tagFirst TimeLearning by the Pool

Learning by the Pool

byLaid71©

I spent the summer before college working as many odd jobs as I could to build up some reserves for the autumn. I painted, built and gardened my way through the long hot summer days, then spent the evenings delivering pizza. Sure my tuition was taken care of, but I didn't want to have to work too much. That way I could enjoy the college experience while I studied. My friends laughed at me, as they spent that last summer of high school taking it easy, and Lisa stopped calling after a couple of lack lustre dates where I fell asleep.

It was early afternoon when I arrived at the Callaghan's house. My task for the afternoon was to mow the grass in the back yard. A largish expanse, easily enough for a ride on mower, but I would have to cut it with the push mower Mr Callaghan provided. I'm sure it was much cheaper for him to just pay me to sweat my way up and down his lawn every week.

The drive was empty when I arrived so I let myself in the side gate and set about my task. It was a really hot day and I was sweating by the time I'd got the mower ready to go. Looking around to ensure no one was watching I removed my t-shirt, letting what little breeze there was dry my torso, sure I'd be sweating again soon enough. I left my t-shirt by the pool, gazing longingly at is cool blue water, how good it would feel to dive in. Day dreaming wasn't getting me anywhere and I began the steady work of putting those green stripes into the lawn Mr Callaghan was so keen on.

I was about half way done, heading back towards the house again, when the sliding doors opened and Mrs Callaghan stepped out. Her hand over her eyes as she looked at who was in her yard, waving as she recognised me, walking round the pool towards the lawn as I plodded towards her cutting as I went. She must have finished work early today as her shapely form was covered in a simple black shift dress that ended mid thigh. Her heels clicking as she moved closer.

"Oh hi Tim, I'd forgotten you were due today," I'd cut the motor on the mower as I got to the end of the lawn were Mrs Callaghan was waiting.

"Hi Mrs Callaghan, I'll be done in 30 minutes or so and out of your way."

"No rush Tim, and call me Kelly, Mrs Callaghan is so formal isn't it?" Kelly; somehow the name fitted her in my mind. "Haven't you filled out since I last saw you topless?"

Suddenly I felt self conscious, looking at my t-shirt lying next to a sun lounger. My family had moved into the close when I was 10 and the Callaghan's were the only house to have a pool at the time. All the kids used to spend Saturday afternoons playing in the pool while the adults drank and barbecued. This was the norm till I was 14, when we had our own pool, and I decided to swim there. This was mostly due to the crush I had on Mrs Callaghan. To a small, shy 14 year old boy she was the height of sexiness and sophistication.

She was always in heels, even at the pool, showing off her shapely, toned calves and thighs when she wore swim suits. Her dresses always showed off her figure to perfection, emphasising the swell of her chest and the roundness of her ass. Her long brunette hair always in a perfect coiffure and her jewellery picked to draw a male eye to all the right places. I was infatuated.

Mrs Callaghan appeared in my dreams whenever they turned dirty, always dressed in a really slinky number she'd worn one Christmas. I could no longer see her in a swim suit without a stirring in my groin and that was just too embarrassing. Enforced isolation was the only answer.

Over time the crush had faded as these things do, my interest captured by girls more my age. Though standing here right next to her, bare chest, I could feel the old urges begin to surface again. I realised I had never really thought of how old she was, late 30's I guessed, a little younger than my Mom for sure. My eyes did a quick survey of her body. It really hadn't changed much in the last 4 years, still as shapely as I remembered, belt highlighting her slim waist and hourglass figure. She obviously worked hard to maintain such a tight body. I felt the hint of a blush form on my face, hoping the heat of the day was covering it.

"Why don't you finish up and I'll make us a nice cool drink and we can chat?" Her hand placed lightly on my shoulder set a further surge of heat through my body.

"Sure Mrs Callaghan, I mean Kelly," I smiled nervously, heart beating faster than it had any business doing.

"Well careful with those stripes, you know how fussy Jerry is." Winking as she turned and headed back to the house.

Watching her walk, hips swaying, wasn't helping me get finished. I had to force myself to get back to work, my mind no longer on keeping the stripes tight and straight like Mr Callaghan demanded.

Finishing the lawn seemed to take forever, a montage of memories running through my mind, making it hard to keep the mower moving forward in a straight line. All my youthful desires and dreams came flooding back. Get a grip, I told myself, as I stored the mower back in the tool shed. Mrs Callaghan was just making polite conversation; even in my mind I couldn't quite call her Kelly, my mind, however, was not willing to let go of the memories just yet.

