Thursday, June 30, 2016

Cuckold Calendar Conflict

We're both at fault.  We both knew about a previous commitment we had for tonight.  When I set up a cuckold date with Paul for this afternoon it was the furthest thing on my mind.  I was really looking forward to it.

I told sissy about it, telling her to make sure her own calendar was clear so she could be around.  I wanted her to be part of the fun.  My excitement grew but turned to disappointment when we remembered today wouldn't work.

The cuckold calendar is her responsibility.  Had she tended to it immediately this disappointment wouldn't be so bad and we might have even been able to select another time.

Instead, I'm in a rather bitchy mood.  That's never good.

Wednesday, June 29, 2016

Chastity Milestone

It was almost 10 PM by the time Diane got home last night, Her tardiness caused by some uncontrollable circumstances at work as well as a couple of days off over the long weekend.  Late arrivals like this usually don't end up with us having extended bouts of intimacy.  Las night was no different.  By 10:30 PM She was showered, in bed and "blowing Z's."  By 5:45 AM, She was on the road and back to work.

While we were both sleeping, an important chastity milestone was reached.  Since January 1, 2015, i've officially spent 95% of my life in chastity.  Since that time, i've been locked in ether the CB-3000, the Jailbird or the newly acquired Holy Trainer.

Most of the time has been spent in the CB-3000.  It was originally Diane's favorite because of it's pink color.  i found the Jailbird to be the superior product, but a Domme's preference in things like this always "rules."  However, Diane's always been considerate when it comes to my comfort and when necessary, i was given permission to change into the Jailbird.

The latest cage, the Holy Trainer, seems to be far superior to either of its predecessors.  Diane not only likes the pink color (a lovely rose that is far more "sissy" than the CB-3000), but believes that its comfort will be very beneficial for "the long term."

We're approaching 18 months of this lifestyle.  Barring any drastic or traumatic changes in either one of our lives, i don't see anything changing.  Chastity is now a way of life for me.  i've accepted it and Diane expects it.

When we started this, neither one of us was sure how it would work out.  The initial goal was for me to spend at least 50% of the time in chastity.  How quickly the bar was raised.  As soon as it was determined i could spend the night locked up, everything changed.

A submissive's fulfillment comes from their Dominant's pleasure.  Diane loves the lifestyle we've grown into and She loves keeping me locked.  She's very pleased.  As a result, i'm a happy submissive.


sissy terri

Tuesday, June 28, 2016

Cuckold Date

It was a very pleasurable weekend alone with Diane, one where i got to both give and receive plenty of undivided attention.  Long and lusty weekends like these are proof that many couples who are involved in some type of cuckolding arrangement can have lots of romance and sexy fun without the bull or lover being present.

That's not meant to be a knock on Paul by any means.  In fact, his presence in Diane's life (and mine for that matter) most often seems to add some spice into our sex even when he's not around.  Paul even responded to one of my daily chastity reports that it was "nice to see you two having so much fun..."

But despite all the fun and sexual satisfaction of the weekend, Diane still has a hunger for the different type of sex She has with Paul and She wasted little time in setting up a cuckold date for later this week.  Thursday afternoon the two of them will be here and i've already been told that my presence will be "required."  i wasn't asked if i had anything planned but instead told that i had to be here.

i also have another golf date with Linda late Friday afternoon with an "appointment" to give her a pedicure on Saturday.  With plenty of housework today along with other errands and commitments, i think i'm going to be a very busy sissy wife this week.


sissy terri

Sunday, June 26, 2016

A Satisfied Sissy Wife

It was sometime around 1:30 yesterday afternoon when Diane told me i might want to head up to the room and "get ready."  Depending on Her mood, "readiness" might mean different thing.  Yesterday, it meant getting ready to take Her strap-on. 

Her timing was excellent as usual.  The maid had just finished with our room when i got there.  The room was ready and soon so i would be also. 

Diane showed the softer side of Her Dominant personality yesterday, opting to remove my Holy Trainer just before She began making love to me. 

"Remember our first time?" She asked me just before She began sliding into me from behind, the question bringing back many memories of our first clumsy attempt with a cheap strap-on and harness. 

"i do.  You took me just like this" i said as my bottom was propped up at just the right height by pillows so that She could kneel behind me and make love to me "doggy style." 

"We've both gotten better at it haven't we?" She said, more of a statement than a question.  i answered Her anyway.  "Yes..especially You" i told Her.

i knew i would cum quickly without the cage.  It had been so long since my last orgasm  She teased me with the head of Her rubber "cock" and i moaned. 

