Karen & The Pool Boy Ch. 02

Chapter 2: Jared's Story

**Note to the reader: This is the continuation of 'Karen and The Pool Boy,' my first submission to Literotica (it is suggested, though not required, that you read that story first). I have decided to write this part of the tale from the male perspective, both as a challenge to myself and as a way to fully describe the kind of character that I personally find most irresistible in the mature woman/younger man genre. This story is my own original creation, but I owe a debt of gratitude to the wonderful roleplay partners I have had over the years – there is a little of each of them in the character of Jared. I hope you enjoy reading it as much as I have enjoyed writing it and as always, feedback is adored.**

My senses were slow to return after the way Mrs. McMillan had made me cum. For a whole minute, I thought maybe I had just died of a heart attack or something, that was how good it felt. But in the next instant I realized I was still alive because I could feel her mouth on my cock, her tongue on my balls as she licked me clean. I was so sensitive after what she had done to me that it almost hurt but I didn't want her to stop. Slowly I struggled to lift my head from the couch and the figure of Mrs. McMillan, on her knees in front of me, came into view.

If what she was doing to me felt good, then watching her do it was pure heaven. She had my thighs spread open and as I watched, she alternated between suckling my balls and licking at my glistening wet shaft with her soft, pink tongue. What really turned me on, though, was that she was watching me watch her, holding my gaze with those amazing eyes that seemed to change color with her mood. She stroked her fingers along my inner thigh and I shuddered. Even though I had just blown the biggest load of my life I was still rock-hard and I wondered to myself, as my head lolled back against the couch cushions, just how I had ever gotten so lucky.

* * *

All those years I had been cleaning that pool and I could count on one hand the times that Mrs. McMillan had ever acknowledged me. Not that I was surprised or anything – she was a grown woman and I could never even get anywhere with girls my own age. Painfully shy and awkward, I was the definition of a late-bloomer: I sprouted to 6'1'' in the 9th grade and besides my unnatural height, I was also sidled with thick glasses to correct my myopia, big ears that stuck out from either side of my head, and terrible acne. I was a notorious klutz, famous for tripping over my own feet, and I was too chickenshit to experiment with cigarettes and pot like the popular kids did. My nerd status was cemented by the fact that I excelled in school and constantly brought home straight A's. My parents praised me as the perfect son and I was proud of my high GPA, but I secretly started to wonder if I was destined to live out the rest of my life as a virginal, scholarly dork.

Then, things started to change. I got contact lenses when I turned seventeen and my skin miraculously cleared around the same time. To top it off, I discovered there were a couple of sports I was actually good at. By senior year, I was on both the swim team and the varsity baseball team and I had finally developed enough muscle to fill out my scrawny frame. I was amazed because suddenly, out of nowhere, girls would talk to me in the halls or smile at me in class and I loved all the new attention. But there were problems. I was still very shy and very studious and worst of all, I was cursed with the stigma of being "too nice" to date. Alot of girls were attracted to me, but once they got to know me, they only saw me as the brotherly type or as the one they could come to when they needed a shoulder to cry on. When they wanted to get laid, I was left home alone to jerk off while they went out with some asshole who would treat them like shit. So it was that by my eighteenth birthday, my experience with women was still limited to a few brief make-out sessions and my own private sexual fantasies.

Mrs. McMillan, ironically enough, had held a starring role in many of those fantasies for as long as I could remember. I had only seen her on a few occasions but when I did, those brief glimpses would provide enough fuel for weeks of erotic fantasy. She had such a hot body - like a pin-up model from those old vintage calendars - and even though she was older, none of the girls my own age could compete with her dangerous curves. I had masturbated many times to the image of her big breasts squeezed into the top of her skimpy tennis outfits and just the fleeting memory of watching her bend over in a pair of shorts would make my cock throb in my pants. My favorite thing was to stroke myself while imagining that I was plowing her pussy with my dick, her incredible tits wobbling on her chest as she uttered a series of sexy moans. Pretending that I was buried inside her to the hilt, I would erupt like a geyser and fill the imaginary Mrs. McMillan with my hot sperm.

