Last Friday afternoon, I somehow managed to have sex with a lady who hired me to maintain her pool this summer. Yes, yes, Jason the poolboy managed to fulfill the cliche and seduce the lonely wife as I cleaned the pool in only my shorts and flipflops. It's not what I set out to do as I pulled out of the driveway that morning; it's not even what I set out to do as I was doing my job at her house, but it did happen, and I'll tell the story.
I'm 20 years old and a scholarship athlete at a small college. Because I can't have a job during the school year, I go back to my hometown every summer and maintain pools. The money's good, it's all in cash, and because we're in Iowa, the middle of summer is the only time pools get used anyway. We have a family friend about ten years older than me who gave me my first job as 'pool boy', and since she knows me well and I do a good job for her, she has referred me to three other people, one of which is Kara.
Kara is 30 years old, is married to a chemical engineer, and has a 3 year old child who often appears outside to entertain me whenever I'm there. I've never seen her husband, and that family friend that gave me the referral told me that they recently separated, and he moved out. Before you put this story right into the groove of the stereotypical poolboy story, I should tell you that Kara's not 'hot', at least not in the same way that Jessica Alba or Scarlett Johansson is hot. She's a little short of five and a half feet tall, has the warm-brown skin tone befitting her Asian descent, and probably rates between a seven and an eight if a random guy was asked to give her a score on the spot. She's one that grows on you, though, and it helps that almost every time I see her, it's in a swimsuit. Her curves aren't 'swimsuit issue' quality, but given the fact that she's out of her twenties and has had a kid, she's still packing some heat: nice ample and shapely ass, nice legs with just enough meat on them; and a few extra pounds and all, a better waist and chest than your average 30 year old in Iowa can boast.
When I started, she was very formal with me, keeping conversation to a minimum. It was safe to say her toddler daughter, Isabella, had formed a closer relationship with me than she had. But, my humor and ease won her over little by little, and I ended up staying longer and longer each time, each of us getting sucked in by our conversation. On Tuesday, Thursday, and Friday, Isabella had a mother's day out program in the afternoon, so it was just the two of us. Our conversations slowly got more intimate and occasionally even racy; I could tell that she enjoyed the banter, and enjoyed being a little bit 'bad' with someone who shared her sense of humor. The more I got to know her, the more she turned me on, my loins stirring each time she emerged from her house in a bikini, which were the only type of swimsuits she ever wore. When we talked, I always worried about the ever-looming possibility that my erection would appear, and I mentally fought it off constantly. In a swimsuit, a raging boner is so obvious that I might as well be naked, but the way I saw Kara look at me, a part of me knew that it wouldn't make her uncomfortable. Maybe I should have seen that there was the potential for something to ignite between us, but no matter what we talked about, even if and when it was about sexual stuff, the idea that we would ever hook up was too far-fetched to seriously consider. I mean, she was a housewife and mother who lived in a $300,000 house with a pool, and I was a small-time defensive back at a small college driving a cheap pickup truck.
Without even realizing I was doing it, in time I scheduled all my visits to Kara's pool on the days her kid was gone, and last Friday was no different. Lately, I'd taken to beating off in the shower while thinking of her in her bikini, and was hoping I'd be getting more material that day. I was there about twenty minutes, maybe ten from being done for the day, and starting the think maybe she wasn't home. Then, I heard the door open and she came out, wearing a tight white bikini with very skimpy bottoms, showing off more of her ass than I'd ever seen before, and a top that squished her breasts back against her body more than normal. She brought out a book and a glass of ice water, setting both down beside her lounger as she got comfortable. We exchanged hellos as I worked on the other side of the pool. Her sunglasses prevented me from knowing if she was looking at me, and mine prevented her from knowing I was staring at her while trying to psych my cock out of sprouting a hard-on in my bathing suit.
Working my way around toward her, I marveled at her nipples, which were telegraphing through her top even though it was 80-something degrees out. Her body looked great. Her smooth belly protruded just slightly over her bikini bottoms, and her legs were great as usual, with just a little extra meat in the thighs. Her feet, perfectly shaped and manicured, featured black nailpolish on her toenails, matching her fingernails. As my gawkfest continued, I heard her voice:
"Jason, can you help me out here? I need to get some sunscreen on my back; I almost burned out here yesterday."
I said sure, and took the bottle, squeezing a large glob of white cream into my hands as she sat up with her back to me. I wish I could describe the visceral jolt that surged through me as I touched her skin for the first time. It was incredibly soft, and warm, and I felt her jump a little at the contact, too. I made sure her entire back was fully covered with lotion, and then I heard her say, "make sure and get it under the strap, maybe I'll unhook it later."
