Enid: Fucking the Babysitter

Cadi has been working from home still, and late last week she decided that she couldn’t be bothered with proper outfits anymore. Instead, she wore jogging bottoms and a nice blouse on the top for Zoom.

The joggers reminded me of that sort of genre of gay porn where there’s two ostensibly straight lads jerking off together, or where there’s an older lad (like a step brother or a brother’s best friend) coercing a twinky guy into jerking off. Cadi was really amused when I made this connection, as apparently she’s not as familiar with the different niches of gay porn even though she’s the bi one! She was also pretty intrigued when I told her that it made me want to suck her strap. That should be less of a surprise, as she knows I am pretty much always thinking of getting my mouth used by a hot girl.

After work she asked me if I would be comfortable with a scene that involved age play and coercion. We don’t really do roleplay with characters…or…that’s not quite right. We used to roleplay more in our late teens/early twenties. I even remember trying something based on the Gerudos when she introduced me to playing The Legend of Zelda. But it’s something that we’ve not done as much in recent years. I was definitely up for giving it a go!

I got into my small pink PJ bottoms and fleecy Barbie jumper, and took my favourite soft toy (Sakura) downstairs. I got comfy on the sofa and started to play with Sakura, letting myself relax and get into the headspace. Eventually she came down the stairs wearing a little tank top and a big flannel shirt. I could already see her big strap stretching out her joggers. She introduced herself as my babysitter, looking after me while my Mama was out enjoying herself, as single Mamas should be able to do! She was mean, dismissive, and totally disinterested in my Sakura. I started to get a little bratty and pouty, in a way that Mama never usually allows!

I imposed myself on her, moving into her space and making Sakura run up and down her leg. Inevitably, this led to me running my hands over her bulge, and her taking it out for me to look at. I love pretending to jerk off a strap, and she drizzled a bit of lube over it so I could get into it. I wound her up enough that she needed me to suck her, and I was very happy to. Usually when we play with a strap I tend to call it that, but during this scene Cadi chose to call it her cock.

She told me she wanted me to “choke on her cock,” and held my head and fucked my throat until I was sick in my mouth, and then made me go to the kitchen sink to spit it out. This felt so gross and dirty, and when I got back from the kitchen she fucked my throat again while calling me her “cock hungry bitch.”

She started to rub her clit underneath the dildo while I sucked it. Eventually, she got too desperate and pulled the dildo right out of the central ring of her Aslan strap-on, then pulled me in so I could get her off. After she came she pretended to freak out, saying she never meant to let it get this far and she had to put me to bed immediately. She made me promise never tell my Mama!

I snuggled down and pretended to go to sleep. When she came back she was wearing a beautiful velvet maxi dress that she must have smuggled into the spare room earlier on in the evening. Inside, I was screaming with laughter at how prepared she was!

When Mama gave me my nightly inspection she found that I was wet and swollen and she immediately guessed what my babysitter had been up to. She fucked me with her fingers and fisted me, and I went into that really special sub space that only fisting can get me to. I’ve got a half-written blog post about how much I love it, that I really must finish! Cadi spotted that in my face, and whispered to me that it was okay to let go, and to give in to it.

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