Me and Sean


When I was in 5th grade, my best friend Sean moved to Melbourne. Before he moved, we would have sleepovers basically every night over the summer, and weekly during the school year; we were really close. We started off shy, but grew together to the point where we would fall asleep on each other’s shoulders while watching movies. More than once, I would wake up in the middle of the night and let my head fall down into his lap, where I could feel his hard on through his boxers on my cheek. I never found out if he noticed this or not, because I woke him up a couple times doing it and I pretended to be asleep until he went back to sleep.

I got his phone number and we still talked all the time after he moved, about AFL and whatever else it is that eleven year old boys talk about. Anyways, my 8th grade year rolls around and my Dad announces that he has a business meeting in Melbourne, and that I can go with him, and that Sean and I could meet at the hotel. I called Sean and told him that I would be in town and invited him to visit me in our hotel room. He eagerly accepted the invitation, and even coerced his parents into letting him spend a few nights there with me. Our hotel room was a suite, so my dad was in one room with the beds while Sean and I would be behind a locked door on the foldout couch.

I was so excited to see Sean. I had grown 8 inches from the time I last saw him, putting me up to almost 6 feet tall. I wondered if he had the same success. Well, no such luck. In fact, he had not changed a bit since the 5th grade. He still had an adorable little baby face to go on his tiny, 5 foot nothing, 90 lb.

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   frame. Anyway, we spent the first day hanging out in the hotel room, watching TV while Dad was downstairs on business. We talked for a while, but I was tempted by his baby face and his skinny little legs in those electric blue basketball shorts. I inched closer to him on the couch and then laid down on top him, putting my head in his lap. We continued talking and watching TV, pretending that everything was normal. But after a few minutes, I noticed that he definitely had a little hard on. I made extra sure to turn my head every time I got the chance, stimulating his little dick. I was so horny then. I decided I needed to make my move if I wanted this week to go the way I wanted it to. I moved my hand towards his waistline and grabbed the elastic on his basketball shorts, ready to move them down.

Dad came back into the room. “Sorry, forgot my papers” he said. He grabbed them and left quickly. As soon as the door slammed, I turned my attention to Sean. He gave me a puzzled look and then burst out into a smile and started laughing.

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   But given the sheepish expression on his face, it seemed obvious that he thought I was just joking. I stretched my arm across the top of the couch.

I turned to watch the upset alert flash across the TV screen when suddenly I felt Sean’s hand grab onto mine. Now I was the confused one, until he moved it slowly downward towards his upper thigh. He pressed it down there and left his hand on top, slowly stroking my hand. I moved my other hand to his chest and started rubbing his flat little chest and stomach. I caressed him for a while as we watched Essendon eke out a win and then I moved my hand up underneath his shirt, continuing to rub. I moved up to his little nipples and swirled them around. I felt them get hard, and then out of curiosity moved my other hand to see if his dick was still hard. It was. I left my hand right there and started rubbing one finger up and down the shaft slowly through his shorts, continuing the nipple fondling. He tensed up as if it tickled, but then slowly calmed back down, signalling that it felt good and he wanted me to continue. I did for about 30 more seconds, up and down the shaft slowly, and then I wanted more. I put my hand on his knee and moved up underneath his shorts until I got to the boxers.

I slid underneath those, too, and then moved upwards until I touched his sack.

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   I groped around and to my surprise, it was still totally hairless. I felt up his balls a little that way but the position got really uncomfortable. I pulled that arm out and tried going into his pants through the elastic waist. But he grabbed my hand as I reached for it. I thought he was cutting things off here. But suddenly, he moved out at my face and started kissing me right on the lips. I grabbed his face, made out with him, and threw him down on the couch, where I laid completely on top of him and continued with the making out. I enjoyed it so much I made a few uncontrolled moaning noises. He started to make some to, clearly mimicking me because he was not sure what he was supposed to do. He was so, so cute. I guess time flew, but we must have been doing this for a good ten minutes, hugging and making out.

Then the uncomfortable click of the door came again, and we both quickly sat up and pretended we were watching AFL. Dad walks in again, glimpses at the tie score displayed on the screen, and then sits in the chair next to us. I was totally pissed at this point, trying to think of any excuse to get away from him.
“You have more work, right?” I asked angrily.

