Please, Daddy? Ch. 03

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Jack tells Bradley a secret that leads to something more.
11.8k words
4.71
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Part 3 of the 5 part series

Updated 06/08/2023
Created 03/13/2017
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If you haven't already, I highly recommend reading chapters 1 and 2 before continuing on with this one.

Many thanks to those who rate, comment, and leave feedback. All is very much appreciated.

Special thanks to my editor, NickJBella, for everything!

**********

Things have been quiet between Jack, Bradley, and Brittany for the past few days. Mainly because Jack has gone back to work and their mother hasn't left the house much. They have been leaving each other subtle hints throughout the house, though. Sometimes slipping into a bathroom together so Brittany can fulfill her cock-sucking craving or the guys will take turns burying their faces between her legs when Beth is in the shower. They haven't dared have full-on intercourse with each other at night while Beth is sleeping, yet. They prefer she weren't in the house at all but they take what they can get.

Brittany can't stop thinking about the two of them having their way with her. She loves having multiple partners at once. She's quite popular among the fraternity houses at school. It's common to find her at a party tucked away in a room running a train as frat boys come and go one by one. Since losing her virginity, she has not had one serious relationship. All the men in her life are strictly fuck buddies.

Bradley can't wait to get ahold of his sister again. She was amazing and he's quite impressed with her skills at such a young age considering she was a virgin when she left for college two semesters ago. But he's a little curious about Jack. Dropping to his knees and swooping in to lick that last bit it of cum off his stepdad's cock was purely out of his control and he's rather surprised he did such a thing in front of Brittany. He's intrigued about Jack saying he was going to fuck him in the ass before he claimed his sister's. He's been meaning to ask him about that but he hasn't had enough alone time to do so.

Jack hasn't been happier. He now has two pussies for his pleasure of fucking whenever he gets the chance and he will hopefully soon have an ass to throw into the mix. He's not quite sure about Bradley. He's had some suspicion but has never really come to a conclusion. Bradley has had a few girlfriends. He even "caught" him fucking a girl during one of his breaks from school. While Jack didn't interrupt then two lovers, he did watch at a safe distance and jerked off ending it with a quite satisfying orgasm. He was very impressed with Bradley's skills as he watched him fuck his sister. He's meaning to get him alone so he can pry into his sexuality just a little bit further.

As for Beth; yup, she's still clueless.

The weekends are the only days Jack gets to sleep in. He and Beth are just waking up for the day. Brittany and Bradley can be heard wandering around downstairs. Jack can only hope they are behaving themselves. Whenever they are alone, he tends to worry if they are off doing naughty little things to each other that he wants to be a part of, too. That girl is a cum guzzler and Jack absolutely loves that about her. She's just like her mother in that aspect.

"Jack, I'm going to take Brittany shopping today. We haven't had much girl time since she's been home and I think it'll do her some good to get her out of the house for a bit," Beth says as she rolls over toward Jack. The two of them are completely naked and only covered with a sheet.

"That sounds great. She hasn't really done much of anything since she got home. I think it's starting to bug her. I hope she doesn't feel like she has to be stuck here all summer long. I don't know why she hasn't gone out with any of her friends," Jack wonders.

"I don't know either. She certainly has changed since she went away last fall. I'm a little worried about her."

"I think she can take care of herself. She's just experiencing a whole new world. As long as she doesn't come home pregnant, I don't care what she does," Jack says.

"I wish the two of them would both spend a couple of days out with friends some time. Maybe they could get a group together and go to the cottage for a night. I just miss having wild, kinky sex with you throughout the house at any time during the day," Beth flirts as she rolls on top of Jack. She straddles his hips and feels his hard cock pressed against her. She moves her hips just right and rubs her pussy along the length. Her slick, hairless mount glides smoothly along it. Her tits hang down in Jack's face and he sucks on one of her staring nipples.

"Like the time I fucked you in the ass outside by the pool? And the times you've ridden my cock in the hot tub? Oh, and let's not forget the times I've eaten your pussy in nearly every room of this house and made you squirt all over," Jack teases.

"You're so naughty," she giggles as he buries his face between her tits. He playfully growls as he clamps down on one of her nipples with his teeth. She lets out a little squeal and lifts her hips from his. She slides down along his cock again without taking him in just yet. Her pussy is so wet, or maybe she's still full of his cum from last night. He isn't quite sure which.

"Show me what kind of dirty little housewife you are. Be a slutty bitch this morning," he grins at her.

