Chereads / Faceless Requests / Chapter 13 - My First Time Was a Setup

Chapter 13 - My First Time Was a Setup

Source: Original

Lead: Male

Tags: Mandom, Gay, Virgin

"Brian Davis Roberts. I'm 22, I guess I have a penis, and I'm gay. I'm Irish American and I guess you could say I'm quite shy, bashful, all those things. I try my best to be kind but sometimes I can explode. Only when my temper is tested to its limits tho. I like reading, cooking and napping. Talking to others is real nice. Going to my favourite cafe for tea and sweets. What I can't stand are rude people and bullies, but who doesn't?"

I enter that information as my Winder bio and select the best photos I have. I'm short and skinny so I'm sure I'll find a good daddy dom somewhere on here. I feel my face redden and a devious smile likens to my face. "What am I doing?" I ask myself in the shelter of my own room.

The first photo I choose is with me and my friend Alea being goofy. I do like that photo but I feel like it shows who I am while defining my features. My dyed red hair acting all wild, my hazel blue eyes shining through in a cross-eyed manner, the elegant earrings that I felt the need to show off.

The next photo I choose is one Alea got of me bringing our ice creams to the bench she was at. Near the fountain, it shows off my favourite outfit in a classy style. My blue shirt, blue jeans and sneakers. The wristwatch and reading glasses I need for the obvious reasons, and a necklace I take pride in wearing. It also defines my height, style and smile.

The third and last photo to describe me has to be my pet. Nothing I love quite like her.

As for kinks, they'll have to find that out themselves, I smile. No way I'm showing myself with a list of embarrassing things. I mean, what if my mom sees this?

[A few events transpire that Brian isn't used to and he grows uncomfortable but struggles to act on that]

In the heat of the moment, Alea pushes herself on me. After a confession, I wouldn't blame her. People usually do these things - can't control themselves. She kisses me passionately with her eyes shut tight. Meanwhile, mine are wide as can be. I don't want to embarrass her but. I don't know what to do.

I kiss her back to be nice, but of course, I want out of this situation. She rushes her kisses down my neck and begins to bite before licking along my collar bones. I don't want to be rude but this is becoming a little much for me. "S-stop," I feel my face rush red as she pulls back and looks at me puzzled. "I'm sorry," she tidies herself and pulls away. "I-I can't do this," I try to explain. She tries to get up to leave but I pull her back down. "Wait," I tell her. I breathe in deeply and harshly exhale, becoming nervous and weak to proceed. "I-I don't know much about this stuff," I start. "And I don't think I, like," I struggle to explain. I've never told anyone about this but if anyone should be the first to know, it should be Alea.

"I'm sorry," I drop my shoulders and hold my face in my hands. "That's okay," she comforts me and holds me in her arms. "That's okay," she repeats. "I ain't going nowhere unless you are," she forces a chuckle to lighten the mood. Both of us have just confessed. And I'm sure this'll take a while to get over. "Hey," she sits back a bit and offers me her hand. I look up through teary eyes and stare at the hand she's offering me. "I ain't going nowhere," she repeats as she flicks me a smile. I take her hand and we both rise into a hug. "Just…forget about all that," she laughs nervously. "I never want to hear about it," she drops the act and points at me. "Nothing from me," I laugh.

I'm circling my room in boredom and switch on the PC at my desk. With nothing much to do, I open Steam and continue my Cookie Clicker. A few mindless hours later I grow bored. Because who wouldn't? Not like it's the most action-packed thing in the world. I stare into my empty cup wishing for it to be filled but being too lazy to go do so. I push it around my mound of completed homework to the other side. Of the desk. I exhale and hold my head in boredom. I check my Winder. No traction. I check my Discord. One notification from dear old Alea, and a whole bunch of nonsense probably in the list of servers I've found myself in. "Hey," she typed. "Come over at 4." Uh-oh. "You here?" There are a few I've missed. It's nearly 5. "Um...ok," "Are you there?" "Pls come," "This is awkward." Crap. Almost an hour late, "Hey. Sorry. I'm coming," I type to her. I wait a few seconds for a response. "Hurry," she replies.

