Brandon The Brat : Part 6 - Chris joins the family

Brandon is small in stature. He is 20 years old but extremely skinny and small. He stands about 5’ 4” and weighs maybe 110 lbs. I think his waist is only 27 inches. His dark brown hair is short in what we used to refer to as a butch cut. His body hair is shaved due to his immaturity. He is also forced to where a chastity device so he will not enjoy personal pleasure. He can only get pleased by his new appointed babysitter (Only with my permission), or by me. Since he chooses to not grow up he is also wearing diapers. He isn’t allowed to use the toilet and must be cleaned up by Josh. He is treated like the little baby he acts like.

Josh is 18 and also extremely small for his age. He stands 5’5”, and maybe weighs 114 lbs. His waist is only 26 inches. His butt is smaller than Brandon’s but still nice. His package though is bigger as the bulge in his pants show. He has blonde/ light brown shoulder length hair, and blue eyes. As far his pubic hair, he is now just trimmed. He has matured a lot and has allowed to wear normal clothes. He, still is required to wear his chastity device.

It is Sunday and Brandon informs us that we have been invited to go to Kings Island with his dad and uncle on Saturday. He begs for me to agree. I do. I think it will be a good test for him. I am less concerned about Josh because he has really stepped up and matured. The way he handles Brandon has impressed me. Also, because he and I have basically become a couple raising a brat. Brandon then asks what he is allowed to wear. I tell him the only change is that he will be allowed to wear tight white briefs and that he can use the toilet when he needs to. I let Josh decide what he will wear.

Josh tells him that he will continue to wear his little boy clothes and that it is final.
“Well, then I am not going!” Brandon says as he stomps his foot and begins to pout.

“OK, then we won’t go!” I say. “But if you throw another little hissy fit, I will have Josh Blister your butt.
“Come on,” He says, “I will be completely embarrassed in front of my family.”

“That is your fault, not ours!” Josh steps up. “Look, I had to face my mom and dad wearing those clothes and look at us now. We are on good terms. They even offered to let me move back in. They asked why the change and I had to tell them the truth. They know that Mike spanks me and they know that I am in a relationship with him. They were uncertain at first, but now that they see what I am doing to improve myself and are greatly pleased. So start growing up and we will treat you like a grown up.”

“But I want to go to Kings Island!” He says.
“Then you will go dressed as I see fit.” Josh says.

I absolutely love the way Josh has taken control of Brandon. It gives me more time to focus on him. We still get into spanking for fun and Josh has expressed an interest in trying some more BDSM sessions.
“Fine, but please don’t pick out something to embarrassing.” He gives in.

Saturday morning comes and it really hasn’t been a good week for Brandon. He has earned spankings every day except for Monday. So, obviously, his butt is extremely tender. Josh decides that Brandon is going to wear a Sponge bob t-shirt, a pair of jeans, and his sneakers. Josh gives him ten smacks on his bare butt before he dresses him as a reminder to behave and be extremely polite.

We have to take two cars because apparently Brandon’s sister was also going. Brandon rode up with his uncle, dad, and sister. That left Josh and me in my truck. We talked about what we thought was being said and then about me and him.
“Josh,” I start. “Are you happy, I mean I am 27 years older than you are, surely you can find someone closer to you age.”

“I don’t want to!” He exclaims. “I really love what we have going on. Even if Brandon wasn’t here, I would stay! I love how you treat me and I think I, uh, love you.”
“Well, I know I love what we do and I enjoy our relationship.” I reply. “I just wanted to make sure that I wasn’t holding you back!”

“Look at how I have changed Mike!” He said. “I am starting college classes, I have a relationship with my parents, and I have matured quite a bit if I may add.”
“Yes babe, you have!” I say.

He kisses me on my cheek and then decides to lie down. He head is resting on my leg as his hand is on my thigh. The rest of the trip is spent like this until we arrive.
We park and everyone gets out and stretches. Brandon’s dad comes over to me and ask me for a moment alone.
“Brandon told me about his rules and the punishments.” He says.
“Ok,” I reply. “These were set up when he…”

His dad interrupted, “I am not mad, actually, I want to thank you. Brandon has never treated anyone with this much respect before. If he is happy with the situation and it is helping him grow up then I am all for it.”
“He said he was happy with it?” I said shocked.
“Well, not that he was happy with it,” Frank said, “But he knows it is what he needs.”

