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In my late 20s I worked at a pretty chill company. My previous workplace sucked the soul out of me and this was a perfect change of pace. The work was easy enough, the pay was decent, and the people there were fun and always ready to either party or go for a drink. We were all self-aware enough to know that the company itself was kind of a joke and was hardly useful to anyone, but we were all fine with it and just enjoyed the easy life.
There were a couple of bars around and there wasn't really a day of the week that was off limits, so being a little hangover on Wednesday was nothing special. People from my department would go as a group and put a couple of tables together, but as the night went on people from every department would mingle together, so we did drink with people from all over the company.
On one such occasion Tara was there as well. I didn't know her that good at the time. She wasn't from my department, but I spoke with her once or twice and we did move in similar circles, so I did get a feeling for what she was like. She was low energy, bitchy in that cynical, snarky way. There was something adorable about her so her somewhat nasty takes were almost endearing in a way, and she was mostly shitting on company and management so nobody really took offense to her complaints.
She was a little older than me, early to mid 30s, barely 5', with small tits and a flat ass. I didn't really think of her in a sexual context, she dressed in a very old-fashioned way and was usually slouched over. As far as I was concerned she existed and worked at the same company as me, and that was about it.
As the night went on the crowd thinned and we got a chance to talk to each other in detail for the first time. We had more in common than expected and we were both a little tipsy at this point so almost no topic was off limits. Others continued to call it a night and eventually it was just the two of us, I figured that we both knew how strange of a pairing this was, but talking to her was a blast and we went on for an hour at the very least.
We breached the topic of relationships and sex, and she took a deep sigh and abruptly started talking about her love problems. Apparently she was in a loooong relationship that was limping on for way too long and a about a year ago she finally decided to end it. After that she had little luck with men, with a shitty date disappointing her every now and then. She was pretty honest that she was dying even for something short term, and all but admitted that she was sexually frustrated. I said that it sucks and that I know the feeling.
She sized me up and told me that she wouldn't take me for a guy with such problems. I laughed and figured that she was entitled to a detailed explanation, so I went over the three years that I spent at my old job and how fucking miserable it was. I admitted that the worst of it was the fact that it fucked with my head so much that I couldn't perform with a girl that I was seeing at the time, and that it took a couple of months to get my mojo back. She said that that sounds fucking terrible and that she's glad that I'm out of there.
She then asked me if I managed to bounce back. I laughed and told her that I was currently making up for lost time, barking up every tree and taking every chance I get. She rolled her eyes and told me that she knew that I was a fuckboy. She smiled while saying that, like the idea was entertaining her, but still made it sound like she was putting me down. She asked me if I'm already fooling around with one of our female colleagues. I told her that I wouldn't tell her even if I was.
Tension started building up, and by the end of it we both had our hands on each other's legs and were really close to one another. I could just tell that she was undressing me with her piercing blue eyes so I decided to make a move. I asked her if she wanted to hang out at my place and after a short pause she shrugged and said sure, why not. I paid for what was left of our tab and we got into my car and drove to my place.
She gave me shit for driving drunk, and while I wasn't "drunk drunk" I was definitely at a point that warranted calling a cab. It was definitely a stupid, irresponsible thing to do on my part. We got through the door and we weren't ready to go just yet, so I put on a movie and offered her a drink, and we sat on the couch. She didn't wait long to get going and within five minutes we were all over each other, making out and grabbing whatever we got our hands on.
She eventually climbed onto my lap and started grinding against my bulge. She laughed and asked me if I'm going to make her regret this, I assured her that a gentleman never kisses and tells. She moved to the side and started unzipping my pants, and soon enough she pulled my boxers down and my big fat cock flew out and slapped against my stomach.
She paused for a sec with a classic "Fuck, that's a big dick" look on her face, but her reaction was strange. She looked at it almost like she was disappointed, then grabbed it with her tiny hand and moved it around a little. Squinting and scoffing she said "You really are an asshole, aren't you?". She continued to jerk me off with both hands, then leaned in to spit on it a couple of times, getting it nice and wet. She did it like she hated it.