"Hey," I speak as she opens the door. She pulls me in and pushes me to the wall with her mouth over my mouth. "Mmf," I can't help but moan. She shuts the door with her leg and leans closer to my ear. "Ew," she shakes her hips in apparent discomfort. I was expecting a kiss in greeting but I suppose not. "I have someone for you," she starts. I look in confusion to the opposite wall and she goes on. "I've been thinking about that day and I think this is a nice fit. He's like you," she tells me. I feel my face redden as I come to realise the situation. She set me up. "I showed him your Winder yesterday and he said you would be perfect for me. We talked some more and I managed to bring him to meet you also. 'Meet' you. Was it wrong that I lied to him? Maybe, But this could be something new for you." She pulls her hand away and tells me to hush and just act surprised when I turn the corner. "I-I…" I struggle to think straight. "We're all in the same school, you'll be fine."

Alea leads me around the corner to her living room. We pass her parents and she leads me upstairs to her room. I've never felt more nervous than when she pushes her room door open, and he comes into view behind a few board games on her floor. Little did I know that it will all spill out tonight.

I can't help but act sassy due to my nature, but also lighten the mood with quick quips. The both of us giggle as we're put on the spot to act upon this dare. We'd just finished playing spin the bottle and Alea both dared us to do something, well, daring. "It's kind of embarrassing," Dylan starts as he chuckles nervously and scratches at his arms. "I mean," I begin responding. "I've never done anything like this. I'm still a…you know, a…" "Really?" He's surprised by the fact and crosses his arms. "Well, how lucky is she?" It takes me a while to piece together what he means but he's still under the impression I'm here to meet and eat Alea. "It's not my place to comment on her kinks but I'm not sure why she would want us to see each other's…you know…behind closed doors." I drop my face in embarrassment at the thought and he stretches and runs on the spot.

"All right," Dylan breathes in deeply and shakes off his thoughts of embarrassment. "Here," I hear him grab his shorts and pull them to his knees before shaking them off. "Only for a limited time," he laughs nervously. I shake and tremble as I feel my body going red, I look up every so slightly and open my eye in a squint between brother and baby finger. He's big.

Dylan kicks off his shorts and sits next to me at the rim of the bathtub. "You don't have to," he whispers to me. "I can just tell her that we did it, don't worry." But I have to uphold a bet. "No," I tell him. I stand, my body still shaking, and grab the sides of my shorts. I can't get a good grip, I couldn't make a fist right now. "Y-you do it," I tell him as I put my head in my hands again. "You sure?" he asks me again. I can feel he's been genuine the entire time so maybe she's right about him. It's just hard for me to come out of my shell."3," Dylan begins a countdown. "No," I tell him. "Just random. Please." "Right," he tells me.

After 10 or so seconds I feel a brush against my ass, down to my tip and pulling the back of my knee. I squint my eyes open again and catch him staring down at me. My limb. I shake in embarrassment and cover my face. I feel myself twitching. Due to my little experience, I can't help but become easily turned on. I hurry my hands down to my cock and cup both my semi and balls out of sight. "Sorry," I tell him as I open my eyes to find him absolutely captivated, and twitching as well. I try to look away but it's difficult. "Nice," he whispers, still staring. His penis rises quietly, beating slowly until I hear him breathing heavier. Dylan pushes his cock to pulsate, holding it for seconds at a time before releasing it to bounce freely. Mnn. This could be my only moment in a while. I want to try sucking.

