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Youth becomes man with older woman

"This is how I first learnt about women, and myself."

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Famous Story
I grew up in a low income family living in a small country town. Travelling anywhere was rare and a luxury for us. Accommodation was always with relatives or friends in the places we visited. My memories of holidays and travel are of sleeping on couches, sharing beds, or mattresses on the living room floor. Growing up in a small hick town had given me fairly sheltered upbringing and very little exposure to the wide world.

One year, shortly after my sixteenth birthday, a family emergency saw a hastily organised trip to another town a few hours away by train. I travelled with my parents and we were to stay with a family friend who had visited and stayed at our house on occasions. I knew her as Aunty Vi, as was the custom then. Children did not address adults by their first name. It was always Mr or Mrs, or if a close family friend, Auntie or Uncle was used, even if they were not related. Auntie Vi fell into this category; she had been married to my father's cousin who had died in the war. She operated a small Guest house for resident boarders. My parents were given a tiny vacant guest room and I was to share with Aunty Vi.

I was sent to bed at my usual time while the adults stayed up and talked. I was woken some hours later with light in the bedroom. Through squinting eyes I could see that the tall standing lamp near the bedside was on. Aunt Vi was standing next to it taking off her clothes. She took off her cardigan and draped it over a chair, then reached behind her and pulled the zipper on the back of her dress down. My heart beat speeded up from fear of being caught watching what I should not have been seeing.

She bent forward and shrugged the dress off her arms and pushed it to the floor before picking it up and draping over the chair. She had on a full length nylon slip under it like my mother wore under her dresses. I watched her through the tiniest eye slits I could make as she slipped the shoulder straps off and down her arms then reached behind her back and unhooked her bra. I’m sure I stopped breathing when she pulled it off her arms and leaned over to drop it on the chair.

The sight of her very full breasts falling free and swinging gently in the lamp light as she leaned over did something to me I had not felt before. She rubbed a hand under each one quickly before she slipped her arms through the straps of her slip and pulled it back on. She bent and reached down again and this time started pulling the slip up her legs. When it was about mid thigh, she put her arms underneath and pulled her underpants down to the floor, stepped out of them and then switched off the lamp.

She gently turned back the blankets and I could feel her slide in and settle down. I lay completely still trying hard to slow my breathing, suddenly very aware that my penis was extremely stiff. Aunt Vi’s breathing slowed quickly and I was getting a faint whiff of sherry from her. I lay there for a long time listening to her sleeping and giving my stiff penis some small squeezes, marvelling at how hard it had become. I eventually fell asleep feeling the warmth radiating across the bed from her.

I woke in the morning to the movements of the bed as Aunt Vi got up. As the Guesthouse proprietor, she was up first to make breakfast for the boarders. My penis was rock hard again and I wondered if it had been like it all night and would now remain that way. I took a sneak peek at Aunt Vi, but she just pulled on a woolly dressing gown and slippers and left the room. I lay there feeling my stiff penis until my mother called me to come for breakfast. Squeezing it created a feeling in me that made me want something more.

That night I lay awake hoping for another glimpse of Aunt Vi’s breasts but she readied for bed in the bathroom and came into the bedroom with her dressing gown on. The best I saw was the silhouette of her breasts from the lamp light when she took off her dressing gown and reached over to turn off the lamp. The following morning I woke early lying on my side facing into the bed.My penis was stiff again. When I moved slightly I could feel it lightly touching something.

I opened my eyes for an instant. Auntie Vi was half turned towards me and I realized that my penis was touching her somewhere on the leg or hip. I lay still for a moment and then gently moved as if in my sleep. My penis rubbed slightly against the silky feel of her night dress and I realized it was poking out through the fly opening of my pyjama pants. The feeling was exquisite but I stopped unless she woke. I couldn’t resist for long and moved again to feel it rub firmly against the material and her leg. I didn’t get to do it again. Aunt Vi stirred and moved her leg firmly down the bed as she awoke, giving my penis a good long rub from her thigh. I feigned sleep while she got out of bed and left the room.

