Evan - My Obsession

Obsession is a weird thing. I was obsessed with a straight guy, who I secretly always thought was bisexual if not gay. He was a stereotypical jock in our high school. He ran with a pack of jocks, who ranged from decent to D-bag. Of course, in the halls or around his bros, my straight guy Trevor would act up and say stupid shit, but then when we were paired up as partners in the classes that sat us in alphabetical order by last names, he would always be incredibly nice to me. I could’ve been reading it wrong, but it felt flirtatious even.

I am not a jock. I’m not a nerd either. I kinda float somewhere in between. I’m a B/C student, I’m in good shape, but not muscular, handsome, but don’t think I’m sexy, and even if Trevor were gay, I don’t think he’d be into me. That didn’t stop me from making a move during a graduation party, though. I tried to kiss him, and it shocked him. He shoved me away and called me a fag. I left the party, went home, and cried myself to sleep.

Two years later, I was at college, finishing a paper, and scrolled over to Facebook to see I had a friend request from Trevor. I thought about denying the request, but I felt like I had grown over the last two years. I came out, I’ve had sex, I’ve fallen in love, I’ve broken up, but a part of me, a particular six inches anyway, was still obsessed with Trevor. So, I clicked "Accept," and did what any sane person would do: closed out the tab. Just kidding, I went straight for his photos and started scrolling. I’m not an insane person. I didn’t like any of them, especially since the hot shirtless ones were more than a few months old, that would be creepy.

It might have been wishful thinking, or reading more into his photos than was there, but I noticed two things in my scrolling; the first was that there were exactly zero girlfriends or women tagged as a girlfriend. The second was how friendly he was with one particular guy in some of the photos, especially the “partying” photos. It was reminiscent of how friendly he was with me, which frustrated me both physically and mentally. Before closing out the tab, I did click on his “about me” info, and scrolled down to see the big, bold words indicating he’s “Straight.” I rolled my eyes and closed out the tab.

Over the next few days, he started liking my posts. Not just one or two, but every single post I put up. Even the “Ugh, Monday…” post, which I didn’t even like posting, but didn’t have anything else to say.

I came back to my dorm pretty late Saturday night, kinda tipsy, very horny, and since my roommate wasn’t back yet, I figured he’d be with his girlfriend all night, and I was free to stroke one out. I pulled up the hub and stripped down to my undies. I know my black Armani hip briefs don’t hide much, but if my roommate did come back in, I wanted to be able to at least cover myself. We’ve caught each other jerking it before, multiple times, but we don’t have any agreement on open-season jerking it in front of the other, so I make sure I’m ready to tuck it back in if I hear the keys in the lock.

What I wasn’t expecting was Trevor to private message me.

Trevor: Evan!!!

Me: What’s up man?

Trevor: oh, you know…Saturday night

Me: Yeah

I didn’t know what to say. I had my dick in my hand and could hear a guy on another tab moaning as he was getting fucked by a much bigger guy in the background. As much as the horniness in me wanted to indulge in a late-night catch-up with Trevor, I also wanted to drain my balls and go to sleep.

Trevor: What are you up to?

I rolled my eyes.

Me: Jerking off, hahaha.

Trevor: hahahaha, really?

I said it as a joke, but since I really was jerking off, I figured I’d just be honest. What harm could it do? He’d get grossed out by the idea and unfriend me? Oooh, the horror!

Me: Yeah! I just got back from a party, had some drinks, didn’t get laid, gotta jerk off before bed.

Trevor: That’s cool, me too!

Me: Wait, for real?

Trevor: hahaha, yeah!

Me: Are you drunk?

Trevor: Kinda

Me: Prove it

Trevor: What do you mean?

Me: Send me a picture of you jerking off. Here’s my number XXX-XXX-XXXX

Sure enough, I got a grainy photo in my texts of a naked, muscled, headless torso and a 6” cut, thick cock hard as a rock lying on some bushy pubes, lit by the glow of the computer as he sat in his task chair.

Me: That’s fucking hot!

My dick was so hard, I kept my phone open and glanced at it several times as I waited for him to message me back.

Trevor: Your turn.

