The good bottle or the bad bottle?

I love games. Don’t you love games?

I totally love games.

I might have thought of a new game. Figuring out logistics will take some work, but it’s possible.

So Sounder is going to be fucked by Kazander. This we all know.

I was talking to Sounder about that today, specifically about how much of an eager sissy cockwhore he is with me, and how much he dreads being fucked by a man.

What, Jen? What would be awesome?

I’m glad you asked.

Okay, so Sounder has never had a real cock in him. He has no idea what that feels like. He doesn’t really know what to expect.

So here’s what I’m thinking. I’ll tie his wrists to his ankles and lay him on his side.

Like this, except with rope and on his side

And I’ll blindfold him, so he can’t see anything.

Then, either Kazander or I will come up behind him and enter him, careful not to touch him except for the cock.

And then, once one of us is inside him, he’ll have to guess who it is.

We’ll have to be careful, though.

Because if he feels a strap-on harness or bare skin, he’ll know who’s in him. He also knows my touch, so if one of us grabs or touches him, he’ll know.

I’ll have to use a new dildo, too. One right about the same size as Kazander’s cock, that Sounder has never seen. Preferably one of the ones that are supposed to feel realistic.

With him tied up like that, we should be able to get almost all the way in him without touching him.

Hopefully. And that’s where I wonder if it might not be feasible. There’s such a tiny margin of error. If he feels or senses or hears anything else, it’ll tip him off.

But if it goes right…

All he’ll have to go on is the cock inside of him.

If he guesses right, we’ll spitroast him, with me fucking his pussy and Kazander fucking his mouth.

If he guesses wrong, we’ll switch. Kazander will fuck his pussy and I’ll fuck his mouth.

And of course, I love the idea of Kazander being the one in him, and then when he makes his guess, I’ll take the blindfold off, and he’ll look up to see if he guessed right.

And he’ll look up to meet the eyes of the man whose cock is inside him right at that moment. Not only will he realize that a man’s cock is penetrating him for the very first time, but he’ll look up and meet Kazander’s eyes, as he feels his cock filling him up.

Whether or not he guesses right, that could be a fun moment.

Of course, if he guesses right, that means Kazander will pull out of him and start fucking his mouth. So he won’t have to be fucked by a man, but he’ll still be facefucked by one, and he’ll still have to swallow his load, and he’ll get to experience ass to mouth for the very first time.

But then again, that may be too easy. Sounder is very much aware of my love of a good mindfuck. And putting Kazander in him is definitely something I would do, just to fuck with him.

So he would likely expect that.

And besides, it would also be amazing if I’m the one in him, and he guesses wrong, and realizes that he could’ve had me fucking him, and instead he gets to deepthroat my cock (which was just in his pussy) while a man fucks him.

But he may expect that, too. Because putting Kazander in him is the obvious choice. He knows I’m not going to go for the obvious choice, so he may expect that it’ll be me in him.

In which case I’ll definitely need to put Kazander in him.

Really, it’s less about trying to determine what’s inside of him by the way it feels, and more about what he thinks I’m going to do.

It’s like that riddle in Sherlock and Princess Bride.

Did I put my cock in him, or Kazander’s?

“Did I give you the good bottle or the bad bottle?”

You know, except no one dies, and we spitroast a sissy.

How many times will I go back and forth before settling on the answer? What do I think he’ll expect me to do? What does he think I’ll expect him to guess?

Like I said, I don’t actually know if it can be done, but if it can, you’d better believe that’s what I’m going to do, and it’ll be so much fun!

Let’s play a game

I love the things Sounder’s depraved sissy mind comes up with.

He had a dream last week, that he shared with me.  In it, I give him the ability to help decide what I will do to him next time I see him.  I do this by telling him to find me a hot sissy caption each morning.  Each picture is assigned a number of points, and if he meets certain thresholds, he’s able to avoid certain unpleasant things.

Which is a fucking awesome idea, m’kay.  Like seriously.

So of course, this week, I wanted to do it. We started on Monday, and I’m going to see him on Sunday.  He sends me one picture each morning, and each picture is given a score between 1 and 5.

