Lessons from an Older Woman

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Even though this story is basically true, I have embellished it with fiction to make it more enjoyable. The truth is though I thoroughly enjoy the recalling these early sexual experiences because they provide me with wonderful fantasies. I hope you enjoy them too.


It was mid January 1987, and I’d just celebrated my eighteenth birthday. Three of my mates and I decided to holiday together so we drove from our home in Sydney to Coolangatta on Queensland’s Gold Coast. We stayed at a guest house called Stella Maris which was right opposite the beach and in between two really good pubs, so there was no shortage of things to do. Like most red blooded young males, most of our time would be spent surfing, drinking and searching for female company.

On our third night we had a big drink and I decided to sleep-in the following morning. On waking I put my board shorts on and headed for the beach to look for my mates. It was a beautiful day and as I was wandering around searching for the boys I noticed a woman sitting to my right and she seemed to be calling me. I had no idea what she wanted so I walked over and said, “Hi, are you waving to me?”

The woman said, “Are you looking for your friends from the guesthouse?”

I said, “Yes, have you seen them?”

“No, that’s why I called you, I don’t think they’re down here, I haven’t seen them today.”

I guessed she was in her mid to late thirties with long black hair and was wearing a cheeky little yellow bikini that really showed off her tan. She was a very attractive lady and was accompanied by two younger girls whom I guessed were around fifteen or sixteen.

“I have no idea where my mates might have gone,” I said, “I might just hang around for a while and wait.”

“You can wait here with us if you like.” She said.

“Thanks.” I said as I spread my towel out and sat down.

“My name’s Kathy and this is my daughter Megan and her friend Tracey.”

“Nice to meet you, my name’s Tony.”

After about fifteen minutes in the sun I decided to have a swim and headed for the water. The water was beautiful and I guess I surfed for a half an hour or so. When I got back to my gear Kathy was by herself. I picked up my towel and dried myself off and I said, “Don’t take this the wrong way but where I can see where Megan gets her good looks.”

She said, “Thanks, I do work at it and go to the gym four of five times per week.”

She started to chat about herself and told me she was thirty-nine and from Brisbane. She was chaperoning her sixteen year old and her friend because she felt they were a too young and inexperienced to let them loose in the male jungle yet. “I remember how naive I was at that age.”

“Yes,” I said, “it is a sort of jungle I guess.”

She told me how amusing it was to watch the boys chasing after the girls. “I went through the same thing as a teenager,” she said, “with them trying every trick in the book to get them into bed. That’s why I’m here as a chaperone.”

I was a little shocked she said that and replied, “Well, surely that’s all part of growing up isn’t it.”

“Well, I guess it is, but life is wasted on the young to some extent.”

“How so?” I asked.

“If I’d known at your age, the things I know now… growing up would have been… let’s say… a lot more pleasurable.”

“What sort of things?”

“Use your imagination Tony.”

“Are you talking about sex?”

“You guessed it.”

“Yeah, I know what you mean.” I said.

We sat in silence for a moment before Kathy said, “It’s my experience that boys in particular, have no idea how to look after a girls needs.”

“Surely that comes with experience.” I said continuing to be surprised at the nature of the conversation.

“Maybe it does,” She said, “but how much better it would be if there was some type of instruction for teenage boys. It’s definitely not the sort of thing your mother will teach you.”

I laughed and said, “No way!”

Kathy giggled and said, “I’m busy with the girls today but why don’t you join me for breakfast tomorrow in the dining room around nine. We can continue the conversation then.”

I was shocked but said, “Sure Kathy, I’d like that.”

With that she picked up her things and left. I couldn’t help wondering why she wanted to have breakfast with me. It did cross my mind she might be making a pass at me but I dismissed it thinking she was old enough to be my mother.

The next morning I arrived at the dining room just after nine and Kathy was sitting on her own near the front window. I made my way past the now mostly empty tables and sat down opposite her. We exchanged pleasantries before I went to get myself a Ataşehir Escort glass of fruit juice.

“Where are the girls?” I asked.

