Schoolboy Adventures

By Uncle Ray

 


Standard Disclaimer: This story contains sexually graphic and explicit material and as such it is not suitable for minors. If you are a minor, please leave now as it is illegal for you to be here. If it is illegal for you to read or view sexually explicit material in the community you view such material, please leave now. This story and characters are purely fictional and any resemblance to events or persons (living or dead) is purely coincidental.

 

 

 

1.     Discovery

 

Ray was out in the fields with his friends, and as is the usual way when a bunch of 10 and 11 year olds get together they were bragging about various things.

 

After a while most of the kids went home leaving just Ray and Pete. Together they lay down in the long grass and Pete got his little dick out and made it hard. Ray was very shy, and although his dick was hard he didn’t get it out.

 

Pete started talking about sex, and how Ray’s sister had let someone put his dick into her cunt to make a baby. Ray was very naive, and said that she wouldn’t do that.

 

Pete carried on stroking his dick until he shuddered a little and it went soft. He tucked it back into his pants and they went home.

 

Ray went to the bathroom at home and dropped his short trousers and pants and looked at his hairless little dick. Immediately it went hard in his hands and he tried to stroke it like he had seen Pete do, but he never got to the shudder stage.

 

 

Monday saw Ray back at school in his school uniform of jacket, shirt and tie and short trousers. His trousers were very tight, but as he was going to a new school in September his mum said it wasn’t worth getting him new short trousers.

 

Every Monday afternoon, it was country dancing in the hall for all the 9 and 10 year old children. This meant that the posh kids got to wear their nice gym kit, and the poor kids had to strip down to their underwear. Ray was one of the poor kids.

 

The very stern Mrs Porter played the piano while the kids danced round in big circles. Inevitably many of the boys got stiffies, and many of the girls pointed and laughed at them. Ray went bright red when his little stiffie poked out of his underwear and Sarah Jenkins shouted out the she could see his pee pee.

 

Ray was dragged out of the hall by Mrs Porter and taken to the headmaster’s office. Mr Stevens was a kindly headmaster and he asked Ray to sit down and thanked Mrs Porter for bringing Ray to him and told her to go back to her class.

 

“Now then Ray, what seems to be the problem?”

 

Ray explained that his pee pee got stiff and it poked out the hole in his underwear.

 

“I see, well that is a problem, let’s have a look shall we?” He asked Ray to stand on a chair facing him, and he felt all around Ray’s dick until it got stiff. “I see. It does get very stiff, doesn’t it?” Ray blushed deep red as Mr Stevens carried on fondling Ray’s dick. “Mine gets stiff as well.” Mr Stevens winked at Ray, and when it does I fondle it just like I am doing to you. Do you like it?”

 

“Oh yes, it feels good.” Ray blushed even deeper red as his body suddenly shuddered and his dick went soft.

 

“There you go then, it has gone soft now. Come and see me anytime you want to when it is hard, and I will make it go soft again for you. Okay?”

 

“Okay, I will.” Ray answered

 

“Right off you go then.” Mr Stevens turned his back to Ray and rearranged his now hard cock.

 

 

On Tuesday lunchtime, Ray rushed up to Mr Stevens office and quietly knocked on the door. Mr Stevens shouted “Enter.” And Ray went in.

 

“Hello Ray, can I help you?”

 

“It’s gone stiff again, and I can’t make myself shudder to make it go soft again Mr Stevens.”

 

“I see, well come round my desk and let’s have a look.”

 

Ray pulled his tight short trousers and pants down and a stiff little 2 inch dick stuck out.

 

“I see. It is very stiff isn’t it?” Mr Stevens gripped Ray’s cock between his thumb and one finger and stroked it.

 

“Hmm, it doesn’t seem to be going down, let me try something else.” And Mr Stevens bent down and sucked Ray’s cock into his mouth, licking all round it with his tongue. Ray almost immediately bucked and shuddered as his body went limp with pleasure.

 

As Ray’s body went limp Mr Stevens held him up and stopped him from falling.

 

“There now, is that better?” Mr Stevens asked as Ray started to recover.

 

“Thank you Mr Stevens.” Ray gasped.

 

“Come and see me anytime, okay Ray.”

 

Ray left, and Mr Stevens went into the teacher’s toilet and wanked himself until he came, his eyes closed as he relived every moment of sucking that little hairless cock.

 

 

 

Everyday for a week, Ray went to see Mr Stevens at lunchtime. And each time Mr Stevens sucked his little cock until he had a dry cum.

 

The following week, Ray was talking in class with Pete when the teacher noticed. “Raymond, stop talking this instant, she shouted from the front of the class. Pete laughed quietly, which caused Ray to laugh.

 

“Right Raymond, go and see Mr Stevens immediately and tell him that you were laughing in class.”

 

Ray went off to Mr Stevens’ office and quietly knocked on the door. “Enter”

 

Ray looked at the floor and told Mr Stevens why he was there.

 

“Hmm, that’s very serious Raymond, right I had better cane you.” Mr Stevens reached for the birch cane.

 

“Oh please no Mr Stevens, my dad will hit me if he sees I’ve been caned.”

 

“Okay Raymond, perhaps a spanking will be better then. Come here and drop your trousers and underwear.”

 

Ray bent over Mr Stevens lap as Mr Stevens slapped his bare bum. Mr Stevens immediately got hard as he saw Ray’s tight little bum hole, and stiff little cock. He reached under Ray and unzipped his own trousers and released his own cock.

 

He pushed Ray slightly further away until Ray’s face was lined up with his cock. “Suck it Ray, or I will cane you!” he said sternly.

 

6 inches of hard cock surrounded by a mass of dark hair pushed up into Ray’s face.

 

Ray put his mouth over the head of Mr Steven’s cock and started sucking and licking like Mr Stevens had done to him.

 

Mr Stevens pushed more of his cock into Ray’s mouth, making him gag, but he ignored Ray’s whimpering and carried on moving Ray’s head up and down on his cock.

