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A Little Leigh-way

Category: Mature
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The day I slept late that July was unforgettable. I had just graduated high school and was gently preparing to go off to college, but mainly that summer I was relaxing – sleeping late and not having many plans.

My sister was travelling somewhere in Europe and my parents were both working long days, probably thinking about my college expenses. We also had a house guest for a few weeks that summer. Leigh Chandler was an old friend of my mother’s from her college days. Leigh had recently started a new job in town and was staying with us while she looked for an apartment.

I didn’t see much of her as she was always gone before I got up and she was always out in the evenings looking at apartments.

I liked Leigh. She was in her early forties and still very attractive with long brown hair and a lively face with excitable features capped off by a narrow pair of glasses that always seemed to be slipping off her nose. Her voice was high-pitched and added to the enthusiastic aura that seemed to follow her everywhere and she was slim, to the point that her jeans slipped off her hips a lot and exposed the first two or three inches of her butt crack to anyone behind her. That was something we all laughed at behind her back, but to me, and eighteen year-old with limited sexual experience, it was a vision from heaven.

I don’t think I was thinking of Leigh when I got up that morning and rolled into the kitchen looking for some breakfast. I settled for some cereal and sat at the kitchen table, spooning it into my mouth while I browsed the sports pages of the daily paper.

After breakfast I went back upstairs to the bathroom and turned on the shower. I spent a few minutes washing myself and when I got out and stood on the bath mat to dry myself. It was no surprise that I had an erection. Back then it seemed like I had an erection every few minutes.

I gave myself a couple of strokes, just idly, with no great intention, but the strokes immediately felt good and I decided to pursue the endeavor with a little more intent. I rubbed a towel over my clock, balls and between my legs, and then stroked a few more times. I closed my eyes, savoring the early arousal sensations that started to wash over my body as I sat on the edge of the bath and stroked myself.

I heard the bathroom door open but had no time to react and pull a towel over me. I had no option but to sit there, cock in hand and mouth open, while Leigh walked through the door.

In hindsight, it was difficult to know who looked more shocked, but we met each other’s eyes with looks of pure horror. Time stood still as the realization of the situation sunk in and Leigh comprehended the scene before her.

“I… I’m so sorry.” She stuttered. “When I heard the shower stop… I thought you were finished.”

I wanted to say sorry too, for leaving the door open, for not knowing she was still in the house, for my nakedness, for stroking myself… but it was a horrible, incapacitating moment and I said nothing. Without another word Leigh disappeared behind the door and I was left in silence with a fast dissipating erection.

Numb, I locked the bathroom door, finished drying off and pulled on my underwear. I was relieved that Leigh had retreated to her bedroom when I exited the bathroom and slipped into my room to get dressed.

I sat on my bed for a while, trying to erase the moment from my mind, appalled at the shame and wondering what the implications were. It was hard to think straight and my world seemed to have momentarily turned upside down. I eventually heard the shower start in the bathroom and at that point I dressed and went downstairs, planning to go out for the day and find a way to forget the disaster of being caught in the act.

I made a couple of quick calls to friends but they were both out working summer jobs. I wondered about walking to my dad’s office to borrow the car for a while, but really didn’t know what to do. I was washing up my cereal bowl from breakfast when Leigh unexpectedly arrived downstairs. Somehow I’d expected her to stay up in her room for a while, as I’d done, so she caught me by surprise for the second time in an hour.

“Look,” her tone was positive and reassuring, “best thing is if we both just forget about this morning and not mention it to anyone. That work for you?” She had pulled on jeans and a green t-shirt but her hair was still wet from the shower.

I nodded, not sure that my voice would hold up to the moment.

“It was just unfortunate, that’s all, nothing to get all worked up about. Her features were softer now and her glasses slipping down her nose. “It’s a natural thing, I understand that, it’s not something you should worry or feel bad about. And, no, I will not tell your Mom.”

“I thought you were out at work.” I offered as a lame explanation for my oversight.

“That’s a fair assumption.” Leigh granted. “I didn’t feel all that great this morning, so I decided to stay home, at least for the morning.”

“I’m sorry…”

“Don’t worry about it.” she reassured. “Let’s just forget it ever happened. You want some coffee?”

Still feeling horrified and embarrassed, I said, “Yes please.”

Leigh busied herself with making coffee and I sat at the table, looking at the newspaper but not reading any of it.

I continued to scan the newsprint when she placed a coffee cup in front of me. I desperately wanted the atmosphere to clear and things to return to normal but the overwhelming feelings that accompanied my most intimate moments being discovered meant normality was a million miles away. Leigh started to make small talk about baseball and school but the conversation was a thin veneer over my crushed spirit and I was pretty sure she could see it.

