Tuesday, June 26, 2012


Taking a weeks vacation on an island, will be spending time on a beach, drink constantly in one hand, Emily in the other. See you all next week.

The kind of threesome I dream about

Perfect panties for hiding his boy clit

"Of course you get to keep your boy clit, sissy, you just don't get to use it."


Source | sissiebondage

Properly Dressed Sissy

There is NO reason a sissy shouldn't be dressed like this EVERY day (I say that, in part, because Emily are in the midst of some chastity play and I've worn lingerie and a chastity cage, daily, for the whole month).

You'd be AMAZED how respectful, compliant, and appropriate a sissy acts when she's feminized by lingerie and emasculated by a chastity cage.

Sunday, June 24, 2012


"How do I look," Emily asked me, modeling the dress she was going to wear to out with her friends last night.

"Like you're going out to get hit on by men," I answered, the first thought that popped into my head.

"Yea," she smiled.

My clit tightened in the cage, not that it mattered, but I hadn't realized it was that kind of going out.

"Wait up for me," she said when she kissed me goodbye, "I've got plans for you later."

I raised my eyebrows and she knew exactly what I was thinking.

"No, sweetie," she looked down at my midsection, "not those kind of plans. I meant I have plans for this," she touched my mouth, "not that," she said, looking down again. 

Encasement = Chastity

They are saying, in effect, no, sissy, you can look, you can touch, you can lick, all for our pleasure, but that thing you want the most, to put your little sissy clit inside one of us, is NEVER going to happen.

Friday, June 22, 2012


He's smiling because there's a beautiful young woman in his kitchen and he assumes she is going to be a great lay.

She's smiling because there is a naked young man in the kitchen and she knows he is going to be a great lay.

My only comment...

Is that it's dangerous leaving a sissy home alone, unlocked. It's the equivalent of leaving a loaded weapon laying around in a house with a child. Certain thing should be locked up (you know the saying, "there ought to be a law...")

Well there should be. Kind of like a leash law, but in reverse. If you're going to leave your sissy home alone, he must, MUST be kept in chastity. It's for his own good and the good of society at large.

Simple Question...

Do you want to cum? Well bend over, then, because if you do, sissy, the ONLY way you're going to cum is with my cock in your ass.

Most guys loving cumming at the same time a woman does...

So does he...you can tell from the look on his face.

Sexiest Picture I Saw Today

Not quite what you thought about when you told her you hope you get lucky tonight, is it?

What...what do you want?

"Well that's pretty obvious. I want your mouth on my cock, sissy."

Mama warned you to watch out for pool sharks.

"It's always painful to lose," she used to say.

"Come on, work it!"

It's more humiliating if she just stands there and makes you do all the work.


"I'm not so sure about this, Amanda."

"Well I am, open your mouth and start sucking."

Black is always classy

Resistance is futile

(Like you really want to resist!!!)

Fucking. Beautiful.

The Opposite of Innocence

And then there is this. Nothing innocent when she dresses like this to go out, is there? She's leaving NO question what she wants, what she will get.


I love the duality of the innocence of her look, even her blouse and skirt, and the sexuality of her stockings. It's a look Emily, too, has perfected.

The thing EVERY sissy dreams about from the time she's a little girl

Interesting coat rack


Protest all you want, complain all you want, but no matter how much you tell her you do not like sucking cock, your sissy clit betrays you every time.


Anyone else look at this and find their mouth watering, thinking how wonderful it would be to get down there and lick that drop off his balls while he fucks your wife.

Or wonder what that is? Is she that wet, your wife, that excited to finally have a man inside her?

Or is that something else? Has he already cum inside her and that's just a drop that leaked out. He's thick, you see, his cock would trap his cum insider her until he pulled out. Of course, once he pulls out, there is going to be a HUGE mess for you to lick clean.


Ready for the day's training

I never have, but I surely would!

Take a good look, sissy...

...you won't be seeing these for quite awhile.

Thursday, June 21, 2012

Alexis Bledel

Rory Gilmore (she'll always be Rory to me), a/k/a Pete Campbell's dirty mistress, a/k/a, a very beautiful young woman.

