Benjamin's Journal - KEEP OUT

This journal belongs to:
Benjamin T. 
Age 21


November 17
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Well, here I am again.

I wasn't sure if I'd be writing another entry in this thing, but... yeah. Something happened. I didn't know what to expect after my time with Ashley and her friends last night, but somehow things got even crazier. Turns out Ashley and the girls were really good at keeping a secret and weren't done playing with me yet. The little trouble makers have become fully corrupted now and just thinking about that gets my hands shaking. Alright, let me calm down so I can write this down.

I called my friend in the afternoon and acted like I was doing him a favor this time. His parents would still be out of town for a while and I offered to watch his little sister overnight again, giving him the chance to spend the night with his girlfriend. Ashley had apparently been talking about how much fun I was, keeping the details hidden, so he agreed and said he owed me for keeping an eye on his sis. I had to laugh and told him not to worry about it.

Of course he was gone before I showed up and Ashley had already invited her friends over, hanging out in the living room. The girls were more excited than ever after the night before and it was easy to tell how worked up they were. The thing about little girls is that they have a lot of energy. I mean they were practically jumping up and down and saying we should play a game in Ashley's room. Last time we'd spent a few hours playing games before they told me what they wanted, but this time they couldn't wait. I was totally okay with this and followed their lead. Jeez, they're just so damn cute. 

We all sit down in a cirle on the floor of her room and I realize I've never really been in there before. There's a lot of pink and posters of cartoons on the walls. I should mention I was getting hard already and my buldge was starting to show through my shorts. I keep catching them glancing down at me the whole time. It was just so adorable how curious they were. Anyway, the game is decided to be Truth or Dare with a twist: if you can't complete the truth or dare, you have to kiss the one who challenged you. Which now that I think about it, is a really tame twist after what had just happened the last time we were all together. Didn't think of that at the time because I was focused on how lucky I was and wanted to go around the circle asking their names and ages first. I already knew Ashley was eight, but two of the others, Sophia and Candice, are seven. The youngest, Amelia, is six. I knew better than to consider her more innocent though, since she was the one who made Ashley deepthroat me last time. Maybe they're a bad influence on her... but I'm one to talk.

Now I knew that if I chose dare, they would want to do more sex stuff... but I wanted to build things up just a bit. So I started the first round and picked "truth." Candice asked me if I had ever fantasized about little girls like them before last night. Which I admitted yes and they giggled like crazy. Candice picked "truth" too, and I asked how she knew about these kinds of adult things. Her answer wasn't surprising, I guess. She said Ashley introduced them all to the cub porn on her brother's computer and they all seemed to like it. I already figured that out, but thinking about it still turned me on. I also knew they didn't understand a lot of it and must have been mostly driven by curiousity. Not that I was complaining. The hottest part was how eager they were to try the depraved things they'd seen.

Ashley, the little instigator, picked "dare." The other girls collectively dared her to kiss me. I figured we were beyond a kiss on the cheek by now, so I leaned in close, wrapped my arms around her, and kissed her deep on the mouth. Pretty sure I surprised her by how fast I moved in, but she didn't fight it. Our tongues wrestled around while the girls stared at us. When I broke the kiss I saw that she was blushing and it just made my heart melt. Then I noticed Sophia staring at my buldge. I didn't say a word, just pulled off my pants, slid my boxers off, and let my cock stand free for the girls to see. Their faces were priceless. I leaned over to Sophia and said "you can play with it, if you want." She seemed timid, but put her hand around my shaft and very slowly started stroking me, the way she'd seen me do to myself last night. She almost seemed afraid of being too rough. I didn't mind, I was just enjoying the sensation. Her tiny hand working my cock was like heaven.

Ashley suddenly remembered we were playing a game and pointed to Amelia, saying it's her turn now. Amelia didn't take her eyes off me and said "dare." Now her friend is still touching me and I think Ashley just wanted to make some trouble at this point. So Ashley stood up and says, "I dare you to let Ben fuck your ass!" Everyone else bursts out laughing. Everyone except Amelia who turned bright red. Maybe she was more shy after all. I felt like I needed to say something so she wouldn't be embarassed, I didn't want these girls to get carried away and start being mean or anything. So I just looked Amelia in the eyes and said I'll take the loss on this one, hoping it turns attention away from her. But instead, that six year old kid just looks back at me and says, "No it's okay, I don't want to lose my dare." 

