Disclaimer: This is a work of fiction. Any resemblance of the characters and settings to real life persons, events, circumstances, etc. is purely coincidental. This file contains depictions of sexual acts with preteens boys and should not be read by minors or by anyone where it is prohibited by the laws of their state or country.

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How to date a family

                                                by Sam The Ham



     Seth thought he should have stayed home as nervous as he was. He was in his thirties, he had been on dates before and this one wasn't even really blind. They had sort of known each other for a while now. Trouble was it was talking online, over the phone and not in person. It had also been a while, at least for Seth to go out with someone. He felt like he was rusty and a bit old, but that wasn't his real fear. The woman he was going to pick up was like him. They both liked boys and she had two of them.

Arriving at the apartment building he looked over the buttons and buzzed Samantha's apartment. There was a moment of silence before the intercom came to life. "Is that you Seth?"

"Yes, Samantha?" he didn’t mean to turn that into a question. There was no reason for anyone else here to know his name. It was his lack of confidence showing. It was definitely something you wanted to show off when you are meeting someone for the first time. Like carrying a credit card statement around, look at how much I owe people.

"Come on in." Samantha said as the door to the apartment building unlocked.

"All right," Seth replied sensing something was wrong.

By the time he made it inside and was walking up to her door, it opened and the face he’d only seen on a screen was now staring at him. She gave him a little smile. "My babysitter canceled at the last minute, sorry."

"Oh," Seth said stopping in his tracks a step or two away from the door. Plans of a dinner and a walk flew out the door. "Well if you like we could take them someplace else with us. Or we could just order a pizza?"

Samantha opened the door a bit further revealing one of her kids sitting on the couch staring at the TV. Seth felt his eyes going there immediately, admiring the little blond boy. It took my second to pull his eyes away and back at Samantha.

"I like you," Samantha said with a smile, fully aware where his eyes had gone. "But I don't want to introduce a string of men into their lives without knowing there's something more there."

Seth nodded in understanding. It made complete sense. He was about to start to walk away when another thought occurred to him. "Samantha, I'm not a stranger to you, we are friends. Would you like to go out just as friends? I would like to be around your boys."

Samantha didn't answer at first but slowly turned her head to look behind her. "Just friends, nothing more tonight?"

Seth nodded. "I know this place. They got a lot of games that kids can play, but it's also a sports bar."

"A place for the kids to play and with alcohol? How have they not taken over the world?" Samantha said chuckling. "Okay, just give me a minute to get the boys ready."

Seth smiled, proud of his amazing way with words as Samantha closed the door. He waited in the hallway. About two minutes later, the door opened again and the two boys spilled out, both of them giving curious looks. They were blond, their hair short, and had the typical summer crew cuts for little boys. The older of the two was a half a quarter of a head taller than his brother. He spoke first. "You’re mom's friend?"

Seth who had only seen pictures until then was taken aback by the crystal tone of the little voice. It wasn't quite what he was expecting, but he smiled. "Yes, and I take it you're Daniel?"

Daniel smiled showing a missing tooth. "Yep."

Seth looked over at the other boy. "That would make you Ethan?"

The younger of the two boys nodded, but didn't say anything as their mother closed the door behind them and put a hand on their shoulders. "This is my friend. He's taking all of us out since the babysitter canceled."

The boys seemed to like the idea of going out as they both cheered. They headed out. Seth described the place and the boys mostly Daniel asked questions. They calmed down after the Q&A was over.  They were fairly quiet after that, whispering to each other. Of course, that changed as soon as Seth turned the car off and told them to get out.

Samantha had them hold hands as they walked to one of the entrances of the mall. The boys continued to hold hands even inside mall. As they kept walking faster excitedly, Samantha told them to slow down. Seth decided to try for a joke. "Boys, keep pulling on ahead and we might have to get you leashes like they have for little kids."

Both boys objected that they were not babies and grownups were just slow. Seth kind of liked that sassy comeback. Samantha leaned in a little closer. "Leashes, maybe some dog collars too. Oh and those little tail plugs they have too." She said in a hushed tone that the boys couldn't hear.

Seth smiled at that, imagining it, happy that she had suggested it. "Woof." Samantha added and they both started laughing.

