Sorry for the delay, I couldn’t get part 2 to post in r/literotica or r/gwstories I finally figured out that it was too long. So I’m breaking the story into even more parts. I’ll post 2 and 3 tonight.

Part 1 ended with Shannon, the 50’s-ish MILF who hired me to replace part of the deck on the back of her and her husband’s huge house, giving me the green light to be naked on their secluded property after she walked in on me in the shower.

It was a bit difficult to focus on my work for the first hour or two. The thrill of being naked at someone else’s home, the anticipation of when Shannon might come back outside, it was too much to think about. Not to mention that it’s just kinda of weird doing manual labor with your dick flapping in the breeze. I did decide to keep my shoes on. My biggest distraction was noticing the dozen or so windows looking out onto the deck where I was working and how Shannon could’ve been watching me through any of them…

She’s always been a little flirty with me in the past. Nothing explicit, just flirtatious in the way that older women can sometimes be. Always touching my arm, calling me “honey” or “sweetheart”. I never thought much of it but after her reaction to seeing me naked, immediately followed by her offer to allow me to be naked on her property, I’m beginning to think she liked what she saw.

After about two somewhat less than productive hours, Shannon emerged from the house to offer me a glass of water (even though we’d already established the previous day that I always bring a stocked ice chest with me). I accepted, if for no other reason than to have an excuse to approach her. She was trying to play it cool but I caught her eyes wandering down my sweaty naked body several times while I drank.

She came back out 2 or 3 more times that day to offer me more water or “just see how it was going”. This was in contrast to the one time she’d come out the previous day. Each time, we’d chat for a minute and I would try (with varied success) to focus my mind and get my cock slightly hard without touching it. On her final visit, as I was packing up, she asked if I wanted to use the shower again. Now this presented a bit of a dilemma. The most direct route to the spare bedroom would take us through the living room where Gary would be parked on the recliner. This meant that I would either be walking through the house naked in front of the potentially unaware husband OR getting dressed to walk through the house, get naked again, shower, get dressed again and leave. Neither option was ideal. Luckily I had a better suggestion and asked if she minded if I just took a quick dip in the hot tub to rinse off. The hot tub was located on a separate deck off the master bedroom, connected to the main deck by a narrow walkway along the back of the house. She said that would be fine and even offered to bring me a towel again, laughing. I joked and said at least this time you’ll know I’m going to be naked.

The next day was remarkably the same. Lots of little visits throughout the day ending with a dip in the hot tub where there was already a towel laid out for me. Drive home, jerk off to the various mental images of her checking me out, go to bed, wake up, repeat. To be honest, the whole working naked thing was getting a bit old but I couldn’t resist further opportunities to stand there while she ogled me. Besides, it would undermine my credibility if I suddenly decided I wanted to wear clothes again.

Day 4 is when things got crazy. Everything was normal throughout the day. I was getting close to being done with the deck despite all the distractions slowing me down and killing my hourly rate. I packed up at the end of the day and made my way over to the hot tub to discover Shannon sitting in it. Surprised I said “Oh I was going to take a quick dip but I can wait-“ she cut me off and said I was welcome to join her, further confirming my suspicions.