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!

Being sick

Isn’t enough to keep an eager cockwhore from being an eager cockwhore.  As I found out the other night.

I’ve been fighting the biggest bitch of a cold that last couple of weeks.  I haven’t felt up to playing at all.

But it had been too long since I’d seen my sissy, and Sounder has been suffering from the same cold.  After a couple of weeks of trying to stay as far from other people as possible, the idea of spending time with him, cuddling, enjoying each other in all our sickly glory, sounded amazing.

I didn’t even bring my toy bag with me.  Neither of us were up for a session.  But watching TV on the couch with a glass of wine was absolutely within the realm of our capabilities.  And for once, I didn’t have to worry about quarantining myself from all human contact.

I got to his house, walked in, and gave him a hug.  He was dressed in boy mode, but when I reached around, I felt the bra band across his back.

Which made me immediately smile.  Even sick, he still thinks of me.

He poured my wine, gave me my Christmas gifts (which became the inspiration for my new absolute favorite insult, “four-day-old tampon slime.” God, I fucking love this chick), and we sat down to watch a show we both love.

I wrapped my arm around him and pulled him close, running my other hand across his chest.  It seems like only a moment passed before my fingers went, almost of their own accord, to the buttons on his shirt.  Once they were undone, I couldn’t help but grope him under his bra (I mean, I’m sick, infirm, and weak.  Of course I couldn’t resist such an attractive temptation), teasing his nipples to little buds, then pinching and twisting them until the pain made him wince.

The way he moves…. you guys have no idea how hot it is, the way he moves.

Next came the button and zipper of his pants, and I reached in, fondling his clit and grinning to find that Tammi Lynn was already wide awake, bursting out of his pretty, lacy panties.

Funny enough, suddenly I found myself feeling quite a bit better.  I rubbed his P-spot, biting his neck and ear, whispering to him about the way it’ll feel when a man first pushes his cock into Sounder’s tight, pink pussy.

“You’ll try not to like it,” I told him as he squirmed and writhed and gasped underneath me.  “You’ll try to keep yourself from loving it.  But it’ll feel so good, having him deep inside you, pounding his cock into you.  You won’t be able to stop yourself, you’re too much of a whore.  You’ll want it.  You’ll push back against him, begging him to go deeper.  Faster.”

I put fingertips of my other hand against his lips.  “And when you feel that second cock push its way into your mouth, all you’ll be able to do is suck it hungrily, wanting it to fill you up just like the other one is filling you up.”

He gasped, parting his lips, and I shoved my fingers in his mouth, forcing them down his throat while I massaged him, while I watched him get closer and closer to the edge.

“You’re going to cum with a cock in each hole,” I whispered.  “You’re going to cum hard and often, and every time you do, it’ll just make you want them deeper inside you.  Come on, show me how much you want that cock in your mouth.  That’s a good girl.  Show me how eagerly you’ll suck it.”

He didn’t disappoint. Writhing on the couch, one hand between his legs and the other fucking his mouth, whimpering and sucking, his hands balled into fists, he came to the thought of being spitroasted by men, his illness, for the moment, forgotten.

I couldn’t help but laugh.  “Being sick isn’t enough to keep such a greedy sissy down,” I said, giving him a moment to recover before rubbing him to another orgasm. Or three.

Sure, we watched TV.  And it felt good, especially as achey and cold as I’ve been, to feel his warm weight against me like that.  It felt especially good to see how easy it is to wake up the slut in him, even when the rest of his body just isn’t feeling it.

My slutty, pathetic, adorable, hungry sissy.