Page 55 of The Biggest Win


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Plus, I haven’t been with anyone in a very long time. But now is not the time to play the numbers game.

She nods. I nod. A silent promise made. I lean down and take her lips, swirling my hips, my cock searching for her opening.

“Tell me if I hurt you. I’ll try to go slow but babe, I’ve never gone bareback before, so I don’t know how much control I’ll have.”

“Just take me. I won’t break.”

My heart screams for this woman. I lean down and lick a nipple. Then take the other. I reach down and feel her wetness covering me. She arches into me, and I pinch her clit.

“Oh god...”

I line myself up and slowly push into her. Our eyes meet and I watch for any tells.

“It feels good. Keep going.”

“Your pussy is incredible.” My head drops to her chest again. She wraps her legs tighter, pulling me in. I push through all the way and we both moan as she adjusts to my size.

“You okay?”

“Perfect. Now fuck me, Jackson.”

An animalistic groan comes from my throat, and I take her lips oncemore, while I rock my hips. Damn, why did I wait so long with this woman? We could have been doing this all along. Her little moans motivate me, and I’ve never felt a connection like what we have. It’s better than any sex I’ve ever had.

Is this whatthe onefeels like?

I still my thoughts.

The one?

What am I saying?

“Hey? Where’d ya go?” She turns my head towards her.

“Right here, babe. I’m right here.”

“You got quiet. Where’s my dirty talk?” she smirks.

“Youdolike it.”

I kiss her bottom lip, then bite it gently.

“I love being inside you.” She shivers. I travel down, taking her nipple in my mouth and grazing it with my teeth. “Fucking you has never felt so right.” She moans, and I lean back and grab her leg, pulling it up tighter to my hip, increasing my speed and changing angles.

“Oh, Jackson, that’s so good. Harder. More.”

“Fuck, I love your body.” I play with her clit and she squeezes me tight. “Woman. Your pussy is unbelievable, keep squeezing me. I can feel you’re getting close. You want to come?” She moans and I slow down. She whimpers.

“Don’t stop. Jackson!”

I give her a smug grin and grab her other leg, wrapping it around my hip, tilting her up so I can plunge deep inside. “Touch yourself.” I thrust inside and she cries out.

“Louder. I want to hear you, Chess. Do it. Touch your clit while I’m fucking you.” She reaches down and just the sight of her hand where we are joined, her tits bouncing with every thrust, her other hand pinches her nipple, it’s enough to end me right here.

“I’m trying to hold off, but watching you is killing me.” She licks her lips and smiles at me. She fucking smiles. And I’m lost to her.

“Come now. Come with me.” I increase my tempo and I’m about three pumps away from blowing. She tightens up and cries out my name. “Jackson! Oh, I’m coming! Jackson!” she cries again, and I explode inside her. We ride our orgasms out together, and it’s amazing.

I collapse on top of her, breathing heavily.