6 comments/ 81021 views/ 38 favorites So I'm a Pool Boy By: JagFarlane Jason leaned back in the chair, flicking through the report he was working on. Every now and then he'd tap away at the laptop, making a few edits to the paper, then lean back to start reading again. When the report was done, he sipped at the glass of iced tea and opened his e-mail to send the report off to his professor. Leaning back again in the chair, he looked past the large pool, across the well maintained grounds and out to the beach and roaring ocean. There were worse ways to spend his summer. Coming into the summer after his sophomore year, Jason had signed up with a temp agency as a lifeguard. He'd worked with them the previous summer and found it decent enough, spending most of it attending pool parties and occasionally working with local pools when they expected an overflow of patrons. The money hadn't been bad, since people were partying most were in a good mood, and it hadn't been an overburden of work. This summer though, he was asked to work at just one pool. A Miss Amber Handley had inquired about hiring a lifeguard who didn't mind doing a little work around the pool during the daytime. He'd not been very interested at first, but was eventually lulled into the idea of having a steady work schedule. Ms. Handley, or Amber as she asked to be called, was a fan of using her pool sometimes several times a day. It helped her to think and clear her mind and considering she was an executive vice president of a large health care company he was willing to give her the benefit of the doubt. The gig was fairly easy as far as the jobs went, she was quite the accomplished swimmer and so there were times that he felt that perhaps she should be the one teaching him not him there to watch over her. During the first week she'd found out about his being in college and had encouraged him to sign up for an online course or two during the summer semesters, assuring him there would be plenty of time to work on the courses. To help with that she'd given him access to one of the wireless networks on the property. Not one to look a gift horse in the mouth, he signed up for a pair of courses figuring at the least his work load over his junior year would be reduced. Just as he was shutting the laptop out of the corner of his eye he spotted Amber strolling out towards the pool for her afternoon swim. When he first got here Jason had been very concerned that he was going to be bored out of his mind watching an empty pool for day after day. Instead he'd found that on her days home she went swimming at least twice and often three times a day, and allowed the rest of the staff to use the pool prior to the workday, during breaks, and after the workday. At first she'd been fairly conservative with her bathing suits, mostly one pieces but after the first two weeks she'd broken out the two pieces and by now had made bikinis routine. He'd admittedly never really given a woman in her forties a second glance before meeting her but the first time she stepped out in a mint green bikini, top filled out quite nicely and her rear well framed by the bottoms he was hooked and by the suits she wore it seemed she very much enjoyed flaunting it. Today it was a bright red bikini, with nails painted to match, and she waved to him as she made her way to the diving board. Three jumps on the end and she plunged in, moved in a well scripted arch that just made her pert rear stand out against the green tree tops. He could already feel his cock stirring, more than once he'd retreated to the pool house bathroom for some alone time after watching her swim. There were days he swore she did it on purpose to get that reaction from him. He sat back in the chair, sipping at the drink while watching her do her usual laps, changing strokes every two laps. Her form was nearly perfect, and considering how much she practiced he wasn't surprised and if he hadn't known her age if you'd told him she was twenty he might have been willing to believe that. It just seemed like she had quite the bit of energy, along with her personality and physical shape there were times he wondered why there wasn't a male or female companion around the house but knew better than to ask that question. It just wasn't a wise idea to go poking around her personal business and he really didn't want to risk losing a good deal. Watching her swim the laps was relaxing in many ways, she always kept up a good rhythm and her movements were fluid, and regular. It was very different than other lifeguarding jobs where he often had to watch kids that were unpredictable and even worse were the drunks at some of the parties he'd had to watch over. At least kids listened to the lifeguards for the most part but drunk adults had a bad tendency to ignore the rules. This was completely different, he really was sure she didn't need him here, but he couldn't blame her if she could afford and wanted the security. After Amber finished her swim, she rose up and made her way towards the tables where Jason was seated. He always did his best to try and keep his eyes looking more towards her face but between age and her body, they always wandered down to take in the sight. What he never saw was the smile