The Babysitter/Dungeon Master 15: Measuring Up[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 15 sliding in! Hope you like this one, I had a lot of fun writing it! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 15: Measuring Up

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(Michael)

That night I had a dream about her, exactly the way she had been when rubbing one out in front of us. Except in the dream, it was just Amy and I. The dream babysitter begged me to help her finish. I reached out to help her out of her panties, but… Unfortunately, I tend to forget my dreams as soon as I wake up. The whole thing became a blur as my eyes opened, and my entire body felt stiff. I stretched my arms and legs as I lay in the bed, slowly waking up. That’s when I noticed I had a raging boner sticking up in my shorts.

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I sat up and looked around. I was alone, Will and Brandon having must already be awoken. I squinted my eyes and grabbed my phone. It was 3 pm. I rubbed my eyes but wasn’t surprised I had slept so late. After watching Amy do what she did, and not being able to let off the steam, I had a terrible time getting to sleep. I moved myself to the edge of the bed and stared down at my boner. It probably wasn’t going away super soon, so I just tried to tuck it back with the waistband of my shorts and made sure my shirt hung over it. I wandered out into the hall and the kitchen.

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“Hey, sleepyhead,” said Amy, sitting at the dining table where we play. She had her legs propped up on the table, wearing a pair of short black shorts left her long legs on display. My boner twitched as my mind was flooded with the memory of touching those smooth legs. She was writing something in one of her DM notebooks, wearing a Taylor Swift t-shirt that hung on her chest as if she wasn’t wearing a bra. “I ordered a pizza.”

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“Double pepperoni, double cheese,” Brandon informed me, sitting at the table with a slice in his hand. He was looking toward the living room, where Will was playing Fortnite.

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“Fuck yeah,” I said, suddenly feeling awake and excited for pizza for breakfast. There was an open pizza box on the table with three slices left. I didn’t even grab a paper plate, just took a slice and started devouring it standing up.

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“Well aren’t you a potty mouth,” Amy said cheekily, not looking up for her notebook, but I could see her happy smirk.

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“What? Fuck?” I said, faking surprise for being called out. I teased her back. “You said fuck five times last night.”

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Amy did look up from her notebook this time, her eyes a little wide. I couldn’t help but grin, as I loved that look on her face. She smiled and laughed. Her face even seemed to turn a bit red. “Well then,” she said, clearing her throat and standing up. “I think I’ll go have a soak. Be ready to play at 9 pm.” She walked away shaking her head, and I turned toward Brandon.

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“She let me touch her boobs again, kiss them, and then jack off onto them,” Brandon said in a matter of fact tone, before taking another bite of pizza. I stopped chewing for a moment to process what he had just told me. “It was awesome,” he added, looking toward me finally and smiling.

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“That’s awesome,” I said and resumed chewing. At first, I felt like I should be jealous, but realized optimistically that my turn would be coming up soon. It was hard to know what to expect to happen next, but I could think of a hundred things I wanted to do to Amy. “What do they feel like?”

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“Incredibly soft,” he explained. “Imagine the softest skin you’ve ever touched, delicate. Touching them really turns her on. Especially when you play with her nipples.”

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My boner twitched again.

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“Fuck, I wanna touch them.” I took another bite of pizza and looked toward the stairway longingly. I wanted to go up there and get in the bathtub with her. I shook my head and looked back toward Will in the living room. “Do you think we’re going to get to fuck her, Will?”

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Will was hiding in a bush on Fortnite. He turned away from the screen and looked over toward us. His face was scrunched as if he’d been thinking about the same thing. “I don’t know,” he finally said. “I mean, I don’t want to jinx it…”

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“Jinxes are just supersti–” Brandon started, but I interrupted.

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“You’re right,” I nodded toward Will. “Best not jinx it, just keep our fingers crossed.”

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“I keep thinking this is all a dream,” Will added, holding the controller idly in his hands. “I mean, we’re just a bunch of teenage nerds. We are not supposed to be this lucky.”

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“If it is a dream,” I said, picking up another slice of pizza, “I hope I never wake up.”

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We didn’t see or hear from Amy for the next six hours. My boner eventually went away, and we spent most of the afternoon playing Fortnite together. I’d almost forgotten about *the game* when suddenly all three of us got a text message simultaneously. I immediately forgot about Fortnite and looked at my phone. It was a message from Amy, I read it aloud. “You are summoned to the castle. No socks, no shirts. Shorts only. Bring your phones.”

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It took a moment for us all to process before we were finally killed by another squad. Some random team member was yelling at us over coms for going AFK. I didn’t even register his comments. I stood up and took off my shirt. I wasn’t wearing socks anyway. I looked at the other two boys, and they followed suit. Together we walked up the stairs, phones in hand, toward Amy’s room.

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Will knocked, and Brandon and I just stood there waiting. Amy opened the door… and she looked amazing.

