I felt his lips on the head of my slowly growing cock. It was the first blow job I’d ever gotten from another dude. And honestly, Jason seemed to know what he was doing as he slowly worked his lips up and down my shaft, flicking his tongue around every so often.
* * * * *
If you are reading this, hopefully you are already up to speed with the events of my first story, “Let’s Make a Deal,” in which I chronicled the mostly true story of the hottest sexual experience of my life. If you haven’t, please go back and read about the camping trip turned sex-fest with my hunk of a best friend who I had secretly lusted after for years, before going any further.
For those of you who have already read about all that, I’m assuming you are here for some closure from the little cliffhanger I left you with. Hopefully this satisfies.
So when I left off, Tyler and I had come home from our camping week and gone back to work and the real world. Me, a manager at a shitty retail chain, dangerously close to hitting the 30 mark. And Tyler, an employee at same said shitty retail chain, still comfortably in the middle of his twenties. For a few weeks things had seemed awkward between us. We weren’t avoiding each other or anything at work, but we also weren’t really connecting and hanging out outside of work like we used to.
Until our schedules seemed to finally align, and we agreed to one of our usual hang out sessions on a night when we were both off work the following day. As you may recall from where I’d left off, I vowed to confront Tyler about our sex-fueled bro-trip that we had previously agreed to never talk about again. Mainly, I was going to call Tyler out on a certain kiss that we had shared on that trip. A kiss that was initiated by him, in a moment that seemed somehow different from the testosterone filled fucking of the rest of that trip.
Well, to make a long story short, Tyler came over that night, we hung out in my parent’s basement watching weird Youtube videos and drinking, and then I called Tyler out on that kiss. He broke down and admitted that it had meant something to him as well, and we fucked like animals on the basement couch. The end.
Okay, so it actually didn’t go anything like that, because, unfortunately, that’s not how life works. Or usually not my life anyway.
In actuality, he came over, we hung out in my parent’s basement and watched weird Youtube videos and drank, and I was too much of a pussy to bring up anything about that kiss or that camping trip. We sat on the same couch, and I kept hoping Tyler would get drunk enough to initiate some asinine deal, like the one he’d originally proposed at my family’s cabin that had led to all the sex and shenanigans. But drink after drink, the topic never came up.
In fact, very late into the night, Tyler hit me with a bombshell of a different kind. Suddenly, out of the blue, he just casually dropped the “G” word on me. Yeah, out of nowhere, Tyler started talking about a girlfriend. Apparently, he’d been texting with a pretty little new girl at work for some time, and right after we got back from our guy’s trip, they’d gone out and were now dating.
Inside, I immediately felt crushed with a mix of confusion and jealousy. Outside, I think I responded to the news by saying “cool cool cool cool cool” way too many times in a row. We drank a little more, I got a little sloppy and I think started whining that we’d probably never hang out anymore now that he had a girl. He assured me that we would always be best bros. I think the cliched “Bros before hoes” phrase was even thrown around.
And for the most part, Tyler didn’t lie. In the weeks and months to come after, we did remain best friends. Sure we didn’t hang out as frequently. There were days when I’d get my heart set on doing something with my best friend, only to hear he already had plans with Rachel. I’d get disproportionately depressed on these occasions, but Tyler would always make up for it and hang out with me another day.
But things never stay the same forever. Eventually, I was called upon to transfer and manage a different location. So Tyler and I no longer worked at the same store.
We still hung out, but it became harder and harder to coordinate the time to do it in. Meanwhile, I was getting lonely. I’d tell myself I just needed to find a girl of my own, but then I’d talk myself out of it, convincing myself that no respectable girl would want to be involved with a recently turned 30 year old who still lived with his parents.
So I took the obvious next step from that, and turned to craigslist hookups. I’d still tell myself I needed to find a girlfriend, but there was no fooling myself about who I was looking to replace with these hookups.
I created a new secret email identity, and only agreed to meet guys at their places and other locations. I obviously couldn’t be inviting strange men back to my parents house.
Yeah, you heard me right. I was looking for hookups with other guys. I was trying to chase those feelings I’d gotten with Tyler. It didn’t make complete sense to me, but I’d find myself doing it anyway. To some very interesting results.
