I used to work with a cool rich guy, let's call him Tim. His parents were loaded and barely home, so he would throw a party every now and then at his mansion of a house. This guy got me laid more times than I can count, there was a tone of attractive women in his friend group and the parties were a blast so it was easy to chat girls up and break the ice. In addition to that there were a lot of rich people attending these, and befriending them led to being invited to even more parties. It was either that or Tim just telling me "Hey, so and so called, wanna tag along?" and I would just say hell yeah and come along.

One time I was attending a party hosted by Ellen. She seemed to have a similar thing going on, rich, mostly absent parents, so she organized stuff at her penthouse, it was this absurdly large apartment. I met her before since she was usually invited to Tim's and there was some tension there already between the two of us, one time she was dropping hints but I actually ended up hooking with somebody else so it went nowhere.

Frankly she wasn't my type personality-wise, she was a spoiled girl that didn't have to work a day in her life and she droned on about strange, irrelevant things. She also adhered to some strange diet that made her super skinny, it was not quite vegan but also had additional strange restrictions, in any case it made her borderline emaciated. She was usually wearing some pretty revealing black dress that looked like it would slide right off her if she turned her arms the wrong way. She was definitely attractive, dark brown eyes, black hair always styled perfectly in a different way, really pretty face, alabaster white skin. But she would've looked much better with at least 10 pounds extra, she had a nice figure but no curves, and stuff like her coral bones and ribs were just too pronounced. She was about 5'5'' but fuck me if she was much over 100 pounds.

In any case that time we ended up chatting, just the two of us. She was always very friendly with me and this time was no exception, she would listen intently to any dumb thing that I had to say and laugh too much at jokes that just weren't that funny. She was also very physical, she would feel out my arm, put her hand on mine, push me when it was opportune, slowly moved very close to me etc. I didn't mind, as I said she wasn't really my type, but I'd lie if I said that she wasn't attractive and at the time I chased anything that moved so I was more than happy to see her like that.

Eventually she asked me about Jenny, another girl that I also hooked up with at one of the parties. I told her what about her, she's grinning and asking me if the two of us are dating, I'm like nah, nothing serious came out of that. She then asks me what it was like with her, I laugh and ask her why doesn't she ask Jenny about that. She says "oh I did, I already know everything", and I say good, happy with what you heard? She smiles knowingly and says oh yeah, it sounded like fun. I think to myself "fuck it, she's hooked" and ask her if she's down to have some fun tonight herself. She's a little shocked, for a sec it seemed like I came on too strong. However she tells me that she will call me when the party is over and to come back to her place then. I gave her my number and shortly after that me and some friends hit the bars.

I glanced at my phone every ten minutes, as the hour got late I guessed that she got cold feet, but just as the clock was about to hit 3AM she texts me to come over. I excused myself and went straight to her place. When I came there she was ready to go, she sized me up and by the look in her eyes I could tell that she was mine for the taking. So I did. I put my hands around her waist and we started making out, but we ended up bumping into some stuff left over on the floor. I lifted her up, carried her across the room to a spot that wasn't so messy and pinned her against he wall, then let her down and continued making out with her. She broke away in a couple of seconds and said "fuck, that's so hot." I moved onto her neck, she shivered and led my hand up, I took the hint and lightly choked her, she moaned like a complete slut and I just knew that I was going to fuck the shit out of her that night. She then lead my hand to her crotch and sure enough there was no underwear there, only a wet pussy that begged for a fingering. She was melting with me kissing her neck and with one hand between her legs, but apparently she had other things in mind because she dropped to her knees and started unbuckling my pants.

She grabbed my cock at the base and took it out, then proceeded to stare at it for a second or two, clearly surprised. She then smiled and just softly said “oh fuck yes” and I laughed and asked her if Jenny told her everything about me. She laughed and said “No, that bitch!”. I wanted to feed my ego some more and asked her if she likes men with big ones, she just smiled knowingly and gave my engorged head a gentle kiss.

I was never crazy about getting head, but she was amazing at it. Worked my shaft and balls, knew not to push herself too hard, used both hands, never broke eye contact. She took it out and slapped her face and tongue, made comments about how she liked the feeling of it in her mouth, asked me to choke her while she was blowing me etc. In a couple of minutes I was about to bust, I tried to break away and change things up but she told me that she wanted me to finish in her mouth so I grabbed her and she pushed it down as deep as possible and I emptied my balls down her throat.