I wandered back to the pool, having decided I'd collect my t-shirt, make my excuses, and leave. My mind was in turmoil and I knew I wouldn't be able to chat casually with Kelly without tripping over my tongue and looking stupid and that was something I didn't want to remember. While I had no more planned until I had to head out to the pizzeria I was sure here was somewhere I shouldn't linger. Rounding the corner and seeing Mrs Callaghan reclining on a lounger my resolve wavered.

She had changed. Gone was the smart business dress, replaced by a black bikini. A flimsy sarong was wrapped around her waist covering her legs, though as it was practically see through I wondered why she bothered. I paused surveying her body, suddenly 14 again, feeling that familiar stirring in my shorts. Time had been kind, sure there was a bit of a belly on show but her legs were still stunning and her breasts as full as I remembered. What was I going to do now? Could I just leave quietly abandoning my shirt, or should I just be adult about this, go over pick it up and leave.

"Tim, you've finished? Come over here, I've made Iced tea." There went my chance to run.

I walked nervously over to the loungers, hoping my baggy shorts hid my arousal. I sat and reached for my t-shirt, wanting to cover as much of my body as possible, sure every bit was giving away how I felt.

"Far too hot for your top Tim, leave it off and cool down," Kelly handed me a glass of tea "and it's too nice a torso to hide."

I took the glass, the situation now well outside my comfort zone, taking a big pull at the cool drink.

"Oh Tim, I should have said it's a bit alcoholic." Kelly was now sitting next to me, rubbing my back as I coughed, the shock of the alcohol in the tea causing me to choke.

"Thank you Kelly, I'm fine." My words sounded weak and silly even to me. But now she was sitting right next to me. The heat of her thigh pressed against mine, her breast pushing into my arm as she rubbed my back gently.

"Well after all that hard work I thought you deserved a treat," Kelly moved away slightly as my coughing eased "and as you're off to college I'm sure you can handle some liquor. You all ready for college now?"

"Yes, all my tuition is sorted and with the odd jobs I've been doing I shouldn't need to work too much."

"Well I was really meaning are you ready for all those girls you're going to attract with that hot body?"

I was dumbfounded, had Mrs Callaghan really just said that. Sure I had done the normal sports at school, kept myself fit, but I was no football star or anything. Maybe the summer of working all those odd jobs had made my upper body a bit more muscular. But what on earth was going on here. Was Mrs Callaghan, Kelly, really saying what I was hearing?

"I'm sure you had the pick of all the girls at the prom." a finger now tracing a line down my chest, red nail clipping my nipple as it moved down.

"Well, sure, but I've been seeing this girl, and well..." Lisa and I had been dating for most of the senior year. We'd got pretty close and I'd thought that come the prom we'd have sex. She'd let me play with her breasts before, pert and firm with large nipples that got really hard, but never any further than that, despite my thinly veiled attempts, culminating in failure when I'd tried to slide my hand under her prom dress.

"Are you telling me that you've never been with a woman?" My mouth moved but no coherent words came out, my mind totally a whirl at Kelly's words, my cock now fully erect straining against my shorts. "Well I think we shall have to fix that for you."

Kelly moved closer and kissed me, her lips soft and warm, I responded, my mind a whirl and my heart beating out of my chest. What on earth was happening here? I should stop this, leave before anything else happened, yet I kissed her back, opening my mouth as I felt her tongue seek a way inside. The kiss seemed to last a lifetime, tongues lazily teasing each other, lips locked till Kelly broke the contact.

"You're a very good kisser Tim, patient and firm, very sexy. Just look what you've done to my nipples." My eyes dropped to her chest, two hard points clearly visible beneath the black fabric. "And I can see just what effect its had on your cock," Her hand moved to touch it, a finger tracing along its length, "Have you ever had anyone touching your cock before?" My silence was all the answer she needed, my cock twitching as her finger moved. "Well then let's change that." Kelly grasped the hem of my shorts and eased them, and my boxers, down letting them fall at my feet. Naked, my hard cock standing proud, I could hardly breathe unsure what was going to happen, but unable, or unwilling, to ask Kelly to stop.

"That's a lovely cock Tim, so very hard," Kelly's hand gently wrapped around me, ever so gently stroking. My mind was on fire, the feel of her hand on my flesh unlike anything I had felt before, my cock harder than I could imagine, then her thumb stroked the head of my cock and I lost control.

