Trying too hard 2
My name is John.
And I’m a gay man.
But I don’t call myself that. I don’t really identify with gay people. Or straight people for that matter. Gender just seemed so limiting. I’ve always been a quiet guy. I kept to myself through my youth until I met Randy. That’s when everything changed. In the terms of what life meant and what my focus would be for the rest of my life. That’s what this story is all about. In the first chapter I recalled how I grew up, how I met Randy, and how sex became a big part of life.
Recently Randy and I began masturbating together and each other. In the last weeks he stuck his finger in my ass when I came. It was amazing. Then two fingers. Finally the head of his cock which hurt really bad. Randy got mad when I made him stop. Yesterday he apologized and gave me a special gift. For a special friend. It was a small butt plug that looks like a small dick. It was call the ‘Raging Hard-on.’ This morning I was experimenting with it when my mom burst into my room. I was able to keep it hidden from her but it ended up firmly in place through the ride to school, the walk to class, and my whole first period lecture hall. Needless to say it’s been a wild week so far.
Having the Raging Hard-on between my cheeks for so long had eased much of the pain and it became both curious and exciting. When it was first inserted it stung. Then the first time it went all in I was shocked but I couldn’t let anyone know, especially my mom as she drove us to school. At school I was planning to take it out ASAP but was caught by the bell and ended up in lecture hall. In a front seat. With the ‘Raging Hard-on’ buried deep. For the entire hour and a half.
At the end of the lecture I remember grinding my ass into my chair when my teacher’s face came into focus right in front of me. His lips were moving as I tried to focus on what he was saying. My ears were ringing so loud I couldn’t hear. That’s when I realized the class was over and people were leaving. But my teacher was still talking to me. I couldn’t hear his words. I just smiled and nodded hiding my condition. The condition of riding the Raging Hard-on for my first time.
The teacher finally let me leave after a stern lecture about paying attention in class and not day dreaming my life away. Luckily that had allowed most of the class to file out and I was able to grunt and moan my way to my feet without being noticed. Heading out I was reminded of how big the Raging Hard-on was. Sitting still I had gotten used to its size. But now it came back to life. The invader was rocking back and forth between my cheeks with each stride. I felt that itch returning. The sensations started rising inside me again.
Luckily my next unit was study hall and I could take my time moving. I was wobbling down the empty hallway having little twitches, finally on my way to the bathroom when Randy appeared. I smiled wide when I saw him and stood up tightening my ass. The butt plug caused me to shake. I was hoping he would be proud of my efforts. However that’s not what happened. After looking me over he recognized something was going on. He knew the look on my face and he could tell I was excited. But things were different. I was obviously dazed. He asked what was up. I cleared my throat and quickly explained the morning’s mishap.
My friend got a devilish grin on his face, “Really!?” Then he raised his eyebrows and looked around to make sure we were alone. I opened my jacket indicating my groin. He looked down and saw the wet spot that had soaked through the front of my pants from repeated deposits of pre-cum. I told him, sitting in class with the ‘special gift’ between my cheeks had caused me to get hard over and over. A weak frown formed from his devilish grin. I saw the change and just knew. He scolded me, “I thought we were going to check it out together. Why didn’t you wait for me?” I felt the pit of my stomach turn and I dropped my head as he went on.
He was right. I should have waited for him. It was a gift from him. He said we would do it together. I nodded my head in agreement. Suddenly Randy grabbed my arm forcefully at the elbow and led me out the doors where we headed across campus. His shaming, coupled with that evil smile made me wonder what he was going to do with me. Was he going to punish me for not waiting? And how would he punish me? I felt guilty. It made me flush. He had a firm grip on my arm. His voice was urgent, “Come on, I want to check it out.” then he looked back at me with that devilish grin back on his face, “Besides you owe me. Remember?” That’s when I realized what his intentions really were.
That was a relief. I thought he was going to be mad again and it scared me. Instead he wanted to jerk off and after this morning, I was ready. I wanted to find out what it would feel like ejaculating with the Raging Hard-on in. I hadn’t forgotten about my debt either and was so excited I followed without hesitation. Randy urged me on as we picked up speed, “Does it feel good when you walk faster?” This morning I could barely walk. Now that Randy was there it was exciting. The faster I went the slicker the plug in my ass got, “Yes.” I muttered with a squeak as another spark jolted through me.
