Re[m]iniscing about a New Years Eve [f]orever ago | 2016

New Years Eve, 1998. I was 22 and we decided to go into Chicago to a $60 all you can drink/eat, etc. club. The place was packed. It was one of those clubs with two levels, one with the dance floor and the constant strobe lights and the other was a sitting area. We got there early enough where we were able to get seats but getting drinks was a real pain. We decided to just constantly go up for about an hour and get cranberry and vodkas and stock pile them. It didn't take long before we had an entire table covered with them and we decided to partake heavily. We all ended up feeling no pain and midnight had come and gone.

A friend and I ended up on the dance floor and just kind of hung around. I'm not a huge dancer but I was drunk and he wanted a wingman so I said, "what the hell". He was dancing and I was just drunkenly standing around. The damn strobes were crazy. There would be blinding light and then seconds of darkness where you couldn't see two feet in front of you. It went on like this for a few minutes and I was starting to think I need to go back upstairs before I got a headache. It was cramped and I was getting tired of not being able to see. In front of me a woman was dancing with some guy. She bumped her ass into me. I thought nothing of it as it was a crowded dance floor. She did it again. I was starting to get annoyed. It wasn't a, "I'm trying to hook up," accident - she didn't even see me. And she didn't even look back to apologize. She did it a third and then a fourth time.

On the fifth time when she did it I grabbed her hips and started to grind against her ass. I figured she would push my hands away and go back to her dancing partner. But, she didn't. She started grinding into me harder. I let go of her hips and she continued grinding into me so I reached up and aggressively grabbed both of her tits and squeezed them hard. Part was passion and part was to see what she was going to let me get away with. Neither one of us knew what the other looked like and we hadn't said a single word to the other. I squeezed her nipples through her dress and bras as hard as I could so she could actually feel it through the fabrics. I did this for a minute or two before I moved up and yanked her hair and tilted her head to the side so I could kiss and nibble her neck and ear lobe. She just grinded away and then I spun her around and a full blown make out session took place. I still had no idea what she looked like, it was so damn dark in there. Even when the lights would strobe, I would catch a glimpse and then darkness again. Couple that with the fact that I had an ungodly amount of vodka. As we were making out I forced my hand up her dress and roughly put two fingers in her very wet pussy. She gave out a breath (and possibly a moan, there was unbearably loud club music) and I could tell part of her was telling herself this was the point where she needed to make her decision of how far she was going to let this go - it was New Years and she was by no means sober. All I heard was basically a whisper, even though she mostly likely had to scream for me to hear her, "let's go back to your place." I had to scream back, "I live in the suburbs so that's out." She just screamed back, "fine, my place it is." In ten minutes we went from me getting annoyed she was being rude to me roughly finger fucking her on the dance floor to going back to her place. And, at this point I still really had no clue what she looked like other than she was shorter than me and had short hair.

She told me to wait for her by the door as she told her friends she was leaving (and the guy she was on a date with - sorry, dude, I kind of scooped up your date, oops). We got out of the club and it was such an amazing calm. Between the lights and the noise it reminded me of that feeling when a concert is over and you have those few first seconds for things to calm down and your hearing to come back to normal after the ringing ceases. This was the first glimpse I got of her. She wasn't anything special. A little chubby, older (she was 34), dark hair, nice eyes, had gorgeous tits, and a really sexy British accent. We grabbed the train to her place. Oh, I probably should mention, I never told my friends I was leaving, another drunken oops.

We got back to her place, it was a shitty studio apartment that probably costs way more than it should but it's Chicago, and she offered me a beer which I gladly accepted. I took maybe one sip of it and we were on full blown making out session again (we had a few on the train as well). I was not shy with her body. My hands were all over her and she pulled her dress off. I went to undo her bras while she was on top of me making out. My drunkenness didn't help so I am not going to make myself sound like an expert. She must have gotten tired of my fumbling and reached back and unstrapped it. Her huge tits were free and she yanked up my shirt and began kissing my chest and rubbing her tits on me. She pulled my pants off and my underwear and teased around my dick with her tongue and licked my balls a minute before she took me in her mouth. She licked and sucked me for a few minutes before I pulled her up by her hair and stood her up and yanked her panties down. I told her to turn around and we were in a full fledge 69 with her sopping pussy in my face as she took me back in her mouth. I must have been hitting the right spot because she began grinding her pussy into me harder and harder to the point that I was licking from her asshole up to her clit. She absolutely loved it and exploded and I could taste a whole new release of her juices. After her release she rolled off me.

