One Shot Deals: The Female Jock

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Middle-aged guy cuts deal with sexy jockette.
7.1k words
4.58
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11

Part 5 of the 6 part series

Updated 08/31/2017
Created 04/22/2005
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Having reached the age of fifty-five and grown invisible to young women, I find myself reminiscing more and more about my former sex life. It was a good one. The list of women I had intercourse with numbers thirty-six, unless I've forgotten one or two. As I created the list, I realized that more than a third of those were "one-night stands." Seven of those relationships were just bad mistakes, "thinking with the wrong head," and quickly remedied. Seven others, however, were among the most spectacular of my life. This is the last of them.

Being in graduate school and professional theater guaranteed that I could not settle down until rather late in life. I was thirty-four when I married and had had sex before my engagement with exactly as many women as my age. By that time, I had dated perhaps sixty women and had met so many zanies that I was relieved to have found a smart, sane, and sexy soul mate. The phrase "I had to kiss a lot of frogs to find my prince" applies as well for princesses.

I was happily married for fifteen years, although we couldn't have kids. And then my wife died after her second bout with cancer. We lived and I still live in a suburban neighborhood that looks like Wisteria Lane in Desperate Housewives. As you can imagine, when my wife died the neighborhood rallied. I did not have to cook for weeks afterward. Among those who brought me food was Haley, the younger daughter of my neighbors across the street. Her name is altered, in the hopes of preserving her anonymity and keeping me from being murdered. On several occasions, Haley brought me brownies. According to her, they were about the only thing she knew how to bake. She seemed genuinely concerned about my bereavement.

Haley was almost nineteen at the time. She had stayed back in first grade. The extra time in school had given her certain sports advantages, and she was a hard-core female jock. In the fall she played soccer. Spring was baseball. She was a starter for both teams in her junior and senior years. Nevertheless, she is naturally pretty. I knew that Haley could have been even more attractive if she hadn't been such a tomboy. She has large brown eyes and high cheekbones. Her skin has always been clear. And despite her masculine dress, one cannot miss the shape of her hips or the prominences of her breasts. She always kept her long, chestnut-colored hair tied back in a ponytail. She wore jeans and tee shirts all the time and usually sported a baseball cap. I never saw her anything on her feet but sneakers or cleat shoes. Revlon and Maybelline would have gone bankrupt if all women were like Haley.

But Haley is far from butch. She actually has a slight wiggle to her walk. Her voice is very feminine. It was all in her attitude and outlook. She certainly had enough sexual allure to attract boys. Her father began complaining to me about it when Haley was fourteen. According to him, she had very hot pants. In her senior year, her steady boyfriend was a huge guard of the high school football team who looked like "Jaws" from the James Bond series. Her parents were not happy with the situation. He was known to be wild, having totaled a car and been arrested for drunk driving.

It was late spring and I was now fifty. Haley's parents had to drive to Ohio for the wedding of a brother's son. They left on Friday morning and planned to be home by about seven on Sunday night. Haley could not go because she was in playoffs for her baseball team that weekend. Her father and I pal around, go to sports events and so forth. Also, when I was married my wife dragged me to church at least once a month. When she became sick, I started to depend on that good community more and more, for spiritual and physical sustenance. Haley's dad considered me a "religious fanatic." Thus it was that, as the moral paragon of the block, I was assigned the task of keeping an eye on their younger daughter. She was not allowed to have anyone in their house. I was also to check on the house each night and that she was there and safe. I really didn't give it much thought.

I work from home. I was in my study, which faces our street, on Friday afternoon when Haley came back from school. She has her own car, a rather beat-up Japanese hand-me-down. I checked the clock as she emerged from the driver's seat. It was five minutes before five in the afternoon. She was dressed in her uniform and had apparently only changed her socks and shoes. She dashed into the house. I was careful to note that no one went with her.

Not more than five minutes later, Haley reappeared carrying a plate with plastic wrap over it. She crossed the street, heading onto my property. I went downstairs to meet her at the front door.

"Hey!" she said, also calling me "Mr." and by my last name. I was thirty-one-plus years her senior and was not the informal kind who encourage children of friends to call me by my first name. She held up the paper plate. "I brought you some of my special double-chocolate brownies. Can I come in?" Her words were run together in a hurry.

