Pleasure Island

by peterholt

5 Jan 2017 8404 readers Score 9.0 (94 votes) PDF Mobi ePub Txt


Pleasure Island Version II

Peter Holt - Jan 2017

It's hard to say how one hears about such a place. A short note from an admiring reader.... a whisper in a bathhouse....sufficient to say that I found myself on a jet to an airport on an island somewhere west of California or east of Florida, and then on a small boat to a remote island minutes, hours or days away. As the boat approached the island, I saw lovely, swaying palm trees and bright bursts of tropical flowering bushes.

As the boat tied up at the short pier, I pulled my 25 year old, 6', 180 pound frame up onto the grayed wooden wharf, and strode towards the native-style villa a few hundred yards away, under the phallic palm trees. Before I had walked more than a few feet though, a young firm figure detached from the villa and hurried toward me. The figure turned out to be a young boy, no more than 17 or so, about 5' 8” tall, perhaps 120 pounds, wearing a thin fabric thong and sandals. The fabric did nothing to hide the fact that the boy, whose face appeared angelic to me, had what looked like  half an erection. I could clearly see the outline of his full 6" of cock, pointing up towards his face, and his small balls beneath.

His beautifully white even teeth signaled his mood, as he smiled broadly at me, his tan skin making the contrast even greater. His long blond  hair, shoulder length in the back, and with a long tuft in the front that would, from time to time, cover his green eyes, flowed with his movement, and curled against his smooth skin where it touched him. "Welcome to Pleasure Island," he announced in his young boy voice. "My name is Oliver. May I take your bag?"

As I only had a small gym bag, since I'd been warned of the dress code, it was very light and easy for Oliver to handle. He immediately took my left hand into his right, and led me toward the building. His touch was warm and soft, and I felt my own 8" cock stiffening at this unexpected contact with such a delightful and lovely boy. He chattered about the weather, the foliage, and so on, but I found my eyes fixed on his warm, slim body, and the very thin piece of fabric slipping between his tight butt cheeks, to disappear between their plumpness. I wondered if I'd be lucky enough to see more of Oliver.

Too soon we arrived at the "Administration Building," whose origin and styling appeared to be French. Inside, I found a small reception desk manned by a beautiful 30 year old woman. She greeted me warmly by name,

"Mr  Mercer, may I call you David? We are very informal here." At my quizzical look, she laughed. "You are wondering why there is a woman at a men and boy's island, yes?" I nodded, and she continued. "The owner discovered that no man could work on the island, regardless of his orientation or proclivities, and resist our boys for long. The first few resort managers were straight men, but, unfortunately for the owner, not for long. So, he decided that a lesbian would make a better choice, and so it has worked out. I live here with my life partner, and we are very happy.

She explained that her name was Noelle, and that this would be the only time other than checkout that I should see her. All my other needs would be taken care of by staff, who were boys ranging in age from 8 years old to 18, with most between 10 and 16 in age. I asked where the boys came from. She replied that the owner was a wealthy traveler who specialized in rescuing boys from desperate situations of poverty or family abuse, and his travels took him all over the world in this pursuit.

Noelle explained that there was little need for clothes. The guests were provided with all that was necessary and most guest went round in at most a shirt and some shorts. At the look on my face, she added, "Our guests find that they have no need of shorts, or pants, or even underwear. Indeed, often those things impede them unnecessarily, so the shirt to keep the sun off is ideal."  "This is pleasure Island" she continued, "the concept here is your  pleasure in the company of young men. We have looked at your resume and we have tried  to match your age and your sporting activities and pastimes with your personal assistant". 

“We think that Oliver who you are already acquainted with is a good match for you. He is 

very skilled in tennis, golf, swimming and running. He is well read and can discuss both politics and finance beyond his years would suggest. He is also a fully trained  butler and masseur. As most 17 year olds he has a high sexual drive and can perform almost any  sexual service you desire."

"You will find there is no mobile phone signal or internet connection here but if we receive  a message for you on the phone number we supplied then you will be informed without delay"

"We do find it necessary to impose just a few rules however", she continued. "We do insist

that all boys are in the our private chambers between the hours of 11pm and 8am. This is to ensure both you and they get good rest!. Additionally we do insist that there are no marks left on the the boys skin and this rules out such activities such as spanking, cutting, biting and burning. We also insist that if a boys says stop he means it. Lastly specific activities are banned such as fisting, sounding and breath control.  Lastly we do ask that there is no sexual activities in the restaurant area. We do have a good security team and any violations of these rules will result in you being dispatched home without delay."

"We have a maximum of 25 guests at any one time and a minimum of 50 boys at any one time. If  you do feel that Oliver is not a match for you then please let Oliver know and we will try and find you a different assistant. The 25 boys who are not assigned to a guest at any time may on your request also be assigned to you. They do have other duties such as cooking and cleaning but  Oliver can help you in coordinating them"

"Now I think that's enough from me so if you have no questions then Oliver will show you to your  room".

With that, she handed Oliver a small package and told him to take me to "Number 7." Oliver eagerly took my hand in his, and led me out, and around the rear of the building.

