This story is about Jennifer, the 43rd woman I slept with, as told by Jennifer herself.

Throughout this journey, I've been fortunate enough to run into some unbelievably awesome women. Some of whom I'm friends with to this day. Jen is one such woman.

We first hooked up in 2017, when I was 26 and she was 37, and have been fuck buddies on and off since then. Basically, if we're both single, we jump right back into it. It's familiar and comfortable and we communicate well, so it just makes sense.

She's been single for a little while, so we're back to hooking up, but even when we're not, she's always taken an interest in my sex life, similar to my other friend Lisa, whom I've mentioned a few times in previous stories.

As a fellow creative writer, she's loved the stories I've posted here, and thought it would be a fun exercise to write one herself, about our first hookup.

So, with that out of the way, I'll let Jen take over from here:

Hey readers. I'm Jen, and I guess I should provide a little backstory before getting to the good stuff haha.

It was 2017, and I was coming off a devastating breakup with my then fiancée. I thought this was gonna be the man I'd spend the rest of my life with, but, unfortunately (or, looking back on it now, fortunately), I found out he was cheating on me, and well, that was that.

I was at my lowest. Bitter and depressed, feeling unattractive. Sex drive nonexistent.

Enter Brian.

I met him at his job (he was working at a bookstore at the time), and a simple question about the book I was looking for turned into a fifteen minute conversation that ended in us exchanging numbers.

Now, I'll readily admit a few things right off the bat. Brian was pretty much the complete opposite of the kind of guys I typically went for.

As a woman that's not exactly petite (5'9 with curves), I gravitated towards bigger men. In terms of height and weight. Brian...well...Brian had neither, haha. I mean him and I can joke about it now, obviously, but that was the reality of it. He was shorter than me, and skinny. I also liked full, thick beards. He was clean shaven. I was into older guys. Brian was significantly younger. I often fell for the loud, boisterous personality type. Brian was more reserved.

I say all these things not as an insult, but as a compliment. Brian broke the mold, and is the sole reason why I expanded my taste in men.

How did he do that? With a quiet confidence, and a genuine interest in me as a person.

He was patient with me. We had gone out a few times without physical touch of any kind. Just hanging out as friends, more than anything. He wasn't throwing out pickup lines or otherwise trying to force attraction. Our conversations were organic and engaging, and not just a means to an end for him.

At the same time, I wasn't oblivious. I knew he was interested in me sexually, but he handled it respectfully. After our third "date" (if you can call it that), he walked me to my apartment, and softly, yet confidently announced, "I'd really like to kiss you right now."

I found his calm, casual, yet direct approach insanely attractive, and when I agreed to the kiss, that's all it was. A simple, tender, fleeting kiss. He didn't get handsy or try to push for more. Didn't try to invite himself into my apartment. He said he wanted to kiss, we kissed, and that was it. It wasn't a deep, sloppy make out, but it was...good. There was a level of, I guess "restrained passion" behind it. A kiss that basically conveyed the message: "When you're ready, I'll show you a side of me you didn't know I had."

That innocuous, yet decidedly hot little moment is what shifted gears for me. It left me curious and wanting more. I spent the rest of that week fantasizing about fucking him. What kind of lover would he be? How skilled would he be? Keep in mind, I didn't yet know he had a ton of experience under his belt, but that kiss made me see him in a different light, and it was the first time I entertained the idea that maybe this dude had it going on. It was "big dick energy" before big dick energy was a thing. That following weekend, all my questions would be answered.

I invited him over to watch a movie, and I think we both knew what that meant. As I prepped the apartment, I couldn't help but feel nervous and excited. I hadn't felt that way about a man since my ugly breakup. I got my hair done and dressed up a little, even though he was just coming over to "watch a movie." I knew he would've enjoyed me no matter what I looked like, but I did it for me. For the first time in a long time, I felt sexy and desired.

"Wow," he said, genuinely stunned when I greeted him at the door, staring me up and down, his eyes wide. "You look amazing."

I hadn't heard someone tell me that in years. I was melting inside, but did my best to keep cool.

And...yeah...didn't work, haha.

About 10 minutes into the movie, I felt bold enough to say the same thing to him that he had said to me the week before. "I'd really like to kiss you right now."

Initially, he shot me a goofy, cocky smirk, but as he inched his way towards my side of the couch, his smirk slowly morphed into a lustful, smoldering gaze. He sat beside me, held my face in his hands, tilted my head slightly, and slid his tongue in my mouth. God, it felt good to kiss someone again. For real this time.

Cue the giddiness and butterflies. In an instant, we went from a tender kiss to the sloppy make out I had been fantasizing about the entire week. I sucked his face off. I don't know how long we laid there kissing, but I know I was out of breath once we stopped, and that was a first for me. So yeah, I sucked his face for a while.

We stripped right there on the couch, I yanked down his boxer briefs, and there it was - easily the most objectively attractive cock I had ever seen. I've never been one to care about the aesthetics of a penis - whatever gets the job done is all I need - but still, it was beautiful. The head is wide with a very pronounced ridge, the shaft is buttery smooth and average in length, nice and chunky in girth.

I'm usually big on foreplay, and love both giving and receiving oral, but during our first hookup, I was too horny and excited to take our time. I wanted that thing inside me.

I laid on the couch and he got between my legs and gently played with my soaking wet pussy, which sent me shivering in anticipation.

