How I [F] Lost My Babysitting Job

So… I’ve always been a good girl. Not a perfect girl — but I don’t sleep around. There was that one guy when I was younger, but he dumped me when he got what he wanted, and I learned from that. Since then, I’ve kept my legs together, and now I’m nineteen. If I’m gonna be honest… guys my age are immature jerks. They are all over me for free handouts, and that’s not as flattering as they think.

And my parents are after to me to figure out what I’m going to do with my life, since I don’t have a college gig planned yet, and I’m not in a serious relationship. I’m doing part time at Hooters (don’t even fucking say it) and babysitting on the side. Hooters is good money — the tips are like triple what you get anywhere else. Yes, I know what the word objectification means, but the guys that eat there are less crude than what I see outside of work. My parents don’t love it, but they are the ones charging me rent, so I have to do something. So I figure it’s a start. It beats saying I’m still babysitting at nineteen.

How I lost my anal virginity in the shower when I was 18 years old…

I’ve got to preface this story by saying that, throughout my teenage years I was convinced that no matter the circumstances I had no interest in ever getting a cock near my asshole. I heard unpleasant stories of friends who told me that it hurts, was not pleasurable in any way and that they only did it because their boyfriends pressured them into it. I never got why I would want my asshole fucked, when my pussy was right next to it, was afraid of it and told myself that I’m not interested in trying it, pretty much ever.

Fast forward to when I’m 18, have a boyfriend and a drawer full of sex toys in my bedside table. By then I got introduced to some kinds of anal play, I loved to get my asshole massaged, have a finger inside during doggy and even got a small plug which I loved to wear while getting fucked. Getting to that point already took a lot of trust and time, but it was well worth it, and I enjoyed it a lot whenever my asshole was involved. I was never pressured into it, so I could always enjoy it to my own accord and got all my wishes respected. I still hadn’t changed my mind about anal sex by that time, it wasn’t really ever talked about and I was happy with the way things were and as far as I was concerned, they could stay this way. That was until I slowly started to have all kinds of fantasies…

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