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 💔

Sissy Golfing Buddies

I think I've mentioned this before but I'm a pretty decent golfer.  Though I don't play nearly as much as I did at one time, I can still shoot consistently in the 70's.  This humble sissy is not bragging, but the game always came easy to me.  Over the last 9 years or so, my largest handicap had been the chastity device that I wear between my legs.

But it didn't take me that long to get used to it.  Another challenge is not being able to stroll into the woods to take a pee.  I have to wait to use a regular restroom so that I can fittingly sit to pee like a gurl should!

Laci is a sissy friend of mine who is an avid golfer...kind of a golf nut to be honest.  I've been trying to convince her to golf while wearing her own cage.  It's taken awhile, but a couple of weeks ago, on Derby Saturday to be exact, Laci did just that.  And the results weren't bad at all.  

Here's the note she sent me...with a couple of pictures to follow.

 

Dear terrie,

I played my very first round of golf this morning in my pink clitty cage!  I have attached a picture of my outfit I wore.

It was on my mind the entire round, and made me think of my Mistress on line the entire day.  That being said this sissy did manage to shoot an 85 which is pretty good since half the time her mind was not on golf!

I also wanted to share a couple of pictures of what I am wearing at home this afternoon, to watch the derby, and a couple of super cute hats I wish I had!

I know lots of stuff, sorry girlfriend!
hugs,
laci

 

 

Too bad we can't see Laci's beautiful smile.  I know she was happy with that score of 85, but I know she has a 78 or 79 in her.   Maybe even an amazing "69" too!

This is actually Laci's favorite golf hat.  The wide brim keeps the sun out of her eyes.  The pink sash at the top is removable and is typically replaced by something a bit more manly when she's playing with "the guys."   Maybe someday Laci....

A Derby sissy favorite....

And another!

Thanks for sharing Laci.  See you on the links!

Love,

sissy terrie 👄

Very Fitting

I didn't write the caption for this, but it does fit me pretty well.

 

The panties?  Not so much.  Most all my "old fashioned" granny panties are size 6.

Hope everyone has a lovely Memorial Day weekend.

Love,

sissy terrie 💓

Thick Thursday - Cuckolding Edition

On most Thursdays in the past I used to post something featuring beautiful women with ample assets and curves.  I'm going to try do start doing this again with some regularity, sometimes with a little added twist featuring other little fantasies I have.  I hope you enjoy them.

The following is taken from the Tumblr blog The Bull's Delight.

Only another cuckold can understand that powerful force within that becomes so aroused when their wives are seeing and bedding other men.

Just the sight of your wife's nude body around the home can enflame passions even the cuck never knew were inside him. All you want and need to do is to tongue her body like the good little beta you are. That your tongue goes where other men fuck your wife just makes it so much more arousing. It's a fever addiction. One that makes the cuckoldress smile. She has the power.

Yes indeed, the cuckoldress does hold the power!

If you have any suggestions for Thick Thursdays just drop me a line.  

Love,

sissy terrie 💕

The Games Sissies (are made to) Play

When Dominant wives and the submissive sissy husbands get together....strange things can happen.

When Dominant wives who cuckold their submissive sissy husbands get together...even stranger things can happen.

When Dominant Wives who cuckold their submissive sissy who are locked in chastity get together...the strangest of things can happen.

I'll let my sissy friend Sierra tall you all about it.

Winners & Losers

           

"8 ball, corner pocket"

We met a long long time ago, in college. I was in the common room playing pool with a couple of my buddies. As I was lining up my shot, I felt a tap on my shoulder. I turn around and this stranger whispers to me.

            "Excuse me, but I thought you should know, the waistband of your pink lace panties are showing. You might want to adjust your shirt"

            My face must have gone pinker than the panties I was wearing. No one knew of my secret until  now! I excused myself and almost ran to the bathroom. After adjusting myself and heading out, the stranger met me outside the restroom. My face was burning with embarrassment. The stranger said hello, and not to worry that my secret was safe. And the stranger let me in on a little secret too, discretely pulling the waistband on his jeans down and exposing blue satin panties. We chatted for a couple minutes and exchanged numbers. I asked his name and he smiled and said, "call me Terrie".

            We now live on opposite sides of the country, but we still get together at least once a year. Not only do we both still wear painties, we've both been fully feminized by our wonderfully Dominant Wives! The four of us have all become very close friends. Our wives often share ideas on feminization, submission, chastity, and yes also cuckolding.

            Today has been the long awaited day I get to see my best and closest friend! We pulled into the driveway of a beautiful secluded home, and were greeted at the door by Terrie with a curtsy. She was wearing just a baby blue sheer nighty that came only to the tops of her stockings, and a thong that only just covered her tiny chastity cage. She gave me a big hug and a kiss on the cheek and pointed me in the direction to the spare room to drop our bags and get changed. I brought a matching nighty in pale pink that I quickly slipped on. I had already been wearing stockings and of course my chastity cage that was only slightly longer than Terrie's.

            When I came out to meet the three of them in the sitting room, Terrie had already gotten our wives drinks and they were quietly chatting when I came in. They were smiling and looking at the two of us who were now sitting on the floor in front of them. Terrie's wife was the first to speak up.

            "Girls, we have come up with a game for the two of you. We've decided to unlock your cages. You're going to play with each other's clitty and try to make the other cum as fast as you can."

            Terrie and I looked at each other with both delight and fear in our eyes. We've played this game before. We knew the rules. The first to cum was the "loser". The loser had to forfeit the keys to her chastity to the other's wife until the next time we saw each other. Since we live on opposite sides of the country, sometimes we only get together once a year!

            We then heard a noise behind us, turning around with shock in our eyes as two handsome, tall men were standing in the doorway. We both recognized them instantly. We were intimately familiar with who they were... It was our wives' lovers! Terrie's wife's lover spoke up...

            "We've also decided on a new rule this year. Not only will the loser hand over her keys, but she will also reduce the size of her cage by a half inch. Oh and one more... The wife of the loser gets to enjoy not only her lover, but both of us for the whole week we're together"

            As he finished the last rule it dawned on us. Whoever the "winner" was, would be denying his wife the pleasure of two hard, thick, cocks.

To be continued on Sissy Sierra's blog "Sub Hubby in Chastity."

Sorry,  you'll have to check back in to find out who the "winner" was.

Love,

sissy terrie 👄👄👄

Ruffled Tennis Panties

My very first pair of ruffled panties were almost exactly like the ones below that "Only Monica" could so sensually model!  

They were tennis panties...and I didn't even own a tennis dress at the time.  I'm showing my age because female tennis players haven't worn this style of panties in years...but I was quite young at the time I purchased them.  Monica certainly shows that they can be worn with just about anything! 

Here's a cute little video for sissies like me who love ruffles...

 To be honest, I wish all my panties were "tennis" panties!

Love,

sissy terrie 💗💗💗

Spanking Panties

"Go get your spanking panties" She said, the tone in Her voice reflecting how irate She was with me.  "The flowered ones."

The list of "things to do today" She'd left me hadn't been completed.  I didn't have a good excuse, not that any excuse would have mattered.

I have two different pairs of spanking panties.   One panty is a simple white panty girdle.  Its firming tightness seems to intensify the sting of the hairbrush, crop or hand when She spanks me.  

The other panty, the flowered one, is a full cut brief with a pink rose pattern on it.  That panty is reserved for spankings administered by Her lover.  Those panties are meant to intensify the humiliation of the spanking.

They always seem to do that.

Love,

sissy terrie 👄