Me and My Best Friend

When I was a young man, I was addicted to masturbating. I mean, addiction may not be a strong enough word. I would masturbate 4-5 times a day on average and I could have done it more if not for all the sports I was involved in. I would jerk off first thing every morning after waking up, 1-2 more times at school, once more when I got home and then a final time when I took my shower at night.

Along with my addiction to beating off, I also quickly took a liking to jerking off in risky situations where the risk of getting caught was high. The first time I did it was in the 8th grade. I would get a ride to school every day from my neighbor’s mom. She had a big late 80’s Cadillac and I would always sit in the back by myself. While driving to school that day I got a boner for no reason (only guys can understand that) and I started to panic that it wasn’t going to go away before we got there.

I quickly grabbed my backpack and set up a barrier between my crotch and my neighbor’s mom just in case she turned around. I unzipped my fly and pulled my cock out and began to quickly tug on it. I had been masturbating for about a year now and I was good at it and quick. Within less than a minute I shot my load all over the back of the passenger seat. I took a piece of paper out of my backpack and as quietly as I could I wiped my cum off the seat and then rolled up the paper and threw it in my backpack. We pulled up to the school a few minutes later and I remember being so turned on by it that I headed straight to the bathroom and I jerked off again before my first class and that was the beginning of my voyeurism fetish.

This continued on the next couple of years as I became more and more adventurous with my masturbation. I would jerk off in bathroom stalls when my mom took me shopping and I would leave the stall unlocked so that people would walk in on me. Now that I look back it probably wasn’t the safest thing to do but I wasn’t thinking about the danger back then just the thrill.

One night during the summer between my freshman and sophomore years of high school I stayed over at my buddy’s house for almost an entire week straight. We lived just a couple blocks apart so I would frequently run back home to change and then go back to his house. We spent most of our days outdoors playing various sports and then came home at night and played video games until his parents went to sl**p then we would watch the cheesy porn shows on their cable black box. We would always get boners and we both always ended up excusing ourselves from the room at different times to "use the restroom". I think we both knew what the other was doing but we never really mentioned it.

One particular night during my week long stay we watched the porn as always and my friend excused himself from the room. I couldn’t wait for my turn so I decided I would jerk off in his room while he was jerking off in the bathroom. I quickly pulled my dick out of my boxers, spit in my hand and began to beat my cock with fervor. I had my attention split between the porn on the TV and listening for the bathroom door to open in the hallway.

I had already jerked off about 5 times that day so this one was taking a little longer. I was starting to get close so I leaned back against the bed and closed my eyes. I was nearing the end but still intently listening for the door. Within a matter of seconds I was blowing my load all over the carpet in front of me. I continued to stroke until all the cum was out and then I let go of my cock and just sat there relaxing as I went limp.

A few more seconds passed and I opened my eyes and to my horror my friend was standing there in the doorway looking at me like he had just seen a ghost. I quickly scrambled for a pillow and put it over my lap and let out a "What the fuck Jason! How long have you been there?" He said he just walked up but I could tell from the look on his face he watched more than he was letting on. I was completely embarrassed and he just walked in his room and jumped on his bed and turned the channel. After a few very awkward and silent minutes he turned the TV off and said good night.

In the dark I sought out the cum drops I spread all over the carpet and rubbed them into it as to not leave any hard spots. Once convinced I found them all I laid down. I was so embarrassed at being caught but at the same time I was extremely turned on. We would see what tomorrow would bring.

He woke up first that next morning and then when breakfast was ready he woke me up. We had a normal day and we both acted like nothing had happened. We did our usual routine of playing outside with our friends all day and then back home at night for video games. Once his parents went to bed that night again as usual he flipped on the black box and we began watching porn. We watched for about half an hour when I finally had reached that time so I got up to go to the bathroom and I turned towards my buddy and he was on his bed and had his hand down his pants rubbing himself.

