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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.

[FF] Playing boyfriend from my insanely hot BFF

Have shared in a long time, but hopefully you’ll like me recounting of one of my few lesbian experiences. You can jump to ***** if you want to skip the preface and backstory.

Let’s start with the fact that I have an insanely hot BFF. I mean, I know I’m not a dude, but even before this experience with her I had always jokingly said that if I were I would fuck her. She is constantly in the gym, naturally has a beautiful face and ass for days, and a few months before the night it happened, she had gotten a boob job. To help you visualize, instead of describing I figured it might be best to just share pictures (with faces blurred because, you know – stalkers): [https://imgur.com/a/XIQOs4R](https://imgur.com/a/XIQOs4R)

Like most insanely hot women, she unfortunately is also one of the most insecure people I know. This never really surprised me, because all of my hot friends are the most insecure people I know haha! At the time she had also been dating a married man for a couple of years (horrible, I know – but let’s not judge, ok?), but every so often they would breakup because she would get sick of the hiding and not being able to be a normal couple out in public. This night was one of those times. Read more »

Steak ‘ N ‘ Shake [mf]

Okay so in my home town there was a notoriously raunchy “Steak n Shake” restaurant. The food would sometimes take up to 20 minutes to come out of the drive thru window. Really really bad service, but still very much drawing a crowd. Being open nearly 24/7 also made it the hangout for many high schoolers and young people who were bored of walking through Walmart. I lived within a 2 minute drive, had disposable income and I would often go there late at night (2-3 am) and smoke weed in the parking lot. Anyway…. when I was 18 or so during one such night during the summer I decided I wanted a shake. I pulled through the drive thru. There was a big red headed woman (she was pushing 250-300) who was always my cashier. Extra nice to me always. One night I asked for her number as she hands me my food because I was working on being more assertive with women (lol)

A week goes by of flirty texts and such. She’s 27. Is named Sam. Has a boyfriend who is in jail. Typical shit. Read more »

Sweet and Dirty [MF] [Oral]

To most people, Layla Larone was the sweetest young woman that anyone had ever met. She had a smile that could light up any room, a feminine figure that rivaled that of any angel, and a spirit that made everyone want to be near her on their darkest days. Aden Stan knew that sweet side better than most. As her lover and fiancé, he drew plenty of envy from those who’d been captivated by Layla’s aura.

“Man, I still can’t believe you’re marrying Layla freaking Larone,” said Aaron Jay, Aden’s cousin and long-time friend.

“Gee, thanks,” Aden said, rolling his eyes. “You make it sound like I’m such a fine catch.”

“Come on! Don’t be like that, cous,” Aaron responded. “You’re an objectively great guy, but let’s not ignore the bigger picture, here.”

“And what picture might that be?”

“The same one everyone has been seeing since high school,” his cousin said. “Some women just have that special something – that perfect combination of looks, charisma, and energy that sets them apart. They could do anything, go anywhere, and be with anyone. She could go to Europe and marry a prince. She could go to any city and win over every heart. Hell, she could go to some remote village in the Amazon and be declared queen.” Read more »

Weeknight [FF]un

This past Wednesday night SOM is away, like he always is, on business. It was just an opportunity for me and the new Girlie to have some alone time. She hosted which was cool because I had never seen her place. It was just a studio, pretty minimalist except the bedroom. Every wall had been completely covered with random framed prints from second hand stores. So cool… There was a nice sitting chair. The bed was beautiful with all white sheets, and it had this amazing headboard that looks like a carved church door.

I was staying the night, and I wanted to cook-in with her. It seems that I am the cook in the family so it was up to me to bringing the groceries and the necessary accoutrements. I wanted to treat nice so it was pan grilled strip steak au poivre with asparagus. The level of attention afforded me while getting dinner together had me blushing and smiles the whole time. The only thing I had to distract her from me was wine and cheese duty. She kept hugging me from behind which I absolutely loved, but I kept having to pry her off because I was in front of the stove and had to be more mobile then she was allowing. Read more »

[F]irst Time [M]y Boyfriend Visits Me [FM]

I’m in a long distance relationship with my boyfriend of 9 months, who’s from the east coast as I’m from the Midwest. Prior to dating him, I was a HOE. Like once I dipped in, I was drowning in dicks. I have stories from my hoe days, so if y’all wanna read that shit, holla at yo girl. ANYWAYYYYYY:

My boyfriend and I haven’t seen each other physically for over 4 months. Needless to say, my pussy was hurting from the lack of dick. On top of that, we made a deal to not masturbate until he visited, which was about 3 weeks out from when we stupidly agreed to do that. I masturbate almost everyday and so this was a challenge for me for sure. Anytime we broke the challenge, (which I did twice because I told y’all I was a horny bitch) we would get penalized. The penalty was up to the other person. We kept this up til the day he visited and it just so happened that we didn’t FaceTime the night before. SOOOOOoooo a girl was fucking struggling. The day finally came and I woke up with my pussy drenched already. SHE WAS READY OKAY?! Read more »

The [F]irst time we [M]et

For years my husband had expressed his interest in seeing me with another man… A man with a large cock who could give me pleasure that he couldn’t.

I questioned him was that truly what he wanted and he always replied “your pleasure is my pleasure”.

So I[F] finally agreed to start messaging another [M]an, one my husband had already been in contact with.

The conversation was casual at first but not for long.

He stated “so I hear you like the idea of being fucked by a big cock?”

I replied ” Yeah I do like the idea of it?” and I really really did like the idea, but hesitant to know if it would actually happen.

He then sent me a picture of his cock. I was astonished. I had never seen a cock that big, other than in porn of course. It was at that moment I knew needed that cock.. I had to feel, taste, and fuck it.

Every time I fucked my husband after that his big cock would be in the back of mind. And my husband knew too. Read more »

I [M] slept with a BBW Granny

So where to begin….when I was 18 (now in my 30s) internet porn and the ease of access was still a relatively new thing. I remember back then I had this huge crush a friend’s mom too and I would jerk it to her literally every day. Well this fetish grew into more and more interest into older women with natural bodies. I already loved big boobs, so whenever I found porn of older women with big tits, I’d beat my dick like it owed me money. Eventually this led to me wanting to actually live the fantasy. I posted an ad on Craigslist casual encounters. Read more »