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“Nope," he answered, “all done for the day. ”
“Oh,” I replied.
I looked into Sean’s deep brown eyes quickly, signalling my disappointment to him. The voice of Eddie McGuire commentating on why Essendon was a favourite for the grand final was the only thing heard for the next few minutes, until finally my Dad popped up from his chair.

“We should pull that couch out into a bed,” he said, and then did so, and then the awkward silence continued for another good ten minutes as I stared vacantly at the television.
“Imma take a shower,” Dad said.

“Sean and I will probably just go to bed then,” I answered without thinking.

I feigned a laugh as he grabbed his clothes out of his bag and headed into the bathroom. Quickly, I closed the door between the bedroom and couch area and locked it, ensuring that we would not be bothered again. Then I stripped down to my boxers, and Sean took this as a cue to do the same. Our feelings were clearly mutual for each other, but I did not know how far I could take things. I figured, though, that I may never see Sean again and I should take things as far as I could when I had the chance. I grabbed the tip of his boxers, stretched them out over his dick and then down off of his legs. There was his dick, completely devoid of hair as I felt earlier, all 4 inches of it throbbing and eager for more.

Without blinking, I threw my face on top of his dick and made out with it as vigorously as I did his mouth.

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   I clearly was not a blowjob master, but I figured I would give him all I had. I started with his balls and slowly worked my way up, pursing my lips around his head and then slowly moving down the shaft until I could not go any further. I did not know how to deep throat, but with him I didn’t have to worry about it. I moved my head up and down, and he started moaning loudly. I swirled my tongue whilst continuing the motion, and he moaned louder still. Water was still running in the shower, I knew we didn’t have to worry about noise, so I moved my head faster. The warmth of his dick in my mouth was a feeling I was totally unfamiliar with, but it was most certainly welcome. I continued sucking him off until he yells;

“STOP I’M GONNA CUM!” Well I certainly didn’t let off, I continued harder and faster, ending with one final downward thrust. I felt a warmer substance inside my mouth and knew that he had cum inside.
And then suddenly, there was a knock on the door. I panicked as we were just getting into it and my hand was slowly peeling back Sean’s foreskin. We quickly sat up right and let Dad in as he was impatiently banging on the door. He didn't say anything, just walked slowly towards us. . .

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There wasn’t much of it, but I was still surprised that he was able to do so at all. Kind of shocked, I spat it out onto his stomach. Then I started rubbing it around, spreading a thin layer across the majority of his abdomen. I gave him a quick kiss on the lips and then lay next to him, running my fingers through his straight, wavy, brown locks.
With me lying on my back, my dick was even more visible through my boxers than his was. He seemed taken aback by its size. I must have been around 6 inches at this point, surely larger than he had ever seen. I saw his interest in me, so I pulled my boxers aside to where my dick protruded through the hole in the front. He moved his hand towards it, wrapped his fingers around the shaft, and squeezed it tightly.

Euphoria spread across my body as he moved his hand upwards with a quick jerk, pulling some pubes out of hiding and into the open. I saw the look of bewilderment on his face. I asked him if he had seen them before to invoke curiosity. Then I stripped to let him see more. I didn’t have a nice bush or anything, seemed more like a little string every now and then, but it was still more than what he had.
He brushed his fingers through my pubes, but then returned to the more meaningful prize, my dick.

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   He moved his head over towards it, grabbed the shaft with both hands, and started licking the head around in circles. It was unlike anything I had ever felt before. It was warm, wet, amazing. I ran my fingers as he continued, but I wouldn’t let him go into a fully fledged blowjob just yet. I didn’t want to blow my load into his mouth or onto his back. I wanted this deep inside his ass, and I was determined to get it there.

Without warning, I grabbed him, threw him down onto the bed whist I straddled him, the tip of my dick brushing up against the head of his in the process. Then I grabbed both of his ankles and lifted his feet up over his head, exposing his tight pink hole. I motioned, asking permission. He opened his mouth to answer, but before a reply I had already licked my left pointer finger and penetrated the little star. He tensed up and his eyes grew to the size of golf balls, but I pressed deeper. I moved in past the second knuckle and then jiggled it back and forth. I pushed in and then out, over and over. He relaxed and let out a sigh of relief and pleasure. I pulled my finger out, licked up my pointer and middle finger on my right hand, and reinserted them.

