Hey! This chapter was tough. When I knew I was going to do more of Caleb's adventures I knew it would have to happen, but I went back and forth on a LOT of the details. Hopefully it's not terrible! Let me know at joejam886@gmail.com.
Once again, this is fantasy. If it bears some resemblance to somebody's real life I'm jealous as hell. Play safe though!
Also, donate at http://donate.nifty.org/donate.html! It's a fantastic service that I'd love to keep around.
The day started pretty normally. I got to work a bit before one, lined up my tasks for the day and eased myself into them. About an hour into it I got a message.
"You working?" It was Trevor, who I hadn't talked to in almost 4 years now. We'd been best friends when we were teenagers, going to nearby schools and meeting at a local queer youth group before we came out to our respective families. I was a dorky kid and he was tall and lanky.
"Yeah. What do you want?" I shot off to him. Thing is he was the best friend I could possibly have...as long as I was single. The moment I got a boyfriend he felt some sort of need, and after I realised that need was fucking my boyfriends I cut him off.
"C'mon man. I wanna make amends. I think I know how to make it up to you." His reply came back pretty quickly and I mulled over it for a short while. He'd been there for a lot with me, my family had cut me off for a while, only making amends when my mum realised she was sick. But when I saw him pin Matt to a wall, his thick black fingers squeezing and pawing at Matt's ass, I knew I needed to end the friendship even as he said it was a bit of fun and tried to pressure me into sharing.
"It'll take a lot." I replied. Before Matt I was with Nathan. I was young and thought he was going to be the one, until I walked in on him on my bed, his face red and his eyes clouded in lust. Trevor's warm brown eyes locked onto mind and his thick lips curled into a smile as he just kept thrusting into him. Nathan whined and made a half-hearted attempt to climb away before just giving in and hanging his head, moaning as Trevor refused to relent.
I was done with Nathan and it took months for us to repair our relationship. I looked past the indiscretion and focused on the good times, only to walk in on him choking my next boyfriend with his cock. I didn't confront either of them, ending things gently and letting Trevor stay in my orbit.
"Luckily I've got a lot." And there it was. The photo came in a second later and it was beautiful. A pointed head, circumcised and suddenly thickening with the shaft. The skin was smooth and black. The sheer girth made my recently fucked hole twitch and my mouth water just seeing his huge hand barely fit around it. It looked like an arrowhead on top of a baseball bat, and my own cock was straining against my pants.
I was lost in gazing at it for at least a minute before I composed my thoughtful reply. "What the fuck do you think you're doing?" My face was red, burning with anger and lust. I was angry. And turned on. And angry that he turned me on. "I don't know what you're trying but you should probably fuck right off."
"I miss you, Cae. You'll like my dick so how about I let you enjoy it? I'm free at about 5." I was trying to figure out how to reply when the screenshot came through. It was a Grindr conversation, and my stomach dropped as I recognised it. My tender, fucked ass, framed by a jockstrap with cum dripping out of me. Then a picture of my torso, still messy after sex, still needing more. "Does Matt know about this shit? I thought you were a big fan of fidelity."
Fuck. He was the stranger I sent pictures to on Grindr, he must have taken screenshots before blocking me. A few tense exchanges later and I'd confirmed that I'd be at his apartment at 5.30, when I normally managed to take my break.
The rest of the afternoon was a strange blur. Anxious energy filled me, moving me from place to place, and before I knew it I was shaking as he buzzed me up to his floor a few minutes early
"It's been a while." His thick lips smirked at me and his eyes twinkled, so smug that I wanted to punch them.
"Yeah. You know why." I fired back, my mood sulky and over excited.
"I do. That was a pretty shitty thing, making moved on Matt those times." Times? Matt only talked about the once when I saw them. "But we were great friends. Brothers. Let's get back to that." He opened his arms wide and I stepped into them, letting his warmth cover me.
I have to admit it felt good. He was probably 6'5", a bit taller than Will and his arms were thick and muscled as they encircled me tightly. He'd been working out, his muscled torso straining against his sweaty gym singlet. My head fell into the crook of his neck like it always used to, and his lips brushed the top of my head. Then his arms loosened slightly, his hands falling to my ass and resting there, his thumbs stroking their way under my shirt to make me shiver.
His head lowered itself and he buzzed my neck, kissing me gently and kicking up my neck, his tongue darting across my war. My whole body felt electric in his arms, surrounded by his scent.
