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?

Sissy Husband Training

When you read sissyphone you should feel yourself turning into a submissive sissified creature, ready to be used, trained, pantied, sissified, domesticated … for the sake of your mistress, and very much like the sissy husband of this story. If you want to show Alexa how servile you’ve become, call 888-411-1230 and tell her how it feels to lose your masculinity, to submit to one woman, to all women, and to try again and again, day after day, to improve your sissiness, your servility, your becoming-wife….
Read this sissy husband story to find out how one sissy slut (with a love of smooth, waxed skin and very big vibrating dildos) spilled it all to his wife one day. Think he was humiliated????

Sissy Slut Training

Sissy Slut Training has rules.. (By the way, are you still loving yourself in lipstick and pantyhose? It would be a very good idea for you to spread that lipstick thick, and a little on each titty, too. Do it now.)

  • Rule #1: You are a sissy and when you read sissyphone  you must be wearing at least one piece of soft silky feminine attire, the daintier the better.Rule #2: When you wear  your dainty you must, must, must tuck yourself back and in, so that you maintain a gently feminine profile….  Wear two or more pairs of panties to secure your femininity…

    Rule # 3: If you feel yourself going femme while reading this sissyphone, you must call me and let me name you as a woman.

    Rule #4:  To be determined during your first call….

Sissy Story

Sissy Story

Why read a sissy story? Let’s say that you are a submissive. You are excited by the idea of submitting to a woman who controls you. You may know that you want to be dominated: but how? How would a mistress dominate you? Would she insult you? Would she call you names? Would she make you feel weak? Would she humiliate you? Would she encourage you to be more feminine?  Would she hypnotize you? These are all very different things.

A sissy story about a woman who controls you through hypnosis, like Pussy Control, lets you imagine yourself as the subject of a Mistress who can talk you into submission. Hence in Pussy Control, Mistress Alexa says:

Look into my nipples and relax. Relax, sink deeper down. You can’t not look, sleep. Your eyes are heavy, but you want to keep them open. Perky nipples, sleep! Stare into my nipples, don’t close your eyes, too heavy, you have to close your eyes. Nipples are too much for your weakening mind. Relax, perky nipples, sleep, bouncing sleep, jiggling, sleep.” He fell deeply into a sleepy trance and slumped in the recliner.

It is by commanding you to do something that the Mistress effects her control.

On the other hand, a sissy story about a Mistress who humiliates you by spanking you in front of your boss,  like Humiliation Mistress,  involves you in an imaginary identity:

And so, Kirk, dressed in a woman’s blouse, skirt and high heels, wriggled helplessly … he was shamed in front of his boss, he was humiliated by being forced into women’s clothes, and he was embarrassed because his tiny penis was getting harder and harder with every downward fall of the paddle.

This imaginary identity, Kirk,  may be exciting to inhabit for the duration of a session with Mistress Alexa, although it is nothing that you have ever experienced before.  Reading the story lets you point to what excites you and inform Alexa  of the kind of images, the kind of scenario  she can use to rock your world….


Call Mistress Alexa

“At mealtimes or when busy around the house, she made him wear a white linen apron,
with his sissy name embroidered on the pockets. It tied with a knot and a bow at the back, so he could not put it on or take it off himself, and so he had the humiliating task of always having to ask politely for it to be tied on or removed. Sometimes, if she felt that extra punishment was needed, she would send him out on little local errands still tied up in his apron, which of course really upset him.”

For our Sissy Beauty Salon callers!

Read our Sissy Beauty Salon story on

Your first session at the Sissy Beauty Salon will be an occasion you will never forget. As a sissy in training you will have submitted to many hours of rigorous instruction at the hands of your Mistress and you will certainly be required to show off all your feminine skills before the appointment is made.
For sissies who love curlers, hair spray, sissy salon gowns, sissy beauty salon chairs with special attachments, makeovers that are also transformations, and more, call 866-57-SISSY for a session!

Feminization Honeymoon

Feminization Honeymoon – what an idea!

Isn’t it inevitable that the airline would lose your suitcase? It is your second honeymoon, and your wife, who always gets exactly what she wants, is perfectly happy surveying the hotel … while you sit and wait for your underwear to dry… and wait… and wait. So there  in your hotel room your graceful wife offers you her panties…  just until the luggage shows up…. just a temporary thing.

But of course, wearing her panties shows you how pleasurable it is to wear sensuous silky feminine panties. And later, when your wife rubs you through them, and keeps them on when you go to bed….. the experience imprints itself on your memory and your libido….

Feminization honeymoon
Feminization Honeymoon

Like a Daughter

Like a Daughter is just one Sandy Thomas story about a mother and a son who check in to a fat farm — then find out it only accepts females!Llike a Daughter

There are other mother/sissy stories that may be of interest to those of you who love the theme of the sissy-daughter, or the mother who transforms her son into a daughter, or the son who earns feminization as a kind of punishment for not losing weight….

Jeff's Humliation
Jeff’s Humliation

or growing his hair long

Mother's New Daughter
Mother’s New Daughter

…. or dressing up in his mother’s shoes ….

A Dress for Danny
A Dress for Danny



Feminine Proposal

Feminine Proposal by Sandy Thomas is another sissy short story found in pdf form on both LULU and AMAZON. Our cuckold clients will love this fantasy: an unemployed husband and his wife try to solve the problem of losing their house by contacting the owner of the loan, who offers the husband a substantial amount of money to go on a date with his wife. The husband does not refuse… and of course, things develop. They do not lose the house. Feminine Proposal

From Husband to Sissy Maid….

When a well dressed wealthy lawyer discovers her husband dressed in panties and pleasuring himself to a hypno-sissification video, she kicks him out of her  bedroom. She makes preparations for a divorce that will leave him bankrupt and homeless, and he asks her to  stay on as her sissy maid.

Determined to humiliate him beyond dressing him up as a housemaid, she  forces him to sign up at an employment agency with a reputation for hiring transgender girls.

What happens at the agency to this cuckolded husband? Call 888-411-1230 and ask for a cuckolding-humiliation session!