In the first chapter, John tells the story of his youth and how his best friend persuaded him to find more pleasurable sensations through masturbation, anal play and much more. John tries very hard to please his best friend.
Trying too hard
My name is John.
And I'm a gay man.
Not flaming mind you. Not some frilly guy that makes you uncomfortable when he walks into the room. No. No flashy walk. No flashy clothes. No. I'm just a regular guy that likes... well... guys. I wouldn't normally even consider myself gay. I've found it's just easier than using one of today's definitions. It's just the way I feel. I always thought it was normal. Some guys chase after sports or money. Other guys are chasing after girls in skirts. Some others like both sides. You know, play the field and enjoy everything life has to offer. I've had some interesting relationships with girls. Still, I've always had an affinity for men.
I'm a smart guy. College educated and worked through some struggles in my life. Spent some time on the psychiatrist's couch. You know, learned a few things. Let go of a few things. One thing I learned was, 'When you have a problem it is important to recognize it and admit it.' My problem is I'm single. I don't like being single. I had a long term relationship that ended last year. I cried a lot. He wasn't the first. For a while I thought I would be fine and just spent some time getting back into me. My hobbies. My artwork. My fantasies. That's when things started all over again.
Being single isn't for me. Not just for the social comfort. I'm not afraid of being alone. I'm afraid of not having a man around for satisfaction. Here is my second problem. Sexual satisfaction. It all started when I was young. I was always introverted. My family just thought I was shy. At school I didn't join many clubs or have special interests. I didn't make friends easily and spent a lot of my youth watching people and feeling left out. So I learned to be OK with being alone. I had some kids that I played with during recess. But not real friends. All except one.
There was one kid that hung around and got to know me. Our birthdays were just days apart. So, we had a connection early on. He was always friendly to me through grade school and middle school. From middle school on we officially became friends. A relationship flourished. The relationship was a little one-sided but I didn't mind. He was good at finding fun and always included me. I on the other hand had trouble seeing out of my books, computers, chores. At home my father didn't really help in guiding me through growing up. So, I began depending on him to guide me to and through things. As our generation rode through puberty we hung out together. We turned eighteen a week apart in February. In the final months of Senior year in high school he became a special friend.
His name was Randy. Puberty was awkward and embarrassing. Things were changing and we vowed to ride it out together. He seemed more confident and could talk about these things. I looked up to him when it came to questions I had. As things went along he told me some stories and showed me some pictures. About sex. All about sex. I started to have feelings, sensations when I thought about them. The stories and pictures made my dick itch and get hard. Rubbing it against things or with my hand felt good. Once I actually masturbated to ejaculation, I was hooked. When I told Randy what I had done he wanted to join me. That started our long strange relationship.
The first time together was right after I told him. We stole away to a creek bed that passed under the road on the way home from school. A dark tunnel was the perfect place he said. The air was cool and I could hear the echos of our breath. It all started with him telling me to do it so he could watch me masturbate. I felt really embarrassed but excited so I did it right there in front of him. Next I watched as he masturbated. His dick was bigger than mine and his cum went further than mine. It felt like a game we played together. We laughed and ran to the empty barn behind his house. There we masturbated again.
This led to regular times when we got together to share the excitement. It was new and felt so good to do. Having a friend made it more exciting. Someone to share it with. It had begun by watching each other jerk off. Progressing to touching each other's dick. Then holding the other person's dick when they ejaculated. Eventually jerking each other off. Even jerking off together in a mutual orgasm kind of way. That's when his rule started about 'cumming before the other person and not finishing them off.' More on that later.
We had been playing with each other for weeks since I first told him about my masturbating. We'd get together and sneak away to a secluded spot and jerk off. It didn't really matter where; the culvert near his house, the old barn on the neighboring property, the Oaken woods. It didn't really matter when either; before school, after school (sometimes both), and of course late at night during sleepovers. We just enjoyed it and I became more physically attached to our friendship. A couple times while we were jerking each other off I groaned a longing moan. Randy would look into my eyes and smile as he squeezed my dick. It felt like he understood my feelings and my needs. The more we met the more often I would feel that connection and satisfaction.
He experimented on me more than I did on him. He always had new and interesting ideas. I hadn't noticed in the beginning. I was just happy to have this special friend. Our masturbating together made for a strong physical connection. We made each other feel so good. Got to know each other's triggers, what got us excited. Tickling, spanking, whatever came up. I liked my ass rubbed. One day he had started rubbing my butt while we jerked each other off. It started by him remarking, “I want to try something.” Then he slid his fingers down my crack saying, “Does this feel good?”
