Moments between me and my older sister growing up

[jllash]

I'm a guy and I have a sister that's 4 years older than me that's fairly athletic. Growing up we've had a few embarrassing moments that I'll share below.

The first incident was when I was about 7 or 8, one warm summer day my parents were gone, she was babysitting me, and so I was hanging out in her room being bored and annoying when she suggested playing dressup. Not really being into girly things I wasn't interested at first, but nobody was around and I was bored so I agreed. With that, she directed me to her closet where we sifted through her clothes hanging on hangers before deciding on an oversized dress.
I pulled it on over my clothes and looked in the mirror with her and it looked silly and we giggled about it. She told me I had to take off my shirt and shorts for it to look right. So I pulled them off while keeping the dress on, and it looked better. She tapped her finger to her chin saying "hmm... it still doesn't look right, here take it off and let me see the dress."
So I pull off the dress and hand it to her, and she examines it. I'm standing there in just my tighty whiteys and white socks and she goes "Ahh I know!", and she pulled out the top drawer of her dresser. In there are all of her bra and panties and socks, and she pulled out a bright pink bra, pink panties, and pink socks, and said I had to put these on.
Now I didn't sign up for this, and I told her I didn't want to and tried to run out of the room but she grabbed my arm before I could escape. She said something like, "Where are you going? Planning on running around the house in your underwear?" while I tried to pull free. But she was bigger and stronger than me and I couldn't escape. Even if I got away I knew I couldn't run away from her forever, but I didn't want to wear girl's underwear, so I wasn't sure what to do.
That's when she hit me with "If that's what you want, I can tell mom and dad that you were being difficult and misbehaving".
Not wanting to get in trouble and knowing I couldn't outrun her I reluctantly agreed to do it. I swapped out my socks, she helped me put on the bra which was oversized for me. Then it was time to remove my tighty whiteys, I hooked my fingers into the waistband and hesistated. I looked up at her and she gave me a nod. Embarrassed, I pulled them off and pulled on her panties as quick as possible, avoiding eye contact.
"Good, was that so hard? Doesn't it feel better now?" she said. The panties material did feel better than the tighty whiteys but I wasn't going to let her have that victory so I said "It feels weird". Next she helped me get the dress on and pulled me in front of her mirror saying "It looked so much better now, you look just like a girl."
After a moment she said "and now for the final touches", and she pulled out her makeup kit and a wig, and had me sit there while she did makeup on my face and put the wig on me before standing me before her mirror again. "Perfect, you're like my little sister now".
I didn't know how to feel about this except embarrassed. Next it was her turn. We went to her closest again and picked out a dress for her. Then to my surprise she pulled off her shirt and jeans in front of me, standing in just bra and panties and put on the dress, and I helped her zip it up. From there we accessorized with random cheap bracelets and necklaces she had and took turns walking down an imaginary catwalk in her room with different clothes. Eventually my mom returned home, my sister insisted we go downstairs together as we were dressed. When my mom saw me she found it hysterical and said she had to take a photo. I said no way and started to run back upstairs, but she insisted I remain there until she got her photo, even using her stern voice to say I'd be in big trouble if I didn't. When she got her camera I begged her not to but she took a photo anyway, and it was humiliating. As soon as I could, I rushed back upstairs and got my own clothes back on and washed off the makeup.

The next incident I was 10. I was sitting in our living room, it faced a hallway and view of the staircase to the 2nd floor, and my sister ran out from the laundry room topless in just panties, using her hands to cover her breasts. I don't think she saw me and in just a few seconds she was quickly gone upstairs before I even realized what I saw. So I decided to quietly crawl up the stairs, not making a sound. When I reached nearly the top of the stairs, I peeked over the steps to see into the upstairs bathroom. In there she was brushing her hair, still topless, and I got a nice view of her breasts from the side. A moment later she glanced in my direction and she saw me and immediately covered her breasts with her hands again and turned towards me looking stunned.
She said "What are you doing?"
Having been spotted, I stood up and started to walk up the remaining steps "Going to my room", acting like I had just been walking to my room the whole time, but having never seen boobs before, I asked her "Can I see your boobs?"
"No you weirdo!" was her reply and she closed the bathroom door.

