It all started with a podcast

21.

There’s an adage in (American) football that says “Keep running the same play until the defense proves they can stop it.” In our case, she kept going to the well time after time running the exact same play: she’d bait me to the point where I was desperate for release, only to delay it until after she got a feminine concession in return.

This “play” had worked with the panties and thigh highs. Shortly after she added toenail polish (pink, of course) and lipstick (same), the lipstick being a requisite prior to going down on her. Then she requested I shave my upper body, her rationale being (correctly) that it looked foolish to be half smooth.

I had been an easy target. Chastity will do that to a person. However, I was growing uncomfortable with the direction. I didn’t like where we were headed. And the pace was quickening.

I sat there a week later, ready to boil over, as she fully made up my face – foundation, concealer, brows, eye shadow, liner, mascara, lipstick and liner, pressed powder, blush, I could go and on.

When she produced a wig and began to fit it with the promise of a reward, I pushed it away.

“Stop! Just stop,” I said throwing my hands up.

She paused, the wig dangling in her hand.

“We need to talk,” I started. “I don’t understand this, I don’t get it, I don’t want it.”

She remained quiet.

I got up from the chair and makeup table in our bathroom and walked away the kitchen, ready for a fight, anticipating her trailing behind me. She never came out of the bedroom.

My defense had finally stopped her play and I was glad I had stood up for myself. What I didn’t realize is I may have won this early skirmish, but the war hadn’t even started yet.
 
22.

Every relationship has tough times. Most people won’t admit it. Even your friends will give you the “oh, yeah, everything is great” nonsense when often the reality is the exact opposite. People have problems. Couples you know have problems. At this point in time, we had problems.

Her insistence on pushing feminization when I wasn’t interested led to a cold war that lasted more than 3 months. During this period we continued to pursue our FLR – I remained in chastity, I still handled the vast majority of the daily chores, still said my daily affirmations and kept my commitment to try and anticipate her needs as her submissive.

Sexually, I continued to please her. She continued to tease and deny me and added a heavy dose of small penis humiliation into our verbal play. It was emasculating, and I could (and probably will) write several posts about how it affected me positively and negatively as well as her reaction to it. For now, all that matters is it became a normal part of our playtime.

(Looking back now, it was exceptionally bold of her to lean into this type of humiliation, given everything we were going through).

My feminization was rarely discussed. But it hung over everything. Neither of us had said what needed to be said, so, while it was back-burnered, it wasn’t resolved. It was ignored, often for a week or more. Then the argument would bloom again, and, like an onion, there were a lot of layers to our feelings.

For me - and I’ll bounce around a little bit here, since it took us time to get this all on the table, and was a learning experience that deepened over multiple conversations – I didn’t understand why she wanted my feminization so bad. Everything had been going so well: our relationship rhythm, chastity, my submission, our communication. We were walking in lockstep down an enjoyable path. Why not continue to stay on that road?

For her, she explained it as a deep need to ramp my submission and to emasculate me to the fullest, which she found incredibly exciting.

For me, the question was “why” – why push me towards something I don’t want?

Her rationale was that she was in charge and there was no way I could know I didn’t want it without actually trying it.

I countered that I had tried it, certainly to some extent – panties, lingerie, nail polish, makeup – and didn’t enjoy it.

She countered that by intimating she was more interested in the mental aspect of it – the deepest submission – and that the physical and visual aspects were only a small part of it.

Keep in mind, these conversations took place over weeks. We’d discuss it calmly for 30 minutes or so, listening intently and being respectful and then it would devolve into clear disagreement or an argument. That led to a stalemate. Then we’d ignore the problem for several more days.

I kept coming back to why … she wanted deep and extreme submission, but there are certainly hundreds of other ways that don’t involve feminization. What about consent? Why push me towards something I don’t want?

Her response to this was similar to her initial answers; I was objecting to something I didn’t have a right to object to yet, because we hadn’t gotten to a place where I was well-informed enough. Her argument was we had only dipped a toe, we were both having fun in the privacy of our own home, so what was the harm?

Eventually I came to her definition of “the deepest submission.” What did that look like in her mind? Did she want me to have an operation? Plastic surgery? Was this a 365 days a year thing?

She claimed she didn’t know.

I accused her of being evasive. We fought for over an hour.

