Date: Sun, 17 Jan 2021 14:06:00 +0000 From: Andrew Passey Subject: The Deal Part Five (Young Friends) Twice weekly homework and cock sucking sessions continued over the next few weeks. Jamie couldn't pretend that he wasn't enjoying it. What boy doesn't enjoy sucking the cock of the boy he had a crush on? He was by now a real expert in giving Tom an amazing blow job and he prided himself on his skills. Tom clearly enjoyed it and it had the added benefit that Tom now let him stay and play PS4 games with him every Sunday. Jamie felt like they were beginning to recapture the old friendship days. He missed those days and hoped one day they would come back. Although there was a nagging thought in his mind that everything he was doing for Tom would make that unlikely. School was also so much better than before. Tom and his bullying friends ignored Jamie and had turned their attention onto other boys in their school year. Unfortunately his friend Pete bore the brunt of it which did upset Jamie somewhat. He didn't know the best way to address it though. Pete would ask why him and not Jamie but he couldn't tell Pete about his deal with Tom. Jamie did want to do something to help Pete though. He just didn't quite know what. It was Sunday afternoon at Tom's. Jamie had just sucked Tom off walking himself off at the same time. They were both hanging out, naked on his bed. Jamie was now comfortable with letting Tom know he enjoyed it and that he liked sucking his cock. He did wonder if Tom could help with Pete being bullied and so he decided to raise while Tom was hopefully in a post orgasm high. "Um Tom. Can you like get your mates to lay off Pete a bit? He's really struggling to cope at the moment. Carl cornered him in the bathroom the other day and threatened to make him suck his cock," Jamie asked, hoping he wasn't stepping over a line. "Can't blame Carl, who wouldn't want their cock sucked? Personally I'm not sure I could live without you doing me twice a week. Maybe we should increase the frequency of your trips?" Tom replied with a smile. "I'm serious Tom, could you have a word?" Jamie asked slightly exasperatedly. "Hmmm I suppose I could but it would damage me in their eyes. I'm able to get them to lay off you by using the excuse of our parents being friends. I say I don't want them to find out and dob me into the school or ground me. It's tricky for me to justify a reason to lay off Pete. I'd be really putting my neck on the line Jamie." "Come on Tom, you know I've done everything you wanted, I think we've become friends again? Could you do this for me?" Jamie pleaded. Tom shifted and lay on his side to look at Jamie, giving Jamie the view he so liked. Jamie felt his body responding as it usually did even though he'd only just wanked himself off. "Hmmm. Alright then. Yes you've been good and yes we've sort of become friends. I'll keep them off Pete but I want something in return." "OK thanks. Um what exactly?" Jamie asked, wondering what else Tom could ask of him. "This," Tom said, reaching over and squeezing Jamie's bum cheeks. "What you want to feel my bum..oh," Jamie said as realisation hit him. "Yes Jamie," Tom said with a smile. "It's time for you to lose your cherry. Time for you to take my big cock up your arse. To be honest I could get you to give it to me anyway as part of our deal. However I appreciate it's a big step for you to take so this first time I'll do something in return for you. So I'll ask them to lay off Pete. Now pass me that hand cream on the table over there." Jamie did as he was told albeit reluctantly. He knew he had no choice and it would help Pete out if he did it. However he also knew that once Tom had lost his virginity he'd probably want to fuck him over and over again. Jamie knew enough about anal sex to know that a cock as big as Tom's would likely hurt at first. It also felt like it was stepping well over a line. Jamie could no longer pretend he wasn't totally gay. In reality he knew that train had left the station a long time ago. However it had been something to hold on to. Once Tom had deflowered him he was fully his. "Um ok. I'm not totally sure about this though Tom," Jamie said as he handed him the bottle. He wasn;t expecting Tom to back down but he wanted him to know he wasn't totally onboard. "That's natural Jamie, but don't worry you'll enjoy it. Not as much as I will obviously but hopefully you will. Now...how to do this, maybe get on all fours, like a dog." Tom suggested to Jamie who did as he was told, feeling a bit self conscious. He was also a bit annoyed at what Tom had said so once he was in position he pushed back slightly. "Like a dog?! Like this you mean although I'm not sure I like being referred to as like a dog." Jamie asked. "Yeah! Like a dog. That looks perfect. You're all fours with your bum out in the air. I'll be like the big alpha and you'll be like my bitch!" Jamie grumbled as Tom said. Great, now he's calling me his bitch but then again I guess I am he thought. "Perfect, wow that looks nice and tight," Tom said, getting behind Jamie and peeling his bum cheeks apart. Jamie heard the squirt of the hand cream. He gasped and recoiled slightly from the cold cream being rubbed on his hole. Tom pushed a finger in to rub a bit inside and Jamie realised how big that felt. With a sinking feeling he reckoned Tom's hard cock was definitely a few fingers worth of size and this would hurt. The finger pulled out and he heard more cream being squirted. "I'm just getting my cock all slick and then we're ready to go. Once I push in that's it. I'll have taken