Eventually she took the bull by the horns and addressed the situation again. “Look, I can see you feel really bad about this morning, but it’s nothing, really.” She gestured across the table, her palms up in openness. “You’re still young and these things are still a big deal to you, but believe me, it won’t seem such a big deal in a few years. You’ll laugh about it.”

Given how I felt at that moment, I doubted she was right, but I appreciated the words.

“Anyway, that kind of thing happens to everyone at some point.”

“What,” I perked up, possibly seeing a lifeline in that I might not be alone in being caught masturbating, “what do you mean, it happens to everyone?”

“Hell, it even happened to me.” She laughed at the recollection. “My ex-husband walked in on me once. Didn’t do the marriage much good as he took it very personally, but there you go.”

I looked over at Leigh’s smiling face with a smirk of my own. I could feel the warmth of her admission and appreciated her trying to make me feel better.

“I mean,” she continued, looking at me over the top of her glasses now, “at the end of the day it’s nothing but a quick jerk off. Nothing to worry about between friends, right?” She offered me her hand across the table. I took it, shook it and she smiled again.

Sitting back now, Leigh took a sip of her coffee and asked, “So, what are you going to do with your day?”

I admitted I had no plans. “Are you going in to work this afternoon?”

Leigh shook her head. “No, I think they can do without me today. I feel better than I did this morning, but I’ve been working hard lately and probably could use a quiet afternoon. I might even take a nap.” I must have looked at her strangely and she said, “Oh, a nap might seem strange to you, but twenty years from now… you’ll get it.”

I laughed at the thought of being twenty years older, or was it the thought of needing a nap? “It’s just an absurd thought, you being old enough to need a nap.”

It was Leigh’s turn to laugh now, “Don’t let this overworked face fool you young man, I’m a lot older than you think, and need every nap I can get.”

For the first time since she’d walked into the bathroom the tension inside me melted a little. Enough, at least, for me to feel human. “Thanks for your understanding Leigh. I really am sorry.”

“No worries, like I said, I understand.” She pushed back her glassed with her finger and looked over to me. “It’s no big deal, forget it, and anyway… you have nothing to be ashamed of. Nothing that I saw anyway.” This time there was a smirk on her face as she spoke.

I felt the red flush quickly cross my face but Leigh’s cheeky comment led me to make one of my own. “well, I guess if it wasn’t for you running around in your tight jeans… maybe I wouldn’t have been…”

Leigh wagged a friendly finger and admonished, “Don’t you shift the blame to me. You left the door open. You like my jeans though?” She looked down at her thighs, hidden from my view under the table. “I guess they don’t look too bad, my thighs I mean.” She stood up so I could see about two-thirds of her denim clad thighs.

“They look good. I nodded slightly in appreciation.”

“My butt’s a bit flabby though.” Leigh turned around and displayed wonderfully shaped butt in those tight jeans, “Don’t you think?”

“No way.” I looked, hard to avert my eyes, “Looks great to me.”

“But here,” Leigh took a few steps around to my side of the table, “here,” she pointed at the bottom of her butt cheeks, “don’t you think that’s flabby? Feel.” She grabbed my hand and placed it where she had indicated.

My fingers traced the outline of her flesh through the denim, half-heartedly at best. “Feels fine to me.”

“You’re just being nice.” Leigh twisted round to face me again. “You don’t have to be nice, I know it’s not like it should be.”

“I’ll take your word for it then. But it still looks fine to me.” I almost gulped before I said the next words that came out of my mouth, “You look great to me.”

Leigh looked down over the rim of her glasses, “Good for my age you mean.”

“No, just plain good.” I felt better for saying it, but immediately felt the tension in the room change from embarrassment to a palpable what-happens-next air.

Leigh sat on the edge of the table and continued to look down at me. “What about those young girls you hang out with? They’re much more attractive than me.”

My heart pounding now, I admitted, “Not to me.”

She looked like she’d noticed the change in atmosphere too now. There was a slight pause, almost like she was weighing up the merits of continuing the dialogue, before she spoke. “You weren’t… thinking about me, when you were… in the bathroom. Were you?”

I answered honestly but with just the tiniest hesitation. “No, but I have before.”

“Wow, really?” It genuinely seemed to take Leigh by surprise.

“Really.” I reiterated.

“That’s quite something to think about. Quite a compliment. I guess I should thank you.”