Does he want me to send him a nude?

Me: For what?

Trevor: I showed you mine, you show me yours.

I clicked on the desk lamp, angled it at my skinny, pale body, and snapped an equally grainy photo of my 7” cut dick. It’s not nearly as thick as his, but it’s mine. I sent it to him and waited for a response.

Trevor: Damn, Evan, I expected a micro penis hahahah

My heart sank. Was he pranking me to get a picture of my dick? Was he going to put it on like…some kind of revenge porn site?

Trevor: I’m kinda turned on, I’m not gonna lie.

My cock twitched again.

Me: Really? I thought you were straight?

Trevor: I am, but I’m also drunk and horny.

I rolled my eyes.

Trevor: Do you like my dick?

Me: Yeah

Trevor: What would you do to it?

Me: Are you naked?

Trevor: I’m wearing my boxers, but I’m hard.

I decided to play his game.

Me: If you were here, I would've gotten your dick out the fly, first with my hands.  Stroking it to that full-size hard dick, rubbing your balls.  Then I'd start licking the head, taking in your flavor.

Trevor: mmmm, go on.

Me: Lick up and down your shaft, then stroke your dick while I lick the area between your balls and your thighs, then move over to your big balls, sucking one at a time.

Trevor: so hot

Me: Still jerking your dick, sliding my tongue below your balls to the tender area just before your ass

Trevor: oh yeah, I’m jerking, keep going

Me: Just to tease you and make you moan, then I lick back up the length of your cock and get your precum on my tongue, tasting you.  Letting you thrust your dick forward into my mouth, taking it all the way down until my nose is rubbing your pubes, and my chin can feel your balls.

Trevor: mmm

Me: It's so big I'd choke and come back up for air, and you'd push your dick back down my throat because it feels so good and because you can.

Trevor: Yeah, I love the sound of someone choking on my fat dick.

Me: I'd start rubbing your balls with one hand, grabbing and pulling your ass cheek with the other, helping you push your dick ALL the way down into my throat.

Trevor: I’m close

Me: Building a rhythm, deep throating, and moaning because your dick tastes good.  Massaging your balls and using one rogue finger to rub your ass hole.  All while sucking your dick like we both wanted.

There was no response from Trevor.

Me: Did you cum?

Still no response.

I gave it another minute; I didn’t want to message again and seem desperate. After a few minutes, I knew he had blown his load and probably panicked and was now ignoring me. I went back to the porn and started jerking off. I pictured it was me getting railed by Trevor, and kept glancing at the photo he sent me. He may not be gay, but that photo was real. It pushed me over the edge, and I blew my load all over my stomach.

I cleaned up and went to bed.

A week later, I went out for a friend's birthday party, where I got really drunk, but again, didn’t get laid.

Back at my dorm, horny as ever, sitting in only a pair of white Jockey Y-front briefs, dick sticking out of the fly as I jerked off to porn, I heard the messages chime on Facebook.

It was the same stuff I had expected, a horny, drunk Trevor looking for me to get him off. The horny, drunk guy in me was mostly ok with getting him off. The idea of him stroking his dick while thinking of me sucking him off got me turned on. So I obliged. Getting him to send me a few more photos for my spank bank.

This routine became a pattern. I would tell him in detail how I would get him off, he’d cum somewhere in the process, and disappear for a few weeks, then pop back up. This particular Friday night, I was halfway through a similar conversation as the last one, where I was describing me giving him a mind-blowing blow job when he upped the stakes.

Trevor: Man, I’m so horny, you should let me come over and put your mouth to good use.

Being a bit drunk myself, I thought he was finally contributing to the conversation and trying to get me off.

Me: Well…that’s what I’m getting at hahaha

Trevor: No, for real. You’re going to Russell Sage, right? I’m over at Albany. It’s not far. There’s a bus that goes right there, I could be at your place in twenty minutes.

My hormones kicked into overdrive. I was already hard, dick in hand, and the idea of finally getting to suck Trevor off was like a fever dream.

Me: For real?

Trevor: fuck yeah, as long as you don’t tell anyone you sucked my dick hahaha

That made me roll my eyes, but the obsessed twink inside me, who never got to do anything with this “straight boy” back in high school, is dying to say yes.

