Check Mate

Get it?  Check... MATE! 

Now
After winning this game and taking him out for that date, I think I’ll up the stakes again.  A blowjob?  Yeah, he loses again and he wraps those luscious painted lips around my cock after our next date.  He obviously wants something like that to happen so why not just go with it?

I’m gonna get back.  This game will start it.  Just one win and I can turn the tide.  Damn, I thought the nails would be annoying to move the pieces around, but this lipstick is even worse… I can’t get away from tasting just how feminine I am.  

One Day Ago
He still can’t see it.  Even without cheating he can’t see that he’s three moves from checkmate.  I wonder…  with his frame, is he going to looks more like Zooey Deschanel or Mila Kunis once his hair is dyed dark? 

Fuck, these nails make it impossible to forget just how much I’ve changed.  Sure, I could see the jewelry before and hear it clank around but I have to change the way I grab the pieces now.  How the hell does he keep winning?  No, don’t focus on that now.  I win this one or I’m gonna have to wear a full set of makeup and color my hair.  I thought he’d prefer me as blonde, but I guess he’s no gentleman.  

A Day Before That
Whoa, he suddenly got better.   Did he watch some tutorials or something?  I should probably let him win this one… but damn, I really want to see how he looks in nails and want to see him in that skirt I picked out for tomorrow.  I mean, what’s the use of all that depilatory cream if I don’t get a look at those gams!?

Okay, so watching The Queens Gambit didn’t help.  I thought maybe that's where he got his moves from, but evidently not.  Well, it helped me into giving up all my guy clothes and having to wear this fucking jewelry all the time.  There really can’t be anything more feminizing than these rings and bracelets.  Well… feeling my now hairless thighs rub against one another might top that.  

And A Day Before That
Nah, he’d probably notice if I changed the rook to white.  He just placed it there a few moves ago.  Oh hey, there it is… change that pawn to white and he can’t trap my king.  Now, if I want to hear those bracelets clank with every move of his I need to figure out how to trap his king.  

It’s perfect.  Sure, it’s hard to concentrate since I can feel my chest jiggle and shake with these damned breast forms and bra on, But I’ve got him now.  At least I won’t have to go hairless.  I win this, I get to take the breast forms off, win the next one and can go back to my boxers, and then we’re back at even!  Wait… fuck that’s not my pawn, it’s his.  Damn it, how did I miss that?  Now I can’t trap his king!

And A Day Earlier
I guess he really wants this.  I mean, why play a second game once he saw how it works.  Maybe he feels better with the charade of betting on and losing games of chess.  It probably hits up the intellectual side of his psyche.  Hey, maybe on the next one I can make him speak like a bimbo!  No… no, he has to look the part first.  After he’s all femmed up, we’ll get him acting like MY perfect mate!  Heh… check mate.  I get it now.  

Damn it, I can’t lose two games in a row to this shlub!  I just have to concentrate harder.  Yeah, that’s it.  It’s this string riding up my ass and this flimsy material holding my twig and berries back.  Wearing panties sucks!  At least if I win I can take them off and I won’t have to add the bra.  And what does he mean by ‘something to fill them out’?

The First Day
“Hey buddy, you gotta check out this chess game I just bought.  I bet I could even beat you with it.  Seriously man, put that book down and check it out.  With this button I can change any of the black pieces white.  How could I ever lose.  Wanna play a game?  We could bet something ridiculous… loser has to wear a thong!”

Why does he always talk to me while I’m reading?  Yeah yeah yeah, a chess set.  It’s cute and all, but I’d just destroy him at chess and we both know it.  It’s not as important as getting ready for this project at work…. Wait what?  “So you wanna play chess with your new cheap board and the loser has to get all girly for the winner?  Hell yeah man!  You know if we keep these games up and I keep beating you, I’ll make you my perfect mate!”

source:  The wonderful Tasha Grey shared this on a discord server.  I did find that the image is of Irina Shayk in a shoot for Harper's Bazaar.