Finally making my next update here...
Over the course of that summer of 2020 things kept amping up between me and Debbie. We were best friends and housemates but it was clear there was so much more simmering under the surface.
It was the first summer of Covid 19, there wasn't a lot we could do in the summer besides go to the beach, we recruited another young (28) Italian female friend to our nude beach outings called Carla and, in fact, Debbie and Carla had sex with each other on a few occasions. At the age of 38 I couldn't believe how lucky I was to be constantly naked with these two beautiful slim girls, I still can't believe it... I'm a lucky guy!
For Debbie's birthday me and Carla combined our money and bought her a vibrator that Carla swore by. It was then often an evening when I'd be at my desk, playing a computer game, listening to the loud moans of orgasms coming from behind Debbie's bedroom door. There was also one time, when Debbie and Carla had sex, when they left Debbie's bedroom door at least a foot wide open. I needed no excuse to get a drink from the kitchen that night.
Debbie had also joined me and started showering naked with the bathroom door wide open, propped on its door-stop. I would be naked also, before work sometimes, and Debbie would come in to shower just after I'd finished. I remember many times brushing my teeth, still nude, sleepily chatting to Debbie while she showered just a meter away. She has the most beautiful slim tummy, possibly the best ass I've ever seen, her stunning long slender back led up to her long, dark hair. In between her legs always some hair of varying degrees of length depending how she felt like keeping it, never in a "V" shape though, it just didn't grow outwards that much, just upwards, if that makes sense. She would comment on her "bush" and we'd both take a good long look and chat and laugh a little at how this most private of areas was looking for her on the day. My penis would frequently end up at least semi-erect, a good 6inches swinging in between my legs.
"Normalising" the nudity and continuing to push the envelope made life so interesting. Me and Debbie just ended up having very few boundaries at all with each other. To the extent that I could come in her bedroom naked and flop down next to her, we'd chat, we'd even pop each others zits, I'm not even joking!
The simmer started turning to a boil by the end of August 2020 as the summer began to wane. Debbie's hands had become more and more adventurous over time and, on the none-too-scarce occasions when I was naked and we were chatting whilst near each other, Debbie would start by stroking my legs, she'd move to my inner thighs, she'd see me getting semi-erect and often I'd just become fully erect in front of her. At first I feigned embarrassment when I became fully erect, because frankly for me there's nothing sexier than a situation not being overtly sexual (digression: I think partly because a sexual situation comes with pressures and expectations that I find to be an obstacle to connection with someone!), feigning embarrassment and pulling away from Debbie, making it seem as if a full erection was the limit I would go to, making it seem as if only then, when I was fully erect, I would become embarrassed, helped the situation at least teeter on the precipice of being full-blown-sexual. But her fingers would then move to begin stroking my erection, caressing my balls, I even once in this pre-sexual moment had Debbies finger inserted in my asshole whilst I continued to chat and make light of the situation, but also groan a little with enjoyment.
Feigning embarrassment over my erections also opened the door to a new opportunity though as well: I would pull away with an "alright young lady that's enough" and sometimes I'd continue chatting and the erection would eventually fade. Sometimes though, at a break in the conversation shortly after feigning embarrassment, I would get up from wherever I was, sitting next to Debbie, and silently make my way through to my bedroom sheepishly, with my head down. My bedroom door was simply never shut any more at this point though and, although my bed was not visible from the communal area, I would lie down on top of the covers and begin to masturbate knowing Debbie could hear if she tried. I remember clearly the first time she walked to my open door and leaned against the wall to stand there and watch me, and I remember exclaiming and feigning the embarrassment again - "don't watch me!" But she would. I remember ejaculating all up my chest as she sat on the side of the bed next to me, her hand running up my inner thigh to help me cum. Then she went and got some tissues to help me clean up.
That's when it all turned to a boil really, there's no pretending after that point. I was sad to lose the plausible deniability of the whole situation but it had to happen. It was a week day evening in September and I remember sitting at the window, playing on my phone, I think I was actually wearing a dressing gown and wasn't naked as usual, but Debbie knew there was nothing underneath the dressing gown. She came over, sat next to me, slid her hands under the dressing gown as we talked and started playing with my penis like usual. I was as solidly erect as I can ever remember being. I simply stopped talking, held her in position so she wouldn't move, then maneuvered my way around so I was behind her and slowly pulled her sweatpants down to reveal her naked underneath, and wet, and so I found her opening and penetrated her slowly at first, then gradually worked my way inside of her until her pussy was filled with me and began stroking slowly, holding her in position.
From then on all pretense was gone. We were working from home and instead of work breaks we'd have casual sex breaks. On multiple occasions she would cross the room on all fours and stick her head in my lap, indicating she wanted to deep throat me. Face-fucking was a new one for me but she encouraged it. We eventually took on a dom/sub style relationship - yet with me as the sub! But alas, and here's the end of the story, it lasted a month or so before it fell apart, for so many reasons, sadly, that I will not go into here because it's just not as fun as the rest of the story. I ended up moving out.
But bizarrely, a year after in 2021, we ventured back to the nude beach again one more time and I possibly cannot remember a more blissful day. The term "frolicked" is rarely used but hell, that's what we did that day, we had goggles and swam naked through each others open legs under water, touching and playing with each other as we passed through. We lay at the sea shore, as the waves lapped at our nakedness and the sun warmed us, exclaiming how wonderful it all was. Back on the beach I remember Debbie asking if I wanted some sunblock on my back and using the opportunity to spend far too much time sunblocking in between my legs! Lastly I remember lying on my back as Debbie sat up, I remember running my fingers through her hair from where I was lying and down her back, it instantly gave me a huge erection and to hide it from other beach-goers I rolled onto my side, facing Debbie. Debbie saw it and lay down facing me, then moved down and simply hovered with her face just a few inches from my erection, breathing heavily, as if it was all too much for her.
A month later Debbie hooked up with someone else and they've been together since. If things ever change I'll get back and update this again.
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