 

“I’m going to cum Raymond, swallow it all!”

 

Ray didn’t know what he meant, until suddenly his mouth filled up with a hot sticky liquid. He tried to lift his mouth off Mr Stevens cock, but he wasn’t strong enough to do so as Mr Stevens pushed his head down.

 

Ray swallowed as much as he could and Mr Stevens let him stand up. Mr Stevens gave him a tissue and let Ray clean his face.

 

“Thank you Raymond, come back tomorrow lunchtime and we’ll sort out your little stiffy. Okay?”

 

“Yes Mr Stevens.”

 

“Good, now go back to your class, and no talking in class, or about what we just did. Okay?”

 

“Yes Mr Stevens.”

 

Mr Stevens gave Ray a kiss on the lips. “Off you go Ray, see you tomorrow.”

 

“Yes Mr Stevens, thank you Mr Stevens.”

 

 

2.     More Discoveries

 

 

Ray was sitting in class, when a teacher entered with a note for his class teacher. His class teacher read the note. “Raymond, you are to go and see Mr Stevens at once.” Ray got up and to murmurs from his classmates he went to Mr Stevens’ office.

 

“Ah Raymond, sit down please. I have a note from your mother, I am afraid one of your aunts has died, I don’t believe you knew her, Aunt Florence in Scotland.”

 

Ray looked confused, having never heard of an Aunt Florence.

 

“Anyway, your sister, Sandra, will pick you up after school, but she can’t get here until 5:00 o’clock, so you will have to stay behind in school until then. Normally I would get one of the teacher’s to stay with you, but no-one is available, so the janitor Mr Perkins has agreed to look after you. Okay?”

 

“I can go home by myself Mr Stevens. I’ll be alright.”

 

“I’m afraid not, your mum and dad have gone off on the train, so there is no-one at home.”

 

“Oh, okay Mr Stevens”

 

“Good, off you go back to your class, and go to Mr Perkins’ office after class, okay?”

 

“Yes Mr Stevens.”

 

 

At 3:30 Ray knocked on the door of Mr Perkins’ office. Mr Perkins was 100 years old to Ray (actually he was a 55 year old, but to a 10 year old everyone over 40 looks like a 100 year old).

 

“Now then lad I want you to sit there, be quiet and don’t touch anything. I am off to clean the sodding toilets after you little buggers have messed them up all day.”

 

Of course, as soon as Mr Perkins left Ray was looking at all the things around the office. It was mostly just paperwork and orders of janitor supplies. Then Ray peeked into the desk drawers. At the back of the bottom drawer he saw something colourful and pulled it out. Ray had found a nudist magazine. As he opened it he immediately saw pictures of naked men and women playing tennis with no clothes on.

 

His little dick got hard immediately and he rubbed it through his trousers. He listened at the door, and as he couldn’t hear any sign of Mr Perkins he sat undid his trousers and underwear and sat back down and tried to stroke his little cock in the way Mr Stevens did.

 

As Ray turned the pages he saw more pictures of men and women naked, and on the next page he saw some boys and girls his own age. He looked really closely and he could see the men’s big cocks and the little boy cocks, and he could even see the women’s pussies and the little girl’s pussies. All perfectly innocent of course, but it made Ray stroke his little cock even harder.

 

Ray was so engrossed in the magazine he hadn’t heard Mr Perkins return. “Do you like that lad?” Mr Perkins gruff voice made Ray stand up suddenly and he dropped the magazine to the floor.

 

Mr Perkins picked it up and gave it back to Ray. “I told you not to touch anything, well too late now I guess.”

 

Ray looked up from the floor, he could see Mr Perkins had a huge bulge, just like Mr Stevens did when Ray was with him. Instinctively Ray reached out to touch it, but Mr Perkins pulled back and looked at Ray quizzically.

 

Ray was still standing there with his trousers and underwear round his ankles and a stiff little cock sticking out. Mr Perkins seemed to make up his mind, he turned and locked the door and pulled a small curtain across the window.

 

“Okay lad, do you want this?” Mr Perkins undid his trousers and pulled out a very large cock, surrounded by greying hair. To Ray it looked enormous, much bigger than Mr Stevens’ cock was.

 

Mr Perkins rubbed it up and down a little making it fully hard. “Do you want it in your mouth or your bum lad?”

 

Ray looked confused, ‘in my bum’ he thought, ‘is that possible’. He started to turn round to put the magazine down. Mr Perkins interpreted that as being ‘in my bum’.

 

 

“Okay lad, bend over the chair.”

 

Ray was totally confused, but he did as he was told.

 

Ray felt something cold on his bum as Mr Perkins spread something on it. The next thing he knew he felt a finger enter his virgin bum. Mr Perkins pushed hard and got his finger in.”Are you sure lad, have you done this before?”

 

“No!” Ray said through a few tears.

 

“Oh well. Turn round lad; I assume you have had a cock in your mouth then.” Mr Perkins withdrew his finger.

 

“Yes.”

 

“Well open wide lad” Ray opened his mouth and sucked on the head of this very large cock.

 

“Tilt your head a little” Mr Perkins tilted Ray’s head up and pushed more of his cock into Ray’s mouth. “Breathe through your nose lad.”

 

Mr Perkins pushed and the tip of his cock went into Ray’s throat. Ray gagged as he did so. “Breathe through your nose lad.” Mr Perkins pulled his cock out and then pushed back in harder. As he fucked Ray’s face, he used his thumb and finger to wank Ray.

 

“Here it comes lad.” Mr Perkins pushed hard into Ray’s throat as he came.

 

Mr Perkins pulled out of Ray’s mouth and started sucking on Ray’s cock until Ray shuddered as he had a dry cum.

 

Ray and Mr Perkins got dressed again. “Thank you lad, would you like to keep the magazine, it will be just our secret, alright lad?”

 

“Thank you Mr Perkins. Just our secret.”

 

“Good lad, Ray is it?”

 

“Yes Mr Perkins.”

