“So let’s set the stage Jake. Tonight I am going to have a good time, and orgasm multiple times. You might have a good time, you might orgasm. But if you don’t, i don’t care. You had a good day, so i will try to make sure you have a good night.
But if you don’t please me, nobody will please you. If you do as well, in future days, as you have done so far today, we will have no need for whips and chains….i don’t mind using such props, but don’t need them. But if you act up, i will use them, and enjoy them. BUT, as today is the first day, i think i need to give you a little taste of what punishment is like, in order to incent you to be on your best behaviour going forward.”
With that, Master lead Jake towards the St. Andrew’s Cross, had him step up, facing the cross, and strapped in his ankles and wrists. Jake could barely move, and was well aware his backside was exposed and open to attack.
“See Jake, if you act up, i will take this perfectly fine ass of yours and turn it into ground meat. It won’t be pleasant.” With that, Mr. Jenkins struck Jake’s ass with a paddle, hard. “When i strike you, you will respond ‘thank you sir, please may i have another’.”
Jake responded as told, and was rewarded with another hard smack on the same cheek. After each smack he thanked Master and asked for more. After a dozen smacks on each cheek, Jenkins put down his paddle. He took some cool cream and started to lightly apply it to the boys buttocks. Jake was strangely aware that despite, or perhaps because of, the spankings he was throbbing hard and his heart was beating. WTF – he was enjoying this?
Next Master started to tease Jakes sides, legs and but with a light feather. Tickling him, making him squirm. The pain from the spanking quickly receded as Jake was distracted by the feather. He was struggling to breath, laughing, not sure how much more he could take.
Master stopped the tickling, and pulled Jake’s body an inch or two from the cross. “I have seen diamonds that weren’t that hard. And damn that is a lot of pre cum Jake. Tell me, have you ever been with a guy before today”
“No” answered Jake. Smack, Master spanked Jake’s left butt cheek. “No, what???”
No, Master. And thank you, may i please have another.”
Damn the new kid was picking things up quickly. Mr Jenkins prided himself on his instincts, when bidding on ‘straight’ boy slaves. Looks like he was right again. This kid was going to be a great addition to the stable.
“Be honest Jake, did you enjoy massaging the boys, and stroking their cocks?”
“Yes Master. I didn’t expect to, but they are all so hot. I have never stroked another guys cock, but it felt good. And i loved making them all moan and squirm.”
“Well Jake, i have one more question for you, before we move over to the bed. And i will be sharing this answer will the boys. Who did you enjoy massaging the most?”
Jake paused. He didn’t want to answer, but knew he had to. Master wouldn’t stand for silence long. But Jake wasn’t really sure. “I don’t know. Tom was my first, and very helpful. Connor cuddled me afterwards. Joe has an amazing ass. And Max took charge of me, which i thought i would hate….but I really liked it. I can’t believe I am saying this, but i think I liked Max most – when he spanked me, and told me off, it made me feel used and cheap – which i really wanted. I know that sounds crazy, but i wanted him to treat me badly. Almost like i think i deserve it.”
“Well in that case Jake, you are going to love tonight. Now let’s get you down from the cross.” Master unbound the boy, and helped him down, leading him to the bed. “I am going to strip and lay down. You can start by massaging me for a bit, before i have my way with that ass of yours.” Mr Jenkins slowly stripped, taking his time to fold each item of clothes and put it carefully on a chair. He exuded confidence, aware that he was in completely charge.
After 30 minutes lightly caressing Master’s back, shoulders, legs and ass, Mr Jenkins told Jake it was time for him to lie face down on the bed. The exchanged spots, and Master started to massage the young slave. His strokes were long and slow, but deeper than the ones Jake used. Jake could feel Master’s hands dig into the knots in his muscles, releasing tension. After just a few minutes, Master started to concentrate on Jake’s ass.
He dug deep into the muscles, and used his hands to part Jake’s thighs – giving him access to Jake’s hole. Master’s touch became lighter, more teasing as he reached under the boy and tickled his taint and balls. Jake was in Heaven. Master tapped his ass, and told him to get on all fours, and prepare for entry. Entry? What? Was he about to get fucked?
Master dribbled some cool lube down Jake’s crack and into his hole. “Relax stud, you have already had a couple of finger up there…this is just a little bit bigger. It will take a couple of minutes to be comfortable, but after that you are really going to enjoy it”. A little bit bigger? Master was 6.5″ hard, but quite thick. This was way bigger than one, or even two fingers. Jake tensed in anticipation. “Relax kid, this will hurt way less if you are relaxed.”
Jake tried, but failed to relax. Master’s cock pushed at his tensed back door, slowly breaching the perimeter. Jake felt full – like he needed to take a massive dump. It was uncomfortable, but not really painful. Master very slowly pushed forward until he was all the way in, he still for about 30 seconds, and slowly pulled back. The next time he was slightly faster in both entry and retreat. He continued on, gaining speed with every stroke. Jake continued to feel uncomfortable, but not pained. He was getting ass fucked by a rich, dominant, master and wasn’t entirely hating it. Fuck this week wasn’t going as planned.
After a good 10 minutes off pounding, Master repositioned Jake on his back and remounted him missionary style. He slowly entered again, and as he fucked Jake’s virgin ass, he leaned down and kissed the boy right on the lips. Jake leaned into the kiss, parted his lips and let Master’s tongue enter him. Master moaned in delight, riding Jake progressively harder before panting “I’m going to cum.” His face pulled back from Jake’s, and he released several ropes of hot liquid into the boys ass. Master slowly rolled off of Jake, and laying next to him, panting. Jake lay silent, trying to decide if he had enjoyed being fucked. He hadn’t hated it. And he did enjoy hearing Master moan and groan.
After a couple of minutes, having caught his breath, Master said “ok kid, you did a good job for a first timer. And you have a great hole. So tight. You can take care of that erection now.” Handing the boy some lube, he lay watching as Jake damn near ripped his own cock off, desperate for release.
With both guys now satisfied, Master informed Jake this would be their daily routine, at least on week days. Weekends for were parties, with guests. Those would be a little more interesting.
“You have had a long day Jake, and you have done well. After you clean up, you can go join the boys in the theatre room. They are probably gaming, that is what they do most nights. Leave all the dirty towels and laundry in the bin by the wall, the girls will come by and grab it. Clean bedding and towels are in the closet over there.”