"Sure," I said, accepting the gift. I noted that the plate was cool, as if the brownies had been refrigerated. Haley had only been inside my house once for a holiday party, and that had been several years earlier. I stepped back and let her inside. Since our neighborhood only has four house designs, she knew the layout. She moved swiftly into the kitchen and plunked herself down at the kitchen table. She looked utterly beguiling in her baseball uniform. She had a smudge of dirt on her right cheek, and her hair was a bit mussed. She blew a strand away from her eye

"Just had a practice, eh?" I noted.

"Yeah. Our last one before the playoffs," she said. "If we win both games tomorrow, we go on to state regionals. Sudden death elimination, y'know."

I nodded, feeling my heart ache for her blossoming youth and mine long past. If she had been in my high school and had given me the slightest time of day, I knew that I would have pursued such a creature.

"To what do I owe the gift?" I asked, taking the seat next to her, so that I wouldn't be looking down from a superior position and so that I could better drink in her lovely face.

Haley shrugged. "I was just baking last night and thought of you."

I opened the plastic wrap and took one. "Thanks. They smell great. Want one?"

"No." Suddenly, she was blushing deeply. "There's something else I want in my mouth." She laid her hand boldly on my knee.

The brownie almost fell from my lips. My heart did a flip-flop.

"You don't see anyone steady since your wife died," Haley correctly observed. "You don't even date."

My wife had been died about eight months before. Because of her lengthy illness and my relatively young age, people could hardly wait to begin trying to set me up with widows and divorcees. This included Haley's parents. As early as Christmas, they had been offering names. I had not been in the mood. And, frankly, forty-five and fifty-year-old women were not what I hankered after. I am an unapologetic worshipper of youthful beauty and was holding out for someone around thirty-five.

I looked down at Haley's hand. "That's true."

"You must get really horny," she said. "I mean, especially after getting it on a regular basis for so many years." She squeezed my knee.

I took Haley's hand in mine. "I think I know where this is going, and I'm very flattered," I said, "but it's not right."

"What's the problem? I'm way beyond legal in this state," she replied. "Most girls my age are screwing their brains out at college." She rolled her eyes. "All I could get into for next fall is the local community college. I have to live home next year, too. I know I'm going to be climbing the walls."

As she rattled on about her frustrations, I began trembling at the salaciousness of what was being offered to me. I did not, however, release her hand. A little nervous laugh escaped me. "The irony, Haley, is that your parents asked me to keep an eye on you precisely so you wouldn't be fooling around."

"I know," she said in an annoyed tone. "They told the entire neighborhood to watch out for me."

This I did not know. We had a Neighborhood Watch against house thieves, so I suppose that using the same watch against nookie thieves made sense. Her parents could not expect me to sit guard day and night.

Before I could react, Haley dropped off the chair onto her knees and went for the zipper of my trousers. "But you're the one living right across the street. You're the one who can tell my folks that I was good."

At that set of ironic words, I shut up and let her have her way, seeing just how far she would go. I certainly helped, as my cock was half hard by the time her hand closed around it. She dragged it into the light with no hesitation and regarded it.

"Nice! And so thick."

"You've done this before, I take it," I said.

"Of course I have." She started pumping it gently, as if she knew what she was doing. "I've given beejays since I was fifteen. But only guys my own age."

I had read how this generation was amazingly unabashed about oral sex. Blow jobs were common "thank you's" after first dates.

"And may I ask how many beejays you've given?" I inquired.

Haley took an investigatory lick up the bottom of my shaft, lingering in just the right place. She made a humming sound of pleasure. "Lots. To three different guys."

"And you've also had intercourse," I ventured.

"With one guy."

"The football player, I'll bet."

Haley stopped in mid-lick. "They really did report on me, huh?"

"Yes." I was simultaneously quivering with ecstasy and curiosity. "Exactly how many times have you had intercourse?"

"Four. Once at his house and three times in cars. Always in a hurry. I'm way behind some of my girlfriends."

I could barely believe Haley was so matter-of-fact and blasé. I had only for an instant allowed myself the fantasy that this teenager had been secretly lusting after me and was taking her first opportunity to satisfy her lust. Clearly, she was looking to suck me off as a bribe to allow her to sneak her boyfriend into the house for a weekend of unrushed and unbridled fucking.

