Measuring Up 1 (T/T+, High School) THE CHALLENGE
James, Alan, Billy and I started summer break from high school and were going to spend the summer at the beach. We were hanging out at James house while planning our summer vacation. It was on this night that the challenge started. James and Billy were arguing when James said, "You are full of shit shrimp dick."
This comment sent Billy into a rage. I don't even remember what they were arguing about. Billy shot back at him, "Who are you calling shrimp dick. I'll beat your dick any time." This caused laughter from everyone. Billy glared at James and said, "You know what I mean. My dick is a "mans dick" not a "little boy dick" like yours." James said, "Yea, right." This made Billy even madder and he swung at James. We had to pull them apart.
We left for the beach on Monday. The four of us were sharing an apartment with two bedrooms. James and I shared one room and Billy and Alan shared the other. We were excited over the trip and looking forward to enjoying the summer. It was Billy who brought up the argument with James again when he said, "You need to apologize to me for you smart mouth." James looked at him and said, "Billy, I just call them as I see them." This caused Billy to get irate again. He said, "You are so full of shit. Let's measure them and then we can call them as you see them."
THE MEASUREMENT
The challenge was on. James would not back down as he said, "What do you want to do; get a ruler and measure them? You want to look at my hard dick? You want to see my hard-on? I don't mind." We watched in awe as James started undressing. As he was removing his jockey shorts he said, "What are you waiting for shrimp dick. You can't compare your cock hidden in your pants. You can get it up can't you?"
Alan and I sat and watched as our classmates stood naked and started stroking their cocks to erections. It was James who said, "How are we going to measure them? I don't trust your readings." Billy said, "One of them should do it. We need a measurement form the same person so they are measured alike." Alan spoke first, "I'm not going to touch your dicks. That would be queer." James looked at me and said, "How about you. Just measure them." I looked down at their rising dicks and said, "What ever?" This was my first mistake.
We could not find a ruler so it was decided that I would put a piece of paper next the dicks at trace them and we could then compare them side by side. I did not say no. This was my second mistake.
I was handed the first piece of paper. It was decided that I would put the paper on top of the dick and push it to the pubic bone at the start of the dick and trace each of their cocks. James said to do him first. I was nervous when I moved the paper toward his cock. I could not figure how to trace his dick. James laughed, "It won't break Robert. Hold it and trace it underneath along the side of my dick." I had to kneel down to trace the erection. It felt strange holding someone else's dick as the pen drew an outline of his hard-on. I was leaning over looking up toward his dick. It was Alan who said, "Shit you have his pre-cum on your hand. You look like a fag playing with James." My embarrassment grew when Billy moved over and took the place in front of me where James had been. He was kidding when he looked down and said, "You want to give me a suck before you start measuring? I won't mind." Everyone laughed and it pissed me off.
I grabbed Billy's cock a little harder as I placed the paper over the top of his dick. I made the second measurement. It was over. Now the two could compare the drawings. Billy's drawing was wet from his leaking rod. Alan said, "Is this drool Robert or is it Billy's cum?" Everyone laughed again. James had the larger dick as his picture was about a half inch larger than Billy's.
JAMES SHOCKED ME
It was a couple of hours later when we were ready for bed. James started undressing. He looked at me and said, "I didn't think you would really play with our dicks. It was kind of odd don't you think?" I don't know of anyone else who would do what you did. You enjoy playing with my dick?" I came unglued, "You were the one who asked me to do it. You said it was not queer." He shocked me when he said, "I didn't ask you to get boned from playing with our dicks." Little did I dream that this would cause so much trouble with James? I tried to argue with James but he just smiled.
James said, "Sleep easy I might need something from you during the night." Billy heard him, laughed, and said, "I guess you'd better sleep light Robert. You know that James wants." We all laughed at that but James was just smiling at me as he said, "Hell Robert, you're going to learn a lot this summer and you don't really mind do you?"
