The Sissy Cuckold Mailbag - My Period

i mentioned several posts ago that i'd been remiss in responding to questions that are posed in the comments left here.  i've also been remiss in following one of Diane's "older" requirements that i respond to every single comment, whether or not it contained a question. That topic came up last night once again as a result of a question that was posed yesterday, and let to an entirely different discussion before bedtime.

In a comment to yesterday's post, No Cuckolding & No Punishment for Diane - Yet, Anonymous asked:

terri, speaking of schedules, I was wondering if you still are required by Diane to have your monthly 'period', where you have to use tampons and or pads? Is that included on your calender also, for Paul to see?

The short answer to the question is "yes" and i suppose i could leave it at that.  However that would only lead to more questions.  It would be the easy way out.  So let me give you a more complete answer and the reasons for not having brought it up before.

If you recall back in mid-January during my first real private meeting with Paul and Diane (Pondering Paul's Rules) i discovered that Diane had told Paul about the blog.  Her secret revelation to him resulted in a very emotional response.  i was filled with anger, shame and humiliation.  It was a carefully calculated step by Diane which in the end, led to where we are today.  It helped Paul gain an understanding about who we are and what made our relationship work.

There were many things that i was ashamed and embarrassed about in the blog with that revelation, none more so than my requirement to "have a  period" once a month.  That was a major issue and understandably caused a tremendous amount of friction and angst between Diane and i.  We obviously resolved our issue but to some extent, the embarrassment remained and i never brought it up on the blog until now. 

All my comments are moderated, requiring approval before posting.  i only did that because of some absolutely nasty and vulgar comments that were left months and months ago which i had to delete.  Once i started comment moderation, the anonymous commenter went away and hasn't attempted any return.  So yesterday, i could have easily ignored the question that was posed and not posted it, but i just didn't feel right about doing that.  It was a legitimate question that dealt with something i'd written about before, was still a part of our lifestyle but something i hadn't appropriately addressed. 

So yes, i am still required by Diane to have my monthly period and it certainly is part of the Chastity report.  It shows up once every twenty-eight days and it's highlighted in red.   Paul sees it and in the three plus months i've been sending the report, has always made a comment about it.  The comments are not hurtful but rather more teasing in nature. 

i feel a bit better about sharing this with you.  It's something that's been on my mind but i just avoided it.  i've come close a few times because it did have some bearing on what i was writing about at the time but just didn't do it. 

So, whoever the anonymous commenter is who left the question yesterday, thank you for prompting me to get this done.  i'm glad i did it and realize i shouldn't have waited so long.

love,

sissy terri

p.s. - i have many other questions to answer and promise i'll get to as many as i can here in future posts!

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Altoids, Riding Crops & Tampons

i had to take a few days off from blogging because of an unexpected business trip to the west coast.  i also stayed there an extra day to visit a former colleague of mine who is now retired and living just outside of San Diego.  i got home last night, just in time to start my period.  Diane had the tampons and pads waiting for me when i arrived.  Any escape i have from being Her sissy wife is always temporary and never a return to full masculinity.

While i was away, Diane and Paul did have an opportunity to get together here yesterday afternoon, with the whole house to themselves, much as they did on Wednesday afternoon while i was out playing golf with some friends.  It was a hot afternoon on the golf course, but probably even hotter in the master bedroom back home.

i came home immediately after Diane texted me.  "Coast is clear" She wrote, meaning that Paul was leaving or had already left.  i was about 15 minutes away enjoying a cold drink in the club.  i excused myself and promptly went home.

Unless you've gone through the experience, it's hard to describe the emotions that run through you when you return to your house, enter the bedroom and view your wife along with the remnants of the lovemaking She's enjoyed with Her lover.  There's the sheets strewn all over the bed, pillows on the floor and your Wife laying there on the bed that may contain one or more wet spots as evidence of their lovemaking.

There are other things that might even be around that provide evidence of the kind of sex they had.  Prominently displayed on the nightstand was a riding crop.  It's a toy we've had for a long time, a toy that Diane's used on me.  This time i knew that Paul had used it on Diane.  i didn't have to see (although i couldn't help but notice) Her beautiful bottom with red swats on it to know She wasn't the one wielding the crop.  Diane had submitted to Paul that afternoon, making me feel even more submissive than usual. 

