Chapter 5: Jacks First Experience

Lewis moved up to and took hold of the front of his shorts. He lifted them up an inch then said, ‘Up or Down?’ ‘Down.’ came the immediate response.

Lewis slid his hand down inside and massaged down over one hip. As the side of his hand slid against Jacks cock, it flexed, and Jack cried out in ecstasy. Then as he came back up, moved over through his hairs and did the same over the other hip Jack couldn’t stop himself calling out, ‘Oh Lewis, that feels wonderful.’

Then instead of pulling out, Lewis slid his hand over into the middle and pressed Jacks cock flat. Then as he started sliding his hand very, very, slowly up the underside, he said quietly, ‘If you felt relaxed enough to lift your hips up, I could slip your shorts off and let your cock wave about free of all restrictions.’

Jack’s hips went up almost immediately. Lewis stopped moving his hand and just held Jacks cock flat whilst he pulled his shorts down with his free hand. Once they were down past his balls, he let go of his cock which sprang upright and waved about.

Lewis slipped his shorts right down and off over his feet. He took hold of his cock and stroked it gently all over. Then he felt Jacks balls which made him draw his knees up so Lewis could get hold of them better.

Lewis let go and looked at the happy smile on Jacks face. ‘I think it’s safe to say you feel very relaxed with me now,’ he said with a grin. ‘I want you to close your eyes and relax whilst I massage from your feet to your head without any questions.’

‘When I’ve done that, you can finish telling me about you and Baron. Then we will easily sort out your problem.’ Jack felt so good at the thought of both the pleasure to come and the relief of his solved problem. He closed his eyes and waited.

Lewis massaged his ankles and moved up his legs slowly. Jacks cock did a dance which got more lively the closer Lewis’s hand got to it. When he took hold of it, it was a struggle to hold it still. Then when he stroked Jacks balls, his cock was doing a very lively dance indeed.

Once Lewis took hold of his cock and stroked it, Jack couldn’t stop screaming out with delight. Then as Lewis massaged through his hairs,

and moved on up his front he was still enjoying the massage.

Reaching his head, Lewis gave a brief massage then took his hands away. ‘Jack.’ he said. Jack opened his eyes to find Lewis with his arms wide open smiling at him. ‘Sit up.’ he said.

Jack sat up and as Lewis took him in his arms, he put his head on Lewis’s shoulder and his arms around him. ‘I feel so safe here,’ Jack said, ‘And I know you are going to sort everything out for me.’

Lewis kept hold of him for a while, then told him to stay sitting up. He moved to sit at the end of the settee, then Jack lay down with his head on Lewis’s lap.

Lewis massaged his head gently with one hand. He took hold of his cock with his other hand but kept it still. Or at least as still as he could. The touch of his hand made it throb regularly.

‘Finish your story about Baron,’ Lewis told him. ‘We had a lovely day out,’ Jack said, ‘Then eventually we went up to bed.’ ‘Go to the bathroom,’ Baron told me, ‘But don’t get changed yet.’ ‘When I returned, he went, after telling me to stay as I was.’

‘When he came back, he smiled at me and said, ‘Now you know I enjoyed it, are you happy about how close we got?’ ‘Yes, I admitted.’ ‘Right,’ he said, ‘Tonight, I want us to get into bed knowing that whatever position we get into we can relax and enjoy it knowing the other one will feel the same. Do you like that idea?’ ‘Yes.’ I said, I was already feeling excited.’

‘There is a big problem we both share,’ he said. ‘We are both excessively shy. We’re less shy with each other than with everyone else, but even so we’re shy. We are both the same age. We have known each other for years and we both know from brief glimpses that our cocks are as good as identical in size. So why do we keep hiding ourselves from each other, it’s daft.’

‘So, here’s my idea,’ he said. ‘Tonight, we are going to get changed for bed standing opposite each other. We will do the same thing at the same time, so we are both doing it together.’

‘I will start if you are game to try it.’ I was nervous but I said, ‘Ok.’ Baron took his top off and threw it on the bed. Then he stood still. So, I took mine off too. We stood looking at each other.’

‘Then Baron started undoing his trousers. I wanted to back out then, but it didn’t seem fair to him, so I said nothing. His trousers dropped to his ankles. I couldn’t take my eyes off the front of his shorts. I could feel my cock growing and see his moving at the same time.’

‘By the time he had stepped out of his trousers and put them on the bed we were both hard. It showed more on him being just in his shorts and I was sure he would be feeling embarrassed, but he stood there still. He said nothing, didn’t rush me.’

‘I watched his bulge moving in his shorts, then as if in a daze I started undoing my trousers. Baron smiled at me and said, ‘It’s ok, don’t worry.’ I felt them drop to my ankles. Now I knew Baron would be looking at my bulge too.’

‘With both of us looking at each other’s bulges, it didn’t seem quite as bad somehow. I kicked my trousers off over my feet, picked them up and put them on the bed.’

‘Now my heart was really pounding. Baron told me afterwards that his was too. He took hold of the top of his shorts. I could see he was struggling. Then I had an idea. ‘How about we turn around and both take our shorts off at the same time,’ I said, ‘Then when we turn back to face each other, we’ll see each other at the same time.’

‘He gave me a smile and mouthed, ‘Thank you’ to me. We both turned our backs to each other and took our shorts off. It was difficult with our cocks being so hard. As I looked sideways and tossed my shorts onto the bed, I saw another pair land with mine. So, I knew Baron was naked too.’

‘We stood with our backs to each other for ages, then Baron had an idea. ‘Back up carefully,’ he said, ‘Until our bums touch.’ We eased slowly back then suddenly our cheeks made contact.’

‘Now,’ Baron said, ‘When we turn to face each other, we can have a hug and be especially close without really seeing each other naked. When I get to three,’ he said, ‘Turn around.’

‘One, two, three.’ he said, and we both turned. Our faces were only inches apart and our cocks which were sticking out hard, banged against each other. It felt lovely.’

‘Baron put his hands on my shoulder. ‘This is very special,’ he said, ‘Put your hands on my shoulder too.’ When I did, he moved even closer, so our chests touched. As he put his head on my shoulder, he put his arms around me and hugged me. I did as he did. It felt so wonderful, so special.’

‘Our heads are touching,’ he said. ‘Our chests are touching, our legs are touching, our cocks are touching. It feels so lovely so why on earth are we shy with each other?’ ‘I don’t know,’ I said. He lifted his head off my shoulder and said, ‘Copy me.’

‘He dropped his arms to his side, so I did the same. He looked me straight in the eye and said, ‘Keep looking eye to eye and take a small step back.’ We did. ‘Now another one.’ We did. ‘One more,’ he said. ‘Then he told me, our shyness with each other ends right here.’

‘Look at me all over whilst I do the same to you.’ We did, it seemed so strange to be watching someone else’s cock, hard and waving about as mine did the same. We looked at each other for a while then he said, ‘Now move back again.’

‘When we were a foot apart, he said, ‘Stop there. Every bit of our bodies has now touched,’ he said, ‘But there is one more thing we need to do. When I say go, I’m going to reach out slowly and get hold of your cock. As I do, I want you to do the same to me.’