The first couple of times I chickened out and bailed. A few times, I could see the guy I was supposed to meet from a distance, see that he was nothing like he’d described or how he looked in his pictures, and I’d turn around and go home. Other times I was convinced the guy would have that same reaction upon seeing me. I mean, I tried to provide pictures that accurately represented myself, but of course I picked ones where I was a few years younger.
One of the first guys I actually followed through with seemed promising at first. We agreed to meet up at the food court in the mall, and I was actually really nervous that he was expecting for us to go off and hook up in one of the bathrooms or something. Instead, we sat there and had some casual, if a little awkward, conversation. We seemed to have some things in common as far as music and movies and things were concerned. We were about the same age, and you could say he was kind of cute, in a dorky kind of way, not unlike myself. His name was Jason, and he came off as maybe being as nervous as I was. That was okay, but i definitely needed him to make the first move here or we’d be sitting in the food court talking about Game of Thrones all night, if it were up to me to take charge.
“Sooo… Did you want to go back to my place or yours?” He finally asked, not exactly making direct eye contact.
“Your place!” I blurted out, probably a bit too quickly. He looked a little surprised at my outburst. “Sorry,” I continued, “It’s just, I’m kind of living with my parents at the moment.”
I felt my cheeks get hot at the admission. Idiot! Why would I tell him that? Then again, why not? I wasn’t looking for a long-term relationship or anything here. The goal here was a hookup. A quick fuck to get my mind off of the last sex of any kind I’d had, some six months ago by now, with Tyler.
“Oh, that’s cool. My place it is then.” Jason responded. I was silently grateful that he didn’t have a comment about my current living arrangements.
I followed him in my own vehicle back to his place. A duplex in a decent, pretty quiet neighborhood.
“Nice place.” I offered up awkwardly as I followed him up the sidewalk to the front door. “Any roommates or anything?”
“Nope, just me and my cat, Binks.”
A Hocus Pocus reference? Cool. I didn’t want to be a dork and ask. I followed him in. He offered a drink, which I accepted, and he went off to make them while I sat on the couch in the living room. While he was gone, I took a look around. Nothing screamed serial killer or anything, which was good. He had some emo band posters on the wall that I actually recognized.
Jason put on some music and I guzzled down my drink probably quicker than is polite while he sat next to me, like right next to me, on the couch. God I was so bad at this, and this was awkward.
Again, Jason came to the rescue, as I felt his hand on my thigh. “So… do you want me to suck your cock first or…?” He asked. He sounded almost as awkward as I felt, but God bless him for actually getting it out.
His hand began inching up my thigh towards my lap as I suddenly had something caught in my throat. I cleared it before croaking out a response, “I have to get… I mean I’m not even… you know… yet?” I stammered out like a nervous middle-schooler on his first date, nodding down in the direction of my crotch.
“That’s okay, maybe I can help you with that.” He responded.
I had no comeback to that, and so I let Jason fumble with my belt buckle and fly of my jeans. Why had I worn a belt and jeans anyway? I knew what this meetup was for, I should have gone with sweat pants, something easy to yank on and off.
After some more fumbling, Jason got inside my pants, only to find me wearing boxer briefs, with no easy access opening to my junk. I had to lift my hips off the couch momentarily for Jason to yank both pants and underwear down past my knees, exposing my lower half in all it’s half-chub glory. At least I’d had the presence of mind to do some trimming down there, leaving only a short stubble rather than the wiry bush that my half flaccid dick usually came poking out of.
I was mortified to be exposed like this in front of a practical stranger. I wasn’t even hard yet. I wouldn’t call myself gifted down there, or anything, but I at least looked respectable with a boner.
Thankfully, Jason didn’t giggle or scoff or anything. Instead, he took me in his hand and started slowly rubbing it around in his palm and between his fingers, cupping and caressing my balls and trying to stroke some life into my cock. I decided not to watch and instead tilted my head back on the couch and closed my eyes. A few moments later I sensed Jason shifting on the couch next to me, and felt his lips on the head of my slowly growing cock.
It was the first blow job I’d ever gotten from another dude. And honestly, Jason seemed to know what he was doing as he slowly worked his lips up and down my shaft, flicking his tongue around every so often, stroking with one hand, and cupping my balls in the other. I felt myself growing harder and harder despite my nervousness.
