Shoulda, coulda, woulda.  

TattooedWolf 48M
72 posts
6/4/2005 8:27 am

Last Read:
3/5/2006 9:27 pm

Shoulda, coulda, woulda.

I’m looking for opinions with this entry. A very close friend of my says I could have fucked this woman and I say there wasn’t a snowball’s chance in hell. I’ll give you the details and let you decide.

Kim was a friend’s little sister. I have known her since she was a sophomore in high school. Petite, Italian girl with dark eyes and a smoking body. Forget all that “never date your friend’s sister” crap. I would have crawled though broken glass on my hands and knees to fuck this girl. Totally and completely infatuated.

Move forward ten years. I’m out of my marriage and “little sister” is all grown up. We ran into each other at the gym and caught up very quickly. She had just been left at the alter. No shit, I know someone who was stood up and their wedding day. I told her I was sorry to hear that and she seemed to have moved on. Since our workout schedules were the same, we saw each other most every day. Conversation was effortless and we developed a friendship. We saw each other outside of the gym as friends. I went over her place, she came over mine, we’d club together on Fridays nights and meet for breakfast Saturday morning. Kim always had a thing for Italian guys who treated her like shit. Don’t know why, it’s just how she was wired. I tried making a move or two but it didn’t seem to go anywhere. I was “THE FRIEND”. The ultimate kiss of death for a guy. The designation that ruins any chance of getting laid by this girl. I might as well have been a gay, impotent, eunuch. The upside? She was pretty cool to hang out with and she had a bunch of hot friends. Plus i was doing quite well myself at this time. I wasn't feeling the pressure to get laid. We would hang out and we swap sex stories. I’d tell her about how I ate so and so’s pussy until she came in my mouth and Kim would tell me that she had rubbed her clit raw the other night because she was so horny. The image of her fingering herself gave me masturbation material for a few nights.

Now down to “THE MOMENT”. The day after Kim’s birthday, I stopped by to see what was new. She was showing me her birthday presents and one of them was a lingerie set from Victoria Secret. Kim held it up and asked me what I thought. I told her that I couldn’t really tell unless she had it on. To my surprise she disappeared into the bed room and came back out with the outfit on.

“What do you think?”

I had been waiting for this moment since high school but had been relegated to being "THE FRIEND”. To be honest the lingerie didn’t look good on her, but it did offer a fairly good view of the rest of her. She had the biggest areolas I had ever seen. I told her I thought she could find something more flattering and that was it. I don’t know if she had caught me during a moment of self-doubt or if I knew that it wasn’t going to happen. Whatever the case may be, if I had a chance to fuck her it was now gone.

Kim started dating a guy a few weeks later and cut off all contact with everyone, including her girlfriends. I haven’t seen her in years, but a mutual friend ran into her about six months ago and said she looks like hell. Kim’s obsessive about her weight and working out. Apparently she’s gone to far with it. The mutual friend says that she doesn’t looked toned anymore, she looks drawn.

So readers, I put the question to you. When Kim came out in the lingerie, was she giving me the green light or was I “THE FRIEND” and she saw it being no different than trying on a dress? I’m curious to hear your thoughts.


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