Chapter 1: Babysitting

Kinsey’s imagination was running wild. She knew she was acting more than a little reckless, but the chance to see (and play with) Andrew and his friends was just too tempting. A few days ago, he had stopped by the house just as she was heading out to the pool. Jason had been naked since he had gotten up (just like she liked him to be), so she had answered the door, a wrap draped around her bikini-clad body. She had wondered why he was there, and if Jason had forgotten to let her know, but Andrew had quickly explained his desire for her to chaperone his party - a bit last-minute because his parents had been called away. If he didn’t find someone they could trust, he’d have to postpone. He had been most insistent and hinted that he would help her get some nice views - if she wanted. She did not let on just how much the idea had excited her, but she had soon gotten on the phone with his parents and (surprisingly) everything was quickly arranged.

She could barely recall the conversation she had with Andrew’s parents as they outlined all the food planned, as well as the tablet with their contact info and emergency numbers. Watching them pull out of the driveway, she could hear the boys playing out back. Even though she was eager to see what sort of games they might be willing to play, she waited a good fifteen minutes to be sure his parents had not forgotten anything. Satisfied they were gone, she double checked the lock on the front door and went through the kitchen to the back yard. As soon as she opened the door, she could hear the yells and loud voices of the boisterous pack of boys. She felt a moment’s trepidation as she walked towards the pool, a bit uncertain still as to the wisdom of all of this.

She caught Andrew’s curious gaze and nodded before heading over to a shaded spot beneath a wooden ramada. She had packed her suit, two of them, but the vague plan she had discussed with the young host had been for him to start things off (if he could) with a bit of daring and one-upmanship. Reclining and ostensibly looking at her phone, Kinsey kept an eye on the boys without seeming too obvious. She caught a glance or two in her direction at first, and then they seemed to be clustered at the far end for a while. After a minute or two, they scattered around the pool, but now there were considerable looks in her direction, as well as a lot of excited banter and nervous-sounding laughter. She noticed Andrew looking at her with what looked like a ‘significant’ look, and she paid a little more attention. She was sure he had slipped his trunks off, and based on how everyone was looking between her, Andrew, and one of the other boys, she was certain his friend had joined him. She deigned not to notice anything going on for a long minute or two, letting them get used to their daring. Discreetly keeping tabs on them, she finally stood up when she thought she detected a third boy joining the first two. She stretched casually, then walked slowly over to the pool, smiling when she saw them herd themselves away towards the other end.

She looked over at them and smiled, “Having fun?”

A chorus of “Yes’s” came back, and she let them think they were being sneaky for a moment longer before she brought things into the open.

“Why are you guys all at the other end? Are you afraid I’d be mad if I found out some of you were skinny dipping?”

She loved the shrugs and rather stunned looks on the young boys’ faces.

“Relax, guys, my brother and his friends do it all the time. I’m so used to it. As long as everyone behaves, you can all do it if you want,” She let that sink in for a moment before heading on to the house. She went inside just for a moment before going back outside and calling for Andrew.

“Andrew, could you come here a second?” She heard them laughing and someone catcalling, ‘Andrew, oh Andrew!’ She turned and headed back inside, but left the door open so she could hear. She was certain that she could pinpoint the exact moment Andrew finished drying off and started towards the house naked (at least that had been their vague plan). The joking and laughter died out, replaced by exclamations of alarm and “Dude, are you?” along with a few choice swear words.

She waited for him just inside the door, smiling as he entered. He was as delightfully naked as he had been the other day at her house, and she could already see him beginning to get as hard as he had been. “Good job. I did say you’d get lots of little rewards for helping me, right?” she said, teasing slightly, reaching out and gently holding his throbbing erection for a moment.

Slowly stroking his delightfully thickening prick, she watched her hand on him as he slowly came to full attention. “Now, go back like this and don’t be shy about it. They may say something, just be proud of it. Stroke it even. When I come out, you say something about proving it, and bring me your shorts. I’ll make sure everyone knows I don’t mind boys with naked erections.

She gave him another tug before patting him on the behind as he went back outside. She gave him a couple of minutes to get back out to the pool and into the water before heading back outside, cold drink in hand. She took her time passing the pool, making it clear she was looking at the boys playing around, and it seemed that all but one boy was without trunks by this time. She got herself situated on her reclining chair and took a sip while watching the boys, not waiting long before she saw Andrew swim to the edge and get out of the pool, his trunks in hand. As he approached, she waved at a spot where he and she would be in profile to those in the pool, and held out her hand to take his wet trunks.

“Now just stand for a minute. Make them wonder,” she said, nodding at his bobbing erection, smiling and making small talk for a minute. After a brief pause, drawing things out slightly, she stood up, patted him on the bottom, and walked back towards the pool. Reaching the edge, she turned and let her hand graze his erection as he passed, before turning back to the pool and announcing, “I just realized, I only know Andrew’s name. Why don’t you guys take turns coming over and introducing yourself? And bring your trunks if you would, that way I can collect them all, maybe I’ll wash and dry them for you guys.”

Kinsey turned away and headed back to her spot, not waiting for them to answer. She didn’t want to have to explain or try to convince them or anything. She just wanted them to think about each one of them walking over and handing over their trunks. She sat down and waited while they seemed to mill about, talking amongst themselves, no doubt trying to encourage one or the other to go first. Finally, the first boy who had joined Andrew skinny dipping moved to the edge of the pool and got out, carrying his trunks. He held them in front of him as he walked over to where Kinsey waited. She held out her hand and waited while he gathered enough courage to hand over his swimsuit. She could see he was already hard and throbbing, and she smiled at him as she put his suit on top of Andrews. “So, you know my name is Kinsey. And yours?”

“Oh, um, Tommy, er Tom,” the dark-haired boy stammered, his hands going to cover himself.

“Tsk-tsk, now don’t do that. I said you guys can skinny dip, but you must behave. No covering up. I like how it looks, so keep it in the open, will you?”

“Um, ok?” he said, moving his hands away slowly, standing on the edge of fleeing. He looked like a frightened bird.

“Relax. I mean it. I like how they look, and I’m sure you’ve always wanted a girl to, you know, see you and stuff?”

He nodded, calming down slightly. Almost imperceptibly, but she thought she was getting through to him.

“Now, good, why don’t you send the next boy over, hmm?” she said, reaching out and lightly brushing the side of his erection before patting his hip.

“Oh, god, mmm, yes, ok!” he said, walking back to the pool, his hands reflexively moving to cover himself.

“No hiding!” she called after him, and she watched as his hands slowly returned to his side.

Kinsey smiled, watching Tom get in the water and quickly swim over to where Andrew and the others were milling about. It only took a few seconds before another boy broke free from the crowd and got out of the pool. Tom must have said something about Kinsey’s rules, as it was clear this boy was working hard to keep his hands at his sides, not covering up his rapidly stiffening prick.

The blonde-haired boy approached, and she wondered idly how he could stand up — he seemed so skinny. He was all arms and legs as he approached, but his carefully exposed penis was anything but thin and spindly. As he moved next to her, he held out his damp trunks and stood still as she looked him up and down, smiling the whole time.

“Thank you,” she said, nodding as she took his trunks and added them to the small pile next to her, “and you are?”

“Co-Colter,” the boy said, stumbling slightly in obvious nervousness.

“Well, Colter, stand there for a minute and show off for me, hmm? You have a very nice...” she added, nodding at his trembling cock bobbing up and down slightly as his blood pumped into its rigid form.