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?

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!

Cuckold Stories

What happens when a wife who feels neglected in her own marriage starts to receive attention from other men?
What about the Beta Husband Blues…
And is it true that Slut Wife, Happy Life?

Call Alexa at 888-411-1230 and ask for a personal exploration of the erotic emotions of husbands watching wives with other men.

Sissy Marriage

A Change in a Sissy Marriage:

As a sissy, it is natural for you to want to change your marriage, to change the way your wife views you, treats you, has sex with you…. to share your sissiness, your softness, your submissiveness with your wife. This is one of the popular themes for a phone session – what happens when your wife

  • discovers you are a sissy
  • knows that you are crossdressing
  • acknowledges that you are not man enough to satisfy her
  • enjoys your submissive sissy self
  • tells you that she is sleeping with other men
  • wants you to watch while she has sex with other men
  • wants to dress you up in front of her boyfriend

and more!

A Change in Our Marriage – The Sissy Cuckold

The story “A Change in Our Marriage – The Sissy Cuckold” starts with  a wife catching her husband looking at cuckold web sites. She decides that she would like to cuckold her husband, and begins to feminize him…  Her “loving accommodation of her husband” is one way to initiate ‘a change in the marriage’. Of course, there are other possibilities. Call me at 866-577-4779 to discuss the many other possibilities….

Injured Dick in Chastity

Now I had to get the nasty image of my wife splayed open on our bed as I sat, restrained, 4 feet away- watching her get pummeled by strange — and better — cock, my meatlocker holding my nubdick tightly — out of my mind!! So I went to the den to watch some baseball. I had a couple cocktails and dozed off in the 5th inning and awoke around 11:30 when the front door slammed. I ventured out to the living room and was greeted by my tipsy wife. Her hair a-jumble, nipples stiff against her torn blouse, lipstick smeared and her panties visible–hanging out of her purse. As she opened her mouth-no doubt to give me some sort of explanation–I was surprised at the words she had chosen for this. “I haven’t sucked that much cock in a LONNNGGG time!”–she stammered proudly. I was aghast and stood with my mouth open as she began relating her ‘apology’:

“We were shooting pool and the guys bought me a few drinks and felt me up and it was all just in fun. Next thing I knew, I was bent over the pool table and held down and had a nice dick rammed up my cunt–oh babe, it was so fucking hot! It turned me on immensely and I started offering blow-jobs and then–!
“WHAT ARE YOU SAYING?!”, I screamed.
“I’m saying that I got fucking pounded by HARD dick, you pathetic eunuch! come here!!”
I did as ordered and watched as she took a key from her purse, tugged my panties down and freed my cock from its recent incarceration. “You’ll get hard and be ready to fuck in 15 minutes or I’ll find more men tomorrow–and YOU WILL WATCH!”
I could hardly believe what she had been telling me. as I brought my eyes up to meet hers, she began grinning and I saw that she was staring at my downed panties–and my rising cock.
“You little slut”, she sneered, “your clitty is swelling! You like this!”–maybe, but it was ending right now, since I was getting a hard-on, right? She reached out and lightly stroked my turgid meat—-“mmmmmm”, was all she said. In seconds I was on the verge of exploding but she wasn’t ready to allow that and told me to kneel and get the strangers out of her cunt.

Wake Up Call

I have been reading your stories of a man being taught by a dominant woman to serve her and men at her will.

I have had life long fantasies of being forced by one or more woman to become the slut I know I am.
If you would be entertained and amused by calling in me in the wee hours of the AM Saturday morning to teach me to serve. I would be grateful. It would be my WAKE UP CALL.

Maybe you could be my neighbor that comes into my house and manages to seduce me into being your slut or you would tell my wife about my unfaithfulness. Making me to be on call and to learn to be a cum slut for you and your boyfriends at your desire (when my wife is gone).

Also making me go on your blog and publish what I have done with these men….

By the way, here is a link to a video of what I want my mistress to say to me:


Kansas City Slut

Sissy Cuckold Johnny needs to be humiliated

“I’m a little sissy bitch,” says Cuckold Johnny, as he talks to me on the phone from Vegas this morning. What is your wife doing right now Johnny.
“Im sure she’s with her boyfriend.”
Does she have more than one boyfriend. No.
One. Its a guy she used to date in school. His name is Dwain.
How does Susan feel about Dwain?
She loves him. He’s a real man.
What makes him a real man.
He has a real cock.
What does that mean, Johnny.
It means he doesn’t have a little 3 incher like me.
You’re not a real man are you Johnny, what are you Johnny.
A sissy faggot.

