Evan - My Obsession - Part III

Thanksgiving came and went, and even though I broke the promise to myself about not letting Trevor fuck me again, and more importantly, not letting him fuck me bareback again, I still enjoyed a few days home with my family.

No surprise I didn’t hear from Trevor for a while. Once he got what he wanted, he was back to being “straight” and had no interest in even being a friend, so fuck him. I returned to my classes for the next couple of weeks before Christmas break began. Even though I was annoyed that Trevor was pulling this bullshit and acting like he was too busy for me, it was still lingering how we shared something so sensual and special by letting him be the only guy to cum inside me. He didn’t seem to care, though, and I think that’s what annoyed me the most.

Right before everyone went their separate ways for the holiday break, there were a few parties, and I tried to get laid, to get it out of my system before going home for a few weeks. I wasn’t expecting Trevor to hit me up during the break, especially since he completely ignored me this time around, not even a “I’m busy” text like last time, but I still wanted to get laid just to keep my horniness in check so that if he did hit me up I wouldn’t be so willing to let him do it again. Keep somewhat of a clear head about me.

I didn’t get laid.

I drove home back to Bouckville; it was a longer drive. Since I didn’t get laid during last night's party, I was horny as hell and found myself edging most of the drive, until I found a napkin in the glove box and finished myself off, trying to make as small a mess as possible while maintaining the speed limit. It wasn’t easy, and I still got a bit of cum in my pubes, but it all dried by the time I pulled into the driveway at my parents' house. Was it a satisfying orgasm? No. Did it take me down a notch on the horny scale? Yes.

My family spends Christmas Eve together; Mom makes a feast, we open gifts, and then we go to bed early. Then we spend Christmas day at Grandma’s house, about an hour drive further west. This Christmas Eve was no different. I received a lot of gifts related to dorm room needs, a few gift cards, and some reindeer-themed pajama pants.

While we were having our last tradition, hot cocoa by the fireplace, I got a text from Trevor.

Trevor: Merry Christmas Eve!

I rolled my eyes. Here we go.

Me: Merry Christmas Eve.

Trevor: Are you back in Bouckville?

Me: Yup.

Trevor: Me too.

Me: I’m with my family right now, can’t talk.

Trevor: Ok, text me when you’re free tonight.

I closed my phone, scooped up my Christmas gifts, and took them all to my bedroom. Then I put my phone on the charger and went to finish my cocoa and laugh at my sister as she pretends she’s not being a bigger slut than I was my freshman year at college. My older brother gets it and keeps rolling his eyes as her obvious stories skip all the good parts, and it cracks me up because she can’t see the faces he’s making at me from where he’s seated.

We all said good night, and I hopped in the shower before getting ready for bed. The hot water in our house is in short supply in the morning, so I usually shower at night and let them fight over the shower in the morning.

When I got out of the shower, I put on a pair of striped BVD briefs that were as close to Christmas colors as I had, then I put on the reindeer PJs and hopped into bed. I pulled out my laptop and started looking for porn. Just wanting a quick jerk-off to help me get to sleep since it’s barely 9:00 pm, but I have to be up at 6:00 am to make it to Grandma's for lunch, and I’m not usually asleep before 1:00 am these days. So a quick tug will certainly help me relax and fall asleep. Besides, when I’m home in my old bed, it’s easy to get comfortable and take my time, knowing I don’t have a roommate who could burst in at any moment.

I had my undies and PJs pushed down to my ankles, dick in hand, getting close to blowing my load when I heard my phone buzz. I knew who it was without looking, and I wanted to ignore him, but…ugh, dick in hand, balls churning, there was no way I wasn’t going to look.

The first message must have come in while we were still sitting by the fire.

Trevor: I have a Christmas present for you.

The one that just came in was much more forward.

Trevor: I’m going to be in front of your driveway in five minutes.

I jolted up, setting my laptop aside as my blood started rushing through my body.

Me: What!? Why?

Trevor: I want to give you your Christmas present.

Trevor: And I was hoping to get one from you hahaha

Me: Dude, I have to be up early, I’m not going to let you fuck me.

Trevor: Just come out, I’m in front of your house.

I peeked out the curtains, and sure enough, I could see the running lights of his Tahoe at the end of my driveway, the brake lights glowing on the snow outside.

