Andy goes on holiday and becomes a man

Part 3 of the Andy stories

 – Much slower and gentler than parts 1 and 2

-     The only sex is boy + girl


Part 1 – The car in the lane

Part 2 - Further adventures of Andy

Andy (12)

Ziggy (Zach) (12)

Bel (Belinda) (10)

Izzy (Isabel) (12)

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.




“Would you like to come on holiday with us Andy?” Anne asked as she was stirring the pot on the cooker.


“Oh yes Andy, you’ll love it, we get to see all our relatives and you get to stay at the resort with us. Please come Andy.” Ziggy bounced round the room.


“I tell you what Andy, I’ll call your mum and arrange for us all to have dinner one night and sort it out.” Anne turned back to the cooker and carried on cooking.


Andy looked at Anne’s naked bum as she wiped her hands on the apron and his cock stirred as he thought about the resort. He had seen the photographs in the magazine that Ziggy had shown him and knew it was a naturist resort.


Eli returned from work and they all sat naked in the kitchen eating their dinner. After dinner Anne got a photograph album out and lay it on the table flicking through page after page of pictures of the resort and the naked people of all ages in the resort playing games and relaxing. Anne pinched Andy’s cock a few times as he looked at the photographs. She pulled Andy’s hand towards her and Andy felt the hair around her pussy brush against the palm of his hand. She pulled his hand in tighter and Andy felt a small hard protrusion buried amongst the hair at the top of her pussy. She pushed his hand against it briefly before letting go of Andy’s hand and turning the page.


Eli drove Andy home and pulled into the lay-by as usual and Andy sucked his cock until Eli came and Andy swallowed his cum.




Anne, Eli and Ziggy arrived at Andy’s home. Andy’s parents, Brian and Suzy, welcomed them warmly into their house. Suzy had made sure that she had cooked something that they could all eat, so a chicken casserole bubbled away on the stove.


They settled down at the big pine table in the kitchen and Suzy and Anne were soon chatting like old friends. While Brian and Eli had a beer they talked about their jobs and sport. Brian was distracted by the sight of Anne’s tits revealed beneath her silk top and the absence of a bra.


Eventually the six of them sat down at the table with the boys talking about school and rugby as they ate.


After dinner had been cleared away and while Brian and Eli washed the dishes, Anne got out the photograph albums of the resort they wanted to take Andy to. The first few pictures showed the general area. Suzy turned the page to be confronted by several naked bodies. “Oh!”


“Didn’t Andy tell you we were naturists?” Anne smiled at Suzy as she turned the page to a photo of the family relaxing round a table. “That’s my daughter, Sophia, she’s away at university at the moment, but she will fly out to join us as well.


Brian and Eli were now peering over Anne’s shoulder. “It, um, looks very nice, the resort I mean” Brian gasped a bit as he said it.


Ziggy turned the page to a photo showing naked kids playing tennis. “It’s got loads of sports clubs and there is always something going on.”


“So I see.” Suzy looked round at her husband, who just shrugged his shoulders. “It looks really nice Suzy. I’ll get some more drinks.”


“Yes, a large glass of wine please.” Suzy tore her eyes away from the sight of naked men and women playing badminton.


After looking through the book, and after it was revealed that Andy had been naked every Wednesday night for the last few months when he had his dinner with Ziggy, Suzy decided that Andy could go and that they would sort out his passport on Saturday.




Andy was really excited; he had never been on a plane before. He sat next to Anne, and Ziggy was several rows back with his father. Anne had decided to keep the boys separate on the plane to minimise the messing around disturbing the other passengers.


The food was better than he expected, and the flight a lot longer than he expected. Eventually they arrived, went through passport control, which he had to do by himself as the others have local passports, and collected their luggage. Andy looked around at the strange surroundings slightly bewildered by the sights and sounds.


A large man hugged Anne tightly and then Eli and Ziggy. He bowed down and shook Andy’s hand. “This is my grandfather”, Ziggy explained, he only speaks a little English.


They climbed into a large car, Anne and the boys in the back and the men in the front and drove out of town and into the countryside until they came to a large rambling house set high up on the hills. “This is my father’s house and we will stay here for a few days before going to the resort” Anne explained.


The car door was flung open by a woman about the same age as Anne. “You’ve grown so much Zach!” She hugged him really tight. “My sister, Sheila” Anne explained. Sheila hugged Anne and Eli. In a broad American accent she asked “and who is this strong looking young man?” She hugged Andy to her more than ample bosom. “My, he is so strong!” Andy coloured up in embarrassment as she continued to hug him tightly. “The girls had better watch out with this strong young man and look how big and strong Zach has grown.”


