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!

6 thoughts on “The good bottle or the bad bottle?

  1. collaredmichael says:

    What a delightful dilemma. I think Kazander should fuck him a little anyways. But I look forward to hearing about it!

  2. greg says:

    Well, to help avoid him sensing who is in him, you can have Kazander wear a harness too. Then, if he feels the leather, he still won’t know who it is. And make sure Kazander has his body hair shaved/cut the same way you do. And make sure Kazander washes with the same soap and shampoo, wears the same, freshly applied deodorant/perfume/whatever that you are wearing. And both of you should stay close together so any sounds either of you make will sound like they are coming from whoever is penetrating him.

    Further, to avoid Sounder guessing by outthinking you, do repeated entries with guesses each time. You can have either you or Kazander go in randomly (you could even generate random numbers or use a lookup random number table), so that say sounder gets entered 10 times before getting fucked finally, in this sequence (K = Kazander, you = J)

    K, J, K, K, J, K, J, J, J, K

    Tally up how well he guessed. Then decide what the consequences will be for getting all correct, getting more of one correct than the other, just random guesses, or really play a mind game and don’t ever let Sounder know if his guesses were even correct or not, just tell him he was wrong and cannot tell a strap on form a real penis!

    Fun stuff!

  3. greg says:

    I saw this today, don’t know if it is true, but it sounds plausible:

    “…The receiving partner can’t feel the difference if a natural lambskin condom is put on the false phallus. Makes it feel, smell, and friction like real flesh, cuz lambskin is the lining of a sheep’s guts and it is real. This was my routine experience at that time in my life for us both.
    Gotta keep lambskin moist, but any water based lube or vaginal fluids will suffice. Sometimes we dripped fresh water from a handy water bottle to rehydrate the skin condom between changing positions. And had extras handy…”

    And, that could be a surprise, he is not expecting. No warning for Sounder that a condom will be involved for the testing part. then, the condom can be removed if that is the plan for the real fucking.

    You could even put a condom on both your dildo and Kazander’s penis, to make it even harder for sounder to tell.

  4. greg says:

    Oh, and don’t forget to minimize the temperature difference by keeping the dido next to your body or in very warm water until ready to use.

  5. soapyone says:

    Hi Domina Jen,
    How about a game of ‘Domme or no Domme’. It is played like ‘Deal or No Deal’? Only you use envelopes instead of briefcases. Number them from one to ? (depends on how long you want to play the game, say 20 or even 100), in each one, have a punishment, a chore, something You like, something Kazander may or may not like.
    Have Kazander take an envelope and ask him to pick an envelope. He never opens his until the end of the game, Unless he trades it in for the last envelope, that is. Giving up whatever task, punishment, reward, etc which was in the envelope. Of course, if he keeps the envelope, then he has to go through with whatever task it is.
    If he selects an envelope from the group, with let’s say a “Flogging” in it, you get to flog him. A “retention enema”, he gets a hot soapy enema, a “Bubble Bath”, you get a bubble bath, or maybe he does?
    These can have numbers, minutes, hours associated with them. A second set of envelopes with times and or numbers. So, if the enema envelope is selected, then a set of numbers from one to five for Kazander to select from. These will be the number of quarts for the enema. Then a third set of envelopes for the duration, say five minutes to sixty minutes. So, if Kazander draws ‘Enema’, then the number ‘2’, then then the envelope with the time of ’20’ minutes, he will be punished with a 2 quart hot soapy enema for 20 minutes. The timer stopping when the bag is empty.
    So, if Kazander draws something he hates or has never tried, but something You think would be fun, kinky, etc., then he has to follow-through with it. Of course, everything within a specific time frame. Obviously, if you put a trip to Paris, France in an envelope, Kazander may or may not need a second job to work up the funds for it. So, the time-frame for completing this task may be further out in the future.
    Items like a trip or a special vacation, need to be removed from the game once picked, unless it is a location close by and within Your budget. But the selections can range from a night, a day, a weekend or even a week or more of a celebration, task or chore for the two or more of you all to enjoy.
    Check out my blog when you get a chance. MM attempted to do a PA piercing on me last night to get me out of a CB6000s and into a Lori’s Tube 5b as soon as it heals, but it did not go as planned. My web site is listed in the send form and it links to my blog as well. It’s not as nice as a blog as You have, Domina Jen, but it’s a web site dedicated to mouthsoaping and the D/s lifestyle in general.
    Would you mind, may i have your permission to allow me to link Your site off of my web site?

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