The List - 8. Chapter 8: Michael Pt. 1

Specimen’s Name: Michael

Height: 6’2

Build: 190, muscular

Occupation: Student (Pre-Law)

Age: 22, junior

Dimensions: 8’ cut

The day after I hooked up with Ben, I was riddled with confusion. Kyle texted me early on in the morning, reminding me that we had plans for tonight. As soon as I saw his name pop up on my phone screen, I felt a pang of guilt.

Why the hell did I think going out with Ben was a good idea in the first place? Why did I think going up to his apartment was a good idea after I’d been drinking with him and getting signals from him all night long? How did I honestly justify giving him a blow job and making out with him when a calendar week hadn’t passed since Kyle said he wanted to try the exclusive thing?

When I got home from my lone Friday class, Spencer was in the room playing Super Smash and trash-talking a kid over his headset.

“Caucus when you’re done,” I said to him, sitting down on my bed and pulling out the list. On the page after Eric, I wrote Ben’s name and his information. I also drew an arrow that curved to the side in an attempt to illustrate he wasn’t as straight as I thought.

A couple of minutes later, Spencer put the game down and asked me what was up.

“I have no clue,” I told him. “I thought this guy was straight, I really did, and then after a few drinks and a few hours, we’re in his room jacking each other off.”

“Is that all that happened?” Spencer asked me. Not willing to confess that after Ben and I’d taken the plunge and blown him, I told Spencer that was all that had happened. “Then I wouldn’t worry about it. I mean, if you and I whipped it out right now and jacked off, Kyle wouldn’t have a problem with that, would he?”

I just shrugged. “Maybe Kyle was right. Maybe this whole dating thing is stupid.”

“Buyer’s remorse already? It hasn’t even been a week. I hope you kept the receipt,” Spencer joked.

“I mean, you were right. The past three weeks, I’ve hooked up with a random assortment of guys while keeping Kyle on the burner. Maybe it’s just easier that way,” I told him.

“You two and your flip-flopping are really giving me a headache,” Spencer said. “The minute you’re ready to give up your freedom, Kyle backs out. Now that he’s in it to win it, you’re ready to jump on the Java Express with this barista guy? You know what, I am going to butt in for this once and tell you to shit or get off the pot. If you want Kyle, then be with Kyle. End of story. If you’re determined to live up this slut phase, then do it and make no apologies. Just pick one and stick with it.”

Spencer was more than right and at that point, the only voice of reason I needed. I had to make a choice, and I had to make it soon— I had dinner plans with Kyle that night.

Even though everything Spencer had said made complete and total sense, I needed a second opinion on whether or not to tell Kyle about Ben. I called David and asked what he was doing for lunch, thinking a third party that didn’t know anyone except me could give me some sound advice. He agreed to meet me for lunch at a wing place just south of campus.

“I think you don’t tell him,” David said. “I mean, I’ve heard you talk about this Kyle guy. You’re crazy about him. This Ben thing was a one-off thing. I mean, you thought he was straight up until you had your lips around his dick. I say you file it away under drunk mistakes and move on.”

For David it was that simple. After being with him, I knew firsthand how easy it was for him to check his emotions at the door. I mean, here we were, still friends after hooking up and nothing was weird. I decided he was older and wiser and probably right. But he was also single, so how right could he be?

I decided the night out with Kyle was going to be a litmus test. The pH paper was in and I was going to read the results come morning. I had to decide if I was going to shit or get off the pot, so to speak, and so I had to make keen observations tonight. Could I date Kyle? Could I really be in this 100 percent like we’d talked about? I knew I didn’t want to hurt him, so if I couldn’t stand up to the pressure, I’d better get out of it now rather than later.

Thinking we were just going to grab dinner and start drinking, I got to Kyle’s at seven, like he said, wearing jeans and a polo shirt.

“Is that what you’re wearing to dinner?” he asked when I stepped into his room. I gave him a questioning look.

“I didn’t think we were going to the Ritz,” I said, confused. “Let’s just grab something quick and then start pre-gaming.”

Kyle had a look on his face that I’d never seen before. It was like he was annoyed for some reason, but not exactly at me.