When I was 14, I had forgotten to bring a towel after a shower and all the other towels we typically kept in the cupboard were in the laundry room, so I was dripping wet naked not knowing what to do. My sister was the only one home so I yelled out to her to bring me a towel. A minute later she knocked on the bathroom and said "I got your towel", and I said "Can you leave it outside the door". She said "Just open the door." but I insisted "just leave it outside the door, I'll grab it after you leave". She said "Whatever" and walked away. I waited half a minute and peeked out the door, grabbed the towel and dried off. Admittedly nothing embarrassing happened, but I've had fantasies about how this could have gone differently.
Like if she refused to leave the towel until I opened the door. Or if she took the towel with her and left me with nothing. Or if she waited outside the door, knowing I would have to streak naked past her to get a towel. Or if she pretended to not be home or hear me, but waited for me in the laundry room. Or if I had just opened the door.

When I was 19, I had been fantasizing about giving myself an embarrassing moment and I decided to put a plan into action. I had taken a shower and wrapped a towel around myself, and went to the laundry room to get a fresh change of clothes from the dryer. I grabbed some boxers, removed my towel, so I was naked facing the doorway. I timed it just right so that I was about to step into my underwear when my sister walked in. She was getting ready for work and the laundry room had her shoes and a door to outside that she typically used. She was bent over untying her shoes to get them on and was so focused on them that she didn't even notice I was naked, just 6ft away from her. I held my boxers in one hand, holding them in front of my penis but to the side, like I was trying to cover myself but not succeeding at it.
I said "Can you get out I'm changing". Without looking up she said "I have to get ready for work, I'm about to leave".
I said a bit more forcibly and a bit whiny "Come on I'm naked, would you get out." With that she looked up at me and saw everything, her eyes widened, and her jaw dropped. She remained frozen like that for 2 seconds. Then without looking away she straightened up and faced me, she had managed to put on one shoe and was untying the other while while she continued to stare at my penis, her eyes still wide, jaw still dropped.
After 4 seconds of this I pleaded "Please". That seemed to make her compose herself, she blinked and looked away before immediately looking back at me, and a small smile spread on her face as she continued to look me over for 4 more seconds before finally with a smirk on her face saying "okay" and turning around and walked out into the hallway carrying her other shoe.
I quickly got dressed and heard my mom say to her from another room "What are you still doing here? You'll be late for work!" and I couldn't make out what my sister responded with.
I went to my room, she went to work, and again, we never spoke of it. All in all it felt like she looked at me for 10 seconds, I was somewhere between flaccid and semi-erect. Not at my best, but not at my worst. It was definitely embarrassing as I experienced it.

When I was 20, she had got in the habit of running through the house naked after work to take a shower because her work made her clothes smell bad. She only did this when nobody is around, but one day she didn't realize I was home. I saw her from across the house, about 20-30ft away, she was running down the hallway from behind. The light near her wasn't on so it was hard to see but she turned around and saw me, instead of covering she gave me a full frontal view, a wave with the fingertips of her hand, then ran into the bathroom, all in the span of a few seconds. I'm still not sure if the wave was a hello or if she was testing if I could see her, but I pretended like I didn't see her the entire time.
Again, we never spoke of it, and there hasn't been any incident since. Since then she has got her own place, got married and had a child, so we're not likely to ever have another moment like these again.

[Skylar21]

Interesting times back then, eh? Do you know if other people saw the photo your mom took of you in your sister's dress? Moms seem to like embarrassing their sons.

How long of a look did you have of your sister's boobs?

I too have set up embarrassing situations for myself where family members get to see me naked or otherwise compromised. Interesting trying to bring fantasies to life. Makes life a thrill! Were there other times when you set yourself up for embarrassment?

