I guess this could be called the sequel to "My First Mutual" which was posted May 12.
This happened mid-summer, several months after my experience with Tom and his buddies. After that, I thought about initiating some play with my friends but was too shy to start anything. I was worried about how they would react and worried about my own feelings. Girls really turned me on but I was confused as to why I was interested in my friends too.
My best friend in Jr. High and High School was "Mike". He lived a few houses down from me and we had been friends since we were little but as we grew we got tight. Where I was an only child, Mike had two older sisters and a younger brother he shared a room with. We had lots of sleepovers over the years, most often at my house. He liked being away from his family and liked how lucky I was to have my own room. My room was upstairs where there was also a "guest room" with a connecting bathroom between them. We would usually sleep in the guest room since it had a double bed, radio, and small TV. As long as we changed the sheets in the morning and cleaned up, my parents were OK with us using it.
This was a typical sleepover and Mike and I were lying on the bed either watching TV or looking at car magazines, or both, it's so long ago I don't remember for sure. Also typical was we were both just in our underwear. Me in briefs and Mike in boxers, which he only wore in bed. I don't remember what we were chatting about until we started talking about this girl we saw at the towns pool that day. She was late teens or early twenties and we had never seen her before. We lived in a small town where you knew everyone or at least recognized them.
She was like a model, tall and well shaped, long brown hair with striking green eyes, perfect teeth, very tan, wearing a yellow bikini that was quite skimpy for this era. All the guys at the pool couldn't keep their eyes off of her as she lay tanning and many went up to her to chat, just to be rebuffed. Mike and I were in awe of her beauty.
Late in the afternoon she finally dove in the pool and swam around for a while and when she got out Mike and I were standing on the deck near her. Our jaws must have hit the pavement at what we saw when she got out. Her bikini had become somewhat translucent and you could see the dark color of her areola and her bush right through the material. She walked toward us as we openly stared at her and she met our eyes and gave us a small smile. Then her eyes traveled down to our crotches and she kind of snickered. Both Mike and I were sporting tents in our swim trunks. Embarrassed, we both quickly jumped in the pool.
As Mike and I were reliving the days event and wondering what she looked like naked and saying what we'd like to do to her we both got hard. No surprise when you're 14. I put my hand in my briefs to re-adjust to be more comfortable and Mike says "That's why I don't wear briefs to bed, too uncomfortable when you pop a boner." My response was that if he wasn't there, I'd be naked since I normally slept that way since my parents rarely came up to my room. He said that's why he envied me. There's no way he could get away with that at his house. His little brother would freak and his sisters would give him a hard time if they found out. And, surprise to me, he blurts out he hardly gets a chance to jack off what with sharing a room and the mad dash to use the bathroom in the morning and evening. Sometimes sharing the shower with his brother so they wouldn't run out of hot water.
It was no secret we jacked off and Mike and our other friends had shared when we became able to cum, but we never really talked about it. And I had wondered how Mike found the time to do it but never asked until now. He said he'd usually wait for his brother to fall asleep or do it real quick if he showered alone. I mentioned his brother would be in the same situation soon, if not already and he said maybe so, he thought he smelled cum one morning even though he hadn't done anything the night before. I mentioned if he was doing it then maybe they wouldn't have to hide it from each other, no big deal since we all do it. He contemplated this idea for a few seconds and agreed, saying maybe he should even show him how to do it if he already hadn't figured it out for himself.
Mike then asked me about my own habits, when I did it, how often, etc. I told him at least once a day, usually before falling asleep, or in the shower in the morning, or both. Most often thinking about girls we knew and if he wasn't here I'd be doing it thinking of the girl we saw at the pool that day and he agreed that she was great jack off material and would be doing the same. Mike then asked if I'd ever seen any skin magazines, the pictures could really make it better and he had seen some at his cousins house earlier that summer.
Seeing the opening I'd been waiting for since being at Tom's I told Mike about the sleepover and Ken bringing real hardcore and even knowing what sex was how seeing pictures of it was mind-blowing and how hard and horny it made me. Mike said it must have sucked having blueballs all night, not being able to do anything about it and I went for it and said "I hope you don't think it's weird or queer but we all jacked off, right there in front of each other."
Mike was quiet for a few seconds and all I could think was "So much for our friendship, should have kept my mouth shut." but he said "WOW, really? COOL!" And that him and his cousin had done it too, but was afraid to tell me thinking I'd think it was weird. We were both silent, probably thinking the same thing, "Maybe WE can do it together, but how to start?"
We were both really hard and my penis had poked out the top of the waistband of my briefs and there was a little pool of pre on my stomach. Mike's boner was sticking straight up in his boxers and I could see it through the fly. Knowing what each other were thinking we both pushed our underwear off and threw them on the floor exposing ourselves to each other. We'd compared in the past and going through puberty checked on each others progress looking at our sprouting hair and putting our hard dicks together to see who was bigger but we hadn't done that in a year or so. All I'd seen is his boner in his boxers in the morning at sleepovers or soft in the after PE showers. We'd both grown and while average in size we both were developing from the small size I remembered.