I didn’t know what to say next and sat there, almost expecting Leigh to smile, wish me good day and leave the ground we’d started to scratch well alone. She had a different idea though. “What do you think about, about me, when you…”

I thought for a moment and offered, “I like to think about your bottom. I like the way it shows when you bend over.”

Leigh laughed a little at the image I presented. “Okay, yes, I’ve been told about that before, but I can’t find jeans that fit!”

“I think about your face, your figure, think about just being intimate with you.” Leigh was looking at me intently now and I felt a distinct warming between my legs.

“That’s very sweet.” Again, I thought Leigh was going to call a halt to this fantasy conversation. “It’s quite a compliment. I’m glad you enjoy those thoughts.” She paused again, almost giving me an option to call the discussion to a halt. “I must admit, it was hard not to think about you when I was in the shower, think about what you were doing and the sight of your…”

All she did then was lean forward a little and offer me her lips. I closed the gap and kissed her, some small brushes of lips first, then an exchange of tongues, nothing too passionate, but full of reassurance and promise.

“Did you finish, when you were in the bathroom?” She whispered now, her lips close to my ear, intimate.

“No.” I admitted.

“Would you like me to…”

Leigh drew her head back to look at me and I nodded. Oh God did I want her to.

Without another word Leigh lowered herself to kneel in front of me, took one last look at my face, and then concentrated on undoing my belt and zipper. I was hard as a rock by the time she got her hand inside my jeans and felt me through my underwear. She felt my length, squeezed my shaft and then urged me to stand up so she could pull my clothes away.

When I sat down again my cock was standing to attention between my legs. Leigh seemed to savor the sight before taking hold of me and pulling away my foreskin, a move that sent shivers of pleasure all through me. With her other hand she eased my thighs apart so she could feel my full length better and access my balls. She seemed fascinated by her handiwork and watched intently as she stroked me a few times.

“You have a lovely cock.” He said eventually. “Do you like it being stroked?”

“Yes.” I was incapable of much else by then.

“Do your girlfriends stroke you?”


“I hope you like this. I probably do it a little differently from young girls. I like to call it the Leigh-way.”

The Leigh-way was delicious. She stroked me slower than any girl ever had, with a firm grip and a definite pause when her hand was over the head of my cock that created a wonderfully sustained building of excitement all through me. I watched her work, one hand stroking me slowly and her other starting to explore my balls by squeezing them and feeling under then and pushing them up towards my cock. By now the morning’s embarrassment at being caught in the act was all gone.

I loved that Leigh seemed fascinated by her hands’ movements on my cock and how she reveled in any indication that her ministrations were pleasuring me. Still with each stroke she varied the pressure she squeezed my shaft and always made that tiny pause when her hand was over the head of my cock. It was a move that seemed to slow the build-up but not lessen the intensity as I felt myself getting closer and closer to climax. Her face was so close to my cock I half expected her to pop it in her mouth at any moment, but she kept on with her relentless, rhythmic stroking.

I felt compelled to let her know that I was about to explode and stuttered, “I’m…”

Leigh calmly replied, “I know.”

She continued stroking me but now cupped my balls tightly as I started to tighten in my chair. “Just relax.” She told me. “Let it come.” No sooner had she got the words out than I started to feel the bursting heat of pleasure as the climax slowly took over my body.

Leigh didn’t miss a beat as I gasped and stiffened more. As my thighs rose up from the chair she pulled harder down on my cock, pointing it almost straight at her face as the first waves of climax started to pulse through me. The climax was shattering, coming from deep inside me and pulsing out, down through my legs and contracting my balls ready for the release of my cum. It was the biggest orgasm I’d known to that point in my life, delivered by someone who knew what they were doing with my body even better than I did.

Leigh continued to stroke me as I started to spurt. The first stream splashed against her neck and four or five subsequent streams of pure white cum landed on her t-shirt. My hips jerked involuntarily as the orgasm continued to bounce around inside me and Leigh just kept on stroking, never varying her rhythm. Eventually I slumped on the chair and Leigh stopped stroking, now holding me tight in her hand and smiling up at me.

I looked down and saw her smile, her face showing some signs of my explosion, but her t-shirt literally covered in cum. “Feels like you had some feelings pent up there.” You sure did cum a lot.” Everything was said with a smile.

“I’m sorry.” I was thinking of how a recent girlfriend had been so careful not to get any of my cum anywhere near her.

“Don’t worry.” Leigh flicked her tongue, trying to reach a splash. “I love it. Makes me feel good that you enjoyed that much.” Leigh stood up now, holding on to me as long as she could and then letting go as she turned away from me and started to pull down her jeans. “Stay hard for me. I just need to sit on you a little.”

