Derek, Babysitter at 15.
Introduction:
This is another true story of what Derek and I done together. Continuing from the end of “My First Sleepover”.
Barely speaking to eachother I got dressed, brushed my teeth and left Derek’s house. And that was all that happened for several months, things continued as normal each day and I visited his house more frequently; straight after school for a few hours whilst my Mom was still at work and sometimes all day on the weekend when both my parents were in a hotel some place. My Mother, being the perceptive woman she was, noticed that I was spending a lot of my time outside of school with my new friend so one particular sunday evening after I had arrived home late (and not for the first time) from Derek’s house she announced that she was going to go and speak to Derek and his parents. So that’s exactly what she did, dragging me along almost crying behind her she paused only for a second to knock on the door – unsurprisingly Derek’s Dad answered the door and, seeing me cowering behind my mothers legs, invited us in. It was then, mid way between sitting and standing Derek’s Mom walked through the kitchen door and started chatting to my Mom. I had no interest in the contents of the conversation so I took no notice of anything that was said, not until my name was mentioned… My heart stopped and everyone in the room seemed to be staring straight at me; I dared not lift my eyes from the patch of carpet that had been the main focus of my sight for the past 10 minutes – it was only when my name was mentioned again did I actually look up and realise that they were not, in fact, adressing me but eachother as though I was not there, merely another empty seat. The sound of my name had aroused my ears and now I listened intently for any more information that might shed light on what the conversation was about, I heard words like “Babysit” and “Holidays” I assumed that Derek’s parents were going on holiday somewhere soon and needed a babysitter; maybe my Mom was going to look after Derek while they were away – I thought about that and it seemed like a dream. The boy that I had shared my first remotely sexual experience with, living in my house, possibly sleeping in my room. I couldn’t of been more wrong.
Nothing more was said about babysitting or holidays that night and I left all the more exciting for the next few weeks. That all changed exactly two weeks after that night, I had just got home from school having not been to Derek’s that day and my Mom said that she wanted to talk to me; We sat down after dinner and she said that she and my Dad were going to go on holiday for a week but that I wasn’t allowed to come, something about it being a work trip and not suitable for children. Then it clicked, they weren’t talking about Babysitting Derek, it was the other way around. Derek’s parents babysitting me. That wasn’t so bad, they seemed like cool people and Derek certainly was. So it was set, my parents were going away on the 2nd of August and I’d be staying with Derek’s family until the 10th; I was excited yet undoubtedly nervous about spending that much time away from my parents. Like I’ve said before, I was a very shy child and a week would definitely be the longest period of time that I’d spent away from them. The days before they left seemed to drag, each one taking longer than the last and the day before seeming to take just as long as the whole week. But eventually it did pass, then the day came and my parents set off for the airport; dropping me off at Derek’s house on the way. The first day was the same as any normal day at home or at Derek’s – Have dinner, play video games, shower then bed. The sleeping arrangements were the same as the sleepover, The spare bed that had been occupied by Steve and Paul was now back in the garage, behind countless bikes, skateboards and paint pots. So it remained the same, Derek and I sleeping in the same bed. It wasn’t until the third day that things began to change. Derek’s parents said that an ‘urgent’ family problem had come up and that they needed to leave the same day; on account of Derek being almost 16, they seemed to assume that he was capable of ‘looking after’ me considering I was 12 and no longer a baby. So that’s what happened, Derek and I were alone for the rest of the time my parents (and now his) were away.
The routine that had been established, eating dinner then playing video games etc.. had long since been abolished since his parents had left and now we were back to what we liked to do. Sitting around in briefs eating junk food and watching TV constantly. I think that I’d almost forgotten about the little thing that Derek and I had done by the time the fourth day came along, I suppose that I’d had so much fun that I just wasn’t thinking about that kind of thing anymore. That was until Derek done something… Unexpected. I’d just came out of the shower and wandered into the bedroom to get dressed and play some video games when I noticed Derek sitting at his computer. I guessed what it was that he was looking at so I made my presence known by giving a slight but defined cough directly behind him, to my surprise he barely acknowledged this; not wanting to see what was on the screen I quickly moved past him and started to get dressed by the bed. I’d got dressed as slowly as possible without seeming like I was trying to be slow, when I finally couldn’t not look at him I had a perfect view of his stretched briefs, a tent rapidly forming in the front. Exactly where I knew his 7″ cock would be growing and tensing at the sight of the porn on the computer, without and prior thought or consideration I moved back over towards him and looked at the screen. Then I stared, for what could of been days; the men were doing something that I’d never even thought about never mind considered doing. That video was my first sight of Anal sex and I’ve loved it ever since. Losing all control over my body, I began to get a tent of my own, obviously much smaller than Derek’s but still enough to be seen. In one swift movement Derek had pulled down his briefs and released his monster cock, throbbing and covered in precum and this only made me harder now causing my briefs to part company with my skin, feeling more embarassed by the second and Derek looking all the more pleased I made a decision. One which I’ve never regretted.