To avoid figging, he must earn 5 points.

10 to avoid ass to mouth.

15 to avoid Kazander Topping him for the entire evening.

20 to avoid being spitroasted.

25 to avoid begging Kazander to fuck him.

And 30 to avoid begging Kazander to be allowed to suck his cock.

The first two pictures he sent me were good, with one earning 3 and the other earning 4.  On Wednesday, the one he sent was really hot, and earned him 5 points.

On Thursday, he went with a different tactic.  Instead of looking for a picture online, he took one of the photos he’d taken for me, and added his own caption to it.

It was beyond hot.  I absolutely loved it.  And I wasn’t expecting it at all.  I broke my own rule, but the reaction he got out of me deserved something extra.  I gave him 6 points.

And that put him up to 18.

That picture shows his face, so it won’t be posted here, but the one he sent this morning is perfectly fine.

And amazing.

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I took the photo last Sunday.  He edited it and wrote the caption, and gave it to me today.

Definitely worth 5 points.  Which puts him up to 23.  And he’s still got two more days, and only needs 7 more points.

Next time we play this game, I’ll have to make it harder.  But isn’t my sissy so creative?

Jesse’s back!

So I don’t know if you guys know this, but there’s this adorably hot sissy I own.  Like, a million kinds of sexiness.

And for the past few months, he’s been dealing with some stuff that make typing about impossible.  So his blog hasn’t been active.  Which is fine, I told him not to worry about it.  It’s not like the blog is going anywhere.

And as it turns out, there are some really cool things he can post that don’t require a lot of typing.

Like sexy pictures that show off his sexiness.

Because I’m just a teensy bit of a fangirl of his sexy, slutty photos. Just a little bit.

And my darling slut is just so accommodating, sending me these amazing, hot, sexy, slutty pictures.  It’s my own personal sissy porn stash.

But you know, it’s selfish of me, keeping a bitch this hot all to myself.  The world should be able to see how unbelievably hot he is.  I should share him with the world.

So I very subtly suggested the possibility of posting them on his blog.  His very own sissy gallery, for the masses to appreciate.

And he, being the sweet, obedient whore that he is, quickly complied, posting three very hot sissy pictures on his blog.

I highly recommend checking them out.  You can find his blog, Sounds Like Jesse, in the sidebar (or down at the bottom if you’re reading this from a phone), or you can click here to see his newest post.

Shopping!!

Okay, so first, it’s been a few days on the antibiotic, and I’m actually doing alright.  Just nausea, headaches, and cramps so far.

And as long as I don’t eat or drink anything, and am not exposed to any kind of strong smell, the nausea is totally manageable.

The point is it’s not sucking as bad as the doctor said it would so far.  I’m keeping my fingers crossed.

And the past couple of days, I’ve had something totally fucking awesome to focus on.

Which would be shopping for a new bedding set for my darling sissy.

What he’s got on his bed now is typical of what you’d find in any normal man’s house.  And my sissy is neither normal nor a man.  So he needs something to better reflect his true self.

He’d be so much more comfortable in something that more closely resembles who he is inside.

Isn’t he lucky that he’s owned by the kind of caring, compassionate woman who would notice such a problem and work to fix it?

Actually, we can thank him for me noticing the problem.  He introduced me to a fantastic new sissy website, thesissystore.com, and I immediately fell in love.

No seriously, I love that site.

But as I was perusing through it, I noticed an unexpected category:  “Bedding.”

Now, the category was actually nothing special.  Just a couple of pillowcases and a pajama set (which my sissy already has).  But it gave me the idea to redo his bed.

A sissy bed for the sissy.  It’s so fitting.

But there are so many wonderful options to choose from!

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Like this one.

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Or this one.

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And isn’t this one lovely?

I mean, there are so many options.

Sooo many options.

And of course, solid pink isn’t the only one available.  There are some very adorable ones with pink and white trim.

 

I mean, just so precious.  And while I certainly love pink, we can’t discount other colors, either.  There are some lovely options in blue

So there is plenty to choose from.  Plenty of options to make him feel like a comfy, cozy sissy all night.