I acted like I had just got up to stretch so I turned and raised my hands in the air and gave him a profile view of the tent I was pitching. I did a couple of torso twists then I quickly sat back down. I sat Indian style with my back against the bed and I pulled my cock out from my boxers. Trying to be inconspicuous I slowly began to stoke my cock with my friend sitting behind me on the bed rubbing his.

I was getting really turned on by the excitement of it all but I was not getting close to cumming as I wasn’t able to stroke myself fast enough. A few more minutes passed and I could feel my buddy move on the bed. I quickly tucked my cock away as best as could and then my buddy’s legs appeared next to me hanging over the edge of the bed. At first I thought he was getting up off the bed but he stayed in that position. I took a glance to my right and my buddy has his cock out and was just beating away as if I wasn’t there. I took this as a cue that he was comfortable with all of this so I untucked my cock and began stroking it again.

Once we were both jerking off we didn’t last that long. I could hear my buddy breathing deep and then within seconds some light grunts and he shot his load all over the carpet next to me. I soon followed and I shot my load all over my lap and legs. We sat there silently for a few seconds and then my buddy got up and grabbed a towel from his hamper and wiped the carpet then handed it to me and I cleaned myself off and threw it back in the hamper. He turned off the TV and we went to bed.

That next morning we woke up and again it was business as usual. However just before noon the weather took a turn for the worse and it began to rain so we headed back to his house. It was the middle of the day and both his parents were at work so we stayed downstairs and watched TV. After watching a rerun of Sanford and Sons my buddy said that he would be right back and he ran upstairs. About a minute later he returned with something in his hand. He held it up and shook a VHS tape in his hand and said "Wanna watch?" I asked what it was and he said it was the "good stuff". I knew what that meant so I said eagerly shook my head yes.

He threw tape in the player and came and sat next to me on the couch. He sat so close to me that our arms were touching. The video started to play and it was a real hardcore porn tape. Not that fake soft core shit they play on the cable channels. Within seconds we both were sitting there with raging hard ons from all the action. We both sat there not reacting and for the first time I got a good look in daylight at how big of a bulge my buddy’s cock was making in his shorts. I was getting so horny and I couldn’t take it any longer so I unbuttoned my shorts and then zipped down the fly. I pulled the band of my boxers down a little bit and then pulled my cock out. There I was sitting arm and arm with my best friend and my rock hard erection was within inches of him. I spit in my hand and then took hold of my cock and began to stroke it.

As I started jerking, my buddy followed suit and pulled his gym shorts down and unleashed his huge cock. It wasn’t the biggest cock in the world but for a 14 year old it was massive. He was also uncircumcised which was something I had never seen in person. The other thing I noticed was that he had massive balls. He began stroking as well and we were both masturbating side by side.

This lasted for a couple of minutes and then my buddy said that he was going to cum. He leaned forward and scooted to the edge of the couch and to my surprise began unleashing rope after rope of thick white cum all over the coffee table. I remember saying "Holy shot that’s a lot of cum!" and he turned towards me with a big smile as if he was proud of it (and well he should be). I followed suit just seconds later and did as he did by scooting to the edge of the couch. I began to cum all over his cum already on the table. I didn’t put out nearly as much as he did but it was respectable in my own right.

He both plopped back on the couch and laid back admiring our work. Both with our cocks out still and wet from our cum. My buddy got out and went to the kitchen and came back with some paper towels. I took them and began to clean up. The table had these grooves in it and it was a bitch to clean up. It took a good 5 minutes to clean the table of all our cum. I handed them the dirty paper towels and he took them back to the kitchen and threw them away.

He came back and sat on the couch next to me (both our cocks still out) and he asked what we should do now. My eyes were glued to the screen as the girl in the movie was getting double penetrated by two big cocks and I couldn’t turn away. I asked my buddy how many times a day he jacks off and he said 2-3. I nodded approval and he asked me the same question. I lied and said the same thing as I didn’t want him to think I was some weirdo or something.

