Cuckold Olympics?

Last week, Sara Girl posted the chart below on his/her new blog (listed on our  favorite blog roll to the right). Looking it over, it seemed to be a "dessert list" for those of us who have dabbled in cuckolding over the years. Some tantalizing choices. Others a little too rich or fruity for our tastes.  It made me think of the various ski events at the Olympics.  Not every competitor does both the  downhill and the slalom. And then there are the frees skiers and mogul mashers, out on the fringe of the sport.  

But since we seem to be on hiatus from the new Boss's arbitrary directives this week, (Has he moved onto to a more pliant couple?) - it was tempting  to do what Sara did and comment on whether Mistress and her cuckold have dabbled in or are intrigued by these various Cuckolding "events":

1. "Voyeur Cuckold"- we've done this a bit , though not many of Mistress's lovers have felt comfortable with PDA's in front of pathetic cuckolded hubby.  Fact is, in our experience not many guys interested in "sharing" a sexy MILF really want the cuckolded hubby looking over their shoulder and taking notes. Nor do I think Mistress wanted me to share in her intimate moments with lovers.

2. "The Waiting Cuckold"- More our style. Mistress goes out on a "date", typically at her lover's home, apartment or hotel room, while the caged cuckold marinates in his own juices back home, waiting to hear all the juicy details and "clean up" afterwards.

3. "The Threesome" - only done it once. It takes the right (and rare) chemistry to pull this off. From this cuck's perspective, not nearly as appealing as #2.

4. "The Cuckold Threesome" - Apparently this would involve 2 guys with Mistress,  and the cuckold watching from a corner?  Mistress has high standards, so the thought of her finding two willing guys she'd be willing to share a bed with at the same time, who would also be willing to do it with the Cuckold lurking -- sounds like Unicorn country.  Plus we'd need to spring for a King size bed.  Forgettaboutit.

5. The "Escort Wife"- this involves Mistress getting paid to share the company of some wealthy guy? Must admit its kind of hot as a fantasy, at least for the cuckold, but can't imagine doing this in real life.

6.  The "Sissy Cuckold" - This involves the cuckold being "feminized". Mistress has never relished the idea of her Slave wearing her undies --would stretch them out too much! On the other hand the Boss recently shared some aspirational photos of a MILF and cuckold in matching stockings.  While the "humiliate the cuck" element has its kinky charms,  it's hard to imagine us competing in this event  any time soon.

7.  "The Gang Bang"-- Not our cup of tea. Mistress needs to be romanced a bit by her extraneous lover, which would exclude this sort of scenario.

8.  "The Bi-sex Cuckold"- Our only foray into the cuckold coming into contact with another man's equipment arose in item #4 above.  I guess you had to be there! It's not something we are likely to revisit any time soon, nor is it something  this humble slave dwells on, even in my darkest fantasies.

9. The "Cuckold Gangbang"- I guess this involves the cuckold witnessing the gang bang.  See response to item #7.

10.  "Dogging"-  Huh?  Maybe a reader can clue us in on this one.

11. The "waiting cuckold gangbang" - See response to #7 and #9.

12.  "The Submissive Cuckold"- This is our sweet spot, though most of Mistress's lovers never got the notion that her seemingly normal hubbie harbored submissive fantasies.

13. "Wife on Vacation with Her Lover"- never done that, but there is certainly a buzz connected with the idea of Mistress spending a "romantic" weekend with a hot younger stud while the caged cuckold  sulks at home, contemplating the slutty things she is up to.

14. "The Chastity Cuckold"- This is also the Molly and mick sweet spot.  Slave traditionally wore his cage when Mistress went out with a lover (or when Slave slept in the guest room down the hall).  But (as far as I know) said lovers were never informed of  my caged status, let alone ask to take custody of the  key (until our recent foray with the Boss).  That remains a pretty hot fantasy, at least for the Cuckold. 

Please let us know if there are other Cuckold Olympics events that we have not addressed here!

On Parole

 In response to all our readers' many questions (well at least one reader's question), Mistress did, ultimately, cough up the key and release her slave from what seemed like an endless sentence oto chastity -- but was actually only about 72 hours or so.  

Once home on Tuesday afternoon, she decided to let my "agony" play out a bit longer.

Fondling my strictly contained package she made her intentions to prolong my "agony" clear. "What's the  rush Slave? ....You seem to be surviving.  And if anything, a few hours in the cage seems to have made you a tad more devoted.... not quite as uppity as your typical macho self."

She also seemed to enjoy seeing me squirm in frustration as I knelt between her thighs, lavishing her with tongue strokes that I hoped against hope would earn her work-a-day cock its freedom and release.  But it's possible her repeated tongue induced orgasms may have  made her even more reluctant to hand over the key.

"You actually do that better with the cage on Slave.....there's a certain added intensity to your efforts which I could get accustomed to....."  Apparently (my) desperation is a spice that Mistress enjoys 

At one point she even blamed it on the Boss.  Which I suppose makes sense, since he put the idea into her lovely little head to dust off the cage in the first place.  

"I really should get his go ahead before springing you loose, Slave...."

After some texting with him that I was not privy to, she passed on an update.

"He wants you to beg, Slave....."

So I did my best grovel for her, kneeling next to the bed on which she was reclining, running through all of the reasons why I would be an even more devoted Slave should she spring me loose and give me the relief I'd been waiting SO LONG for. (By now it was Wednesday afternoon, and I'd been in that infernal contraption since Monday morning.

"No silly, he wants you to beg HIM...."

Huh? Had I really gone from Editor in Chief here at UCTMW to the point where I was begging our former Western Correspondent - the guy who's expense account abuses I used to point out- for the simple right to pee while standing up again.  Let alone fuck my wife the manly way? 

