My Milf System-Chapter 155. I want you

(Asher’s POV)

I don’t know if it was the alcohol or the tension that had been building between us for months, but the second we stepped into my room, something changed. The moment Anna threw her bra away and stood before me in nothing but her snug yoga shorts, I felt the last bit of restraint snap inside me. She looked absolutely irresistible.

Her titties weren’t as large as her mother’s, but they were perfect, firm, perky and so damn alluring. She pushed me onto the bed and climbed on top of me, showering me with hungry kisses. But just as suddenly, she stopped. Her thighs still straddling me, she stared deep into my eyes with a flicker of hesitation.

"Can... I see it?" she asked softly.

I knew exactly just what she wanted to see, so l gave her a nod as permission for her to go ahead. My cock bounced up when she pulled my pants and underwear down my legs.

She gasped. "It’s so...big!"

I chuckled. "It’s just a little above average."

She stared at it for a moment, then asked softly, "Does it hurt?"

"Not really. Maybe just a little," I murmured.

Without another word, she reached out and wrapped her fingers around my dick. Her hands were small, and they didn’t quite close around my huge cock. The sight made me throb even harder.

She glanced up with that breathtaking smile. "Does it feel good when I touch you like this?"

I couldn’t speak. I just nodded, heart pounding.

She shifted, and slept beside me, her left hand still stroking my cock, her small, sweet lips coming back to mine and her tongue once again dancing with mine. I reached my hand down and wrapped my hand around hers on my cock, then began teaching her how to jerk me off. I moaned under the kiss, the soft press of her breasts against me slightly overwhelming.

I’d never thought I’d end up like this with Anna. I only ever wanted to protect her. But now, as her touch pushed me to the brink, I felt myself losing control.

I broke the kiss, breathless. "Anna... stop. If you keep going, I won’t be able to hold back."

She knelt beside me, eyes unwavering. "I told you... I want to do this. I want to go all the way."

I hesitated. "But... your first time should be with someone you love. It’s something special."

Her smile was soft. "That’s exactly why I want it to be you, Ash. Because I love you."

I swallowed hard, silent, not sure what to say to her confession. She sat down on the bed, eyes locked on me and with one finger, she pulled the leg of her shorts to the side. She didn’t even have any panties on, making me wonder if she came prepared for this. I gazed upon her delicate, small, and red lips of her pristine pussy and gulped again.

"Do you like it?" She asked coyly, curiously watching my reaction.

"You’re... perfect," I breathed, staring in awe.

She trembled under my gaze but didn’t stop. Her fingers moved to her virgin slit with the hand that wasn’t holding her shorts to the side, awkwardly touching her tiny little clit with two of her fingers. Then, she closed her eyes, moving the tips of her fingers slowly up and down the nub, while I watched it in amusement.

"That’s beautiful..." I said under my breath, the sight getting me extremely horny. I didn’t waste time to move toward her, gently easing her onto her back as I slid her shorts off, leaving her now completely naked. I stared at her for a while, admiring her soft, gentle body that clearly showed me it had never been touched by another man except me. My eyes lowered all the way down to her shaved, clean pussy. I couldn’t resist leaning in to kiss her there, then ran my tongue along her slit, tasting her hot juices. She groaned softly as l pressed my face deeper, flicking my tongue between her folds until l found her clit again.

Anna jumped and her hands slapped down onto the bed on either side of her hips as my tongue lapped at her clit.

"Oh! Ash..!" She cried out and spread her thighs even wider for me.

I smiled at her reaction, knowing she was enjoying my mouth job. I started to lick and suck at that tiny little nub between her puffy pussy lips.

I flicked my tongue around and over her clit harder and faster, working it up and down on either side of the sensitive little nub. All the while, l watched her face, studying her to see what she seemed to like the most.

I wrapped my lips around her clit and suckled at it gently at first and then a little harder, alternating the suckling with flicks of my tongue against the little nub until suddenly she seemed to tense up. I knew what was about to happen.

I redoubled my efforts, my tongue lashing and suckling faster over that sensitive little nub, determined to drive her higher. Suddenly, something squirted from her, splashing hot against my bare chest and dripping down my chin. My cock throbbed painfully, straining as if it might split in two from how hard I was, her intoxicating scent growing thicker, sweeter with every desperate, wet burst of release pouring from her. It was wild, raw—like she was reaching a real orgasm for the very first time, her body surrendering completely under my touch.

