Keeping Aunt Eleanor happy
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My aunt Eleanor is loaded. She lives in a big house packed with antiques and works of art. I was never quite sure what the relationship between my parents and Eleanor was, or what made me her nephew, but I knew she wasn’t a direct blood relative. I was never sure if she’d been married but there were rumours there’d been men in her life. For some reason she seemed to take a liking to my father and my parents wanted to make sure that when Eleanor met her maker something of her wealth came their way. They were constantly saying that “we must keep Aunt Eleanor happy.”
I was twenty five and living away from home in a flat when my father called me. He told me that Aunt Eleanor wanted help with cutting up a dead tree in her garden which had fallen over, and carrying the logs to a woodpile. That made sense as we lived the closest to Eleanor and I was a guy who kept himself fit and strong in the gym. Of course I agreed. I called at my parents’ house on the way. My father gave me an odd look and a wink, as if he knew something I didn’t, and as always he reminded me to “keep Aunt Eleanor happy.”
So off I went to Eleanor’s house. I’d last seen Eleanor a couple of years back. I guess she was in her mid-fifties, about ten years older than my parents. She was a quiet spoken reserved woman. She’d once obviously been a beauty. She’d kept her looks and age had given her an air of elegance and sophistication. She had a friendly face, brown eyes and perfectly styled dark hair down to her ears. She opened the door to me wearing a light blue thin shoulder strapped summer dress, rather low cut between her big but firm-looking breasts and ending just on her knees with bare legs and white sandals down below.
She greeted me with a warm smile and thanked me for coming. But as she thanked me I felt her eyes exploring me. I was in a tee shirt and jeans, and the look she gave me made me feel as if my clothes and underwear had evaporated and I was standing there stark naked. I’d often looked at girls like that, and now I knew just how they felt.
She turned to lead me into the house. I followed her with my eyes locked onto the bulge of her dress clinging to the curves of what was obviously a nicely rounded bottom and the backs of lightly tanned shapely legs. I’ve always liked mature women in porn, and even though she was twice my age I felt that familiar stirring down below.
I got on with the job of cutting up and shifting the tree. It was a blazing hot day and I soon stripped off my tee shirt. I keep myself fit in the gym and I had a well bronzed six-pack chest. Under my jeans I was wearing a black male thong, which was peeping out of the top of my jeans. I’d worked on my six pack and bought the thong with the hope of exciting girls.
I hadn’t had much success with girls but I could tell my chest and my thong were certainly having an effect on Eleanor. I could all but feel Eleanor’s eyes on my bare chest and my thong and knew I was naked again in her eyes. Even more than that, as she brought me cold drinks from time to time I was sure I occasionally felt her hand on the backside of my jeans.
My interest in Aunt Eleanor was steadily rising. As she moved around in the garden, when the sun was behind her I saw her dress was thin enough to show the outline of her body through it. That outline made it obvious she’d kept a good figure, perhaps ever so slightly plump. It also made it very clear that she had nothing on underneath. Her nipples poked under her dress and with the light angled just right I could even make out the dark outline of her hairy pussy. It was a hot day but it wasn’t just because of the sun that I was getting hotter and hotter.
Eventually I finished moving the tree. Eleanor came up to me and thanked me profusely. Her eyes undressed me yet again, and she gave me a mischievous smile.
“You’ve worked very hard and got all hot and sweaty,” Eleanor said. “Why don’t you go and take a shower?”
I wasn’t saying no to that. With my eyes locked on the outline of her body through her dress and as much of her bare legs as I could see up it Eleanor led me upstairs to the big luxurious bathroom. She left me to it. I discovered the key to the bathroom door lock was missing, but I guessed that as she lived alone she hadn’t bothered to replace it.
As you can imagine, by now my penis was straining up erect, but what I saw as I glanced around the bathroom racked my erection up a couple of notches stiffer. There was a washing line stretching above the bath and hanging from it were several pairs of women’s panties, some of them much briefer and more sexy than anything I’d ever known any girl my age to wear.
