Have not heard from her

My imagine runs wild. She was smart to keep me in chastity.

Missed Call

Ring, ring, I heard iPhone chirping. I glanced over to my office, I was standing in the hallway talking to one of the senior partners, ring, ring. Then silence.

Sixty seconds later, a text.

Still, he droned on.

Fuck. As soon as he was done, I hustled through the door, feeling the tug of my garter straps on my stockings with each step.

Missed Call from Emily.

Text from Emily.

I called her back before reading the text, but she didn't answer.

So, the text:

Sorry I missed u, he wants to go to dinner, so can't call till later, jumping in shower to get ready. Think I should put on the babydoll you picked and tell him we should just get room service when he gets here? Love you!

Lunch

“Oh my god,” Emily texted me a bit ago, “lunch was like so weird.”

“Why,” I asked.

“It was like, idk, I was talking too fast, babbling, and acting like a schoolgirl with a crush. And I swear my panties are going to be damp now all fucking afternoon.”

Yea, and that made my cage fucking tight as hell. "Jesus, Em..."

"You better be sure, sure, Sara, cause I don't know if I can wait till tomorrow night!"

Texting

Sara: Morning, miss you.

Emily: Hey, miss you too, love, sleep well?

Sara: So, so.

Emily: Same, too excited.

Sara: For?

Emily: Silly, Adam gets here today, we're having lunch.

Sara: Oh, I thought he got there tomorrow.

Emily: Today. Tomorrow going to club, remember...if that's still okay :)

Emily: Sara?

Sara: Yes.

Emily: Is that still okay, sweetie? You haven't change your mind, have you?

Sara: It's all I can think about, Em.

Emily: I know, me too. And not just him, love, you thinking about it. So, is it still okay? If I decide to...?

Sara: You know I can't say no.

Emily: No, you CAN say no, Sara, you don't WANT to say no. There's a difference. So, yes or no?

Sara: Yes, of course yes.

Photolubitel

Source | Photolubitel

Who do you think is drinking that?

Something tells me it's not the woman holding the glass.

Source | dirty little tranny whore

Sandra

Source | Imaginary Wife

Encouragement

"That's it, sweetie, four inches down, four to go, just relax, you can do it.

The Heart's Dark Desires

"Oh, good, you're home..."

"He was just saying how badly he needed a drink, sweetie, why don't you slip on your French Maid's uniform and bring us something in the sun room."

Source | Mommy was a MILF

I want this!

You know, so I can suck cock while she's riding my face.

Source | GAG 5 - Penis Gag with Dildo

Flowers

Emily left for a work meeting this morning, a week out of town, one of her quarterly things.

First, I’m in chastity. Like, still in chastity, like, fuck, I’d have to look at a calendar to figure out how long it’s been (I looked, today is day fucking 23!)

Last week I’d hinted for several days that it would mean so much to me if she would release me before she left—it got so bad that on Thursday I begged her to let me fuck her, begged her to even just unlock me and jerk me off. Of course, I picked this fight at like eleven at night when we were both tired and about to fall asleep. Needless to say, picking a fight with your wife at eleven at night and angrily asking for, almost demanding, sex, is NOT going to end well. It’s not going to end with sex.

Emily didn’t talk to me Friday. Didn’t return my phone calls. Didn’t return my texts. Didn’t come home after work on Friday until about midnight. Well, when she got home, her sissy was waiting—with flowers and a sincere apology. I apologized for starting a fight at eleven at night, apologized for being bratty and needy, but reiterated my point that it wasn’t just sex I missed, it wasn’t just cumming (I missed them both) but intimacy, too, cuddling, touching, kissing, talking.

Emily thanked me for the apology and the flowers, explained herself, agreed that whatever I felt, picking a fight at night was not acceptable. But she kissed me and cuddled me and I don’t think her hand left me all night.

So, fast forward to Saturday night, dinner, wine, candles, music, simply a relaxing environment, classic Sara seduction of Emily. And it worked!

We found ourselves in bed Saturday night, kissing, touching, smiling, giggling; my body was almost shaking with anticipation. Until just before I started to kiss my way down her stomach, on my way towards kissing her inner thighs, to licking and teasing and making her...