It was true, my ass was getting more excited with each step. The pain was almost completely gone and I could really feel it wiggle around deep inside which made my dick get plump and sensitive again. The shaft of the Raging Hard-on was rolling back and forth across the root of my dick as I walked. It reminded me of how his fingers felt wiggling inside me. It caused me to feel little sparks, like little orgasms every few steps. The pain had turned to tingling and surging all around my groin. The farther we walked the more excited and dazed I got.
In what seemed like forever we finally arrived at a single stall bathroom near the teacher’s lounge. My face was flushing, my dick was throbbing and my ass was buzzing as Randy pushed me through the doorway. I fell against the sink trying to hold myself up as my weak legs shook. A buzzing rushed over me in waves. It started in my balls and ran backwards up my dick into me ass right to where the head of the Raging Hard-on wiggled. There it flooded out to my face, hands and feet. It was different and my body liked it. My excitement flushed as I tried to regain my composure. Dazed and in a fog I barely recognized the room. My ass was pulsing and twitching. I heard the door lock behind me.
Inside he said, “I feel excited too. Let’s jerk each other off.” He dropped his pants to reveal his already stiffening dick. I was excited and dazed from the brisk walk and just reached out blindly and started stroking his hard shaft just the way he liked it. It felt heavy in my hands, thick warm and alive. I looked at it and thought about its size and what he had said about needing a little practice. The ‘Raging Hard-on’ wasn’t that big. His dick still looked too big and my knees almost buckled thinking what might happen behind locked doors. I thought to myself, I’m going to need a lot more practice.
He loosened my pants and let them drop. Then he slid my briefs off my hips and let them hang just bellow my butt. My dick drooped but it was twitching and oozing after the long morning of self abuse. The cold air made my nipples tighten but I hardly noticed. My attention was focused on his hot meat. I owed him and I wasn’t afraid of paying my debts. Randy’s dick felt good in my hand as I stood there half naked stroking it with the ‘Raging Hard-on’ in my ass. I could feel my butt tighten around the shaft as he touched my dick.
As he started to play with my dick he put his other hand on the butt plug and began teasing it. My body shook. I looked in the mirror and watched both of our dicks as we played. My body was jerking and twitching from my heightened sensitivity. His face lit up as he looked it over. Randy pushed his hand down my dick until he pressed against my pubic bone, “Bend over so I can see the butt plug.”
I was already starting to bend over from the sensations down there. Especially with one of his hands pressing against my pubic bone and the other teasing the ‘Raging Hard-on.’ Then he pulled at the plug letting it slide out part way. The veins on it’s sides rippled across my sensitive hole. Oh what a feeling! My body shook and when he pushed it back in I groaned and bent over further. He smiled, “Pull your cheeks apart. I want to watch it.” I was so willing I did exactly what he said without thinking.
I let go of his dick and grabbed my cheeks to pull them open. Then I looked in the mirror to watch his expression. He stared at the butt plug as he moved it in and out all while squeezing my dick. I could feel the ridges as they slid through my weak quivering hole. It was a very different feeling from sitting on it for two hours. He smiled as he played with it. His stiff dick was still sticking up in the air. The tip glistened and my mind was beginning to wonder what it would feel like after a little practice. His hips thrust forward as he pushed the plug in mimicking the movement. I watched as he fucked the air while he pumped the ‘Raging Hard-on’ in and out of me.
I could almost imagine his dick in there instead. His big shaft fucking my poor tight hole. My face flushed as I watched him continue fucking the air while the ‘special gift’ fucked my hole. After a few times I began moving my hips with the rhythm. Fantasizing about how it might feel. It felt crazy. The sensations were different than anything I had ever felt before. My young body was heaving to the new experiences.
That’s when Randy urged, “Let me try putting my cock in there again. I really think you’re going to like it better this time.” That was the first time he called his dick a cock. My body was so excited I wanted it. My mind on the other hand reeled as I looked at his cock and thought about what he was saying, “But its so big.” Randy just chuckled. His voice continued, “I know you’ll like it. It’s going to feel amazing. Trust me.” I did trust him and I wanted him to be happy. Just the thought of it caused me to whine.
He pulled the plug all the way out then shoved it back in. It took my breath away. The veins on the plug rippled across my hole causing me to shake and groan. I felt flush and my legs went weak. All the while he was stroking my dick in time. His words echoed in my mind as my body indulged in these new sensations, ‘you’re gong to like it better this time. Trust me.’ But I was still uncertain of his request, fearful of the pain I felt the last time.
