The Babysitter/Dungeon Master 11: Advanced Roleplay[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 11 comin at ya! I was really sleepy when I proofread this, so send me a message if you notice any typos and I’ll fix them. Or if you just want to reach out, comments appreciated too! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 11: Advanced Roleplay

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(Brandon)

We were all up around noon, and Amy made pancakes. The game items were all put aside for once, as we all sat around and had breakfast together. Amy had awoken a bit earlier than the rest of us, and had done some tidying up. We all ate rather peacefully, the house lit up by the afternoon sun.

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“You boys sleep okay?” Amy asked, before gracefully pulling a slice of pancake off her fork with her lips. She had a glow about her this afternoon, and I couldn’t help but to stare at her for a moment.

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“I did, for sure,” said Michael, with a mouthful of pancakes and a glass of milk primed in his left hand.

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“Oh, I bet you did.” Amy giggled as she took a sip of milk. “You told them about it, I’m guessing?” Michael nodded without hesitation, clearly without any expectation that he was supposed to keep anything a secret. Michael had told Will and I about what happened between him and Amy last night. Apparently, she had him give her a foot and leg rub, and then proceeded to let him ejaculate into her panties. A white pair of panties with a picture of Squirtle printed on the front. Supposedly she put them right back on afterward, and then went to bed.

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I wasn’t sure if she was still wearing them at that moment. However, she was wearing a rather tight white tank top with Pikachu printed on the front. So, the claim of the Squirtle panties seemed legit. Amy had chosen to wear her hair in two high pigtails, which was a choice I’d not seen her make before. I liked it, it made her seem rather playful. The Pikachu tank top hugged her tightly, and the outline of a bra holding her breasts was quite visible. I could also see the bra straps not properly aligned with the straps of the tank top, a distinct blue. She also wore a pair of tight jeans, the kind with intentional ripping along the front.

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“It’s okay,” Amy said, with a small smile on her face. She seemed happy enough, as she put down her utensil and picked up her phone. There was a dinging, and I looked toward my phone but there was nothing. Michael picked up his, and looked at it quizzically. “Your experience points for last night,” she said, in a matter of fact way.

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“Experience points?” Michael questioned, and swallowed a big gulp of milk.

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“For last night,” Amy explained, putting her phone back down on the table. “I had the idea last night, and wanted to talk to all three of you about it.” I stopped eating, as this had me entirely curious. Suddenly the game was involved in what had happened. “Basically, I was thinking we could lean into the actual *roleplaying* aspect a little more, and get away from the table for a bit.” She picked up a single D20 die, and held it in her hand as she spoke. “Especially concerning the rituals you guys will need to complete for Ameliah that aren’t based around combat. You can still earn rewards and experience points, but we will only use die sparingly.”

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I tilted my head a bit, as I tried to process exactly what she was getting at. Whatever it was sounded quite exciting, but I wasn’t sure exactly what was going through her mind. I wondered if we would all get to rub her legs for experience points, but knowing Amy’s DMing style she would probably mix things up. I wondered if she had a plan, and how detailed it was. I thought it too bad there wasn’t a source book that I could read up on.

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“It’ll make sense once we do it,” Amy reassured, nodding her head ever so slightly. “Oh, and Michael, you really missed a chance at extra experience by not taking pictures or videos.” She looked at him rather seriously, but not harshly. Michael’s eyes went wide, as if he had just now realized he’d missed a fantastic opportunity.

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There was a moment of silence at the table, and Will’s and my eyes met. As soon as we had heard that Michael got to masturbate, we knew we had to ask to do so as well. The idea made me way too nervous, so Will had agreed to ask for the both of us. As I looked at it him, I hoped he realized this would be a good time.

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We seemed to be on the same wavelength.

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“So, speaking of that,” Will said, putting down his utensils and clearing his throat. “Brandon and I were wondering if we could… ya know, have our turn today too?” A less than graceful approach, but sufficient I supposed.

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“I figured you’d ask,” Amy said, with a bit of a smile. She nodded, “Yes, fair is fair. We’ll try out the new system. Ameliah came to the barbarian last night alone. This afternoon she will come to the wizard, and tonight she will come to the paladin.” Amy pushed her chair back, and stood up from the table. “Give me about an hour, Brandon. Then come knock on my bedroom door.”