I watched as Leigh’s jeans slipped down her butt and thighs, way lower than I’d ever seen before. As soon as they were at her ankles she took a step back towards me and reached or my cock and started to lower herself backwards onto me. I tried to see through her legs but I felt the red hot lips of her pussy before I saw it as she positioned herself over me. Before I could savor any moment of anticipation, she sank on me, swallowing my youthful, hard cock in her slippery sheath of heat.

Leigh wasted no time in starting to raise herself up and down, sliding on my cock as she sat in my lap and built herself a rhythm, just like she’d done for me. I watched as my cock kept appearing below her ass, then covered by her hot pussy again. For a moment I wondered if I would cum again so quickly, but then I realized this was all about Leigh and I took hold of her sides and guided her on and off me at the pace she liked. With each downward thrust she ground hard onto me and I got the impression that she was fingering herself as she rode me.

I was left in no doubt when Leigh was cumming. She gave a high-pitched shriek and paused her stroke when she just had the head of my cock inside her. When she cried again and slid all the way down on me I could feel an escalation of the heat inside her and some definite contractions as her climax was passed between us. After two shaky strokes on my cock she slumped forward, resting her elbows on her knees, breathing heavily and said, “Fuck, that was so much better than going to work. God, you felt so good.” She tried to turn around but failed and stood up in front of me.

By the time she’d turned to face me Leigh had pulled up her jeans and was wearing a big smile. “You have a lovely cock young man, and it fits so well inside me. That was so hot.” She kissed me on the cheek. “However, I don’t believe you’re finished, come on.”

Leigh was all business suddenly, taking me by that hand and leading me out of the kitchen, upstairs and into her bedroom. I sat on the bed, not sure what my next move should be but loving the view as she pulled off her t-shirt, bra and jeans with no delay and no pretense. As soon as she was naked she crawled past me and lay on the bed.

“Why don’t you take that shirt off and come lie next to me.” she invited.

I was a little self-conscious of my deflating cock as I pulled my shirt over my head but as soon as I lay next to her Leigh’s hand reached out and took my in her hand, erasing any concern I had there.

“So, how did you enjoy the Leigh-way?” She smirked as she played with my cock in her fingers.

“It was amazing.” I answered truthfully.

Leigh gave a laugh. “Older women still have a few advantages I think. And… you did feel great inside me. I hope you didn’t mind…” A thought obviously occurred to her. “You weren’t a virgin were you?”

I shook my head. I may have been inexperienced, but at least I had been intimate with a couple of girls.

“Good,” she sighed, “That wouldn’t have been a very romantic way to lose your virginity.”

“I can think of worse.” I thought out loud, thinking about my own virginity loss, in the dark back yard of my first girlfriend as we fumbled through making each other cum.

“You do have an awesome recovery rate.” Leigh held my stiff cock vertically and admired it. “I do think you should pay a little attention to me before we have you cum again though, what do you think?”

I needed no invitation and turned over on the bed so I could look at Leigh. She had taken off her glasses and was smiling up at me as I looked at her breasts. They were flat with smallish nipples, but still looked good for her age. I reached over and cupped on breast in my hand, feeling the soft flesh as it gave to my touch and finding the nipple with my fingertips.

“I really like them sucked.” Leigh’s voice was much deeper in tone than I’d heard before.

I dipped my head and took one of her nipples in my mouth. The nipple was already hard and I felt her squirm and I sucked hard and rolled it between my teeth. I lifted my head off for a moment and licked at her, flicking the nipple and making Leigh squirm. I was about to use my hand on her other breast when Leigh cut me off, took hold of my hand and guided it down between her legs.

Leigh had no pubic hair and my fingers found her wet pussy folds with a slight surprise. I stroked along the length of her slit gently, parting her pussy lips very gently as I explored her. Leigh’s hand left mine when she’d guided me but now she was reaching to stroke my cock again. The easiness of our moment was compelling, Leigh offering only pleasure and me intent on only delivering pleasure; it was a new sensation for me, new and wonderful.

I was still sucking hard on her nipple when I slipped my finger inside her. I heard Leigh gasp and felt the heat of her pussy on my finger as I pushed hard inside her. I tried to withdraw but Leigh’s hand caught mine and urged me to stay inside her. I got the message and managed to push a second finger inside her, a move rewarded by a gasp of pleasure.

“God, I haven’t felt this turned on in years.” Leigh whispered in my ear, her voice still deep with passion. “Come inside me now. I want to feel you cum inside me.”