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She was wearing… I didn’t know what it was called. It was lingerie though, my extensive researching time on Google confirmed that. It was purple, with floral lacing along the hems. Two thin straps held up a makeshift bra, folded fabric tied with string in the middle, just underneath the ample cleavage. So much skin on her chest was bare. The robe continued down to her thighs but hung open in the middle front. I could see most of her belly, and the dark purple panties she was wearing. They were sexy but modest panties, that covered everything that needed to be covered well, unfortunately. She wore a necklace too, stones on a string, mostly purple, white and deep green. She wore purple dangling jewels from her ears and had a distinctly pink shade of lipstick on. She was wearing some makeup, with her hair loosely tied back.

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My boner immediately returned, and she spoke. “Welcome my brave knights,” she said as she ushered us in and closed the door behind us. The room was dark, the only light on was the main bulb in the center of the blanket fort we called the castle. It was dimmed with a teal light that lit up the castle with an eerie glow. She hunched through the entrance, and we followed her into the castle. It was brighter inside, and the only furniture was the mattress and scattered pillows. Amy sat on the edge of the mattress, and we stood before her.

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I wasn’t as nervous as I would have expected myself to be, but my boner was present and accounted for. My eyes couldn’t help but keep looking her up and down. Having seen her breasts before, my mind tried to imagine what they looked like under that robe. She looked so perfect that it was intoxicating. I could feel my heart beating quicker.

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“My dear boys,” Amy said, using the voice she does for the goddess in character. “You have bravely assisted me in restoring my castle to its full power. The walls are mending, and the ghosts are retreating. I can feel it’s power growing in my veins.” Amy kept biting her lower lip as she spoke, and I was driving me wild. Her face went a little more serious. “There is more work to do, but first you must pass a trial.”

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“Yes, your grace,” Will said, and went to one knee. Brandon did the same, and I stood there for a moment. It felt like an unnecessary move, but going along with Will always seemed to work out. So, I knelt too.

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“What is the trial?” Brandon said as we remained on our knees.

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“A test of stamina,” She answered, as she reached underneath a pillow on the mattress. She pulled out a short object… a wooden ruler. “But first, each weapon must be measured. Withdraw your weapons!” She said with an excited pitch and held up a fist. We each stood up slowly, with confused looks on our faces. She giggled, and said, “Take off your shorts.”

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I looked down, and my boner was already poking through my shorts, there was no hiding it without my hands in front of my crotch. We all hesitated… and finally, I made the first move. I hooked my thumbs into the bottom of my shorts and pushed them down. I stepped out of them and kicked them to the side of the castle. I stood there, feigning as much confidence as I could, with my cock hard and pointing up toward the dungeon master.

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Amy smiled, and the other two boys took off their shorts as well. I decided to get over the awkwardness quick and just glanced over at their dicks. They were both hard as well. Amy didn’t say anything for a moment, just sat there staring at us. Her gaze seemed into, eyes shifting from one boner to the next, and her mouth hung open just a bit.

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My boner twitched visibly.

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“Okay,” she said, shaking her head as if she was collecting herself. “Now, we measure them.” She slid off the bed, and onto her knees before us, wooden ruler in hand. She came to me first, and my eyes went wide. I opened my mouth to say something, but nothing came. Will and Brandon just watched, as her left hand came to the bottom of my shaft, and held it still. My toes curled to grip the carpet, and it took everything in me to stifle what could become a very quick orgasm. I felt the ruler against the side of my cock and felt Amy’s close gaze upon it. The bottom of her hand brushed against my balls, and I grunted a bit embarrassingly. “Six inches.”

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My heart slowed for a moment, as I heard the number. I had remembered my dick being five and a half inches long… It must have grown. Leveled up, even. I couldn’t help but smile. She let go of me and moved over to Will. “Five and a half inches,” she said and moved lastly to Brandon. They both seemed to have the same difficulty I had, with trying not to blow a load on her face. “Almost five inches, we’ll say five.”

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She tossed the ruler to the side of the castle and sat back down on the bed. The three of us stood there naked, clearly none of us sure what to say or do. Amy sat there, all that skin visible in the soft teal light, smiling.

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“Okay,” she said, shaking her head. Her face went a bit more serious. “The rules of the trial are as follows. You may not touch your cock. You can walk around the bed, but you cannot leave the castle and you cannot look away. You may not touch me, or the bed. You may use your phones to record or photograph me. If you can last until the end without touching yourself, and without climaxing, you will have passed.”

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My hands were at my side, and I retrieved my phone from my discarded shorts. The other two did as well, as we stood before her, and nodded. I didn’t know exactly what to expect, but I knew it would be a challenge. I gripped my phone tightly and curled my free hand into a fist.

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Amy slowly pushed herself back onto the mattress, her head coming to rest on a couple of pillows. Her head lay toward us, and her big brown eyes met mine. There was a look on her face I’d not seen before, something urgent. I followed her eyes as she looked at each of us, and then at each of our crotches. Her right hand slowly slid down between her cleavage, and down her tummy. The hand flattened and slid underneath those purple panties. I saw the impression of her knuckles as her hand slipped down between her legs… Then I saw her knuckles begin to move in slow circles. Her eyes closed, and her mouth opened a bit.

