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Dillon - Part VIII -Boyfriend Material
🕑 Added 2025-12-13 21:29:00 +0000 UTCAfter my hookup with Elliot, I felt insanely guilty and started to spiral. With the holidays coming up, there was no way I’d be able to have sex with LeeAnne with a clean conscience. We stopped using condoms early on in our relationship because she has an IUD, and…that was all the convincing I needed because we were committed to each other. Now I’ve broken that trust. Of course, I can’t be sure she has been faithful either. Especially since I keep seeing more and more pictures of “Gary” on her Facebook page, and it seems like he’s a little too flirtatious for my liking.
My phone buzzed; it was a text from Elliot. “The other night was so hot, I want to do it again.” I ignored it and text LeeAnne, “Call me when you can.” I had a text from her the morning after, apologizing for not calling me back and saying she had a busy day yesterday. I don’t usually hear from her on Friday nights because she’s in a sorority, and they often do things together on Friday nights. “Safety in numbers,” or whatever. So I didn’t expect to hear from her today either.
I spent the night at the house, the guys tried to get me to go out, but I was still kicking myself for letting Elliot fuck me and cum inside me. Sure, it was the hottest sex I’ve ever had, but it was fucking stupid, and I know better. I pulled out my phone and text Elliot back, “It was hot, but I shouldn’t have let you cum in me.” I hit send, thinking it read like a ‘I don’t want to do this again,’ but when he text me back, I realized he read it entirely differently.
Elliot: It felt so good, I’ve already jerked off three times thinking about doing it again!
Me: Hahaha, three times and your dick still gets hard?
Elliot: I never have trouble getting hard. Especially when thinking about how hot you are, and that sound you make when my big dick pushed into your second ring.
Me: My second ring?
Elliot: Oh yeah, that tight second ring deep inside you that grips the tip of my cock with each thrust, there’s no better feeling in the world.
Elliot: I must have been your first because it didn’t go in easily, but God, it felt so good, I’m surprised I made it more than two pumps before shooting my load.
His words got me hard despite wanting to wallow and feel shame for what I did. He’s right, though, it felt so good, there’s no way I could’ve stopped him…I was way too horny and dick-drunk to think of anything but pleasure. I’m not now, though, so I know I need to lay down the law.
Me: It was hot, but still should've used a condom or not at all.
Elliot: Aww, don’t worry, I get tested regularly, and your ass is the only one I’ve been in raw since my last tests all came back negative.
That was somewhat reassuring. Not enough to clear my conscience with LeeAnne, but enough to unclench for my own sexual health.
Me: Next time, you have to wear a condom.
I hit send without thinking, and as I read my text, I realized I just agreed to another round with him. He picked up on it right away.
Elliot: Next time? I was worried I scared you off.
Elliot: I thought my dick might have been too big for you, even though I tried to go easy.
Me: It was definitely the biggest I’ve ever had.
Me: It was definitely a challenge, but I’ll admit I like a challenge.
Elliot: Hahaha, that’s the straightest way a guy has ever told me he likes my big dick.
Me: Hahahaha
Fuck, am I flirting with Elliot? Wait, is he flirting with me? I don’t think I’ve ever had a guy flirt with me before. All the sex I’ve had with other guys was always spontaneous as a result of overwhelming horniness, or a planned hookup from the internet.
Elliot: I don’t suppose you want to come jerk off together, again?
Me: I’m not falling for that again.
Elliot: I swear, just jerking off.
Elliot: Scouts honor
Me: You were a Boy Scout?
Elliot: No hahaha
Me: Hahahaha
Elliot: I’ll be honest, I really want to fuck you.
Me: You know I have a girlfriend.
Elliot: I won’t tell her you like having my dick deep inside you.
Me: Hahaha
Me: That’s kind of you
Me: A real bro
Elliot: Come over, I know you want it too.
Me: Do I?
Elliot: Are you hard right now?
I realized I subconsciously had slid my hand into my underwear and was squeezing my hard cock, leaking a wet spot through my briefs and sweatpants already. Fuck.
Me: I am.
Elliot: So am I. Let me get in that tight ass again.