I was still at full mast and ready for the next thing, she smiled and commented on it after I pulled her up and continued to make out with her. She then abruptly apologized to me and said that she’s tired, I was kind of taken aback but couldn’t really be mad, if anything it felt like I owed her one. She then told me that she wants us to meet sometimes next week, I was more than happy to hear that so we exchanged numbers and after I put my pants back on asked her if she needs help cleaning up. She gave me the wildest look and I figured of course, she has somebody who does that for her.

She reached out to me in a couple of days and we arranged to meet again at her place after I was done with work. Her place was on my way home so it was pretty convenient, if anything it was a little early in the day for a meetup like that but I didn’t mind. So I arrive there and she’s wearing a black dress and tells me that she’s been waiting for this all day and I’m yeah, me too. She takes me to the living room and lifts her arm straps up and moves them to the side and her dress just fell to the floor, she was wearing no bra nor underwear and looked really proud of that little display she just pulled off for me. I managed to take off my shirt before she pounced on me and told me to carry her towards the sofa.

She was all over me and insanely horny, to the point of it feeling weird a little. She was fully naked and I still had me jeans on and she grinded against my crotch like crazy, she didn’t seem bothered by that one bit. She had long polished nails and made a point of pushing them into my back and chest as she trailed all over my body, and she moved down my neck to my nipples and sucked, squeezed, and lightly bit them. The nipple play was never my cup of tea but she loved it and gave me such a look while doing it that I was perfectly fine with it. She really took me by surprise and started of things in a very dominant way, in any case I was all for it.

This took a while but eventually we started talking dirty, about the anticipation and stuff we would do to one another. We were going in detail when she locked eyes with me and asked me if I want to do anal. I was taken aback for a second and told her sure, we can do that at some point. The moment after I said that she got off me, grabbed my hand and took me to her bedroom. In a second it turned from a pretty steamy foreplay to this awkward walk to another room, and once we were there she had this huge smile on her face, she looked kinda crazy with that smile and her wide eyes. She pointed to the bed and told me that we’ll do it here, then just... assumed the position, laid on her stomach against the edge of the bed and pushed her ass out. Mind you I still had my jeans on, she just told me to get naked and fuck her ass (I’m not paraphrasing here). Despite still being pretty shocked I had a solid erection, and the moment she saw my cock she bit her lip and told me to that she can’t wait to get fucked hard by that thing. I’ve asked her if she’s prepared herself, she just got somewhat annoyed and told me sure, let’s do it already. I’ve tried pushing in one finger, then two, she wasn’t lying, she obviously did her prep. There was no lube though and she was so fucking horny so I just said fuck it, applied some spit to my cock and around her ass and pushed the tip in.

It was like she got possessed. She went “Oh my fucking god!” the moment the tip of my cock slid in, then just became louder and louder as I worked my way deeper. It felt just so... off, compared to my previous experiences with anal. I wasn’t a fan of anal at the time, but I did at that point fuck my fair share of asses already so I knew what to except, or at least so I thought. Ellen was just completely consumed by the sensation, moaning like a slut and telling me to fuck her asshole, fill her up, push that fat cock deeper etc. She didn’t react to anything else, I tried touching her around her body but it didn’t really register for her so I stopped, and reaching around I found that she was already finger blasting herself so there wasn’t much to do on that front. The rest of the world didn’t exist for her, just my big cock plowing her tight ass as it throbbed all around it. Eventually her second hole opened up after I put her in a face down, ass up position and fucked her at a better angle, and she went silent and started letting out a quiet “ooh... ooooh... oooooooh....” before falling silent again. I managed to push about two thirds of my cock in when she came super hard and tensed her ass up even harder, my cock felt like it was about to be snapped in half, luckily that didn’t happen.