!
My heart fluttered as I reached a hand underneath to slather the covered skin. Even though there was nothing different about this skin, the idea of getting underneath any of Kara's clothes, no matter now minor, was exciting and erotic to me. Then, I heard,
"While you're doing this, reach around and get my front, I don't want to move right now."
!!!
While I was still coming to grips with this new request, my hands had already filled with more lotion and were reaching around her waist to rub into her belly. In order to get both hands around, I had to get close to her, so I swung a leg over the back of the lounger and leaned forward, close enough to smell her hair. As I covered her front in lotion, I felt my fingers sink into her soft stomach. All the while, I was trying to keep my hands from going too low or high, reversing their direction whenever they hit fabric at either end. I reloaded, reaching up past her breasts to get lotion onto her chest and the front of her shoulders. As I did, I could hear Kara breathing heavier. I could see her shoulders rise slightly as she inhaled. By now, of course, there was no stopping my erection, which was now pressing the fabric of my swimsuit straight out, less than a couple of inches from the exposed small of Kara's back.
I knew now that something was happening, I just wasn't coherent enough to piece it together yet.
"Jason, I'm going to sunbathe topless a little later," she said breathily as I kneaded sunblock into her chest. "I may regret this.....oh jesus," she whispered to herself. Then,".....Jason, makes sure you get the suntan lotion under my bra," she stammered as my heart jumped into my throat. Even I wasn't so clueless as to miss this alarm bell, hurrying to get the lotion and slip my hands under her bra before she came to her senses.
Kara gasped loudly as my fingers snuck past the elastic boundary at the bottom of her bikini top and made contact with the wonderfully milky soft, cool skin of her breasts. Her nipples were hard as a rock against bottom of my palms as I rubbed the lotion into her skin, kneading her tits as I made sure no spot was missed. She reached back and undid her top, making my job much easier. Knowing she was fully sunblocked but not wanting to stop caressing her, I moved my hands down to the bottom of her belly then back up to her breasts. Kara's moan broke the silence that I knew better than to spoil with words, taking my hands in hers and guiding them across the front of her body. My dick was almost starting to hurt it was so rigid and sensitive. As soon as I scooted up enough for it to press against her ass and back through my swimsuit, a new wave of electricity shot through my body and I heard her moan again, acknowledging the stiff rod digging into her back from behind.
Taking the initiative, I leaned in to kiss her neck, smelling the sweet nectar of her perfume mixed with her natural smell. "This is what a real woman smells like," I thought to myself, "not whatever scent of the week was given away in mademoiselle magazine, like most of the girls at school use." Continuing to grip her tits with both hands as my tongue flickered on the nape of her neck, I was now getting more and more moans out of Kara as my hips ever so slightly bucked my hard penis against her body. I gripped her waist, feeling her soft skin give way between my fingers, and held her close as I took her earlobe in my mouth and massaged it with my tongue.
Kara grabbed my left arm, and pulled it toward her, signaling me to come around to the front of her. As I did, I saw for the first time her bare breasts, slightly paler than the skin around them, and a little bigger than I pictured them. They had a slight sag, which I'm guessing is normal for a 30-year old mother, but the nipples stuck straight out at attention. Her legs, bare all the way up to her small bikini bottoms, were parted slightly, allowing me to slip between them as I lowered myself over her.
For a 20-year-old guy, I'd say I've got a fair amount of sexual experience: I had sex for the first time at 16, then did it with three other girls before moving on to college. In two years there, I've been with four different girls. Some were better than others, and a couple were really good, but I'd never experienced anything like the feeling of being intimate with a mature woman, or what I would consider a 'woman' at all. Now, many of you would consider 30 to be really young, but for a guy used to high school and sorority girls, she was definitely an 'older woman', in all the best senses of the phrase. There was an electricity between us, for one thing, but I also sensed I was in good hands, like my skills as a lover would be at least matched, if not bested. I loved the way she moved her body, confident and sure; and I loved the way her body looked: filled out, graceful, but not overweight. Her hands and feet were beautiful and immaculately cared for, same with her hair and face, the latter of which showed just the faintest lines of sun and wind over time.
