As so many hookups do, this one started on Craigslist. It was late afternoon, and I was kind of bummed after a date I’d had planned earlier that day. I’d waited at the coffee shop for about an hour and my date had been a no-show. I’d texted him several times, but he hadn’t replied, so I went home and jumped on CL hoping that a hookup might quell my annoyance. I got the usual slew of emails from guys who were way too old for me or who just wanted a quick blow-and-go. I mean, I’m all for quickie sex, but nothing but a blow job? I’m not leaving the house for that! A guy has to have standards.

Eventually, I got an email that caught my attention. The guy lived in the next city over, and he was hoping for something that was just slightly more than a hookup. He definitely wanted sex, but he wanted to enjoy a night together with someone as if they were actually dating. The pictures he shared were tame, just a couple of shirtless pics, and one of his face. He was about 10 years older than me, in his mid-30s, and he didn’t look half bad, so I said why not and sent him a couple photos of me. He sent me his address and told me to arrive around 8 PM. I had a couple of hours, so I decided to shower and choose something nice to wear if he really did want to be classy. Of course, I figured I should hope for nothing more than maybe a drink before the fucking started. Thank GOD I was wrong.

I showed up to his place right at 8 PM, looking pretty good in my nicest polo shirt and jeans. I was nervous as fuck, of course. I mean, what random hookup doesn’t get someone nervous? He answered the door, dressed pretty nicely in a button-down shirt and slacks. He has a light beard and short-cropped red hair. Gingers - my only weakness.

“Hi,” I said, offering him my hand. “I’m Myles. From Craigslist?” I said, as if he must have invited a bunch of different guys over.

“Nice to meet you. I’m Charles,” he said, taking my hand. “Come inside.”

His house was pretty nice. It was sparsely decorated, and he told me that he’d bought it a couple of years earlier and was slowly renovating it. He led me on a quick tour, showing me the living room and then dining room where he’s set two places already. As I went to sit down, he pulled out the chair for me. A proper gentleman. In this day and age? Who’d have thought it was still possible?

Charles had prepared a light meal - a salad and a simple pasta dish. As we ate, we started to chat.

“So what do you do for a living?” I asked him.

“I work for the city. Nothing fancy, just administrative work mostly, but it’s good work. How about you?”

“I do a lot of data entry right now, but I’m planning to go to grad school and get my teaching credential in the next couple of years.”

“Oh yeah? What do you want to teach?,” he asked.

“High school literature, hopefully. I don’t know. I’ve been kicking around a few ideas, but that’s my main goal right now.”

“Well, we could always use more teachers,” he said.

“That’s my thinking, too. So, do you live alone? No boyfriend or husband…?,” I asked.

“No, it’s just me. I don’t really have time to date anyone. I kind of work a lot of odd hours, which tends to turn guys off of dating me. My last relationship ended because the guy couldn’t stand me not being able to go out a lot. I’m also kind of in the closet at work, which he couldn't accept, and we fought about that a lot.”

“That really sucks. I’m sorry to hear that.”

“It’s fine. I deal. What about you? Do you live on your own?”

“I have a couple of roommates,” I told him. “One is my best friend that I’ve known forever, and the other is a guy I met in college.”

“You ever hook up with either of them?”

I hesitated for a moment, not sure how much to share with him. But then I figured that we were separated by an entire city, so there wasn’t a chance of him even meeting anyone I knew and telling on me. I ended up telling him all about how I’d hooked up with Calvin a few years earlier, and how my other roommate and I had flirted off and on the entire time we’d known each other, but nothing had ever happened.

We spent the next hour sharing dinner and good conversation, not to mention a great bottle of Merlot. Charles turned out to be a really sweet guy, and I was kind of enamored by him. When we were all done, he cleaned up the dishes, and staunchly refused my help when I offered it. Once he was done, he took my hand and lead me to his bedroom. I guess the date part of the evening was over.

The bedroom was big, with a large California King sized bed against one wall. He lead me over and sat us both down on the edge. Charles grabbed my face gently, pulling me in close for a kiss. It was quick and quite sensual. I had to have more, so I kissed him back, trying to infuse every bit of that kiss with passion. Slowly, his hand ran down my neck, then down the front of my shirt, getting ever closer to my crotch. I returned the favor. When I finally reach his crotch, I can feel that he is hard as a rock, which makes me go from half chub to full mast very quickly.

