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?

After my chastity training with Mistress Alexa

Mistress Alexa

You asked me to write you and describe my orgasm last night. I have always masturbated regularly most of my life, very often daily.

When I first spoke to you and you told me to use the candles and stroke myself 5 times daily without having an orgasm, i thought it would be impossible. But, knowing that I need a mistress, I told myself I would obey your every demand to the fullest degree. The first day was a new sensation, 5 times the first day, getting so close and having to quit. The part that excited me the most was knowing I was owned by you and I had no choice but to do as told.

The second day was rough, my mind trying to convince me that this wasn’t what I wanted, what i wanted was to have an orgasm, but, when i went to the next town and bought the panties, i realized I was under your control.

The third day, putting on the panties in the morning, doing my daily exercise, I wanted to be your slave. Wearing them under my jeans on the farm, all the other men working around me, i felt ashamed and aroused, but, it was worth it knowing i was pleasing you. I was worried someone was going to notice that i had a hard on most of the work day.

When we spoke the third night, I was so happy to hear your voice. Deep inside i was hoping you would let me cum, but, i assumed i would not be allowed to. As i knelt in my bedroom with my candle and closed my eyes and saw you holding me as i was used, i knew how much you loved me, you knew what was best. I was so hard, 3 days of no release, i could barely touch myself. When you told me i could cum while watching you getting serviced a rush filled my body. I almost didn’t feel worthy but at the same time i wanted you to see what i had saved for you.

i knew i didn’t deserve to be inside you, but, i knew you would be so pleased to see how much i came. as i watched and stroked i couldn’t hold back, the cum covered my thigh. large amounts fell on my leg, the warmth spread throughout my body and the warmth on my leg was like a gift to you. now as i shower and wash my pussy i can actually feel it getting looser, more accustomed to being used. I hope i’ve pleased you with this letter and that i can please you more often.

Your slave

Keyword: Chastity Training

The Viriguard: Athletic Chastity Wear for Sissy Husbands

One of my darlings telephoned last night with much enthusiasm for this new chastity training system implemented by a correctional facility for wayward males. One of the testimonials on the VIRIGUARD site reads:

We operate a large (600 bed) secure campus, with most residents referred for corrective reasons by the court system. Life at TCYAC is not punishment but a positive life-transforming experience that gives residents the opportunity to become fully enabled adult human beings. Our physicians discuss the athletic protection and health benefits of Viriguard with each new resident, then assist with the private fitting and installation…— Marshall Strickland, Chancellor, Tri-County Youth Attention Center

To install the Viriguard, the wayward sissy in training is stripped naked from the waist down and stands before you with his hands behind his back. It may help to have an assistant hold the sissy from behind. Alternatively, Purity Athletic also provides various restraints for use with those sissies who have not developed the self-discipline necessary during this procedure.

It is a fascinating web site, with pictures of the correctional building, a competitive analysis of the more sophisticated chastity restraints on the market, and a touch-tough approach to the re-conditioning of cuckolds, sissy maids, and weak hubbies.

The athletes pubic hair should be clipped off. Many installers find that electric barber clippers do a quick and adequate job, The Viriguard installation kit includes a hypoallergenic, tissue friendly surgical glue which meets all FDA requirements. .. Attach leg straps…Using the enclosed measuring rings and ruler, measure the circumference and length of the athlete’s flaccid penis.
…Apply viriguard urinal sheath applied to wearer’s penis… and then, my favorite bit:

Finally, using the Viriguard electric screwdriver, tighten the eight snap-head screws though the pre-drilled holes in the cup to the belly plate. When the proper torque is reached, the heads of the screws will break off, leaving no surface for any screwdriver or other tool to gain purchase.


To remove the Viriguard, contact Mistress Alexa. She will email you the instructions.