Hey guys! Here with chapter 4, from Will’s perspective. Hope you guys are still into this series, I know it’s a bit slow going. Anyhoodles, leave me a comment or a PM if you like! More to come.
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# The Babysitter/Dungeon Master 4: The Paladin’s Sword
“Man, that must have hurt,” I said, as I leaned forward and inspected the wizard’s blackened eye. Michael sat on my bed, and Brandon in my desk chair. It was Sunday night, and my friends and I hadn’t seen each other since Friday. I stood, shaking my head and feeling angry. Brandon had previously told us over messenger that someone pushed him, and he was sent home. His face, and the bruise on his torso told a harsher story. “I’m sorry we weren’t there, man.”
“And do what, Will?” Brandon said, looking up at me and rolling his eyes. He hadn’t seemed angry about it at all since he showed up this afternoon, and I supposed that was a good thing. “We were going to fight Johnny and his orcs? It’s not a big deal, I doubt they’ll do anything else now that they’ve gotten in trouble for it.”
“Hopefully,” I said, and did sincerely hope he was right. I pushed the topic from my mind, but somewhere in the back it was still bouncing around. I looked over at Michael, he was laying back on my bed looking at pictures of Amy on his phone. The story he told us about what happened the night prior still seemed unbelievable. “You really want us to believe you gave Amy a foot massage while looking up her skirt, and then jizzed into her milkshake?”
“Fuck yeah,” Michael said, sitting up on the bed and finally taking his eyes off his phone. “That shit happened. I should have taken a picture.”
“Pics or it didn’t happen, bro.” Brandon said, with a boyish chuckle.
“God she is so hot,” I said out loud, as I began to pace a bit. I spent so much of my mental time thinking about the babysitter/dungeon master. Whenever we were at her house my eyes were always fixed on her, following her every move as well as I could, without being obvious. I disabled the shutter sound on my phone’s camera and got quite proficient at snapping pictures without her realizing that’s what I was doing. Yet I was not satisfied with what I was getting. I laid in bed at night and dreamt of capturing something more; A nip slip, a good upskirt, any manner of wardrobe malfunction. I always tried to notice whether I could tell if she was wearing a bra or not. “I’m gonna get a picture of her naked someday.”
“Oh, please do,” Michael said, his eyes returning to his phone and looking at her pics again.
“Will!” My mom called from downstairs, loudly but not harshly. “Time for the boys to go home. School in the morning!”
“Okay, mom!” I yelled back, and then sighed. They both stood up and collected their things. We each fist bumped in turn, and then they headed down stairs. “See you guys.”
I shut my bedroom door behind them and sat at my desk. I had Algebra II homework, so I got out my text book and notebook and began solving the incredibly boring equations. I only got through a couple very slowly, before I realized I couldn’t focus. I kept forgetting the numbers in my head as I found myself ever distracted by thoughts of Amy. I look over at my phone and began to think about it again. I’ve considered anonymously sending Amy a picture of my dick for a few months now. I had the idea one night while jerking off in my bedroom to pictures of her on the drive. Every time I really considered it, I’d get jitters throughout my body and become very nervous.
The feeling was rather intoxicating though. I reached out and grabbed my phone, and the jitters already started to come back. Just the idea already sending blood rushing to my dick. I pull up an app I’d downloaded that sent anonymous and encrypted text messages. I just sat there for a moment holding the phone in my hand, thinking about the logistics in my head, just in case I decided to do it. I’d have to make sure it was taken in such a way that she wouldn’t be able to tell it was me. I walk over to my dresser opposite my bed and push it to the side a bit. I frame myself with the camera on my phone, so that only my crotch area was visible, and the pale blue wall behind it.
My heart starts beating fast, as I listen for a moment… I stay very, very quiet and I hear nobody immediately nearby. I just start to do it, unbuttoning my pants and pushing them and my boxers down. I pull my shirt up with my left hand and hold my phone with the right. My erection stands tall, with just a small making of a bush at its base. Five inches, I remembered the measurement, throbbing but without any veins popping out or the such. I was uncircumcised. All in all, I didn’t feel bad about my dick, but every boy my age wanted something bigger than they had.
The camera was at an odd angle, having not practiced it before. I snapped three pictures with slight adjustments, and then immediately pulled my pants back up. I sat on my bed for a moment and reviewed the three pics. I stared at each of them several times, before deciding to go with the third. I pulled up the texting app and attached the pic to a text. I typed in Amy’s number, which I had memorized, and then hesitated.
My hands were shaking, and I was incredibly nervous. I thought about deleting them, uninstalling that app, and going back to my math homework. I didn’t do anything for a few minutes, just sat there nervous as hell. Finally, my thumb just pressed send. I almost did it without even thinking about it. I zoned out for a moment, and then when my mind was blank, my thumb just seemed to move on its own. I just sat there looking at the ‘message sent’ screen, nearly paralyzed.
I waited nearly ten minutes with no reply, before I was finally able to go back and sit at my desk. I put my phone in my pocket and tried not to think about what I had just done. I began to feel super nervous about her knowing it was me and telling my parents. What would they think? I just knew I’d be in tremendous trouble. What if they made her stop babysitting and DMing? The thought was too much to bare, I just tried to push it out of my mind and solved some equations. Time seemed to move slower than it ever had before, as I pushed myself through boring equation after boring equation.
Then, nearly an hour later, I felt a sudden ***buzz*** in my pocket.
