Hey guys! Chapter 7 here for you! Thanks everyone for being patient and sticking with me, things are moving along in the story. As always, feel free to leave a comment or send me a little orange envelope, always love to chat. :)
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# The Babysitter/Dungeon Master 7: Cum Brothers
(Will)
“Alright… I’m gonna do it.” I said, holding my phone tenderly in my fingers as I sat on the edge of a hammock. It was past midnight on Friday night, and we hadn’t seen Amy for almost a week. She was out of town to visit a friend is what I was told. Her absence was felt by all three of us. Brandon, Michael and I were in the tree house in Brandon’s back yard. My parents were out of town, and Brandon’s mom was going to be working all night. “What should I say?”
“Just send her a picture of your junk again,” Michael suggested rather bluntly, arms folded as he leaned against the wooden ship’s wheel. The tree house was a rather expensive professional job, not terribly big, but made to have some of the features of a pirate ship. It felt a little juvenile perhaps, but I still rather thought it cool. We’d been hanging out in the ship for several hours. Michael had been eager for me to message Amy all night, and had done nothing but bring it up since we got here. “Maybe she’ll send you pictures back.” He was obviously very excited, and perhaps unjustifiably optimistic. “I want to see her tits so bad.”
“He’s already done that,” said Brandon, sitting at a small polished table and furrowing his brow in the way he does when he’s thinking. Brandon had been a bit more reserved about the possibility of sending her a message, not wanting to be found out. I couldn’t really blame him there, but the idea was stuck in my head and wouldn’t leave. “Maybe he should just focus on talking to her at first.”
“That makes sense… I think.” I swiped my thumb over the phone, and brought up the ongoing conversation with Amy. She hadn’t said anything since I sent her the tribute on Monday. “I’ll just type… ‘How’s it going?’” My fingers carefully type the three simple words, and I hesitate only for a moment before hitting send. There was a noticeable silence in the room, as if the three of us had collectively sent a request straight to the mainline of the cosmos. You could almost feel the tension in the air. The wind picked up a bit outside, and it seemed darker than it had been just a few moments ago. I grabbed a cold soda from the mini fridge, and looked outside. The stars burned bright against an extraordinarily black sky. It was almost foreboding. I was nervous, and the other two probably were as well.
“What if she figures out it’s you?” Brandon asked, and I could sense the concern in his tone.
“I don’t know…” I said, really not wanting to put words to my expectations. “Our parents probably wouldn’t let us go over to her house for D&D anymore if she told anyone. Who knows what our parents would do. She’d might even move to get away from us.” Perhaps it was a bit extreme, but what I knew for sure is that I didn’t want to be found out… Not if it meant losing Amy.
“I don’t think she’d move,” Michael offered, “She likes us a lot, why else would she spend so much time with us?”
The phone fell out of my hands and onto the floor when it ***buzzed***.
My stomach leaped upward, and my heart started pounding. I quickly reached down, picked it back up, and opened the message frantically. I read it out loud, “Getting drunk with my best friend! How about you?”
“She’s getting drunk…” Brandon repeated, and I could see the gears turning in his head. “…Like *Girls gone wild*?” We were all familiar with *Girls Gone Wild,* and the idea of Amy getting drunk and pulling up her shirt was a beautiful thought. I let myself believe that if she was drunk enough, it would actually be possible.
“I’m hanging out with my best friends too,” I type and read it aloud simultaneously. “We’re getting drunk as well!” It was a lie, obviously, but I was trying to make sure she didn’t know it was us. I looked at Brandon and Michael, but we only had expressions of uncertainty to pass around. The phone buzzed again, “Sounds fun, do your friends like to jerk off to me as well?”
“Tell her yes!” Michael asserted quickly, so I did. The message was gone, and we were silent for half a minute before a reply came.
“It’s a picture…” I said, butterflies in my stomach spinning around like a tornado. The other two boys jumped up to stand beside me with nearly super speed, and the image loaded. It was Amy, and what I had to assume was her best friend, taking a selfie. Amy was as beautiful as ever with her dark hair and soulful brown eyes. She was smiling wide, and her noses was wrinkled a bit like when she’s getting the better of us in D&D. Her friend was remarkably beautiful as well. She had very light blonde hair, and big bright blue eyes that seemed almost to sparkle. The blonde was looking at the camera with a rather sly smile, and her arm was around Amy’s shoulder.
“Wow, she’s hot too,” Michael said, leaning in to get a good look at the picture. “Make sure that goes on the drive! What’s her name, I want to look her up!”
“What’s your friend’s name? She’s cute too.” I typed.
“Marley Faith,” Amy’s response said, arriving rather quickly. “She says thank you, she bets you and your friends are cute too. I showed her your dick. She said it was nice!”
The butterflies in my stomach fluttered around again. Now two, very beautiful, older girls had seen a picture of my dick. I wasn’t sure entirely how to feel about it, though a bit of embarrassment came through at first. I wondered for a moment if I should feel upset as I didn’t give Amy permission to share the picture… But I didn’t seem to quite have it in me to become upset with Amy. She was simply too beautiful. Plus, there was a bit of pride at Marley saying it was nice. My phone buzzed again.
“Send us a pic of your dicks…” I read the message aloud, my eyes going wide as I read the words. “All of us?” Michael questioned, and Brandon replied “Dicks, plural.”
I held the phone in my hand, and looked at the two of them. I could see they were as nervous as I was, and I knew they were reluctant. “We can do this guys,” I say, trying to sound motivational. “If we send her a picture of all of us, maybe they will send one back. I mean, no guts no glory, right?” They both took a moment, but the nodded. There’s a bench built into a wall on either side opposite the door. We all awkwardly pulled down our pants and shorts, and underwear, and sat down. I tried not to look down at the other two’s dicks, but of course there were momentary failures. They were both hard, as was mine. The idea of sending this picture to not just Amy, but Marley as well… just seemed like too big a quest to pass up.
