In the days after Mrs. Reid gave me my first blowjob and then continued messing with me, I started having some serious qualms. These qualms mostly centered around Mr. Reid, and what would happen if he found out that his wife was sucking me off on a daily basis. I was also concerned that when my father found out that this older woman was messing around with son, he hadn't told me to knock if off because of what might happen if Mr. Reid found out. I was puzzled.
I was puzzled because Mr. Reid was not the kind of person you typically wanted to betray or lie to or generally fuck around with. He had treated me like a buddy since we moved in, and I really liked him a ton, but he was a formidable guy in almost every department. Dan Reid had been an offensive lineman at a Division I school, and at 56 carried about 235 pounds on his 6'4'' frame. He started losing his hair when he was in college and by the time it really started to go he started shaving his head. On him it looked good, it made him look even more intimidating.
He owned a company that manufactured some kind of electronic switching equipment made seriously good money. Once I'd heard my father mention that Mr. Reid made "well" into six figures, and on another occasion I heard a neighbor at a party say that Dan pulled down around $450,000 a year. Now, we lived in a nice neighborhood, and the Reid's had a very nice house and drove nice cars and Mrs. Reid shopped like a champ, but they certainly didn't live like people with big bucks. They didn't have kids, didn't seem to toss money around. Where did it all go?
At the end of July my parents decided to have new carpets put in our house. The whole place was going to be torn up for 3 days. My folks decided to take advantage of this to run off to Cancun to their time-share condo. They were going with another couple so I wasn't exactly invited. I was fine with this, for 3 reasons. One, the Johnson's flowers had all faded out and they were desperately trying to save them. Two, because of this, Mrs. Reid had hinted that I had earned the right to enjoy the pleasures of the mysterious place between her legs. And three, Mr. Reid was going to be out of town for five days on a business trip. I would be more than happy to stay home.
Two days before my folks planned on leaving Mrs. Reid intercepted me while I was mowing the lawn and pulled me inside her house. I knew Dan was inside talking to my dad, so we were alone. Jackie slipped her hand down my shorts and caressed my instantly hardening cock.
"I'm in the mood for some skinny dipping. Dan is going to a retirement dinner and I'm going to tell him I have a headache You want to stop over?"
I was fully erect and she was moving her hand up and down the shaft. I groaned and leaned against her. I lifted her blouse and slid my hand underneath. I caressed her big breast as I ground my hips against her teasing fingers.
"Can we fuck tonight?" I begged.
"No, not tonight. Because I have a new job for you, and if you succeed, then I'll fuck you. Then I'll take you to my bed, and get that gorgeous cock hard like a rock, and I'll put it inside me. You want that, don't you?"
"Yes!" I sobbed.
"I want it too. But you need to help me first."
"What, anything."
"Dan is talking to your parents because he wants to invite you to go on a business trip with him. Just a few days, have some fun, show you what he does."
She leaned against me and thrust her other hand in my shorts. Her tongue darted in and out of my ear. "Andy, I know he's cheating on me. He's got a whore stuck away somewhere. I want you to find out who it is. Bring me the proof, Andy, and I'll fuck your fucking brains out."
"But, what if he isn't seeing anyone?"
"He is!" she exclaimed, squeezing my balls hard as emphasis. "I know it, Andy. I'm positive. I need the proof. And if he asks if anything is going on between us, deny everything."
"What! You mean, he suspects something, did he say anything or do anything?!"
She pumped me harder. "No, he doesn't suspect, of course not. But he might say something, just kidding around, trying to embarrass you. Just tell him that he's crazy. Deny everything."
I was quivering all over. "I'll do it. Please, I'm going to come, I'm going to shoot."
She yanked her hands out of my pants. "Save it for tonight, honey. I want you balls filled to the brim. And Dan will be home any second. How about midnight?"
I said I couldn't wait. And about five seconds later Dan charged through the screen door and bellowed "Road trip!"
"I'll leave you two to sort out the sordid details," Jackie said.
"Come on baby, it's only going to be a little bit sordid," Dan said. She walked away shaking her head and Dan said, "Just kidding, it'll be out of control!"
He gave me the itinerary. The city we were going was home to 3 of his biggest customers, and he'd have meetings just about every afternoon. "But at night, we'll be two guys out on the town. We'll probably hook up with some of my clients too, but it'll be good experience for you, to see how things work in the real world. It'll help put all that college bullshit into perspective for you."
On the way back we'd stop at the town where I was going to college in the fall, which was also Dan's alma mater. "I'll take you on a tour of campus, show you the best places to live, the best places for meeting girls..." His laugh was a deep rumble, and as I accepted I wondered if he planned on dumping my body on some back road in the middle of our trip. How much did he know?