"Beg for it" She said.  i did.  Fortunately, She didn't make me beg for very long and soon She filled me.  Her strokes were slow and loving.  Then She hit the right spot and my long awaited orgasm finally arrived.

By 3 PM we were back on the beach, the Holy Trainer back on,  my long orgasm drought over and with another stretch of not being allowed to cum just beginning.  

The long wait was worth it.  i was a very satisfied sissy wife.


sissy terri

Saturday, June 25, 2016

Pride of Submission

Diane had multiple orgasms yesterday on multiple occasions, causing both of us to lose count of them.  There were some in the morning, some in the afternoon and some just before dinner.  All of this made for some inaccurate reporting on this morning's Daily Chastity Report and the following comment from Paul:

"...and you're a very lucky cuckold Terri.  I haven't COME close to giving Diane that many in a single day.  But, I have COME!"
A nice little tease from the lover.  It's one of the joys of cuckolding. 

Thanks for all the suggestions from our loyal readers about how my next orgasm should come about.  Diane's also very appreciative, though i sense that She's close to making up Her mind if She hasn't already done so.  That doesn't mean that i'm close to having an orgasm. 

i'm not complaining about it though.  There's a certain sense of pride in staying locked and chaste for Her.  It's a pride only a submissive cuckold can appreciate.

Short post today.  The early morning fog has lifted, we've both worked out at the gym, had breakfast
and are already down by the beach.  

Have to run.  Diane's signaling that She needs more sunscreen.


sissy terri

Friday, June 24, 2016

Big Decisions

Free from the stress of the workplace, sex is always better.   I've had two orgasms this morning and the day's just begun.  Who knows how many I can pile up today.

Sissy?  We'll see.  She seems so comfortable in her Holy Trainer and this dry spell of hers is turning into a very impressive streak, why would I risk changing anything now?  Sure, an orgasm really wouldn't hurt but....neither would a little longer period of abstinence.

If I do decide to let her enjoy an orgasm, should it be in or out of her cage?  I have no idea how long it's been since she's enjoyed one while free from one of her chastity devices.  I'll have her look that up for us :) 

So these are the big decisions facing me this long weekend.  Should she be allowed an orgasm?  If so, should it be in or out of her Holy Trainer?

It's not as weighty a decision as the one our British friends faced this week, but it's important to me.  I want to get it right.


Thursday, June 23, 2016

Sissy Toy Boy

With a few days of R&R by the ocean just ahead, Diane's put me in charge of something very important:  Making sure Her favorite sex toys are packed.

The list isn't exhaustively long but instead pretty short and succinct.  i also wouldn't call all of the toys either but who cares about the semantics of things.

Here's Her list in the order in which it was written (the editorial comment that accompanies each one is my own):

The Magic Wand - Other than going to work, this technological marvel travels everywhere with Diane.  i haven't witnessed it first-hand, but She tells me Paul has even seen it put to use.  Pretty impressive considering She is also enamored with Paul's cock!

The Dildo Gag - Ever since Leeanne suggested this wonderful toy, my face has been ridden more often than ever before.  Looks like there will be more riding this weekend.

The Strap-on and harness - It may not rank at Diane's top of the list but it's steady and reliable.  Once a woman finds a harness She likes and a strap-on that works for Her submissive, it's a combination they're not likely to give up easily.

The CB-3000 - my pink chastity device hasn't been used since the Holy Trainer arrived.  The comfort difference between the two is significant, with the HT being superior in that area.  Nothing good can come out of bringing the CB-3000 along.

The NJoy Butt Plug  - Another delightful (Diane's term) suggestion from Leeanne.  i'm to wear it at all times unless told otherwise, or after receiving permission to remove it.  i guess this falls under the "toy" category because Diane gets enjoyment out of my having it in me. 

The riding crop - Again, not really a toy except that She enjoys playing with it.  It's also been a staple of most of our trips including cruises.  Diane usually leaves it out for the maids to see.  Who knows, they might even have some fun with it themselves.

The Vixen - This last one was a pretty big hit until the dildo gag arrived.  Since then it's been used sparingly and always in a "solo mode."  When it's attached to the head of the Magic Wand, Diane doesn't like to hand its control over to me.  What a surprise.  It's used primarily for my viewing pleasure.  Guess i'll be doing a bit of "watching" this weekend as well.

That's the extent of Her list.  She did give me the option of adding my own favorite toy (or two) if i wanted to.  i think i'll pass.  Her toys should be plenty to keep both of us busy.


sissy terri