I was hoping with everything for another undressing in the bedroom that night and my prayers were answered. I positioned myself on my side with a good view across the bed to the chair. When Aunt Vi came in she took off her dress and slip and dropped them on the chair then moved over to the bed and pulled her night dress out from under the pillow. I had never seen any woman except my mother in only a bra and underpants and my penis was reacting accordingly.

I remained motionless, peering through eyelashes as she unhooked her bra and dropped it onto the floor. Her breasts seemed to tumble out when released and I had a really clear view of them. I remember seeing the detail of her nipples with their rounded points. They also looked bigger without clothing over them and I watched as they swayed around from her arm movements. She pulled her night dress over her head and let it fall before putting her hands under it to pull her underwear down and step out of them. She turned off the lamp quickly and slid into bed.

I lay there, my mind visualising what I had just seen. Those beautiful breasts, poking out and swaying from her movements, and the pulling down of her underwear. I suddenly became aware that she was practically naked next to me and my penis was so stiff it would surely burst. I soothed myself by wrapping my hand around it until I fell asleep.

I woke next morning from unusual dreams, my penis stiff again. I wriggled in the bed and felt it pressed against something warm and soft. My opened eyes looked directly into Auntie Vi’s hair. She was facing away from me and lying practically next to me. My penis was pressing into her bottom. I moved it slightly back and forth and it felt wonderful. I stopped and waited for any response from the sleeping body next to me. Nothing. I moved gently again, and revelled in the feel of my penis head rubbing into the warm softness of her behind wrapped in her silky nightdress.

Only fear of her waking stopped me from continuing and pushing harder. This was wonderful. Surely there must be something more. Auntie Vi eventually stirred softly and shifted in the bed. Her movements caused more friction on the head of my penis which became even harder. I lay completely still; an immovable object, while this glorious behind rubbed itself against the head of my penis. She arched her back and pushed her behind backwards into me. I pretended to be asleep, so I couldn’t be blamed. For what I wasn’t sure, but best not to know about it I figured.

Shortly after, Auntie Vi moved considerably as she woke up, moving her behind against my penis quite a lot. The feeling of it was something I had never experienced before. I remained motionless with eyes tightly closed as she got out of bed and left the room. I put my hand around my penis and held it tightly, squeezing it, until I was called for breakfast.

The next night played out the same with Auntie Vi undressing in the lamp light and me peering through eye lashes. She was dressed differently today, wearing a top with long pants, which was unusual for women in the day. When she undressed she removed her top and bra together, giving me another sighting of those beautiful orbs bobbing in the lamp light. I was startled when she pushed her long pants down taking her underpants with them. For the first time, I saw her full bare behind and it was beautiful.

She bent over to retrieve the clothes from her feet, pulled the underwear from the pants and dropped them on the floor. After laying her pants over the chair, she rubbed both her hands up and over her breasts a couple of times as if rubbing out the constraints of her clothes. She took a couple of steps to the dresser and picked up a hair brush and stood brushing her hair firmly and quickly. I opened my eyes fully while she was side on to the bed brushing her hair, and soaked in the beauty of her shape.

All of this presented a wonderful viewing for me. A full rounded behind bending, walking, and standing. Breasts bobbing, swaying, and being rubbed. The ultimate for me was when she turned from the dresser and took the few paces to the edge of the bed. Even through hooded eye lashes, I was having my first view of a fully naked woman front on. Her breasts were clear to me, but what impressed me most was the triangle of hair at the junction of her legs.

I couldn’t see anything else except this lightly hairy triangle, but it made my penis as hard as a stick. I could practically smell her as she pulled her night dress from under the pillow and dropped it over her head. She switched off the lamp and slid gently into the bed. I lay as still as a dead man, my stiff penis pulsing in time with my heartbeat until I fell asleep.

When I woke in the morning, the images from what I had seen last night flashed into my head. The swaying breasts, the mysterious triangle of fluffy hair at the join of her legs and that wonderful rounded bottom as she bent over to pick up her clothes. It was the image of her bottom that stiffened my morning erection to its hardest. I felt it with my hand and pulled it through the fly opening of my pyjamas. I couldn’t believe how hard it was. I lay quietly, squeezing myself gently and rolling the images of her nude body over and over in my head. I had urges I didn’t know what to do with.