At first I thought how dirty that was. After all, my poop comes from there. But just rubbing it wasn't that dirty. I relaxed as he tickled and poked. It felt good so I didn't complain. He started touching my asshole as part of our ritual excitement. After a couple sessions I got used to it and it really got me exciting. I groaned my satisfaction as he rubbed my dick and explored my puckered hole while we jerked each other. Then one time when he could tell I was getting close to cumming, he abruptly stabbed a finger into my puckered hole just as I came. It stung a little but I came hard. Randy asked how it felt. I said it was a shock but it felt so amazing when I came.
The next time we were playing he began poking at my hole again. My emotions were mixed and I tightened up. He reminded me about the last time he put his finger in my butt and how good I said it was. I flashed on the experience and my face lit up and I turned beet red. It did feel good. His finger pressed against my hole. My hand blindly squeezed his dick as I stroked it. Randy asked, “I wonder what would make it feel even better?” I froze for a moment. It could feel even better!? My mind was frantically looking for ideas but as usual my mind was blank. But not Randy's, “If a finger made it feel that good, what about two.” I could feel a stirring as he slowly rubbed my dick. He continued to brush his fingers in the crease of my butt. My tenseness faded and I was drifting off on the rush of sensations.
His big dick was hard and oozing in my hand as I stroked it. Mine was stiff but not as hard as his. My mind was still trying to imagine the possibilities. “I want to try something.” he said. That made things easier. He always had exciting ideas and I looked at him with peaked interest. I watched as Randy licked two fingers before he pressed one against my hole. I wanted to let him in but the last time it stung so my butt quickly tightened again. He wiggled his slick finger around my rim. I could feel it slip around as his fingertip urged on. I felt my butt tingling and itching as it pressed in. It slipped against my dark doorway. Easing through my tight hole I felt it inside me. This time it wasn't quite a shock. The spit on his finger did the trick. His fingertip just slipped in and out of my tight butt.
What stinging there was didn't last for long and my hole relaxed with the strange but exciting sensation. To my surprise his slippery finger went deeper and deeper. I couldn't believe how easy it was. My dick was pulsing and started to ooze from the tip. His finger slid in and out so easily as he kept up the experiment. Soon he was pushing his strong hand against my butt cheeks and I could feel his finger touching something inside. He had stopped stroking my dick and was just holding it while he lifted his hand up and down between my legs. I could feel his finger slipping in and out while wiggling around deep inside me as he pumped and pushed, “Does that feel good?” My mouth was slack. I couldn't speak as the rush of sensations flooded my brain. His hand began lifting me slightly with each full finger press. My body was moving with his strong thrusts and I arched my back, it felt so good I just moaned and groaned. Any trepidation I had melted into the rhythm of that finger rubbing my insides. When he lined up a second finger and pushed in, I shook all over. My dick was throbbing and my mouth fell open as my hole stretched, “OH! Wait!”
My ass clamped down hard trying to halt the sudden stretching. I could feel both fingers wiggle just inside my tight hole. The shock made me try to stop him. But, my efforts were useless. His slick spit made his fingers unstoppable. Quickly both fingers were in too far. No amount of tightening my hole could stop them. Randy held my dick firmly exclaiming, “Wow. They both fit!” My ass twitched. My voice squeaked as I tried to plead with him, “It kinda hurts.” I tried to continue my struggle against the intrusion as he wiggled his fingers deeper inside me, “But... Oh! Uh!” Nothing I could do seemed to keep his fingers from invading deeper. The sensations flooded my body as a tingling traveled up my spine.
My mind was also losing the fight to keep him out as the wiggling in my ass melted my resistance and I began to relax. It did hurt but I couldn't deny that it felt exciting. He hooked his fingers in my ass and pulled. My hole stretching as I gasped and shook. Then sliding his fingers around the tight ring, he smoothed out any final wrinkles in my nerves. It felt crazy. Sliding his fingers in and out I started to shake and twitch. When I arched my back he pushed the two fingers deeper. It was melting my concerns. I groaned and looked at him. My mouth open and shaking. Lust in my eyes.
