Date: Tue, 10 Mar 2020 17:06:00 +0000 From: Andrew Passey Subject: The Terrible Twin Part 8 (Young Friends) I started to tremble, I did not want to have sex with James for money. I can't deny I was mildly intrigued by what John and Pete had said but there was a difference between that and taking someone's dick up your arse because they paid your brother to do it. James got close and smiled at me, then he spoke softly.. "No of course I'm not going to rape you. I just wanted you to see how far gone your brother was. He's a gambling addict. He's a thief. He'll do anything for money. He was going around the arcade offering people a blow job from you if they paid him. I got wind of it so made a high bid before some of the more interested boys could pay up." "Why?" I asked "I've had my eye on him for a while. I knew he'd stolen money from Mrs Kent and Dean told me about what you'd done to pay them back" he said. I blushed. Great. Someone else who knows I suck dicks. "I never expected to see you here but once I did and I heard what he was up to I thought it was a good opportunity." "Ok, so why are we naked?" i said, still confused. "Well we had to make it look natural,h e's outside, he'll be expecting me to do it, he might be expecting the sound of grunting and squealing", he said. "Er......so we still have to have sex?" I said pretty reluctantly. Whether it was paid for or not, I still didn't really want his dick up my arse although, as I looked at it I got more interested. Life was about experiences after all. Shit, stop it, control yourself Tim. "Don't worry Tim, you're going to fuck me first and then if you think you want to then I'll fuck you afterwards. Don't worry, I'll be gentle, I know what I'm doing" he said with a wink. "Oh ok, are you gay?" "Yeah think so! I've been messing around with Dean for years and sometimes Arron. And the odd boy at school although that's trickier, I am in the closet after all" he said. "You've had sex with them?" I asked in shock, I really was innocent and inexperienced it seemed. Although working on improving that! "Yeah lots with with Dean. not Arron though.I think Arron is saving himself for someone special ' James said with a grin and a wink. I blushed, did he mean me? "Ok, well I have no fucking idea what I'm doing so you better take the lead" I said, James took me by the hand and led me into his tiny bedroom. He drew the curtains, rummaged in his bag and got a tube out. "Right so I'm going to use this to make it easier for us, so I'll rub some on your dick and some on my bum hole. That should help you slip in and make sure it isn't painful" he said. He rubbed it up and down my dick, particularly on my head which caused me to harden. "Mmm looks good" he said with a wink. He got on the bed on his back, lifted his legs and did his hole and then told me to get between him. "Ok, just line up your dick head with my hole and push it in" he said. Sounded simple and it was, with a gentle push and a gasp from James I was part way in, then gentle I pushed more in until I was all the way in. "You ok?" I asked, "Yeah good, it was a gasp of anticipation, not pain!". I started to move in and out of him although I slipped out a couple of times, I wasn't used to this. Luckily James hooked his legs around me, pulling me into him and holding me place. It felt amazing but was really surprised me was that James was clearly enjoying it, making moaning and squealing sounds as I thrust in and out of him. I'd assumed it would hurt or at least not be enjoyable but I could see from James noises and his face that it felt really good. There was no doubting it felt really good for me, James's hole clamped on my dick, the friction from the tightness felt amazing as did the warmth of being inside him. It wasn't long before I felt I was going to cum, a few thrusts later I saw stars as I had an earth shatteringly good orgasm, firing all my cum into James. His dick was rock hard and he told me how good it had been. "So it doesn't hurt?" I asked. "Not really, if you're big like Dean it can hurt a bit at first but every time it hits your prostate it feels amazing. It's a little thing up your bum, that's why I was squealing as your dick hit it". I nodded, it sounded confusing but there was no doubt he enjoyed it, as did I! He cleaned us up and then looked at me, "So........." he said leaving it open ended. He looked so cute and like a lost little boy, I couldn't say no to him. "Ok but be careful and stop if I tell you to" I said. Why not let myself get fucked, he knew what he was doing, he was nice and I wanted to know what it felt like. James got me to lie down and pull my knees up to my chest which he said would help me take his bigger dick. He lubed me up well, liberally smearing it on my hole. using lots of it over my hole. He then positioned himself at my hole and gently pushed it. It slipped in and I let out a "OW FUCK!". It hurt but he held it there and he very gently pushed further bit by bit until I could see he was all the way in. He gently moved in and out of me, ""Fuck...soooooooooo tight" he said as he smiled at me. His dick head my hitting my prostate again and again and I started to really enjoy it. I was hard again and he put his hand on my dick wanking me slowly. "You......Ok?" He asked between gasps of breath. "nnnggghh.....yeah.....mmmpppphh.....hurts....bit..but.....feels.... good.....nngggg...though........." I said, in between grunts and groans. He kept going with his hand and his dick in me until I shot over James's hand and James came in with a loud cry of "uhhhhhhhhhh!". I bet Steve heard that I thought. James pumped in me a few more times before pulling out. "So......better or worse than you thought?" He asked. "Much much better! When can we do it again." I asked with a grin. I wasn't sure I did want to do it again that soon but it was definitely much better than I expected. "Soon" he said smiling. "Now go and get cleaned up in the shower" he said giving me a towel. He left the room and I followed him out, he stuck his head out the door, "Am done Steve, well worth the money. I'll let him clean off in the shower first, come in while he does" he said and I went to the shower....