she'd flash when she realized he was looking at the rest of her body. She had a larger than average chest that bounced just a bit with each step, muscular legs, and a taut tummy. It was a body that she'd worked hard to get and maintain and so having a much younger man appreciate it always made her feel good and every now and then she caught a glimpse of how much he appreciated it when something outlined itself against his swim trunks. She picked up a towel and slowly began to dry herself off, "Good morning Jason, hope this day finds you well? Classes going alright?" As she finished drying off her body, she settled into the chair next to him and began to towel dry her shoulder length blonde hair, still blessedly natural in color. "G'morn Miss Handley, well it's a pretty morning with sun and no chance of rain so seems like a good day to me. The History course is going ok though I'm going to have to work a little harder on the English papers in order to get a decent grade. Apparently he's not a huge fan of my writing style." Jason frowned a little as he thought of the last review of his writing, he was passing but not the sort of grades he normally pulled. He poured her a glass of the sweet tea and placed it in front of her. She nodded, "You know, I asked you to call me Amber." A little smile crossed her lips. "English can be a difficult class sometimes, there are a lot of nuances to the language and in some ways it's one of the most complex to learn. We borrow words from so many languages. If you want to borrow any books from the collection in my office, there's a couple on writing in there." Amber leaned back into the chair, picking up the tea and taking a sip of it. "In my world being able to write clearly with a command of the English language can often be the difference between a done deal and a lost deal, or more pertinent for your after school, a good paying job or having to work a few extra rungs of the ladder." He smiled a little, "Yes, Miss Handley." Then listened partly out of politeness as he'd heard this sort of advice coming from professors before, but still coming from someone working outside of academics it did carry more weight. She liked to dole out advice, but it usually was general and mostly guiding in the direction of how he could help himself with things. In some ways that annoyed him, it didn't give a direct answer, though he was slowly learning that by having to go find the answer himself, he was more likely to recall the answer or at least how to find it himself. She patted him on the knee, something she'd only started a week ago and it seemed her hand was slowly making its way up his thigh. At first it had kind of bothered him, he just wasn't used to being touched by a client, but he'd gotten used to it. After the pat she rose up and made her way back to the house, leaving the towel draped over the chair she'd been in. He watched her walk back inside, distracted by her tight rear as she walked inside. When she paused and glanced back at him, he snapped out of it and tried to act as if he'd not been staring at her. She just smiled at him, "Remember, call me Amber!" Then into the house she went. He sighed and opened the laptop back up, doing his best to ignore the tenting of his swim trunks. By Friday he was getting used to her in bikinis, or at least that's what he told himself, but his cock always had other ideas and figuring out how to keep it hidden from her without being too obvious had become quite the chore. Often times he used towels over his lap to try to hide it, though that really made it seem like he was hiding something. Jason had even tried jerking off before coming to work, thinking if he offloaded ahead of time then maybe he would have some resistance but there was something about her that made him throbbing hard within seconds of seeing her. Perhaps it was her carriage, the calm confidence of an experienced woman that drove him crazy. After her morning swim, instead of drying off and going straight back inside, she waltzed over to a lounge chair, laid it out, and laid her front side over it to let her back catch the sun. He was split in his feelings, part of him was elated to get to gaze upon her a bit longer while the other part of him was stressed at having to keep his swollen member a secret even longer. Unfortunately for him, she had other ideas and soon called over, "Jason, would you be willing to do me a favor? I don't want to get burnt on my back, just a little tan. Would you be willing to put the lotion on my back please?" A mix of elation at getting to rub her and concern about her figuring out what his state was crossed him, but not wanting to disappoint her he responded, "Sure Ms. Handley, I'll be there in a minute!" Using the mesh of the trunks to the best that he could to try and pin down his cock, Jason grabbed the lotion and walked towards her, approaching from the direction of her feet, walking alongside of her right side till he was about her waist. The lotion top was popped and he poured a little into his hand, then leaned over to begin to rub the lotion upon her back and shoulders. "Here, let me help," she said while reaching back to undo the strap of her top, letting them fall to her sides and exposing