My heart was racing, and I kept looking around to make sure none of the other guys had come home and could see my texts, even though I was in the living room alone and would’ve seen anyone who came home walk through the door.
Me: Did you get condoms?
Elliot: No
Elliot: My roommate is out, so I can steal one of his if you come over.
My hormones had kicked into high gear. This hot guy who fucked my brains out was asking for round two, and I was running out of reasons not to. That’s when my phone started ringing. It was LeeAnne.
I took that call, and we had a short conversation because she had just returned home from dinner with the girls, but they were changing to go out for drinks, so she couldn’t talk for long. When we were off the phone, my erection had gone away, and so had my horniness. My guilt was back, so I didn’t even look at the unread texts, which I assume are from Elliot. I decided to hop on my laptop and do some studying.
About ten minutes into studying, my phone chimed, letting me know I had another new text message, and I didn’t look at it. I knew it was going to be Elliot tempting me to cheat again. Instead, I pulled up Facebook to see if LeeAnne had posted anything new. Sure enough, there was a picture from the dinner she said she went to with the girls, and who was sitting next to her? Gary. Fucking Gary.
I’m not the jealous type, I’m not one to get emotional, but for some reason, this sent me through the roof. The way his arm was draped over her shoulder, the stupid fucking grin on his stupid fucking face, which was awfully close to her face, too close for comfort. There’s no fucking way she’s not cheating on me with that guy. Of course, Gary is one of three people who already ‘liked’ the picture.
I went over to Gary’s profile. There are almost no girls other than LeeAnne in his photos. Otherwise, it’s mostly shirtless photos of him, and I’ll be honest, I have a much better body, and so does Elliot. That sparked the passing thought that the guy I cheated on LeeAnne with is hotter than the guy she’s cheating on me with. I would’ve laughed at the idea if it didn’t frustrate me so much that I was here feeling guilty about my…indiscretion, but she’s probably out riding Gary’s dick right now, not giving a shit about my feelings or sexual frustration. Did she even go out with the girls, or did she just go straight to his place after we got off the phone?
I flipped open my phone.
Elliot: Unless you don’t want one.
Elliot: That was a joke. I know you said you want to use one.
Elliot: To be clear, I’m cool with using a condom if you want to come over.
Elliot: I’ll pull out to cum if you want.
Fueled with rage and still horny, I decided to text him back.
Me: I’m coming over.
One quick cab ride and I was in front of his place, this time sober, and deliberately making bad decisions. But in my defense, if LeeAnne is going to get fucked by Gary tonight, I’m going to get fucked by Elliot.
I buzzed, and Elliot let me in from the cold, taking me back to his room right away, closing and locking the door behind us. “My roommates both came home,” he spoke in a low voice.
I raised my eyebrows, a little surprised. I hooked up with Tank several times at the Frat house while other guys were around, but that was different. None of them knew we were having guy-on-guy sex. I assume Elliot's roommates know he’s…gay? I think he said he’s gay. I sat on his bed, and I felt nervous all of a sudden. Somewhere between being angry with LeeAnne and getting into this room, I didn’t really give myself time to think about what I’m actually doing here. “Do your roommates know I’m here?”
“No,” he shrugged, “but we don’t have any house rules about this kind of stuff. We could go fuck on the couch, and I don’t think they would care. I think Richie would watch,” he grinned.
That made me chuckle, “I do not want to do that.”
He smiled. “I just wasn’t sure if you want them to know you’re here since…you’re in the closet, right?” I nodded and shrugged. “What do you want to do?” He asked, sitting next to me on the bed, putting a hand on my thigh, his Hugo Boss cologne wafting into my nose as he leaned in close enough that I could see the gold flecks in his eyes again. I had two thoughts: the first was to get out before I do something stupid. The second was to do something stupid. Stupid won, and I kissed him.
Up to this point, I don’t think I’ve hooked up with a guy completely sober, but I had come this far, and horniness was already winning out. He kissed me back, his tongue dancing with mine as his left hand raked fingers through my hair and his right inched closer and closer to my crotch.
