A Letter From My Harley-Riding, Crossdressing Submissive

Deep down I always knew that I would one day have a profound impact on the crossdressing community. Reading the below article from my submissive this morning, touched me in ways that I never thought possible.

I wanted to thank you for being such an invaluable part of My life and My learning process and for allowing Me to spread My wings and challenge Myself in order to become a better Domina.   

May we never forget to live our truth. 

Something stood out for me in the article, however, and I wanted to use this as a teachable moment. I am all about learning, opening my mind, and challenging notions, so when my submissive wrote "It didn’t make me less of a man; I was still very much attracted to women," I thought I'd take this time to remind everyone that your sexual orientation doesn't make you any more or any less of a man. There are heterosexual men out there who in my eyes will never be real men because of their actions and the same can be said of certain homosexual men, too.

Always remember that "HETEROSEXUALITY DOES NOT A MAN MAKE." 

And with that, I hope you enjoy this story - my submissive's very personal account of his life as a cross-dresser. 

Namaste!

Mistress Sara xo 

 

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"I’ve always envied women; I’ve always admired them as well. The

clothes they get to wear; the way they accessorize their outfits. Perhaps it’s

my admiration for women that made me submissive so many years ago.

Today, I live to serve Mistress Sara. I learned early on that her approach to

dominance is subtle but firm. She doesn’t raise her voice and make

demands or give orders; she suggests and recommends with a confident

certainty that her words will be heeded; clear directions absent any

ambiguity. Recommendations from Mistress Sara are an opportunity to

excel and are not to be ignored. And that brings me to our current

adventure.

 

Mistress Sara “recommended” that I write about feminization;

specifically, my perspective and experience on the subject since my

Mistress has started to feminize me. I will say a subtle foundation was set

decades ago when, at the insistence of my then girlfriend, I started wearing

panties. Panties progressed to pantyhose. Wearing pantyhose led to me

shaving my legs every other day. And, if you’ve ever put pantyhose on your

freshly shaven legs you have to acknowledge it is a very sensual

experience. Does that make a man effeminate or a candidate for full

feminization? Not necessarily, but it certainly plants the seeds.

Imagine if you will, a stereotypical biker: over six feet in height, a fit

individual with shoulder length hair and a full beard, dressed in leathers on

the back of a Harley Davidson motorcycle. Would you suspect he was

wearing pink panties and pantyhose layered beneath his jeans? Probably

not. But, it’s that contradiction, that stark contrast that convinced my

previous life-partner to push my limits by convincing me to cross-dress from

the waist down. We shared a Dominant / submissive lifestyle. She was the

former, I the latter. Not in the bondage and discipline sense, mind you, in

fact she rarely tied me up. We were both hedonists and due to my

submissive nature, I would do anything to please her. Yes, I wore high

heels, stockings, and a garter belt but it always led to a happy ending for

both of us; I couldn’t complain; and she loved it. It really was about making

her happy.

 

Unfortunately, as so many good things do, the relationship ended. She

moved on, leaving behind a man dependent upon dominant women for

some sense of structure. After months of wandering aimlessly, I met

Mistress Sara and she accepted me as her submissive. As our relationship

evolved, she recognized I had certain tendencies: my love for feminine

apparel, the collection of high heels and lingerie I had amassed, my desire

to cross-dress from the waist down even when sex wasn’t involved. Clear

indicators I was a candidate for full feminization. It wasn’t just a fetishist’s

love for something silky brushing against his genitals. And thus she

decided to feminize me completely. Feminization is not something that

happens over night; at least not for me. When she first mentioned it I was

excited by the thought. I’ve been wearing panties and hose under my

normal clothes for ages but I never once thought of going all the way.

Mistress Sara has a very compassionate approach to domination. Her

skill is in reading the individual and intuitively understanding their needs

and then shaping their needs to fit her desires. It inspires obedience to

such a depth, I dread the feeling of disappointing my Mistress. When she

first mentioned feminizing me, while I was excited, there was some

apprehension. But, She made it clear we would do it together, in stages,

and if ever I was uncomfortable, we would stop. How could I say no?

