Evan - My Obsession - Part II

I spent a lot of time jerking off to the idea of Trevor fucking me back in high school. In practice, he had no finesse; he barely was inside me before he was blowing his load, and even though it filled a fantasy I had about him, it was lacking all of the things I liked about sex with other guys, like kissing or getting pleasure out of the experience. 

Still…the further from the experience I got, as days turned into weeks with no responses from him, I sort of paid no attention to him treating my hole like a fuck toy, and when my test results came back clean at the clinic, I started really leaning into how hot it was that Trevor shot his load inside me. It started to become the part I focused on when I knew I only had a few minutes to jerk off before my roommate got back from classes.

It wasn’t until Thanksgiving break, when I was back home visiting my family, that I heard from Trevor again when he shot me a text.

Trevor: Are you back in Fuckville?

Trevor: I mean Bouckville?

I had just finished unpacking and was getting ready to hop online and see who else was back in town for the weekend that I used to hang out with.

Me: Well, well, well. You’re alive?

Trevor: Yeah, sorry, I got busy with classes.

Me: Sure.

I wasn’t trying to let him off easy. He treated me like shit, and I know why he’s hitting me up now. I’ll be damned if I’m just going to be a hole for him to use…again.

Trevor: Come on, don’t be like that, Evan.

Me: Be like what?

Trevor: like some girl that didn’t know she was a one-night stand.

Me: Oh, was that a one-night stand?

Trevor: Well, it sure wasn’t a date hahahah

Me: I don’t know that I would call you shooting your load in two pumps a one-night stand.

Trevor: Damn, I thought you liked it.

Trevor: Was hoping you wanted it again.

Trevor: I need to get laid hahaha.

Me: I’ve had better, to be honest.

Me: And I just got in town, so I’m not really looking to get laid.

Trevor: Damn. Ok.

I thought that was the end of it. I took a shower and told my parents I was going to meet up with some friends. My friend Cassie picked me up to go to a small gathering at the go-to party house. I only had two drinks when I felt my phone vibrate with a text message.

Trevor: In my defense, I’ve never done anal before.

Trevor: Your ass was so tight, I couldn’t go as long as I normally do.

I thought this was funny and was feeling tipsy, so I had to respond.

Me: I’m sure that’s what you tell all the girls.

Me: “I’m sorry, baby, that’s never happened before.”

Trevor: Well…now that I know what I’m in for, you should give me another try.

Another try? Like my ass hole is a PlayStation game?

Me: Nah, to be honest, it didn’t live up to the fantasy.

I felt a little like a dick for sending that one, but I was trying to have a conversation with Cassie about what it’s been like since I came out because she’s still in the closet but in a relationship with a girl back at school.

Trevor: You fantasized about having sex with me?

I rolled my eyes.

Me: Yeah, but it was way better in my head.

Trevor: How so?

“Wow, you’re popular tonight,” Cassie said, with a heavy subtext.

“Sorry. One of the downsides to being out is all the booty calls.” I half-joked, then put my phone in my pocket.

“It’s alright. You have a man back at school?” She asked, her big brown eyes twinkling, ready for the gossip.

“Nah, I’m too busy to be dating,” I told her.

“Oh, so who’s blowing up your phone?” She crossed her arms.

I let out a heavy sigh, “Just some guy I hooked up with that…I guess is hooked on me.”

“Evan, you slut, giving it out for free,” she joked.

I laughed, “What can I say? I’m in demand.”

My phone buzzed again. I didn’t check, I just kept going.

About fifteen minutes later, Cassie had an alarm on her phone go off. “Sorry, it’s time to call Katie. Are you ok to float?”

I shrugged, “Yeah, of course.” She walked off, and I pulled out my phone.

Trevor: OK, I’ll admit I miss how good you suck dick.

Trevor: If you don’t want to hang out for sex, we could just hang out.

Trevor: Are you blowing me off now?

I couldn’t help but chuckle at how transparent he was.

Me: Of course, I fantasized about you, especially back in school.

Me: In those fantasies, you would look me in the eye when you fucked me.

Me: And kiss me.

Me: And then let me fuck you.

To my surprise, he texted me back within a minute.