In hindsight, I have now come to trust she didn’t know the exact direction we were headed and still doesn’t completely know now, although the picture is much clearer for both of us. But during this time, it felt like she was being coy. It drove me crazy. The stalemate did too. She wanted something. I did not. She wasn’t backing down. Neither was I. A lot of nights, even though we went through the motions of having some drinks and segueing into a session, I could feel the chill underneath it all.
 
23.

There is nothing helpful about being hurtful. During this time I said my fair share of hurtful things to my wife. We had issues to resolve, but some days I just wanted to ignore it. I wanted to see her smile, to flirt with me, to be her “old self” – but her frustration with me was deep rooted. It felt like we could splinter at any time. While this was the last thing I wanted, feeling that way worked counter to how it should have. Instead of driving towards her, I’d be kind one minute and unkind the next. I’d want to avoid the topic completely one moment and then dive into a discussion the next. If she wasn’t ready for the discussion, I’d storm off, flinging some hurtful comment over my shoulder as I did so. It was unproductive and wrong.

I give her credit. She kept her cool the entire time. I think she used small penis humiliation as her anger outlet. It’s actually kind of funny. Looking back, she was relentless with it. Even with everything going on, she made it clear it was “tiny,” “useless,” and “not where your pleasure should come from.”
 
24.

Fear. We all face it. Rational or not, if we look inside ourselves, we will always find fear. Its why people make choices, or don’t make choices. It’s why we deflect, procrastinate, lose sleep, make excuses and hundreds of other non-productive actions/non-actions.

Her question that began the end of over three months of fighting dealt with my fear head-on, even though it seemed innocent enough when she asked it:

“What are you afraid of?”

We hadn’t broached the subject in five days, but I knew she was referring to my feminization, and if she wanted to talk about it, I was prepared to give her both barrels.

“I’m afraid you know why you want this so bad, but aren’t telling me because it ends with you leaving me,” I said. “So much of what you say is ‘you’re not a real man’ or ‘you are so small’ or ‘you’re such a princess.” Those strike me as things you say to someone when you have lost respect for them. When you aren’t happy in a relationship,” I continued.

“OK.”

“My biggest fear is that you will continue to lead us down this path to the point where I am – if I’m not there already – no longer a romantic option for you. Then you’ll go seeking for someone else, find him … and leave me.”

“And what if I told you there was no chance of that happening?”

“I’d ask you how you know,” I said.

“Because this is our journey. Your submission and devotion to me makes me love you more every day. This isn’t about finding someone else. It’s about finding ourselves.”
 
25.

Eventually I found myself.

How I came to this life-altering realization was the culmination of the worst 100 days of my marriage. It came from fear, uncertainty and doubt; from not knowing myself as well as my wife knew me, and by putting my trust and faith into her vision for our marriage.

I hated our silences. I hated disappointing her. Why did I not see me how she saw me? What was I afraid of? I was so scared of charging down the feminization path she so desperately wanted because I was afraid of losing her. I never stopped to consider that perhaps the opposite was possible. What if my reluctance ultimately pushed her away? I couldn’t let that happen. She demanded my complete submission. Why was I reluctant to give it to her? I had put myself, my heart and my trust in her dominance and it had been the most thrilling year of my life. I needed to push towards her, not drive her away. I needed to accept who I was, what I was, and what I wasn’t. I couldn’t lose her. I’d never forgive myself.

I woke up crying, all these thoughts swirling in my head. My back was to her, but she heard me sobbing and pulled us close.

“What is it, baby?” she whispered. “Tell me what’s wrong.”

“I’ve been so selfish,” was all I could get out. My face clenched as new tears came.

“Go on.”

“I need to focus on you. I need to trust you.”

“You do.”

“You won’t leave me?”

“Never.”

“This is the right way forward?”

“It is.”

“I’m so sorry.”

“It’s OK. We needed time to get here.”

She held onto me tight as I wailed. The release of it all was overwhelming. I've never cried harder. I wanted my wife back. I craved her control. I needed it like oxygen. This had all gone on too long.

“What was it?” she asked.

The words came quickly. “I’m not a man.”

“No baby, you’re not.”

We laid there for several minutes, her rubbing my back as I cried.

“Say it again,” she said.

“I’m not a man.”

“Again.”

“I’m not a man.” I kept repeating it as I rocked in her arms.
 
26.

Submission comes naturally for me. I try to do the right thing, have the answers and not look to her for direction. If she needs to course correct, she will. If she wants me to go in a different direction, she’ll order it. We’ve always worked with the unspoken “rule” that if she isn’t providing instructions, it’s because whatever I’m doing is pleasing and acceptable to her.