Ugh, shit. I guess the least I can do is go see him to say ‘Merry Christmas’ in person.

I put on an old grey thermal shirt from the GAP that was in my drawer, then some socks, and snuck downstairs. I slipped on some snow boots and then put on my heavy winter coat as quietly as possible as I slipped out the garage door and ran down the driveway.

He rolled down the passenger side window as I walked up. His music was low, the heat wafted out of the SUV, and I leaned on the window. “Get in,” he flashed me that smile, and I listened.

He put the Tahoe in drive and turned the lights back on.

“Where are we going?” I asked, quickly reaching for the seatbelt instead of the door handle.

“You’ll see,” he smiled at me, then kept heading straight, which took us onto a D.O.T. road.

“You know this is a dead end, right?” I looked over at him.

He chuckled, “Yeah,” then he licked his lips and his smile curled up to his eyes. “I want us to have some privacy. So I can give you your Christmas gift.”

I scoffed, “Dude, I told you I’m not going to let you fuck me.”

He chuckled, “I know. I’m going to let you fuck me.” He turned to gauge my reaction, and I probably looked like I just had a stroke.

“What? Are you for real?” I stammered, blood instantly rushing towards my dick.

He couldn’t stop smiling, “Yeah, I have been thinking about it since our last hookup. I want to try it and I want to try it with you.” He kept darting his eyes from me to the road. “Unless you don’t want it,” a look of concern splashed across his face.

I was in a bit of shock. My cock was already reacting; I could feel a drop of precum leak out into my BVDs; thankfully, my winter parka was hiding my erection well. “I…umm…yeah. If you want, I mean. I don’t want you to do it just because you think I want you to.”

His head fully turned toward me, “Oh, I want to. I’ve been practicing with my fingers on my own and…I want to,” he smiled, then turned back to face the now one-way road. He turned off the headlights and slowed down as we got to the end of the road, where they store the snowplow trucks and rock salt. It has security cameras, but they are only checked if something goes wrong. I wouldn’t expect them to look on Christmas Eve.

Trevor did a U-turn and then backed the Tahoe up, parking it between two massive plow trucks so we were hidden. He shut off all the lights but left the music on and the heat on. Then he unbuckled and grinned at me. Without saying anything, he hopped out, and then as quickly as the driver’s side door closed, the door to the back seat opened, and he climbed in.

Oh shit, this is happening, and it’s happening right now. My heart was pounding out of my chest as I watched him strip off his jacket and put it in the front seat.

“Get back here,” he smiled.

I quickly unzipped my parka and shed it like a layer of skin in my seat, then I kicked off my boots and poured myself between the bucket seats into the back bench seat with Trevor. He quickly leaned in and started kissing me. Gentle at first, but as the seconds ticked over, he got more aggressive, and I felt myself getting hotter and hotter.

I started pulling his T-shirt off, revealing his toned chest, and he pulled my thermal shirt off. He kissed me again, and his hands went for my pajama pants, yanking them down easily. He broke our kiss, taking in my mostly naked body. I could see the lust in his eyes as his hand traced down my happy trail and slipped into the waistband of my briefs to grab my rock-hard cock. “Mmm,” I breathed in. His hand was a little cold on my cock, but it didn’t matter; I was about to fuck Trevor.

I hooked my thumbs in my BVDs and shoved them down around my ankles, spreading my legs to give him more access as he mustered up the courage to take me in his mouth again. This time around, he had a better idea of what he was doing, but it still wasn’t one of the top ten blow jobs of my life. I did enjoy his effort, though, and tracing the muscles in his back as he leaned over and sucked my dick for a few minutes. I decided to do my part and slid my hand down his back into his jeans and boxer briefs, letting my middle and ring finger slide right between his cheeks and trace his hole. He hummed on my cock but didn’t pull off. He was serious about trying this.

His free hand reached for the button on his jeans and then undid the zipper. He reached back and shoved both articles of clothing down his ass, letting me have full access to play as I wanted, as he continued to slurp on my dick. I wet my fingers with saliva and put them on his pucker, adding more than I usually would, and slowly inserted just the tip of my middle finger. He was tight as hell, but not squirming, so I slipped it in deeper to the second knuckle. That got a reaction out of him, but not an unpleasant one. His tight ring was clenching on my finger like it wanted to snap it off my hand, but he wasn’t fighting me either. He was willing, but his muscles were tighter than most guys I’ve fucked, and he was going to need some extra prepping.

