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Babysitting for a Nudist Family

by Spank4Fun

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 07 Feb 2018

Babysitting for a Nudist Family


I was home from college for the summer looking for work. The previous summer, after my freshman year, had been filled just about perfectly with a combination of some lifeguard hours and, surprising to many of my friends, babysitting. It happened somewhat serendipitously when I was 15. My dad had been approached by one of his colleagues at work asking if I’d be interested in babysitting his young sons. I pulled some regular spots on a couple of weeknights and weekends taking care of his two boys. Apparently, I did a good job taking care of them. Dad’s colleague praised my work and when he got transferred about a year later, actually gave me a $200 gift card as an extra thank you.

Last summer was even better because I was 18 and had three years of babysitting experience. I even had business cards and postings on a couple of babysitting service websites. I got a couple of longer gigs, one which included accompanying a family on a weeklong trip to a beautiful resort. The parents wanted the freedom of outdoor recreation plus evenings with friends. I was well paid and got to swim and waterski with the kids.

I started posting my availability and contacting former clients a couple months before the semester ended. I was surprised when my dad texted me and told me he’d been contacted about a special babysitting position – and suggested I keep the first three weeks of June open – at least until he could tell me about the gig.

I was anxious to find out what this was all about, so I asked dad about it within a few minutes of arriving home. We grabbed a couple drinks and sat down to chat. Dad told me that he’d been contacted by someone that knew I babysat and wanted to know if I’d consider a three-week job, living at their house and babysitting his three boys, ages 15, 12, and 10. I told my dad, Sure, but why did they contact you instead of contacting me directly? Well, that’s the interesting thing, Jeff, and why we’re talking about this directly. Mike and his boys live a nudist lifestyle at home. Dad paused at that point and let me just sit back in shock. My mind wondered what it might be like to babysit three boys who were naked all the time. After a couple minutes, all I could say was WHAT?

Yes, said dad, they’re nudists. The house is big, and it’s located on a very private piece of land. There’s a lot of outdoor wooded space. There is a pool and a gym. Wait a minute, I interrupted, OK it’s a nice place, and they’re nudists. So, I’d be spending three weeks taking care of three naked boys, a 15-year-old, a 12-year-old who’s probably started or is starting puberty, a 10-year-old, and...? And you’d have to agree to be naked too! said my dad. What the fuck?

Just a few years ago, I’d be getting smacked a couple times on my bare butt for saying that but once I started college dad accepted cursing and cursed more himself in front of me. Dad was pretty sure that nudity itself probably didn’t bother me much, but a nude lifestyle was different. Dad has seen my younger brother and me naked around the house regularly. We’d seen each other naked at the swim club and at the gym. We’d always been naked when we got spanked which didn’t happen that often – particularly now that we were older. There was also a pretty open attitude about masturbation in our house. Dad talked to us about it even before puberty hit. He’d seen both my brother and me jerking off several times, and we both knew he jerked off.

Anyway, I was still in a little bit of a WTF mode and was just a little frozen sitting there looking at dad. He broke the silence a couple minutes later, saying: Look, Jeff, the decision is up to you, but I think you should at least consider it – plus you should know that the money will be pretty good. You’ll have no expenses for three weeks with all your meals, etc. included. Plus, he’s offering you $5000 for the three weeks. I wanted to utter another WTF? but I stopped and just said What? Look, son, it’s up to you and whether you’d be comfortable with it. Think about it. I say you should at least check it out. Mike wants you to come by for a visit, an interview I guess, meet the boys at lunch tomorrow. I told him I’d call him first thing in the morning if you were interested in checking it out.

I went out with some friends that night and didn’t say a word about the rather unexpected job offer. I told my friends I’d likely be spending the summer lifeguarding and doing some babysitting gigs. I was unsure when I went to bed. When I woke up in the morning, I had a couple of new things to think about but told dad that I’d be willing to check it out.

