My Discipline – Part 7 [m/f] [Humiliation]

Timmy wasted no time trying out his newly vested authority over me. A few days after the dinner mom announced it, Timmy said “Rob and Dean are coming over. I want you to be polite and accommodating. I don’t plan on making you show off, but be anything less than pleasant and I’ll make you sorry”. I nodded. His two close buddies from school arrived a little while later. Mom had gone out for a while. I’d known Rob and Dean for years, but never really talked to them other than pleasantries about school or the weather.

They were in the living room playing video games for a while before I heard Timmy yell “hey Heather, can you come in here?”. I come into the room. I have on a grey tee shirt with an American flag colored heart on the front. I had on jeans, and my dark brown wavy hair was in a pony tail. I wasn’t sure what to expect but I put on my best fake smile and cheery disposition and said “hi guys. How’s things? Did you call my name Timmy?”. Timmy said “yeah, Rob didn’t believe I was your boss now. Will you tell him?”. I sighed. Then I said “well….its pretty much true. When our mom isn’t home Timmy is in charge. I am apparently not as responsible even though I’m older. So I guess you could say Timmy is my boss at the moment”. Rob said “how do we know she isn’t just playing along?”. Dean piped up saying “yeah, if it’s true Tim, tell her to do something”. I wished they hadn’t challenged Timmy, but I knew he’d be more than eager to demonstrate his position over me.

Timmy said “fine. Watch this guys. Ok Heather, tell us what your bra size is”. I gave Timmy a scowl, but that was all the protest I dared at the moment. Timmy knew, because mom made sure to make a big deal about It, that I recently replaced my 32A bras with 34B because the old ones got tight and this is the size the measurement lady said I was. Of course that teenaged girl milestone was rung in with a boobie spanking when we got home for not being as polite as mom thought I should have been to the lady. I said to the group of boys staring at me “I recently grew out of my old ones so I have new ones in a 34B”. I couldn’t help blushing a bit. Timmy’s friends seemed partially satisfied I told them my size, because pretty much all girls keep it a well guarded secret. Then that jerk Dean said “how can we know she isn’t making stuff up?”. Rob nodded in agreement. Timmy said “Heather, take off your bra so we can look at the label”. I gave him a look that asked ‘seriously?!’. I figured he thought I’d take my shirt off and maybe turn my back to them. Instead I reached up one sleeve and pulled out the strap, then the other. Finally I reached under my shirt behind me and unclasped my bra then pulled it out from under the front of my shirt. The boys were wide eyed like I just did close up magic like David Blane. I tossed the yellow cotton bra in Timmy’s lap. I asked “anything else?”. Timmy shook his head no and I left the room.

I went to my room and masturbated thinking about how it felt to be under my little brother’s control and sharing my bra size and giving them my undergarment. I think they might have taken turns jerking off to my bra too. I found it a few days later crammed in the bottom of my hamper. I didn’t dare inspect it for fear of what I’d find.

I guess the trust experiment worked because nobody at school mentioned any rumors or anything. I did pass Dean in the hall once and he had a weird smile, like he knew a secret about me. But that was the only weird thing that was different since the bra incident. Now that Timmy knew he could trust these boys I figured the bra incident was just the beginning, and of course, I was right.

I had on a hoodie and the low rise skinny jeans I got on sale at the mall. The boys were in the living room playing video games again before mom got home from work. I was trying to straighten things up so I wouldn’t incur mom’s wrath. I bent down to put away something on a shelf and apparently the back of my undies was showing. Dean nudged Rob, then Rob nudged Timmy. Timmy said “nice undies Heather”. I quickly pulled my hoodie down in the back and stood up. Timmy said “don’t be shy. If you want to show off your underwear go ahead.” I said “no, that’s ok. It was an accident”. Timmy said “accident or not, Rob and Dean only saw the waistband sticking up. I think you owe it to them to show them the rest don’t you?” I said “no, not really”. He said “well, I’m in charge, and I say get those jeans down and let’s see the entire back.” I knew he was being relatively restrained with his power so I just grumbled “fine” and turned my back to them. I undid my jeans and slid them down to my knees. I had on a cotton thong with horizontal rainbow colored stripes. Dean and Rob were beyond impressed with Timmy’s control of me. “Let’s see the front too. These guys don’t have sisters, so they don’t know much about girls underwear.”. I turned to face them with rosy embarrassed cheeks. Then he said “Ok. Pull them up. You can go”.

It became a bit of an afternoon routine after that. The boys would come over after school and play video games. If I stayed in my room doing homework, they left me alone. But if I stopped down for a snack I’d be asked to show them my bra or my panties I had on that day. All three boys learned the difference between thongs, bikini cut, and boy shorts as well as bralettes, sports bras, and soft cups by asking questions as I was forced to show off.

After mom let Timmy spank my bare ass with a ruler one night after dinner, he told me we were going to a little pond to swim after school the next day. He said he’d already picked out what I’d wear and to have it on under my clothes. After school I followed them to a secluded pond. When the boys took their jeans off, they had swim trunks on. When Timmy said “Heather, get ready to swim”. I slowly undressed until I was wearing just what Timmy had picked out, a thin white tank cami and a pair of thin plain white bikini cut cotton panties. I jumped in, and we had a fun time actually. But my embarrassment kicked in when it was time to get out. The white fabric had turned translucent. My pink nipples were hard and poked obviously as the wet cloth. Not to mention how my panties clung to me and my pubes were not very hidden between my legs. The boys gawked at my near nakedness. But for as embarrassing as it was, it still made me incredibly horny. I knew Timmy wouldn’t keep me clothed in front of his friends much longer.

Source: reddit.com/r/sexystories/comments/6z5ek9/my_discipline_part_7_mf_humiliation