The boys gave them a weird look not getting the joke. A minute later though, they were at their destination. There was a little sitting area outside, out of the way of the crowd. Before going in, Seth explained how the place worked. He showed both boys a card and told them it had to be scanned. It wasn't until he told Ethan he could go play the games that he realized he had taken charge without consulting Samantha.

Seth ventured a look at her as he stood up, Ethan bouncing up and down with excitement. He waited for her to say something but when she didn't, she just gestured towards the door and said. "Let's get going."

To say the place was loud was a bit of an understatement. It was like a sudden thunderstorm falling on a quiet spring day. Ethan seemed a bit overwhelmed. He stood there staring at everything for a while before Seth gave him a nudge and said that they should just walk around to get a look at everything. The boys made it about halfway through before Ethan found something he wanted to try and after he did it was Daniel's turn. They bounced back and forth trying different machines, winning tickets and playing games. There was a two player thing that both boys wanted to try and eventually they came across a four-way air hockey game.

Seth let both boys score on him and targeted most of the shots either at a blank spot or at Samantha. He did try to keep the boys on their toes and Daniel’s victory was just by one point as time ran out. Of course, the boys wanted to do it again right away. After that both boys wanted drinks and although they could have carried them around, Seth wanted a break from standing. Samantha said they would probably just spill them if they didn't sit down.

The restaurant portion of the place offered booths and tables so they took a booth. To his surprise both boys wanted to sit next to him. So, it was mom on one side and the three of them on the other. They were now relaxed talking directly to him. They even asked for French fries as a snack and when they arrived both boys squeezed closer to him, not caring about the contact. Of course, the two boys rubbing up against him had the obvious effect.

Samantha knew what was going on because she was smiling and her foot found its way over to his leg. Being a bit of a foot guy it was distracting. He must've been letting the kid’s side of the conversation down because he felt a little poke in the stomach and looked over at Ethan's who was frowning.

"Sorry?" Seth said after realizing he had missed the question.

"Can we go back to playing?" Ethan asked.

"Um... Sure, I just need to go to the bathroom." Seth said after a moment realizing how hard he was.

"I need to go too." Daniel chimed in. "Can I come?"

"You don't want to go with me to the girls’ room?" Samantha teased.

Daniel didn't find it funny because he straightened. "I'm a big boy."

Seth smiled at that. "All right, I can take you here; take the card with you." He said handing the card over to Samantha.

It was a little difficult, but thankfully Seth had decided not to wear tight pants and he was able to reposition his erection as he scooted out of the booth. At least he didn't think it was obvious as the two of them walked over to the bathroom. The noise in the bathroom dropped by 95% as the door closed behind them. Both made their way over to the urinals. There was a kid sized at one end, as Seth walked by them so did Daniel. Not sure what to do Seth picked the one on the far side and then Daniel picked the one right next to him.

Seth turned a little as he whipped his out, he actually did need to go, it's just he was so hard. As he let go, Seth felt some of the pressure be released. Looking over at Daniel, he was surprised to see the little boy staring at him. He was a bit too far from his urinal his pants partly undone.

"If it's too high there's a kid urinal over there." Seth said.

Daniel shook his blond head stepped closer to the urinal having to stand on his tippy toes. "I'm good."

By the time Seth finished up, he was feeling a bit softer but still tucked his penis under his waistband like he did in grade school. He made sure Daniel washed his hands before they left. Surprisingly Samantha and Ethan were not playing a game, but just standing a little away from the bathroom waiting. Ethan was whispering into his mom's ear and she stood up as Seth approached.

"Ethan said he needs to use the bathroom. He wants you to take him." She rolled her eyes a little.

Seth smiled and gestured for Ethan to follow him. The younger of the two boys immediately ran towards the bathroom Seth following after. Ethan picked one of the little urinals and as Seth waited for him to finish he asked. "Are you having fun Ethan?"

"Yeah, lots." Ethan said turning a little. "We can come back with you, right?"

Seth wanted to say yes, but "It's up to your mother."

"She will say yes." Ethan said turning a little as he finished up giving Seth a glimpse of his little penis as pulled his pants back up.

Again, Seth was about to remind Ethan to wash his hands, but Ethan automatically did so. For some reason he found that cute and gave him a playful rub on the head as they headed back out.

