He's fairly comfortable around me and (briefly) managed to be free with my sister's family too, which is why I think he might be open to the idea of wearing a swim brief in public. Like most boys, he grew more modest when he hit puberty. He'd always hide his body at home, but, since he was a minor and his dad wasn't around, I'd accompany my son to the doctor. His general practitioner and dermatologist both had him undress completely, so I'd get the occasional look at him nude growing up.
Last summer, my sister and her husband invited us to spend a week at the lakeside cabin they'd purchased a few months earlier. She has two boys, 5 and 7, and a 3 year old girl. Before we went up, she warned me that her husband and the kids had taken to swimming nude. She'd make sure her husband covered up while we were there, but couldn't make any promises for the kids. I told her it would be fine.
When we got there, we found that the kids were practically nudists. My son, of course, wore his shorts. They wanted to know why their dad was dressed, but he just told them he felt like doing something different. They were persistent in their questions, however. My son and I were sharing a room with two twin beds. The first night, before we went to bed, I asked if he'd mind his uncle swimming nude, since that's what they prefer. He said he didn't care.
At breakfast the next morning, I told my sister that her husband was free to dress (or not!) as he wished. He went swimming nude that day and for the rest of our visit.
The following day, my son slept in. I came in to wake him up and tidied up a bit. Without thinking about it, I tossed a pair of underwear that was next to his bed into our laundry. He was awake, but still lying in bed, so I asked if everything was okay. He said yes, but confessed that he'd been sleeping naked. He'd been intending to slip on the underwear I'd thrown in the laundry. I laughed, and left to give him some privacy.
That night after we got ready for bed, he was a bit awkward. He was probably remembering the encounter from that morning. I sleep nude at home, so I told him. Then I asked if he'd mind me sleeping nude, since he'd already broken the ice. He said okay. I undressed and slipped under the covers. My son waited a moment, then dropped his briefs and quickly got into bed. I turned out the light and we went to sleep.
So it went. Each night we'd undress and each night we'd linger for just a bit longer before getting into bed. One morning towards the end of our trip, I'd finished my shower. I wrapped my towel around my body and went to wake him up. I'm not sure what compelled me, but I figured what the hell, took off the towel, and wrapped it around my head. When he woke up he was surprised, but not offended, at seeing my body. I told him it was his turn in the shower, then went back into the bathroom to finish getting ready.
He followed shortly after and hurriedly got in the shower. When he was done, he reached outside and grabbed a towel. He pulled the curtain aside and was wrapped in the towel. My son used the sink next to mine, occasionally stealing glances at me. I thought perhaps I'd gone too far, but almost to answer my fears he casually let his towel drop and didn't pick it up. We finished getting ready and went out to join the others for breakfast.
It was the second to last night at the cabin. I undressed as soon as we got to our room and my son did too. Before I turned out the light, I told him that I was sure he was welcome to join the others and swim nude if he preferred. He said he'd think about it. The next morning, he didn't need any encouragement to get out of bed and we got ready together again. After breakfast, my son and I went for a walk. When we got back, the others were down by the lake.
We went inside to change into our swimming clothes. After we'd undressed, but before my son had pulled on his shorts, I reminded him that he was welcome to go without a swimsuit. I'd asked my sister earlier, and she'd given her blessing. He seemed to be considering it. To push him over the edge I added that I was thinking about going nude too and we could do it together. This did it.
I led the way down to the lake. My brother-in-law and the kids were in the water. My sister was watching them from the shore. She turned and saw us when we got close. My son looked nervous, so I suggested he get into the water. I joined my sister on the shore and explained everything. Then I went to swim with the others.
Eventually we tired and came up onto the shore. I was glad to see my son had relaxed completely. My sister was wearing a bikini, but on seeing the rest us nude decided to join the fun. We spent the rest of the afternoon swimming and lounging until it was time to go inside for dinner. My son seemed disappointed when it was time to get dressed.
We had to leave the next morning. I thought my son might continue to be more open with his body at home, but went back to his old ways. It was nearing the end of summer, and he had a dermatologist appointment scheduled. I was due to see her as well, so I scheduled an appointment for myself at the same time.
When the assistant took us back, she asked if my son wanted to be seen first, so he could wait outside during my exam. I told her it was okay for us to be seen together. She instructed us both to get undressed and left some gowns on the counter. My son was a little nervous, but we both took off our clothes. I picked up the gown and said we probably didn't need them. He looked a little worried, but nodded.
The doctor came in to see us. She was a little surprised at first to find us both naked, but finished our examinations without incident.
Having opened the door again, I asked my son during the ride home if he'd be okay with my being naked occasionally at home. He said okay.
School started a week later. I'd showered before he woke up. Thinking back to our experience at the cabin, I wrapped a towel around my head and went to his room to wake him up. The next morning I did the same thing and even started coming to breakfast every once in a while similarly clad.
He remained modest until one day I was picking up laundry. He was in his room wrapped in a towel. Before I left, he stopped me and handed me the towel to wash. I gave him a big smile and then left.
Since then, he's been a little more comfortable around me. It's not like we're nudists, but we don't bother to hide.
Sorry for the length, but hopefully you enjoyed learning more about our situation.
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