I let my hands drop and leave it waving in front of his face. "C-Can I…?" Dylan fails to ask his question, but I assume it was something to do with the member I taunt him with. I don't want to rush things. "Sure," I feel out of breath from how embarrassed I feel. I cover my eyes with my hands and continue shaking in embarrassment. I feel my dick touch his lips on the way past and stop against them on the swing back. My breathing stays unsteady and unreliable. He opens his mouth to lick from my balls to the tip of me, covering all four inches and a half in a layer of his spit. "Mmnf," I can't help but moan in a prolonged manner. He flicks his tongue under the ridge of my head before taking it into his mouth, and sucking slowly. "Fffffuck~." My hands drop to his head and I feel my body guiding itself into him while the drool fills in my mouth. "Mnf," I pull his head back and pull my pelvis away. "Sorry," I tell him before sitting next to him. "That's okay, " he tells me. "That was great." He smiles back to me. I sigh, fill with guilt and he leans his head on my shoulder.

I pull away and slip into the bath, pulling one of his legs along with me. I feel embarrassed, sure, but I'll feel even worse having my first experience go one way. I see his giant soft and sleeping but it's still enough to make me twitch. I begin to rise and so does he when he notices my offer. He's seated on the rim with one leg in the tub, one out, and his member leaning my way. "Don't look," I tell him with a huff. "R-Right," he stammers and turns away. I feel a buildup in my mouth before I move forward and pull on his foreskin between my lips. As I've seen often in certain videos, I open wide and let the saliva slick his member, from tip to base. I then pull back to the tip, suckle on the foreskin and pull it into my mouth while pushing forward slowly. Taking his penis down my throat as much as I can, I only manage to get halfway I see before I pull back to cough and sputter and drool into the tub. "Hey, hey," he grabs my shoulders and pats my back. "You okay?" I rub my lips dry and look up at him with an awkward smile.

We dress and leave to see Alea sitting in the far corner with her eyes widened and acting clueless. "Hey," she clears her throat. "How was it?"

Dylan and I look at each other and he shrugs. "It was fine," I turn away and scratch my temple with closed eyes. "Brian's a bit shy," Dylan adds. "So you'll have to use your imagination." Alea turns red from bottom to top, covers her face and wriggles as she sits with her legs crossed near the bottle on the floor. "Oh my," she tugs on the scruff of her shirt. "Yes, don't tell me. Gross." He walks forward and joins her around the bottle, and soon enough I follow too.

It's nearing 7 pm now. We've blasted through Truth or Dare, Spin the Bottle, Cards Against Humanity and the like. It's been fun. Alea excuses herself a moment to go get snacks, and she sends us both a message as she's gone. Something along the line of "MAKE A MOVE. USE THE BED." I look up at him in surprise to see him looking back with the same face. It was like I was mirrored. That forces a giggle out of me, and I cover my smile. He shows off his attractive features and doesn't mind showing me some quick teeth before hiding his smile behind his shoulder. "Cute," he tells me. I feel myself die inside as I nearly faint and drop backwards. "T-thanks," I stutter. I don't know what she told him, but she's clearly trying to get us hooked up.

(A while of conversation)

I find myself being kissed, allowing him to do as much, and I kiss him back. My first kiss, I'm not sure what to do about it or how exactly to do it but he directs his tongue against mine and shows me the way. Dylan's leaning forward on his hands and knees to kiss me closely, while I'm sitting as stiff as I can and taking it. A long string of spit hangs between us to the floor as I slowly pull away and stare into his eyes. I feel hot, like I can't think straight, like I want to do things I shouldn't. I bounce to my feet and sit at Alea's bed, wriggling my hips and becoming more nervous as to what's next. "What's up?" Dylan asks me. For once, Alea tidied her room, I notice. She's made her bed, it looks fresh. A floral decorated beige duvet with a purple mink blanket at the lower end folded in thirds. As well as four puffy pillows along the top of her queen-sized bed. And a queen she is for this. I notice a moderate-sized chest centred atop the mink folds, and Dylan joins me at the other side of the bed. We both look at each other with the same intent and sneak the box a little closer. The key sits underneath and is made obvious when moving it. Dylan grabs the key and edges it along the slot in tease. "I've known Alea for years," he tells me. "She won't mind." He turns the key to a sudden click and I pull the lid slowly upward. Dildos, butt plugs, ties, everything you could need - and a letter written "HAVE FUN ;)". I swallow and grow unsteady. Fuck…

