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Dillon - Part VII - Cheating Is Cheating
🕑 Added 2025-12-06 04:04:51 +0000 UTCDuring summer break, I felt a weird sense of disconnect from who I am, who I was, and who I want to be in five years. I realized I had become a bit obsessed with sex with other guys, mostly with Tank, and when I realized I had grown an emotional attachment to Tank, not just sexual, it kind of scared me. So I did the very healthy thing of deciding I wouldn’t hook up with men anymore.
When I crossed paths with a girl I briefly dated in high school who was also back for the summer. We caught up, hit it off, and started a summer romance that I dove deep into. I let myself get wrapped up tight in the security of a heterosexual relationship, which felt safe, comfortable, albeit a bit boring at times, but it gave me the sexual gratification I needed to focus on other things, like my future.
That relationship didn’t fizzle when we went back to our respective schools. She was going to Yale, and I was going to BU, so we weren’t so far from each other that we couldn’t get together over a three-day weekend or something special. It was really good to be in a locked-down relationship for my third year of college. Since I had been elected house treasurer, I moved out of the dorms and into the frat house. I focused on classwork and my major, which turned out to be finance, because I was good with math and terrible with most other subjects.
I won’t pretend that I went the entire year completely ignoring my bisexual side, but I had put it mostly on the back burner. Living in the house with the rest of the guys, who were completely unaware of my bisexual side, with the exception of Alessandro, who also moved into the house, it helped me not get too distracted by a flirtatious alpha-type or a cute twink whose massive dick flopped around in his boxers. Any time I would get horny, at least after 9:00 pm, I could call my girlfriend LeeAnne, and we would have some hot phone sex.
When summer break 2005 rolled around, we both went back home; she went to her parents and I to mine. We spent an entire summer completely absorbed with each other, and I thought I had found my place in life. I had aced all my classes in the fall and spring semesters, and things were really looking up.
Senior year started for me in the fall of 2005, LeeAnne was back at Yale, and I was at the frat house. Kicking off the year right, we had a big party, and we were all getting wasted.
Somewhere around midnight, I found myself in a circle with Alessandro and two other seniors, Max and Stephen. It was mostly mindless conversation until Max asked, “Oh, are you guys on Facebook?”
I chuckled, “No, what is it?”
“It’s this fun place to meet other college students, sort of. You get your own page for all of your info, you can upload photos, and treat it like a blog, but it’s exclusive to college students.” Max said.
“Sounds like MySpace,” Alessandro said.
Max held out a flat hand and teetered it from side to side, “Kind of, but you need to use your BU email account to register, so they know you’re a college student. I signed up a few days ago, and it’s loaded with hot women who go here.” His eyes got huge, as if he were remembering a specific beauty.
I rolled my eyes, “Sounds like you’re just being a creeper perv, jerking off to your classmates' photos,” I joked. They all laughed.
“It’s not just girls. I just became friends with Tank on there today and requested to be friends with some of the other guys who moved on to another school. From the photos he uploaded, it looks like he’s living the dream at NYU,” Max tossed that info out, probably expecting it to roll off but prove the point he was trying to make. Just the mention of Tank made my asshole clench, and I couldn’t follow the conversation after that. My brain became obsessed with thoughts of the last time I saw Tank, and how good the sex was. It was like a floodgate of horny thoughts had suddenly been opened. It took every ounce of willpower I could dig up to keep myself from getting an erection.
I eventually snuck away from the party, went up to my room, jerked off and went to sleep.
A few days passed, and I tried to push away the temptation of signing up for Facebook and getting in touch with Tank, but one late-night conversation where LeeAnne casually mentioned her and her friends were on it made me think I might be missing out on something altogether. I justified that LeeAnne being on there meant that I should sign up to be that much more in touch with her. It didn’t mean I was signing up just to get in touch with Tank. In fact, I’m not even going to become Facebook friends with Tank.
I signed up, became friends with LeeAnne, and some of the guys in the frat house. Then I logged out and didn’t log in again for almost a week, when Lee told me she uploaded a new picture of herself from a party she went to, and that I should take a look when we get off the phone. I did just that. It wasn’t the photo of her that caught my attention, though. It was a friend request from Tank that immediately caught my attention. Of course, I accepted and started looking at all of the photos he had uploaded.