I pulled up and began pounding into her missionary. This was very primal. We barely even knew each other's names and had very little concept of what the other really even looked like, we went from dark club, dark walk, a few minutes in a lit train, a dark studio apartment. But it didn't matter, we both wanted it to be animalistic and it was. I continued pounding into her and couldn't help myself and exploded in her. I fell into a pile of dead muscle and rolled off her. She wasn't done as she frantically began working her clit and brought herself to a second orgasm. That was the first time I ever saw a woman masturbate and it instantly started me on round 2 (you got to love alcohol and older women - a whole lot of inhibitions gone and knowing how her body works).

We just laid there and I instantly started getting handsy again. This time, I used my finger and slowly started to circle her asshole. She just kind of laid there as I entered her ass with my finger. She let out a moan and I pushed in a little deeper as I followed her moans which definitely increased in volume. Unfortunately, I had too much to drink and didn't think my actions through so I didn't properly lube her so what started out as that, "this hurts in that good, naughty way," to, "this just kind of fucking hurts." She just said, "ok, I can't take that." Those words for some reason really turned me on. The thought that I had brought her to a place where she had to submit. If I had to look back at my sexual history, I would say this was the woman that made it clear to me that I like being in charge and dominating in the bedroom.

I was instantly hard as a rock again and didn't even say anything. I just turned her over and put her on all fours and entered her from behind. I began pounding again and got a little bolder and started slapping her ass. And, I mean hard. Bright red hard. I said to her, "you love me spanking your ass don't you," which she answered a very excited, "yes!" I said, "you love me pounding you from behind," she responded an orgasmic, "yes!" And she exploded again. It didn't take long before I couldn't take anymore and pulled out and came all over her ass.

At this point, I had to call my friends. My pager was going off every five minutes and it was just getting annoying. I asked if I could use her phone and, of course, she didn't have one. Damnit! She said there was a pay phone at the laundry mat on the corner. This was before everyone carried cell phones. So I got dressed and ran down to the corner, called my friends, and told them I was fine and started walking back. Fuck, every one of these building looks the exact same and I didn't write down the address. Drunken luck somehow made me remember which one was hers. If not, I would have spent the rest of the night in a Chicago cell.

Walked back in and she laid on her stomach falling asleep. "Hell no," I thought and stripped and laid down next to her. I pulled my hand back and slapped her ass as hard as I could. She instantly yelped and came to from the sensation. Before she could even get a word out my tongue was down her throat and my hands were exploring her body again. Her pussy was still soaked from all of the activity and she was already aching for me. I roughly fingered her and teased fingering her ass again which she would ease towards my fingers and then pull back. In the morning we talked about that and she said it was really exciting not knowing if I would do what she asked me not to or if I was just so into the moment I was going to do whatever the hell I wanted. It gave her a real thrill of being completely out of control due to my passion. After a lot of teasing she got on top and put me in her. She rode me and rubbed her clit. She also rubbed her ass hole and at one point put one of her own fingers in as she rode. Her moans had turned to borderline screams and she rode me and fingered her ass. I took over rubbing her clit while she took care of the other end and she rode faster before she exploded again. She rode me awhile longer and I got one last orgasm out of her before I had to admit, I wasn't going to cum again. Too much sex+too much alcohol=I was spent. She said that was ok since she was unbelievably sore and, "a broken woman," from the spanking, the ass fingering, and the pounding her pussy took.

We fell asleep and woke up the next morning with plans to meet again (we never did). I then came to the realization that I had no fucking clue where I was and still a little hammered. She gave me directions to my friend's house which was seven fucking miles away. I spent most of the morning getting lost before I finally found it. When I got there and rang the bell, one of my jackass friends stuck his head out the window and yelled, "hey man, did you get laid!" It was loud enough where neighbors could hear. The answer was fine, a resounding yes!