(Unpacking, looking at all the toys, talking about them, giggling)

(Practicing with the toys, growing hornier)

Dylan removes my watch to tie my arms to either side of the bedpost. "Mnf," I sound, excited to explore with him. "The magic word," Dylan tells me again, "and I'll let off." "Thank you," I tell him softly, surprised by the kindness and care he's shown me thus far. It'll be interesting to see what he does when he has his way. He pulls up above my necklace with his shorts absent, forgotten on the ground somewhere, and he holds my head in place as he teases me with his meat. With knees under either of my armpits, Dylan's cock rests on my chin.

After a moment of staring into each other's eyes, he smiles at me as he slips his cock under my glasses. Between those and my nose, he rushes the blood to his tip to pull the glasses from my eyes. I giggle and feel a lot more comfortable knowing he can be humorous at a time like this. We comfort each other in the awkward silence and I nuzzle at his dick while wriggling my hips again. Dylan's arm gives in and he falls back with my glasses wrapped around his penis. It hurts as his back impacts my stomach, and my breath escapes me in the instant, but I can't help but laugh at his accident. "Hey," he giggles. "Don't laugh," Dylan rolls off me and crawls back up to face me. "Don't laugh," he laughs before raising his head and staring. I'm not comfortable without my glasses, but it seems that he finds me more captivating. "Hot," he whispers. "No." I feel my heart pounding faster. "You."

I begin twitching into full mast. I've been hard all night, on and off, and he knows. Dylan kisses me deeply, holding my cheeks for the while and lowering his fingers to gently cover my throat. "Mmn," I moan as I begin moving my hips automatically. I can't help it. He drops from my lips to kiss and lick along my jawline, then my neck, then my collarbones, then my chest, then my nipples. He stays a while, bouncing between them and never keeping short of a moistness at his lips due to him keeping them wet with his tongue. "Ooh~," I go to hold his head as he explores me but my arms are held short. Dylan lowers down my stomach and bites at my shorts. He pulls them back and looks at me, and it's a look that could kill. "Ffuh," my voice fizzles. He tugs my shorts back and exposes my pulsating member. I'm still embarrassed about it but a little less that I know him. All I can think about is having it in his mouth, and having his in mine.

He slaps my 4-and-a-half inches of glory against his cheek with a duck face and pursed lips, blowing bubbles and drooling over my balls. Again, he opens wide and takes my length - I see it disappear behind his upper lip. "Fuck~!" I never could've imagined a blowjob would have me like this. I couldn't imagine what proper sex would feel like. He slops and slobs all over my prize, kissing and sucking at the sides while his glob of spit rides down the tip and over the fingers of his clasped hand around me. It leaks from his pinky to my sack and I feel it tickle smoothly over the veins of my balls. I feel it build near my asshole as time goes on, and wet the blanket underneath me. 'Girl, you're a soldier,' I think of Alea's sacrifice. I'm writhing, having a good time and he stops sucking to beat me off for seconds. Only a few seconds but they're good ones. The wetness of his mouth paired with the grip of his hand does well in turning me on as I almost cum from how his hand glides along. He holds me off as he lets go and climbs back up to his initial position. I guess he wants to have some fun.

With a knee on either side of my arms, he pressed his foreskin to my lips. He's been leaking. Excited for my first taste of semen, I lick around the head before sucking it. Dylan pulls back his foreskin as he enters it in my mouth slowly, and my tongue tingles around his precum. The taste is salty but sweet. I try to hold off any expression of slight disgust but it's bitter. I like it though. "Mnf," I moan as I drool along his cock. He bundles my hair in his hands to guide it into me, pulling at me lightly. After a while of sucking him softly, Dylan decides to pick up the pace. Faster after every few seconds, he builds up to a real quick facefucking. I feel it rushing against my tongue and his hands tighten their grip. "Uuh, fuck," I hear him moan as he rolls his eyes back while driving into me. It nears my throat but never passes too far for me.

