The boy and I have been texting and chatting off and on for a week. He is very confused about his feelings. He was very scared when I tied him up and face fucked him. He hurt when I dicked his ass for the first time. His ass hurt for days after.
But, part of him liked it. Part of was excited by a powerful man. Part of him wants to make Daddy happy. And he thinks of me every time he feel his boy hole ache.
The boy relaxed a little when I told him I knew other Daddy's and boys. It was comforting for him to know he wasn't the only boy with these feelings. That there were other boys who knew what he was going through and other Daddies to help. So we agreed that I would set something up for him; to meet another Daddy and boy.
"Ray, you dirty dog..." Daddy Jim said after I asked him the favor. "You just want to double team the poor boy."
"Hell yeah!" I replied "That boy's ass is tight. It needs to be stretched."
"Good enough for me. Who do you want the other boy to be?"
"Any of the sluts. Who's the youngest?"
"Brendan."
"Then bring Brendan."
When I told the boy about Daddy Jim and Brendan, he got excited. We arranged a late night meeting. My boy had to sneak out of his house after his parents went to bed. Then I'd pick him up and we would head over to Daddy Jim's.
When I get to the boys house it is dark, a good sign. I park down the street and wait. After five or ten minutes I see the boy sneaking through the bushes towards my truck.
He opens the passenger door and sits next to me. "You're late boy." I say somewhat sternly.
"Sorry Sir."
"It's OK this time boy. We're gonna have fun together." I put my arm around him and pull his head into my lap. Then I started up the truck and we drive off.
I tap the horn once when we arrived at Jim's house. The garage door opens and I pull in. The door closes behind us. I grab the boys hand and we make our way in. Jim is sitting on the sofa, puffing on a cigar. Brendan is naked at Jim's feet, licking Jim's boots.
"Hey. Welcome in." Jim says
The boy nervously looks down at Brendan.
"Come here boy." Jim orders. "Come talk to me."
The boy looks up at Daddy Jim and sheepishly says "OK." He carefully walks next to Jim.
"Relax boy." Jim says in a very friendly tone. "Tell me your name."
"Stuart." The boy says. Fuck, I've been chatting with the boy for a week and I've never asked him his name.
Jim grabs the boy's hand. "Good to meet you boy. Welcome to my house."
"Thank you Sir."
Ray turned to Brendan and says. "Boy, get Daddy Ray a drink and cigar." Brendan stands up and walks off. Jim turns back to Stuart. "So, tell me about you. I've heard that you want to meet other Daddies."
Stuart slowly nods his head.
"Did Ray tell me anything about me?"
"No. Just that you were a Daddy and that you had a boy."
"That's right boy." Jim says. "I have to tell you a few more things." Jim takes a puff on his cigar and then continues. "In my house there are three rules that all boys to follow. First... boys must always call me 'Daddy' or 'Sir.' Second, boys must always be naked. And third... boys do not say 'no' to me. They can plead, they can beg, but when I tell a boy to do something, he does it, or gets a beating. Understood boy?"
I could see the boy choke up. "Yes Sir."
"Good boy. Now what are you going to do for me?"
"What? I'm not sure you want."
"What was the second rule boy?"
"... that boys must always be naked."
"That's right boy. Strip."
Brendan returns with some scotch and a cigar. I sit down, lay back, lite up and watch the show. Jim points at his boots. Brendan returns to licking them.
Stuart, slowly pulls his shirt off. Then he takes his shoes off, drops his pants and then his underwear.
"Not bad boy." Jim says. "But you can do better than that. "Get dressed again."
The boy looks a bit confused but dresses again.
"Now, one of the reasons your going to be naked around me is easy access right?" The boy nodds. Jim continues "When you strip, you're going to give me what I want first... your ass. Understood boy?"
"I think so Sir." The boy sounds uncertain.
Jim takes his cigar out of his mouth and then says "This is how you strip. Stand in front of me. Where I can see you." Jim pointes at the ground in front of him. The boy takes two steps to his left. "Now, let's get started. Drop your pants."
"Yes Sir." The boy unbuttons his pants. They fall to the ground.
"Now boy, turn around and bend over." The boy does so, exposing his creamy ass to Daddy Jim. Jim reaches for the boy's ass and spreads the cheeks. "Keep stripping boy" Jim ordered. "Take your shirt off, then your shoes and socks, then get out of your pants. Jim fingers the boys hole while the boy finishes stripping.
Jim looks at me. "Damn. That is a tight hole!"
"Do you think a good spanking would relax it?" I ask.
"That might work."
"Please don't spank me Sir!" the boy shouts.
"Why boy? Why should I listen to you?" Jim asks.
"Because it will hurt Sir."
Jim and I look at each other and simile. Of course a spanking hurts. That's the whole idea-- to train the boy to submit his whole body to service men, even if it hurts.
"How about this boy... do you think you are as tough as boy Brendan?" I ask.
Stuart looked at Brendan and then said "I think so Sir."
"So if Brendan takes a spanking, then you could take one as well?"
"I don't know, I'm not sure Sir."
"Answer me sissy boy. if Brendan takes a spanking, could you could take one as well? I promise you that you won't feel anything that Brendan doesn't can't take."
"OK Sir."
"Good boy!" Brendan looks nervously at me. He knows how firm my beatings can be.
"You two, get on all fours in front of me!" I take my belt off and wait for the boys to get into position.
I give Brandon a good hard strap and the ass. Brandon calls out "Oh!"
Stuart is very nervous. "Please don't hit me Sir." Whack! I give Stuart a strap in the ass. "Oh!" Stuart is on the verge of sobbing.