We walked down a wide path which was walled in by beautiful foliage, as colorful birds flew to and fro overhead. On the way, oliver took my hand, and, unexpectedly, placed my hand on his smooth  warm rear end. I could feel him wiggling his butt inside my grasp, and he looked up happily at me. My hand closed over his hairless orbs, and then we paused. Oliver folded himself into my arms, and buried his face in my chest. He lifted his face up to mine, and we were soon joined in a passionate kiss, his warm, soft lips pressed against mine, his wet tongue sliding against my lips as he sought entry into my increasingly hungry mouth.

I opened the cane door to the bungalow, and Oliver  entered first, spreading his arm in a flourish, and grinning madly. The accommodations were sumptuous, but entirely in keeping with the tropical milieu. A small cane settee, chairs and coffee table, accompanied by a cane and wicker bar, made up the seating area. Oliver  eagerly led me to the partially divided bedroom suite beyond it. I was very much impressed by the king size bed which held court in the center of the room.

"Please sir, " Oliver said, "may i make some suggestions as to the schedule for the 

rest of the day".  With that he undid the small package containing a shirt and  shorts. "Can I suggest we take a shower and freshen you up after your long journey. After that we can take a walk of the grounds so you can see the facilities. I have taken  the liberty of ordering us an evening meal of lobster in the restaurant, unless you would rather eat alone ?

He continued, "After that we can come back here and see if you would like my company for the  rest of the evening if you wish to do so?"

I asked Oliver how it was he had ended up in such a place. He looked at me confidently, and said softly, "Sir, I haven't ended up  here. I'm making my way up in the world, and this was my best chance. You see, the owner of this island discovered me living in a house in in rural London, that was turned into a crystal meth lab. My chances of surviving the next year and avoiding either being blown up or drugged to death were very slim. This opportunity has saved my life, and after I accumulate enough money, I am going to business school. The owner thinks that should be in another year or so. That is, if one of the guests doesn't fall in love with me and take me away first, as often happens here!" With that, he looked deeply into my eyes in a way that moved me profoundly.

"Sir , I have been assigned as the person to turn down your sheets at night. You are free to acquaint yourself with any of the boys you meet here, in any manner you choose, but I will be here at night to tuck you in, and anyone else you may choose. We do have a few toys such as balls and dildos which you are welcome to use on  me or I on you. If you feel the need then we do have a supply of viagra which may  help revive some parts which need a little help!!!"

I thought that Oliver calling me “Sir” was a bit over the top so  I  asked him to call me by my name “David”.

With that he moved towards me and started to undress me in preparation for a  shower. He undressed me without any sexual contact. He laid my clothes on the chair and beckoned for me to follow him into the bathroom. There before me was the most magnificent triple size walk in shower I had ever seen. Oliver removed his little  white brief thong and walked into the shower and fiddled with the controls until he  stretched out his arm to join him under the warm stream.

The stress was beginning to fall out of me. I was in heaven. In a shower with a gorgeous boy with god only knows what to follow!

Oliver was still business like. He reached over to a shampoo holder and put a handful of 

cream into his hand. He said "close your eyes, we don't want to get this into your eyes do we?"

I did as I was told and closed my eyes and with they he massaged the cream into my hair and started to wash my hair. The cream fell all over my body. His hands were all over my body - back, chest, legs and my dick was rock hard. Oliver did not touch it however. After a couple of minutes the soap as gone and he stood in front of me and looked up into my eyes. He said "kiss me David". With that I took him in my arms and kissed him on the lips. His mouth was open and his tongue was mine to play with. He was a great kisser.  I could feel him slowly kiss his way down my chest until he reached my dick which he gently 

took into his mouth. He took a second to look into my eyes and he swallowed by dick to the root without gagging at all!! After a couple of minutes I could feel the cum rising and not wanting to come yet I pulled him upwards again.  He stood up and turned round  pressing his butt against my stiff dick. He looked round and into my eyes and said "David - fuck me please". He bent over slightly as an invitation. Not wanting to hurt this  beautiful boy I gently pushed forward with my dick. Oliver reached back with his hand a guided my rock hard dick into his tight boy hole.


My cock was rock hard and my balls full of cum. He leaned a little further forward to give me good access to his bottom so I could push all my 8 inches all the way to the root. I took both his hands in my hands and pulled them backwards and he was like a penguin impaled upon my prick. He was purring in delight. This boy really did like to get fucked. I fucked him gently but strongly. This boy was pure pleasure!


It was not long before I felt the cum rising through my balls and into my penis. I exploded with a roar deep into his rectum. After a minute when I had stopped shaking i pulled out. Oliver turned round and took my cock into mouth and cleaned my cock once more.


"Thank you so much" he said. "It's been a while".


He led me out of the shower and fetched two towels from the wall and gave one to me to put round  my shoulders. With the other he dried my entire body. Oliver handed me my regulation pleasure  island short  and a skimpy pair of shorts. He put on some white very brief briefs!


"Shall  we take a tour of the facility?" , he said smiling at me


He led me by the hand and out onto the terrace into the garden. We walked around the gardens, the swimming pool area, the gym, the bar. We passed some of the other guests either relaxing with their assistants or just alone in the bar or pool. Most of the guest were much older than me and it seemed they were with boys much younger than Oliver!


"Oliver". I said, "Why did you say 'it’s been a while' after we were in the shower? Don't you have a lot of sex here?  He looked at me a little sheepishly.