We sat there watching the porn and within a couple of minutes I was starting to get hard again. He looked over and was shocked. I saw him looking at my now half erect cock and I told him "I bet you $5 I can cum again before you do." He sat there for a second thinking about it and then said "You’re on!" He stood no chance.

Before he was even fully erect again I was already reaching for the paper cup sitting on the coffee table and I blew my second load in 15 minutes into the cup. When I finished my buddy exclaimed "I’m impressed" and that he couldn’t cum that close together. I said "I’m a pro" and lifted my glass as you would during a toast and I downed my cum. His jaw dropped. With this surprised look on his face he said "You eat your own cum!?’ I asked him "You don’t?" He was just kind of stumped. I told him it’s easier than cleaning up and he kind of had that look like he never thought of it that way. I wasn’t about to tell him that I also thought it was kinkier than hell to do that as well.

He gave up jerking his cock and we both put our cocks back in out shorts and sat there on the couch watching TV. I told him that he owes me $5 and he said that he would buy me lunch. We ended up walking to McDonald’s when the rain stopped and the rest of the day went as usual.

Night time came again and we retreated to his room to play video games. Again, as was the routine, as soon as his parents’ lights went out he turned on the black box and the porn. This time he sat on the edge of the bed immediately. This time I dropped my pants down to my ankles and sat right next to him on the bed. We both had our cocks out before we were even hard and we jerked ourselves erect.

This time I didn’t care about the porn. I laid back on his bed and had my cock pointing straight at the ceiling and continued to jerk off. My buddy like my idea and he too laid back as I did and jerked off that way. In no time at all I was ready to cum and I pulled my shirt up to my neck and shot my load all over my stomach and chest. My buddy was watching me as I sat up and scooped up all my cum off of me and ate it. Once I had finished that I tuned on my side and watched my buddy jack off. Watching him stroke his big cock was getting me super excited and I decided to take a chance.

I reached over and began to play with his balls. He stopped jerking off and pulled his hand away and I immediately pulled mine away. I apologized and said I got caught up. He told me not to worry and he wasn’t mad and was just startled. He said it even felt good. I took his cock back in his hand and began stroking again. I looked at him and he gave a little nod of approval and I reached over and began playing with his balls again. It was almost a two hand job but I managed with just one.

I then decided to take it the next step and I took his cock in my hand. He pulled his hand away but this time I did not react. For the first time ever I had another man’s cock in my hand. It felt awkward to stroke it since it felt completely different than mine and the angles were weird but I managed. I finally found somewhat of a groove and I began to get a good rhythm stroking his cock. I could tell that he was enjoying it as his hips starting to move in rhythm with my hand.

He couldn’t last at all and I could feel the familiar jolt of a cock about to cum in my hand so I pointed his cock straight up and he began to shoot thick gobs of cum 2-3 inches up in the air and then come crashing down back on the head of his cock. As I continued to stroke him it started to spread the cum all over his dick and it was now acting as a lubricant. I began to squeeze tighter as he was finishing cumming and I pulled back his foreskin and wiped it clean with my thumb. He looked up at me with a look of pure enjoyment and I asked him if he would be weirded out if I tasted his cum. He hesitated for a second and then said "Be my guest." I stuck out my tongue and touched it to the thick cum that was on my hand and then pulled it back into my mouth. It was a little more bitter than mine but much thicker with its own distinct taste. It didn’t taste bad so I began to lick the rest of it off my hand and ate it. He then grabbed a towel from his hamper and cleaned off his cock. I stood up, pulled my boxers back up and laid down on the ground. He turned the TV off and the night was over.

That next morning we woke up and it was already raining again. By the time we woke up both his parents were gone and there was a note on the table saying breakfast was in the oven. We ate and then laid on the couch. The rain subsided later that morning and the sun came out in full f***e. We called a couple of friends up but everyone was either already doing something else or not in the mood to play anything. So we decided to just spend the afternoon in his backyard playing in the pool.