It felt so good as my ass hole stretched to fit his fingers. He kept pressing deeper, I could feel his fingers sliding in until his hand pressed against my bare ass again. When I felt it my eyes rolled back in my head. There was a subtle itch deep inside that this seemed to scratch. My knees shook as I tried to get his fingers to scratch it more. He started pumping them in and out. Quicker and harder. I had completely forgotten about jerking his big dick. My body on autopilot moved with his hand as it began quickly and repeatedly spanking my ass. His fingers burying themselves to the last knuckle with every spank.
Suddenly he stopped with his hand lifting me up by my cheeks. He held them deep and wiggled them around. I turned to look at him with weak eyes. My open mouth had begun drooling. It was so weird. He asked if it felt good. It felt so good. Again he said, “I want to try something.” Then he suggested that it would feel even better if he put his hard dick in my ass hole. Then we could both get off at the same time. My eyes shot open and my motion stopped as I thought about what that meant. His hand still holding me up on my toes. He wiggled his fingers scratching deep inside. My legs got weak and shaky as I thought it through. My hand gripped his hard shaft. It was much harder and bigger than his two fingers. Randy encouraged me to try it as he roughly jerked his hand around, “You said it feels good.”
My whole butt was being jerked around by the two fingers in my hot wet hole. His fingers moving around deep inside made it hard to think rationally. I was unsure but so excited, and he was my special friend. So, I reluctantly agreed. He let me down as I let go of his dick and he moved behind me. He pulled his fingers out with a jerk. Then he rubbed his dick head and placed it against my tight virgin butt-hole. After a little work it finally entered with a lot of pain. “It's too big!” I whined and shook with the stinging. Even as excited as I was the pain brought me down to earth.
He stroked my dick and encouraged me to relax. It would get better he said, “Just relax.” My body was shaking with the pain. He put his hands on my hips and held me still with his big dickhead just inside me like a harpoon. The sharp barbs held it in place and I didn't dare struggle for fear of causing permanent damage. After a little pause he wiggled around and was able to pump it in me a few short strokes before I had to make him stop. I was so tense with the idea of his dick in my ass, I couldn't relax. The pain seemed to override everything else. Then Randy's voice changed. He sounded disappointed, even angry. He said I didn't even try as he pushed my hips away letting his dick pull free with a pop.
My ass stung but now it felt empty. The relief was double edged. All the excitement drained away. Randy had some strong words for me. He made me feel ashamed and inadequate. He stepped back, away from my still excited heaving body. I turned to look over my shoulder. I wanted to see his face. I wanted to see his expression and find a way to resolve the guilt I was feeling. He looked disappointed, almost angry. I pleaded with him, “I tried. It really hurts. Don't be mad. I tried, really I did.” He stared at me for what seemed like forever. Then he changed his tone. He smiled through his scowl. He said it probably takes a little practice.
I kept trying to explain. But he ignored my pleading after that. We didn't hang around for a couple days. My heart was sinking. I knew I wanted to make things right. I just didn't know how. Randy wasn't talking to me. He ignored me in the hallways at school. I was lost. Then Thursday after school he stopped me and asked me to forgive him, He didn't have to say anything more. I was ready to put this whole thing behind me, so to speak. The next thing I knew he was giving me a paper bag. Inside the nonde*********** bag was a real looking dick of a butt plug. 'The Raging Hard-on' it said on the package. A smile was back on his face and I felt a sense of relief. I looked over the little phallus with great interest. After all he said I just need a little practice.
He told me, “A special gift, for a special friend.” It looked like a shorter version of his stiff dick. He continued by saying the next time we got together he would help me with it, we could do it together. After hearing him say 'special friend' my mind had drifted off. My eyes were looking at the phallus as my thoughts wandered. I wanted to make him happy. I tried to remember the good parts of our last exploration. His fingers slipping in and out of my ass did feel good. Maybe I do just need a little practice, I thought to myself. I just didn't want him to be mad. The tone of his voice the other night when he got angry pushed me to want to please him. That mixed with my deep desire to find greater sexual experiences urged me to try it as soon as possible.
It was the next day, early on Friday morning before school when I tried it out. I had looked it over last night and by morning I was determined to make Randy proud of me again. We had to leave for school soon. But I was so excited I couldn't wait. My clothes were mostly on and I had just returned from the bathroom and a good bowel movement. I held the special gift in my hand. Small compared to the size of Randy's big dick it was still bigger than my poops. I was beginning to understand why they called it the 'Raging Hard-on.' Still, I was determined to try. I had stolen a little lubricant from my parents stash and was figuring out the geometry of reaching my arm around behind me and guiding the head of the butt plug towards my ass.