Next to the crop sat an opened and half empty box of peppermint flavored Altoids.  The powerfully flavored candies weren't used as breath mints; that much i knew.  Diane told me Paul likes the feeling they provide after She's had a few of them and puts his cock in Her mouth.

It was now my turn to have a few of the mints.  Diane loves them as much as Paul does when i lick Her.  Despite their strong minty taste, the taste of Paul's semen was still present and powerful; another reminder of my cuckold status.  i finished my duties by kissing and licking Diane's reddened bottom for a very long time. 

"It's been quite a satisfying afternoon" Diane said after enjoying the second orgasm She had from my oral attention.  She also allowed me to cum while i licked Her bottom.  Slowly moving my sissy clitty back and forth against the sheets while i tongued Her butt led to my own orgasm.

Satisfied with me, Diane got up and showered while i changed the bed sheets.  There were several wet spots on the sheets.  At least one of them was mine. 

love,

sissy terri

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FemDom and Sissy Cuckolding

My oh my.  It's been a week and a half since i've posted and with no real good reason, other than probably a mix of emotions that come with being 1) a submissive male, 2) a sissy male, 3) a cuckold and 4) a "wife" to a Dominant Woman. 

Diane's Dominance doesn't waver anymore.  If anything, it increases incrementally in its intensity.  Gone are the peaks and valleys we've gone through in the past, where certain expectations would just fall by the wayside and be forgotten. 

Here's a good example.  Diane used to make me wear tampons and pads for one week each month.  She would determine when i was to start "my period."  We'd gone through this ritual for awhile before it seemed to be forgotten.  Last Wednesday morning, upset that i had forgotten to make the coffee and set the timer on Tuesday evening, we got into a little spat.  She felt i was being bitchy.

Diane's solution?  She dug out the tampons and pads, laid then out on my side of the bathroom and proclaimed that my period had started and i knew what had to be done.  i spent the three days with a tampon and pad and the following four with just a pad as per Her instructions. 

Diane and Paul have also raised the intensity of their relationship.  They met here yesterday afternoon as is their usual Wednesday routine.  i was out at the country club in the searing heat playing nine holes and enjoying a cold drink before i could return home at "4:30 PM promptly."  On my way home i received a text from Diane that said simply "Hurry up.  you've got some cleaning to do."

i got home within a minute or two before 4:30 and found Diane laying in bed reading her Kindle.  "Strip down to your panties and open the nightstand drawer" She said as she pointed to the nightstand on my side of the bed.  After stripping to my pink panties i opened the drawer and found a baby bib with different designs on it (pacifiers, toys, stars, etc.). 

"Come here and I'll put it on you" She said.  Tying it around my neck as i knelt before Her She added that "this is sort of a special occasion and I wanted you to look cute.  Now please me."  i didn't understand what She meant but when i lay down, put my lips to Her pussy and began to lick i understood fully.

Paul and Diane hadn't used condoms that afternoon and i could immediately taste and feel Paul's semen inside of Her. 

"Taste it?"  She asked.  i hesitated briefly but told Her i could indeed taste his semen.  "Like it?" She asked with a giggle.  i admitted that i did.  i was aroused and continued to lick Her. 

Diane can tell when i'm quite aroused, even though my penis was out of Her sight and encased in my pink panties.  Suddenly She told me to stop and knees in front of Her and between Her legs. 

"Ooooohhhh, a little excited aren't we?" She asked as She stroked my penis through the panty i was wearing.  "Does my sissy like it that Paul came inside of me?" She asked.   i responded "Yes" but it wasn't good enough for Her.  "Yes what?" was Her next question.  "Yes Mistress" i said and noticed some raised eyebrows so i then added "i'm happy that Paul came inside of You."

She continued the teasing, calling me a good sissy cuckold and made me thank Her for the opportunity to clean Paul's semen out of Her.  All of this while She continued to fondle  and i eventually came in my panties. 

"That's a good sissy" She told me.  "Now finish what you started."

It was the most submissively intense experience i've ever had.  As i cleaned Diane and She enjoyed Her orgasm, i realized that that afternoon, Diane's lover Paul had cum inside of my wife while i had cum in my panties.  How fitting. 

