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?

The Virtual Chastity Belt

The Virtual Chastity Belt

From a story about a rich, rude, unfaithful husband whose clever wife locks him into a virtual chastity device…

Doug visits a sex therapist and explains that he can no longer engage in all the sex that he is used to: sex with the three lusty assistants at his office who take turns giving him blowjobs at work. “I am the exec VP and own a lot of shares at Trinity Industries. I can do what I want. I just love to dominate my assistants. I make my girls come to work in short dresses, tight blouses and high heels. I get fellated by each assistant once a day. It’s just great!”

He also has a few out of town hotties who serve and service him whenever he goes to conferences …

And then, suddenly, he tells the doctor, his prick just stops working…. at least stops working for every women other than his wife. And his wife has taken over his sex and has become a little dictatorial:

“If I did just what she asked, we had a good fuck every couple of days. If I ‘disobeyed’ her, I would have to wait a long time. Pretty soon, I learned that I better not displease her in any way.”

When the beautiful sex therapist asks him what he has to do, he says:

“I have to be attentive all the time. Not play golf. Take her to the ballet. Go shopping with her. Suck her pussy. She made me read books on cunnilingus and practice on her until I was expert. She makes me give her massages and paint her nails. I’m giving her a lot more money to spend. Really, I cannot do anything that displeases her in the least.”

There is no key to this kind of chastity belt… except maybe the one that a real Mistress has…

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.

teased, tormented, denied…

Hello Mistress,

I realize that i haven’t called in a while but I haven’t stopped thinking of you. Lately, i have been fantasizing about you taking away my ability to orgasm. Well, not so much the ability to orgasm, but taking away my ability to have any pleasure other than yours. In this fantasy, I am locked in a chastity device for an indeterminate length of time, with only you as the one with the ability to remove it. I am teased, tormented, denied, for periods far longer than I have ever gone before. I don’t know where this could lead, and that is the thrill of it, not knowing. I just wanted to share with you. I hope life is beautiful and good for you and that I may have a chance to speak with you soon.

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She left her panties….

Good morning Mistress,

I just wanted to relate our most recent foray into chastity and humiliation.  I was off yesterday so S made sure to lock me into her cb3000 before she left for work.  She wanted to make sure that I didn’t waste my day touching myself.  So I did my honey-do list as required and she was very happy with my work.  She had a business meeting that she had to attend with several of her peers and she looked absolutely gorgeous in her black A-line skirt and white tailored oxford.  She left for the meeting and needless to say I was feeling the pinch as my cock strained in its prison.  In her meeting there was several men and women but one of which she is quite fond.  She had worked with him before and had repeatedly talked about how handsome he is.  Anyway, as I’m at home watching the news she texted me and told me to go look at the bed and I did.  When I got there I texted her back asking if she had taken her panties off before going to her meeting.  She responded that she had and that she was soaking wet looking at her handsome muse.  God I got hard as a rock!  She teased me a little bit more by saying that she saw the outline of his bulge when he walked in and he was very large, this only furthered my humiliation as I sat in my chastity prison.

When she got home the fun continued.  She got the Kept-for-Her dildo attachment for my cage and affixed it to the ring around the base of my balls and then led me to the living room where she grabbed the computer.  When attached the dildo is much larger than I am and I was somewhat embarrassed by the whole thing.  She lifted her skirt and backed up to me while I was on the sofa.  She opened her legs and straddled my lap and slowly lowered herself onto the dildo.  As she did she said, “Wow, now THAT is a cock!”  She told me that she was sure that the phallus in her was about the same size as she imagined her friend’s to be as she fucked herself to several orgasms.  I was well and truly almost crying from frustration at this point.

When she was done she turned and kissed me and thanked me for letting him fuck her so well.  How humiliating!  She then finished undressing and she led me into the bedroom.  I was sure that I was going to be allowed to fuck her at this point but she had a surprise for me.  She handed me a little gift bag and I opened it to find a Fleshlight that looked like a pussy!  She released her cock from the prison and told me that I could fuck the fake pussy while she watched!  I begged her to let me inside of her but she was firm that that wasn’t going to happen for a while and that if I wanted to feel a pussy that my little cock better get used to the fake one!  I was so humiliated!.  She sat on the edge of the bed while I knelt in front of her and stroked myself to orgasm with the Fleshlight feeling completely useless.  When I was done she had me reattach her cage to her cock and we went to bed.

I don’t know what came over her last night but I loved it and hated it all at the same time.  Maybe a case of be careful what you wish for!


Deliberation by Teased and Denied: A good one

Deliberation Ch. 01
by Teased and Denied ©
Mistress Stephanie grabs my hair and pulls my head back. She looks me square in the eye, a very serious look on her face.

“Slave, are you sure you want me to do this to you?”

“Yes Mistress,” I say, almost regretting it already.

“Say it. Beg me for it.”

“I want you to hold the key to my chastity belt, Mistress. Please take it and use it to tease and torture me. Please teach me how to be a good boy and not a pathetic wanker slut.” Mistress slaps me in the face lightly, smiling a little.

“Tell me why you deserve it, slaveboy.”