I leaned back and watched Haley working. She was licking, sucking, and pumping rather expertly, but she was also hurrying. This did not please me, either physically or mentally. My cock was the key to what she really wanted, and she approached the exercise with workmanlike efficiency. I was damned if I would give her the satisfaction of coming in a rush. She seemed confused after about two minutes of uninterrupted attention to my member because I wasn't exploding like a sixteen-year-old. She rocked back on her heels and regarded it.

"Man, it's not that long, but it's so thick!" she observed.

My cock is six-and-a-half inches, measured from the top. I understand this is well within normal proportions. My girth around, however, seems to be about a third more than most men. It has served to keep me tight in the saddle when women begin to get wet.

"Different from your boyfriend?" I asked.

"Yeah. His is about this much longer." She held up her hand and indicated another two inches. But it's skinny. I tell him it's like I'm being humped by a dog. Or like being poked by a stick."

I refrained from quoting 'It's not the size of the wand but how you wave it.' "You want me to look the other way when you bring him into your house," I confirmed.

"Right."

"And this is the bribe."

"Don't you like it?"

"I like it very much, but it's not enough," I said, having made up my mind. I was not protecting my neighbors' daughter from losing her virginity. The barn door, so to speak, had already been opened. She was hot to be fucked. I was convinced that, even at my age, I could please her better than her boyfriend. I had let several excellent sexual opportunities slip away when I was young. Knowing this was probably my last chance to fulfill an opportunity of fantasy proportions, I leapt at it.

Haley let go of my cock. "I can't do anything more than this," she said, looking over her shoulder in the direction of the street. "I've been in your house too long already. I'm sure you don't want the other neighbors talking about you."

"I do not," I agreed. "But if you want a long, uninterrupted time with your boyfriend, you've got to please me first." I bent forward, lifted her under her arms, and brought her face to mine. I kissed her fully on the lips. Her eyes went wide, but she did not look disgusted. She smelled like an afternoon of baseball practice.

"That was a good kiss," Haley judged, smiling as I let her go back down into a catcher's squat. She ran her fingers up and down my shaft. "Let me get this straight. I have to make love to you first before I get to fuck my boyfriend."

'That's right. You shouldn't be screwing around all night tonight anyway," I said. "You have games to win tomorrow."

"How would we get away with it?" Haley asked, ready to play by my rules.

Lust coursed through my veins like liquid fire. "Leave right now, get your car keys, and drive down to the CVS. Park in that overflow lot toward the back of the store and wait in your car."

A sly grin broke across the teenager's lovely face. It was an expression never to be forgotten. She was evidently up for this unexpected adventure. "Yeah, okay." She stood.

I went upstairs to the master bedroom and began putting it in order, watching every few moments through the window. Haley walked casually across my property and onto hers. She entered the house. About two minutes later, she got into her car and drove away.

I took my time neatening up. Ten minutes passed before I went down to the garage, carrying a blanket. I have always had a habit of keeping the cars garaged, to preserve the paint jobs. I pressed the automatic opener on the wall and got into my wife's four-door sedan. I used the remote to close the garage door after me. I cautioned my eager self to stay within the speed limit as I drove to the pharmacy. Haley's car was exactly where I told her to put it. I pulled parallel. No one was in that part of the lot. She opened my front passenger door.

"No, get in the back," I told her. "Lie down on the floor and pull the blanket over you."

"I feel like a spy," she said, obeying.

"Lie still!" I said sternly. "I'll be back in five minutes."

I locked my car and left Haley lying like a beautiful prize in the back of my car while I went inside and grabbed several mouth care products as decoys and then selected a package of three condoms with ribbed sides. If I was going to betray my neighbors' trust, the least I could do was to make sure I didn't also impregnate their daughter. I pulled away from the drugstore after making sure the blanket had a large shape under it.

"You've done this before, to cheat on your wife, haven't you?" she asked as I drove back home.

"No, but I once had someone else's wife do it with me. I was where you are. It was a long time ago."

"You're not that old," she said. "I've always thought you were attractive for an older guy," she graciously shared.

I told her I was glad for her sake.

"How long will I be with you?" she inquired.

"I guess for a couple of hours."

"A couple of hours? How long can one fuck take?"