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Suddenly, I felt the pit of my stomach drop as a torrent of butterflies began swarming around in it. Amy walked away toward the stairs, and the three of us were just left staring at each other over pancakes. No one said anything. I looked down at my pancakes, and shook my head as I tried to process this. In one hour I was going to meet Amy so that I could roleplay a wizard performing a sacred love ritual with a goddess.

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I barely paid attention to what transpired over the next hour. I know the three of us did the dishes and cleaned the table. Then we settled in the living room. Will and Michael were playing games on the XBox, and I mindlessly scrolled through my phone. All I was really doing was distracting myself so I could check the time every few minutes. The final five minutes were the longest, but finally the full hour elapsed.

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“I’ll be back,” I said, standing up from the couch. The other two boys just watched as I turned and made my way up the stairs, my phone in hand. I was incredibly nervous, and my palms were sweating profusely. Climbing the stairs felt like I really was my wizard, climbing the mountain to get to Ameliah’s castle. I reached the top of her stairs, and tried to control my breath in front of her door. After a minute, I finally worked up the courage to knock three times.

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“Come in!” I heard Amy call from inside the bedroom. I took in a deep breath, turned the doorknob, and stepped in opening the door. She was on the opposite side of the bedroom, standing at her sliding glass door. I closed the door behind me, and when she finished blowing smoke outside she closed hers. She smiled as she stepped toward the center of the room. “Thank you for coming to my quarters, my dear wizard.” She said, still dressed as she had been downstairs. Her voice had dipped into that more sultry voice she used when she was quoting Ameliah in character. “Please, take a seat.”

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“Yes, your grace,” I said, remembering the courtesy I was supposed to use. She pulled out her desk chair, and I agreeably walked over and sat down.

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“You have been an irreplaceable asset to the party,”she said, as she stood in front of me, her big brown eyes staring down at me gently. “Your intelligence allows you to look deeply into a situation and understand all it’s complexities and variables. Your judgement is trusted and respected by your team members. Also, by me.”

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“Thank you, your grace,” I responded, looking up at her and happily receiving the praise. I already had an erection.

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“As you know, time is always of the essence for those with great power.” She turned, and took a few steps toward the bed, her hands together behind her back. “To protect ourselves and others from what is to come, the power of this castle must be returned. The first ritual will be held soon, and I’m entrusting you with a very crucial duty.”

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“Yes, your grace.” My eyes, which had been focused entirely on her cute butt in those tight jeans, went down to the floor. I couldn’t help but doubt myself as soon as she mentioned assigning me a *crucial* duty. “What is my duty?”

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“First…” she said, turning back around to face me. Her hands went casually down to the bottom of the Pikachu tank top, her eyes locked with mine as I tilted my head back up. “You must help me disrobe… partially.” My eyes went wide, and my heart started to race a bit. My erection throbbed. She began pulling the shirt upward, and everything seemed to happen in slow motion. My eyes were glued to her in front of me, but my thumbs managed to unlock my phone and bring up the camera. I looked down only for a moment to press record, and brought the phone up at Amy.

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The shirt traveled up over her stomach, which was tight and flawless. As the shirt moved over her chest, I smirked cheekily. Her bra was white, with two small Squirtles printed over where her nipples might be. The straps were the same blue as Squirtle. The tank top went all the way over her head and pig tails, and then she dropped it in the floor. I just stared at her chest, holding my recording phone at it. Her breasts filled the cups of the bra nicely. They weren’t humongous, but definitely weren’t small. She had to know I was staring.

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“Stand up,” she said as she turned around for her back to face me. I stood as she requested, finally ending the recording and sliding my phone into my pocket. “Very gently undo the clasp of my bra.”

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“Yes, your grace,” I said, swallowing hard as I wiped my sweaty palms on my shirt. I knew this was a test. How well I did this would impact the amount of experience points I got. I shook my head, and tried to focus. Leave it to me to be thinking more about the game, then the half nude woman in front of me.

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I stepped closer to her, and looked at the back of her bra. This was something I had never researched before, and definitely not something I had practical knowledge of. How complicated could it be though? I couldn’t see anything helpful on the outward face of the straps, so gently I brought up my hands and grasped the straps on each side. I pulled them each toward the center gently, and then I could see the clasps on the inside. I pulled a little more so the clasps could come free, and then it was done.

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That was pretty easy, I thought proudly to myself.

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“Good job,” Amy said, and I took a step back. With the now loosened bra, Amy shrugged her shoulders and pulled it off. She tossed it onto the bed, and her hands came up to her chest. She turned back around. She was topless, but with arms crossed, she covered her breasts with her hands. “My breasts are integrally important to the success of the ritual. They must be treated delicately, and symmetrically.” She looked down at her chest, and back to me. “You must reveal them yourself, gently grasp my wrists and pull my hands away.”

