Wanna Bet? 2: Higher Stakes - Sex Stories

Wanna Bet? 2: Higher Stakes

... when I told her to stop. I certainly was, but I needed to cut things off there. I didn’t want her to cum. I had to keep her excited. The second picture had her on her knees, ass to the camera, but with her face visible, turned back with a smile. This time, the hairbrush was in her ass, all the way. I told her to imagine it was my cock, and she rolled her eyes a little, but it went virtually all the way in. The picture I chose had her hand on the head of the brush, as though she was fucking her ass with it. But I didn’t take it right away, I let her actually fuck herself with it a little more, until she seemed to be starting to grunt. “Okay, that’s enough,” I typed. “You really have a nice ass Lara. I can’t wait until you lose the bet and I own it and can do the job myself any time I want… I’d make you cum so hard you wouldn’t be able to stand afterwards. I got the pictures I wanted though. 2 down, 8 to go. Good night.” I liked the idea of leaving her hanging like that, even if it was abrupt. It made sense to me. Either it wasn’t turning her on very much and it was better to end it, or she’d want to take care of herself with the brush… and I could just bet she’d be thinking of me while she did it, what it’d be like to be my sex slave. I had to wait for the next batch of pictures, since I wanted to get them in person. I don’t know if it was because she was busy or because she was having second thoughts, but the next time I had a chance to see Lara was on Thanksgiving. Last ...

... year we took a trip to see the other branch of the f****y tree, but this year we stayed close to home and we planned to have it at Uncle Bill and Aunt Sharon’s place. We arrived pretty early, because my Dad and Uncle Bill enjoyed watching football. They considered it part of the whole Thanksgiving experience. Personally, I never warmed to football, something about it always seemed kind of gay. Guys wrestling against each other over a ball and patting themselves on the ass. I was more into basketball. My Dad drove us, even though I had my own car. As soon as we pulled into the driveway, we had to pull out again, because my cousin Todd arrived in his BMW and wanted to pull it into the garage. There was almost a fight over it, since my cousin’s abrasive and pushy, but once it was settled he acted like there was no hard feelings. Arriving with Todd was a woman I’d never seen before, probably around my age, maybe a year or two older. She was quite pretty, slim but tall, with dark brown hair just past her neck. Todd introduced us around. “Jeannie, this is my Uncle Alex, my Aunt Bonnie, my little cousin Mark, and my littler cousin, Faith. This is Jeannie, my girlfriend.” I would have just greeted her normally, but being referred to as a “little cousin” when I was s*******n and in my last year of high school pissed me off, so when it was my turn to shake her hand, I said, “Nice to meet you,” and then stage-whispered, “You could do so much better.” She gave a brief laugh and a warm smile ...