Trevor: Oh, that’s pretty gay hahaha

I rolled my eyes.

Me: I’m gay, dickhead.

Trevor: I’m not gay, I just get horny and like to get off.

I huffed and started angry-typing on my phone.

Me: That’s why you’re jerking off tonight instead of fucking me.

Trevor: Awww, come on. You know I’m straight.

Me: Didn’t feel like it when you pumped your cum into my ass.

Me: Bareback.

Trevor: Oh, I remember, it felt soooo good.

Trevor: I’ve never fucked a woman raw, that was a first for me.

His moment of vulnerability reminded me of our one-on-one time back in school, when he would let his walls down and be a real person instead of a jock d-bag.

Me: Well, I never let a guy fuck me bare before.

Trevor: Wait, was I the first guy to cum inside you?

I felt my dick throb in my briefs at those words.

Me: Yeah

Trevor: Did you like it?

I wanted to lie and say no, but my horniness was already getting the better of me.

Me: Yeah

Trevor: Do you want me to cum in you again?

I swallowed hard, looking around to make sure no one could read my phone.

Me: No. I shouldn’t have let you cum in me that time.

Me: I never do that, and it was stupid.

Trevor: Damn, I was thinking I could let you kiss me if you let me cum in you again.

I laughed out loud at that text. He really is full of himself. I shook my head.

Me: I’m not even taking my clothes off until I’ve had a hot makeout.

Me: I’m not letting you fuck me until you’ve sucked my dick.

Me: I’m not letting you fuck me until you’ve rimmed my hole.

Trevor didn’t immediately respond. Not that I expected him to give in to my demands. Which was fine because Cassie came back in just as I flipped my phone closed.

I had another drink while Cassie explained all of her reasons for not telling her family about Katie. In the meantime, my phone buzzed in my pocket a few more times. I assumed they were messages from Trevor, but I wasn’t going to give him the satisfaction. 

People started showing up as I was getting ready to leave. One of those people caught my attention as he walked in with his backwards ball cap, square jaw, five o’clock shadow, and a U Albany sweater. I rolled my eyes so hard that Cassie picked up on it and looked.

“I forgot you’re friends with Trevor,” she said casually.

I nearly spit out my beer. “I wouldn’t call us friends.” I tried to reel in my emotions towards him. I may be tipsy, but I’m not about to out anyone either.

“Oh, I thought you guys were friends back in school?” She sounded genuinely confused.

I shook my head and plastered on a fake smile, “Yeah, we were, sort of. I don’t know, we weren’t exactly the ‘sleep-over type of friends,’ is what I mean.” My eyes followed him across the room until his eyes met mine, and the surprise on his face let me know he wasn’t expecting to see me any more than I was expecting to see him. He quickly dove into a conversation with someone else to avoid coming any closer to me.

I looked at my watch, it was 11:00 pm, and I have to be up tomorrow morning to help my mom prepare Thanksgiving pies. I let out a fake yawn, “Oh man, I think we need to head back.”

She cocked her head to the side. “Are you serious? It’s still early.”

“Early? It’s eleven,” I scoffed.

“Don’t be such an old man. I’m still waiting for Marryanne to get here. She text while I was on the phone, said she’s on her way.” She gave me her sad eyes, and I couldn’t argue.

When Marryanne finally arrived, Cassie went running over to her, essentially ditching me. Leaving me open for Trevor to swing over to the wall I was leaning against and start a conversation.

“Evan, long time no see,” he said louder than a normal person would.

“Ah, Trevor, I haven’t seen you since we graduated,” I said in an almost robotic voice, matching his volume.

He chuckled at that, then dropped his voice as he leaned against the wall with me. Putting a foot up like he was modeling. “I wasn’t expecting you to be here,” he said.

I chuckled, “I can tell.”

“Can’t say I’m not happy to see you, though.” His smile turned slightly devious, but his body language was still hitting high on the brodometer, as if we were talking about sports or something.

I watched him wet his lips with his tongue before putting the bottle of beer to his mouth. “Yeah, too bad you got here so late. Cassie and I are about to leave,” I said in a normal volume. Then, and this was definitely the alcohol talking, not me, but I leaned in and decided to tease him, “Otherwise I would’ve let you get what you want,” and gave him a wink and walked over to where Cassie and Marryanne were still catching up.