I'm able to stammer out, "are you sure?" I mean, she's a very petite girl and I didn't want to hurt her. She just climbed up onto Ashley's bunny-themed bedsheets, stripped off her pajamas, and told me she practiced at home with the toy she found in her mom's bedroom. Very curious girls, indeed. I don't need to be told twice, so I get up there on the bed and helped position her down on her hands and knees. Now I'm not sure if Ashley knew her friend would agree to it or not, but Ashley jumped up and said she can help. She scampered over and propped a pillow under her friend's hips so Amelia's ass was sticking up into the air in front of me. I told Candice to find my pants on the floor and bring me the small bottle of lube I'd brought in my pocket. See, this time I came prepared.

I took the bottle while Amelia was adjusting herself to get comfortable and rubbed my cock down with lube until it was nice and slick. Their eyes were locked onto my dick. I was rock hard at this point... if only you could have seen the view in front of me. Then I squirted some lube on my fingers and slid them into this adorable girl's ass while she squeeked in surprise. The other girls got close so they could see better. I didn't want to leave anything to chance, so I finished up by sticking the end of the bottle into her tight hole and squeezing some more directly inside so she'd be fully lubricated. 

As a side note, I need to buy myself more lube for jerking off because it's damn good stuff.

"Don't worry about me, just make yourself feel good," were her exact words before I grabbed hold of her hips and started pushing in. She must have known it would be intense. I actually got halfway inside, gliding pretty smoothly, and she starts groaning out loud. Sort of a 'wow that's a lot' kind of groan. Such a tiny girl... her ass was not used to something like this and clenched hard. I gripped tight with my hands and gave myself enough leverage to push in further. Now I was moaning out loud because... Geez, I wish I could describe what it felt like in a way that would truly bring the memory to life. This kid was so tight, hot, and slick that every inch deeper felt more amazing than the last. Her ass kept trying to push back on my cock, which just made it feel better. As I was almost all the way in she lets out some very naughty words I didn't expect from her and started sobbing. Ashley got down in front of her face, still wanting to help, and gave her some kisses while I pushed in until there was no more to give. I was up against her perfectly soft cheeks and Amelia was more than full. Sophia and Candice were watching all of this with silent excitement.

I wondered if she was regretting it at this point, but before I could ask she just says, "You can go harder now." What a precious little trooper. So I slid out... and slammed right back in. I just started pounding her. She yelled out fairly loud, but Ashley kissed her mouth and any noises she made were being muffled by Ashley holding their lips together. Every single time I pushed back in, her ass cushioned the force and was making a very distinct slapping sound with every thrust. Her other friends were clearly enjoying the show and it encouraged me to keep going. I remember the nightlight in the room catching her back at just the right angle that I could see her sweat and it was all just so fucking sexy. 

I managed to last a while before the pleasure pushed me close to the edge. I was just holding this poor girl's ass firm and going to town. She asked for it, right? I think I said something like, "Hey girls, I'm about to fill her up." Hoping they had a vague idea of what that meant. Then I unloaded inside her. Fuck, my whole body locked up and I had the hardest orgasm of my life. Just filling Amelia to the brim, my cum gushed out because it had nowhere else to go. I rode it out before I finally stopped thrusting. Had to catch my breath and heard a wet popping sound as I pulled out. Her ass was actually gaping with my cum spilling out onto the bed. I hate to think I was too rough, but when I looked around to her face to ask if she was okay, she actually pulled me in and kissed me. Which was impressive since her body was still shaking. What a sweet, naughty child. Safe to say she was okay with the treatment, thankfully. 

The girls seemed satisfied with that. As if watching me fuck the youngest in the ass made them all shy again. I thought it was cute, and after the cleanup, I was pretty spent anyway. Nothing too eventful happened before bedtime and we managed to get some sleep. We've all agreed to keep our fun to ourselves, especially if they want to play more. It still doesn't feel real. Like, how many guys find a harem of little girls to play with? My buddy thinks I'm a great babysitter, so I'll have to think of some more activities for us soon. It feels wrong to admit, but I can't wait to see them again. For now, this journal will have to serve as my confession. I'll hide all my guilt away with it.