I knew that Haley had a lot to learn.

"When you get to my house, I want you to call your boyfriend," I said. "Tell him that I'm really keeping an eye on you and that he can't come over until tomorrow."

"Okay. I brought my cell phone," she said.

"When we get into my house again," I instructed.

I pulled the car directly into the garage and got out as I normally would. When the large door had finally descended all the way, I opened the back of the sedan and whisked off the blanket. Pretty Haley grinned up at me.

"I'm all sweaty," she said. "I'm not sure you want to be with me."

"That's what showers are for," I answered.

After Haley made her phone call, I took her by the hand and led her upstairs to the bathroom with the shower. I have always enjoyed having a totally naked woman in my arms while I am fully dressed. I closed the door of the bathroom and moved Haley against it, pressing myself to her and kissing her slowly and deeply. She gave back the right responses. While I continued kissing her, I began to slowly unbutton her uniform. She kept her hands at her sides, allowing me total control. Under the shirt, she wore a stretch sports bra. I got this off in rather a hurry. I was very interested in seeing her breasts.

I have always favored women well endowed in the bosom. My wife was a 36, between a C and D, depending on fluctuations of weight and the time of the month. Haley was also a 36, but she was a well-rounded B cup. What she had, however, was wonderful for her young, athletic shape. Her breasts were perfectly taut. I could tell that she would increase to a C when she no longer exercised every day. They were without blemish. Her nipples and areolas were light pink. Her breasts had just enough subcutaneous fat in them that they felt good to the touch. I played with them for perhaps a minute but had so much else to do that I abandoned them for future attention.

I undid Haley's belt and skinned down her pants and panties with one movement. Without stepping back, I let my hands tell me about her secrets. Her body was long, muscular, and smooth. Her ass felt small and incredibly tight. When I inserted my hand between her legs, I was surprised by the quantity of pubic hair I found. I lowered myself slowly, kissing my way down until I knelt on the tile floor. While I worked off her sneakers and socks, I stared at her pussy. She had thin outer labia. However, they ran long. The crack of her cunt started high and extended down so far that she had almost no perineum between her vaginal split and her asshole.

"Now you," Haley said anxiously when I stood. She guided me around against the door and undid my shirt, trousers, and underpants while I worked off shoes and socks. She could not resist fisting my cock again when it sprang out and would have begun sucking if I had not lifted her and guided her to the shower stall.

As a gentleman, I entered the stall first, took the cold water upon myself, and adjusted the temperature before guiding her in with me. I knew this must be Haley's first liquid experience with a man, and I determined to make it utterly sensual. I handed her the soap and invited her to wash me. She took her time exploring, remarking at how much more hairy I was than her boyfriend. She spent many minutes running the soap around my ass and into the crack. She spent less time lathering up my cock and balls, but as soon as she was finished rinsing me she took my cock into her mouth and, using one hand as well, gave me a spirited blow job. Finally, I allowed her to make me cum. I gave her plenty of warning, but she resolutely kept her mouth tight to my cock as it began to pulse and shoot out long-pent-up strings of pearly cum. I leaned back against the stall wall for support as the last jerks of my ejaculation bounced my prick up and down inside her lips. I was not surprised when she opened her mouth and let the torrents of cum run out. Then she turned her face up toward the shower head, still on her knees, and let the water clean out her mouth. She turned her head slowly from side to side and languorously kneaded her breasts and nipples. The sight of her was so sensual that I barely went limp.

I pulled Haley up and kissed her deeply. Then I went to work on her. Alternately standing and kneeling, I covered every inch of her with soap. I was mesmerized when she lifted both arms straight over her head and offered her arm pits. Her breasts rode high on her chest, and her neck looked so vulnerable. She obligingly spread her legs when I came to her pussy. The soap bar was well used and small, so that I could slip it into the furrow of her vagina. She moaned as I worked first the soap and then the nappy washcloth back and forth along her slit and up over her clitoris. I turned her around and lathered up her ass. I pushed the soap into her asshole, making her sigh and noting well her pleasure at this. Then I used the pulsing showerhead to rinse her off, making her squeal with the pleasure of the vibrations. My main pleasure came from having her repeat over and over, "Oh, Mr. ---!" No other sound could be as effective in driving the age difference home.

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