It pays to be a nice guy - based on true events.
I am so glad I found this site. I've enjoyed it for so long, I felt I should give back with a story of my own, from a very exciting time from my past!
I was an abnormal teen - abnormal in that I was athletic, with an athletic body that made me look older than I was. However, I was known to be a nice guy - not one of those stereotypical jocks, but a good guy that was known to be good with children. I often got asked to babysit because kids liked me, and being a guy, parents liked hiring me to look after their sons (who probably misbehaved for other babysitters, as boys often do).
One Saturday I was asked to babysit for a family I had never met before through friends of friends. The family were wealthy with a big house that was great to play hide-and-go-seek in. In one of the rounds, I found myself hiding in the master bedroom (last minute decision). While hiding, I don't know what made me do this, but I opened the top drawer of the dresser. My heart immediately jumped as I found a pile of porn mags. I quickly leafed through some, but put them back quickly when I heard footsteps. I couldn't wait until the boys had to go to bed, so I could sneak back into the master bedroom, and spend more time with those magazines.
When the anticipated time came, I opened the drawer and got hard while I looked through the pictures of the magazines. However, while rummaging through the drawer for mags, I found some video tapes. Could this be what I think it is? I grabbed 1-2 videotapes, as well as a smaller videotape that I hadn't seen before (I wasn't sure if this was a Beta tape - was giving me options), and ran downstairs to the TV / VCR. YES! it was. It didn't take me very long to rip my pants down, and stroke my cock to the images I was watching on TV. I stroked my hard cock to two girls in a hot tub. I came a couple of times to a mom catching her daughter fucking her boyfriend when supposedly studying, and then joining in. I lost count how many times I came that night, so many times that I didn't have any cum left, and my poor young cock was worked out! I loved both video tapes, but I didn't know what to do with the smaller video. It obviously wouldn't fit in the VCR, so I just left that one. I lost count of time, so I thought I better clean up and put the videos back before the parents came home.
A week later, I got another call to babysit for the same family. I couldn't wait to stroke my cock to more porn! There were many videotapes to watch. I couldn't wait for the kids to get to bed and fall asleep, so I could watch the porn. Figures, the kids were not sleepy, and were having a difficult time getting settled. Why couldn't they just get to sleep so I could masturbate to porn. I was so excited when they went to sleep, that I didn't think about the time being late. I grabbed a VHS tape, and one of those smaller ones again to see if I can figure it out. But first, at least one cum to with the VHS. I ran downstairs, threw the video in the VCR, pushed my pants down and started to stroke as I hit play. I was rubbing my cock up and down with a big smile on my face, when I heard the front door open. SHIT - They were home!! Fortunately the TV was in a back room, so I had seconds. I pulled my pants up while punching the Eject button. I ran toward the stairs, passing the mom (the father waited in the car to take me home). I hid the video behind my leg as I ran past the mom.
"David, is everything ok?"
"Yes", I answered, "I just told the boys they could listen to music but I'm going to tell them to turn it off because you're home."
I sprinted up the stairs, put the video back in the dresser, then went back down to say bye.
I was so nervous going home, I was glad to get in my own home. Then it hit me - shit, I left the smaller videotape downstairs. If I wasn't already busted, I will be now! I just hoped the parents found it before the kids did, not that it wasn't easy to just pop in and watch. Well, I guess I'll never get called back to that house again!
A couple nights later, I did get another call from the mom. Oh no - I'm going to get in trouble! I was suspicious of nice she sounded on the phone.
"David, you are so good with the boys. We really appreciate you. Are you available this weekend? My husband and I are going away overnight - could you stay over? And David, you can even sleep in our room."
"Um, sure, ok" is all I could stammer out.
My excitement to be able to pump my cock to videos all night long, without the worry of getting caught superseded my surprise to getting caught.
Saturday night came. The mom brought me to the master bedroom, and showed me the en-suit bathroom, and the TV and VCR in the bedroom. "Feel free to watch movies in bed." she said with a grin - hmm..interesting thing to say ;)
After the kids went to bed, I stripped down naked, popped in a video, and wrapped my hands around my cock. I was rubbing my cock slowly, as I wanted to make this an all-nighter.
I was enjoying this so much, I didn't hear the door open, or footsteps coming up the stairs. I did, however, hear the bedroom door open, and was scared shitless to see the mother standing there. No way of getting out this - no time to get clothes on or under sheets, and the girl moaning on the TV was obvious!
"Mrs. Smith - I'm so sorry!" I yelped, as I stumbled to get sheets around me.
"David, it's ok - shhh. I know. I know. I wondered what you were up to last time, but when I found the video you forgot downstairs, I knew you found our videotapes. It made so wet to know you watched me on video."
"You - I didn't see you. I couldn't get the smaller video tapes to work."
The mom giggled. "David - those are personal videotapes. You need a special VHS case to put the tape in so you can watch it in a normal VCR. Would like to see one?"
I could only shrug, still freaking out about what I should do. "What about your husband?" I asked.
"David - we are swingers. My husband is with one of our friends, so I could come home and see you." I realized I had been set-up, and my pumping heart changed from scared to excitement.
The mom chose a smaller video and put it together with the VHS shell, and added it to the VHS.
"Before I hit play, do you want to watch this?" she asked. "Yes" I stammered.
"Well, you don't seem to want to. Come on, show me you're excited. Let me see that young, hard cock!".
I couldn't believe this. Only my girlfriend had seen my cock, but this isn't a teenager - this is a sophisticated women!
After she urged me again, I pulled the sheets off to the side, and slowly stroked my hand up and down my cock.
"That's better" she said, as she pressed play. OH my - there she was, standing in front of me, but also on TV, naked, sitting sprawled out, fingering her pussy while sucking 2 guys' cocks.
My hand immediately started pumping faster with the images I was looking at.
"Hot, isn't it" the mom said, taking off her blazer, and unbuttoning her blouse.
"Oh Mrs. Smith - you're so hot." I answered, staring at her wet pussy on the TV.
"Hmm, we need to slow down." She said, while taking over. The mom replaced my hand with her own hand, and her tits, caressing my cock between both her hands and and cleavage. Being a sophisticated, older women, she definitely knew what she was doing, changing her speeds and intensities.
Finally, while I watched her on TV, she picked up the pace and I couldn't hang on anymore. I shot more cum than I had ever did before all over her breasts.
I felt so comfortable and at ease while we laid there together, watching the video.
"Do you like what you are watching?" she asked.
"Oh my, your pussy looks so wet." I responded.
"Well, why don't you get first hand experience" she responded, sliding off her skirt and panties.
Being young and new, I copied the video in how I touched her. She was so warm and so wet - I'll never forget how it felt.
We spent the whole night touching each other, and watching each other. We didn't have sex because of the age, just stroked and fingered, and came over and over.
She slipped out as the birds were starting to sing, before her kids woke up.
I never got a call again from the family - I wondered if she felt guilty of taking advantage of a young, naieve high school boy, but I didn't care - it's a memory I'll never forget!!!
Sorry this was a long story - hopefully I'll be rewarded with some comments.