Odd as it sounds, With my head tilted back and eyes closed, I found myself not thinking about Jason, or anyone else for that matter, sucking my dick. Instead, I found myself remembering the times I had sucked Tyler’s dick. Somehow, I was getting off on thinking about the pleasure Tyler must have felt similar to the pleasure I was feeling with Jason’s mouth on my cock.
Whatever weird reversal of thoughts were swirling in my head had gotten me rock hard. Jason pulled his head out of my lap with a wet plop and then I heard his panting voice next to me.
“I’ve got some lube and condoms if you want to do me in the ass with that hard cock?”
My eyes shot open. Woah! What? That’s not how I was hoping this would go down. If I was chasing those feelings I’d had with Tyler at the cabin, then this was all somehow going the wrong way. It was like I was hooking up with another me, rather than a Tyler, if that made sense? Clearly I had not read the terms of our hookup carefully enough.
I scrambled in my brain to find a way out of this. I already felt my hard-on starting to lose some of it’s stiffness as my nervousness hit me all over again. I wasn’t Tyler. I didn’t know the first thing about giving a guy’s ass a good pounding. It was my ass that was supposed to be taking the pounding.
I decided on a plan, and before I could second guess myself, I was at Jason’s crotch with my hands, fiddling with the draw strings of his pants while I blurted out, “Let me get a suck on your dick first!” Umm… that didn’t come out right, did it? What was I saying, ‘get a suck on your dick?’ That wasn’t a thing people said.
Whatever I said, Jason seemed to buy it as he helped me yank his pants down out of the way, revealing his already hard cock in the center of a tight little bush of pubic hair. He was actually longer and thicker than I was anticipating and I almost blurted out a compliment on the size, but stopped myself from saying something else idiotic.
With thoughts swirling in my head, wondering if I still knew how to do this, I lowered my face down into Jason’s lap and took him into my mouth. Damn, he actually was pretty thick. I felt my jaw stretching to fit him in. I heard him let out a content sigh up above me as I let instinct take over and I began going to work on his cock with my mouth.
Bobbing my head up and down, working up as much saliva as I could to get him nice and slick, stroking up from the base of his shaft as I lowered my lips down from the head, I did my best to give him the kind of blow job that had seemed to drive Tyler over the edge.
For Jason’s part, he remained slumped on the couch with my head bobbing up and down in his lap. I could hear him panting and sighing above me, but he kept his hands to his sides.
I thought back to the times I’d blown Tyler at the cabin. His hands would always find their way to the back of my head, forcing himself further into my mouth as he humped his hips into me, face fucking me until his cock was gagging me and sliding into my throat.
I longed for Jason to take that kind of control of me, but he left me in control. I could still tell by his soft moans and sighs that he was enjoying it. I needed him to enjoy it even more. I needed to get him off and satisfied to avoid having to try to fuck his ass.
Taking my hand away from the base of his shaft, I started bobbing my head down further, gagging myself a few times as his thick cock reached my tonsils. Steeling myself, thinking back to when I had Tyler down my throat, I took Jason all the way in, burying him down my throat, nearly gagging as my nose pressed into his pubes. Up and down my head went, deep-throating him in and out as he began to moan and groan louder, squirming his hips around on the couch.
“Easy there man, you’re gonna make me blow already,” Jason warned.
That was the idea, buddy. Instead of easing up, I went faster, bobbing up and down, my nose jamming into his pelvis each time I swallowed him. I was making a slobbery mess in his lap. Jason was absentmindedly rubbing his hands into the fabric of the couch cushions on either side of him, squirming around frantically now in his seat.
“Uh! Uh! Uh! watch it, I’m gonna cum, man! I’m gonna cum!”
He was polite enough to give me the warning, and I felt his last second panicked attempt to draw his hips away from me to pull out. But by this time I was fully engrossed in the blow job. In my mind it was Tyler’s cock in my mouth, not Jason’s, and I wanted to taste his cum down my throat again. I grabbed the slobbery base of his cock before he could pull away and out of my my mouth. Meanwhile, I frantically bobbed and twisted my head, my lowering lips meeting my raising fist in the middle of his shaft each time.