"Well it's like this, I am 17 and soon 18. Many of the guests here like to be with boys much younger than me. It makes them feel young and wanted. There is nothing wrong with that. I have not been with a guest for 3 weeks and so I have been assigned to the kitchen and garden activities. When you came along the management thought that because of your profile you were looking for more of a  friend rather than a young play thing.


I looked sympathetically into his eyes and said "well they made a good choice, I am very happy with you".


Oliver said "the thing is that boys can be without clients for a few weeks but if it continues for week after week then their  future here is in doubt. I could become a gardener or cook or security guard but the future is a  little limited. I really want to start some sort of education and find a future for myself. I really hope  I can give you the pleasure you are looking for. If for some reason you are not 100% happy then please  just discuss it with me first before thinking of changing me out for another boy.”


"Don't worry Oliver", I said, "I cannot see any reason to change you and if I do then I will talk to you first".


With that we walked hand in hand to the restaurant. A lovely young nearly naked blond 15 year old greeted us and we sat in a discreet corner cubicle.


Oliver was a great conversationalist. he knew surprisingly about politics, finance and of course his first love sport. I was impressed by his range and quality of knowledge.  We ate a fantastic meal of lobster. He drank  water but I enjoyed a cold glass of beer.  


An hour or so went by. Oliver reached his hand across the table and put his hand in mine. "Shall we go back to your apartment now? Its 10pm and I have to leave you by 11pm. I would like you to make love to me again and I would really love you to make me cum."


I smiled. It seemed I had lost my embarrassment. "Of course Oliver, let's go".


With than we rose from the table. I noticed his dick was hard!!  Mine was quickly beginning to follow suit! We walked along the shadowed pathway. Oliver took my hand once more and put it behind his back and down into his briefs and onto his left boy cheek. He smiled at me. "OK he said?".  "Ok", i replied.


Oliver cleared his throat. There was something he wanted to say. "Can I ask you a question?", said Oliver. "Sure" I said, "ask away".  


"Well this is place is called Pleasure Island. We have been taught to pleasure our clients in any way we can. Will you tell  me what you would really like to do in a sexual way. I mean what is your fantasy,  would you like me to be passive or maybe active, would you like to be massaged or maybe massage me, do you like oral sex or 69 or maybe to have several boys in your bed. Would you like to play with some toys?”


This made me think a bit. "well I am not very experienced sexually, I have spent most of my life studying and doing sports. Basically I like to be with a well built boy older teenager like yourself. I am not really into young boys. Actually you are the youngest I have ever had!  You are really the expert so just lead me through your sexual skills and let's agree on the way. If anything I guess I like to be the giver rather than the receiver, but let's see what happens.”


"Great" said Oliver, "perfect answer". With that he turned and pointed his head upwards and waited for  a kiss which i easily gave him. His cock rubbed against my cock. We where both hard and pre-cumming. 


"Shall we do it here?" he asked.  "No" I said. "I prefer the softness and privacy of a bed".


With that we turned and walked quickly towards my room number 7.


We reached my room. Oliver led me by the hand into the bedroom and hopped onto the bed  with a big grin from ear to ear.  He looked up at me and said "please come to bed and fuck every hole in my body.  I need to cum  so badly."


Well that was an offer I could not refuse. I moved next to him on the bed and wrapped my arms around him. "Slowly tiger", i said, I am here for two weeks. "lets slow down and get to know each other".


I kissed him long and slow. Our spit mixed and he melted into my arms. I moved down to his groin and took his hard cock in my mouth for the first time. It was warm and  throbbing. He gasped as I took it all the way in.  


"I have not come for three days", he said. "May I cum in your mouth."  I had never tasted cum but for some reason  this suddenly turned me on. "Sounds good to me tiger", I said. I sucked hard on his cock. I pulled back a couple of times when i sensed he was close. He groaned and begged me to let him cum.  I looked up at him and said "ok give it to me". I moved my mouth back over his cock and within 10 strokes he almost screamed and exploded in my mouth with his cum hitting the back of my throat. It tasted strange but not unpleasant. I swallowed the warm present  and lay back by the side of him waiting for him to recover.


"Thankyou", he said. "I really needed that". With that he turned his back to me and guided my hard  cock to his boy rectum and i only  had to push a little and it popped inside his hole.  I moved gently back and forward. I was beginning to like  this boy! It was more than just a fuck. I fucked Oliver for 10 minutes. It had been a long day and the time was approaching 11pm. Once more the cum rose from my balls and I shot my load deep inside him.  He pulled off me, turned towards me and kissed me on the lips. 


The 11pm bell rang and he got out of bed and put on his white briefs. He picked up my travel clothes from  the chair and said "I will return at 8am if that is ok with you? Sleep well he said". 


And with that he faced the door and walked smartly out.


I reflected on the day. had I died and gone to heaven ?  Maybe I was dreaming?  I drifted off pretty quickly. I had been traveling for 20 hours and had sex twice. I was knackered.