She let me know that she would never let me have her if she wasn't so desperate. I had other girls do the whole "you know that you just got lucky" angry talk, plus I've always found a little animosity during sex hot as fuck, so I just leaned back and enjoyed the sight of a little vixen working my cock while pretending not to love it. Eventually I told her to stop fooling around, she rolled her eyes and started blowing me.
It was obvious that she had no chance of taking it deep so she sucked the tip while stroking the shaft. She wasn't outstanding at it but she knew how to spice it up, she kissed it along its full length, slapped her face a little with it, cupped my balls and sucked on them, all the while shooting me nasty looks every now and then. I made her raise her ass up while blowing me so that I can give her a proper slapping, after which she told me that I'm by far the biggest asshole that she had to deal with.
We stood up and got completely naked, after which I made her kneel in front of me and continue where we she left off. She continued putting on a show for me, and I loved how small she looked next to my throbbing cock. It was fairly obvious what my kink was and she picked up on it, at some point she smirked and said something to the effect of "I would never let you treat me like this if your cock wasn't so fucking huge.". It made the sight of her little mouth being stretched and stuffed all the more enjoyable.
I picked her up and carried her off into the bedroom. I played around with her pussy, pinched the lips, fingered her, and eventually eaten it like it was my last meal. At this point she was completely drenched. Still, I could barely fit the second finger in and it was obvious that the penetration will have to go extremely slowly. Her faked anger seemed to subside somewhat, and she told me that I was "not so bad". I made her come at least once and soon it was time for the real thing.
There was lube involved, but my size and her tightness slowed things down considerably anyway. She tensed up which made things worse and at first I could barely get the head in. It was obvious that she was anxious and her trashtalk completely stopped, so I tried to make her as comfortable as possible and told her how hot she is and slowly moved my hands all over her body. My cock gets wider at the base and also has a very pronounced upward curve, so I kept adjusting the angle and slowly pushing it in.
We made good progress, half of my cock was still hanging out, but we were at a point that was enjoyable for both of us. Her bitchiness came back, at this point I focused on resizing her pussy and trying to make it as stretched out as possible. I leaned in and whispered how great it feels, how firm the grip is, how much I wanted her etc. She altered between telling me to shut up and moaning with pleasure, "you piece of... fuck, you're twice as big as... I fucking hate you..."
She came a couple of times, each time she would push me away when she started climaxing and started touching herself until she was done. It would take her a minute to get her bearings, after which we would continue where we left off. Each time I could go a little deeper, until after almost half an hour I told her to raise her ass up and climbed on top of her. I had several women tell me that this position unlocks "secret inches" for them, as I said my dick is curved and at this angle I could use my full length. With Tara that wasn't really necessary, since I already couldn't fit in entirely, but she loved it anyway and was soon coming yet again, this time with my cock still inside her. Bottoming out in her sent me over the edge and we both collapsed on the bed and took our sweet time before getting up.
We eventually managed to crawl back to the couch, she was completely exhausted so I went to the kitchen to grab us a glass of water. When I came back she was completely spaced out, dead silent, just staring into the distance and not reacting. She finally moved and said "fuck, I really needed that...". She glanced at my dick and mumbled something about "that fucking thing...", then smiled at me and told me that I really know how to fuck a girl. I asked her if she's okay and she said that her body is on fire, but in a good way.
I asked her about the whole "I hate you" spiel, and she looked pretty embarrassed about the whole thing. She apologized for springing it on me out of nowhere, I told her that it was really hot and that she shouldn't worry. There were a lot of things happening in her life and she just needed to vent, plus she was really annoyed by certain things that I said and she just wanted to call me an asshole a couple of times. I could also tell that she was second guessing her decision, we talked about that as well and she made me promise not to tell anyone at work. I said sure, and she said that she'll kill me if I do.
