u/Fabulous_Walrus_7619

Honestly I have no words for how well received my story was. Shocked doesn’t cover it. I’m pretty certain I said it was really vanilla, so I’m dumbfounded how many people have expressed interest and wanted to know more. I can’t promise this will be the update you hoped for. In fact I can guarantee you this isn’t the update you want. But I figure since there is more to come, I’ll give you an update now to make my next installment easier to get out.

Again I’ll disclaim, if you want a wild sex story, give this one a miss.

For those that stuck around, this is how things went from where we left off.

My neighbor and I agreed to go sailing the Saturday after, if you recall the start of things happened on a Monday afternoon. The drive up there was cordial, but things seemed tense, almost closed off if that makes sense. We talked, don’t get me wrong, but it just felt like the walls were up. And this continued while rigging the boat, and finally pushing off away from the jetty and out into the water.

Once we were separated from ear shot of people, he looked and me and it was clear he was nervous, maybe stressed, but definitely uncomfortable. I asked him if everything was ok, and what he was clearly hesitant to open up about. It took a bit of encouragement, but a gentle gust of wind filling the sails and catching us both a bit off guard helped break his shell.

It’s hard to remember the exact dialogue, but it went something along these lines.

I assumed you wouldn’t come today.

Why wouldn’t I?

Well, I mean, after last Monday, I mean, you’ve had 5 days to think about it and regret it I guess.

- I smiled - Why would I regret it?

I get it, don’t get me wrong, caught up in the moment, it’s easy to run on impulse, but I guess I just expected you to kinda wish to forget it ever happened.

Are you saying you want to forget it?

No, not at all. It was amazing, but, I mean.

It was clear he didn’t have the words, or at least didn’t know how to articulate his thoughts and feelings. I looked at him deep in the eyes with a smile and said, I loved what happened, and don’t for a second regret it. Smiling coyly I looked briefly over my shoulder to the shore line which wasn’t that far away, and there were a few boats closer still. ‘If this helps you believe me,’ I said, and shimmied my top off, slid my shorts down, and leaned forward to stash them in the locker, once again revealing I had opted for a thong bikini. Not the same one, a light pink and white one, very cute I think. It wasn’t a deliberate effort to pose for him, but enough to let him see what I was wearing. ‘I don’t regret it, and I love that you got to see what’s underneath this,’ I smiled.

From that point, the atmosphere shifted 180°. No more tension, no more awkwardness. We flirted and enjoyed each others presence and conversation. Nothing overwhelmingly sexual or inappropriate, just fun. Lunchtime came around, so I threw my shorts on, left my shirt off, and we hopped off at the jetty, tied the boat up and grabbed some lunch and watched others sailing around. Saw a couple capsize, laughed as they righted the boat and flipped it back over the other side, and just people watched while we ate.

After lunch, I headed back out, this time I was in control with him acting as a mentor. We enjoyed some gusts and he continued to impress me with his ability to count down the wind and time it right. He says he can see it on the water, but it just looks like ripples to me. Anyhow, we got to talking and I finally asked if we could address the elephant in the room. Could we talk about what we both want, don’t want, what we should, shouldn’t make this, what ever this was. ‘A candid raw outpouring of unfiltered words,’ which honestly I was impressed with myself for saying.

I’ll spare you the back and forth, but we agreed that neither of us want a relationship with each other. The age gap is too high, my parents would freak, it was get super weird. I also said, ‘and I don’t think we should sleep together either,’ which made me nervous to say, not knowing what his response to that would be. I mean up until a week ago, I hadn’t even been in a 2 piece bathing suit in front of him, let alone a thong, let alone having him give me a wedgie in his basement, or openly inviting him pull it down, but yet a week on and I’m talking about the possibility of us having sex! He smiled and agreed, ‘as much fun and as amazing as that would be’ he said. But what we both loved what happened on Monday, and we were both eager to relive it.

So here’s what we both wanted. I wanted him to see me naked. He wanted to see me naked. I wanted him to feel comfortable looking at me, and commenting on me. But we also didn’t want it to feel like an arrangement or an expectation so to speak. He was also keen to make me comfortable, not to push me into something I would later regret, so he wanted to let me lead things. When I would let him see me, where, how, frequency….. basically all was in my control. His only request was that I was understanding that it was a huge turn on for him, and it would be unfair if I had the expectation that he hid it, ‘if [I] knew what he meant. He eyed and chinned down to his crotch with his deliberate positioning to showcase his erection. I giggled, ‘of course I don’t mind, don’t hide it or make any attempt to.’ The wind fortuitously stalled, so I took my chance to rip my shorts back off and flirtatiously threw them at him to stash in the locker.

