When I woke up on New Year’s Eve, I assumed I’d be spending the evening completely alone. I had been talking to some guys on Tinder, and most of them already had plans. A few invited me to come out, but being with a stranger from Tinder and his friends just didn’t sound appealing to me. Honestly, a glass of wine and a book sounded like good enough distraction from knowing I wasn’t going to be with my kids on the first day of the new year for the first time in their lives.
I went to work as usual, and we were all getting excited because the store was closing early because of the holiday. Someone was going around inviting a few people to dinner, which I graciously accepted.
We closed the store, finished everything up, and were out the door before 7. We all decided to meet at the restaurant, and I drove straight there. All in, there were just four of us. It was a nice time and a good distraction. As we finished our dinner and split the bill up, I was intending on going home, but then one of the girls asked me to join her with some more of the crew at the bar that was just around the corner. I was hesitant, but she insisted since I didn’t have anything going on.
It was close enough that we both just walked together. Once we got there, there were a lot more coworkers, and we had a good time. There was some dancing, but mostly drinking, and it was pretty easy to have conversations. It didn’t take too long before almost everyone I knew was gone. I think everyone just did the ol’ Irish Goodbye and disappeared. At this point, there were only 6 of us left, and we took a seat at a table and ordered one final round before we were going to part.
Three of them downed their drinks quickly and took off, and then it was down to just the three of us: Jade, who was the one I came with from dinner, and Alex, a slender, younger guy in his very early 20’s that I didn’t know too well. I still had a good 2/3 of my drink left when Jade got a text and told us she had to leave. She said I could join her, but it felt more like a pity invite than anything else, so I told her that I was completely fine and she should go have fun.
We’re down to just Alex and I. For some more context, we had talked about how he’s working full time at the store while attending community college part time. He’s a bit of a loner, he’s really close with his family, and he also didn’t have plans for the evening. He doesn’t have many friends, he’s not really into the whole party scene that a lot of his classmates are into. He just wants to get through school so he can get into grad school and become a pharmacist.
He asked me if I wanted to keep hanging out. I declined. We both finished our drinks and walked out together. He asked where I was parked, and I told him it was a few blocks away at the restaurant, and he told me he’d be happy to walk with me to make sure I was safe. I kind of laughed in my head, because this gentle guy wouldn’t protect me against a fourth grader, but it was a great gesture and I accepted after a bit of a fight about it.
Once we got to my car, I realized now I should drive him back to the bar, so I asked him if he had parked there as well. He laughed, told me that he had taken the bus here so he was just going to walk back. I asked where he lived and it was pretty far, and I volunteered to drive him home. Just like me, he fought it a bit but then caved.
We sat there in relative silence for a bit, and then when we started getting close and he was giving the turn by turn directions, he said that he had a bottle of champagne that was a few years old and he had some white wine, and if I wasn’t doing anything we could just watch all the Times Square stuff together. It seemed quite harmless, and this guy had not one single ounce of flirt in his body. It almost felt like a girlfriend asking me to come over. I agreed.
We went upstairs to his apartment and he quickly ran around picking up the few things that were out of place. He asked if I wanted the champagne or the wine and I laughed and said we should save the champagne for the new year’s toast, so let’s get the wine.
He grabbed the bottle from the back of his cupboard. It was pretty obvious that it had been there for a while and he was saving it for a “special occasion.” He didn’t have wine glasses, so he grabbed us each a pint glass and filled them up. I laughed and asked if he was trying to get me drunk, and he blushed a bit then told me he could pour some back. I told him it was fine and that I can just sip.
We turned on the TV and watched some of the New Years Rockin’ Eve. We basically both just made fun of the people because neither of us really keeps up with this kind of thing. We drank, we sat in silence, and occasionally we dove down a rabbit hole of conversation. One of them ended up finally switching to sex as the topic.
On this topic, I learned that he’s had sex with one girl, and he’d gotten a blowjob from a different girl, but these were both over 3 years ago. Since then, he’s been single and he never has enough confidence to talk to women. We had already discussed that I’m newly single, we had talked about my relationship, how I was married to the same man and had been with him since high school, and that I’m finally enjoying my newfound freedom, just now getting to explore my own sexuality with others.
One of those “freedoms” is being able to do whatever I want, when I want, as long as it’s a weekend or the kids are at school, I don’t really have the responsibilities I used to have. It was at this time that I looked up at the TV and saw that there was a little over 12 minutes left before the ball dropped in Times Square.
He had been fairly uncomfortable all night. I continuously caught him sneaking glimpses at my body, but he was a complete gentleman. I could tell he wanted to say something but feared rejection. I just knew it, deep down. I didn’t know how to suggest anything with him. Prior to now, the topic of either sex or a blowjob came fairly naturally from the guy, and I fed off that. So I just decided I had to take the lead.
So I asked if I could make a suggestion, for the ball drop and the rest of Rockin Eve. Of course, he agreed, having no idea what the suggestion was.
