You know how some things just don't turn out the way you were expecting them to? Well, this was one of those.
I'm Dave, 21 yrs old and recently moved into my own apartment (it wasn't much but it was all mine). I was hoping for a much better sex life but apparently that wasn't meant to be - unless you count maybe once a month as a good sex life. Of course the internet never said no, so a lot of my evenings were watching/reading porn and then I found live cams. They were the closest things I could get on a regular basis to actual sex. I had an ok job so if I really liked one I'd buy some tokens and see what they'd show/do in a private session.
There was one girl I really enjoyed watching and would do a private session with occasionally (she'd fuck herself with a toy until she came while I directed). She never showed her face which was ok with me...her tits were awesome and I loved the closeup's she'd give me of the vibrator going in and out of her pussy. She pretty much knew if I was on, I'd be watching her cam so sometimes even if I didn't have any tokens she'd do a bit of a free show for me. I'd even been fantasizing about meeting her - at one point we'd been chatting about a news story and she let it slip that it was in her city which was not only just a half an hour away but also the city I grew up in.
One day she was playing with herself for me and bumped the webcam - it was only for a couple of seconds but enough for me to see the room behind her and holy shit it was my sisters room! Janet still lived at home with just mom, unfortunately dad had been killed in an MVC a few years ago. My mind went through a fuck ton of emotions in about 10 seconds - shame for knowing I'd been watching and fantasizing about my sister, arousal because even knowing who it was I was still hard, curiosity as to why she was doing it and disappointment that I'd been actually considering seeing if we could meet and now there was no way I'd be able to do that.
The more I thought about it, the more I thought this could turn out good after all. We'd never gotten along - she was just under 2 years younger than me but was what I'd consider 'pleasantly plump' and a lot of ppl thought she was older than I was (which really pissed her off). When we were both living at home, she was always trying to boss me around, tattling on me or getting me blamed for things she'd done (or not done), she always whined and got her way but did everything she could to make sure anytime I wanted anything that it didn't happen. All this was one of the reasons I'd gotten my own place as soon as I could afford it - basically she was usually a bitch to me unless she wanted something. Whenever I popped by to see mom, Janet did her best to be out with friends so I'd only seen her for her last birthday & Christmas and if she was around she did her best to avoid me.
She'd always been the 'good girl' - no drinking, smoking, hanging out with wrong people and was good in school (me not so much) so I thought this could be a perfect opportunity to get back at her. I started recording our video sessions and sure enough a couple more times there was enough of a slip to clearly identify her bedroom. The more we chatted the friendlier she got and I 'let it slip' where I lived knowing it was close to her. By now we were online almost daily - I'd tell her how much better it would be to feel her hand around my cock instead of mine and she'd play with herself and tell me she wished it was me fucking her with her toy or my tongue in her pussy instead. Apparently my sister was kinkier than I thought because occasionally our messages drifted to things like anal sex, facials/cum play and even light spanking.
.
Janet had mentioned that one of her fantasies was to be masturbating somewhere and be 'caught' by a stranger. Wow...I don't think I could have come up with anything better to have some fun with her but didn't want to sound too eager so I just said that sounded cool and didn't pursue it any further. About a week later, I brought it up and said if she really wanted to get caught masturbating, I'd love to be the one who caught her.
That started the ball rolling and we spent our next few sessions describing what she'd be doing (finally decided on her on her hands and knees fucking herself with a vibrator), what I would do (at first she just wanted to be 'caught' but then admitted it would be fun to have me take over the toy and play with her until she came) but to keep it as a 'stranger' doing it, she wouldn't look back - perfect! The hard part was finding a location but then I remembered a spot by the river I used to go to when I actually got a date or more often just to lay in the sun and jack off.
As soon as I started describing it, she knew the spot I was talking about (hmmm, maybe not so 'good girl' after all). She said late morning worked best for her so we planned on her getting there first and getting started and I would show up just before noon to 'catch' her doing it. My plan was to get there early with a couple of trail cams that I borrowed from a buddy and have them set up before she got there and then use my cellphone to video the look on her face when I told her it was me. I knew there'd be some yelling and likely some tears but it would be amazing payback for all the shit she'd put me through.
Everything started perfectly - it was a nice warm, clear day. The cams were in place aimed where I'd told her to put her blanket. I knew I shouldn't be but I was horny as hell knowing that even though it was my sister, I'd soon be seeing her playing in person, have it on video (maybe to jerk off to another time) and the best part would be the video of her face when she realized what had happened. Of course there was also the fear that she wouldn't show up but nothing I could do about that.
I'd considered hiding nearby to watch her arrive but figured the cams would get her arriving and starting to play so once everything was set up I left until my planned arrival time.
It seemed like days but actually less than an hour later it was time for me to 'accidentally' find her so cellphone already recording I headed toward where she was. As I got closer, I could hear her before I could see her, it's a good thing not many ppl came back here because her moaning was loud and clear - perfect - I hoped the cellphone would pick up the audio.
When I came into the clearing, she was kneeling on a blanket with her ass toward me just like we'd arranged and I could easily make out vibrator she was fucking herself with. I was sure she knew I was there because the next thing she said was "I'm so horny, I hope no one comes back here and sees me fucking myself"
Wow was she ever playing it up! As much as I knew I shouldn't be, I was hard as hell and knowing she couldn't see me, I couldn't resist unzipping and pulling my hard cock out and stroking it as I moved towards her. The closer I got, the more I could hear/see and the harder I got. Now I just had to decide how long I'd watch before shocking the hell out of her by saying "yes you got caught - and by your brother!"
