This is the only time Ian and I masturbated together.
While Ian, Cory, Kevin and I had our mutual fun every few months you'd think Ian and I would do the same since we were so close but we never did. Our group action seemed to satisfy our urges and the topic never came up on the many sleepovers Ian and I had. Usually, we'd jack off in the shower before going to bed. Only once did we jack off together.
It was mid-summer between our Junior and Senior year of highschool. Ian's dad had us rip out some plants and part of the lawn in their backyard so he could build a new deck. As pay he would take us on their boat to Catalina so we could fish and sightsee. Along with his younger twin brothers we made quick work of it and ended up really dirty and sweaty, spending most of the day shirtless.
After a dinner of pizza Ian's dad says we need to be asleep by nine and he'll wake us about four in the morning. (What teen can fall asleep at nine!?) He shooed us upstairs at eight and being dirty and stinky we all needed showers and playfully fought in the bathroom connecting their bedrooms, pushing and shoving each other as we tried to pull off our clothes to be the first in.
I'd seen the twins naked from time to time over the years as they became comfortable around me and I'd seen Ian naked countless times having gym class together the past two years and during our mutual fun. But this was the first time we'd all been naked together at the same time. The twins didn't follow Ians bloodline, he was more like their dad with fair skin and black hair where the twins followed their mothers with a more olive skin and light brown wavy hair. They were almost 16 but not shaving yet and had little body hair. A thin line in their pits and a bit on their legs and inner thighs and just a triangle of pubes over their penises. Like Ian they weren't circumcised but unlike Ian who had a lot of skin hanging off the end they were more average with the skin just covering their heads when soft.
It was decided the twins would go first, sharing the shower, then Ian and I. We shaved and brushed our teeth to pass the time and when the twins got out Ian suggested we shower together since the hot water would probably run out by the time I got in. Seemed sensible to me and I didn't even think twice about it and agreed. It was a bit cramped but we managed and it was nice to have someone scrub my back. After the shower we lay on his large bed just in our towels and talked about whatever while trying to calm down to go to sleep, mainly bitching about how early it was and that we weren't even close to being tired. Hell, the sun had barely gone down.
Ian shushed me and we could hear one of the twins beds squeaking rhythmically, obviously one of them was jerking off. We snickered as the squeaking sped up and heard a quiet moan and the squeaking stopped. I'd slept over many times and never heard this before. Ian said it started recently after the twins and one of their friends were roughhousing on the bed and broke something. Since then he'd heard it almost every night. I never really thought about it until then but wondered if the twins jacked off at the same time since they seemed to do everything else together. Ian said they did, he'd peeked into their room once and they were in their own beds going at it so he figured that was their routine before falling asleep just like we did on our own.
We then talked about our own masturbation habits and how we both figured it out for ourselves, thinking we'd discovered something no-one else knew about. And how Ian, when caught by the twins, showed them how to do it. Also, how we beat off before dates so we wouldn't get hard at the drop of a hat. All this talk got us boned and we were tenting our towels and I really needed to rub one out but didn't want to use the bathroom and figured since we'd done it together before I'd suggest we go for it to get rid of our hardons and calm us down so we could sleep. Ian said he was thinking the same thing.
We unwrapped the towels from ourselves and started to stroke, Ian mentioning he liked to take his time making the orgasm better. I liked to do this too, saying I'd get close and stop for a bit. We watched each other and as always I marveled at how his skin glid over his glans, jealous to a degree. Going slow I produced a lot of pre which I used for lube and could see Ian was doing the same with the clear fluid coming out the tip of his foreskin.
I'd always wondered what it was like to have skin and came up with an idea. Ian had so much I figured he could cover my head and I could feel what it was like. When I told him my idea he didn't hesitate and rolled onto his side facing me and I did the same, touching our wet cocks tip to tip. He pulled his skin all the way back and pushed it back up, covering my glans with the softest, warmest feeling. He used his hand to hold it on and just jacked both our heads slowly. I could feel our pre mixing, lubing us both and was real close to climax at this new sensation and I told Ian he'd better stop or I'd blow all over us. He said he was ready too and we should just go for it. He stopped stroking and held both of our heads in his hand and just fingered under our glans and I couldn't hold out any longer and came in torrents. I could feel my cum fill his skin and it came out along my shaft. Ian came too and I felt each spurt as it shot over me and also leaked out down my shaft and onto the towel between us. Ian rubbed our mixed cum over our shafts and we parted and lay on our backs, Ian saying 'That was fucking ammmmazing!' I said it was my best orgasm ever and how lucky he was to be intact.