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   He again tensed up, but after some movement relaxed again.

My dick, still very wet from his tongue, couldn’t take anymore. I got up on my knees, stretched his legs up far, and then placed my dick right on his asshole. I moved it around a little, spreading the moisture from the tip and onto the skin around his hole, and then with one thrust pushed downward.

The entire head penetrated. Sean gasped, clearly in pain. But I wouldn’t come this far to worry about him. I slowly pushed in, deeper and deeper and deeper. His face wrinkled in pain and closed his eyes shut tight. I thought the wrinkles made him look even cuter. I pushed all the way in, until I felt I couldn’t go any further. Then I grabbed above his hips and pulled him away while pulling back with my dick. And then suddenly I pulled him towards me again while thrusting back inwards. He let out another breath, but this one sounded more pleasurable and less pained. So I repeated, out and in, over and over, quickening the pace and increasing his pleasure each time.

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   And after what couldn’t have been more than a minute, I was ready to blow my load. I pushed as far in as I could, pulled him toward me tight, and squirted once, twice, thrice, and then a fourth and final shot. He let out a loud moan, then opened his eyes, and looked back into mine.

I pulled out slowly, looking admirably at the hole I had just wrecked. Cum oozed out of it. I figured that needed to be cleaned up, so I picked up his boxers off the floor and used it as a rag. I wiped off what was left of cum and saliva on his chest too, and then threw the boxers into a wrinkled heap by the bed stand. I lay down next to him, both of us butt naked, and we dazed up at the ceiling until we dozed off. I woke up at about 3:30 AM, looked around and realized that I hadn’t just had a good dream, and then noticed Sean’s typical hard on while he sleeps. He was such an angel, so peaceful in his sleep.

I figured I should give him a hand and wrapped my lips around his dick again. He moaned a little in his sleep but didn’t wake up, just like the old days. I finished the job quickly and more efficiently this time, and he again blew his load right into my mouth. I thought about spitting it out on him again, but he was asleep and that’d be gross. So I just swallowed it.

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   I thought about what I had done. It seemed gross at first, but having Sean’s seed inside of me turned me on so much that I lapped up the little bit that dripped back down onto his dick and swallowed that up too. I tickled his balls a little until he rolled over onto his side, and then I lay behind him in a spooning position and dozed off again, arms wrapped tightly around him and dick rubbing up between his cheeks.
When I awoke the next morning, my Dad had already left for another meeting. I jumped on top of him, straddling his chest and letting my already hard dick dangle in his face. I shook him awake and yelled;

“READY FOR ROUND TWO?” He smiled, and I grabbed his legs up, ready to go again. Then he said, “This time, I want to be on top. ”
“Fair enough,” I replied.
I sucked off his dick, got it nice and moist, and then lay back on my back, lifting my legs up for him. He seemed nervous at first, but he looked into my eyes and clearly had a new life rejuvenated in him. He eagerly licked two fingers and shoved them in at once. I grimaced. It was another totally unique feeling. For a while I thought he had torn my butt apart, but I quickly got used to the feeling as he moved in and out with his, just as I had done. Soon after, he was ready to go and put his dick inside of me.


   It felt huge if I hadn’t seen it before I would have sworn it was a coke bottle or something. But again, my ass adjusted and I was able to take it. He wasn’t, however. After about 45 seconds, he gave one final push and came inside of me.

“Yeah,” he said, “I definitely liked taking it more. ”
“Well, let’s take care of that then,” I answered jumpily, and we were at it again.

That turned out to be the shortest but best week of my life. We experimented, doggy style, cowboy, and a few others. We must have had sex ten or eleven times in those few days. We spent every second touching for the rest of the trip, showered together secretly while Dad was at meetings, slept spooning, and even secretly held hands as we walked to get food from the restaurant downstairs. When it came time to go, I was devastated. He pretended to leave his phone in the room so we could return for one final goodbye quickie.
But, finally, we said our goodbyes and parted. I kept up with Sean on the phone for months after that. But we were in high school, more work, more responsibilities, more friends, and we slowly drifted apart.

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   My dad got laid off, money got tight, and we weren’t able to make another trip to Melbourne. Daily calls switched to weekly, then monthly, and I haven’t heard from him in two years now.


Credits go to Anonymous. .



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