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 💔

Cuckold Sundays

Happy Sunday!

When Diane's Lover spends the night, I always have to make sure I'm up early enough to serve them coffee when they wake up.

Diane might simply open the master bedroom door and shout out "Coffee please?" or something similar and I make my way upstairs with two piping hot cups of coffee just the way they like them.

I'm also dressed appropriately.

Not very sissy, but very "fitting."

Love,

sissy cuckold terrie 💗💙💗

Frilly Friday & Cuckolding

Happy Friday everyone!  A few pictures t

I think this is a good analogy.  How many times have we, members of the sissy sisterhood, purged our panty collection hoping that it would rid us of this "habit?"  How many of us were successful?  I rest my case.   

Not only are we trapped, but panties make us do the most feminine and submissive of things.  I never thought I would actually (fill in the blanks)...

I couldn't help but make this the featured panty today on Frilly Friday.  This handmade gem is from Strumpet & Pink, a designer of handmade silk lingerie in Great Britain.  The company was featured today on Ellen Lewis' Lingerie Briefs.  Get yourself on Ellen's email list.  You won't be disappointed. 

I don't think a week goes by without my having one ore more bridal or wedding fantasies.  Sure, most of them involve my wearing a beautiful wedding gown.  Others, not so much....

Tonight's a date night for Diane.  Karl will be here for dinner and more.  Drinks (an extra dry Bombay martini for Him and a glass of Sauvignon Blanc for Her) are at 6.  Dinner will be served at 6:30.  After that, the schedule is open.

Love,

sissy terrie 👄

The Panties Make me Do "IT"

Earlier this week Diane's lover Karl stopped by.  It was a planned visit with the purpose of seeing one another before we left on our vacation this weekend.   Their intimacies began as soon as She got home from work.  There was a break for dinner, a swim in the pool and he stayed the night.  They both got their fix.

In the "middle" of it all, some time before they both drifted off to sleep, I was called to the master bedroom to serve the two of them as a good sissy cuckold often does.   My duties involved oral service for the both of them after they'd had sex.  Karl was first but only for a brief moment before he suggested I tend to Diane, which I did.  

Diane's satisfaction from the sex with Karl was evident, as was Her surprisingly elevated state of arousal.  I've spent enough time between Her beautiful thighs to be able to tell when She's highly aroused.  This was one of those times and it didn't take long for Her to have another orgasm.  This time from my oral attention as opposed to Karl's more manly ways.  I thought my time with them would be called "over" but it wasn't.  Karl wanted, and needed attention.

"What about me?" he asked in a more demanding than asking tone of voice.  It surprised me.  Apparently, laying by Diane's side and observing as I attended to Her made him "rise" to an equally elevated state of arousal.  "It's my turn" he said.

It was more of a direct order from him than any I'd ever experienced.  It wasn't said in a demeaning or angry way, but his intentions were certainly made known.  I made eye contact with Diane and Her smile was all I needed to know that I should follow through with it.  I did.   While Diane watched and teased me a bit, Karl held my head in place, moaned with evident enjoyment and in what seemed like a longer time than Diane took, had an orgasm.  Diane urged me to take it like a "good girl."  

They both thanked me for my services and I was dismissed.  

Similar scenes have played out like this before, but not in such a powerful way.  Part of it was the timing of it, the element of surprise, Diane's active/passive role, my own willingness and Karl's firm but understanding demeanor.  

It led to some pretty deep reflection on my part.  Beginning with my earliest crossdressing experiences I thought about how I would never have thought about doing such a thing with another man.  I would go out of my way to avoid and even decry any hint of bisexuality and insist I was one of those "totally heterosexual crossdressers" I had read about.  I realized that as I matured and experimented with increasing levels of dressing and femininity, a change had come about.  Eventually, I went through with the urges I was experiencing.

I also realized that for me, my bisexual urges have everything to do with femininity.  I could never, and Diane knows this, do what I did with Karl if I wasn't dressed in a feminine way. For the record, I was in a short pink sleeveless nightgown with white Vanity Fair Lace Nouveau panties.  If I were dressed as a "male" I couldn't go through with it.  

When I slip on a pair of panties, I feel very femme and become very submissive...

Simply put, "the panties made me do it."

Love,

sissy terrie 👄