“Sara,” she interrupted me, “just a second.”

“You want me to stop,” I said, hurt creeping into my voice, the emotions from the last few days and weeks flowing into my mind.

“Stop, no, god no, just before you...before you start...”

“Yes?”

“I appreciate the flowers yesterday, and the apology, you wouldn’t be doing this...”

“I know,” I interrupted her, wanting to get back to what I wanted to do, knowing where it would lead.

“You should have apologized, I’m glad you understood that, you were acting like, well, a spoiled child.”

“Yes, I...I know,” I said, feeling my sexual excitement start to ebb ever so slightly, which was sometimes a relief—it took the pressure off the swelling in the cage.

“And while the flowers were nice, your behavior was completely inappropriate and disrespectful and I think you need a consequence, too.”

OH FUCK, my mind was suddenly very alert, very focused, and very scared.

“You do?”

“Don’t you?”

“I...” I started to say that I supposed, but that didn’t seem strong enough, because she was probably right, was right. “Yes,” I looked down, very aware of just what that consequence was likely to be. “We’re not going to...”

“No,” she shook her head. “I would have, I planned to, but no, not now. Not until I get back.”

“Nothing,” I asked, seeking clarification, I suppose, if she meant no sex or worse, and more likely, that she wouldn’t unlock the cage at all.

“No, sweetie, not for you, anyway, you’ll finish what you started,” she grinned, “but that stays on until I get back on Saturday.”

My stomach sank—another week? Another fucking week? Worse, she wasn’t being evil or arbitrary, like a child, the consequences for my actions flowed naturally from my actions themselves. There’s a time and place for everything and that fight was the wrong time and the wrong place. I fought about being unlocked so I was not going to be unlocked before she left.

Which led to the second thing.

See, Emily has this thing where she asks my advice on outfits she picks up—kind of a Sunday ritual before she goes out of town. She models each outfit she’s selected to wear and wants my opinions on the outfit, the shoes, the accessories. Yea, she’s married to a sissy, so of course she asks me my opinion.

How's it go?

Well, she'll come out of the closet wearing something like this:

And I'll give my opinion (this one, needs jewelry or color)

Or something like this:

My comment, add the pink/black scarf.

Red skirt suit, easy, add a bracelet and a necklace, pearls or silver

We went through all her outfits for the week, then she came out of the closet wearing a dress similar this, no bra, and obviously, from the clings, no panties either.

“Emily, you can’t fucking wear that to a work event,” I gasped, “Jesus Christ, not even dinner after your meetings.”

“Obviously,” she frowned.

I just looked at her, waiting for an explanation.

“We don’t have anything scheduled on Thursday night and,” the frown disappeared and she looked down, almost shyly, almost ashamed, but not quite, “and, well, Adam, you remember Adam, my old boss, Adam will be there the second half of the week and...and he asked me if I wanted to go to this club, and so...it’s just us and...you know I have a little crush on him and...

“By crush you mean you’re attracted to him, isn’t that what you told me before?”

“A little, yea.”

“And how you used to banter with him? And flirt a little...more than a little...he’s going to think...you know what he’s going to think...are you really going to...” I started to ask, knowing she would not answer, knowing she loved to tease and torment, knowing that...

“Yes,” she whispered softly.

“What?” Did I hear her right? Yes? Yes? Did she say yes?

“Yes,” she said again, “I...I want to...I...I’m going to...you...,” she looked down at my midsection, where my cage was, where I was locked up, knowing without asking that I was swelling, that locked up, denied release for weeks, I’d never say no, I’d never beg her not to, that I would want it as much as she did.

I swallowed, looked down, too, ashamed at my own excitement, excitement magnified by weeks of denial. “You...you should pack something pretty to...to sleep in...”

“Will you pick something for me, Sara, something pretty,” she asked, looking at me with such tender eyes, eyes I can barely describe, the beautiful, lovely, loving eyes of a woman who knows, KNOWS how much I love her.

