I was frequenting a pharmacy near my apartment, I had a minor rash on my arm which refused to go away and ended up going through a couple of ointments before my PD managed to guess the right prescription. Lucy was working at the counter, she was the sweetest girl and always had a big smile when I walked in. She had this adorable awkwardness about her,  like she was slightly nervous all the time but tried her best to help you out. I had a sneaking suspicion that she liked me and her colleagues also started to notice what’s going on, but I was in my late 20s at the time and swore an oath of never bothering women at their workplace after realizing that I was pretty obnoxious in the past.

I was pretty attracted to her. First off I’m gonna sound like an asshole, but she wasn’t conventionally stunning. She was about 5’2’’-5’3’’, chubby and blocky, with a slightly crooked nose, and I could tell that she was self conscious as hell. But again, there was something about her that made all that superficial stuff irrelevant. An extra thing  was the fact that she was basically a carbon copy of my ex-coworker with whom I had a short fling that I  fucked up, and it very much sent me for a loop the moment I saw her. That girl had a no-nonsense, take-no-shit attitude and a curly, red hair, while Lucy was meek and had straight brown hair, but everything else was eerily similar.

I continued being cordial with her, with no intention of making a move, until one day, I think it was my  fourth visit there, as she was ringing me up she awkwardly slips me a piece of paper and makes the phone hand sign. I smiled at her and nodded and she just bolted to the back of the shop, her coworkers were laughing and I could hear her telling them to shut up so I smiled at her colleague who was also holding back laughter and headed out.

Around evening I figured that her shift had to be over so I decided to call her and she answered almost instantly. I tried to joke around a little, asked her if she remembers me and so on, but she was a nervous wreck so I just went down to business. I told her that I’m not looking for anything serious and that I don’t want to waste her time if that’s not ok with her, there was a long pause but she just said that’s fine. I suggested a time and place and she said “Sure, that works for me.” like she didn’t even think about her schedule, and before we said our goodbyes she asked me if I really want to do this. I asked her what she meant and she told me that I don’t need to do this to make her feel better, that she understands if I want to bail out of the date, she went on for some time before I cut her off and told her that I simply wouldn’t have called her if I wasn’t interested. That assured her enough and we awkwardly ended the call.

She was almost half an hour late for the date, I figured that we wouldn’t get far right away and didn’t expect for it to last that long, so this was a sizeable chunk of time. When she finally arrived I could tell that she spent way too much time in front of the mirror overthinking things, her makeup was slightly overdone and her choice of clothes just felt a little off. I normally don’t give a shit about these things, but with her it was just too obvious. She apologized and sat next to me, and it was up to me to carry the conversation for the entire date.

Yeah... it didn’t seem like it would work. I would get her to talk for a minute at a time and then would have to restart the conversation the moment she ran out of things to say. If it wasn’t obvious by now she was nervous as always but while it was a little charming in the beginning it became a major drag. When she did say something unprompted it was a self-deprecating joke along the lines of “can’t believe you wanted to go out with me, haha”. Just off-putting and a little sad. The whole thing lasted way too long before I told her that I need to go and offered to walk her home, she thanked me for that and apologized for being boring. I didn’t mind really, I’ve had bad dates before and it wasn’t really that terrible, but her lack of self esteem was really something else.

When we got to her door I felt bad about the idea of just leaving her, especially after how badly everything else went. I could tell that she was fine with a goodbye kiss so I leaned down, and oh boy were we both fine with it. By the end of it we were making out in the hallway, eventually we did come back to our senses and I broke away. I didn’t want to push things any further so I smiled and told her “Wow, that was great”. We wished each other goodnight and off I was.

Without that third act twist I would’ve never suggested a followup meeting, but there was definitely some tension between us. I intended to call her again, but she was way ahead of me and texted me asking if I want to meet for a coffee. So our next two dates were little cafe meetups after work.

Both of these went much better than out first time. She was a LOT more confident and playful, we had a decent amount of common ground and by the end of the third date she even started being a little naughty with me. I said something pretty harmless and she hit me something like “oh you just want to get me naked, don’t you”? I played dumb and told her “well I thought that the feeling was mutual”. She got a little shy after that, we didn’t push it any further, but we did afterwards arrange another proper date.