Me: That sounds cool. Just a blow job?

Trevor: I’m not going to blow you, if that’s what you’re asking.

I decided not to push my luck.

Me: Yeah, cool, come over. My roommate is out for the night, most likely, so we have the dorm to ourselves.

Trevor: Awesome! The next bus is in 5 minutes, I’ll be there soon.

Then he logged off, and I ran to the showers to be prepared for anything, even though I’m sure he’s just going to cum in my mouth and run away.

I slipped into some Hanes white briefs in the hopes they would conceal my excitement… in case he gets weirded out about another guy being hard, then covered the tighty whities with some silver gym shorts and a ribbed tank. I heard my phone chime when he texted me to let me know he was downstairs. I slipped on my Adidas slides and took the stairs two flights to get to the door as quickly as possible to let him in.

He looked hotter than ever. Backwards fitted baseball cap covering overgrown, dirty-blonde hair, a baggy Albany hoodie that was unzipped, his white t-shirt clung to his pecs with his biceps stretching the sleeves. I could tell by his glossy eyes that he must have smoked some weed or something before coming over, but that doesn’t bother me. He looked nervous, so I didn’t waste time and just brought him right up to my room, locking the door behind us.

Trevor was just as hot as he was back in school, if not hotter now that he’d filled out a little more, and he’s got a little five o’clock shadow going on to accent his jawline. 

“So…how does this work?” He asked, with a nervousness in his voice.

Being the more experienced in late-night hookups, I assumed my position and dropped to my knees. I didn’t want to say the wrong thing, so I just felt my way through, glancing up with every new movement to make sure he was comfortable. Having his eyes locked on mine as I undid his belt, then his jeans, and pulled down the elastic waistband of his GAP boxer briefs with a tropical pattern splashed all over. My heart was pounding as I felt the warmth of his skin against the tips of my fingers while slowly pulling down to reveal his dick.

My heart was thumping in my chest. He was hard as a rock, so all six inches of cut meat sprang free, and for the first time, I was able to get a good look at my crush’s meat up close. My excitement level was so high that my tighty whities were not doing their job to contain my excitement. I could feel my precum pumping into the cotton fabric, and it was only a matter of time before you could see the wet spot through my silver shorts.

I took him in my hand, giving him a few strokes, hearing the air escape his lungs as I took control of his body through his joystick. I gave him a few pumps before bringing my face in, drinking in his scent, a smell that took me right back to when we’d sit next to each other in school and I’d get whiffs of his scent off his hoodie when he’d take it off, or when he’d put an arm around my shoulders before he asked me to do something stupid. Here, in his crotch, it was concentrated, and I was in heaven.

I gave his head a lick and gave him a few more tugs to get a drop of precum to pool in the slit so I could taste it directly. It was sweet, and I wanted all of it. I took him into my mouth and heard him groan. He put his hands on his hips like Superman, unsure how he’s supposed to get his dick sucked by another guy. Lucky for him, he’s not my first “straight dick,” and I dove deep, taking him into my throat as quickly as possible. I wanted him to compare every future blow job he gets from a woman to my expert skills.

“Oh shit, Evan, that feels so good,” he mumbled, flexing his ass in my hands as I held on to his cheeks and let him rock into my mouth as I bobbed up and down.

I looked up at him, looking down on me as my nose went into his wiry pubes. I felt a rush of pride in getting those words from Trevor. I pulled off his dick and gave him a few strokes, “Guys suck dick better,” I grinned, then put him right back into my mouth.

“Mmmm, fuck, you’re not lyin’,” he put his hand on the back of my head and started rocking his hips to meet my head. He was getting a little rough, but I wasn’t mad at it. “Oh fuck, that feels real good,” he grunted, and then, without any further warning, I felt his ass cheeks tighten in my hands and his cock throb in my mouth as a wad of hot cum splashed the back of my throat. I tried to swallow as much as I could, but had to pull off and take the last few spurts on my tongue so I could breathe. He tasted tangy, but I loved it because it was Trevor’s cum on my tongue, finally.