I did, a black and mocha fly away babydoll with matching thong panties, something tastefully pretty because Emily is tastefully pretty. Yet purposefully skimpy, so that if...when...she put it on for a man, for Adam, she’d do so in the bathroom while he waited for her in the bed, waited for my wife, knowing he was going to fuck her. She’d get dressed in the bathroom, that’s just something she’d do, come out to the candle lit room, and ask him nervously, “do you like it?”

Of course he would, both—the lingerie and her body. And she’d know, as he stared at her, as he stiffened, as stared at her with lust in his eyes, that she was wearing what her sissy, the love of her life, picked for her to wear. That her sissy, me, was home, locked up, imagining her in this moment, knowing the shy look she’d have on her face as her old boss started at her, welcomed her into bed.

Diet

A few things:

1. A sissy should eat her own cum. This is a given, something taken for granted, no? It doesn't matter the method or place of orgasm (a blow job, fucking a woman, a hand job, jerking off onto a woman's feet, whatever), sissy cum should, no, must, be cleaned up and recycled.

2. Many sissies don't want to eat their own cum. Oh, they do BEFORE them cum, then, suddenly, right when they do, they lose all interest. This is a bad thing.

3. One solution? Prostate milking, of course. This works particularly well with those sissies who find themselves in chastity, as a proper milking produces a weak, almost non-orgasmic release of cum, and more important, does so without that dreaded loss of libido that makes eating cum so difficult for most sissies.

4. What about a sissy who just simply refuses to lick up ever drop? There are clinics for that:

Chastity, obviously, is on my brain

Want

The dress and the figure

Source | The Art of Inspiration

Caged and Plugged

Perfect!

Understanding

Her friends didn't understand why she stayed with him after she found out he was sexting with one of the women he worked with. 

"We have an understanding," she'd tell them, waiving off their concerns.

"Once a cheater, always a cheater," one of her friends insisted.

"Oh, he'll never be doing that again, trust me."

"How can you be so sure," they insisted.

She laughed, "Why don't you girls come over Saturday night before we go out, you'll understand then."

So Saturday night, before their "girls night out" clubbing all her friends stopped by. "Let me go get HIM," she smiled, returning several minutes later with her husband in tow, "Say hello to the ladies, sissy."

"Jessica," her friends all shrieked at once.

"Think any woman would want to mess around with this," Jessica laughed, proudly holding onto her feminized husband, his little penis safely locked in a chastity cage.

Love the girdle, but...

That little thing NEEDS to get tucked away immediately!

Source | Sissy Incorporated

Introductions

Source | sissiebondage

The Reason She Cuckolds You

You can't even hold on long enough to get it in her.

Source | Cuckold Marriage

Mom's Helping Hand

Yes, her mother is the best person to help a new wife to get her marriage off on the right foot.

Duh!

"Um, do I have a date tonight? What do you think, I got dressed up like this for you?"

Love this picture

Because I love licking her through pantyhose and panties. It's like so naughty, licking and kissing and tasting a woman's intimates, and such a tease, denying access to her naked pussy.

Ohhh, the possibilities

Submission

Cuckold Marriage:

Nothing exercises a cuckold’s submission more than seeing his Domme collared, leashed and kneeling at her Dom’s feet. And, for the Dom, such an expression of submission on behalf of the cuckold’s wife is an incredible turn-on and source of pride in his pets.

So true, so fucking true!

His New Rule

I walked into the master suite carrying the try of drinks, heels clicking and clacking on the hardwood floor, the petticoats of my French Maid’s uniform rustling softly. My wife looked at me as I set down the try, caught my eye, so I took a chance and mouthed the words. “Is there anything else,” I asked her silently, hopefully, mentally begging and pleading.

She bit her lip, looked down as if embarrassed, and while he may not have seen me ask her the question, it was quickly obvious that something had passed between my wife and I, something that bothered her.

“What is it,” he asked her, putting an arm around her possessively.

“It’s…it’s nothing, don’t worry.

“What,” he asked again in that tone only a man, a real man, an alpha man could use.