Perhaps I’ve got a fetish istanbul travesti thing about women’s panties which started when as a teen I discovered the contents of my mother’s and my older sister’s lingerie drawer. Later, at wild student parties where everyone got nude, we boys picked up and put on panties which girls had taken off. The game was that if girls wanted their panties back they had to come and take them off the boy wearing them. Some girls had been too shy and I’d acquired several pairs of panties that way. But at the same time I’d discovered how much I liked the feel of the thin cloth of girls’ panties taut against my hard up cock, and also how sexy other boys looked in them.
When I got naked for my shower I couldn’t resist taking a pair of Eleanor’s panties off the line. It was a tiny thong in red see-thru lace with a little decorative bow at the front of the top hem. The taut lace felt delicious against my straining cock. Looking at myself in the big wall mirror the see-thru lace showed the outline of my penis head and shaft in fine detail. The tiny triangle of cloth at the front was too small to cover my eight inches of hard up cock and the big round purple-grey head of my erect penis poked out above the little bow. I carefully replaced the panties on the line and stepped into the shower.
Soon I was nicely relaxed, all except for a part of me that was getting stiffer and stiffer the more I thought of Eleanor, especially that hint of her pussy through her dress, and of course of those panties. My erection was almost vertical. Suddenly, the shower curtains opened and into the shower stepped Eleanor, completely nude. She instantly snuggled her naked body against mine so her nipples were brushing my chest and my penis head was poking her belly between her navel and her cunt.
She was more than twice my age, but right then I didn’t care. I’d been without a girl for some weeks. My sex life consisted of porn and masturbation, and now pressed against me was a naked woman. Eleanor’s naked body was everything her dress had hinted at: curves, big round breasts, smooth thighs, a nicely rounded bottom and a triangle of dark soft cunt hair between her legs. We were both as frantic as each other, and our hands were instantly all over each other.
I started kissing her breasts and licking her nipples, then worked my kisses down her front till I was squatting down in front of her. I held her spread thighs and kissed her right on her cunt hair. She spread her legs wide and I eased the tip of my tongue between her vagina lips. From above me I heard her gasp with pleasure and nuzzle her hairy pussy against my face.
She gave me the same treatment. She licked the soap suds off my balls, out of my pubic hair, then off my erect penis. Kneeling in front of me she licked the erection-swollen head of my penis all over then into her mouth and massaged it with her lips and tongue. In the exquisite burst of sexual pleasure I involuntarily grabbed her head and tried to push my penis as far down her throat as I could. But instead she slid her lips off my almost exploding cock and looked up at me.
“That’s what boys like isn’t it? You looked so sexy in my knickers!” I realised she’d surreptitiously opened the bathroom door and watched me wearing her panties. Then she giggled like a little girl. “Your dad looks good in my sexy knickers too!”
I felt as if an electric shock hit me. I was fast learning about Aunt Eleanor, and what that odd look and wink my father had given me signified. But I didn’t care. Right then all that mattered was that I was naked with my cock up hard, and a sex-mad naked woman was playing with it.
Eleanor took me by the hand and pulled me toward her bedroom. It was as sumptuous as her bathroom with a big wide double bed in the middle. Eleanor fell onto the bed, lay on her back and spread her legs wide. Her big breasts flopped sideways and quivered with her excited breathing. Her hand slid down her belly and through her bush of cunt hair. She slid two fingers into her vagina slit and began to gently masturbate.
“Play with me! Kiss my pussy and tits!” Eleanor gasped, reaching out her spare hand toward me. I joined her on the bed.
I was frantic to get my cock up her, but I’d long since learned girls are at their best when they’re hot and wild. I guessed mature women would be too. I knelt next to her with my cock poking her thigh. I kissed her tits. Her nipples were peaking really hard and I licked and flicked them with my tongue. I leaned over her and reached down between her spread legs to caress her inside thigh tops, her groins and to reach down between her legs to finger istanbul travestileri her arse.
The way she strained her legs even wider and thrust her pussy against my hand told me I was treating her to what she wanted. I decided to treat her to something more exciting. I got into sixty nine position on top of her, straddling her head with my sex kit right above her face. I leaned forward and kissed and licked her from her navel down to her pussy.