"Slutty bitch, eh?" She says with a playful tone. "I want you to lick your cum out of my pussy from last night. You failed to do that afterward, you know." She lifts her weight off from him and he slides down on the bed a little bit. She crawls up so she is now straddling his face. He can see his liquid love from last night beginning to slowly drip out of her. He can't imagine there's much left in there but he can't wait to lap up all that he can. She lowers down onto him just far enough for her pussy lips to lightly graze his lips. He sticks his tongue out and runs it along her entire slit. He can taste the faint traces of last night's fuck fest still lingering.

"Watching you lick your cum out of my pussy is so fucking sexy," Beth says as she looks down and watches his tongue explore every fold. She places her hands on the headboard and starts to slowly rub her pussy on his mouth. He starts licking her clit and listens to her moans of pleasure. He slides a finger into her pussy and gathers up as much wetness as he can. He drags his finger back along her crack and slowly pushes it into her ass. It clenches his finger tightly but quickly loosens and lets him inside. He wiggles his finger and she starts riding his face harder. Her body tenses and she lets out a scream as her orgasm takes over. He can feel her pussy juices dripping down into his mouth. Mmm,... he tastes so good.

She climbs off from his face and remains on all fours. She sticks her ass in the air and he kneels behind her. He slips his cock inside and starts fucking her hard. He grabs ahold of her hips and spreads her ass cheeks wide. He can see her little rosebud slightly winking at her. He'd love to slip his cock in her ass but not this time. He's waiting for someone else's instead. He spits a large wad of saliva and watches it land on her ass. He takes his thumb and swirls it around her hole all while never missing a stroke with his cock. He eases his thumb into her ass and she lets out a moan. He loves the feeling of her wearing a plug in her ass while he fucks her pussy but his thumb will have to do for now.

"I'm going to cum. I want your mouth," he instructs.

She quickly turns around as he strokes his dick. She opens her mouth and sticks her tongue out. Her big tits hanging down below her are slightly jiggling with the movement of his hand making long, quick strokes. He places the tip of his cock on her tongue and fills her mouth. It coats her front teeth and gathers on her tongue. She looks him in the eyes and swallows his deposit.

"You are one sexy MILF, you know that?" He says as she licks the last bit of cum he has milked out for her.

When Jack and Beth make their way downstairs they notice that the kids have already eaten a quick breakfast. Bradley is on the couch with his tablet and is wearing earbuds. Brittany is outside sitting at the edge of the pool with her legs dangling in. Beth makes her way outside to where Brittany is and asks if she would like to go shopping. Spending Daddy's hard earned money always makes them feel better. They both walk into the living room and Bradley removes his earbuds.

"Where are you going?" He asks his mom.

"I'm taking Brittany out for a while. Do you need anything?" Beth asks.

Bradley glances at Jack who is standing in the kitchen with his back turned to them. "No, I'm good," he says with a smile. He's a little-excited knowing he'll be home alone with Jack for once.

Brittany hurries upstairs and gets dressed. Beth approaches Jack who is standing near the sink with a glass of water. She leans in close to him and gives him a deep, passionate kiss.

"Excuse me, ma'am. Is that my cum I taste in your mouth?" Jack whispers into her ear.

Beth giggles and responds, "Why, yes. Yes, it is. I didn't brush my teeth afterward. I want to savor the taste of you as long as I can."

"Sinner," Jack laughs. He gives her another quick kiss goodbye as soon as Brittany reappears downstairs.

Bradley makes his way back up to his room. He knew his parents were fucking this morning and went downstairs because hearing them was going to send him over the edge. It wouldn't have been the first time he's played with himself while listening to them, though. He flops down on his bed and rubs his hands over his face. He is still in disbelief as to everything that has happened recently. He doesn't regret one bit of it but his appetite is growing and he wants more. It's been four days since he fucked Brittany and just the sight of her is enough to make him crave her like she's the last female alive. She's so fucking sexy and he doesn't care that she's his sister. Just as he goes to reach his hand down his pants, he hears a light knock on his door. He nearly jumps out of his skin since he's deep in thoughts of his own.

"Come in," he calls out. Jack slowly opens the door and peeks inside.

"Are you decent?" He jokes.

"Were you expecting me to be indecent for any reason?"

"Well, with all the crazy shit that's been going on around here, I wasn't quite sure. Are you ok?" Jack asks.

"Yeah, I'm fine. Are you?"