 

“Well Ray, come after school anytime you want okay, I’ll find some more magazines for you. You can come to my bungalow next to the school if you want.”

 

“Thank you Mr Perkins.”

 

 

A very pregnant teenager knocked on the door. Mr Perkins opened it and Ray’s sister came in. “Come on Ray, you are coming to my flat tonight.”

 

“Bye Mr Perkins, see you tomorrow.” Ray smiled at Mr Perkins as he and his sister left.

 

Mr Perkins went back to his job; cleaning up after the ‘little buggers’ as he called them.

 

 

 

That night after dinner, Ray sat in Sandra’s flat wondering what to do. Sandra was having a bath, and there wasn’t much on television. He pulled the magazine out of his schoolbag, and his little cock got stiff very quickly as he looked at the pictures. He especially liked looking at the hairy men with their soft cocks and heavy balls hanging down, as well as the women with hair all round their privates.

 

He heard the bathroom door open and hurriedly put the magazine back in his school bag. Sandra came in wearing a dressing gown, and with a towel wrapped round her head to dry her hair.

 

“Mum left some clean clothes here for you before she went and some pyjamas for you, if you want to have a bath and get ready for bed.”

 

Ray was hardly listening, or even breathing. His eyes were transfixed by the sight of the first adult pussy he had ever seen. As Sandra was nearly 8 months pregnant, she was slouched back on the sofa and her dressing gown had fallen open a little.

 

“Did you hear me?”

 

“Um yes, bath, okay.” Ray reluctantly lifted his eyes up from Sandra’s pussy.

 

“Well go on then!” Sandra said as she leaned back trying to get comfortable.

 

Ray stood up and his stiffie poked the front of his trouser out.

 

“Ray, come here a second!”

 

Ray walked over to his sister.

 

“What’s this in your pocket?” Sandra poked Ray’s stiffie with her finger. Ray went a deep shade of red.

 

“Oh! I’m Sorry Ray! I didn’t realise you were older and could, well you know. Oops!”

 

Sandra laughed loudly and Ray rushed from the room.

 

 

 

 

3.     In town

 

Ray’s sister walked him to school. “Remember, I can’t pick you up tonight, so here’s some money for the pictures okay. I will pick you up outside at 6:00 o’clock, don’t make me wait!”

 

Ray went to his lessons, although he didn’t go to Mr Stevens at lunchtime, and he didn’t see Mr Perkins.

 

At 3:30, he said goodbye to Pete and walked into town alone.

 

He was wearing an older pair of short trousers today, and they were definitely a bit tight on him.

 

As he walked, he noticed that men were looking at him. He checked his flies several times to make sure nothing was wrong, but he carried on walking in his too tight short trousers and his school jacket.

 

As he walked across the park, he decided that he needed a piss, so went to the park toilets. They were a bit old and smelly, but he needed a piss, so he had to go in. Luckily there was no one else in there. His trousers were tight so he decided to go into a stall. Of course the door lock was broken, but there was no one else around, so he pulled down his trousers and underwear and sat down to piss. As he sat there he started noticing the drawings and writing on the walls. The first ones he noticed were of women with their legs open and a drawing of their pussies wide open.

 

Ray’s had finished pissing, but his cock was now very hard. Then he noticed the pictures of men wearing stockings with their hard cocks being sucked by other men.

 

Ray was stroking his cock hard when the door opened and a really old man stood there.

 

“Having fun lad?”

 

Ray tried to cover himself up, but the old man stepped into the stall and shut the door behind him.

 

The old man unzipped himself and pulled out an old wrinkled fat cock. “Carry on lad; I’ll join in as well.” The old man starting stroking his cock as it grew harder and even fatter.

 

“Have you ever sucked a cock lad?”

 

Ray nodded yes.

 

“Well go on then, get on with it.”

 

Ray was trapped, so he knew he had to do what the old man wanted. He leaned forward and started licking all round the old man’s cock before sucking the head into his mouth. It was by far the fattest cock Ray had sucked so far, and the old man grunted with satisfaction as Ray worked his tongue around it. The old man pulled on the back of Ray’s head to face fuck him harder.

 

“Fucking Hell!” the old man grunted as his cum flooded into Ray’s mouth.

 

The old man let go of Ray’s head, put his still dribbling cock away, and was gone really quickly. Ray pulled up his trousers and ran as fast as he could into town.

 

 

Outside the cinema, Ray decided to see a western that was on, mainly because it finished at 5:45, so he wouldn’t be late for his sister.

 

He bought his ticket and looked longingly at the drinks and popcorn on offer, but his sister had only given him enough money for the ticket.

 

He went in the theatre and headed for the back, where he would normally sit on a Saturday with his friends. As he sat down, a young man of about 25 sat down with him. “Here kid, you can share my popcorn, I saw you looking at it outside.”

 

“Thanks mister.” Ray replied.

 

“Call me Jimmy, what’s your name kid?”

 

“Raymond.”

 

The lights went down and Jimmy offered Ray some popcorn. As Ray reached over, Jimmy moved his hand so it was resting on Ray’s leg under the popcorn.

 

Ray didn’t mind, Jimmy seemed quite nice anyway.

 

After a while Jimmy moved his hand a little higher and started rubbing the inside of Ray’s thigh. Ray liked it and opened his legs a little wider. Jimmy lifted his hand off of Ray’s leg and took hold of Ray’s hand and put it on his own leg. Then he went back to gently rubbing Ray’s thigh.

 

Ray sighed as nice feelings ran up his leg, making him feel relaxed. Jimmy moved his hand a little higher, reaching Ray’s tight shorts. “Can you take your shorts off Ray? They feel really tight on you. It must be uncomfortable.”

 

Ray reached down and undid his shorts and slid them down, along with his underwear. “That’s better, they are too small for me.” Ray said as Jimmy reached over and put Ray’s hand directly onto his hard cock. Jimmy had released his cock from his trousers while Ray was struggling with his shorts. Jimmy moved Ray’s hand up and down, wrapping Ray’s fingers around his cock, and then once Ray had got the knack, he used his fingers to start wanking Ray.

