As with everything my mother found I disliked, it got incorporated into my discipline. For instance, I complained that I didn’t want leftover meatloaf for dinner. I spent that mealtime in the stocks with a large carrot up my ass. After they finished dinner she made me eat the carrot before sending me to bed. My dad didn’t care for that sort of thing so he stuck to just my flogging and spankings. But Timmy, Rob, and Dean also got a kick out of making me taste my own was. If we were playing video games, and I lost, I’d get a finger up my bottom then it would go right in my mouth. It was disgusting, but I knew I deserved it. That didn’t make me gag any less though.
The most impactful moment I had was one night when the boys were having a sleepover. Timmy and Rob were in the middle of some major video game tournament. Dean had been knocked out of the competition so he sat back on the couch with me. I had been wearing just a thong, but he said “take those off Heather. I like you fully naked best.” I said “but I’m on my period. I have a tampon in”. He said “I don’t mind”. I slid my thong off and spread my legs so he could see the string and know I wasn’t lying. Timmy and Rob were oblivious to us, caught up in their game. Dean grabbed the long thin butt plug that usually got used in my pussy on nights like this. Then he guided me onto his lap with me laying on my back across him. He propped my head under a pillow and played with my breasts with his left hand.
After tracing his fingers through my pubes and touching my string he took his right hand and began gently pushing the plug in my ass. Instead of pushing it in until it locked into place he began to slide it in and out like they normally did to my vagina. His left hand rubbed my tummy and went back to squeezing my breasts in a good way. Our eyes locked and varied speed and angle and depth of the plug as it moved in and out of my ass. It felt different than how it felt in my pussy, but it felt good. As Timmy and Rob played, Dean worked my ass until he perfected the technique and was actually getting me close to cumming.
He fucked my bottom without stimulating my pussy or clit at all. I humped the air with my crotch fruitlessly until I was on the edge. Then I saw him grin before I felt the full length of the plug suddenly fill my bottom. It began an incredible orgasm that originated not from my genitals, but from in my ass. It was a deeper and more powerful orgasm I felt all through my insides. My breath caught in my lungs As I shuddered with pleasure. As the initial wave of the orgasm started to decay, he suddenly pulled the plug fully out. The unexpected void in me and the stretch of my asshole inexplicably began a second peak of this new kind of orgasm.
I started to moan as the second wave came over me, only to have the plug that was just fucking my ass pushed into my mouth. I stared into Dean’s eyes as I instinctively sucked at the plug while I continued to orgasm. My earthy dirty taste mixing with my endorphins in an unintelligible blend between extreme pleasure and extreme disgust. He took the plug out of my mouth and dropped it on the floor as my body went limp.
It was an amazing experience and I have Dean to thank for it. I curled up in my side with my face against his tummy and he rubbed my back until I fell asleep. I don’t believe Timmy or Rob had any idea what happened behind them that night. But it changed Dean and I forever.
Epilogue:
My life continued on like it had until I finished college at 22. The constant nudity and loving spankings I got kept me off drugs and helped me focus on school and do well. The time I spent with Timmy, Rob, and Dean kept me from sleeping around and I stayed a technical virgin, never having had an actual penis in me, until my wedding night. The humiliation and shame I felt through my teen years led me to become a strong and independent woman after I graduated and moved out.
I was promoted quickly through a company and have a leadership role. Not being shy or passive like some women helped me excel even above my male peers. I owe a lot of my success to my parents who have me the type of parenting I needed versus the kind that was socially acceptable. I go to dinner with them a couple times a month and we get along great. They don’t discipline me anymore, but we speak of my childhood often, with fond memories all around.
I mentioned I got married, and it was to Dean. We fell in love, had great chemistry, and so many shared experiences over the years. We still hang out with Tim and Rob about once a month, and things there stayed pretty much the same. The real difference is only Dean can fuck me with his cock. We all turned out fairly successful and very happy.
Oh, and Dean and I have a baby on the way. She will be born early next year. At the baby shower my mom gave me ‘the book’ as her private gift. In it was a note that said “In case you get a daughter just like you. -love, mom and dad.” So who knows what will happen in the years to come.
About this story:
This was a completely fictional account and not a word of it ever actually happened. I appreciate everyone who read it and sent me nice messages. I know we went some weird places together, but personally I got a lot out of the exploration. I hope you did too. I am always open to PMs to discuss this story or ideas for a future story. I’ll be taking some time to figure out what I want to experiment with next. Thank you for reading.
Source: reddit.com/r/sexystories/comments/70gmc7/my_discipline_part_11_final_mf_atm_light_period
https://www.reddit.com/r/sexystories/comments/70cnku/my_discipline_part_10_ff_humiliation_light_period