She looked up at me, her eyes silently apologizing for what she was about to say, for the imminent betrayal. “It’s nothing, Jason, she just asked me if there was anything else, that’s all. But there isn’t, this,” she pointed to the tray of drinks, “this is all we need.” Her words were meant to diffuse the situation, to diffuse something, but her tone betrayed her. And me.

“That’s not what he’s was asking, is it,” Jason challenged my wife, purposefully referring to me as a ‘he’ instead of a ‘she’ something he did when he was displeased with me, knowing it only reinforced my humiliation.

She paused before answering, but did just the same. “No,” she said quietly.

“He’s asking about the key. Again.”

“Yes, but please, don’t worry about it Jason.”

“You didn’t tell him, did you?”

“Jason…”

We looked at each other again. Tell me what, my eyes asked, but she looked away again.

“I told you to tell him, didn’t I?”

“Yes,” she whispered.

“And if you didn’t, I would…is that what you want? For him to hear it from me?”

“It’s just hard Jason, I mean, I know he’s just a sissy cuckold to you, but…but I still love him.”

“As you should,” Jason said, “but that has nothing to do with this, so again, do you want me to tell him?’

“No, no, Jason, I…I need to be the one,” she sighed, then looked to me again. “Honey, Jason’s upset with, well, I guess I told him you’ve been bugging me to unlock you when he and I are together and…”

“Pestering you,” Jason chimed in, “you said he’s been pestering you non-stop, even after you said no.”

“Yes, well, he…he said that sissies shouldn’t pester their wives, I mean, you can ask, but, well, he’s right, I said no and you still keep asking and…”

“Go on,” Jason encouraged her.

“And he doesn’t want to hear me complaining about it anymore, you know he doesn’t like to hear me complain about anything about you, so…” She paused, looked me straight in the eyes again, seeming to steel her will, then rushed ahead and finished quickly. “He’s going to be holding the key from now on.”

My eyes widened, the walls of the room seemed to rush in quickly, smothering me. He was going to hold the key? Jason? My wife’s lover (a bad word because she did not love him), boyfriend (perhaps a better description), fuck buddy (also accurate, as he and he alone fucked her)? He was going to hold the key to the lock on my chastity cage? He was going to…to…

He snorted. “Obviously I’m not going to tolerate you pestering me to unlock you,” he said with a smirk.

“But when will I…will you…,” I started to ask, quickly thought better of it and shut my mouth.

He decided to answer just the same. “Rarely. Depending on your behavior, very rarely, and much less than you are now.”

Now was once a month, minimum, at least once a month she would unlock me and play with me, once glorious time a month, though often more, often twice a month, sometimes three or four times.

“But…but…I…one should…should

He held up his hand, stopped me. “Rarely,” he said with finality, “you’ll be unlocked rarely, a few times a year, maybe, and if you pester me like this, like you did her, never.”

“I…” I composed myself, tried to take hold of the terror running through my brain at the thought of my wife’s lover holding the key, controlling my chastity, determining when I was unlocked, when I could cum. I felt terror because I knew I could play on my wife’s love, on her sympathy, to let me out if I really, really wanted to, but Jason would never listen to that, would not care. “Sir,” I started again, knowing addressing him by title, formally, was ALWAYS a good start. “May I…may I say something.”

“Yes.”

“We, she, unlocked me monthly because, well, I know because I liked it, I know, but…but for health reasons, too.”

“I understand,” he said, “she told me. And I agree, completely. She’ll still drain you monthly, you’ll just remain locked.”

“He said I can milk you, honey, you know,” she lowered her voice as if ashamed of the words she was about to say, “massage your prostate until you…squirt."

Three Simple Rules

I may not cum unless:

1. I'm feminized

2. I'm in chastity

3. I have her cock inside me

Last time I was unlocked...

...I was not inside her and I was not allowed to cum. She made me rub it all over the outside of her lips, all over her clit, over and over and over, making her cum again and again and again.

And when I could take it no longer, when I was about to thrust into her, no matter what she said, she told me to stop, pushed me off her, and made me sit there next to her until I shrank enough to go back into my cage.

The perfect way to relax at the end of a long day

Forget the stress of the office, forget the comute home, forget everything. All you need to do is go to your room, change out of your boy clothes into something feminine and pretty, and go kneel by your master's favorite chair, drink in hand, waiting for him to get home.