"Yeah, I'm ok. I just don't want things to get weird or anything," Jack says.

"I don't think it can get any weirder than it already is. My own stepdad and I took turns fucking my sister. What's not weird about that?" Bradley laughs.

Jack joins in with his own laughter. "Actually it can."

"What do you mean?"

"Son, are you gay?" Jack asks matter-of-factly as he sits on the edge of Bradley's bed. "I can't stop thinking of you licking the cum off my dick after we came together all over your sister's face."

"Dad, I'm not really sure what I am. I'm sorry if that bothered you. I mean I love women, I love eating pussy, and I love fucking them. But, I also love sucking cock and I love being fucked in the ass. I've also fucked a few guys," Bradley admits. "I've never kissed another guy, though, and I definitely don't want to be in a relationship with one. It's just a whole new world of sex."

"Do you want to fuck my ass?" Jack doesn't beat around the bush at all.

"Honestly, I thought about it while I was watching you and Brittany pulling a sixty-nine. Have you ever been with a man?"

"No. Your tongue on my dick has been the only sexual contact I've ever had with another guy," Jack explains. "I can't stop thinking about it."

"So, how do you know you'd like to have my dick stuffed in your ass?" Bradley asks.

"I have a secret to tell you. Don't say anything to your sister because your mother would kill me."

"I promise," Bradley assures Jack.

"Your mom pegs me. She fucking loves it!"

Bradley's mouth falls open. "Mom?! You're fucking with me, right? There's no way in hell my mom does that to you." The look of shock on his face is priceless and Jack lets out a laugh.

"No, I'm not fucking with you. It's true. She loves wearing a big cock, bending me over, and fucking me hard with it. She gets off on whatever sexual domination comes from wearing a dick."

"I don't believe you," Bradley says with a raised eyebrow.

"Come here; I'll show you." Jack stands and walks towards the door. He looks back at Bradley who is still sitting on his bed shaking his head. "Get your ass up and follow me."

Bradley follows Jack to the master bedroom. They walk through the master bathroom and into the walk-in closet. Located at the back of the closet is a cabinet that Bradley always thought was where his mom's jewelry was kept. Jack opens the bottom drawer and pulls out a strap-on harness. Attached to it is a large nine-inch realistic-looking cock. It's flesh colored and very detailed. The girth is bigger than Jack's actual cock. Bradley's mouth falls open once again. He can't imagine his mother wearing this let alone fucking Jack with it; the same mom who bakes cookies for his friends and goes to church every Sunday.

"You seriously take this whole thing in your ass?" Bradley finally spits out.

"Yeah, all the way to the fake balls. It took a long time to stretch my ass to accept it but I have no problem taking it now after your mother warms me up."

"Why do you want me to fuck you if you have mom wearing this massive thing?"

"Because I want to feel the real thing, don't get me wrong; this thing is fantastic, but I want to know what it's like to have a real dick," Jack explains.

"And just when do you plan on pulling this off?" Bradley asks with intense curiosity. "I'm not fucking you in front of Brittany; at least not until you know whether you'll like it or not."

"They're gone for who knows how long today. You know how they are when they go shopping," Jack says with a grin. "I'll return the favor."

"What makes you think I want your dick?" Bradley replies with a slight bite of his lip.

"Because of the way you were looking at it when we were both jerking off on Brittany. I saw the way you were watching me," Jack smiles. "And you didn't flip out when I said I was getting your ass before I get ahold of Brittany's."

"You're right. Not only would I love to feel your cock hitting the back of my throat but I'd also love to feel it pounding in my ass. Stretching me; fucking me hard," Bradley teases.

Jack just had sex with Beth this morning but his cock is twitching eagerly and is ready for round two. Bradley can see it flexing inside of his pants. His own cock has been hard since Jack showed him the strap on. He's tempted to see if he can fit that in his ass, too. Like Father, like Son?

"You're the old pro at this. How do we get started?" Jack asks.

"Strip and get on the bed. I have to go get a condom," Bradley says.

"No need. Your mom keeps a supply in here for my big friend," Jack laughs as he gathers a couple of out of the toy drawer just in case they need more than one. He also grabs a huge bottle of lube. Bradley can only wonder what else might be in there but he's eager to have his way with his stepdad first.

