Oral sex to ring in the new millennium. [m/f] | 2016

A few months before I met the girl from this story, I was single and home from college for the holiday break.

Even though it wasn't technically the millennium -- I know, there was no "year zero" -- everyone was treating like a big deal, and I wanted to have a date and have some fun that night. So just before Christmas, I called Kelly to ask her if she wanted to have dinner. We had gone to different high schools, but we lived near each other and we'd gone out on a few dates in high school. Physically, we'd been pretty innocent -- made out a few times but nothing further. My hope was that we'd have a fun date to get re-connected, and that I could end the date by asking her to go out with me again on New Year's Eve.

So on December 23rd, we went out. A fun dinner in which we re-connected and realized that we still got along really well, and enough talk of college and relationships to make it clear to each other that we'd both had some experiences. Because Kelly and I had never dated, there was no awkwardness here, and the conversation allowed us to flirt with each other and enjoy some sexual tension. After dinner, I told her that I wanted to give her a Christmas present before I dropped her off. It was dark out, and I parked a little bit down the way from her house so that we could talk without anyone seeing us from the home's windows. I gave Kelly a bottle of perfume that I'd purchased that morning. She was thrilled that I'd thought of her, then a bit ashamed that she didn't have anything for me.

"Well, I have an idea... how about a kiss goodnight, and you let me take you out again on New Year's Eve?"

"Those both sound like good ideas," said Kelly as she leaned in to kiss me. After a few minutes of necking and french kissing, we had to stop so that she could go inside. But we were both turned on and looking forward to New Year's Eve. "We should have done this more when we were in high school, but we'll make up for it on New Year's" were Kelly's last words to me on her doorstep, as she gave me one last kiss and went inside.

The Christmas week flew by as I was thinking about the New Year's Eve date. My dad -- a superb wingman -- had thought ahead when I hadn't and booked me a reservation at a local (and very nice) Italian restaurant for New Year's Eve. "I thought you might want to go out, but that you'd forget to think about it until you got back from school, at which point it would be too late." So Kelly and I made plans to go to dinner, and then head downtown to our city's New Year's Eve "block party" kind of event.

I realize I haven't described Kelly yet. She was a cute redhead -- very "girl next door" pretty with a petite body that I'd always wanted to see more of. For our NYE date, she was wearing a tight green dress that matched her eyes, and showed off her tight ass and great legs.

Kelly and I had another great meal and it was obvious that we were attracted to each other but we were at colleges at least 1,000 miles apart and we knew that we wouldn't start any serious relationship, which meant we could have a bit of fun and then both head back to our separate colleges still friends. My biggest problem was trying to figure out what we could do after dinner that would lead to us having a chance to fool around a bit.

It turns out, Kelly was way ahead of me. As we were leaving the restaurant and heading to the car, she stopped me, thanked me for dinner, and gave me a playful kiss on the lips. "My parents are spending the evening with friends an hour away, so they probably won't be home until 1:30 or 2 AM. How about we go back to my house and watch a movie?" This being 1999, it's worth pointing out that this is how people said "Netflix and chill?" before streaming video existed. The glint in her eye confirmed it.

Kelly was a bit older than I was -- she was 21 and I wasn't yet -- but I hadn't thought that through, so I was surprised (in a good way) when we got to her house and she pulled two bottles of champagne out of the fridge. "I bought these the other day, and put them in the fridge after my parents left and before you picked me up."

Kelly brought me into her family's TV room, which had a nice leather couch and lounger, as well as a giant beanbag (it was the 90s) in front of the TV. It was only about 9:15 or so, meaning we had plenty of time until midnight. We started watching "Jerry Maguire" and drinking the champagne. We continued to talk and flirt during the movie, cuddling up a bit on the couch, running my hands over her legs a bit, kissing and teasing each other -- we'd be starting to make out more, and she'd say "wait, I really like this scene" and we'd sit very proper and watch the scene. Cute stuff, that wouldn't have been possible if we didn't already know each other. It was like we were pretending to be boyfriend and girlfriend for a night since neither of us wanted to be alone on NYE.

By the time the movie finished, it was getting close to midnight and we'd gotten through most of the champagne. We were both tipsy and horny, having gotten more passionate with our kisses and more free with our hands as the credits rolled. She had let her hand move over my crotch a few times, and I'd been cupping her ass while we were making out. We both took a minute to use the bathroom, and then had the last bits of champagne while we watched the fireworks on TV.

"Happy New Year," Kelly said. "I'm so glad you asked me to spend the evening with you." We were still standing in the TV room. She kissed me and pulled back, still standing very close to each other. She smelled fantastic -- it was the perfume that I had given her for Christmas.

"We should have done more of this when we were in high school," I replied with a smile and a laugh.

"But then we couldn't have included the champagne", she replied. And then after leaning in and giving me another kiss, she said "so, how do you want to start the new millennium?"

This was the moment -- Kelly had been as forward with me as she was going to be, to let me know that she wanted more. But it was up to me to make the first move that solidified it. The alcohol and the flirting game me more confidence than I might have had otherwise, so I went for it.

"I think it would be fun if my first memory of 2000 was seeing what you had on under that sexy dress."

She smiled. "I was hoping you'd say something like that!"

"I've been working up the courage all night -- I wasn't sure if you'd want to, since we both have to go back to college in two days."

"Let's make a fun memory that we can both take back to school, then," Kelly said as she took my hands and kissed me more passionately than before.