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Wifey Stuff

My part-time consulting commitment has been rather slow lately.  It should have given me more time to blog but it hasn't worked out that way.  A couple of other things came up this past week which kept me away from the computer.  And, my consulting thing is going to heat up in a couple of weeks when the next phase of the project starts.

In the meantime, Diane's kept me focused on more "wifey things" as She likes to call them.  The list of to-do's seems to get longer every day.  Our house looks spotless, with not one thing out of place.  Washing floors, walls, windows, and anything else you can think of that can be washed keeps it looking that way.  There's also plenty of reorganizing, filing, cleaning out the garage, etc.  It never seems to end. 

Since i'm dressed all the time when at home, all of the housework is done en-femme, which definitely puts me in the housewife mood, but doesn't take away from much of the drudgery.  i change into more suitable attire when i go out to run errands, only to get back into my women's clothing when i return home.

i made a couple trips to the dry cleaners this week to bring some clothes Diane took out of our large cedar closet that She plans on wearing this fall.  She would take them out and lay them on the bed before She left for work, telling me they were to be taken to the dry cleaners.  Yesterday, amid the half dozen or so items She left, was one of my maids uniforms that i hadn't worn in a while. 

"It could use a cleaning" She said.

It's a satiny black uniform, with a flared skirt edged with lacy ruffles.  There are also ruffles at the arms and neckline and a sewn in white ruffly bib front.  It clearly has the look of a costume more than a working maids outfit.  Someone seeing it would definitely know it wasn't meant for everyday maids work.

It was embarrassing to bring it to the dry cleaners.  The young girl (probably a high school aged teen working a summer job) smiled and said "Oh this is so cute" when she took it.  i had a nervous giggle and couldn't help blushing a little.  i wondered what she thought.  If she only knew what i was  wearing underneath my shorts and shirt!

Yesterday was also the start of my "period", two days earlier than i had planned.  The tampon and pad i were also set out by Diane yesterday morning.  Those two items are far more telling of my lifestyle and status than the  maids uniform i brought to the dry cleaners. 

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A Cuckold Night

Tonight's a cuckold night.  I'm home alone and Diane is spending the night with Brian and a rather upscale hotel downtown.  She's been primping for it all week; purchasing new lingerie, getting a pedicure and manicure at the spa, and overall just being obsessed with seeing Brian tonight.

i traveled a bit this week on business and this part-time job is becoming a grind for both me and Diane.  She wants me to quit and has given me an ultimatum.  Either my hours reduce dramatically or i'll be forced to resign.  "Your housewife duties are suffering and I'm not going to put up with it" She said.  i understand our contract and She's right.  "Don't you miss being a full time housewife?" She said laughingly.

Her teasing might be the same but it seems a little more pointed lately.  Maybe i'm just being overly sensitive.  She's also becoming more dominant and in some ways, i feel She's being a little less "careful" about Her affair with Brian.  Meeting him at the hotel tonight is an example of what I mean.

Before She left this morning She reminded me that i was due to start my period today.  The box of tampons and a pad were left on the vanity for me to use.  Maybe that's why i'm feeling overly sensitive.

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Meeting a "Wife's" Needs

Other than going into the office just briefly yesterday, Diane decided to take the entire week off.  It's been nice.  We got to spend time together, talk, shop and just enjoy being together while our "boyfriends" are away on their own family vacations. 

Despite having my period this week, we've been rather sexually active.  Diane's teased me about how horny She's been all week and how much She misses manly sex with Brian.  i've pleasured Her as best i could (at least twice each day) orally and a few times, using a hand held vibrating dildo on Her as She fantasizes about Brian.  This form of pleasure for Her has given me an insight into some of their lovemaking.  Diane might be exaggerating some of the things She talks about while i pleasure Her this way, but there's clearly a change in Her approach to sex since She's been with Brian. 

She hasn't made love to me with Her own strap-on since i started my period on Sunday.  However, there have been multiple "sissy masturbation" sessions, even a few while i was still "fully pantied."  It does make for a little bit of a mess and Diane laughed and told me since i lacked so much control that "maybe you should wear a diaper instead of panties."  She's also been teasing me by saying that She hopes my period is a short one so that She can make real love to me before the weekend.  That's a good sign.  I'm expecting Her to let me know today that my "time-of-the-month" has come to an end.