That said, you can imagine my surprise when I entered the backyard for what I thought would be just a regular afternoon of pool cleaning, only to find Mrs. McMillan there in a white bikini that looked like it was two sizes too small. My dick went stiff the minute I saw her and if anyone had told me that I would be shooting my load into her mouth a little less than half an hour later, I would never have believed them. Apparently miracles did happen - either that or this was the best fucking dream I'd ever had. When I managed to lift my head from the couch again, she was still watching me, wearing what could only be described as a Cheshire cat grin. I felt suddenly shy.

"Hi," I said stupidly.

She laughed. "Hi yourself, stud." She had such a sexy way of talking, her voice was so warm and sultry yet sweet, like audible honey. Her next words caught me off guard. "Was that your first blowjob, Jared?"

I couldn't help blushing and I dropped my eyes from hers. "Uh, yeah. How did you know?" I must have been even lamer than I thought if she could already tell.

"Don't be embarrassed," She was stroking my leg tenderly, as if she sensed my insecurity. "I just figured you'd never had a woman suck your cock because you seemed to take such pleasure in each sensation. The way you moaned, the way you squirmed... I could tell you loved it and you just don't know how much of a turn-on that was for me."

"Really?" Between the way she was touching me and the way she was talking, I was about as hot as a lit firecracker and as hard as I had ever been. This fact was not lost on Mrs. McMillan, who reached up and gave my cock a gentle tug. It felt so good – I shuddered and grit my teeth to keep from moaning loudly.

"Yes really, Jared. It's been so long since anyone has made me feel as sexy as you just did," She purred, giving my cock a couple more strokes before rolling gracefully to her feet in front of me.

At this point, I was totally confused. What was she talking about? I hadn't done anything except cum in her mouth and I had no idea how that could be sexy. From what I gathered, most of the girls I knew thought it was really gross. Then again, this no schoolgirl. This was Mrs. McMillan and I wasn't about to challenge her opinion, especially when she shrugged her way out of the see-through robe-type thingie she was wearing and draped it over the armchair. Now nothing hindered my view of her bikini-clad body. Mrs. McMillan turned to smile at me. "You know, I bet I can think of something else we can do that you'll enjoy."

More than the blowjob? I couldn't fathom anything I'd enjoy more than that. But as I watched, she slid her thumbs under the straps of the bikini top, stretching them forward so that her big tits threatened to spill out. She wore a knowing little smile as she paused. "Would you like to see me naked, Jared?"

My naked dick gave an involuntary twitch at her words and I reached for it, stroking myself as I nodded wordlessly. She shook her head at me. "No... remember, if you want something, you need to ask for it."

She was playing with me. I knew it and I didn't care. In fact, my cock swelled again when she said that. "Yes, Mrs. McMillan. Can I please see you naked?"

"Good boy, Jared." Her smile widened and she acquiesced, pulling the straps down over her shoulders and baring her breasts to me. It was a wonderful sight – in stark contrast to the rest of her tanned body, Mrs. McMillan's heavy tits were milky white where her bikini top had covered them and each breast was topped with a caramel-colored areola the size of a silver dollar. Centered squarely between that was a luscious pale brown nipple. I longed to suckle one of those nipples, to just bury my face between her naked breasts and then cum all over them. I stroked myself, moaning softly as I watched her reach up and squeeze her own tits in her hands. "Mrs. McMillan... you're beautiful..." I was dimly aware that I sounded like a love-struck dumbass.

"And you, Jared, are so sweet..." Her smile radiated sensuality and it was the first time ever that I didn't resent being called "sweet" by someone of the opposite sex.

Meanwhile, Mrs. McMillan's private show continued. She untied the bikini top and tossed it away, her heavy breasts swaying with the movement, and her hands went next to the strings at either side of her hips. She had such wonderful hips – they were wide and even further emphasized by her narrow waist. I wet my lips as she slid the bikini bottoms off, moving her hips from side to side to work them down her legs, past her knees. Leaving the bikini bottoms in a small heap on the carpet, she stepped towards me and I could see her pussy at the apex of her taut thighs. Dark curls of pubic hair hid most of it from me, but when she walked I could see the glistening pink slit of her labia, and above that, the throbbing bud of her clitoris. My hand moved faster, stroking along the shaft of my throbbing cock, and my eyes narrowed to slits.

"Oh, fuck..." I moaned, squeezing my cock to keep from cumming right that second. I was caught in a haze of pure lust and Mrs. McMillan was watching me.