As they walk through the bathroom, Jack grabs a couple of towels out of the hamper. They walk into the bedroom and simultaneously strip. They stand to face each other and admire one another's body. Jack is hairy with gray hairs throughout his chest and pubes. Bradley is nearly hairless except for the patch from his belly button to his cock. He shaves his region completely smooth. Jack gets aroused at the idea of a twink fucking him; and not just any twink; his own stepson. Jack spreads the towels on the bed and tosses the lube and condoms on top of them.

"Where do you want me?" Jack asks.

"Lay on your back," Bradley instructs. Jack climbs on the bed and lies right in the middle. Bradley kneels in between Jack's legs and starts stroking Jack's cock. He spits on it to lube it up just a bit. Jack watches with extreme interest. Bradley leans down and licks around the head. Jack hisses through his teeth at the feel of Bradley's tongue. Bradley looks up at Jack and lowers his mouth onto him as far as he can. Jack can feel the head of his cock pressing against the back of Bradley's throat. Bradley pulls back and sucks hard. Jack is soaking up every little movement. He moans as Bradley licks up and down his length. Bradley puts his hands behind Jack's knees and lifts them towards Jack's chest. He's opening his dad up wide so he can lick and taste every bit of him. Jack grabs ahold of them and keeps them up as high as he can.

He licks and sucks Jack's balls one by one and flicks them with his tongue. He lifts Jack's ball sack up as he licks the line that runs to his ass and Jack's cock flexes. He stops to admire Jack's begging hole. The thought of slipping his dick in there and claiming his dad's ass is driving him wild. He circles the hole with his tongue before making long licks along Jack's crack. Jack loves the way Bradley's tongue feels. It is wider and stronger than Beth's and his toes curl when it penetrates his ass. He can't explain the feeling of his stepson using his tongue to stretch his ass; making him loose enough for a finger.

"You want me to warm you up while you're on your back or do you want to stick that sexy ass of yours in the air for me?" Bradley asks.

"I want to bend over and spread myself wide for you to do whatever you want to me." Jack rolls over and gets on all fours. He spreads his knees and his ass cheeks follow suit. His asshole is nearly winking at Bradley already and he hasn't even slid anything in there yet. It looks like it won't take much to get Jack prepped and ready to fuck. Bradley reaches for the lube and squirts a good amount right onto Jack's crack. He flinches when the cold substance hits his sensitive area. Bradley drags his finger through the thick gel making sure to coat it sufficiently. He lightly prods Jack's ass with it and it slides right in. It's obvious his mother has quite a bit of fun with that big toy of hers; Jack's ass doesn't clench around his finger one bit. He lubes up the second finger. This time there's a little resistance but not much. Jack moans as Bradley moves his fingers slowly in and out. Bradley notices a dot of precum on the end of his eager cock.

"Slide that dick of yours in there. I want to feel your balls bouncing off me as you fuck me hard," Jack begs.

Bradley quickly opens a condom and rolls it on. He slathers his cock with a large amount of lube and presses the head against Jack. He feels resistance for about two seconds before Jack's ass swallows every inch of his cock. He's always thought of himself as having an above-average dick and is amazed at how easily his Jack's ass has opened up and accepted him. "Very impressive, dad." He smirks as he makes long, slow thrusts making sure his ass has adjusted well.

"Don't take it easy on me, boy. Fuck me like a little bitch," Jack hisses. With that, Bradley grabs Jack's hips and starts fucking him with all he's got. The sound of his hips slamming against Jack's ass is very arousing for both of them. Bradley looks down and watches his cock every time it disappears into Jack. His ass feels amazing the way it grips Bradley's cock.

"Fuck! Fuck! Fuck!" Jack wails each time Bradley shoves his cock in balls deep. His head is buried into his pillow and he's white-knuckling the sheets.

"Tell me how good this dick feels, Dad," Bradley says between breaths. Jack is too busy moaning that he can't get the words out. He answers by reaching back with both hands and spreading his ass even wider for Bradley. This gives him a clear view of Jack's asshole hugging his dick tight. Jack's toes are curling with excitement.

When Jack is finally able to catch his breath he lifts his chest off the bed. "I want to ride your cock."

Bradley pulls away from Jack and Jack moves so Bradley can lie down in his spot. Bradley uses his thumb to stand his cock up tall while Jack straddles his hips. Jack slips himself down onto Bradley and starts riding him. As he moves up and down, his cock is bouncing and staring at Bradley. Bradley reaches down and starts jerking his stepdad's cock. Jack throws his head back as Bradley starts bucking underneath him. His eyes squeeze shut and he grimaces as his dick is ready to explode all over Bradley.