I was to receive punishment for breaking the ‘only allowed to edge’ rule that Miss Lois had given me, which ended up involving some forced orgasms. When Miss Lois started training me, one of the rules was that I always had to wear heels while touching myself (this had to do with how she wanted to train me to always become aroused when wearing heels) and that if, I was only allowed to edge. I wasn’t allowed to come unless she gave me permission. Additionally, if I noticed that I was wet or aroused, I had to edge myself (while wearing heels of course).
I’m not sure how to explain this one exactly as I don’t remember it very well… but at some point, I broke this rule and instead of edging, I made myself come. (more than once?!) Miss Lois had said something which was kind of vague (in my opinion) and it contradicted the previously set rule and so I thought I was allowed to actually come in certain circumstances (without her permission).
She wasn’t happy when she found out… (luckily I had only done it maybe two or three times?) by the time she found out… Naturally, I had to be punished.
She said that my punishment had to fit the crime and that it would be in threefold (so I guess I must have made myself come three times then… oops…)
- I was to masturbate and cum five times in a single day, wearing the heels every single time. I was to leave at least 1 hour in between the time I masturbated and I had to write down what time it was after I had done so each time, how it felt and how long it took.
- I was to masturbate for a whole hour and to try and cum as many times as I could. I was to push through the sensitivity of my clit (which is very sensitive!!) I had to write a report on how often I managed and how each of them felt. She added that if I failed to reach a reasonable number I’d get punished in a different way.
- I was to get ginger and to insert it in my bum. Then I was to masturbate and cum as often as I could. I had to cum at least once and the ginger had to be in for at least 10 minutes. I also wasn’t allowed to stop masturbating once I’d come once and before the 10 minutes were over.
During all of these, I was to wear heels.
I still have the reports I wrote after finishing the punishments so I’ll include them below.
Punishment 1: Cum 5 Times
Number 1: 8.23: It took me 13 minutes and it felt… em… sensitive to touch my clit directly, which made it harder to get there. My muscles tensed a lot and my body was shaking, trying to get there and then finally coming.
Number 2: 10.58: The second one took me 17 minutes. I didn’t lie in my bed out of fear of squirting, but it was too much to stand up and it hurt to directly touch my clit. However, I tried to push through while I was standing, but I had to stop and decided to then lay down on the floor. On the floor, I was able to touch it just slightly above, which also felt kind of nice.
The feeling is like a tingling sensation and whatever it is, it’s slowly growing, building up towards the orgasm. It feels like running after someone and almost catching them, but not quite until finally, you manage and then it feels like a release. And it’s like the vagina is throbbing or something? And then immediately after, it’s too sensitive to touch and then my body relaxes and I need a few seconds to catch my breath.
Number 3: 18.01: … took 5 minutes lol. It felt like it took a lot longer and it felt like it was difficult. I squirted before coming. It felt rather intense when I cummed, as well as before getting there, keeping up the movement of my hand. I also felt like I was unable to breathe as good as usual while my body kept arching up.
Number 4: 20.34: It took 10 minutes. The tingling building feeling only came really late and very quickly and lasted just a few seconds before cumming. I did loads of squirting before that but all in all it just kind of felt like a job I had to do.
Number 5: 22.34: Took 11 minutes. I wasn’t wet at all and scrolling through Tumblr did not help at all so I just kind of found a spot and moved my finger really quickly to try and force it but I really do struggle to breathe somehow because when I really need to focus I automatically hold my breath or something? So every so many second my chest hurts and I’m reminded to force myself to breathe and as it goes on like my body itself aches. Like my back and neck and limbs because they’re getting so tense I guess so I’m trying to force my body simply to come and touching hurts. There was even more squirt this time and it just hurt to keep trying to force it and then when I managed to force myself to cum it had the good feeling thing very very briefly and intensely. It now feels sore and it hurts to pee.