Aunty Vi was asleep on her back. I rolled gently onto my side closer to her and pushed my hips forward until the tip of my penis rested against her. My heart was beating furiously, but I had to feel that soft silkiness of her nightdress rubbing on me. I pressed gently into her hip and then stopped a moment. There was no movement from her. I pressed again in a slight rubbing motion and once again felt the beautiful sensation of that nylon covered flesh rubbing on the head of my penis. It was amazing and I didn’t want to stop. There was still no movement from Auntie Vi. She seemed to be sound asleep.

I continued my slight movements against her for a while until she suddenly moved and rolled over onto her side facing away from me. I froze. Was she awake? She settled after curling her head down and curving her body backwards towards me. I was in heaven. Her big, beautiful behind nestled directly onto my rigid penis. I couldn’t believe my luck. Just the warmth emanating from it made me twitch. I waited, holding my breath in case she woke. Her breathing was deep and slow.

I plucked up the courage to press forward into her. Her bottom was so soft; I could feel the flesh move when my dick pressed into it. I rolled slightly to rub against the nylon, waited, and then did it again. With no movement from her, I got bolder and did it a couple of more times in a row. The sensation in the head of my dick was very intense and I didn’t want to stop. So I didn’t. I kept rubbing into her gently, revelling in the springy softness of her flesh.

When it happened, the shock was so great, I froze where I lay. Aunty Vi suddenly reached her hand around behind her and gripped my cock tightly in her hand. I had been caught. The fear rose in me and I just lay there; still. After a moment, she relaxed some fingers from me and squeezed me between her thumb and two fingers. She pulled them forward towards her, rubbing my foreskin over the head of my cock and then slid it back again. The feeling was the best I had ever felt. She did it again, slowly, and still I didn’t move. She repeated this again and again, pulling on my cock and rolling the foreskin back and forth over the head, gripping me tightly between her thumb and fingers.

A feeling was building inside me I didn’t recognise and my breathing was harder. I didn’t want this to stop. She rubbed faster and faster. I was in well practised hands. Suddenly the feeling got too intense and I started pulling away. Her skilled hand followed me backwards and gripped my knob tighter. My cock spurted and her practised hand was waiting for it, rolling her palm over the tip of it to catch my cum and then rub it back onto me as lube while she stroked me through to the end. She kept rubbing until I had to stop her. The feeling in my cock was too intense.

I put my hand down on hers and pressed on it as a signal to stop. She did and just lay there holding my softening cock. I didn’t speak. I was overwhelmed by the intensity of the feeling she had just given me. When my breathing had slowed, Aunty Vi lifted the blankets and reached out of the bed with her wet hand. When she turned towards me she was holding the undies she had left on the floor and used them to wipe the mess off my cock and her hands. Without saying anything she got out of the bed, dropped the undies on the floor and then kneeled on the bed over me with her breasts swaying.

I looked at her, unsure of what to say. She was smiling at me and just said,

“Is that better?”

I just nodded my head at her. I tried to answer yes, but only a gurgling sound came out.

“There’s no need to tell anyone about this. Ok?” she said.

I nodded again and she got off the bed and put her dressing gown on.

“Have a sleep in now. I’ll call you when breakfast is ready.”

She picked up her wet undies and left the room. I lay there, excited beyond belief, knowing that this was a lifetime first and hoping not a last.

My thoughts were consumed by the mornings event for the rest of the day. I looked at Aunty Vi in a different light now and watched her more during the day as she went around the house. I remember looking at her rounded bottom as she walked and down her blouse to glimpse her cleavage when she bent over. She acted completely normally with me, but one time she looked up and caught me looking down her blouse. She gave me a quick smile and winked at me. Watching her bottom moving around kept my dick hard most of the day. I was still amazed at the feeling she had produced in it and wanted to feel it again.

A toilet visit found me holding and squeezing it again, marvelling at how hard it could be. I put my thumb and two fingers on it and rubbed my foreskin back and forth like Aunty Vi had done. The effect was pretty immediate, with the special tingle starting quickly. I knew I couldn’t stop and kept going until it felt like it was about to explode.

