Chapter 5: Greggs Secret Path

He stood up and pulled his shirt off. He tossed it over onto the armchair and then dropped his trousers, stepped out of them and did the same with them. He was wearing a pair of light blue underpants.

As he lay down on his back, Lewis studied him. He was an average build with shoulders that looked strong without being remotely like a body builder. His hips were slightly smaller and although not fat, he had padding all over him. He had a good patch of black chest hairs.

The bulge in his shorts now much clearer, was still soft. But Lewis could tell he was probably just slightly smaller than he himself was. Gregg saw him studying him and didn’t seem bothered. ‘Not a body that would fill a girl with desire, is it?’ he said.

‘Don’t do yourself down,’ Lewis told him, ‘Theres plenty of girls would be happy with a boyfriend like you. And in any case, whilst your body might arouse desire in them, it’s your personality that will eventually be the deciding factor to match you to your life’s partner.’

‘That would be nice,’ he said sounding wistful. ‘Now,’ Lewis said, ‘When I said take your top things off, I meant literally your top. But being as you are now’s so much better. It’s a really big jump forward and is excellent progress, just as long as you feel ok about it.’

‘It’s only like I was in my swimming trunks at the pool,’ Gregg said. ‘Ok,’ Lewis told him, ‘Turn over when you’re ready.’ Gregg turned over immediately. Lewis massaged his head and Gregg said ‘Go,’ without prompting. He was anxious to feel a massage on his bare back.

As Lewis massaged his shoulders, he called out saying, ‘That feels lovely, you were right, it is so much better on the skin.’ ‘The more I can get you relaxed, the easier you will find it to tell me your problem.’ Lewis said as he moved down onto his back.

‘Where there any problems with the raft?’ Lewis asked. ‘Well, I sailed around the pond quite happily,’ Gregg said, ‘But when I came to get out, it wasn’t stable enough to let me stand up.’ ‘What happened?’ Lewis asked as he reached his waist. ‘It overturned, I got thrown in and ended up soaking wet.’ Gregg said laughing about it now.

‘So, what did you do then?’ Lewis asked as he moved up onto his cheeks. ‘I crawled out,’ Gregg said. Then he stopped and cried out in delight. ‘Oh, wow,’ he said, ‘That feels so lovely.’ He remained quiet apart from some happy sounds whilst Lewis massaged all over both cheeks. It wasn’t until Lewis moved on to the bare skin of his thighs that he managed to continue.

‘I pulled it up out of the water and went home to get dry,’ Gregg said. ‘Then the next day, I went down in my wellies and dug the bank back two feet for a foot longer than the length of the raft and five inches below the waterline.’

‘Then I tried again. Being able to pull the raft into the side over the ledge was great. As soon as I got in, the raft went down an inch and rested on the new ledge I’d just dug. I was then able to walk about on it easily, as long as I kept away from the outer edge.’

‘Once I was sitting, I floated off the ledge with half an inch clearance. I paddled round the pond. When I came back, I pulled myself into the side over the ledge. I could just stand up then and step out.’

‘That’s brilliant,’ Lewis told him, ‘Simple and easy, but very clever.’ He had been down to his feet and come back up to his underpants. As he moved onto them and massaged his cheeks Gregg was making much louder happy noises. Clearly, he was thoroughly enjoying it.

Lewis gave his cheeks a long massage as he was enjoying it so much, then moved up onto his bare back. ‘How do you get on with the girls at school?’ Lewis asked him.

‘Ok,’ Gregg said, I have never fallen out with any of them, and I have been invited to a couple of birthday parties. I asked a couple of them to go out with me, but they said no.’

‘After the second one said no, I didn’t risk asking any others.’

‘Do you dream about any of them at night?’ Lewis asked as he reached his shoulders. ‘Yes,’ Gregg replied, ‘There are two in my year I would love to have as a girlfriend.’

‘Sonya is in my form and Tanya is in the class below. They are both lovely and have a good figure. But they are also very popular with the other boys.’