“Well, thank you.” I reply, “I have only tried to do right by him. Today it is going to be your four together. Josh and I are going to go on our own and let your family enjoy the day. The only thing I ask is that you let me know if he misbehaves. Now let’s go ride!!
“We most definitely will.” He says.
“Call me when you all are going to do lunch and we will meet you if you all want.” I say.
“OK.” He responds.

We went our different ways and the day went great. Josh and I had a blast. We rode the rides we wanted to over and over again. We saw Brandon’s family several times throughout the day and they seemed to be having a great time. I got a call that everyone was tired and that they were ready to go so we met up at our vehicles. Frank let me know that everything went well and he behaved like a little gentleman. He back-talked a couple of times and cussed at his sister, but that was it. We said our goodbyes and headed home. Brandon rode with us so they wouldn’t have to stop by the house on their way home.

The drive home was spent with Josh crashed leaning on me and Brandon crashed leaning on Josh.
We finally got home at 7:00 P.M. Once inside. I told them that I had a three for all planned but since Brandon did what he did he was to be bathed, diapered, and put to bed. I removed Brandon’s cock cage and then allowed Josh to jerk him off. It only took about three minutes since he hadn’t orgasmed in a while. Josh then left him standing there nude as he went and ran his bath. It is funny to see how self-conscious one can be when he is being made to stand there completely naked.

‘How did you like getting double penetrated last week?” I asked him.
“It was pretty good after the hellish pain eased.” He said.
“We are going to do something different tomorrow.” I said. “You also are going to be completely nude anytime you are inside. Always ready at our beck and call.”
“I can handle that.’ He said.

Josh came in the room, grabbed Brandon, bathed him, and then put him to bed. He came out and I asked him if he was up for a little fun.
“Of course.” He quickly answered.

I took him to the bedroom, stripped him down, and told him to lay down spread eagle on the bed. I grabbed a cushion and placed it underneath him so his butt was sticking up in the proper position. I tied his hands and feet so he couldn’t move.
“You’re gonna get a show tonight Brandon!” I say as I grab the strap.

After positioning myself I take the first swing without letting Josh know it is coming.
THWACK!!!!
“Holy mother of Gatsby!” Josh yells.

I continue on pausing about fifteen seconds between each blow to his wonderful rear end. He groans then starts to get vocal with each impact. His cheeks are turning a nice shade of red as I continue the assault.
THWACK!!!! THWACK!!!! THWACK!!!! Come the next three
“OOOWWWWW!” He bellows.
I drive him close to crying but don’t cross that line as this is about fun, not punishment.

I crawl in between his legs, spread his cheeks, and start to rim him as I toy with his balls.
“OOOOHHHH YEAH!!” He moans as give him a feeling of pleasure that he has never experienced before. I grab a butt plug, lube it up, and push it in.
“AAARRRGGHH!” he grunts.

I get up, grab my riding crop and start slapping him up and down his body. He twitches with every blow. They aren’t extremely hard hits, just hard enough to make him feel the sting. I continue the onslaught until his entire back side is a nice shade of pink.
I remove the plug and slowly insert my throbbing cock, I kiss his neck as I suddenly thrust all the way in.

“AAAAUUUGGGHHH!” Josh groans as I hit his prostate. I stay there for a few pushing in as much as I can. I then start pounding his ass as fast and hard as I can. He is moaning loudly and encouraging me to hit it harder. I go until I know I am gonna shoot.
“Holy shit!” I yell as I feel my balls draw up and expend my load inside my 18 year old lover. I collapse on top of him and start kissing him all over his face until our lips meet. We french for a while and then he tells me that we are going to have to change the sheets cuz he shot while I was pile driving his ass. I laugh as I climb off him. I untie him and we go shower. We are both spent so we climb into bed and cuddle. It isn’t soon until we fall asleep.

We wake up the next morning before Brandon and decide that it is time to give him his torture. After we cover the bed with a plastic sheet we grab him and bring him to the bed. We tie him spread eagle and then wish him a good morning. The tickle torture starts. We tickle him all over as he struggles and laughs. We continue the onslaught until he loses control and pisses allover himself. We then start drenching him in our own piss from head to toe. The plastic sheet is fixed so none of the fluids leak to the floor. We then fix it so all the piss is pooled around Brandon. We decide to go eat and leave him soaking in our pee.