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I took my hand off and waited for the squirting, only to be disappointed as the feeling subsided. I quickly started again and kept going until liquid squirted from the tip onto the floor. I kept rubbing until it stopped coming out and it became too sensitive again. How much of this stuff does your body have I wondered. I wiped the floor up with toilet paper and flushed it away. This was definitely going to be a repeat pastime.

I had knots in my stomach when I went to bed that night. Some anticipation of what might come, some fear of what might not and feeling awkward. The excitement had me rubbing myself again, my dick as stiff as wood. I stopped when Auntie Vi came in and pretended sleep as I had every other night. I listened to the sounds of her shedding her clothes until I chanced a glimpse through squinted eyes. She was standing in front of the mirror without a stitch on, brushing her hair. Side on, I could see the magnificent curve of her bottom and the points of her breasts as they swayed gently from her arm movements. This was the second time I had seen her completely nude. The effect on my penis was startling. I didn’t think it could get any harder than it was, but it stiffened until it felt like it was going to split. I lay completely still, too scared to relent and rub it.

She eventually put down the brush and turned to the bed looking at me before taking the couple of steps over. I couldn’t help myself and opened my eyes fully to take in what I was seeing. My eyes roved quickly over her breasts and down to the hair between her thighs. She stopped and stood still next to the bed for a moment watching me while I looked, then reached up and flicked off the lamp. I felt her sliding under the blanket. She had not put anything on. She had always worn something to bed before. She nestled towards the centre of the bed and lay still. I could feel the warmth radiating from her body. My penis was still rigid. The urge to squeeze it was so intense I had to give in.

My hand slid down and gripped it, intensifying and calming my urge at the same time. I was conscious of my other arm resting against Aunt Vi’s. The thought of her being naked next to me with her breasts just inches away was almost too much to bear. My hand squeezed tighter and I gave my cock a few rubs. As soon as I did, I felt Aunt Vi’s hand close over mine, then push it away and close her fingers around my stiff cock. I sighed and relaxed. She was going to make it good again.

She stroked it gently and slowly, not squeezing as hard as she had in the morning. She varied her stroke and pressure, sometimes sliding her hand, sometimes squeezing and rubbing my foreskin over the knob. I didn’t care what she did, so long as she didn’t stop. She continued gently until my breathing became fast and I was jerking my hips up into her hand. She speeded up her rubbing and the special tingle started again. I was ready this time, anticipating, wanting to feel the end. It erupted quickly, spurting into her hand. She cupped her palm over the knob again as I squirted, catching all the cum and then rubbing it back down onto my cock as lube while she stroked the last spurts from me. She lay still holding my cock until my breathing returned to normal, then squeezed it from the base to the tip to wipe off the cum into her hand. I then felt her rubbing her hand. It seemed like she was rubbing it into the side of her leg.

“Was that good?” she asked.

“Yes, thank you” I croaked.

“Good. Did you do it yourself today?”

“Y…Yes” I stammered, unsure of myself.

“I thought you would. It’s good isn’t it?”

“Yes, I love it”

“That’s good. You have a sleep now.”

I quickly sank into a deep and restful sleep. I have memories of rousing several times during that night, aware of the softness of nakedflesh lying against me. It was still dark when I woke in the morning. The memories of the night before came to me quickly and my cock stiffened. I chanced to rub my arm against Aunt Vi. She was lying on her side facing away from me, with my shoulder resting against her back and my arm squeezed between us.

I moved my hand gently and felt it rub against the softness of her behind. There was no silky feeling from the nightdress this time, just the smoothness of her soft skin. I rubbed gently again, in a slightly wider motion. She lay still, her breathing deep and slow. I rolled gently onto my side facing her, allowing my body to rest along her back and feeling her beautiful behind pressing into my erection again. The feeling of her bare skin rubbing on mine was impossible to believe. The warmth travelled directly from her behind into my cock. I could feel myself twitching and was torn between leaving it there to feel her on me or roll over and rub it myself.