I awoke the next day at 7am. I managed to make myself a cup of coffee and went on the private terrace to enjoy the morning sun. A newspaper had already been pushed under the door and I happily glanced through the Daily mail"


At 8am Oliver knocked on the door and entered the room. He was wearing the most gorgeous blue speed swim suit. Not too full and not too brief.  He was followed by a much younger boy of about 15 who was pushing a  trolley full with breakfast choices. The boy was also dressed in blue as though they were a pair. The  younger boy was Arron who efficiently set two places on the terrace for breakfast. Oliver thanked Arron he them left the room. Oliver could see me looking at Arron and said "if you would like Arron I can arrange for  him to come back a little later. He has the tighest little bum and really moans when he gets fucked."


I thanked Oliver and said "Maybe but right now lets have some breakfast". Oliver was standing beside me and I put by hand on his bum. He moved to face me and his cock was just in front of my face. I moved  my head forward and my mouth engaged his half hard cock. Oliver took his cock out of his speedos and i sucked on his cock for 5 minutes until he gushed into my mouth once more. I greedily swallowed the warm load.


"Lets have breakfast" i said.


Oliver and I spent a leisurely next day, although I was anxious to explore his sweet, smooth body, and so, between trips to the beach and nude swimming in the lagoon, we spent the rest of our time on just my second day at Pleasure Island, in each other's arms. I loved to feel his 6" cock stiffening under my caress, and the feel and taste of his pre-cum. I tried to torment him all day, by exciting him, then letting him cool down, but even with such restraint he still came 3 times during the course of our play. But given his youth, and randy nature, being 17 years old, he was soon ready for more action.


At one point, lying on the beach naked together, Oliver was lying on top of me, his dick pressing against mine, a thin thread of his pre-cum drooling onto my hard cock. I had my hands on his smooth, round ass cheeks, as he wiggled into me, causing his ass hole to flex open under my inquisitive fingers. As he felt my index finger penetrate his tight rectum, Oliver brought his soft, ruby-colored lips to mine, pressing them to me in a warm and passionate boy-to-man kiss. I opened my mouth, to feel his warm tongue searching against mine.


I slowly lowered Oliver down, and he reached behind himself with his left hand, and between his legs with his right, to grasp my hot cock and guide it to his young boy's hole. I felt his puckered anus briefly resist my soft cock head, but as he continued to descend, my hard dick soon pierced through his token resistance, and I felt Oliver’s 17 year old rectum gripping my cock, like a warm, wet glove gripping me. Oliver sucked his breath in at the initial pain, but continued to lower himself, as it was apparent the pain was fleeing before his growing pleasure.


"Ohh, god David! I feel so full!  but it feels so nice when I move up and down! Uhh! Uhh! Fuck! Fuck me, Matt! Fuck me HARD! I want to be your hot whore!! Fuck me like the slut I am, Matt!! PLEASE FUCK MY HOT HOLE!! FILL MY CUNT WITH YOUR CUM!!" As Oliver got hotter and hotter with his description of what he wanted, his dick got harder. As he moved up and down faster and faster on top of me, his dick was wildly leaking cum all over my chest and stomach. I thought about how nice it had tasted the previous night, and soon was ready to shoot inside him.


 Oliver was wildly bouncing up and down, impaled on my huge cock, ramming me as deep inside himself as he could. His cock, as hard as I'd ever seen it, began shooting out long jets of his beautiful white semen, the first shooting across my mouth and chin, the following jets falling closer to my stomach. His hairless balls pulled together, and I reached out to cradle them in my hand. They felt warm and soft, the wrinkled skin welcoming my touch.


I could almost feel my own cum being sucked out of my balls, through the shaft of my penis, exploding out of my cock head, to bathe his boyish rectal walls in my sweet, white fluid. My balls pulled up tight behind my hard cock, then slowly relaxed as they were drained. Oliver slowly slid himself back down then, to remain filled with my cock, still hard and warm inside him. Oliver lay against me, his head on my chest, my arms around this warm, sweet boy.


We dozed off, my cock inside of him, for about a half hour, then woke up together, and gathered ourselves to return to the bungalow. Hand in hand, we strolled up the winding path. Oliver would look up at me shyly every few minutes, and we'd each tighten our grip on the other's hand and smile. The flowers looked so colorful to me then, and smelled so fragrant, and I know the feeling was the same for Oliver. We entered the hut, as I held the door open for my young lover.


"Can we snuggle together, David?" Oliver asked hopefully. I smiled and took him in my arms, leaning down to kiss his sweet, warm lips. We embraced, naked, and then I led him to the sofa. I sat down in one corner, stretching out my legs to the other end of the pillow. I held my hand up to Oliver. He took it in his, then gracefully lay down between my legs, to make himself comfortable in the warmth of my crotch. My hands rested against his smooth, hairless back, and Oliver snuggled into my firm pecs. Once again, we both

fell asleep, and this time slept for at least an hour and a half, just as darkness fell.


We heard a knocking at the door, and roused ourselves to see who it was. It turned out to be  Oliver's young friend Arron, with a cart containing our dinners. "


Oliver looked over to me and said "would you like Arron to stay a while and have some fun?". I wanted to eat now but the boy was lovely. So i asked if he could come back in an hour after we had eaten. "No problem", said Arron and he left the room wiggling his little bottom on the  way. He looked back as he left the room giving us both a grin of expectation.


Oliver said "Arron is a very sexy boy" he he very flexible and can get into positions I could not contemplate. It is unusual for him to be available. You are very lucky."


