Johns Story 4

Chapter 1

My name is John and I am Sarah's older brother. As she has shared her sexual adventures with you she thought that I ought to do the same, so here goes. I went to an all boys boarding school on the south coast of England which is where I found my love of sailing and by the time that I was 19 and ready to start university I was a qualified yacht skipper, looking forward to a summer working on boats in the Aegean Sea for the business owned by the parents of my best friend, Simon:

I pulled my bright yellow Suzuki motorcycle to a stop on the drive at Simon's house, I had a couple of days until I headed off my summer assignments and wanted to chill with him on a glorious late-spring afternoon. As was my habit, I wandered around the side of the house to where there was a swimming pool which would make the perfect chill location with a few beers. I was not expecting to see Mrs. Rogers, Simon's mum lounging by the pool and certainly not topless! Before I could beat a hasty and discreet retreat she looked up and spotted me. "Oh hello John, I am afraid that Simon is not here at the moment, he has popped into the office to see his dad." "

"No problem, Mrs. Rogers," I said, "I will come back a bit later."

"There is no need for that," she said, "stay and keep me company, and please call me Jean."

"OK Mrs... Jean." I said as I sat on one of the other loungers, struggling to stop staring at her boobs.

"Is my being topless a problem for you," she asked, "you must have seen a girls breasts before, surely?"

I blushed a very deep shade of red, I had never been able to talk to girls, let alone get them to let me see their breasts, the downside of single sex education!

"Nooo, not a problem," I managed to say, "but I have never seen real breasts before, only pictures in magazines, I have always struggled with girls since one made me look stupid in front of everyone when I asked her out on a date."

"What a little bitch she was," said Jean, "well, feel free to look at mine all you want, you are a good looking young man."

"You breasts are very beautiful," I said

"Look, you obviously came here to relax by the pool with Simon, why don't you get changed and relax with me?"

I dashed into the pool hut and changed into swimming shorts, only realising as I was about to step back onto the patio that I was sporting a semi hard-on. I draped a towel across my middle so that it would not show and lay down to enjoy the sun.

"Would you help me with some suncream on my back?" said Jean.

"Yes, of course," I replied and swung off the lounger to apply the cream to her bare back. Once the cream was liberally applied, I was about to return to my lounger when Jean rolled over and stared straight at my crotch which was bulging even more as a result of touching her bare skin.

"You appear to appreciate my body," she stated.

"Y Y Yes," I stammered.

"Good, because I very much appreciate yours," she said and proceeded to stroke her hand along my bulge, causing me to become fully erect.

"Simon won't be back for a while yet," she said softly, "would you like to see that not all females are horrid bitches?"

I just nodded, unable to believe what was happening. Jean took my hand and placed it gently but firmly on her right breast and I felt her nipple harden under my hand as I inexpertly massaged her flesh. I then felt her hand undo the drawstring of my shorts and put her hand inside and grasp hold of my rock hard cock.

"My God your big," she said, and with that pulled down my shorts and took the head of my 8" cock into her mouth, slurping up and down the shaft as far as she could go. Given my complete inexperience, I was never going to last long and within a few moments I felt the unstoppable urge to ejaculate.

"Oh fuck, I am going to cum!" I shouted. Jean kept her mouth locked onto my cock and I shot about 3 ropes of cum into her mouth. She managed to swallow most of it but some escaped and dripped onto her breasts.

I dropped onto the lounger, my cock now deflated but shiny with Jean's saliva and the remnants of my semen. Jean was looking flushed, her nipples were like rocks and she was breathing heavily. "Would you like to see my cunt?" she asked.

"Is the Pope a Catholic?" I managed to joke.

She stood up and in one fluid movement removed her bikini bottoms revealing herself to me. Laying back she spread her legs and said, "come and look closely so that I can teach you how to please a woman."

I lay between her legs, my face a few inches from her pussy as she parted her lips and proceeded to show me her most private parts in graphic detail.

"Now, lick my clitoris and put a finger into my vagina," she instructed.

I was only too willing to comply and set about learning how to satisfy a woman. Judging by the sounds that she was making and the amount of liquid leaking from her pussy I guessed that I was doing OK. Her groans increased and her hips bucked and as I licked and fingered her, "Oh fuck, is your cock hard again yet?" she asked. I did not need to look as I could feel that it was already fully erect again, "yes" I mumbled into her pussy.

"Then put it in me and fuck me," she said.

I climbed on top of her, and she guided my cock into her vagina, its soft wet walls squeezing me as I penetrated her. I kissed her for the first time, our mouths crushing together and our tongues wrestling. "You taste of me," she said, "well you taste delicious," I replied.

"If only I had known that this was going to happen today, I would have trimmed my pubes, I am a bit hairy down there, did you mind?"

"No way," I said, I cannot describe how good licking you was, and hairy is natural right?"

"It is," she agreed "but shaved means you don't get hairs in your teeth.