I was 95% sure that the boys and their father would be dressed when I arrived for lunch. Nudity wouldn’t start until I accepted the position. So, the first shock was Mike, opening the door when I rang the doorbell, naked. Mike was maybe 40, but he looked 30. He stood a couple inches over my six feet, weighed noticeably less than 200 pounds, and was in excellent shape – clearly a guy that worked out. It was impossible not to notice his large, soft cock with neatly shaved pubes. He knew who I was, so he immediately greeted me with a Hi Jeff, thanks for coming by. I could only stutter a thank you for considering me for the position. He invited me into a beautifully furnished den, telling me that the boys were in their rooms and would join us for lunch in a few minutes. Jeff sat down in one of two nice leather chairs in front of a large desk and gestured for me to take the other. I’ll admit I was struck by how obviously comfortable he was nude.

Mike quickly told me that he really didn’t have many questions for me. He’d talked to my dad and checked with several of my references. He knew I was very professional, highly recommended, and great with young guys. He didn’t pursue it in any detail, but he did say that he assumed I was at least considering the idea of nudity. I told him, Yes sir, I’m comfortable right now considering it. I guess I’m interested in knowing more about your expectations. We’re not nudists at home, but my dad, my brother, and I are open and see each other naked regularly. It’s an all guy house and dad has said for years that none of us have anything we don’t know about. I know nudity all the time would be different but...

With that, Mike changed the subject and laid out some clear expectations. He told me he was fairly strict with the boys and while summer was a time for lots of fun, it also included expectations for reading and limitations on computer games, television, etc. He actually handed me a page of rules that the boys would be expected to be followed. I read it quickly and saw that they were expected to treat the babysitter with respect, obey the rules, etc. Then he asked me if I’d be comfortable disciplining the boys. After all, he said, They’re great kids but two are teens, and the youngest is a bit of a wise ass at times. They can be pretty rambunctious at times. So, are you willing to spank them when it’s needed?

I was a little shocked by that spank them question. I thought that the nudist lifestyle might be matched with a more new age we never spank attitude. But I stated that yes, I would. I told him that several of the babysitting assignments I had over the last few years involved parental orders to spank the children as needed. I told him that for my very first year of babysitting at 15, there was a boy whom I ended up spanking almost every time I babysat. I did ask: Sir, how would you want them to be spanked? Mike smiled a bit: Obviously they don’t have to take their pants down when they already naked. If they earn a spanking while dressed for some reason, every so often they’ll have friends over, and the guys are dressed, then you need to make them bare their bottoms. For most of the spankings, you can take them over your lap or, with Kevin, the 15-year-old, I’ve started making him bend over on a chair or grab his knees. I’d want you to spank them by hand until it stings and burns a little. I don’t want them beaten. They know that spankings are more intended as minor punishment and reminders, rarely anything more. Kevin has gotten a couple sharp swats from a belt. Tim, the 12-year-old, has been threatened with it a couple times. I’ll trust you to make that call if what they do goes beyond what you think merits just a bare bottom spanking.

I told Mike, Sir, I think I understand that perfectly. That’s pretty much how I got spanked except I had the added embarrassment of having to take down my pants. I’ve also gotten a couple licks from my dad’s belt, but it seems like you and my dad are a lot alike on what a spanking should be.

Great, said Mike. It sounds like you’re still interested enough, at least interested enough that you would like to meet the boys. It’s OK if you’re not comfortable yet, but I do have to ask if you’d be OK being naked with us for lunch. I wasn’t sure how I felt about that, and Mike sensed by hesitation. If you not comfortable, don’t worry, it won’t change my mind. I’ve already decided you’ve got the job if the boys are OK with it and you want it. Then in a casual voice that provided another surprise, he said: By the way, Jeff, don’t worry if you think you’ll get aroused. Two of these boys are running around the house with hardons half the time and even Josh, the 10-year-old, is starting to have pretty regular erections. They see me hard at some point almost every day. I breathed a little sigh of relief, saying Thanks for telling me that. My dad, my brother, and I are used to seeing each other aroused, particularly with morning wood, so... With that, I removed my clothes and Mike had to notice my semi. He didn’t say anything except: let’s go get the boys.

We headed toward a beautiful, large kitchen and as we passed the stairway to the upstairs bedrooms, Mike hollered for the boys to come down for lunch – plus he added: your babysitter for the next three weeks is here too! In just a manner of minutes, three naked boys came bounding down the stairs. The boys were bouncing with energy and their cocks were bouncing too. I immediately knew what Mike was telling me about Tim, the 12-year-old. He was clearly starting to show some significant pubic hair, and he was aroused, probably for no other reason that boys at that age are often hard. Every one of them was thin, Kevin was developing some very nice muscles – he wasn’t aroused but had good size soft cut cock for a 15-year-old and a full bush. I could see his cock start to grow a little, probably just because I was standing there exposed. They all had great tans, obviously all over from being able to spend time outside naked. I was embarrassed knowing my ass was so white compared to the light tan I just started for the summer.