My buddy asked if I needed to run home and get my trunks and I told him not to worry. He ran upstairs and got his trunks and when he came back down I was already in the backyard. He came out onto the patio and I was just standing there completely naked. I turned around, ran towards the pool and yelled "Cannonball!" as I jumped in. When I had resurfaced I could see that he was in the process of removing the trunks he just put on and followed my cannonball with a cherry bomb.

We spent the next 30 minutes or so playing various stupid little games that we have made up over the years. After I defeated him in a game of pool basketball he yelled for a break and he got out of the pool and ran back inside the house. He came back out a minute or so later with a couple of glasses of water. He walked up to the edge of the pool and reached down and handed me my drink. He then sat on the edge of the pool right in front of me. I don’t know if it was by accident or by design but my face was just a few inches away from his cock.

At first I tried to act like I didn’t notice but it was too hard to hide my curiosity. I sat there staring at it as if it was an inspection. Forgetting that I was staring at it I looked up and he was just looking down at me with a big shit eating grin on his face. By now I was beginning to play with my cock under the water. I leaned over and put my cup on the pools edge and I scooted closer to him. By now he was starting to get hard so I took his cock in my hand and began to stroke him. He put his cup down and put his arms back behind him and leaned against them.

Now that I was in a better position to play with his cock I continued to stroke him with my right hand and began to play with and squeeze his balls with my left. Every time I squeezed he would throw his head back in a mixture of pain and pleasure. I was starting to get the urge to take this to the next level so I took the opportunity when it presented itself. I gave his balls a good squeeze and when he sent his head back I leaned forward and gave the head of his cock a lick. He immediately whipped his head back and looked down at me unsure of what just happened. I acted like everything was normal.

This time I gave him a squeeze again but this time I took the head of his cock into his mouth. I could feel that his head whipped back in place again but this time I did not stop. All I could hear him say was "Wow" and I could feel his cock twitching in my mouth. I did not know what to do as my only experience with this was what I’ve seen in pornos. So I began to bob up and down on his cock. I could only get about 3-4 inches of him in my mouth but it didn’t matter to him. No more than 30 seconds after I put his cock in my mouth he told me he was going to cum and so I pulled his cock out and began jerking him off.

Within seconds he began to spasm a little and he began shooting his cum onto my face. I figured it was the right thing to do since it was what they did in pornos so I opened my mouth wide and tried to aim as many of the shot into my mouth. Only a couple got in my mouth while the rest ended up on my face or in the pool. When he had finished I took the head of his cock back into my mouth and pulled his foreskin back and cleaned everything up with my tongue. Once I was done I swallowed all the cum I had collected in my mouth as he just sat there and watched me in amazement.

We sat there silent for a few seconds and then I asked him if that was his first blowjob. He said that it was and then he apologized for cumming so quick. I just laughed and said it was ok. He then asked if that was the first time I had ever given one and I said yes too. He then asked if I was gay and I told him I didn’t think so, and that I was attracted to women. I said that I was probably bi-sexual. He let out a little chuckle and said that he can’t believe that his first ever blowjob was from his best friend.

Over the next handful of weeks we spent practically every day together. I gave him on average 2-3 blowjobs a day when we hung out. The more and we did this the better I became at giving head and the longer he could last. We also kept working towards me being able to deepthroat his cock. It was a slow process but every day I could get a little more down my throat and eventually my gag reflex began to subside as I learned how to control it.

Our breakthrough happened a couple weeks after the first blowjob when we watched a porn where the girl laid on the edge of the bed with her head hanging off and tilted back as far as possible. The guy then had a straight line from her mouth to her throat and he basically had sex with her face and was going all the way in and the girl had no problems. As we were watching this happen we both looked at eachother like a revelation came to us at the same time.

