, but every time we finished a topic, and it was “right” to make a move, she started up another conversation.
It finally got to 4:00 in the morning, and I tell her that “I’m just a little shy, so I’m just going to go ahead and lean in.” And then we start making out. Finally after 2 hours!
Well, this was a pretty good make out session! Your typical “kissing, groping, fumbling around trying to unhook the bra, she goes ahead and does it herself” type of make out session. And I started to kiss her on her neck and her ears, and she tells me that she has thing about her ears… and I go back to the “deaf thing” or “possible hearing aid thing “I was thinking before… maybe true?
Anwyays, we continued, and then she pushed me back and crawled on top of me and started kissing me passionately while dry humping me. I was quite content! So, I suggested we go to my bedroom. “Sure!” she says.
And as we start heading there, I pull her in and start making out some more.. still standing there, still in the hall, hadn’t gotten to the bedroom yet.
And as we get to the bedroom, she mentions “I don’t normally do this on a first date” (ahem, yeah right!) and we make out and grope a little more. And then she asks me “if we do this, do you have protection?”
Me: “Yes I do”
Melissa: “Well, you’re going to call me, right?”
Me: “Yes, I promise I’m going to call you!”
Melissa: “You’re not going to be a bastard, are you?”
And at this point, I kind of stop and ask her “You’ve had some guys treat you badly before, right?” She nodded. “Well, I’m not going to treat you like that.” And we continued to play around until nearly 6 am! I’ll put it this way, I’m absolutely certain that she enjoyed herself, and I never even took my shorts off!
So, around 6 am, we try to get to sleep. I don’t know how well I slept, but around 9:00, I’m awake again. And there she is. So, I start rubbing her back, and she wakes up, telling me that it felt good! And I rubbed her back some more, and then she rolled over. And I rubber her front, and she starts to become a little more boisterous (as she had done during the first play session). And I go ahead and put my hand inside her panties.
Well, I play around a little down there for a while, and then she takes them all the way off. And she climbs on top of me, rubbing herself on my leg, and she tells me “I want you!”
Yeah, I heard what she said. But I acted like I didn’t. I kept on making out with her, and doing what I was doing. Until she said it again. OK, I have patience, but I was ready before she said it the first time.
And we had sex. And it was not good!
Oh, it was not good. It was vanilla. It was plain. She wouldn’t let me get all the way in. When we changed positions, she still wouldn’t let me get that far in. And, although I tried, it was only 2 positions before she went back to the first one. Oh, boring.
But I kept at it. And, just like when I was on the anti-depressants, I could not finish to save my life. I finally layed down beside her and said that we should try again later.
And then we both went back to sleep.
Oh, this was the most sexually-incompatible encounter I’ve ever had. She even mentioned that she didn’t like oral — giving or receiving! Ugh! I love both. How can I try again later with this girl when I already have no hopes that it will ever be good?!? Ugh!
And I was sooooo bothered. I told her that I’d call her. And that I’d see her again. But that was before the sex! Buy you know what? Sex is like pizza — even when it isn’t that good, it’s still not that bad! Bad sex is probably better than no sex, right?
And in the back of my head, I’m thinking “Do I really want to call her?” But I said I would. And when I tell someone that I’ll do something (especially when feelings are involved), I have to do it. That’s personal integrity.
So, I called her up Tuesday night and set up something for Wednesday night. And, since I guess I was thinking that it would be just like Saturday — no work involved on my part, I have NO PLAN going into the call. So, I ask her what she wants to do (again in the back of my head thinking that she’d say, come over to my place), and she says that I needed to figure out something — it’s the guy’s job.
And then I realized that although we had sex, I was already taking her for granted. I quickly squashed that thought, and told her not to eat anything before I picked her up, that I’d take her out.
So, on the way to pick her up, I ask her if she’d eaten, and she said that she hadn’t. And I tell her that I’d like to take her to Don Pablo’s, close by where she lives. She mentions that particular Don Pablo’s wasn’t all that great, but she’d go.
I immediately ask her where else she’d like to go, and she says that she’d go to Don Pablo’s. And I tell her “Look, if you don’t want to go there, just tell me. It’s OK”. To which she replies “Well, I was kind of hoping that we could go to Macaroni Grille.”
“Perfect! I’ve never eaten there, and am looking forward to it.” Point: Ladies, just say what you want — don’t beat around the bush!
Well, when I pick her up, she’s wearing some cute, low-rider, patched jeans and a sweater that showed her tummy. Melissa does have a nice body!
We go out to Macaroni Grille, and have a decent dinner. Afterwards, I ask her what she’d like to do. We could play mini-golf, or darts, or get a movie to watch at her place. Well, Melissa decides that she wants to see “BoogeyMan” which had just come out. And we head out to Blockbuster and back to her place.
She changes out of her cute clothes into some “South Bark Jammies” (not so cute) and then we watch the movie. And when it’s over, it’s nearly 11:45. And I know she has to work relatively early in the morning. And so do I. And then, just like Saturday, we begin to talk and talk and talk.
And in the back of my head, I’m thinking that I just need to lean in and start making out. And then she mentions that I could “spend the night if I wanted to.”
And I ask her “Is that what you want?” And she says “I don’t care.” (not quite the answer I was looking for). So I ask her again “Well, do you want me to spend the night?” And again, she replies that she didn’t care. So, I avoid the topic for a few minutes.
And then she said that if I spent the night, I could sleep on her couch. ***(sound of brakes screeching!!!!!)*** I don’t know if she was joking, but I wasn’t buying it. She had just lost her chance at having me spend the night there that night!
I make up some excuse that I should probably head back that night, so I wouldn’t have to fight the traffic in the morning. And then we talked a little more.
And she asks me something like “How did you feel about what happened Saturday night?”
I told her that I had a good time, and that I hope that she had a good time. She said that she did. And then she says that she told her sister about what happened, and that her sister says that she shouldn’t be ashamed about it.
And immediately, I get a little freaked out. Maybe she hasn’t ever done that on a first date before!!! And maybe she was feeling guilty (or similiar) about what had happened.
Well, we talked a little bit more, we kissed a little, and I came home.
And I think I did the right thing by not spending the night for a couple of reasons. First, if she was thinking that I was using her for sex that night, I certainly didn’t need her to think that it was the only reason I called her back. Secondly, we had a nice night together, and it didn’t involve sex. And I’m still not going to be a bastard to her, and I’m going to see her again. Lastly, I’m thinking that this might leave her wanting more.
My female co-workers have assured me that the whole “I don’t care if you spend the night” line was her really wanting me to stay over, but that for some reason, she just didn’t want to come out and say it. Like it would make her sound too eager or like a slut or something. They also say that because of all of the potential sensitivity involved (she’s definitely sounding like she’s been mistreated before), that by not sleeping with her and still wanting to see her, she might feel better about herself.
Well, she has to work this Saturday, but she’s going to meet me at Brittany’s again when she gets off. We’ll see how the poker goes. But I’m more interested in how the “Melissa” situation will play out.
The last thing I want to do is to hurt her. But I’m really confused about the whole situation. Maybe the sex will be better next time.. I don’t know. I will say that the conversation “improved” on the second date — didn’t seem quite so simplistic.
I guess we’ll just see how it all plays out! I’m definitely intrigued by the fact that I don’t have Melissa figured out yet. But something is telling me that I might not want to figure her out. I just don’t know. I don’t see a “long-term” future here. But don’t think I want to cut it off at this point yet, either.