“They’re on a day cruise to Stradbroke Island and won’t be back till later this afternoon,” she said, “they do need a bit of independence at their age.”

We chatted while she finished her coffee. When she’d finished I said, “I can’t help wondering why you wanted me to join you this morning.”

She laughed out loud and said, “You’re a very good looking young man and I love being in the company of handsome men. Besides we didn’t finish our little talk.”

“I don’t understand.” I said.

“We were talking about young men and their lack of understanding of a womens needs. I’m sure it works both ways but in my experience men can be satisfied easily but a girl needs a lot more attention.”

“So where are we supposed to get that information?” I asked.

Kathy stood and said, “Come with me.”

My heart was racing as she led me up the stairs and down the hallway to her room. She opened the door and I followed her in. The room was much larger than mine, overlooking the beach. There was a lounge, a television and a double bed with a separate bathroom.

Kathy was dressed in a blue patterned sun dress and she looked stunning. She walked to me and put her arms around my neck and kissing me gently on the lips. I was in a spin, ‘Shit, does she want to fuck me?’ I thought to myself. I felt my cock stir beneath my shorts. We kissed passionately and she thrust her tongue deeply into my mouth. I nearly passed out as I felt her hand grasp my hard cock. “Wow!” She said under her voice.

She led me across the room and we sat on the edge of her bed. She sensed I was nervous because she whispered, “Relax Tony… I’m not going to hurt you”.

She continued, “I was attracted to you when I first saw you and I figured there’s a few things I could help you with.”

“What sort of things?”

“How to really satisfy a girl in bed for a start.”

With that she stood and let her dress slip to the floor. She wasn’t wearing a bra, only brief red knickers. I was amazed at how good she looked. She was quite tanned and her tits were smallish but beautiful, “Do you want to remove these?” She said lifting the elastic on her panties. “You can take them off.”

I moved cautiously forward and slipped her panties down. She stepped out of them before turning to face me. My balls were aching for release, I’d never been in a situation like this before.

“Stand up.” She said.

I stood and Kathy pulled my tee shirt off dropping it to the floor. She undid my shorts and as she slid them down my erect cock bounced like a spring board. She laughed and said, “Turn around. Let me have a look at you.”

She eyed me from tip to toe before saying, “You’re really something Tony. Have a look at that cock of yours, it’s beautiful.”

Embarrassment overwhelmed me and I could feel myself blushing. She reached for my cock and pulled me to the bed. We sat on the edge of the bed for a moment while she fondled my dick.

“You’re wet!” she smiled.

“I’m sorry it’s just that… “

“That’s okay I understand.” She interrupted.

I asked, “Are you married?”

“Is that important?”

“Guess not.”

Kathy lay back and patted the bed so I lay beside her. Her nipples were erect as I started rolling them between my fingers. Suddenly she stopped me and said, “How much experience do you have with girls Tony? Do you have a girlfriend?”

“Sort of, There’s a girl I take out back home.”

“Have you had sex with her?”

“Not really! Not properly!” I said.

“Have you ever had sex with a girl before?” She asked.

“Just once, last year when we were on holidays I met a girl and we did it. But I used a condom.”

“Did you enjoy it? Did you have an orgasm?”


“Did she?”

“I’m not sure.”

“You see, that’s what I’m talking about,” She said, “the boy gets to blow his load and the girl is left high and dry.”

“I guess!”

“Do you know what a clitoris is?” She asked.

“Not really!” I said.

“It’s the key to a girl’s pleasure and far too many men don’t know or don’t care.”

She took my hand and placed it on her vulva. I was out of control with excitement and my head was spinning. She took my hand and guided my fingers inside her cunt lips and rubbed them on what felt like a small shaft of skin at the top of her slit. It was small but firm to touch.

“Don’t press too hard,” she said, “that’s my clitoris and it’s quite sensitive like the head of your cock.”