But in this case, I was lost and needed her direction.

“So what should I do?” I asked.

She smiled. And at that moment my life as I knew it changed forever. It was clear she had anticipated me “breaking” and accepting this direction long before it actually happened. She instructed me to retrieve a large storage container from the basement and then handed me a list, in love letter form, of what was required each day. We keep everything from our journey (I wish more was written down) in a lingerie box under our bed. Here is the exact note:

Darling, in order to be the best “you” please follow this schedule:

Work Days (Remote):
6:30am – wake up, yoga (look inside box) and affirmations (see below)
7:00am – cardio and the feminine body/booty
7:45am – dishes, cleaning, vacuum, eat something
8:15am – shower, shave (no face), smooth (inside box)
8:45am – work, bitch – you will use the mullet strategy here (*note, that’s what we call the typical remote worker outfit, when you wear a dress shirt or blouse for Zoom calls, but you’re in your pajamas and slippers from the waist down. In my case, she put me in a skirt or leggings and high heels and I had to ask permission to remove the shoes)
12pm – Anything listed on the kitchen counter or that needs to be done ad hoc. Always be cleaning during any breaks – museum quality, princess!
After work:
Shave face, moisturize, light foundation, mascara, lipstick, hair, clothes I’ve laid out
Dinner and related
7:30pm – Affirmations and Femininity training (assorted, with wine)

Work Days (In Office):
6:00am – wake up, yoga (look inside box) and affirmations (see below)
6:30am – cardio and the feminine body/booty
7:15am – dishes, cleaning, vacuum, eat something
8:00am - Out the door
After work:
Shower, shave face, moisturize, light foundation, mascara, lipstick, hair, clothes I’ve laid out
Dinner and related
7:30pm – Affirmations and Femininity training (assorted, with wine)

Weekends:
7:30am – wake up, yoga (look inside box) and affirmations (see below)
8:00am – cardio and the feminine body/booty
8:45am – dishes, cleaning (museum quality), vacuum, breakfast
9:15am – yardwork / housework / projects / errands (look inside box)
3:15pm (at the absolute latest) – shower, shave, smooth (inside box)
3:30pm – full makeup (includes nails) I will help you at first, but you need to learn.

Plan to spend the remainder of each weekend embracing your femininity, princess. We have lots of training to do!

Your Affirmations:
I am blessed to serve my Mistress
I will embrace my femininity everyday
This is the right path for us
It’s better this way
Smiling is prettier
It is important that I always strive to be the best me
I will consider everything I put in my body
Sexiness is an attitude
Girls are better than boys
My Mistress knows what it is best for me

My love, embrace everything in front of us. The best is yet to come!

Endless devotion,
Me
 
I think this story is particularly compelling because it could be categorized as forced feminization, or at least coerced feminization. In most feminization fantasies, the person has a deep, perhaps innate desire to explore their femininity, and even transition. But in this case, it sounds like you were not really onboard, but ultimately manipulated your own psychology via submission and devotion to accommodate. Being 'broken' is not entirely inaccurate.

I think these stories concern (and admittedly compel) me when they venture into permanent decisions. Now that I'm spending more and more days essentially asexual (not due to anything regarding feminization - completely circumstantial), and absolutely hating it, I get a bad feeling that someone will manipulate their hormones in a way that seemed like a good idea, but oops, things are absolutely no fun anymore and the game is over. But you can't end the game - it's permanently stuck on forever. Maybe I'm hoping these stories will give me reassurance. I'm a sadist, tbh, and a pretty dark sadist sometimes too, but it *always* has a core of love and true benevolent consideration. I guess I'm more comfortable when I can sense the same in other dominants, but I'm nervously curious when I don't.
 
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27.

I am not a sissy. It's never been how I view myself. Submissive – yes, of the highest order. Woman – not biologically, but definitely how I feel. I don’t like labels, but I make the distinction because of my mindset and my wife’s mindset on our life.

My wife believes women are superior to men; smarter, more capable, better communicators, etc. I’ve come to learn her desire was to emasculate me and push me down as hard as she did because she planned to build me back up in mind, body and spirit once she was done. I’m her sub, and she owns me. To the rest of the world, I can come off as opinionated, even bossy. The rest of the world doesn’t own me and I have been taught to stick up for myself, think for myself and to be confident in who I am. Transitioning is hard. I have some bad days. Less so now, but some real awful doozies in the beginning. Get knocked down, get back up. It’s all a person can do.

