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This story actually happened and I’m telling it only from memory.
New Year’s Eve 2008, my friends and I got invited to a party in Chicago at another friends house. It was a high school friends place who I didn’t talk to that much anymore but had seen recently and she had invited a group of us to go down there. I actually hate NYE. It’s a big to-do, expensive, usually a let down, and usually more fun if you’re dating someone. I was 100% single at this time.
I dated a ton around those years but I never could settle on anyone. I’m a pretty good looking guy, athletic build and tan skin. I wasn’t picky on looks, I dated girls of all ages, sizes, looks, etc. Anyway, I was in my 20s and single, hooking l up with women pretty often.
A group of us drove down to the city to go to the party. I was actually wavering on going, I didn’t want to have to drive back that night and HATE the hungover drive home the next day. It’s the worst.
I ended up going and having a pretty good time overall. Lots of old friends and some new ones at this party. It was about 11pm when things got weird.
I started talking with my friend’s cousin. She was much older than me, likely 42-43 years old, was single, but I had always liked her. I was about 25-26 years old at the time. She was funny and we hung out every once in a while wi th my friend and his family. Big Irish family and they love to booze. I had zero romantic aspirations with her. In fact, she wasn’t even that attractive. Not a great face, but had a big fat ass and huge tits. I didn’t really check her out too much because we were literally just two people who occasionally hung out and laughed a lot. She was just that, my friend’s funny cousin.
We were doing our thing that we always do, arguing about whether or not we liked tequila or Jameson better. I was pro tequila and she loved to shove Jameson down my throat. She was funny and a big drinker. I remember we were in the kitchen with 3-4 other people in a group when she asked me if I wanted a cigarette with her. I of course said yes, not thinking too much of it, so we went outside on the balcony and had a smoke. I remember she asked “How old are you again?” I answered and I remember her saying “ugh your a baby.” I said something after that that made her laugh but I honestly don’t remember what, I think it was some sort of innuendo because we always joked like that. Like I said she was really funny. Her reaction was definitely different this time. She said “Oh you have no idea what I would do to you.” I remember laughing but being intrigued by that response.
Backstory: my buddy had told me a crazy story about her getting arrested and her whole family being ashamed because she had gotten caught fucking at the Holiday Inn near where we lived. I guess they were in the hot tub outside, had gotten a little horny and when the cops showed up she was butt naked l in the grass behind a tree getting drilled from behind. It was a hot story and I think I had jerked off to that image before.
I remember I replied something along the lines of “I could handle myself. I know you would love it.”
After that she gave me a look. I’ll never forget that look. I think in her mind she was thinking, “I think I want to take him home.”
As she looked at me I turned to her and kissed her on the lips. I remember asking “Are you okay with that?” She replied “definitely.” Like I said earlier it wasn’t even midnight yet and the party was still going. I remember she asked me, “Do you want to get out of here?” I replied “Yes, let’s go.”
Fortunately, or unfortunately, she said we have to sneak out of here though. We cannot be seen leaving. I nodded and said “okay, I’ll wait for you out front.” She had to grab her bag, since I think she was staying the night there or somewhere else in the city.
I waited out front while she did got her bag. When I was walking down the balcony stairs my friends saw me. I told them I was leaving and they busted out laughing. “With who?!?!” They all said. “With Kate(not her real name).” I laughed and said “Yes but don’t fucking say anything.”
I knew they wouldn’t stop talking about it all night but I said fuck it and left anyway.
I met her out front a few minutes later and she had her bag. We walked for a bit to find a cab when she got a text from her friend “why did I just see you leave with —-?” We laughed and she said “Oh shit.” But we left anyway.
We got a cab a few streets down and headed back to the suburbs. She lived in the same town as I did. It was about a 45 minute ride from the city. When we got in the cab she immediately started kissing me. She started grabbing my dick in the car and actually took it out. The cab driver was ignoring us but I could see him watching occasionally from the rear view mirror. I remember she kept looking at my dick as she jerked me off. After a minute or so she said “I want it in my mouth.” She proceeded to blow me right in the car. She sucked a great dick. She was so experienced. I didn’t cum, but I did start to grab her ass as she did it. I pulled up her dress from behind and started rubbing her pussy. I will never forget how loose she was. I don’t know if it was from fucking a lot or just naturally but she had a big pussy.
We fucked around the whole way home and when we got there we were both ready to just take our clothes off right there. We got to her place, walked in the door and she immediately ripped my clothes off. She said, “Fuck, I’ve been wanting to do this for so long. All those times you were at family parties I wanted to take you home but I couldn’t.”
We started fucking right there in her foyer. I bent her over and just railed her. She was sooooo into it. I slapped her ass a bunch, each time she moaned louder and just kept talking dirty. “Oh my god, fuck me hsrder, just like that, your cock feels so fucking good.” It was incredible. After a while we went to her couch and she rode me for a bit, again she was really experienced and knew exactly what she wanted. I was sitting on the couch while she rode me facing away from me so I had her big fat ass in my face as she hopped up and down. I was grabbing her ass and her tits at different times, and at a certain point I decided to start fingering her asshole. I took some of her wetness and stuck my middle finger right in her asshole. She didn’t even stop for one second and I stuck my middle finger deep in her ass. I fingered her asshole so fucking hard. It made her moan so much. She was basically screaming right in her living room.
After a while I said “I want to fuck you in the ass.” She said “Go for it, I want to feel you fucking my ass.” I stuck my dick in her ass super easily and proceeded to fuck her so hard. It was incredible. I’ll never forget looking out of her sliding door into her balcony, our reflection in the window, her on her hands and knees while I stuck my cock deep in her ass. Such a hot memory. I was so horny and we’d been fucking a while that I was about to cum. I remember at that point she had me pull out and she proceeded to suck the cum right out of my cock. Straight ass yo mouths. That was the first and only time I ever did that. Fuck that was hot. She swallowed every last drop.
We ended up fucking a few more times that night. In the shower, in her bedroom and even on the balcony. She just have a kink for public sex because it was her idea to go out there and fuck.
She was amazing.
I never fucked her again after that night. I remember she drove me to my place and as we walked down the street to where her car was, one her cousins, my friends sister, texted her and asked “Why are you walking down the street with —- at 830 am?”
We both laughed and said “oh well, it was worth it.”
I saw Kate a few years later after I was married and she was walking down the street with an older guy. They were drunk and we chatted for a bit. I could tell she was reminiscing our crazy night together. Not sure if she wanted to fuck again, but I had my wife with me. I didn’t tell my wife that we fucked, but the rest of the night I could only think about that crazy NYE a few years earlier.
Kate. What a fuck we had. I hope you are married and hopefully still a sexual goddess. I’ll never forget that crazy night.
This is 100% true. Feel free to message me with any questions or additional details. I will respond.
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