[jllash]

If your sister put you in a dress when you were around eleven years old, that would have been the perfect time for it. Much more
embarasssing than when eight years old.

Yeah it would have been more embarrassing if that happened when I was 11, but by that age there was no way I'd ever play dressup.

Interesting times back then, eh? Do you know if other people saw the photo your mom took of you in your sister's dress? Moms seem to like embarrassing their sons.

How long of a look did you have of your sister's boobs?

I too have set up embarrassing situations for myself where family members get to see me naked or otherwise compromised. Interesting trying to bring fantasies to life. Makes life a thrill! Were there other times when you set yourself up for embarrassment?

She put it in an old photo album and once in awhile she'd flip through it when our relatives visited, I don't recall much reaction other than some light chuckling before they moved on. I do recall one of our previous neighbors, a girl that used to live next door before we moved away that was my sister's age was visiting, and my sister showed her the photo. Once I realized that my sister had the photo album out I bolted out of the room and hid in my bedroom until it was time for them to leave so I didn't see her reaction. When they were leaving my mom told me to come out and say goodbye, so I reluctantly walked out and when I made eye contact with the neighbor girl she bursted out into giggling which was embarrassing.

I only saw my sister's boobs for about 3 seconds, she noticed me surprisingly quickly, and since I saw her from the side I couldn't make out her nipples. I was about 10ft away too.

Sorry to say I didn't have any other times where I set myself up for embarrassment. When I lived in a coed dorm floor there was a single shared bathroom for each gender, and female cleaning staff, so there were lots of opportunity for embarrassing moments. It would be simple to wear a towel after a shower and let it drop on the way back to my dorm, or step out naked and dry off at the same time the female staff cleaned the bathroom, but I could never bring myself to do anything like that. But I have heard of other guys doing it, or girls seeing guys stepping out of the shower when another guy enters the bathroom and opens the door.

I did have an unexpected embarrassing moment when I rented a house with some friends, we were a few weeks away from moving out and the landlord had scheduled viewings for new tenants that I forgot about. I tend to stay up late and my friends had early classes, and when I woke up there was a young 20s blonde girl standing in my bedroom. I was under the blanket wearing just boxers and she was standing there just grinning looking at me and around the room. Still half asleep I asked "who are you?" confused and groggy, she says "I'm thinking of renting this place". That jolted me awake and I remembered the viewings today, I was thinking shit I need to get out, so I quickly climbed out of bed and pulled on a pair of pants and a shirt while apologizing to her, saying sorry I forgot about the viewings, that I overslept, that I'll get out of her way, all while she stood with a grin on her face watching me. I went downstairs and ran into a few of her friends that were also planning on moving in, and they later approached me to ask me a few questions about the place, which I happily answered.

Writing about my experience with my sister has made me want to broach the topic with her, to see where we stand with each other regarding it, but also to maybe try to instigate some kind of nudity between us again, but I don't know how I would do it, I don't see her outside of family gatherings, rarely in private, and it feels awkward to hit her up out of the blue. Even bringing up this topic is difficult.
Fantasizing about it, I imagine we're hanging out at my place, and I ask her how she likes having nudist neighbors (since she laughingly mentioned that she accidentally discovered that when she first moved in and introduced herself) and ask her if she still runs around the house naked and laugh about how she used to do that after work. Then bring up how I saw her one time, and she could bring up that time she saw me naked too. Maybe she interrogates me and ask what I was doing showing off and I explain that I was experimenting with nudism and found it too embarrassing to commit to outright. Or if she doesn't bring it up I simply say that I've always been interested in nudism but always felt too embarrassed. So she teases me for being shy and encourages me to do it with her right now and we both strip off and see each other. Or she encourages just me to do it and I strip off in front of her.
Or alternatively, we're hanging out, she's been practicing mario kart and is convinced that she's better than me at it now and challenges me. I haven't played it in awhile but I've always won so I raise the stakes and say if she's so confident then lets bet on it. I'd admit it would feel bad taking each other's money so I suggest betting our dignity, strip mario kart, until one of us is naked. Not just down to undies, butt ass naked.
If she calls me a weirdo for suggesting that I can claim that she must not be confident after all and try to goad her into it. Or maybe that will make her try to flip it on me, suggesting that only I play by strip rules if I feel so confident then. I'd argue that then the rules aren't fair, maybe we'd compromise on a handicap, if I lose once I strip naked, if she loses she only removes one article of clothing, and maybe I'd agree to it just for fun.
Then commence much teasing and taunting toward each other about how we will have to strip as each round goes by. I can see it being thrilling no matter who wins at that point.

