My Best Friend’s Son

I turned the key in the lock as Matt stood behind me, shifting his balance from one side to the other in nervous movement. His parents, and thus my best friend Kayla, were on a weekend trip for their anniversary. I’ve known Kayla since junior year in high school, back when we were both still shy and curious, when we were supposed to be in our rebellious teenage phases. Matt is nineteen now, which is crazy to think about when I remember that I was there the day he was born, holding his mother’s hand as his father was out of the country on a business trip.

So, it was no shock, that when he’d accidentally locked himself out of the house, he’d called me. I live barely fifteen minutes away and have always had a spare key to the house, and even if I was a bit annoyed by the late hour, I would never let him stand outside with nowhere to go.

“Thank you so much Miss Wilson, I really don’t know what I was thinking. I was just heading out and then the second I closed the door I couldn’t find my keys; I just don’t know where my head’s at, I’m never this forgetful I swear.” He awkwardly explained himself, probably feeling a bit guilty seeing my state, knowing I was about to head to bed. I was simply wearing my underwear, a nightgown, and a long jacket on top of it, I knew there wouldn’t be anyone out on the street this late, it’s a very polite neighborhood after all.

“Don’t you worry dear; lord knows I wasn’t doing anything important. Come on, get in, you can’t be comfortable out there.”

He followed me inside and shook off his jacket which he hung by the door, before kicking off his shoes and heading into the living room. I followed him as he plopped down on the couch to say my goodbyes.

“Okay sweetheart, I’ll be going now then, don’t you forget your keys again okay? Be safe and sleep well.” I kissed his forehead and turned around to take my leave when I felt a strong hand grip my wrist.

“Wait! Can’t you stay? It’s so quiet now, and you’re so much more fun than my parents to hang out with.” Blatant flattery or not, it was working. I chuckled and threw off my jacket and put it on the kitchen counter before setting my shoes beside it. I walked over to where Matt had now turned on the TV to sit next to him.

“You sure know how to charm a woman.” He looked at me with a smile and crept closer to me, his side touching mine.

“Have you seen this one? It’s apparently really old school, right up your alley.” I laughed as I lightly hit him on the shoulder.

“Jerk, I’m not that old.”

“You’re the same age as my mom.”

“And your mom is in the prime of her life.” I settled back down again and felt my face flush as I realized I had actually seen the movie before, back when it was still playing in the theaters even.

“Sure, Miss Wilson, whatever you say.” Matt had a grin on his face as he turned towards the screen again, body not moving away from mine.

When I said I’d seen the movie before, I didn’t mean it was a good one though. The plot was boring and the acting was bad, I was half-dozed off not even a quarter of the way in. I contemplated closing my eyes for a bit when I suddenly felt a hand on my thigh. I suddenly froze as I looked over to Matt, only to see that his eyes hadn’t wandered from the scene in front of him, seemingly enraptured by the main character’s monologue.

I decided to not think too much of it and leaned back into the couch, trying to focus on what was happening on screen. It worked for a couple of minutes before I felt the hand start to move. At first, it seemed innocent enough, just repositioning himself to be more comfortable, but then it just started creeping up higher and higher, until his pinky finger was resting over where my thigh met my crotch. I knew I shouldn’t, but I could feel myself start to get aroused. Something about the way that it felt so secret and sneaky as if it was something we weren’t supposed to do. To be fair, it had been a rather long time since I’d been intimate with anyone, the pent-up energy is bound to boil over at some point right?

Apparently, he took my silence as a sign to continue, because now he was slipping his fingers in between my thighs, rubbing me over the fabric of my nightgown, barely concealing the heat that was radiating from my most private parts. Oh god, I could feel myself getting wet, that wasn’t supposed to happen right? When your best friend’s teenage son started rubbing your crotch on the couch?

His administrations got rougher, more confident, and this time when I looked over, he was staring right at me. I couldn’t help it, the heat in his gaze was enough to make me melt. He suddenly pressed down, and I couldn’t suppress the gasp that left me.

“Matt-” He continued rubbing his fingers in circles over where my clit would be if only those last two layers weren’t in the way.

“You really think I wouldn’t notice? You coming up here wearing basically nothing but lingerie? You’re shameless.” His other hand came up to undo the string around my waist. Letting the nightgown fall as he pushed it to the side, cupping my breasts before gently pinching my nipple between his fingers. I couldn’t help but moan as I turned into putty under his hands.