Punishment 2: Forced Orgasms
I started at 2 PM and finished at 3 PM. Since the first punishment yesterday it has been feeling like something in my vagina hurts. Like, it’s some small spot somewhere on the left, feels as if there is a small cut on the inside or something.
I chose to lie on the floor again because of my usual tendency to squirt a lot. The first time took 12 minutes and it was kind of alright, but it felt more difficult to get there than normal. I got wetter as I was masturbating. The build-up was kind of slowish and then suddenly really fast just before coming. I only semi-directly touched the clit because of it being already sensitive.
I can’t remember the second time too well, but I managed to cum around 2.24. It was kind of like the first one, except everything hurt a little bit more and it felt as if that little cut started to expand. Then someone rang the doorbell twice and my grandma came into the house with her spare key, which I know because she shouted, asking if someone was home. I ignored her and pretended I wasn’t there, but my heart started racing twice as fast as i was lying on the floor of my dad’s attic. Thankfully, she left 10 minutes later.
The third time happened at 38 past and was really painful. It felt as if this cut through all of the left side of my vagina and the more I sped up or the closer I got to potentially cumming, the more the feeling intensified and it felt like it started to burn really badly. At the same time, it seemed like I was becoming less wet. I had to push through though, but the release was really short.
I don’t know how I managed to come a fourth time because the burning cut intensified even if I moved my finger really slowly. I tried to just force it out, four times but I had to slow down because it hurt too much and my eyes started to tear up. I kind of tried to put my mind on zero and to pretend I wasn’t really there so then finally, at around 5 to 3 I managed to cum and it just really hurt – and to still keep on masturbating after – I don t know how I managed that. I moved my finger really slowly and slowly tried to get a slightly faster rhythm but I felt like I really did not want to be there.
My crime which caused this punishment was 100% x 6 not worth it.
I again tried to properly speed up my movement to see if I would maybe be able to force one again but then the time was up.
It huts to sit now and it’s burning constantly. You told me I could insert something into my vagina or bum to distract myself from the sensitivity but I did not want to insert anything because it hurts and would probably hurt even more right now… it’s probably why it feels like I’ve been cut anyway. I kind of wished I could’ve hurt my nipples instead as a distraction. I didn’t really squirt today though. I feel exhausted.
Punishment 3: Ginger and Masturbating
I remember that these 10 minutes were quite a challenge for me. It was difficult and felt intense and long even though it were only 10 minutes. While I was doing it, I kept repeating in my head how I deserved this for what I’d done and that I should embrace the pain now, as it would mean I’d be forgiven afterwards.
I wrote the following report on it back then:
“I really don’t want to do this…
15.40: I set a timer on my phone with the idea that I wouldn’t have to pay attention to the time. The ginger in my bum is so intensely painful and the more time passes it kind of intensifies at first and it doesn’t feel like it levels or becomes easier to deal with. I can’t get used to it at all. It also surprises me how intense the feeling is right from the start. It’s not a slow burn.
The tightening of my bum around the ginger as a result of masturbating – which becomes worse the longer and closer I get to cumming is very unpleasant. Interesting though, I guess…
I managed to cum with 2.5 minutes left to go, so after 7.5 minutes and the tightening afterwards was sooooo much worse. It was horrible. It made me wish that I’d waited with cumming although I know I wasn’t allowed to anyway, and if I had I wouldn’t have properly executed my punishment.
It was really hard to continue masturbating afterwards because of how much it hurt, and also of how sensitive I get after. I started watching the clock for those last 2.5 minutes which made time slow down even more. I didn’t manage to come again. I’m very lucky that it only lasted 10 minutes, but it felt like an eternity regardless.”
Once I finished this third and final punishment I instantly felt relieved. It literally felt like my sins had been washed off of me and I was very grateful that Miss Lois had given me these punishments to do that. When I still had to do the punishments, I felt like I was carrying some weight with me. I felt very bad about what I’d done. I certainly never broke the rule again! (And coming 4 times in the hour was enough, so I didn’t get punished again, thank god!)