She groaned as l pulled my mouth away from her, watching her pussy glistening.

Positioning myself in between her legs, which she promptly opened wider for me, I took my hard member in hand, and started rubbing its tip up and down her little slit. Another squirt of her juice burst right out of that opening and sprayed across my cock, drawing a long groan of hunger from my lips.

"As you may already know, the first time hurts... but I’ll try to be as gentle as I can." I muttered.

She closed her eyes, nodding. "I trust you."

With that, l rubbed her soaked pussy lips one last time before l began pushing the head of my cock in very slowly, back and forth, trying to be as careful and gentle as I could, gently as she deserved it to be. Anna’s entrance was as tight as I could imagine, if not even more. Even though she was naturally lubricated, she was still very tight, and her body kept resisting my penetration just a little.

I didn’t want to rush, though. She clenched her teeth, and the discomfort of it was all over her pretty face. Until, suddenly, the head of my dick went inside of her.

"Urgh..." she let out a painful cry, squeezing her eyes shut.

I stopped moving, holding myself in place. Leaning in, I kissed Anna’s forehead, then her lips, her shoulders, her collarbone—anywhere I could reach—as she breathed heavily, trying to endure the slow, careful intrusion of my thick dick into her tight entrance. Part of me ached to look down, to see how my rod was stretching that tiny, virgin pussy of hers, but making her feel loved in that moment mattered more than any selfish urge. I wanted her to know this was about her, not about dominance. After a while, I rested my forehead gently against hers and whispered, "Can I start moving, baby?"

She breathed heavily before nodding "yes". So, I pushed a little deeper into her, watching as her cute face twisted in pain, a soft moan escaping her lips. Then again. She was unbelievably tight—tighter than anything I’d ever felt before.

"A-Ash..." she whimpered, her voice trembling with the edge of tears. "I feel l-like you’re a-about to rip me open..."

"Do you want me to stop?" I asked, my voice husky, barely able to keep still as I moved in and out just a bit, drawing another grimace from her.

Her watery eyes met mine, and I held my breath, waiting. For a moment, she just looked at me. Then, with a shaky nod, she whispered,

"No... I w-want it too..."

"What do you want, baby?" I murmured.

"I... I want you to fuck me," she said, her voice trembling yet full of desire.

"Really?" I asked, slowly sliding in deeper—until I felt something stop me.

We both knew what it was. Her final barrier. And to spare her the drawn-out pain, it had to be broken in one swift move.

Gripping her thighs gently but firmly, I kissed her one last time... then l thrusted forward, all at once, pushing past it.

She grimaced with another cry, but l was already inside. I stopped gently for a while, and let her get used to the pain.

After that, l began fucking her no longer virgin pussy, slowly at first, then picking up momentum, plunging in and out. My groin slapped against her little butt and my testicles slapped against her clit and vulva.

"Oh... f-uck...fuck!!" I heard her grumble, gripping the sheets tighter.

After a few minutes of thrusting, l pulled all the way out. Just when she thought maybe l was done, l made her lie down on her back and raise her legs so far back that her knees rested on her little boobs before l began thrusting her from the back. My thrusts were even deeper in this position.

I could feel tension building in her pelvis like a spring being wound and craving release. Instinctively, she reached her hand down and started rubbing her clit erotically as my thrusts continued like the piston of a race car nearing the finish line. Suddenly, her little body was racked by a powerful spasm centered between her legs. Her vagina quivered uncontrollably and clamped down on my penis like a vise. She wailed, starting low in her throat, her voice rapidly rising to a soprano squeal of ecstasy as l continued to make rapid rabbit fucks into her pussy, her orgasm ripping through her, shaking violently beneath me. Her voice cracked as she called my name, her fingers digging into my skin as she shuddered through the wave of pleasure.

This was also too much for me. I felt a sweet sensation engulf my balls. Throwing my head back, l let out a loud grunt, my cock erupting inside her, spewing my sex juice into the deepest reaches of her vaginal walls.

We both collapsed on the bed, breathless, tangled in each other, our bodies still trembling from the intensity of it all. I held her close, my arms wrapping around her protectively as she buried her face in my chest, still catching her breath, her heartbeat racing.

"I... love you Ash." She whispered. "You’re my everything."

And that’s when the post-nut clarity guilt hit me like lightning.

TBC