Monday, December 5, 2016

An Early Christmas Present

Perhaps it was just to prove a point.  Her point.

Just one week after allowing me to enjoy an orgasm (my only one for November) while locked in my cage, i was granted the same privilege once again. 

This most recent orgasm was indeed a surprise since Diane thought it would be a good idea to put me on an "orgasm cycle" similar to a menstrual cycle:  one orgasm every twenty eight days.  If She'd stuck to that schedule, my next orgasm would have taken place on Christmas Day.

Yesterday's took place while i remained locked in the Holy Trainer, which seems to be the standard operating procedure for my orgasms now.   The surprise came after i'd pleasured Diane and She told me to lie on my back on the bed.

"Move up a bit" She said.  "Closer to the headboard.  Right there" She said when i had moved up maybe a foot or two away from the headboard.  She straddled my face while grabbing the headboard with both hands, a perfect position to enjoy more oral attention.  i reacted instinctively and did my thing.

After a few minutes She let go of the headboard, grabbed Her Magic Wand and handed it to me. 

"Here, play with yourself while you please me" She said.

In the "old days" i would simply touch myself using the prescribed "sissy masturbation technique" and i would ejaculate in no time.  Yesterday, i had to rely on the vibrations of the Magic Wand against my pink Holy Trainer to bring about my climax.

Yes, it took a little longer but the length of time did not lessen it's intensity. 

The orgasm itself culminates in a very visual physical reaction as my sissy juices fill up and spill out of the "cute little pink prison" (Diane's term for my Holy Trainer.  The varying levels of vibration also play a physical part in the kinky sex scene.  However, there's far more that feeds the Diane's verbal teasing.

Yesterday, i made my mess shortly after She reminded me how sexy it was how Paul gets to cum in Her pussy while i get to cum in my cage.    It was a lovely early Christmas present.

The brain indeed is the most important sex organ a sissy has at their disposal.


sissy terri

Saturday, December 3, 2016

From the Sissy Mailbag: Turtling in Chastity

It's a very busy Saturday for both of us.  Though it's not all drudgery as i'm due to give Linda a pedicure at 4:00 PM.  Some tasks are just more enjoyable than others.  Pedicures are one of them.

So i'm taking the lazy way out of posting today by sharing a letter i got from "sissy Shirley" asking me for some chastity advice.  Here it is, totally unedited:

Hi Terri,
Firstly, that you for sharing your blog. I have been following for quite some time. You are very lucky to be in the position you are in, and you seem quite happy about it.

Just a real short background, I am 40, interested in chastity, denial, am into very low level closet feminisation (mainly just wearing female knickers, etc.), and the idea of cuckoldry. Unfortunately my wife of 12 years is not into any of this at all, so for the moment I just "play" with all this on my own. Hopefully one day this will change, but I am very cautious not to force my wife into something she isn't interested in or comfortable with. We have a bit of an agreement I will not bother her with my "kinks", and she will leave me to it. Perhaps she will come around one day.

 At the moment I am very much into male chastity. I have had a Holy Trainer (pink, of course, V2 short, smallest ring available) for a little over a year, and while my efforts are not even close to comparison with yourself, I self lock for periods of up to a month at a time, only allowing myself out for a few minutes a day for cleaning. I find for successful use, I need to lube the inside of the tube daily, which makes things always moist, which is fine, but I am very aware of hygiene. I have tried wearing it without lube, but I tend to "turtle" inside during the day, particularly when sitting, so when I go to the loo it goes everywhere as nothing is lined up. I work a fairly physical/active job which sees me sit/stand/move about most of the day. With lubrication inside, I never have this issue as things can slide around and always seem to go back to normal position. In general, I love the HT, and actually miss the confined feel when I am not wearing it. If I didn't have to remove it daily for cleaning and lubing I would be in heaven.

I have read with interest your comparisons between your HT and your Jailbird. I am very interested in the JB, mainly because I think it would be possible for longer term use without the need for removal for cleaning due to the open design. Obviously I will need to measure carefully, but I am thinking along the lines of one of the smallest options available, so everything is snug at all times. I am quite small (hence the "turtle effect" in the HT when dry). I guess the risk is without lubrication I will still encounter the same problem.

Am I at all on the right track? I note Dianne is not overly attracted to the less feminine look of the JB, but as I play alone I am not too concerned by that. I guess my main brief is long term wear, so hygiene and comfort are top of the list.

I thank you in advance for your response, and thank you once again for a most enjoyable blog.
If you feel any of this discussion would benefit your other followers, please feel free to share any of it on your public blog, all is ask is I remain anonymous.