Of course, we also talked about my size. She told me not to get arrogant, but that it was the best cock that she ever experienced, and that she was caught off guard by how much she loved it. It did hurt at times, but according to her it was mostly the good kind of pain. She could tell that I was being careful with her and the idea of a hung guy having to slowly work around her tightness made her feel really dainty and feminine. The biggest shock though was how much she loved blowing me, oral was always a chore for her, but having my throbbing cock in her mouth was exhilarating. She loved feeling the veins with her tongue and struggling to fit more than the head in, and just the sight of it made her feel like she had no choice but to kneel and open her mouth. Just the act of sucking it almost made her orgasm, and she called me an idiot for picking her up just as she was about to climax. Stoic guys who barely react during sex also pissed her off, so having a guy who moans, talks dirty, and bites his lower lip was a nice change of pace.
She essentially confessed to being turned into a size queen over the past hour or so and it got me pumped for round 2, but she told me that there is no chance of that before her lady parts heal a bit. Naturally, she suggested oral instead, and knowing just how much she loved it made me finish super quickly and she milked a fat load directly into her mouth.
We overslept by an hour. I dropped her off at work, then waited for about 15 minutes so that we wouldn't rise suspicion. Again, the company was a joke and my boss barely commented on me being late.
She avoided me for about two weeks, then reached out to me and we arranged another meeting. The first time she was really friendly, she welcomed me in with a warm smile and during sex there was no bitchiness on her part. Don't get me wrong, it was still great. Roughly at 20 minute mark she was too sore and I had to take it out. She then proceeded to give me a sloppy blowjob and continued to do so two more times, commenting how her jaw is killing her, but that she just couldn't stop. This was our usual routine, first sex, then repeated blowjob sessions until I couldn't get it up anymore. At first she was decent at it, but over time she became insanely good, choking and gagging on it, trying and failing to jam more than half of it down her throat. Sometimes I would facefuck her and she would come and seeing her eyes roll back was just insane. In the past I did come a couple of times from eating pussies and asses, but I never had a girl who came from blowing me before I met Tara.
In time however she did get annoyed with me, and it would be a coin flip on any given day if she would be mad when I met her. When she was she liked me to be a little rougher and to take a lot of shit from her, and I allowed her to spit, slap, punch, bite, and claw, while I would usually slap her ass, slap her face with my cock, grab her hair, and generally physically move her around. One time she was especially nasty and I could tell that she wanted me to be a massive dick to her, so I said fuck it and went all out. I made her kneel in front of me and beg for a chance to taste my cock, then when she did I denied her and started to order her around, made her shake her ass for me, spread her cheeks, stick her tongue out and act like a little slut. She called me an asshole for making her act like a whore and I grinned knowing full well that she loved being bossed around by a big cock.
All in all we had a great thing going, I was a total manwhore and loved the arrangement we had while she was brutally honest that, while loving the sex and my size, she couldn't see me as boyfriend material in a million years. She had a thing for artsy poet types and I couldn't have been more of an opposite, so she liked having me as her fucktoy and a bootycall while she was out looking for the One. She did admit, while she wanted this hypothetical Prince Charming to be almost nothing like me, that she hoped that he would have one thing in common with me. She also liked the fact that I always used protection and was getting regularly tested, which put me ahead of 99% of guys already. Truth be told I wouldn't have minded hanging around with her when we were not having sex, we had a couple of interests in common and she was smart and a lot of fun, but she made it clear that she doesn't want to see me with clothes on.
At one point she stopped reaching out and I assumed that she found her catch. I was at a party one evening and she texts me asking me where I was and if I could come see her. The party was close to her place and I said sure, but that I wouldn't be able to stay for long. She said that's fine and told me to hurry. When I got there she was pissed and just wanted to do it right away. She kept telling me to be rougher and rougher and calling me more names than I go by, until I decided to pin her down and fuck her like she stole something. When we were done I took my things and went back to the party, while she was still passed out in her bed. When I saw her at work two days later she was walking with a limp.
This went on for some time until one day she wanted to talk with me. She called things off and told me that she needs to think some things through, and that she will reach out to me when she's ready. It was kind of odd but nice of her, FWBs would usually just stop calling and fade over time, so having a definitive closure was a nice change. I was hoping that we would start fooling around again, two times she did reach out just to change her mind at the last moment, and we never set up anything again. After I switched jobs I didn't hear from her again.
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