Woman Seduces Ex’s Best Friend On New Year’s Eve

“Josh" was looking to get laid to kick off New Year’s Day, but he wasn’t expecting his best friend’s ex-girlfriend to land in his lap. Read his story, as told to The Naughty American, and find out how she gave him more than a New Year’s kiss.

It was New Year’s Eve 1999, and my three good friends “Mike,” “Brandon,” and “Ryan” and I wanted to celebrate in style, so we rented a hotel room at a high-rise in Chicago and invited a bunch of people to party with us. We arrived early to decorate the place, set up the music system and the bar, and got our pre-party on.

My girlfriend and I had recently broken up, and I didn’t have a date with me that night, so I was searching for that New Year’s Day kiss – and then some. I stood out that night, because I was the only person wearing a shirt and tie, plus I had bleached my hair to give myself a little punk-rock edge.  I was trying to combine the “bad boy” and “suave” images to increase my chances of getting laid.

There were only a handful of people there when we kicked off the party around 6 p.m., including my three buddies, two of whom had girlfriends who also came along for the party. As the hours went by and we drank and ate, more and more people began to trickle through the door. Pretty soon there were about 20-25 people in this medium-sized hotel room, which made for a rather cozy setting. We had the music up high and the curtains drawn to expose the skyline, and everyone was drinking, eating and having a good time.

I had been keeping my eye out for single women that night, and from what I had noticed, there weren’t too many of them there. The women who were available weren’t up to my standards, but at that point I had thrown my standards out the window; it was a new millennium, and I wanted to celebrate it with hot sex. The one chick I knew I might have a chance with was “Christine,” the ex-girlfriend of Brandon, whose current girlfriend was there, too. Christine was hot, especially in the tight black dress she was wearing, along with her high heels. But I wasn’t going to try to hit on my best bud’s ex, especially right in front of him. But she was a little firecracker with a high libido, which was illustrated the time she fucked both Brandon and Ryan at the same time in a car. I wanted a piece of her, naturally, but I wasn’t about to become my buddy’s enemy. So, I turned up my game about an hour and a half before midnight to see what I could get from any of the single women. By the time 11:30 p.m. came around, I hadn’t received any favorable responses. I decided to just keep re-upping on the beer and see what happened. If worse came to worst, when the ball dropped, I’d just grab some lonely chick and plant one on her.

Well, worse came to worst and I was empty-handed at 11:59 p.m. Oh well. I stumbled over to the table of plastic champagne flutes, filled up with some cheap Brut and stood before the television to countdown. Looking around, I saw a few rather unattractive women standing alone. I picked the best of the litter and decided she’d be my New Year’s kiss. When the countdown came, I turned to walk over to her but was stopped by … Christine!

She looked up at me with sex tigress eyes and said, “Where are you going?”

When the ball dropped, she tugged on my neck and pulled my lips to hers. This was no peck. She lashed me with her tongue, all over the inside of my mouth and on my lips. Locked, we staggered over to the kitchen and continued making out while everybody else shouted “Happy New Year!” and drank champagne. We pulled away and looked at one another before kissing again. She hopped up on the kitchen counter and wrapped her legs around me.

After she playfully bit my nose, we kissed some more and I began to play with her pussy, which was soaking wet. I rubbed her clit so much her legs began to quiver on the kitchen counter. Fingering her was even better, because it wasn’t even close to discreet. She moaned so everybody could hear her, right as kept dipping my two fingers in and out of her next to the plate of Jell-O shots.

A few minutes later, she hopped down, kissed me again and said, “I wanna go down south. Brandon told me to fuck you.”

My eyes popped out of my head, just as my dick was popping out of my boxers. I knocked on the bathroom door – busy. I went to the bedroom – busy, people mingling about with glasses of champagne.

For a split second I considered unbuckling right there in the kitchen, but I didn’t want to cause a ruckus. Instead, I took her to the only safe place I could think of: the stairwell. I took her by the hand and pulled her out the door. Once in the stairwell, I dropped my trousers and she immediately dropped to her knees. She slobbed on my knob for a good five minutes or before she told me to sit down. Then she hiked her dress up above her big ass (She wasn’t wearing underwear.) and sat right down on top of my stiff cock.

She bounced up and down on it for a few minutes before we switched to doggy style. As I drove my dick into her from behind, she clasped onto the stairway rail with all her might. Our skin was slapping so hard, the sound echoed throughout the stairwell, as did her loud screams. When I told her I was going to come, she pushed me back and dropped to her knees again. She wrapped her lips around my cock and sucked on it, pumping her mouth back and forth until I blew it all down her throat. The entire stairwell encounter lasted no longer than 12 minutes – some of the best 12 minutes of my life.

We buttoned up our clothes and went back to the hotel room, where we partied with the rest of the crew well into the morning. Brandon smirked at me the entire time, full well knowing what happened. I told him everything the next day, and he congratulated me and said, “Happy New Year.”