Why Do I Put Myself in These Situations?

I kissed Kyle back as softly as possible, but he pulled my hips forward as he lay back on his bed, I was now straddling him my hands going threading through his hair. Kyle giggled as I pulled away, I kissed his lips again but pulled away. My face went automatically to his neck, his back arched, I kissed his neck, biting and sucking. He moaned as I nipped his neck and our hips moved. I removed his tee-shirt, and threw it on the floor, I grinned before leaving wet kisses from his neck, right down to his stomach.

"Jack..." Kyle moaned, pulling at the hem of my tee-shirt, I nodded as he threw it on the floor with his.

Kyle trailed soft kisses from my stomach to my nipple, he took it in his mouth and sucked rolling it in-between his teeth. I groaned and arched my back, he giggled and continued kissing up till be reached my lips. Kyle sat up, my legs still at either side of him, I rubbed my crotch on his, he let out a loud guttural moan. I fumbled with his belt buckle, I finally got it undone and dragged his skinny jeans off and threw them somewhere on the floor.

I rubbed his crotch through his boxer shorts, he gripped the bed sheets and bit his bottom lip. I pressed my lips too his as I rubbed harder, he moaned into my mouth, I thrust my tongue into his mouth, our tongues touched and massaged each others as our kiss got hotter, our hips began to move together in sync.

"Jack, please...I need this." Kyle whispered in my ear, before licking my earlobe and biting it.

"Ah-ah-are you sh-sh-sure?" I sputtered trying not to moan.

"Yes Jack, just fuck me." Kyle groaned impenitently.

I laughed and pushed him back onto the bed, he took the liberty to undo my jeans button with great difficulty, I laughed and tried to help him but he pushed my hands away and giggled, when Kyle finally got them off we were both sitting in our boxers.

"Kyle are you totally sure you want to do this?" I asked getting up to get a condom. "I can suck you off or give you a hand job or something if you'd prefer?"

"Jack! I want you to fuck me." Kyle yelled, "Please!"

I nodded as I went back over to his bed and taking off my boxers, he took the condom out my hand and opened it with his mouth and rolled it onto my erection, slowly. I bit my bottom lip so hard I drew blood, I moaned as his hand skimmed across my pulsating erection. Kyle took off this boxers and lay down, I positioned myself.

"You do know, this will hurt?" I whispered. "If it's too much tell me, okay? And I will stop."

Kyle squeaked as I thrust into him, he cried out in pain and dug his nails into my back. I moaned as I tried to get him used to the feeling of me being inside of him. His eyes screwed up in pain as I moved, I pulled out.

"You clearly aren't ready Kyle." I said softly. "It's alright."

"Jack, please. I want this you cock." Kyle laughed softly before kissing me. "Trust me."

I sighed and pushed back into him, he moaned this time. I looked at him He nodded for me too continue. As my thrusts built up a rhythm we moaned, I put my face in his neck and his went on my shoulder, our bodies slick with sweat, I moaned as a pleasure built up inside the pit of my stomach, It shook down from my stomach to my hips as my hips jerked forward and Kyle arched his back and moaned as he connected our lips together and our tongues touched and danced together. I cried out as I came, soon Kyle came shortly afterward, I looked down at him and grinned, pulling out and wrapping the condom up and throwing it in the garbage bin beside his bed.

"How was it?" I asked kissing him.

"Not so bad.." he giggled and blushed.