As our sex drives both build over time, I don't mind him hitting my throat and force my lips over him until he gets the hint. I think I can take it. He throats me for the next while and I begin loving the feeling. I thought I might but I wasn't expecting to this much. Hearing his breathing, feeling the strength of his hands and pelvis doing what they will with me, seeing him in pleasure. He's checked all my boxes so far. I feel him ram my throat with his last thrust and tap on the back of my head while he keeps it in for a few seconds. He pulls out to me coughing and spitting up down my chin and falling to my neck. "Guh…" I struggle to catch my breath. "Oh fuck," I feel used and look up to him with hearts in my eyes. "You okay?" Dylan pets my head and kisses me on the cheek. "Good." He unties my wrists and flips me over, a little rough but good. He ties my hands again and I shake my ass in the air, teasing him.

Dylan readies himself behind me and spanks my ass. We both chuckle as he does it but he spanks my ass red. I feel the blood rush around my cheeks with a pleasant sting. He reaches down with a gag and slips it into my mouth, tying it around my head. I feel his member grow against mine and he pushes me down to take it. He reaches to my neck to remove my necklace and slips a belt around my neck to pull against me. Dylan drops it to my back and grabs my hair. Pulling my head up to show his dominance, he shoves it around some before pushing my face into Alea's pillow. I hear him kneeling upright and rise behind me, smacking my asscheek once more. I'm absolutely nervous but I'm sure all I practice has prepared me for this much. He presses against my hole, tight, puckered and pulsing - wet from his collection of saliva. He pushes and pushes lightly while pulling my ass down against his dick.

After only a short while of warm-ups and taking him slowly, I find myself being fucked relentlessly while breathing unsteadily between his choking and feeling his harsh punishments against my cheeks. I feel him thrust into me with all of his length and pull my hips into him. I feel him throb within me, tickling my insides and I drool profusely through the gag throughout the entirety of our session. "I'm close." Dylan hurries the ties from my hand and throws my leg around to twist me onto my back. I land halfway off the bed when he pulls me to the centre. He shoves his way into me again while looking down at me in pure bliss. "Don't fight it, that's good," he dirty-talks me. "Show me your obedience."

He runs his hand from my neck to my penis before drooling on and stroking it. I can't get over the fact that I'm being fucked. After so long of wanting and dreaming, I finally get to experience the thing. And it was worth it. I'm close also so I lower my hand and take over for him, letting his hands rest at my waist so they can pull me in. With my other hand, I strip the gag away, wanting him to hear me. "Nnf, unf, fuck," I moan with each push of his. "I'm," Dylan begins to say. I can barely finish his sentence as I let out a choppy, "Uhnnfua-a-a." Choppy because of how hard he's forcing into me now. "Fuck!" He grunts loudly as I feel him releasing his load. I can't describe a feeling quite like it - like you're being filled. After being drilled. "Nnnng," I moan as I feel myself building to climax.

Starting softly, I drool from my cocktip before shooting harshly toward myself. After the first shot, Dylan grabs my member to face him and I shoot a string upward to his face. The next following shots burst up his chest, down his stomach, and then to mine. I twitch and throb as my penis is milked and he lets go once there's nothing left. "Nnh!" I force a beat in my cock to push the rest out slowly, and it pools at my waist. "God damn," Dylan lets out, absolutely out of breath. He feels the cum struggle to be free as it leaks down my hole. He plucks his dick from me and I hear an awkward sound of bubbling from my hole as it seeps out slowly. He drops next to me and holds my hand. "That's it," he tells me. "I'm fucked." Before I know it, he falls asleep. I kiss him on the cheek and just lay there, catching my breath. With my spare hand, I grab at my phone to message Alea. It seems she's sorted everything for tonight with messages like, "Don't worry, take it for the night." "Sorry," I tell her. "Maybe you'll wanna clean these sheets." I see her typing… "No way. That's all you."

-Berserker x 💙❤Inky❤💙