And some of them look very cute and youthful, but there are more “grown-up” options, too.

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Isn’t it so elegant?

And here’s the plan, I’m totally excited about the plan.  He’s going to order the set, but he’s not going to have a single clue about what it looks like, and it’s going to be shipped to my house.

When it gets in, I’m not going to tell him.  I’m going to go to his house, while he’s at work, and put it on his bed, and make it look all pretty.  Then I’m going to leave, so he’ll have no idea I was there.

He’ll get home, walk into his house, completely unsuspecting, then walk into his bedroom to see his new gorgeous sissy bedding there, waiting for him.

Of course he’ll know it’s coming, but he won’t know when.  He’ll just come home from work like any normal day, and there it’ll be, in all its pink, lacy, frilly glory.

I’m unbelievably stoked.

But now, it’s not all about just picking the prettiest picture.  There’s more to it than that.

First of all, the whole reason I’m doing this is to make him feel like a sissy.  All of these bedsets would certainly accomplish that… at first.

But he’s going to be sleeping in it every night.  He’s going to have to deal with it, day in and day out, indefinitely.

So that’s something to keep in mind as I’m shopping.  Some of those sets look absolutely amazing, but with all the bows and lace and frills, much of a pain in the ass is it going to be to take care of?  Can it be machine washed or does it have to be dry-cleaned?  How big and heavy is it?

And on that note, he’s a hot sleeper, so that’s something to take into account as well.  Super thick, heavy comforters may look pretty, but they’ll be just stifling to actually sleep in.  We live in Las Vegas.  It’s a desert.  It’s 120 degrees in the summer (that’s 49 degrees celsius, for my readers outside of the US).

It’s freaking hot.  Massive, thick, heavy comforters just aren’t going to work.

I don’t want the discomfort and the inconvenience of any set to start overshadowing the sissy factor.

So maybe something a little lighter, a little simpler, would be the way to go.

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And it being lighter doesn’t necessarily make it any less frilly.

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Isn’t this precious?

These are all super feminine and sweet.  So maybe a less-is-more approach will be more practical in the day-to-day, while still driving home the fact that he’s a sissy.

And then there’s another approach.  I could go with something more trendy and modern, something you might find in a normal, everyday woman’s house.

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Like this, isn’t this pretty?

And since Paris-themed bedding is all the rage now, maybe something like these.

So I mean, there are so many options that may be a little lighter.

But then again, I do love the more ornate ones.

So those are some great options.  But still, there’s more to think about.

Some of these are only available on sites like aliexpress or dhgate.  If you’re not familiar with either of those, think Amazon, but for Chinese sellers.  And not all of those sellers are reputable.  Also, most of them don’t speak English, or speak very broken English.  I’ve gotten a couple things from aliexpress, and I know some people who have had mixed experiences with either aliexpress or dhgate.  It’s a legitimate risk if you’re not buying from an established seller, and none of the sellers that provide these sets have enough of a history and enough customer feedback to make me feel comfortable buying from them.

And then there’s the issue of price.  Some of these are over $500.  And most of them are duvet cover sets, that only come with the duvet covers, bed skirts, and decorative pillows/pillowcases.  So I need to get the duvet insert and sheets separately.  I mean, that’s just insane.

So there’s a lot to think about.  And then of course there’s the humiliation sissy factor (ie, the fun part).  Eventually his entire room is going to be a beautiful, pink, sissy heaven.  It’s exciting.

I’m beyond excited, dude.

I can’t wait.  It’s going to be so epic when it gets in, and he comes home to see it on his bed.  I’m actually tempted to time it so that I finish up just as he’s getting home, so I’ll be there to see his face.

I’d have to do something with my car if I go that route, though.  I still wouldn’t want him to know, I’d want him to be surprised.  Seeing him walk into the bedroom, seeing the look on his face as he sees his new sissy bed for the first time would be epic.

And how awesome is it going to be the first time a man comes to fuck his mouth on his new sissy bed?  Man, it’s just an obscene amount of awesomeness.