“Take these off,” I said, pulling at his boxers and jeans.

He sat up quickly; his face was dark, but with the moonlight reflecting off all of the snow, I could see both the nervousness and excitement in his eyes. He quickly slipped off the last of his clothes, and I slipped mine off my ankles and set them in the front seat.

I grabbed his muscular leg and spun him in the seat so his back was to the door, and put his right leg up on the back of the bench seat, spreading his legs. I picked up his other leg and pushed his knee up towards his head, “Hold this up,” I instructed, and he did it without hesitation. I dropped down and started sucking his dick. All six inches of thick meat went quickly into my more experienced throat, and he moaned and flexed all of his muscles. I only wanted to get his mind off of what was about to happen to help him relax, but I could tell he was quickly getting a little too excited, and pulled him out of my throat. Kissing my was down, I sucked one of his nuts into my mouth and he groaned. I deliberately sucked a little too hard to get him to speak up and tell me, “Ahh, too hard,” and I dropped it out of my mouth and gently sucked the other nut. I wanted him to know he could tell me what felt good and what didn’t.

I pushed on his thighs, exposing his hole even more, then I sucked just below his balls for a second, slipping lower, and lower, and then let my tongue drop into the crevice of his crack and right over his hole. 

“Oh fuck,” His breath hitched.

I quickly did it again, tracing the tight pucker, feeling it pulse in reaction to my touch as Trevor squirmed and pulled his legs tighter to his chest so I could keep doing what I’m doing.

“That feels so good,” he mumbled.

I lifted my head slightly to see the pleasure on his face, “You like that?”

“Uh-huh,” he breathed heavily.

“This is rimming,” I told him, then dove back into his hole, this time, pushing my tongue into the tight ring.

“Oh God, that feels so good,” he banged his head on the armrest of the door.

My tongue pressed harder and harder until his sphincter relaxed enough to let me push in, and he moaned in pleasure. I licked and pushed deeper and deeper until I had no tongue left, and he squirmed and moaned under the power of my tongue.

“Jesus, Evan, I…mmmm, that feels so good,” he mumbled.

I took that as a sign to step it up a notch and wet my finger, slowly pushing it into his hole with my tongue. Gently, yet firmly, until I was able to insert two fingers and start separating and stretching the tight outer ring. Listening to his body, making sure I didn’t get anything less pleasurable than a hiss, no painful groans. I wanted him to keep wanting more and more until I could slip my seven inches of cut cock into him.

That time came quicker than I expected. He started jerking himself off while I was eating his hole, and I recognized the change in his tone when he said, “That feels so good.” I knew he was on the edge. I pulled my tongue from his hole and adjusted myself right between his legs. The tip of my dick is able to tease his pucker, and I do.

“Mmm…fuck, Evan…fuck me,” he mumbled under his breath.

“Are you sure?” I asked, knowing he was in heat and wouldn’t deny me at this point.

“Oh yeah,” he moaned.

“Do you have condoms and lube?” I asked.

He pointed at the center console. I leaned over and lifted the hatch. There was a bunch of junk and a Dougherty Pharmacy bag, containing two items. I pulled out the bottle of Astroglide and the Trojan ENZ Spermicidal Lubricated condoms. “Afraid you might get pregnant?” I asked, half joking.

He shrugged and puffed out some air, “Those are the ones I always buy…for me.”

He didn’t feel the need to remind me he’s “straight” in that sentence, so I took it as growth.

I lubed up some fingers and then leaned over him to kiss him. He was hesitant at first, probably because I just had my mouth on his ass for the last fifteen minutes, but when my lubed fingers started probing his hole, he heated right back up and started sucking my tongue out of my mouth. He moaned when I inserted a second lubed finger, but didn’t resist. His hand came around to the back of my neck, and his left leg wrapped around my naked waist as my two fingers sank as far into his hole as they could go.