I tried a few times to insert myself into their conversation with no luck.

It was only seconds later that I felt the taller, heavier arm of Trevor come over my shoulder. His familiar scent clouded me like a soft, sexy blanket. I wanted to squirm out from under him, but Cassie would’ve read right through that, and it would’ve outed him in one way or another. Both Cassie and Marryanne stopped talking and stared at Trevor as if he had let out a big fart or something. Cassie’s eyes got big as if to say, “Can I help you?”

“Sorry, I didn’t want to interrupt. I just wanted to say I was heading home, and if Evan wanted a ride, he’s on my way,” Trevor said, pulling me tighter to his very firm, very warm torso.

Cassie got excited, “Oh, really? I thought you just got here?”

“Yeah, I was just popping in to say hi to Corey, but I told him I had to be in and out and that we’d catch up at Christmas,” he lied casually.

Cassie, dumb bitch, didn’t read through his blatant lie and jumped on the opportunity to unload me so she could keep flirting with Marryanne. “Oh, well, if you’re already going that way, I mean, as long as you’re cool with it, Evan?”

“He’s cool, he was just telling me he wanted to get home but didn’t want to ruin your night,” Trevor answered for me.

I plastered on a fake smile and nodded my head slowly, no words popping into my useless brain to stop this rollercoaster from leaving the…whatever the launch is called on a rollercoaster. Shit, I might be more tipsy than I thought.

Very quickly, goodbyes were said, and I was in Trevor’s Tahoe, and we were heading down the country back roads with the music bumping.

“You didn’t have to give me a ride home,” I broke the conversation's silence.

“Hmph, I know, but I was hoping you’d be down to…you know,” he winked and fired off his kilowatt smile.

I raised my eyebrow, “No, I don’t know. I’m pretty sure I told you no.”

“Yeah, but it wasn’t a no, it was… a negotiation,” he smiled.

I was a bit confused, but pretending just being in his car, surrounded by his musk, knowing what he really wants from me, didn’t turn me on would be an absolute lie. I bit my upper lip, then asked, “So…where are we going?”

“You’ll see,” he said, making a left turn.

We drove for another ten minutes before he pulled into the driveway of a house I know isn’t his. He put the Tahoe in park and immediately shut off the headlights and engine. “Let’s go,” he said, quickly getting out of the SUV and heading towards the gate that leads to the fenced-in back yard of the dark house. I instinctively followed him, curiosity getting the better of me.

I turned the corner of the house to see him pushing the sliding glass door open and walking in through the venetian blinds, leaving the door open for me to follow him.

Inside, it was pretty dark, but the windows let the street and moonlight stream through. The house was furnished, so someone clearly lived here. I whispered, “Dude, what the fuck?”

He whispered back as he closed the sliding door, “Relax, it’s my Uncle’s house. They went to visit my Grandma in Vermont for Thanksgiving, and it’s warmer than my treehouse,” he grinned.

My heart was pounding in my chest. “I don’t know if…”

“We have two options, the bed my uncle and aunt fuck in, or the bed my fifteen-year-old cousin jerks off in,” He grabbed my hand and started pulling me upstairs.

“Umm…your cousin, I guess,” I chuckled at the options.

“I thought the same thing,” he pulled me into the first room on the right, closing the door behind us. The room was dark but had two windows letting light stream in. It smelled like a teenager’s room. Trevor pushed me down on the twin mattress, the bed squeaking as my full weight landed gracelessly on it. I sat up on the side of the mattress, and Trevor got between my legs, quickly reaching for his belt and undoing it.

“Wait,” I started to say.

“Oh, right,” he cut me off, then leaned, his hands cupping my head from the ears back, pulling me tight, and put his lips to mine. I felt his tongue part my lips and enter my mouth, a soft moan escaping my body and entering his. He was a fantastic kisser—the gentleness of his lips in contrast to his rough stubble on my skin. I went from “I probably shouldn’t” to “I need his pants off” really quickly, reaching out and finishing the unfastening of his belt. I quickly fumbled at the button of his jeans and then the zipper, yanking the dense material down his muscular thighs until it pooled around his ankles. I felt around his boxer briefs to massage his ass, which got him breathing heavier into my mouth without breaking our kiss.

