Thursday, June 25, 2009

Fiends with Benefits, Part I

Auto-posted at 11am while I am on a flight somewhere over the Atlantic. More auto-posts coming, and I'll be returning tomorrow evening.

March, 2008:

Beward the Ides of March! It's my favorite holiday, actually. The one where the people revolted and took down their monarch. What is better than revolution? I prefer peaceful revolution, of course, but it's still a holiday to celebrate.

I was semi-seeing Lena. She was a mix of 16 races and I'd say she had the absolute best combination of each. She wasn't pretty, really. She wasn't hot. She wasn't cute. She wasn't what I normally considered someone I'd date. But she was sexy as hell and looked good in EVERYTHING. Lena was my most recent sugar-baby. We had some sex, here and there, but I didn't really get into her as much and I think she sensed it. It was good sex, but nothing mind blowing (not for me at least).

I still loved seeing Lena in great outfits, and when I had particularly good jobs, we'd go out and splurge a bit. After returning from a trip to South Africa (I was TANNED and I was CUT because of surfing for 5 days straight), I called her up and asked if she had found any digs she liked. "Nothing much. Oh, wait, I did find something!"

Lena was the perfect sugar-baby: she never asked for things, and when I proposed shopping, she rarely bought. When she did, it was always something we both loved.

"Shoes!" Uh oh. Shoes are a tricky part for me. If I buy a woman shoes, she's getting fucked in them, that day. I don't care WHO the woman is, but shoes are a line drawn in the sand. Usually with Little Fire Hydrant. Shoes?

"Yeah, I found this little boutique in the city. And I'm horny. And I know you're horny. Let's get shoes." Let's! We made plans to meet around 1pm at her place, and I arrived a few minutes early. She was dressed for success, and I was excited to see what shoes she found.

We drove down to one of Chicago's many boutique neighborhoods and popped in the shoe store. She went to find her shoes while I browsed other women's shoes to see if I saw anything I liked for her. The store had tons of great smaller boutique brands, but the styles were just boring to me. As I wandered down the long and thin boutique searching out Lena, I passed the check-out counter lodged in the middle of the store.

"Hi!" said a young-looking brunette. I turned to look at her and replied back. "Looking for something for your wife or girlfriend?" No, just a friend. I pointed at Lena down at the end of the store. "Oh! She's been in here before. Does she have something in mind?" I think so. I look at the gal closer, and she reminds me of a friend of mine from high school. So I ask her name.

"Kari." Nice to meet you Kari. She smiles and I turn to see what Lena is trying on. Sadly, she doesn't find her shoes, which happened to be on sale and were already sold. Neither of us is sad, so we prepared to say goodbye to Kari when she added "We can order you shoes, even those that are on sale." Lena jumped up at the chance after looking at me for approval, brought over the style she wanted and asked for her size. "You're going to love these, they're really comfortable. Who should I call when they come in?" Me.

I wrote my number down and made a joke about being the most frequent customer at women's shoe stores it seems. Kari laughed at it and let her hand glance mine that was holding the paper. Interesting. I looked up and her eyes were twinkling and her smile was wide. I didn't break the glance as I pushed my name and number towards her.

"Thanks, I'll call you next week when it comes in." Lena and I left and went to her apartment. We fooled around a bit on her couch but didn't have sex. It had been over 2 months since we had last fucked. I liked seeing her in pretty things but I didn't really like fucking her. Ugh. I was horny, too.

We made out for a bit, went and grabbed a bite to eat, and I told her I'd give her a ring when the shoes appeared. A few more kisses (she WAS a great make-out buddy) and off I went.

2 days later, I had a call: it was Kari. "Your shoes, err, your friend's shoes are in." Awesome, that was fast! "We had another order from the same company so they put them in the boxes. When should I expect you?" Later today.

I zipped over there, Lena was at work and she had a first date with a guy later that night who she met online. I was on her ass to date more, and I figured good shoes wouldn't hurt her chances of meeting a decent guy. When I got to the boutique, Kari was working solo again. And she looked better than just a few days ago.

"Hey, Chicago!" she said, remembering my name. I go by Sane, if that's OK with you. "Sure Sane. Again, I'm Kari." I remember.

We chit-chatted while she rang me up. "So she's not your girlfriend?" No, not at all. "You buy your friends shoes?" It depends on the friends. Clothing, usually. Not shoes generally. "Your girlfriends, too?" Rarely. I haven't dated a lot lately, so it's mostly friends. "With benefits?" Something like that. Whoa this gal is forward. Her eyes were twinkling still, and she had the cutest smile.

"Want to hang out sometime?" AND STRAIGHT FORWARD. I wouldn't have expected that from her, but she did show the signs of interest. I accepted. I asked for her number and said I'd call when I was free. "Hopefully soon, I've been bored lately." Me, too.

I grabbed the shoes and zipped to Lena's. "Was that gal all over you again?" Haha, the shoe girl? "Yeah, she's cute and she digs your shit." She asked to hang out. "Ohh, you should TOTALLY do it." Maybe. "No, she's cute and she's your type. Why, don't you think she's cute?" Definitely. Eh.

Lena tried on the shoes and she looked great in them. Awesome purchase. She was meeting her date at 8pm for a late dinner and asked me to check her over. I thought she looked lovely and told her so. "Oh, Sane, you're so fucking precious. We should fuck, soon." Sounds good to me. In truth, we never did again.

The next week Lena had told me about her date (crash and BURN touchy-feely dork). She reminded me to call Kari, who I had honestly forgotten about. So I did, on a Tuesday evening. Her phone rang 3 times and she answered it. "Hi?" Hi Kari, it's Sane. "Ohhh, hi! I was just thinking about you today, wondering if you were going to blow me off." Why would I do that? "Guys have been weird lately." Tell me about it.

"So are we getting together today?" Again, aggressive. I like it when a woman CAN be aggressive, but not when she's ALWAYS aggressive. I told her tonight was bad, but I was free Wednesday and Thursday. Two options, friends. "Wednesday! What do you want to do?" Afternoon or evening, I asked. "I work until 6 at the shoe store, so maybe 8? Food or beers?" I don't drink beer, but drinks is fine. Food is, too. "How about somewhere quiet?" Done, I'll pick the place.

She gave me her home address (a good sign of interest, actually) and I promised her I'd see her at 8. I was a bit concerned by her enthusiasm (don't get me wrong, I love when the ladies like me!). I had a recent history of breaking hearts and was trying to get over that. It's not that I played around a lot, but I dated a lot and found myself bored a lot.

I never understood it until recently: when a gorgeous guy dumps a gal, she usually accepts it. She knows he's out of her league and at least she "got with him." When an average-looking guy decides not to move forward, it hurts the woman's self esteem. Maybe it hurts more. I decided to play it cool with this one, let her come to me if she wants it, and see if I want it, too.

More in Part II auto-posted later today. Yes, I'm a tease.