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?

Wife forces Tiny Dick to Suck Cock

Mistress: Just read this story by and want you to know that this is the kind of thing my wife would do to me. She began to bring men home about a year ago and is now making me take them in my mouth. I think soon she will make me do more….

Jim then removed his fingers and I then felt the tip of his cock against my
ass. He rubbed his fat cock over my ass and then he slowly began to work
it in. The pain as the fat head of his cock slipped into my ass was
unbelievable and I screamed out, causing Bills cock to fall out of my
mouth, Jim started to pull his cock out and then drive it in again. His
fingers had been nothing compared to this and I thought I was going to be
split in two as he drove into me again. “All in” he shouted and I could
feel his heavy balls against the back of my legs. There where tears
running down my cheeks and my legs were like jelly but Jim started to set
up a rhythm in and out, I could hardly believe it I was getting fucked in
the ass by another a man a very big man.

Jim was properly fucking me now pulling his cock nearly out of mass only to
ram it home again. Bill grabbed me face again and forced his cock back in
to it. I began bobbing up and down on Bills cock in time to Jims fucking,
sucking as hard as I could and licking his shaft as it slipped between my
lips. Jim kept on pounding my ass. I felt like I was a human kebab skewed
on these two big cocks. I could see my wife fucking herself with the
dildo as these two men gave me the fucking of a lifetime at both ends. All
the while they were calling me names like slut and bitch and telling me to
suck better or how I was gonna swallow their cum. This just turned me on
even more, I was loving being used like a slut by these two men and it was
making my own cock rock hard.

After a little while Bill starting moaning and then placed his hands on the
back of head pulling it forward further onto his cock and then suddenly his
cock began to twitch and then he let out an almighty groan as he began to
cum in my mouth.

My mouth was soon flooded with hot salty tasting spunk. Bill held my
head firmly and I had no choice but to swallow as wave after wave of spunk
hit the back of my throat. I was swallowing as quickly as I could but
still some spunk began to dribble from the corners of my mouth and down my
chin. Slowly Bill slipped his cock out of mouth “clean it slut” he said and
I began to lick and suck the last traces of cum from his cock.