“Sit down,” he said. I sat down on the side of his bed. Kyle smiled at me, knelt down and put his hand on my crotch. He didn’t break eye contact as he started rubbing back and forth, eliciting an immediate reaction from my pecker. “I have a confession to make, and I don’t want you to be upset at all.” A confession? What the hell kind of confession?

“Explain,” I said, leaning back a little. Before he continued, Kyle undid the four buttons of my jeans and lowered them slowly. I had no clue what was going on, but I liked it.

“So I didn’t want to tell you before because I didn’t want to freak you out,” he said. By now, he had his hand wrapped around my dick and was stroking it back and forth slowly. I let out an “okay” mixed with a soft moan. If he didn’t get to the point quickly, I’d lose it. “We’re going to dinner with my brother tonight.”

I immediately grabbed Kyle’s wrist to stop him from stroking my dick. Sitting there with a hard-on and my boyfriend’s fist pumping my cock, I couldn’t believe I was stopping him, but I had to object. “Absolutely not,” I said. “Are you kidding? You weren’t going to tell me I was having dinner with your family tonight?”

“It’s not a big deal,” Kyle replied. “It’s not like you’re meeting my whole family, just Jason. And he’s really excited to meet you.” After a silence, Kyle continued. “I told him that I was seeing someone and he said he wanted to meet you. No big deal.”

“This is the second time you’ve ambushed me, Mr. Wriggs,” I said. Kyle’s hand was still on my dick, which showed no sign of going down despite my frustration.

“And last time, if I remember correctly, you hooked up with a friend of mine. I think you owe me, Mr. Carpenter,” Kyle replied. I took that moment to assess the position I was in. I did owe him for the whole Asher debacle— not to mention the Eric and Ben debacles that followed. Plus he was kneeling between my legs, my rock-hard cock in his hands. He could have gotten away with anything at that point. “Now, because I’m a nice guy, I’m not going to blackmail you into changing clothes and coming to dinner with my brother and me. What I will do is suck you off, right now, really quickly, in an attempt to compel you to come to this free, five-star dinner of your own free will.”

Before I had a chance to answer, the entire length of my dick disappeared into Kyle’s mouth. I felt the head of my dick hit the back wall of his throat, and I immediately rolled my head back and let out an “oh shit.” My hips involuntarily lifted upwards and I was inside Kyle’s mouth as far as I could go.

I leaned back on my elbows and let my boyfriend go to work. When I say that Kyle gives the best head, to date, I’ve never had head better than that. His sheer enthusiasm about tasting my dick was enough to drive me crazy. He kept alternating speeds, bobbing up and down really quickly and then slowing down and taking my entire shaft into his mouth. His tongue seemed to be everywhere at once, from the underside of my cock to the ridge just under my head to the slit that was oozing precum like it was getting paid.

When Kyle said it was going to be quick, he meant it. After a couple of minutes of bobbing back and forth, Kyle really went for the gusto. He put the entire length of my dick into his mouth, looked up at me with big eyes that made me wonder what was about to happen and then he sucked on me as hard as I’d ever felt. He started turning his head in a circular motion, creating an entirely new sensation. It was like a whirlpool jet was massaging my dick.

A second later, I spewed every ounce of semen I had inside of me. Kyle let out a loud grateful moan as I felt his throat swallow squirt after squirt of my cum. To be completely honest, I was so enthralled by the feeling his throat was making on my dick I didn’t even realize I’d stayed hard even after I’d stopped coming.

Kyle stood up, wiped his chin and grinned down at me. “Now, what do you say, Coop? Will you or won’t you come to dinner with me and my brother tonight?”

I had no idea how I could even say no to anything he asked me after that. I would have gone to the moon with this guy if he had wanted me to. Instead of answering, I just stood up and kissed him, tasting myself on his breath.

“That’s what I thought,” Kyle said when I let go of his lips. “Let’s get you dressed.”

Kyle pulled out some things from his closet he was convinced would fit me. He explained that we were going to a steakhouse in uptown, and so a polo and jeans wouldn’t cut it. I think he was more interested in showing the famous Jason Wriggs that he’d landed a good catch.

I stuffed my still semi-hard cock into a pair of black jeans that required me to lay horizontal in order to button them. We went through three button-down shirts until we found one that I could button all the way down, although I still had no clue how I was going to manage eating without popping. To hide the give, my boyfriend-turned-stylist made me wear a vest. I’m not a big guy and take pride in the fact that my metabolism allows me certain freedoms, but I didn’t realize just how tiny Kyle was until I was stuffing myself into his clothes.

