Jumbo

This is a continuation of the previously posted stories on this site.  My first story about my first orgasm will give the most history and help provide context to this adventure.  

 
A brief history is when I was 13 by best friend Jeff and I used to make out with our pillows and masturbate together when we had sleepovers.  We were never embarrassed nor were either of us attracted to each other.  It was just discovery we shared and enjoyed together.  We were both straight teens learning how we worked.    

 

After the first couple of times he and I had our pillow sessions which are documented in my stories as well.  That summer Jeff and his family went on vacation for nearly a month so I no longer had my friend to share these moments with.  

 

I had another friend, Brian that was also the same age as me. About two months older and we also hung out often.   We had a sleepover planned at my house and I was really excited to share with him what I knew about how good I could make my body feel.   I wasn’t old enough to feel ashamed or feel as if what Jeff and I did was taboo.   So I had no hesitation about sharing this amazing discovery with Brian. 

 
The weekend came and on Saturday we did all the regular things teens do. Eventually my parents went to bed and Brian knew I had what we called “The Tape”.  It was a copy of a VHS tape one of our older friends compiled from the tv at his uncle’s house.  His uncle had a satellite dish and with it the porn station American Exxxtacy.  (This was the 80s remember). So this compilation tape had hours of recorded porn.  In another story, I describe the first time Jeff and I watched it together. 

 

Anyway Brian asked when we could watch The Tape, and now that we knew my parents went to bed, we were in the clear. My bedroom was in the basement which was nice because nobody could ever sneak up on you because you’d hear them upstairs stomp across the floor on their way to the basement.    

 

My bedroom had a double bed and to the right I had a roll-away cot for Brian.  I had a small 16” tv with a VHS  machine in my room. That’s where we’d view The Tape.   I popped it in and Brian settled under the covers in the cot wearing only green track pants.  I got into my bed to his left with boxers and a t shirt.  As we watched the video, we fast forwarded through scenes I knew were boring and watched the ones I knew were good.  My favourite movie on The Tape was called Perfect Partners with I think Joey Silvera and Amber Lynn. I was so in love with Amber Lynn back then.  As we watched the flick we were both not shy to note we were groovin on ourselves under the covers.   I was excited to tell Brian about what I discovered with my pillow and I asked if he wanted to see something cool.  I told him I knew how to orgasm and I use my pillow to do it.  To my surprise he also said he knew how to come.  He was the first person I knew who called his orgasm a “come”.   I asked him if he came anything yet and he told me he did.  I was jealous because of all the orgasms I’d had with my pillow thus far I didn’t see anything come out.  Brian said it only stated a few months ago.  

 

Brian turned to me and said “show me this pillow thing”. So I took my favourite pillow, removed the pillow case, kicked off my blankets and maneuvered my erection through the slit in my boxers.  Note if you haven’t read my previous stories, my method at the time was to lie on my back, and place the pillow flat on my chest, to the left of my penis.  The right edge of the pillow would be in contact with the left edge of my penis.  I did this for two reasons.  One being that the sensitive part of my head is the left side, and with the pillow on one side as opposed to the middle, I was able to slide it up and down my torso, letting the right edge rub back and forth against my erection. This was my method from my first orgasm a few months ago until this night. 

 
As I started to pump the pillow up and back, Brian sort of giggled and told he he just likes to rub like the men in the pornos did. I had tried that method before but since my first orgasm the tried and true technique for me was the pillow.   We continued to pleasure ourselves, him under the covers and me above with the pillow.  I was lying to his left, and he had a perfect unobstructed view of my cock as the pillow was on my left side.  I was getting curious to what was happening beneath the covers as he stroked so I asked him if he could show me his technique. 

 
 Now, up until this moment I had been pretty confident with showing my body. I was smart enough to know my cock was average and that it would never look like Joey Silvera on the Tape.  I also had measured it with a wooden ruler that I had in my room. I marked it with a marker and everything.  5-1/4".  It has a slight right curve so I had to pull it flush with the ruler to get the measurement right to the tip.  It was also slightly longer and a tad thicker than my other friend Jeff’s so the only other erect penis I’d seen in person, was 2nd place to mine. 

 So when I asked Brian to show me his technique I was honestly more interested in how he did it, and not what he looked like.  So when I requested his demonstration he said “okay” and pulled the covers away from his legs.   I noticed his green track pants were pulled part way down to his knees and his erection rested against his stomach.   I remember the flush that came over me when I saw it.  I will tell you to the God’s honest truth.  Brian had a huge penis.  I remember actually gasping and pronouncing “Oh God that’s huge Brian!”  He smiled and lifted it from his stomach so it stood straight up.  He looked down at it and back at me.  I remember the dark black pubic hair covering the base and his balls.  His erection was longer and thicker than mine for sure.  It’s hard to tell being 13 then if it was thicker than my full grown cock, but it was defiantly a shock to me.  He started to pull at it and show me how he stroked it, but I still couldn’t get over it’s size.  I asked him how big it was and he shyly said he didn’t know.  I rolled to my left and got out of bed and took the ruler from my desk and a marker.  I walked it over to him and threw it on his cot and said “measure it”.   He looked a bit embarrassed as I stood next to the end of his cot with my rock hard cock sticking directly out of my boxers.  I thought maybe he wouldn’t want to continue our adventure but the light from the tv and the low volume of the porn was likely too much for both of us to turn back. 

