The Cuckold Challenge

Even the most experienced "pussy-free" cuckolds often have thoughts of perhaps, maybe just one more time, being allowed to make love to their wives, or at least try.  If they did allow us, and that is a big "IF", it could be a very humbling experience.   

On the other hand, supposed they actually "challenged" us to do it...something like this...

From Miss Watson's Handmaiden

"Go on then, I dare you. You said you could fuck me just as well as he can if only I gave you a chance.

Well, here I am, this is your chance. Fuck me. Oh, I'm not joking. This isn't a trick. I'm not going to pull away at the last moment.

Fuck me. Show me what a man you are, that I was wrong all this time, that you're not a sissy at all, that you're a man, who can fuck me the way he does.

Show me I don't need him or his big cock. Go on, do it. Fuck me like he fucks me and I'll be yours forever. I'll do everything you want me to. I'll let you fuck me whenever you want to. I'll suck your cock. Let you cum on my face. Anal. Everything you ever dreamed of doing to me. I'll call him, tell him it's over, that I've found someone better, a real man, that I'll never need his perfect cock inside me ever again. I'll marry you, have your children, all of it.

But, if you fail, it's over between us. If you stay soft, if you cum too soon, if you don't fuck me to within an inch of my life and make me cum over and over on your cock like he can, then that's it. We're over. All of this, the clothes, the cage, the intimacy, our entire relationship, done.

So, what are you waiting for? Afraid? Afraid you won't be able to do it? Frightened your little sissy penis won't get hard after being locked up for so long? Worried you'll squirt as soon as you touch me? That your small, slender little penis won't fill me and fuck me the way he does? Afraid you won't be able to make me cum? That you'll disappoint me, the same way you disappointed that poor, nice girl that gave you a chance before we met? That I'll laugh at you. Tell you that you don't deserve a woman like me. That'll you'll never satisfy a woman, never be inside a woman ever again.

Or, my little sissy, you could accept who you are. Not a man, not even a boy really. A sissy. My sissy. My gentle, soft, tender, kind, pretty little sissy. Who loves her mistress and does as she's told. Accepts that she'll never have what he has. Never know what he feels when he's inside me. That soft, warm, wet sensation. Never feel me tightening and gripping as I cum on his cock.

Oh, gosh, his cock. Kiss me, darling, kiss me and lick me where his cock goes. That's what you're good at. Oh yes, like that. You can't fuck me like he does, darling. Don't even try.

This is what you're for. Licking, kissing, sucking. Oh yes, you're so good at sucking. Be my sissy. Let him be the man. Let him worry about fucking me, about dominating me, about dicking me down when I need to be put in my place. You just accept yours. Your place, beneath me, below me, on your knees, licking and kissing and sucking.

Good girl. That's better. You see? You see how much better it is? No more stress or worry, no more fear thar you'll never be enough. Just acceptance. Acceptance that you won't. Not like that anyway. Not like a man. But you can be enough like this. You can be soft and pretty. My girl. My handmaid. My sissy."

Hope you enjoyed.  Stop by Miss Watson's Handmaiden Tumblr blog.  She has some very interesting pictures, thoughts and captions.

Love,

sissy terrie 💔