I swallow, remembering the words she made me memorize earlier, after the Interrogation and Confession session. “Because I’m a pathetic wanker slut. I can’t keep my hands off my filthy prick, and I can’t control myself. I need to be locked up so I don’t have the opportunity to disappoint you.”

Mistress looks at me deeply. “I’ve been very displeased with you recently. You can’t seem to follow orders not to cum. I bring you close to the edge and hold you there, and you find some way to spill over, spraying your disgusting seed all over yourself. Furthermore, you have confessed that you masturbate every day, sometimes twice a day. I find this unacceptable. An orgasm should be special, something you treasure and look forward to. Your endless wanking has made it mundane and commonplace. For this, I will take them away from you. I believe that once you really know what it’s like to suffer for one, you will come to thank me.”

“Yes Mistress,” I say. Mistress nods and kneels down between my legs. My cock is throbbing inside the plastic cage. The lock is in place but isn’t closed. Mistress smirks to herself as I hear it click shut.

“I am going to make your life a living hell, slave.”

“Yes Mistress,” I breathe, sweating. My stomach tightens – this is going to be really hard. Mistress Stephanie knows just what my private thumbscrews are. In the interrogation, she squeezed out all my secret fetishes and desires, and I just know she’s going to use them against me. Get inside my head. Turn me inside out. I’m going to be completely hers. Owned. Property. Not a person, just a toy.

Mistress Steph unhandcuffs me from the chair. “Give me the key now, slave,” she commands, snapping her fingers. I scurry, naked, over to my backpack, where the key to the chastity belt is hidden. I hold the small key in my hands, turning it over. This is my last chance to turn back.

“Give it to me,” she commands again, impatient, tapping the toe of her sexy boots on the floor. My guts are turning in knots. I don’t know if I can handle this.

I DO have a masturbation problem. I am a young male in at the height of my sexual potency. I can get off two or three times a day without depleting myself. My mind is constantly on sex, always looking for something dirtier or something more twisted to get off to. Mistress has slowed me down a bit, but in private, I still jerk off – in the shower, before I go to bed, sometimes even at work. This is going to be a big change.

She had an air of annoyance in her voice. “Now, slave. The longer you wait, the worse I’m going to be on you.” She held her hand out, her palm open.

I tried to plead with Mistress yesterday when we were talking about this arrangement. After that brutal interrogation scene, and then that humiliating confessional session, I was really in no place to disagree with her, only acceding to her wishes. I begged her that we should take this slow – that we should start off with only a few days and then slowly increase – so I could get acclimated. In a dismissive tone, she said she’d consider it.

“One,” she counted. I knew much better than to let her get to three – but would the punishment for backing out now be worse than the treatment itself?

“Two,” she said sharply, her foot still tapping. This is really the last choice I get to make for some time. I know that this, too, is an illusion… even if I don’t give her the key, she’ll find some way of torturing it out of me. Oh god this is going to be awful. I swallowed. I handed her the key.

“Good boy,” she said. A feeling of helplessness came over me, a sort of rush of the loss of power. With it, there was a brief sense of serenity, but it was in the midst of near panic. Mistress Steph sat down in the chair in front of me. I was hers now, no question about it. She had my key and I was her lock.

Mistress Stephanie snapped her fingers and pointed at her pussy. She lifted her skirt and said casually, “well, get to work.” Her breath was longer, deeper. I could tell that she was really getting off on the power she was just handed. Waves of submission brought me to my knees, a tide against which I am helpless. My face pressed against her pussy, my wet tongue snaking out my mouth to contact her gorgeous shaved sex. She was soaking wet already; I teased her with my tongue, flashing over her lips and flicking her clit very softly.

“No slaveboy, I need you NOW.” Her hand tangled in my hair, she pressed my head forward into her, burying my face in her delicious folds, intoxicating me with her bouquet. She smelled like sweat and leather and orgasm and ecstasy. I could feel her alabaster thighs clamped around my head move with her breath, deep and moaning, coming up into a crescendo as I attacked her pussy with my expert mouth. She must have been close to cumming before I had even touched her. Nothing turns me on more than knowing my submission is getting my Mistress off.

As her cries fell off, she jerked my head back by the hair. Her face was flush, breathless. She grinned at me, “good boy,” and then pressed my face back into her. Pushing her hips forward into me, I worshipped her with my tongue. My cock was swollen, painfully crushed against the plastic cage.

“I almost feel bad for what I’m going to do to you,” she said as I squirmed under her skirt.


I just wanted to thank you for our session Saturday night. You helped
me focus more clearly on putting my wife’s needs before my own silly
desires to some great results. We spent a great day together with
lots of teasing and sexual innuendo. That night, after being locked
up for the weekend, she allowed me to pleasure her orally and fuck her
with her favorite dildo. I love watching her cum! She was so happy
with my attentiveness that she actually unlocked my cb-3000 and let me
masturbate! What an erotic and humiliating night we had! She watched
as I stroked my little clitty and reminded me that it was a shame that
I couldn’t satisfy her myself. That sent me over the edge and I came

Anyway, I just wanted to thank you for your guidance, you truly own my sex.