Source | Bohemea

Wednesday, June 20, 2012

Sexual Harassment

"Oh, Mr. Emmerson, I thought you liked looking down my blouse, why do you have that look on your face? What, does looking at my breasts make you swell in your chastity cage?"

Would it have been better if she had reported you to management instead of telling your wife? Depends, management might have fired you but they never would have done what your secretary and your wife thought of.

His first pair of panties

Jockey 3329

Not a bad pair for a woman to start with when she wants to feminize her husband. Smooth, not overtly feminine (you don't want to scare him, you want to ease him into it), and tight enough to tuck.

If you want to go for a set, at first forgo a bra (you'll have him in one later, don't worry), and instead try something like this camisole and panty set.

Again, subtle, it's like the tee shirts he wears, just a bit more feminine and flattering to his trim figure.

"Honey," you can tell him, "it's not that I want you to wear women's underwear, it's just that this set fits you so much better than anything in the men's department."

A couple of things. First, make sure you call the camisole and panty set 'underwear' not 'lingerie'. That may scare him off. Men don't wear lingerie, but they do wear underwear. Yes, he'll be wearing all sorts of lingerie, later, but start slowly. Second, make sure you continue to emphasize that you don't want him to wear women's underwear (yes, of course you do) but that he's doing it for a practical reason (better fit).

You'll move to more feminine colors, over time, and more feminine cuts and materials, for feminizing him, getting him into lingerie, is the goal. Just start slowly, remember, the frog will not jump out of a cold pot.

Again, don't worry, your ultimate goal is to have him looking like this every day:

There is no better way to start your day than with a girdle and stockings like I did today.

How we'd all like to dress for work...

...and some of you, I know, hope to catch your the eye of your boss. Your male boss.

Did I post this? Because I meant to.

I love encasement!

Tuesday, June 19, 2012


The only time a wife should wear pretty lingerie around her submissive husband is when he's in chastity.

Look at the balls

Cuckold Marriage:
This image reveals much about the thoughts of her cuckold when he took it.
One might easily assume he took this to capture their coupling; the intermingling of sex organs, but that would be wrong. The subject of this shot, for her cuckold, isn’t the length of bare shaft left stuffed inside his wife while the picture was taken, but more importantly the testicles hanging beneath it and what they hold - soon to be released inside his wife.
Her cuckold knows she is eager for that release - a pleasure he has yet to be allowed with her.
I kind of thought that, too. Like, "Oh my god, he's going to cum inside her!"

Something I have not done for weeks and weeks.

Something I rarely do.

She wants me, sexually, but for my mouth, nothing more.

And then I thought, she'll want me when he's done, she'll want me once he's cum inside her, she'll want to there between her legs, to lick, to suck, to taste.

The Look I Want


Start with her stocking covered feet, sissy, her wet panties, too. You're a long, long way from earning anything more.

Chastity Clinic

When a wife wants to put her sissy husband into chastity, but doesn't quite have the heart to do it herself, she can send him to the Chastity Clinic.

The upside for the sissy? One last orgasm to make sure her boy clit is as small as possible before being fitted for a cage. (Don't worry, wives, your sissy won't be fucking the nurses at the clinic, they simply instruct sissies on how to masturbate to orgasm.)

The downside for the sissy? The smallest cage possible means even a slight erection is impossible, so any future orgasm will be possible only through other means (i.e., prostate stimulation).

50 Shade of Grey

Emily (finishing the book): Fuck that was hot!

Me: You think (I have not read it).

Emily: Um, yea, do you know how wet made me? I swear that's all I could think about for the last week.

Me: What?

Emily: Submitting like that, being told what to do, surrendering.

Me: I guess I never thought about being the dominant...

Emily (shaking her head): No, silly, not to you, submitting to a man.

Pony Girl

Now taking applications...

Telling you she's 'working late'...

...is a quicker way of saying 'I'm having dinner with my boss in his hotel room and I won't be home until after midnight because he's going to fuck me silly and you're the best husband in the world for understanding.'


Monday, June 18, 2012


Start with a dildo, it's less threatening to a confused sissy. Eventually, you can replace it with the real thing.


Stunning (and I wish I looked like that)

Insert Sissy Clit Here

Well you certainly didn't think she was going to allow you to insert it anywhere eles, did you?