‘Tell you what,’ I said, “I’ll sail us over there,” and indicated a point at the opposite side of the reservoir, “if I get us there with no mistakes, and no guidance from you obviously, you buy me dinner on the way home.” I smiled and the wind picked up a bit but I didn’t do anything with the sails and just let them flap a bit, ‘but if i either make a mistake, or get us there way slower than it should she taken, I’ll come over Monday again, in my smallest g-string, strip down to just that, and you’ll give me a wedgie again, but this time you break it on me, and that’s how I’ll end up naked for the first time.’ In my mind I was already going to. The idea sounded erotic, and though I didn’t detail my plan as pictured in my mind, I had already committed myself to it. I wouldn’t just stand there like last Monday, I would pose. Maybe one pose, maybe many poses. The idea of being head down, ass up, knees parted, giving him a carnal view of the g-string pulling up between my labia seemed intensely sexy. He of course readily agreed. And though I think I did a damn good job getting us across the water, he made every excuse he could as to why I lost the bet.

I handed the boat over to him to sail us back, being sure to brush my ass over his hip as we moved around on the boat. I teased him with not putting my shorts back on until we were dangerously close to the boat ramp. Pretty sure people saw but whether they would have been able to tell it was a thong bottom I’m not sure.

Fast forward to Monday, (and yes, he bought me dinner anyway, he’s a gentleman and a scholar lol). By now, my hormones have settled a bit, and I’ve all but talked myself out of it. Not going over and undressing, but the wedgie. I mean, I certainly don’t have a strange kink or fetish about it, and I’m sure he doesn’t either. It was just a way of riffing of our previous encounter, and a way to break the touch barrier again. I definitely wanted to pose and make sure he could see me from every angle, but I had relatively low interest in him giving me a wedgie by this point. So I decided I would leave it up to him and just ask. If he wanted to do it, I was all in, if he also didn’t really feel it was sexy, I would just undress. I would tell him my plan for posing, and let him decide if that was an experience he wanted or not.

So after classes Monday I showered, dressed, my smallest black g-string, a black bra, jean shorts, white tank and dark blue tee. Took a breath, and walked over to his house, straight to the backyard and straight to the basement door. Knocked, and be appeared pretty soon after.

And this is where the story goes entirely vanilla and I leave you high and dry, I’m sorry I’m advance. He was on a phone call, and checked countless times to make sure it was on mute. His work day spiraled and he couldn’t do anything. He was desperate for me to come in, even suggesting it would be amazing for me to sit naked in the corner teasing him while he worked, on a video call (which he was on while we talked, while he checked repetitively to make sure he was safe), but he knew he “wouldn’t be able to enjoy himself.”

So things didn’t pan out, and with the holiday weekend, we didn’t go sailing either. I might swing over to see him tomorrow, all I know is he worked till past 10 last Monday. And the rest of the week wasn’t much better. So I might go check in on him, but if not, we have a standing sailing date this weekend, and I’m certainly ready for some more excitement.

Jumping right into it, and up front, this isn’t the most wild story that exists here, so if you’re looking for that, maybe skip this one.

I’m 20f, attend a local state university, live out home with my parents and younger sister. My neighbor 57m across the road lost his spouse several years ago, not that you would ever know. He’s always happy, friendly, outgoing, and I can’t even recall him mourning at all. He’s just always positive and vibrant.

Anyway, he has a small sail boat that he keeps out back, and it always intrigued me. Last summer, I caught him washing it, so decided I would talk to him about sailing. The conversation was that he was maintaining/restoring/upgrading it, so not sailing much that year, but if I helped him with the project, he would give me sailing lessons next (this) summer. I was excited, so spent most of last summer hanging out with him working on the boat. Fiberglassing, polishing, repainting, running new lines, repairing water damaged parts, servicing pulleys…..etc. It looked better than new by the time we were done, and we even restored the trailer.

Fast forward to a few weeks back, we planned to get it out on the water. This is where things get fun.

He’s not some old perv, and everything leading up to this was well above board. I knew I had to wear white soled shoes, if I wanted to wear shoes, but he let me know I would likely get wet, so anything that couldn’t get wet (watch, phone etc) should stay in the car, or risk it but that was on me. He also let me know that the reservoir he sails on can be busy at times. Im free to wear what I want (again reminder about getting wet) but the possibility of guys gawking (his funny word) was pretty high. There was a moment of awkwardness as he tried to not say that I was pretty and me in a bathing suit might likely result in attention. Made sense why he was sharing it, but still funny to watch him try to sensitively tell me not to wear a bikini without saying it.