Kathy went on to explain that a woman’s clitoris is like a penis; Anadolu Yakası Escort it becomes erect when she’s aroused and is the main source of a woman’s pleasure. “The truth is Tony,” she said, “most women need more than a guy thrusting his cock in her to bring on an orgasm. In fact a good lover will always ask his partner how she likes to be touched. And a wise girl will know exactly how to teach her partner what she needs… what she likes.”

I still had my fingers inside her and realised how little I knew. I had a wave of embarrassment flow over me.

“If you get between my legs, I’ll show you,” she said matter of factly, “in fact you can stay there and watch what happens while I pleasure myself if you like.”

I positioned myself between her legs no more than eighteen inched from her cunt. She used both hands to spread her outer lips and pull back her clitoral hood.

I couldn’t help thinking this was my first close up encounter with a cunt and how surreal the situation was. I took the opportunity to touch it ever so lightly and couldn’t resist sliding my fingers into her before she removed my hand and said, “Watch what I do and see what happens when I have an orgasm.”

She began a slow circular movement with her middle finger, not directly on her clit but just around it. After a minute or two she began to speed up the stimulation making more contact with the shaft of her clitoris. I remember thinking when the head popped out of its hood as she stroked, how much like a tiny miniature penis it was. Kathy steadily built up momentum with her fingers now rubbing quite firmly. I was frantic with desire and could barely contain myself from joining her and jerking off. Seconds later she moaned, “Oh fuck Tony this is beautiful.”

It was obvious things were heating up because Kathy began slowly thrusting her hips as she worked on her swollen vulva. Her cunt lips were now large and red, engorged with blood. “Oh Tony!” She mumbled, “I’m so close… I’m going to cum Tony, watch what happens.”

Suddenly she arched her back and as she made a strange gurgling sound at the back of her throat, “Ahhhhhhhh!” As she moaned her vagina and anus began pulsing and contracting, vigorously at first but slowly subsiding. The whole show only lasted maybe fifteen to twenty-seconds. I watched in amazement as every once in a while another strong contraction puckered her cunt and anus. I was completely blown away… Here was this beautiful mature woman, old enough to be my mother, having abandoned any inhibitions and sharing her orgasmic ecstasy with me. I couldn’t help feeling a strong emotional bond with her right at that moment.

After a few seconds she regained her composure and blushing with embarrassment, “God that was wonderful, did you get to see it happen?”

“I did, it was sensational… can I…?”

“You want to fuck me?”

‘Was this really happening?’ I thought to myself. “I do Kathy.”

As horny as I was I couldn’t concentrate, I looked down and noticed a strand of pre-cum dripping from my rod. My mind was swirling as I positioned myself between her legs. She took hold of my cock and guided it to the entrance of her cunt. Just being there, with my throbbing cock at the entrance to her love hole was almost enough to send me over the top.

Kathy snapped me back to reality, “You’re okay now Tony, you can push it in.”

With those words I pushed my cock into her as far as it would go. My head swam with euphoria as I felt her hot wet hole envelope me. I was at maximum arousal, and even though I stayed completely still, I felt the contractions at the base of my cock start as a wave of orgasmic ecstasy flooded my groin. I closed my eyes and groaned with pleasure as I pumped load after load of semen into her wet warm hole. As I lay there enjoying the last of my orgasmic contractions I was overcome with emotion as a few tears rolled down my face.

I said, “I’m sorry Kathy, I couldn’t hold back.”

“I’m not at all surprised.” She said.

I put my hand between her legs and was amazed to find the bed saturated with our juices. I could see them oozing from her slit. “Can I touch you again?” I asked.

“Of course Baby.”

I thought I’d try my hand at what she’d shown me so I turned my attention to her clit, using our fluids as a lubricant. She immediately responded by widening her legs to make it easier for me. I made the same small circular movements over the hood of her clit until I detected her arousal kick in once more. “You bugger!” she said with a grin. “You’re a quick learner.”

We kissed and I increased the tempo of her stimulation. In no time at all she started to climax again pushing her groin Kadıköy Escort hard into my hand as she experienced her second round of ecstasy. I suddenly realised I was so involved in what I was doing; I hadn’t noticed my cock was almost hard again.