I fingered his hole until I felt him stop trying to push me out. That's when I slid my fingers out and reached for the twelve-pack of condoms, tearing it open. I ripped off a condom, then tore the wrapper with my teeth, spitting the torn part out somewhere into the Tahoe as I pulled the latex out of the packet. I stroked my dick a few times, making sure I was at full strength before rolling the condom down my cock, then lubed up the condom covered shaft. I added a dollop more of lube to his hole, then I positioned my cock right on his pucker.

“You ready?” I asked, adding the slightest amount of pressure and feeling his pucker instinctively tighten. He nodded, yes. I put his left leg on my shoulder and added a little more pressure. “Jerk yourself off,” I whispered as I added a bit more pressure and felt his ring tighten even more and his face scrunch up. He quickly reached between his legs and started stroking his dick that softened pretty quickly as I nudged my tip at his hole. “Just relax and let me in,” I kissed the calf on my shoulder. He stroked his dick back to life, and I felt his pucker relax ever so slightly. That’s when I pushed hard enough to get the head to pop in.

“Oh fuck,” he managed to growl at me as I heard the air escape his body.

“Just relax, man, it only stings for a second,” I told him, not pushing any deeper. I felt his hole clenching hard on my cock head, but I didn’t let him push me out.

“Ungh, no, fuck, I don’t think I can handle it,” He groaned.

I rubbed his thighs, “Just relax, I promise you can handle it, and it’ll feel good in a second. Just breathe.”

“Fuck, Evan, I don’t…ungh, I think you’re too big,” he mumbled, his face scrunched up.

I tried not to laugh, “Just relax and push out, like you’re taking a shit.”

He did as he was told, and his hole allowed me to sink in about two inches before I hit more resistance, and he clenched again. That was all I needed to be able to hold myself inside him, and I leaned over him and started kissing him. His lips were tighter than before. I could feel the struggle in how tense his kisses were, but he kept kissing me. He wrapped his arms around me, and I started rocking my hips gently, just micro thrusts to massage his hole and keep him opening up. “Fuck, you’re so tight,” I mumbled into his mouth and continued kissing him. I rocked my hips to push another inch into him.

“Ngh…fuck,” he gasped into my mouth, but continued kissing me.

I had half of my cock inside his tight hole; the pulsing and clamping of his chute around those few inches kept me hard as a rock, but I needed more. I pulled out a quarter of an inch and pushed in a full inch. He sucked in a sharp breath and then let it out as a low groan. “That’s it, open up for me, Trevor,” I kissed him again and again rocked my hips out a quarter of an inch and in a whole extra inch.

“Oh God,” he groaned, this time with pleasure instead of discomfort.

“That’s it, you feel my dick inside you?” I moaned into his mouth and pulled out a little, then sank the rest of my cock into him.

“Ungh, fuck,” he hissed.

“Mmm, my entire cock is in you,” I whispered and felt his hole pulsing around my cock. I kissed him some more. He relaxed quickly, knowing there were no more inches to push in. His kisses became more passionate, and he reached between us to start jerking his cock again. “That’s it, feels good, doesn’t it?”

“Uh-huh,” he breathed, holding his hand on the back of my neck, my forehead on his as he closed his eyes and started stroking his dick with mine inside him.

I couldn’t wait any longer and started rolling my hips, gyrating my cock in his hole to stretch him out a little. He groaned and moaned, unsure if it was pleasure or pain he was feeling, but his cock was loving it. He was hard as steel in a few strokes. I pulled out an inch and buried myself in his ass. “Ungh, mmmph,” he moaned a beautiful cry of pleasure. I did it again, two inches this time, and the pitch of his moan became a little more feminine, and I loved it.

“That feels so good,” I told him. I started giving him half of my cock, balls deep, and then pulled out halfway. I stroked gently into him, always giving him my full seven inches, making sure to flex my cock on his prostate with each stroke.

“Mmm, that feels good,” he mumbled, stroking his dick faster.

“Yeah? You like taking my dick?” I whispered into his ear and kissed his neck.

“It feels so good, Evan,” He stroked even faster.

“Are you close?” I asked, stroking longer strokes into his tight ass.

“Yeah,” he breathed out and kissed me. “Are you?”

I started thrusting harder into him, kissed him, “Yeah,” moaned, and thrust a few more times, “You’re so tight, it feels so fucking good,” I kissed him again.

He stroked his cock faster, “Oh God, it feels so good,” he moaned. 

