It was Friday after school, and Rob and Dean were supposed to stay overnight. I was showing them my pink cheekies as was my routine the past several weeks. But instead of being told I can pull my jeans up, Dean asked “so Heather, if Tim can make you pull your jeans down or your shirt up, what else can he make you do?”. It was a setup. It was pretty obvious that Timmy already told Rob and Dean and they just wanted to hear me say it. I played along hoping it earned me more lenient treatment. I said “Timmy gets to decide what, if anything, I’m allowed to wear. I also have a selection of discipline butt plugs he may make me wear.” All three boys looked excited. Timmy said “Let’s start with you wearing just those underpants Heather”. I had a feeling I was in for a long evening, but with the authority given to Timmy, I had no choice. Who knows what mom would do if I disobeyed. Soon I was in nothing but my panties giving my younger brother’s friends their first look at real boobies.
The boys seemed to quickly bore of just looking at boobs, because after some whispering as a group, Timmy said “Heather, you know you are a bad girl right? And do bad girls deserve underwear?”. I could have argued I’d been ok and didn’t deserve to be stripped. I could have even stopped all of this and be grounded instead. But I went along with it because I was almost painfully aroused having my bare tits out already. I said “no. Bad girls like me do not deserve panties or any other clothes. Should I take them off?”. The guys looked at Timmy like he was a long getting ready to make a proclamation. Timmy said confidently “yes. You may not wear anything at all until noon tomorrow”. I nodded and said “yes sir” as I slowly hooked my thumbs in my panties and slid them down my thighs. I was two years older than these boys, but here I was completely naked, and the defacto entertainment for their sleepover.
When mom got home Timmy informed her of my clothing restrictions. She was actually proud of him for taking a firm hand with me. I was left alone except some staring during dinner until mom went upstairs to bed. Timmy and his friends went to the basement to keep from waking her up. I was invited down too. It was quite mortifying at first. They made me do tons of jumping jacks because they liked how my boobies flopped around. Later I had to crab walk around because it gave them a great view of my slit. Then Timmy brought down my collection of plugs. After much debate about whether they wanted to see me with the rough throats, or the really thick throats, they opted for one with a thin throat but the longest bulb that would go deep into my anus. Their ridicule peaked as I squatted precariously over the long unlubed plug trying to get it up my ass. Inch by uncomfortable inch I finally did it. My pussy was almost dripping wet but this time. I was exhausted though and the guys were getting tired. We went upstairs and Timmy had me lay tummy down over their laps across the couch. There was a movie on, but I was focused on the feeling of three erections poking at me through their jeans, and their hands on my back and bottom. They wiggled the base of my plug almost constantly. I would have been mad if it didn’t feel so good. The evening ended when I had a restrained orgasm across their laps from the anal stimulation. I convulsed slightly and I left a wet spot on Dean’s pant leg. Timmy let me go up to bed and take out the plug.
I slept good, but it ended up being quite late for me. What I had forgotten was that I told mom I’d take tha garbage out last night. With being stripped all evening, which is not a valid excuse for not doing chores, I planned to get up early and do it before the sun came up instead because I was tired. With my unexpected orgasm I slept too long and mom saw I didn’t get the trash taken out. On the bright side I finally figured out why my dad built that little ‘table’ before he left. When mom took off the table cloth, it revealed that it was a sort of pillory, that I could be locked into in a surprising variety of positions. Without even getting to eat breakfast, I got locked in with the table at my midsection and me folded I half with my hands and feet touching the floor. My wrists and ankles were fastened so my legs were spread highlighting my pube covered labia. When the boys came up for breakfast they were pleasantly surprised to see me like this. I could feel their eyes on my upturned and very personal feeling genitals. Mom said “I need to go shopping for a bit. I want you to help teach Heather a lesson about responsibility while I’m gone. Since I’m not getting through to her maybe you will come up with a better way. Use the paddle, the plugs, whatever. But let her out at noon like you originally set for her naked time.” Timmy said “Ok mom”.