Then, as if his kissing skills weren't enough on their own, he pulled a move that eliminated all doubt about his level of experience.

He laid on top of me, hooked his arms under my thighs, and slid his smooth, chubby cock inside me without using his hands.

Without. Using. His. Hands.

There's just something so incredibly hot about that. He didn't fumble around looking for the hole. He didn't use one hand to spread my lips and another to guide his shaft in. In an instant, he was inside me with his hands on my tits and my legs on his shoulders. It was a subtle move, but one that made me realize I was dealing with someone experienced and that I was in for a good time.

He began grinding and gyrating, his thick head methodically rubbing up against my walls in a circular motion. It felt like he was massaging my pussy with his cock. I reached around and dug my fingers into his tight ass, feeling his muscles clench as he gyrated. I remembered the feeling of those muscles. But on bigger, thicker guys. Jocks. Gym rats. Brian didn't develop those muscles playing sports like they did - he got them from fucking.

Every so often, when he wasn't kissing me or sucking my tits, he'd just look at me. Our eyes locked onto each other as he dug me out rhythmically. No beard to speak of. No chiseled jawline. But no doubt about it, I was getting fucked by a real man. All the previous hangups I had were gone in an instant. He knew how to fuck. He knew how to handle a taller, thicker woman. It clearly wasn't his first time. I was in good hands.

As all these thoughts are bouncing around in my head while I'm simultaneously trying to let go and enjoy the moment - another quick move.

Just as he put me in missionary with a blink-and-you-miss-it quickness, he pulled me off the couch and leaned back while still inside me. He was now sitting on the couch and I was sitting on his dick. I guess it was time to show off my skills.

Now, I'll say for the record that I'm not the biggest fan of cowgirl. I know it might be boring, but my favorite position was missionary (it's a classic for a reason!). Partly because I just feel so vulnerable up there, but also because I'm not at all confident in my actual riding skills.

And then...I sat on this guy's dick. Ha.

It's funny reading his previous stories and hearing him say that most women end up loving doggy the most, because I personally feel that cowgirl is far and away the best position when it comes to sex with him specifically.

Don't get me wrong, doggy is great, but sitting on his cock is honestly the best sexual sensation I've ever experienced, and the most powerful orgasms I've ever had have all come from sitting on it.

One such orgasm came that night.

I lowered myself all the way down, and gyrated the same way he did me, grinding back and forth, letting that thick cock head rub every area inside of me as he firmly squeezed and spread my ass, which felt fucking amazing.

In that moment, it wasn't about skills. I wasn't in my head about my performance. I just did what felt good. And god, did it feel good.

I could feel the build up, not just deep inside my throbbing pussy, but all over. My senses became heightened. My chest got tight. The simple act of his hands squeezing my ass gave me goosebumps. I was on my way to a serious, serious orgasm.

I honestly don't even remember moaning, screaming, or otherwise signaling that I was getting close. All I remember was saying "Oh god" in a voice a few octaves deeper than my usual, like I was possessed. I stopped riding immediately and just sat on his cock, letting the O wash over me, too scared to do anything that could alter the high I was suddenly on. I remember my pussy spasming around his cock as the orgasm surged through me, and him calmly running his fingers down my back, and giving my ass a soft pat, as if to say "I know. I felt it."

"Oh my god what the fuck was that hahaha," I panted nervously, in shock that my body could have an orgasm that deep.

"Haha, that was fucking awesome," he said casually, once again rubbing my lower back and ass in approval.

I had to suck his face off again. The moment called for it.

I stayed sitting on his dick and we kissed for a few minutes before we both jumped back into it. I was set after that massive O, but he needed to get his.

He got up, put me on all fours, and there I was, about to experience his famed doggystyle pounding for the first time haha.

Like I said, doggy with him feels fantastic, but since I had just experienced the O's of all Os, I was able to focus on some of the other aspects of the position.

He would give slow, deep, confident strokes. Strokes with a little mmph behind them, but at a casual pace.

Every time I let out a moan, he'd give me a soft pat on the ass. Not a hard, "Rawrrr I AM A DOMINANT MANLY MAN" type of smack - which, there's certainly a time and place for - but just like when I was riding him, it was more of a confident acknowledgment. Like "Yes, I know (smack). It feels good (smack). Of course it does (smack)."

I'm definitely a fan of vocal men, especially since they're so rare, but I also found the contrast of our reactions super hot. Here I was, on all fours, getting progressively louder and more excited - cursing, bucking, moaning - and his rhythm never changed. The hand he kept on the small of my back to hold me steady never moved. The soft pats on my ass with his other hand never stopped coming. He was completely unfazed and in control. He was taking good care of me, and he knew it. He was unsurprised by my reactions, and in a way, made him only more attractive in my eyes. Nothing I was doing was new for him. He expected it.

As he got closer, his rhythm picked up speed, and once he started grunting for the first time all night, I knew he was close.

"Go for it," I encouraged him, wanting him to cum deep inside me, which he did, and it was as rewarding and satisfying as you'd expect.

Once he shot his hot, thick, sticky load inside me, we laid on the couch and cuddled up.

We kissed yet again, tenderly this time, as I felt his cum slowly oozing out of me.

A few minutes prior to that, I felt great sitting on his cock. Now, I felt safe in his arms. I wasn't expecting either of those things, but there I was, pleasantly surprised and completely satisfied.