Usual Rules Everyone
You're in Trouble
Part 2 -- Timmy's interesting Weekend
When all the boys were in the basement at Saladin's house they stripped to shorts and put on their masks. They stripped Mike to just his briefs for effect and secured him in a chair, but in comfort. Then they took the blindfolds off both but kept them restrained, the earplugs were put in and then Tony started his brief.
"Now listen very carefully cunt," talking to Timmy, " You are going to do everything we tell you during the weekend. Every time you disobey an order, or comply with it too slowly you are going to get spanked.
You will leave here on Sunday evening with your mate, whether you do it walking normally or hobbling because your butt is so badly bruised is entirely up to you."
Nodding to Jack he continued.
"Take his gag out. Do you understand your brief you little shit?"
Timmy struggled against his captors as he replied.
"You let me go or I'll get my brother to fucking kill you."
Tony nodded and Timmy's two captors bent him over a chair. Tony delivered five smacks with his bare hand onto Timmy's backside but with so much force that even through his jeans and boxers it still hurt like hell. Stood up and facing everyone again Tony repeated his question.
"Do you understand?"
Timmy nodded and the boys released him. Of course he made a dart for the door which was locked even if he had managed to reach it, which he didn't. Over the chair again and another five which had him seriously squealing now.
Stood again and with tears in his eyes Timmy waited.
"Take your trainers and socks off."
The order brooked no argument so Timmy did.
"Good boy, now your T-shirt."
Very reluctantly Timmy did.
"You appear to be learning so keep it up and remove your shorts."
No action so he was over the chair again for his third set of five.
The shorts were off in a millisecond after that.
"Now your boxers, and when they are off stand with your legs wide spread and your hands gripped behind your head."
Amazingly Timmy did, instantly.
"Your ass is already starting to glow a little so think how much worse it is going to get if I spank you on it again now that it is bare. So listen carefully. Whatever happens now, you are not to move unless specifically told to. You are to acknowledge every instruction by simply saying `Yes Sir'. Do you understand?"
Timmy looked at Mike who just shrugged.
"Yes Sir," followed.
While this was going on the boys were all walking round Timmy scoping him out. No doubt about it he was a seriously cute kid. Todd realised how different they were then. No doubt Timmy was his mother's child and he was his father's. Dad was an ex football player and mum had been a cheerleader, her quite petite and dad huge.
A nod from Tony, and Saladin and David moved in and started stroking Timmy. They avoided the groin and ass for a few minutes and Timmy started to relax a little so then they moved to his ass which they stroked, David started to bone up, it felt so erotic, fortunately for him Saladin did as well, particularly when he ran his finger down the crack to one very soft and inviting rosebud.
"This man cunt is as soft and sexy as any girls, I'm going to enjoy fucking this."
Timmy was shocked, 'they wouldn't would they?' was his thought, then ass and groin stroking followed. It was obvious Timmy was torn. He wanted to move but knew there was nowhere to go. He started to blush and also to elongate. His erection when it was complete was typical of a sixteen year old with raging hormones. It was hugging his belly and looked very pretty.
Todd thought, 'fuck the little bastard is as big as me'. Both he and Timmy were circumcised and mustered a little over six inches, the only apparent difference between them was that Todd was thicker.
With his solid erection Timmy was blushing like mad.
Some of the boys looked at Mike who was blushing as well because he was sporting a solid erection as well which he couldn't cover up. It looked smaller than Timmy but nothing to be ashamed of.
Todd had filmed all of the action so far and was taking stills as well. He stood in front of Mike and whispered.
"Would you like Timmy to give you a blowjob and later fuck his little ass?"
Mike nearly wet himself at the thought and nodded his head vigorously. Todd grinned, he had it correct. Mike was a little faggot, which he stowed away for future use. You see Todd was into boys as well, that was probably why he was so soft on Timmy.
David was still stroking Timmy's ass and letting his finger worry his rosebud.
"Time for him to use his mouth other than to razz his elders don't you think."
Tony nodded at Jack, "Want to go first?"
Jack grinned, "Yeah, let him take my shorts off and I'll get comfortable."
Tony grinned at Timmy, "Ok sexy boy, take his shorts off," pointing at Jack, "And then you can give him a blowjob. Don't fucking hesitate or I'll give you ten on your bare bottom."
Timmy was mortified, this was only the start of the weekend and he was already being asked to go down on one of these guys, it had to be planned to get worse and the comment about fucking him was now frightening. He did however move over to Jack and removed his shorts. Jack sat in one of the old armchairs and spread his legs. He was already nearly erect thinking about this and he knew he had nothing to be ashamed of. Seven thick inches would feel good with Timmy's mouth wrapped round it.