I was getting ready for the date when she told me over text that she’s not feeling like going out, but we could still hang out at her place. She really should’ve told me earlier, this was 20 minutes before we planned to meet, but I knew what her calling me to her place meant so I really couldn’t be mad. I was already dressed for a night out but being overdressed never killed anybody.

When I got there she was dressed very casually, a gray tracksuit that seemed to be one size too small, but it looked so fucking good on her. It accentuated all the curves, her big juicy ass, I’m not usually a fan of large tits but on her frame they looked great. She commented how she feels a little silly next to me in my shirt and jeans, but I just told her not too worry about it. She offered me a drink and we ended up on the couch, I think that the idea was to play some game she had but the air was electric and we ended up making out before she could explain the rules to me.

The chemistry was as good as the last time, her mouth was wet and hot and she was mumbling and moaning as I worked my way across her neck. She wasted no time and immediately put a hand on my crotch and started feeling my bulge out, I responded in kind and started grabbing her ass and tits. I put one hand down her pants and grabbed her cheek as hard as I could, she was either wearing a thong or her ass swallowed her panties. She squealed and laughed, I continued playing with her ass while she slowly started unbuckling and unzipping my pants.

When my cock was out in front of her she stopped and stared at it for a couple of seconds, it was obvious that the size took her by surprise. She slowly grabbed it and moved it around a little and said “Ummmm... okay...”. She looked at me like she was unsure what to do with it, I told her to jerk it a little but soon she lowered her head down and started blowing me.

It was one of the worst, toothiest BJs that I ever received. Like she was being horrible at it on purpose, just comically bad. I tried guiding her a little but she was either too nervous to take my advice or didn’t want to, in any case I told her to stop and we got up and awkwardly took the rest of our clothes off. She sized me up and I could tell that she was comparing herself to me and that it was destroying her self esteem. I proceeded to finger her and she seemed to like that, when I moved to eat her out she stopped me and told me that I don’t need to do that. I told her that I really want to, but she wouldn’t let me. She took me to her bedroom and we had some terrible sex in pitch black darkness. I got used to younger girls insisting on doing it with lights off, but this was just laughable, she even closed the door behind us completely so that there wasn’t a speck of light illuminating us.

Even when pretty bad, sex is pretty good, but like I said this was just awful, me bumping against her in missionary. She couldn’t take me at all, she was wet but still not enough and tensed up completely, after a couple of minutes we both faked an orgasm and went back to the living room. We sat down on the couch and I tried to lighten the mood a little and joke around, but it was like that first date again. I hated the idea of excusing myself, but she was just in a complete shutdown.

Then she turned to me, made a face like she’s summoning courage to say something, and hit me with this:

“Look, don’t take this the wrong way, but you do know that you have a huge penis, right?”

That question had me hyperventilating for a solid minute. It was just such a perfect icebreaker too, she was embarrassed by me laughing so much and punched me a couple of times but it did wonders for her mood, she was much more open about sex-related stuff and we spent the next hour or so just talking about sex, life, and relationships.

She apologized for forcing the sex to happen so soon, it normally took her a lot to open up sexually and trying it out with a guy like me who was at the time playing the field  was way out of her comfort zone. I told her that I would be fine with waiting a little longer, but she said that she wanted to prove it to herself that she can do it. And to her coworkers, since they originally encouraged her to make a move on me, she told them that I was cute and they told her that there’s nothing to lose by giving me her number.

I asked her about that big chip on her shoulder and she wouldn’t budge at first, but she opened up pretty quick. She told me that she had zero confidence in her looks all her life and that she finally decided to do something about it not that long ago, trying to date was one of the things on the list. She was only with one guy before me and she felt unwanted during all of it, and both before and after that guy she felt looked over. Other guys would sometimes make her feel like she has to do something for them to earn their affection so apparently she also had shit luck and ran into her fair share of psychos.