This isn’t a kink. It’s my life. It’s not my “clit.” I am not inferior or “for use.” I am a maid in my own home only and I don’t own the cliched outfit. I’m not part-time or full-time or “dressed” or “not dressed.” My name is Alexandra. I am a woman, with a job I obtained as a trans woman, with an “F” on my driver’s license and a father who sends me flowers on Valentine’s Day.

This journal has a long way to go before I get to present day, but it felt like this was as good a time as any for a “status check.”
 
The last time I was "in the mood", which was probably a couple years ago now, I had a full weekend all to myself and remembered my wife had a sexy French maid costume, and I was excited to do some planned chores in it. Unfortunately it turned out she had thrown it out, so it never happened. Dissappointing.

Have you really not wanted to wear one even once? I'd recommend you get one :)
 
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That's terrific. If she wanted me to wear a maid's outfit, I would. The closest I come is an apron for cooking. She'll "theme" me occasionally. We use variations on the Spice Girls. So, depending on what we're doing or where we're going she'll instruct for "Sporty Spice" or "Slutty Spice" or "CEO Spice." At this stage, we know what works for me, so she doesn't dictate my clothing very often. The only real parameter I have is she demands I'm dressed for a professional office environment even though I work remote. Other than that I'm fairly free to choose for myself.
 
At this point in time how often were you permitted a release and was PIV still allowed?
 
I was definitely rewarded for the choice I made and PIV was still allowed. All of this would change shortly, which I had trouble with, but was ultimately the right call by her.
I'm trying soooooo hard to be patient and wait patiently for your next installment. Really! Very, very patient! :):):)

[The damned smiley faces seem somehow disrespectful of the very serious content you are sharing, so please forgive me.]
 
Omg what a story. I am so envious of your journey. Understandabley there are time you may feel uncomfortable. But the overall journey would be total heaven for me.

I would love to find a compatible woman for me and take that same journey

Thanks for sharing
Can't wait for the next installment
 
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I love feminization/transformation stories, especially when they involve reluctance and seduction.

My wife is more affectionate with me when dressed and I am not sure how aware she is of this. It is counterproductive for me to talk about it too much. Maybe it reflexes me being more relaxed.
 
28.

A “trust fall” is an activity where a person deliberately falls, trusting the other person to catch them. Once we started down the femininity path, my life became one big trust fall. I put my faith in her, scared and excited for the future, still somewhat skeptical despite my agreement with our journey forward. I remember looking in the mirror – my male self staring back at me and wondering how the hell it was all going to work.

And then I got to it. Day 1 didn’t start with yoga the way it was written on her instruction sheet. It started with a razor and a long shaving session, so long the hot water had run out by the time I was done. I wasn’t starting from scratch, I had shaved most of my body many times before, but during our “cold war” I paid less attention to keeping to a regimen, a silent, passive-aggressive protest that ultimately did nothing for me beyond draining our hot water tank.

Then it was done. Aside from my eyebrows and the hair on my head, I was smooth. Next up was a tanner – Jergen’s Mouse for medium to dark skin tones (a product I still use today). She wanted it all over me, from my toes to my hairline. It says it dries in 60 seconds, but it took more like 5-6 minutes before I felt dry enough to put clothes on. I also realized it can stain sheets if you sweat at night. My wife often refers to me as a “destroyer of fine linens,” but I’m addicted to the stuff. It works great for smoothing out skin tones, in addition to giving me a tan. I like the way it smells too.

Some light foundation followed (Cover Girl, Soft Honey) and she told me to make sure to give it a moment to set. I remember thinking it odd that I was using makeup prior to a workout, but she knew exactly what she was doing – catering to my Barbie Doll sensibilities … that I didn’t even realize I had. Mascara followed and that was pretty much “it” for makeup that morning.

Panties were next. After so many months of rebelling against this whole thing, it felt good just to put them on and keep going.

And that’s when I had my first real enjoyable moment as a “female.” Whether you call them yoga pants, leggings or something else, they’re the most comfortable piece of clothing in the world. They’re just … cozy. They’re sexy. They made me feel sexy. They made my legs look good. They made my butt look good. They made me look good. I loved them from the moment I put them on. Still do. These were black.

