Fitted Cum Stopper

After trying for a long time and using a lot of special gel I have managed to insert the cum stopper into my penis. It wasn't easy at first. Fitting the glans ring on over the head then inserting the ball end into the hole. 

It was OK entering the hole but the hardest bit was getting it past what I call the little door to the shaft. With a lot of gel and a gentle push it would pop through without any pain at all. Once in its very comfortable to wear.

I think the shaft with the ball on the end is a bit too short and needs to be a little longer to do any stopping.

The picture is not to good. I will upload a better one when I get a chance.

Fitted Cum Stopper

Cum Stopper

Just taken deliver of my new Cum Stopper. I must admit I am very apprehensive about this little item as i have never had any item pushed down into the head and down the shaft of my penis. It may take me a bit of time to actually get to wear this item, but to please Mistress I guess I am going to have to a least try and insert it.

Cum Stopper

Pleasure Update 2

My reply to the previous post:

Remember Michelle this is a big reminder of what you can expect when you cannot control your sissy cock from ejaculating. 

I have made it quite clear in the rules of our relationship that you will not be allowed to orgasm unless I give you explicit permission to do so.

You can expect to be severely chastised if I see even the slightest showing of ejaculation.

Punishment is inevitable

No Satisfaction

Its been about 3 weeks now since Mistress has allowed me to have an orgasm. There has been a lot of sexual activity between us but Mistress stops me right at the critical point. 

Mistress has informed me that I have about another week to go before she considers allowing me to ejaculate, but it all depends on how obedient I have been. 

Mistress also informed me that if she decides to allow me any satisfaction my small doggie food bowl and some yoghurt will be involved. 

Well Caned

I am now being punished on a daily basis. My buttocks and thighs are now starting to suffer with bruises, red marks, cuts and welts that last for days on end. 

Serious punishment

After the last few punishment sessions, I have recently started to become erect while being punished and after quite a few strikes I have noticed quite a bit of precum, and so has Mistress which inevitably leads to being punished even more as any precum no matter how small is strictly forbidden and all precum has to be cleaned up with my finger and then licked clean.

Precum while being punished

Orgasm Denial

I now think Mistress is getting in some practice ready for when the new Chastity cage arrives later next week. For 3 days now I have been denied an orgasm. Sex between us has been good, but as soon as I get to the point of ejaculating she has stopped me. Last night after serving Mistress and giving her complete satisfaction, I was denied an orgasm, she then waited a short while, made me kneel in front of her and masturbate, again only to be stopped right at the crucial point. An hour later she did the same again. She told me that there would be no more orgasms for me unless she thought I was worthy of having one, and that the only way I would now be able to ejaculate was through her milking me with a prostate massager that would empty me without having an orgasm.