I let him lean us both back onto the mattress, his right leg swooping over mine, spreading my legs as he half rolled on top of me as we continued to make out. I started letting my hands feel up his torso, under his t-shirt, feeling the sinewy muscles I remember him having the last time we hooked up; they feel even tighter now. The growing bulge pressing against mine through our clothes reminded me how much bigger his dick is compared to mine.
I enjoyed our makeout session for a few minutes before I slipped my hands into his pajama pants, sliding them off his ass and copping a feel of his tight ass from outside his grey ribbed briefs and making him moan into my mouth. He broke our kiss, “Shit, I need to go get a condom,” he said, grinding his hard bulge into mine.
“Not yet,” I pulled him tight to me. Kissing a guy, kissing Elliot specifically, was so hot I could be satisfied with just being devoured by him like this. There was something about the way he was attracted to me that felt different from when LeeAnne and I kissed. There was an urgency, a need that didn’t exist with her, as if his mere survival depended on continuing constant contact with me through touching or kissing. His breath, trading with mine, our bodies grinding as more clothes were shed, and we rolled around on his bed, humping against each other in just our briefs.
After tens of minutes of just lustful kissing and heavy grinding, I found myself on my back with my legs wrapped around his hips, him grinding against me, his cock threatening to break through the cotton fabric of his underwear, through mine, and penetrate me with one fierce thrust. He broke our kiss again, pulling himself from me, even though I was holding on tight, my hands slipped from his back as he made himself upright and took a breath. “I’ll be right back,” he hopped off the bed, his cock tenting in his stretched underwear. It looked bigger than I remembered. He cupped the tip over the strained fabric and opened his bedroom door, darting out, the door pulling itself mostly closed save for the latch tongue.
I took the time to look around the room; it was both masculine and somewhat gay, old-fashioned but with modern things mixed in. It was cozy, warm, and inviting; it felt like a real adult lived here. I sat up on my elbows, looking down at my mostly nude body. My abs were crunching, the happy trail leading into my underwear where my dick was still rock hard, then my legs were still spread, waiting for Elliot to return. I felt a pang of guilt, knowing I’m once again choosing to cheat on LeeAnne, but I reminded myself she’s doing the exact same with…Gary.
The door flew open and then closed in a flash with a push of the lock on the door knob as a skinny but sexy Elliot came back in, holding a condom like he was Charlie with the Golden Ticket to the Wonka Factory. He crawled back into bed, waggled his eyebrows at me, and the grin on his face was sexy in an adorable way; he really wanted this. Possibly more than I did. He sat up on his knees and shoved his briefs down his thighs, shifted one knee, then the other as he continued to shuck his underwear. I followed his lead, lifting my ass, shoving my briefs down and off my legs, and setting them just off to the side of the mattress. He reached for the lube and handed it to me. I smiled; he was not trying to waste any more time. I poured some lube into my hand and started rubbing it onto my pucker, then slipped a well-lubed finger inside, swirling it around as I watched him tear open the condom and roll it down his shaft with a bit of difficulty. His roommate must have a smaller cock.
In the light, his cock looked even bigger than I remembered from our drunken hookup. With the condom rolled out, it looked intimidating as hell, and I felt myself clench a little around my finger. I punched up my hole prep to two fingers and started doing my best to relax my hole the way Tank had taught me, so I could quickly take his cock when time was against us.
Elliot lubed up his condom covered shaft, then grabbed a rag to wipe his hands clean. “You ready?” he smiled devilishly.
I nodded and spread my legs into the air, like I was landing a plane with my sock-covered feet as the marshalling wands. He leaned forward, placing my legs on his shoulders, a hand on the mattress to the side of my chest, his other hand reached down to guide his cock to my hole. I felt the latex-covered rod swirling at the center of my pucker. “Right there?” He asked. I nodded, and he started pushing. The head popped in with excruciating pain, and the crinkling sound of the condom being stretched to its limits as I gripped his comforter in my fists, hissing and pushing my legs against his shoulders. “Just breathe,” he cooed, leaning heavier on my legs, slowly folding me in half as half of his cock sank into me. When he had my ankles up by my head, he kissed me. The sparks started to fly as his tongue danced with mine, my breathing syncing with his as I began to feel the gentlest pumps of his cock. A millimeter in and out, just nudging its way deeper into my hole.