Jason surrendered his squirming attempt at escape, went rigid, and with a grunt I felt my mouth filling with his hot cum. I milked and sucked every drop that I could out of him and let it slide down my throat before pulling my head out of his lap and gasping a breath while wiping a forearm across my messy mouth and chin.
Jason sat slumped back into the couch with a slightly comical euphoric look on his face. His slick impressive hard-on was already deflating in his lap. For my part, I was already standing up and pulling up my underwear and jeans, stuffing my softening junk back in and zipping up while Jason attempted to recover on the couch.
“Wow, that was great, thank you.” I offered. Was that right? Should I be thanking the guy for blowing his load down my throat? It seemed like the polite thing to do anyway.
“Wait- where are you going? We don’t have to be done yet-” Jason seemed confused, finally losing the post-orgasm glaze in his eyes. He attempted to stand up, but with his sweats bunched up around his ankles, he almost tripped and fell. As he righted himself, I started for the door.
“Yeah, it’s getting late, I should get going. But really, thank you,” I made it to the door, “You have a lovely home.” Okay, now that sounded really awkward.
And then I was gone. My heart finally stopped racing by the time I’d driven home. I went straight to bed, where, obviously, I furiously masturbated into a crusty old pair of underwear that I kept balled up under my bed like every grown adult. Cute as he might have been in his own right, it wasn’t Jason I thought about as I stroked myself silly. It was Tyler and his sometimes ridiculous verbal abuse that he spouted while I had sucked him or he’d fucked me that I thought about while I blew my load into my cum-briefs.
That proved to be enough sexual adventuring for me. When I checked my secret hookup account, I saw I had an email from Jason. He wanted to know what had happened, was apologetic about anything he had done wrong. He wanted to possibly meet up again. I had to chuckle, because it was such a ‘Me’ thing to do. I actually started composing a response. I wanted to explain that he was great, that it wasn’t him it was me. Ultimately I deleted it and decided it’d probably be best to just leave him alone, rather than fucking with his head any further. We were clearly too similar. Hooking up with him was like hooking up with myself, which was a really weird feeling to wrap my head around.
I thought my brief foray into anonymous hook-ups was over. All it took was one night of me sitting at home wanting to hang out with Tyler, only to see pictures of him and Rachel happily hanging together on his Snapchat for me to decide to give it another try.
Before I jumped back in, I decided to do a little more internet research into the lingo involved, so that I hopefully didn’t end up trying to hookup with another mirror version of me when that wasn’t what I was looking for. I learned all about m4m, top and bottom, sub and dom, ISO, NSA, DDF, as well as more specific, and stranger things such as ABR (don’t ask).
Armed with more knowledge, I went back at it. Eventually, I stumbled upon Colton. Through a few back and forth emails I learned that Colton was a dominant younger fit guy. It was obvious from all the pictures he shared of himself posing and flexing with his shirt off that he was really into showing off his fitness. I had to admit, if the pictures were actually of him, he was maybe in even better shape than Tyler. A fact that sent a certain thrill through me. Colton also seemed to be into, or at least not care that, I was a good 8 or so years older than him and not nearly in as good of shape.
After a few more messages back and forth, in which time I learned all about his workout and dieting regimen, we had agreed on plans to meet up. Colton was a senior at a nearby college and shared an off-campus apartment with a roommate whom he assured me had gone home to visit his family for the weekend.
After calming myself down numerous times, and having a few drinks, I worked up the nerve to head over there and meet him.
He answered the door in a skin tight sleeveless Under Armor top and gym short shorts. His pictures were indeed an accurate portrayal of himself. He was every bit of muscled, square jawed, college jock as advertised. My heart rate instantly elevated. The main room of his apartment was littered with various weights, work out gear, and tubs of protein powder. He had a few posters of extremely jacked and oiled up body builders posing in little speedos hanging on the wall, I assume for inspiration and future goals. On another wall was mounted a full length mirror.
Colton took a swig of a thick chalky liquid out of a protein shake bottle and asked if I wanted one. I declined. He offered me a vitamin water instead, which I accepted. I stood there awkwardly in the middle of a small living room that looked more like a gym, with one uncomfortable looking couch against one wall and a workout bench in front of it in place of a coffee table. Various weights and dumbbells were scattered around it on the floor and gathered on a rack against the other wall.