"I mean shit, if I knew that hot little ass was open for business I'd have just ridden you instead of your boys. Nathan was a lazy fuck." My face burned at his words. My emotions ran through the range of jealousy, anger, hurt and lust, with only the last one gripping me to the core. "If you warm me up a bit I'll get you feeling real good." His voice was husky, his hot breath blasting my ear. I only moaned in response and let him cup my head, guiding my face.
Soon my face was pressed into his wet armpit, the damp, curly hair smothering my face so he was all I could smell. My tongue tentatively darted out to taste him, a moan escaping my lips as his hands flew over my fly to undo it.
"When was your last dick, baby?" He asked as his hands returned to my ass and kneaded my bare flesh causing my legs to part involuntarily.
"Th-this morning." I replied, gasping as his thick finger dipped into the crack of my ass and rubbed against my entrance. My face returned to his pit to lap at him with my tongue and rub his sweat into my face.
"Fuuuuck yes. He breed you?" The pad of his finger started pressing into me gently to open me just barely a fraction and I pushed against it, yearning for more that he wouldn't give me yet.
"Uh-huh" I moaned as my tongue worked busily under his arm. Suddenly he moves to learn into me, his thick lips smothering mine and his wide tongue filling my mouth as he forced his finger all the way into me. I breathed in sharply, the air coming straight from his lungs.
My cock couldn't be harder. My legs straddle his thigh, my body pressed against him as his finger pushes itself up to the knuckle, my hole twitching and making me accommodate him.
"It wasn't enough for you." He states this as fact locking his eyes onto mine as he slowly withdraws his finger to the tip before plunging it back in, my whole body shaking with a mindless moan. "Say it."
"It wasn't enough for me." I breathe out, my voice clouded with lust, my body grinding against him,y nuts squeezed against his thigh as his finger plunges into me again and again, my hole no longer resisting the intrusion.
"What do you need, baby?" My teenage crush, my former best friend, my relationship destroyer asks me. My anger and lust both spike as I voice what I need.
"Your cock. Please, I need your cock." He grins at me, his warm brown eyes enjoying the desperation in mine. "I've wanted it for years." We both identified as tops pretty early on and slipped into friendship despite being horny teenagers. He'd be out there playing the field and I'd try to hunt down that elusive true love.
"Strip." He pulled away from me. "On all fours." He commanded, and I obeyed. My cock was painfully throbbing as I released it and precum dripped down to the floor, my heart ready to burst through my chest as I got onto my hands and knees in his living room.
Then his wide, pink tongue was on my ass. Swiping up and down, tasting my sweat and brushing against my sensitive hole. It felt like he was there for hours just savouring my taste and making me wish he could get deeper. He grunted as he pushed his tongue into the ring of my asshole, his spit dripping down my taint and off my heavy nuts.
I could only moan mindlessly as he traced my fuckhole with his tongue and pushed it as far into me as he could go. His massive hands roamed up the sides of my body to tug on my nipples, twisting them sharply before he stroked down my sides again to rest on my hips.
His tongue abandoned my ass and I heard a bottle cap clicking open and shut, the sound of lube on skin filling the room, then I felt the heat of his wet cock pressing against my hole.
"I told you, Cae. This is my gift. I'm gonna just stay here and let you take my load." His voice was soft and commanding, his words filling my lust-addled mind. He said I could do what I wanted but we both knew this was going to end with him breeding me. "Use my big black cock to make it right."
It burned there forever just waiting as I prepared myself. I started to rock back onto him, letting the flared tip start to open me, gasping as I felt it pop inside of me and suddenly his shaft was thicker.
Slowly pushing backwards I opened myself up, adjusting to his wet girth slowly, holding myself there as I needed to. I finally stopped when I felt his tight pubes brushing against the sensitive skin around my obscenely stretched hole and I looked back at him.
"You like that cock, baby?" His grin was smug and I wished I was in the position to smack it off his face, but I was stuffed full of his immense cock, looking at his broad muscled torso, his huge arm and the phone he held in the end of it. It was pointing at my hole and I knew he was fucking filming this.
SMACK. His free hand made my right cheek sting as he slapped against it. I scowled at him and my hole convulsed around him for a moment, and it felt so damn good as he shifted into me slightly deeper with the movement.