the sides of her breasts. Jason had to bite down hard upon his lower lip to stifle the pleased groan at the sight. "You know it might just be easier if you straddle over me, you could get a little more force into the rubbing." A little mental prayer was said in hopes that the mesh would hold against the strain, he raised his leg and slowly straddled over her pert rear. The movement caused his cock to slip free from the mesh and strain against the fabric of his trunks. Slowly and carefully he worked the lotion upon her back, doing his best to avoid any areas that he mentally deemed dangerous to touch upon her. Granted, he was well aware that straddling his client's nearly nude ass while rubbing her naked back with lotion was fairly well into the dangerous area and there was no helping it. To make matters worse, she seemed to really enjoy arching her back and grazing her rear against his thighs. Just as Jason was beginning to think he couldn't take much more of this torture and how quickly he could run to the pool house after this was over with to relieve himself Amber flipped herself over. Her top fell to the wayside, revealing plump breasts tipped with small rosy nipples. As he blinked, unsure of what to say, she reached up and pulled down the waistband of his trunks, taking the head of his cock into her mouth as it popped out. It took her only a few bobs of her head and a strong suck to coerce his cum to flow from his balls and fill her mouth. Releasing the tip, she swallowed and looked up at him, "So think you could start calling me Amber from now on? Or slut if you prefer while I'm sucking on this lovely cock of yours." After the shock of what had just happened finally sunk in, he slowly pulled his trunks up in a bit of modesty. Amber came up to a seated position and gently tapped the lounge chair next to her, waiting till he took a seat. "Now, doesn't that feel better? I couldn't stand the idea of you suffering anymore, it was quite obvious and I think this is a much more pleasurable outcome thank you wanking off in the bathroom." She just smiled and patted his leg softly. That she was taking this like nothing at all just added to the confusion in his head, women always seemed to like to play hard to get unless they were trashed. Amber instead, had just blown him and acted like it was a normal thing to do, she'd even swallowed it right down. And just, yeah...she apparently also knew about him jerking off in the bathroom, though she was at least right that he much rather enjoyed blowing his wad in her mouth. His eyes followed her as she got up and strolled to the table he'd been at, picked up his glass of tea and took a couple of swallows. He had to admit that her breasts were quite perky for her age with not a lot of sag but it didn't seem like she'd had a breast job done. She rinsed out the taste of cum, while he was about average for what she'd tasted it still wasn't her favorite flavor to let linger in her mouth. Amber leaned against the table, putting together in her head how to present this to him and letting what happened fully sink into his brain. Judging by the fact it seemed that he was rising again he was enjoying the view and the probably burned in his brain mental image of her sucking his cock. From the little she'd seen of it, and felt of it, he had a nice one and if he was willing to let this continue it might just be a very nice summer indeed. When he looked like he was about ready, she took another swallow of the tea and strolled on over, retaking her seat on the chair. "So, I'll take by now that you've more or less accepted what happened and since you haven't reacted in a negative manner then you fairly well enjoyed it. I'm sure by now that you've noticed that I don't generally have any male or female companions coming by. The reason is fairly complex but it boils down to having some money and not wanting to deal with people my age feeling their lack of savings and a bit greedy from partying their youths away. You, I've noticed, never mention having a young male or female companion of your own and you tend to show up early and have never shown up late, which I'd normally expect from someone your age during the summer. After all, it is party season and a chance to enjoy not having studies, sound about right so far?" He nodded slowly, kind of having the idea where she was going with this and wondering just what she was going to want and what she was planning to offer. Of course he was intrigued, if it meant relieving his aching balls through sex instead of sitting at his computer wanking to a tube site then he was interested, within reason. "Well then, I propose we allow this relationship to progress and include regular sexual activity." She then rolled her eyes, "Geeze I sound way too professional with this. Basically what I'd like is to get shagged on a regular basis, preferably daily and if you can provide it, two or three loads of cum a day. In return I'll teach you the art of sex cause God knows you've probably got stamina like no one's business but need to learn some of the techniques. I don't expect much more than that but if something develops then so be it. I'm completely open to the idea and considering that's how some societies