“I wasn’t- I didn’t mean to-” I cut myself off with a groan as he slipped his hand inside my panties, giving me the skin-on-skin contact I so craved.

‘No? Does that mean you don’t want this?” He pulled his hand away, wiping it down on his jeans as I realized for the first time that he was still completely dressed as I was sitting in nothing but my underwear just above my knees on the leather couch. He looked at me expectantly when I whined at the loss of his fingers. He was expecting an answer.

I didn’t know what to say, knowing that I shouldn’t, but god if I didn’t want to.

So instead of verbally replying I surged forward and captured his mouth in a kiss, which he eagerly returned. There was nothing sweet about it, it was all teeth and tongue as if he was trying to devour me whole, I would probably let him. I let him manhandle me into his lap and now I felt the bulge of his erection press against me. I ground down and swallowed the groan Matt let out my covering his lips with mine again.

After that, there was no more teasing. He tore off my panties, almost ripping them in the process, as I undid his belt and fumbled with his button. Eventually, he helped me and pulled off his own jeans and underwear, letting his dick spring free. It was bigger than I expected, but not in a crazy way. He was thick, uncut and the tip of his head peaked out from underneath his foreskin. I wanted nothing more than to feel it inside me.

I wrapped my hand around it, sliding down to cup his balls as I resisted the urge to get on my knees to worship it with my tongue. He didn’t let me continue for long though, soon enough he shifted to lay down on his back, with my things straddling him. My aching pussy inches away from his cock. Matt hadn’t even taken his shirt off yet, still, I couldn’t bring myself to care, he didn’t seem to either. He grabbed my hips tightly and moved me, so I was hovering over him. I grabbed him to help place the head at my entrance before I felt him move me down, encasing his cock in my tight heat.

“Oh my god!” I let out a shout as he groaned and immediately thrusted up further into me. I could feel him stretching me open, God it felt so good. I was fucking my best friend’s son and I was loving it.

I reached down with one hand to rub my clit as he continued with his brutal pace inside of me. I knew I wouldn’t last long. I rubbed circles over the little bud of nerves as I felt him hit deep inside me, filling me up.

He let go of my hips with one of his hands to come up and caress my breasts again.

“Fuck Miss Wilson, you feel so good, so tight around me.” He pinched my nipple hard at the same time he thrust up into me and I couldn’t contain myself anymore. I cried out as I came, convulsing and clenching on Matt’s dick as he continued to fuck into me.

“Fuck! Fuck Miss Wilson, I’m gonna cum. I’m gonna cum inside you!” I continued to let him use my body to let him chase his own pleasure. I felt his thrusts growing irregular and his body go taut. And then within seconds I felt the hot spilling of liquid inside of me, as he filled me up with his cum. It seemed to keep going forever, but eventually, he collapsed back down and helped me lay down on top of him after he slid out. I could feel his cum start to leak out of me, and he seemed to sense it. His fingers trailed down my back only to push his fingers into my pussy to push the cum back in again.

I stuffed my face in his neck to muffle my moans. He didn’t stop, but I was too sensitive, his fingers so big and rough, it was too much.

“Matt…” I tried to roll off, but my strength had left me. Thankfully he seemed to understand what I wanted because he sat up and helped me do the same. He smiled at me as he handed me my panties which I put back on again, followed by my nightgown to cover my now sweat-covered body.

I looked at Matt’s face as he grinned at me, moving to put on his own underwear, not caring about his pants.

“So… Would you wanna do that again sometime?” The smug expression on his face made me want to hit him and then I suddenly came back to my senses.

“Oh my god, Matt! I’ve gotta go, I can’t believe I- Oh my god what about Kayla! I’m going, I’ll see you sometime else, goodbye.” I rushed to put on my shoes and jacket as I quickly made my way to the front door, hearing his footsteps rush after me.

“Miss Wilson wait!” I didn’t stick around to hear what he had to say, I got into my car and pulled out of the driveway without a second thought, determined to get home as fast as I could.

By the time I was in my own bedroom again it was late into the night, and I was exhausted. I laid down preparing to go to bed in the hope that this was all a dream, when I heard my phone buzz with a notification.

Matt Anderson (Kayla’s boy)

You know, my parents are gone again in three weeks, dad has a business trip he wanted mom to come with