I'm 16 and lost my virginity to a carrot when I was younger (around 12) and since then I've been masturbating on a regular basis ever since, at least 3 or 4 times a week. My mother used to have a couple of vibrators and dildos which I used to 'borrow' until I got caught and then she got rid of them. So I had to stop using them, until I bought my own of course.
The story I wanted to tell you about happened over the Christmas holidays when I went to stay over at my aunt's place. She just lives down the street from us, but my baby sister and I had to stay there because our folks went on a trip. My Aunt Jenny is pretty cool. She's about 32 but is always busy and I don't see her date very much. Knowing this, I took the opportunity to look through her drawers and stuff for a dildo or vibrator but there was nothing. In one other closet though, I found the most awesome machine in the world. It's this thing called the Sybian. At first I didn't know what it was because it just looks like a rounded machine, but I found some attachments that were all these dildos and stuff for your butt and a video tape. I knew this was something she must have used to get off with, but since I didn't have much time and because my sister was downstairs watching tv, I just put everything back.
That night, I got so wet just thinking about what that thing would do that I masturbated and must have came about 3 or 4 times in a span of only a few minutes. The next day, Aunt Jenny wanted to take us to the water park, but I made like I had an essay to write, so she and my sister Lisa decided to go anyway.
I pulled out the videotape and stuck it into the vcr and I couldn't believe what I was seeing. This was like a tape to teach you how to use it with women sitting on this thing and cumming all over. My hands were trembling, thinking about what I was going to do as I went upstairs and pulled out the machine. I set it up using one of the smaller dildos and turned it on and WOW! I COULDN'T BELIEVE IT! I must have cum about 20 times at least and by the time I got off I had tears coming down my face because it was so good. I had never in my life experienced that kind of orgasm before. After I had rested a bit, it put the butt plug part on and used both at the same time and I was going crazy again.
After that, I took every opportunity to use the machine whenever Aunt Jenny went out. She eventually found out and once asked me if I was feeling more 'relaxed' staying at home and grinned at the same time and I acted like I didn't know anything. But she said it was okay if I was using her 'boyfriend in the closet'.
Towards the end of our stay, Aunt Jenny went to something and I was home alone with my baby sister Lisa. I badly wanted to use the machine, so I decided to take a chance and use it while Lisa was downstairs watching tv. Thing is, I didn't expect her to come upstairs and catch me. I forgot that I was not alone and made a lot of noise and my sister came upstairs to see if I was alright. When she saw me, I was right in the middle of cumming, so I couldn't hide it.
Lisa asked me if she could do it too so I said okay, as long as she didn't tell mom or dad. She's only 11 but I know she also broke her cherry using her fingers and my mom's dildo last year. I told her that the attachment was probably too big for her so we put the butt part in the front and she jumped on. This was the first time I've ever seen my little sister cum as she rode it. She arched her back with her eyes closed as she came multiple times in the space of a few minutes. My pussy was dripping wet watching her, so I stood there masturbating as she got herself off.
My folks returned from their trip the next day, so that was the end of staying over at Aunt Jenny's house. Being in high school, my activities for this semester have been busy, so I don't have the chance to visit Aunt Jenny except on weekends. Lisa, on the other hand, since she gets out of school around 2:30 everyday, got my mom to let her spend time over at Aunt Jenny's house until they got home around 5. So my little sister has that thing all to herself. I hope she doesn't burn it out until I can use it again!