That was the spark. We started making out heavily. My hands were on her back and reaching up under her dress while I kissed her neck and earlobes. It was obvious that she was wearing a tiny thong, and that she'd been planning on this part of the night all along. "Take your pants off," Kelly ordered me while she was unbuttoning my shirt and pulling it off of me. After a few moments, I was down to just my boxers (and clearly hard). She gave it a look, and then gave me a smile and a small nudge indicating that she wanted me to go sit on the couch.

So I sat down, and she stood a few feet in front of me, and then turned around. Her back to me, I watched as she unzipped her dress and let it fall to the floor in a puddle around her feet, leaving her in a light blue thong and black strapless bra. She gave me a moment to check out her ass, and then she reached up and unhooked her bra, tossing it onto the floor and then turning back around to face me.

With her shoulder-length red hair and small tits, she looked a lot like this picture. "Fuck, you are gorgeous" was the best I could utter, but that was good enough. She came back over to me and got on top of me, and we kept making out. I was leaning back into the couch, and I could feel her wetness and hotness through her thong even through my boxers while she was grinding on me. I was paying special attention to her breasts and nipples, and enjoying hearing her moan and watching her squirm.

I would have been willing to do anything at this point, but I wanted her to make the next move to make sure that nothing happened that she wasn't ok with.

"What do you want?" I asked her.

Kelly's response was simple and sexy: "I really want to cum tonight."

"Then we're going to need to get that thong off of you next..." A fun idea hit me, based on the furnishings that I described earlier. "Have you ever fooled around in that beanbag?" She shook her head no and laughed.

So we moved to the beanbag. On the way I took a glance at the clock -- about 12:30, so we were still ok on time. She was on top of the beanbag and I was on my knees in front of her, leaning over to kiss her lips, her neck, her breasts, and her belly. I ran my hands down her legs and inner thighs, running my fingers over her thong and pussy, eliciting shivers and little moans from her that let me know how turned on she was. I could feel her wetness. I kissed her belly button and made my way down from there, stopping at the fabric of her thong. Then I slid her thong off, revealing her wet and beautiful pussy, trimmed but not quite bald with just a hint of red fuzz matching her hair, a lot like this -- http://i.imgur.com/fR8SxQI.jpg

We were both still incredibly turned on, but I could tell she was a little bit nervous to be completely naked in front of me for the first time. "You are beautiful, Kelly. I want to make you feel so good tonight." I moved back up and started kissing her lips again, giving her nipples some attention and leaving my hand near her upper thighs but close to her pussy, until I felt her take my hand and move it directly on to her slit. I kissed her nipples and fingered her while she enjoyed herself. I still had my boxers on and I was hard as a rock, but right now I was all about her. I figured this would be my only chance with her, and I wanted to give her a great memory of me.

After a while making out and fingering her, she stopped me. She'd been feeling good, but I didn't think she'd cum yet.

"You didn't finish, did you?"

"No, but I want to."

"I want to make you cum, Kelly."

"Are you willing to go down on me?" She was nervous asking.

What Kelly didn't know was that even though this encounter was pretty early in my sexual career, I had already developed a taste for pussy, and going down on a woman was (and still is) my favorite sexual activity.

I answered her question with actions and not words, smiling at her and running my fingers back over her slit and slightly inside her, just to make sure that she was still wet. I kissed my way back down her chest and stomach, pausing over her pussy but not touching it, only slowly exhaling while she squirmed, and then finally giving her slit a long lick that brought a pleasured moan out of her. From there, I picked up the pace and followed the cues of her body, telling her how good she tasted and how much it turned me on to be eating her out. She was pretty primed from all our previous fooling around, and it wasn't long before she pushed down on my head and I could tell that this time, she was getting that orgasm she'd been craving and she was covering my face in her sweet juices.

As she came down from her climax, she pulled me up and I kind of lay next to her, halfway off the beanbag, which couldn't really support two people comfortably.

"Was that a good start to the millennium?" She just laughed and nodded in response.

"It's almost 1:00. I don't know how long we have until your parents get home."

"We've got enough time for me to take care of you too," Kelly said as she rolled off the beanbag and moved me over to the middle, finally pulling off my boxers. I could feel myself sitting on the wet spot from where she had cum, which I thought was really sexy.

Kelly stroked my penis with her hands for a little bit, and then leaned forward to kiss my nipples. I was a giant pile of nerve endings at this point, so the touch of her lips made me gasp and buck my back a little bit. Her kiss turned into a smile, and she kept going, quickly moving her head down and taking the head of my cock into her mouth. She took about half of my length into mouth, and used a combination of hand and mouth to blow me and jerk me off at the same time, while occasionally moving her hair out of the way to make eye contact. I was so turned on from our previous activities that it didn't take more than a few minutes before I could feel myself getting ready to finish, and I gave her a warning.

"Cum whenever you're ready," Kelly said, and put the head of my penis back into her mouth while continuing to stroke my shaft and balls. I held her hair out of the way so that I could watch my cock disappearing into her mouth, and after another few seconds I was in ecstasy. She held on through my orgasm, taking several ropes of cum, swallowing it down as I finished and then kissing the top of my cock clean.

"That felt amazing," I told Kelly, not wanting to get up but knowing that I needed to get dressed and out of her house relatively soon.

"I'm glad you liked it," she said as she got up and went to find her underwear.

"Let me get one last look at your sexy body before you get dressed," I said, still on my back on the beanbag recovering from her blowjob.

Kelly walked directly in front of me, and gave me a direct view upward of the pussy that I'd just eaten, and looked down at me, the lips that had just taken my cum smiling. Our eyes met, she giggled and said "Happy New Year" one last time, then stepped away to start getting dressed.

Life took us in different directions -- as we both knew going in that it would -- and we never saw each other again after that night.