Hey guys! Here with Chapter 5! Hope you are all still enjoying it. I’m gonna start putting less specifics in the brackets in the title, as to avoid spoilers. Let me know what you think in the comments, or feel free to send me a PM if you want. Until next time!
———–
# The Babysitter/Dungeon Master 5: Amy Makes a Wisdom Check
My eyes opened like heavy steel shutters, and the dim lighting of my bedroom seemed blinding at first. The back of my head felt like it held the weight of a bowling ball in it and ached terribly. My legs and arms were sore, terribly sore. It felt as if I had just completed a decathlon in the past twenty minutes with a body that was not prepared. I was terribly thirsty, craving water. I grunted as I laid there for a moment, my hands coming up and rubbing my eyes. I felt terrible, and it was quite clear I drank too much last night.
I finally summoned the strength to sit up in my bed. My vision was a bit blurry at first, but things began to come into focus. I looked down and found myself quite naked. My comforter was all out of whack, twisted up and half hanging off the bed, and my sheets were quite wrinkled up. I noticed Little Cthulu laying on the bed next to me, and then became aware of the slight ache between my legs. I took a hand gently between my legs, fingers delicately touching my lips. Seemed I was sore down there too, I must have really gone at it last night. I picked my vibrator up, and began to slide off the bed, and that’s when I noticed my bedroom TV…
The TV was mounted on the wall opposite my bed and was rather large, and something was playing on it. I rubbed my eyes, my vision still quite blurry, and the picture came into focus… It was a video of some guy masturbating over top of a picture of me. That was about the time that I really began to realize how badly I had blacked out, as I had no memory of this. I pushed myself off the bed and walked closer to the television. I had absolutely no idea what this video was, where it was from, and didn’t recognize the penis in question… Not that I had been familiar with any penises at all for a while… I just stared at the television, confused, and then the unfamiliar dick began ejaculating onto the picture of me, quite generously. The penis disappeared from the frame, focusing on the aftermath for a moment, before the video began to replay. It must have been looping all night.
“What in the hell…” I said out loud to myself, turning and scanning the room for my phone. It too had been lying on my bed next to my pillows. I tossed Little Cthulu in my panty drawer, and then got my phone to check my messages. Once I unlocked it, I could see the video being cast to the TV, so I stopped that. Sure enough, there was a text conversation that I had last night but did not remember. It had started with an unsolicited dick pic. I stared at the picture for a moment, again definitely not recognizing it. I didn’t take a moment to admire it, and read the following conversation. That conversation ended… with me saying ‘Looks delicious’. I literally face palmed and felt both embarrassed and ashamed, though I always did have a big thing for cum… I didn’t recognize the number the texts had been sent from, and just prayed to any god that might exist that it wasn’t someone I knew. “Looks delicious? You’re so fucking weird, Amy.” I walked over to my desk where sat the bottle of tequila I had bought the previous day. I threw it in my waste bin next to the desk and shook my head. I almost exclusively drank rum, but yesterday I had been in a good mood and felt like changing it up arbitrarily. “This is why we don’t drink tequila… ever.”
I tossed my phone onto the bed, unable to handle this. I at least felt a bit proud of myself for not sending any nudes back to the stranger. I slipped on a pair of panties and a t-shirt and went downstairs to the kitchen to eat something and take some ibuprofen. I made myself eggs, bacon and toast, and washed down the ibuprofen with orange juice. I took a long steamy shower while listening to music, and then zoned out playing video games for a while. It was a few hours before the hangover effects were all but gone. I had a few errands to run that Monday; A bit of grocery shopping, getting the oil changed in my car, and a couple other boring things. I was home around 2pm after it all, but all during the day I kept finding myself having flashes of the dick pic in my mind. I opened my phone and looked at the pic and the video several times, whenever I was sure no one was could see my screen. I definitely had no idea who sent it to me, but something about the video was bugging me… I just couldn’t place my finger on what it was.