 

“Oh that’s nice Ray.” Jimmy breathed heavily.

 

Ray moved his hand up and down carefully in long slow strokes. Jimmy put him arm around Ray and pulled him in tight, with one hand around Ray’s shoulders and the other hand wanking Ray.

 

Gradually, Jimmy pushed Ray closer and his head down, until eventually Ray’s face was close enough to Jimmy’s cock that he could easily push Ray’s face onto it. Ray opened him mouth wide and sucked Jimmy’s cock into it, using his tongue he licked all round it.

 

Jimmy suddenly pushed Ray down hard forcing his cock into Ray’s mouth as he shot spurt after spurt of cum into it. Ray swallowed as fast as he could, managing not to spill too much.

 

Ray sat up and watched the rest of the film, shuddering after a while as he had a dry cum while Jimmy wanked him.

 

As soon as the credits began to roll, Jimmy was gone, leaving Ray to struggle to get his shorts on before anyone noticed.

 

 

 

Ray left the cinema and looked around. There was Sandra talking to someone. Sandra waved, and the stranger turned around. “Ray, this is Jimmy, he is coming home with us tonight because Jimmy and I need to talk. Okay?”

 

“Hello Ray, I am pleased to meet you.” Jimmy winked at Ray so that Sandra didn’t see. “Come on, my car is just round the corner.”

 

When Sandra wasn’t looking Jimmy put his fingers to his lips so that Ray knew not to say anything.

 

 

 

 

4.     The first time

 

That night Ray was woken up by Sandra’s and Jimmy’s voices coming from Sandra’s bedroom. He could hear Jimmy saying “yeah baby suck it good.”

 

Then he heard Sandra complaining that it was too uncomfortable.

 

Then he didn’t hear anything for a while until his bedroom door opened.

 

“Ray, are you awake? Ray I need to fuck someone and it’s going to be you as your sister can’t.”

 

Ray was aware that the covers were pulled off him and Jimmy sliding into bed with him. He felt Jimmy’s hands on his bum, probing, until a finger was inserted.

 

Jimmy pushed his finger in and out for a while, until he pulled out and inserted two fingers.

 

Ray was silent the whole time. He could hear Jimmy spitting on his fingers and a third finger being inserted.

 

Suddenly Ray felt empty as Jimmy pulled all three fingers out of his bum. Then he felt Jimmy’s cock pushing at the entrance. “Relax Ray, this will hurt a bit, then it will be fine okay little fella.”

 

Jimmy pushed hard, and about 2 inches of his cock entered Ray. Tears filled Ray’s eyes as Jimmy pushed again and another inch disappeared into Ray.

 

“Relax Ray, it will be okay.” Jimmy pushed hard and all six inches of his cock were now inside Ray.

 

“Okay Ray, hold still for a while, then I’ll start okay little guy?”

 

Through his tears Ray managed to mumble “Okay.”

 

Jimmy started moving in and out of Ray, and after a little while the pain eased off a bit.

 

“You okay little fella?” Jimmy asked

 

“Yes.” Ray managed to say. He was still crying a bit, though not as much.

 

Jimmy started moving faster in and out, making moaning sounds as he did so.

 

Suddenly Jimmy stiffened his back and Ray felt cum spurt into his backside.

 

Jimmy pulled out and went back to bed with Ray’s sister.

 

Ray went to the toilet and expelled the masses of cum from his bum, cleaned himself up and went back to bed.

 

 

 

Ray woke up with sun streaming through his windows. He washed and went downstairs to find that his sister had gone to work and Jimmy was sitting downstairs drinking coffee.

 

“Hey there Ray, are you okay?”

 

“I’m a bit sore.” Ray replied.

 

It will be easier next time Ray, you are lucky I’m not that big so it wasn’t too hard for you. Come on, I’ll have a look and apply some lotion okay?”

 

“Okay Jimmy.”

 

Jimmy applied some lotion which helped make it easier for Ray.

 

 

 

Later, Ray’s sister returned from her job and told Ray that Mum and Dad would be home on Tuesday after the funeral. She asked Jimmy if he could run them over to Ray’s to get some more clothes for him.

 

“I’ll take him if you give me a list of what to bring back.” Jimmy offered.

 

Sandra prepared a list and gave it to Jimmy.

 

When they arrived at Ray’s house, Ray rushed up to his bedroom to get some toys to take back as well as the clothes on the list.

 

Jimmy arrived in Ray’s room and looked around. It was a typical small boy’s room, although everything was a little bit old and worn.

 

“How are you feeling Ray? Because I need to fuck you again, right here in your bedroom.” Jimmy already had his cock out and was stroking it.

 

“Um, I’m okay I guess” Ray answered.

 

“Get undressed then and bend over the end of your bed.” From his trouser pocket he produced some Vaseline he had taken from Sandra’s

 

Ray was bent over the end of his bed and Jimmy applied some Vaseline. He eased his hard cock in slowly. “See it is going in much easier this time.”

 

Jimmy was soon fucking Ray hard. Ray himself had a stiff little cock as Jimmy pounded him.

 

Jimmy took his time, stopping every now and again to make himself last longer. Each time he stopped he reached round and wanked Ray’s cock.

 

After a while Jimmy slammed into Ray as hard as he could, shooting cum inside him.

 

He pulled out and rolled Ray over, engulfing Ray’s cock in his mouth and sucked hard until Ray shuddered with a dry cum.

 

 

“There you go, come on let’s get the things on the list.” Jimmy said as he stuffed his cock back into his trousers.

 

An hour later they were back at Sandra’s. “I’ll see you tomorrow Sandra, I’m off to see my mates.”

 

“Okay Jimmy, I’ll see you tomorrow.” Sandra replied.

 

 

 

 

5.     Tight fit

 

Mr Perkins brushed past a lot of kids including Ray in the corridor. “Bloody kids” he muttered under his breath.