“You look amazing,” he said to me.

“Really?” I asked. I felt like I looked ridiculous. I would have given anything to be in a pair of jeans and a polo, but apparently that wasn’t good enough for the Wriggs. Kyle himself was wearing a pair of dark slacks, a striped button-front shirt and a blazer. Feeling gayer than I’d ever felt before, we left and met up with Jason at Two Forks in uptown.

When we walked into the restaurant, Kyle was greeted by the host as if they knew each other.

“Is Jason already here?” Kyle asked. The guy led us to a table for three in the center of the dining room. When I first saw Jason Wriggs, I almost stopped dead in my tracks. The guy was a fox. He was 6’ tall and had the most perfectly-coiffed head of blonde hair I’d ever seen. His skin was fair and smooth and the only imperfection was a small beauty mark on his right temple. When he stood and shook my hand, it was so firm and warm, I thought I might melt. His smile was more inviting than I’d ever seen. He reminded me almost immediately of Brad Pitt circa Ocean’s 11.

“So you are Cooper,” Jason said in a deep voice that sounded like it belonged on the radio.

“That would be me,” I said. As we sat there getting acquainted and making small talk, I got the sense that Kyle and I were passing a sort of milestone that I couldn’t even begin to deny. I was meeting his brother; that meant something. As the night unfolded, I relaxed more and more and let the combined Wriggs charm win me over.

And boy were they charming. If I thought Kyle was great on his own, it was ‘cause I’d never seen him with his brother. They had a million inside jokes that I was slowly but surely getting familiarized with. Kyle clearly looked up to Jason, but at the same time, they complimented each other perfectly.

“So are you two doing the Sigma auction tomorrow?” Jason asked just as the waiter was dropping off another bottle of wine and clearing our dinner plates.

“I forgot that was coming up,” Kyle said. “No one asked me this year.” Noticing my confused look, Kyle explained. “Last year, the Sigmas asked me to be in their annual auction. They always pick a couple of brothers to sell off to the highest bidder for a night of ‘servitude’ so to speak. They mostly end up going to either a girl’s house so they can clean in their underwear or to someone that has a crush on them. Sometimes brothers chip in to buy forced labor.”

“Kyle here was bought by a girl who made him dance to—“

“Total Eclipse of the Heart,” Kyle interrupted. “For an hour. She had it on loop and she wanted me to strip, but I was so nervous I couldn’t even get my shirt up. And then she pounced and took advantage of me.”

“Oh, come on,” Jason interjected. “You loved it, and you still owe me for getting you in the auction in the first place. Kyle was my pick, so imagine my big brother pride when he got the highest bid.”

“What can I say?” Kyle responded. I enjoyed watching the Wriggs show at work. It was no wonder the Sigmas were so taken by Kyle even though he wasn’t a member yet. When he let loose like he was in front of Jason, I couldn’t think of a single person that wouldn’t like him.

“Say the word and you two are in the auction,” Jason said, taking a sip of his wine. “I hear this year, they’re dressing everyone up as a statue and people are placing silent bids. It’ll be a lot of fun.”

I hesitated and just let Kyle do the answering. I wouldn’t even know where to begin being in a Sigma fundraiser. I wasn’t sure that Jason’s influence even extended to me.

“Give me the go and I’ll call Rusty right now,” Jason said, pulling his phone out. Kyle just looked at me, his eyes asking if I wanted to do it.

“You don’t have to be a Sigma to do it?” I asked.

“Not when you’re represented by Wriggs and Wriggs,” Jason said smiling.

“LLP,” Kyle finished. They burst into laughter and I just smiled at them.

“How about this,” Kyle said. “Why doesn’t Cooper here do the auction and I’ll just make sure I’m the highest bidder.”

“Really?” I said giving him a wicked smile. “You think you can afford me?” It was equal parts question and equal parts challenge.

“Of course I can,” he said.

“Okay, I’d better get the check before things get too hot and serious around here,” Jason said, flagging a waiter over. A few minutes later, we were leaving Two Forks and Jason was on the phone.