I reach up to the top of his shirt with my other hand and start unbuttoning it. As his chest is exposed, I see that the pictures he sent me have done him no justice. He looks even more well defined in person, with a nice six-pack under his unassuming shirt. I start to play with his nipples, tweaking them lightly. This makes him moan hard, and I can feel his cock start to jump around in his pants. We disengage long enough to take each other’s clothes off.

As we stand there naked, I feel completely inadequate next to this man. He is gorgeous with an amazing body, and I wonder how anyone could turn this down. I quickly get to my knees and start taking his cock into my mouth. He is about 7” long and kind of girthy, so it’s a bit difficult for me to get him all in. I start jacking him off slowly as I work my lips around his cock head. With my other hand, I grab his firm ass and start massaging it, slowly working my hands closer to his hole. He moans as I slip in first one finger then another.

“Will you eat me out?,” he asks.

“Yeah,” I tell him. He turns around and bends over the side of the bed. I move in close, finding his ass is utterly hairless and squeaky clean. I start to tongue his ass slowly, running circles around his hole before sticking it right in. This drives him wild and he’s moaning even louder now. After a few minutes of this, he announces that it’s my turn. We switch places, and soon he’s eating me out like a starving man. His tongue seems to have no end as he tongue-fucks me right there. I have to stop him as I feel myself about to burst and I want to enjoy the rest of this.

I crawl into the center of the bed and he climbs on top of me, his body right above mine. He looks me straight in the eye for a moment before meeting my lips for another round of kissing, this time rubbing our dicks together. After a bit more of this, he pulls back, reaching into a dresser drawer for a condom and lube. After prepping my hole with a lot of lube, he started to enter me slowly. It takes a couple of minutes before he’s fully inside, but when he is, I don’t want him to leave. He feels perfect up there. He starts thrusting slowly, but quickly ramps up his speed until he’s like a jackhammer. With other guys, this might be a little insulting or unwanted, but with Charles, there’s real passion in there. We might have just met, but it’s like we’ve been fucking together for years.

Somehow, without leaving me, he maneuvers us so that he’s lying down and I’m on top riding him. We stay like this for a long time. Every time it feels like one of us is close, he slows down and we find a new position. There is sweat dripping off both of us, and I don’t care. Every thrust, every touch, is filled with sensuality and passion, and I wonder again how this man can be single.

After what seems like an eternity, we’re both close, and neither of us is able to hold back anymore. I’m back on top of him when I can feel the familiar sensation. I have just enough time to warn him that I’m cumming before I end up emptying my cum all over his chest. My hole clenches tightly around his cock and this sends him over the edge as well. I feel him pulse inside me.

I slowly get up and nearly lose my balance my legs are so wobbly. Charles pulls the condom off, discarding it into a small trash bin next to his bed. He’s still covered in my cum, and there’s plenty more still on his dick. He reaches down and wipes some up, along with some of my own, then drips it all into his mouth. He pulls me in for a kiss, which I hungrily return.

“That was fucking amazing,” I tell him.

“Yeah,” he says breathlessly.

After a few minutes, we’ve both finally come down from our cum high. Charles gets up to grab a towel so we can clean up. As we do, I start getting dressed, pulling on many underwear, but he stops me.

“Do you have somewhere to be?”

“Not really, but I figured you’d want to get to sleep after all that, so…”

“Do you want to spend the night? I know this sounds weird, but i usually sleep better when I’m holding someone. Stay?”

He’s been so sweet, and I really don’t have anywhere to be, so I say yes. I send Calvin a quick text to let him know I’ll be home in the morning and not to worry about me. Charles and I fall asleep next to each other fairly quickly after that, both of us just in our underwear. I know this is just a one-night stand, but it still feels really intimate to be doing this. I wake up early the next morning, not really intending to. Charles is still sound asleep. I get dressed and show myself out, being as quite as I can so as not to wake him. I never saw Charles again, but every once in a while I still think about that amazing night we spent together.

Thanks for reading and I hope you enjoyed this latest entry. As always, names have been changed to protect privacy.