As I was slowly jacking him off with my left hand and finger fucking his butt with my right hand I watched him lay his chest down on the mattress and arch his back trying to force my finger deeper up his ass. This is what I was waiting for he was starting to get into it now, “Is it starting to feel better Mark?” I asked.
Whimpering he answered, “OHH YEAH I CAN FEEL YOUR FINGER IN MY BUTTHOLE, IT FEELS GOOD STEVE!!!!!”
“Your asshole feels good wrapped around my finger Mark, I can’t wait until I get my cock in you!!!!” I teased.
“OOHHH YEAH!!!!” Was all he moaned.
I fingered his ass for a few more minutes giving him time to loosen up and get a little more turned on before popping his cherry. It was going to hurt and the hornier he was would help him with the pain. As I pulled my finger from his asshole I could see that it had definitely come into contact with some of his shit. I had a couple of pretty thick dark brown smears on my finger. I smiled to myself and wiped my finger across his right butt cheek leaving a nice brown streak across his ass check.
Reaching down with my left hand I picked up the tube of K Y and started lubing my cock jacking myself off working the lube up and down my shaft. Mark had turned his head back around and was trying to watch me over his shoulder, “You are really going to fuck me up the ass aren’t you?” He hesitantly asked.
“Yes Mark I am really going to fuck you up the ass!!!!” I answered.
I took my right hand and laid it on his back and began rubbing his back trying to soothe him a little as I got my cock ready to penetrate his little virgin butthole. As I rubbed his back I began rubbing my cock up and down his butt crack working it in between his cheeks letting it push on his hole as I rubbed over it. Each time my cock touched his asshole he would flinch and nervously utter, “Uhh, UUM!!!”
I very slowly and gradually pushed a little harder each time I rubbed over his hole until I could feel the head of my cock starting to open him up a little. The more he opened up, the more I worked my cock into his asshole. He had turned his head back around and dropped it down onto the mattress in anticipation of what was going to happen.
I had started rubbing his back with both hands now, just letting my cock rest inside the ring of his asshole. I very nonchalantly placed both my hands over his shoulders gripping them gently but yet firmly and began pulling him back onto my cock. “OOHH, OOH MY BUTT OHH FUCK IT’S GOING TO HURT!!!!!” He squealed as he felt my cock trying to penetrate his sphincter.
“It’s going to hurt for a few minutes and then it’ll get better!!!!” I warned him as continued pulling him back onto me keeping steady pressure against his sphincter waiting for it to relax and open up.
“OH PLEASE STEVE DON’T HURT ME!!!!” He squealed.
I continued pulling him back onto me not forcing him, just holding him against my cock giving his body time to adjust and open up, “I am not going to hurt you, try to relax and let me in your ass!!!” I told him trying to calm him down, he was starting to tense up and tighten his asshole from the pain he was feeling in his sphincter.
“Mark I want you to try and bear down like you are going to take a shit!!!” “I know it sounds gross but try, it’ll help you!!!” I said as I leaned forward over his back still making sure to keep my cock pressed up against his asshole.
I waited until I heard him grunt then I rolled my hips forward pushing my cock further into his sphincter this time it went through and into his rectum. He wasn’t expecting to be penetrated like that all I heard was, “UUUHHH, OWWWW!!!!” “OH MY GOD MY ASSHOLE IS BURNING BAD PLEASE, PLEASE STOP!!!!!”
“Shh, Shhhh, you’ll be fine in a few minutes just relax I know it hurts!!!!” I said trying to soothe him.
“Oh my God my asshole hurts, it fucking burns!!!!” He whimpered all the while twisting his hips and trying to pull away from me. I still had my hands on his shoulders pulling him back against me pulling him onto my cock like before the only difference was now my cock was buried all the way up his rectum. I could feel his asshole clenching my cock as he squirmed and struggled trying to away from my invading member.
The warmth inside his rectum was incredible it felt like my cock was wrapped in warm gooey meat. I knew my cock was pushed up into his thick creamy shit and that was adding to sensations I was feeling. I also knew once I started actually fucking him I wouldn’t last long. I could already feel myself getting close to cuming just from putting it in his ass. As he started to calm down I gently wiggled my hips just enough to move my cock inside of him, when he felt my cock moving he tensed up and his butthole clenched again “UHH, UGH!!!!” He grunted twice then stopped dropping his head back down as if he was ready to take some more.
This time when I felt him relax his asshole I pulled back a little bit and waited for a few seconds then pushed back in. He didn’t make any sounds just stayed with his head down. I pulled back again a little further than before, waited a second or two then pushed back up into his rectum this time a little PPPFFF!! Escape his asshole making him groan, “Uuh I’m sorry I didn’t mean too!!”
“It’s alright it’s part of getting ass fucked!!” I answered calmly hoping to keep him relaxed and calmed down hoping that he wouldn’t tense up and clench again. I was ready, I just had to be patient with my young neighbor and give him time. I was planning on literally fucking the shit out him and I didn’t want to hurt to him the sight of him kneeling on the bed with his ass stuck up in the air and my boner buried up his young little hole was making it very hard to control myself.
“My balls ache Steve, My balls ache and I feel like I need to go to bathroom, you know what I mean Steve?”
“I know Mark, I know how you are feeling, you feel like you need to shit and you want to cum!!!!”
“It feels weird I want you to make it feel better, PLEASE STEVE!!!” My young was whimpering and grunting as he was struggling to accept my cock.
“I will Mark, I will make it feel better, your rectum feels really nice and warm you feel good Mark!!!”
“I feel good Steve?” “My ass feels good for you?”
“Yes Mark your ass feels really nice to me!!!” I answered softly as I began to rock my hips back and forth very gently.
“OOHHH GOD YOUR GOING TO FUCK ME NOW!!!”
“YES I AM GOING TO FUCK YOUR BUTTHOLE NOW, RELAX AND TAKE MY COCK!!!”
“YES SIR I WILL TRY!!!” He groaned as he curled his hands into fists and gripped the sheets.
As I began to very slowly and gently pumping his butt he arched his back and pushed himself back against me. Feeling him pushing against me I started moving a little faster gently picking up the rhythm, “Reach back between your legs and jack off for me Mark, jack off while I fuck you up the ass!!!”
“Yes Sir I will try?” “I still feel like I need to poop!!!” He half moaned half whimpered.
“I know, it’s my cock in your rectum making you feel like that, don’t worry you won’t shit, not yet!!!” I soothingly answered.