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Handjob from my Neighbor

When I was in high school, I used to baby sit for a family a couple streets over. The couple had two youngsters, who I used to watch when they went out for dates or to visit other couples. I spent several months watching them about once a weekend – I would send the kids to bed in the evening, and then usually have a couple hours to myself to just relax before the parents arrived home. About once a month, the dad would hand me a wad of bills before sending me on my way.

One night, after watching tv for a couple hours, the mom came in through the back door, alone. She was pretty tipsy, apparently after a night out drinking with another couple. Her husband was still at the bar with the other guy, and both wives had shared a cab back home. I came out of the living room and met her in the kitchen.

She started chatting brightly with me, asking what colleges I wanted to go to and how classes and sports were going. That shiny look in her eyes never disappeared the whole time. Eventually, I was about ready to head out, so I got to saying goodbye. She started apologizing for her husband not being there, as it was my “payday”, and she couldn’t send me home with any money. I said it wasn’t a problem; they could just pay me next time. She walked over and gave me a huge hug, saying how thankful she was that I was available to watch their kids, and that I was so nice and didn’t mind not getting paid. She was squeezing me tight against her tits, with no space between us. I was trying to extract myself, knowing that I was instants away from an awkward situation, but it was too late. I got a boner pretty much on the spot, and trying to pull away probably made it all the more obvious.
She released her hug, and said “Oh”. She put her hands on her hips and tilted her head at me, sort of the look you’d get when you’re caught with your hand in the cookie jar. She then said, “Maybe I can pay you tonight after all.” Then she put her right arm around my shoulder, and with her left hand reached down and started undoing my belt.

I remember stammering and choking a bit as she released my belt. She asked me to take my pants down for her, which I quickly did. So there I was my pants and boxers around my ankles, my dick out, and this sexy mom with her arm around my shoulder. She spun me around so I faced towards an open spot of the floor in the kitchen. She then reached down and put her hand around my dick. She started jerking me off, and I knew I wasn’t going to last long. Maybe a minute later, I told her I was going to cum, but it came out more like “Uh… uh…”

I think she knew what I was trying to say, and kept on stroking. I came all over the floor, and she giggled lightly as I did. When she finally stopped jerking me, she pulled her hand up to look at it and show me. It was streaked with cum. She walked over to the sink and grabbed a towel, wiping off her hand and kneeling down to wipe the floor. That’s when she said “Well, thanks again for your help tonight. We’ll see you next week.” So I pulled up my pants, and walked out, leaving her down on her knees cleaning up my cum from her floor.

It wasn’t my first handjob, but it was the first time I’d ever cheated with someone.

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