We were shopping the other day and Diane picked out a cute little summer nightgown for me.  i also pointed out something that i thought would look good on Her.  Her first comment was "Do you think Jake would like it?"  i told Her i thought he would, but that i really liked it.  We bought it and She wore it for me the next night. 

As we were shopping i thought about how each of us works hard to please each other as their "wife."  In our relationship, we really are each others "wife."  i don't sexually pleasure Diane like a real man would, and we're both more than okay with that.  But She definitely pleases me like a wife gets pleased.  She's even back to calling me "wifey" more and more.  i am loving all of it.  The more She does these things, the more submissive and feminine i feel.

By all indications, She's loving it too. 

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Downer of a Day

Yesterday turned out to be somewhat of a downer.  When the woman at the front desk at the gym scanned me in, she told me to wait a second before i went into the locker room because i had a message.  She found an envelope that had my name on it and handed it to me.  The message was from Jake, apologizing that he couldn't make it to the gym Thursday or Friday, that something came up at work and he'd be out of town.  "Let's try Saturday" was how the message closed.

The message really bummed me out.  As nervous as i was about having coffee with him, there was also plenty of angst and constant worry about whether or not i was reading this right and even if i was, how i was supposed to act.  Now with this cancellation, i would be filled with at least a few more days of nervousness. 

This isn't like someone you meet online where you post an ad that, if written properly, should explain the type of person you are looking for.  When you do that, the people who respond aren't usually surprised by your interests and fantasies if you've been honest.  This situation with Jake makes me feel like a teenage girl in high school!  Even if i am reading this correctly, and he is interested in me sexually, i still have to somehow make sure he's okay with my femme side.  It's possible he suspects it because of my smooth legs, but somehow i doubt it.   i've gone over ways i can bring it up in a conversation (if our conversation ever gets far enough) and will continue to fret over it.

I also started "my period" yesterday.  When i walked into the bathroom yesterday morning, Diane had set out my box of Maxipads, a non-verbal signal that i should put one on immediately.  By my calculations, i wasn't due to "start" and mentioned it to Her.  "You must have miscalculated" was Her answer.  i wore the pad.

Leaving the box of Maxipads out on the bathroom vanity was a clear message from Diane.  She didn't have to spell it out either.  i shouldn't expect to be exempt from having my period just because i was seeing Jake, now or in the future.   It had nothing to do with my miscalculating.

i know i'm getting ahead of myself, probably way ahead.  But, if things work out with Jake and we do get together, i'm either going to have to make excuses during "my time of the month", or i'm going to have more explaining to do.

i feel a little better today.  i went to the gym early and am back at home getting ready to do some ironing.  After my shower i'm going to wear something nice to do the housework.   Maybe something different like some tight ladies jeans and heels.  i may even put on a little bit of makeup.  Just because a girl is having her period doesn't mean she can't look pretty.

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Tampon Time

As per my "contract" with Diane, I started my period the other day.  After I showered that morning I inserted a sanitary napkin in my panties and went about my business.  I was a little disappointed that Diane didn't say anything that day or in the days leading up to the time when I'm supposed to start.  Her little snide remarks about how I must be getting ready to start my period because I'm bitchy or moody always make me feel more feminine.

This time, there was none of that and when the day came, I just did what I'm supposed to do.  I was also very disappointed that she hadn't even noticed it in the evenings when we were changing or in bed.  I really was in a very different and down mood because of the lack of attention.

That changed this morning though.  I was up first and got the coffee going before heading back into the master bathroom.  Diane was still in bed and got up just a few moments later.  She came over to kiss me on the cheek and ran her hand down to the front of the panties I was wearing, stroked the outline of my penis and  reached down a little further.  She felt the pad.  "Too bad you have your period, I was hoping to fuck you tonight" she said.

Her touch and her words got me very aroused.  The neglect she had displayed for the past couple of days was soon forgotten. 

"You seem to be flowing heavily too.  I think it would be a good idea to use a tampon again this month.  Get me one and I'll help you with it" she said.  I went to the cabinet to retrieve a tampon and gave it to her.  After lubing a little, she slid it into my bum.  "There, that should help" she said and put her arms around my waist.  "You'll have something much nicer in there in a few days.  I promise." 

As I go about my housework today, I know it may sound strange, but I'm finally enjoying my period. 