Dan told me I would need to bring at least 3 suits, since we would be going out to dinner every night and "I'm not a Burger King kind of guy." I only own 3 suits, so that made the decisions easy. He liked my suits, very conservative, blues and grays, like the fashionable cut. But when he looked over my casual clothes he frowned. "You need clothes to wear out for the evening, entertaining, that sort of stuff. A gray suit won't cut it at a club or anything like that. Come on."
"What? Dan, I'm only 18, I can't get into a club"
He ignored me. "Gotta go shopping."
We walked over to his house and he told Mrs. Reid we were going shopping. She pretended to pout, complaining that SHE never got to shop anymore, but then she laughed and asked when she should have dinner ready. As we left she winked at me and mouthed the words, "Deny everything!."
We went to this extremely expensive men's store downtown. By "extremely" I mean that a dress shirt and slacks cost more than my monthly car payment. Dan picked out stuff for me to try on, and Leon, the head tailor at the store, slashed at me with chalk to mark where the alterations were needed. I didn't even get the chance to say, "Wait a second," or, "This costs more than my first semester tuition."
In the end I got five suits, three sport coats, four pairs of slacks, eight dress shirts, a dozen casual polo and button down shirts, twelve ties, four pairs of shoes, suspenders, belts, socks, underwear. When the overjoyed salesgirl rang everything up and I saw how much it cost, I almost puked on the counter. No lie, this little spree cost more than my car. When it was new. With a full tank of gas.
I saw how casually Dan handed over his credit card, like this was no big deal, and idly stared at a wall display, "Uh, Dan, I don't get my allowance until Friday, so I won't be able to pay you back until then. Well, a Friday in 2028."
He grinned. "Don't sweat it. But, uh, don't tell your folks we spent this much. They'd probably object."
"Maybe a bit."
"And don't worry, you'll earn it."
"Earn it? How?"
"You'll see."
Before we left Dan told Leon that everything had to be ready in two days, and Leon practically licked Dan's shoes as he promised it would be so. We went home, and Dan told me he'd pick the clothes up and load them in the car the morning we left. I went home, ate dinner, and tried to figure out how exactly I was going to earn my new wardrobe on this trip.
Dan went to a retirement party for a friend of his, and I went over a friend's house to play cards. Just before midnight I made an excuse, cashed in my chips, and headed home. I parked a block away from my house and walked to the Reid's house. I cased the joint. The house was dark; so was the pool. As it should be. I cut around the side away from my parents house. The gate to the pool was cracked open. I took a peek. There were a dozen small candles ringing the pool, casting just the faintest illumination.
"Are you just going to stand there, or are you coming in?" Jackie's head was just sticking up above the lip of the pool. I could barely make out her smiling face in the pale candlelight.
I silently moved through the gate and tiptoed over to a chaise lounge. I stripped off my shorts and shirt and walked to the steps leading down into the pool. My erection stuck out in front of me like a divining rod.
I stuck in a curious toe. "How's the water?"
"What, you're going home if it's too cold?" She swam over to me and slid her hand up my leg. She couldn't reach up high enough to touch my cock, so I crouched down and she diddled my glans with her long, red nails. "Come on in."
I walked down the steps into the delicious, blood-warm water. I paddled over to Jackie and gathered her in my arms. I pressed my erection against her stomach.
"You seem happy to see me," she said as I rubbed myself against her.
"Jackie, can we do it tonight? Have sex?"
She turned and kissed me hard. She pushed me backwards, into deeper water, and I lost my footing. She swam after me, her slippery heads moving over my ass, my stomach, my cock. I surfaced and grabbed the wall. She wrapped her left arm around my waist and kept caressing my dick with her right. Her thumb gently circled the tip of my glans, her nails scratched my stomach. I was on fire. She leaned up and nibbled my earlobe. "We can't fuck tonight. Not till you get back from your trip with the evidence I want."
I was disappointed and it must have shown on my face. "Oh, you can wait a few more days!" she said, cupping my balls in her hand. "I promise, as soon as you get back, I'll let you put your cock inside me. I'll make it worth the wait."
We swam back to the shallow end. "You didn't say if you like my new bikini." It was so dark that I hadn't notice it. But she stood and raised her arms high above her head to let me admire it, and her curvy body. It was shiny and black, her big heavy jugs swelling out the cups so that the straps were stretched an inch away from her chest. I took her wide hips in my hands and lifted her out of the water. The thong bottoms barely covered her pussy, and a barely-there string did nothing to cover her ass. Usually when we fooled around I sat in a chair and Jackie did all the work. But now my hands were free to explore her voluptuous body, and she seemed to like it. I turned her around so her back was to me and I let my hands wander, over her stomach, her ass, her tits. I slid my fingers inside the cups of her bikini and fingered her nipples.
"You can take the top off, if you want," she said.