My first sports bra followed (pink). A minor thrill that would become more enjoyable over time. And then my first pair of women’s ankle socks (white) and women’s trainers (also pink).

With that, I added some pink lipstick and a spritz of perfume (D&G, Light Blue).

The last piece was something that I came to love over time – feminine hair. A wig wasn’t my own hair, but it really made a big difference to the image staring back at me. She had done a great job picking it out. A long bob in dark cherry, so definitely saucy, but it went great with my eyes and coloring and really seemed to fit. It felt so strange at first. My male hair was fairly short, so this felt substantial. If I looked down, some of it covered my face. I could flip it. Style it. Wrap it. Use a headband with it. Tie it back. Let some pieces fall. The possibilities were endless. I was hooked on that hair from the moment I put it on. It would become indispensable to me as I grew my own hair out, which seemed to take forever.

And with that, I was the new “me.” As best as I could be. As best as Day 1 could have been.
 
Thank you for sharing. Your story is so powerful to me - the totality of your submission inspires me to give more myself.

I'm curious and hope you will answer one question, or rather a couple of related questions. I took away from your posts that you were never really interested in feminization, much less transitioning, when you met your wife. Nor were you interested in it during the frosty period just before this. In Post #25, however, you say you found yourself. And you also quote yourself saying "I'm not a man." Post #28 is the first time I noticed you describe feminine clothing as appealing. And about yoga pants you say, "and that’s when I had my first real enjoyable moment as a 'female'." So my questions are 1) do I have the above about right - your disinterest in cross-dressing and feminization, and 2) so as you started this trust fall you were suddenly able to enjoy women's clothing and enjoy feeling sexy wearing yoga pants? I guess I'm trying to understand how you completely avoided revulsion or resentment and just got right to joy in dressing femme. Does your "I'm not a man" quote mean that you were willing to revoke your maleness to follow your wife? Or does it mean you finally admitted to yourself that deep down you've always needed to be female (and she got you to the point you could say it)? Forgive the impertinence of my questions, and ignore me if you don't want to answer.
 
Hi there. Thank you for the questions and your interest in my journey. I sincerely appreciate it. To answer your questions, and I hope I do a good enough job doing so ... let me explain: I'm trying to capture moments from the past the best I can. With all people, we feel one way one day and sometimes a little different the next (or occasionally very different). Right before I "broke," which was detailed in post 25, I had a lot of conflicting thoughts. I was mad. But I also wanted our relationship back. I was "against" the idea of feminization, but my stance had softened because again, I wanted my relationship back. As a person and a husband who genuinely loved/loves his wife, I began to rationalize the idea of trusting her/exploring this path/giving in. I was done fighting, and if going the direction she wanted would end it all and get us back to what we were, then I was open to considering whatever that was going to take. So there's shades of grey with this (as with most things) that can be hard to capture in a journal. I've begun keeping one now, since I've come to realize how important having a record is, so this journal - once I get to present day - will have more random thoughts and feelings than it currently does. Hopefully this will give a reader greater insight.

With all that said, 1) yes, you have it right. I was definitely disinterested. There was no revulsion, I just didn't really understand the point. Things were going so well, and this was a radical shift. So I was afraid of change. 2) I don't know if at that moment I "revoked my maleness." But I was very upset, wanted my submissive life back, and if this is what she wanted then I had made the decision to genuinely try. It went way beyond "going along" or something along those lines and instead was an authentic desire to dive into the deep end. Once our communication had resumed, I knew that if I needed a timeout or to talk through something, then that was going to be available to me. So I approached our new direction with enthusiasm, which is something I had to work out in my head. But once I decided, I was "all in" in terms of putting my trust in her and letting this happen. So I did it with a smile, a sense of wonder and it all came from a really good place.

Lastly, I don't know if I always "needed to be female." What I do know is I have found a level of comfort and peace as Alexandra that never existed before. My wife is my true north and my submission to her guides me every day.

Hopefully this helps you understand where my head was at during this time. Thank you again for taking an interest.
 
Thank you for your reply. You did answer my questions.

Your strength in your submission is an inspiration. WAY. TO. GO.
 
29.

“What do you have to work with?”