I gently moved my hand over the softness of herbottom and gently pushed my penis into it. I stopped and waited a moment for any signs of her being awake and then did it again. I don’t know how long I was doing this before Aunty Vi’s hand came over on top of mine and pressed it firmly against her arse. She rotated her bottom gently against my hand and pushed it around in a circular motion before taking her hand away. I continued rubbing, feeling all over it, running my hand down to her other cheek and then following the curve into the crack between them. Aunty Vi lay still and let me go about my exploration. I put both hands into play, rubbing and then squeezing her bottom. The urge in me was too strong and I pressed my erection into her bottom, only to feel it slide into the crack between her cheeks. I lodged it there and rubbed gently. The feeling was exquisite.

Aunty Vi’s arm came over again and took my hand. This time she pulled it over her and placed my hand onto her breast. I pressed into it. I didn’t think anything could have been as soft as her behind until I felt her breast. It was absolutely the nicest thing I had ever felt. I gorged my senses on it, then dropped my hand to her other one to feel it too. I switched back and forward between them while rubbing my cock into the crack of her arse. I was in heaven. Nothing in my life so far had been as good as this. Suddenly, the special tingle was in my cock and I rubbed into her crack faster and deeper. Sensing something, Aunt Vi curled and pushed her arse back into me. Suddenly my cock was getting a much deeper and softer rub and I was over the edge, spraying myself into her arse crack and sliding into my own wetness. It felt so good I thought I would pass out.

When I finished I rolled onto my back, panting. Aunty Vi rolled over to me and asked if I was ok. The smile on my face was her answer. She wiped my cock with her hand again, the same way she had the night before, and rubbed my residue into her leg again. I learned later that this was a method she had found in her youth of hiding the evidence from playing with boyfriends. I remember telling her how nice she had felt, and that nothing could be nicer than that. She chuckled and said

“Oh yes there is. You’ll see.”

I wanted to see her breasts and tugged the sheet down on her a bit. She realized what I was after and pushed it down to her waist while I feasted my eyes on her tits. I put my hand on them, rubbed and squeezed and watched as her nipples grew. I never knew they could do that and felt their hardness between my finger tips. She told me how nice that felt and then said

“Feel this."

She pulled my face to her breasts and rubbed me into her. I was suffocating in their softness, not wanting to take my head away. I squeezed them with both hands and pressed them against my face. Nature took over and I licked at them before settling on the nipples and sucking them, one and then the other while they hardened.

I felt her hand reaching under me. I hadn’t thought about my cock being hard again until she touched it. She was testing it, to see if I was hard again. She kicked the sheet down further, reached over and pulled my pyjama pants off. She leaned over me, looking down at my stiff cock for a moment as if thinking, then dropped her head into my lap and I felt the most divine feeling I had ever had. It took me a moment to realize it was her tongue and lips around my cock. The warmth and softness was indescribably good as she bobbed her head up and down my shaft. After a while, she rubbed her tongue down the underside of my cock onto my balls and swirled it around before sucking my sack into her mouth. I could have lain there all day and taken this, so I was a bit disappointed when she stopped and sat up. She sat listening intently for any sounds in the rest of the house. Satisfied there was nothing she bent over and sucked me again for a while before sitting up and asking

“Do you want to see me?”

“What?”

“You know. Do you want to look at me? Here.” She pointed down to her crotch and leaned back a little.

Did I ever. I leaned over her as she sank back onto the bed, parting her thighs. I looked down in between her legs. Frankly, I couldn’t see much but her hair and sort of shrugged my shoulders.

“Here” she said, and lifted a leg over the top of my headand swivelled herself around until I was lying between her thighs. She raised her knees and then put both her hands between her legs and pulled at her flesh. I could see her crack between her legs, but when she pulled the flesh apart; what a difference! What I had known of girls as a thin slit between the legs suddenly blossomed into a large mass of flesh with ripples and bumps. I stared at it, mesmerised. What I had thought was a single slit became four lengths of flesh. She pulled on them outwards and then upwards letting me look inside it.

“Do you want to hold it?” she asked.

I reached forward with both hands and gripped the edges like she had and then stretched them open. They were slippery and both slipped from my grasp. I quickly grabbed them again, more firmly and stretched them open. The view was amazing and I put my head closer to take in the detail. A strange aroma came to me. Not unpleasant, not familiar but somehow arousing. Aunt Vi slipped her hand betweenher stretched lipsand said

“Look here.”

