B's Dating Life

This is pretty sad: going to bed the last couple nights I’ll lie there and try to think of some clever lines for the hot 40ish woman at the gym (who hasn’t been there this week, bitch). No matter what I come up with it sounds gay as hell, cheesier than a shirtless fat guy at a Packer game with his cheese head foam hat on. I have two things going against me.
1. She has to be at least 9 or 10 years older than me.
2. I’m a shy pussy (at least when sober).
These two conditions will ruin any chance I have of actually asking her out to dinner or something. First the age thing, what do 40ish women do for fun? I know she plays softball and likes to workout, but what about after 5:00? Go home, do laundry, cook dinner for her 20 year old daughter (wonder if she’s hot, little mother/daughter tag team action? Gross, I’m sorry), read a book and go to bed? Whereas I get off work, go to the parents for free food, go home and maybe go jogging, sit on the deck and write stupid shit on the internet while drinking vod/lems and downing three pitchers at the corner bar, finally going to bed in the 11:00-12:00 range (a boy needs his sleep). I’m guessing her life is completely different from mine, everything from her goals to her interests (well, we share the common interest in getting butt ass naked together and having hot Bruce Banner sex at first and then The Hulk/porno sex to seal the deal, I haven’t asked her yet but I’m sure about this one). Is she going to get pissed at my almost 30 and still can’t date anyone longer than two months mental state and rip me a new asshole (trust me, I shit enough as it is) when she thinks everything is going well and I’m screaming at the guardsman begging him to let me out of jail? (Please, I have Snickers and Twix for you if you let me out!) (Actually, you’re looking thinner lately, have you been working out? I have a granola bar in that case.)

Or, on the other hand, maybe she’s one of those older women like Stiffler’s mom in the American Pie movies, the kind that just wants the younger man for hot steamy sex and that’s it (oh I could totally go for that). Usually older women know what they want and go for it, but I’m afraid if that were the case she would have said something by now. Really, I’m not that innocent, I just look it, I’ll gladly screw you and leave promptly after. And I’m pretty sure you’ll be calling back for seconds. Unfortunately I think she’s too nice to have this dark side in her.

Then there’s the shy pussy thing. When sober I’m not the greatest with people I don’t know too well, usually try too hard to either think of something funny or to explain something without going on and on like a broken record. This goes for both sexes. I catch myself stammering a bit thinking of the right words to say. When drinking shit flies out of my mouth like sperm from Ron Jeremy as he cums on ten women in one shoot. (If you don’t know who Ron Jeremy is please look him up, just not at work. I actually saw him in Vegas once.) I’m not exactly sure what shit will come out of my mouth, but usually it’s entertaining and the only black eyes I’ve gotten lately are from falling on my face in an effort to walk. I mean hey, I must be saying something right in order to get women from the bar to go home with me (once every three months). So I lie there at night, trying to go to sleep, thinking up conversations with this woman and replaying them in my head, and I’ve come to the conclusion that everything I’ve come up with would only would while we were both semi-intoxicated and in the bar setting (please remember I’m thinking this shit up while trying to pass out). This is the only real courting I’ve done in, oh I’d say 8.5 years since I turned 21 (legal drinking age in the States). After age 21 I stopped trying to do the traditional dating thing as I just don’t have the patience for it and don’t want to spend the money for a kiss goodnight (geez that sounds bad). I’d rather pull some random woman home and pretend to be in love with her and we have drunken sex on my bed (or on the floor after we fall off). I can pretend pretty well. This way I don’t have to deal with calling the next day, taking her out to dinner, meeting the parents, or attending lame family functions like Thanksgiving and such.

But I’m getting off track, I don’t know if the proper word is “shy” but I think I might be more afraid of letting the real B out and try to sugar coat it a little. Would people find the real B entertaining and interesting if they really got to know me? I’m getting more comfortable with the old lawyer as I asked him if he thought hot 40ish’s boobs were real or not. That’s just part of the real B coming out, or Brian to him. I guess only time will tell, I’ll give the 40ish woman some shit about not using enough weight or something lame like that and see where it goes. Like I said, I’m a pussy.