Chapter 4
Hey, folks, I’m gonna tell you about this wild thing that happened to me when I ended up hooking up with a femboy. First off, I gotta make it clear: I’ve always been straight as an arrow, never had any interest in guys. But that night, I slipped up – and damn, I gotta admit, it was one of the best times I’ve ever had. Who hasn’t, right? This story’s from my point of view, so if it comes off a bit rough around the edges, sorry in advance. Let’s dive in.
In prep school, my class had at least 150 people, all kinds – different beliefs, colors, orientations. We were always trying to flirt with the girls, but between practice tests and endless study hours, there was hardly ever time – and when there was, we were wiped out. Of course, every now and then we’d skip classes to sneak out. It was on one of those that I met this group of four girls who always hung with a little gay dude in tow. He was a guy who dressed in this super unique way, all dolled up, delicate like a girl. He always kept to himself, but I’d catch him side-eyeing me sometimes.
I never dug guys, but I never treated anyone like shit either. We studied together, swapped notes on stuff we didn’t get, and he never tried anything with me. At most, he’d toss out a joke or two when he was with the girls, but it was all light, chill vibes – I always handled it fine.
In a chat with that group, I mentioned I was stressed ‘cause my roommate couldn’t cover his share of the bills and headed back to his folks’ place. As soon as they heard I had the apartment to myself, the girls got hyped right away and started planning to come over Saturday for some drinks. Of course I was stoked – a bunch of chicks at my place, something was bound to go down for me. The catch was, my spot was a total dump – barely any furniture, I slept on a mattress on the floor, but my dad covered it so I could stay close to the prep school, and I’m grateful for that.
But as Saturday rolled around, I noticed something off: all that excitement from the girls just fizzled out. They confirmed they’d show, swore they were coming, but in the group chat, they sounded less and less into it. On the day itself, they all ghosted. A total bullshit flake.
I spent Saturday glued to my phone, waiting for a text, some confirmation, but the group went dead silent. I was pretty much convinced I’d been stood up when, right on time, the intercom buzzed. The doorman said one of the girls was coming up. My first thought: if even one shows, it’s a win.
I rushed to open the door, kinda pumped, but the second I saw who it was, my buzz killed dead. Him. The femboy.
He just stood there, adjusting his bag on his shoulder, like he was waiting for me to say something first. The way he looked at me, all uncertain, sizing up my reaction, already gave me a weird vibe. Out of all the girls in class, he had the most style in how he dressed – anyone looking from afar would wonder if he was some butch chick, you know?
“Hey, bro, you good?” His voice came out a bit higher than usual, almost hiding a thread of nerves.
“All good. You?”
He took a deep breath, tried an awkward smile.
“I’m cool…”
But he wasn’t. The way he rubbed the back of his neck, avoided looking me straight in the eye, gave it away.
“Where’re the girls?” I blurted, trying to figure out what the fuck was going on.
He fiddled with his phone, glanced at the screen without real interest, then tossed out the answer like he was winging it.
“Oh… they should be here soon…”
But the hesitation, the pause before answering, made me clock it right away. He was lying. And lying like shit.
“Come on in, man…”
He walked in casual, like he’d been there before. Headed straight to the kitchen, opened the fridge, stashed the beers he’d brought, but didn’t touch them. We cracked open mine, which were ice cold.
While he rambled about random shit, I just watched. I’d already pieced it together. The girls weren’t showing. Obvious as hell. They must’ve set something up, schemed to leave the gay dude alone with me. But honestly, I wasn’t pissed at all. He was part of the crew, my buddy just like them.
What cracked me up was the act he was putting on. Even with the lie plain as day, he kept up the charade, playing dumb like someone might ring the bell any second.
I took a swig of my beer, eyed him sideways, and cut the bullshit:
“Dude, cut it out. Just fess up.”
He blinked fast, his glass shaking a little in his hand before he let out this fake-ass laugh, all forced.
“Fess up what?” His voice dripped with over-the-top drama, eyes faking outrage.
“The girls set you up to come here alone, right?”
He clutched his chest, all dramatic, like I’d accused him of murder.
“Oh, that’s mean of you to say…”
Well, I was in my own place, no one would know. And if he blabbed? I’d deny it hard. In the end, a blowjob’s a blowjob, and I wasn’t turning down some head just ‘cause it was from him.
I looked at him with a sly grin, my hand sliding slow to the bulge in my pants, making it crystal what was on my mind. He clocked it right away, his eyes lighting up with anticipation.
“Look, too bad I don’t go for guys…” I teased.