Not the same thought Timmy had, his was more, `Oh my God have I really got to take that in my mouth?'
Answer was yes but only when he was told to.
"Ok little cock sucker, start by licking my balls and using your hands like I used mine on you."
Straight or gay, the remainder of the team were sporting erect penises in their shorts and looking at each other's groins to check them out.
Saladin and Tony got the most attention. There was no doubt that Saladin was sporting a good twelve inches, it looked incredible, and Tony was only a couple of inches shorter.
"Fucking hell bud, where have you been hiding that." Todd blushed as he said it but he was so turned on by the size of this monster he couldn't help himself.
Saladin grinned.
"I've been saving it for a special occasion but now that you've all seen it I might make every day a special occasion and let you all play."
Everybody rolled around laughing but Todd, Mike and David wanted to play with that piece of equipment, and some, so Saladin's next comment had them almost salivating.
"I'm not gay, but I don't have any problem with man on man sex. I've heard that boy pussy is better than girl pussy and this weekend I'm going to try it. If it is I'm going to fuck some ass and get some serious blowjobs and any takers will be guaranteed secrecy."
The others were all amazed and Timmy looked at the cock that he thought would kill him if it entered his ass.
Laughter over and they all returned to the business in hand. Jack was doing a great job teaching Timmy how to give head. He wasn't very enthusiastic but he was doing as he was told.
"Nice going slut, now use your tongue to caress my cock head, check out the piss slit as well."
Jack was loving it and Timmy was not.
"Good boy, now lick all of it, piss slit to base, top and bottom. Every time you get to the base take my balls in your mouth and swab them with your tongue."
David was getting so turned on he knelt down beside Timmy and started to caress his body. He stroked and tweaked his nipples making Timmy gasp before moving down and stroking his penis with one hand and his butt with the other. What a difference that made, Timmy got considerably more enthusiastic on Jack's cock.
"Get up on your knees Timmy and spread your legs."
Instant obedience pleased David, he then started seriously playing with Timmy's ass, stroking it and licking the cheeks. He slicked up a couple of fingers and after playing with his rosebud for a few minutes slid the first finger in. Timmy gasped and then continued blowing Jack as though nothing had happened. When the second finger went in he wriggled his cute little butt a bit and then nothing.
The others were all fascinated by the action at both ends. David couldn't remember ever being so hard and nor could Todd as he filmed everything.
Three fingers and then David grabbed some lube and using that went to four fingers which he used to fuck Timmy with.
There were a lot of cocks straining to get out of overstretched shorts by this time. The final which had everyone mouths agape was David slipping his shorts off, lubing his cock and entering Timmy very gently, just getting over his sphincter.
Timmy came off Jack's cock and looking totally shocked twisted his head to see what was happening. Then he burst into tears.
"Please don't fuck me. I beg you take it out."
David looked at Tony and Todd both of whom shook their heads.
"Keep sucking me slut or I'll turn your ass blue." Jack was too far gone to want any interruption, he was about ready to fill one boy mouth with sperm.
Timmy did as he was told sobbing for the first little while until the pain went away. David picked up on it and slid more cock into him. Within ten minutes he was able to start long stroking Timmy to the obvious delight of both. Timmy couldn't believe how good it felt as David kept hitting his prostate on every in stroke. When Jack orgasmed he held Timmy's head and just said, "Swallow it all." Timmy did and started cumming himself, tensing his gluts and taking David over the top at the same time.
David's orgasm was stupendous Timmy was a seriously hot guy, as he went soft he slid back onto his haunches pulling Timmy with him and cuddling him. He whispered in his ear.
"That was incredible little one, you are forgiven all the crap you have given me over the years. That was a wondrous experience."
Timmy was crying with the humiliation of his friend and these anonymous men witnessing him being fucked and still being able to cum as he took a mouthful of someone else's cum but it had been incredible for him as well.
"I know it's you David, thank you too, I promise not to tell anyone."
David was gob smacked, how had the little toad guessed?
David continued to stroke Timmy gently as all three of them calmed down.
"Very nice guys, so it looks like we can go two at a time."
"Good idea, why don't we let him suck his mate while you try his ass Tristan?"
Tony realised what he had said.
"Oh fuck, sorry mate."
David piped up then.
"Don't worry about it, I think Timmy has soused us out already, he knows who I am and over the weekend he is bound to guess several more of us so I'm removing my mask."
"Ok, let's not do anything to help him, but if he recognizes any of us we'll unmask, don't help him by using names like I have just done."