Fences do make good neighbors

Required Reading

The Waiting Room

Ahhh, the fantasies an image can bring to mind. What better place for a sissy cuckold to spend a few hours, hours when his wife is entertaining a man in the other room, then on the punishment chair. Bound tightly to the chair, in a chastity cage, gagged with a cock gag, and a thick cock filling her sissy hole.

There's no escape, cock fills her mouth, cock fills her pussy ass, cock fills her mind, cock, everything a reminder, reinforcement of her place.

Work

Having a little work done on the house, wanted the contractor to do us a couple of favors that were beyond the scope of the contract. "Want me to talk to them about a change order," I asked her. "I'm sure they'll do that for an extra hundred or so."

"No, I'll ask," Emily said, "I think I might be able to persuade him to just take care of it."

"Really," I responded, "and how's that."

"I'll just ask him really nicely and say please.

Yea, something like that. So on Saturday afternoon before he showed up, she told me to make myself scarce. "This isn't something I should ask him when you're home," she said, coming out of her closet wearing short, like, really short shorts, a tank top, hose, heels.

"Fuck, Emily," I said, stunned, "you planning to fuck him, too?"

She chuckled, "not for a hundred dollar change order...but we've been talking about doing a new deck," she smiled.

So, yes, he agreed to do the extra work. Fuck, why wouldn't he if he has customers that dress like that. No deck this year, though, so I presume stayed dressed.

Pictures of You (2)

Since I'm thinking about it, this is what I picture when I think of Emily and her last boss, the one she had a huge crush on, the one she would often meet in hotel rooms for "meetings."

She'd tell him she didn't know if it was a good idea, if they should be doing this, she'd tell him this as the head of his cock touched her wet lips, she'd tell him, biting her lip, torn, torn.

"Tell me to stop then," he'd respond, holding, tense, wound, an animal, ready to strike. "Because if you don't..."

There's nothing, no words are spoken, five seconds, ten, she just breathes, heavier and heavier, unable to tell him yes, unable to tell him no.

And then he uncoils and drives forward, one thrust, she's so wet, he enters her in one thrust, deeper and deeper, filling her, opening her, possessing her. He says nothing, no words, simply grunts, as he pushes in, pulls out, pushes in, pulls out, over and over and over.

Pictures of You

When I picture Emily with Evan, this is what comes to mind.

Hard, rough, animalistic, intense, sex.

Not love making, not sweet, tender love, not soft kisses, not light touches.

No.

Sex.

A man. Fucking a woman. Hard. Making her cum. Over and over and over.

The eyes

When a man goes down on a woman and all she can think about is how badly she wants his cock inside her, her eyes will be open, she'll be staring at him, begging him to fuck her.

When cuckold goes down on a woman, she enjoys it, she really does, because he's so good at eating pussy, but her eyes are closed, she looks away, because all she can think about is how badly she wishes her lover were there right now. She doesn't look at him as he licks her because her thoughts are elsewhere, her thoughts are on another, counting the days until she gets to see him, gets to touch him, and gets to feel a real man inside her.

Bump

I can't tell what the bump is from, all I know is that I want to lick those panties and find out.

Sheer Panties

Love them...so sensual to look at, so erotic to lick, and thick enough to keep anything inside yet thin enough to suck anything through.

And by anything, I mean either her sweet nectar or his strong cum.

This is a long standing fetish of mine-the first woman who ever cuckolded me had a very pretty, very feminine sheer cream bra and panty set from Victoria's Secret that she used to wear when she "went out with the girls" and many Saturday nights I was awoken to the sight of her sheer panties hovering over my face, the scent, the musky scent of the mixture of pussy and cum, the feel of the dried crust, and the taste as she pulled my face up to her.

Feminization of Sally

Source | Feminization of Sally

Watching

Source | Lusty Inspirations

Well, you are fucking her...

...so no complaining, right? Sure, the eroticism is overwhelming and your little boy clit must be so swollen and tight inside your chastity cage, but, it's sex, and that's what you wanted, that's what you begged for.