Tank must have been a user for a while because his photos and posts went all the way back to the spring semester. It wasn’t lost on me how he had trimmed down a bit, and his beach vacation photos from the summer showed off a body I wasn’t familiar with. A body that I want to see more of. His wet trunks didn’t hide much either. Even shrivelled from the cold water, his bulge was enough to trigger my horny memories of our sex. How good it felt the last time he pumped his hot load inside me.
I hopped up and locked the door, dropped my pants, tucked my underwear under my waistband and started jerking off, looking at the pictures of Tank in his boardshorts.
I felt guilty after I blew my load. I have obviously jerked off thinking about past sexual experiences, but this felt different. Almost like I cheated on LeeAnne. I couldn’t rationalize why I felt that way, blamed it on the beer, and went to sleep.
Over the next couple of months, I slowly slid out of my comfortable heterosexual lifestyle and started doing things that scratched that itch inside me that was very bisexual. It started with private messages between Tank and me. Those were pretty basic at first, but one drunk night, I asked him if he ever thought about me when he jerked off, and he told me he did. That was all I needed to continue my spiral.
Some nights when I wasn’t able to have phone sex with LeeAnne, I would hop online and have cybersex with faceless men in chat rooms. Those chats fueled my need to explore my bisexual side again. That brought me to phone sex with guys I met in chat rooms. I tried to convince myself it wasn’t cheating; they were just random, faceless guys that I would never really cheat on LeeAnne.
Then, when I started narrowing my search in chat rooms to guys in the Boston area, knowing I wanted to have phone sex with them, it became easy to have repeat sessions with guys who sounded hot.
One guy had an incredibly sexy voice and got me off so easily that I started looking forward to the next session with him. One particular night, I was stumbling back to the frat house after celebrating a classmate turning 21. Back in my room, I locked the bedroom door, dove onto my bed, and pulled the covers over me to muffle my conversation as I hit send on my phone.
Elliot answered on the first ring. “Hello?” His voice was masculine; he didn’t sound like an old man, which was good, since he claims to be 22.
“Hey,” I said, trying not to sound drunk or overexcited.
His timbre changed when he moved into his bedroom; it smoothed out a bit, a little sexier than when he answered, and a hint of a midwestern accent. “Mmm, it’s nice to hear your voice.”
“Yeah, I’ve been thinking about you,” I chuckled.
“Mmm, yeah, you’ve been on my mind too,” he said without a trace of laughter.
“Thinking good things, I hope,” I felt my blood already rushing toward my dick.
“So good. So good that I’m already hard thinking about you. Hell, I’ve been hard since you told me you’re at BU…I don’t know if my dick will ever go down,” he said.
I swallowed hard, my hand squeezing my dick in my underwear. “Yeah, it’s a small world,” I managed to say without my voice cracking.
“I’m surprised we haven’t met already. You’re… bi, right?” He asked.
“Yeah,” I breathed out. Heart pounding at the idea that we might’ve crossed paths.
“You said you mostly hook up with girls, but sometimes hook up with guys?” He pried, probably cross-referencing my answers with the mental notes he already had on me since he’s asked these questions before.
“Yeah. Only when I’m really horny,” I squeezed my dick again, tighter.
“Are you really horny right now?” He asked, picking up on the horniness in my tone.
“Mmm…yeah,” I breathed out.
“Are you stroking yourself?”
“Kinda,” answered honestly. I felt like he could see me.
“What are you wearing?” He asked, taking a step back.
“Ummm, a t-shirt, sweatpants, and underwear,” I rattled off.
“Take off the t-shirt and sweats for me. Are you wearing boxers or briefs?” He asked.
“Briefs,” I said, feeling my face flush.
“Mmm, sexy. I’ll bet you fill them out nicely. How big did you say you are?” He asked.
“I’m only five and a half inches,” I told him, not feeling the need to exaggerate.
“Mmmm, that’s plenty for me to put in my mouth. You like getting sucked?” He asked.
“Sometimes,” I huffed out some air, thinking of how good it always felt when Tank would suck me off, mostly because he was the only person to suck me off that would also play with my balls and eat me out.
“Pull your dick out, let me put it in my mouth,” he said.
I quickly pushed my waistband under my balls and started stroking it.
“How’s that feel, Dillon?” He asked.
My name, coming from his voice with that sex laced tone, had me waving my legs back and forth as I stroked myself. Something I did when I was stroking myself like this, the tension from the waistband of my underwear would add pressure to my balls, and it felt similar to having my ass played with. “Feels so good,” I breathed out quietly.
