
As unpleasant as parts of my hookup with Tyler were - the smell of his ass while we 69ed - he was the best head I'd ever gotten. For a while after our rendezvous, I bragged about sucking his dick for forty-five minutes straight, how I was the person to get him the closest to orgasm; of course, I hyped him up, too. I didn't know what it was about him that had made the experience so great, but he had a lifetime license to give me head; I'd never say no.
While I found myself enamored with my coworker - Rylan - Tyler found himself embroiled in drama over the next several months. Firstly, he quit McDonald's to work at a gas station; he was ultimately fired for retail theft, even though it was accidental. On one of the occasions that we caught up via Messenger, he explained that he had grabbed something that the store needed, set the tag beside his register, and then forgot to ring it into the system as a store necessity. He was worried that would be prosecuted, but nothing ever came of it, though he ended up being unemployed for a month and a half, having to pawn his belongings to stay afloat. He eventually got a job at Taco Bell, but it took them a month to actually get him in; after three days of working, he quit and hired in as a manager at Burger King. He'd also been struggling with a situation involving someone who was his closest friend ghosting him and the fallout from that. Although I tried not to wish misfortune on others, a part of me was relieved that I wasn't the only one going through it; it's true what they say, misery really does love company.
I found all of that out in July - nine months after our first hookup. The most exciting thing to happen to me in that time was my infatuation with Rylan and the high I'd get whenever he smiled at me, made us food, or texted me. Even so, by July, everything had gone to hell and I was once again heartbroken and alone.
Tyler wanted to meet up again, but once we made plans, he had to take a raincheck - they were making him cover the morning manager, meaning he couldn't be out late sucking my dick. I was disappointed, but I also understood that work had to come first; I've always dropped what I was doing if work called and needed a shift covered. I had recently started to warm to the idea of filming blowjobs - giving and receiving; Tyler was okay with the idea but insisted that it would have to be on his phone. He told me that one of his coworkers had had her nudes shared on Facebook - by her petty ex.
We weren't able to meet up again until the beginning of August. Tyler was horny enough to drive out to my grandma's h0use in the middle of the night. We made the plans while I was still at work and timed it so that I'd be able to get home, eat, and shower before he got there.
When he got out of his car, he looked pretty much the same as he had the last time I'd seen him. Despite our easy interactions online, in person we were still awkward and stilted - I was never good at having random sexual encounters. How was I supposed to start it? I didn't enjoy just getting to it, but I also didn't want to kiss and cuddle with someone I wasn't romantically interested in.
We made our way through the early August chill to the Blair Witch house. I had been going back there a lot to smoke; I knew that my grandma wouldn't catch me out there - the last thing I wanted was for her to lecture me on how stupid I was being. I knew the risks involved but didn't care. It had also become the go-to spot when I was able to sneak a guy over late at night.
Tyler and I sat for a while just talking, catching up. He seemed to be doing better than his messages had portrayed him to be. I found it interesting that we got on the topic of a guy I'd hooked up with a few months previously; Tyler knew him and said he was crazy and clingy. The guy had seemed nice enough to me; the only time I'd ever been annoyed was when he got snippy at me for trying to get him to ride me. I suppose my cold and detached demeanor kept people from getting too attached to me. It was always interesting to hear another's perspective though; according to Tyler they'd hung out a few times, and the guy had become "obsessed." Even though, Tyler kept telling him that he was going through a lot and didn't really want to be around anyone, the guy kept whining about how he wanted to hang out until Tyler finally snapped on him and told him that he didn't owe him anything and demanded to be left alone.
I filled him in on everything with Rylan, how we had been attached at the hip all winter, but then the minute he got a girlfriend he'd basically cut me off completely. I was still deeply emotionally attached to him, but I couldn't bring myself to confront him about it, to ask him why I was suddenly persona non grata. Every day, it felt like my heart broke a little more as the rift between us grew wider and deeper.
We sat out in the Blair Witch house for a long time catching up. Crickets and cicadas chirped around us as the moon shone down through the hole in the ceiling. As I listened to Tyler, I looked around the building; I started to fantasize about having the money to fix the place up and make it my own "apartment." It was far enough from the main house that I would have privacy but still be close enough to be with my grandma when she needed me. The foundation was brick, which had held up wonderfully; it would need a new roof, doors, plumbing, and electricity, but it would make a great little studio apartment for me - if only I had the money and the means to make it so.
It was obvious that Tyler really needed to talk through all of his issues, so I didn't push the sex stuff. I listened and gave my opinions as needed. I started to suspect that we wouldn't get to blowjobs; it was almost midnight - we'd been out there for over an hour; I would need to go to bed soon, assuming I could get in the house without causing too much of a commotion - my uncle slept on the couch in the living room, so getting past him would be a herculean task, unless I got lucky and his narcolepsy knocked him out.