When his ass unclenched, I knew his orgasm was over, and I cleaned his cock before savoring the last drops of his load and swallowing like the slut I always wanted to be for him. I stood quickly as he pulled his shorts and boxer briefs back up, tucking his quickly deflating dick away with the snap of the elastic waistband.

He glanced down to see my seven inches straining to be set free from my briefs, and got a terrified look on his face. I slid my hand into my briefs and gripped my dick, not wanting to scare him off, but I was drunk with horniness and let myself push his boundaries a little to see how far I could go. I asked in a breathy voice, “Do you mind if I take care of this?” I didn’t wait for an answer and tucked my waistband below my balls, letting my dick stand out in all its glory.

“Oh, uh…yeah, go for it,” he said, crossing his arms but not taking his eyes off my dick as I started stroking it.

I slowly stepped backward towards my bed and pushed my briefs and shorts down to my ankles as I lay back on the bed and started putting on a show for him. Knowing he was watching me turned me into a bit of an actor. With other hookups, I would typically just stroke myself off quickly and blow my load all over myself, but I wanted Trevor’s post-nut clarity to wash off and have him remember what it looks like to watch another guy pleasure himself.

I spread my legs, running a finger over my hole, letting out soft moans with every new touch. Constantly stroking, edging myself so it didn’t end too quickly, keeping my eyes on him the entire time to remind him this was all for him, and available to him. I’m not a robot, though, so even with my focus on him, I still managed to push myself over the edge as I tasted the lingering flavor of his cum in my mouth. My balls tightened, and I flexed my legs and let out one last soft moan to make sure he was paying attention, pushing my shirt up dramatically so he could watch my cum splash onto my abs and chest with a slightly dramatic, “Ungh,” with every new spurt from my nuts until I was spent.

“Shit, Evan, that was intense,” He chuckled, pulling his hat off to push his hair back and putting it right back on.

I took a deep breath, “Yeah, what can I say… You turn me on,” I huffed. “Can you hand me one of those paper towels?” I pointed to the roll on top of the mini fridge. He grabbed it and tore one off for me, getting close to me to hand it over, his eyes taking in as much of my body and the cumy mess as he could before stepping back slightly, uncomfortable.

“Umm…I’m gonna head out,” he said, zipping up his hoodie.

“Oh sure,” I pretended not to mind as I sopped up cum from my stomach with a half sheet of paper towel.

“Thanks, though, I really needed that.” He said, then let himself out before I even got my underwear back on.

Over the next couple of weeks, I became even more obsessed with Trevor. Liking all of his posts, trying to chat with him every time he came online. He no longer seemed interested. His responses were always short, curt, and seemed like I was bothering him.

It was more than two months after I swallowed his cum, that I decided to give up and get laid by someone more…gay.

I went out with some friends from the campus LGBT group I joined. Hoping to get a few drinks and get laid, but by 1:00 am, everything was winding down, and I found myself heading back to the dorm to jerk off.

When I got there, my roommate wasn’t in, so I at least had the privacy to take my time and rub one out to internet porn instead of quietly under my blankets while he slept.

I was halfway through a longer session, had been stroking myself for the better part of half an hour, and was about to let myself cum when I got a message from Trevor on Facebook.

Trevor: You’re up late.

Just the sight of his name made me annoyed since he spent the last few weeks ignoring me completely.

Me: Yeah, just got back, going to jerk off and go to sleep.

Trevor: Fun, can I join you?

I sat up in my chair, still stroking my dick, and typed with one finger.

Me: I thought I freaked you out the last time.

Trevor: No, it was really hot watching you jerk off.

I hadn’t expected him to phrase it that way.

Trevor: And that was the best head I’ve ever gotten. I wouldn’t mind repeating it, if you’re up for it.

If I’m up for it?!!!

Me: Yeah, ok, if you want. Can you come now?

Trevor: I’ll head over right now!

He logged off before I could respond.

Shit. I hopped up and ran to the shower, just in case. This time, I put on some boxers, trying to look as heterosexual as possible. I even put on a Buffalo hat that I bought as a joke. Then I put on some grey sweatpants and a white t-shirt as I waited for him to text that he was here.

