An open door

The conversation starter is a good point.
Meanwhile I strongly tend to the dom/sub event and we are definitely newbees about that and I hope for a good conversation and some humiliation and pain for him.

 

Thanks for the compliments.
I just read again my post from the past. I did not often slapped his balls since then. Maybe I should do this more often.

 

Tomorrow the four of us will visit sauna again.

 

I unlocked him on Saturday night, told him that he is not allowed to orgasm before Monday. Was a playful night and I told him how much I love that he concentrates on my satisfaction and his discipline, not being focussed on his joy too much.
He entered me from behind, didn't move but fingered me to orgasm.

On Sunday I told him that I wnt to see him at his dildo stool and he prepared for that. I fixed his cuffs to the stool, blindfolded and gagged him. He had a boner the whole time.
I told him that sister and brother in law will pick us up for sauna and that I want her to come upstairs shortly, while he will be sitting there. If that was a no go he should shake his head. He didn't.
I texted her to come upstairs shortly, but just her alone.
When she came to our flat, she saw him sitting there. Looks nice, she said, what is it done for? She asked.
He will tell you later, I said. I whispered into his ear, that it won't happen if he doesn't tell.
He will never know, which sister stroke the boner meanwhile.
We unlocked his cuffs and told him to hurry up, then we went downstairs, told her husband that he will follow shortly.

I asked my sister if I could take off the cage from her husband, because I want to see how the looker insert works. I did this the last time, when we visited the sauna. There are changing booths, don't worry. So we mixed the couples for undressing.
I asked my brother in law, when he got his last orgasm, it was at the Carribean at their honeymoon around three weeks ago. I asked him about hygiene, he told that they are having two cages meanwhile and change weekly for hygiene and minimal interruption. You are kidding, I said, but he showed me the second tube from his bag. He barely managed to remove the base ring because he stared at my pussy which was shaven a week ago.

When we met my husband and my sister I saw the first time that her baby belly was starting to grow and she mentioned that I lost some hair down there. I told her that this was a unique event and that I will let it grow again. While I keep my lips shaven or waxed she wears the full bush. But we both let it grow in the arm pits. As crazy as it sounds but it feels powerful.

We spent a nice day at the sauna, visited different locations, fell asleep in the resting areas and when it got dark we went to the outside pool. I reminded my husband that he did not tell my sister why he was sitting on a big dildo. It took him a while to answer. Under water I shortly touched our penis and told him that I felt that he was enjoying the moment. So he admitted that he want to get fisted on his birthday.

The rest of the evening was almost surreal. While sitting naked at the pool bar end enjoying non alcoholic drinks we admitted that almost one year of male chastity we did together was an interesting thing and that we will develop this in the future.

At the end I put on the Looker to my brother in law, It felt like impaling his penis and they dropped us at home.

The night was great again and I sent him to work today with the mandatory remark, not to jerk off at the company's toilet.

 

I just texted him and asked if he was behaving well. So he did, he responded.
I told him that he has been a good boy all the time and I offer him a fisting already today.

 

I will have to shorten my finger nails.

 

He didn't mention it. Maybe didn't even notice.

 

When he came home yesterday, he thought that we would jump into action immediately. But I said, that I will take him out to dinner first.
When we retuned home, I told him to go to the bathroom and prepare himself. Meanwhile I prepared our bedroom, candles, pillows, lube and even more lube.
I asked him to lay down and find a comfortable position. Laying on the side, with the upper leg pulled up seemed to be comfortable. He was already leaking, I placed a towel under our penis. We won't care about our penis during the session I told him.

I had to find a position in which I could please him but looking into his eyes as well. I fondled his butt cheeks and started to finger his ass. He was really enjoying it. It took us some time but we both felt that he was relaxing more and more and I stretched him continuously. Our penis remained rock hard and leaking the whole time. Finally I was able to insert my hand completely but I kept it pointy and didn't made a fist. Mooving was not possible but i was able to turn it slightly.

I asked him how it felt, unknown but nice, he answered. He was enjoying it, felt himself on a rising slope but it started to hurt a bit. I withdrew partly and very slowly. Finally I took off my hand, cleaned the lube from him and told him to relax. I went to wash my hand and returned to ride him. I whispered into his ear that we will try fisting again soon.

He asked me to interrupt, because his body seemed to be confused between pain and excitement. We interrupted, I made us two glasses whine and we talked about the session. He said, that he enjoyed it but it was overwhelming. We agreed to continue on that. I told him that I won't cage him this evening but tomorrow in the morning after PIV.

It was a remarkable experience, that I didn't gave him orgasm at release date but we laughed about it.

The morning started with PIV and I asked him for a second round and now he is caged again.

 

His birthday will be in two weeks and he is very motivated to train. We will try again at the weekends, but I will keep im caged, maybe that helps to take attention away from there.

 

Meanwhile I am quite sure about his birthday present. I will tell him that I invite him to a sum/dom event, where he will be naked and locked all the time and that I expect that we both will behave as expected in our roles. He will get three days to decide and if he agrees, I plan to ask my sister to attend as 2 + 2.

 

https://www.chastitymansion.com/forums/index.php?threads/remote-control-estim.55151/#post-683466

I just found out, that FancySteel will attend at the BoundCon here in two months.

If he our dom / sub event goes well, this collar might be the next step.

 

Short update on our fisting adventures. We tried it again this weekend, kept him locked and didn't care about our penis.We tried a different position, on his knees, head down, hands and feet locked together. He calmed down and just let me do my thing.
Went a bit better than last time, he didn't feel pain this time. But I didn't gave him a chance of to finish.

 

Meanwhile we upgraded again and now he sits on a 5 cm wide dildo.
This locking period I won't unlock him for stamina training. I want him to loose focus for our penis and shift to his butt.

 

One week left till his birthday, will celebrate one year in chastity. Anal orgasm would be a nice present.

 

I just re-read how our journey started almost a year ago. The four of us went a long track.

 

Did anybody got edged anally ever?
I guess my husband is mellow now to get fisted to orgasm.
We changed from doggy position to laying him with his belly on two chairs and having his knees moved back a bit. This way all muscles around his butt are relaxed. His arms are cuffed behind his back and he gets blindfolded and gagged.
I did it slower than before, he almost started to bend towards me. I told him not to move, that I am in command and that I will decide about his relief.
Meanwhile I can keep my hand omfortably inside him, take it out and in repeatedly and move a bit inside. But i am not able to close my hand to a fist inside him.
He seems to really enjoy it and offers his body to be used. I didn't care about our penis but it didn't seem to be very hard. But it was leaking intensely.
At some point he seemed to get increasingly aroused. I stopped moving, withdrew slowly and just circled a fingertip on his gaping hole. This seemed to arouse him further, so I interruped at this point. It's not your birthday yet, honey.