Pretending to Sleep

By Terrance Phillips

Published on Apr 21, 2005

Gay

My name is Ron and I'm 17 about 6'1" tall. Since I was about 14 years old, people have been telling me that I'm extremely good looking. I work with my dad on the weekends clearing building lots and between all of the lifting, and my mother's obsession with healthy eating, I've gotten a pretty good physique. I'm not overly muscle bound or anything but I've got pretty broad shoulders, a washboard stomach that tapers into a 29" waist and yes those cool lines that separate my legs from my torso.

More than one girl has told me that she cries herself to sleep over me. What a line! Unfortunately for them, I'm gay. No one knows I'm gay, I've never been with another guy or anything (not that I haven't been tempted especially with one guy in particular) but I just have the feelings other guys do for girls for guys.

My family and I moved here about a year ago but I still don't have many friends. I think the other guys are jealous of me because of the way I look. Pretty much my only friend is John. He is also 17 about 5'8" tall and is really cute, even though he doesn't think so. I've heard more then a few girls comment about how cute they thought he was and it was all I could do not to tell them to stay away from him.

John called me the other day and told me his parents were going away for a week and said they were going to let him have a friend stay over while they were gone. He wanted to know if I'd like to stay. At first my parents were hesitant to let me go since John's parents weren't going to be home, but John's dad called my dad and somehow convinced him it would be okay.

Since John's parent were catching a late flight out, they picked me up pretty late on the day they left, so I didn't get to John's house until after 9:00pm or so. Even though it was dark, I could tell the house was huge. John and I went up to his room, which was about half the size of my parents' house, and played video games until we got tired enough to go to bed. I bet him that that whoever lost the most games would have to give the winner a full body massage. I was eager to have him give me a massage and trounced him.

"I can't believe I lost the bet" said John.

"A bet's a bet John" I answered.

"Isn't this, well a little gay?" he asked.

I was a little annoyed at this point and asked "No, and if you thought so, why'd you bet in the first place, are you a chicken or something?"

"I don't know," he answered "I guess I didn't figure I'd loose."

"Well you lost so get to it!" I told him.

"Oh alright." He answered.

I started to undress while John just stood there with a dumb look on his face staring at me.

"Hey, you don't get to keep your clothes on you know." I told him.

"Oh, yeah right." He said coming out of it.

I'd only seen other guys in their underwear briefly in Gym class mostly wearing boxers or in clothing catalogs, so I was doing my best to control my tool as I got undressed.

When John took off his pants, I noticed he was also wearing Hanes briefs. I almost lost control at that point. I loved seeing guys in white briefs. They have to be the kind with the standard fly though. I don't like those man panties a lot of guys call briefs.

"Hey, you wear briefs too?" I asked. "I thought I was the only guy that still wore them."

"Uh, yeah. I don't like the way it feels when everything swings around." He answered.

After that remark, the stirring in my crotch made me decide to change the subject quickly.

"I've never slept in a waterbed before." I told him as I got into bed lying down on my stomach to hide my growing tool.

"I've had it for awhile. It's great in the winter when it gets cold." He answered.

John straddled me and sat on my butt and began rubbing my shoulders slowly working his way down to my legs not even touching my butt. His fingers did rub up against my nuts a couple of times though, as he rubbed my inner thighs.

"Okay, all done." He said.

"No, you're only half done." I told him pretending to be sleepy. "You still have to do the front" I said as I flipped over.

"Where am I supposed to sit?" he asked.

"Same as the back" I answered.

"I'm not sitting on your dick!" he exclaimed a little too quickly.

"You don't have to sit on my dick." I said. "Just straddle me."

My tool was about three quarters hard at this point and I noticed John checking it out while trying not to seem like he was.

He quickly worked his way down the front of my body.

"Okay, all done." He said, in about half the time it took to do my back. He got up, turned out the lights and nearly jumped back into bed. It was at that point I noticed that his alarm clock threw off enough light to see by.

John quickly fell asleep on his left side facing me. As I stared at him peacefully sleeping I could feel a burning in my eyes. A wave of despair fell over me as I realized that he would probably never know how much I loved him. I was too afraid to tell him how I felt about him because I knew it would be the end of our friendship. He had never given me any definitive indication that he was gay.

After about a half hour of watching John sleep, he turned onto his back. It was at that point that I wondered if it would be possible to touch his tool without him being aware I was doing it. Suddenly the little head started doing the thinking for the bigger one and I found myself ever so slowly moving my hand toward him.

It took about two minutes for my hand to make the journey toward him, this way if he woke up I could just claim I had been sleeping. My heart sped up when my hand hit his hip. Ever so slowly I moved my hand up across his hip and toward his cotton sheathed crotch. This journey took far less time. His tool was rock hard and felt to be about the same size as mine.

I got quite the fright when John rolled back over onto his side facing me but had the presence of mind to quickly move my hand away from him. After my heart started beating again, I decided to see how heavily he actually slept. I turned over onto my left side facing away from him and moved back until he was spooning me. After a couple of minutes like this, he put his hand around me and rested it on my stomach.

"Perfect!" I thought. This would make it a whole lot easier. I pushed out my stomach which moved his hand out and then quickly pulled my stomach back in. His hand slipped a little further down my stomach until it was resting on my underwear waistband. I moved up a little turning slightly so his hand would continue its journey toward my crotch. After a bit of maneuvering his hand was resting lightly on my very hard tool. I nearly yelled in shock as his hand closed around it. His hand must have closed involuntarily he probably thought it was his own tool he was grabbing.

After about 5 minutes like this I convinced myself if I moved slowly enough, I could put my hand in his underwear and touch his tool without anything between it and my hand. If I was really careful, and lucky, I might even get a chance to feel how big his nuts were. They looked way bigger than mine based on the bulge in his briefs. The thought of being able to pull this off sped up my pulse and my breathing.

Ever so slowly I began to turn onto my back forcing him (since he was so close to me) onto his back. When he was finally lying on his back, I reached over and slowly slid my hand into his briefs and encountered nothing. I was a little surprised. His tool should have been there! I moved my hand slightly to the right and finally struck gold. I used my index finger to slowly measure the size of his tool being careful not to wake him up. He, like me, was cut, and seemed to be about the same length as me, around six or six and a half inches, except it was perfectly straight.

My tool has a pretty sharp bend to the left about 3/4 of the way down the shaft. I always figured this was the way everyone was and it had to do with the path it took inside a girl. I slowly moved my hand back down his shaft until I came to his nuts. I was right but still surprised. Each one had to be about three inches long and about two inches wide, almost twice as big as mine. I have pretty big hands and I could barely fit them both in one hand at the same time.

I moved my hand back up to his shaft and closed my hand around it. It was about the same width as mine so that put it around five and a half inches or so around. Ironically both of us were about average in size, except for maybe his nuts. After about 5 minutes of feeling his tool pulsing in my hand, I decided I had better jerk off before John woke up and found us holding each other's tools.

I slowly pulled my hand out of John's briefs, made sure he was still sleeping and got up and went to the bathroom. It only took a few quick tugs thinking about how I probably could have gone further and maybe even tried to blow him, for me to shoot my load. I cleaned myself up and went back to bed. It didn't take too long for me to fall asleep this time.

As you can see, I decided to write this and the next chapter or two from Ron's perspective. We have long since gone over what happened so I know exactly what he was thinking about during our first few times together.

Next: Chapter 5


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