Mike told the boys to get the food out of the refrigerator, grab the plates, etc. Let’s grill the burgers and hot dogs on the grill outside. With that Mike directed me outside. As the boys came outside with trays of food, drinks, and utensils, Mike fired up the grill, and I realized how great I felt being naked outside. There was an immediate level of comfort, even more than a locker room, just five guys standing around. I took the time while Mike cooked to introduce myself to each of the guys, asking them about their favorite sports, video games, and what book they were reading right now. In just a few minutes, we were sitting around a picnic table eating lunch. I wasn’t keeping constant watch, but as the guys moved around getting second helpings, etc., erections subsided and the fact that we were all naked meant nothing – for the moment.

Mike pretty quickly got serious. He said: Look, guys, I’ve talked to Jeff, and unless you guys aren’t comfortable for some reason, he’s hired. So, if you have any questions, now’s the time. I’ve gone over all the expectations and rules, so fire away.

Tim went first, perhaps because he was the most nervous with another nude person being added to the household, even for only three weeks. Jeff, you’re naked now, but are you going to be naked the whole time you’re staying here? I quickly responded: Yes, if I have this job I’ll be nude the entire time – I think it’s only fair. That seemed to be Tim’s only question as he gave his dad a thumb’s up!

Kevin hesitated a little bit but wanted to ask something. I said: Look, guys, I don’t live nude at home, but my dad, my little brother – he’s your age Kevin – are comfortable seeing each other naked all time. My dad talks about the naked truth. He says that when you’re naked, it’s actually easier to be open and honest with each other. There are mornings we all stand around the kitchen naked and talking about stuff, so we’re not nudists like you guys but maybe a little bit at times.

With that Kevin asked: I know dad told you about the rules. Are you going to spank us?

I’m going to follow your dad’s expectations and rules exactly as he’s asking – and paying – me to do. If that means you do something that your dad would spank you for, I’m going to spank you.

Kevin turned a little more serious, perhaps thinking I might not be comfortable with his dad’s orders for spankings. Have you ever been spanked? he asked. Yes, I responded, pretty much the same way you guys have been spanked – except I had the added embarrassment of having to take my pants off to bare my butt. And Kevin, I’ve gotten a few licks with my dad’s belt a couple of times I really fucked up. That generated a nervous laugh from Kevin, but he also shot his dad a thumb’s up.

Mike told the guys to clean up everything after lunch, then told them that he and I had a couple of things in terms of schedules, plans, and payments to discuss. But he told the guys that unless something didn’t work out, I’d be moving in just a few days later for my three-week stay.

When we got back to Mike’s study, he handed me a folder with schedules and other information. The boys would all have some things outside the house where they’d get dressed, and I’d be responsible most of the time for getting them there and picking them up. There were other times where someone else would be picking them up. He then gave me a debit card, showed me the pin number and told me to use that for expenses, food, etc. I was trying to think of questions, and one popped into my head: Do they ever have friends over? Yes, responded Mike, but most of the friends they have are aware of our lifestyle and will be naked while they’re here. The boys will let you know if there are any exceptions. You can probably expect a few guys are coming over to swim every couple days. Let’s face it; guys love skinning dipping so...

At the point, Mike’s expression clearly changed, and he said: One more very important thing, Jeff. I don’t tolerate swearing around the kids. If you and I are chatting, I don’t care how many f-words you use because I’ll do the same. I’ve gotten a little more understanding with Kevin if he says shit as long as Josh isn’t around. If he said: fucked up as you did, he’d be bending over and getting about ten on his bare bottom. Mike’s statement was very clear, but I didn’t sense anger. It seemed he just wanted to let me know or maybe I sensed a little disappointment.

I had a very strange reaction to Mike telling me that. My cock stirred a little bit. And I made an instant decision that shocked even me. Sir, I think we need to go back and talk to the boys. They need to know that I’m expected to follow your rules just like they are. But Jeff, you didn’t know I felt that way!