 

Ray’s day passed as usual, including a visit to the headmaster’s office at lunchtime to suck Mr Stevens’ cock.

 

As Ray was walking home he was rummaging in his pocket trying to find a penny to buy a sweet when he found a note with two pennies in it. The note was from Mr Perkins, it said ‘I have found some nice magazines that you will like, try and come to my bungalow at the weekend’.

 

Ray remembered Mr Perkins brushing past him earlier; he must have put the note in his jacket then.

 

 

 

On Saturday, Ray told his mum he was off to play in the park. Instead he went to Mr Perkins’ bungalow. Ray knocked on the door and a scruffy looking Mr Perkins opened the door. He saw Ray, looked around very carefully to make sure no-one else was around and pulled Ray through the door.

 

“Well Ray, have you come to look at my magazines then?”

 

“Yes please Mr Perkins.”

 

“Very well then, come inside.”

 

Ray walked into the back room, it was dark and the curtains were pulled. Mr Perkins turned the light on and rummaged around in a cupboard. “Here you go, try this one.” He put a nudist magazine on the table. This one was a family edition, with lots of young children of Ray’s age and younger. Ray flicked through the pages looking at all the smiling children showing their bodies to the camera.

 

Ray dick was hard, and he absently rubbed it through his shorts.

 

“Take your shorts off Ray, you will be more comfortable.” Mr Perkins rubbed Ray’s shoulders as Ray undid and took off his shorts and underwear.

 

“Try this one.” Mr Perkins put another magazine in front of Ray. The cover featured a body builder type man in a loin cloth. Ray opened to the first page and there was a picture of the man naked. On the next page, the man was naked, but his cock was hard and pointing right at the camera.

 

Ray turned the pages excitedly, seeing page after page of men with hard cocks smiling at the camera.

 

Mr Perkins put down another magazine. This one had a plain cover. Ray let go of his cock and opened the cover. There was a small boy of maybe 5 or 6 years old, standing next to a man with a large erect cock.

 

As Ray turned the pages, he saw the small boy sucking not one, but two cocks, then he saw the boy bending over a table with a cock being pushed into his bum. The boy was smiling at the camera.

 

The next picture showed the boy with a cock buried deep in his bum and another cock deep in his throat.

 

“Bend over the table Ray.”

 

Ray turned and saw the Mr Perkins was naked and his very large cock was purple and hard.

 

“Bend over Ray, this is going to happen.”

 

Mr Perkins pushed Ray down onto the table and put something cold onto Ray’s bum.

 

As Mr Perkins pushed one then two fingers into Ray’s bum he said “Good, you have been fucked before.”

 

Mr Perkins lined up his 9 inch cock and started to push in.

 

Jimmy had taught Ray how to push out a bit to make it easier and the first 2 inches of cock went in easily. Mr Perkins’ cock was much fatter than Jimmy’s cock and a lot of force was needed to get the next 2 inches in.

 

Mr Perkins rested for a little while, and then he pushed again and another inch disappeared into Ray.

 

“It’s too big!” Jimmy tried to say through tears as pain ripped through his body.

 

“Relax Ray.”

 

Mr Perkins shoved hard and inch by inch the full 9 inches went into Ray.

 

“Hold still Ray.”

 

Mr Perkins pulled out a little, and then pushed hard back in.

 

Each time he pulled out a little more before pushing back in hard.

 

After a little while it stopped hurting quite so much and Ray got into the rhythm.

 

His little cock was rock hard as Mr Perkins was now pulling almost all the way out and slamming back in.

 

Mr Perkins pushed in really hard, grunted and flooded Ray’s bum with cum as pulse after pulse went deep inside Ray.

 

Sweat dripped onto Ray’s back as Mr Perkins reached round and fondled Ray’s cock. He pulled out, picked up Ray and sat him on the table and sucked Ray’s cock into his mouth, sucking until Ray came.

 

“The toilet’s through there; go and clean yourself up.”

 

Ray went to the toilet and expelled more cum than he thought was possible.

 

Ray went back to get dressed again and Mr Perkins handed him a cup of tea. “You’re a good lad Ray. Well Done! You can come and look at the magazines anytime Ray.”

 

“Thank you Mr Perkins, I would like that.”

 

“Okay kid, anytime.”

 

Mr Perkins sat there naked stroking his cock, which soon resumed its full 9 inches. “Do you want to suck it Ray, before you go? I’ll let you keep the nudist magazine if you do.”

 

Ray got down on his hands and knees and sucked as much cock as he could into his throat until Mr Perkins came again. Ray swallowed every last drop of cum.

 

“Thank you Ray, I’ll see you soon.”

 

“Thanks for the magazine Mr Perkins.”

 

Ray walked home via the park, avoiding the toilets. He had had quite enough cum for one day.

 

At home he carefully hid the magazine at the back of his cupboard.

 

 

 

6.     Summer holiday

 

It is the summer holidays, and that means long days in the company of Pete. The two of them relaxed in the long grass on the hill above the town. As usual Pete had his cock out and was slowly wanking. Ray leaned across and whispered “Can I suck it?”

 

“What?”

 

Ray leaned across further and sucked Pete’s cock into his mouth. Pete lay back and enjoyed this new sensation. After a very short time Pete shuddered to s dry orgasm.

 

“Are you going to suck mine?” Ray asked as he pointed his little stiffie as Pete.

 

“I guess so.” Pete sighed and tried to suck Ray’s cock, but he wasn’t very good at it and in the end Ray went soft without a dry cum.

 

 

 

Ray opened the back door to his parent’s house. “Oh there you are, come on, we need to pack, Dad got his overtime paid.” Ray’s mum was fussing around trying to get clothes washed and ironed.

 

 

 

The family bundled onto the coach, Mum, Dad, sister and new baby and Ray. The baby cried most of the way. Eventually after a taxi ride from the bus station they all arrived at a caravan park in a big field next to the cliffs.