I put some lube on the butt plug and then touched my ass hole with it and my legs shook. Closing my eyes I imagined it was Randy's finger rubbing my tight hole. The lube felt good and I slid the tip of my finger in. My leg shook again. I pulled my finger out and looked at the phallus, 'Your turn.' Then I lined up the Raging Hard-on and closed my eyes. The lube helped as the tapered tip parted the way then stretched my hole as I gently pushed it further. It felt like I was pushing harder and harder but it wasn't going any deeper. My hole was tight and resisted being intruded upon. I could feel my hole lift up into me a little as the pressure built. My body was excited and my legs shook with anticipation. I wiggled it around trying to loosen up a little and my face turned red. Then pushed on. It started hurting just a little when something popped. My eyes shot open. A cold sweat formed on my brow. What had I done?
My body twitched. I quickly popped it back out with another twitch and looked it over. No blood. Thank heavens. Looking it over I realized, that was just the head! I swallowed hard. I hadn't even made it to the shaft which was thicker than the head with raised veins on the sides. A flush came over my face again. Randy's cock was much bigger than this. It was going to take a while before I'd be able to work up to something that big. Or so I thought. After all his cock head was in there once. I added some more lubricant determined to try again. Then I took a deep breath and pushed the head back into my ass till it popped. Stage one. I wiggled it around some more until I got over the initial shock.
It felt better with lubricant and I was popping it in and out trying to get used to the size. It didn't feel that bad and I was completely focused on it. Nothing else mattered at that moment. After a few tries I was thinking about working it deeper when I heard my doorknob rattle. I had lost track of the time. I let go of the phallus stuck in my butt and pulled my pants up, startled. Lifting my pants forced the Raging Hard-on to press against my tight hole and it slid past the head with a shock, “Mom!” As expected my mom appeared at my door with a scowl. I looked myself over to make sure nothing was exposed. My secret was covered, I hoped.
I'm sure my face was bright red. I was quick to pretend I was just getting ready for school. I kept pretending to straighten my pants and belt. I wondered if she suspected anything. Mom had caught me masturbating before but just shrugged it off, nothing seemed to phase her but I didn't want to know what she would think of what was up my butt at that very moment. I fumbled around hoping to delay her orders. I cleared my throat and raised my eyebrows at her.
She just looked at me sternly, “We're going to be late. Again. Let's go!” I straightened my pants and tucked in my shirt. I felt the butt plug slowly moving around as my butt moved in my pants. I lifted the belt and my pants tightened against my butt cheeks, adding pressure against the Raging Hard-on. It was being held firmly in place by my clothes and every action transmitted through it into my ass.
My mind still wondering if my mom suspected anything. I rushed around my room to collect my things. With pressure and movement along with that thin coating of lubricant, the shaft began working it's way deeper into my dark tunnel. It was painful and cold as it inched it's way along. What am I going to do? I hid a grunt by clearing my throat when it shifted. The feelings grew as I imagined what was happening down there. Strange sensations emanated from my hole. Each of the veins on the Raging Hard-on must be passing through my tight hole and felt like wiggling worms as they slid past my tight opening. I could feel it like a turd, not quite in and not quite out. I squeezed it but it wouldn't give. I couldn't go to school like this. I had to do something.
“But mom, I gotta... go to the bathroom.“ I pleaded, hoping to escape to the bathroom for a minute to remove the invader. I was feeling the Raging Hard-on as it kept working it's way deeper with every move. It stretched my hole which stung and burned. I was so embarrassed and in pain. My face flushed again as I felt the head pushing up inside of me where Randy's fingers had been not too long ago. I gave mom my best puppy dog eyes. She wasn't buying it.
I had been lagging in my senior year and was on thin ice as it was. Little did she know what I had in my pants. That didn't matter to her. “You know the rules.” she said “If you're not ready on time, you go as you are. So, let's go!” I knew the rules. But, like this? This was never thought of when the rules were created. I slowly waddled past her and could feel everything moving around down there. She followed close behind urging me towards the car. At the laundry room door I squatted down to pick up my gym bag.
As I did, mom suddenly and forcefully lifted me by my belt and the butt plug was forced all the way in. “Mom!” My body shook and I saw a flash of light. I coughed and braced myself on the door jam. Oh, was that a surprise. It was so deep now. It still stung but I couldn't reveal the secret. Not to my mom. I didn't dare touch it or draw attention to it. I couldn't even stop and let it settle in. I just kept moving feeling the 'Raging Hard-on' wiggling back and forth with my steps. At that moment it felt like a hard painful bowel movement waiting to be relieved. One you need to run to the bathroom for. But that wasn't going to happen and I struggled to keep moving.
