The Milking Game

I first played the milking game when I was younger. I would often go to my friend Tony's after school. His older sister was sort of supposed to keep an eye on us, but she pretty much came and went as she pleased and we often had the house to ourselves. One afternoon we were playing Mario Brothers in the basement when she came down and announced she was going out. She had barely reached the top of the stairs when Tony turned to me.

"Want to play a cool game"? he asked.

"Ok", I said. "What"?

He hesitated. "Its called the milking game my cousin taught it to me. You can do it with Mario Brothers", he continued. "You play it like normal, but the loser gets punished by getting milked".

"Punished"? I asked suspiciously.

"The loser has to get on all fours, and the winner is the farmer and milks him like a cow". He paused and continued in a low voice by the wiener.

A little tingle ran through mine. I knew little of sex and nothing of masturbation, but I always knew there was something awesome about my penis. The thought of having it milked was simultaneously stimulating and frightening.

I pressed a bit, but Tony was eager to start playing. "Its really cool, you'll see", he insisted. He loaded a short game and we sat back to play.

"This is for all the marbles for a milking"! he announced grandiosely.

"You mean for the loser, right? It's a punishment"?

"Uh, yeah", he said.

We played. Now, this is a game he almost always won because he'd played it so much more than me. But I won this time, and the game went quickly due to uncharacteristic mistakes by Tony. I trash-talked up my victory. Then we were silent for a moment.

Tony seemed embarrassed. "Um the loser has to get bare naked" he stammered.

He started to undress, glancing at me tentatively. I just stared. When he pulled off his whitey-tighties, he revealed a rock-hard boner. I was hard too. Neither of us were developing yet; he sported a bare stiffy of little more than a couple inches. He assumed the position, bare naked on all fours in front of me. "Ok", he was still red. "Now you milk my wiener".

I wasn't quite sure what to do. I raised my hand tentatively for his little penis, then froze in midair. He flinched visibly. We both cracked up giggling.

"Okay, okay", he braced himself again. I gently laid my thumb and two finger tips on his wiener, but he squirmed and pulled away. We repeated this several times.

I was getting frustrated. "What's so cool about this"? I asked. "No, no, I'll show you" he said with a hint of desperation. But I sat back cross legged, so he explained, still in the cow position.

"It's like you get tickled, but you fight it by relaxing so you don't laugh or spaz out", he said. "It's really hard my cousin taught me how to do it. The game is you get your wiener milked, but you relax and don't let yourself spaz out for a long time", and then all of a sudden he said looking at me, "You are completely spazzed out".

I felt another tingle, vaguely perceiving how this might work. I was ticklish all over, and my penis was the enervated center of my hyper-ticklish body. But that wasn't quite the same. I mean, getting tickled most places makes you squirm and laugh, but on your wiener you would completely freak-out. Its just too ticklish. That's why no one tickles you there, right? But suddenly the prospect of getting ones wiener tickled and spazzing out seemed strangely appealing.

He continued, "and you milk. Milk"? He nodded. My cousin squirted milk out of his wiener. I didn't, though. I just got this weird milking feeling when I spazzed out. He says I'll squirt milk when I get older.

I didn't quite understand how the milk got into Tony's cousins wiener, but I was definitely getting a weird feeling in mine. Tony urged me to commence his milking.

I made an okay sign with my thumb and forefinger and started gently milking his downward pointing penis like a cows teat. He would withstand a few seconds at a time before pulling my hand away or squirming out of my grasp. I thought he must have spazzed out, but he insisted on continuing. "You have to go for a long time to get the milking feeling", he explained.

Tony made a herculean effort to maintain his composure, though he was breathing sharply and almost quivering. He got this faraway look when a minute had gone by.

Suddenly he clasped both hands around mine and pulled his knees to his chest. He rolled into a fetal position with my arm sticking in. He was giggling and vocalizing unintelligibly, and his penis twitched rhythmically in my hand. He was spazzing out. The twitching subsided in just a few seconds, and he sat up with a spent, triumphal grin. I knew what I wanted to do next.

"Milk my wiener now, Tony", I said.

Soon I was bare naked, feeling weirdly vulnerable in the cow position while Tony, still naked and erect, milked my little wiener. At first he did it too hard, and then too pinchy, and I could not force myself to be still. But then Tony hit a rhythm, and with difficulty I consciously relaxed my pelvic muscles. Tony was right, it was like resisting getting tickled. After a minute, I grew confident that I could relax through a milking for as long as I wanted, and that that might be nice. I decided, smugly, that I was much better at getting milked than Tony.

But another sensation was welling up from deep inside. It held a certain urgency, like having to pee, except it felt really good. It grew stronger and stronger, making it increasingly difficult to maintain a state of relaxation. Still, I stubbornly practiced my new skill right up until the very point I thought I would explode.

Suddenly my entire body spazzed out. I experienced the rhythmic twitching in my penis that I had just felt in Tony's. My whole being was wracked with pleasure and pandemonium. I had a peculiar recollection of the cuckoo-for-cocoa-puffs bird, and suddenly felt that I understood his joyous freak-outs.

The milking feeling was all over in a few seconds, but I already knew I wanted to feel it as much as possible from then on. Tony and I milked each other several more times that day, and we continued the practice for several years. We made up juvenile jack-off games about milking cows, going cuckoo for cocoa puffs, and other themes. And eventually we really did squirt milk out of our wieners.