I was conflicted. It really hurt the last time. But now it felt so good and I didn’t want him to be disappointed with me, so I agreed. Randy told me to spit on my hand and lube up his cock. Yes, lube is good I thought to myself. I had real evidence of that fact. I did as he said remembering how the lube helped this morning. My mouth was dry but my saliva was thick and slippery. I spread my spit around his cock-head and stroked its length. It didn’t take long to lube up his long shaft to make it slick.
Then he pulled the plug out and quickly pushed his cock against my red ring. My tender hole wasn’t giving in easily. It pressed against my hole and slowly split my cheeks. He watched us in the mirror with an evil grin. His cock head was much bigger than the plug and I winced as the head passed through my tight ring. Randy pulled back out after seeing me wince, “Maybe this is too much for you…” That was just the head. My mind snapped into focus. Maybe it was too much. I was questioning the whole day’s events.
But after an hour and a half period of riding the ‘Raging Hard-on’ I was willing and ready for this. I didn’t want him to stop now. I had to try, “Wait.” I wanted to feel the real thing. He was watching me intently in the mirror. He made me feel inadequate. I pleaded with him not to stop, “Your cock is just so big. But…” I looked at him over my shoulder, “…don’t stop.” After this morning my ass needed something to replace the missing plug. Something real.
So he pushed the head against my ass hole and I bent forward. Once again it popped in. My body jerked and my face flushed again. After a short pause he pulled it back out then pushed it back in again. I could feel the head as it passed in and out. It was big but knowing it was Randy’s cock I tried to smile. I watched us in the mirror. I could see his desire building. He was sighing each time the head sunk in, “Yeah. That feels good. Don’t you think so?” I could feel myself relaxing with each pop. The pain was easing and I felt proud to take his cock. I nodded, “Yeah.”
The size was a big challenge. I was still fearful of the pain it was causing. But I knew what I had to do to make him happy. So I thought about how it really felt. It felt different this time. Better. The stretching wasn’t as painful as before. Riding the butt plug had numbed me a little. The head slid in and out of me hole before pressing in. I could feel it filling me up. He watched my face in the mirror as it softened from pain to pleasure. It didn’t sting nearly as much now and his cock felt better than the plug. The shaft squeezed in as Randy gently pushed. I could feel the head of his cock slide to the depth of the butt plug. Right where the current itch was. He looked at me in the mirror, “There. Just as deep as the butt plug. That wasn’t so bad was it.”
My eyes rolled in my head, “Ugh! Yeah.” Then he let it slide out a little. Randy put his hands on my hips and slid his cock in to the same depth and grunted, “That’s the real thing.” Yes, it was. My knees knocked together as I shook knowing it was his very real, very big cock. I remembered stroking it with my hand and how big is was, how heavy and stiff it felt. Now that big heavy stiff cock was in my ass. It excited me and I was determined to get used to it for him. He pumped it into me a couple times as he found his rhythm. The feeling of his shaft slipping in and out was becoming erotic. The real thing was so much more exciting than the plastic plug.
“Doesn’t that feel better?” he said as the movement settled in. It did. My voice was as weak as my legs, “Yeah.” I whimpered. He kept pumping, “My cock is almost halfway in.” That made me think. It still hurt a little but it was half of his real cock. This morning I would never have thought that before lunch I would be able to take that much of his big cock up my ass. It made me feel proud and special. He was my special friend. I followed his motion as he pumped. The feeling of his cock sliding in and out was distracting. Suddenly he let go of my hips and stopped saying, “Now you do it.”
My brain was drooling like my mouth. I know what he said but it was foggy. I didn’t know what he meant exactly. I rocked weakly. His cock felt stuck. I just stood there flushed and excited feeling his cock pulsing with his heartbeat inside me. I wanted more but I wasn’t sure what he wanted. Then he pulled on my dick and slid his out of my hole a little. When he stroked down on my dick he pushed his cock back into my ass. “Doesn’t that feel good? You do it now.” Then he held perfectly still.
Now I think I understood, he wanted me to jerk him off with my butt. His body leaned back slightly. He let the shaft slide out most of the way. I could feel his cock near the edge and when he stroked my dick I pushed back on his hard cock letting it slide into my butt under my control. The head returned to that itchy spot. It felt so good. Much better than the butt plug. I squeezed my cheeks around his cock when it got deep. Not that I could or wanted to stop it. But I could feel it inside me. His cock was throbbing, my brain was numb.
