Cuckold Husband Letter: Chastity Training

Good Morning Mistress,

It has been far too long since I have shared with you the humiliating, and yet exciting things that S has been doing to me as I continue my decent. I would like to share with you a recent evening that we had that actually began at Christmas. A few days before Christmas, S found my Aneros Helix and asked me what it was for. I was very embarrassed as I explained how it massages the prostate and can actually cause me to ejaculate without actually touching myself or could be used to make myself have an incredibly powerful orgasm with tons of cum. She was wonderful about the whole thing and listened intently but we decided that it was something that I should use myself.

For Christmas, she said that she was going to give me 1 month as my chastity keyholder and we have had so much fun since. Albeit, she has had much more fun in terms of her orgasms. I want to share with you our most recent evenings events.

As I stated before, I have been locked for just over 3 weeks as of today and it has been incredibly torturous and exciting all along. A few nights ago S stated that she wanted to play and that she wanted to experiment with me wearing the Aneros. I immediately got hard. . . well, tried to get hard given my chastity cage. Anyway, we got into bed and she asked me to roll over and I did and she very slowly and methodically lubed the device and my ass and began to slowly work it in. I thought she was going to be rough as we have never really tried much in the way of anal play, but she was very teasing about the whole thing, slowly working it in and then gently pulling it back for several minutes before she finally let it settle all the way in. She instructed me to stay on my stomach as she moved around and put her pussy just inches in front of my face. She instructed me to gently begin to lick and I did as instructed, taking great care to enjoy what was going on and on delivering delicate pleasure to my queen.

She began to ask me how I was holding up after being locked up for so long and if it felt odd to have the toy in my ass while my “dicky” was all locked up. I ensured her that I was happy to have been given the opportunity to show my devotion to her. We made small talk for a few more minutes and she then told me that she wanted to play with the newest dildo that I bought for her. Over the years I have purchased several for her but the latest was by far the biggest. It is 9 inches of insertable length, as big around as a RedBull can, has a full set of balls, and it vibrates. Til a few days ago she was apprehensive about giving it ago but this night was different. She brought it out and just held it for a minute staring in amazement at its prodigious size. She asked if I was sure that I wanted her to use it because she had never had anything that large in her before, well, not since we’ve been married. That stung a little, but I caught myself and told her yes, she should.

Cuckold Husband Letter: Chastity Training

At this point she told me to lick it, slowly while she described how funny it was to see me, locked and plugged, licking the cock that was about to make her cum. Got I was starting to really work the Aneros in my ass and was getting very hot. After I had licked it sufficiently, she said she couldn’t wait anymore and told me to work it into her pussy. I slowly guided the head to her sopping wet whole and began to work it into her. I have never heard her make the sounds that she made as it slowly disappeared into her waiting pussy. After a few minutes of my gentle manipulations, she grabbed the base from my hands and told me to lick her clit while she began to fuck herself like a woman possessed with the giant phallus. She gave herself several world moving orgasms before she was done and it was then that I realized that I had ejaculated, but not orgasmed all over the sheets to which she found great interest. She said that since I had “blown my load”, there was no reason to let me out next week as previously planned and that we have many more nights of her exploring her new “lover” with me worshiping her pussy.

What have I done?

Author: alexa

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