I went to my room and got the bottle of tanning oil I used for lube and locked both the bathroom and bedroom door, even though I knew my parents were asleep, I was just paranoid. Mike asked about the oil and I figured everyone used lube and was confused and asked what he used. He said "Nothing, what's it for?" I told him it made it soooooo much better and he'd see. I lay down next to him and put some oil in my hand and rubbed it over my cock and began to slowly stroke, handing the bottle to Mike. He didn't use it right away and just watched me while playing with his balls. I scooted over next to him so our hips were touching and put my left arm behind his head over his shoulders and told him to go at it, try some oil. He just squirted it on his dick, way more than enough and a bunch ran down into his hair and between his legs. I told him it was too much and grabbed my briefs and wiped the excess out of his pubes and around his balls making him flinch and gasp. I said sorry and he said it was ok, felt good, he was just stunned I touched him there.
Mike started to stroke like me and we just watched each other, sometimes making eye contact. He said the oil was great and going slow was even better and how lucky I was to be able to take my time. He never had the chance to go slow and always had to rush. And how much bigger our dicks were since the last time we'd seen each others boners. Back then, they weren't much larger than a big felt marker but now we could put our hand around it and still have the head stick out.
Even though our hips were touching, Mike pushed up harder next to me and switched to using his left hand and lay his right on my left leg, slowly running it up and down. I looked at him and his eyes were closed so I didn't think much of it but wondered what he was thinking. His hand ended up slowly going up over my stomach and down my leg in kind of a circle and kept creeping closer to my crotch. It finally got close enough to get into my pubes and he'd spread his hand so the base of my dick would be between his thumb and index finger as he felt my pubes. I was starting to wonder if he wanted to jack me and spread my legs a little and his next circle he stuck his fingers down around my shaft and felt up my balls.
I pulled my arm off his shoulders and stuck it under Mikes right and ran my hand over his stomach lightly, back and forth. He had some hair growing from his navel down to his crotch and I used my index finger to tickle it and ran it through his pubes and around the base of his cock, too scared to do much more yet. I was just following his lead in a way. His eyes were closed this whole time but mine were wide open in wonder at what we were doing.
I think my actions of reciprocation made Mike go farther and on his next pass he held the base of my penis, giving it a few light squeezes and matching my stroking so I did the same. He more or less pushed my hand off my dick with each upstroke, working his way up, so I let go of myself and he opened his eyes and looked at what he was doing and just felt me up at first. Squeezing me, feeling my head, milking out some pre-cum and smearing it around and down my shaft.
I had stopped doing anything to Mike during this and he picked up my hand and put it on his dick. I got the message and felt him up like he was doing me and to me his dick was softer than my own. Even though we looked the same, his skin felt softer and looser. I tried to milk some pre out of him but he didn't have as much as me. When he started stroking me in earnest I did the same and we made eye contact and smiled at each other. The oil was drying out by now so I drooled some more on us and I still remember the sloppy, squishy sound of us getting each other off, and the pungent coconut smell of the tanning oil.
We had sped up our stroking since we were so close and I figured Mike wanted to orgasm as much as me. I don't know how long this all went on but I'm guessing a half hour or so, much longer than if I did it to myself. Mike started to tense and stopped stroking me and grabbed me kind of hard so I figured he was ready and really went at it and he shot more and farther than I ever had. I had his dick pointed at an angle up toward his head and the first shot hit the headboard over his head with each other shot hitting from his shoulder to his chest. I could feel each volley as it came up his shaft and was kind of scared of all the grunting noise he made, I feared it might wake my parents.
After his first few shots he started stroking me fast even though he was still cumming and as soon as he was done shooting I too came. Not as much as Mike but still the best orgasm I'd ever had in my life. I've never been much of a long distance shooter so most of my cum just spurted out all over my stomach.
Coming down after our orgasms we both sighed and looked at each other, smiles on our faces. I grabbed my briefs and cleaned off the headboard and ourselves and threw them on the floor at the foot of the bed. I asked Mike if he always shot like that and he said no, maybe it was because he hadn't jacked off in several days but more likely it was because I was doing it and it wasn't his own hand.
Mike then asked if I ever came more than once, could I do it again? I said yes I'd done that before and once did it four times in a row but quit because my pecker got sore. "So you can do it again at least one more time, easy?" I told him yes and after a short while we both got hard again. Really, we never went completely soft. We did it one more time that night and many other nights over the years, even when we had girlfriends. As we got older the frequency lessened but out of all our experiences this first with my best friend is still fresh in my memory. And we did experience things with our other close friends which I will share in the future.