I managed to get out and get up. I checked her afterwards, there was no tearing but she was in a rough shape, extremely red and with a slight rash around the entrance, eventually she fell to the side and looked back at me with an expression of pure bliss, she looked happy and had a wide smile on her face. The whole thing barely lasted five minutes, but more than enough for me to fuck her brains out. She barely got up and laughingly commented how I fucked the shit out of her, then did that bow-legged limp to the bathroom. I sat on the edge of the bed and took a moment to come back to my senses, she came back and told me to sit back and enjoy, then got on her knees and started tasting her ass off my cock. She was amazing at giving head and it didn’t take her long to finish me off, after that I gave her a sloppy kiss and took a bathroom break myself before we finally laid on the bed.

Much like everything else, the pillow talk was also weird. She seemed obsessed with my cock, balls, and midsection in general, said how she can tell so much about me by those parts of my body, and I was like okay, but here I am, you can just ask me like a normal person. Having her rave about my looks felt amazing for a short while, but it became weird eventually, she was essentially doing palm reading but with my dick instead, and talked about really weird things. I would say something back and she would look me in the eye but barely respond, if at all, then continued her monologue while staring at my cock. As weird as it was being objectified like that was a massive turn on so I got hard, she jacked me off and I finished on my stomach, after which she lapped up every single drop of cum.

I excused myself shortly after that, she didn’t mind. Next day I got up and still felt like my dick is being choked around the middle, as if it was still in her ass. Like I was wearing a cock ring that was way too tight. Later that morning I was at work and my phone fired up, sure enough it was Ellen. She messaged me about how her ass is on fire and how I fucked her brains out, I remember grinning to myself and texting back that she knew what she was getting herself into, she’s like not really, didn’t try a dick this big before. She knew how to stroke a guy’s ego, I asked her if she’s learned her lesson, she said no and insisted for us to meet again next week. The way she was acting I was fully expecting her to suggest that we meet right away.

So the day arrives and I’m finishing things up and my phone starts ringing. It’s her. I ask her what the hell, it’s 2PM, she says that she needs to be fucked hard and that she’s been preparing herself for me all day. I tell her to wait and hang up. Five minutes later, same thing. I blocked her and went about my business, but at point I could no longer concentrate for shit so I said fuck it and headed out. My job at the time was kind of a joke anyway.

I got to her place and she let me in with crazy eyes and a crazy smile. She looked like she was ready for a night out on the town, black dress, makeup, she put some effort into the whole thing so it actually made me think that I might get some foreplay this time around. The moment we were both in though she took me to one of the rooms and just got on the floor, lowered her head, raised her ass up and pulled her dress up as well, just offering her ass to me. At this point I wasn’t that surprised so I just stripped down, by the time I was naked she was spreading her cheeks apart and telling me to hurry up. So I just shrugged and proceeded to destroy her ass.

It was the same thing all over again, she prepared herself ahead of time so I just applied some spit and the moment my engorged head overcame that initial resistance and slid in she went ballistic. She screamed and yelled, told me to fuck her like a whore, to fuck her hard, to be rough. It was painfully obvious that my cock and her ass just weren’t in the same weight class so I held back, she didn’t seem to care. As I went deeper she eventually started to quiet down until she came, this time I could see it coming so I pulled out before she clamped hard. I continued to finger her ass and pussy as she came even harder this time, then left her with her ass still up in the air.

I made sure that she was okay and left her to drool a little on the floor, when she managed to recover somewhat I grabbed her by the hair and made her slowly crawl on all fours. The moment I did that she started grunting and moaning, we slowly made our way back to the bed, then I sat down and pressed her face against my shaft and told her to get to work. She locked eyes with me and laughed like crazy, then proceeded to suck my cock like a pro. It didn’t take long before I was shooting thick ropes all over her face and her black dress.

After that we settled into this raunchy foreplay => anal routine. She liked being debased and manhandled, wanted to spit on me and having me spit on her, and absolutely loved being slapped and choked, either by hand or by cock. She also had other demands, but I drew the line at those. She also had a shitload of sex toys, I’m not the biggest fan of those, but if a lady was into them I would oblige. She would put a leash around my cock and balls, and also one around her neck. She would sometimes ask me to fuck her with a dildo, surprisingly enough the ones she had were on the smaller side, not that long and pretty thin.