"I don't want to fuck him, but he can give me a blowjob later."
Tristan was very definitely hetero and had come along out of curiosity. Several of the team had not wanted any part of it but Timmy still had eight guys to satisfy.
Adam was the closest to Timmy's age but still a big guy he volunteered to fill the other end but looking very embarrassed.
"Way to go guy, let him feel another real man inside him."
Tony knew that would make Adam feel better.
"Why don't you let him suck you for a few minutes first to make sure you are solid and Mike can finger him before you change round?"
That was Todd who wanted this all on film.
It all looked very good as Timmy took Adam's shorts off revealing a nice seven or so inches and then Mike's briefs confirming a neat five inches, quite slim. The action then looked great. The pleasure on Mike's face was testament to his enjoyment fingering his mate, he was up close and examining Timmy's anus closely, stroking it and sliding a finger in at intervals. That pleasure increased a hundred fold when Timmy's lips slid over his glans. The action then continued the same as before and Todd realised he needed more variation to make the video look good. He whispered to Tony.
"With the next two let's have him in a different position so that the film doesn't get boring."
The rumpus room bed was perfect. All it consisted of was a huge mattress on a wooden base raised about twelve inches off the floor. A guy kneeling on cushions would be at a perfect height to fuck ass. If Timmy then rested his head on a pillow and turned it another guy could kneel comfortably while being blown. Saladin chose to be sucked and Wayne was going to get a fuck.
Crikey, did he ever get a fuck. He went at Timmy like a little jackrabbit. But hardly anyone really noticed. They were all goggle eyed watching Timmy trying to suck Saladin. The cock was a monster but David and Todd were almost wetting themselves thinking what it would be like to replace Timmy. Wayne came very quickly and Saladin noticed.
"I'm going to the other end, maybe his ass can do a better job on my cock than his mouth."
Timmy went ballistic and tried to get away. Of course there was no chance of that but it earned him another spanking. The boys loved this one. He was stretched over Tony's knees and held in place by his arms and legs while Tony stroked his bottom
"That is such a pretty little boy cunt Timmy, I really don't want to bruise it but you have to learn to do as you are told."
He then administered five hard slaps with his bare hands again, only to a bare bottom this time, eliciting screams of pain from Timmy. Back on the bed for Tony and Adam to hold his legs wide and back while Saladin prepared to fuck him. Timmy looked terrified as Saladin lubed his penis liberally and then Timmy's ass.
The cock head resting on Timmy's rosebud was photographed extensively and then Todd swapped to the camcorder to record the penetration. The sight was incredible as Timmy's little anus gradually stretched as Saladin increased the pressure until his glans slid over Timmy's sphincter. The pain was obvious and Saladin didn't move for about ten minutes until Timmy calmed down and stopped sobbing.
During the next fifteen minutes four guys creamed their shorts without touching themselves as they watched Saladin's cock slowly disappear inside Timmy. The slow fucking after that was just totally amazing. Tristan decided to get his blow job then and almost choked Timmy with the volume of cum he shot into his mouth. Not surprising really. Timmy's butt was small and rounded, Saladin's cock had to be nearly three inches across, it was just amazing to see it moving in and out between the two little cheeks.
"If I talk to you guys while I fuck this little hottie I can probably last an hour."
Timmy looked aghast at what he could see happening to his ass.
"Please David, make him cum I'm getting so sore."
Todd and Tony piped up together, "Yeah buddy, remember we have two more days."
That was enough said. Saladin powered in for an incredible orgasm taking Timmy with him but also eliciting screams of pain at the ferocity of the last thrusts.
Everybody calmed down and Tony suggested they order food and then showered and called it a night on the sex front.
"We leave boy cunt here and we can watch some TV before bed. I suppose we had better feed him. Mike you are staying here with him for the night."
With that they all left locking the door behind them.
Mike led Timmy off to the shower and pampered him.
"I'm sorry I took part Timmy but you are such an incredibly sexy guy I couldn't help getting hard and then I had to do what they said."
Timmy looked at his friend not quite sure of the sincerity of his words.
"Would you like to do it again now that no one else is here?"
Mike fell into the trap.
"Oh God yes Timmy, can I blow you as well."
"You're a faggot aren't you Mike? Are you in on this with that lot?"
Mike blushed almost scarlet.
"You are aren't you, all the pain and abuse I take this weekend is your fault. I fucking hate you, don't you ever come near me again or I'll tell Todd and he'll kill you."
Mike wanted to retaliate at this verbal battering and couldn't resist.
"Huh, I doubt that, who the fuck do you think is taking all the video and photos?"