Doesn’t matter, I should have known better and been more careful, particularly knowing that Tim and Josh were sitting there. I think Kevin thought it was cool and he’s probably heard it and using it a lot with his friends, but....

The boys were still outside, having put everything away, sitting at the picnic table probably talking about whether or not they were happy with me staying with them for three weeks. I walked up to the guys and said: Look, guys, I said something during lunch that I shouldn’t have said. If any of you had used that kind of language, your dad would have spanked you. Your dad’s rules are your dad’s rule, and they apply to me. Without saying another word, I moved closer to Mike, spread my legs apart and bent over grabbing my knees. My naked butt was totally exposed. Mike spanked me fifteen times. The first was pretty sharp, but overall, I could tell it was the kind of spanking that was intended, as he’d told me earlier, to be a reminder, not a serious punishment. I stood up and said: thank you, sir, I’m sorry I swore in front of your boys. I think the boys were speechless, but I also suspected I’d earned their respect that might make a big difference in the next three weeks.

What did concern me a little bit, however, was that I had gotten a noticeable hardon from the spanking. I decided, time to go, guys, I’ll see you next week. I headed toward to den to get my clothes. Mike accompanied me, and as I dressed, he said: I’m really happy to have you take care of my boys. What you just did showed a lot of maturity. At that very moment, Mike’s cell phone sounded, and I shook his hand quickly and headed out of the den. As I left the house, Kevin came running up to me. Somewhat quietly, he said: Don’t worry Jeff, I get a hardon every time dad spanks me now – it’s no big deal – although in your case it is a bigger deal.

When I moved into the house the following week, the three boys ran to meet men, grabbed my bags and ran upstairs with them to show me my room. The minute I walked into the room, they all started saying c’mon Jeff, get naked. It’s funny how quickly I felt uncomfortable being dressed. In locker rooms, some guys would be getting dressed, some guys getting undressed, some guys standing around naked talking to each other. It was the same thing at home. I’d be dressed, and dad would walk by naked, or I’d walk into the kitchen naked, and my dad and brother would be dressed – no big deal. But here I felt immediately uncomfortable with my clothes on. As I was stripping, Mike walked in, naked of course, asked if I had any questions, then said: I’ve got to get dressed and get out of here. He gave each of the guys a quick hug and headed to his room.

I had decided that spankings would occur quickly if they were deserved so that the guys knew I wasn’t going to do anything except follow their dad’s rules. And they did occur quickly. For some reason, I didn’t think Kevin was going to test me. His reaction and comment after I got spanked on our first meeting had me thinking we’d already connected – after all we weren’t that far apart in age. Right after dinner the first night, the guys were supposed to spend some time reading, and Tim basically told me he was going to play video games instead. I gave him a simple: Tim, it’s reading hour! When he ignored me, I pulled him over my lap and landed 10 spanks to his bottom. The first one was hard enough to make him jump a little, but then I lightened up – trying to mimic the spanking I’d gotten from Mike. I think it worked in setting the tone.

These three boys were every bit as rambunctious as most boys their ages, but the fact that I could spank them made them easier to control. I had a regular babysitting gig for a family with boys very similar in age to these guys last year. They got away with way too much, and I’d been specifically told I could only discipline them with timeouts. When I finished the job, I actually told the parents they might want to reconsider how they disciplined their kids. I told them each of their boys deserved a good spanking.

It was certainly different because of the nudity. Three energetic boys were playing video games, reading, swimming, playing basketball – always with butts on display and cocks bouncing. Over the first three days, I ended up spanking each of the boys at least twice, typically fairly mild just to keep them under control. Josh was exactly the wise-ass his father told me about, and I started to think he thought a quick spanking was worth it as he’d say something that kept his brothers laughing. I’d pull him over my lap and spank his bottom just enough to calm him down a bit and turn his butt pink.

Tim seemed to be the one wanting to avoid getting spanked, but he still wanted to break some of the rules, and he tried to get away with stuff without getting caught. It didn’t work because I was familiar enough with most of the tricks. I’d probably tried most of them myself and probably got spanked for most of them too.