"Oh god, Kelly, oh Jesus, umm..." the words spilled out of my mouth about as fast as the jets of spunk were shooting from my throbbing cock. Her grip tightened, pumping my flesh as if to help empty my balls. My pulse slowed as my orgasm ended. The shock quickly replaced by embarrassment, she had hardly touched me and I'd cum, a sticky trail of shame all over my chest. I tried to stand. All I wanted was to be away from here.

"Sit Tim," Kelly let go of my subsiding cock and gently pushed me back onto the lounger, "it's perfectly normal for that to happen, especially as you've never had anyone play down there before." I watched mesmerised as she lazily put her fingers into her mouth, licking the drops of cum off them. "mmm, tastes as good as your cock looks, would you like me to clean you up?"

"Er, Kelly, I not sure what to..." the words tumbled out of my mouth, out of control and no idea what to do. Run and hide, or stay and see what happened next. All I knew was that I'd just had the most intense orgasm I'd ever felt, her hand on my cock felt so good and the sheer spark of pleasure when her thumb had touched my tip.

"Shush now Tim," sent bent in and kissed me, which ceased my desire to leave pretty quickly. "Now let me clean you up". She moved slowly over my body, cleaning me with her tongue. The weight of her breasts pushing against me, feeling her hard nipples as she moved over my chest down towards my groin. She took hold of my cock, slowly licking over the tip, cleaning the final drops of spunk. My cock twitched and I moaned as her tongue finished its task. "Oh that's wonderful, but I think I deserve some attention before we get back to you, would you like that Tim?"

"Mrs Callaghan, err Kelly, I'm kinda out my depth here." I wanted to try and say so much, what had just happened was so wrong and yet so very right, that I should leave. Yet here I was sat naked next to a woman who'd just stroked me to my first orgasm, even if it was an awfully fast one. "What about Mr Callaghan?"

"Oh forget about him hunny, right now you just think about me and how horny you've made me." her hands moved behind her back, and in a swift move her bikini top was undone and discarded on the floor. "See how hard my nipples are? Come here and show me what you know about making them harder still."

I just sat and stared down at her smooth breasts, so much larger than Lisa's, Kelly's nipples seemed smaller, the areola darker somehow. Kelly's hands found mine and lifted them to her chest. I cupped her breasts, feeling their soft heavy weight in my hands, nipples pushing into my palms. I began to gentle squeeze them, thumb moving over and around the hard nipples, feeling the contrast between the smooth flesh and rough areole. Sensing Kelly's arousal grow as my hands moved, a soft moan escaping her lips and her body moving involuntarily as I worked.

"That's nice Tim, take my nipples and pinch them with your fingers and thumbs, pull them, god that gets me wet." My gaze moved to her face to see if she meant what she said but her eyes were closed, then as my fingers moved to comply her mouth opened and her head moved back, a deeper, sensual moan of delight escaping her. My cock twitched in excitement. Had my hands really just made this woman moan like that?

"I'm sorry, was that too hard? Did I do something wrong?" Kelly's hands had found mine and gently moved them off her breasts, I suddenly felt worried I'd gone too far, too hard, ruined everything. My heart racing and mind a whirl again.

"Of course you haven't Tim. Your hands felt wonderful on my breasts, pulling at my nipples. But I think it's time for a little more, be a dear and sit at the bottom of the lounger." She stood and moved to the far side, her back to me as I scooted to the foot of the lounger, watching her ass intently as she moved. She undid the knot at her waist and the sarong slipped down her legs to pool at her feet, my eyes following it as it went. Now I understood the point of it. My gaze slid back up her toned legs, seeing her looking over her shoulder at me, impish smile on her lips. Her hands were on the string of her panties, bows at the side that had been hidden before. A simple pull at them both and her bikini was gone.

Kelly sat on the lounger gracefully, legs firmly together as she brought them on, knees bent, feet level with my thigh. My cock was getting firmer with every move she made. "Ready to see what effect you've had on my pussy Tim, see how aroused you've made me?" all I could do was nod, her words running round my head. She smiled as her legs began to part, the left moving over my legs, her heel perilously close to my cock as it moved. Her legs now spread wide, feet flat on the floor, hands sliding along her inner thighs drawing my eyes to her sex. I'm sure my heart missed a beat as my gaze arrived at her sex. Her pussy was hairless and smooth; glistening slightly with what it assumed was the wetness she had mentioned. Her hand arrived, briefly hiding her pussy from view. Then Kelly began to stoke her lips with her index finger "see how swollen my lips are? Move closer Tim, I want you to see how horny I am, how I play with my pussy." I moved nearer my gaze never leaving her hand as it teased the length of her sex.