Each step was a new sensation but I kept it hidden. By the time I got to the car my face was red, my ass was stinging and getting hotter. My dick swelled a little and was becoming very sensitive. When I plopped down in the car seat as I normally would, I grunted and whimpered. The head of the little butt plug had driven itself deeper then I'd ever expected for my first time. My organs settling down around the stiff intruder as I tried to settle in. I just kept reminding myself, I was doing this for my special friend. Not to mention how good it might feel when I came.
The drive to school was an education on pain and pleasure. Accelerating, braking, turning, stopping, and then there were the bumps. Oh, the speed bumps. Not to mention potholes! Each one bounced me in my seat causing the phallus to feel like it was pumping in and out. I didn't know what it would be like to have Randy put his dick in there again. But I was getting an idea. By the time we made it to school I was buzzing with energy. My dick was throbbing. The head of the Raging Hard-on had punished my virgin insides. The shaft had been vibrating in and around my tight hole and I had gotten spasms a couple times during the ride.
My eyes were glazed over and I was hoping to quickly go to the bathroom at school as a second attempt to take the intruder out. I said goodbye to my mom and walked slowly towards school. I tried to ignore the feeling of it rubbing my insides with each step. My foggy brain was busy mapping out the quickest route to the nearest bathroom. When my hand landed on the door I felt a sense of relief, like I was going to get away with it. I walked into the building focused on the nearest bathroom. Just my luck, there was a group of tough kids hanging out around the bathroom doors. I didn't want any of them finding out what was going on either. So, I skirted around their group but just as I locked eyes with one of them the bell rang and we all headed straight to class. Like a herd of cattle everyone turned and wandered away from the bathroom. The group formed a barrier to my goal and forced me to lead them to class. The butt plug will have to stay there until end of class. If I can keep my composure.
My first class on Fridays was in a large lecture room with stadium seating and I always sat near the front. A choice that only today I regretted. The room was already full and my face felt bright red. I hoped no one could tell. I lowered my head and worked my way towards the open seat the other students had left for me. Once I sat down it felt better. At least everything stopped moving. I took a breath and realized it didn't feel that bad. Good, to tell the truth. With all the excitement I hadn't realized the pain had eased and it felt different. Like when Randy's fingers worked their magic to ease the pain.
That's when I noticed it. An itch had been forming deep inside. I felt it when Randy had his fingers deep in there. The drive to school had pushed me past the initial pain and now I could feel it. That itch grabbed my attention. I ground my ass into my seat and prepared for note taking. But there wasn't much note taking except in my head. Making notes like; not wear this thing to class again and other notes on how good it felt to wiggle around. The teacher started his lecture but I was already glazed over.
Every little move was transmitted deep. Deep inside. Right to where the itch was growing. I was drifting in and out of the lecture. The teacher droned on and on but I wasn't able to concentrate on the subject. My mind was thinking about the Raging Hard-on touching my insides. Rubbing the root of my dick somehow. No matter how I tried I couldn't put it out of my mind. Every time I looked at my notes or tried to focus on the teacher it clouded my attention. I couldn't sit still and that wasn't helping either.
Every few minutes I would adjust my seat and gasp. I tried to cover it up by clearing my throat. Other times I would arch and slouch working the Raging Hard-on around inside as I silently moaned. I felt an itching like poison ivy and I was trying very hard not to scratch. At least not surrounded by my classmates. By the end of an hour and a half class I was wrung out. My dick had been hard multiple times. My butt itched and I could feel my pulse throbbing around the plug in my ass.
Every little move stirred my emotions. My face was red and my eyes just stared off. 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. 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. The sensations started rising inside me again.
I had to stop and catch my breath when a sudden wave overtook me. It started in my balls and traveled backwards up the root of my dick ending right were the Raging Hard-on's head sat. Then it surged outward to my face, hands and feet. It was weird but it felt exciting. It left me dazed and I struggled to keep my composure hoping not to be noticed. I leaned casually against the wall and put a smile on. As I stood there with the special gift from my special friend twitching in my butt. I wondered what Randy would think of my efforts.
Little did I know how Randy was going to respond. Or what plans he was going to implement next. All I knew was our special friendship was exciting and growing and I wanted to keep it going no matter what it takes. Especially if it feels good.