Timmy was stunned but needed time to think.
"Ok, if that's true you can do anything you like to me tonight, but if it isn't I get to fuck you with the biggest dildo I can find or ask Saladin to do it, agreed?"
"Oh yes Tim, I want to fuck you but will you fuck me as well?"
Wow what a night. After the food had been delivered Timmy went 69ers with Mike, but before either of them came he let Mike enter him. It did feel good after Saladin's monster, Mike's little five incher was perfect, hitting his prostate regularly enough to make him last a long time but not spoil it. He was soon erect again and nearly hit the roof when his glans slipped over Mike's sphincter.
"Oh yes Tim, that feels incredible. I love you so much please fuck me hard for getting you into this."
Timmy didn't want to, he wanted this to last all night it just felt so incredible. His mind was thinking about other things while this was going on. He wondered what it would be like to have Todd fucking him, but doing it with love. Or the pair of them 69ing and eating each other's sperm before lying alongside each other kissing and cuddling. Ok it was incest but Todd was such a super brother even if he did give him an incredibly hard time. Then it came, he felt his orgasm coming up from his balls like a jet plane before blasting Mike's inside with cum and squealing with pleasure.
All cleaned up and lying together on the huge bed Timmy said.
"All wagers are off Mike, I won't hold it against you that you set me up and you never tell a soul that I knew, deal?"
"Oh yes Tim, are we still friends then, and can we do this again?"
Timmy laughed, "Yes to both, now let's get some sleep." -----------------------------------------------------------------------------------------------------------------------------------------------------Saturday morning breakfast was delivered to the two youngsters at ten. At eleven all the boys piled into the rumpus room for the start of the day's sex.
"A quick round robin of sucking to start I think."
Tony had discussed this with Todd, it was so that he could get a blowjob from his brother.
The reality astounded Todd. Timmy gave him an incredible one, far better than any of the others. He had watched them all and none had been as erotic and sensual as his.
"Oh fuck Tony, if his ass is half as good as his mouth he will be the best fuck in the universe."
Timmy visibly preened at that comment completely confusing Todd. During the rest of the time to lunch, everyone got a fuck and some got second blowjobs. Todd had religiously filmed everything and the boys had taken Timmy in as many different positions as possible. Todd was going to be last. He cleaned his brother up completely because he was going to make love to him properly.
"Ok guys, make yourself comfortable, I'm going to show this little hottie what man on man sex is like when done with love."
Timmy was crying with happiness being totally pampered by Todd. He was kissed and caressed everywhere that was sensual. Todd sucked his cock and his balls, slurped on his rosebud before nearly sucking his insides out and then he took him doggy fashion. He was getting really turned on watching his cock slide in and out of his brother's anus until Timmy whispered to him.
"Please turn me over Todd, I want to watch your eyes when you cum inside me."
Todd couldn't believe that Timmy knew it was him. He did turn him over and re-entered him before looking him in the eyes. He gasped. Timmy's eyes were full of tears but the look was love and happiness.
"I love you so much Todd, I'm sorry I've been such a total shit. Please love me like this often and I'll be a good boy for you forever."
The orgasms from both of these brothers were heart stopping. The other boys couldn't believe what they were seeing and hearing.
Todd didn't pull out of Timmy until he was completely soft. Then he took Timmy in his arms and stroked him, totally oblivious to anyone else.
Timmy was the first to speak. He looked round at all the other faces.
"If any of you want to fuck me again can you please do it in private," then looking at Todd he started to cry softly, "Please Todd, I'm sorry I've been a pain to everyone I promise I'll be good from now on, but please don't let anyone else fuck me this weekend, I'm so sore."
Todd looked with love at his brother and then looked at all his mates.
"Your call guys but can we knock this on the head?"
Tony looked round and each face he saw looked back at him and nodded.
"Yeah, I guess so Todd, I think we have all had much more than we expected from this little hottie." Then looking very stern he spoke to Timmy.
"If you give us any more razzing though you get this again only we'll invite the baseball team as well ok."
He was grinning which kind of killed the seriousness of his statement.
Timmy was happy with this outcome and let his fun side show.
"Ok, but can I razz you a little bit if I want a fuck?"
Everyone collapsed with laughter and didn't hear David say.
"You can razz me the same as always if I can fuck your cute butt every week."
Timmy grinned and thought how lucky he was, Todd would make love to him frequently he was sure, as would Mike and David, if he felt very brave he could go to Saladin for an incredible fucking and he thought two of the others wouldn't take a lot of persuading to go to bed with him. Hmm, life was about to get much more exciting.