I was worrying about that when Tyler stopped talking for a second and then said, "Well, do you want me to suck your dick? We've been out here for over an hour now."
"I mean," I shrugged, "if you want to. No pressure."
"Well, that is why I came here, right? I owe you a blowjob?"
"You don't owe me a blowjob..."
"I had to cancel last time."
"I know, but..."
I didn't want Tyler to think that I just talked to him because he would suck my dick - and do great at it. Although I wasn't attracted to him, we had kind of become friends - or at least friendly - since our last time hooking up. He was someone to talk to, someone that I knew outside of work, someone I could be myself around without having to put on the facade I'd adopted since I started working.
Tyler reached out his hand and put it on my crotch, slowly moving it back and forth. I looked at him in the scant light, trying to see if he was doing it because he wanted to or because he felt like he owed me. He looked like he was into it, so I kept my mouth shut. I figured, if he wanted to suck my dick that badly, who was I to deny him?
It didn't take long for my sweatpants to come down. I laid back against the mineral tanks that my uncle stored out there; I'm not sure why he had them or what they were for, but they were cleaner than the cold concrete of the floor. Tyler sat down beside me and then leaned forward, grabbing my dick and slipping it in his mouth.
I laid there, enjoying the warmth and all of the pleasurable sensations that washed over me as Tyler worked his magic. I wished that head felt that way for me every time, not just with him. I'd like to think that it would feel just as amazingly if it was from a guy that I was attracted to and loved, but since I had never been fortunate enough to experience that, I could only speculate.
It didn't take long for me to cum. my hands buried in his wavy hair. I was reaching for his cock before the waves of pleasure had even waned. I knew from our messages that Tyler was still "lasting like steel" and that I wasn't going to make him cum, but that didn't mean that I couldn't have fun, after all, it wasn't often that I got to play with another penis.
I pulled his cock free from his fleece joggers, my mouth watering as it grew harder in my hands. I imagined the feeling of it filling up my mouth, the taste of his salty precum drizzling my tongue. I wanted him, even if it did leave me with a sore jaw. Deep in my heart, I wished that it was Rylan out there with me, his hard cock in my hand, but if Rylan wasn't going to give me what I wanted - and needed - then I had no choice but to find someone else who would.
I'm not sure how long I sucked him off, but it wasn't long enough for my jaw to start to hurt. I was fully committed to trying to make him cum this time, but while I was laser focused, Tyler stood and pulled his fleece pants back up.
"Sorry, I'm getting tired. I don't want to risk falling asleep on the drive home."
My feelings weren't hurt; I knew that he had quite a drive ahead of him and, it being Michigan, the deer were out in full force.
As we headed back to the house, I thanked him and told him to drive safely. I watched him back out the driveway, unsure when - or if - we would see each other again. I was hopeful that I could somehow turn things around with Rylan, to fix whatever issues ate away at us, but I knew that hooking up with other guys wasn't going to solve the problems we had.
I messaged Tyler a few hours later to make sure that he made it home safely. He let me know that he did, but he had had to stop a few times and yell at some wayward deer that had decided to try to cross the dark roads in front of him,
Tyler and I haven't talked since that night. By November of that year, he was dating an attractive guy named Wesley. They own a house together and have cats; from everything I can see on his Facebook, he looks like he's happy and thriving. I hope that Wesley treats him well and is able to make him cum - he deserves a good orgasm.
I'm fully aware that the biggest obstacle in the way of getting what I want in life is myself; you can't expect to find love, happiness, and a fulfilling life when all you do is work, when you hide away in your house in your spare time and talk to strangers online - safe from ever forming any real attachments. The problem is, I don't know how else to be; I've never been a go-getter, never been someone who wants to go out into the world and do things. I know that I'm weird and awkward, that that isn't appealing to guys, but I've never learned how to pretend to be normal, at least not convincingly. All my life, I've believed that home equals safe and good, while the outside world equals scary and bad; I'm not sure how to rewire my brain into believing otherwise. At the end of the day, I'm stuck being the me that I've always been and probably always will be. Maybe one day, I'll find someone who can see through my peculiarities into the kindhearted, loving person within, but I will never stop hoping, never stop questioning, never stop letting the romantic in my heart occasionally take the wheel.
About the Creator
Gabriel Bradshaw
I've been dating for twenty years, and I have some insane stories to share. Join me on my quest of love: romantic love and the love of labels. The dating world is savage, but I won't give up until I get what I want.
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