The Night I Became a Woman… or Maybe a Slut?

Matt and I were both 18, dating for three months. He was tall, handsome, athletic, and always horny around me. We were both virgins, but we’d been talking about losing our virginities together for weeks. We’d done a lot of fooling around, like heavy making out, him playing with my big boobs, fingering, handjobs and blowjobs, then we finally decided to do it after a party.

It was a house party hosted by one of Matt’s friends, so I wanted to look really hot for my boyfriend. I spent forever getting ready. I did my makeup sultry and sexy, smoky blue eyes, long fake lashes, and glossy pink lip gloss that made my lips look extra pouty. I straightened my long brown hair so it fell smooth and shiny down my back.

I wore a tight baby-pink crop top that was way too small for my heavy chest. It was super low-cut, showing inviting cleavage, with the black lace of my push-up bra peeking out. My big boobs were practically spilling. I paired it with a short black mini skirt that barely covered my round ass, and black heels. I felt like a naughty tease, and I knew Matt was going to lose it.

At the party, we drank, danced, and made out. I got pretty tipsy, giggly, warm, and super horny. Matt couldn’t keep his hands off me. He kept grabbing my ass and squeezing my tits through my top while we made out in the corner. By the time we left the party, I was feeling bold and ready to finally have sex for the very first time.

We went back to his dad’s house to do it before his dad got home from the pub. As soon as we got inside, Matt pushed me up against the wall and started kissing me hard, his hands all over my body, telling me how badly he wanted me, shaking with excitement. I was nervous but also really turned on.

“You sure you wanna do this, Kate?” my boyfriend asked.

“Yeah, I’m ready,” I purred.

He practically pulled me upstairs to his bedroom, both of us laughing and stumbling because of the alcohol and excitement. Once he’d closed the door, things got intense fast. He frantically removed my crop top, then fumbled with my bra before finally getting it off, letting my heavy 32E bust spill out.

“I know I say it every time I see them, but fuck me your tits are perfect,” he groaned, full of awe. He then buried his face right between them, sucking on my sensitive nipples and squeezing my big boobs together while I moaned.

I helped him take his shirt off, then we both struggled with his jeans. His cock sprang out, rock hard and throbbing. He reached into his nightstand drawer and pulled out a condom. I could tell he was nervous because his hands were shaking as he tore open the foil wrapper and rolled the thin latex down his dick. It took him a couple of attempts before it was on properly.

He pushed me back onto the bed, flipped my skirt up, and pulled my black thong down my legs, exposing my plump, shaven, mound. I was soaking wet. He got between my thick thighs, rubbed the head of his sheathed cock against my virgin pussy a few times, then pushed inside me slowly, groaning long and desperate.

It hurt. A sharp, burning stretch as a hard cock entered me for the first time. I gasped and gripped his shoulders tight, wincing but enjoying it. I trusted it would quickly feel amazing. It did.

“Oh fuck… you’re so tight,” my boyfriend moaned, his voice strained like he was trying so hard not to cum right away from the excitement. He kept pushing until he was all the way in, then started thrusting too eagerly and a little clumsy, full of raw energy.

My big boobs bounced wildly with every stroke. Matt couldn’t stop staring at them, groping them as he fucked me in the missionary position. I was moaning loud, the mix of pain and pleasure making my head spin and my pussy even wetter. I had no regrets.

But then Matt’s breathing got really ragged, and he suddenly groaned that he was going to cum, after only five or six minutes. He thrust a few more times, then lunged into me, burying his cock to the hilt before filling the condom. I wasn’t angry or frustrated, with him, more secretly disappointed.

Even though it was over too quickly and I didn’t cum, it was still special because it was with the guy I loved. Matt pulled me close for a cuddle, but within minutes he was fast asleep, snoring in my ear, while I remained wide awake. In need of some water, I quietly slipped out of his bed, pulled on one of his t-shirts that came down just past my ass, and left his bedroom.

On the landing, I bumped straight into Tony, Matt’s dad, grinning right at me. He must have just gotten back from the pub, I assumed. He was a big, rugged guy in his late 40s. I liked him, but right then he looked menacing. I froze, suddenly very aware that I was literally only wearing a t-shirt, and my nipples were poking against the fabric.

He looked me up and down slowly, then gave a low, dirty chuckle as he leaned in a bit closer and whispered with a mocking smirk, “He didn’t last very long, did he? I listened to all five minutes of it. Looks like he left you bewildered and unsatisfied. Tragic.”

My face went bright red. I didn’t know what to say as Tony looked past me into the bedroom at Matt snoring. He shook his head and looked genuinely disappointed in his son’s performance.

“Don’t worry, Kate. Boys his age are always like that. All mouth and too excitable. You deserve a real man,” he said, grabbing my wrist firmly. “Come in here with me. I’ll treat you right.”

“Tony,” I whispered harshly in shock, my heart pounding. But he pulled me into his bedroom and closed the door behind us. “Are you crazy? I can’t be in here. This is insane. Let me go.”

Tony put me with my back up against the wall, looking me up and down again, hungrily, his eyes lingering on my busty chest and my hard nipples poking through the thin t-shirt.

