This occurred when I was just starting college and I still cannot believe it happened to this day.
First I need to set the scene. I'm 20, I'm still living at home, and I've been wearing thongs for a couple years now (hiding it from my parents). I was unsure of my sexuality back then, I know I'm bi now, but I had always been interested in trying thongs.
Even before that thought, started my love of performing arts. I'd been doing theatre for 5 years at this point, and still do today 10 years later. I knew I really needed to improve my singing, so I started taking vocal coaching. My teacher will remain anonymous, but we can call her Coach N. Coach N is a Colombian in her late fifties, very kindly and sweet, and is the owner of one of the best bubble butts I've seen. Her at 25-35 must have been stunning, as even then she was hot (bad hips and all).
I had been taking lessons with Coach N for about a year at this point and we had a great rapport. We were always ball busting each other back and forth. It was not uncommon for us to really goof around while we worked. While I was hiding my thong wearing from my parents I'd always change into them while I was out. the timing worked out that I almost never wore one while with Natalia, I took a class with here, then commuted to college or out on the town on weekends. I'd always change after leaving her studio.
Today though, I had stayed over with my boyfriend at the time the night before. We both got tanked and banged all night. For this lesson I had on a long sleeve t-shirt, bootcut jeans, and a new thong I just got. Let me tell you, I did not buy the right size underwear. I was super paranoid getting caught by anyone I knew at the time. In my rush to buy it and leave I didn't even notice the size discrepancy, but I sure noticed it that morning.
We started with vocal warmups and I had already developed a seriously bad wedgie. I was trying to figure out how to pick it without her noticing. Then a devious idea struck me. I was going to visibly do it and show her my thong.
We got toward the end of our lesson, and I was struggling get the nerve up to follow through. I was worried she wouldn't notice if she wasn't paying attention. I have no idea where I got the balls to do this, but i decided right there I needed to tell her what I was doing. I can remember the whole conversation clear as day.
Me: (finishes singing the last song we were working on) Oh my God
N: What?
Me: Oh sorry, its nothing...its just...I know this is super rude...I'm sorry...I just have the worst wedgie right now and I have to pick it
N: *starts cackling* Just how bad could it be?
Me: Real bad
N: But why?
Me: Its the type of underwear I have on
N: What is it tighty whities?
Me: Its easier to just show you *I pull down a side of my jeans and show her a strap* its a thong
N: *dying laughing at this point* Oh my god are you kidding me? You like those?
Me: Yeah I wear them all the time
N: I hate them, my late husband had me wear them to the beach all the time. It felt like I was getting anal sex. How can you stand those wedgies?
Me: I just like how they feel, besides, whats wrong with anal? My boyfriend loves these.
N: Damn, hes a lucky man. His boyfriend is already so comfortable getting things shoved up his butt.
We are both dying laughing at this point. I'm still faced away from her, my pants sagging LOW at this point.
N: Can I see your butt?
I don't hesitate a moment to drop my pants entirely. She immediately starts grabbing a cheek in each hand as I start moaning.
N: Naughty boy
And with that she starts spanking me, we went on to hook up for the rest of the time I saw her.