I swallowed my pride and engaged in a pathetic and lengthy text exchange with the Boss, during which I was required to apologize for all those times I called him on the amount of UCTMW cash he'd burned on high end lubricant.  Ultimately,  satisfied (or bored) with my humiliation, he texted Mistress and let her know she had the discretion to pop me loose. 

She showed me his "all clear", and I breathed a big sigh of relief.

"But before I actually exercise my newly granted authority, Slave....there's one more thing I'd like you to take care of.....

Key? What Key?

 So where were we?

Mistress, wearing her "peek-aboo" tights,  had been spanked and manipulated to orgasm in the rear of the Boss's car in the dark recesses of a parking garage somewhere in the 'burbs of the Mile High City.  We were safely checked into a roadside motel half-way to our Southwest Hideaway. Slave was caged at the Boss's "request", and before they traipsed off to his SUV for that little punishment session, Mistress had surrendered the key to my cage to her new Boss. 

The unanswered question: when the dust settled and Mistress had caught her breath following a firm hand spanking and a bracing cum, what happened to the key to my cage?  Had the Boss retained it for his collection?  Did  Mistress have the composure to ask for its return? Was Slave in store for a longer period of chastity that I had ever experienced? (After all I have been a pampered house slave up until now).

When I had raissed the subject in our drive south, Mistress had been coy.

"All in good time Slave...."

But she was clearly enjoying the chance to keep meet in suspense.  And when her hand occasionally wandered up my thigh and landed between my legs, she seemed to relish finding that hard steel lump containing her work-a-day cock. 

Over a light dinner,  her foot sliding up my leg as I squirmed in my chair, she confessed. 

"The Boss said I should tell you he kept the cage and was giving it to B [his long suffering wife, who knows about his kinky interactions with us].  But I actually have it....back in my purse."

I breathed a sigh of relief. So I get out of this thing tonight?"

"Not so fast Slave....he said no orgasms for either of us tonight.  And I kind of like the way you get desperate and more respectful  when you have that 'thing' on....."

"You mean?"

"I mean the cage is staying on, at least until we get home tomorrow."

It turned into a restless sleep for me.  Mistress kept those infernal tights on, and she seemed intent to press her legs or ass against me through the  night. The natural result was too frequent efforts of her work-a-day cock to grow, banging against its tight, steel confines.  Ouch. 

In the morning, with her own cum restrictions expired, Mistress made sure her slave worshipped her to a few satisfying orgasms.  But  that didn't loosen her grip on the key.

" I think you actually do that better when you have the cage on, Slave..... you seem more desperate for me....."

I couldn't argue with her on that.

Mistress's "Punishment"

 Mistress and her Cuckold / Slave  got back to our SW Hideaway yesterday at mid-day.  While it was nice to host our youngest for 10 days, we were more than ready to get back to "normal" life, including the right to engage in our sexual rituals without fear of embarrassing ourselves or our little darling. 

As we drove home, Mistress received a text from the Boss directing her to post her personal reflections on the events of Monday afternoon, including her "punishment".  But Mistress (believe it or not) is a little gun-shy about exposing her personal feelings on the blog.  That's why it's always fallen to her Slave to "tell the story".  So, risking her further discipline from the Boss, it's fallen to me to fill in the blanks, after fully interrogating Mistress at the point of my tongue.  Consider this an "oral history" that was surrendered in our drive home with some details filled in during the throes of oral ministrations  on Tuesday morning and afternoon.  Mistress was still cloaked in her peek-aboo tights!

.

Where we left off....

Mistress and the Boss disappeared into the recesses of  the darkened parking garage, heading toward his black SUV.  Slave slid into the driver's seat to wait.  About 15 minutes later the passenger side door opened, Mistress climbed aboard with the Boss looking over her shoulder at me....."Have a safe ride home, Cuckold".  He then leaned in and gave Mistress what was a lingering kiss on her generous lips, one that she returned with a little embarrassed enthusiasm.  After all, she's not used to kissing another guy in my presence.

She buckled up, the Boss waved goodbye, and we headed out of the garage.  In my mind there were two issues: what happened?  and where was that fucking key?

Over the next 24 hours, and with a little badgering from me, Mistress "came clean" about her private conference with the Boss.  Here's the download:

"So what happened Mistress....?"

"First, he spanked me, Slave...."

In his car?"

"In the backseat....."

"Over his lap?"

Yes.....he pulled me over his lap, held me down and pulled up my dress...."

"Through your tights?"

"That's right.....and it actually HURT, Slave.   He was mad I was laughing at first. But...

"So hard he stopped you laughing?"

"Yes......"

"Is your bottom still sore?"

"No.....it's OK now.  But he made his point."

"Did that turn you on.... the spanking?"

".......it was hot. He didn't hold back.  I was squiriming in his lap, but he said he could smell my arousal....  With those tights on, he could just reach in there between his spanks.  So he knew I was turned on and horny."

"What happened after that?"

"He pinched my nipples....making me squirm some more...."

"Through your dress?"

"Yes, Slave.... through my dress.  That hurt too, but not too much...."

"And then?"

"He fingered me....made me come....made me ask permission to come...."

'Awww.....poor Mistress....."

"He also says I can't cum again until tomorrow morning...."

"And you agreed to that sort of control?"

"I did Slave.....he can be VERY persuasive....."

Having gone through Mistress's experience, I had to ask my next question...."

"What about the Key, Mistress.... did he give it back?"

"I guess you'll just have to find out in due time, Slave......Now why not pay attention to your driving....."

To Be Continued.....