Monday, June 13, 2011

A sissy Milking, Then Chasity

Yesterday I mentioned that having tammy out of chastity all weekend gave me the opportunity to see how easily aroused she is.  Never was this more evident than last night with Carol as our dinner guest.  It was quite embarrassing to see sissy's reactions to several of my comments and instructions in front of our guest.  Had I known it would be that bad, the chastity belt would have gone on much sooner than it did!  

When Carol arrived, sissy was busy preparing dinner in one of her maids outfits.  I still had her in diapers and plastic panties for the weekend and pointed this out to Carol in case she hadn't noticed (it was pretty easy to see since the combination of the short skirt of the maids uniform and the puffiness of the diaper and pink plastic panties made it quite noticeable).  I lifted the skirt portion of tammy's uniform to show Carol and sure enough, when I put my hand over sissy's little privates, her clitty was just about at attention!

My plans to eat outdoors on the back deck never materialized because of the rain and cold weather so we enjoyed some outstanding service in the dining room.  While we were on the cruise, our dining companions often commented on how spoiled they were becoming because of the great service they were receiving.  Jay and I just glanced at sissy when some of those comments were made, acknowledging that we were quite accustomed to this type of treatment.  I did allow sissy to have dinner with Carol and I last night since it gave us an opportunity to discuss Carol's involvement over the next several weeks while I'm away.  Jay's going to be stopping by often during the week but Carol is going to be spending weekends here while I'm in The Netherlands.  

I decided to wait until after dinner to give Carol a key to sissy's chastity belt.  As sissy was cleaning up after dinner, I went upstairs to get the CB and a key for Carol and told sissy to meet us in the living room when she was done.  I also brought down an afghan from sissy's room and laid it out on the living room floor while Carol and I waited for sissy.  Carol shot me an inquisitive look and asked what the afghan was for and I told her to "just be patient."  I wanted to have sissy put on the CB in front of Carol to make sure she knew how it worked and, as a little sign of a "partial transfer of authority",  have her snap the lock shut on the CB.  Before I could do that though, I wanted to have sissy lay on the floor in front of Carol so I could take her diaper off.

Stupid me.  I should have realized that my plan wouldn't work.  For starters, when sissy entered the living room and I told her to lie on the afghan so I could remove her diaper, my command, in the presence of Carol, had what by now was the usual effect on sissy's clitty.   Those of you who are familiar with the CB-6000 and most other chastity devices know that they are sometimes difficult to put on, even under the best of circumstances.  Also, while I sometimes "assist" in putting the belt on sissy, the responsibility lies with her.  It's just easier and more efficient that way.  However when one is in a state of arousal, forget it.  The thing isn't going to go on.  So there was sissy, ever the exhibitionist, in a state of semi-arousal in front of her newest babysitter on the living room floor as I took her diaper off.  How cute. 

"You are such a naughty girl!" I told her, which of course only made things worse.  I held the CB in my hand and looking at Carol said "We'll never get this thing on now."  Carol's giggling made tammy turn beet red and the embarrassment probably added to her arousal.  

"Well, what do you suggest we do?" I asked tammy teasingly as I looked down into her eyes.  she was at a loss for words.  "Well?"  I said, "I'm waiting."  Finally, she said "We could wait a little while."  I had to laugh at that one. "We don't have all night" I said as I stoked her little clit.  "Besides, it seems to have a mind of its own.  I think we'll have to help it to go down."  tammy looked up at me with pleading eyes as if to say 'please don't.'  

"Why don't you show Carol how you play with yourself for me?  you always enjoy doing that for me don't you?" Would you like me to help you?"  I asked.  I got up, took her diaper with me and sat down next to Carol on the sofa.  "Follow me" I told sissy, "I want you to stand in front of me and we'll stroke your little thing together."  she made her way to where I was sitting and stood in front of me.  "Lift your skirt" I told her and began slowly stroking her rigid clitty with my hand.  After a few strokes, I took the diaper and wrapped part of it around her clit and continued stroking.  "You like cumming in your diaper don't you?" I asked her.  "Show Carol how you cum in your diaper."   Even I felt naughty about what I was doing.  I'd never put her through her paces like this before.  she came in less than a minute.  

It wasn't like I planned it, but I eventually told tammy to go upstairs and change into one of her nighties.  I went online and ordered a little gift for Carol.  I've attached a picture of it here - a cute little key chain to hold the key to sissy's chastity belt.  I wouldn't want her to lose it while she's out and about!

A little while later, Carol and I got comfortable and the three of us settled in to watch the NBA Finals.  With sissy in her CB, there was no danger of her getting too aroused,  although I'm sure she enjoyed sitting with us to watch the game ;)  Congratulations to the Dallas Mavericks for their victory over the Miami Heat.  Has there ever been a more hated team in America than the Heat?  At times I can see where the Patriots might have have been, but now it's not even close!  

The TC (trophy cock for any new readers) is back tomorrow night.  I can't wait.  I'm going to get as much of it as possible before I leave Thursday.  I'm going to miss "it", and quite a few other things as well. 


  1. It certainly is impossible to put those devices on under those circumstances. I can see how Tammy was both turned on and embarrassed under those circumstances.

    The Mavs made the day for a lot of folks in Cleveland yesterday. It's nice to know that the biggest paycheck does not always prevail.


  2. Sounds like Carol is going to have fun with sissy in your absence.


  3. Go Mavs!!

    Yes, my biggest complaint with the CB6K is the difficulty in putting it on. More than once i've pinched my sissy accidentally. Very frustrating - and my sissy isn't even well endowed!

    Sounds like a very exciting night for you all. Lucky Carol!


  4. Pretty hot Suzanne,

    The back in town,


  5. Once I took off my cb6000s without being authorised, just to clean my clitty and yes, play a bit....(found the key laying around)
    I heard my Mistress coming up the stairs (I was under the shower)
    Although my little friend was hard, by squeezing a lot of shampoo over it, my little friend slid in quite easily!

    Unfortunately, like with Ms Marie, I pinched myself as well.

    Have a great trip to our lovely country Suzanne!
    Unfortunately the weather isn't so great.


  6. enjoy The Netherlands. Looks like tammy will be well taken care of.

  7. Anonymous6/14/2011

    What will Jay be doing when he pops in to check on Sissy?

  8. Mick - I'm sure tammy appreciates having someone else out there that's familiar with "those devices."

    FD - Carol is looking forward to it!

    Marie - sissy's don't need to be well endowed right? ;-)

    Welcome back WC! baths and showers do make it much easier to put on according to sissy.

    grissom - I most certainly will...but I'll miss sissy and Jay!

    Anonymous...well, that would be up to Jay.