 

The caravan was small with fold out beds and a small kitchen. After quickly unpacking, the whole family set off to walk into town and a fish and chips supper.

 

Ray looked longingly at the fun fair, but he knew the family couldn’t afford the price of the rides. They all walked back along the sandy beach, laughing at the few evening bathers running into and quickly back out of the North Sea water.

 

They stopped off at the clubhouse, and Ray’s parents had a drink while Sandra took the baby back to the caravan to feed him and get him to sleep. Ray was allowed in the clubhouse, and marvelled at the noisy smoky atmosphere. Everyone was laughing at a comedian on stage and even his parents looked happy.

 

Eventually they all went back to the caravan and Ray slept really well until the baby started crying. Ray got up to go to the toilet, and saw his sister breast feeding the baby.

 

“Can you get that towel please Ray? Ray?”

 

“What, oh yeah, sorry!” Ray handed the towel to Sandra.

 

“It’s a tit Raymond, nothing special, it’s just a tit.” Sandra swapped the baby over to the other side while Ray stood with his mouth open. “Come and sit down Ray, I want to talk to you.”

 

Ray tore his eyes away from Sandra’s tits and sat down.

 

“Is everything okay Ray? I don’t see much of you these days, and now Jimmy has gone back to sea, I could do with some company now and then. I’ll always be your big sister Ray, you know that, and I would like to see you more often.”

 

“I promise I’ll come over more often.” Ray looked up and he could see a tear in his sister’s eye. “I promise I will.”

 

“Thank you Ray, I look forward to that.” Sandra gave Ray a kiss on the lips. Her tit brushed against Ray’s chest as she did so. “Thanks Ray. Go on, off to bed with you.”

 

Sandra carried on feeding the baby as Ray went off to bed with a very stiff cock poking out the front of his pyjamas.

 

 

The next day, the sun was shining, and the family had a quick breakfast and headed down to the beach. Ray’s mum held a towel while Ray got changed into a much too big pair of swimming shorts. Ray and his Dad ran down to the water and jumped in, and very quickly ran back out of the cold water. Inevitably, Ray’s shorts dropped down exposing his tiny cold-shrivelled cock to everyone on the beach. Ray pulled them back up really fast and ran back to his mum followed by his dad laughing behind him.

 

“We’ll get you some that fit tomorrow Ray.” His mum laughed as she purposely leant over and pulled them down in front of everyone. “Well there isn’t much to look at yet anyway!”

 

“Mum!”

 

Ray’s cock had got hard with all this unwanted attention and was now sticking straight out for the full 2 inches.

 

“Well perhaps we had better get some today.” Mum laughed again, “Since Raymond is pointing the way to the shop.”

 

Everyone laughed including the family next door. Ray went a deep red colour.

 

“I’ll take him if you can watch the baby for me.” Sandra volunteered.

 

 

A little later, they returned with Ray sporting a tight pair of swimming trunks.

 

Ray and his dad went back and spent a long time jumping in the sea, with Dad picking Ray up and throwing into the waves. As his dad picked him up, he often grabbed Ray crotch to hold him before throwing him into the sea again.

 

By the time they went back to the family, Ray was sporting a hard cock which showed very much in his tight trunks. His Dad also sported a nice semi hard bulge in his trunks, though not as obvious as Ray’s.

 

Sandra smiled when she saw his cock in his trunks and Ray tried to cover up as best he could.

 

They had sandwiches on the beach for lunch.

 

Ray went off to the promenade to use the toilet while the family dozed in the sunshine and Sandra fed the baby.

 

 

Ray went in the toilet block, there was a bit of shuffling by the two men in there as one came out of a cubicle. Ray pulled down the front of his trunks, his cock leapt out and back to full hardness as it seemed to do every time he used the toilet.

 

He looked to his right as he pissed to see a man of about his dad’s age slowly stroking his hard cock while looking straight at Ray. A head popped out of the cubicle and popped back in again.

 

Ray finished pissing, but his cock was still hard. The man had moved over and was now right next to Ray stroking his cock and showing it to Ray.

 

“Nice cock you’ve got there kid.”

 

“Um, thank you.”

 

“Do you like mine kid?” The man pointed it straight at Ray and let go of it so Ray could see all of it.

 

Footsteps outside caused the man to move away quickly and turn away.

 

“Ah! There you are Ray.” Ray dad stood at the urinal and pulled out his own semi hard cock and started pissing. A long hard stream of piss hit the pan. While he was pissing the other two men had quickly left.

 

Ray was still standing there with his hard cock jutting out of the top of his trunks.

 

His dad finished pissing and started stroking his cock to hardness. “I see you are still hard Ray, do you know what to do to make it go down?”

 

Ray started to wank his cock to show his dad.

 

“Yeah that’s right son.” Ray’s Dad carried on stroking his own cock which was now very hard and a full 7 inches.

 

Without saying anything Ray reached across and started to wank his Dad.

 

“You shouldn’t be doing that Ray. But it is nice, but, Let’s go into a cubicle son.”

 

They went into a cubicle and Ray resumed wanking his dad.

 

Dad picked up his son and put him on the closed lid of the toilet and started wanking his son until Ray had a dry cum.

 

“No cum yet? It will be soon enough.”

 

Dad carried on wanking his own cock until he suddenly said he was cumming. He grabbed Ray and quickly shoved the head of his cock into Ray’s mouth just as spurts of cum shot into Ray’s mouth. Ray swallowed hard until nothing was left.

 

“Lovely Ray, I needed that badly. Don’t tell your Mum okay?”

 

“Okay Dad.”

 

“Come on, let’s get back.”

 

As they left the cubicle they saw another man and his son at the urinals. The son looked to be around 6 or 7 years old. He had both his hands tight around his dad’s 8 inch cock which was very hard with a large purple head. The man winked at Ray’s dad as he pulled his son’s face to his cock. The son opened his mouth wide and immediately started sucking.