“Ohhh! You dirty boy!” Eleanor gasped, squeezing my bum and then giggling.
I began smoothly and rhythmically stroking her vagina lips up and down with my fingers. She began to whimper and squirm as her arousal and excitement rose.
As I knelt astride her head I could feel her kissing and licking my balls and cock. Her tongue and lips against my cock head were turning my straining shaft to steel. As she got more and more excited her hands reached up to grab my bum and pulled my cock and balls down against her face.
I slid my fingers into her vagina slit, which was juice-sodden by now. I found her clitoris, a hard peak near the top of her vagina, and began to circle and criss-cross it, the last step in fingering a woman to orgasm. Her whimpering got more frantic, then finally her entire body tensed and her back arched to thrust her hips up. She uttered a long sobbing cry, her legs folded up, she thrust her pussy upward, then she writhed and squirmed in the pulses of her climax. I’d watched plenty of girls orgasm before, and I could tell Eleanor’s orgasm had been explosive. I can still hear her orgasm cry to this day. It was one of the most erotic things I’ve ever experienced.
After she’d climaxed Eleanor flopped back with her eyes closed, panting and holding her hand cupped over her pussy mound as her afterglow throbbed. I climbed off her. My penis felt taut enough to snap. I wanted release. I began to stroke her inner thighs and to prod her thigh with my hard penis. She quickly got the idea. Her eyes opened, she looked up at me and spread her legs incredibly wide.
“Want you!” She gasped, making it sound like an order, and tugging my arm to pull me on top of her.
At her age I knew there was no fear of pregnancy. I could all but feel Eleanor’s pent up lust and will power pulling me to her. I moved to kneel between her spread legs. She folded her legs so her knees were near her shoulders. Her spread thighs and gaping juice-glistening pubic hair ringed vagina pulled me irresistibly. As if acknowledging my surrender to her hungry body I bowed down and kissed her vagina, darting my tongue between her labia.
Then I moved up her body till I was on top of her with her naked body against mine. She was soft and warm under me with her belly against mine, not like some of the size-zero girls my age I’d fucked. I felt my cock head poking her between her legs and her cunt hair brushing me. I made the final thrust and entered her full length, discovering immediately that she wasn’t a virgin. Eleanor gave a long deep sigh.
“Ohhhh! Its been so long!”
Then her arms wrapped over my back and her legs folded over my bum as if she was trying to pull me even deeper in. My hips almost involuntarily started the rhythmic thrusting movement. Her vagina was looser around my hard penis than younger women I’d fucked, but she was so deliciously smooth and warm. My whole body was enjoying her.
Perhaps because of her looseness I took ages to cum. She was still throbbing and aroused from me masturbating her. While I was fucking her she suddenly gasped, juddered under me, gave a little cry and her arms and legs gripped me tighter, with her heels beating against my bum. I’d given her another mini orgasm.
Then delicious minutes of thrusting later my own orgasm came, building slowly then exploding. I remember her firm thighs hard against mine as I rammed into her in my orgasm thrust and filled her with my semen, and of course I grunted “Eleanor!”
I lay on top of her for a while, enjoying her warm softness under me before I rolled off her and lay beside her with residual semen trickling down my side.
“Mmmmmmm!” Eleanor purred. “You were so good. Thank you.” Then she giggled. “You were even better than your father!”
We lay on the bed naked together afterwards. Eleanor snuggled next to me and started gently fingering my chest, my belly, my cock and my balls, and right down between my legs. We chatted. She wanted to know all about my sex life, my masturbation habits and what I liked in porn. I kept her happy. I’m pretty hairy down below and she seemed to like running her finger through my pubic hair. Soon I had an iron bar erection arching Travesti istanbul up over my belly again.
“Will you do something naughty for me?” Eleanor asked, giving me a mischievous smile as she flicked my stiff cock with her fingers.
I remembered my parents exhortation to “keep Aunt Eleanor happy,” but in addition to wanting to please my parents I guessed that if a sex mad whore like Eleanor asks a boy to do something dirty, it’s likely to be fun.