After getting home and settling in, I walked upstairs to my bedroom and retrieved a joint I had laying on my dresser. I stepped outside onto the secret smoking spot on my balcony, and lit it up. It was quiet, so I took my time smoking. The head change came pretty quickly. I always had a special affinity for getting really really baked after a night of heavy drinking. It felt like the world really slowed down, and my thoughts flowed nice and crisp. There was a small breeze outside that felt nice on my face, and I just let my mind go blank as I finished the joint.
Once done I went back inside, closed the screen door behind me, and stretched my arms. That’s when my phone my phone started to ring. It vibrated on my desk, and I walked over, feeling quite nice, and answered it. “Hello?” My tone was nice and perky.
Turns out it was Michael’s father. Apparently, Michael had somehow contracted a virus onto his laptop which had rendered it unusable. His father’s laptop was at the office, so they asked if Michael could come over for a bit and use mine to redo some homework. I obliged, of course, and made my way downstairs. Michael made it over very fast, knocking on the door almost as soon as I made it to the living room. He had a big grin on his face when I opened the door, I said “You look excited.”
“Oh,” he said, as if I had caught him in some naughty act. “I’m just excited about game night tomorrow, I suppose.”
“Me too,” I giggled, and closed the door behind me. I made my way toward the stairs, and nodded for him to follow me. “Come on, laptop is in my bedroom. I usually prefer to keep it at the desk, don’t really move it around much.”
He followed me to the bedroom, and I left the door open. I noticed the roach leftover from my joint, and rushed to hide it in a drawer. The room was rather clean otherwise, but I did pick up a bit of laundry and tossed it in my hamper. He made himself comfy in my desk chair, and I stood behind him. “If you need to login to an email account or anything, just do it in an incognito window so it won’t save any of your passwords.”
“Okie dokie, Supreme Leader Snokie,” he chuckled at his own joke, then proceeded to open up word and began formatting with his name and class information. I giggled at the joke, and that’s when my phone ***buzzed*** in my pocket. I looked away from the laptop screen, pulled out my phone, and saw a text from the dick pic number. A few butterflies swirled in my stomach, which was not the reaction I expected.
“I’ll be right back, just do whatever you need to do,” I told him, walking out of the bedroom, across the hall to the bathroom. I shut the door behind me, and opened the text. It was another picture of the stranger’s penis. I sat down on my toilet seat, and full screened the picture. I just stared at it, forgetting that I was high as a kite. It was hard to judge the length of it in the picture, but it wasn’t tiny. It stood fully erect, circumcised, the head just a bit larger than the shaft. It looked smooth, the skin looked soft despite the dick obviously being hard. The pubic hair at the base wasn’t unkempt, short and not quite turning into a guy bush. It made it look rather youthful, and I wondered how old this person was. My first thought was a young college kid, probably a virgin who needed an anonymous outlet. I used to get dick pics all the time when I was in college. I used my fingers to zoom in on it, admiring every detail. Though I knew I should think it rude, I just felt flattered and girlishly excited.
I minimized the pic, and my eyes scanned up. I saw the last text from last night which just said ‘Looks delicious.’ I couldn’t help but imagine what this dick would taste like. My eyes closed, and I imagined it was in front of me. Being quite high, I found my imagination extremely vivid. I imagined rubbing my face against it, feeling the stiff warmth on my nose and my lips. My mouth opened a bit as I imagined taking the tip of it between my lips, into my mouth. I always had a thing for blowjobs. Whereas most girls thought of it as an obligation to their boyfriend, or shied away from it altogether, I loved giving them… As long as the dick in question was cleaned, groomed, and not sweaty. I imagined the stranger’s dick releasing it’s orgasm in my mouth. I also loved what they produced. I actually really enjoyed the taste a lot of the time, though some guys had funky cum. The feeling of it on my body or face always felt nice, and I would often be quite playful with it.
I snapped back to reality when my phone ***buzzed*** again. My eyes opened, and I read a new message from that number that said, “Still like it?”
“Very much so,” I replied, with a girlish smile plastered on my face. I sat on my toilet, hiding in my own bathroom, like I was fourteen and secretly sending texts to a crush.