"Mmmm, you're getting so very excited, aren't you, baby?" She crooned softly as she came forward, standing right near where I sat on the couch and extending her hand to rake her fingers through my hair. I imagined I could hear excitement in her voice too, but I was so far gone I could no longer distinguish between reality and my own horny delusions.

"Yes," I groaned, eyes closing as I turned my head towards the gentle touch of her fingers.

"Let me watch you play with yourself, Jared..." Her voice was breathy, but demanding, "Show me what you do when you're all by yourself and you want to make yourself cum."

I groaned, feeling embarrassed but so turned on by her request. I was already stroking myself, the fingers of my right hand curled around the stiff pole of my shaft. I let my knees fall even further apart and I reached down with my other hand to tug at my balls, rolling them around against my palm as I manipulated my cock.

"Mmm, yes... that's it, Jared. Stroke it for me..." I could heard Mrs. McMillan breathing heavily beside me, and when I opened my eyes, I saw that she had lifted one leg and she had her foot resting against the couch cushion beside me. Her thighs were spread open and I could see her pussy up close - the dark curls of her pubic hair framed the thick, glistening wet lips of her labia, which were parted by her perfectly manicured fingers as she delved them inside of herself. I could detect the musky scent of her arousal in the air between us and I was held captive by the sight of her two fingers plunging in and out of her juicy pussy, while her thumb teased her engorged clit. Her hips rocked forward and she murmured soft, aching little sounds of pleasure that made my cock twitch. Her eyes lifted from my crotch just as I gazed up at her. It was sensory overload and suddenly, I felt that familiar, almost overwhelming tingle in my balls. Helplessly, I blurted out: "Oh shit, Mrs. McMillan, I'm gonna cum again..."

Without warning she reached down and pulled my hands away from my crotch. I whimpered, not expecting this, and my ass arched up off of the couch as she linked her fingers with mine. My hips seemed to have a mind of their own and bucked wildly, my cock desperate for some kind of friction to relieve the deep ache in my balls. Mrs. McMillan, meanwhile, had climbed up on top of me, one knee on either side of my thighs. I felt the soft brush of her full breasts against my chest, hot nipples burning into my skin, and then she slowly dropped her hips into my lap. This caused the juicy slit of her drooling pussy to make contact with my hot, hard cock and I squeezed my eyes shut at the delicious sensation. I tried to control myself but I couldn't – I humped fervently against her and the feeling of naked our sexes rubbing together was bringing me to the brink of orgasm once more.

"Oh Jared..." Her voice was breathless, her breathing labored, and she squeezed my hands against her own, her hips rolling forward just as mine did. I couldn't believe something could feel so good – the swollen lips of her labia, slick with her musky juices, coated my eager dick and in the next moment, she had lowered her mouth to mine. We kissed hungrily, her tongue pushing gently past my parted lips to stroke along my own; I responded by mimicking her movements, rolling my tongue over hers and tasting remnants of my own cum in the process. The kiss deepened, then broke off when neither of us could breathe any longer.

"God... you feel so good..." She whispered hotly. I couldn't even find the words to respond. Our naked bodies were still rubbing lewdly together, and the moment I opened my eyes, I found her staring at me. She was beautiful – her dark hair like a halo around her flushed face, her lips swollen from our kisses and her golden-hued eyes burned with a desire that matched my own. She leaned in to kiss me again, slowly and languidly this time, and then pulled back, gazing into my eyes. "Have you ever been fucked, Jared?"

Between us, my cock throbbed at that lurid question. I shook my head. Then, remembering her rule, I panted out: "No, Mrs. McMillan."

"Do you want me to fuck you? Right now?"

"Ohhh yes..." It was almost a whimper.

"Yes what, Jared? Tell me what you want..."

It almost pained me to respond but I would have done anything she asked me to at that moment. "Please, Mrs. McMillan..." I begged, "Please fuck me..."

That satisfied her. She released one of my hands and then her mouth found mine again. She kissed me so tenderly, her hips rocking against my own, and then the next thing I felt was her hand around my cock, guiding me to the entrance of her juicy cunt. She shifted her weight forward, lifting herself a bit before impaling herself on my cock with a low, guttural moan. I could feel the head of my dick nudging its way between her wet lips, parting them just before her tight pussy drew me in and swallowed me whole.

