It had been two days since I had sucked my stepdad Bill’s cock and I have not stopped thinking about him. I was home alone after college catching up on my workload when I heard a key in the front door, he was home from work (a construction site not too far away from our house. All of a sudden I heard footsteps traveling up the stairs pausing outside my room. My heart was beating so fast. The door handle turned and Bill walked in, grinning like I had never seen before. Fresh from the construction site, he was wearing dirty sweatpants a tight scruffy orange tshirt and his high-visibility jacket. It was the first time I had seen him in his uniform since he caught me, I always used to jerk off so I could concentrate on school work. He walked over to my desk “hey! What are you doing tonight? Got plans or are you just doing work?” He smiled. “Not really I just have a paper to finish” I replied. I saw his hand reach over and started to massage his cock through his sweatpants.
“Jack I have been thinking a lot lately and I would like to show you something, it’s in mine and your mums room”. I could see the anticipation in his eyes. “Um ok…” I replied, curious as to what it could be. I followed Bill into his bedroom, sitting down on the bed. I watched Bill walk around to his bedside cabinet, opening the door and pulling out a bottle. He turned to me “Now, I bought this for your mother and I but she has never been keen on using it. It’s anal lube and I wondered if it is something that you would like to use with me. I mean this stuff isn’t cheap so I would love to at least try it once?”.
I looked up at him. Did he just ask to fuck me? “I don’t know Bill, I’m really tight and I haven’t lost my virginity yet” I really wanted to do it but the thought of having anal for the first time made me nervous. “It’s ok if you don’t want to but I promise I will be gentle” he winked, climbing onto the bed. “You know what I’m not even going to pretend I haven’t been fantasising about this for a long time, let’s do it”. “There’s a good boy, now sit on daddy’s lap”. I couldn’t wipe the smile off of my face as I climbed onto his lap. I started grinding on his crotch, feeling his cock pressing up against my ass. I felt his massive hands grabbed hold of my cheeks. “Is daddy exited?” I teased. “I think you know the answer to that” he winked. I felt his hands move up to the waistband of my gym shorts. He edged them down slowly until all that was left was my bare ass, pulling by briefs down with them. We looked back each other, both as exited for what was to come. I got up pulling my shorts and underwear off, quickly dumping them on the floor before teasing down his sweatpants to his calves. I sat on top of his underwear grinding my cheeks between his shaft, feeling it grow to the size I had worshipped. “Fuck, you know just how to get me hard son” biting his lip and with that he grabbed the bottle of lube beside him, coating his fingers in the clear thick liquid. He moved his finger around the lips of my hole. I could not help but moan “uhhh daddy”, I saw his expression change with a grin creeping across is face. I could feel his cock throbbing under me, I was rock solid by this point. I couldn’t pretend that he wasn’t turning me on.
Suddenly I felt the tip of his finger penetrating my ass. I winced at the pain/shock. “It’s ok boy, once we get you loosened up you will be riding my cock in no time” whilst moving the tip of his finger around the rim of my ass before rubbing more lube on my boy pussy. I could feel my anus relaxing tightening around his finger. “Right son, one deep breath in”. I did as I was told, filling my lungs with air. As I released he pushed his whole finger up there. “Oh shit” I yelled. At first all I felt was discomfort before my body relaxed once again as his thick, manly finger loosened my hole before adding another. After fingering my ass for a good few minutes, he pulled out, reaching into his underwear to take out his cock. I watched him slather it in lube, making eye contact with me as he massaged his cock. It turned me on so much I dribbled, before I could stop myself the saliva landed on his tip. “Is daddy making you horny while he rubs his fat cock son?” He asked smugly. “Yes daddy, I want your dick inside me. Use me as your little fag and don’t hold back”. I don’t know what came over me but it must have worked because the expression on his face only grew more intense.
I moved to sit in front of his cock again, Bill took the opportunity to rub his cock across the rim of my ass, moistening it before sliding it into my hole. “Fuuuckk! Your so thick” I moaned. Moments after he grabbed my waist, forcing his cock deep inside my ass with my rim now touching the base of his shaft. It was painful at first but I knew that if I wanted to carry on having sex with Bill, I would have to put in a good first performance. Squatting on his cock I moved up and down, stroking his hairy muscles as I went, grinding on his ball bag every so often. He started moaning, a manly deep growl. Before long he was controlling my movement holding my ass in order to bounce it on his cock making me go deep each time. “listen here boy, you need to be used like the little whore I know you are. Now put your legs over my shoulder and get ready to be pounded until daddy says so”.
I complied with his orders, he shuffled to the edge of the bed and lifted me up. Once again he used his hands to support me, keeping my body as close to his chest as possible. Without warning, he started smashing my ass against the base of his cock, massaging my prostate vigorously. This was everything I had dreamed it would be, maybe even better. Treating me as if I was a sex doll, the rough pounding was almost too much… just the right amount. He pressed my back against the wall before repeating the pounding session. Barely able to hold me due to the intense pleasure of my tight hole, the wall steadied his movements as he penetrated as far as his cock would allow. “Take my fucking cock boy, your mine now so you better get used to this” he managed to demand in between his deep moans.
It wasn’t long before hot jets of cum filled my ass. He quickly transferred me to the bed where he could lay on top of me while his orgasm continued to leave him out of breath. His cock still firmly implanted deep inside my hole. “Fuck son, you have the best fucking pussy a man could ever wish for” he smiled, elated after his orgasm that seemed to have waited a lifetime to be released. After dismounting, Bill became the “responsible” stepdad I knew before we started hooking up… well not quite. “You go get cleaned up and then get back to work on that paper, if you don’t get an A then my cum will make a reappearance in your ass” he winked. “Yes sir I understand” I grinned before limping my way to the shower. He fucked me so hard I couldn’t even walk straight, I may just have to get a D on that paper.
