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

(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.

The Babysitter/Dungeon Master 14: The Early Wizard Gets…[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 14 is FINALLY here! I know some of you have been waiting patiently, and for that I’m thankful! These don’t always come out as quickly as I would like, but I’m hoping to get back into the groove for the next few chapters. As always your comments and messages are very motivating! Enjoy! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 14: The Early Wizard Gets…

(Amy)

I woke up the next morning feeling like a million bucks. I thought things might go slower between myself and the boys, that I’d be way more nervous, but the three of them had only been here for six days so far and I’d already let them physically help me to masturbate. It was amazing. Lying in bed wearing only panties, just staring up at the ceiling of our blanket fort, all I could do was think about what had happened last night. Michael’s hands on my legs… His hands felt strong, and I loved the way he squeezed my thighs. Brandon’s hands on my breasts… His hands were soft, and his actions delicate. Every tough on the sensitive skin of my breasts felt like a tease. And the kisses from Will… It had been so long since I had been intimate with Will. Despite knowing it was wrong, I couldn’t help but feel a real emotional connection when we made out.

The Babysitter/Dungeon Master 13: Restoring the Castle[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 13! This one was fun to write. So glad you guys have been sticking with it, hope every enjoys this entry! Feel free to comment, or shoot me a PM if you enjoy the story. Thanks in advance! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 13: Restoring the Castle

I heard Will shut my bedroom door, and suddenly I felt like I couldn’t catch my breath. My heart was racing, and my fingers a bit sweaty. Despite having quite planned it, I couldn’t believe what just happened. I just laid there on my bed, Will’s cum scattered all over my face. I felt it on my nose, and running down the sides of my cheeks and underneath my eyes. I felt it on my lips, and when they parted I tasted it on my tongue. More sweet than salty, I used a finger to slide more into my mouth. I savored it, swallowed it, and sucked on my fingers.

The Babysitter/Dungeon Master 12: It Comes in at the Eyes[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 12 has arrived! Thank you all for your continued support and compliments. You guys really make me feel special :) I hope you enjoy this chapter, and as always feel free to drop me a comment or a message! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 12: It Comes in at the Eyes

“What do you think they are doing up there?” I asked Michael, as we sat on the living room couch. Amy and Brandon were still upstairs, had been for at least twenty minutes. Michael and I waited downstairs, him more patiently than me. My curiosity was overwhelming me, and nothing could distract me from thinking about what was happening upstairs. I found it hard to sit still without fidgeting. “Think they are in character?”

“I dunno,” Michael said, as he chewed on a stick of beef jerky. He didn’t seem to be fretting. After all, he had gotten to jack off today. Going three days without cumming shouldn’t have been a big deal, but every time Amy was in the room I could feel myself getting worked up… but there was no release. “Maybe the Wizard is casting a ‘life seed’ spell on her face, with his ‘magic wand’.” He chuckled at his own, joke and I rolled my eyes.

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

(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.

“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.

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

The Babysitter/Dungeon Master 10: The Restless Barbarian[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Chapter 10 incoming! Thanks so much for continuing to read, glad to have this installment out to you guys without too much of a wait! As always, if you enjoy leave a comment or feel free to send me a message. Until next time! *(This work is entirely fictional, as are the characters portrayed in it.)*

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# The Babysitter/Dungeon Master 10: The Restless Barbarian

(Michael)

The night that Amy dropped the bomb on us… that she knew about our secret drive… changed everything. I didn’t have the time or precious mental attention to process why as she said she was going to bed. I watched her scamper off upstairs, and then looked back to my phone screen. The picture that was just taken a moment ago was still full screen. I wasn’t sure how it even happened, she made this… face… and then suddenly the top of her shirt was around her waist. It had to be an accident based on how red her cheeks were, she definitely seemed a bit embarrassed. Regardless…

It Was. Glorious.