So we head out a couple weeks ago, I had opted to buy a simple one piece bathing suit, dark blue not that it matters, and some pink shorts that can get wet. We get out on the water, talk about some basics, but there is basically zero wind. We talked about what items we could, and hypothetically other sailing scenarios -not that they made sense to me at the time. As we’re floating around aimlessly, I jokingly/sarcastically brought up how busy it was….. we were 1 of 2 boats there, and the parking lot was pretty empty. We laughed and I mentioned that I specifically bought a one piece just for this. Then said of course if I had worn a 2 piece it would have been busy, that’s just how life is. It was at that point that he reaffirmed that his only concern was for my comfort, but he was ok with me wearing whatever on the boat.

So we made plans to head out this past weekend again. Come the weekend, we meet up at the park, and almost as predicted, it was really busy. We had to wait in a line of cars for the ramp, and even then the jetty area was swarmed with boats.

I decided to push the envelope and just have the fun, so was wearing blue shorts that can get wet, a white swim shirt, but under that, I had a thong bikini on. Figured I could feel things out. Maybe just leave the shorts on but lose the shirt, maybe let my neighbor in for more skin than he expected just for a laugh. So I stayed covered until we finally got out into the water, and he addressed the elephant in the corner that I was right to stay covered again, it’s busy today. At which point I let him know I had layered, and was actually in a bikini (first time saying bikini not 2 piece), meaning I could feel things out. I didn’t immediately do anything, we had some wind, did some sailing, learned some things, and got a bit wet. Once the swim shirt got wet, you could clearly see the black bikini top under it. So I pulled it off and stashed it in the small locker. It felt nice to have the sun on me.

We sailed around a bit more, headed back in for a lunch break, and maybe I drew a bit of attention, maybe? I certainly didn’t feel like I was being stared at. After eating, we went back out, he had me take control and make mistakes. Teaching by doing, and learning as I went. After a bit, I handed it back to him, I swapped positions, and I decided to be brave. “You said I could wear what I wanted, right,” he said of course, and for what it’s worth you look nice, not to be weird, something like that. I continued, “I mean, is this too much,” and I pulled the side of my bikini bottom up and out, enough to indicate it was a thong. His face was almost a loss for words.

Composing himself he said, “well like I said, it’s up to you, you can wear whatever you’re comfortable in. Admittedly I wasn’t expecting that, but” he paused, “as long as you know I won’t be able to stop myself from looking. I’ll try not to stare, but,” then we both laughed about ending on but, an appropriate word considering. “I’m ok with you looking, would be surprised if you didn’t. Look, comment if you need to, just thought it would be fun to do a 180 and go from 1 piece to thong.”

With that, I removed the shorts, stashed them in the locker being deliberate to give him a bit of a look. Beyond “very nice” that was the last that was said or mentioned for a while. He looked at me here and there, but nothing overly cringy. We sailed around for another hour or so, chatting, having fun, him teaching me every thing and anything he can think, me trying different maneuvers. And the wind inevitably calmed. We sat in silence for a while listening to the sloshing of the water on the hull, and he asked if he could as me something random and possibly inappropriate. Curious I said he could. “Aren’t they uncomfortable, I just imagine it’s a wedgie you can’t pick.” I laughed. Certainly wasn’t the inappropriate nature of a question I thought it would be. I shared that you get used to it, but it’s also not a wedgie. “It’s hard to explain, it’s in my ass, but not in my ass, you can absolutely get a wedgie in a thong.” He did not understand but accepted the answer.

The wind picked up, we moved a bit, got some speed and splashes, had some laughs, leaned out to balance the boat and started heading back towards the ramp. As the wind died down, acting entirely on impulse, I said, “tell you what, why don’t you quiz me on what you’ve taught. If I get it all right, you buy me dinner on the way home, if I lose, you give me a wedgie and see if you can tell a difference.” I blushed as my mind caught up, but he agreed, “you’re on,” before I could back out. I did myself proud, first 8 questions, perfect, 9, pretty close, 10, no clue. It was a pretty obscure question about a small rope between the boom and mast, the kicking strap.