[Skylar21]

If only it was as easy to pull off a self-humiliation fantasy as it is to think them up! Your Mario Cart scenario with your sister has merit. Easy enough to arrange the terms so you don't win.

[Lola]

Really nice memories. Thank you for sharing. It would be interesting to hear the same memories from your sister point of view. I'm curious. I think she likes to be embarrassed just like you.

[jllash]

If only it was as easy to pull off a self-humiliation fantasy as it is to think them up! Your Mario Cart scenario with your sister has merit. Easy enough to arrange the terms so you don't win.

Thanks, that's true, it is hard to fulfill them. I did write a fantasy of losing to her in strip mario viewtopic.php?t=5024
and her encouraging nudism
viewtopic.php?t=5073

Really nice memories. Thank you for sharing. It would be interesting to hear the same memories from your sister point of view. I'm curious. I think she likes to be embarrassed just like you.

Thanks, I agree it would be interesting to hear it from her point of view, but I don't think she's into being embarrassed like me. She's more of a free-spirit I'd say, a little into spiritual stuff but it isn't her entire personality, so I think she's a bit more open about nudity, but not entirely. While I can only think of a handful of times where I was in the same room as her when she was in her underwear, she was mostly indifferent to me seeing her in it, on at least 2 occasions stripping down to panties/bra when I was right there talking to her. Anything below the underwear she's always been very modest about though.

Even when she was doing her naked run after work, she didn't go out of her way to be seen by anyone, and it really did make sense for her to do it naked given the layout of our house and the really terrible smell she'd be covered in after work - if she and her clothes weren't immediately washed the rest of the house would have smelled.
It's not like she was always entirely naked as well, one time I stepped out of my room to go downstairs, and as soon as I stepped out she was right there coming down the hallway towards me to get to her room. I tried to walk past her but she blocked my way. I tilted my head and gave her a questioning look like "huh?", she didn't say anything and instead just gestured with her finger to tell me to turn around. I looked her over and realized she was holding a towel in front of her, so I figured she must not have been wearing anything else, and not wanting to make it more awkward or be a creep, I turned around and walked back into my room.

She knew her butt would be exposed if I walked past her and looked back, so she blocked my path, surely if she was into being embarrassed she would have just walked past me in that case, right? Or set herself up to be seen in other ways. I feel like she had countless opportunities for more embarrassing moments but they never happened, which makes me believe she isn't into being embarrassed. But maybe she was just testing the waters and felt the same cold feet I felt about doing anything like that. Maybe she fantasized about me yanking her towel off? Funny to think about, I have a hard time believing it.

I think a lot could be gleaned if I knew why she turned her body towards me and waved during her naked run the one time I saw her. I've come up with these reasons as possible explanations (and maybe it's a mix of them).
(1) it was a "happy-go-lucky" spur of the moment kind of thing, where she was just having some fun. she happened to notice me and i was a fair distance, there wasn't much light, and she was right at the corner so she could quickly disappear, so it was a fun safe thing to do. Thrill seeking or mild exhibitionism.
(2) she really couldn't tell if i could see her in the dark, she wanted to know if she was seen, so she waved to see if there was a reaction.
(3) she remembered that time she saw me naked, so in her own way she wanted to pay me back or equal the playing field by letting me see her.