In one motion, I lowered myself over her, reclining us both in the lounger until she was laid back against the reclined backrest, then moved my lips toward hers as we joined in a deep kiss. Almost immediately, I felt her tongue reaching into my mouth, massaging mine as she moaned softly. A new wave surged through me as I felt her legs rub up against mine and her feet caress my calves. I felt the heat of both our bodies as our chests met with every breath she took in. I pulled forward enough to bring the bulbous head of my cock, rock hard and throbbing beneath my swimsuit, into contact with the crotch of Kara's swimsuit. She moaned as my hardness pressed against the lips of her opening, which were surely beginning to moisten by now. I started a rhythm, repeatedly knocking against the thin fabric between her legs as my hands explored her body and my tongue explored every inch of her mouth. I noticed that she was starting to move her hips in response to mine, dry-humping me on her pool lounge chair! Was this really happening?
I reached behind her, grabbing two handfuls of her ass and pulled her up onto my lap so that my hands could better explore Kara's body. Her bikini top was now laying on the concrete deck, and her bare breasts, reddened from excitement and contact, heaved as she breathed in and out. She wrapped her legs around my body, pressing the shaft of my penis against her groin as it stood straight up between us. My hands felt every part of her body: the muscles of her upper back, the softness of her shoulders, the subtle bumps of her backbone, the extra skin around her waist, her soft breasts, and her luscious ass, partially hidden below her swimsuit. I kissed her neck again, watching her face express a mixture of lust, satisfaction, and anxiety. Her eyes were closed and she moaned as my big hands secured her tightly on my lap. She was completely in my sure grasp, and we both knew it by this point.
Kara reached between us and felt the hard head of my cock through my swimsuit, but soon reached into my suit to wrap her fingers around my bare shaft. We both moaned as she ran her fingers around it, then made a light fist around its width and began to pump the top three or four inches of it. She broke the kiss to look down between us at the large organ she was now caressing.
"I should take these off, give you better access," I said, all the while pumping my hips below her in concert with her hand job. She nodded as I lifted her off my lap so I could stand up. My penis sprung forward as I lowered my swimsuit down my legs and kicked it to the side. Kara appeared to be mesmerized by my unleashed erection, taking it carefully into both hands and staring intently at it. I knew I wasn't hurting as far as penis size goes, but I wouldn't exactly say I've got porn-star size. Either way, this 30-year old woman appeared impressed.
I throbbed each time the insides of her hands rubbed up and down my shaft, leaning my head back in ecstasy but looking down again quickly to capture the image of Kara worshiping me as I stood naked in front of her. This wouldn't do for long, though. As much I'm into pleasing women, I'm just as horny as the next young guy, and I've been fantasizing about fucking Kara for the last month or so. Now that it was bizarrely within reach, I was getting impatient. I leaned into Kara, once again gently reclining her, but this time I adjusted the seatback so that the entire lounger was flat. I slipped in between her legs and insistently poked my penis at her vagina, only a thin layer of fabric coming between them as I lowered my weight onto her body.
"You're so big, Jason....I can feel you making me wet...oh jesus," she said with frustration and lust. I snuk a hand down there and discovered that, indeed, it was getting very warm and wet down there. Her lubrication was leaking through her swimsuit and onto the end of my dick as she gyrated against me.
"Oh..." she moaned as I lifted myself up to my knees, grabbed the sides to her bikini bottom, and pulled them through her legs and tossed them on top of my swimsuit. Both of her ankles rested on my shoulders, and I looked down between her legs to see her treasure. She had a small but thick bush that gave away to small pink lips below, reddened some by the friction of our dry-fucking. I took one foot in my hands and caressed it, noticing the soft skin of her sole and the smooth surface of her nails. Then I licked up along her instep and each of her toes, admiring their perfection and how much they turned me on. She rested the other foot on my face, lobbying for equal attention.
"You like my feet don't you?" she asked with a slight smile as I rubbed up and down her calves and ankles.
I nodded, then said, "I love your whole body. You are so sexy."
"Tell me that again," she said, this time with her eyes closed.
"I love your sexy, wonderful body, Kara."
With that, I lowered her legs to each side of me again, and crawled up her body, my big dong wagging between my legs, as if it smelled her pussy and was guiding the rest of me toward it. I rubbed the length of my erection along her pubis in anticipation of penetrating her, and soon. I could feel a combination of the wiry texture of her pubic hair and the slick liquid of her lubrication as my member sawed across her opening over and over again. Kara looked to be hyperventilating, and her face and chest were flush with excitement. I looked her in the eyes as I positioned my head at her entrance. I could feel the heat of her chamber as my cock gently pressed on her labia, ready to penetrate. She gripped my biceps from below, preparing to brace herself.
"Jason, I shouldn't do this...." she said, in almost a whisper, "but,....UUNNNGHHH!!!" she moaned loudly as I pressed my swollen head into her chamber. I was enveloped in intense warmth, and held it there just to get used to the feeling, and let Kara get used to it too.