She asked me to honestly tell her if I found her attractive, I said I did. She asked me to explain what exactly attracted me to her, I told her that I really don’t know, I just definitely felt an attraction towards her and that was about it. We talked about “rating” people and how she feels like she has to make up for her physical shortcomings, I was direct and told her that I can see where she’s coming from, but that if I found somebody sexy I’m just attracted to them, I don’t grade them against myself and then force them to make up the difference.

She also asked me if she was annoying me with the questions. If you didn’t figure it out by now, I was at the time and still am a very vain man with a huge ego, and it’s a good  thing that I’m tall, well endowed and conventionally very good looking (my coworkers used to describe me as “that hot guy at the office”). I told her as much, and that I love being complimented and reminded of my good looks and other blessings, but that her constant need to put herself down was really grating and the only real turn off for me. That segued us into debating the importance of a woman’s personality when it comes to sexual attraction, after that it was something about her job etc.

By the end of it I asked her if she wanted to try again, she wasn’t ready to go all the way, but she wanted me to make her feel good so I ended up making her come with my hands, and it didn’t take that much to do it. She told me that she doesn’t really know how to handle my size (apparently I was much, much bigger than that first guy), I instructed her how to jerk me off with two hands and in a minute or two I covered her little hands completely in white. She laughed about how much came out and was very happy knowing that she can make me finish. We cuddled after that and she told me that I can stay the night.

We continued seeing each other after that, we did manage to find a common ground in the bedroom and she overcame a lot of her mental blocks. We had to take it slow most of the time, it took her a bit to get ready both mentally and physically. After having sex a couple of times we reached a plateau of sorts, truth be told while we did enjoy each other’s company we weren’t that compatible sexually. She did overcome some insecurities, but masked others by joking around them. I’m fine with a little humour in the bedroom but I want the mood to be hot and heavy for the most part and we just didn’t vibe in that regard. In addition to that the actual sex was pretty vanilla, I tried to push her a little and encouraged her to be rougher, but it just went nowhere. I was also meeting a female colleague at the time who also had some self image issues, but sex with her was mind blowing, so it was doubly obvious with Lucy that our chemistry just wasn’t that strong.

As for my size she was an odd one, it impressed her visually but she wasn’t much of a size queen. Physically the size didn’t to much for her, she did say that she loved feeling filled up, but I could tell that it wasn’t her cup of tea. She described how my dick “squishes” her pussy, i.e.  with the most of it in she felt funny, like there was just too much cock inside of her. I was able to make her come but it did take  a lot to get there, on the flip side she came really hard during penetration. Then again, there were some hiccups, if I went too deep it would kill the entire thing. Also, most of the time she would queef like crazy, again something that I didn’t really mind, but it was really embarrassing for her.

She loved playing with my cock though. She would size it up from time to time and say “that’s how a dick should look like”, sometimes after having sex and laying next to one another she would grab it and dreamily comment “it’s just so pretty...”. Some of her requests were also a little weird. She would spoon me from behind, both of us standing up, then reach around and start jerking me off. We would do this in front of a mirror and she would glance over at my cock, the whole thing did very little for me but she loved it and I had no issues playing along. A less crazy thing that she liked was the two of us sitting in bed facing one another and touching ourselves, she would come really quickly while looking at me stroking it.

As a sidenote, much like myself she really liked asses. I was told a couple of times that I went too far with my ass fever, so being on the receiving end of that gave me a new perspective haha. But yeah, she was crazy for my ass, she clawed, spanked, grabbed, even bit me a couple of times, I had to tell her off a couple of times.

This went on for a couple of months, it would probably end much sooner but she was also great to hang out with, and we would even go out together with her friends. It was pretty obvious that she was showing me off in front of them, being a self-absorbed asshole I couldn’t get enough of it. There was also one girl in the group who seemed to be really pissed off that she found somebody. One time when Lucy wasn’t around she approached me and started bitching about Lucy and asked me how come that I couldn’t find someone better than her. I just smiled and told her to fuck off.

Still, at the time I was hyper focused on getting laid and just chasing the muff around all day, and Lucy just didn’t scratch the itch as much as I wanted. It was also obvious that she wanted something more serious so she decided to date other people as well. We never really called it off, but we just stopped reaching out and setting up things. I did see her in the neighbourhood a couple of times and we would keep in touch that way, but nothing came off it.