“What if I dropped down lower? Would you like that?” He asked.
“Oh God, yes,” I hummed.
“You like having your ass eaten?” He asked, his breathing getting heavier.
“Yeah,” I breathed, my breath heavier and my strokes faster.
“You want my tongue to push into your tight hole?” He asked as though he was already licking my pucker.
“God, yes,” I mumbled, spreading my legs wider on my bed and rocking my hips.
“Mmm…how long has it been since you’ve had your ass eaten?” He asked.
I had to think for a second, “a long time.”
“A month?” He asked, teasing in his voice. “Two months?”
I faught back a smile, “I’ve been dating a girl for a while, she doesn’t do that,” I admitted.
“Oh, that’s right, you’re bi,” he teased a little more obviously.
“I am,” I felt the need to reassert.
“Does she know you’re bi?” He asked, a shift in the air of our conversation.
“No,” I shrugged it off, not wanting her to become a talking point while my softening dick was in my hand.
“Do you… sneak dick in… on the side?” He asked, while setting himself up for the obvious next question.
“No,” I shut it down quickly.
“That’s unfortunate, if I eat you out, I’m also going to want to slip my dick into your hole,” his tone swapped again, and my cock jumped back to diamond hard.
“Mmm…I don’t cheat,” I said as I squeezed my dick.
“Well, my tongue is already in your ass. How long has it been since you’ve let a guy have the privilege of pushing into your tight hole?” He asked.
I breathed out, “Too long, more than a year,” I said honestly.
“Daaaamn…that makes your hole practically a born-again virgin,” he chuckled. “I’ll bet you’re so tight it needs to be pried open to get my tongue in.”
I held the phone to my ear with my shoulder so I could sneak my fingers down to my pucker as I continued stroking with my other hand. “It’s so tight.” The desperation in my voice was audible.
“What’s the biggest dick you’ve ever taken?” He asked, not out of horniness but out of genuine curiosity.
I immediately thought of Tank. “Seven inches.”
“Not bad, did you take it like a champ?” He asked.
“What do you mean?” I could feel my horny fog taking over my ability to think clearly.
“Did you struggle to take seven inches, complaining like a little bitch… or did you take it like a man and enjoy it?” He asked.
I chuckled, “It was a struggle at first, but by the third or fourth time, I was able to get used to it pretty quickly. I enjoyed it every time, though.”
“Multiple times, huh? Was he a boyfriend before the girlfriend?” He asked.
“Not exactly, just a horny friend,” I tried to leave Tank out of it.
“You liked it when he fucked you?” His question was more direct.
“Mmm…yeah,” I breathed out, feeling the sense memory of Tank's cock in my guts as I stroked myself.
“Did he make you cum while he fucked you?”
“MmmHmmm,” I felt my hole again, and a shiver of excitement went through my body.
“Did you let him cum inside you?” He asked.
“MmmHmmm,” I moaned, remembering all of the orgasms I felt Tank having while balls deep inside me.
“What about condoms?” He asked.
“What about them?” I stroked my dick faster, clenching and unclenching my ass.
“Did you wear condoms or did you let him fuck you bare?” He clarified.
I bit my lower lip, pumping my dick, thinking of the two times I let Tank fuck me without a condom, and how he pumped all that cum inside my hole. I managed to mumble, “condoms.”
There was a pause, “Always?”
“Not…” I breathed heavily, “Not always.”
“Mmmm, he’s so lucky,” Elliot groaned, the pattern of his breathing changing as he stroked his dick on the other end of the line. “Did you let him cum inside you?” His voice was getting ragged.
I huffed, “Let him?” The words rolled around in my head as I stroked, thinking about both times Tank came inside me.
“Yeah, did you let him or make him pull out?” He asked again.
“I guess I let him,” I admitted.
“Would you let me cum inside you?” He asked breathlessly.
“Are you already fucking me without a condom?” The mental image of what I think he looks like, pumping his dick inside me raw, came to mind, and I stroked a hundred times faster, clenching my hole tighter around the idea of his thick cock stroking my guts.
“Yes, and it feels so good,” He breathes out.
“Are you close?” I fed into his fantasy as I stroked my cock closer to orgasm.
“Real close,” he said in a voice laced with orgasmic tension.