I told him that I thought it would be fun to see if I could get him to cum right at midnight as the ball dropped. That’s all I said for now, and I just looked at him.
He said “uh” and “um” and “uh yeah” like 50 times each, I swear I could actually see the gears turning in his head trying to formulate a sentence. He awkwardly shifted on the couch while muttering, and I told him I’m going to take that as a yes.
He shook his head and said yes.
I sat my wine cup on the side table and crawled in front of him. I told him I had a rule, that this is a one time thing, and neither of us could speak of this again. After tonight, this never happened. He shook his head and said yes, that worked for him.
I slid his pants down, and his underwear as well. He was already as hard as a rock. I palmed it and gave it a few strokes, looked up at him and reconfirmed: we will never talk about this again, and you won’t tell anyone. He agreed.
I started slowly. I pulled his cock to the side and started kissing it, and he started breathing incredibly quickly. I told him to relax, and he said ok and leaned back. I told him that was more like it, and then I gave one very deep suck, all the way down. I hadn’t had a guy moan like that on the first few seconds before, and somehow his cock felt like it got just a little harder.
I started sucking, moving up and down slowly, and he felt like he was about to cum. Knowing that it wasn’t yet time, I slowed down a bit, switched to my hand, and looked at the TV. There was only about 2 minutes left, and I asked him if he could last another two minutes. He shook his head without saying anything, just breathing hard.
I told him if he can’t last that it’s fine, and then I went back to work. After no time at all, I heard them starting the countdown and I took a quick break and told him I wanted him to cum at zero, to which he nodded and looked visibly shaken. When zero happened, the music started playing, and he didn’t cum, so I started sucking harder and faster. His moans started getting louder and his breath sounded like he was running a marathon.
After maybe a minute, possibly a little less, he exploded. He grabbed the pillow and shoved it into his face while he started moaning these quick little moans, it almost reminded me of a puppy yelping. I continued to suck until his cock stopped throbbing, and then I slowly slid it out, kissing it a few times as it lost a little bit of its hardness. I reached up and pushed the pillow to the side, giving him a smile and asking how it was.
Still not forming a complete sentence, he basically mustered out that it was the best thing that’s ever happened to him. He told me he felt like he won the lottery. I smiled and shook it off, I told him I was so glad and that I had a lot of fun.
He actually apologized for not cumming right at midnight, and I laughed pretty hard. I was actually finishing off the last gulp of my wine and nearly spit it out. I reassured him that it was completely fine, I didn’t actually expect it to happen, I just thought it was a fun little game. He seemed relieved.
I had the early shift the next day. Luckily, we opened a few hours later than normal because it was New Year’s Day, but I still had to be there at 9. I told him I needed to get going. He awkwardly said something like “Can I, uh, can I do something for you too?” while he was getting his pants back on.
I smiled and told him that I’m sure I enjoyed it every bit as much as he did, and that he needed to remember the rule. This never happened. He told me absolutely, and he did the dorky motion like he locked his lips and threw away some invisible key.
I winked and turned to leave. He said “wait!” in a loud voice, and I turned around. He wrapped me up in a hug and said thank you. I smiled, and said “no, thank you,” and pushed my finger into his chest and walked out. I got out to the parking lot and looked up, I saw that he was watching me through the window, and as soon as I did, he quickly backed away. I laughed and got into my car.
Looking back on it, I absolutely shouldn’t have driven, but I didn’t feel very buzzed at all. It took me about 10 minutes to get home, luckily his place is almost exactly halfway home from work, so I knew right where I was. When I got home, I immediately crashed.
The next morning, January 1, my alarm went off at 7. I had a text from one of my kids and a text from Alex. I replied first to my daughter, wishing her a happy new year and telling her I couldn’t wait to see her tomorrow, and then I read the text from Alex. He told me it was amazing, the best he’s ever felt, and he would love for a round two, or would love to return the favor.
I reminded him of the agreement, that we’d never speak again, and he said yeah, he remembered, but just wanted to throw it out there. I said let’s just stick to it, and he said okay.
I got ready and went in to work. I was glad he had the day off, because I didn’t want to risk anything.
During my lunch break, I saw I had another text from him, where he basically said the same thing again. He said he was super horny and that he wanted to meet me that night. I was pretty firm in my response, I said that he’s not living up to his end of the deal that we never speak about it again, and I told him I already had plans that night.
He asked what I was doing, and I ignored him. This is actually when I made a Reddit post. I didn’t reply that day, and he didn’t text me again.
Afterwards
A few days went by, and we hadn’t spoke. We were friendly, just sort of saying hello in passing at work, nodding, and smiling. In passing one time, I stopped him and asked him how he was doing, and he said he was great. He apologized for breaking the rule, and I said I understood, but it can’t be broken again. He said he completely understood and respected it, and it’s now just a really good dream he had. I thanked him and got back to work.