operated, older woman with hot, young stud it's not a new idea. Now if this sounds like something you'd like, I'd really like to see that cock again and if you're willing, to get my poor, unused pussy pounded by it." Amber blew out a breath after the rant and waited for his reaction. At first, how she was treating it was a turn off, even for a very horny young man, and mentally he laughed as the only reason he even understood the word shagged was thanks to Austin Powers. There was a wave of relief when she started the rant as she was now acting a bit more like a normal person instead of so business like. Slowly he nodded as he listened to her rant, most of it made sense, he didn't have a summer fling going on just yet and who would really turn down the offer? Up he stood, moving to stand in front of her, thumbs hooked into the waistband of his shorts and down he yanked them. Stepping out of the shorts, he threw them off to the side and stood up straight, letting her take the look she'd asked for. A smile crossed her face as she watched him remove the trunks, she could feel her slit grow a little more damp in anticipation. It wasn't so much that she was completely desperate, there was without a doubt an attraction there. Whether it was more than lust remained to be seen, but for now she was fine to deal with lust, she craved the feeling of carnal activities again, it had been too long since her last girlfriend had done her good with a strap-on. As his cock was revealed again to her gaze, Amber took her time to look it over, she'd only gotten a glance the last time. He'd need to use a pair of trimmers, that was for sure, but most young men seemed to lack a little in the manscaping department. She traced a fingernail along the half-hard member, noting that he was uncut and pleasantly endowed. His cock slowly began to stiffen in response to her tracing the fingernail along him, Jason could only watch mesmerized as she leaned forwards, opening her mouth and taking him all in one smooth motion. Her nose was buried in his bush, he could feel her begin to softly suckle him, her tongue working the underside of his cock. She bobbed her head, moving about half of his cock in and out of her mouth while working to get him throbbing hard again. When he was again fully erect, she reluctantly let him free of her mouth, then moved to all fours on the chair, pulling her bikini to the side, "Fuck me, NOW!" Without hesitation, he stepped up behind her and guided his hard cock into her waiting pussy, grabbed her hips and slammed into her. With her urging him on, Jason held onto those muscular hips and began to jackhammer her, pulling back hard as he thrust in. She screamed as her needy pussy launched into waves of orgasms, she was multi-orgasmic and when she was in the zone they could come one after the next seamlessly. Hands gripped the fabric of the lounge chair as he pounded her, hips swaying naturally with the rhythm. It was a bit animalistic, just what she'd needed at this moment, a young man caught up in the lust of breeding her. When he finally did fill her with his second load of cum, she disengaged and collapsed on the lounge chair, panting and savoring the blissful feeling of a sore but well fucked pussy, it had been too long. Amber moved a little bit on the lounge chair and motioned him over a step or two, then leaned up to clean his cock of their juices. Once he was clean she snuggled down into the lounge chair to take a nap. When she awoke, Amber stretched out and for a moment wondered at the soreness she had between her thighs. A slow grin formed upon her face as the memory of what had caused it came back to her and slowly she looked over to where Jason was. He'd put his shorts back on and still appeared a bit shocked and maybe a little shy mixed in, it was an emotion that looked cute on him. It reminded her of why she liked younger men, the enthusiasm was oft mixed with a bit of shyness, even the most boisterous of men tended to have a shy side to them, well at least most did. When Jason had snapped back to reality after getting his cock sucked clean, he'd panicked for a few minutes. This was a major violation of the rules and the thought of losing his job was not a pleasant one indeed, he depended on the money to cover things like his textbooks and meal plan while he was away at school. She'd been the initiator though, and he hoped and even thought of praying, that she would keep it a secret from his employers. As he sat there, he contented himself with the idea that since she started it she would probably keep it quiet, other than that he wasn't about to complain about what had happened. She'd surprised him with just how quickly she took over the situation, it wasn't something he was accustomed to and it was the only reason he wasn't worried about having cum inside of her, she just didn't seem like the type to be unprotected. So I'm a Pool Boy As she awoke he held his breath, waiting to see how she would react to everything. All of his fears about losing his job returned to him, all the scary stories he'd ever heard of women decided that the consensual sex they'd had was suddenly not so spooked the hell out of him. It was part of the reason why he had so little experience in