I felt him shifting his weight as he slipped his foot out of one shoe, and then the next. Stepping out of his jeans, he pushed me backward onto the mattress, shifting us around so we could both fit onto the twin bed. His weight on top of me as his lips found mine again, his bulge in his underwear unmistakably hard and in need of release. I let him reach for the belt on my jeans, undoing the button and less gracefully pushing my jeans down to expose my white Calvin Klein briefs. I was surprised and turned on by how quickly he grabbed for my package, massaging my cock and balls through the thin cotton fabric. Another heavy breath escaped my mouth and came out as a slight moan into his.

I wasn’t sure if I should let this continue, but my cock had already decided for me that it needed this attention. I kicked my jeans off my legs and pulled him on top of me, spreading my legs to give him room to rub his package on mine. Our cocks were begging to be set free, but I wanted to continue kissing Trevor and feeling his muscles through his t-shirt. He tasted so good, and fuck me, he’s a good kisser, better than I fantasized he would be. He started sliding his hands up my thermal shirt, his rough fingers on my soft skin sent shivers up my spine, then he started to kiss down my chest, my abs, and just above the waistband of my underwear. “Can I?” He asked quietly.

I breathed out a “yeah,” and lifted my ass as his fingers hooked into the waistband of my briefs and pulled them down and off. I quickly pulled off my thermal shirt and gave myself a few strokes as I watched him take off his t-shirt. The moonlight reflected off his pale skin, kissing each muscle just enough to see him flexing slightly as he put the shirt down. I instinctively wrapped my legs around his waist and pulled him in for another kiss. I didn’t let him linger, though, and started pushing him back down my body to suck my dick.

He went slowly, painfully slowly down my body, kissing his way down, then took my 7” cut cock into his jock hand and started stroking it against his scruffy cheek. I could tell he was nervous, but even in the moonlight, I could tell he really wanted to do this, so I grabbed the back of his head and gently pulled him down. His lips parted, and my dick went into his mouth. It was dry at first, but I didn’t mind. All it took was one gag on the head in his throat for him to start salivating, and my cock was quickly lubed. He tried several times to get me into his throat, then bobbed up and down. I wasn’t going to let him off with good behavior, so I kept dropping a few, “Mmm, that feels so good,” for him to keep up the effort. I even slipped my hand down to my ass hole and rubbed it in his perif so he knew what he was really working for.

I could tell he was getting tired after a bit, but he didn’t complain or give up, so I asked him the question I knew he wanted to hear. “Do you have any lube and condoms?”

His lips pulled off my dick, a string of saliva stretching a few inches as he pulled away before it broke and went down his chin. He stroked my dick and grinned, “Umm…I’m not entirely sure,” he hopped off the bed and walked over to the tall dresser with no drawers entirely closed. He started digging in the top drawer of the tall dresser, “Hmm, nothing but boxers and an athletic cup in here. Let me go check my uncle’s room,” he darted out of the room, his silhouette showing a boner that looked like it was painfully stretching the lycra in his boxer briefs.

I heard drawers open and close down the hallway, then the sound of an exhaust fan turning on and off, before I heard his heavy footsteps coming back down the hall. “No condoms, but they had vaseline in the bathroom. Is this ok?”

I rolled my entire head dramatically, “Dude, no condoms in the entire house?”

His head fell to one side. I could barely make out his face in the light, but his body language was clear. “Are you really going to make me wear a condom? We already did it without.”

I puffed out some air, “Yeah, and we shouldn’t have.”

“Well…fuck, what do you want to do?” He asked. “Do you just want to blow me?”

My heart thumping in my chest, my balls arguing with my brain and my instincts, “No,” I grabbed the Vaseline from his hand and popped it open, scooping a generous amount out with my finger and spreading my legs. “Just don’t cum in me, ok?”

