Chapter 3: Relieving a Relaxed Rupert

‘Wow,’ Rupert said as he imagined it, making his cock give a good flex under Lewis’s hand. As Lewis moved on up over his stomach he asked, ‘Have you ever held someone else’s erect cock on the bare skin?’ Rupert went red and said, ‘Pass.’ ‘Has anyone else ever held your erect cock directly on the skin?’ ‘Pass,’ Rupert said once more still glowing red and looking unhappy.

‘Looking at your problem,’ Lewis asked, ‘Apart from yourself, how many others were involved?’ ‘Just one.’ Rupert answered quietly. Lewis moved up onto his head, gave it a massage then took his hands away.

Smiling at him, he said, ‘You’re doing exceptionally well. Now, when you turn over again, I’ll go down your back as before. But when I reach your waist, I’ll take hold of the back of your underpants and lift them slightly.’

‘If you say stop, I’ll let go and carry on down over the top like last time. If you say nothing, I’ll massage your cheeks directly on your skin. I’ll leave you to imagine how relaxing that will be.’

‘Turn over whenever you feel ready.’ Rupert turned right away. He felt excited at the idea of Lewis massaging on his cheeks, even though he didn’t know if he’d be able to let him when it actually came to it. He thought about the last pair of hands that held his bare cheeks and shivered.

‘More bad memories?’ Lewis said quietly, ‘Just remember nothing is going to hurt you today.’ ‘I know,’ Rupert said. As Lewis massaged the back of his head, he said ‘Can you tell me the Christian name of the person who hurt you?’

As he moved down onto his shoulders Rupert was silent. Deep in thought. He remained silent as Lewis moved onto his shoulders and massaged them. As he moved on down his back, Rupert said, ‘Ray.’

Then Lewis changed tack, asking, ‘At the home, how come it was you who got the downstairs room?’ That threw Rupert’s chain of thought. As Lewis reached his waist and lifted the back of his underpants, he was busy concentrating on his answer.

When he said nothing, Lewis slid his hand slowly down inside and rested it over one cheek. As he started massaging, Rupert let out a happy shriek as the lovely sensation ran through him. Then as Lewis moved over and did the same on the other cheek, he cried out again. ‘That is so lovely,’ he said, ‘I’d never have believed I could enjoy anybody’s touch there.’

Lewis slid his hand out, then massaged over the top and down the back of his legs. Rupert got round to answering at last. ‘It’s just a custom at the home,’ he said, ‘The youngest resident always has downstairs. If one of the older lads moved out, I would then move upstairs, unless the new one was older than me.’

‘So was one of the lads now upstairs, living downstairs just before you arrived at the home?’ Lewis asked. ‘I have no idea,’ Rupert said, ‘I knew nothing about the custom until someone mentioned it about a year ago.’

As Lewis started back up, he asked, ‘Over the next week without attracting attention to it, will you try and find out who was downstairs before you. A name and his phone number would be great too. Don’t worry, he won’t know the information came from you.’

‘How old would you say Ray is?’ Lewis asked as he massaged over his cheeks again. ‘About thirty I think but I’m not a very good judge of age.’ Rupert managed to get out in between making excited happy noises.

Then as Lewis moved up to the top, he was expecting the top of his underpants to be put back down. Instead, he felt them sliding down to uncover his cheeks. He wasn’t sure whether to be scared or excited. Before he had decided, Lewis put a hand on both cheeks at the same time and massaged them.

Rupert let out such a scream of delight, that Lewis kept massaging longer than he had intended. As Lewis came up off his cheeks, he said, ‘When someone tries to do anything to you that you don’t want them to do, that is wrong. If they carry on and do it even after you tell them no, that is an attack.’

‘So how many times has Ray attacked you?’ Lewis was moving up his back as he spoke.

Then as Lewis reached his shoulders, Rupert answered, ‘Three times so far.’ As Lewis reached his head, he gave it a short massage and said, ‘Turn over.’ When Rupert was settled on his back, Lewis saw the top inch of his hairs where his underpants had slid down a little. His cock was still rampant. Neither of which seemed to be bothering Rupert.

‘You’re very close,’ Lewis told him as he massaged his head. ‘I think by the time we come back up again you will be ready. I’m going to go down your front just like I’ve done on your back. When I reach your waist, I’ll do the same with your underpants.’

‘On the way down, or on the way back up, if I go inside and you feel relaxed enough, lift your hips so I can slide them off and massage you all over. If you don’t feel able to do that yet, it’s ok.’

As he put his hands on Rupert’s stomach and massaged it, Lewis said, ‘When you play with yourself in bed at night, do you ever have any difficulty firing.’ As he finished speaking his hand reached Rupert’s underpants. Trying to concentrate on the question, as well as feeling excitement as Lewis’s hand lifted the front of his underpants, he said, ‘Up to about four months ago, no. After that yes.’

Lewis let him finish speaking and then as he didn’t add anything else, he slid his hand down the top of the thigh nearest to him. Rupert was making a string of happy noises at the feelings he was getting. Then when the side of Lewis’s hand slid alongside the side of his cock, he let out such a screech of pleasure and his cock did a dance.

As much as it could within the confines of his now very tight underpants anyway. Lewis slid his hand out, getting another happy screech. Moving over to the other thigh, Lewis repeated it. His hand sliding down the other side of Rupert’s cock had the same result.

Instead of sliding his hand back out the same way, Lewis reached down deeper, moved his hand into the middle and hooked his fingers gently over Rupert’s balls.

After his next scream of excitement faded, Lewis drew his hand out very slowly, letting his fingers run up the whole length of the underside of Rupert’s cock. Before his fingers reached Rupert’s tip, his hand was completely out of his underpants.

When his hand came off his tip, the top inch and a half of Rupert’s cock was sticking out above the waist of his underpants. Even that showing didn’t seem to be bothering Rupert now. Lewis massaged back down over the top of his underpants and down onto his legs. As his hands touched the top of his thighs, Rupert’s cock gave a flex, making him cry out happily.

Then Rupert realised that he had been so engrossed in enjoying all the lovely feelings he had forgotten to lift his hips. ‘Sorry, Lewis,’ he said, ‘I forgot.’ He lifted his hips up, so Lewis slid his underpants down to his ankles then off over his feet.

Freed from restrictions, Rupert’s cock stood up straight and waved about happily. Lewis looked at it, trying to decide if it was the same length as his or possibly even longer. ‘I think we might have to measure each other later,’ he said, ‘I can’t decide which of us is the biggest.’

The mental image that conjured up in Rupert’s mind made his cock do a lot of flexing. Lewis massaged his ankles and started up his legs. ‘When I reach your head we will be ready to talk about your problem,’ he said.

‘How many times in the last four months have you successfully fired yourself,’ Lewis asked. As he reached the top of Rupert’s thighs his cock was waving about again. ‘I haven’t,’ Rupert told him. ‘I’ve tried occasionally but even on the occasions I started to stiffen up, I never got fully hard, so nothing happened.’

As Lewis took hold of Rupert’s cock in one hand and played with his balls with the other, Rupert’s cock was throbbing madly. ‘I haven’t been this hard for months.’ he said sounding very happy about it. Lewis started sliding his hand up and down it, still playing with his balls too.