"Well lets see" I said. "I am not really into boys so young"


The food was good. I was hungry and the hour passed quickly.


Once more there was a knock on the door and Arron in his little blue briefs walked into the room. Oliver  and I had moved to the lounge and were relaxing in the deep soft chairs. Arron stood in front of us. 


"What is your pleasure sir", said Arron. I was gobsmacked - not used to hear such was words for such  a young boy. Oliver stepped into the silence and said "Arron - get on your knees and give David your best blow job of your life, With that Arron got onto his knees. When I made no sign of resisting he moved his head down to my groin and  took my half hard cock in his little mouth. Just like Oliver he could deep throat without gagging. I was impressed.


After 5 minutes he came off my cock and said "would you like to fuck me now sir?". "yes please", i gasped. With that he led me by the hand into the bedroom. He lay on his back with his legs in the air. I mounted the bed and quickly got into position to put my weapon into his little anus.


I entered Arron and he gasped. The pain was obvious but he held it in and gradually got used to it. I thrust  back and forward slowly not wanting to hurt him. He said "fuck me deep , i need you cock and cum inside me". God this boy was horny. It was not long and within 50 strokes I had exploded deep into his bottom.


Oliver came into the room smiling. He sat on the bed next to Arron and me. he stroked Arrons hair as if to say well done!  Arron rose from the bed and said "I hope that was good for you sir?". "it certainly was" I replied. I think you can come back another day and teach me some more".


"Certainly sir" said Arron. You only have to ask Oliver. With that he left the room.


Oliver looked at me. "was the ok with you?" he said.


"Well to be honest I feel a bit like a pædofile. I know Arron does this of his own free will but in London its illegal to have sex with a boy of his age. It makes me feel a little uncomfortable. I feel better with a  boy of your age. I guess I am just old fashioned."


Oliver looked at me again. "Don't be ashamed, Arron knows exactly what he is doing. He is my brother!"


My jaw dropped. "Of course - i see the resemblance".  I made a bad joke - "I suppose you wanted to keep  things in the family".


Oliver laughed.


It was 11pm, the bell rang. Oliver got up to leave. "May I suggest that we go and play some golf tomorrow?. I have a handicap of 6 and you have 7 so we are very evenly matched".


"Sounds good" i said. "I think i have to cut back on the sex a little and give my cum a chance to  recover".


"Good" said oliver. "I will come in the morning with suitable golfing attire".


With that he kissed me and turned and left the room.


I slept very heavily. The days were busy and tiring and I slept like a log and  didn't even have to get up and  pee.


I half awoke the next morning and was surprised to find I was not alone in bed. I was lying on my right side  as usual and Oliver was in my bed facing me with his lips right up to and gently touching mine. "Hello sexy" he said. I was still drowsy!   Then I suddenly realised that we were not alone. I look round and I saw Arron lying up against me with his arms hanging over my chest. More than this his hard little cock was pressing into my bottom. I made no effort to resist!!!


Oliver looked at me and said "today you get a special treatment, I hope you like what we have planned". 


At that very second I felt a movement from below the sheets. I tried to look down and see what was happening but Oliver held my head and said "go with the flow".   Somebody was sucking on my rock hard dick. At that moment a little blond headed god popped his head out of the bedclothes. I was one of the little waiter boys I had seen as the restaurant. A real little beauty. 


Oliver said "may I present my youngest brother Peter".  


"How many brothers do you have i remarked?"  


"We are only  three", said Oliver.  "Peter is 13 and I do my best to keep the family together. I would rather he is here with you and me that with some overweight 50 year old getting his bum buggered to hell. When I was rescued I convinced them to take us all 3 since we had no significant parents and I would not leave Peter and Arron. That  was a couple of years ago and Peter was only 11."


"He seems very young to me" , i said.


Oliver replied "well we would rather be here than lying dead in some ditch after a drug overdose. We are all here of our own free will and we really do like you. You have become more than just a client to us. Therefore this is your special day on pleasure island. We are going to pleasure you"


And with that Oliver kissed me, Peter went back to sucking my cock (deep throat style) and Arron was holding me tight and pressing his cock into my bum cheek crack.  This had to be heaven......


Oliver kissed me deep with his tongue. He broke off for a second and said "David , we know you are a virgin  with anal sex but you are missing so much pleasure and today little Arron is going to take your cherry.  He is not very big - yet - and he will take it easy. You are going to love it."


Losing my cherry to a 13 year old i thought. That's gonna  be new ground.  


Arron slid down the sheets and engaged his tongue at my bum and began to entice my anus into submission. At first I was hesitant but as the minutes went  by I opened up to him and let him slip his tongue deep into my anus. Shortly after he reached over to the bedside cabinet and took hold of some lube which he massaged into my hole and then with his finger entered my private bum. A little 13 year old was sliding his finger in and out of my bum. Pure heaven. When he could see I was comfortable he slipt two fingers in and then three. Oliver was in full control and nodded to Arron. It was time for my fucking!!


Arron put the tip of his cock against my hole and gently pushed. I gasped briefly but I had been warmed up and  without realising it I was pushing back towards him. within a few seconds he was rocking in and out of my bum. I was getting fucked for the first time in my gay life and by a 13 year old!!!!