As I/We looked at the totality of femininity, this was one of the first questions we began to seek answers to. She asked it, and she had clearly already considered it, because she drove most of the conversation. What came from all of this exploration and my struggle to answer this question, may be of help to others here, so I’ll capture what I’ve learned:

(Note: femininity comes from within. We tend to focus on the outward facing stuff, and doing so truly is backwards. But this was my first day, so truly getting in touch with my feminine side wasn’t possible. It’s definitely a journey.)

First, we all have strengths. Yes, men look like men and women look like women – but why? I’ll come back to that in a moment. Men look like men, but where do we overlap with women? In my case I took stock of what I had to work with: I’m 5’9”, so tall, but within range of a typical woman. That was helpful. I was in fairly decent shape and knew enough about exercise to know women and men often care about different things when they exercise, so I could get after it with a more feminine regimen to help areas of my body look more feminine. That was also helpful. My hair was short, but thick. I was in no danger of going bald. And I could grow my hair out. Natural hair. That was good. Women I had dated before my wife, my wife and some of her friends had all said I had “better legs than most women” several times in my life. Good legs? Check! I had/have cheekbones that would become more prominent if I dropped some pounds. I have pretty eyes. Check and check. My hands have always been feminine. My wedding ring is a size 8. This was good. As I began to tick through the boxes, I realized there was a foundation to build from.

And this is where I want to interject because it may be helpful to others out there. Yes, men look like men and women look like women, but we, as males, have attributes that overlap with females (and obviously vice versa). Take stock of what those are. Accentuate them. Play to your strengths.

Second, we all have weaknesses. My feet are larger than I would like. I have a thin top lip. Problems. I don’t like my neck. My shoulders are broader than I’d prefer. My chest too. These were issues.

I’ll interject again to illustrate my point: my legs were good, but my shoulders broader than I’d like. So that led to me to dresses that accentuated my legs (shorter) and downplayed my shoulders and chest (sleeves, higher and/or slimming necklines). Again, accentuate your strengths, minimize your weaknesses.

I mentioned I don’t like my neck. My wife insists it’s actually quite feminine. So much so that one of the only style choices she dictated was my use of chokers. I wear them all the time, unless she chooses to replace it with a collar for playtime (or anytime).

Here’s another example: As I mentioned, I love leggings. They compliment my body from the waist down, which is a strength (decent booty, good legs). I pair curve-hugging leggings with flowy tops and pullovers that minimize a weakness (shoulders).

As I (and you, if this helps) begin to understand your body type and its good points and not-so-good points, I/you begin to develop a style. Having a style sets a direction. You gravitate towards certain clothing options and away from others. It really helped me and I hope these examples are helpful to you.

At the risk of rambling, I’m going to keep going, because femininity isn’t about clothing. It’s inside you. It’s emotional, it’s a mindset, it’s a belief, a guiding principle and a million other inside-of-you factors that have nothing to do with how high your heels are or how short your skirt is.

Nowadays I’m deeply in touch with my feminine self. It’s who I am. Back then, I didn’t know much or any of this, so I freely admit to the “fake it til you make it” principle. What I mean by that is, if I was doing “this” (going femme) then I was going to fucking do it. I wanted to fit the societal norm (you can argue this as right or wrong, your mileage will vary), I wanted to “pass” as they say, I wanted to be “pretty” and I wasn’t ever going to stop. And I quickly learned the clothes only get you so far.

Examples of this include: it doesn’t matter how pretty the gurl is (I dislike the “u” but I need it to illustrate my point), if she opens her mouth and her voice is masculine, the whole thing can blow up. It doesn’t matter how pretty she is sitting down, if she gets up and walks like a dude, then it all blows up. So aside from what’s inside (far and away the most important and really the only thing that matters), and what is outside – clothes, hair, makeup, etc. – are all the other “essence of female” factors that don’t receive the attention they deserve: walking, running, moving, smiling, sitting, standing, talking, coughing, laughing. All of these need to be 1) not a caricature, 2) naturally feminine, and 3) authentically you.

The only way to accomplish movement, mannerisms, posture, speaking and all the rest is to practice. It needs to feel natural and be authentic and come from inside you. It takes time, but it is time well spent.
 
30.

The double life. When we usually hear about a double life it’s typically through some tawdry news story of how so-and-so had two families in two places or something similar. My double life was the opposite. My wife had full knowledge of what was going on, but our family, our friends and my employer had no idea.

During the week I followed the schedule she had laid out. I’d wake, put my wig and workout clothes on, do yoga, say my affirmations to her, exercise, clean up and then jump in the shower. If I was going to the office, I’d wear panties over my cage, and, besides my toes being painted, that was it. I had work to take care of and her weeks were busy too.

