Cam Connection

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!"

I'd been so wrapped up in my plan that obviously not everything was registering but bit by bit I noticed a few things - her hair was much shorter than she'd ever had it, it was lighter in colour, she looked like she'd lost a few pounds and her voice didn't sound quite right. Apparently my brain figured things out before I realized it and as often happens, the words came out of my mouth before I could stop them. "Mom! What the fuck are you doing here?" And if that wasn't bad enough, before my mouth stopped, the next thing out was "I was expecting Janet". Oh fuck, did I wish I could pull those words back but it was too late!

As soon as she heard my voice she rolled over and I certainly got the shocked look I'd been anticipating except that it wasn't my sister I was looking at, it was my mother. We were both surprised as hell and while even though seeing a naked woman with a vibrator in her pussy and totally hard nipples on very nice tits aren't exactly things that will help a young guy go soft - I quickly did.

It took her a few seconds to function but when she did, her first words were "Oh my god...noooo" and she quickly pulled the blanket up to her neck, covering everything that I had been enjoying seeing. As she processed things she got a puzzled look on her face and her next words were, "what did you mean you were expecting Janet?"

Oh boy, I'd hoped she'd been too shocked for that to register but I guess she wasn't. I sat beside her on a corner of the blanket and after a long strained silence we started talking. I told her that initially I was just enjoying the cam shows and told her how I'd seen the room and recognized it. Thinking it was Janet I put the plan together to meet with her and embarrass the hell out of her as payback for everything she'd done when we were both at home.

Then I asked mom why she was playing on cam and she said since dad died she hadn't felt like a relationship with anyone but got so horny that she masturbated a lot. She'd heard of ppl doing live cam shows and the idea of being watched turned her on even more. One day she decided to try it and knew that Janet had a webcam because Janet used to talk to her cousin in Australia and that's why she was using Janet's room. She quickly realized it was a huge turn on to know people were watching her naked, playing with herself, telling her how hot she looked or that they'd love to be there with her and she thought it was perfectly safe and anonymous. Now any time Janet was out, she'd go onto her computer and play on cam. One day when she was on, I had messaged her and things went from there.

Of course mom then asked if I'd been planning on doing anything sexual with Janet and I said no, I was just planning on embarrassing her and having it on video to ensure she never did anything shitty to me again.

"Then why were you standing there with a hardon in your hand when I turned around?"

Now I was getting embarrased again but answered "Well seeing/listening to a naked woman playing with herself is pretty hot so I thought I'd get a few strokes in first."

"Even thinking it was your sister."

More embarrassment, "Wrong I know but yes, that still turned me on and got me hard thinking it was Janet"

"Would you have still gotten hard if you'd known it was me?"

As we'd talked, the blanket had slipped down to her waist so not only was I able to see her still firm tits again, her nipples were hard and sticking out.

"Nevermind, I guess the fact you're getting hard again answers that question" she said with a bit of a smile.

Looking down, I realized that not only had I forgotten to tuck myself back in but the sight of her half naked had certainly got me rising again."

I figured at this point things likely couldn't get worse so I looked at her nipples, then up to her face and said, "not as hard as I'd get if I could see all of you naked again and definitely not as hard as I'd get seeing you play with your toy some more."

"Seriously? You'd get hard watching your own mom naked, playing with herself and fucking herself with a toy until she cums?

At first I thought she was mad but then realized she was staring at my cock to see what my reaction was and it was pretty much immediate - from firm to fully hard and pulsing. I wasn't sure but thought I heard a very low moan as she looked at my cock so I thought I'd see where things would go and asked, "how about you...would your nipples get even harder and your pussy wetter if you watched your son play with his cock until you finally see my cum shoot out?"

I could tell by the look on her face she liked the thought and this time I knew I heard a bit of a moan. On a whim, I reached down, started stroking my cock and said, " go ahead, watch me stroke it and let me see all of you, let me see you touch yourself, let me see you fuck yourself with the vibrator, let's both cum watching each other."

At first I wasn't 100% sure what her reaction would be but her eyes stayed glued to my cock while her hands slowly pulled the blanket away. If I hadn't been fully hard, the sight of her wet pussy with the toy still sticking out would certainly have done it.

Almost like she was in a trance, she watched me stroke my cock and at the same time resumed sliding the toy in and out with one hand while the fingers of her other hand teased her clit.

Even with the shock of what had happened, both of us were excited enough that it didn't take long. I came first with spurt after spurt of cum shooting out. I'm not sure but I can't remember shooting that much or that far. One spurt landed across her belly and another right across her thigh, hitting her hand and the vibrator.

That was enough to trigger her orgasm and with a loud moan, her hips arched up and she shoved the vibrator in as far as she could. She didn't squirt but I could see her cum oozing out around the toy and trickling down her thighs.

After we'd both calmed down, mom looked at me and said, "Oh my god, that was intense. I can't remember the last time I had an orgasm like that."

"Me neither - that's the first time I've watched a woman using a vibrator on herself - in person at least - and that made me cum even harder. Soooo...what do we do now?"

"Well, pretty sure we both know that no one else can ever find out about any of this so just to be safe let's delete what you filmed on your phone - but not until we've had a chance to watch it." she said with a smile.

I was hoping to keep that video but realized I'd still have whatever was on the two trail cams that she didn't know about and could hopefully copy this one first so I agreed and asked if she wanted to play for me on cam again or if she'd be too embarrassed."

"Oh I definitely plan on playing online ...it's a huge turn on for me."

Hesitantly I asked, "Any chance you'd like to do it in person again sometime?"

I was expecting a 'no' to that one so was pleasantly surprised when she replied, "well, it'd be totally wrong but once the initial shock of knowing my son's been watching me masturbate on cam wore off I enjoyed this even more than cumming on cam. So yes, if you're ok with cumming while you watch your mother cum - or (and there was a slight pause) maybe even us helping each other then we could try doing it again."

As I was absorbing that welcome news, I was even more surprised when she continued with, "In fact, how about right now" as she reached down and grabbed my quickly re-hardening cock.

I don't think either of us knew exactly where things would go from here but I was pretty sure it would be a lot more fun than I'd have had just shocking Janet!