After breakfast we walk back in to have him beg us to get him out.
I tell Josh to go bath him good, shave him bare, and then to bring him back in and strap him back to the bed face down. While he bathes him I clean up the plastic and take it to the garbage.

Outside I see one of the boys that lives in the neighborhood. He is 19 years old and gorgeous. I never see him with any girls. His name is Chris He is 5’9” tall, weighs probably 150 lbs., has blonde hair and blue eyes, and from what I can tell he is well gifted.
“Hey Mike!” He yells as he comes over to the fence.
“What is up hot stuff?” I jokingly say.

He blushes a little and then asks about Josh and Brandon. I take a chance and tell him all about it. He stands there and then ask if we really did that stuff. I tell him that we do and I can tell he is interested because of the tent he is trying to hide.
I invite him in and he accepts.

I ask if he has ever been spanked and he says of course, just not for fun. I tell him the basics and how far we go. I do tell him that there is sex involved if the participants want it and then ask if he has ever done something with other men. He says a little but doesn’t offer details. I tell him that we are going to spank Brandon first and he can watch. Then we spank him if he is interested. He says ok. We walk in the bathroom as Josh is still bathing Brandon. Brandon moves to cover himself but I order him to relax and to not hide himself. I introduce Chris to them and tell them that he will be joining the fun today.

Chris and I are in the room when Josh leads Brandon to the bed. Both of them are completely nude. I tell Josh to warm him up over the knee before he gets strapped to the bed. I watch Chris as Josh bends him over his lap and starts spanking him all over his butt. It is turning pink but Brandon doesn’t move. After about 15 more spanks I see Chris adjust his hard on. I reach back and give him a squeeze. I was right, he is well gifted. He jumps a little at my touch but doesn’t move away.

Ok Josh, strap him in. I pick up the strap and right after Josh straps his last leg I bring it down on his bum hitting right in the middle.
“Thwack!!”
“Holy mother!” Brandon yells at the shock.

I give him five more decent hits and give Josh his turn. Josh chooses the paddle and takes his time delivering his hits.
“Well, what do you think?” I ask Chris. “Think you could take a spanking?”

Nervously he says, “Yes, but I don’t know how much I could take right off.”
“Want to find out?” I look at him.
“Yeah.” He smiles.

I tell Josh that Brandon is all his as I strip off my clothes and sit in the chair. I pull Chris over and tell him to take his shirt off. He does and his tanned chest has very little hair and I can see a light trail leading down from his belly button. His pinkish nipples are about the size of a dime. I reach under the waistband and pull down his shorts and underwear. His 7” cock jumps up and slaps his stomach as his low hanging balls bounce in the freedom. His pubes are trimmed and this makes me happy.

“Wow, young man!” I exclaim, “We could have fun with this.” putting my hand around it and stroke it a few times. He shivers as I rub over his head. Alright, let us see what you can take. I bend him over my lap so our cocks are touching. He moans. Josh and Brandon are watching as I start rubbing his small white furry, but very spankable ass. I start of slow and give him medium hard smacks. He took them so I went to the sit spot and gave him 5 good smacks on each cheek. A low level “Ow” came out. Josh started back on Brandon and I told Brandon and Chris that they are to face each other the entire time.

Josh grabs the strap and I grab the brush. I ask Josh if he is ready and He says “Yes sir.”
I don’t hold back and proceed to give him five hard smacks to each cheek. As Josh lands 5 good hard hits to Brandon’s now red butt.
“OOOOOOOOWWWWWWWW!!!” Cries Brandon as he squirms before each hit.

“Crap!” exclaims Chris. He is grabbing my ankle but his dick tells me all as I feel some pre-cum drip off the tip.
I tell him that I usually fuck the one I spank after I am done and I ask him if he wanted me to impale him when I am finished.

“Yes sir.” He says right before I start the assault on his reddening buns.
SMACK!!! SMACK!!! SMACK!!! SMACK!!! SMACK!!!
“OOOOWWW!!” he yells as his voice quivers and he is starting to move about. I reach under and grab his cock and pull down.
“UUUNNNGGHH! He grunts.