I raise my arm and strap Brandon again. I hear another beautiful cry of pain. Then I strap Stuart with equal force. Stuart has started sobbing.
"Let's do this right" Daddy Jim says. Jim has rope in one hand and a ball gag in the other. Jim passes me the ball gag and then turns to Stuart. "Hold your arms together boy."
Stuart starts to ask "What are you..." But I cut him off when I shove the ball gag in the boys mouth. Jim quickly binds the boys arms together and hangs the boy from a hook in the ceiling. He then turns to Brandon and says "You too boy!" Before long both boys are gaged and hanging from the ceiling.
Jim lights up another cigar and admires the two boys. He runs his hand over Brendan's back and ass and says "This needs to be bright red."
I start belting the Brendan's back. I take a good twenty swings at it. Each swing leaves a nice red stripe. Brendan whimpers the whole time.
"Nice work." Jim says. "My turn. Stuart needs to be just as red." Jim takes my belt and starts whaling on Stuarts back. The boys delicate skin turns red more quickly than Brandon's but that doesn't stop Jim. Jim gives Stuart at least thirty belts.
I can see the tears fall from Stuarts eyes. I kiss him on the forehead and say "It's OK boy. You are doing great. Just hold on a little longer. We have to beat your ass now."
With that, Jim takes his belt to the boy's ass. He strikes the same spot over and over. I feel my cock get hard as I watch the boy squirm from pain and struggle. Soon, complete submission will come naturally to this boy. But, right now, I enjoy breaking him in.
Jim backs off and admires his work.
I grab hold of the boys ass and squeeze it tight. "That's so nice boy. Would you like me to fuck you now? Fuck you instead of beating you?" The boy eagerly nods his head. I say "You'll be fucked in a minute boy. I need to whip your ass first." I take my belt and strike the boy's ass over and over. The boys squirms and moans. "That's a good boy!" I say. Take your beating and be proud of it. You are making Daddy very happy."
My cock is throbbing. With each lash against the boys ass my urge to fuck the boy grows stronger. I ask the boy again "Do you want to be fucked boy?" Stuart eagerly nods his head.
"Good boy." I say as I rub his head. I walk behind the boy and drop my pants. I spit on my cock and spread the boys cheeks. I grab the boys hips and plunge my cock into the boys ass. The boy moans loudly. I feel his boy hole spread as I shove my cock in all the way to the bone.
Jim smiles, takes a good puff on his cigar, picks up his belt and starts beating Brendan's ass. I roughly fuck Stuart. He grunts every time I shove in deep.
I look over. Jim is whupping Brendan very hard. I hear a muffled scream from Brendan with every lash. "Five more!" Jim says just before he strikes Brendan again.
Brendan moans loudly.
"Four more! Three! Two! One!" Jim sets down his belt. Brendan is sobbing. Jim unzips his fly and pulls out his cock. It's rock hard and ready for Brendan's bright red ass. Jim doesn't bother to spit on his cock. Brendan's hole is well trained from years of daily fucking.
After a few minutes Daddy Jim turns to me and says "Swap? I wanna try that tight ass." I nod and pull out of Stuart. Jim steps over and thrusts his cock into Stuart. "Ohhh nice" he says quietly under his breath.
I start fucking Brendan. Brendan may not be as naturally tight as Stuart, but he is a well trained bottom. Stuart clenches his ass muscles when I want him to be tight and relaxes them when I need his ass to be open. He is a beautiful fuck.
I hear Daddy Jim moan. He's cumming in Stuarts hole. I can tell Jim is having a big orgasm. Finally, after a minute Jim stops fucking Stuart. He rests a moment then pulls out. A line of cum runs from Jim's cock to the boy's hole.
I love sloppy seconds. I love fucking a slippery, cummy, tight boy hole. I pull out of Brendan and start fucking Stuart again. This time I don't hold back. I ram the boys ass hard and deep. My cock deserves every ounce of pleasure this boys hole can give. I'm not going to let up till I'm satisfied.
When I do cum, my load flows easily and naturally. I don't have to tense up, or concentrate, or force it. I just shoot my load in the boys ass like it was the most natural thing in the world. My orgasm is wonderful and long.
When I pull out, cum dribbles down the boys leg.
I untie Stuart and remove his mouth gag. The boy is sobbing. I hold him close. I lay back on the sofa with the boy's head on my chest. "Good boy." I say. "I'm proud of you." I stroke his hair. Stuart quietly sobs in my arms.
Jim unties and ungags Brendan who collapses at Jim's feed. "What do you say boy?" Jim asks.
"Thank you Sir." Brendan weakly answers.
I push Stuarts mouth to my nipple and tell him "Suck boy. Gently suck." The feeling of his lips excites me again and my cock becomes plump. I turn to Brendan and say "Blow me." Brendan obediently crawls between my legs and start sucking.
I close my eyes and relax as the two boys service me. I put my hand on Stuarts head and push him down to my crotch. I say "Suck too." I look down at the two boys licking my cock. I also see that Jim is fucking Brendan.
I grab both boys heads and alternately fuck their faces. Then I push Stuart onto my balls and let Brendan take my dick. Brendan is a very talented cocksucker. Stuart will be great one day, but for now, he only gets my balls.
Brendan gets me close. I grab his head and start throat fucking him. It feels wonderful. I blow my second load so deep in Brendan's throat that he doesn't need to swallow. When I finally pull my cock out, Brendan gasps for breath. I see Jim shudder. Jim is shooting his load up Brendan's ass. Brendan moans with pleasure as he receives Daddy Jim's cum.
I pull Stuart close to me again. "Good boy. What do you say boy?"
"Thank you Sir."
"That's right boy. I guess we should get you home soon."