They tried out some more games, but soon Samantha said that they really should go back home. Seth let the boys spend the tickets they had won. Actually they spent some of his he had stored up, but he didn't mind since they got one prize each. On the drive home the boys fiddled with their new toys and talk to each other about what had just happened. Seth enjoyed eavesdropping on the two boys’ conversation occasionally making a comment.

Seth was expecting to drop everybody off, but as he pulled into the parking spot, Samantha leaned over. "Why don't you come in? We can have a drink before you go."

"You know I don't drink." Seth said.

"I have orange juice." Samantha said giving him a little nudge. The boys must've overheard at least part of that because they made kissing noises before the car. Then once both doors were closed she added. "I could also get you a blow job."

"I thought this wasn't a date?" Seth said with a little smile.

Samantha smiled. "You were good; you're not just after my boys. You didn't feel them up once."

Seth briefly wondered what the other men she dated were like, but decided to put it out of his mind. So they got out of the car and he followed the three of them inside. Samantha excused herself once they were inside saying the boys really needed to go to bed. Seth would've liked to help with that, but keeping in mind the last comment decided not to say anything. He stood in the family room looking around as Samantha disappeared with the boys for five minutes before reemerging and pouring them each of them a glass of orange juice.

"Did you get a good look at my boys in the bathroom?" Samantha asked before taking a long sip.

"Not really." Seth said honestly. "I think Daniel got a better look at me then I did him."

"Yeah, they’ve mostly seen latex dildos. I wonder if Daniel was wondering what it tastes like or what it feels like." Samantha said with a little sigh finished her glass.

"Is that what you're thinking about?" Seth teased.

"Like mother like son." Samantha said. "Let's put an end to the curiosity. My room."

Seth wasn't going to argue and let Samantha leave them down the hallway. She opened the door to her bedroom, but it wasn't empty. Both Daniel and Ethan jumped to their feet standing on the bed completely naked. Both giggled at Seth's face.

Seth gave Samantha a look. She smiled and casually sat in the chair. "They wanted to show their appreciation. They had a lot of fun."

Smiling he looked back at the boys. They were brothers obviously, with cute little circumcised penises and completely unashamed of being naked. Ethan pointed and laughed a little. Seth realized that he was becoming hard much more so than earlier. His cock was straining against his pants.

Daniel broke the silence. "What would you like us to do Seth?"

Seth had an idea what the boys were used too. Butt plugs and vibrators, many of them shaped like a penis. Still it had been a while since they had had a real thing or at least that's what Samantha had told him. It took a little effort on Seth’s part to realize how much the boys were probably not just okay with this, but eager. Still, a test would make Seth feel better.

"Both of you get down on your knees." Seth ordered. Both boys immediately obeyed dropping down to then their knees side-by-side. Seth told them to face each other about arm’s length apart.

"Here, is what we’re going to do. You two are going to wrestle. No punching, no biting just grappling. The first one who pins the other down, gets it up the butt from me. The other one is just going to have to suck. Any questions?"

Neither boy had a question and Seth told them to begin. He was pretty sure Daniel could win easily, but if he wasn't really enthusiastic about getting it in his butt, he would probably let Ethan win. At least that was his analysis on the matter. Still, the match was not quite one-sided. Ethan was trying to win but his older brother had a little height and weight advantage. Daniel was eventually able to pin his little brother down. Seth slapped the bed and shouted "winner!" Daniel raised his arms up and then rolled over kicking his feet into the air and showing off butt.

Timidly, Seth asked Samantha where the lubricant was, but it was Ethan who grabbed it. Daniel was pulled to the side of the bed and rolled over, his butt in the air, a pillow underneath him. Seth undressed and squeezed a dollop of lube on his fingers. He told Ethan to get to work.

The younger boy was enthusiastic but not the most talented. Ethan managed to open his mouth wide enough to get the head of Seth’s erection into his mouth. After realizing that was going to be it Ethan pulled off and started kissing and licking the shaft. The whole time Daniel was getting his hole stretched. First by Seth’s index finger slowly circling around followed by a second. Daniel had obviously felt that before and pushed back against the intruder letting out a few groans more like pleasure then pain.