I gave him a few more deep thrusts and then started focusing on my orgasm. I had been on the edge before I got in the Tahoe with him; now my balls were boiling with need to burst.

“Oh fuck,” he held on tight as I started really fucking him. “That feels so good, Evan,” he moaned, letting off his dick for a second so he could pull me tighter to him. I put my hand on the door between his head and the hard plastic so I could fuck him harder and not hurt his head. He reached back down between us and started pumping his cock. “I’m so close,” he warned.

“Mmm, me too,” I pegged him harder this time, and he squealed a little.

“Fuck, I want you to cum in me,” he moaned, fisting his cock in time with my thrusting.

“Yeah?” I gave him a few more deep thrusts. “You want to feel me cum in you?” I breathed into his mouth between kisses.

“Oh yeah, so bad,” he mumbled in half-breaths. “Take the condom off and cum in me, Evan. I want to feel it.”

I pushed myself up further off him so I could look into his eyes, “Are you sure?” I bottomed out, and his eyes rolled into the back of his head.

“Mmmm, yeah, do it, cum in me,” he mumbled.

I reached down, fumbling to pull the slick condom off. I hooked a thumb in it and ripped it off with a snap. I’ve never fucked a guy bare before, and just thrust back into him, his tight, velvety skin was smooth on my skin.

“Ungh,” he groaned and clenched, his toes curling instantly.

“Sorry, you ok?” I asked, sliding gently out and adding spit for lube, then pushing slowly back in.

“Yeah, just, ungh, just cum in me,” he said, pounding his dick, his hand placed on my chest as his leg wrapped around my waist, pulling me into him.

I rocked my hips a few more times and felt myself getting back to the edge. He was clamping down hard on my cock and stroking himself faster. He looked so hot taking my dick, his muscles flexing, the pleasure on his face, I can’t believe I’m fucking Trevor…bare, in his Tahoe.

“Oh fuck, I’m cumming,” he whispered, and I felt his ass clamp down on my cock as his entire body lurched and cum shot out of his dick, hitting the door behind him with the first wad, the next couple splattering on his bare chest and abs. “Ungh, fuck,” he moaned and trembled under me.

I continued fucking him, pushing through his ever-tightening ass. I felt my balls tighten and heard him groan at my thickening cock pushing him past his limits. “Oh fuck,” I thrust, “I’m gonna….UNGH,” I pushed hard into him and unloaded deep into his guts. My next thrust was the slickest I’ve ever felt, no friction, just tight, juicy sliding of skin on skin as my cock continued to pump hot semen into him. He moaned in pleasure with me as I slowed my thrusting to a halt, barely holding myself up. I huffed, “shit,” I huffed again, “that felt… so good.” I chuckled.

He huffed, and his smile grew, “Jesus, Evan, you’ve been holding out on me.”

I smiled, leaned down, and kissed him, then slowly pulled my dick from his slimy ass and felt his soul escape his body as the tip left his pucker and the elastic ring clamped shut, holding my cum inside. “All you had to do was ask,” I breathed into his mouth and kissed him one last time before sitting up straight.

He kept lying there, catching his breath, slowly stroking his dick, and looking at me. Rihanna’s “Don’t Stop The Music” was thumping on the radio, and Trevor thumped his now fully hard cock on the pool of cum on his lower abs. “I don’t suppose you’d let me fuck you?” He asked with a vulnerability in his voice that melted my grinch-like heart.

I don’t usually let a guy fuck me after I’ve cum, I’m a one-and-done kind of guy, but looking at Trevor in the moonlight, coated in his cum, glistening with sweat, and horny with lust for me, how could I say no?

I positioned him sitting up in the center of the seat and straddled his lap. I grabbed the lube and squirt it on my fingers and pushed it into my hole, then grabbed a condom.

He chuckled, “You’re going to make me wear a condom?” He raised an eyebrow, “Your cum is in my guts, Evan,” his eyes pleaded with me. I caved instantly, leaning in for a kiss and stroked his cock with the extra lube on my hand, mixing it with the cum from his pubes, and lift my ass right above his thick tip. I put his head right on my hole, dancing my tongue with his in his mouth, and tried to relax as I bore down and slowly slide my ass down his shaft. We both moaned one long moan as all six inches of his thick meat slowly disappeared into my hole. “Oh fuck,” he whispered into my mouth.

