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Upwardly Mobile By Natty Soltesz
My life wasn't bad. I had a job, a roof over my head, friends. An ex who stayed out of my business and a three-year-old son who made my heart swell just to look at him.
But, you know, it was less than perfect. I was working my ass off, five days a week waiting tables, and still I was losing ground, money-wise, seemingly by the day. Like: my car broke down and needed a new goddamn engine. And then I came down with pneumonia -- had to be hospitalized, didn't have health insurance, so insane bills I'd be paying off for the next five years. Add child support, car insurance, etc, etc...you know how it goes.
It all seemed to be coming down at the same time. So sure, I still had my son and in a way I was happier than I'd ever been, but in another way I was miserable. I'm talking about peanut butter and jelly sandwiches for dinner on my nights off. Not going out, not doing anything for months because the money simply wasn't there.
So one crushingly-slow Friday night at the restaurant this man, Henry, came in. And Henry, the thing about him is he's this dashing older man -- you know, handsome, well put together. He comes in like once a week cause he likes our beer selection, and all the girls flirt with him, which should tell you something, because he's in his late 40s, maybe even early 50s. They love him. But for whatever reason, that night he got sat in my section in the back.
"Evening, Henry," I said when I came up to his table. He smiled this perfect confident smile at me and reached out to shake my hand.
"We've never met," he said, and I told him my name, shook his hand -- and it was a normal handshake, not the alpha-dog death grip. I took his drink order, a glass of Piraat. The restaurant was dead, so I kept stopping by and chatting with him, and I learned that he's an actual C.E.O., like the real deal, for this local company that's nationally successful --you've heard of it, no doubt. And I just got the sense that he was a good guy, down-to-earth. Funny.
He was still there when my shift was up so he suggested I sit at the bar with him and have a beer. And I was like, sure, cause I get one shift drink on the house anyway.
So I'm sitting next to him and we're talking, I guess pretty intimately about our lives. He's divorced. I'm a single dad. All that. He bought me a second beer and I was insanely grateful, not only because it was good conversation and company but also the last thing I wanted to do was to go back to my empty place, which was freezing cause I had yet to settle my gas bill from last winter and my state energy-assistance application was lost in the bowels of bureaucracy.
The beer was flowing through me, warm and good. And I found myself noticing things about him, like the heft of his solid hands and the subtle smell of his cologne. But my mind hadn't quite gone "there" yet.
Here's the deal -- I've considered myself bisexual ever since I had this thing with my roommate after I dropped out of college. He never considered himself bi, though at the time we'd done pretty much everything two guys can do with one another. I think he basically couldn't deal with it, but to me, it just happened, and I dug it, and that was that. I've dated girls and even knocked one up and proposed to her, though thankfully that didn't pan out. But I've never really "dated" dudes. Beyond my roommate it was just the occasional jack- or suck-off with friends, always guys my age or around my age. You know -- enough that I felt I had to relinquish my straight card, but never anything more.
So yeah, the idea of that with Henry didn't...present itself to me, but it must have been taking shape in the back of my mind. Cause we were on our third beer, and the conversation got quiet and he looked at me and I was like, "what?"
And he said, "I hope I'm not off-base here..." And my heart started quickening. "...but you're quite a handsome young man."
I wasn't shocked. I was surprised. I didn't really know what to do. So I was just like, "Thanks."
"That doesn't make you uncomfortable, does it?" And after a moment I was like, "No."
"Good. Cause I'd like to take you out sometime."
"Okay," I said, just sort of hearing the word come out of my mouth.
"Can I have your phone number?" he asked, and by god I gave it to him.
I couldn't stop thinking about it, how confident he'd been, how really attractive he was once I considered it. He called me the next night, my night off, and asked me out on a date. This man, this C.E.O., asking me out on a date. It was just too surreal, the sort of thing I had to go through with, had to try, even though it scared me.
He suggested this ridiculously pricey restaurant downtown and I said that'd be fine. He said he'd pick me up at seven. I gave him my address, and I hung up before I realized I'd have to get a babysitter for my son, or have Trisha keep him an extra day, and that I had no idea how I was supposed to dress at a place like that.
As it turned out, getting Trisha to watch Clint was no problem, and when she asked me if I was going out on a date I said yeah, I was, and she was sort of funny about it, like playfully grilling me for the details but I wouldn't tell her and I wondered what she'd think if she found out I was gonna get wined and dined by this older man.
I wore a nice polo shirt and a pair of pants that hugged my butt pretty tight. I found myself choosing my underwear really carefully and realizing I really wanted to look hot for this guy. When all was said and done I did look hot, I gotta say.
He picked me up in a Lexus and he wasn't in a suit or anything, which was a relief. He wore a short-sleeve button-down shirt, kinda stylish.
Dinner was great. I was looking over the menu and everything looked tasty but I was pretty sure he was buying and I didn't want to, like, overextend my invitation. "I'm going to order three appetizers if that's okay with you," he said. I was like, "That's fine."