If I was working remote, the morning routine was the same. Any video calls for work were done in typical male “business casual” attire – normally a button-down shirt. From the waist down, what couldn’t be seen on camera, were either leggings or one of the two skirts that were in the box of goodies she had prepared for me. I’d wear the one pair of heels I owned, black 3” pumps she got for me on clearance at a DSW (shoe store) near our house. I still remember the first day and feeling like everyone on Zoom knew. It took me weeks to shake the thought. If I moved in my chair, I could hear a pointed high heel click seductively on the floor. I’m sure I blushed once or twice. It was a whole new world.

After work, I’d shower and shave my face and use a light makeup routine of foundation, concealer, eye liner, mascara, some finishing powder and lipstick. It felt like a lot to accomplish and a waste considering a few hours later I’d have to strip it all off before bed, but she was adamant about my routine.

(Note, from a double life perspective, makeup removal became a source of anxiety for me. Anyone who has used it knows that mascara doesn’t completely come off – lashes remain darker; foundation is absorbed and then expelled – staining shirt collars; eye liner likes to stick around – requiring a lot of effort to remove, etc. I was dealing with this every night and morning).

Sexually, we built upon the D/s foundation we had already had. Pleasure for her came from oral and toys. Orgasms were mandatory unless she chose otherwise. I would be teased and denied. Beyond a blissful week of PIV sex after I accepted my feminization path, she made it clear any thrusting into her was going to be detrimental to my development. At this time, she would occasionally tie my hands to the bed, remove my cage and ride me to orgasm. I was required to lay still. When I got close to cumming, she would move very slow, teasing it out of me. I would go gently over the edge.

Weekends became an ever-expanding feminine existence. Outside of general maintenance and landscaping – anything taking place outdoors – I was expected to live “en femme” from Friday after work through Monday morning. Friday and Saturday nights were a full makeup regimen including brows (a disaster at first) and blush, lip liner, eye shadow, etc. I’d also put my nails on for the weekend and I had to deal with them for any outside work that was needed. I’d wear gloves in case a neighbor wanted to talk in the driveway. We experimented with everything: scents, moisturizers, razors, makeup, colors, clothes … and there was endless practice around moving, sitting, standing, talking, laughing and on and on. Parts of it were tedious – I’ve already talked about the makeup – but we were together. She was right there with me; helping, teasing, encouraging, laughing, kissing. I still wasn’t completely sure where all of this was going, but our sense of closeness provided reassurance.

This was also where the “wooden spoon” became a thing. She had used corporal punishment on me in the past, but it was not a favorite of mine or hers, so it wasn’t used often. We have a couple of paddles and riding crops, but one day when I was too slow with the dishes, she spanked me hard with a wooden spoon. It hurt so bad I buckled. I wasn’t expecting it. And that wooden spoon became a threat and occasional deliverer of discipline that continues to this day.

It was also around this time “we” named “me.” My male name wasn’t going to work and I wasn’t enamored with being called “Princess,” so we needed a solution. We kicked around names for a few days and eventually she gave me three to choose from. I didn’t love any of them, so she came back with three more. Alexandra just fit. It felt right. My screen name here is a play on it, since I was “Now” Alexandra after being named, and I’ve heard “NOW Alexandra” as part of her dominance plenty of times.
 
31.

“I want to go out tonight.”

It was a Friday. We had just wrapped up work and I had poured her a glass of wine. I was about to jump in the shower to begin my weekend feminization process. I had been Alexandra for two weeks, a name she used from the moment we agreed on it. It took me a moment to comprehend the ramifications of “going out.”

“Like, out out?” I asked.

“Yeah. Out. To a bar.”

“I don’t know,” was all I could manage.

“It’s settled then.” She smiled. This wasn’t a negotiation. She handed me my chastity key. “Pour some wine, jump in the shower and clean up down there. It’s time for some fun, Alexandra.”

I’m sure my eyes were wide in disbelief. But a command was a command so I did what she asked, pouring what amounted to probably 10 ounces of Chardonnay. I filled it right to the top of the wine glass. Then I took a long swig and headed for the bathroom. She followed me to supervise my unlock, surveying me from the makeup chair. I put on a half-smile and stepped into the shower to start the process.