There was an Interesting and different discussion with Tim and Kevin on the third day of my stay. We were sitting around the family room, just relaxing, with a baseball game on television. Josh seemed very tired, and I suggested he go upstairs, shower, and get to bed. After a few minutes of silence, Kevin asked: Jeff, did you ask dad to spank you the first day you were here?

Yes, I did – for exactly the reason I told you. He didn’t want to. He thought it wouldn’t be fair because I didn’t know about his rules on language. When he finally agreed, he wanted to spank me in his study, privately. But I said no to that. You guys needed to see me get spanked – bare bottom and embarrassed.

Tim asked: Did you get spanked a lot growing up? I responded: No, not really. I guess I was a pretty good kid. But when I did get it, it was different than what you guys get. I wasn’t naked all the time like you guys. My father would order me to take your pants down. That would sometimes seem worse than the spanking itself. The whole thing seems very different here with you guys having your butts on display all the time.

One thing I quickly learned in the first few days. My dad’s insights on naked truth were very true. It was somehow easier to talk openly and honestly about anything when you’re sitting around naked. I also realized something else that was different. These guys stayed cleaner than some of the boys I’d babysat for – including a few I struggled with trying to get them to shower and wear fresh clothes. Kevin, Tim, and Josh would quickly rinse off after swimming. They always came down for breakfast freshly showered and they almost always showered again at some point during the day. I thought the nudist lifestyle made them more aware.

The most significant, and serious spanking did occur about halfway through the three weeks. Josh and Tim were both gone for the afternoon, enjoying afternoons with several of their friends, including some who didn’t know about their nudist lifestyle. Kevin was home alone, wanting to enjoy perhaps some alone time that I certainly understood. I asked him if he wanted to make a grocery run with me, but he declined. I told Kevin I was also going to stop at my house to just quickly update my dad on how things were going and grab a couple DVD’s I thought the guys might enjoy.

The grocery shopping took a little longer than I expected, and I decided to skip the home visit until another day. When I returned to the house, it was immediately obvious that Kevin was no longer alone. When I walked into the kitchen, I could see Kevin and two other guys out by the pool. If they’d just been skinny dipping I might have let Kevin go with just a little warning that he should have told me, but they were not just skinning dipping, they were sitting around on the edge of the hot tub masturbating each other. The fact that they were jerking off didn’t bother me at all. I’d jerked off with other guys a few times. Once my dad even caught us. My younger brother was away at camp when it happened so my dad actually just kind of laughed. He did warn me later that if my brother had been home, I probably would have gotten a pretty serious spanking. So, I was mad at Kevin for the same reason. His brothers might have come home at any minute, and that was not going to be tolerated.

I walked out to the pool, and the three guys jumped up and tried to cover their hard cocks. I told them it was pretty obvious what was happening and there wasn’t much point in covering the obvious. Kevin was immediately more comfortable letting me see his hard cock – because I’d seen it several times already – but the other two guys wanted to cover up. I said, You know you’re getting your butt roasted for this Kevin – I can’t believe you’re out here jerking off with the possibility of your brothers coming home at any minute. How tough would your dad spank you if he caught you? Kevin, I think, wanted to lie, but he said: I’d get spanked – hard — and I’d get the belt too.

Well, that’s the same thing you’re getting from me unless you want a pass today and I’ll tell your father and let him deal with it when he gets home. No way, Jeff, Kevin pleaded, I’ll take the spanking from you! I looked at the other two guys and said: You guys get dressed and get out of here. I’ll get your parent’s phone numbers from Kevin and let them deal with you. Any modesty these guys pretended to have dropped away immediately, and they both started pleading with me not to call their parents. One of them, Steve, begged me, saying please don’t call my dad, he’ll whip my butt raw without even caring that we were just jerking off. He’s whipped me a couple times I was just jerking off alone in my room. I didn’t like the sound of that if it was believable. I looked at Kevin, shrugged my shoulders.

Kevin said: I suppose knowing what will happen to Steve isn’t good enough to let us all off the hook. I’m sorry. I didn’t think that Josh or Tim might see us. Then, he almost smiled, and I knew why he did. Jeff, I think both of these guys would let you spank them. I know Steve will because I know how bad his dad spanks him. Both guys quickly agreed that I could spank them. I could tell from the look on Kevin’s face that he was going to endure the spanking, even the belt because he was going to see two of his friends get their butts spanked.