“Mmm-hmm,” I kissed him back and started slowly rocking my hips in his lap. My balls were getting sticky with the cum dripping down his torso as I rocked up and down. I started stroking my dick between us and rocked my hips on his lap.

“Fuck…mmmm,” he moaned between kisses, rocking his hips up to meet my ass.

I know he’s not going to last long, so I focused all of my attention on getting a second nut and stroked my dick furiously to the feeling of his raw meat stretching my hole.

“Jesus,” he panted, “Evan…you feel so good,” he mumbled into my mouth, holding my hips as he rocked up into me.

“You’re dick feels so good,” I mumbled back, clenching my ass at just the right time to get maximum pressure on my prostate as he pushed up into me. It only took a few of those perfectly timed strokes for me to be on the edge again. I could tell from his thrusting he was already there. “Cum in me, Trevor,” I whispered and stroked my dick faster, my ass pulling his cock in and out as I rode up and down on his shaft.

“Fuck,” he thrust hard, “fuck,” he thrust faster, “I’m cumming, I’m cumming,” he breathed into my mouth, and I felt his dick pulsing inside me. I rocked my hips on his cock, feeling his juices squirting into my guts as his shaft massaged my insides. It pushed me over the edge, and without any warning, I let my cum squirt up his chest, hitting his chin and then coating the already cum slicked torso with each additional shot. I continued to rock my hips on his sensitive cock, making him squirm, but the pleasure inside my hole was too good, and the aftershocks of my orgasm had me pumping more and more cum onto him as it blew my mind and I moaned and squirmed. He couldn’t take it anymore and clamped his hands on my hips to stop me from squirming. “Fuuuuck…” he huffed out of breath. “Trevor…fuck,” he caught his breath for a second. “That was so hot,” he relaxed his grip on my ass and let his head fall back onto the back of the bench seat between the two headrests.

I know he’s spent and about to lose his horny fog, so I took one last kiss from his soft lips and then slowly climbed off his sticky body, letting his cock fall from my ass, and tried my best to hold his cum inside.

“Umm, do you have any napkins?” I asked.

His head popped up, “Uh, yeah,” he pointed behind the seat to a roll of blue paper towels. I reached back, pulled out the roll, and ripped off a sheet, handing it to him. “Thanks,” he breathed out, still trying to come back to life.

I pulled a sheet for myself and wiped off as much cum as I could feel on my chest, then my well-lubed cock, and lastly my slimy ass hole. I watched him slowly and meticulously clean himself with the one sheet and then tossed it in the back when finished. I tossed mine back there with his. Then we dressed slowly as “All I Want For Christmas” came on the radio, and I couldn’t help but chuckle. I pulled up my pajama bottoms over my BVDs and watched as he slipped on what turned out to be black CK hip briefs and not boxer briefs. I had to say something. “Oh, look who’s wearing briefs now,” I chuckled.

He shifted around, reaching for his jeans, putting one foot in, “Yeah, I told you I’ve always worn briefs, just not when trying to get laid.” He grinned at me.

“Tonight the exception?” I grinned, pulling my thermal shirt over my sticky body.

He chuckled, “Tonight was a lot of firsts.” He opened the door, and a rush of cool air blasted into the Tahoe. The dome light seemed incredibly bright as he found his t-shirt and pulled it on.

“Good firsts, I hope,” I said, feeling a little pang in my chest.

“Too good,” he shrugged and hopped out of the Tahoe, closing the door gently before getting into the driver's seat.

I poured myself back into the front passenger seat, slipping my feet into my boots as I sat properly. I didn’t want to press further on “what that means,” so I slipped my arms into my parka and pulled my seatbelt, knowing this experience was done for now. He was obviously trying to figure out “what it means” for him, and I’m not here to pressure him.

The next morning, I woke up to the sound of my sister banging on the bathroom door, complaining about my brother wasting all the hot water. I realized I was covered in Trevor’s sex and wasn’t going to get a shower before heading to Grandma’s for Christmas dinner. Hopefully, she can’t smell it on me. Though when I went downstairs to have breakfast and my dad said, “You look like shit,” I just shrugged and told him, “I feel a little sore, must have slept weird.”