He looked less nervous this time, standing in my room with an air of confidence that I was used to and found sexy on him. I sat on my bed with him standing in front of me and pulled down his black sweatpants, as he unzipped his hoodie and tossed it on my desk chair. His dick was hard and pushing against the fabric of his light blue Old Navy boxer briefs with dark blue piping around the seams. He groaned as I rubbed him from the outside, and I looked up to see him smiling down at me. He inched forward, putting his knees between mine. I pulled his underwear down, that beautiful dick sprang free, and nudged against my cheek. The warmth was familiar, the scent was intoxicating. I took him straight into my mouth. I’m not sure who moaned louder, him or me, as I buried my nose in his pubes. “Fuck, Evan, you’re so good,” he mumbled and put both his hands on my shoulders.

I hummed on his dick and didn’t let up. I wanted to get him on the edge but not let him cum. Make him want it so badly he begs me to finish him off. When I felt his ass cheeks flexing in my palms, I could tell he was getting closer. I pulled his muscular ass apart and let my fingers tickle his hole, just to give him a taste of something I’m sure a woman has never given him. He let out a breathy, “Oh fuck,” and his hands clamped down tighter on my shoulders as his ass flexed. I knew he was close, and I pulled off, making him groan in need. When I didn’t immediately put him back in my mouth, he opened his eyes and looked down at me. “Why are you stopping?”

I shifted back on the bed and pushed my sweatpants to the floor, my hard dick poking through the fly of my boxers. I started stroking myself slowly as I looked at him. “I want to get off, too,” I told him.

He grinned at me, “Oh, ok,” he took his dick in his hand and started stroking himself.

“Is this ok?” I asked, leaning back on an elbow to make sure he got a good view of my dick.

“Yeah, it was really hot watching you play with yourself last time,” he whispered like it was a dirty secret.

“Yeah?” I grinned at him.

“Oh yeah. I’ve never seen anyone play with their asshole like that,” he grinned and pumped his dick.

“Do you… want me to play with your hole?” I asked as casually as I could.

“Oh…I don’t know,” he got even quieter.

I sat up and pulled his hips closer to me, pulling his dick back into my throat. I gripped his right butt cheek with my left hand and let my right hand slide between his legs and play with his balls for a little bit before I continued deeper and let my middle finger play with his pucker.

“Oh shit,” he groaned.

I pulled off his dick quickly, “Feel good?” Then put him back into my throat just as quickly.

“Oh yeah,” he mumbled, and his ass cheeks clenched around my finger when I tried to push in. He let me play with him for another minute before he asked, “Do you like having your hole played with, too?”

I pulled off his dick again, “I love it, it feels so good,” then dove back onto his dick for a few more bobs.

“Can I watch you finger yourself?” He asked.

My heart started racing as I pulled off his cock again. “If you want.”

His grin spread across his face, “fuck yeah.”

I didn’t hesitate. I leaned back on the mattress, lifted my ass, and yanked my boxers off and dropped them to the floor. Then I reached for the plastic bin under my bed that had my lube and condoms and pulled out the lube, quickly spreading it on my fingers and hole, then adding some to my cock.

“You put it on your dick?” He asked in surprise.

“Yeah, feels good to stroke with lube,” I told him, then handed it to him to try.

He applied some to his dick and started stroking as I lay back and started stroking my cock with my right hand and rubbing my middle and index finger on my pucker. I spread my legs wide so he could watch as he stroked himself. This was slightly new territory for me, so I just kept going, sliding my middle finger into my hole and watching the excitement on his face as it went deep.

“That’s so hot,” he whispered, putting a knee on the mattress and his free hand on my knee so he could get a better look as he stroked him self.

Feeling encouraged, I slipped my index finger in with my middle finger. The feeling was excellent, but his watching me pleasure myself in such a way had my hormones in overdrive. If I weren’t careful, I would’ve pushed myself over the edge and ended this entire thing too quickly.

“Does it feel good?” He mumbled.

I nodded and breathed out a quiet, “yeah.”