Peter was still sucking on my cock and pulling on Oliver's dick which was just beside mine. Oliver said out loud "I want us all to cum together".  He could sense the cum rising in our bodies. I was beginning to tense my groin and was about to cum. Arron could basically cum at any time and Oliver made sure he could finish himself off just at the right time. Oliver made a countdown 10, 9, 8 7,6, 5, 4, 3,2,1   blast off.,,,,,,,,,,,


We all three tensed our bodies at the same second and gave our cum. Arron gushed his sperm  into my bum, I gushed into Peters mouth and Oliver gushed all over Peters face.  We all lay in silence for a few seconds to recover.


Once again Oliver took the lead. "to the shower I think", he said


The three buck naked boys got out of bed and helped me to my feet. Arrons cum was dripping out of my hole. We all went into the shower and I was washed from head to toe by three gods of beauty.


"I hope you enjoy please island" said little Peter. He was so cute! He fell to his knees in front of me and gently washed my cock with his tongue!   I pulled him up since I was a little embarrassed by this little  boy giving me another blow job. 


"Did i do something  wrong?" Peter asked.  "Nothing" I said , "it's just a little difficult to get used to".  he smiled and was relieved that he was not at fault.


"Now" said Oliver "time for a quick breakfast and then off to golf for the day. We have to take a short boat ride to a public golf course so we need to have normal golf clothes. You will find them in the next room."


And with that Oliver and I sat down to breakfast and were served by Arron and Peter.  I suggested that Arron  and Peter also joined us and they sheepishly said yes. It seemed that where not used to being treated with such  kindness and respect.


Food consumed we said goodbye to Peter and Arron and made our way to the boat and the golf course. After 30 minutes boat ride we arrived at the luxery course and we played in sunny conditions. Oliver was as good as his handicap. He hit the ball longer than me but his drives were a little wild. I hit the ball  straighter but lost most of my shots on the second shot where I missed the green. We stopped after nine holes  at the bar and enjoyed a beer together. There had developed some kind of bond between us. Not just  prostitute and client but friend and lover !  Was I in love with this boy?  It was possible!!


The game took us over 4 hours and we where just about even in scores and I suspect he even let me beat him on the last hole. I  was gracious enough to accept his last deliberate putting mistake without too much  comment.


We both wanted to get back to pleasure island and declined a drink at the bar !

 

We arrived back at the bungalow and I invited Oliver in to take a shower with me after the long day. This was  the first time I had taken the initiative for sex and it was noted by him and his smile. We entered the shower. He wanted to bathe me but I pushed his hands away and I started to wash him. He did  not resist and I assured him that everything was quite ok. I went down to his groin and took his cock in my mouth and sucked him off until he was empty of cum.


He pulled me up again and kissed me deeply. 


We left the shower and put our small clothes on. I then invited him to eat with me at the restaurant. I suspected Arron and Peter would be there.  I was not disappointed. Evidently it was yellow day and the three brothers we clad in tiny yellow briefs. I noted how some of the other guests fondled Arron and Peter even though  sex was not allowed in the restaurant. For some reason this angered me. 


Oliver saw this and mentioned this was exactly why he tried to guide their activities. 


We walked back down  the path and as we entered the door the 11pm bell went. Oliver kissed me on the lips and said goodnight. "Is there no way you can be here overnight" I asked. "No", he nodded, "Sorry".


And with that he waved and walked back to his quarters.


I slipped into my bed and thought about the day. It was highly possible I was in love with Oliver and much too fond of his sexy brothers.


The days went on very much in the same way. We played some tennis, went swimming, discussed politics and current affairs. Oliver realised i was have problems in keeping up with his sex drive and even took some viagra  so I could fuck him more than once a day. I was 25 and viral but could not manage six times a day like him. I never asked but on various occasions he brought Peter or Arron or both and the little boys almost demanded I gave them a good fucking. 


My stay at pleasure island was coming to an end. It was 8am and Oliver slipped in beside me in bed. Arraon  was on the terrace setting up breakfast for us.


I could see Oliver was troubled. "What's the matter" I said. "You don't look your normal cheerful self".


"I’m Sorry" said Oliver "I know we are only paid rent boys to you but I know this is your last day. Soon you  will go home and we will never get to see you again. We have come to care for you very much and we don't think of you as a client any more - more like a brother and lover."


I look back at him and there were tears in his eyes.  "Now , now" I said trying to hold him and settle him. The tears started streaming from his 17 year old eyes and down his cheeks. 


After a few minutes his sobbing stopped. We got out of bed and put on a shirt and briefs. Arron was waiting  to serve.


Could I help Oliver ?  I did not really know. 


"I wonder" I said. 


"Wonder what" said OLiver.


I continued "Well do you ever get a holiday from Pleasure Island? Do they let you leave?"


"Yes" replied Oliver. "Actually in four weeks time pleasure island closes down for 4 weeks for decoration.  We can either go to the mainland or stay here and help with maintenance without clients."


I took a deep gulp of air. I had no idea if I was about to make a fool of myself or not.  "Well I know you all  have english passports. Why don't you three boys come and have a holiday with me in London  for a while?"


"We don't have enough money for flights" said Oliver!!