“OK. What?”
“I love watching men masturbate. I watch men doing it on those dirty web sites. It’s been ages since I watched a boy do it for real. You wank over pictures of women in dirty poses don’t you. Go on, do it over me while I pose for you!”
I was masturbating a couple of times every night in bed, most mornings, and sometimes during the day. I didn’t reply but I guess my face gave her the answer she wanted. As she spoke she was visibly getting more and more excited. I was discovering this mild-mannered elegant woman’s exhibitionist fetish and secret sex life. I decided to enter into her exhibitionism.
“You dirty slut!” I said. “Get on your back, get your legs apart and stick your tits out and I’ll cover you with cum!”
“Oooooh! Call me a slut again, and a whore!”
She flopped onto her back on the bed, spread her legs wide and thrust her hairy pussy at me in a movement that wobbled her breasts.
“Cum over me!” she gasped excitedly.
I knelt wide-kneed astride her leg. My straining cock was arching up in front of me and my balls were brushing her bare thigh. Kneeling like that is one of my favourite masturbation positions. I love the heavy feeling of my erect cock sticking straight out like that and I knew it looked good like that when I was showing off to girls. Spreading my legs like that as I knelt pulls my muscles deliciously taut. Also if I’m masturbating with someone they can reach under me from behind to play with my arse and balls while I wank.
Masturbation is every boy’s ultimate pleasure. Porn adds excitement. But even better than that is a real live naked woman to ogle and play with, and to play with me, while I masturbate. As I knelt astride her Eleanor reached up to lightly caress my balls and slid her hand between my legs to stroke the inside tops of my spread thighs, my groins, to tickle my anus and to reach so far under me she was caressing me between my bum cheeks. I soon discovered she knew exactly how to tease a boy’s hungry penis to the peak of erection stiffness and pleasure sensitivity.
My pre-cum was dripping onto Eleanor’s thigh and I could hardly take any more of her finger pleasure on my sex kit by the time I wrapped my hand round my shaft and began the rhythmic stroking and tugging. I thrust my cock forward over Eleanor’s belly and made sure I put on a good meaty show. I’d learned how to do that at student parties surrounded by squealing naked girls clamouring to watch us boys wanking. I grunted like an animal and stroked my cock full length with my fist sliding right up over my cock head. With my spare hand I played with Eleanor’s smooth warm thighs, ruffled her cunt hair, and reached forward to fondle her big soft breasts.
I took my time. I edged, holding myself on the exquisite, almost agonising, brink of orgasm to prolong and increase my masturbation pleasure. Finally I couldn’t hold back any more. I guess my strangled grunt and the way I thrust my cock forward told her I was rising. Then, as I rammed my hips forward in my orgasm thrust Eleanor gripped my thigh and pulled me toward her.
“Take that, you dirty whore!” I grunted in the final moments of stroking my exploding penis.
Eleanor shrieked with excitement as in an exquisite orgasm I spurted a huge splash of cum over her belly and right up her front to her breasts.
I stayed kneeling astride Eleanor’s leg with my penis swinging above her leg and dripping a strand of semen onto her thigh. My cock was still mostly erect. Eleanor wrapped her fingers round my cock and gently stroked my shaft to send a last pulse of orgasm pleasure through my cock and a final spurt of semen that landed right on Eleanor’s hairy pussy.
“Was that good?” Eleanor asked. “You wank just like your father. Did he teach you?” I didn’t answer her.
We left it at that for that day as my parents were expecting me to drop in at their house on my way back. She gave me that pair of red lacy panties to keep.
“To help you remember me,” she said as she handed them to me. I guess she knew how I’d be remembering her, with her panties in one hand and my hard cock in the other till I soaked them. “You’ll be back again won’t you? I’m sure I can find lots of jobs for a big strong boy to do” were Eleanor’s parting words as I left her.
“Did you keep her happy?” were my father’s first words to me when I arrived at my parents’ house.
“I certainly did.” I replied, giving him the kind of wink and look he’d given me.
I think my father understood.
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