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My cock twitched twice, and I shook my head. My heart raced, and the desire to wrap my fist around my cock was fierce. I immediately pulled up the camera on my phone, and decided to, of course, record video instead of taking pictures. I hoped to focus on that even partially, which would help me make it through this. I pointed the phone at Amy hurriedly, not wanting to miss a thing. My hand shook unless I held the phone with both hands, and I started to slowly walk around the bed as I watched her with wide eyes.

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Her knuckles kept circling in her panties, and moment by moment I could tell she was getting more into it. Her legs would twitch or move just a bit, and her shoulders would arch ever so slightly. Her eyes opened again, she would stare at one of us. She moved from cock to cock, and from eyes to eyes, all the while her knuckles circled.

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I kept stepping around and happened to notice a small empty glass on the backside of the mattress, sitting on the carpet. My brain went to register it but was immediately interrupted by a soft moan that Amy let out.

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She leaned up a bit, and her knees came together. Her eyes were now glued to my cock, as I stood still and pointed my phone out to her. She kept rubbing herself, and another moan came out. Her finger began to pick up the pace, and her shoulders wiggled. She let out a third soft moan. Her eyes rolled up to meet mine, and there was a hunger in her eyes that I could feel. My cock began to twitch over and over, and I tightened a fist in my free hand. Her eyes stayed with mine, and she whimpered and kept rubbing. My cock kept twitching, and her eyes rolled back down toward it.

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I thought I might break that moment, my entire body tensing up as I fought an orgasm that was coming without any physical stimulation. I got a moment to breathe when her eyes finally left my cock, and she looked toward Brandon. My body loosened up a bit, and I just tried to regain my composure. My focus shift when her free hand began to move toward her chest. My eyes followed that hand carefully, as it came up and gently grasped the purple string between her tits, and pulled. A knot began to unravel as her hand pulled at the string until finally, it loosened. The fabric on her chest suddenly began to slip to the sides. I watched intently, cock twitching, as her body twitched and wiggled in her pleasure. The robe kept slipping until I could see a nipple, and then suddenly it felt completely to the sides. Her large breasts pointed toward the light, pink nipples pointing as well.

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When her hand came to a breast and pinched the nipple, I squeezed my fist so hard I thought my fingernails might draw blood. Her gaze shifted to Will, and her moans began to come more frequently until it was continuous. I watched in awe, as her sound seemed to go from pleasure to pain over and over. My fist kept tight, and I fumbled my phone. It fell to the floor, but I didn’t even care. Both my hands were fists now, as I watched her.

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Her back arched, and her knuckles were moving wildly inside her panties. Her legs shook, and her toes curled. Her whole body moved as if she was bouncing about waves on an ocean. Her eyes went wide, and she looked toward the light. Her mouth went agape, and her back arched. She came upon her heels a bit, as her hips began wiggling uncontrollably. A moan became a long, passionate cry.

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My cock was throbbing, and again I knew I was about to burst at any moment… and then she relaxed. The cry faded off into a long whimpering sigh. She was breathing heavily as her body came to a still, and her hand finally retreated from her panties. There was a faint glisten on her fingers, as her hands went up into her hair. Her chest rose and fell with her breaths, nipples still standing stiff. She closed her eyes for a moment, before finally managing to sit up.

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“Well then,” she said, as her eyes scanned us. All three of us had made it through, without touching our dicks, and without cumming. Though, Brandon and Will both had the luck to still be holding their phones. She smiled with a tired glee, “You have all passed the trial. I never doubted one of you.” She managed to move her body toward the back of the bed and reached for that glass cup that I had forgotten about. She sat on the bed and held it for a moment. “Now, it’s time for a tribute. Your life seed into the chalice, just like before.”

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She held out the cup, and just looked at us with a smile. It wasn’t lost on any of us what she was asking, and my throbbing cock didn’t need to be told twice. My first wrapped around it, and I shuddered with relief. I instantly started jerking and stepped up toward the cup. Brandon and Will did the same, and it took less than ten seconds before we were all unloading into it… It wasn’t the cleanest ritual. Most of the cum went into the glass in thick ropes, sliding down to the bottom. Some splashed along the edges, inevitably getting on her fingers.

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When it was finally over, I stood there almost in a daze. My heart began to slow down, and my cock had finally quit twitching. It took a moment after my release before my eyes finally went back to Amy. She sat on the bed, both hands holding the glass cup now filled with our cum. She just looked it, biting her lower lip. Finally, she looked up at us and smiled. She brought the glass up to her lips and tilted her head back. I watched intently as every drop of cum from the three of us slid out of the glass, and into her mouth. Just a bit dribbling down the side of her lips, and some dripping onto her chin.

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“Oh my god,” Amy said, her voice shifting out of the tone she used for the goddess. She began to giggle quite a bit, but I didn’t see what was funny. “I am a cumslut,” she finished and licked the rim of the glass.

Source: reddit.com/r/sexystories/comments/cvqjdq/the_babysitterdungeon_master_15_measuring