My buddy asked if I wanted to try that and I gladly said yes. We were at my house this time and my parents and s****r were home but they were all doing their own thing. I got up, quietly locked the door and stripped my clothes off. Jason followed suit and he too stripped down and revealed his semi-erect cock. I sat on the edge of the bed and pulled him towards me and took his cock into my mouth. I played with the head a little and massaged his balls until he was hard as a rock.

I pushed myself back onto the bed and swung my legs around so that they were at the head of the bed. I then laid back until I was flat on my back. I wasn’t quite in the perfect position so I moved a couple inches towards the foot of the bed. I titled my head back and the edge of the bed went perfectly into the crook of my neck. I looked up at Jason and said I was ready and opened my mouth wide. He placed the head of cock in my mouth and I wrapped my lips around it. I gave him a little nod and he slowly began to inch his cock into my mouth. To my surprise, he was able to slowly slide his cock all the way into my throat without any real resistance.

Once he was all the way in he just held it there for a few seconds almost as if he was savoring the moment. I couldn’t see anything as his huge balls were covering my eyes. He slowly pulled out about halfway and then slowly pushed all the way back in. He did this for about a minute or so and then I pushed him back a little so that I could talk.

He asked if everything was ok and I said it was good and that he could go faster if he wanted. He reinserted his cock and went back to slowly sliding in and out but within a few seconds he began to pick up the pace. Every he would go a little faster he would ask if I was ok and I would give him the thumbs up. After a few minutes he reached a fairly swift pace and he was officially fucking my throat. Without his asking I gave him the thumbs up again and he asked "Faster?" I held my thumb up again and he increased the pace of his thrusts.

By now the sound of his balls slapping against my face was starting to get a little loud so I felt around for the remote control on the bed and was able to grab it and turn the sound up on the TV to mask it. When I did this Jason leaned forward and put his arms on either side of me to hold himself up and began to really pump his cock in and out of my throat. I increased the volume a little more as I was beginning to make sounds with my throat on every deep thrust and the slapping was getting louder as well.

He was fucking my face so hard that it was driving my head into the side of the bed and causing the bed to creak and hit the wall.

Within about 30 seconds of hard face fucking Jason gripped the sheets on the bed and I could feel his cock start to quake. He pulled out and was going shoot it on my face but I reached out and grabbed his cock and took the head into my mouth and began jerking his cock until he exploded in my mouth. I did not break the seal that my lips had around the head of his cock and I took every thick rope of his cum in my mouth. While this was happening I began to cum all over my chest and I hadn’t even been stroking myself. I was so excited and turned on by what was taking place that I came hands free.

I finally felt in my mouth that he was no longer cumming and I opened my mouth to show him his work and then I swallowed the entire load. Once I had swallowed it all I took his cock back into my mouth and he stuck his cock all the way back down my throat and kept it there until I was out of breath. His cock went limp and I released it from my mouth. He leaned forward and began scooping up all my cum from my stomach and chest with his hand and fed it to me as well. We got dressed and we went to sl**p.

This carried on the entire summer that year. We began to get more and more adventurous. We even attempted anal at one point but he couldn’t even get the tip of his cock into my ass so we gave up on that and just stuck to me giving blowjobs. We began to seek out situations where I would give him head in a public setting as we were both into the rush you get when doing that. I gave him multiple blowjobs at the movies. I gave him head on a public bus when we were the only ones on it. The bus driver saw us but said nothing. We live near the mountains so we would go biking and pull off the path and I would give him head within view of the trail. Most of the time people would just give us a disgusted look and move along, on occasion the guys would stop and jack off while watching us.

Once the school year started back up we didn’t do it as much due to being at school all day. However from time to time we would meet up in the bathroom and I would give him head in the stall. One time we almost got caught as he made a noise as he came in my mouth. It was a teacher and he yelled out "Who’s in here?" Jason yelled out it was him. The teacher asked what was going on and he said his stomach was hurting. Satisfied with the response the teacher entered one of the other stalls and Jason and I quickly made our exit.