There was a slight pause before he squeezed my knee with his free hand and asked, “Can I try it?”

I wanted nothing more and nodded quickly. He picked up the tube of lube and wet his fingers. I spread my legs and continued stroking myself as I felt his lubed fingers feeling between my cheeks and quickly finding my hole. He slipped two fingers in quickly and with little finesse. I tried not to wince, but I did inhale sharply as he went into his thick knuckles. He didn’t notice, too busy, focused on his fingers entering my hole. “It’s so warm,” he grinned at me.

I smiled and let out a soft moan for his benefit. “It feels so good,” I said, despite the discomfort, and started stroking myself faster.

“Yeah?” He smiled, his eyes darting from mine to my hole and back.

“Oh yeah,” I said, then pulled my t-shirt up above my nipples as if I were getting close to shooting my load even though I wasn’t quite there yet.

“It’s so tight on my fingers, way tighter than a girl,” he said, laced with suggestive unspoken words.

“It’s so much tighter,” I told him, hoping this was going where I wanted it to go.

His eyes kept going from my hole stuffed with his fingers to my hand stroking my dick, and then up to my eyes and back down. “Can I try it?” His voice was barely audible, but the room was so quiet aside from our breathing.

I was afraid I’d shout “yes, please,” so I just nodded and watched his eyes light up. He climbed onto the bed and got between my legs. He didn’t add any extra lube, and I was afraid to say anything because I didn’t want him to change his mind. He fumbled around for a bit, unable to figure out the angle and probably afraid he was going to accidentally touch my dick, before he asked, “Can you go on your stomach?”

I nodded and quickly rolled onto my front. He spread my cheeks and put the head of his dick on my lubed hole, “right here?” He asked and started pushing. I groaned and tried to relax as his head popped into my tight pucker. I’ve been fucked many times, always safe, and always with more experienced tops, but my horniness had me dick drunk, and my obsession with Trevor allowed me to let him push in raw without a second thought. I groaned as he continued pushing his thick six inches into me without giving me time to adjust. My hole struggled around his girth, but I’ve wanted this for years, and let him push forward. “Oh fuck that’s tight,” he whispered, then leaned onto my back. He pulled his shirt up a bit so his skin was against my skin as he lay on top of me.

He didn’t wait for me to adjust like other guys do; he just hooked his arms under my chest and held me tight as he started slow, deep pumps into me. Grunting with each thrust. “Fuck that feels good,” he grumbled. I clenched my teeth and tried to relax. I was getting everything I ever wanted. It both hurt like hell and was terrific at the same time. His raw cock pumped into me a dozen times, and each time he bottomed out, he would flex his ass muscles and dig his dick a little deeper. It only took him a minute before he mumbled a breathy, “You’re so tight.” I got two more hard thrusts, and a quiet, “mmmph,” before his dick throbbed inside me, and the burning sensation of his dick rubbing against my sensitive skin was suddenly traded for a warm, Trevor-made lube that coated my insides. He relaxed on top of me, breathing heavily in my ear as his body twitched and his cock flexed.

“Shit, did you cum in me?” I asked, suddenly realizing I just let a “straight jock” fuck me raw.

He moaned out a low breath in my ear, “Yeah, it felt so good, I couldn’t help it.” He pushed himself off of me, his deflating dick slipped from my hole, and I felt him get off the mattress.

I propped myself up on my elbows and looked back to see him grabbing a paper towel to wipe the cum from his dick. Then I rolled onto my back and started quickly jerking myself off as I watched him getting dressed. I could tell the post-nut clarity had already settled in, but my horniness was still in overdrive, and I could feel his cum warm in my hole; that’s all I needed to blow my load. I barely pushed my shirt up fast enough before my load pumped out. One shot still rocketed onto my shirt, the rest pooling on my abs and belly button. 

Trevor ripped off a paper towel for me to clean up with. “I gotta head back,” he said awkwardly as he zipped up his hoodie.

I just nodded as I cleaned myself up and watched him leave. I felt instantly guilty for letting him bareback me. Knowing I let my high school obsession get the better of me. I had told myself I would only go bareback with a guy I was in love with, but I guess obsessed is a close second.