She pressed a finger at herself and before my eyes, it slid into her. I hadn’t even recognized the spot as a hole. She rubbed her finger in and out for a moment, slipped it out and asked

“Want a go?”

I let go of one side of her and tentatively poked my finger at her. It slid in quite easily. I was now feeling the softest warmest place I could imagine. Oh, the secrets of women. Everything I had felt this morning was softer and better than what I had felt before it. She pressed herself up at my finger until I had pushed it all the way in up to my hand then slid herself up and down on it. I soon picked up the rhythm and poked my finger in and out. Aunty Vi sighed and moaned softly while she watched me staring between her legs. After a short while she reached down and took my hand away, only to group two fingers together and push both of them into her. Amazing; they both slid in easily. I continued my fingering with both of them while she joggled around to meet my thrusts.

She was looking at my face while I fingered her. Suddenly she reached up and pulled me down to her by the shoulders. I was lying on those magnificent breasts.

“Feel this” she said.

She reached down between us and I felt her fingers take hold of my cock and pull it towards her. She started flicking it up and down against her body with her hand. She was rubbing it between her legs where I had just been looking and I could feel it sliding in the dampness between her lips.It was wonderful and making my cock feel really good. I lay heavily on her, not moving, letting her make me feel good. She stopped and told me to lift up a bit. As I lifted up she rolled her hips up more and pulled her knees back. She pulled my cock back to her and rubbed it around her slit again until she found a spot.

“Push” she said, and pressed on my back. I pushed my hips down and felt my cock slide into the most wonderfully wet and warm cavity imaginable. She rolled under me and pushed on my bum until I was completely lodged inside her. She stopped and held me there for a few moments as if to let me indulge in the sensation. Something in me made me feel like I wanted to move and I started sliding and rocking in her. She kept both her hands pressing on my bum to control my youthful inexperience and keep me locked into her. Soon I was thrusting into her as nature took over. The feeling was so intense; my cock started tingling very quickly. I kept pushing it into her as the feeling mounted until I was suddenly over the edge and squirting inside her. Aunty Vi’s experience took over and she held me tightly on the bum so I would not separate from her in the final moments. She let me have my pleasure inside of her and held me until I had completely finished and was lying still on her.

I was overwhelmed by this and couldn’t believe anything could feel so good. I just knew I wanted to do it again, all the time. My shrinking penis slid out of her.She rolled me off her onto my back and propped herself up on an elbow to look at me. Then she did the most exquisite thing. She put her face down to my cock and took it in her mouth. She sucked it all the way into her mouth and swirled her tongue around it before drawing her mouth off it with pursed lips. I learned that this was another method she used to hide the evidence.

I leaned over her and looked between her legs. I wanted to see where I had just been. She opened her legs for me, sensing my curiosity. I was bold now and grabbed her lips to pull them apart. She was a dark crimson colour, wet, with some liquid leaking out of her hole down to her bottom. It was a beautiful sight that was etched into my mind forever.

This was the best holiday I ever had. Aunty Vi was available to me for the next eight days. I enjoyed her every night and every morning, a few times in the middle of the night and a couple of quick times in the afternoon. She told me that she knew Ihad beenwatching her get undressed at night and rubbing my cock on her behind in the morning. She had decided to give me a show at night and to sleep nude to see what I would do, although she vowed she wouldn’t have touched me if I hadn’t responded.

I learned a lot from this most generous woman who showed me how to have sex in many positions, how to pleasure a woman by rubbing her clitoris, and allowed me to indulge myself in exploring whatever I wanted of her. She showed me how to give oral sex to a woman, penetrate her anus and how many fingers I could fit inside her. She showed me the pleasure of receiving full oral sex where I emptied myself completely into her mouth while she swallowed everything, leaving not a trace. I was so sad to leave. She visited us several times over the next few years and I was able to indulge myself with her again each time. She was always just as generous with herself, giving me access to her body foranything I wanted, whenever I wanted.

Published 
Written by Slickstick
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