As we neared shore, I put my shorts and shirt back on, “just for now,” I joked. Boat back on the trailer, back in the parking lot packing up and packing the boat away, I asked how he wanted to go about this. He said it was up to me, but he was buying me dinner either way as a thank you for spending time with him and sharing his hobby. I offered to do it there and then if he was comfortable, not knowing if he was concerned with me in a thong in that situation, or indeed yanking it up my butt and analyzing it so to speak. I then offered if he preferred we could delay until tomorrow (this past Monday) and I could come help wash the boat off in his yard and we could do it there, a bit more private if not a bit more of a risk for me. I mean it was secluded enough down by his shed where the boat gets parked, and no one had walked back there randomly all last summer. But you can imagine the fall out if a neighbor or my parents came back while he’s fully dressed and I’m in a thong bikini in close proximity to him. But it also seemed like a far better option for us both, and he agreed.

So the following Monday, as promised, I went over after classes. The boat honestly didn’t need much more than a rinse off. “So you still want to satisfy this curiosity?” I asked playfully. We ended up stepping into his basement, need not risk it. And he checked probably 15 times if I was truly okay with all of it, which I agreed.

We step inside the basement sliding door, close it behind us, and didn’t go much further in. I unbuttoned my shorts, unzipped, and pushed them down, stepping out. To his surprise, it wasn’t the bathing suit, just a simple white and blue striped Victoria’s Secret thong. “I hope that’s okay,” i said knowing it would be. He took a bit of a look front and back and then said, “ready?” He stepped in front of me, reached both arms around, gripping it in his fingers on either side of the V, and gave it a pull. It wasn’t a hard pull, just a gentle but firm pull, pulling until he felt resistance. Without a word, he helped me spin around, pushed me forward a bit to create some distance and took a look. “I really can’t tell a difference,” he said, “I mean I can feel a difference,” I laughed, and span back around to face him. While looking his way, I adjusted it back into its position.

I walked closer, “here,” I said. I stepped right up to him but turned side ways, “try this.”

I took his right hand in mine, led it to the back of my thong and looped his finger around both sides of the V again, same as before but only with one hand. He tried to begin pulling by I said wait, “not yet.”

Then I took his left hand, slowly led it towards the front of my thong. My heart was pounding in my chest. I found the front of my thong and looped his fingers around it completely, so that he was gripping the entire front firmly in his hand. I let go of his hand and manipulated the fabric over my crotch to narrow it and centralize it as best I could. Then I looked at him. “Try lift me up,” I said softly.”

Not sure if he had any hesitation or second thoughts, but he began to gently pull. The pressure of my thong tightening almost as if a single rope had been run between my legs and was beginning to take my weight. We heard the strain of stitching being pulled, “keep going,” i said. It wasn’t comfortable at all, and maintaining balance was a challenge. It felt like I couldn’t be lifted with any more effort at this point, like the fabric wouldn’t take my weight. “Yank it, if you can’t lift any higher.” So he counted down, “3, 2, 1” and then he gave it a yank as hard as he dared. I let out a small yelp and I felt the sharp pressure between my legs.

I assumed it would rip, but it didn’t, and I’m not sure if I wanted it to or not to be honest. This was all on impulse, nervous energy, and a long lead up of on one one time. “Well,” I paused, “take a look,” I paused again and swallowed knowing exactly what I was inviting him to do, “back and front.” I stepped sideways away from him and let him begin to circle around me. I kept my hands raised to give him an unobstructed view. He started at the back, taking my shirt and lifting it slightly so he could see the straps that were now clearly out of place on my sides, and then moved to the front. My pussy mostly uncovered, the fabric pulled very much into my labia. “Well now I clearly see you have a wedgie,” he laughed, still holding my shirt up. “I’ve got to say, thongs look far better when they’re as they should be.” I laughed.

He watched as I adjusted it, pulling it out from my pussy, pulling it back into place in my ass. “Better” i asked. “Not really,” he said jokingly.

“This really has to end,” I said, “before we do something we can’t come back from.” He breathed deep and agreed. “Take a peek,” I said, “and we’ll call it a day.”

I lifted my shirt for him just below my chest. Confused, he went to lift my shirt higher. “Not that silly,” i said flirtingly, “but if that’s what you want,” and lifted the shirt over my white bra. Still confused I said “you saw most of it,” and eyed down. With that, he got the hint, and cautiously moved his hands to the front of my thong, he began pulling the front down, looked at me for assurance, “go on,” I said. He then moved his hands to the side, and pulled it down entirely letting it drop to the floor. He looked at me and smiled, “told you I couldn’t resist.”

I let him look for what seemed like forever, and that’s all it was. I stood there with my bra showing, my thong around my ankles, and he kept his hands to himself.

We’re headed out again next weekend if the weather holds.