Chapter 7: Best Of Both Worlds

‘It would also need to be someone who was available, and someone who knew what they were doing. Not having to explain to anyone why I wanted them to do it to me would be a big bonus too. But I only know one person who would fit that description.’

‘Then all you need to do is to ask him.’ Cliff told him, smiling at him. Shane looked at him, amazed that he felt no embarrassment, ‘Cliff, would you do it for me please?’ he asked. ‘Of course I will,’ Cliff told him. ‘I will be delighted to be the one who got rid of your nightmares.’

‘But I’ll always feel so proud that you felt able to ask me and trusted me to do it. Also, I know that because we’ll both enjoy it, we’ll feel even closer to each other afterwards than we do now. So, here’s what we’ll do. Next, I’ll give you your lesson.’

‘During that, you’ll get to see and feel my cock like I promised. You will also see that my cock is quite small, so that will make it even easier to go inside you. Then when we’ve finished the lesson, I’ll ask you again if you still want to try it before we do.’

‘Thank you,’ Shane replied, ‘But I feel quite sure about it.’ Shane’s cock was still very hard with all that they had been talking about. ‘Ok,’ Cliff told him, ‘Stand up now and I’ll play the part of the girl. I’ll take you through from first date to waking up after you’ve made love.’

‘You’ll have to pretend I’ve got breasts to feel and that my cock is a vagina.’ he added, grinning. Shane laughed, he was feeling very excited about it all and his cock wouldn’t stay still. ‘Now, when I describe taking an item of girls clothes off, you take it off me.’

‘When I describe taking an item of boy’s clothes off, I’ll just go through the motions of undressing you. Let’s start off with a short hug and a kiss.’ They did, and Cliff told him, ‘That was the end of your first date.’ Then he took him through the next ones.

Soon Cliff was stripped to the waist and they had another hug, a long kiss on the lips, and ran their hands up and down each other’s bare backs. Cliff told Shane to take his trousers off. He undid the belt and top button but looked for reassurance before sliding the zip down.

Getting a reassuring nod and smile from Cliff, he did so. As it went down, he could see Cliff’s underpants. Then Cliffs trousers dropped to his ankles. Shane was looking at the tiny little bulge of Cliffs soft cock. Even so, he found it very exciting and as he helped Cliff step out of his trousers, he couldn’t take his eyes off it.’

‘Have a feel of my cock,’ Cliff told him, ‘But remember if this was real, you’d only be feeling the girl’s hairs.’ As Shane rested his hand on Cliff’s bulge, he felt it starting to grow. He kept his hand on it until it was hard. It was the most exciting thing he had ever experienced.

‘That wouldn’t happen of course,’ Cliff reminded him, ‘But there’s no reason why you can’t enjoy it. It’s certainly feeling lovely to me.’ Encouraged, Shane had a good feel round. Then following instructions, he stood up and they had another hug and kiss.

‘Remember that your cock would be inside your underpants and trousers. But it would still be pressed against her hairs, with just her panties and your clothes between you.’ Cliff told him. Shanes hard cock did a lot of flexing, which made cliffs cock copy it.

‘Now I will take your trousers off,’ Cliff told him as he mimed doing it. He gave Shanes cock a quick stroke as he did, making him howl in delight. They had another hug, and Cliff knelt down as if to help him step out of his trousers.

He gave his cock a feel and a kiss. Then after Shanes cry of delight faded, he added, ‘Remember that was over your underpants.’ They had another hug. ‘Now you are hugging with just your underpants on,’ Cliff told him. ‘She has just her panties on.’

‘Your cock is hard and flexing against her and her breasts are pressed against your chest. Now it’s time to take her to bed. Just wait a moment.’ Cliff instructed as he opened the settee out into a bed. ‘Offer her your hand, and if she takes it, lead her over to the bed.’