"sissy Shirley"

"Shirley's" request for anonymity resulted in my giving her some advice and asking if i were to publish her letter, what name would she like me to use.  Hence, i went with her selected femme name.

i'll share the advice i gave her in a day or two, but i'd be interested in hearing from others in chastity about the problems they've had, either in general or with specific models. 

Oh, and by the way...if you're not familiar with the terms "turtle" or  "turtling" check out the following link:  Turtling: What it is, and How to Avoid It.


sissy terri

Thursday, December 1, 2016

"Once Every 28 Days?"

A fellow sissy (is that an oxymoron?) who's been experimenting with chastity asked me this morning when my last orgasm was.  It was a timely question.  i had planned to post something today about my last (and only) orgasm in November, a month that will go down as having been locked in my Holy Trainer 100% of the time, excepting for hygiene purposes.  Those hygienic breaks include cleaning up after a sissy orgasm in chastity. 

The last orgasm took place last Sunday evening, after the kids were gone and on their way back to their own little love nests.  It was a nice way for the holiday weekend to come to a close.  Diane wanted to thank me "for being such a good sissy wife." 

Dressed in nothing but black heels, white thigh highs and a short white babydoll nightie (i don't count the Holy Trainer as a piece of clothing) i waited patiently for Her to come in the bedroom.  i had everything else ready for the kind of lovemaking She had in mind.  All She had to do was strip down and get strapped in.  i assisted Her with both those tasks. 

i offered to please Her first but She would have none of it.  "I just had an orgasm yesterday I think" She said.  She didn't "think", She knew.  "It's been awhile for you" She chuckled.  "Let's take our time.  I want you to enjoy this one."

We did.  And i did.  There was plenty of foreplay while She wore Her strap-on.  Lots of kissing, licking, and yes...some sucking.  Plenty of straining in my pink little cage as well.  The Hitachi lay on the nightstand fully charged for a long time.  i wondered when She would finally put it to use. 

Diane made love to me slowly, sensually, patiently and very deftly.   It was clear that She wanted me to orgasm solely from Her expert use of the strap-on, relying on Her finding my P-Spot at just the right times.  When She knew i was getting close to ready, She had me turn over and get into the doggy style position.  It's not Her favorite but the one that seems to work best for Her to reach that "special place."

It didn't take Her long.  Soon, my sissy juices began to ooze out of the cage.  It seem to take forever.  i continued to leak well after She'd withdrawn and lay by my side.  She may have wanted to thank me, but i was thankful to Her as well.

As orgasms go, is was one of my best.  When they're so infrequent, they tend to be that way.

In contrast, Diane had one or more orgasms on twenty-four days this month.  There have been some very busy days and as numbers go, it wasn't one of Her best.  i'm not pointing out this disparity between our orgasms as much as i'm just stating a fact; data that somehow helps support the lifestyle we've chosen.

"You really seemed to enjoy that orgasm" Diane said later. 

"i did.  Very. very much" I told Her as i gave Her a hug and kiss.

"Maybe once a month is a good number" She said.  "Or how about this:  Once every twenty eight days?" She asked rhetorically, not giving me time to answer.  "Just like a menstrual cycle."

Who am I to argue.  "Sure.  Something to look forward to" I responded.

Then a few minutes later, this...."If I'm counting right, twenty-eight days from now will be Christmas Day.  Now wouldn't that be special?" She asked.

There was no need to answer.  It would be special.

Should i buy something really pretty for the occasion?

Or maybe Santa will leave something under the tree.


sissy terri

Sunday, November 27, 2016

Sounds of Sex

Having a large home has its advantages.  Not so much when you're the sissy wife who has to do much of the housework but when it comes to sex, distance between the master bedroom and some of the guest bedrooms is a big plus.

For a cuckold being sent to the furthest corner of the house like i used to be can be erotically frustrating (and humiliating).  We have this desire to at least hear the sex sounds emanating from the love nest and when we can't hear them, the frustration mounts.

When there are guests in the house, having stay in the guest bedroom that's farthest away allows Diane to be worshiped on a schedule that meets Her needs. 

Our recently married daughter and son-in-law were here this weekend and Diane told me to get that "room on the other side of the house" ready for them.  When they arrived late Wednesday night, my daughter asked "Why that room?  Why not my old room?" 

Diane had the right answer:  "I thought you'd enjoy some privacy."

And my daughter's retort:  "Are you sure it's not you guys who want the privacy?"

There were a few laughs and Diane quickly changed the subject.

Later that night Diane was ready for some worship after long and stressful day.  However, before i began my duties i couldn't help but ask Her if She thought our daughters had any inkling of our kinkiness.

"I don't know.  Maybe.  Doesn't matter anyway" She said nonchalantly.