“Fuck, me too,” I teased.
He breathed heavily, “Jesus, Dillon, I’m so close, I don’t think I can pull out…” he trailed off and started grunting low and deep.
I knew he was cumming and the mental image of him shooting inside me, the feeling I can only remember having four times in two years, more than a year ago, and something tingled inside me, triggering my balls to tremble and my load shot all over my abs in a few strong bursts. I could hear Elliot recovering from his orgasm on the other end of the line as mine was dribbling out of my cock over my thumb and into my pubes.
“Did you cum?” He asked, his voice regaining its strength.
“MmmmHmmm,” I managed. With other guys, I would just hang up as soon as we both blew our loads, but Elliot was hot on the phone, so I gave him the respect of not hanging up.
“That was hot as hell,” he said. Even though I couldn’t see him, I could hear a grin in the way his voice changed. “Maybe we could try this… in person.”
I squeezed the last of my juice out and breathed a heavy sigh. “I have a girlfriend,” I reminded him and myself.
“I don’t mind,” he said. Then, before I could say anything, he added, “It’s not cheating if I’m giving you something she could never give you.”
I chuckled, “sex with someone else is cheating, Elliot.”
“If you say so, but she doesn’t have eight inches of thick cock to fuck you with…does she?”
I chuckled even harder, looking down at the cum pooling in the crevices of my abs as it liquified even more. “No, that’s true.”
“Maybe we can meet up and just jerk off together, that can’t be cheating, right?” He negotiated.
I couldn’t help but smile and shake my head, “Maybe, I don’t know. I’ll think about it, but I have to clean up my mess.”
He let out a heavy breath, “Yeah…me too. I don’t live far from the Yard House if you find yourself over there and want to grab a drink or something…you know how to reach me.”
“And I know what you’re looking for if I do,” I joked.
“Heeeeyyy, we both enjoyed it. I’ll be good, I promise,” he said.
“We’ll see. I’ll talk to you soon,” I said.
“Talk soon,” he said, then hung up.
Two weeks went by. I must have jerked off a dozen times thinking about Elliot. I only had phone sex with LeeAnne once, and admittedly didn’t enjoy it nearly as much as with Elliot. I also had a hard time just getting her on the phone over those two weeks. She’s been busy prepping for her finals and keeps turning her phone off. I get it, I’m studying hard as well, but clearing my head of sexual tension always helps me study.
I missed a call from her while I was at the library, then tried to call back while walking in the freezing cold toward the bus stop that gets me back to the frat house.
“Dillon, can you hear me?” She shouted.
“Kinda. Where are you?” I shouted back, plugging one ear to listen.
“It’s Gary’s birthday, we’re all out celebrating,” she shouted.
Something about this guy, Gary, I keep hearing about rubs me the wrong way. “Oh, tell him I said happy birthday,” I said.
“Sorry, babe, I can’t hear you. Let me call you back in a few minutes, I’ll sneak out,” she said and hung up.
Not knowing if she was calling in a few minutes or later tonight, standing in the freezing cold, I started walking toward the bars where it’s warm. When I started to think of which one would be fun this time of evening on a Wednesday, this close to finals, I realised how close I was to the Yard House and found myself wandering that way. As I walked, I rolled it around in my head if I should just grab a drink and wait for LeeAnne to call or if I should…call a friend to come hang out.
I called Max as I walked and got his voicemail. I called Alessandro and got his voicemail too. Everyone else would already be at the frat house or on the other side of town, and nobody wants to come out in this cold. I turned up my collar and walked the rest of the way to the bar, phone in my hand in my pocket.
I was on my second Jack and Coke, having not eaten, it was hitting me harder than usual. I was annoyed that LeeAnne hadn’t called yet and that I was wasting my time. I could’ve been home, warm, and hanging out with the guys. It was already 10:00 pm on a Wednesday, so I should be in bed already. My phone, sitting on the table, started vibrating on the bar just as I was about to get the bartender's attention and cash out. I flipped it open quickly, “Hello?”
“Were you expecting me?” A man’s voice asked.
I couldn’t place the voice with a name over the loud music. I pulled the phone from my face and looked at the number; it was Elliot, and the voice locked into my head. “I might have been thinking about you,” I swirled my empty glass, the ice spinning inside.
“Mmm…what are you wearing?” He immediately started.