I relaxed my cheeks and rocked back and forth in short motions stroking his cock with my ass. It was so strange. But it felt so good. Controlling the depth increased my confidence. So, I was cautious not to take too much. It was already deep enough. And the rhythm was very satisfying as I stroked his cock between my cheeks. He wasn’t moving except to occasionally stroke my sensitive dick. Randy grunted, “Can you squeeze it tighter?”
My mind was lost on the feeling of his shaft sliding in and out. His words just passed right by my ears. Then he spanked me on the ass, “Come on. Grip my cock.” Instinctively I tightened down on his shaft as my butt stroked it. It felt slippery and alive, “Does that feel better?” I asked weakly. This made him happy, “Yeah, just like that. Doesn’t that feel good?” Oh yeah. He was right when he had said it before, I liked it. I picked up speed and was lost in the sensations. I did this for just a short while before suddenly and most amazingly cumming, “Fuck! Yes!”
My load squirted farther than ever and it felt incredible. Randy covered my mouth and pumping his cock in me as I kept cumming, “Quiet! Someone will hear you.” He kept pumping his cock at that depth as I ejaculated. It was deeper then I had ever felt before. But I didn’t care. At that moment I was cumming the best I’d had to date. Before I finished cumming he pulled out leaving me empty, “That was only halfway in. Imagine what we could do.” I looked over my shoulder at him with wanting in my eyes and his hand still over my mouth. He had that evil grin on his face again.
He kept his gag hold on my mouth and pulled me close to his face, “You weren’t supposed to cum so soon, I didn’t get to cum yet.” he whispered in my ear as he scolded me. “You should have waited until I was ready to cum too.” My face was already red but it must have gotten redder when he scolded me. It was one of Randy’s rules; ‘if you came and the other didn’t, you had do all the work to jerk them off solo the next time.’
I already owed him and I wanted to please him. He’d taught me so many exciting, sexual things. This was over the top amazing. “Now we’ll have to wait. Classes will start again soon.” he said as he quickly wiped himself, put his cock back into his pants and zipped them up. I felt guilty, empty and wanted to be absolved. “Let me try again.” I said breathlessly hoping to do it again soon.
He looked disappointed but hopeful, “If you want to try again, ride your bike over to my house tonight. Then, if I’m feeling up to it we can try again.” The rest of the school day was clouded by my twitching ass and thoughts of what would happen next. The Raging Hard-on in my jacket pocket was tempting but after cumming with Randy’s cock in my ass, now I wanted the real thing. Suddenly I was completely focused on anal sex. I didn’t know it then but Randy had been grooming me to be his anal fuck buddy. I remembered the last thing he said, “And put the butt plug in before you do.” I was going willingly.
I wanted to please Randy so much. Partly because of all he’d shown me and now because it felt so good to cum with his cock in my ass. I had to do it again. But also because he just shamed me in the bathroom. I felt so guilty that as soon as we finished dinner that night I put the Raging Hard-on back in and rode my bicycle over to his house just like he had directed. I ignored the pain knowing it was only temporary.
The ride was quite exciting as I had never ridden my bike with a butt plug in before. It was different than riding in the car. The vibrations of the bicycle seat reached deep inside. Like quick little fucking strokes. I almost lost control a dozen times as every little crack in the road shook me to my core. Peddling my bike really got me going and I longed for Randy’s very real cock. My ass was stinging in a good way and my heart was pounding with excitement as I turned into his driveway.
When I arrived at Randy’s house my face was red and flush. I was catching my breath and bracing myself against the side of the house when the door opened. He grinned that devilish grin and invited me in. He followed me watching my strange waddle and unsteady knees. The bike ride over had left me weak and sensitive to the movement of the Raging Hard-on. I wiggled and wobbled through the entryway. My ass kept tightening and quivering every other step causing me to twitch and shake.
Across the living room sat Randy’s mom reading a book. I was glad she ignored us. My face still flushed with the sight of her there. I felt embarrassed and vulnerable not knowing if she had a clue as to what Randy and I were really doing. I said ‘Hi’ to her as we crossed the room trying to act normal. She nodded and looked over her book. Randy indicated we were going to catch up on some experiments downstairs. She didn’t respond but returned to her reading.
Usually we would just go to his room and study, hang out or play with each other, but this time we headed towards the back staircase. He directed me downstairs. It felt different knowing what we were about to do. I wanted his cock instead of the ‘Raging Hard-on’ in my ass. Right there in Randy’s house with his mother just upstairs. His brother had made a private room in the basement where he used to bring girls, smoke pot and listen to Rock and Roll music away from his mother’s prying eyes. He called it ‘the Vault.’ It was secure, soundproof and private.
