This is going to be a multi-parter chronicling a series of escalating events that happened to me in September

I (38M) am a contractor. A little over a week ago, I started on a deck project for an older couple I’ve done a lot of work for in the past. The husband (we’ll call him Gary) is probably in his 70’s, overweight and in somewhat poor health. The few times I’ve seen him up on his feet walking, it stressed me the fuck out thinking he was going to have a heart attack. His wife (Let’s say Shannon) is probably in her 50’s and still looks pretty good. Comparable to one of the older ladies on those Real Housewives shows. Gary did pretty well for himself, owning his own business and their house is pretty huge, so I’ve always imagined it was sort of a trophy wife situation even though I don’t actually know how long they’ve been together.

So, first day of the job, I’m packing up my tools and Shannon comes out to talk to me. I asked her if there’s a hose somewhere nearby that I can use to rinse myself off. I don’t like getting in my truck all sweaty for a 30 minute drive home so if possible, I’ll usually rinse of my head and torso with a hose first. She asked me if I would rather just use one of the showers in the house and I said “Yeah, if you don’t mind”. She leads my inside to one of the guest bedrooms that has its own bathroom and leaves me to it saying “Let me know if you need anything.”

Now I’m a bit of an exhibitionist. I’m always looking for opportunities where someone like Shannon might “accidentally” see me naked. It’s a difficult thing to do without being super obvious which is creepy and not the vibe I’m after, not to mention bad for business. You really just have to wait for the right opportunities knowing that most of them won’t pay off. But when they do…

I closed the bedroom door 95% of the way and got naked knowing that she probably assumes I’m getting undressed/dressed in the bathroom itself and that there’s is the tiniest sliver of a chance that if she were to come back for some reason, she might not think to knock on the bedroom door. Based on the layout of the rooms, this was my best shot. So I proceed to take my shower. I played with myself a little thinking about how hot it would be for Shannon to walk in on me but I didn’t go all the way. Step out of the shower and grab a towel from under one of the cabinets and walk out into the bedroom. Disappointed but not surprised that Shannon didn’t pay me a visit, I start getting dressed. I had my pants and shirt on when I noticed the sound of shoes coming down the hallway. Heart racing, I stripped faster than anyone has ever stripped before, grabbed my towel and stood directly in front of the door, pretending to dry my hair. This was it…

She. Walked. Right. In.

I had the towel up around my head mostly obscuring my face so I pretended to not notice her for the first millisecond before she quickly backed out of the door and said “Oh my God Im so sorry!”. But in that brief moment I got to watch her take it in the full picture. Even as she was backing out, she was staring at my cock which thankfully, was still partially chubbed from the shower. I acted only mildly startled and assured her it was ok as I moved my towel to cover up. To my amazement, she wasn’t running down the hall in embarrassment but still standing right outside the door with her gaze averted. She kept apologizing and going on about how she just remembered there weren’t any towels hanging up so she was just going to lay one on the bed but didn’t think to knock etc. I assured her again that it was no big deal. Once she realized I was covered and not upset she looked back at me and said that she promised she wasn’t trying to sneak a peak. I laughed and said “More power to you if you were”.

Day two started off pretty normal. I typically don’t knock on the door or anything to let them know I’m there. They know about what time I start so I just let myself into the backyard and get to work. After 30 minutes or so, Shannon comes out to say good morning and ask if I needed anything. Then of course she apologized again for the shower incident and I once again assured her that it wasn’t a big deal, going the extra step to tell her that I’m actually a nudist, so literally hundreds of people have seen me naked. (This is mostly true although I’m not sure if I actually qualify as a nudist since I get off on it. More of an exhibitionist wolf in nudist sheep’s clothes if you will) She was intrigued and started asking questions. I told her about the naturist resort I visit once or twice a year (that part is true). She asked “What about at home?” and I told her that yes, most of the time Im naked at home (not true at all. No audience = no fun) and that I even mow and do yard work in my backyard naked (also not true as should’ve been evident from my tan lines). She laughed and said:

“Well you should move out here (gesturing towards the trees that surround the large property). We’re so secluded, you could be naked all the time”.

I said “Oh if I lived in a place like this, I would never put on clothes”.

She said “Well I’m not quite that adventurous. I’ll go out to the hot tub without a swimsuit from time to time if it’s dark out here but other than that, I stay dressed.”

“I get it. It’s not for everyone.” I said

Then she really surprised me and said, “Well there’s no neighbors around and we don’t care so if you feel like being naked while you’re out here, feel free.”

My jaw almost dropped.

“You mean that?” I said. “It wouldn’t make either of you uncomfortable?”

“I don’t mind.” she said “And I doubt Gary will be back here while you working. If he does come back here I’ll just explain it to him. I’m sure he won’t care.”

That part seemed doubtful to me. Gary is a nice enough guy but has never struck me as so laid back he’d be totally on board with a younger guy walking around naked in front of his wife.

“Well, I might just take you up on that.” I said.

Might? Who am I kidding? I’ve just been given the ultimate green light OF COURSE I’m taking this opportunity. But I didn’t want to ruin the vibe by appearing too eager. A few minutes after she went back inside, I grabbed my sunscreen, stripped down and began my first day of nude, exhibitionist carpentry.

It gets even crazier from there. I’ll try to post part 2 in the next couple days.

EDIT: Thanks for the response everyone. I have part 2 typed up and saved as a draft but every time I try to post I get the “Something went wrong. Check your post and try again” message. I can’t figure out what the issue is so I’m moving the whole thing over to r/literotica. I’ll give the folks over there a day or so to be enticed by part 1 and then I’ll drop part 2 over there tomorrow night.