Seducing The Ugly Duckling

I’ve flirted with this girl on and off as she transformed herself through diet, exercise, and mental improvements.  This is the story of finally closing the deal on her:

You know that girl that’s cute and just needs to lose weight? The one that tries really hard to make a change and loses that weight (keeps it off) and the girls get a little jealous because now she’s getting some attention and people are remarking at how much better she looks?
Yeah, used to work with her doing events, she stopped working for that company but I kept on. Was supposed to go with her roommate and my girl friend (after work, we all worked an event together last night) to visit this chick at a bar local to my place where she was watching a band perform (she knows the drummer).

Her roommate bailed as I was driving home separately, my friend parked in front of my place and we walked over to the bar. On the way there, chick texts me saying if I’m still coming over they’re in the back and she would appreciate if I walked her to her car afterwards (late at night she didn’t want to wait for band to break down their equipment). My spidey sense started tingling or maybe that was just the drinks I’d had at the event and the long island I downed at my house.

I’ve been wanting to bang this chick more and more as she went through her semi-transformation. Because I want to and because it’d be kind of a reward for all her hard work. It sounds right in my head at least. Arrived at the bar, it was remarkably empty, walked past the bouncer no ID check for my friend who didn’t have anything on her (did I mention we were in full costume still from the event we worked?). I have this place mostly on lock. Get some beers from the cute bartender and I make a mental note to try to work on in the future.

Rest of the time at the bar is flirting, having fun with both girls and eventually getting them all dancing which looks ridiculous in the costumes my friend and I have on. The band sits with us on their break then play our requests in their last set as we have a blast on the dance floor. Pretty damn good time for a nearly empty bar (compared to any other week). I walk them both back to my place and hand out waters. My friend hugs me and goes home and the chick asks me for another water. I oblige, we flirt trying not to wake up my roommate and then I just grab her and start making out.

Things start getting hot and heavy, I’ve got my hand down her pants and she’s rubbing my crotch. She asks if anyone else is there/lives there and I take it as my queue to answer her by grabbing the back of her hair and making out/fingering her while she is forced to walk backwards into my bedroom. One of the rare ocassions when my bed isn’t made and there’s shit EVERYWHERE (had to turn my room/closet upside down looking for my costume) so I just push her down on the bed and shove shit off as things get hot and heavy and we have some treats for halloween.

Favorite moment is when she starts cumming and lets out a sexy but loud moan/gasp and quickly puts her hands across her own mouth to try to stifle it but can’t quite. She offers to go home after but I tell her to just crash as she has to be up in 4 hours. I pass out then walk her to the door when her alarm goes off, pass out again, then get up and put a couple huge steaks in the slow cooker and douse them in pepperoncinis/juice for me to feast on tonight after it’s been simmering for 8 hours and will be fall apart tender.

Did I mention I have plans to get drinks with the hottest girl working the event from last night too? It’s a good day to be a man. Happy Halloween motherfuckers.


~ by aneroidocean on 10/31/2013.

3 Responses to “Seducing The Ugly Duckling”

  1. congratulations man! great story. was it as easy as it sounded, or were there some moments of doubt or resistance?

    • It was pretty easy if you count flirting with her on and off for the better part of a year or two easy. Never really made a move on her, just left it flirty and capitalized when she wanted to be alone with me. Would’ve totally banged her sister instead but this is what presented itself.

    • I didn’t get much resistance more like incredulity and she probably feels a bit of a slut since I haven’t heard from her about hanging out since.

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