I was still dressed so I pulled the belt out of my pants and walked over the picnic table. Get over here guys; you’re first Kevin. This is your fault even if you didn’t start it. Kevin didn’t even hesitate for a second. He bent over with his hands on the picnic table, his ass perfectly exposed. I spanked him harder than I had any time during the first days of my stay and I spanked him longer. He wasn’t crying, but he was grimacing to hold it in, and I turned his butt a pretty clear shade of red. I then took the belt and gave him two whacks that made him cry out and jump. I’d actually planned on giving him more with the belt, but I was actually impressed by how he admittedly took responsibility for being stupid.

Steve looked relieved when he bent over to get the second spanking. I guess he knew it was much less severe than what his dad would have given him. I didn’t give him the two licks with the belt – something I knew I’d have to explain to Kevin later. Vince was the third, and he seemed a little more reluctant. He also appeared to be closer to tears than either Kevin or Steve. Perhaps he wasn’t spanked or wasn’t spanked very often. Another thing I’d probably discuss with Kevin.

With the spankings concluded, I ordered Steve and Kevin to get dressed and go home, warning them that if I caught them again, I’d tell their parents with no hesitation. As the guys left, I went back into the kitchen and unpacked the groceries. I also quickly ran up to my room and removed my clothes. I knew I had to talk to Kevin and I knew it would be unfair for me not to be naked. I’d told Kevin to go to his bedroom – We need to talk.

I wasn’t hard when I entered Kevin’s room, closing the door behind me, but I was definitely showing a little arousal. Kevin was sitting on his bed, and he was hard. Are you hard from the spanking or because you got aroused seeing your buddies getting spanked? He just shrugged and said Both! I’m sorry, Jeff, I know it was stupid, but the guys were just skinny dipping, then Steve popped a boner, and we just couldn’t resist jerking off. I know I should have just told them we needed to come up here and close the door, but...

I said: Hey, I understand, but you’ve got to be more careful. If you’d been up here, I probably wouldn’t have known, and even if I did, I’d probably understand. Your dad told me he saw you masturbating a couple of times and told you it was OK – as long as your brothers didn’t see you. And you know because you told me that you’ve been getting hard whenever your dad spanks you, and you saw me get a hardon. No big deal, remember? Maybe I shouldn’t tell you this, but my dad caught me jerking off with a friend of mine. We were in my room with the door closed. He came in without knocking. He actually just laughed, and later he apologized for not knocking. But if my brother had seen me, I’d have gotten my butt roasted! I’d stopped in my room before going to Kevin’s room. I tossed him a bottle of my favorite lube and suggested he rub a little on his still red butt and then you’ll know what else it’s good for... I closed his door as I left and went to my room. I was fighting not to be totally hard from the entire incident but once I got into my room, I could without worry jerk off. Wow!

This nude lifestyle was proving very interesting. In the first week, I found out it was easy to learn a lot about the lifestyle itself and these boys because of their comfort with being naked. I also learned a lot about some of their friends. I even learned some things about some of the friend’s parents. Kevin seemed to have the most friends that were comfortable naked although Tim was a fairly close second. I was a little surprised at the 15-16-year-old teens being so comfortable, but I tried just to extend the comfort I had at home with my brother although I thought that was different.

Anyway, one day Kevin and Tim told me that two of their friends, also brothers were coming over for the afternoon. I always wanted them to let me know. When the doorbell rang, Kevin and Tim raced to the front door. Their two friends, Andy and Dave, were naked in seconds. All four boys came over toward me in the kitchen so that I could be introduced to Andy and Dave. I was then shocked to see Andy and Dave’s father follow them into the house. He was dressed in a t-shirt and a pair of shorts. I usually kept a pair of shorts and a t-shirt handy so I could get dress quickly if needed, but I hadn’t done that today. He headed right toward me and introduced himself. I started to apologize, but he stopped me and said: Don’t worry, I’m used to being here, usually with Mike. If I had more time, I’d strip and enjoy the pool myself. I did want to talk to you a little bit, however.