 

 

Ray’s dad pushed Ray out the door. Both of them did their best to hide their now hard again cocks in their tight trunks, but several men stared and winked at them as they went back to the beach.

 

 

 

Ray and his dad went to the clubhouse while Mum cleared away. They were sitting in the corner when a man approached with his son. “I thought it was you, we met briefly this afternoon. I’m Derek, and this is my son Del.”

 

“Oh, er, hi. I’m Don, this is my son Raymond, I mean Ray.”

 

Derek sat down and went through the usual stuff about whether they were here for one week or two weeks and so on. All the time he was talking Del was sitting on his lap fidgeting.

 

After a while Derek leaned back and Don could see that he was holding Del’s little stiffie, and Del had his hand under him rubbing Derek’s cock.

 

“Anyway”, Derek said as he leaned forward again, “It’s bingo for the girls tomorrow night in the club house, maybe you and Ray would like to come over for a beer or something? We’ll introduce the missus’s when they get here. I’m sure we will have a lot of fun.”

 

“Well, er, I...”

 

“Daddy, can I sit on Uncle Don’s lap for a change and maybe Ray can sit on your lap.” Del asked as he jumped off Derek’s lap

 

Without waiting for an answer, Del jumped onto Don’s lap, and pulled Don’s arm over so Don was touching his little stiff cock.

 

Don gasped as he felt his button fly being undone.

 

“Well, er ,... Ray sit on Derek’s lap for me please.” Del shuffled down and slid down his shorts, and back up and inserted the end of Don’s now hard cock into his bum.

 

Ray sat on Derek’s lap, unaware that Derek had released his own cock. Derek pulled down the back of Ray’s shorts, and positioned his cock at the entrance to Ray’s bum.

 

By now Del had eased most of Don’s cock up his bum. He began twisting around to the music on the jukebox. Don became flustered as his cock was in the tightest hole it had ever been in. The feeling was intensely pleasurable.

 

Derek had been easing his cock into Ray, and was pleased that it was sliding in so easily. Ray also began dancing to the music as Derek’s cock eased the rest of the way in.

 

Don’s wife appeared almost at the same time as Derek’s wife. They almost bumped into each other. Even though Derek had his cock all the way into Ray’s bum, he made the introductions without standing up. He reached into his pocket and produced a fiver and asked his wife Cynthia to get a round in. Valerie, Don’s wife offered to help.

 

It was too much for Don as he shot a large amount of cum into Del.

 

Seeing Don break into a sweat before relaxing, Derek pushed hard into Ray and shot his cum into him.

 

By the time Cynthia and Valerie returned everything was buttoned back up again, and the boys had gone off to the toilets to unload.

 

 

 

 

 

7.     A new School and a new discovery

 

 

Ray was all prepared for his new school. A grammar school boy! Ray’s mum was so proud.

 

He had new shoes and long grey socks, new short grey trousers, white shirt, purple tie and a purple jacket.

 

Every single one of Ray’s mates was going to the two local schools. Ray has hardly seen Pete since it was announced that they were going to different schools.

 

 

The first day of school involved walking to the bus stop, and two buses later walking into the big school.

 

There were about 200 ‘new’ kids looking bewildered and 1200 kids from 12 year olds up to 17 year olds.

 

Ray looked around and found a group of kids his age and tagged onto them. Gradually over the course of 20 minutes he knew at least some of them.

 

School assembly consisted of all the new kids at the front in a big hall, and all the teachers up on the stage. Ray could see a few of the teachers checking out the kids sitting at the front. Some were checking the girls in their skirts, and some checking the boys in their shorts.

 

After assembly, the new kids stayed behind, and in groups of 30 they were taken by a teacher to their classroom, given their schedules and settled down. Kids that already knew each other tried to stay together, but the street-wise teachers broke them up so that very few kids were sitting with someone they already knew.

 

The morning passed easily enough, lunchtime in the canteen was remarkably well behaved, although the teachers walking around with canes in their hand probably kept things quiet.

 

At 4:00, Ray began the journey home, having made some friends, a few enemies, and mostly kids who didn’t care about him either way.

 

 

The first week passed really quickly. His first taste of rugby came as a shock, as did the communal showers, with the teacher showering with the kids, to keep things quiet. The Welsh rugby master was huge in every way, a large pendulous cock hanging down from beneath his large beer gut.

 

In the second week, Ray got his first taste of trouble for talking in class, and was sent to the headmaster, Mr Forth, A large old very stern looking man.

 

Ray waited outside his office door, until he heard his name called out “Smith, Raymond” He opened the door and started to enter. “Go outside, close the door and wait until you are called. Then you knock on the door and wait until I say enter!” Mr Forth bellowed.

 

“Smith, Raymond!”

 

Ray knocked on the door.

 

“Enter!”

 

Ray entered the room and stood very still.

 

“Well? Why are you here?”

 

“I was sent here by Mrs Clark”

 

“You address me as ‘sir’! Now why are you here?”

 

Mrs Clark sent me Sir, for talking in class Sir.”

 

“Much better Smith. We’ll knock some manners into you by the time you leave.”

 

The headmaster looked at his notes. “You had Mr Stevens at your last school I see.”

 

“Yes sir.”

 

“Well things are done differently here. It’s only your second week. I don’t expect to see you again this term for bad behaviour. Do you understand Smith?”

 

“Yes sir.”

 

“Well go back to class and behave.”

 

“Yes sir, thank you sir.”

 

The term passed uneventfully.

 

 

Christmas came and a present for Ray. A new bike, well a repainted old bike, but Ray was delighted. It meant that he could cycle to school instead of taking the long bus journey.

 

Another secret present for Ray was the first few hairs round his cock. Ray of course measured his cock every day and it had grown to an impressive ‘nearly’ 3 inches.

 

 

 

January and February saw Ray either on the bus or cycling to school depending on the weather. With the first sunshine and slightly warmer days in March Ray started to explore the areas around his journey to and from school. He found a small park with an old toilet block right in the middle.