‘Where they the two you asked out?’ Lewis enquired as he massaged his head, took his hands away and told him to turn over. ‘Yes,’ Gregg admitted as he turned.

Once he was lying on his back, Lewis smiled at him. ‘Don’t worry.’ he told him, ‘There are lots of boys your age with the same problem. You just need a bit more confidence.’

‘I’m going to go down your front again now. I’ll be asking you about sex so remember what I told you about your cock. You don’t need to say go any more, I think you’re relaxed enough now. But if you say stop at any time, I’ll immediately return to your head and start again, ok.’

‘Ok,’ Gregg said, thinking everything so far had been far too nice to want to stop. Even the questions hadn’t been bad, apart from a couple he hadn’t meant to answer.’

As Lewis massaged the front of his shoulders, he could see a happy smile on Gregg’s face. ‘When you dream about them at night,’ Lewis asked, ‘What do you dream you are doing with them.’

Gregg went red then he said, ‘I’m in bed with them.’ ‘Doing what?’ Lewis asked as he massaged through his chest hairs. ‘We’re having sex.’ Gregg said sounding surprised.

‘Ok, suppose I knew nothing about sex,’ Lewis told him, ‘Can you tell me exactly what ‘having sex’ is.’ He moved down onto his slightly padded stomach as Gregg said quietly, ‘I put my cock in her vagina and moved in and out until I shot all my cum into her.’

‘Suppose it hadn’t been a dream, but had actually happened,’ Lewis asked, ‘How do you think the girl would have enjoyed what you were doing?’ It was so obvious from his reaction that the girl’s feelings had never crossed his mind. ‘Oh er, I don’t know.’ he said as Lewis’s hands moved onto the front of his underpants.

‘Tell me,’ Lewis asked, ‘Where did you get your knowledge about sex from?’ ‘We had a lesson in school.’ Gregg answered. ‘Did you understand it all completely?’ Lewis asked as he moved over his bulge. ‘No, not every bit.’ Gregg admitted.

‘So how many questions did you ask?’ Lewis enquired. ‘None,’ Gregg said quietly, ‘I’d have been far too embarrassed in front of the rest of the class.’ As Lewis’s hand moved around over his cock Gregg felt it start to grow a little.

After a moment of panic, he remembered what Lewis had said and relaxed. ‘Did you get any sex knowledge from anywhere else?’ Lewis asked. Feeling his cock growing he stayed on it a little longer. ‘Only from what I heard lads talking about in the playground.’ Gregg told him.

As Lewis moved on down his bare thighs, Gregg felt disappointed, the feeling of Lewis’s hand on his cock had felt amazingly nice. ‘How about Mark and Billy?’ Lewis asked, ‘Did they ever offer any advice?’

‘Oh yes,’ Gregg said, ‘We would often talk about things we would do with different girls. But I never really believed that they knew any more than I did.’

‘Just suppose you met a girl tomorrow who became your girlfriend,’ Lewis said as he reached Gregg’s feet and started back up. ‘Suppose a few months later she told you she wanted to spend the night with you. How do you think you would feel?’

‘Over the moon,’ he said, ‘Very excited and absolutely terrified.’ ‘Explain the terrified.’ Lewis told him. ‘Well, I’m not really sure how close what I dream is to reality,’ Gregg told him. ‘I’d probably make a complete mess of it, and she’d be off.’

‘Well from what you’ve said so far,’ Lewis told him, ‘I think you’re right.’ Then as Gregg looked horrified, he continued, ‘But don’t worry, you’re not alone. If you want me to, once we have sorted your problem out, I’ll give you all the sex education you need.’

Gregg’s face lit up, ‘That would be great, thanks.’ he said. As Lewis’s hands reached the bottom of his underpants he said, ‘In your dreams how many different girls have you had sex with?’

As Gregg added up in his mind, Lewis’s hand moved towards his bulge. As Gregg replied, ‘About ten,’ he saw and felt Lewis’s hand move over his cock.