The Babysitter/Dungeon Master 9: The Oath of Devotion and Bondage[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! As always, sorry these aren’t coming out quicker! Also sorry if I haven’t been able to message anyone back in a couple of weeks, it’s been hectic irl. In case anyone is at this point unaware, these stories and characters are **completely fictional**. Thanks again for those who have been reading, I hope you enjoy! If you do, feel free leave me a comment or send me an orange envelope!

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# The Babysitter/Dungeon Master 9: The Oath of Devotion and Bondage

(Amy)

My lips curled considering, as I checked myself out in my bedroom mirror. I stood close to the mirror as I examined my tank top, pop music playing in the background. It took me a while to find this *specific* white tank top, it was buried in my closet. I washed it, and threw it on to see if it still had the same problem it had before. The neck of the shirt was cut low and wide, probably made for a woman with bigger breasts. Mine weren’t small, but nevertheless, the tank top held them awkwardly. I twisted my shoulders a bit, and casually bent forward. Without a bra on, bending forward revealed my breasts perkily hanging there. And if I leaned forward enough… you could basically see everything. I stood back up, and carefully placed the straps of the tank top on the edge of my shoulders. With my arms down, I gently gripped the bottom of the tank top and held it. With a deliberate shrug of my shoulders, and a tug to the bottom of my tank top, it slid down exposing my breasts entirely. I smiled, and decided this would work for the first game night of our summer alone together. I threw on a rather simple black skirt, and let my hair down.

The Babysitter/Dungeon Master 8: The Chalice[Fmmm][Ageplay][Dungeons and Dragons]

Hey guys! Another chapter in, sorry that it’s a little shorter than the rest. Thanks for continuing to read and letting me know what you think. As always, comments and PMs always welcome. Hope you continue to enjoy!

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# The Babysitter/Dungeon Master 8: The Chalice

(Brandon)

It was Tuesday afternoon, and it was finally game night again. I had been overly excited all day, as had Michael and Will. We met at Amy’s house at 4pm. She ordered pizza, and our parents agreed to let us stay until 10pm. I was elated. It was hard to take my eyes off Amy as she once again donned the mantle of Dungeon Master, and began leading us on the next branch of the campaign she designed. Not getting a boner was especially difficult for two reasons; I had been watching the video of Amy flashing us her tits over and over, and Amy looked and was dressed extra sexily that night. She had tied her hair up into pigtails, something I had never seen her do. She wore a little white tank top that was open on the sides, and left just a tiny bit of side-boob. It was not difficult to see the edges of her bra, which was red. Any time she’d lean forward we’d get way more cleavage than we were used to, and her bra was just loose enough in the front that each time I expected to see a hint of nipple. The shorts that she wore were very short, and definitely would not pass the ‘finger tip’ rule they had at school. It seemed like she had even put on just a little makeup, enough to make her look beautiful, but also be possible to think she hadn’t any on at all.

The Babysitter/Dungeon Master 7: Cum Brothers[Fmmm][Ageplay][Dungeons and Dragons]

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?”

The Babysitter/Dungeon Master 6: Amy’s Best Friend[FF][Ageplay][Dungeons and Dragons]

Hey guys! Sorry Chapter 6 took so long! It’s been a hectic month (Game of Thrones is over! Quite a let down, honestly…), but I’m trying to get back into the swing of things. Hope you enjoy the chapter below, and as always, feel free to comment or PM me, always love those little orange envelopes!

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# The Babysitter/Dungeon Master 5: Amy’s Best Friend

*(Amy)*

The warm afternoon air felt good whipping through my hair, as I drove zooming out of the city. My windows were down, and my music was cranked loud. The newest Taylor Swift single, *ME!*, was playing, but I hadn’t quite memorized all the words to sing along yet. My GPS led me along the highway for a bit, finally exiting onto a quite secluded road slanted upward into the hills. It seemed like I was driving forever as all signs of urban sprawl seemed to fade away until nothing but trees lined the winding road. I had a lot of time to think while I drove.