I looked down, “A red sweater, black jeans, teal briefs, snow boots, socks…”
“Oh, you’re out at the bars…on a school night, naughty, naughty,” he teased.
“Yeah, I’m over at the Yard House, actually,” a part of me knew what that piece of information sounded like I was offering. A part of me was tipsy, horny, and frustrated with my girlfriend. A larger part of me hadn’t wasted any time rubbing two brain cells together to think through any of that.
“And you weren’t going to invite me?” He asked, feigning hurt.
I chuckled, “I wasn’t planning to be here at all.”
“I see. Will you be there long?” He asked.
I looked around, took in a deep breath, then looked at my watch. “Probably not. I’m almost done with this drink, and then I’m heading out.”
“Ah, ok, well, enjoy your drink and give me a call when you get home,” He said.
“Maybe I will,” I grinned, knowing what that meant.
“Later,” he said.
“Bye,” I said, hanging up. Then I gestured to the bartender for the bill. He gave me a thumbs up and went over to the other side of the bar. I looked around, the bar was more dead than I expected. Probably the cold, but mostly because they get most of their business from college students who are all noses in books right now.
The bartender brought over my bill and placed another drink on the bar. “This one’s on me,” he said, then walked away to make a cocktail that looked intricate. I paid cash, tipping beyond extra because of the free drink, then started sipping my ‘free’ drink.
I was enjoying listening to "Boulevard of Broken Dreams," playing loudly, seemingly for me and a handful of other twenty-somethings scattered through the large bar, when a cool breeze wafted by from the door opening and closing. I glanced toward the door to see a handsome guy in his early 20s. He’s probably six feet, maybe a little taller. On the thin side, but it’s hard to say with his heavy winter coat. His fine brown hair was parted down the side, wind-blown but freshly showered, and his face looked very English, as if 20-year-old Prince William and 20-year-old Tom Hardy had a baby who was wearing his best Oxfords. When he untied his scarf, he smiled at me, “Is this seat taken?”
I looked around dramatically. There was literally no one but me seated at the bar, and this guy wanted to sit next to me? I chuckled, “Nah, it’s all yours.” I picked up my drink and watched him take off his coat in my peripheral vision. His thin V-neck sweater and collared shirt combo clung tight to his body, showing off his lean muscles. I took another sip of my drink.
“Can I buy you another?” He asked.
I spun slowly on my stool, wondering what game this guy was playing. “What?” I smiled.
He leaned in, placing a hand on my back and his lips close to my ear, “I would like to buy you a round, on me.”
I recognize that voice and swallowed hard, slowly pulling back to give this guy another look. The grin spreading on his face was infectious, and I felt my face returning the smile. I half squinted at him, trying not to smile, “Elliot?”
His cheeks turned pink, his grin showed off all of his teeth, “in the flesh,” he flagged down the bartender, pointed at my drink, then held up two fingers.
I took a big sip of my drink, then set it down before asking, “What are you doing here, Elliot?”
He reached out and squeezed my shoulder, “You invited me. I couldn’t let you drink alone.”
I pursed my lips, fighting a smile as I slowly shook my head, “I…don’t recall…inviting you.”
“Oh,” he scrunched up his cute face. “I must have misunderstood, how…silly of me,” he grinned as two drinks were set in front of us. Then he slipped the bartender some cash and told him to keep the change.
I downed the last of my third Jack and Coke, then picked up the new one, “Cheers,” I clinked my glass against his. Taking note that his eyes were hazel with flecks of gold throughout.
The conversation was light. We talked about the music mostly; he seemed to have an extensive knowledge of every song that came on, and I just enjoyed hearing him geek-out about it. As I finished my drink, he put his hand on my knee and leaned in, “I’d love to take you back to my place, show you my… record collection.”
With liquid courage running through my veins, horniness increasing with every subtle touch from him, I couldn’t help but be bold, and I leaned in, sliding my hand down his back, tracing the shape of his tight body as I whispered in his ear, “I think you want to show me something else.”
He chuckled, nodded his head, “Well…that’s up to you, but either way you should come over.” Then he pressed his thin lips together, no smile, just a clear indicator he was waiting for an answer.
I looked into his eyes, the gold flecks hypnotizing. I knew what he really wanted, and at least five and a half inches of me wanted it really badly, too, but I knew I shouldn’t. “Just to see your collection, then I’m going home.”
“Of course,” he grinned, standing and reaching for his coat.