Tonight Randy took me down there directly and locked the door behind us with a solid clunk. “You owe me. You know that, right?” Now I was having a sudden sense of servitude. I eagerly shook my head. Yes. He looked me over and I just stared at him. “I’m not excited yet.” My heart sunk. I wanted it bad. But I didn’t know where to start. My mind was blank expect for the thought of his cock replacing the butt plug.
Then he said, “Take off your clothes and show me the butt plug.” I did so without a thought and standing there naked I turned around to pull my cheeks apart exposing the ‘special gift’ he had given me buried to the hilt. “Nice. Now help me take my clothes off.” I knew it was my turn to do all the work and make him cum. It felt different this time. I never needed to undress him before and I fumbled with the buttons on his shirt as my excitement grew. Then I loosened his pants and slid my hand inside.
When I did I found his cock getting thick already. My hand embraced his growing shaft. It had never felt so alive before. I explored it’s shape and straightened him as I slid off all his clothes until we were both naked. When I looked at his profile I was reminded that his cock was bigger than mine. It may not all fit in, but I was determined to try. I wiggled my ass thinking about it. “You know the rule. You came and I didn’t get to, so you have to make me cum.” I shook my head eagerly again.
“Stroke my cock.” he said standing there in front of me. I did as he requested. We’d done this enough that I knew exactly what he liked. He smiled and grunted, “That feels good. I always like the way you do that. Do you like stroking my cock?” My mind was in a daze as I tried to focus on what I was doing. It felt warm and heavy, smooth and alive. “Yes.” I watched his cock get hard and shiny in my hands. It made me wonder how it would feel this time.
Randy moaned, “Did you like the way it felt in your ass today?” My legs went weak as I remembered his cock in my ass and how hard I came. He quickly turned me so he could put his hand on the plug and wiggled it around. I started moving up and down, “Yes.” I wasn’t looking at his face, just his cock as it glided through my fingers. This morning was incredible and I shook as he wiggled the ‘special gift.’
He pointed to a jar of lube, “That is for you. Take it home so it will be there if you need it.” Then he told me to try it on his cock. I put some on his shaft and let it slip through my hand. Randy groaned, “Use both hands.” I did as he said and he started moving the butt plug in and out of my hot wet hole. His big shaft was now slippery and hard. He wasn’t touching my dick as I focused on his needs. That was the rule. I was so ready.
Randy’s cock began to ooze from the tip, “Are you ready to pay your debt?” I knew what he meant and nodding my head I let go of his cock and turned around. I wasn’t sure how to get started and looked over my shoulders for directions. “You’re really going to love this. I just know it.” he said as he jerked the Raging Hard-on out of my ass and pressed his hard slippery cock in. It stretched my ass open as the head popped in. It stung but I wanted it so bad I just took it. My body shook, “Fuck! You’re so big.”
He just held it in for a minute as he chuckled then pulled it out. My body shook again and I whined. I looked over my shoulder at him, “Don’t take it out. It’s OK. It’s just so big.” He pushed in again with a smile. He slid the head in and out a couple times, “Doesn’t that feel good?” It did, “Yes.” I joined in and started moving with his rhythm. I could feel his cock as it worked it’s way in. Each pump slowly increased its depth. It felt so good as it sunk in deeper. The head passed the point of no return and kept going.
My body shook and my legs bent. I couldn’t have stopped him now. It felt like it kept getting deeper and deeper. The deeper it got the more I was lost in the sensations. I imagined his big cock pushing its way through my guts. I could feel my organs move around as it slid deep inside. It felt so strange. I remember stroking his cock with my hand and how the shaft and head felt as I jerked it. Now it was in my ass and I could feel it slipping in and out.
The swollen head was like a big bulb that moved around inside stroking my innards as I was getting more aroused. The thick shaft was rubbing that spot at the bottom of my dick. My legs started shaking with excitement. I could feel every inch of it. I just moved with him as the feelings took over. He could tell I was enjoying it. It was like finally giving in and scratching that poison ivy itch.
“It’s my turn to cum. So, you jerk me off.” Like today in the bathroom, he just stopped moving and stood perfectly still. I knew what he wanted this time and I wanted it too. I kept stroking his cock with my butt. I squeezed it a little as I jerked his cock. It felt so good and I didn’t want to stop. My body became his toy. I started out short and slow but with the slick lubricant it didn’t take long before I was stroking it longer, deeper. Randy’s cock felt so good as I worked it. “Oh fuck.” I groaned as his cock hit a new depth.