I want you to know Jeff that you have my permission to spank my boys if they misbehave. I don’t know if Mike told you that. He’s definitely spanked them a couple times when they were over here. And I’ve spanked Tim and Kevin at our house. You should treat them exactly as you’d treat these guys you’re babysitting. My boys know that misbehavior means a spanking on their bare bottoms. I gotta run, but if I can get back early, I’d actually like to talk to you about your availability to babysit my two boys.

After a week and a half, I’d noticed something about Tim that concerned me. He was clearly showing some signs of stronger feelings. He wasn’t necessarily uncomfortable being naked but I sensed he was getting a little sensitive about the frequency of his erections – despite the fact that Kevin would be sporting a hardon at different times throughout the day – and so would I. I thought I knew what the problem might be but I tried to decide if I should talk directly to him, have Kevin talk to him, or wait for his dad to deal with it.

Before deciding what to do, the problem solved itself, sort of, the next morning. When I called the boys down for breakfast, Kevin and Josh bounced down the stairs as usual. When I asked: Where’s Tim? Josh started giggling, and Kevin glanced down at his own cock. I got the idea, so I just walked over to the stairway and called for Tim again. At that point, Josh, giggling even more, said: Tim’s in his room playing with his dick. Kevin just looked at me and nodded.

Tim came down for breakfast but was quieter than usual. As they headed away from breakfast, I looked at Tim and said: Tim, please go up to your room. I’ll be up in a couple minutes. Tim actually looked at little scared. I was almost betting he was worried I might be the one who was going to give him the first taste of a belt on his butt.

I tossed all the dishes, pans, and stuff in the dishwasher but before going upstairs, I looked for Kevin and said: If you OK with it, I’d like you to join me talking to Tim. There was a momentary Really? but he then said: Sure.

We walked into Tim’s room, and I closed the door behind us. Tim was just sitting on the edge of his bed obviously contemplating a reality that he was sure would result in a spanking. But he reacted quickly with: Why’s Kevin here? It wasn’t the spanking. They’d been spanked together, they’d watched each get spanked – but this was different. I just responded with: Tim, I think Kevin being here is a good idea, trust me, kid!

I then started the mini-lecture: Tim, you’re going to get a spanking but not for the reason you might be thinking. I’m not going to spank you because you were jerking off. I looked at Kevin: Kevin, did you ever get spanked just because you were masturbating? Never, responded Kevin, In fact, Tim, one time Dad walked in on me and he just smiled. He came back later and apologized. If you haven’t already figured it out yet, Tim, dad still masturbates. I’ve seen him.

Tim, as I said you are getting spanked – but the reason is that you didn’t close your door and Josh saw you. Your dad says he’s already getting pretty curious, but he didn’t need to see you beating off. Stand up kid – grab your knees! I intended the first contact of my hand to his bare bottom to be a sharp, memorable swat. Then I backed off a little, then quickly a little more. I wanted Tim to feel it and remember to close the door. He was crying by the time I stopped, something I hadn’t seen before even though I’d probably given him one harder spanking before this one.

When I stopped, Tim stood up. He didn’t move to rub his butt, so I figured I didn’t bust it too bad. But as he tried to get the crying under control, he uttered: I’m sorry Jeff. I’ve just been feeling so darn horny lately — it’s like I can’t stop playing with it.

I know kid – it’s pretty normal at your age. Why don’t you talk to Kevin about it for a couple minutes? He’s been through it, and the only person in this room who’s masturbated more than Kevin is me? Kevin started laughing. I looked at Kevin and said: Can you make sure he’s got a box of tissues and some hand lotion in here?

Josh’s only more serious spanking came just a couple days before their father was due home. He was clearly the young wise-ass that Mike had told me about, and almost daily I’d have to give him a couple quick smacks because of something he’d say – or because he’d just wouldn’t settle down during a meal. I wasn’t sure if Mike would approve, but I actually let Kevin spank Tim twice. Kevin was only a few months shy of 16, and at that age, I was already babysitting for other families – and spanking some bare bottoms at the direction of parents. I thought two things. Kevin might be able, with his father’s permission, to do some babysitting for his younger brothers. Similarly, I started thinking about talking to Kevin and his father about Kevin being part of my babysitting service.