I carried on pumping into her, she reached between us and started playing with her clitoris and I could feel her fingertips touching my cock as it went in and out of her. Her gasps increased and she shouted "I'm cumming, oh fuck, I am fucking my son's best friend and I'm cumming." I felt her vagina spasm, gripping my cock and a flood of juices coated my cock, balls and pubes. "I'm cumming too!" I shouted and released another load of semen into her.

After a while I felt my cock start to soften and it plopped out of her, releasing a flood of my come and her juices all over the lounger. "I think that we had better get cleaned up before Simon gets back," said Jean. "That is probably a good idea" I agreed.

The pool hut had a shower and we both got into it and washed each other, me paying particular attention to her breasts and her to my cock but there wasn't time for anymore fun and we both quickly dressed and returned to the loungers just before Simon returned home.

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Two days later I caught a flight from Gatwick to Corfu and found my way to the marina where I would be living and working for the next 2 months. I got accustomed to my new boat "Solstice" and took her out for a quick "shake-down" to make sure that everything was OK before my first clients turned up, I did not want disappointed customers as Simon had told me that the type of person they got for the day charters often gave very generous tips if the sailing experience was good for them. Checking the schedule, I seemed to be pretty well fully booked most days for at least the first 3 weeks, just a couple of gaps here and there to allow any maintenance issues to be dealt with.

Most days mainly consisted of taking either couples or small groups out for a days sailing in the beautiful blue waters, dropping anchor for lunch and swimming etc, returning back to base in the evening to give me just enough time to re-stock for the next day, grab something to eat before falling asleep.

It was on a Thursday in my third week that things changed a little. I was expecting an American couple, George and Dionne, for a days sailing, setting off at 10.00. At 10.30 there was no sign of my customers and I was just about to go and phone base back in the UK when a very attractive, petite lady in her 40's appeared, looking flustered. "Hi honey, I am so sorry that I am late, I'm Dionne."

"Hi Dionne," I said, "my name is John and I am your skipper for today, welcome onboard Solstice. I was expecting 2 of you, er, George is it?"

"That's right," she said, "but George has decided he doesn't want to go sailing, so we had a row, he has gone to play golf so here I am ready to enjoy what you and this boat can offer me." There was a definite twinkle in her eye as she said this and I realised that this could be a good day after all.

"OK, stow your stuff in the cabin and we will get off straight way," I said, "before George changes his mind and decides to join us!"

"Great idea," said Dionne, laughing, "let's get away as quickly as we can."

I started the engine and proceeded to release the boat from her moorings, in no time at all we were away from the marina, I shut down the engine and hoisted the sails as the breeze took hold and we powered our way out to sea.

"This is fantastic!" said Dionne as the boat ploughed through the sea, making good speed.

"We are not far from the bay where we will be stopping for lunch," I told her, "it is pretty secluded and you can only get to it from the sea, great for swimming and soaking up the sun."

"That sounds heavenly," she said.

"If you can take the helm for a minute, I will get the anchor ready, just keep pointing her towards the bay."

I took back control as soon as the anchor was ready and guided Solstice to within about 30 yards of the beach. "Drop the anchor" I instructed Dionne and as soon as I felt it bite, I dropped the sails and went below to prepare lunch. "The water is completely safe for swimming," I told her, "You can easily get to the beach if you want to." She looked at the beach and then at me, "not much fun on my own," she said, "can you come with me?". "Sorry", I said, "I am not allowed to leave the boat."

"Oh well, we can just enjoy looking at it from here, but I do fancy a dip. I suppose swimming is classed as leaving the boat as well?" She said.

"Afraid so, but you go ahead, I will put the ladder down so that you can get on board easily."

With that, she pulled off her tee shirt and dropped her shorts to reveal the smallest bikini I had ever seen, 2 tiny triangles of fabric to cover her nipples joined by strings and another small triangle to cover her pussy with a thong string up her bum crack, unsurprisingly, I felt my cock start to stir.

Dionne noticed my furtive glances and blew me a kiss, "sure I can't tempt you?" she said, indicating the water.

"I would love to, but I can't" I said.

With that she turned and performed a graceful dive off of the back of the boat, leaving me with an image of her pert bum cheeks as she entered the water. I busied myself with lunch preparations, checking every few minutes that she was OK. "Lunch is ready!" I called just as she got to the ladder and climbed back on board.

I handed her a towel and in my best Parker from Thunderbirds voice said, "Your towel M'lady, I wouldn't want you getting too cold and wet"

Dionne giggled and muttered something about hot and wet and sat at the table in the cockpit.

"I bet that you have some great tales to tell about the people who come on your boat?" she asked.

"I do, but I have to be careful, client confidentiality and all that," I said.

"You don't have to name names," she said.

"Well mainly its couples, sometimes small groups, occasionally single men who want to learn to sail, you are my first solo female. Would you like a glass of Prosecco with your lunch, it's very good and great with the seafood?"