I rolled onto my back and stroked my dick until it was fully erect. Kathy was rather amused by this and took over the stroking. She lifted herself and crouched over me before slowly lowering herself onto my rod.

“Can I move yet?” she asked and I nodded yes.

Kathy began long slow strokes from the tip of my cock to grinding it in as deep as it would go. She kept this up for some time before asking if I wanted to enter her from behind. I agreed and we changed position. She was on the floor bent over the bed so I quickly found her hole and started thrusting away. We must have fucked for ten minutes or so before I started to feel the first signs of orgasm. The intensity built and my whole groin throbbed with pleasure as I slammed into her. Whack, whack, whack! Then, almost delirious and dizzy with ecstasy, the contractions deep inside the base of my cock began and my orgasm overwhelmed me. Moaning loudly I began squirting into her once more.

I was completely spent and as I withdrew from her swollen cunt a cocktail of our juices dripped onto the floor. We laughed and got back into bed. “You really are a fast learner Tony, I enjoyed that.”

We curled up together and must have dozed off because when I woke it was almost 2 pm. Kathy was asleep on her back so I pulled back the sheet and started to suck lightly on her right nipple. She woke and said, “You ARE a horny young man aren’t you! Are you are ready to fuck again already?”

“Me? Horny?” I said feigning surprise.

“Okay, here’s lesson number two.” She said with a cheeky grin.

Kathy leant over and kissed me and started thrusting her tongue in and out of my mouth in a simulated sex motion. She worked her way down my neck and chest nibbling and sucking using her teeth and tongue. She continued teasing me until she settled on my left nipple. I closed my eyes and savoured the moment. A few minutes later she travelled down to my navel flicking her tongue in and out to tease it. I was amazed how nice it felt and how sensitive it was. Then she moved lower and stopped at the edge of my pubes. I knew what was coming next as she lifted my half erect cock off my abdomen and took it into her mouth.

“Oh fuck that’s nice Kathy.”

“Is this the first time you’ve had your cock sucked?”

I nodded.

“I can smell and taste us both. It’s beautiful.” She said.

Kathy sucked and licked my swollen rod, paying attention to the underside of my frenulum. I lay there with my eyes closed absorbing the wonderful sensations until I felt the first sensations of orgasm. “Jesus Kathy,” I moaned, “I’m going to cum again.”

She lifted off enough to say, “You can cum in my mouth, I’d like that.”

She went back to work on me and before long the pleasure peaked once more and I started pumping into her mouth. As soon as I’d finished she lifted herself up and kissed me. I was completely blown away as she let my semen run into my mouth. “How’s that?” She asked.

“I don’t like the taste all that much.” I said.

“Have you never tasted your semen before?”

“Yeah, I’ve tried it a couple of times when I’ve been… you know… jerking off.”

“It’s an acquired taste I think.” She said with a laugh. “I’m going to want you to do that for me too.”


“Please! Use your mouth and tongue on my clit in the same way you did with your fingers.”

I buried myself between her thighs and began working her clitoris with my tongue, occasionally running my teeth over it ever so lightly. “Oh my fucking god!” She groaned. Moments later she started a rhythmic motion with her hips and I had difficulty staying with her. Then with a throaty moan she pushed her cunt hard up against my face and I knew she was there.

We lay there motionless, me with my head resting on her pubic bone.

I was brought back to reality when she said, “I really need to shower and tidy up now Tony. The girls won’t be too far away and I need to be ready for them.”

“Of course,” I said, “when can I see you again?”

“If you like we can get together later tonight after dinner, maybe about nine, once the girls are settled for the night.”

“It’s a date.” I said.

“You really are a performer aren’t you?” Kathy said, “I do believe you came three times today. Not bad for a beginner!”

“Four actually!” I said, “I had a wank in the shower this morning as well.”

We both laughed.

I dressed and made my way down to our room. None of my mates were there and I lay on my bunk staring at the ceiling. I felt quite strange, almost as though the experience was some sort of dream.

I felt my cock twitch when I thought about what she had in store for me later that night.

“Now what time was it she said?”

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