"I asked you a question, bitch. You like that cock?" His voice was harsher and he pointed the camera directly at my face. I looked back down at the floor and burned with shame.
"Yes, Trevor. I like this cock." I begrudgingly admitted. Another smack, and suddenly he withdraw most of his length, my hole gripping it so it felt like he was dragging my insides with it, my hungry ass not wanting him to escape me.
"Look at me when you say that." And so I did. Looking at the lens on his phone I angrily spat the same words out. He put the phone away then and rubbed my ass cheeks with both hands, pulling them apart, and I sank back onto him. "Good little slut."
I kept looking at him as I started rocking back and forth on him, loving the feeling as the dull pain slowly gave way to the intense pleasure of being stretched again. I gazed up at his handsome face with lust-clouded eyes, letting the rage melt away as I built the rhythm up. The room was filled with wet slapping noises as he reached up to his round, bulging pecs, and tweaked his thick nipples, groaning.
"You're gonna make me cum if you keep that up." He moaned from behind me, still trying not to move as I ground and slammed myself back onto him, using his manhood to tease every nerve inside of me just how I wanted.
"Good." I slowed my pace a bit but increased the pressure, my ass slamming against him as hard as physically possible.
"Fuck. I have to." Suddenly his weight was on top of me. His powerful hands moved my limbs like I was his play thing, pushing me down, spreading my legs wide and pinning me to the floor. His powerful arm wrapped itself tightly around my neck and his other hand rested on the back of my skull as he started slamming into me at his own pace, pulling back and then letting gravity help drive himself into me hard and deep and fast.
He slammed into me relentlessly and all I could do was moan with my throat squeezed by his strong arm muscles as his balls smacked against my taint with every thrust.
Before I knew it I was screaming wordlessly as I exploded from my cock pinned beneath me. My load smeared against my stomach and the carpet. My ass convulsed around his massive cock as he continued his onslaught.
It wasn't much longer when I felt his cock grow impossibly thick inside me and he pulled back, leaving just the tip inside of me and flooding my passage with his hot load. When his orgasm had subsided he let his cock sink back into my used ass hole and he relaxed his weight, smothering me with his body and letting his arms unwrap themselves from my skull.
His thick lips kissed and grazed their way from my shoulder, up my neck, to my ear. His darted into me and I felt my ass twitch. He moaned into my ear.
"Hope that last part didn't ruin it for you, buddy." Fuck no it didn't. "You were just working that pussy so well." He breathed into my ear, his hands roaming up the exposed sides of my body, his full weight pressing onto my back as his cock stayed impossibly hard inside me, simmering in his cum.
"I might be able to forgive you." I said, my voice sounding laboured underneath me. "But you're gonna have to do that a few more times before we can call each other best friends again."
"I'm okay with that. So really, does Matt know about all this?" He asked, pinching the side of my ass to emphasise the last word.
"No. And it'll fucking stay that way." I replied, pretending like I had some sort of control in either thing at this point.
"All good, buddy. I really did miss you." He kissed the side of my neck again. "I'm gonna be a lot better this time." And with that promise he pulled himself off me. His hardness suddenly abandoned my aching hole, quickly replaced by his tongue again.
He slowly, leisurely lapped at my ass, loudly slurping up the cum he'd just deposited. His tongue swiped up and down my crack, digging into my hole whenever he passed it, and I spread my legs apart on the floor as I grew hard again. It was too soon when he stopped and walked in front of me. I looked up at his heavy, dangling cock, and I was drawn to it.
My mouth wrapped itself around him, tasting the sweat and cum and everything else. My jaw ached as it opened wide so my tongue could explore him. He stepped back, his cock slipping from my mouth, and he leaned down to kiss me.
His soft lips covered mine, his tongue darting across mine, his hands exploring my sweaty torso.
"You should probably tidy up and get back to work." He said and I did just that, lost in my thoughts for the rest of the day, trying to figure out how I felt about everything. Despite all the shit, Trev had helped me through some real tough times and he felt more like a brother than a friend. He was like family and it was time to forgive him.
When I got home it was a tense evening. I don't know if it was just me, or something was happening with Matt, but it just felt off. When we were in bed I lazily trailed my hand across his belly, reaching for his cock, but he just pulled my wrist off him and rolled over.
"Not with Dan in the next room. I'm sure he'll be out of the house soon enough." I mumbled agreement and rolled over myself, ignoring my erection. For now.