Less than a minute after Derek I had pulled down my briefs and taken a seat on the bed next to Derek. I felt nervous again, not knowing what might happen in the coming moments. Wanting to reach out and suck on Derek’s member until he exploded inside me but I didn’t. I couldn’t. I didn’t have to, because he had made the first move for me; he leaned over and kissed me hard on the lips, pushed me onto the bed and explored every part of my mouth with his tongue. We stayed in that position for seconds, maybe minutes before I felt the sticky precum from his cock oozing over my stomach and then I made my move. Pushing him off I stared at his dick, the thick pulsing veins and sticky head and I thrust my mouth towards it. Wanting him to erupt and fill my mouth with his cum, but no? He had pushed me off. Did he not want this as much as I did? Had I misread what he was intending to do? No. He wanted it the other way around. We changed positions and he enclosed my twig of a dick into his mouth, having grown and being about 5″ now it seemed more difficult for him to accept it all. He did it though and I could feel him gagging on it as his throat massaged the tip and my preteen body jerked with pleasure; I stopped though, I didn’t want to be finished so soon. Not again. It was my turn to push him off, a look of disappointment creeping across his face as I did so.
“Derek, I want to try what the men in the video were doing.” I whispered.
“Are you sure? I’ve never done that before and I might hurt you.”
I replied with a nod and got onto my hands and knees, ready to accept his cock into my ass. I dared not look, the sight which awaited me couldn’t look pleasant. It was his breath that I felt first – warm and moist his lips slowly caressed my ring. Then his tongue circled my hole, slipping through once or twice. Then as rapidly as he had kissed it, he stuck his tongue in as far as possible, maybe 2″. That shocked me, I had not been expecting such a releasing feeling. As quick as it had begun, he retracted his tongue and sat on his knees.
“Ok Ben. I’m going to try and put it in now. If it hurts then tell me and I’ll stop straight away”
He had barely finished the sentence when I felt the throb of his dick pressed against by hole. Squashing it’s way past my muscles and delving into my moist insides. There was pain, as I had expected but it was nothing that couldn’t be hidden by groans of pleasure eminating from both our lips. Evidently this felt as good, if not better, for Derek than it did for me. After several minutes of Derek thrusting his 7″ cock into me he said something totally inaudible alongside both of our moans. I had guessed what was coming, as it came. Literally. He flopped onto my back with his dick still enclosed in my ass; his warm teen boy juices running out back along his cock and down towards my balls. I pulled myself off of him and turned to sit and admire his softening manhood, when a thought occured to me. I bent over and stuck all of him into my mouth and down my throat, feeling him getting erect again as I went. I gagged and took it out of my mouth, smiling with his own cum spread around my mouth up at him. Knowing from the last time we’d done anything like this that it was now my turn to feel the pleasure of the insides of a boys ass. Sensing this at what seems the same time he spun around and lay on his back, spreading his cheeks for me to delve my lips into the hairy mass of what was his ass. I done as he had done, moving in circles around his hairy hole with my tongue and forcing it through his strong muscles once or twice. Then sharply pushing my tongue all the way in, swirling it around and getting a taste of his flesh, my nose now pressed into the hair at the bottom of his balls. Then I sat back, gazing at the hole that was about to be penetrated by my preteen twig, now wet from the cum wiped on from my ass and balls. Without and prior warning I jabbed at his hole, slowly fucking his virgin hole with my throbbing and tensing dick. It must of been obvious to Derek that I didn’t jerk off at home regularly, I was ready to cum within minutes. Almost shouting that I was ready I jerked and thrust yet deeper into him feeling my immature seed shoot even deeper into his now stretched hole. Not wanting the moment to end, we lay together on the bed; now covered in both of our cum and slept. My now soft dick still pressed against his no longer virgin ass.
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