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.

[TeenFan]

The clothes swapping videos on Youtube used to be a big thing. Often it was a brother/sister doing the clothes swap, with a parent shooting
the video. These swaps could have gotten more interesting if the kids were home alone.

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.

[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.