I needed no further encouragement, my cock now rock solid and pulsing fit to burst. I maneuvered between Leigh’s legs and she reached down to pull me towards her by the cock. There was no delay from her this time as she positioned me between her pussy lips and then placed her hands on my butt cheeks to pull me into her.

I literally fell inside her with a big slide of pleasure, captured again by her molten hot pussy.

“You are so hard.” Leigh was gasping, seemingly lost in the moment and making me feel like she was needy. I took this as my cue to start thrusting into her.

Leigh was anything but passive as I started to build up a rhythm, pushing into her harder and harder, pulling out as much as I dared to make my strokes long and deep. She raised her hips to meet my strokes, not only making our pubic areas grind together, but enhancing my pleasure as I got deeper inside her. She continued to pull me into her with her arms around me, whispering in my ear as we coupled, “Fuck me. So good. Deeper Baby. That feels so good. Cum for me.”

I was just settling into a rhythm where I was sure I was going to climax when Leigh seemed to come out of her passion-induced trance and squirm away from me and onto her side. The smile on her face told me there was nothing wrong with what I was doing, just that she wanted pleasured a different way.

“Come in here baby.” She smiled, hitching her top leg a little to indicate that I should kneel and slide into her sideways.

Straddling her bottom leg and with her top leg out at right angles, I took my cock in my hand and pointed it down between her butt cheeks and towards her pussy lips. “I’ve been thinking about you fucking me like this for days.” She admitted with a wicked smile.

I pushed into her. She felt tighter and hotter than ever as I thrust up to her butt with my pelvis. I watched her eyes close with pleasure then open to show me she approved of the move. “Deeper.” She mouthed, urging me.

Looking down, I could see my shaft disappear deep into her. Leigh’s face was contorted with pleasure now, her breathing deep and her eyes closed as I plunged faster and harder into her than I’d ever done with a girl before. Quite suddenly the sex felt pure and unsullied by wondering what the other person thought – we both knew this was what we wanted and were lost in the moment, locked in pleasure.

I knew I was going to cum only seconds before the climax started to build in me. “I’m cumming.” I managed to breathe out for Leigh’s benefit.

“Don’t stop.” Was all she replied.

Another look down at Leigh’s face and I felt the orgasm burst, huge waves of pleasure that pulsed through my tummy and legs. I paused for just an instant, immobilized by the climax, and Leigh pushed hard back against me, encouraging me not to stop. I started thrusting hard again just in time for the first spurt of cum to jet inside her. Several times I spurted, flooding Leigh’s pussy with my cum.

“I feel you.” Leigh gasped and pushed back onto me harder than ever. “Make me cum, hard.”

With the climax still pulsing around me I thrust inside her again and again, willing her to cum for me. When Leigh’s eyes opened wide and looked up at me I knew she was there. “Oh God.” She moaned and her whole body twitched with the pleasure. Again and again I felt her pussy contract around my cock. Her face screwed up and it was a full thirty seconds before she was able to relax enough to look up at me.

“Good.” she breathed. “Amazing.”

I moved to pull out of her but Leigh stopped me. “Stay there.” She urged. “Come lie with me but stay there.”

I carefully lay beside her, somehow managing to keep my cock fully inside her as our heavy breathing seemed to synchronize.

“Tell me that was good for you.” It was a command, but it was easy to answer honestly.

“It was amazing. You are amazing.”

Leigh sighed deeply. “That was so good. It’s been so long since I had a man so young, so virile. Thank you.”

I said nothing rather than get into a discussion about who should thank who, even though I was sure I would win. My head was swimming with emotion and my senses were swimming in stimulus as I snuggled up to Leigh and I closed my eyes. I’m sure we both fell asleep at the same time.


I woke alone in the bed and under the covers. I heard footsteps on the stairs and Leigh came into the bedroom, still naked and carrying two glasses of water. She sat on the bed and handed one of the drinks to me with an affectionate smile.

“I told you I needed a nap.”

“You also told me I’d come to appreciate the good a nap can do.”

Leigh’s head bounded up and down as she considered my point. “True. How was the nap for you?”

Very good.” She stooped to kiss me on the lips. “Very good… but not quite as good as your pre-nap workout.”

“That’s fair.” Leigh conceded. “But the great thing about naps is that they recharge us, ready for a post-nap workout.”

“You’re serious?” I watched as Leigh slipped under the covers next to me, already feeling for my cock.

“Oh yes,” she smirked, “I have a little more Leigh-way to show you.”

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