Unfair or well deserved?

Sissycaitlin77 · Mar 26, 2018

Miss anne said: ↑

I thought i'd post a little update after the weekend together. Overall progress is good, I started this never expecting it to be an overnight success I knew it would be a long process possibly a few months or maybe more, I'd just like to thank all of you here for your support, encouragement and concerns. All those words give me the resolve to see this through until the end goal is achieved!

So Saturday went very well, and then after yesterday's great start he seemed to slip back into the habit in the afternoon, we had a morning play and I left him bound to the bed for a few hours then released him with the anal beads locked on while he completed the list of jobs I had made for him, it was very amusing watching him walk round naked doing the jobs around the house, the highlight for me was evertytime he bent down,watching his facial expression as the anal beads had a move around! I can defiantly recommend their use for anyone who hasn't tried them on their lockee.

He didn't even have one cigarette while they were locked on him and he completed all the jobs so I thought I'd release him at around 4pm, we had our evening meal then he couldn't resist the after dinner cigarette even with me offering encouragement not to have it, I easily think he could have gone the rest of the evening not having one but he gave in and over the course of the next few hours he had 5 more.

He seemed to think that I would get bored before he stops, so I thought that I'd give him another lesson seen as I was in the mood for a play, we went to bed and I allowed him to pleasure me with his tongue and my favourite vibrator and he seemed eager to be released, I told him 'you know what happens if you cum'
Still he wanted out so I tied him to the bed.

I've decided the only time I will release him is when he's bound to the bed just to ensure there's no escape for him, plus I can leave him to get soft so he can re-attach the cage, then I decided to start of by using a dildo on him for around 15 min seen as though he was nice and stretched after the beads earlier, we did a few other things and I thought I'll make this an evening he will remember, just a little reminder for him so he knows my resolve. Out once again came the open mouth gag.

I first made him cum which didn't take long even with him trying his best not too, and I slowly dripped it into his mouth from mine he tried his best not to swallow, which didn't work it just made me smile knowing all he was doing is savouring the flavour until the inevitable, so I carried on my plan was to give him more than one dose, the second time took a very long time, him trying his best not to cum along with the added longer 2nd time made it quite the workout for me but I was determined and then it happened this time it was over his stomach so I scooped up his juices bit by bit and rubbed my finger on his tongueuntil all was consumed all the while whispering ' you did so well until this evening, but if you carry on you better get used to the taste'

I left him for a while to soften and enjoy the taste then had him re attach the cage, I felt the little reminder went well, after he got over the taste we cuddled and had a chat he said he was still enjoying it and he is really trying and reminded me of how much he didn't like the taste, I said well you best try your best not to cum tomorrow then as I've enjoyed tonight and I expect to have some fun then aswell...... so this week I may try and test him every night pleasure for both but a bad taste and reminder for one. Today he didn't have his morning cigarette again so I defiantly see that as progress I told him if he holds off as long as possible with his first one it'll be a lot easier for him to kick the habit.
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Mistress Anne curtsey.

thank you so much the update. I loved reading all about how your training him to kick the habit great touch on the anal beads hehe and tieing him up when you let him cum and he has to eat it. this brought back alot of good memories from my ex gf/mistress so thank.you again for the update I look forward to more.!!!

sissy Caitlin.

Miss anne · Mar 30, 2018

Well the week has been a very intresting one and it seems his attitude towards smoking is slowly beginning to change, through the week I'm made him suffer the consequences of having an orgasm twice and he now seems determined to get released. Although it's very amusing for me I feel that a change of tactic may be needed as he still hates the idea of having cum in his mouth but I'm not sure if he will become use to it after a while? Does anyone else have any experience on this concern of mine?

While at home on an evening he has cut down to just one or two cigarettes which I can cope with and is a vast improvement so I think the time has come to extend the time from 6 hours per cigarette to possibly 12 or maybe even a day?

The Easter break is upon us and we have 4 days together surely this will be a good test and I hope to keep him busy with a list of jobs to do followed by a few pampering sessions for myself, I don't think I can resist the opportunity for 4 massages in a row.

A few ideas to keep him off of the cigarettes this weekend I have thought of is a padlocked spider gag on him for short periods of time and the usual of keep him tied and teased but I'm open to any other ideas you can think of.

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Unfair or well deserved?

Sissycaitlin77 locked sissy slave.

Miss anne Member