His apartment was a few blocks away. The wind was whipping and going right through my coat. I was shivering by the time we got to his place. He pulled me into his room, shushing me so I didn’t wake his roommates, and locked the door behind us. He helped me out of my coat as he dropped his on a beanbag chair, then pulled me in for a hug, running his hands all over my back and arms. “Let’s get you warmed up,” he said.
Feeling a bit drunk, I let him feel me up as I pressed my body against his, wrapping my arms around his narrow waist, and let his body heat radiate into mine. I don’t know what came over me, but I inhaled his scent so deeply that it was audible, and it made him chuckle.
“You’re only here to see my…record collection,” he chuckled.
“Sorry, you smell good…and who has a record collection in 2005?” I chuckled.
He squeezed me tight, “I’m not a…guy who does things because they are trendy. I do what I like, and in this case, I love vinyl records.”
“Mmm…ok, which is your favorite?” I asked, pulling away before his Hugo Boss and masculine scent take me down.
He quickly bent over, his undershirt rising, showing off a small patch of skin, the waistband of Armani underwear and a nice, worked-out ass in his pants. He quickly pulled out a record without showing me the cover, then flopped it down on his record player and spun it up. He adjusted the volume knob, then dropped the needle, and it started playing, a riff I recognized right away. “Secondhand News” by Fleetwood Mac. He spun back around, standing tall and lean, pulling me to him, and he kissed me. It was a deep, passionate kiss, with his tongue exploring my mouth and mine his. He pulled my sweater and undershirt off.
I followed suit and pulled his shirt off, the cuffs of his button-up trapping him for a second, and I just yanked harder to pull it off. Drinking in his body for a moment. It was narrow, thin, but firm, defined pecs and abs, his V-cut snaking into his underwear, the faintest whisper of hair trailing from his belly button down into his waistband. His hair was puffy with static, but his smile was award-winning and when he kissed me, pulling my naked chest to his, the warmth of his body and the thumping of the record player had me in a daze. Slipping off my shoes as I undid his belt, button and zipper, his pants fell off his hips, revealing a pair of red Armani hip briefs and a bulge that was already stretching the will of the fabric.
My heart started racing. I know he told me he was eight inches, but I didn’t believe him. Now that he’s growing in his underwear from my groping, I’m getting nervous.
He undid my belt, and my jeans fell to the floor. I stepped out of them and sat down on his bed in just a pair of teal Hanes briefs with a white waistband. I was hard and wanted to get off with him. As I watched him pull off his shoes and the pants around his ankles, I started to think about LeeAnne and felt suddenly very guilty. When he got on the bed, he spread my legs with his knees, putting his hands on my knees and sliding them halfway down my thighs, and the guilt really settled in. “Just…jerking off, right?”
I could see the disappointment in his face. He leaned over and started kissing me. “If that’s all you want,” he left it at that, breaking the kiss and leaving me wanting so much more. He sat back upright, his long arms reaching down and grabbing my underwear, hooking into the waistband and pulling. I lift my ass and let him pull my undies off. I watched him quickly shuck his briefs; his dick looked even bigger now that it was set free.
He started stroking himself, and I started stroking myself. The silence between us was broken by the sound of “Never Going Back Again” on the record player. I watched his hand flying up and down his shaft. He leaned over to the nightstand, pulling out a tube of lube, slicking up his dick, he smiled, “I don’t jerk it dry, do you want some?” I shook my head no. The slickness of his cock shines in comparison to the rest of his pale skin. I watched his stomach puff out with each breath, then sink back in, and all of his abs became visible again. I couldn’t help but reach out to feel his taught stomach, which only encouraged him to scoot in closer, spreading my legs wider until his dangling balls were rocking against mine.
He pushed my legs back and looked down at my ass. “Mmm, it looks so good,” he smiled, then rocked his hips so his dick dangled between my cheeks and then traced up my crack to my balls, sliding to the side and rubbing along my cock.
“Mmm…just jerking off, right?” I reminded him.
“Can I lick your hole? Just a taste?” He pushed my knees up to my shoulders, exposing my hole to him so quickly…how could I say no?