“Listen, Rus, you know Kyle’s friend Cooper, right? Yeah, he said he’ll do it. Well if you pick him, he’d better win or you’ll break the presidential streak. You have a lot of faith in this kid, huh?” I winced at the thought of what Rusty was telling Jason, but figured he wouldn’t implicate himself like that. I whispered to Kyle that I had no idea Rusty was the new president and he just winked at me. “Yeah, do what you have to to get him in. I’m sure this guy could raise over a thou, are you kidding. Ok, I’ll see you tomorrow then.” He hung up the phone and told me I was in.

“Rus told me to tell you to do some sit-ups before you show up tomorrow. He has a special outfit in mind for you,” I stopped in my tracks. Kyle was giving me a wicked grin and Jason looked amused as well.

“I can imagine what Rusty has in mind, and I’ll need more than a few sit-ups,” I protested.

“That’s not what Rusty thought,” Jason said, giving me a wink. I guess Rusty had told Jason everything. “Kyle here might have some competition if he wants to win you.”

“I can loan him out for a night if I have to,” Kyle said. I punched his arm.

As Kyle and I were driving back to campus, he asked me what I’d thought about his brother.

“Ya’ll are so awesome together,” I responded. “It was like dinner with Frank and Joe Hardy.”

“You didn’t think he was too amazing to be my brother, did you?” Kyle asked, looking over at me. I put my hand on his thigh.

“What is that even supposed to mean?” I asked him.

“I dunno. I guess I’m being stupid. I just always end up in his shadow. Even my friends think Big Wriggs is the cooler of the Wriggs brothers,” he confessed.

“Well I’m glad I got the brother that I got,” I said. At that point, I decided I wasn’t going to tell Kyle about Ben at all— ever. Sitting there in his car, talking and sharing and getting more intimate with our lives than we had been in the past month, I was content. And I wanted to stay content for as long as I could.

“So you’re sure about the auction thing?” he asked me when we were getting closer to campus. “You don’t have to if you don’t want to.”

“Are you kidding?” I said, looking at him. “It’ll be a ton of fun. And as long as you promise to win the auction, I’m game.”

“I mean, these things get pretty pricey. I don’t know if I can devote my entire allowance to winning you for one night,” he said.

“You bet your ass you will,” I said, laughing.

As we neared campus, I texted Spencer: Any chance Kyle and I can get the room tonight?

A minute later, from Spencer: All night? You do realize it’s November Crunch. Do you two study ever?

Emboldened, I texted him: It’s hard to memorize dates and facts when your boyfriend is dicking you really good.

Spencer replied: You’re insatiable and disgusting. Use lube. Don’t touch my bed.

I smiled, turned to Kyle and told him that we had my dorm room if we wanted it.

“Oh course we want it,” he said, putting his car in park in a garage across the street. As we walked back to my dorm, Kyle grabbed my hand and held it inside of his. I smiled at him.

When we got back to the casa, I wanted nothing more than to strip out of the too-tight clothes and climb into bed with Kyle.

“Wait,” he said as he saw me begin to undo my pants. “Let me.” I couldn’t help but smile as Kyle walked to me, and began undressing me. We didn’t once break eye contact, something so sexy, I thought I might cream right then. Kyle’s movements were slow and deliberate and for someone whose rock hard cock desperately wanted to be free, it was excruciating.

Kyle’s assisted striptease left me wearing nothing but his vest and a hard on. When I was as naked as I was going to get, Kyle kissed me deeper than he ever had and pushed me down to the bed. My dick was sticking straight up and slapping against my abdomen.

And then Kyle began his own striptease. I couldn’t quite figure out what music was playing in his head, but he slowly ran his hands down his torso to the beltline of his jeans. He unbuttoned them and lowered them slowly. Then he ran his hands up his torso, taking off the tight shirt that revealed the tight body underneath. Kyle stood there in front of me, stark naked, looking sexier than anyone I thought I’d ever get my hands on.

That night, we did more than just have sex. It sounds like a bad daytime soap opera cliché, but really, we made love. We weren’t in any rush and Kyle was adamant that we take our time. Any time I started humping him too fast, he’d slow me down or even stop me from moving completely and we’d lie there, with me inside of him, feeling every last inch of him.

After the striptease, Kyle turned around and lowered himself onto my lap. He sat between my legs, wrapped my arms around his torso and chest, and slowly guided my dick into his ass. We sat there like that, Kyle almost off the side of the bed, me holding him close to me, for what felt like hours.

