So, I was locked back up right after my release last week. Since them many things have happened. As mentioned before, I toyed with the idea of a card-game for my KH and me. I was very reluctant about the idea since I did not want to introduce any form of dictation into our chastity play. However my KH found the idea very good. She said it would give her more initiative to play with me and make it easier for her to decide When, How, etc.
Actually from my childhood I had like hundreds of empty playing cards somewhere in a dusty drawer. This must be like 20 years ago and I did not remember them but stumbled upon them when digging around the drawers searching for dices, etc.
So I painted some cards. I asked her if she wanted some "tasks" as well for her and she agreed. So basically our game was the following. I made one "chance" card and 7 blank cards. She also wanted to randomize the events that can happen on playtime. So i mixed up various kinky things she could do to me that could end with just a tease or a ruined orgasm or rather rarely an orgasm.
Each morning she would decide tasks for me I had to fulfill during the day. If she decided I did them well, she would let me draw from this chance deck and from the playtime-deck. In case I drew the "chance" card I would be let out this evening for what was on the playtime-card... however I would not know until the evening if I had drawn the "chance" card or not... and I would not know how it would end...
She herself would draw a task-card that she had to fulfill during the day. Those included small teases, sending dirty SMS, doing some verbal teasing etc. I also included as many blank cards in this deck so she would get lots of nice days without having to do anything.
Ok... this all sounds awfully artificial when it is written like this. I told her over and over again that it is just a stupid game and she did not have to do anything on those cards. She just smiled and said: "Oh yes, I have to... why not?" ... I tried to explain that it might just be some sort of "idea" giving and nothing that should force her or me to do anything... but she seemed really fine and wanted to give things a go...
So we started to play and on this Saturday after a week of lockup (and no teasing) I drew the "chance" card. I did not know until afternoon when she came to me and said... Sweety, we need to talk about this card-game ... I told her of course and if she would like to stop playing this stupid game and stuff... she blushed and said No, that's not it ... but you drew the chance card and the playtime card says stuff I have never done before and don't know about ... I had to smile with her and embrace her and asked her what was written on the card...
Ok the card read ... She could decide if I was to do some anal-dildo-play with myself or if she would do it ... and it would end in one or more ruined orgasms ...
I had to grin a bit because this card is rather "heavy" for her. We have never done anal-play together. She was always afraid of it being dirty and stuff. She kept insisting that since my coming-out to her and our lots and lots of talking she has changed her mind and wants to do this with me, but we have never done it, since over a year now... and she did not know much about ruined orgasms at all ...
So we cuddled together and I explained things to her. I told her what a ruined orgasm is, how it works, what the difference between a fulfilling one was etc. I also told her she did not have to touch me, I would do it myself if she was afraid and stuff... she could just watch and learn ... and if she really did not want to do things I would not do it ... I did not want to make her afraid, or disgusted or anything... she said that she wanted to go to the bathtub with me ... we would see where it would lead later...
While she put some hot water in the tub cleaned myself thoroughly ... and I mean thoroughly. You can not imagine how afraid I was that I would somehow confirm her fears that anal-play could be dirty etc. In my head I knew it would not be so, I have played with myself a thousand times and when I clean/flush myself, there is no dirt or stench or smell or anything ... however even knowing this I was afraid that something would happen exact at the moment I would play with her...
I was set free from my Steelheart and we went to the bath-tub together. We relaxed and I started massaging her and she soon was very aroused. We preceded into our bedroom and continued there. Soon I was eating her and it was not long before I brought her to climax... She rolled over and said ... now it was my turn and she wanted to give this ruined orgasm thingy a try ... I told her I was "THOROUGHLY" clean and if she wanted we could play a bit there as well? ... before she could reply I whisked the smallest buttplug into her sight and told her it could stay in during the playtime, she would not have to do anything with it...
At first she could not believe it would stay in until I explained that the form of the plug is exactly for that etc. I had to smile because she really was so unknowing about all those things. Well, I was allowed to continue and soon was laying beside her with the plug in me... and she took control of the remote ... switching it up a notch ...
She started exploring me ... touching me and fondling my balls and dick and even touching the buttplug... she seemed to start enjoying this a lot... She said she wanted to try to find the right moment to stop herself and I told her I would tell her when to stop if she did not...
She played with the butt-plug settings, turning them up to maximum, making me moan in bliss. I was so highly aroused by the whole situation... by her fondling me, my lockup time, the butt-plug for the first time together ... etc ... it did not take me long until i felt the edge. However I always said "stop" a tiny moment too early ... since I was afraid of going over the edge and getting a full orgasm. So we repeated this a few time without me having any orgasm... We edged ourselves closer and closer to the perfect point when to stop and then she hit it ... I dripped cum ... no squirting, no hip-rocking, no back-arching ... just the cum slowly dripping down my cock ...
I have not experienced ruined orgasms myself before. I have tried in the past, but could not stop stimulating myself ... and always ended up with a real orgasm

... I guess my self-control is lacking a bit

Anyway, so this was my first ruined one ... it was strange ... it WAS pleasurable ... it WAS frustrating ... it WAS making me even more horny ... very fascinating ... and my cock would not loose the erection ... it kept standing, ready to go ...
She found this very fascinating. It was a totally new thing for both of us. She then said that I have been so sweet the last week and have done so many things for her, that she wanted to relieve me and give me a full orgasm. That one ruined orgasm was enough and she wanted to give me a real one ... I had earned it she said.
I was totally happy to oblige her in this, so she continued to stroke me and after moments I felt myself edging again. It was wonderful and I was in bliss and steering towards a huge orgasm. I felt the edge and I drove past it and in that moment she said: "Or rather ... I have changed my mind" ... and stopped again ... I was like WTF!!! and then felt another dripping of cum on my belly ... which she commented with a delighted laugh and a comment like: "I did it! ... I really did it!!!" ... I slummed back into the pillows and moaned. She had hit the point of stopping so exactly... even more accurate than I could have told her. really really felt cheated of my pleasure.

... and I felt very very proud of her because she has managed this exact point all by herself. She just added an "So, its time for lockup again... " to seal my fate...
Later when I was back in we talked about everything. I asked her if she felt the right point to stop and she said yes it is feel able. The first time when I said stop she said she would not have stopped but the second time when I said nothing she could feel it... my contractions and their frequency and that I was about to cum. She said that the anal-play was not making her feel bad or anything ... she was a bit ashamed for not trying it sooner ...
I just kissed her and we cuddled close ... and I could feel my erection in the cage again. I silently found it fascinating that the ruined orgasms really had taken nothing of my arousal or hornyness but perhaps even added to them... and I was glad she "changed her mind"
The next day ... she would draw for me and would draw the "chance" card again... Even though that is highly unlikely we changed the rules. Instead of a deck with blanks and one chance card, we made a deck with numbers. I would draw a number and this would be the days of my lockup until another tease ... this way we can vary the amount of small and high numbers (to modify the chance of something happening sooner or later) and she would know days in advance when and what would happen ...
So ... we will see where this game leads us ... I would like to hear from you if you are interested in further postings and details about this plunge into chastity