I held my phone awkwardly out in front of us, and snapped a picture. The lighting wasn’t perfect, but it seemed to cover the necessary content. Not wanting to stare at my friend’s penises any longer, I went ahead and sent it. Again, there was silence. You’d think we all would have stood up and put our pants back on, but no… We all sat there with dicks hard and at attention, waiting on a reply. No one said a thing.
Finally, a reply came in. “Those are three awesome cocks,” I read aloud. “You guys going to jerk off together? That’d be so hot!”
Almost as soon as I finished reading the message, Michael’s fist wrapped around his dick. Again, I tried not to look at it, but from what I saw his was definitely the biggest. My heart pumped a little faster, as I had never thought about what it would be like to masturbate side by side with my friends.
“This is it,” Michael said, his dick in his hand idly. “Tell her we’ll do it if they send us a picture to jack off too.” Brandon nodded his head in agreement, he added. “Yeah, I suppose it’s worth a shot at this point.”
“We can, if you girls would like that,” I typed, reading aloud as I did. “Why don’t you send us a nice picture to jerk off to.” I added a smilie and heart emoji on the end, and hoped for the best. This time the silence was more deafening than previously. We felt so close… So close to something we’d wanted forever. Part of me didn’t think it was possible, that Amy was going to reply refusing as she had the first night I messaged her.
What was sent back to us wasn’t a picture though. My phone buzzed, and I opened the message hurriedly. I could vaguely see a girl’s figure standing in the frame, obscured by the large ‘play’ button in the center… She’d sent a video. I press play, my eyes wide, still half believing that it would be nothing like we wanted. The video started to play. Marley must have been filming it with Amy’s phone, because Amy stood in some strange living room.
“She’s not wearing any pants…” Brandon commented on the obvious. My dick twitched, and I held my phone up with one hand, my free hand reaching down and squeezing. I could tell with my peripheral vision that both of the other guys were holding onto their shafts as well.
Amy stood there wearing panties and a t-shirt, and almost seemed embarrassed. “Go on!” An unfamiliar voice called out to Amy, obviously it had to be Marley’s voice. “Go on, flash them!” She said it playfully, and the command made my dick twitch again. It took everything in me to not start stroking immediately, but I was worried I’d bust my nut as soon as I did. My hand relaxed, and I kept watching.
“Hang on.. hang on!” Amy said, hemming and hawing as she stood there, obviously conflicted about it. I could see the slight blush on her face, as her hands went down to the side of her t-shirt and gripped it. My heart was racing, possibly faster than it ever has before. She slowly pulled her shirt up, exposing her tummy up to her belly button, and then hesitated. Time seemed to crawl at the pace of a snail. I couldn’t help but notice Michael was already stroking, though hardly vigorously. Brandon was shaking just a bit, but was resisting stroking. “I can’t!” Amy rebuffed, but kept her shirt pulled up a bit.
“Oh, come on!” said Marley, clearly trying to motivate Amy in our favor. Suddenly, the camera turned around and we could see Marley’s face. She addressed us. “Hold in there, boys, she’ll do it. She’s just shy and has to build up to it!” I was reminded again how beautiful Marley was as well. If their places had been traded, and Marley had been our babysitter and dungeon master, I imagine we would have fallen equally in love with her. The phone flipped back around to Amy, Marley had stepped a bit closer. I could definitely see the blush on Amy’s face now. “You know you want to, just a little flash for them.”
“Fine!” Amy said, in the tone that made you think she was grumpy, but she really wasn’t.
That’s when it happened. Amy’s hands lift her shirt up a bit more, then I could see her fingers gripping underneath her bra. It took only a moment, and then she pulled her shirt up toward her neck. Her tits resisted for a moment, rising up with her bra and shirt, before the finally dropped down into view. I couldn’t help it, my hand immediately started stroking my throbbing erection. They were gorgeous. Not too big, but definitely not small. Pink nipples like ripe cherries, standing at attention and begging for attention. Amy bounced on her heels three times, and those beautiful tits bounced with her. Then suddenly they were gone as Amy pulled the shirt back down, her face red and flush. She giggled, and the video ended.
“Play it again!” Michael said, between breaths as he was stroking full speed now, as was Brandon. I didn’t have to be retold to replay the video however, obviously. My mind raced with everything I wanted to do with those tits. I wanted to touch them, squeeze them, plant kisses all over them, and most of all suck on those nipples. I started stroking quicker and quicker, and this time when Amy’s breasts dropped down, we all unloaded at once. My head leaned back, and my eyes closed. None of us had thought about a strategy, and just let it go loose. Most of my cum landed on my stomach, but I wondered if that was all of it, as I was pretty sure some of the cum that had hit my thighs and forearm weren’t mine. I didn’t care.
I took a moment to breath when it was done. Michael was laughing. “I guess we’re cum brothers now,” he said, raising up his forearm to show foreign cum. I blushed just a bit, but none of us really cared. Seeing Amy… it was worth it. We cleaned up as best we could using socks, our shirts, and a few paper towels.
“We’re off to bed, hope you guys had a good jerk!” I read the last message of the night. I wasn’t sure if it was Amy or Marley who sent it, not that it mattered. I uploaded the video to our drive, so we’d have it forever. We watched it at least twenty more times that night.
Source: reddit.com/r/sexystories/comments/bzfhp0/the_babysitterdungeon_master_7_cum
Hot, fun, sexy story.
So is the dungeon master going to fuck these boys? I bet they could go 3-4 rounds, since they’re only 14, before being spent