Fumbling The Bag- Missed Opportunities that Still Haunt Me Pt 1

I've had some great highlights in my sex/relationship life, but I've had some low one's. Here are a few:

-Young Angela ("She Keeps on Passing Me By" 2008):
I worked for an apartment complex and was trying to f**k anything that looked good that lived there or visited, and I did have success. One in particular, however, was sexy as hell single mom but I opted to play it cool and not make any move on her. She looked liked a young Angela Basset. She wound up moving in below my apartment and surprised me one day with a plate of food she prepared. I figured that was my cue so we exchanged numbers and would talk on the phone. I'd try to invite her up or myself over but she never bit.

She had a line up of about 3 guys that would spend the night on occasion and I'm wishing I'd have my turn with her. So one day, my dumb ass decided to invite her out for dinner, thinking if I wine and dine her, maybe that'll work. We go out, come back, but she declined my offer to extend the night further.

Of course, barely an hour later, one of her guys pull up to spend the night.

I had what was easily the most pathetic jerk session of my life that night... To top it off, it started raining like crazy, like a scene out of a movie. Down $100 with my d**k in my hand after watching someone else getting ready to f**k her in real time.

-Da Brat:
A lesbian couple moved in and the one that was the more "boyish" one kept flirting but I didn't pick up on it right away. She was actually very cute and still dressed like a girl in form fitting clothes, but she'd wear hats and Jordan's, for example. By the time I realized what was going on, I had my nose open for a crazy Latina that lived there that I had started seeing. Not that I wanted to stay exclusive, I was just so sprung that I didn't have the time and energy, which I wish in hindsight that I had done it. She wound up moving early after they broke up, and lamenting on the failed relationship, on her way out told me that she still likes guys but she just got tired of getting her heart broken.

I ran into her a few months later, but she was looking like she had lost the weight that gave her a gorgeous shape and looked more boyish and bummy. I got her number but never could bring myself to call after what I had seen. Saw her again some years later but she was now looking like a real boy and we just spoke briefly and kept it moving. She still remembered my name and I had forgot hers in the moment.

-Ren and Stimpy:
A pair of roommates moved in and offered me a massage as reward for taking care of them professionally. They reminded me of Rem and Stimpy because one was tall and chunky and the other was short and skinny. I wasn't interested. I was picky and didn't want to f**k big girls and the other had the body of an 11 yr old boy. As time when on though, I started to realize that the big girl was actually really cute (chunky with proportions not Jabba the Hutt fat) and the skinny one started dressing sexier and fixing herself up, and the potential for my first threesome (and only, as time has thus far proven- Oh yeah, also blew it with the lesbian from the previous account) with them would be a win. The door was now closed though, and my advances with the small one got shot down and the chunky one now had a bf she was into.

-My Drake Ambitions:
We had a young 16-17 yr old girl come in trying to figure out what she had to do to get an apartment or who she could use. She was semi-homeless, very advanced and street smart. Her body was amazing and drove me nuts. She was looking for any angle she could play and somehow I couldn't resist giving her my number. If you had asked me then, I would've said that I'd never mess with a young girl, but all bets were off with this one.

She wound up crashing at my place on a semi-regular basis but never let me do anything with her, see her naked or anything. At one point, she offered me sex for $80 because she was in need and I turned her down. I only had about $140 to my name at day, and plus, I didn't want to feel like a trick (even though I always was at that point basically). The only thing I got out of the arrangement was a DVD she let me keep of some modeling photos she had left my place to have done, so I did get to jerk to pics of her bare ass and areola slips as a consolation prize.

Turned out (no shock) that selling p***y is what she did to get by. I have paid a few times since, but then, I was young and thought paying was for guys that couldn't get any on their own merit.

A few years later, she was legal and wound up moving into another complex I now worked at, but I never tried her again. I was pretty much friend zoned so she'd come into the office just to run her mouth to me.

I was at a work conference out of state on Bourbon St. about 5 yrs later and I stumbled into one of the strip clubs and lo and behold, guess who worked there? That turned out to be a horror in itself as I got wasted and was ordering myself and her stripper friends top shelf drink concoctions I had ordered at home, but at this place, come to find out when the tab came, they charged me like $70 a pop! I lost about $500 in there and damn near had to run out of there and escape those teasing succubi. I was making pretty good money then (even though that $500 could've been better spent) so the impact was more to my pride, and the embarrassment of my conference mates finding me disoriented, humiliated, and having to help me back to my room.

Had to have been Voodoo some something, I thought I had evolved to the point where I couldn't get caught like that. I haven't gotten that drunk anymore after that night.

-The Wyatt and Josie Love Story from Tombstone That Never Was:
A cute teacher that was my age got an apartment for her brother that had gotten out of jail and had got a job and trying to get his life on track. She flirted, I got her number and we had some really great chats on the phone. Before things could get to the next level, her brother was murdered at his apartment. One of my coworkers got an apartment for his thug nephews that his sister was trying to get rid of. They were breaking in everyone's apartments and broke into her brother's apartment. He stormed into the office pissed, said he knew who did it and stormed out. He confronted the boys and they let loose on him, fatally striking him as he ran back into his apartment. Some of those bullets actually passed through his apartment, the one behind him, went across the street and into the building on the other side. Needless to say, me and her fizzled out. Not my fault but still a tragic way for me to miss out. RIP to him, though. It sucks that the good guy lost that one.

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