When my mom told me that Mrs. Reid had called and had some chores for me to do, I was both excited and nervous. Excited, because Mrs. Reid usually rewarded my hard work with a long, slow handjob that would leave me coming in quarts. Nervous, because more and more of her "chores" were stunts devised to get me into embarrassing situations for her amusement.
She was bored, Mrs. Reid was. Her husband made tons of money but was away a lot on business, and since she didn't work and had a wild streak in her Jackie Reid did things that the typical 50-year-old suburban housewife didn't do. Like fool around with her 18-year-old neighbor. And have that neighbor, me, do stupid things to stir things up.
The first time she had masturbated me was in May, and for the rest of that month and June she had me over a few times a week for "chores". For example, she and her husband didn't subscribe to the Wall Street Journal. But she enjoyed reading it, so if I wanted her to put her hands all over me and have her tickle my balls with her sexy nails and come all over her big tits, I had to bring the day's WSJ. In our neighborhood there were maybe 15 people who subscribed, so I had to get up at like 5AM, sneak out of the house, and steal the paper from some hopefully unsuspecting house. I targeted different houses on different days, so that suspicions wouldn't build up too fast. I was careful, very careful, because how could I explain what I was doing? I mean, did I have an investment fetish or something?
But it was worth it when I showed up at Mrs. Reid's door with the paper and she would say, "Oh, wonderful, I think I'll read it after I take care of something first." And that "something" would be the big erection in my shorts. They had a big leather chair in their living room and Mrs. Reid would strip me and then take off her clothes and get some lotion or gel from the bathroom and cover my cock with the slippery stuff and then, oh God, she would jerk me off. She had forbidden me to jack off myself, telling me that got off seeing me dump a giant load on her tits, so when she stroked me it never took long to get me to the brink.
She would wrap both palms around my shaft and slide them up and down, slowly, so damned slowly that I thought my cock would just rupture and spray come all over the place. She would look me in the eyes and say, "I can feel your heart beating, through your cock. I can feel how bad you want to come. Do you want to come?" I would whimper yes and she would slow down even more and caress my balls with her nails and she would say, "You'll come when I'm ready for you to come."
I never lasted longer than five minutes. She was too sexy, I was too ready to ejaculate from the moment I saw her. One I apologized for coming so soon and she laughed and kissed me and said, "Honey, I'm glad I can still make a boy like you that excited! I like it when you come fast." If that was true, then she found the right guy to diddle with. I tried to come over every day, but when Mr. Reid wasn't there I couldn't very well ask to have a few minutes alone with his wife, and there were other days when I couldn't arrange to get over there. Those were the days when my balls filled with semen and I got on edge knowing that this incredibly sexy woman was waiting to drain all that built-up energy out of me.
The last week of June, after she accepted her stolen paper and was preparing to give me all that pleasure, I asked a question that I wanted to ask since that first day but was too afraid to. "Jackie?" I said, making my voice as calm as possible.
"Yes, honey?"
"Could you, could we, do something different?"
"Different? What do you mean?"
"I mean, instead of using your hands, could you, I mean, could you put your mouth…" I couldn't say anything more, I was too scared.
"You want a blowjob?" she interrupted.
"Um, not if you don't want."
She smiled at me. "Andy, if you want a blowjob, just ask me and see how I answer."
I swallowed. "Will you…do that?"
"Call it what it is. If you can't ask for it, do you think I should give you one?"
My mouth was dry. "Will you give me a blowjob?"
She leaned forward, pulled me forward, and gave me a long, deep kiss, her tongue slipping into my mouth and sliding along my teeth. "No," she said. "I'm taking a big risk already, jacking you off. I have a lot to lose. My husband, my reputation. I have you stealing papers so that you have some risk involved too, so I know that you're willing to do something dangerous the same as me. But I could maybe explain giving you handjobs to my husband. You're just an excitable boy, I liked playing with you, I'm a bad girl and I shouldn’t have done it. But sucking you off, that would be much more serious. So, you'll have to just content yourself with this." She sprayed lotion on my cock and began working me over.
I was disappointed, but my bad mood instantly vanished as the hot molten waves of pleasure began radiating out from my groin. She wasn't holding me back this time, she was trying to make my come fast. And I was there in less than a minute. She was pumping so fast that her big tits bounced magnificently and that just totaled me. Just as I started to orgasm, Mrs. Reid looked me in the eye and said, "You know what, maybe there is something you can do for me that will earn you a blowjob. Are you interested?"
"YEEEEESSSSSS," I shrieked as the tip of my cock split open and a geyser of semen shot toward the ceiling and covered my chest. I was almost hyperventilating as I tried to calm down, and Mrs. Reid scooped up some of my come with her fingers and brought it to her mouth. She'd never tasted my come before and I found this terribly exciting and puzzling at the same time.
"Mmm," she said, "I want more of that. I think maybe I will have you do that little job I've been thinking about."
"What job?" I asked, willing to commit murder for her if that was what she had in mind.
"I'll tell you tomorrow," as she cleaned me up with a towel. It was only after I was home and had time to think about it, that maybe the price for the pleasure of her mouth was going to be quite high.
The next morning I almost got caught swiping the paper. I chose a house I hadn't hit in a few weeks and when I helped myself to the paper the driveway lights came on. I guess they have a motion detector set up and the paper was thrown closer to the house than usual and bang! On came the lights. I bolted and just as I found a bush to hide behind the front door opened and Mr. Claiborne came out. He looked up and down the street and when he didn't see anything he picked up his paper and went back inside. I waited five minutes to make sure he wasn't peeking out a window scoping things out before I got the hell out of there. I strolled down to the Peterson's house and took their paper. Mr. Peterson was pretty oblivious so I figured stealing his paper two days in a row wouldn't be that big a risk.
When I delivered the paper to Mrs. Reid and waited for her to turn me inside out with her pumping hands, I received a rude surprise. Sitting on her kitchen table was the day's issue of the Wall Street Journal. She lit a cigarette and turned the page. "Wait," I asked, "you get the paper delivered?"
She nodded. "For the last two weeks, yes."
"Then why do you have me stealing them? I almost got caught today!"
"I wanted to make sure you were willing to take risks, remember? And to keep our little arrangement a secret you have to be crafty and devious. You have to fool your parents, be sneaky around them. So you've shown you can be like that. That's good. I think that's sexy," She smiled and put her cigarette down. "But now you want to raise the stakes. And so do I. Come with me."
She took me by the hand and led me out her front door. "See how nice my flowers are?" she asked, pointing to the long bed of tulips and marigolds and God knows what other flowers she had planted.
"They look great," I said.
"I love my flowers. I work hard to make them look nice."
"You know what you're doing, because they really look nice," They did, but even if they had been brown and wilting I would have agreed with her.