He didn’t miss a beat, tilting his head a bit, biting the corner of his lip before answering, his voice sweet, almost syrupy:
“But I can be a girl, if you want…”
That made me laugh. His ballsiness amused me. I leaned forward, like I was sizing up the offer.
“You suck dick like one?”
The way he flashed that little smirk told me the answer before he even spoke.
“Better… Wanna see?”
I ran my tongue over my lips, feeling the mix of thrill and playfulness.
“Bro, just one thing… I don’t kiss guys on the mouth.”
He rolled his eyes, pouting all cute and fake, but the challenge came quick, loaded with mischief.
“Oh, you homophobe… Let’s make a deal? If you like it at the end, you’ll give me the biggest kiss of your life.”
I busted out laughing. Idiot. A blowjob was just a blowjob. I could easily say it wasn’t that great and fuck off. But tongue kissing? With a dude? No way in hell. That wasn’t happening.
He took a slow pull from his beer, tilting his head slightly while fixing his hair, tucking it behind in this natural, almost rehearsed move. His eyes, full of intent, scanned me up and down, like he already knew where this was headed.
And then he crawled.
The moves were weirdly hot, slow, like a cat stalking its prey. He stopped between my legs, knees on the floor, breath picking up a notch. Face down, delicate features, lips parted like he was about to beg for something. But he didn’t say a word. Just stayed there, staring at me in a way that made my cock throb harder in my shorts.
This was new, forbidden, and maybe that’s why it had me so fucking turned on.
I kept the beer in hand, pretending I had it together when I was hanging by a thread. I let myself soak in that moment, the tension building between us. And then, without a word, I just nodded, barely noticeable.
He got it instantly.
The little giggle he let out was pure glee, eyes sparkling like he’d just unwrapped a gift. No hesitation, he slid his hands up my thigh, tracing slow to the waistband of my shorts. His fingers worked with insane skill, popping the button, easing the zipper, and in one smooth pull, he yanked down both shorts and boxers, freeing my rock-hard, pulsing cock right in front of him.
He let out a low sigh, eyes devouring every inch. And then, with obvious hunger, he leaned in, lips eager for what was next.
He didn’t hold back. The second my cock was out, he licked his lips, like he was tasting the sight before the feel. His gaze, full of naughty intent, flicked up to mine, like waiting for one last go-ahead. I just leaned back on the couch, beer still in hand, making it clear he had free rein.
His delicate fingers wrapped around my base first, exploring slow, feeling every throb of my arousal. He gripped firm, no rush, sliding his warm palm along the length while his mouth inched closer. The first touch was pure tease: the tip of his wet tongue tracing a lazy path from base to head, taking his sweet time. My body reacted instantly, and he noticed, smirking before going on.
His lips parted and the wet heat swallowed me in a flash. He took me in slow, inch by inch, tongue swirling around with crazy skill. The warmth, the suction, the soft glide… it was fucking perfect. He sucked with precision, switching between deep, slow pulls and quicker thrusts that stole my breath.
His hands didn’t idle. While his mouth worked, one trailed down my thighs, scratching lightly, the other steady at the base, stroking in sync with his lips. He let out these muffled moans, like he was lost in it, like getting off on this was as big a deal as making me feel good.
I wasn’t faking calm anymore. My hands ended up in his hair, gripping tight, guiding the rhythm, feeling that hot mouth take me deeper with every bob. The wet slurps filled the room, mixed with my heavy breathing and his low moans.
He looked up at me from below, eyes shining with lust, like he was hooked on this, dying to see me lose it completely. And when he picked up speed, sucking harder, tongue flicking the tip between sucks, I knew I wasn’t lasting long.
I felt the climax building, body tensing, breath hitching. He sensed it, letting out a low moan, still sucking greedy, not letting up. Hollowed cheeks, perfect rhythm, total surrender.
And then I came, hard, deep in his throat. And he didn’t stop. Swallowed every drop, sucking through the last spasms, eyes locked on mine, hand firm at my base, like he wanted to drag it out forever.
When he finally pulled off, tongue sliding slow as he backed away, he grinned all satisfied, wiping his mouth with a finger before licking it clean, teasing as hell.
“So… what do you think?” he whispered, still breathless, looking at me like he already knew. “Worth a kiss?”
I laughed, still catching my breath. He knew how to play. But tongue kiss? I needed more.
“Turn that ass around,” I ordered, voice steady, full of anticipation.
He didn’t hesitate. With the same ease like he knew the drill, he grabbed a small bottle from his bag. Then, no more words needed, he got on all fours on the couch.