"I will, thank you," she said, "will you join me?"

"Sorry, the dammed rules again," I replied.

"These rules are a pain in the ass," she said, "do they stop you from doing everything?"

"Only things that can endanger the boat or the clients," I said. "let me tell you about 1 incident that happened last week. Mostly I have lunch with clients and chat to them whilst we are anchored, but these two asked if I had could eat lunch in the cabin and leave them up top. Well, I thought that perhaps I had offended them in some way but, whatever keeps the customer happy as they say. So, I went below to have my lunch and after about 10 minutes I heard the unmistakeable sound of them having sex on the sun deck!"

Dionne laughed, "I bet you wish you had a video camera handy!"

I laughed in agreement, "I could have made a bit of money selling that, but they tipped very well, so no problem."

Dionne suddenly stood up, "do you mind if I sunbathe topless?" she asked.

"Not at all, be my guest," I replied.

"My tits are tiny, only an A cup, I hardly ever wear a bra," she said.

I gulped as I looked at them, small, yes, but with very long nipples, "they look perfect to me" I managed to say.

"I bet you have a scorecard as long as both arms," she said. "The girls must be fighting each other over you."

"It might surprise you, but I was a virgin until a few weeks ago and have only had sex once."

"Lucky girl to take your cherry," said Dionne.

"It was actually the mother of my best friend." I said.

"Wow, spill the details skipper!"

So, I told her about what had happened, leaving nothing out. When I finished, I could see that Dionne was breathing more heavily than before and her nipples were hard, sticking out about an inch.

"How was it going down on a hairy pussy?" she asked.

"It was heavenly as I had never done anything like it before, but it did feel as if I was flossing afterwards," I admitted.

"My pussy is completely bald," she said "would you like to see it and compare it to your friend's mother?"

"I would like that very much," I said.

She removed her bottoms and lay down on the deck, spreading her legs for me. "Now skipper," she said, "if it is not against your dammed rules, you need to take your clothes off as well, I can see a large bulge in your shorts and I am dying to see what you have hidden in there."

I quickly stripped and admired her naked body, so different from Jeans. "Now M'Lady, what would you like me to do to you?" I said as I leant down to kiss her softly on the mouth.

"Lick me and finger me until I cum," she instructed, "and if you want to play with my butt hole, I won't mind at all."

This was a new one, Jean and I had not even thought about any anal play, but I was keen to give it a go. I traced my tongue down her body from her neck, stopping to suck on her gorgeous nipples before moving lower, licking her belly button before moving to where her pubic bush should have been, it felt wonderfully smooth, no stubble at all. I went lower and my tongue made contact with her slit, her labia were very pronounced and she was leaking juice like a tap, some of it running down her crack to pool around her bum hole. I re-positioned myself and lay between her legs, licking her slit from clitoris down to her vagina and sometimes further on to tickle her anus with my tongue.

"Jesus, for a novice you are fucking good at that," she said, "your friend's mother is one hell of a teacher."

I kept on licking and probing with both my tongue and fingers, at one point I had my mouth on her clit, one finger in her vagina and another in her bum. She was squirming and I knew that she was about to have a massive orgasm. "Oh YESSSS" she screamed as a flood of her juices squirted from her. She rolled over onto all fours and said "now fuck me as hard as you can."

I positioned myself behind her and slid my hard cock into the welcoming embrace of her vagina.

As instructed, I began thrusting in and out of her, just as I was about to cum I pushed my thumb into her bum and she screamed as another orgasm hit her and I emptied my balls into her quivering vagina.

We stayed locked together like two rutting animals for a few minutes until my cock slipped from her with a plop, followed by what looked like a lake of my semen dripping onto the deck.

"Be a darling and clean me up," she instructed.

I laid on my back and positioned myself under her pussy and licked her clean, although that seemed to start her off again and she sat on my face, grinding her pussy into me and came again!

"Oh shit that was good," she said as she finally levered herself off of me "I haven't been fucked like that for decades!"

"I am glad that you enjoyed it, I know that I did," I said. "But, it is getting late and we need to head back to port."

"Thank you for everything," she said, "not just the awesome sex, it has been a wonderful day."

When we got back to port it was staring to get dark, as Dionne stepped onto the pontoon she handed me an envelope, inside was $500, a huge amount. She shushed my protests that it was too much saying that George was very wealthy and if he couldn't or wouldn't give her a good screwing then he would have to pay for someone else to do it for him.

"I am going to see if I can book another day with you, if that is OK" She said

"I will look forward to that," I said, "If you want to, you can book a 2 day trip where we stay out overnight?" I suggested.

"That sounds fabulous," she said, "I will book a 2 day trip for me and a day trip for me and a couple of friends, if you think that you can handle 3 horny ladies who also have rich husbands?"

"If they are anything like you, it will be my pleasure," I said.