Brandon is yelling as Josh drives him close to crying but doesn’t push it.
I continue “breaking” in Chris’s ass as I land ten more making sure to cover it thoroughly. He yells but isn’t crying. I stop and start to rub his cheeks. I feel the warmth and notice the ever dripping pre-cum that is freely coming from Chris’s cock.

“You ok?” I ask. I am not wanting to push him too far and scare him away.
“Will you use the strap on me sir?” he asks.
“Are you sure?” I ask surprisingly.
“Yes sir!” But if it is too much I will let you know.” He says.

Josh hands me the strap as I tell Chris that all he has to say is the word purple.
“Yes sir!”

I feel his grip on my ankle tighten as I rub the strap around his butt.
Any bets on how much he can take?” I ask.

Brandon says five as Josh says ten and then we hear Chris say fifteen.
I start in hard and fast.

THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!!
“OOOWWWWWW HOLY SHIT!!!!!!””” He yells as he squirms.
THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!!
He starts crying as he wails but he doesn’t quit.
THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!!
“Mother of pearl son of a gun!!!!!!!!!” He yells as tears roll down his cheeks. He still doesn’t give up
THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!! THWACK!!!!
“Purple!!! He yells ass his body falls limp over my lap and he sobs.

I motion to Josh to get me a cool wet rag and some lotion.
I caress his back, spread the lotion on, and then lay the wet cloth on his fire red ass.
“Damn boy, you could have quit before then!” I say. “Are you ok!”

I had to push myself to see if I could take it and still be interested in getting spanked.” He said as he calmed down.
“Well, by the feel of your cock I would say that you are.” I reply. “Yes sir. “He replies.

I tell Josh to unstrap Brandon. He does and Brandon gets into position as I help Chris up and put him in the same position. (Doggy style)
Josh and I lube up and then at the same time thrust into Chris and Brandon.

“The both moan loudly and we pound them both until we shoot inside their tight asses. Right after, Brandon shoots but Chris doesn’t which is fine because I want his 7 incher in my ass. I slide underneath him on my back and raise my legs. He smiles, uses his pre-cum as lube and thrusts inside of me.

“Holy mother!” I yell as I feel him push all the way in. He wastes little time and starts pounding my hole. He bends down and kisses me on the lips as he thrust. He is pounding harder and all I can do is moan. I feel him tense and then lose his load inside me. He is spent and collapses on top of me.
“Oh my goodness!” He says. I have never felt an orgasm that intense before!”

We all laugh and say welcome to the world of spanking.
“Need another room mate?” He asks.
I tell Brandon to go clean up and I have Chris just stay as he is.

I take Josh into the Kitchen and we discuss this. I tell Josh of my longings for Chris and how I have wanted him for a while. He tells me that he is feeling the same for Brandon.
We come back into the room and Brandon in his bed and Chris as he was. I sit back next to Chris as Josh squeezes next to Brandon.

I start by handing Chris a set of the rules and have him read over it. I say that some of the rules are outdated and will be changed. I then tell Brandon that he is now Josh’s property and will obey his every word. Any punishment spanks will be given by Josh. The extent of the punishment will be completely up to Josh.
I look at Chris and ask if he understands the rules.

“Yes sir.” He says. “I am ready to follow them, sir”

I tell him that he is mine. He is to have no contact sexually with anyone else but me and must do what I say. I tell all of them that when it is just us in the house, no clothes are to be worn.
But that starts tomorrow night. I get Chris dressed and then dress myself.

I take him outside and we talk.

I ask what his folks are going to say. He lets me know that they kicked him out and that he was actually coming to my house to ask if he could stay until he found someplace. I told him he could stay as long as he wanted. I tell him that tomorrow we can go get his stuff. He tells me that He had a full size bed and that Brandon and Josh could use that. I thank him for his generosity. I also tell him that he doesn’t have to call me sir unless we are role playing.

I do ask why he got kicked out and he tells me that he got busted drinking and that they got in a fight. I let him know that he will need to be punished for that but will wait for another time. He says “Yes sir” as I put my arm around him and pull him close to me. He hugs me as we sit on the front porch and enjoy the night air. We head back inside to hear Brandon and josh going at it again. This is going to be a long night as I am hard again and Chris is tenting his shorts.

Attention readers: As I bring in the last character to this series, I am going to most likely break it up to Chris and me and Brandon and Josh as far as the stories go. There will be stories of all of us throughout the series but they will be spread out.