your cherry," Tom said, sounding delighted about the whole thing. Jamie was fully aware what was going to happen although he had a worry that it would be of a bursting of a cherry rather than a taking. "Ok here we go!" Tom said, unable to hide the excitement in his voice. An excitement Jamie didn't share although he did feel some anticipation. A curiosity as to whether this would be ok. He knew gay people loved anal sex. He could never quite work out why you'd want something so big up you. The bigger it was surely the more it hurt. In any case he knew he was about to find out all about it. Jamie felt Tom's dick part his bum cheeks until the tip was pushing against his hole. Tom pushed but Jamie's hole was staying firmly closed even with the cream rubbed over it. Tom might want jamie to do it but it seemed that part of Jamie's body was saying no. For now anyway. "Come on. Open up Jamie! Try pushing back like you're having a shit," Tom said. Jamie tried but it didn't work. Then with a powerful thrust Tom pushed and his cock head slipped in. "FUUCCCKKK!" Jamie screamed in pain. He'd never felt anything like it. It felt like he was being ripped apart from the inside. How could something as relatively small as Tom's cock cause so much pain? He hoped Tom would leave it there for him to get used to but no, he pushed in until he was all the way in. That hurt as his hole screamed with the pain of it's unnatural expansion. Jamie could feel Tom's pubic hair up against him and he knew that Tom was balls deep all the way in. All six inches of thick hard cock was now buried inside him. His eyes watered with the pain and he gritted his teeth to prevent him screaming out. "Fucking hell. Oh my god this is so tight. Why hadn't I done this until now? Can you feel my fat cock in your Jamie? Filling you up?" Tom asked with excitement evident in his voice. Jamie whimpered in pain. He certainly could feel it. It definitely felt like it was a lot lot bigger than it really was. He managed to squeak a reply of "yes" and then whimpered again as Tom started to thrust in and out. The pain was intense particularly at first. His hole felt like it was on fire as Tom slammed his hard cock into him. He jumped at the pain at times and continued to whimper. Not that Tom seemed to notice or care. He made long grunts and groans as his cock slammed into jamie and his balls banged against Jamie's arse. However the longer it continued in between the pain there was....something else. A feeling of something pleasurable. Sometimes when Tom thrust in Jamie would whimper in enjoyment not pain. The pain started to dissipate slightly as the act went on. Jamie then realised his dick was hard and dripping. He started to wank himself as Tom thrust in and out. Partly to take his mind off the pain but partly because he realised he was really starting to enjoy this. The feeling of that hard cock inside him was answering all those questions he had about himself. Jamie's slight enjoyment was nothing compared to Tom's though. As Jamie approached his orgasm from his hand, Tom was getting close from his anal penetration of Jamie. What was grunts and moans of enjoyment became words as he got closer to cumming. "Uhh....so goood..........fuck..........ooh....shit..............oh yes....yes......oh god this is.....amazing....fucking hell..........mmmmm.....shit.....oh.........I love you Jamie.....fuck...fuckkkk...........ahhhHHHHHH,". Tom almost screamed as he unloaded his cum into Jamie. He kept thrusting until he'd shot it all and stayed in Jamie until he eventually softened and slipped out. Neither of them said anything. Jamie was overcome with what had happened and it seemed Tom was too. They cleaned up in silence in the bathroom. Jamie had the slightly embarrassing situation of sitting on the toilet while Tom's cum dribbled out of him. Afterwards as they finished getting dressed Jamie finally broke the silence, asking a question on his mind. "Um...Tom. When we were...you know....did you say you loved me?" He asked hopefully. "No I fucking didn't. You must have been hearing things. I'm not a gay boy like you now get the fuck out of here and I'll see you Wednesday," Tom said. The anger in his voice was evident and Jamie was shocked. Why was he being like that? He'd just taken Jamie's cherry and lost his virginity. Jamie thought Tom would be nice to him. Why was he being an arsehole to him? Jamie quickly got his stuff and left, wondering if he should have said more. Jamie lay in bed that night thinking of what he'd done with Tom. He couldn't lie. He had really enjoyed it. The feeling of Tom's big cock filling him up despite the intense pain at first. But he was conflicted, was he in love with Tom? He knew now that he was but was Tom falling for him too? Despite his denial he clearly said he loved Jamie but maybe that was just the lust? Tom seemed so angry when Jamie reminded him of it that it just left him really confused.. Jamie wondered what would happen on Wednesday. He guessed they would do it again but did he want to? Yes I do he thought but he'd want Tom to be nice to him afterwards. He didn't want him to be like the angry boy he was earlier. He cleared his mind and thought back to what had happened earlier. His hand snaked down to his dick and he started to wank himself off. He wished that Tom was there behind him thrusting his hard dick into Jamie again and again. He came on his bedsheets and cleaned up slightly. It had been an exhausting day and he fell asleep wriggling slightly from the slight pain in his bum that he hoped would be gone by morning.