But maybe there is a (4) she liked being embarrassed and decided to let herself be seen naked.

[Lola]

But maybe there is a (5) reason.

When she saw you naked she took some seconds and smiled to you. I likes to see boys embarrassed naked and I'm quite sure that she likes it too. That day she thought she had been lucky. She had a look, smiled and went away. She would have apologized and run away as soon as her eyes fell on your penis if she wouldn't like to see you embarrassed asking her to go.

Since she likes it she wants it to happen again. With her fingers wave she wanted to remember you that moment and suggest you to make it happen again. You've seen her and now is her turn to see you. I think she did that wave without thinking. It was a symbol: Look! it's ok to be naked around the house, you can go naked.

I'm not saying that she liked to be seen in that moment but since it all happened in a couple of seconds and accidentally, she took the occasion to send you a message out of instinct.

You tell me that she's a free spirit. It makes sense to me but it's impossible to tell the truth...

By the way if i were her i would have tried to make it happen again, tired to see you naked.

I don't know if i've been clear but it makes sense in my head

[jllash]

But maybe there is a (5) reason.

When she saw you naked she took some seconds and smiled to you. I likes to see boys embarrassed naked and I'm quite sure that she likes it too. That day she thought she had been lucky. She had a look, smiled and went away. She would have apologized and run away as soon as her eyes fell on your penis if she wouldn't like to see you embarrassed asking her to go.

Since she likes it she wants it to happen again. With her fingers wave she wanted to remember you that moment and suggest you to make it happen again. You've seen her and now is her turn to see you. I think she did that wave without thinking. It was a symbol: Look! it's ok to be naked around the house, you can go naked.

I'm not saying that she liked to be seen in that moment but since it all happened in a couple of seconds and accidentally, she took the occasion to send you a message out of instinct.

You tell me that she's a free spirit. It makes sense to me but it's impossible to tell the truth...

By the way if i were her i would have tried to make it happen again, tired to see you naked.

I don't know if i've been clear but it makes sense in my head

That makes sense and it's an interesting point, I hadn't considered that. My thinking was always she was on "I'm late and have to get ready for work" autopilot, and seeing me naked suddenly short-circuited her brain, so she kept getting ready while she was processing what she was seeing. Although admittedly she remained looking a few seconds longer after she realized what she was seeing and smiled, so maybe you're right she did enjoy seeing me in that moment and wanted it to happen again. Maybe letting me see her was a safe way to indicate that, since obviously it would be too awkward for her to outright say it to me. The laundry room wasn't exactly a private room in the house like a washroom though, there's no lock, the door was open, it's uncommon to be changing there or to have/expect privacy, so I imagined she also felt justified being in there and being asked to leave was so removed from her mind it took a few seconds to process.

Regardless, our parents were almost always home so it was rare to ever have that kind of opportunity, even if I wanted it to happen again it wasn't an easy thing to do.

[Lola]

If she's a free spirt and a bit more open about nudity all the five reasons seem to be reasonable!

Wouldn't it be hot if she truly liked to see you naked? It's hard to tell. We need more clues.
Are you sure there isn't any more in your memory? You may have removed from your mind some really embarrassing and traumatizing moment. Try to relax and think to the past. It's hard but sometimes it happens to remember more.

Maybe your sister used to say or do something to induce you to be seen naked. Some joke, some prank, a verbal tease... I don't know. There can be more clues in your mind to understand your sister's behavior. It's up to you!

[jllash]

If she's a free spirt and a bit more open about nudity all the five reasons seem to be reasonable!

Wouldn't it be hot if she truly liked to see you naked? It's hard to tell. We need more clues.
Are you sure there isn't any more in your memory? You may have removed from your mind some really embarrassing and traumatizing moment. Try to relax and think to the past. It's hard but sometimes it happens to remember more.

Maybe your sister used to say or do something to induce you to be seen naked. Some joke, some prank, a verbal tease... I don't know. There can be more clues in your mind to understand your sister's behavior. It's up to you!