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A Cuckold's Big Day

Today's the day.  Diane told me last night that Brian will be in town today and tomorrow.  She's going to be meeting him in his hotel room this afternoon after work.  I asked her if this just came up yesterday or if she'd know for awhile.  She knew since the middle of last week but didn't want to tell me until last night.  She thought I'd worry too much about it unnecessarily.  She's right, I would have.

I've spoken with Diane four times today.  She's called me to reassure me that she still loves me and I've called her to do the same.  That's helped.  It's an emotional day for me.  Yesterday began "my time of the month"  so today, I'm not only wearing a maxi pad but the tampon Diane inserted this morning.  I'm to replace it as needed throughout the day.  I've spent the day doing housework (there was plenty of ironing to do today) and running other errands.  Now it's just a matter of waiting for her to come home later tonight.

This morning Diane took longer than usual to get ready.  She looked sexier than I've ever remembered.  Of course she's probably looked just as good or even better before but with the circumstances of this day make her sexiness more pronounced.  I'm sure she'll raise eyebrows at work. She's wearing a black lace bra, matching panties, garter and thigh highs.  The black bra is very noticeable under her white blouse, but is covered quite nicely by the black jacket she's wearing.  Her black skirt is just tight enough to accentuate her shapely ass and thighs.  A tad more makeup than usual, a hint of perfume and a pearl necklace and earrings made her look irresistible.

When she was getting ready to leave, she had me retrieve the Magnum condoms I bought for her to use a couple of weeks ago and put them in her purse.   After I put them in the purse, I wondered how many she would use tonight.  I was daydreaming when Diane came over and gave me a big hug and kiss.  She promised to call me today and also tonight when she was on her way home.

Brian is going to be one lucky guy.   All that's left for me now is to wait.

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A Sissy's Hormones

My wife Diane's involvement in my feminization has always varied over the years.  There were times when it seemed constant, for days or weeks at a time.  At other times, it was as if she could care less about it.  I'm not saying that in a bad way at all.  I'm very understanding of the fact that it shouldn't be a high maintenance thing for her.  There are times when she definitely enjoys it more than others.

I can usually tell when her moods are changing.  She'll make a few comments about what I'm wearing, how I'm acting, my looks and generally just act different.  The little subtle comments she makes in public sometimes in front of friends are those that have the most profound effect on me.  We both know exactly what she means, but our friends don't get the true meaning of her comments.

Last night we got into a very tiny spat over something quite insignificant - coffee filters.  I'll leave the subject at that so as not to bore you with what are ridiculous details.  The discussion we were having didn't make any sense at all and at one point Diane said "I can tell you're getting ready to start your period this week just by the way you've been acting!"  It was a not-so-subtle reminder about my feminine role in this household as well as a warning that come Tuesday, I better be wearing some feminine protection.

The comment stopped the argument dead in its tracks.  She walked towards me, hugged me and gave me a big wet kiss.  Without another word, I finished making the coffee for Sunday morning and met her in our bedroom where she proceeded to make love to me.

When we were done Diane told me how much she loves it when my sissy hormone's kick into high gear just before my period.  I guess she's back in one of those moods!

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"Femmespace"

Under my contract with Diane, I spend 7 out of every 28 days having my period.  It's a lesson in femininity, humility and obedience.  During that time, sex is limited to my providing her with oral relief.  I imagine this is very similar to what many women go through when they have their period.  Still pleasing their husbands or boyfriends with their mouth while their pussy is off limits.

Doing these things and acting this way has in some ways become routine for us but it never loses it's intended effect:  to remind me who I am and of my role in this relationship.  The fact that Diane doesn't "fuck" me during this seven day period with one of her strap-ons often makes me want it more.  The fact that I'm obligated to please her with my mouth reinforces my obedience.

Last night was mostly typical of the type of sex we have during "my time of the month."  I say mostly typical because Diane's urges seemed to be heightened, most likely because of her Friday lunch with Brian. Diane took full advantage of my role and had me kissing her all over, and I do mean all over.  There was more verbal teasing than usual and during her moments of passion was much more vocal.  From my viewpoint, much of this is very satisfying since it provides me comfort in knowing Diane enjoys what I provide for her.

