My first date, which was my first hookup.

This was written February 7th, but I set the date to December 2, so that I can keep a proper timeline.

It was December 1st, 2002. I was talking to an old friend of mine, Steph. She and I were talking about my divorce (of course) and that I should get out there and meet new guys. “You’re only 40, you need to get out there.” I disagreed. I was in a relationship since I was a Junior in High School. I needed some “me” time.

She insisted. But, she didn’t know how to help me. She didn’t know anyone, she had been married for 10 years herself, but her coworker Kelly was younger and was always talking about dates, so she called her so that we could have lunch.

We met for lunch the next day, Steph introduced Kelly and I, and we hit it off well. I’m a lot older than her, so it was a bit awkward for me, but she didn’t seem to notice at all. She’s in her mid twenties, maybe 24-25, and she’s loving the single life.

This is where Steph decided to chime in and ask if Kelly knew of any guys that could go out with me. It was super weird watching these two women talk about me hooking up, but Kelly was incredibly helpful. Awkward for me again, but for her, just another day. Kelly insisted that I go out with her friend Nate, she said he’s a super good looking, muscular guy who people say is a great lay.

I brushed her off, said I’m not really interested, but Steph said that was exactly what I needed, and Kelly agreed. Basically they said that I just need someone who will fuck my brains out to get me into “the game” and get me completely engrossed into the single life. I absolutely insisted that I was not committing to hooking up with someone, but that it could be fun to go out. They both harassed me about that, but I stayed strong.

Kelly texted Nate, and showed me the texts afterward. Basically, she said she had a super hot MILF friend that he needs to go out with ASAP. It was only 3-4 texts and then she asked me for my number to give him. I gave it to her, he texted me “Hi, Kelly says we should meet tonight, are you free?”

Steph grabbed my phone, insisting that I didn’t get to be a part of it. She laughed a bunch and I kept reaching for it, trying not to make a scene over the table, but eventually handed it back. Steph suggest we meet at fucking Applebees.

“Applebees?!” She laughed, and said it was the first place she could think of.

We thank Kelly, and we head back to my apartment so I can get ready. Since it was a Saturday, the kids were with their father. This was only the 2nd weekend of our arrangement so I was a little hesitant in case they needed me, but Steph insisted it would be fine – I have a phone and could leave at any time if needed.

I have no idea what to wear. So, we played dress-up with my clothes for a while. We landed on this and Steph took a picture to send to Nate, but I absolutely wouldn’t let her. As I was changing, she sent it anyway, saying “so you know who you’re looking for.”

He replied with a thumbs up. Hmm. Curious response.

After we decided on the outfit, she was ready to go home, but I was an absolute nervous wreck. I still had 2 hours until we were meeting and I insisted she stay to distract me. We drank wine and watched tv until it was time to go. I drank a few more than she did. She dropped me off at Applebees, and I was even more of a nervous wreck.

He arrived just a minute or two later and immediately recognized me, I mean I was wearing the exact same clothes and everything, I had taken my jacket off to make sure of that. We talked to the hostess and then grabbed a high top table in the bar area. We ordered appetizers to share and some drinks.

Nate absolutely lived up to the hype from Kelly. He was tall, in very good shape, and handsome. He looked like a frat boy to me, but he was telling me how he had graduated a few years ago, so at least he wasn’t still a frat boy. It was after a few drinks that we started getting into the real conversation rather than just talking about the weather and local stuff.

He seemed genuinely curious about my relationship and how I lost it. He said that although he is loving the single life that he wants to settle down and get married and have kids. I joked that I’m absolutely not that for him, and he said something along the lines of “well that’s also ok by me for today.”

After our fourth drink, he asked if I wanted to go back to his place to get another drink that is much cheaper. I agreed, and we took an Uber. It was on the way that I really started getting nervous and he saw it. He didn’t need me to say anything, he just said “hey look, there are no expectations except that we have a drink, ok?” I just half smiled and nodded, and we were there in no time.

We walked in to his one bedroom apartment and it was better kept than I thought it would be. Still sort of a mess, but tidy enough to not be embarrassing. He made us a drink and we sat on the couch. He put some music on, I kind of chuckled because it seemed incredibly cliche.

In the middle of our second drink at his place, he leaned over and kissed me. He stuck his tongue into my mouth and I was in shock. I hadn’t had a deep kiss like this in over a decade. Not knowing what to do, I just sort of swirled my tongue back on his. He reached up and grabbed my boob, and I kind of laid back on the couch. He started squeezing it a bit harder and then he started grinding his erection on me.