I was nervous as I slept in the room with James. You have to know about James to understand my nervousness'. James was an exhibitionist and just before we went to sleep tonight he stripped and walked around the room naked. He said it felt better to swing free. I didn't feel attracted to James body but having him naked around the room unnerved me.
James looked at me and said "I sure could use a bottle of water Robert." I went to the kitchen and got the water for James. As I was heading back to the room Alan yelled, "You had better hurry; James might need his ass kissed too." Both he and Billy laughed at me. I felt "as low" as one can get.
When I entered the room, James was sitting on the side of the bed with his legs spread wide with a "semi". I looked down at his hardening cock. If you could imagine my humiliation watching him as he started jerking off. It was if I was not even in the room. I watched as James shot his load all over his abs. He looked at me and said, "Get me a washcloth."
I went and got the wash cloth, I handed it to James. He said, "Thanks man I'm a mess." I looked down as he started to wash the cum from his groin. It was like I was living a bad dream as he cleaned the last of the sticky cum from his balls. My humiliation was growing. I stood there as he jerked off and Alan and Billy knew that I had watched him. I watched as James washed his groin. I entered my bed with an erection.
MY HUMILIATION GREW
The next morning Alan and Billy wanted to know everything that went on last night. I didn't want to talk about it but James did. He watched my reaction at breakfast as he told Billy that I had helped him jerk off and had even helped him clean up. I can still hear Billy as he said, "Shit that's gross guy." I was nervous all day as we walked the beach and hung out. To my relief everything was back to normal. James was actually nice to me all day but just to play it safe I kept my distance from him.
Things were pretty normal until bedtime tonight. I hurried to get in my bed hoping James would leave me alone. He stayed up late playing cards with Billy and Alan. I never heard him as he entered the bedroom. I felt the first shake and heard James call my name, "Get up." I was still groggy as I said, "Leave me alone I was asleep." He kept shaking me. I eased out of my bag and mumbled, "What do you want?" He laughed and said, "We are all in the sitting room, get you're butt up." I moved toward my pants when I heard him say, "No like you are, it's just us guys here." That's when I noticed that James was naked. I looked at James and he had a look that said, "You like this shit don't you?" When our eye's met his smirk said everything.
I entered the sitting area. Everyone laughed as I looked down James naked dick. I think I turned a dozen shades of red and I started back to the bedroom when James said, "Who said you can leave?" I looked over at him with a questioning look on my face. I never answered and he said, "Come over here and sit on the floor."
I am now sitting on the floor but I keep trying to look away from the group. My glaze kept coming back to James's semi cock not a foot from me. I can tell the game is about to end. Thank goodness I can go back to bed. I looked over at James and could see the lust in his eyes. His dick was hard and pointing toward the ceiling. James said, "You mind helping me tonight." Fear was frozen on my face but I never answered. Billy said, "Is it OK with you if I watch." This surprised me as I had not answered or agreed to do anything. James was sitting on his bed in the same position as last night when he jerked off. I glanced down at his erection. Billy was staring intently at me and at Robert. I think he wanted to see how far we would carry this.
MY FIRST SUBMISSION
James jumped when he saw me slowly reach my right hand toward James cock. I did a pretty good job of jerking him off as Billy cheered him on. He said, "Now go get the wash cloth."
I guess I was drawn in today by James. Not only did he make me get out of bed tonight as they played cards but he had me jerk him off as Billy watched. I can still hear Billy say as he left our bedroom, "Man, I can't believe you did that. You should have told James to eat shit." Yesterday I watched him jerk off and now I had actually jerked him off. I slid into my bed and was asleep again when I heard James, "Robert wake up, and I need you." I realized that it was daylight as I pushed back the covers. I moved around the bed and asked James, "Now what do you want?" I saw him look down toward his crotch and as I followed his glaze. I saw the tent in his sheets. He had a morning erection and expected me to jerk him again. A smile came across his face as I moved the sheet back from his body. I was watching my hands move toward his hard-on as if it were someone else grabbing the hard teen dick. I stroked him as he squirmed on the bed. I heard Alan and Billy in the
sitting area as I jerked off James the second time. James cum burned as it splashed on my hand and arm as he shot his morning load. I had made another mistake.
