I had gone to public school all the way up through middle school. When I began high school, though, I had some bad experiences and eventually transferred to a local boarding school spring of my freshman year.
Because we lived in town, I didn't board there but only attended school there. During my time there, I heard lots of rumors of mutual wanks among the boarder, but never saw any evidence of it myself, even when I boarded for a week once when my parents were on vacacation.
The spring of my junior year, my parents said we would be moving before fall because of my dad's work. I, however was able to convince them to let me board at my current school for my senior year. They were fine with it because it would only be a half-day's drive away.
It actually had nothing to do with the rumored jack-off scene, I wasn't even thinking about that at the time. I just liked the school and wanted to spend senior year with my friends.
The first day, I was assigned to one of the medium-sized rooms with about eight other guys. That night in bed, I thought of the possibility of the mutual wanks. That whole week, I kept my ears peeled for clues, nothing.
I was so disappointed.
Most Fridays, we'd get the afternoon free to do whatever. One Friday, I got a group of guys together to go see a movie. When we had gotten about a block from the school, I realized I had left my wallet. I ran back to school and up the stairs to the room. I stopped short when I saw the door closed and voices inside.
I listened for a minute until I heard what sounded like 'Let's initiate Chris tonight.'
I didn't know exactly what they they meant by that, but I was pretty sure I would be joining the wank club.
I quietly retraced my steps a ways back down the hall then walked loudly toward the room to announce my entrance. I coughed before I opened the door. I walked right past the group of guys, got my wallet, and walked back out.
After the movie, we returned to school in time for dinner and the evening activity, tonight it was games on the lawn. When the game was over, we went back inside to get ready for bed. I got in bed, but didn't go to sleep. I was sure it would come soon. I caught myself dozing off once and checked the time, it was a quarter 'til midnight. I was sure it would have happened by now. I reassured myself that it was the other Chris who was 'initiated' tonight, or else I misheard what they said. Then I went to sleep.
The next morning, I awoke to the sound of someone talking. Wait, it wasn't morning, it was still dark. 'Put on boxers, shorts, a shirt, socks, and shoes; and meet us in the room next door.' I heard Matt say as I continued waking up.
I did as instructed and found all twelve guys from my floor sitting in a circle. Matt motioned toward an empty spot in the circle and I sat down. Matt pulled two decks of cards out of his pocket and explained: 'Ya'll know the drill. Dave, Chris,' he said turning toward me and another guy who I gathered was being initiated too, 'You know how to play strip poker?' We both nodded. 'First one butt naked has to jack off everyone else. When you're, I mean when he's done, there's a treat.'
From that last comment, I was pretty sure they had the thing rigged, but I wasn't about to say something, I was loving this. The group was split up into two circles, with Dave in one circle and me in another. Matt was the dealer for my circle. Matt lost the first hand, romoving a shoe. I lost the second, removing my shoe, too.
I glanced over at the other circle and Dave had all his clothes on. The game continued until 4 of the circle of six (including me) were down to their skivvies and the rest in very little. The other group had a similar configuration. A hand was dealt in the other group, and Dave lost, remvoving his boxers. 'Okay, wait 'til they're done.' I heard the other group's dealer say.
I was guessing someone would lose their boxers in this hand, probably me. But Matt lost and was now down to his boxers. One more hand was dealt and, you guessed it, I was left in my birthday suit. Matt stood up to give instructions. 'Congratulations, Chris and Dave: you've lost. Now, between the two of you, you have to get every guy in the room to spurt before we're done. You can quit, but you won't be able to join the club, and you won't get the treat at the end. If one of you quits, you both lose.'
I started to pull my clothes back on, but Matt gave me an 'oh no you don't' look. We did it the easy way, and I took the guys in my circle, Dave those in his. Everybody opened up their packages, but didn't get totally naked, just pulled up shirts and scooted boxers down to the knees.
I got started right away with Matt. He was quick. He sat back and I got going on another who took a while longer. When I had finished my third, I looked over and Dave was on his fifth. I kept going then saw Dave finish the last guy in his group and move to one of mine. We finished these ones about the same time and sat back to get some rest.
'You quit?' asked Matt.
'No, just resting,' I said.
'Get back on it.'
I finished my last guy a few seconds before Dave did. I saw everyone pull up their boxers and lean in a little waiting. At first sight of cum, everyone pounced Dave and me, sending us to the ground. Matt took my hard cock and started stroking. Another started massaging my balls while another took my nipples. I pulled my legs up a little to allow a fourth to finger my anus. Two others tickled my sides, chest and stomach. I could see the other half of the group was giving Dave the same treatment.
When Matt felt I was about to cum, he lifted his hands off and everyone else followed suit. 'We're gonna make this realy great.' he said. I could see the other group do the same for Dave. They waited until my boner just started to go down (which took awhile) before they went at it again, this time a little stronger. Again, they stopped just before I went over the edge and restarted. When at last I climaxed, I let out a groan and shot a huge load all over everyone.
They started cleaning me up with their own shirts, it felt almost as good as being masturbated.
Everyone went back to bed, leaving their clothes in a pile in the floor. From that point on, we were all really tight and totally comfortable around each other. We had different mutual wanks almost every night.
I always hear people talk about how great their senior year was, but I always think mine was the best.