 Brian took the ruler and pressed it against his pubic mound and pressed the tip of his head against the numbers etched on the ruler. “Seven and 3/4.  Right on seven 3/4”. I got back on my bed and looked over and just as he said, it was exactly seven and three quarter inches.  I couldn’t believe it. He threw the ruler back at me and he said “I’m not marking it”. So I took the marker and made a small mark at 7-3/4" It was almost more than two full inches longer than the ruler mark I had made a few weeks prior to etch my manhood into the measuring stick.  

 
A side note. I had this ruler for years and as I matured I always wanted to see if I would reach his mark.  I never did.  My full grown male erection is 7", and I always wonder if his continued to grow like mine did.  I wonder if he made 9”.  I wonder if it got thicker.  As we got older and started relationships with women, the word got out about Brian’s cock. It was even turned into a nickname among our small friend group.  We called him “Jumbo” in high school. He hated it but there were worse things to be known for in high school.  To this day I bet if I go back to my childhood home, I’m likely to find that ruler I my desk with those two nondescript marks that only Brian and I know the meaning of.  

 
Okay. Back to the story.  So after getting over the shock of seeing Brian’s penis we turned our attention back to the tv.   I resumed my pillow work and Brian covered himself back up and started to stroke under the covers.  We focused our attention on the porn and I felt my orgasm getting close.  I would speed up and slow down to make the feeling last longer. Sometimes I would stop and just watch the tv as my penis throbbed to the beat of my heart against the pillow.  Brian would also jerk fast then slow under the covers.  We didn’t know what we were doing at the time, but we later learned it was called “edging”.  

 
At one point Brian looked over at me and said “I have to take my covers off or I’m gonna make a mess”.  I told him “Do what you gotta do” (or something like that) and he pulled the covers down again.  Green track pants now balled near his ankles and giant erection wrapped with his right hand.  “Are you sure you want me to do this in the bed?” Brian asked.  He continued “I can’t really control it.”  I replied with something like “Who cares?, just have fun”.   

 Brian looked back at the tv. Joey Silvera was fucking Amber Lynn from behind and the faint sounds of her moans were so exciting. I always loved how she moaned in her movies from the 80s.  I watched Brian as he sped up slightly and strengthened his legs.  Then I saw the first person ejaculate of my entire life.  As he stiffened, white streams of cum shot from his erection, landing on his shoulders, neck and the pillow by his head.  The next few spurts hit his belly button and stomach.  He convulsed and sort of shook his penis as if he was trying to get everything out.  His hand was wet too.  It looked so strange.  I’d seen porn where the man came on the woman, but never seen anyone with their own cum on their body.   Brian looked at me and said “I made a mess” and sort of giggled.  I told him not to worry about it and that I had to orgasm now too. 

 
I laid back down and started my pillow technique and within moments my back was bucking and hips trusting and my orgasm hit me.   As usual nothing came out but I had all the convulsions of an unmistakable climax.  As I stopped rubbing the pillow, I laid on my bed and looked to Brian who said “that looks so weird”.  I have no doubt it did.  

Right after the post climax blissful feelings subsided, my next emotion was panic as Brian was still in his cot with cum all over his body.  What if some got on the covers or sheets?  Would my mom or dad find out? I told him not to move and hopped out of bed, making my way across the hall to the bathroom to get a towel.  I came back in and tossed it at him telling him to clean up. He wiped everything off his body, and the only evidence my parents may have found was the two spots on the pillow next to his head.  We tried to clean that up but agreed that we would just tell them it was “drool” if they asked. (Like we would have fooled them). 


We turned off the porn and just talked. I asked if he knew his dick was so big and he said he always thought it was normal.  I asked him what it felt like when the cum came out and if it shot out before or after the tingles.  I asked if it felt like peeing, and did it always shoot so far by his head.  He explained all the things I would experience myself eventually. How far it shoots is related to how horny you are or how long you were masturbating. Sometimes if he was quick he said it just dribbled out. If he did it many times in one day the amount of cum reduced each time.  I asked him how often he did it and he said every day. I said the same.  He asked me if I always used the pillow and I told him yes.  I told him most of my masturbating was on the floor of my bathroom with the pillow so my parents didn’t know. I explained that when I performed multiple sessions in one day the edge of my cock would get irritated from the rubbing and I’d have to stop for a day or two.  He laughed and told me to use his method so it didn’t hurt. 

I didn’t switch methods until I started to actually ejaculate with my orgasm. That was a couple months later.  I knew that I couldn’t hide the stains on the pillow, so I had to learn to do things the “standard” way. 

Brian and I never did it again. Never even talked about it. But I will always remember the first time I saw someone ejaculate in person. 

More to come.