Finally she let Andy go and they walked into the house to be greeted by two naked young girls. “This is Izzy and Bel, my daughters, and this strong young man is Andy” Sheila announced as the girls shyly greeted Andy and Zach.


After lunch the girls decided to walk down the hill to the village. Anne persuaded Andy and Zach to go with them so the adults could catch up.


With both the boys and girls dressed in nothing more than t-shirts and shorts they wandered around the village. Izzy explained that they had come over on holiday from America; that their parents were divorced and they were living in California. Mom was a professor at the university.


The girls were pestered by some boys making fun of their American accents. It got a bit rough and one of the boys tried to grab Izzy’s t-shirt. Zach tried to intervene and was shoved as well. Andy got involved and a fight broke out which left two of the bullies bloodied, and Andy’s clothes torn and dirty.


On the walk back to the house Izzy grabbed Andy’s hand and wouldn’t let go.


They returned to find the adults relaxing in the garden drinking wine. Anne looked at Andy and frowned, but before she could say anything Izzy pushed him behind her and explained that Andy was protecting her from the bullies and explained what had happened.


“Okay, let’s get you into a bath and see what the damage is.” Sheila took Andy’s hand and started to lead him indoors.


“I’ll help” Izzy held Andy’s other hand and the three of them walked into the house.


“I’m all right, honestly.” Andy tried to protest as Sheila undressed him and looked at the grazes on his arms and legs. Sheila made him stand naked in the bath as she carefully washed him. As soon as he was dry Izzy applied ointment onto the grazes, while Sheila made sure that there was no serious damage. Soon, an embarrassed Andy had been dressed in a loose t-shirt and loose shorts and was back in the garden with the others. Izzy was by his side holding his hand tightly.


As they sat at the big table in the garden, which was laden down with lots of different fish, bread and a huge salad, Izzy insisted that she sit next to Andy. She kept touching his arm, making sure he was okay, and telling him how the different fish tasted and which ones he might like to try and making sure his plate was always full.


Over the next couple of days wherever Andy went Izzy, Ziggy and Bel were close by, although Izzy was always the closest. It seemed perfectly natural to Andy to lie naked next to Izzy in the sunshine in the garden while equally naked adults either sunbathed with them or went about the business of preparing food or tidying. Andy looked admiringly at Izzy’s small developing tits and the small amount of fine blonde hair surrounding her pussy. Izzy for her part, equally admired his muscular body and the large, for his age, cock nestled in among the brown hair.


Andy noticed that Sheila kept her own pussy hair neatly trimmed in comparison to Anne’s wild mass of hair.




After a long drive Eli drove the hired minibus through the gates of the resort. He checked everyone in at reception and parked outside the lodge where everyone was staying. Sophia, Anne’s daughter, rushed out to greet them. She had arrived earlier that day and taken a taxi straight to the resort. Sophia eventually greeted Andy as he took in her slim body. All traces of hair on her body had been removed apart from her head of course, where her long blonde hair hung down past her waist. Izzy quickly stepped between them, to say hello of course, but also to prevent Andy looking for too long at Zach’s sister’s much more developed body. “I see you’ve gone blonde again” Sheila greeted Sophie with a laugh.


With four bedrooms, the boys were put in one room, the girls in another, Sheila and Sophia in the third and Anne and Eli in the remaining room.


Soon they were all undressed and sitting on the balcony sipping wine and fruit juice in the evening sun. Izzy beat Zach to the seat next to Andy. People of all shapes, sizes and ages walking past greeted them with a wave or a friendly hello.


After a while they went to the onsite restaurant and ate. It seemed odd to Andy to see so many naked people in one place, all of them so unconcerned. With Izzy one side of him, and Zach the other, Andy was included in the conversations as much as possible and in private conversations with Izzy and Zach when the wider conversations turned to people he didn’t know.


Several girls and boys of similar ages came over to renew acquaintance with Zach and the girls. Izzy made a point of holding Andy’s hand tightly whenever one of the girls showed too much interest in Andy.


Everyone was chatting away when Andy felt Izzy’s hand on his cock. She gripped it firmly and started to move her hand up and down. Andy looked nervously at Sheila who seemed not to notice. Nonetheless he was anxious and his cock didn’t immediately respond which only caused Izzy to peer under the tablecloth. She moved her hand slowly and gradually Andy’s cock responded and started to get semi-hard. “Not in the restaurant Izzy, find somewhere private if you want to and only if Andy wants to” Sheila whispered at Izzy. Zach looked down and smiled as he saw Izzy’s hand gripping his friend’s cock. “Okay mom” Izzy let go of Andy’s cock and moved her hands back onto the table. “Well? Do you want to?” she whispered into Andy’s ear. “It felt like you wanted to” she whispered again.