When I got to grooming my unlocked “tiny thing” as she called it, I stretched it out to shave any rogue hairs along the shaft. I looked up, feeling her eyes. She smiled. “It’s so small even when you pull it.” I went back to the task at hand, humiliated.

Once done I stepped out and toweled off. Then I grabbed the now clean pieces of chastity, dried them, lubed the ring and tiny cage, pushed into it and locked back up.

_____

There were considerations to going out as Alexandra that I hadn’t considered until I came face-to-face with them that night. Here are some of the practical ones:

Going out:

Requires a handbag. She let me borrow one of hers. It also requires making sure whatever makeup you need for touchups makes its way into the bag. I also needed a wallet. I needed my license and credit card in that wallet. Anything else I would need that night needed to be in the handbag. Hairbrush, hair tie, perfume, etc. Handbags get full fast and then you can’t find anything when you’re looking for it!

Requires a coat. I didn’t own one. She let me borrow a wrap since it was warm and a coat wasn’t needed. It would be shortly, when the weather turned.

Requires consideration of where you’re going. In this case we were going to a trans-friendly bar in Boston. I needed to consider I wasn’t just going to magically teleport from wherever we parked to a barstool. I was going to need to walk. In public. In heels. Over uneven streets. For however far it was between the car and the bar.

Requires consideration of what you should wear. I would be seen. I needed an outfit that would work, that would blend, that would be deemed appropriate. (I came to learn that this consideration was much less important for this particular bar. It’s a trans place, it’s pretty much anything goes, and most of the girls dress like hookers).

Two other quick notes: 1) she drove that night, but driving in heels is a skill as well. Takes practice. 2) everything in long nails is harder.

_____

This was the first time I wore an indispensable part of my “being” – a hook and loop waist cincher that pulled everything in and gave me the hourglass shape I coveted. She had bought two, and my feminine ego definitely smiled when I fit into the smaller one. Besides the heels, I wore black thigh highs (Hanes lace top, still a staple, color: Jet), a high waisted black skirt with some flow and flare so my cage wasn’t visible, a dark green colored blouse with three buttons at the neckline I agonized over because two buttons undone seemed a bit too much, but one button undone made me look like a nun, and a black lace choker. She had gotten me some cheap rings and some bangles as accessories, so I added those to my wrists and hands … and I was ready. The waist cincher really helped. It gave me great contour from hip to “boobs” and I genuinely looked “thin.” I did not wear a bra that night.

_____

My head spun as she parked the car. Leaving the house wasn’t bad. I eased my way into the passenger seat, swung my legs in and closed the door. Then she backed out of the garage and I kept my head facing straight as we drove down the street. It was twilight, but it felt like every neighbor could see me.

And now we were here. In a parking lot down the street from the bar, an easy two blocks away.

“You ready?” she asked.

I just nodded. My heart was racing. All I wanted to do was get from where we were to where we were going as fast as possible. It was clear she could read me.

“Get out. Walk slow. Slow, Alexandra.”

I nodded again.

I grabbed the door handle and pushed out into the Boston night. My whole body was on overload. I was nervous, excited, scared. I had taken all of 10 steps and was breathing heavy. Boston has cobblestone streets and they’re murder on heels. I never caught one between cobblestones thankfully, but I was unsteady. I kept trying to focus on my posture. Every time I felt like I was improving, something would put me slightly off balance. I tried to walk slow and failed miserably.

Finally, we were there. She stepped in ahead of me and paid the cover charge. Then I stepped in and the doorman smiled.

“New here?”

“Yes,” I squeaked out.

“You look great.” He smiled. I managed one back.

We made our way to the bar and thankfully there were some seats. I slid onto a stool as gracefully as I could. The wait for the bartender felt like an eternity. After ordering, the wait for our drinks felt even longer. I was grateful when they finally arrived.

Over time I relaxed. The alcohol helped. We met some regulars. I used the ladies room for the first time. I got sort-of hit on by a guy for the first time as well. I’ve come to learn that my wife gets plenty of attention at trans places, but sometimes guys have a sweet tooth for us girls and our cis-sisters are not what they’re hungry for. It’s a fun dynamic.

I’m at home on a barstool. My legs look great. My movements are natural. My voice, when I’m not petrified and it actually works, is fun and flirty.

It took me about an hour to get myself under control – I think I had 3 drinks in that first hour – but the night ended up being a blast. My confidence grew. My smile came out. We had some great conversations. We got home safe.