I pulled the phone out of my pocket furiously, my hands trembling. It was a text message from Amy’s number, reading just “Wrong number, I think.” I didn’t move for a moment, almost taken aback by the neutral response. It didn’t seem angry, and it didn’t seem to indicate she knew who I was. She had seen it though… Amy had seen my dick. That thought was blowing my mind, and my erection came back in full force.
“Hey son,” my dad said, as he opened my bedroom door. I jumped in my seat and dropped my phone onto the floor. I immediately picked it back up, locking it as I did so the screen would go blank, and looked up at my dad. I tried to look normal, but he looked at me with a raised eyebrow. “Sorry… didn’t mean to startle you.”
“It’s okay…” I said, my breathing finally slowing down. “Just finished my math homework, was probably gonna just go ahead and go to sleep.”
My dad nodded in approval. “Good, your mom and I are heading in too. Make sure your alarm is set, I’ll see you tomorrow.” He looked around my room for a moment, and then back at my almost quizzically. He seemed to let it go though, shaking his head and saying “Goodnight.”
He shut the door behind him, and I sighed in relief. My erection was already down to half-mast. I stood up and took my pants and shirt off, lazily throwing them in the floor next to my bed. I turned out my lights, and crawled up onto my comforter, and wiggled underneath it. My room was nearly pitch dark, but then it glowed a bit when I unlocked my phone, the light bouncing off my face. I opened Amy’s message, and wrote a reply. “I’ve got the right number, you’re Amy, right?” I tried to play the part of a random stranger who stumbled upon her Instagram profile.
I waited in my bed nervously, just staring at the phone’s home screen. It took less than a minute this time for the phone to ***buzz*** again. Amy’s response, “Yeah, I’m Amy. Do I know you?”
“No, I ran across your Instagram,” I typed in quick response, not sure where I’m going with the message as I’m typing it. I felt oddly bold, but at the same time immensely nervous. “I thought you were beautiful. Sorry if that was rude, I’ve never done anything like this before.”
“It is a bit rude…” Amy messaged back a few minutes later, followed by another message almost immediately. “It’s okay though, I’m not offended or anything. No need to apologize.”
I breathed just a tad easier after that last message and could barely believe she wasn’t angry. I thought about just leaving it at that, but instead I wrote a reply. “Awesome, you are as kind as you are beautiful. So, if I may ask, what did you think about it?” I almost began to realize that, without really meaning to, I was replying more like my D&D character than myself.
It felt like an eternity passed, and I was sure she was going to end the conversation there… but then the phone ***buzzed*** again.
“Well, since you asked so nicely.” I smiled nervously as I read it, “I quite like it. Looks smooth and super hard. Looks clean, which is a necessity haha.” My dick throbbed as I read the words. Amy liked my fucking cock; this couldn’t really be happening. I sat there, staring at the message, not sure what to do or say next. I decided to go for it, and just ask for what I wanted.
“You like to share naughty pics?” I sent the message before I had time to debate for twenty minutes if that message was too cheesy. Her reply came quickly, as if a blessing to not torture me.
“No thanks,” is all it said. My heart sank, my dick still throbbed, but I wanted to see her naked so badly. Another text came through, “I don’t mind looking though.”
“Want to watch me cum?” I replied, almost without even thinking about it. I was so hard now, my left hand went into my shorts and squeezed hard for a bit of relief. Before even having her reply, I was thinking about how to do it. The idea to print off a picture of her face and cum onto that came to me almost immediately. I wasn’t thinking, I pulled up a picture I had taken of her that was saved on the drive and sent it to my wireless printer. It printed photo quality; the last setting having been used by my mom to print out portraits we had taken. The picture of her looked fantastic. Her big beautiful brown eyes looking away from the camera, she was sitting in her kitchen wearing a blue tank top, a few of her dice just visible in front of her.
Amy eventually responded, “Sure, why not?”
The message may have been a bit neutral, but all I could see was a big ‘Go’ light. I put her picture in the seat of my desk chair and turned my desk lamp on it. My dick just a couple inches above it, I began stroking it with my right hand. My left hand opened the video recorder on my phone, and held it awkwardly pointed down to witness my actions. I watched myself jerk off on the camera screen, as just the idea of what I was doing was about to get me off. I could feel the cum swell up, it didn’t feel like normal this time, it felt like more intense than ever before.
I grunted as the first thick stream shot hot out, as I tried my best to aim. The thick white stream landed on her face, a long white line down over her left eye and cheek. The next one shot dead center, leaving a thick wet rope from her hair down to her nose. The next few spurts shot out in slower, but thicker, onto her lips, her right cheek, and a weaker stream landed on her chest. I breathed heavy as the last few came out, and then pulled my hand away from my cock. I took them out of the frame, and just lingered on the aftermath upon the photo, then stopped the recording. I immediately sent it.
Once it was sent, I crumbled up the photo, and buried it in the bin in my bedroom. I suddenly felt huge wave of relief, and my shoulders felt lighter. I turned my lamp off and crawled back into bed. I sat in the dark, eagerly waiting for another response. Just one more response… I hoped with everything I had that she liked it, but my insecurity suddenly made me start doubting myself. The thought that she was just being super nice, but was uncomfortable, crossed my mind. My mind tortured itself with doubt for at least twenty minutes, before my phone ***buzzed*** one last time.
“Looks delicious.”
Source: reddit.com/r/sexystories/comments/bcbt5u/the_babysitterdungeon_master_4_the_paladins_sword
[Part 3](https://www.reddit.com/r/sexystories/comments/bb4bsy/the_babysitterdungeon_master_3_the_barbarian_is/)
More… Its staring to get good