He shoved his underwear to the floor, his dick sprang free, “Yeah, ok, no problem.” He got back between my legs and grabbed the jar of Vaseline, scooping out a big glob and smearing it on his erection. I watched him stroking himself with the grease as I started fingering my hole with two greasy fingers. The thick lubricant actually felt pretty good and made it a little easier for my fingers to slide in. Trevor grabbed my thermal shirt and wiped his hands off.

“Dude, that’s mine,” I said, a little annoyed.

“Sorry, I can’t wipe it on Daniel’s bed,” he chuckled, then handed me the shirt. I pulled my fingers from my hole and wiped them off.

He adjusted himself between my legs. I pulled my knees up to my chest, exposing my ass for him. He put his hands on the backs of my thighs, leaning his weight on them as he let his dick seek my hole like a divining rod looking for water. It was too dark for his nonsense, so I reached for his dick and put the head right on my hole. “There?” He asked in a low, deep voice.

“Yeah,” I whispered back.

He started pushing hard, and the head popped right in with an unbelievable sting. “Ahhh, fuck, gentle dude, gentle,” I groaned and hissed.

“Sorry, sorry,” he whispered soothingly, but not retreating the two inches that popped into my tight ring. I could feel his heart throbbing through the blood flowing into his thick cock. It almost massaged my hole to let him push gently deeper. The Vaseline definitely helped my hole to not be ripped open by his girth as the entire six inches sank into me as he breathed out an “Oh fuck,” from his lips as his pubes hit my ass.

I clenched my teeth and tried to breathe. “Wait, just hold it there, let me get used to it,” I told him.

“Ok,” he said, then immediately started flexing his cock inside me. I’m not sure if it was a conscious movement, but that little movement quickly started to feel good.

I took another deep breath and said, “Go slow, gentle,” and squeezed his thighs.

He nodded, the moonlight twinkled in his eyes as he locked them onto mine before looking down at his dick as he slowly pulled five of his inches out of my chute and then slowly pushed all the way back in. I groaned, and he breathed out nothing but pleasure. I reached for my dick and started stroking myself back to life. The gentle strokes were slow, but deep; his eyes stayed locked on his cock, amazed by the image of it sliding into my tight hole. With each thrust, he let out a breath of air and a low hum of pleasure. 

I took another deep breath and started stroking my now hard cock, and flexed my ass around his slow-moving cock.

He felt my hole flexing around his strokes, and his eyes darted up to mine, “That feels so good.”

“Mmm, so good,” I reassured him. “Kiss me,” I said, spreading my legs so he could lean down and continue to fulfill my needs. His mouth had a new hunger as his tongue wrestled with mine, each stroke of his cock inside me making him breathe faster.

“Fuck that feels good,” he moaned into my mouth.

“Don’t cum yet,” I warned him and started stroking my dick faster.

He stopped thrusting and started kissing me harder. You could hear the face sucking and lip smacking echoing through the quiet room as I stroked myself off with his dick, putting pressure right on my prostate. I couldn’t help but moan into his mouth and rock my hips up and down on his cock, getting every ounce of pleasure from him as I could. “Mmmm,” he broke our kiss and put his forehead on mine. “I’m gonna cum if you keep doing that,” he breathed out.

I felt that meat inside me starting to swell, and my prostate enjoyed every micro thrust from the blood pumping in that thick meat. I couldn’t help but moan out, “I’m so close.” Beating my meat faster, I clamped my ass on his cock for a few strokes and then released my grip on him.

“Fuck, you’re gonna make me cum,” He mumbled, pulling his cock most of the way out and thrusting back in. The swelling of his cock head running over my prostate opened my floodgates.

“Oh fuck, I’m cumming,” I said, flexing my thighs around his waist and my ass around his cock. He quickly grabbed my thermal shirt and put it over my cock as I felt my cum rocket out of my dick and paint the underside of my shirt. I flexed my ass on his cock some more, riding out this incredible orgasm as my shirt continued to get coated in my load.

“Fuck, I’m so close,” he said, leaning over me and kissing me as he started giving me a slow thrust, adding more pleasure to my orgasm. “Can I cum in you?” He huffed as he thrust again, “I don’t want to get cum on Daniel’s bed,” he mumbled between kisses as he thrust harder and faster into me.

“Umm, ok,” I couldn’t process any of it as my orgasm was still pushing cum drops out of my dick with each of his thrusts.