As we lay there Ian said since he did that for me I owed him a favor but if it grossed me out it was ok if I didn't do it but I couldn't mention what he was about to ask to anyone, ever. Since he was my best friend and we had no secrets and I was curious I agreed. He asked me if I ever played with my asshole, other than just rubbing it on the outside. I never had and told him it never occured to me to do any more. He said he liked to stick a finger in himself just as he was about to cum and it made the orgasm so much better. But it was awkward to do and would I do it for him, just once, so he could feel what it was like without having to reach around. The idea did gross me out a little but he was my best friend and would do it if he wanted.
As I lay there he got himself hard again and jacked off. I rubbed his nipples and cupped his balls as he did so and his pre started again. He put up his knees and spread his legs so I massaged the hard area under his scrotum and his anus. He told me to spit on my finger to lube up and he'd tell me when to stick it in. I did so and rubbed around his anus and probed the hole delicately, feeling the muscle clench and relax, quite odd and exciting at the same time. He said to get ready and sped up his stroking. I could tell he was ready and without him saying so I stuck my finger in and it went easily. He told me to wiggle it so I did and he started to shoot onto his stomach. I could feel the muscle clench with each spurt, suprisingly strong, and then relax as he finished. I pulled my finger out, expecting it to be covered in crap, but it was clean. He rubbed his cum over his stomach and chest and sighed saying it was awesome and much better than doing it to himself. Curious, I asked why it felt so good and he couldn't explain and I should try it. I was hard again and Ian said he'd do it to me if I wanted, and if it felt wierd he'd pull his finger out right away. I figured, 'What the Hell, why not?' and said go for it.
Still slick with our cum from earlier I jacked quickly to get to orgasm fast, I kind of wanted to get it over with. Like Ian I spread my legs, bent at the knees and he played with my balls and used the cum on his chest to lube my anus. I clenched every time he rubbed it and he told me to relax, it would make it easier. I could feel as he probed me to the first joint in his finger and it didn't feel so bad. He kept talking quietly, incourgaging me to relax and let it happen and I got to orgasm quickly and said 'Just do it' and he plunged his finger in quickly and wiggling it a bit(didn't know about the prostate then) and I shot all the way to my face. It felt great and I knew I'd try it on myself in the future. Ian rubbed my cum all over myself and even wiped the shot off my chin.
Both spent after two orgasms each we lay there and Ian again said it was our secret, Cory and Kevin might not understand or freak out if we tried it together but he trusted me. I agreed and laying there we talked about how much better could sex with a girl be if we could feel so good just doing this stuff with ourselves? We both had girlfriends and the minor stuff we'd done with them wasn't all that gratifying. We'd both let them fondle us and fondled them, through clothes, and it left us both frustrated with a case of blueballs we took care of when the date was over. We both got hard again and said how about one more? I was spent but still horny and said the most I'd ever done was five in a day but they were spread out. Ian claimed seven in a row but the last two were dry.
We decided to do each other and went head to crotch facing each other and didn't waste any time jerking each other off in our last orgasm of the night. The loads were small in comparison to the first two and we were both spent, covered in each others cum and now tired. We lay there figuring we both needed another quick shower to clean off the mess and stench of cum. I wanted to just relax a bit and wait a few minutes to calm down and dozed off, figuring Ian would wake me when he was done with his shower.
Ian never did get his shower and also dozed off. Sometime during the night one of us pulled the sheet over ourselves and we were rudely awaken early in the morning by someone turning on the light and pulling it off of us. I figured it was one of the twins but to my horror and Ians it was his DAD! I still remember the way it was stuck to my body and how it made a noise as it came off. All he said was 'You two stink, get a quick shower' and he left to wake the twins.
Going downstairs after showering was hard, we figured we were busted bigtime and expected the worst. Ian's dad picked up on our apprehension and said 'I was your age once, you know' and that was the end of that.
Ian and I never did it together again. Not because of getting caught, it just didn't happen. We had a few more mutuals with Cory and Kevin our Senior year but our focus was more on girls and we kind of outgrew our fun.
Ian moved to Australia with his family after graduation and still lives there. We haven't seen each other since '83 but still write to each other from time to time. Kevin got a scolarship and left home at 18 like he said and has never come back and I haven't talked to him since we were 26. Cory and I are still close, even though he now lives out of state. I feel our mutuals made us all closer friends and don't regret anything I ever did with any of them.
Next, Kevin and I. (Surprised me too!)