Randy had been quiet as I worked his cock with my ass until he said, “This feels better than when you jerk me off with your hand. I really like it.” I was never so happy to hear that. He said he likes my efforts. I liked it too. I squeezed my cheeks around his shaft and stabbed it into me. He sighed, “You’re good. It’s almost all the way in. Do you like it? Can you feel my long cock stroking inside you?” I did. I could. It was scratching an itch I never knew I had. I turned to look over my shoulder. He was smiling. It felt amazing and he was happy. Randy was grinning ear to ear as I jerked his cock with my ass. My ass felt like it was having an orgasm, “Oh fuck it’s good.”
Randy was enjoying his payback and encouraged me, “Do you remember cumming with my cock in your ass today? Well, just wait until you feel me squirt in your ass when I cum.” Oh god, he’s going to cum in my ass! At first the idea frightened me. The thought of his cum being deposited in my ass. What’s going to happen? Then he said, “You’re going to want to do it again. Trust me.” I do. I thought about his big cock as I worked it in my ass. I felt the itch return and no matter what, I wanted to scratch it.
My desire overrode my fears and I went wild and stroked like a mad man. The poison ivy paradox, the more you scratch the more it itches. As I kept it up I could feel his pubic hairs brush against my bare cheeks. His big cock was almost all the way in. I was so caught up in the moment, I hadn’t realized it had gotten so deep. I was just scratching an itch. Randy was grunting with each stroke when he said, “I can’t believe you did it. We’re all in now!” He put his hand on my shoulder and thrust his cock all the way to the root. The hairy base of his cock was pressing against my ass cheeks.
His thrust lifted me onto my toes. I could feel the head up in my belly pressing into my organs. His pubic bone ground into my tailbone. He jerked his hips again. Randy made sure his entire cock was in my ass. That’s when I had a huge ass-gasm quivering tightly around his cock. My back arched with the realization and I yelled, “Fuck me!” I felt his shaft surge and the head deep in my ass pulsed. He’s going to cum in my ass! I clamped down as my mind echoed, ‘We’re all in now.’
I couldn’t have believed it when I started out this morning. My mind flashed on my mother walking in on me when this all started. The butt plug hidden from sight, hanging by it’s head in my ass. The ‘Raging Hard-on’ barely fit in my virgin ass. It hurt and I figured it would take a while to get used to it. Then everything changed when my mother interrupted me. It was trapped in my pants and it pressed me to my limits. I fought against it. But it ended up all the way in, deep inside me. I tried so hard to remove it and now I wouldn’t want Randy to take his big cock out. What would she think of her little man now. Naked, sweaty and writhing in my friend’s basement being fucked in the ass. It felt so good. I wanted more.
“Here it comes.” he said and I felt something deep inside me squirt. He’s really cumming inside me, I thought to myself. I’ve watched him ejaculate before when we jerked off together. He always had a huge load and it squirted really far. My ass squeezed his shaft. This time I could feel his cum squirting inside me. It felt hot as it filled my ass and began to run down my leg. The more he ejaculated, the more I wanted it to keep going. It charged me up. Excited me. I clinched and stroked following each pulse. Then without touching my dick I spontaneously started to cum.
He pulled back a little and slammed in with each squirt saying, “Yeah, you like that don’t you. Then take it… All of it.” He was right I did like it and I wanted all of it. His cock pounded my ass as we kept cumming. I followed his movements like a dance. Squeezing and riding his thrusts. It was amazing. Stroking his cock with my ass till he came made me cum the best I’d had yet. Randy was right, I was going to want to do it again. I just kept jerking his cock with my butt as we both ejaculated over and over.
Moments later he interrupted, “I told you, you were going to like it.” Then he wrapped his hand around my neck and pull me against his hard body. He mock choked me. It gave me a rush. He spoke very close to my ear, “But, you came. You still owe me. Again.” I didn’t care. I didn’t want it to stop. My head was frantically shaking, yes. He backed out then smoothly pushed his cock all in again, “How about tomorrow night?” My legs still weak and shaking. My ass still clinching his big shaft. That will work. Saturday would become our regular anal night.
It was now obvious that his huge cock would fit in my ass. From that day on I only used the ‘Raging Hard-on’ for fun or when Randy told me to have it in for something he ‘wanted to try.’ I didn’t need to practice up anymore. No more avoiding the intrusion. I knew how good it could feel and I wanted to do it over and over.