Andy looked at Sheila and then at Anne who both nodded that it was okay. “Where?” Andy whispered back.


“We’re just going for a walk on the beach Mom.” Izzy grabbed Andy’s hand and pulled him up. Bel started to get up as well but Sheila told her that it was late and she was sure that Izzy would be back really soon. She emphasised those last words for Izzy’s benefit.


Sheila got up and whispered in Andy’s ear. “Don’t get too carried away, okay?” Andy nodded as Izzy dragged him from the restaurant.


There were several couples walking along the beach. Izzy dragged Andy into a quieter spot among the dunes. They could hear other people nearby, but couldn’t see anyone else or be seen unless someone walked directly into the same spot. Izzy pulled Andy’s face to hers and kissed him on the lips. Her hand rolled across his stomach down to the fine hair surrounding his cock. She pulled his hand onto her developing tits and showed him how to move his hand around her nipples which quickly hardened as he got the hang of what she liked. His cock was now hard as Izzy moved her hand slowly up and down the shaft, running her hand to the very tip before gently rolling back his foreskin to reveal the head.


She moved his hand down to the soft down covering her pussy and showed him how to stroke the slit with just one or two fingers. The tip of his finger slipped inside her as her pussy got wet. Their mouths closed together and she pushed her tongue inside his mouth and their tongues met.


Izzy let out a small moan as Andy’s fingers found her small hard clit. Her hand moved faster up and down his cock until a few drops of clear cum splattered onto her fingers. Andy rubbed her clit harder and Izzy let out a longer moan as her body shook a little as she came. She kissed him hard as she came, before she relaxed and they lay together side by side looking at the stars. Voices nearby caused them to sit up. “We had better get back” Izzy stood and dragged Andy up to his feet.


There was a whispered conversation between Izzy and her mom when they returned to the restaurant.



At breakfast the next morning Andy, Izzy and Bel were missing. Anne and Sheila crept into the boys’ bedroom and found Andy asleep in his bed under the covers with his body pressed against Izzy’s back. Bel was asleep pressed against Andy’s back. Sheila carefully pulled back the covers and lifted Bel out of the bed and carried her into the breakfast room as she slowly woke up.


A sheepish looking Andy and Izzy wandered into the breakfast room some thirty minutes later. “I’m sorry Sheila; I didn’t even know Izzy had crept into my bed last night.” Andy stared at the floor but Sheila hugged him to her chest and told him everything was fine.


“Come on Andy, we’ve got tennis this morning and then football this afternoon.” Zach was ready to go.


After a full day of activities; Andy and Zach showered under the rudimentary outdoor shower before going back to their bedroom as they had a little time to relax before dinner at the restaurant. Andy found something new on his bedside table with a note. “Just in case, Love Sheila.” Andy picked up the packet of condoms and quickly hid them and the note before Zach saw them.




That evening some old friends of Anne and Eli sat with them for dinner, their 12 year old daughter firmly attached to Zach’s side.


Izzy squeezed Andy’s hand and together they slipped away from the table to go for a walk. Sheila saw them go and continued her conversation.


“Mom says it is okay if we, well you know.” Izzy walked towards the lodge holding Andy’s hand. “She says she left something for you, so we would be safe. Do you want to Andy?”


“I do.” Andy couldn’t reply any other way. His cock was already hard just thinking about it.


“Mom said she would keep everyone in the restaurant for another hour or so.” Izzy opened the door. She stopped and pressed her lips against Andy’s. Her hand grasped Andy’s cock and she dragged him into her bedroom. She pulled Andy down onto the bed and kissed him, her tongue pressing against his. She guided her hand down to her already wet pussy. He felt the soft down and rubbed his finger along her slit “Go and get what my Mom left for you” Izzy gasped as a first little shudder went through her body.


-   - -  - - - -


Where’s Izzy and Andy gone?” Bel looked around the restaurant.


“They’ve gone back to the lodge” Sheila explained.


“Can I go too?” Bel started to get up.


“Stay here Bel. Izzy and Andy just need a little time together” Sheila pulled Bel back to her chair as Zach sniggered. “Be quiet Zach!”


-   - - - - - -



Andy returned with the packet and tried to read the instructions in the dim light. Izzy turned on the sidelight and they read the instructions together. “Well it doesn’t sound too difficult” Izzy pulled Andy to her. “We’ll put it on when we’re ready to, well when the time... Stop laughing Andy!”