"God I'm so wet," Kelly's finger had slipped between her lips and disappeared up to her knuckle "oh that feels so good in my pussy." Her finger began to move in and out and my cock twitched with every thrust. "So Tim, I think you need to learn how to do this, but first I need to show you my clit I think." Her left hand moved down and spread her lips wide, exposing herself fully to my gaze. "So you see how the folds of my lips meet here?" the finger leaving her pussy and moving slowly up her sex. "And this little hard nub, that's my clitoris, and when it's teased the feelings are intense." Her finger began to circle her clit, a moan escaping her lips, her hips moving to push against her hand. "Now I think you should try Tim."

I moved a hand onto Kelly's thigh and slowly moved it towards her sex, trying hard to stop it trembling as I did. Kelly continued to hold her lips apart and I slid a finger onto her pussy. So warm, soft and wet. My heart was pounding so hard as I stroked around the entrance to her pussy, then slide my finger inside.

"Oh that's good Tim; now make your finger stroke the walls of my pussy." The heat of her pussy on my finger felt wonderful, stroking the smooth walls inside till i found a spot that felt rougher to the touch. "Oh god yes rub there." I felt Kelly's finger rubbing hard at her clit as I moved my finger as she asked. "Put another finger in and fuck me with them Tim." I moved without hesitation to comply, two fingers now moving rapidly in and out of Kelly's pussy. Her finger now rubbing fast and hard on her clit as her whole body began to move in time to the movements. Kelly's moans were fast and loud now, my fingers moving in time with the thrusts of her hips. I looked up, her eyes were shut and her face was contorted in what I assumed was pleasure. I was suddenly aware of just what was happening here, I'd been masturbated by a woman for the first time and now my fingers were buried in the first pussy I'd ever seen or touched.

"Fuck, yes." Kelly almost shouted as her body shuddered and I felt my fingers get even wetter. I stopped moving my fingers, guessing this was what it was like when a woman came. "Let me suck your fingers, I love to taste my own juices when I've cum." I slid my fingers out and lent forward to let Kelly do as she wished, my cock growing harder as she sucked my fingers clean.

I felt a hand grasp my cock and begin to stroke it slowly, carefully avoiding the tip for now. Kelly removed my hand from her mouth and moved forward to kiss me. Her tongue forced its way deep into my mouth, urgently pushing against mine. Kelly broke the kiss and looked deep into my eyes.

"So Tim, would you like to have sex with me? Put this hard cock into my hot pussy?" her hand continuing to stroke me slowly.

"Kelly, what about, I mean Mr Callaghan..." the words blurted out of my mouth. My mind a mess of what I felt, wanted and thought.

"Well I won't tell him if you don't," Kelly giggled, "and Tim you've got me so very horny and only feeling your fingers down there just won't do." Kelly's hand moved up my shaft and teased the tip. I groaned as an intense bolt of pleasure burst through me. My mind was made up I wanted her, now. "So Tim, why don't you come here between my legs?" Kelly knew I would, and I did. Her hand letting me go as I moved to kneel between her thighs hands on either side of her chest as I moved nearer until my cock was brushing her sex. I froze, suddenly unsure what to do next.

"Let me help you Tim," Kelly's hand took my cock and guided the tip to the entry of her pussy, "Push slowly now." I did as instructed and felt my cock slowly ease into her warm and welcoming pussy. My mind was on fire as I moved deeper; the warm slick feel of her on my cock was setting my mind on fire. My groin met hers and I was fully inside, my eyes closed and breathing hard.

"Just lie still Tim, that feels so good." Kelly's legs came up and rested on my thighs, pushing against my ass, holding me deep inside her. I felt my cock growing as her pussy pulsed, gripping my cock harder each time. The silky warmth enclosing my cock felt amazing. As I lay I could feel my cock begin to twitch, my orgasm building.

"Oh god Kelly I think I'm going to..." My hips began to move by themselves, my cock now as hard as I'd ever felt it before, all my efforts bent on holding back.

"Fuck me Tim; I want to feel you cum deep inside my pussy." Her legs moved from my ass and I began to move faster in and out, straining to make the moment last as long as I could, but knowing I was fighting a losing battle as the intense feelings built to bursting point.

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