I stopped him and told him I had no idea what I was doing, that I don’t know what to do and he said he would take the lead if I wanted, or we could stop. I told him that as long as he’s okay taking the lead and showing me the ropes that we could keep going, but if I said we need to stop that we would stop. He completely understood.

So we’re making out on the couch, he’s grinding his erection on me and playing with my boobs, and he slid his hand under my sweater and bra. He asked if he could take it off, and I nodded. He unclasped my bra with one hand and then we worked together to take my top off. As soon as my boobs were free, he cupped them both and then sucked on one of them.

He laid me back down, and then took his own shirt off, showing off his absolutely perfect body. I think this was finally when my nerves started subsiding and I started just really getting into it. He then slid his hand over my crotch, still over my pants, and rubbed a bit. We were both breathing hot and heavy. He asked if I wanted to feel his cock, and I nodded. He rolled over to the side so I could reach it, and I gave it a few strokes over his pants.

I noticed it was incredibly hard, I remember that being the first sensation of touching another man’s cock. My husband hadn’t been that hard, maybe ever.

After a few more strokes, he unbuttoned my pants, sliding them down while I lifted my hips so he could slide them off. I’m now just in my panties, he’s still wearing his jeans. He rubbed my crotch a little bit over my panties before asking if he could take them off. I said yes, and he slid them off.

He started rubbing me, then slid a finger inside, rubbing against my clit a few times before inserting his fingers up inside me. He did this a few times, and then he asked me if I would want to go into his room, that’s where he keeps his condoms.

I told him I did, and he stood up. I stood up, and he grabbed me, pulling me in close while holding my ass, and kissed me. He said “I’ll be gentle if you want, but I can be as rough as you need.” I smiled, and then he led me into his room and said to lay down.

He watched me crawl onto the bed, told me I’m incredibly sexy, and then opened his drawer and pulled out a condom. I was on my back, watching him as he unbuttoned his pants and pulled down both his pants and his underwear in one motion, and I watched his cock spring as it was free.

I didn’t see it for more than a second or two before he was rolling the condom onto it. He looked at me, caught me looking, and asked if I liked what I saw. I said I very much liked it, and he asked if this was all okay. I told him I wanted him to fuck me, and I told him that he didn’t need to go slow.

He smiled a huge grin and climbed on top of me. Immediately he thrust inside me and started pumping. We were in missionary position, and he was grabbing my ass with one hand while supporting his weight with the other. After just a few minutes, he said he was getting close, and I said something like “Yeah baby, cum,” and he pulled out of me, ripped off the condom, and started coming up.

Without thinking, I leaned in, taking his cock into my mouth, and just sucked. He came pretty much instantaneously, and that’s of course when the reality sunk in that I’d never done this before. I had never had cum in my mouth. I had always thought the sound of it was gross, my husband had only asked about it maybe twice in our entire relationship, so it just never had come up.

Well, lucky for me, I loved it. He was moaning, I could literally feel his orgasm happening, and it flipped a switch for me. I had never felt this “responsible” for the pleasure of another person before. But, not knowing what the hell I was doing, I just kept sucking.

He kept wriggling and writhing but it all seemed pleasurable, until finally he pulled back and said he couldn’t take it any more. I asked if it was good because that legitimately concerned me, and he said it was one of the best feelings he had ever had in his life. I took that as a compliment, because I know he had been with multiple people.

We laid there naked for a little bit, talking about something I can’t really remember, and then I said I should probably be heading out. He said he was getting tired so that was probably the best anyway.

As I was getting dressed, I hit the Uber button, and we exchanged our pleasantries, he said he’d be willing to show me more anytime. I left, went home, and couldn’t fall asleep. I was sitting there reflecting, and even though we had sex, my favorite part of the night was the very end, when I was sucking on him.

That’s when I realized that I missed out on a lifetime of something I now love, and that there’s no more holding back. I don’t have as much life left to live, and I can’t wait around.

I’m now just going to be me, whatever that means.

A month later

About a month later, I made my first Reddit post about this. Basically, I didn’t have sex again with someone but wanted to know if this was normal and something to expect. I gave three more blowjobs (which I’ll tell about later) but not sex until after the post.

For some clarity, after the Reddit post, I texted him and asked him a few things. First I asked about STI testing, which he told me he had just gotten tested the week prior and was completely clean. Second, I asked him why he assumed I would swallow, and he said he didn’t. He was intending on cumming on my chest, but then I took it the rest of the way. He and I haven’t communicated again since.