Elliot held me tight as he slowly pushed all eight inches into me, and fuck was that a struggle. The worst part was the friction from the condom, but he was so hot and caring, I couldn’t help but enjoy 100% of the experience. By the time his hips were flat against my ass, I was already hard again. He broke our kiss, pushing himself up enough that I could sneak my hand between us and start stroking my cock as he gave me slow, deep thrusts of his cock. He hyper-focused on my body language, noticing when and how he made me moan and the things that made me hiss. Feeling his long cock pull back and then push in slowly, stretching my anal walls and putting constant pressure on my prostate as I stroked myself until he gently penetrated my second ring, which was a sensation only Elliot had managed to provide for me. I was going insane, stroking faster and faster. He seemed to enjoy making me moan, steering his attention to those aspects and avoiding the things that made me hiss until I found myself rocking my hips up and down on his cock even when he would stop thrusting to hold off his orgasm. I was in heaven.
“That feels so good,” I panted. My free hand was holding onto his neck, pulling him as close to me as he would let me, passing one sex filled breath between us as his mouth hovered inches from mine. He maintained constant eye contact as he continued to pummel my ass gently. The sting of his first entry was long gone, and nothing but pleasure seemed to wash into my body. I could feel my toes curling behind his back as my heels tried to pull him deeper into me. He resisted letting me control his fucking and continued to just hammer me with one long, deep thrust after another. I was going insane, and trying to keep his roommates from hearing how much I was enjoying getting fucked by him.
Pumping my cock, I warned him I was reaching the point of no return, “I’m close.” That triggered his hips to start thrusting with power again. Pulling out about two inches, then grinding all of his cock deep inside my guts, busting through that inner ring and sending me over the edge after only a few more minutes of pumping. “Oh fuck,” I whimpered, pumping my cock, flexing my hole around his thickening cock. “I’m cumming,” I panted. He picked up the pace and, after only a few more thrusts, couldn’t hold off any longer. The intensity of his cock deep inside me sent waves of pleasure through my body. I was shooting my load all over my chest, one glob of cum splattering after another.
Just as the tide of my orgasm was heading out, I felt him grow thicker inside me, letting his bare chest press against my cum-covered torso to kiss me as he hunched up inside me for a few more deep thrusts, each one more greedy with the need for release than the last. “I’m about to cum,” he panted, “do you want me to pull out?”
“No,” I pulled him down to kiss me, and hooked my legs around his waist even tighter.
He moaned into my mouth, thrusting deeper into my ass for a half dozen uncoordinated thrusts, then a sudden halting and an almost inaudible moan as every inch was buried inside me, followed by twitching inside me as he filled the condom with his load. He groaned into my mouth, sucking the air out of my lungs for his own survival, as he continued to throb inside me, his release filling the condom so much I could feel the tip ballooning ever so slightly inside my guts.
He relaxed on top of me after a minute. He kissed me gently, but passionately long enough for his cock to soften inside me and be forced out by the tightness of my hole. Breaking our kiss with a chuckle from the sensation, he looked into my eyes and said, “Jesus, you’re tight as hell.”
“Well…a little less thanks to your battering ram,” I joked.
He gripped the base of the condom and pulled the reservoir tip from my hole, and that weird feeling of the last of his warmth was pulled out of me. He used his rag to clean the cum off my chest, and we fell asleep after a quiet few minutes of cuddling.
The next day, I had a nasty phone call with LeeAnne. I accused her of cheating on me with Gary, which she denied. We broke up, and that was that. I did see on Facebook a few weeks later that she was, in fact, dating Gary. I’m not sure if I caused that or what, but I was regularly getting fucked by Elliot, so I didn’t have feelings on it either way. I had a pretty good feeling my regular sex with Elliot, always safe, of course, was becoming way more than just sex, which… I kind of wanted to see where it would go.
Comments
Brendan Gavin
I can’t wait either. Has been been a wonderful transformation of Dillon