Izzy pushed Andy onto his back and rubbed her hands all over his body. His cock strained upwards as she guided his hands to where she wanted to feel them. First he rubbed her tits and then her stomach until finally she pushed his hand between her legs and he felt the warmth and wetness of her open pussy. “Push a finger in!” she instructed Andy who pushed a long finger into her wet pussy. He felt some resistance. “You have to push through it.” Andy did as he was told and he felt something give as his finger suddenly went further. “OW!”


Andy stopped and pulled his finger out. “Did I do something wrong?”


Izzy pushed him back onto his back. “No you did everything just right. Now let me put this thing on you.” She carefully opened the packet by the light from the sidelight. They looked at it together to try and work it out before she placed the end on his cock and gently unrolled it. Satisfied with her work she moved across him and lined up her pussy with his cock. The tip of his cock entered the soft warmth of her pussy and she gasped at the size.


Slowly she lowered herself onto his cock until it was halfway in. “Shoot that hurts!”


“Perhaps we had better stop, maybe something is wrong.” Andy tried to pull back out but Izzy’s legs gripped him firmly.


“It’s fine.” A tear was in her eye as she pushed down a bit more. “Stay still!” Izzy gasped for breath and stayed very still until her breathing became more normal again. “Here goes!” She pushed down hard and all of Andy’s cock disappeared into her.


Izzy rested with Andy’s cock fully inside her. After a little while she started slowly moving around, getting used to having this foreign object inside her. Tremors ran through her body every time she moved.


Andy felt wonderful, the tightness gripping his cock was the best feeling ever and he lay back and let Izzy control the movement and pace. He knew there would be other times and for now he was content to let Izzy feel safe and comfortable. She gradually picked up the pace and worked against his body. She dragged his hands up to her tits and encouraged him to rub around them and squeeze the nipples.


Izzy shook violently as an orgasm swept over her. Andy pushed up and felt a few drops of cum spurt into the condom. He rolled Izzy onto her side and allowed her to relax before pulling his cock out. He was shocked to see blood on the condom as he pulled it off and looked for somewhere to put it. “You can’t flush anything like that in the resort.” Izzy handed him some tissues to wrap it in and to clean up his cock. She used some other tissues to clean herself up and told him to put the tissues and the condom in the trash bin


Izzy then explained about the blood to a somewhat confused Andy.


Andy got back onto the bed and they held each other tight.



Sheila looked in when the family returned, checked the empty wrapper on the side table and the tissues in the waste basket before removing them. Satisfied that everyone was safe she pulled the cover over the two sleeping bodies, turned out the light and shut the door. “You can sleep with me tonight Bel. Do not disturb Izzy and Andy okay?”



“Mom!” Izzy coloured up as her mom tried to question her.


“I just want to know if it was special, if you felt safe. I don’t want details, just to know that...”


“Mom” Izzy interrupted. “Yes it was special, yes I did feel safe, yes Andy was a perfect gentleman, yes we used protection and yes it was his first time as well. Okay?”


“Okay then.” Sheila turned away trying to suppress a laugh only to be faced with the grinning face of Anne. They both couldn’t suppress it any longer and laughed loudly.


“Mom! Auntie Anne!” Izzy stormed outside and Sheila and Anne collapsed into fits of laughter.




Over the next week Andy and Izzy slipped away from the restaurant most nights. They spent an hour each day exploring each other’s bodies and working out what they liked and how to make it last longer.


Goodbyes at the airport are never easy, and Izzy had red eyes from crying by the time she boarded her plane back to America. Because they come to the airport early, Anne to say goodbye to her sister and her daughter, Sophia, who was going to stay with Sheila for a week before going back to university, and Andy to say goodbye to Izzy, the family settled down in a restaurant for a meal and then wandered around the duty free area. Anne helped Andy buy his parents gifts.


Andy found himself alone with Eli as Anne helped Zach buy some things. “So you are a man now Andy. Do you know what that means?” Andy shook his head. “It means no more messing around with me or other men, only girls and women from now on. Do you understand Andy, you are now a man.” Andy nodded yes. “Good, I know Anne is looking forward to helping you learn more.” Eli ruffled Andy’s hair. “There is so much she wants to teach you.”


Anne returned. “While Zach is in the toilet, Sheila asked me to give you this.” She handed Andy a handwritten note.

 “Dear Andy, thank you for being so wonderful and considerate with Izzy. I would really like you to come to visit us in America in the summer, with your family of course. I will phone your parents next week to see if we can arrange something. I’ll pay for the flights, and you can stay in my house, so it won’t cost you anything. Please do come. Love Sheila. xxxx


Andy looked at Anne open-mouthed. “Quick put the note away, and please don’t tell Zach yet, until Sheila has spoken to your mother. Okay.”


Andy hugged Anne tight. “Thank you for everything.” Tears of happiness rolled down his face. “Be a man!” Eli cautioned him.







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