“Don’t get shy now, Kate,” he said in a low, rough voice. “We both know what a little tease you are. Always coming into my house looking like sex on legs… your big fucking tits spilling out of every top and dress. Parading that body around, begging to be noticed.”

“Tony…” I gasped. “No… no I don’t.”

“Yes you do, and I fucking love it,” he growled, stepping closer and grabbing the hem of his sons t-shirt. “God, I’ve been dying to see your big tits bare.”

He pulled the t-shirt up and then over my head in one swift motion, exposing my bust. It bounced free, heavy and full at my boyfriends dad. He groaned and immediately cupped them in his large hands, squeezing them firmly.

“You’re built for this. A body like yours isn’t meant for quick fumbling with boys. It’s meant to be used properly. Tits bouncing. Your young pussy filled by a real man, fucked and bred deep.”

His words made my face burn with shame and fresh arousal at the same time. Before I could respond, he kissed me. It was deep, confident, and commanding. His tongue explored my mouth while his hands continued kneading my heavy breasts, thumbs brushing over my sensitive nipples. He broke the kiss only to lower his head and devour them, sucking hard on one nipple, then the other, licking, biting and slapping my soft flesh lovelessly, so they jiggled for his amusement.

I moaned inside my boyfriends dads bedroom, while my boyfriend slept like a baby next door. Matt had never played with my tits like that before, so rough yet so skilled. It sent jolts of electricity straight to my pussy. I was soaked, trying to catch my breath.

“I thought you’d like that,” Tony grinned. “Girls with big tits always do.”

He pushed me onto my back on his bed and spread my legs wide. When he lowered his mouth to my soaked pussy, I gasped. His tongue was experienced and relentless, long, slow licks up my slit, then focused circles on my clit while he slid two thick fingers inside me. I had to bite my lip to stay quiet. The pleasure built so fast, I had an intense orgasm within minutes.

“Oh fuck,” I trembled, clamping my thighs tightly around his head.

I was still trembling when he stood up, stripped off his clothes, and climbed between my legs. His cock was thick and veiny. He rubbed the bare head up and down my slippery folds, teasing.

“Condom?” I whispered weakly.

He shook his head, eyes dark with lust. “No. I’m going to feel every inch of this tight little pussy. You’re going to take me raw, Kate. Are you on the pill?”

“Yes, but…” I worried.

“Good girl, though it would be more fun and dangerous if you weren’t,” he said, pushing inside me slowly.

The stretch was so intense. Tony was noticeably thicker than Matt. Once he was fully buried, he lifted my legs over his shoulders and folded me in half. He then started fucking me with slow, deep strokes, grinding against me on every thrust. The angle hit something deep, making me moan uncontrollably, my toes to curl and my pussy to clench.

“You feeling that, Kate?” he growled quietly. “This is how a real man fucks a girl like you. You’re a sexy little slut… you just don’t know it yet. But you will once I’ve finished ruining your cunt.”

His dominance was hot and sharp, the pleasure overwhelming. I moaned loudly and repeatedly with every deep thrust of his cock, while my big boobs bounced between us. Tony kept the slow, deliberate pace until I felt another orgasm building perfectly.

“Oh fuck, I’m gonna cum…” I whimpered.

He didn’t speed up. He just kept fucking me deep and steady until I shattered. My pussy clenched tightly around his bare cock, as waves of intense pleasure washed over me. Only then did he let go. He started pounding me harder with powerful, deeper thrusts that made the bed creak and my tits bounce wildly.

Dirty, wet slapping sounds filled the room as I came again, even harder this time, my body shaking uncontrollably as I tried to muffle my cries. I didn’t think of anything else but the pleasure.

Then Tony grunted. “Fuck… take my load like the good little slut you are.”

He buried himself as deep as possible and came hard, flooding my pussy with thick, hot spurts of cum. I could feel every pulse as he filled me up completely. He then stayed inside me for a few minutes, letting me feel the warmth spreading deep inside as I lay there panting, sweaty, and satisfied.

The mixed emotions hit me hard once the orgasm haze faded. Intense guilt because I’d just let my boyfriend’s dad fuck me bareback and cum inside while he slept nearby, but also this deep, glowing satisfaction and thrill from being truly fucked properly.

“Go on, get yourself back to Matt’s room,” Tony instructed, pulling out and rolling over.

I said nothing and quietly pulled Matt’s t-shirt back on. Tony watched me with a smug little smirk and lit a cigarette as I slipped out of his room and crept back into my boyfriends room and bed. He was still snoring but had rolled over, the used condom on the floor.

I remained awake for half an hour, feeling Tony’s warm cum slowly leaking out of me onto my thighs and then the bedsheet. My pussy felt sore, used, and wonderfully satisfied, but the guilt... I had betrayed Matt in the worst way on the same night we lost our virginities. I felt dirty and ashamed, yet strangely empowered.

That night changed me. I rubbed my clit slowly to another, gentler orgasm, and tasted Tony’s cum on my fingers, mixed with my juices, knowing I wanted to feel that dominance over me again. Matt was the first guy to ever put his cock inside me, but his dad was the first guy to fill me with warm cum.