Benjamin's Journal - KEEP OUT

This journal belongs to:
Benjamin T. 
Age 21


November 8
Okay, so I haven't used this journal in a long time, and this entry is going to be a big one. I can't help it though, something happened and I need to get it down so I don't forget all the details. I'm good at keeping prying eyes away from this thing, so it should be okay. I still can't believe I'm writing this, but... here I go.

It was last night when my buddy calls me up to ask for a favor. We've known each other since middle school and if I'm being honest, I'm the only one he can really count on to do things for him. Some people call me a pushover, but I like to think I'm just nice and like helping people out. Anyway, his parents are out of town and my buddy wants to take this opportunity to visit his girlfriend overnight. The only problem is, he's got a little sister who's only ten years old and can't leave her alone for that long. So there you go, I'm now a babysitter.

I show up in the evening and his sister Ashley answers the door looking cute as a button. I have to admit, I've always thought she was really adorable. That is to say, I've always been attracted to her. I could never tell anyone, but her little body and friendly innocence drove me wild any time I'd see her. So Ashley invites me in and I'm asking where her big brother is. Turns out he already left before I showed up, which is just typical. I just sent a quick text to him, letting him know I'd arrived and called him an asshole (mostly joking). As soon as I walk into the living room, I found myself surprised to see three other little girls sitting around and eating junk food.

Surprise, I learn that as soon as her brother took off, Ashley invited three of her friends over for a sleepover. I guess this happens all the time and the parents thought Ashley's brother would be there to watch them. It wasn't even a party or anything, since none of them were older than ten, just Ashley and her girl friends hanging out and playing games. I'd never met any of them before, but I introduced myself as Ben and they seemed really sweet. I just rolled with it and half an hour later I'm just playing some video games with them, laughing and chatting and having a good time. If that had been the entire night it would've already been pretty nice. But they'd been planning something before I arrived and I had no idea.

Right before they're ready to wind down and go to sleep, Ashley declares a "girl meeting" and they go into the bathroom. The sleeping bags were already set out, so I crawled into one and taking my pants off inside so I don't get too hot. Just laying there in my t-shirt and boxers thinking how fun this was. Something like 20 minutes go by and I start wondering what they're doing, and then also decide I'm really horny and I want to jerk off. Look, I was surounded by cute little girls all evening, it got me going. Yeah it was careless, but hormones are a powerful thing. Only after I've gotten myself hard and get some strokes in do I look back and see them looking at me through the partly opened door. Which then closes. I have now entered panic mode, because even though my bottom half is covered I'm wondering if they knew what I was doing. I consider putting my pants back on quickly and getting out of there, but I can't leave these young kids all alone.

While I've got a hundred thoughts going through my head, they come out into the living room being super giggly. They seem oddly excited about what they've seen and are pulling their own sleeping bags closer to mine and sit down around me, very close. At this point two things very quickly occur to me before my brain goes fuzzy. 

1 - They are up to something. 
2 - I was really glad it was dark in that room because my face must have been bright red. 

Ashley leans forward and and admits to me that she found her brother's cub collection while sneaking through his computer earlier. She was showing her friends before I came over and they'd started to make plans to play around with me like in the cub porn they'd seen. My heart skipped a beat when I heard that. I also felt validated about knowing that little gremlin was up to something. Then she says they know I was playing with myself, and it's okay if I want to keep going... if they can watch me. I'm fully hard now and wasn't going to turn them down, so I mummbled something like "Oh sure, that sounds fun." Jeez, even with these devious little girls I was socially awkward.

After I get the sleeping bag unzipped and fumble my boxers off, I start slowing stroking myself while they're absolutely transfixed on what I was doing. Nobody is talking, they're just watching me, eyes wide and curious. I'm taking it nice and slow because I don't have anything to use as lube, giving it long and steady strokes. I'm pretty sure that was helping me not to cum right away, but another reason is that my body was numb from how hot this all was. Now Ashley, bless her for this, asks me if it's okay for her to try something. I put my arms down and just nod at her, I very distinctly remember she flashed the cutest smile I've ever seen before she got down and started working me over with her tongue. I wish I could describe the sensation, but my body gave a little shiver and I'm pretty sure I let out an unflattering groaning sound once she took me in her mouth and got a rhythm going. Trying her best to mimic what she'd seen on her big brother's computer.

I can't take my eyes away from the sight of her head bobbing up and down on me with more enthusiasm than I could've expected. By the point she's almost deepthroating me, really giving it all she's got, I can't hold it back anymore and say I'm going to cum. One of her friends, the youngest at seven years old, gets this wicked smile on her face and actually puts a hand on the back of Ashley's head as she goes back down, holding her down on my cock all the way to the base. Just keeping her there with Ashley gagging on my cock down her throat while I start to ride out the strongest orgasm of my life. I could actually hear Ashley forcing herself to keep swallowing for what felt like half a minute. When I had nothing more to give, I actually had to tap on her friends arm so she'd let Ashley back up. The image of her lifting her head up with strings of spit and cum connecting her mouth to my dick is burned into my memory forever. Still red faced from the blowjob, she gave me a little thumbs up to let me know she was okay.

After she cleaned up in the bathroom, those sweet girls didn't ask anything more of me that night, maybe they weren't as brave as Ashley. Maybe they were satisfied with just watching something they didn't quite understand, but knew was exciting and naughty. Or maybe they could tell I was spent. Either way, they went to sleep without a fuss and Ashley's friends went home the next morning. My friend came back while his sister was eating cereal and thanked me for keeping an eye on her. I actually had the nerve to tell him "my pleasure" before leaving. It felt a little awkward since I knew what kind of porn he was enjoying in his free time. Guess he's as much a sick deviant as I am?

When I got back to my apartment I found myself hoping he would ask me to babysit again soon, but also hoping Ashley was good at keeping a secret. That brings me to now, writing all this in my old journal. How could I not? I don't know what's going to happen from here, but I'll wait it out and see if I find myself making another entry soon.