“I could stay like this forever,” I told him, not even thrusting into him. He just leaned his head back, craned his neck and kissed me.

Next, Kyle leaned us back so that I was lying down, my feet up on the side of the bed and my knees up. Kyle had possession of my hands and stretched them out as far away from our bodies as they would go. He leaned over me, arched his back, and ever so slowly rose off my dick and then slid back down. I’d never had the person I was fucking control the pace so expertly, but underneath Kyle in that position, there was literally nothing I could do but let him ride me.

He wanted me inside of him for as long as possible, so his moves were slow and calculated. I was helpless and the feeling of slow long strokes on my cock was enough to drive me absolutely crazy. To distract myself from how amazing Kyle’s tight ass felt on my dick, I preoccupied myself with his ears, sucking and biting down on them as if they were my own personal chew toy.

After what felt like an eternity but was actually a more like a minute, Kyle moved us so that we were both lying on our side. Without ever letting my cock slip out of his ass, he positioned us so that he was spooned perfectly inside of the nook my body was creating for him. In this position, I felt Kyle in a completely different way. It was like I was so deep inside of him, I was feeling new parts of him that I’d yet to explore.

Again, he had my hands intertwined with his and this time he used our hands to massage his own dick. I thought the heat radiating from our combined bodies would ignite us both into a huge ball of fire. At that moment, with Kyle in my arms, I felt more content than I ever had in my life.

And then my body couldn’t control itself any more.

“I’m gonna come,” I whispered, afraid to ruin the mood by being too loud. I let out a soft moan and arched my head back.

“Wait,” Kyle said. I felt his ass pulse onto my dick. If he didn’t want me to come yet, that wasn’t the best move he could make. “I want you to come inside of me.”

He turned his head and I could see his expression. At that point, I was still wearing a condom, but it was clear what Kyle was asking me to do. It was the ultimate test of trust, and looking back, it was stupid. But at the time, I was an 18-year-old romantic on the brink of love with the guy in my arms. For the first time in a couple of hours, I pulled my dick out of Kyle’s ass, pulled the condom off my cock and then effortlessly slid my dick back into Kyle.

The feeling of being inside of him bare was sensational. Every nerve ending on my cock was on fire. Kyle could probably feel my dick pulsing because for the first time that night, he moved with some sort of sexual urgency. He leaned us back into the position with him on top, back arched, and thrusting upwards. I wished to God I could see his face as he moved up and down slowly, fucking himself on my rod.

It only took a minute of actual fucking to put me over. And then I realized what Kyle was trying to accomplish. He wanted us to come together. At the exact moment that I felt my balls tense up, my toes curl over the side of the bed and a wave rush from my head to my cock, I felt Kyle’s body go rigid on top of me. His cock lurched and spit a continuous string of cum up his torso and to his neck at the exact same moment that my cock let rip deep inside of him.

Involuntarily, Kyle let out at an “Oh fucking god,” that resembled a roar more than a moan. Unable to control myself either, I simply grunted “Aaagh,” while digging my nails into Kyle’s chest and arching us both upwards.

The orgasm was unreal. It was like someone had tied me up and hadn’t let me come for an entire year and then suddenly touched my cock and I exploded. It was out of body. The sounds, the feelings, the smell, the intensity of finishing inside of Kyle while he came on top of us was unbelievable in the most pleasurable way. I noticed we were both screaming and panting after the fact. If my neighbors Chris and Jeremy didn’t know I was gay before tonight, hearing Kyle and I lose our loads with each other would do the trick.

“I think I’m dead,” I said to Kyle, pulling out of him but not going far. That night we fell asleep with him spooned inside of the shell my body formed, like I was our protector.

I woke up at some point in the night, too nervous that moving would wake up Kyle. Instead, I just lay there, trying to match my breathing to his. I took the time to notice how he slept, with my arm around him and with his hand pressed over my hand, both of them planted firmly near his heart. We were in perfect sync that way. He had also done something I hadn’t noticed before. Somehow in the course of falling asleep, Kyle had put one of his legs between mine so that it was like our feet were intertwined just like our hands were. I dozed off again feeling like I never wanted to wake up and that I could sleep this way every night…