“Oh fuck,” he put his forehead back onto mine. “Oh fuck,” he thrust. “Oh fu—ungh,” he thrust hard into me, and I felt his cock throb and the immediate warmth of his load coating my insides, “Fu—ahh,” his body trembled between my legs as his torso stiffened above me, and he stopped breathing as his cock continued to unload inside me. Then he stopped altogether with a very quiet, “shit.”

I felt my own orgasm subsiding as we both caught our breath. I felt his dick quickly going soft inside me.

“Shit,” he sat up straight, grabbing my thermal shirt and putting it under his dick as he pulled out quickly. “Don’t leak onto my cousin's bed, I put a big load in you,” he chuckled.

I felt my whole clamp down, and chuckled, “I won’t make a mess.”

“Ok,” he huffed, getting off the bed and grabbing some tissues from the dresser to clean up his dick.

I got up, “Where’s the bathroom?”

“Down the hall, but don’t turn on the lights, I don’t want the neighbors to see lights come on,” he said.

I nodded and went down the hall, my eyes already adjusted to the darkness. I just wanted to wipe off as much Vaseline as I could before getting dressed.

When I came back to the bedroom, Trevor was already back in his boxer briefs and jeans, zipping up and thumbing the button together. He held out his white t-shirt, “Here, since you’re shirt is coated in cum and stuff.”

I don’t know why, but this sort of made my heart flutter. I slung it over my shoulder, searching the bed for my underwear.

“Looking for these?”

I turned to see Trevor holding my undies, a finger from each hand hooked into the waistband to show them off to me. “You still wear tighty whities?”

“Yes,” I snatched them from him.

“That’s kinda gay, isn’t it?” He snickered.

“I’m gay,” I said, almost tripping as I put my second foot through the leg hole and pulled them up quickly.

“I’m just fucking with you, I have several pairs I wear to the gym, but not when I’m trying to get laid,” he shrugged, then pulled his hoodie on and zipped it halfway up his bare chest.

I was still putting on my jeans as I watched him slip his feet into his sneakers. “Well…I hadn’t planned on getting laid, but I happen to like the look and feel of briefs.”

He chuckled, “You do look good, but I think you knew we’d be fucking tonight.” He leaned over and smacked my denim-covered ass.

I couldn’t help but laugh at his bravado. Then I gave his shirt a quick sniff without thinking, then realized how weird that was and pulled it on, hoping he hadn’t noticed. It was a bit baggy on me, but comfortable, and his scent was intoxicating. I slipped on my shoes, and we started walking down the stairs.

“Shit, my thermal shirt,” I said, running back up the stairs.

I fumbled around on Daniel’s bed, but didn’t find it, then started grabbing at clothes on the floor, most of them not mine. Then I saw a little shoe box half under the bed, pulled it out, sure enough, a box of Trojans and three off-brand condoms he probably got from school or something, along with what I can only assume are letters from a girlfriend, and something that looks like an almost empty baggie of weed. I shook my head, tucking the box away, and started pulling at what I thought was my thermal shirt, but turned out to be a very dry, very stiff washcloth, and chucked that back under the bed. Thankfully, the next thing I reached for was my thermal shirt, and I ran down the stairs to find Trevor waiting by the sliding glass door.

“Did you get it?” he whispered.

“Yeah, I got it, let’s go.”

On the drive home, I kept going back and forth between “fuck it’s late, I have to be up early,” and “I can smell Trevor on this shirt and I have his cum in my ass,” and the miles flew by.

When I got home, I went to put my phone on the charging cradle when I saw I had unread text messages and flipped it open. I had three text messages from Trevor from before he got to the party.

Trevor: I wouldn’t mind kissing, I’m a good kisser.

Trevor: I can’t say I know what rimming is.

Trevor: If I have to let you fuck me, I will, but I can’t say I’ll enjoy it.

Damn…I think I missed a big opportunity. I flipped the phone closed and put it back on the charger. Then I pulled off Trevor’s t-shirt, gave it one last sniff, and tucked it into the top drawer of my dresser so it didn’t get the scent washed off any time soon. I hopped into bed and passed out.