“Just a taste,” I repeated, watching his head dip below my line of sight as he dove right onto my asshole. “Oh…fuck,” I moaned, grabbing my knees and holding them for him so he could use his hands to spread my cheeks apart and get his tongue deeper into me. The record switched to “Don’t Stop”, and I swear he was humming it in my hole as he tongue fucked me. I was surprised by how quickly he was able to get it into me, but God, it feels good. I hadn’t been touched sexually in weeks, and it had been well more than a year since I was touched there. “That feels so good,” I mumbled.
He sucked my balls, licked my ass, then took my dick into his mouth for a few expert seconds before tonging his way back down my nuts and into my hole. It felt so good, I was struggling to hold my reserve and not give in and have him pound me.
I reached my hand down, running my fingers through his hair, “That feels so good, don’t stop.”
He gave me another song of ass eating, but when Side A ended, he pulled his tongue from my hole and sat back up. He hopped off the bed, flipped the album over, then jumped right back in the bed as “The Chain” started playing. He got back between my legs, grabbed his lube and added more to his cock, then rubbed the excess onto my hole with a grin. “Do you want to make me feel good?"
I smiled and raised an eyebrow, “I don’t think we should...”
"Just let me poke the head in for a second," He added pressure, and it felt amazing as his fat head breached my pucker. The sting was there, but my drunken horniness ignored it because the feeling of his cock stretching my hole was too good to ignore. He leaned over me and kissed my neck, then hunched his hips a little, pushing an additional inch into my tight hole. “Ahhh…that’s more than the head, Elliot.”
“Mmmm…it feels so good too,” he mumbled into my neck, trying to get another inch in, but my ass was resisting his girth fiercely.
“Ungh…wait. Do you have a condom?” I asked, clearly giving up on leaving here with just a circle jerk.
He kissed my neck again, scooping his arms under my back and holding me tight as he groaned out a whiny "No.”
I groaned, “Mmm…we gotta stop, then.”
He sucked on the thin skin of my neck, "Mmmm, " he rocked his hips, another inch sinking into me. “Just let me get a few pumps in. I just want to feel you," He pressed in deeper.
The intensity of his cock, having half of his eight inches inside me and getting thicker as he went. I groaned and held him tighter, spreading my legs instinctually as I tried to relax. It’s been such a long time since I had a dick in me; this dick was huge and spearing me like a sacrificial lamb. “Ungh…wait,” I groaned.
“Almost there,” he whispered.
“Ahhh, fuck, I don’t think it can go any deeper,” I groaned, feeling him hit what felt like the end of my ass.
“Just relax,” he said, “this part is going to feel weird, but I promise it’ll be good.” he kissed me, rocking his hips out and then slamming them deep into me. I practically screamed into his mouth; it felt like he tore a hole into my guts. He held himself there, and I whimpered under him until he let me break the kiss.
“Fuck, you’re so big, dude,” I groaned and hissed, still trying to relax around him.
"It’s not so bad," he reassured me, planting another kiss on me. I ran my fingers through his hair, feeling fully impaled, feeling the sting subside and the pleasure rushing in as the warmth from his cock spread deep into my guts. He rocked his hips gently, his dick kept poking deeper and deeper. He made out with me frantically. I could feel my heart beating like crazy. His raw dick started pumping slowly inside my ass, and I closed my eyes to the feeling of his skin sliding against my insides.
I moaned as he bottomed out, “Ngh…ok, we should stop," I huffed.
"Yeah, we should," he said without skipping a beat. Kissing my lips, then looking into my eyes, those gold flecks catching the dim lamp light just right. He didn't even slow down his thrusting, just slowly pushing all the way in and pulling most of the way out. I felt his balls against my ass. "Mmmm…your ass is sucking me in, though," he mumbled in pleasure, his half-lidded eyes locked on mine. "It feels…so good."
"Are you…tested?" I asked, feeling myself cave to the pleasure of his cock.
"Yeah, of course," he said quickly, still slowly fucking in and out.
I felt his cock deep in my guts again, "Wait, we shouldn’t," I groaned, struggling to accommodate that last inch in my guts.
"Mmmm…it’s ok," he said softly, grinding his hips against me as his head swirled deep inside me. "God, you feel so good.
"We should have a condom on," I said, trying not to sound whiny, but also suggesting he should pull out.
"It's ok, I trust you’re clean," he said, fucking a little harder. The bed was rocking against the wall with a thump that matched the drums of “You Make Loving Fun,” on the record player. Then he started to piston fuck me, grunting in my ear with each deep thrust. It was the most intense fucking of my life.