“Want another video tonight? Do you like seeing it on your face?”
“Sure,” I replied, and then put my phone to sleep. I could feel myself starting to get worked up, but I remembered my guest in the next room. I looked at the time stamp on the dick pic, and realized I had zoned out in here for almost half an hour. I stood up, and took a moment to compose myself before heading back to the bedroom.
“I’m all done,” Michael said, standing up from my desk quite quickly as I walked back in.
“Oh,” I said, a bit surprised. I had expected him to be over for a couple of hours, but he already seemed to be making his way rather hurriedly toward the stairs. “All right then, I suppose I’ll see you tomorrow afternoon?”
“Yep, thanks Amy!” He called, and was down the stairs and out my front door quicker than I realized. It seemed really awkward, but I shook my head and figured it was just because I was really high. I sat down at the desk, and looked at the laptop. It was on my desktop so I had assumed he had closed everything down, but I noticed a Chrome window open. I clicked on it, expecting it to be a tab that I had left open, but it wasn’t. It took me a moment to realize what I was seeing… and then my jaw dropped a little.
“Holy shit…” Open on my laptop was an online storage drive full of pictures of… me. I took my mouse in hand and began opening them one by one. Some where pictures that I had posted online, but others were pictures of me that I’d never seen before. There were rather normal pictures, but then there were pictures of me from behind and pictures that where I obviously wasn’t aware they were being taken. My heart began to beat a little quicker, as I took this in. A picture down my blouse really stood out, along with another picture of me from the back wearing just a t-shirt and panties. I clicked around on the profile settings, and sure enough I was logged in under the username TheBarbarian. Two other names were listed as having permission to the drive; ThePaladin and TheWizard.
I slumped back into the seat, and tried to process this. The three boys obviously had a crush on me, which was normal enough and I had wondered about anyway. But this seemed obsessive, almost stalker-ish. I knew I should feel violated and mad… but I didn’t. Much like with the dick pic guy, I found myself just feeling flattered and girlishly excited.
That’s when a thought crossed my mind, and my eyes went wide. I pulled up the video I had received from the dick pic guy, and began playing it on my phone. I paused it immediately, and looked at it intently. I wasn’t looking at the dick though, but at the picture of me. I looked back to the laptop and scanned the drive, the picture was there. I opened up all my social media platforms, going through every picture I had ever posted… It wasn’t there.
“Oh fuck,” I said, confirming that the dick in the video must belong to one of the three. As that cataclysmic meteor of information hit me, I noticed something else in the corner of the screen. I clicked a gray bar, and a chat window popped up. I scrolled up the long history a bit, and I couldn’t believe what I was reading. It was messages of them discussing me… They talked about how sexy they found me, things they wished I would do to them… or them to me. They discussed ways to get new pictures, and much more. My heart raced, and I really didn’t know what to think or do.
Suddenly, ‘You are typing…’ showed up in the chat window, followed by a message from TheBarbarian.
TheBarbarian: Just got home… uploading two new pics. I stole a pair of her panties, they smell so good. I also took a picture of something I found in her drawer.
It seemed Michael had logged in from his house, and the drive didn’t seem to have a problem with the username being logged in from two locations. The files on the page refreshed, and sure enough there were two new pictures. One was Michael holding a pair of green panties that I recognized. I stood up from my desk and checked my drawer. Sure enough, they were gone. I couldn’t believe it. I sat back down and opened the second new picture, which was a picture of him holding Little Cthulu in my room. The butterflies in my stomach swirled again.
I immediately stood up from the laptop, and nearly ran downstairs. I had to have a drink.
Source: reddit.com/r/sexystories/comments/bevxee/the_babysitterdungeon_master_5_amy_makes_a_wisdom
[Part 4](https://www.reddit.com/r/sexystories/comments/bcbt5u/the_babysitterdungeon_master_4_the_paladins_sword/)
Can’t wait to see how Any handles this! Loving the slow buildup!
Great stuff keep up the great work