"I want the stuffed figs but pick whatever other two you want, I can't decide," he said. That was when I realized that this date was turning out pretty cool. On one level we were just two guys, hanging out, in this comfortable way. But there was another level...and I wasn't quite sure where it was going to lead, but it was interesting at least.
He asked a lot about my son. Said he'd always wanted to have kids but it hadn't been in the cards. I was answering his questions and listening to him and simultaneously eating all of this amazing food that kept coming to the table. Then we were just sitting there, drinking and talking, and I knew I was gonna let him kiss me if he asked. Before I'd been unsure, but now I knew I was gonna kiss him, maybe make out with him, maybe other stuff, maybe, maybe.
We got the check and I'm ashamed to admit I tried to peek at it, but he was slick and managed to pay it without me getting a look. We left and got in his car and I was a little anxious that we hadn't said what we were going to do next, when he turned to me. We were just sitting in the parking garage. He leaned into me and his lips met mine and oh man did I give it back. His mouth tasted like the mints we'd had after dinner and he was kissing in this perfect way, being aggressive but not too much. His hands went around my waist and I was just swooning. My cock was really hard and when I could catch my breath I said, "Let's go somewhere." And he said, "Let's go to your place."
We got to my apartment and as soon as we got in the hallway he took me in his arms and I dropped my coat on the floor. He ripped off my shirt and he was marveling at my body, kissing me.
"I'm taking you into the bedroom," he said in my ear. "I'm gonna strip you down, lick every inch of you, and make you cum like you never have before."
I was like, jesus christ. I mean, speech was beside the point, I was so turned on. I was trying to get at his clothes as he pushed me into the bedroom but he more or less threw me on to my bed. He had this smirk on his face, like he knew he was in control, but knew I was into it, too. He ripped off my pants and groaned when he saw me in my tight little undies. He ran his hand over my package like it was his to open.
Then he stood back and stripped off his clothes, watching me the whole time with that smirk. Of course I was curious. I figured he had a nice body but I hadn't expected him to reveal this totally cut, toned body that, well, you just don't see much on a guy his age. It didn't look anything but natural, though -- he was so tall, and virile, with this graying hair across his broad chest. He whipped off his belt and pants and what I saw bobbing inside of his boxer briefs sort of made my eyes pop out of my head. I guess he saw my jaw hanging open cause he walked up to me sitting on the bed and, still with that smirk, held his briefs open so I could see.
It was more than a big dick. It was a goddamn Roman column. I stroked it for a minute then reached forward to take it in my mouth. He really dug getting blown. He would've let me suck him for hours, probably. But we were too horny. I was trying to cram it down my throat and I didn't care. I wanted it, everything he had to give.
He got on top of me on the bed and tore off my briefs. He stroked me while he kissed me and felt me up all over with those big hands, he was just all over me, I never had a second to think of anything. He got a fat finger wet and pushed it up against my asshole. He got it inside of me and was pumping me with it. He was like, "I wanna fuck you," and I was like, "Okay, yeah, absolutely," I mean, no doubt. I got him a condom from my bedside drawer and my jack-off lube and he lay down on his back and let me straddle him.
Which I was grateful for. It wasn't easy. At one point I thought it was a hopeless case, not that it wasn't fun trying. He seemed into it either way. I got the head inside and it was stretching me so intensely that I had to back off. Then I got on my back and he got over me and put my legs over his shoulders. He got the head back inside, and I was thinking of telling him to stop, that I wasn't going to be able to take it, and I was still thinking it when I realized he was all the way in me. Then he pushed even more and I realized I wanted even more.
I didn't last long. He got maybe a good dozen pumps into my ass and then he made the mistake -- or maybe he meant to do it -- to stroke my harder-than-hard dick which was all it took. I started blowing all over the place. I mean it damn near shot the wall behind my bed. I think me cumming must have set something off in him because he pulled out and ripped off the condom and already he was shooting, just spraying it all over my body. He collapsed on me.
I was still catching my breath. He was so heavy and his weight felt right, like warm blankets in winter. Something seemed to settle in me, something dense, and I found myself wanting to cry. Then I was crying and he was kind of startled. But he just got beside me and held me really tight. You know, in his big arms. I was embarrassed and I had to bury my head in his chest but I just kept crying, and I didn't even know what I was crying about. I wasn't ashamed. If anything I felt better than I had in months, maybe years, like his dick in my ass had released some tension in me.
I ended up telling him everything. I mean, as best as I could through my sobbing. How I was living, getting by barely day to day, wondering if I'd be able to pay my bills before the shut-off dates. Just spending every day in this low-level panic.
I realized I never said this stuff to anybody, just kept it all inside. But then I started to feel weird.
"I'm not telling you this to like, appeal to you," I said. "I didn't mean to lay all this out."
"No, don't say that. We both know this is true. Nobody can keep this stuff inside. If anything, I feel privileged." His voice was deep and it thrummed through his chest and against my ear. I wasn't crying anymore, I was cried out. I felt clear. He started to get up. I sat up too. He started putting on his clothes. He threw me my pants.
"Get dressed," he said.
"What are we doing?"
"We're going out. We're going to go out and spend a ton of money. Where do you want to go?"
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