NEW LEVELS
Well we have been at the beach a full week now and each day has been pretty much the same. We hang out during the day, looking for girls and working on our tans. I have become accustom to James giving me orders. I guess I have even become used to the nightly ritual.
This morning the ritual took a little different turn. After I finished the morning chore with James, you know what I mean, he tells me to kneel beside his bed. "As he starts stroking my hair with his right hand, he starts a pep talk, "You have done pretty well so far, Robert, maybe you are ready to help during the day. What do you think?" He never let me answer as he kept on talking and rubbing my cheeks and chin with his right hand. I was so intent on his conversation that I did not realize that he was now rubbing my lips with his index finger. "I think you are ready don't you think." Sometime during his talk he had pushed his finger past my teeth and was rubbing my tongue.
I keep playing the conversation over and over in my mind. Why did I let him push a finger in my mouth and what does he mean? I keep thinking, why did I let him rub my face. It was if he was marking his territory. I couldn't believe it. He thinks I'm a queer. Yet, I wouldn't have jerked him off unless I was one. I said, "Please James, don't make me do anything else. This could get to my parents. I'll do anything you want, just stop."
I realized that was the wrong thing to say as soon as I had said it. "Anything", what was I thinking? James already had control over me half the time. He didn't miss the "anything" though. He said, "No one will find out, I'll not tell." My face started turning red as I looked at the sneer on James face as he said again, "But who knows how far you will go?" Hell I even started to bone. What is wrong with me? Why do I keep getting into these situations?
BILLY TAKES PART
I had given in to James over and over. I sat in the sitting area as James showered and got ready for tonight. I was daydreaming when Billy came out of his bedroom just wearing his jockeys. "Hi Robert, I didn't know you were here." He looked kind of nervous as he said, "Will you help me with something a minute in my room."
I followed Billy into his room. He was speaking quietly as he said, "James said you do anything to keep us quite. Is that right?" This was something I never expected. I had even forgotten that Billy had watched James and me that time. "I don't know man; I'm not going to do any thing. You know that James made me do these things." Billy laughed as he said, "Did James ask you to wake him up by beating his meat every morning? He said they way you lick your lips you would probably suck his cock before the summer is over. Is that right do you want to suck his dick?"
I came unglued for the second time on this trip. "I'm not gay and I'm not going to give anyone a blow job." As I was pulling away from Billy I glanced down and saw the head of his cock was poking toward the band of his jockeys. He had a hard-on. This trip just keeps getting worse and worse. As Billy grabbed my arm and I felt him start to push me toward my knees. He said, "Listen, just kneel here and jerk me off like you do James and this time I won't say anything."
I was kneeling in front of Billy's crotch as he pushed his jockeys to the floor and stepped out of them. His cock was fully hard and sticking at an angle toward his belly button. His bushy brown pubes looked like a forest compared to James. He was hairy all over even on his legs. He looked more gorilla like than teenage boy. I had never jerked off James kneeling in front of him. This was strangely exciting being this close to the hard cock. I thought, "Hell all this talk of being gay is causing me to doubt my own sexuality. I'm not queer. I'll just hurry and get it over with."
I grabbed Billy's cock and began to jerk him off. He moaned and humped my hands as I stroked his rod. It was only a short time before he told me he was ready to shoot. I caught all the blasts in my right hand. I wiped the goop on his stomach and in his bush. He looked down at me in the kneeling position and ran his finger over the tip of his cock.
He caught one last string of cum on finger and looked down at me. He smeared his cum on the outside of my lips. I even parted my lips when he pushed the end of his finger in my mouth. Billy looked down and said, "That's what I thought." I guess Billy had marked his territory this time too.