I wouldn't go as far and say she's entirely a free-spirit, we spent more than 16+ish years living together and there was only 2 times I saw her in anything less than underwear and each time it was a brief moment that she immediately ended, so she definitely had a sense of modesty. It's just there's kind of a sense of free-spirit to her. Like not full hippy, not fully spiritual, not fully country, not fully city, somewhere inbetween. She's spiritual in the sense that she claimed to sometimes see ghosts, has some belief in those sorts of crystals/stones but not crazy into it, she's hired an animal whisperer once every few years for her pets, but it's not her entire personality, she's a hard worker, not really religious, maybe wiccan if at all, enjoys nature, always doing stuff outside and trying new things.

and yeah it would be hot, and I do think she would likely find it amusing or encouraging if I was naked in a non-sexual context in a way that made sense. But if I suddenly stripped naked in front of her without any reason I think she would find that creepy and weird (and likewise I'd feel uncomfortable doing that). I think that's why the strip mario kart and encouraging nudism fantasies make the most sense.

Trying to remember everything, I'll put down everything I can think of and some things I've omitted.
- when I was 2-3 years old there's a home video of me naked saying "I'm nakey" that she teased me about a few times growing up but I haven't seen this home video since I was about 12.
- when I was 7 for some reason I wouldn't get changed in my room, instead I'd carry my change of clothes and run to another room in the house in my tighty-whiteys to change in. one time she saw me and chased me down, so I hid under the dining room table and she followed me under and basically trapped me there between the chairs while she interrogated me, asking me why I kept doing it. I found that scary and embarrassing and admitted I didn't know why, and that I guessed it was just for fun. I stopped doing it after that.
- when I was around 10 or 11 she was in the doctor's room with me and my mom during a medical checkup when I had to get naked, this was deeply humiliating to me but she was instructed to face the wall, which she thankfully actually did and didn't see me.
- sometime when I was between 9-12 my sister got into something like hypnotism and wanted to try it on me, so we went in my room and she instructed me to relax in bed and close my eyes while she sat on my bed's headboard beam above me and tried to put me into a trance. I don't really remember much except at one point she blew on my ear, and another point she was telling me I was on a beach and picking up seashells and asked me if I heard seagulls. I tried to visualize it and play along, and I think I may have got a boner, but I was fully clothed the entire time and didn't understand it or remember much, I think I told her it felt weird and that it didn't do anything, and we went our separate ways afterwards.
- when I was around 12 I walked into the living room, standing next to the couch watching tv when my dad pantsed my shorts down, exposing my tighty whiteys to my mom and sister sitting on the couch. I found that embarrassing and immediately pulled them up and jumped on my dad to attack him (to not much effect), but I wasn't pantsed by anyone since.

When I was 14, one time I was hanging out in her room, I can't remember why, it was unusual because by this point we mostly kept to ourselves. At one point she said she had to get changed and I just said "okay" but I stayed in the room. She shrugged her shoulders and stripped down to her underwear/bra and got changed while I sat on her bed and watched her. I think I left the room right after that.

By the time I was 15 she had went to college, and only stayed with us for a few summers, before moving back in for a final few years before moving out and by that time I was off to college too, so we didn't talk or see each other very much, only a few months during off semesters, or holidays or odd weekend.

I do remember, one year's christmas morning we had, months after I had my embarrassing moment, she burst into my room (which she never did, and not in previous christmas mornings either, nor since) and urged me to wake up, ripping the blanket entirely off my bed, revealing my entire body. I wore pajamas to bed so nothing was seen, and I told her to get out and let me sleep a bit more, which she eventually relented and left. I kind of wish she had made a habit of this, I would have made a habit of sleeping naked.

