The Predicament of Chastity

Continued from: Time for a Recap

I don't operate a rub n' tug. You don't just roll in here for a blowie or a handie...silly boys!

If you are male and a client of my Facility it means you are in a 24/7 chastity device with no access to the keys. You better believe you're going to pay for your orgasms, when they're permitted! Both financially and psychologically. 

"Aww, is someone crying little chastity tears? Would you like Mommy to unlock you?"

As described in the post called: Remember, be girly, I began to offer a service at my Facility where chaste males who had just been spanked and had finished their 20-30 minutes of cornertime, could be jerked-off to orgasm. 

To be eligible for this service, the silly male would have to be in their cock cage for 30 days minimum and pay an additional fee of twenty dollars, on top of their overall session fee (which is quite a bit more than that).

The other dreadful condition, is that my sissy Secretary, Kaylee, would perform the handjob. Yes, Kaylee is almost 100% passable as female, but my male clients still know Kaylee is a dude and that they're being jerked-off by a dude. 

They usually hold-out beyond the 30-day mark, trying to fight their desperation with their own machismo and homophobic ideologies. But by day 38-ish, they're calling the Facility, sniveling and whining to be unlocked, begging for a spanking session with handjob ending. 

In comes Kaylee, I personally remove the cock cage from the client and my sissy works the cock until there are ropes of hot cum all over their stomach, all over Kaylee's face or both. 

I mentioned in a previous post that I keep an elegant, feminine pair of leather gloves in the refrigerator. Immediately after the client cums, these gloves get handed to Kaylee to be put on. He will continue to handle and fiddle with the client's cock until it's dreadfully cold, shrunken and limp. The chastity cage is locked back on, I retain the keys and the client's session is over.

Time to fuck with their minds just a little more! 

We began to advertise and offer a blowjob program, BUT! Here are the conditions as it was written in our feature-sheet we sent out to the clients:

My caged boys who have been locked for 30 days or more, know they may ask for a handjob to orgasm at the end of their session, for an additional cost of $20.00.  However, if you can hold out just a little longer for Mistress, you'll have a soft, delicate, warm mouth...to cum into!

That's right my little pets, any client who has been locked for 60 days or more, may ask for a blowjob!

Wouldn't that feel nice, can you make it 60 days for me?

It's only an extra $50.00, added to your original session rate. 

Mistress Andrea xoxo

What a mind fuck huh? Hehe

Do they hold out for 60 days, can they hold out, just to get a blowie? Or do they jump the gun and just take a handie by day 30? 

They all know it's going to be Kaylee doing it, so they have that mental hurdle to deal with too. I've said it before, chastity and denial does wonderous things to silly boys.

Or...they safeword out of this mental torment completely, their chastity keys are returned to them and they are no longer clients.

This was fun! So enjoyable that Summer and I put a bet on who would break first. Not who actually...but when. Closest to the number of days without going over was our terms. 

Our wager...which I still can't believe I suggested, was a bare naked, very real, hairbrush spanking for the person who loses the bet, administered by the person who wins. 

Summer has never ever spanked me and never Domme'd me before, but it didn't matter. I wasn't loosing this one. I know my clients better than she does.

I had someone in mind, my winning horse! We weren't picking names of people, just the time it takes them to break, but I had a specific person in mind. I took the cocky route and chose 60 days, exactly. 

Summer knows a few of my clients but not all of them. I think she just randomly picked a number. She settled on 67 days, we both smiled and shook on it. 

To make things a little more real, we both agreed on the brutally severe, antique, ebony hairbrush.

Even I started to feel a few butterflies, questioning my cavalier selection of 60 days. This is gonna fuckin' suck for whomever loses this bet!

Just to rub some salt in it, we deliberately displayed the vicious brush on the fireplace mantle of our room, where it would stay, as a reminder, until the bet is "settled". We wrote down

Andrea: 60

Summer: 67

on a little piece of paper and slid this note under the backside of the hairbrush. I guess if she really wanted to be a bee-otch, she would have just picked 61 days, and cock-blocked me. A client could hold out for 200 days and Summer would still win, as she didn't go over and is closest to 200. Remember those losers on the Price is Right? That first bid thing and some jackass would fuck everyone and just bet a dollar. I'm glad my darling Summer is too young to remember that show, I doubt she's ever seen it. 

Haha! 

I loved how poor Kaylee didn't even know he and his mouth are now being wagered on for sport! The end result of all this shenanigans will be a 60+ day, pent-up river of ejaculate, being blasted into his mouth from an erect cock. Poor poor sissy! 

We decided to bring Kaylee upstairs to break the news to him. He knew that client cocksucking was now being offered but I wanted to explain my expectations. 

We didn't mention our bet but I touched on the 60-day minimum and a few of the other rules. 

I explained that after the clients had finished their full session, whether it be spanking or dungeon domination, they would be taken to a small blowjob room. In this room they would be bare naked, bound, gaged and blindfolded. Only then does their cock cage get removed. 

"I'll come and get you Kaylee, to lead you into this room and you will suck the client's penis until they cum into your mouth ok?" I said cheerfully. 

"Then it's cold-glove time, the cage goes back on and they can go collect their things from the locker room".

Kaylee lowered his head in shame and groaned in defeat. 

"No spitting. You will swallow every drop of cum!" Summer added. 

Hehe, that's my girl! She beat me to it. 

Speaking of Summer beating me...lets fast forward shall we? 

This little twerp in my waiting room is named Edward, he was the horse I bet on. When our notice about blowjobs went out he was at the 23-day mark, since his last unlocking, not even eligible for the handjob program.

37 days later, on day 60, I was waiting by the phone for the call to come in. That day came and went with no sign of the desperate Edward. 

 

This little fucker went 71 days, before calling to book a session and asked for a blowjob ending! 

Summer won the goddamn bet, because of this little puke. Now what? I'll tell you now what. 

Kaylee is about to suck his first cock for money...

And I have to go see Summer, to "settle" this bet she just won. 

*sigh*

Mistress Andrea

xoxo

 

Continued in: I lost the bet