Chapter 2
Max: “I was thinking more like an hour. If you are as immune as you claim, you can give me more than 30 minutes, can’t you?”
We agreed to split the difference at 45 minutes. A compromise.
Max: “Any other ‘ground rules’ you’re forgetting?”
Me: “Probably, but nothing else I can think of right now.”
Max: “Well, I have a few more. First, I get the whole 45 minutes. No matter what. There is no quitting allowed. It doesn’t matter if you feel a loss coming on. You can’t forfeit the win over to me. We are going to see this through.”
Me: a sheepish “Okay.”
Max: “Also, you may not physically block or deflect my efforts in any way. You can do whatever you want mentally, you know, think about grandma, or piles of garbage, whatever distracts you from arousal, but no twisting or moving of any kind. You only move when, where and how I say to.”
Max: “No matter who wins, this is just between us. I don’t want our other friends or the other people on or floor to know about this. Bragging rights are just between us. Even between us, it might be better that we never mention this again. This is a one-time only thing that begins and ends tonight.”
Max: “My last and most important ground rule. This cannot affect our friendship. This silly bet is just for fun. You are a good roommate and friend. That’s more important to me than winning a bet. I want you to know that I am not trying to convert you. I respect your heterosexuality. I am going to win this bet, bet, but after, we have to go on as normal. After tonight, this never happened.”
He had clearly given this some thought. I said, “Deal.”
Max said, “Go lay down on your bed, on your back.”
I asked, “Should I take off my shorts or anything?” Despite it being November, like many other resident college kids, I wore shorts most days.
Max walked over to our door and turned the lock. We were friends with most of the other guys on our floor and sometimes they felt free walk right in without even knocking. Tonight would not the night for that surprise. Max answered, “No. I’ll take care of everything.”
He went to the sink and wetted a small wad of paper towels. He placed the wet towels, a dry towel and a bottle of massage oil on my nightstand next to my bed. He looked down at me and said, “Slide down a little and put your feet up on the bar at the foot of the bed. Now reach your arms up hold onto the bars of the headboard. Don’t let go until I tell you to.”
This was an awkward situation. What had I gotten myself into? I already felt vulnerable. With my arms raised over my head, I felt my shirt ride up a little, exposing a strip of bare skin above the waistline of my shorts. Max noticed it too and couldn’t resist swiping a finger across my tender lower abdomen. I flinched and gasped at the sensation. I said, “Hey, we didn’t talk about that! I think we need to make ‘no tickling’ one of the ground rules.”
Max giggled. “Sorry. I saw that and couldn’t help myself. Don’t worry. This isn’t about tickling. I promise.”
He took his phone out of his pocket, tapped at the screen and showed me the display. 45 minutes had begun to count down. He set his phone down on my nightstand by the massage oil. Then he went and got his desk chair and set it at the foot of my bed. He sat, untied my right sneaker, slipped it off and began to massage my foot. This must be part of the foreplay he had mentioned. He soon did the same with my left foot. The massage was feeling good. After a minute, he removed my socks. My feet had been trapped inside my shoes all day. Now they were free, exposed and sensitive. I don’t generally have a foot odor problem, but I had a flash of worry as Max’s face was just inches away. He didn’t seem to react so I guess I was okay. Max gently stroked up and down my arches. It was a very light tickle that felt nice. He wasn’t torturing me. He kept his promise.
Next, he began working his way up massaging my calves. He worked his way higher and higher while rotating between my left and right legs. When he made it up to my shorts he continued inside the legs. He worked my thighs. I was relaxing more and more. He was good at this and I couldn’t help but enjoy the attention. Either his knuckles or fingertips grazed my scrotum a couple of times causing me to jerk a little with each shocking touch.
He stood and unbuttoned and unzipped my shorts before pulling them completely off. He moved his chair to the side of the bed and sat. My underwear was still on, but he turned his attention higher. He began to unbutton my shirt from the top down. After undoing the bottom button, he spread the shirt completely open, revealing the full expanse of my smooth, lean chest and stomach. He let me lay there a moment, feeling both the cool air of the room as well as his peering eyes on my exposed skin. Max and my round innie belly button were staring at each other. Well, my belly button was usually round, but with my arms reaching up, it was more like a vertical oval.
He began to run his fingers around my chest. I was worried about what was to come. He had promised no tickling. Soon his fingers slid down to my sides and stroked lightly up and down from my arm pits to my hips. Again, it was just a light tickle, but I couldn’t suppress a physical response. Goosebumps sprang up over my whole body. I saw Max smile, pleased with himself.
Next, he lightly swiped strokes across my lower tummy. This didn’t help the goosebumps go away and I quivered with each pass over the sensitive area. Then he drew circles with his fingers around my navel. He hooked a finger under the waistband of my underwear. At this point I was surprised and ashamed to realize that I had a growing bulge just south of where Max was currently focusing his attention. He was sliding his finger across my skin under my waistband and working lower. He eventually made it to my pubic hair, which I kept neatly trimmed to a quarter of an inch, and he explored the region.
Max stood up, moved to foot of the bed, reached up and pulled my underwear off. He cast the underwear aside as my partially erect penis sprang free. He climbed onto bed, kneeling between my spread legs, and stared down his awaiting prey. He reached over to the nightstand and grabbed the massage oil. He lubricated his hands and then, leaving my shaft alone for time being, he surprised me by stroking my balls. My sack instantly tightened in response and my shaft grew another degree firmer. He continued to work on my scrotum, careful not to mishandle the sensitive organ.
I was trying to think of anything else. I really was. Any type of mental distraction. It wasn’t working. I was fascinated by what Max was doing to me. My cock jumped up another notch. My partial erection was now close to a full and he hadn’t even touched the shaft yet. Max was looking at it, though. Appraising it and proud of his accomplishment. I began to think for the first time that I might lose this bet.
Done foundling my balls, he reach both hands back up to my armpits and slowly dragged his fingers down my sides, strumming my rib cage, across slight mound of my lower belly and finally he ahold of my awaiting shaft. The touch of someone else’s hand, to me, is so much more exciting that of my own. Maybe it was because I’ve never been touched this was by a man before, but Max’s touch was electrifying and I gasped. It felt like a jolt and I had now completed my journey to full erection.
He began with simple up and down strokes with his well-oiled right hand. It felt amazing. He reintroduced his left hand to my ball sack, twirling lightly. I was definitely going to lose this bet. His strokes began to change. He was now continuing up over the sensitive mushroom cap and finishing with a swirl. This was driving me crazy and it was killing me to maintain my grip on the headboard bars. Next he pressed his palms together and enveloped me inside of this makeshift cavity created with his two hands. He slid up and down and used a twisting motion that almost did me in. He must have realized I was close and, possibly not wanting his fun to end too soon, he changed tack.
With Max kneeling between my legs, the sensitive underside of my throbbing shaft was facing him. He gripped my shaft in his right hand again and began twirling his thumb in clockwise circles around my most sensitive spot – just under the head. The fingers of his left hand resumed a light tickle on my scrotum. The combination of the two sensations was proving to be too much. I was about to burst and powerless to stop it. I threw back my head into my pillow and arched my back as I exploded my load onto my stomach and chest. Max kept up his relentless circles until I was milked dry. He seemed to know exactly when to stop, before pleasure turned to pain.
Without a word, he reached to the night stand for the wet and dry towels and cleaned up the mess I had made. It was an oddly intimate act. To this point neither of us had yet spoken. I began to sit up and Max said, “Where do you think you’re going?”