She left a few minutes later and I knew I had just over two hours alone with the boys locked to what dad would later refer to as ‘ the stocks’. Timmy got the ruler and showed his friends his skills at swatting my ass and thighs. They were delighted with my yelps and winces and the red welted stripes the ruler left on my pale skin. Timmy let his friends take a turn making the ruler crack across my tender inner thighs. Then Timmy showed them how they could ‘pinken me anywhere’. My breasts weren’t super accessible in my folded over position, but that didn’t stop him from smacking my side boobs to prove his point. Soon all three boys were quite comfortable using the ruler to discipline me. With comfort came a more adventurous spirit. Timmy showed them how my dad would spank just my anus sometimes. I howled as they hit my little pucker over and over. Then they moved on to my labia. It was the perfect target with me in this position and I felt the ruler smash against my genitals. It gave my butt hole a break, but it would be a tough call to make about whether pussy spanks were any better. They used the ruler on me for probably an hour off and on. It was never any tougher than I could take or any worse than I’d gotten from dad, so I appreciated that at least.
They got bored, as teenaged boys do, as my skin became fully striped with pink welts. Rob said “what about the plugs?” Timmy said “Good idea”. Dean opened the drawer and pulled out the short stubby thick one saying “Let’s use this up her ass”. It was my least favorite plug because the uncomfortable stretching sensation never subsided like it typically did with the others. Timmy allowed me to spit on it, which was a kind gesture. Then between the three of them, two of them grabbed my butt cheeks and pulled them apart and the other lined the plug up with my spanked asshole. I felt it pushing and my butt hole had no choice but to stretch open. I felt painful streching as the thick part of the bulb went in. I was groaning and grunting until the throat finally locked into place with my anus trying to close around it. It felt thick inside me even though it was the thinnest part of this fat plug. They enjoyed wiggling the base hearing the noises I made. Then Dean said “what if…..we put this one in her…..other hole”. He was holding up the longest thinest plug that had been up my bottom last night. Timmy thought for a second and finally said “well, mom left me in charge, and I think it’s a good idea. Don’t you Heather?” It was my chance to put a stop to this. I was a virgin, it would probably hurt. It wasn’t right. There were a million reasons I could have for making them stop. But instead I said “You are in charge Timmy. It’s your call. I know I misbehave all the time and deserve whatever I get”.
In hindsight I’m glad I didn’t stop them. The next half hour was a defining moment of my life. All three boys had a hand on the base of the plug as they put the tip against my pussy. I had butterflies in my tummy. I’d masturbated a lot, but I’d never been brave enough to put anything inside me like a hairbrush handle or whatever. They pushed and I felt my hymen tear. My brother and his two friends just popped my cherry. It hurt like nothing I’d felt before. In no time, the plug was fully inserted into my vagina which was as wet as it’s ever been. The boys took turns ‘fucking’ me with the plug. I orgasmed over and over as they did. They seemed to love my squeals that were a mix of pain and pleasure. In my orgasmic haze I had an epiphany. My body didn’t recognize pain and pleasure as distinct sensations. They were variations of the same that fed and enhanced each other. I realized that the shame and embarrassment of being used by these younger boys was just another mental facet of this complicated pain and pleasure jewel I had inside me. At noon I was a sweaty, exhausted, welted pink mess, with my own juices and vim dripping down my thighs. The boys had fucked me with the plug nearly continuously for 30 minutes. I had more orgasms than I could count, or perhaps it was just one extended orgasm they didn’t allow to stop.
In any case, they let me out right at noon, and I wasn’t bothered by anyone the rest of the day. I took a long nap and spent time in my room quietly reflecting. I would bet most girls would hate knowing that the time their cherry got popped was so rough and unromantic. I actually liked it and was glad it happened exactly as it did. Plus, it gave me a special connection to my brother and to Dean and Rob, who I’d known for years. I felt like a lucky girl for being able to be treated the way needed deep down instead of the way that most girls my age were raised because that wouldn’t have been right for me.
Source: reddit.com/r/sexystories/comments/6zna5n/my_discipline_part_8_mmmf_spanking_humiliation
https://www.reddit.com/r/sexystories/comments/6z5ek9/my_discipline_part_7_mf_humiliation