So, one night, just as I was preparing dinner, Josh was running around the kitchen and after a couple of warnings to settle down, I called Kevin over and told him to get your brother to settle down. Give him a couple of smacks. I was sure that Kevin knew exactly what that meant. I wasn’t worried he take the chance to beat his little brother. He was as near perfect as a spanking could be. He stopped Josh as he ran by him, took him over to a chair and pulled him over his lap. He calmly said: Cool it, Josh, stop running around when Jeff tells you to. With that, he spanked Josh about five times, just hard enough to calm him down – at least for a while.

The more serious spanking for Josh started with a phone call. Josh had gone swimming with some friends as part of a day with a small group of his friends. Around 3 o’clock the phone rang, and it was one of the parents telling me that he was bringing Josh home early. Apparently, the boys started causing a lot of trouble at the local pool, so much that they got kicked out. And while all the boys were part of the problem, Josh and another boy were the ringleaders. Just a few minutes later, Josh walked into the house. He didn’t look very happy. I sat him down in the living room and listened to his side of the story. It wasn’t much different from what I’d already heard.

Josh, you know this means a harder spanking than any I’ve given you. I pulled his t-shirt up over his head and then said: Take your pants off, kid. I could see the tears starting to form on Josh’s face. He’d seen his brothers getting tougher spankings from their dad – and from me – so he knew he was about to really get it. I helped him get over my lap with his bottom positioned for what was going to be a harder, longer spanking. I spanked him for about ten minutes, it probably felt like twenty to Josh. I made sure his butt was a good shade of red, showing through his dark, tanned butt. He was crying pretty much from the start, but he didn’t try and get away. I knew from the instructions Mike had given me that the boys knew it was important to accept a punishment, or...

After the spanking, I didn’t say much. Josh knew what he did was wrong, and he’d paid the price. I told him to go to his room. Kevin had come inside from the pool when he heard Josh getting spanked. As Josh headed to his room, I just nodded to Kevin in the direction of Josh. He knew what it meant to have a burning butt from the sting of a tough spanking. I knew he’d get Josh to cry it out and calm down.

The last three days of my assignment were, not surprisingly, fairly quiet. A lot of the days over the three weeks were like that. The three boys were boys. They had a lot of energy but the majority of the time they treated each other, the friends they had over – rarely during my three weeks – and me respectfully. When dad arrived home, he was attacked by Josh, Tim, and Kevin – with enthusiasm, probably because it was obvious he’d brought some presents with him. I went up to my room to get dressed, grabbed my bags, and headed back downstairs.

I heard the last couple minutes of a de-briefing that Mike was holding with his boys. They were praising my time with them, asking their dad if I could babysit for them again. There were also a couple of comments made by Kevin and Tim that I spanked just as hard as you do dad!

Mike told me to join him in the den. He joined me after just a few minutes that he took to remove his clothes. When he entered the den, he laughed: Sorry, three weeks of being dressed most of the time was almost too much. I was again amazed at how comfortable this man was nude – with me sitting there clothed – even though I’d just spend three weeks naked myself. With that he handed me a check for $ 5000, adding Thank you. I heard some really good things from every one of the boys. I’ve got another trip coming up. As soon as I get some details, I’ll be in touch. I hope you’ll be available.

With perfect timing, Mike said: One more thing, Jeff, as Kevin walked into the room. He stood next to his father. Kevin told me that you told him to spank Josh, is that true? I didn’t even think about denying it because I’m sure it was verified by Josh. Yes, sir I did. Honestly, it was twice that Kevin spanked Josh. I found it difficult to read both Mike and Kevin’s expressions at that point. I thought Kevin seemed nervous. I was hoping Mike wasn’t mad because I didn’t want to think my last day was going to be like my first day except for this time I’d be taking my pants down for another spanking from Mike.

But he then calmly said: I’m happy you saw that it might be time for Kevin to take that responsibility. I’ve wanted to talk to him about that so that he could take more responsibility for shorter times during the day or when I out for a short time. Kevin told me you were confident he wouldn’t spank Josh too hard. He also told me you let him handle a situation with Tim very well. Let’s talk just a bit for now about this idea that Kevin might take some babysitting jobs with your service.

Kevin was excited about this possibility joking first I should have told you right when I walked in Jeff that you were going to get to keep your pants on! then just a couple minutes later Are there any other families that are nudists?

I had to think about adding Kevin to my business, so I told Mike and Kevin that maybe we should meet again in a few days. That turned into something very interesting.

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