Mistress and I (D’s Story)

Hello Mistress,

Here we go. . .

Mistress and I have been talking on the phone for several years and she has helped me come to terms with my hidden femininity and we have built a rather good relationship over those years. I let her know that I will be on a business trip near where she lives, (I live a long way from her), and beg her to meet me in person. After several weeks of begging she agrees but that I must complete some assignments first. First, I am to buy some items to bring with me on the trip, a pink corset that will attach and lock to my chastity belt, a pink collar with the word “SISSY” on the front and a lock on the back, a Bettie Page wig, pink bra and matching frilly panties that fit over my chastity belt with a ruffled sheer back, stockings and pink 5 inch heels that can be locked around the ankle. Also, I am to bring my 2 favorite dildos, both of which are quite large. I am to also purchase and download a hypnosis mp3 that she has recorded just for me and this trip and to begin listening to it every day, 3 times a day, until our arranged meeting time. I eagerly comply with all of her instructions in my bated anticipation of finally meeting the goddess that I have worshiped from afar for so long.

2 weeks of eternity pass and the time has come for my meeting with my Mistress at the hotel that I have been staying in while on business. During the past 2 weeks I have been very diligent in listening to the file that Mistress has recorded for me and have found myself feeling not only very feminine in my thoughts and emotions, I also have begun to feel as if I have nothing to hide from Mistress, as if I have hid things from her that I have no reason to hide. I feel as if she should know everything about me and that if she should ask, I would have no choice but to tell her. This last bit was exhilerating and frightening all at the same time.

About 2 hours before the scheduled meeting time, in my room, Mistress calls and simply says, “D, I want you to go take a bath, shave everything from the ears down, and then put on the items that I instructed you to bring, locking all of them in place. Place the keys to the locks in an envelope and place on the nightstand by the bed. Next, lie down on the bed and put your hypnosis session on play through your earphones and relax as you listen. I want you in trance when I arrive. Do not disappoint me ducky, you only have one chance. Bye.”

Wow here we go. . . Well, I followed the instructions to the letter and began to go into trance. After a few minutes I began to lose consciousness. I don’t know how much time had passed but I sensed someone else in the room with me. It was the most beautiful voice, the same voice from the recording, speaking in such soft yet demanding tones. I was helpless to move, unable to open my eyes, move my arms or legs, or do anything other than listen to the all-surrounding voice that enveloped all of my world. Mistresses voice began by letting me know that after all of this time, of her taking her time to train me, mold me, dominate me, now she wanted more. She wanted more than I had ever been able to give before and asked if I was willing to give her what she wanted, no, what she deserved from a little sissy like me. In my current state, all I could do was to answer in the affirmative. I felt myself mouth the words but was unsure if the words actually came out. I heard Mistress say, “Good, good my pet.”

What seemed like merely a few seconds later I awoke, feeling amazing and sore. My jaw ached and my ass, my ass was on fire, but felt empty all at the same time. I looked around at my surroundings and noticed that my stockings were twisted and had a tear in them near the top. I was still dressed head to toe and I slowly pulled myself off of the bed to look in the mirror and noticed that the hair of my wig was completed mussed and even had what appeared to be, CUM, in it. Oh, GOD! What happened? I looked around the room for clues and found a large manilla envelope with some papers, some pictures and a DVD in it. I quickly pulled it out and went completely white with fear and humiliation. There I was, on my knees, dressed every bit as the perfect sissy, with what has to be the biggest black cock in my mouth, apparently sucking with wild abandon. I had both of my hands around the shaft and my pink lips were struggling to get around the tip of this monster. I quickly looked over the several other pictures of me, my face clearly visible in all of them, in various stages of sucking, or getting impaled by this monster and I began to feel my world come crashing down around me. I opened the letter and began to read.

Dearest d,

As you undoubtedly realize, you have been a busy girl this evening. These COPIES of pictures are for you to keep, I have the originals with me and will keep them safe, for NOW. I appreciate your willingness to give me all of the information about you and your family and friends that you did last night, it will come in handy with what I have in store for you. Also, with the banking and credit card info I now have, I think I’m going to go on a little spree! I so look forward to all of the things that I will have you do to serve me and to entertain me. Please do your best to get cleaned up and ready to go home. I hope you have a safe trip and I will be in touch, soon.