NVS-11 December 2025: Taking a Second Chance on S

My current FWB, and frequent HNW collaborator, is a lady I refer to as “Sâ€. She’s a wonderful FWB. Personality wise she is, easy-going, fun, and adventurous (MOST of the time – read on). She is also more than eager to pose for, and even suggest fun twists to, naughty photo ideas I’ve had. Physically she is a petite, blue-eyed, blonde with the rocking body you’d expect on a former yoga instructor, though she has fake bewbies like so many women her age. Speaking of which, and to top it all off, she is entirely “age appropriate†for me, being just 3 months younger. Regular readers probably know most of this. But what you might not know is that this is my second go-around with S as a FWB.

We first met in about 2015 via her (legitimate) massage business. If you know me at all it will not surprise you to hear that OF COURSE our chit-chat got naughtier and naughtier during those sessions. Eventually it evolved into a massage followed by sex. Hand job happy endings came first (pun intended) of course, then oral, and later full on intercourse. But she was quite meticulous about the full hour of massage business being concluded and paid for, before two fiends started having sex. (This was how she avoided feeling like she was being paid for sex, and her rate for the massage was EXTREMELY competitive regardless.)

Things continued to grow more comfortable between us so one day I asked her to accompany me to a nekkie resort. She was hesitant at first but eventually found someone to watch her birds and her dog and agreed to go. The resort is a full day away and the early parts of the trip did NOT go well. It’s a testament to how badly I wanted to go that I didn’t just turn around and head home! When we finally got there, she hid in the room for all of the first afternoon, and most of the second day. When she was still hiding in the room I went to the office to tell them we’d be leaving a day early. Late in the afternoon of the second day, when I noticed I was alone at the pool, I went to the room and told her “NOW is your chance. NO ONE is there, and you don’t even need to strip down totally!†She relented and enjoyed the pool while topless.

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The next day she went full-on (or should I say “full-OFF†ðŸ˜&sbquo nekkie. We broke the cardinal rule at nekkie resorts, got out my camera, and got some fun shots like this one of me

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and possibly my favorite shot of of the two of us together from that trip.

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And ( now, who could have seen this coming??!! 😂 ) she seemed like she was actually enjoying the social interaction with other guests at both at the hot-tub and later at the BYOB club ( where everyone drank and danced while dressed in their best “slut clothes†). The next morning she told me how much fun she was having. I told her it was too late and I’d already told them we were checking out. I drove to her home, dropped her off, and didn’t speak to her again for almost 4 years.

When the pandemic hit in 2020, and I was not traveling at all, I needed a local FWB so I gave her a call. She agreed to see me and rather quickly things took up right where we’d left off. But I never again was foolish enough to suggest any activity more than a visit to a nearby restaurant or a quick shopping trip to a local sex toy, or lingerie, store.

So second chances can work, sometimes even with the same partner. The key I guess is in managing expectations and recognizing and accepting the boundaries.