bed and now he'd gotten caught up in the moment, worried that a little bit of pleasure was going to cost him a lot. He watched as she strolled over to him, still topless, taking that as a good sign that she didn't immediately cover back up. He watched as she took a seat just across from him, crossing her legs as she sat down, obviously quite comfortable with being mostly nude in his presence. He was just used to some women his age, who seemed to love to throw on a t-shirt and bottoms and by Amber's actions he was guessing she was only wearing her bottoms because she awoke with them. For a few moments he was purely in awe at how comfortable she was acting, at her level of maturity, she was on a different level than he was used to. She changed the way her legs were crossed, not because she was uncomfortable but more because she'd always wanted to do it the way that Sharon Stone had. Seeing his stare she briefly wondered if he would be good for a third round today, then thought the better of draining him on the first day and that she'd much rather a larger load the next time. The thrill of the chase was like nothing else, and feeling so sexually attractive was like an elixir of youth, combined it was the best high she'd ever had, and at her age she'd had quite a number from various sources. Amber poured herself a glass of iced tea and leaned back into the chair, "So any questions? Concerns? Requests?" She couldn't help the business side of her, it was her life and habits had been formed. Was that part of the reason she didn't necessarily date men her age or older, she wasn't sure, all she knew is who she was and how she lived her life. And what she knew right now was that she wouldn't mind, no, she would welcome feeling this lovely sore feeling every day that she could get it. If he had a halfway decent idea of how to eat pussy she'd be more than content to let him warm her bed if he so chose to. She smiled at how he blushed, he'd probably had a few requests go through his mind though she doubted that he would be willing to mention them, for now at least. Young people were like that sometimes, lots of talk but when it got serious she noticed they tended to get shy. Nothing wrong with that in the least bit, it intrigued her and made this all the more fun. A little chuckle when the first response finally came, asking that she not mention this to his bosses. She should have considered that at first, lips turned to a slow smile, "It wouldn't be the best for me to have it go back to your bosses either, so no, none of this will make it beyond the property line." He sighed in a bit of relief at the confirmation of it going no further, almost not realizing just how wound up he'd been over that. A little bit passed as he mulled over the original question, wanting to give it a little bit of time before he responded and needing to sort out what was flying through his head. Finally he looked up at her and asked the most honest question that was nagging at him, "So...I guess I need to ask, why me? What is it about me that you want? I mean I know you kind of answered that before but I'm still lost." She sighed a little at the question, he didn't know just how deep the answer could go. Arms crossed over her chest as she worked on how to best answer the question. Teeth bit down a bit on her lower lip, "Well the most honest answer is that you most likely wouldn't be fucking me with your mind really being on my money or as a business contact. I just grew really sick of dating those around me who are more concerned with my title, my bank account, or both. Really, I just want to feel like a normal woman, lusted after, craved for, and enjoy having sex. Does that help?" Mentally she crossed her fingers, not really wanting to get much further into it as it could drudge up a lot of old feelings. He just nodded slowly at her answer, well that made a bit more sense at the least and considering how her face had moved as she spoke he felt it best not to press her any further on the topic, at least not today. "So what exactly did you have in mind then?" Teeth slowly let go of her lip as her face lit up at the question, "Hmmm oh you know, the usual, you eating me out, getting to suck on you till you fill my tummy with cum. Ummm, of course fucking me in every position we can imagine, and well if you're up for it, occasionally giving it to me in the ass. I think that should suffice, don't you?" Eyebrows were raised as she responded, while the first few ideas were not that unexpected, the last one was foreign territory to him. Jason had heard of that though, and well the idea of getting the chance to try it wasn't as unappealing as it might have sounded. "Yes, I think that should suffice then." He gave her a little smile. She rose up from her chair and turned to make her way towards the lounge chair, bending over to pick up her discarded top. Glancing over the back of her shoulder, "Well back to work. I'll see you later!" Amber strolled back to the house and entered in, looking over Jason as she slowly closed the door, it was going to be quite the fun summer, and she just had a feeling in her gut about that. She grinned while heading up the stairs back to her office, yes quite the fun summer ahead.