A Sissy Cuckold's Chastity Progression

Nearly three years ago i wrote a post entitled "Too Much Work" where, after i'd brought up the idea of keeping me in chastity at times to Diane, She immediately dismissed it.  She felt it was too much work for the Dominant partner in any relationship and preferred "low maintenance domination."  How times have changed.

Fast forward to this past June when during a phone conversation we had while i was away on a short business trip, Diane was the one who brought up the chastity discussion.  Her hinting at it and the suggestion that maybe She'd make me wear one only when i was at home or when She was with Her lover Paul aroused me.  She was teasing me and though i enjoyed it, never thought that the idea would go much further.  i was wrong.

Then this fall Diane surprisingly and suddenly set chastity as a condition of my seeing Jake again.  Jake had contacted me and wanted to get together again but i needed Diane's permission.  She took Her time in making up Her mind.  i wrote about Her decision and how shocked i was when She said:

"You can see Jake" Diane said.  i immediately thanked Her but was quickly interrupted.  "I'm not finished.  There's a condition attached to my decision.  If you're going to see him, you're going to be wearing a chastity belt when you do."
More shocking was the fact that She'd already ordered a chastity belt for me; the pink CB-3000.

Then in late December, when the time i was spending with Jake became less frequent when he began dating a woman after his divorce, Diane took it a step further.  On New Year's Eve while we were on a ski vacation, She announced that as part of "our" New Years Resolutions, i was to begin a daily calendar that would log how much time i spent in and out of chastity.  Each day i provide Her with the updated calendar.  It contains daily, weekly and month-to-date percentages of my time in chastity, along with notes.  The notes explain why i was out of chastity as well some of my own personal thoughts.  Yesterday marked four full weeks under this new regimen.  i've spent approximately 88% of 2015 in chastity.

Another surprising, and peripherally related, event took place on Monday, January 12th.  We hosted Diane's friend Linda that night to watch the Ohio State - Oregon national championship game.  Diane delivered another shocker, telling Linda:

....that Paul would be coming over on Wednesday afternoon like he usually does but this time, "terri will be here and won't be hiding this time.  It's all in the open now between the three of us."
The announcement was a shocker to me, though Diane made it seem like i knew all along.  It was difficult to hide my embarrassment and shock, but i was aroused.

Then just two days after that on Wednesday the 14th, i sat down with Paul and Diane and listened to his "rules" for me as a cuckold, two of which related directly to my chastity.  They are:
  • When the three of us are together i must always be in chastity and he will determine if i am allowed out of it.  At all other times, that's up to Diane.
  • i am to send him a copy of the daily chastity report i send to Diane. 
And finally last night, Diane added one more small but not insignificant requirement to my daily chastity report.  Beginning on February 1st, i will also be required to keep track of those days on which either of us has an orgasm.  There's to be a column for each of us.  If Diane has an orgasm (or more than one) on that day, i am to highlight it in green.  If i have one, it's to be highlighted in pink.

This most recent command from Diane made me realize just how few orgasms i've been allowed to have this past month.  i don't even remember when the last one was.  i think it was two weekends ago.

i hope i haven't bored you with this post which is more or less just a summary of how my chastity has progressed, a timeline of sorts that helps put this part of my life in a different perspective. 

Orgasms are indeed an important part of someone's sex life.  We tend to view them as some type of "mark of success" of any particular sex act.  For many, i suppose it's impossible to separate sex and orgasms.  Seems like you need one with the other. 

i'm beginning to understand how that isn't necessarily true.  i can't quite explain it but i can feel it. 

It's almost unbelievable how things have changed, Diane's attitude towards chastity in particular.  i also can't help but wonder when, in the course of the events i've just described, Diane might have decided to connect or link my chastity to the decisions She's made in the past several months. 


sissy terri