I was also made to feel more feminine when Diane surprisingly told me to get her strap-on dildo and harness and help her into it.  It was another tease, but one I enjoyed.  Once strapped in, she lay back on the bed and had me take the make believe cock in my mouth.  It's what many wives do for their spouses when they're in the middle of their period.  "Why should you be totally deprived of cock during your time of the month" she said.  "I know how much you like cock."

There's lots of references to the term "subspace" in D/s literature and blogs.  As submissive as I often feel during moments like last night, I prefer to refer to that feeling as "femmespace."  I haven't really seen that term anywhere.  I'm sure it's probably out there somewhere.  It's a feeling that I get often and many times it comes from different things.  It's a feeling I love very much. 

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Feminine Emotions

The past few days have been very emotion-filled for me.  As instructed by Diane, I made an appointment for her to have her nails done using the gift certificate I bought her.  In some ways I was hoping I wouldn't be able to get her an appointment since it was at the last minute.  I was still bothered by the fact that no sooner had I given her the gift certificate that she decided to use it to get her nails done for her lunch date with Brian today.  It's a date that could eventually lead to her cuckolding me for the second time in our marriage, the first time with my full knowledge.

The lady at the spa had a cancellation and was able to squeeze her in, but not until 6:15 PM.  I thought it was a little later than Diane would have liked but made the appointment anyway.  The lady also surprised me when she asked me "Is this for any special occasion coming up this weekend?"  I hesitated and the lady added "You know, like a wedding, anniversary or something like that?"  I told her that it wasn't, that my wife just felt like treating herself.  Obviously I lied.  Had I been truthful I would have answered in my most submissive sissy voice that it was for an important lunch date with a potential lover of hers.

Wednesday was also the day that according to the contract I have with Diane, I was due to start my period (all part of my feminization and our Female Led Relationship).  I had forgotten about it and so had Diane.  I think it was only the second time I had forgotten about it, proof that my emotions were getting the best of me.  Also, Diane always seems to either remind me or check to see if I'm wearing the feminine protection I'm supposed to.  She must have forgotten as well.  No doubt she has other things on her mind.

Diane didn't get home until nearly 8:30 last night.  I had prepared a salad with grilled chicken for her and waited until she got home so we could eat together.  Her nails looked beautiful and I told her so.  "Don't worry, you'll get to enjoy them too" she said with her beautiful smile.  We spoke little, but we both seemed to know that today's lunch with Brian was on our minds.  Diane is very perceptive and before dinner was over, looked at me and said "Don't worry so much about tomorrow.  Think it through and you'll realize it's something you've wanted.  You knew it would be difficult at first.  If it's meant to be, it will work out fine.  Who knows, I may decide against it."  She was right.

As I cleaned up the dishes after dinner, Diane asked me if I had started my period.  "I forgot to check with you yesterday.  I hope you didn't forget to wear your pad" she said.  "I did start." I told her, but didn't add that I forgot about it and hadn't put a pad on until today.  It would have been another lie. 

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"Wear Something Pretty"

Those were Diane's instructions this morning before she left for the office.  They came immediately after asking me in a very teasing manner if "my period" was over.  I told her that it was and she followed up with the order that I be wearing something pretty when she got home tonight.  If you recall, each month I am required to wear sanitary pads for a seven day period, all part of the contract I have with my Dominant Wife Diane (DWD).

I tried to get more specifics out of her about what she would like to see me in, but it didn't work.  Whenever I get such an order struggle with it, even though I really love it.  I don't know if I should wear something like just lingerie, or dress to the nines with one of my wigs, makeup, jewelry, etc.  I prefer being told what to do, with little left for me to decide.

I'd love to be dressed like a 1950's housewife for her.  Maybe that Barbara Billingsley look in "Leave it to Beaver."  I'm sure by the time she gets home, I'll think of something.  

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My "Time of the Month"

Last night as we lay in bed after I pleasured my wife Diane orally, I cuddled next to her as she held me close.  I have very sensitive nipples and she played with them very sensually.  I moaned softly as she touched them a pinched them a little bit.


"Are your breasts a little sore?  You should be starting your period soon right?" She asked me.

"They're a little sore" I told her.  "I'm due to start tomorrow."

She knew very well when I am supposed to wear a sanitary pad.  It was just one of her little subtle reminders of how much things have changed.

I loved it too.

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