"Mmm, ungh…wait, no, stop," I insisted. Feeling him getting thicker with each thrust, knowing his raw cock was dumping precum into me and the only reason his cock is gliding so easily inside me.
As if he could read my mind, he kissed my neck and mumbled with labored breath, "I'll pull out in time to cum… I promise.” He grunted and picked up the pace, matching “I Don’t Want to Know” on the record.
I gave him a few more strokes before I realized this was beyond cheating and not safe. “Ungh…fuck, we should stop,” I said with a seriousness in my voice.
He pumped deep into me, his pubes against my balls, lifting his head to look into my eyes, “Just one more song, let me fuck you for one more song,” he pleaded in a desperate whisper.
I felt his cock twitch in my guts, “One more song.”
He smiled, and the record switched over to “Gold Dust Woman,” as he started digging deep into my guts. I held on tight, spreading my legs wide as he continued pummeling in and out.
"Fuck, that feels good," I mumbled a confession.
His eyes lit up, "Yeah, you like my raw dick in you. Don’t you?" He thrust deep as he kissed me.
"MmmmHmmm," I moaned into his mouth. Taking his dick and opening my hole for him. He gave me a few piston fucks, the bed smacking into the wall, no doubt waking his roommates as I moaned into his mouth and he moaned into mine. I spread my legs wider into the air for him to have easier access and get even deeper into my hole. The feeling of his head popping into my guts like it was had me in a cloud of horny bliss.
Without slowing down, he mumbled, "I'm getting close."
"Oh fuck," I moaned, gripping tighter to his back as he continued to pump into me. I wanted to shout into his ear to pull out, but the words didn’t come out.
He gave me a few more deep thrusts and then slammed into me as he grunted a stifled, "Fuuuuuck," in my ear, and I felt him unloading eight inches deep inside me. His grip on me was so tight a laser couldn’t separate us as he twitched and spurt after spurt of hot cum shot into me. “Oh…fu…uck,” he sing-songed as life reentered his body. “Oh, shit,” he pulled out quickly, his cum leaking out of my hole onto his bed sheets. “Fuck, I didn’t mean to…” he looked at me in a panic.
I was wasted and fucked into submission. I grabbed my own cock and started jerking for dear life, “Stick it back in me,” I instructed. Without hesitation, he grabbed his cum slicked cock and slammed it back into my cum soaked hole. I pumped furiously on my cock as he watched and slowly rocked his hips back and forth, sliding his hardening cock in and out of my guts. The idea of his cum smearing my anal walls, combined with the pleasure of his cock still fucking me, sent me over the edge. “Oh…fuck,” I grunted, firing my first wad past my shoulders onto the pillow.
“Oh fuck, yeah,” he moaned, feeling my ass clench down on his cock. He thrust hard into me, each thrust triggering my next wad of cum as the orgasm kept rocking through my body. The cum kept shooting out, my balls kept tingling, and I kept stroking as he pummeled my prostate. My body twitched, powerless, destroyed, blissfully fucked out. “Fuck, I’m gonna cum again,” he said, leaning over me and fucking harder into me.
The thrusting deep into my guts after I shot my load was intense. His cum kept me lubed up, but I was quickly fading out of my horniness. “How close?” I asked, unintentionally pushing against his chest to push him off of me.
He leaned in and kissed me, “I’m about to cum. Want me to pull out?”
I hesitated, but he kept pumping into me.
“Dillon, do you want this load too?” He pumped faster, and it felt incredible for a brief moment as his cock grew thicker and stretched my insides. “Oh…fuck,” his torso trembled on top of me, and his hips slammed into me. I felt his cock twitching in me for the second time in five minutes. “Ungh…mmmmm,” he groaned in my ear, his sweaty body held tight to mine as he finished unloading. He relaxed on top of me, taking a deep breath, “fuck, that felt good.”
I couldn’t help but chuckle, gently pushing him off me. Feeling his cock slide out of me and the cum tried to drip out, but I clenched my ass instinctively. I put my arm over my eyes, blocking the light. The guilt rushed in. I can’t rationalize this as anything but cheating. I groaned and grumbled until I felt his arm cross over me and pull me in for a cuddle. “Just enjoy it,” he said. Words of wisdom that floated through my head as I drifted off to sleep, naked, next to a guy who just made me his in the most intimate way possible.
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Brendan Gavin
He’s had his best fuck yet