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I took everything I had to keep my hands from shaking, as I stepped back toward her and reached for her wrists. I grabbed them very gently. There was a tiny bit of resistance that Amy’s arms gave. I pulled only a bit harder, and they began to move. Her arms uncrossed slowly, and her fingers slid away from her breasts. My eyes were entranced on the close up view that I was getting, as I pulled her arms away and to the side. My heart raced, and my erection throbbed. I could feel precum leaking onto the pitched tent in my shorts. They were absolutely perfect. I stared at them intently, knowing full well Amy couldn’t expect much more. Almost instinctively my phone came out of my pocket and took a picture.

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“Come…” She said, and she turned and walked toward her bed. The comforter was big and black, she crawled onto it, and laid on her back. Her head came to rest on a fluffy white pillow, and from underneath it she produced a black sleep mask. She put the mask on, covering her eyes, and laid there. Her palm padded a spot beside her waist. I took that to mean where I was supposed to sit. I tentatively crawled onto the bed, sitting on my knees next to her.

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“Play with them,” she said, her arms raised above her head, her hands underneath the pillow. “Gently… delicately, one hand on each breast, symmetrical motions.” The symmetry part was a bit unexpected, but I couldn’t imagine it would be difficult to make sure my hands moved with the same motions.

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I gulped silently, and reached my hands out toward her chest as she lay on the bed. My fingers came in contact with the supremely soft skin of her breasts on the side, and I felt more precum leaking out from the tip of my dick. I tried to keep my touch very soft as I gently cupped the bottom of her breasts. As delicately as I possibly could, my hands began slowly exploring them. Every inch and curve of her breasts made my erection twitch in a new way. I absolutely could not believe this was happening.

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Amy’s eyes were covered, but the way her mouth hung open just a bit made me think I was doing well. My hands kept moving, and then I finally allowed my thumbs to brush over her petite pink nipples. The tiniest of gasps escaped her lips when that happened, and I smiled.

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I lost track of time. I may have forgotten who or where I was. The entire cosmos faded away, and the only things that existed were Amy’s breasts. Entranced, I slowly grew more vigorous. Caressing turned into gentle groping, and Amy began to get more expressive. A small moan escaped her lips, and she bit her bottom lip again. I began teasing her nipples more with my thumb. They grew quite stiff and more pointy. I started pinching them sever so softly between my index finger and thumb. I gently pulled on them.

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Just as Amy started to get a bit worked up, her body squirming just a bit, she pulled of her masked and said, “Okay, that’s enough.” My hands left her breast and went to my lap, as I sat there hoping I didn’t screw anything up, still rather in disbelief that this was actually happening. “Very good job, my wizard.”

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She smiled, and slid off the bed. She grabbed her bra from the floor, and walked around and handed it to me. “Deposit your tribute into that, try to get the same amount in each cup.” I took the blue Squirtle bra and just looked at it, before looking back up to her. She smiled and began to walk toward the door. “You have one minute,” she said, as she stepped across the hall to the bathroom.

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I immediately pulled down my shorts, right on Amy’s bed, and began stroking. I put the bra down on the bed, my plan just to aim it down. It didn’t take long at all before I began to swell. The sensation and memory of what had just happened was fresh in my mind. I moaned a bit as I leaned forward, one hand resting on the bed, and aimed the first couple of squirts into the left cup. My hand still stroked, as I changed directions between spurts, and began to get the other bra. By the time I was done, I was out of breath. I stood there on the bed for a moment, erection still resting in my hand.

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“Time’s up,” I heard Amy say, as she walked into the room. She looked right at me, and I quickly pulled my shorts back up. She scrunched her nose, but definitely got an eyeful. She was still topless as she walked over and examined the bra. There were two distinct pools of cum, that hadn’t quite began to dry up yet. She carefully reached down and took the straps. I watched her intently as she brought the bra back up to her chest, and began to place it on. A bit more cum came out in my shorts as I imagined my life seed being pressed onto the soft skin of her breasts. She reached behind and clasped it, then put the Pikachu tank top back on.

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“I’ll go add up your experience points now,” she said, with a little wink. We both walked back down together, but I was completely at a loss for words.

Source: reddit.com/r/sexystories/comments/cfjhcw/the_babysitterdungeon_master_11_advanced