"Think she'd sneak out of the room and listen?" i asked, the thought on my mind because of her earlier comment. 

"She is a bit mischievous" Diane smiled.  "But I'm not going to worry about that.  Now get down there."

i didn't worry about it either.  i must have given Diane pause though.  When She came, She was a bit more subdued than usual.


sissy terri

Thursday, November 24, 2016

This Thanksgiving, Grab a Breast

A rather curious day yesterday.  The submissive (moi) got more satisfaction than the Mistress (Diane).

"More" is a relative term.   Simply put, i got my submissive fix in the morning when i gave Linda a pedicure before she ventured out into the Thanksgiving travel madness.  i was quite satisfied with the finished product when i was done, but slightly disappointed that she has TSA Precheck status and wouldn't be removing her shoes at the airport for all to see. 

There was a little surprise at the end of my morning task; a request to plant a kiss on her pretty feet once the polish had dried.  It caused more than a slight tingle inside the Holy Trainer.

On the other side of the FemDom coin Diane was a tad disappointed that She had to cancel Her date with Paul.  Duty called at work and She wasn't free until late in the day when the cuckold window of opportunity had closed.  She got home just minutes ahead of one of our daughters and new son-in-law as the Thanksgiving holiday was set to begin.

From the texts Diane shared with me, Paul seemed to be the most disappointed of the day.  Trying to match wits with our President-turned-comedian, Paul whined that "now the only thing I'll get to stuff this holiday is a turkey."  There were a few more, each of them showing his eagerness to reschedule the date soon.

Diane's long day at work led to an earlier than usual bedtime.  The crispy clean sheets, meant for the two lovers, didn't go unnoticed.  "Thanks for changing the sheets" She whispered sensually, a tease of sorts given the reason for the change.   She was soon sound asleep.

Happy Thanksgiving to all our readers.  Have a great day and......

...behave yourselves!


sissy terri

Monday, November 21, 2016

Cuckold Wednesday & A Pedicure

Last year Diane spent a night at a hotel near the airport with Paul before he flew out for the Thanksgiving holiday.  This year he has no such travel plans.  Instead, he's let me know to have "things ready" for he and Diane on Wednesday afternoon here at our place.

i've already put their date on the cuckold calendar and will make sure the bed has a clean set of sheets for their sexual rendezvous.  Other than that, i'll just have to wait for more specific instructions if there are any.

It's been awhile since Paul's been here with Diane, and probably even longer since i've been involved in any intimate way.  It remains to be seen if i'm to be included on Wednesday and if so, just how much.

Diane's best friend Linda also wants a pedicure on Wednesday morning before she leaves for a long holiday weekend.  i'll be giving her the pedicure here and should be done well before Paul and Diane arrive.

Until Wednesday, i'll be busy doing the grocery shopping for Thursday, getting the house all cleaned up and doing other domestic chores.  Following tradition, Diane takes care of the cooking on Thanksgiving and gives me the "day off" though i'll have done much of the prep work for Her ahead of time.

It's usually the one day of the year when you can find Her borrowing one of my aprons!


sissy terri

Friday, November 18, 2016

A Sissy's Satisfaction

Contrary to what many might think i've not been banned from blogging or been hit with a "gag order" by my Loving Mistress.  i can see why readers would think that because it's been a month since i've written anything here.

There are a couple of reasons for my absence.  The first, which isn't likely to change much, is that i've become very busy with a couple of things.  i'm putting in more volunteer hours and even working some.  From a time commitment view, this is the major reason for my failure to blog.

Nonetheless, i've come close to blogging several times in the past month but found myself just not quite sure what to write.  i put together a few lighthearted "sissy fashion" posts but ended up deleting them.  Those deletions were reflective of the type of mood i've been in.  Call it a "sissy funk" of sorts.

Diane's post yesterday more or less "spilled the beans" for me.  For the past several months i've been reflecting on both Her increasing Dominance and control over me as well as my own escalating submission to Her.  At times, it seems as if both are growing exponentially.

In Her post Diane made it known that She no longer sees me as a male anymore, at least in a sexual sense.  Yes, those are strong words but truthfully, why should She?  While Her revelation was very straightforward and to-the-point, it shouldn't come as any surprise to readers as She's hinted at this several times when it comes to discussing our sex life.

i believe the "tipping point" of our relationship came when She finally agreed to experiment with a chastity lifestyle.  Soon, She was in love with the lifestyle and the experimentation was over.  It's how we live now.  She loves the emotional and physical changes that have taken place.

i can't remember the last orgasm i had while fully erect.   i will probably never have another.

i'm not unhappy.  Far from it.  i love being a sissy wife to Diane.  i just get my satisfaction in very different ways.


sissy terri ❤