1. Babysitter's First Time


    Date: 2/18/2016, Categories: First Time, Mature, Taboo, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    vampire, sorta, but a good one. But who ever heard of a vampire named Charli anyway? She had long, long black hair and very white skin. Charli's skin was so white you could see the little blue veins even, and her eyes were blue, which looked really cool. Bright blue too, but she liked to put a lot of eye shadow and makeup around them. And lipstick, really red lipstick. She told me she was the original Goth Girl and I believed her. She even had tattoos on her shoulders, like big black wings that almost covered her whole back and I'd wondered if she was an angel when I was real little. After about a month of babysitting my mom was finally comfortable enough with it so that Charli and her husband could convince her to go out with them once in awhile. They had always been asking my mom to come with them, and I always wished she would, because I know it was hard for her to be alone sometimes. I mean even with me there she was still sorta alone. My mom is very pretty too, but more like me, all blonde and tan and smiling. She was 28 years old, but didn't look like it at all. At least not to me. She looked more like she was 16 maybe, because she dressed just like the girls I saw going to high school. In fact one Saturday night when she was going out with Charli and Charles my mom was wearing a schoolgirl outfit, a real one like the catholic girls wear to school. It looked nice, but sort of small maybe and when she walked I could almost see my mom's underwear. I asked my mom why she ...
    was wearing the uniform and she told me they were going to a costume party, but she looked kind of nervous, or embarrassed maybe saying that, I'm not sure. Anyway, the more comfortable my mom got, the more she started going out with Charli and her husband, and pretty soon it was several times a week, not just on Saturday and Sundays. Tuesday nights were costume party nights, I guessed, because that was mostly when my mom wore the schoolgirl clothes, or sometimes her Girl Scout uniform, which wasn't really hers. She bought it at the thrift shop and it looked cute, but kind of funny on her. My mom looked like she was my s****r for sure when she wore that. One Tuesday mom was wearing a cheerleader outfit, all white and red, just like the high school girls wear for the football games and stuff. It looked cool, except she didn't have any cheerleader shorts I guess, since she was wearing red panties. I told her she better be careful if she started jumping or everybody would know. That just made her laugh a little and then she really surprised me. She had a dog collar and she was putting it on. &#034What's that?&#034 I asked, knowing what it was, but not sure why my mom would wear it. &#034What does it look like?&#034 My mom smiled at me in the mirror. &#034A dog collar.&#034 I said. &#034Then that's what it is.&#034 My mom shrugged. She'd been acting sort of weird ever since I started babysitting. &#034Charli gave it to me, do you like it?&#034 &#034I guess.&#034 It was black and ...
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