Once Jason got his license our favorite thing was road head. We would even drive to fast food joints a couple of cities away and we used love seeing the reactions of the people at the drive thru window as he pulled up with my head in his lap bobbing up and down. Most of the time people would just laugh. No one ever really got mad. We would go to restaurants and I would jerk him off under the table. This one night we went out to eat at a sit down restaurant and we sat on opposite side of the booth. Throughout the meal I was rubbing his cock with my foot under the table. Towards the end of the meal we both ordered dessert. He got cheesecake and I got a scoop of chocolate ice cream. As we were waiting for our dessert I was able to get him arm with my foot. I was wearing flip flops that night and I had my bare foot up the leg of his shorts and was skin on skin with his cock.

Jason at this point put his arm under the table and began to jack himself off. A minute or so later the waitress showed up with our desserts. Jason kept jacking himself under the table as she set down the desserts and asked if there was anything I needed. We said we were good and she left. Just as she left he grabbed my ice cream and put it under the table. After about 30 seconds I could see that familiar look he got on his face and I knew what was going on. Another 15-20 seconds passed and Jason brought the ice cream back up and sat it on the table. As clear as day, my chocolate ice cream was almost completely covered in his thick white cum. It looked as though he poured marshmallow sauce all over the top.

I began eating the ice cream and surprisingly enough it was actually a good compliment to the chocolate ice cream. The salty and slightly bitter taste of his warm cum mixed well with the cold sweet flavor of the ice cream. By now I had my hand under the table and had pulled my cock out of my shorts and was jacking myself off while eating the ice cream. About half way through the scoop I was about to cum so I grabbed the empty glass that my soda was in and came into it. Once I was done I placed it back on the table next to my ice cream.

When the waitress came back to drop off the check she started to take away some of our dirty dishes. She grabbed the glass with my cum in it and asked if I was finished. I held out my hand asking for the cup and said "One second." I tilted my head back and lifted the glass. It was a clear glass and you could see the cum slowly pour down the inside of the glass unlike any liquid they sold. As it reached the edge of the glass it began to pour into my mouth and only a complete idiot would not have known what it was. As I was doing this I could see her do a double take looking at my ice cream. By now she knew what was going on. She didn’t know what to do at first. I finished drinking my cum and I handed her back the glass. She took it and quickly walked away. Jason and I both let out a laugh. We paid the bill and left her a hefty tip.

We had many adventures like that but none as blatant as that was. By the end of high school it was becoming a more rare occurrence for us as I was getting ready for college and he was working getting ready to be next in line at his dad’s cement business. The last time we had an encounter was the day I went off to college. He drove up with me to drop me off. I gave him 3 blowjobs that day and the last one occurred in my dorm room after he helped me get settled in. That was the last time I ever gave my best friend head. We are still best friends to this day but he is married with a wife and k**s and I’m still as kinky as ever!

100% (33/0)
 
Posted by handiman1980
6 months ago    Views: 17,320
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26 days ago
I wish I had a friend like that growing up!!
5 months ago
great story loved it
6 months ago
I love to masturbate
6 months ago
I've had a very fulfilling sex life to this point in my life. I've taken a lot of chances and with those chances have come many memories I'll never forget. If you read my other stories/post they are all 100% true. Most of my stories from here on out are going to be about my past experiences. I am currently in a relationship with a transsexual and I love her and am planning on marrying her. I have stopped all my other "extracurricular" activities but I still have many stories from my past worth writing about that I hope to post over the next couple of months. Glad you enjoy!
6 months ago
So hot! I'd love to have a friend like you did, I'd love to experiment like that, sounds like it was amazing!
6 months ago
I hope its true. Loved it
6 months ago
very nice, question is how would you rate that part of your sex life compared to the rest?
6 months ago
Love it!
6 months ago
well told
6 months ago
nice story
6 months ago
@handiman1980 when I was younger I used jerk off with my best friend when we were in the same room as me when we stayed together but we never went as far as touching eachothers cocks, nice story tho bud reminded me of when I did, got anymore stories?