Sometimes she was down for vaginal sex, under the condition that I kept her ass stimulated during all of it. That wasn’t  a problem for me, putting a thumb up a girl’s ass during doggy was hot as fuck, but that was not quite good enough for her, she wanted me to use one of her dildos. Now for those who don’t know, there is a rather thin membrane separating the two, if you’re doing what I was doing you feel like your cock and finger are touching. And if the girl is too tight, you can actually push your finger out with your cock. Ellen was extremely tight, and while I tried to make things work, the dildo just wouldn’t stay in all the time. She eventually got frustrated and we switched back to anal.

She had one thing that would get her off hard and would insist on us doing it every time. I tried spicing things up with different things and positions, frankly I liked missionary the most because I could see how she reacted while I was pushing deeper and deeper, but face down, ass up position worked the best for her, so that’s what we were doing. She was very selfish and annoying in that regard, but no way close enough for me to call things off. It was low effort, guaranteed sex for me.

Most of our encounters were pretty much the same, one time that stands out happened when I got drunk the day before, not shit faced, but enough to be hangover. Funny thing about me, when I get drunk I’m super horny the next day, and luckily for me I had a meeting arranged with Ellen that same day. So the moment I got there her I pushed her to the floor and stripped down, meanwhile she assumed the position and spread her ass for me. The moment I pushed it in she went crazy, this time I was at my absolute biggest and fattest and hard as a rock. I fucked her into submission and decided to show that ass no mercy,  while she could normally last at least 3 minutes she was done in 30 seconds this time around. I made short work of her ass and she clenched hard, but I barely felt it, however I could tell that she wanted me out so I pulled out. I came to my senses as I saw what a complete mess she was and immediately got worried. I asked her if she was ok, she eventually turned around and said something to the effect of “Holy shit, why don’t you fuck me like that every time?”. Still, she was in no shape for round 2, so I had to settle with getting sucked off three times in a row before my erection finally died down.

What eventually made me call the entire thing off were Ellen’s increasingly weird demands. She suggested some things that I wasn’t ok with and she would normally took the hint immediately, but she insisted on some things repeatedly until I gave her a pretty decisive NO. The first such thing was her insisting that we make a home video, I basically laughed in her face when she first brought it up, but she wasn’t joking. She told me that it’s fun and that I would love it, she apparently did it before and offered me to show some of it to me. I told her fuck no, she promised she wouldn’t show our homemade porno to anyone (after just offering to show me some of her previous works...) and I eventually had to yell at her to fucking drop it. She finally accepted that no means no.

What killed the whole thing for good was her last tone-deaf suggestion. She suggested that we have a threesome, the two of us plus a male friend of hers. I immediately rejected it, just told her that I’m not into that, she insisted that I should give it a try and that she was sure that I would like it. Apparently she told the guy about me and they've already had a similar thing arranged in the past, it boiled down to the two of them getting fucked by the third guy, in this case I was to be that third guy. Her friend didn’t like it that much before (he prefers women, but was open to bottoming), but she told me that he was very much interested in meeting me and getting the same treatment as her. I just told her that I’m not bi and that there was zero chance of me doing this.

She seemed to have dropped this one as well, however one day I got to her place and she wasn’t alone, there was, you’ve guessed it, another guy there. She told me that it’s her friend and that he was about to leave, she just needed to get something for him and that she would be back in a minute. I was ok, let’s give them the benefit of the doubt, but I could tell from the get go what they were trying to pull. I tried talking to the guy, I say tried because he was really slow and slurred almost every word, I barely made his name out. I think he was trying to tease or provoke me, but in all honesty he seemed like he has some sort of mental insufficiency, or was at least on some kind of a drug. In any case Ellen came back, sat down and after a very brief and awkward silence turned to me and said “So uh, wanna do this?” I just got up and left. I was calm at first, but as I continued walking my heart just started pounding like crazy. It’s so fucking funny to retell now, but that whole thing freaked me out back then.

I stopped meeting with Ellen after that, blocked her, and never again attended a party at her place. I would still see her a few times, one time she approached me and tried to smooth things out, but I guess she got the hint. I also saw her friend once, he ignored me and eventually almost got into a fight with another guy there, eventually the host told Ellen to get him out of there. A couple of girls noticed my change of attitude towards Ellen, they teased me about it and told me that I’m not the first guy to get burned, I just laughed it off, hoping that they didn’t know too much.