What happened next was pure instinct. Before I could even say shit, he arched up, offering the most obscene, inviting view I’d ever seen. His ass was… different. Still had that male build, but damn, I’d never seen anything so smooth, so flawless. Skin like silk, not a hair, not a blemish. A tiny black thong barely covered anything, holding his balls and dick, which were half-hard, forming this pink, swollen lump of pure horniness.
But it was his hole that hooked me for real.
Almost colorless, so pale and soft it looked carved. Round shape, fine smooth folds, the kind of sight that demands you stare. And he knew it.
He squirted the lube into his hands and started spreading it over his body, sliding the slick stuff over every curve, making his skin glisten all tempting. He did it slow, eyes never leaving mine. And then, with a boldness that made my cock twitch harder, he focused on his hole, fingers gliding light, teasing the rim before spreading himself open for me.
He stayed like that, in that porn-star pose, holding his cheeks apart, showing me everything without a shred of shame. But it was his eyes that got me most. He wanted my reaction. He wanted to know what this was doing to me.
And fuck, it was doing a lot.
I’d already cum, but my dick stayed hard, rigid, ready for this guy who challenged me with every move, every look. The way he exposed himself, like begging for more without words… pure fucking heat.
That’s when he lifted his hips a bit more, tossed his hair back, and hit me with a half-smile. His voice came soft, laced with naughtiness:
“Can I just ask one little thing?”
I figured it was some plea for gentleness, some delicate request. I nodded, expecting anything… but not what came next.
“Go slow when you fuck me?” I teased, my voice rough with want.
He laughed, shaking his head, fingers still holding his ass open for me.
“No, babe… the opposite. Fuck me hard. If I say no, you take it as yes, got it?”
That threw me. The guts, the surrender, the way he wanted it raw, no holds barred. My cock throbbed hard, the lust ramping up.
I knelt behind him, hands gripping his slim waist firm. The sight of that arched ass, spread for me, slick with the lube he’d slathered on, had me losing it. I dragged the tip of my cock over his tight entrance, feeling the hot skin, the muscle clenching at the slightest touch.
“Ready for this?” My voice came out gravelly, thick with desire.
He just moaned in response, low and needy, pushing his hips back to offer more. I gripped his waist tighter and, no more waiting, thrust in.
The squeeze was insane. His hole gave way slow, the heat pulling me in like a tight, scorching grip that sucked my cock deeper with wild hunger. He gasped loud, fingers digging into the couch cushions, body shaking under me.
“Fuck…” He moaned, voice breaking.
I didn’t give him time to adjust. Remembering what he’d asked, I slammed in hard, feeling the tight resistance break under my push. Our skin slapped together in a wet smack, and he let out a long groan, nails clawing the couch as his body molded to mine. The grip was unreal. Every inch of me wrapped in that suffocating heat, the involuntary spasms dragging me deeper, like he wanted to lock me in. I found my rhythm, pounding deep, feeling him open up with every thrust.
He moaned, rocking back, begging for more. And I gave it. Held his waist harder, slamming forceful, my balls smacking against his. The impacts made this hot, hollow sound, that direct skin-on-skin contact keeping me even harder. Feeling our balls touch on every stroke was an extra kick, a different pressure that cranked the intensity.
“Yeah… fuck… yeah…” He gasped out, breathless.
I didn’t ease up. I railed deep, harder, faster, until he was totally gone, arms giving out under him. He collapsed onto the couch, but I yanked him back by the hips, keeping him up, fucking relentless, his moans getting louder, more desperate.
The couch creaked, our sweaty skin stuck together, the wet slaps of each thrust filling the room with our heavy breaths, muffled groans, the repeated smack of balls on balls.
I felt my peak hitting. The pleasure surging like a massive wave, about to drown me.
“You’re gonna cum, aren’t you?” He whispered, panting, voice full of filth.
I grabbed his hair, twisting my fingers in the soft strands of his ponytail, yanking his head back to make him look at me. He grinned, lips swollen, eyes blazing with want.
And then, without thinking, without fighting it, without giving a damn, I pulled his mouth to mine.
The kiss was starving, desperate. Our tongues crashed in a perfect lock, a moan slipping from him as I claimed him fully, deepening it while my cock pulsed inside him.
And then I came again. Deep, hard, spasms ripping through me with pleasure as he moaned into my mouth, his whole body quaking under mine.
When I finally let go of his hair, he laughed against my lips, way too satisfied.
I pulled back a bit, still huffing for air, and he licked his lips, all teasing.
“So… it was just a blowjob, huh?”
I laughed, wiping the sweat from my face.
Son of a bitch.