James and I left the room later and Billy yelled, "Hey Robert I'll see you tonight." James looked at me and said, "What was that about?" I looked over and said, "I guess you told Billy about him not talking. I guess he wants a price for his silence; he wants me to give him head. He also said you thought I would suck you off before the end of summer. Did you say that?"
"Yea, he and I were talking and he was asking me about what, you know, what you do. I told him it felt a lot better than my doing it with my right hand. He then asks me if you had sucked my dick. I said no but I thought you would soon because I thought you wanted too. I thought you would take a little persuasion." I was mad as I said, "I'm not going to suck you or Billy, that's queer." He looked at me and said, "We'll see."
THE NEXT SUBMISSION
As we left the room we walked toward the ocean. As we passed the dunes I thought I had to talk James out of continuing. It was OK to help him out or even help Billy but the blow job talk made me nervous. We had entered and area that was not as populated as the beach area the hotels were located. We were in the dunes just a few minutes when James said, "What would you do if I told you to suck my cock?" This was not the conversation I had expected. I hadn't answered him when he continued, "You did say you would do anything for me earlier today." I was confused as he had turned the "anything" around. I didn't mean that, did I?
"This morning when I put my finger in your mouth you sucked on it. You were kneeling beside my bed with a hard-on and you were sucking on my finger. I told you that you have done pretty well so far, maybe you are ready to take the next step. You know sucking my finger is not a lot different from sucking my dick. It is still just skin and bone. Except I can shot with one and can't with the other."
I knew I had turned red and stared at James he reached up with his index finger and rubbed my lips. "You going to open up and suck me again, just for practice. What do you think?" He never let me answer as pushed his finger past my teeth and was rubbing my tongue for the second time. "Come on suck on my finger; just imagine what it would feel like to try this on my cock." I actually sucked on his finger. I heard his snicker.
I knew what he wanted. He wanted me to suck his dick. My face started turning redder as I looked at the zipper and saw the sneer on James face as he said again, "Pull it down you are almost there." I even saw his bone. I did as I was told and pulled down his zipper. James moved up and let me lower his jeans. I even removed his tennis shoes and pulled his shorts off his legs. When I moved back into the kneeling position I saw his hard-on in his jockeys. I hooked my hand in the band and started down with his shorts.
James moved up so I could get the jockeys over his hard-on and below his hips. I pulled them off. As I rose back up I saw his rod. I had jerked him off a few dozen times since we had reached the beach. I had never really been this close to his hard cock. James looked down and said, "Its time. Watch the teeth and I expect you to swallow it all."
I made the decision that would change my life. I looked at his large balls and I knew how much cum they had spew when I jerked him off. I knew they were ready to fill my throat with a large dose of his boy sperm. I saw the black pubic hair that I had stroked each morning and thought of the first time I woke him up by jerking him off. I think I wanted to do this then but I couldn't.
I placed my mouth over his cock and I was sucking my first cock. I started moving my head up and down on his rod. Just and inch at a time to start. I wanted to please James and I started opening wider and taking more and more of his cock into my mouth. One inch at a time he entered my mouth. I looked like I was a sword sallower. He never moved but let me do all the work. I think he wanted to make sure I gave his cock the proper worship. My lips caused the only force in this blowjob as I stroked the soft spongy shaft as it slid in and out of my mouth.
My lips could feel a large vein like tube running the length of his cock. I wanted this to last forever so I pushed further down each time I took his cock into my mouth. After a few tries I felt the pubes at my nose. I had his whole cock in my mouth and I had only gagged a few times. I did not have to wait long before I felt James start to spasm and I knew my task would soon be complete.
As James started jerking around in the sand I felt his first blast of cum hit the back of my mouth. I clamped my lips tightly around the mushroom head of his prick and let it shoot into my open mouth. I was not going to let a drop spill. My first blowjob was going to be completed just as James had told me. After James cock stopped shooting I slowly swallowed. He looked down at me and said, "Shit that was awesome."
I have just given my first blowjob to James but I guess it will not be the last. I had given in and did as he asked.