When the time finally came, Daniel lowered his head and raised his butt further up. Seth voiced a string of encouragement to both boys. Telling Ethan how good he was, how soft his lips were on his cock. Telling Daniel he was going to be next and how beautiful he was. Seth meant every word. He lined up his cock and began to push against Daniel’s anus, telling him again how good he was. Beyond the initial resistance he found it easy to slip inside. Seth stopped when he was about halfway in giving Daniel a chance to get used to it.

Ethan was very curious of this. He stood beside them fairly close gently playing with his little boner. The next second, Seth noticed Samantha kneeling next to her son, sucking his stiffy as he continued to watch.

He started to move inside Daniel, pulling back before sliding back in deeper. Daniel arched his back at this and Seth could see the boy’s toes curling. Seth stopped a moment waiting for Daniel's toes to relax before repeating the process. It was slow going at first, but he ended up burying his shaft completely in the boy’s butt. He could even feel his pubic hair brushing up against Daniel’s ass. He stayed there for a moment enjoying the position and letting Daniel get used to it to the full length.

For a moment, Seth wondered if he could go at it harder. He glanced at Samantha who was too busy giving a blowjob to Ethan. Sliding out of Daniel, Seth pushed forward again burying most of the shaft causing the boy to squeal and moan and even shake his butt. Slow thrusts became faster and Daniel started pushing back definitely enjoying the feeling of fullness with each new determined thrust. Seth started to hear the boy whine, "Ooooh, please, yessss, ooooooh"

Seth felt his climax building, but before he could reach the peak Daniel tensed up. His little butt hole constricted and in the middle of a withdrawal Seth felt himself climax. Instinctively he reversed direction bursting deeper into Daniel who buried his face in the pillow letting out a moan.

Seth felt his cock spurt, deep into Daniel and it was damn satisfying. After the last jolts of his orgasm, he pulled out. He could feel the sweat on his forehead begin to cool as he stepped back. Daniel stretched out his body, leaving the pillow behind. The boy turned his head a little and smiled.

Samantha had stopped sucking Ethan’s little erection and the boy was stroking himself. Seth turned his stare to him. Ethan looked up and instinctively his hand fell away as Seth leaned down to pick him up, by putting his hands under his knees and dropping the boy on the bed. There was a little spit from mom still left on his dick, but Seth didn't care as he gobbled it up.

Ethan must have been close. Seth only worked his cute boner for a minute before he could feel the kid on the edge. Ethan raised his hips meeting with Seth’s sucking mouth. To Seth's surprise something came out of the boy’s penis. He recognized the salty flavor and pulled away. Ethan squirmed and giggled.

Seth stood up reminding himself that urine was supposed to be sterile. Not sure if Ethan meant to pee in his mouth, he just tried to laugh it off with the youngster. Of course, sucking Ethan off even after plunging the depths of Daniel’s rear was enough to get him excited already. Seth felt half his age and was already partly hard again.

He stood there before realizing there was still one member of the family who needed a little attention.  He walked over to Samantha who had her hand down her panties. Samantha stopped and stared at him for a minute before realizing what was going on. Seth held out a hand and Samantha took it, out of her panties first.

Seth pulled her close and gave her a kiss, kissing her with the same mouth that had just suck Ethan. Breaking the kiss he started to pull on her clothes. Samantha understood and started to undress, Seth helped her along, tugging and pulling when needed. When Samantha was naked, Seth walked her over to the bed and had her lay down between the two boys on her hands and knees.

Of course, Seth knew he couldn't go bareback this time. Going to his pants he retrieved his wallet and the condom. The boys scooted a bit away to look at the scene. They were used to getting things put in their butts by their mother, but now they were going to see her get it for a change.

With Daniel, Seth had been cautious not wanting to hurt him. With Samantha, he didn't need to be that gentle. He slid into her wet pussy and started fucking her right away, listening to her moans. Having seen the boys cum kept Seth’s cock hard. He plunged inside her fast and hard. Their orgasms were intense and when Samantha climaxed it was the type that made her shake with pleasure. She lay spent on the bed for a while.

Both boys were already falling asleep. Daniel was curled up next to Ethan sandwiching the youngest boy between himself and his mother. Samantha was still awake of course and she gestured for Seth to join them. He did, dozing off in the same bed as his lovers.

The End 

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