 

Ray stopped off every day and looked at the pictures on the wall while wanking himself to a dry cum.

 

One day Ray was in one of the cubicles and he heard a noise. He looked through a hole in the wall and could see someone wearing stockings and nylon panties. When they turned round Ray saw that it was a man of with a hard cock that they were wanking. The person saw Ray looking and hurriedly came into Ray’s cubicle. He immediately bent down and sucked Ray’s 3 inch cock into his mouth and expertly rolled his tongue around giving Ray the most intense pleasure. Ray humped against the man’s face until he shuddered. Ray fell to his knees and wrapped his hands around the man’s cock and sucked him until he came.

 

“Thanks kid, see you again, same time most days.” The man pulled up his nylon panties, and then some normal men’s trousers. As he left he looked like a normally dressed man.

 

Ray’s cock was hard again, the feel of the nylon on his face when he was sucking the man had felt incredible. Ray cycled home with his fly open, feeling the cold wind rushing over his still hard cock.

 

 

Ray couldn’t get the feeling of the nylon out of his head, and although he didn’t go back to the toilets for a few days, he craved that feeling again. He looked in his mum’s underwear, but there was nothing remotely like it.

 

Ray had been going to see his sister more often, and after a quick peek in the dirty washing he found exactly what he wanted, some thin nylon panties. He put them in his pocket for later.

 

As it was Friday Ray often stayed over as Sandra’s so his parents could enjoy a night out.

 

Ray went to bed, and slipped on the stolen nylon panties. His cock immediately got hard and he tried wanking through the panties. The feeling was incredible. He must have moaned out loud, because the bedroom door flew open and his sister wearing a nylon negligee burst in.

 

Ray opened his eyes and saw his sister naked under the negligee and he came. A small wet patch formed on the front of the panties. Ray had his first wet cum.

 

Sandra looked shocked and then she laughed. “I wondered where I had left them. Stay there Ray and don’t move.” Sandra rushed out of the room. She returned with a bra, a suspender belt and stockings.

 

“I’ve always wanted a sister, and now I’ve got one.” Sandra touched the small sticky spot on the front of the panties Ray was still wearing. “How long have you been able to cum?”

 

Ray’s cock immediately got hard again. “It’s the first time!” Ray croaked deeply embarrassed as his sister ran her fingertip along Ray’s cock.

 

Sandra got Ray to sit up and clipped a bra round him along with the suspender belt. She got him to lie back again and she pulled the stockings onto him and attached them to the belt.

 

“Stand up Ray!” Sandra ordered.

 

Ray stood there. His cock was harder than ever, pushing out the front of the panties.

 

“Not bad, we’ll have to do something about this though.” Sandra gripped Ray’s cock and he let out a little moan.

 

Sandra pushed Ray onto the bed and pulled his cock out of his panties and sucked it into her mouth. She licked all round it and Ray tried to push it further into her mouth.

 

Sandra looked at Ray with a curious look on her face. She then lifted the negligee off her, she was completely naked. She moved up and lowered her hairy cunt onto Ray’s cock, which slid in easily. She pulled Ray’s hands onto her tits showing him how to rub and tweak her nipples.

 

She gyrated on Ray’s cock; rubbing her clit furiously to make herself cum. Ray just lay there not knowing quite what to do. Sandra bounced up and down on him until she cried out as she came. Ray pushed up and a tiny amount of cum came from his cock.

 

Sandra collapsed onto Ray breathing heavily.

 

“Come on, you’re sleeping with me tonight, and every Friday and Saturday night from now on. You are going to be my sexy little sister.”

 

She dragged Ray into her bedroom and into bed dressed exactly as he was.

 

 

 

When Ray woke up in the morning, there was a clean set of clothes for him, clean panties in a sheer red nylon, stockings, bra complete with some padding to give him small tits. A see-through blouse, a very short skirt and a pair of high heels completed the picture.

 

Ray rushed to his bedroom, but his own clothes were nowhere to be seen.

 

Reluctantly, but also in a state of excitement Ray got dressed and went downstairs.

 

“Fucking hell! You look so sexy Ray.” Sandra hugged him and kissed him on the lips, her tongue darting into Ray’s mouth and swirling around his tongue. Her hand tweaked his hard cock. “I can feel how much you like it Ray. We’ll do some make up later, before we go out.”

 

“I can’t go out like this!” Ray said quietly.

 

“I have a wig you can wear, no-one will notice. We won’t go far. Now, what shall we call you? You look like a Betty, so Betty it is. My cousin Betty, yes I like that.”

 

 

Very reluctantly Ray followed Sandra out to the local shops. Walking unsteadily on the 3 inch heels that Sandra had given him, he gradually got the knack of walking in them. Sandra introduced Betty to several people they met. Ray couldn’t help but notice the way the men in the shops looked at him, some of them were openly squeezing their cocks while they did.

 

He had to admit, when he saw his reflection in the shop windows, he did look sexy, as well as much older than his 11 years.

 

As soon as they returned to Sandra’s flat, she pushed him onto the sofa, pulled both their panties down and fucked him again.

 

 

 

Ray stayed at Sandra’s every weekend from then on, sharing Sandra’s bed and her clothes.

 

 

8.     Epilogue

 

Ray is lying with his head in Sandra’s lap idly rubbing his fingers around her hairy cunt. The strong smell of the sex they have just had in his nostrils.

 

“Ray, I’m sorry if Jimmy hurt you, I was pregnant and I couldn’t stop him.” Sandra strokes Ray’s head. “No one will ever hurt you again I promise. I love you Ray.”

 

“It was fine, I understand. I love you Sandra.”

 

“Jimmy won’t be back again anyway, he has jumped ship in Singapore and married some whore, so I hear.”

 

Ray leans over and kisses Sandra’s cunt. “Good!”

 

 

 

Ray has moved in with Sandra permanently following a serious illness for his mother. He is doing well at school, and since he and Sandra sleep together every night, he hasn’t felt the need to chase adventures anywhere else.

 

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