We did go on a trip to finland when I was about 23, it was a big family vacation, extended relatives and everything, and I ended up having to share a hotel room with my sister and another (male) relative. At one point everyone wanted to end the day by going to a pool but I just wanted to stay back at the hotel to workout and relax and watch a movie, and admittedly I knew they required everyone to strip naked when they showered before going into the pool, I was ashamed of my body and I didn't want my relatives or dad to see my dick, nor did I want to see theirs.
So I stayed back, watched a movie, worked out, showered, but when I was showering I heard the door open and someone come in. Then they made no noise. Not knowing if it was my sister or one of my relatives, I decided to play it safe and just put on the clean clothes I had brought in and walk out. As soon as I stepped out, I saw my sister sitting on the edge of the bed immediately turn her head to look at me (I suspect she may have been expecting to see something right there).
We talked a bit about the pool, she made some remark about how good one of our aunts looked for her age, and plans for the next day. I settled into bed, looking at my phone, when suddenly she got undressed right there, down to her underwear and bra to change into pajamas. As soon as I saw her in her underwear I laughed and said while smiling something like "nice going, getting changed right out in the open." She replied also smiling with "it's just underwear, no big deal", and I agreed with something like "yeah it's no big deal, just thought it was funny that I looked up and *boom* you're in your underwear", and she laughed a bit, and we left it at that.
In hindsight it was a missed opportunity for my own embarrassing moment, I could have walked out naked with the explanation I didn't think anyone was back yet, or just wrapped a towel around myself and gotten changed right there and had the towel fall. But having just got off in the shower I was completely flaccid and just not into the idea of embarrassing myself at the moment, especially not in front of the male relative (who I thought it could have been). We didn't really have any other moment without that relative around, and I didn't see her changing again during our stay.
I kind of wished she had teased me about not going because I was shy, and when I claimed I wasn't, she would call a bluff on my bravado by having me strip, but that never happened and seems more in the realm of fantasy.
I think it's possible she hoped or expected to see me naked, since she was in perfect viewing position, she looked at me immediately so quickly as if expecting to see something, she was so quiet while I was in the washroom too, it's almost like she was trying to be quiet hoping I would assume I had the room to myself.
And maybe it's possible she stripped down to undies as if to tell me it's okay to get naked, or maybe that was just her being herself.

In terms of her saying or doing something to induce me to be seen naked, it's hard to think of anything. The closest thing to teasing that comes to mind is once I think I was probably 17 or 18, I was walking to our laundry room in just a towel after a shower, which was rare, normally I took clean clothes in with me but for some reason I didn't that day, and I passed her in the hallway.
She said something like "nice manboobs" (yeah I'd put on some weight).
I shot back and said "thanks, are you jealous?".
and she responded with "yeah, I am actually."
That was the only one verbal teasing I recall.

There were a few times when she went out of her way to tell me directly when a friend was coming over, or one of her younger students was coming over, almost as if to warn me to not be naked when they'll be around. I always said "okay?" as if I didn't know why she was telling me that. This makes me suspect she thinks it was intentional and was trying to discourage me from doing something during those times. It felt out of place since it's not like I was constantly naked, none of her friends or students ever saw me undressed, and she had only seen me naked as an adult that one time. Her telling me about her friend/students coming over certainly wasn't encouraging as well, that would be insane.

With that said, it's hard to imagine a phrase she could have said that would have induced me to want to be seen naked.

Maybe if she said something to indicate we'd have the place to ourselves, but again it was rare that our parents would be out, but I did often overhear her discussing her work schedule with our parents. Even then though, it's not like we walked into each other's rooms all the time, we mostly stayed in our own, so being naked was pointless unless I walked into her room and that would be too creepy.
That I managed to pull it off the first time when my parents were home was a huge risk on my part and not a risk I wanted to repeat.
So to even repeat the situation, I would have had to time it when nobody else was around and be seen when she was either coming home from work or getting ready to leave.

Regardless, I feel like I would have keyed in if she was hinting at getting me naked again. I would have remembered if she talked about nudity, or nudism, or being free in nature, or anything like that, but that wasn't something she ever brought up (besides her neighbors one time).