Words fail to describe how it felt to have my dick inside her, or to capture my own excitement at that moment. Her pussy was hot and wet as it enveloped my cock and her inner muscles milked me lovingly the way that her mouth had, only this new sensation was so much more intense. I could feel it spread all the way into my thighs and my lower belly - a hot, tingling feeling that made my asscheeks clench involuntarily. My hips rocked up against hers, wanting to get as much of my cock inside of her as I could. Mrs. McMillan's arms came around my shoulders and it was all I could do to sit there, my face buried against the place where her neck met her shoulder, my hands gripping her womanly hips as she controlled the rhythm of our lovemaking.

"Mrs. McMillan..." My moan was muffled against her neck and she nuzzled her way along my hairline, kissing both my closed eyelids and the tip of my nose. As she kissed me, my hands explored her body, trailing my fingers along her sides, all the way up until I reached her breasts. I eagerly captured one in each hand and she gave shuddering intake of breath when I squeezed tentatively. Her tits were so soft and deliciously heavy, her erect nipples twin pinpoints of heat that burned against each of my palms. I lowered my head, my hands sliding away under her arms to stroke at her back, and my searching mouth blindly found her left nipple. Instinctively, I began to suck it.

"Jared... ooohhhh..."Her head fell back between her shoulders, exposing the slender column of her neck. I heard her whimper when my lips formed a tight seal around the soft flesh of her breast, my tongue undulating against her nipple. She rolled her hips faster, her pussy milking my cock wetly with each sucking motion of my mouth. I struggled to hold out, to make my first time last, but I could feel her mouth nuzzling at my ear, her tongue tracing the shape of it as her breath fanned against my neck. "Mmm, it feels so good to fuck, doesn't it Jared?" she whispered, her words broken by something that sounded like a whimper or a sob, "Oooh, that's it, baby. Fuck me like a good boy and make me cum on your cock..."

When I heard her talking to me like that, it was all over. I moaned deeply, her nipple slipping from my mouth with a wet "pop" and my cock gave a single throb before it exploded, blasting cum deep into her pussy just like I had so many times in my fantasies. Only now it was finally real and I could feel her soft breasts, I could taste her skin with my tongue. I could hear her voice at my ear as I sent spurt after spurt of hot jizz deep into her womb. Her commentary made my toes curl: "Oooh, that's it, honey... Oh, fuck yes... you've got so much cum for me, don't you? Mmm, give it all to me, baby boy..."

I felt like I was never going to stop cumming for her, my entire body trembling as hot pleasure reeled off of me in waves. Mrs. McMillan's arms tightened around me, her body seeming to go completely still in my arms for a moment. Then, I felt a rush of wetness flooding up around my cock; her pussy was spasming around my dick as it was wedged inside her, and the clenching sensations of her hot cunt served to prolong my release. Somewhere, in the back of my mind, I was filled with wonder at the fact that she was actually cumming.

"Ohhhh Jared... Jared, Jared..." My name was litany on her lips, repeated over and over again before dissolving into helpless cries of pleasure. She bucked her hips wildly against me as our bodies writhed together for several long moments, both of us overcome with the pleasure of our own orgasms.

It seemed a long time later before I could breathe again. Mrs. McMillan was still sitting on my dick, her hands sliding along my bare shoulders as she kissed my collarbone. Wordlessly, I let my hands do some traveling – with fingers spread, I smoothed my way along her bare back, then down to her hips again. She murmured softly as my hands trailed along her sides, over her ribcage. Her breasts were my goal, wanting to feel the weight of them again, but she leaned back and stopped me with a kiss to my mouth.

"Jared, darling, that was wonderful," Her hands came up and grasped my wrists. "But my husband will be home soon. You have to go before he catches us like this."

Given the fact that I had known this was coming, I was surprised by how disappointed I felt. I was still buried inside of her but I was starting to go soft and she pulled her hips back to allow my cum-coated cock to slide out of her oozing cunt. Her pussy lips seemed reluctant to let me go, clinging to the meat of my wet shaft as she swung her leg over me to stand. Enthralled and still very horny, I gazed up at her. "Mrs. McMillan... can we please do this again next week?"

She smiled and leaned down to kiss me again, a wet, lingering kiss. "Maybe," she murmured against my mouth, "But only if you promise to be a very good boy and not tell anyone about what we've done this afternoon."