"Oliver, Oliver" I retorted "I am a very wealthy man. I trade in stocks and shares and trade mainly from home except for a limited number of business meetings. All I need is your full names and I will send you three return tickets to London. I have a large house in the center of London and I can show you around. You can stay with me"


Oliver looked at me and said "Why would you do this for three prostitutes?"


"Oliver" I replied, "You have come to mean a lot to me. I have no family and few gay friends. I would be very happy  to have you stay with me. I have a large house in which you can all get your own bedroom. I would not in any way ask you  to have sex with me"


"Ok but we like having sex with you" Oliver said, "We have become very fond of you like  a brother".


"Nice " I said but we have to remember that it is illegal for me in England to have sex with anybody under the  age of 18". 


"Well its just as well I am 18 in two weeks time" said Oliver. "And I can  guarantee you that Peter and Arron are not  going to tell anybody!!!!"


Arron had been listening. he came over crying and put his arms around me. "Are we really going to go on holiday with you?" he asked.


Oliver broke the silence "I don't think how much this means to us" , he said.  "We have been well treated here and well trained in many things but nobody has really trusted us before enough to ask us back into their homes.”


Now he had me going and the tears rolled down my cheeks as well.


Arron left the room and within a couple of minutes can back with Peter. Peter sat in my lap while Arron and Oliver sat on the arms the chair. All four of us were in tears.


The rest of the day went quickly. I told Oliver of my house and life. I assured him I would send him plane tickets on my return to London.  We were not so focused on sex but more about a normal lifestyle.


It was my last evening and I asked for the three boys to be present in my room for evening meal. At 7pm Peter and Arron turned up  with the trolley and joined Olver and me on the terrace. We had a wonderful meal talking of everything apart from sex. They wanted to  know so much about London the place they had not seen for 5 years and could barely remember.


The meal was over and Oliver stood up and said "We want to take you to bed now.   We all want to be fucked by you for the last  time”


Hów could I resist. I was well tanked up with viagra and I met the challenge with delight. I fucked all three of them. First little  Peter sat on my stomach. He was still very tight and wanted to control how quickly a cock went up his arse. After a few minutes without me cuming he pulled off. Arron lay on his back with his legs in the air and demanded I fuck him. "Fuck me, fuck me" he said. Five more minutes and Oliver tapped Arron on the shoulder. "He is mine now little brother" said Oliver.


Oliver lay on his stomach legs apart and invited me to enter him. I gently pushed into him. I could also see that Arron was now fucking Peter in the same way. Oliver was groaning and moaning with my strokes. "Give me your cum he said".  Well that took me over the edge and I shot a tremendous load deep inside his rectum. I had nothing  more to give. Not a drop of semen left in my ballsack to offer. 


I pulled off Oliver and Arron pulled off Peter. We all smiled. 


"I hope you have enjoyed your stay at pleasure Island" said little Peter. "I hope you mean what you say about inviting us on holiday?"


I pulled Peter into my arms and said "of course little one, how could I manage without you?"


Well that was the last night of my stay. I slept well that evening and at 8am Oliver came to fetch me to lead me back to reception. The receptionist asked if my stay had been satisfactory. I said it had been a wonderful experience and I was totally happy with  Oliver. She smiled and wished me a safe journey.


With that I got into the buggy and rode the short trip to the harbour and the boat back to the mainland. 


I slept for most of the 15 hours flight back to Heathrow. On returning home I tried to search the internet for signs of the three boys and their parents but I never found anything except their entries in Somerset House. They did exist and had exactly the right ages specified on their passports. Their parents were listed as unknown. It was a mystery.


So with a little hesitance and worry I ordered 3 business class return tickets from Miami to London and hoped I would not regret it. I sent them by first class post to pleasure Island along with a letter asking Oliver to email me when they would arrive.   I wondered if I would actually see them again or they would simply cash in the tickets and have a good laugh at my expense !!


Two weeks later an email popped into my mailbox.


Dear David,


We will be arriving at Heathrow at 10am on friday 14 June on BA617. We are so looking forward to seeing you.


Love Oliver, Arron and Peter.



My jaw dropped. It was really going to happen!!!   The 14th June was only three days away and I had alot to get ready. I had to make sure I had three bedrooms and three extra beds made up and had plenty of food for three hungry lads. I had to get the place properly cleaned and make sure the house was spick and span.  I quickly ordered a cleaning firm to give the large town house a good going over !!!


The three days dragged. I made a pile of cash on the stock markets to make up for it but I couldn't really concentrate.  the day arrived and at 10am I was at Heathrow at arrivals in Terminal 1 looking for three boys !!   The time passed and by 11am they had still not arrived. I was beginning to wonder if I had been made a fool of.   


Then at 11.30 the three boys came through the gate with big smiles on their faces. Oliver met me with a big grin and a hug and then so did Arron and Peter. “So sorry” said Oliver but we have lost Arron’s luggage”. 


“Never mind” I said “ we can always buy whatever he needs”.


And  with that we strode off to the taxi rank.  I wanted to take them in with style and show them London and my kensington palace gardens town house. Within 45 minutes I opened the door to my house and said “home sweet home guys”.


They surrounded me in the hall and hugged me all crying their eyes out. “We are so happy to be here” said Oliver. “Thank you for letting us holiday here”.


I showed them to their rooms one by one. “Are we not sleeping with you?” said Peter. 


“Well I would rather you at least had your own rooms you could go to when you need to be alone” I said.


With that they unpacked their few things and I said they should come downstairs when they had freshened up.


Within 10 minutes they were all downstairs and had changed into very brief white shorts.


“Boys” I said , “I think we need to make some rules here just as there are rules on Pleasure Island.  Firstly you are not rent boys here. You are on holiday. If we have sex then it will only because you want to and not because you have to.  Next I need to see you back in this house by 11pm and Arron and Peter are not to be out by themselves.  London can be a dangerous place for pretty blond boys who are a little green about London. I would worry about you all if you were on your own.”


“Remember that it is illegal for men to sex with boys under 18 so please do not talk about pleasure island or consider having sex with men over 18. Peter and Arron that means you!!”


“I will give you pocket money so you in no way should feel you have to sell your bodies whilst you are here.   I will be taking plenty of time off work and we will be seeing London together!!”


“Please enjoy yourselves and consider this to be your home.”


The boys had been silent up until now. They were still sobbing. Little Peter reached up and touched my face. Through his tears he managed to get out the words “Will you fuck us now please?”


“Peter”, I said. “that's not necessary, you don't have to give me your body”.  


“No, No” said Peter “I love you, I want you inside me”.


And with that Oliver nodded and he pulled me by the hands up to the master bedroom where we all four fucked and fucked the arse of each other for several hours!!


In the following days we “did London”. We saw the the lot - Tower of London, Piccadilly Circus, all the museums, Harrods, Downing Street, Buckingham Palace, Big Ben.  I lavished clothes and phones and other teenage items on them. 


Each evening was passed by a good meal in some restaurant in town and back to my house for several hours of fucking and sucking.


After 5 days I felt I wanted to have a serious discussion with the boys.


“Oliver, what plans do you have for your future?”


“What do you mean?” he said.


“Well - you are well read, good at sport and seem well informed about politics and business but you can't go on being a rent boy at Pleasure Island for ever. For one thing your bodies cannot take it. If your brothers are there more than a few months they will get their bodies buggered to hell. An accident is bound to happen and they will get injured.


“Well we don't really have any option do we. We don't get any real schooling at the Island. None of has have had maths or english lessons for several years now. They teach us things like butterling and sex but that's it.   I am just lucky to have a natural talent for sports. I might do something with that. I am 18 now and something has to happen pretty quickly. I have made some applications to business schools but so far I have had only rejections and beside now education is no longer free in the England. It cost about 9K per year at least.” On top of that we have nowhere to live!!!


“I have a suggestion” I muttered.   I have really fallen for you all and I feel we have something in common. I would like to suggest you continue to live with me. I will pay for you to go to school. Oliver you will need to catch up and do A level exams  and Arron will also need to catch up for O Level exams. You are both at least two years behind in schooling but you are both very bright and can catch up.  Peter is younger and has not fallen too far behind.  You can all live here as my bothers and come and go as you please.”


The boys had fallen silent. Their jaws had reached the floor!!!


Oliver was the first to react. He came over and hugged me. He was quickly followed by his brothers.


“May I have a moment with my brothers” he asked.


They moved a few steps away and went into a huddle whispering for a minute or so.


They returned to face me with huge grins their faces and tears on cheeks. They were up to something.


Oliver as usual being the oldest broke the silence. “David, we cannot thank you enough for your kind offer. We can't quite imagine how lucky we are to have met you. You have only ever shown us kindness and respect even though we have only ever been rent boys to you.  Of course we will accept - but with just two  conditions.”


“What is that?”,  I responded.


“We are trained butlers - house boys if you like.  We will run your house for you. Cook, clean and wash. We will study hard to pass exams as a mark of respect for your help”


“Secondly we ask that you continue to have sex will of us - not as rent boys but because we love you and we know you love us”


“It's a deal” I said.   Pleasure Island had moved to London


With that the three boys led me upstairs to the big walk in shower. They washed me and then led me onto the king bed and we fucked the cum out of each other the rest of the evening.



The Prologue


Well 30 years or more have passed now. I am 55 and can remember those days as if they were yesterday.  All three boys caught up  with their schooling and turned out to be very bright students. They all went to London university and continued to live with me  whilst they were in full time study. 


Little Peter turned out to be be very musical and continued to the royal college of 

music where he plays the piano. He now travels the world giving concerts. 


Arron was more science orientated and did Astrophysics and is now working for the English Space Agency in Oxford.  Both boys have found their gay life partners and live not far from here. 


Oliver  followed me into the stock markets and is a successful trader in his own right. He still lives with me and we were married shortly after he got his masters in business studies from London University. Oliver and I live happily together after more than 20 years together.


I taught the two younger boys to play golf and now the four of us play at least once a month at my club in Surrey.


I never once regretted my trip to Paradise Island or my decision to basically adopt the bothers.


Now Oliver and I  have a sexy young 17 year old blond  butler called Harry to do some of the daily chores. He cannot cook for toffee!  He is another lost boy and we help him  through schooling and university. He livens our day up now and again when we need it. Oliver who is now 47 has turned out to be a real “older brother” to him. Harry fucks like a rabbit and has the tight arse of an 12 year old virgin.








by peterholt

Email: [email protected]

Copyright 2024