First came the high heels. I’ve been wearing high heels in private for

quite some time. My former partner bought me my first pair - black double

dorsay pumps with six inch heels. How many people actually know what a

double dorsay is? I spent hours learning to walk in those heels; she spent

hours laughing at me trying to walk in those heels. As I learned to walk, my

love for heels grew and so did my collection of shoes. Mistress Sara

designed a pair of heels for me. The first open-toe shoes I’ve ever had. Of

course no proper lady wears open-toe shoes without polishing her toenails.

The first step in my feminization was to buy some burgundy red nail polish

and paint my toes.

 

Painting toe nails wasn’t new to me. I painted my former lover’s toes on

numerous occasions. Why painting my own was such a challenge, I’ll never

know. In one evening I painted them four times. Each time I managed to

get more polish around my toe nails than actually on them. I was a dismal

failure at painting my toes. I’m still practicing.

 

Although I’ve been cross-dressing from the waist down for years, I’ve

rarely had the occasion to wear a bra. My previous partner had me wear a

sports bra now and again but Mistress Sara made it clear she doesn’t care

for those. So we went shopping on line to find a bra suitable for the “new”

me. There were complications since I’m flat chested and finding a bra to fit

my chest would definitely require a cup size larger than I could fill. That led

to our discussion of breasts and hair.

 

Hair was an issue. No, not the hair on my head, the hair everywhere

else. Mistress Sara suggested I visit a waxing salon to remove unwanted

hair below the panty line and shave or wax the rest myself. Researching

the local area the only waxing studios I found didn’t cater to men. Not to be

dissuaded, Mistress found a waxing kit on Amazon; I ordered it

immediately. At the same time, I continued to search the local area. As luck

would have it, I found a waxing salon that catered to both sexes and would

do a full Brazilian. A full Brazilian removes ALL of the hair around the

genitals and the butt and butt crack. I made an appointment. As I stared at

the waxing kit Amazon delivered it only made sense to add the chest,

stomach, and back to the waxing appointment. I would rather have

someone else pulling each strip of wax then attempt it myself.

The salon was unremarkable. It looked like any other store front in a

strip mall. I checked in at the desk and was told to sit in the waiting area

which faced the sidewalk outside. At that point, I started to consider the

possibility of encountering someone I know walking by and what I would

offer as a reason for being there. Fortunately, the young lady performing

the waxing introduced herself and moved me to a private room before an

excuse was needed. Once in the room, I was instructed to disrobe and lay

on the table. The technician was very professional; she explained what she

was going to do and in what sequence. As she put it, she wanted to do the

harder parts first, so she started with the Brazilian. Slathering hot wax on

my pubic area, she used her hand to press the wax against my skin to

collect as much hair as possible and to get close to the root. Giving it

seconds to harden, she instructed me to take a deep breath and exhale

forcefully. She pulled the wax and attached hair free as I exhaled. I’m not

sure if timing the wax and hair removal in such a fashion was meant to

mitigate pain or keep a person from screaming as their skin was being

ripped from their body. It was very painful - perhaps not as bad as depicted

in the “Forty Year Old Virgin” but, in my view, not far from it.

 

The technician really was wonderful. During the Brazilian, while she was

manipulating my penis (Yes, she waxed that as well) I developed an

erection. Being self-conscious about it, I apologized to her. She said “it’s

not unusual” and “don’t worry, it’s no big deal.” Of course the erection only

lasted until she pulled the next strip of wax but as I stopped screaming I

couldn’t help wonder if the “no big deal” was in reference to my size or that

it is a common occurrence when she waxes men. She left me totally

hairless from my collarbone to my toes. I have to say being hairless feels

amazing. Mistress Sara now has me moisturizing and exfoliating regularly;

my skin feels as soft as any woman’s. Running my hands down my chest,

across my abdomen to my pubic bone never felt so stimulating - I feel

feminine!

 

While shopping to find a bra for me, Mistress noted that because of my

body size and structure I would need a “D” cup. Except, wearing a “D” cup

would require padding or breasts. Padding would fill out the bra and might

even look nice but, beyond the visual would it contribute or enhance the

“female experience”? Mistress Sara recommended we explore web sites

that sold breast forms; silicon prosthetics that are attached to the pectoral

muscles with the look and feel of real breasts. Surprisingly, there are a

number of sites that provide breast forms in different shapes, sizes and

colors. After carefully researching various products we settled on the

“Amolux Diamond” sold at thebreastformstore.com.

 

They arrived in less than a week. My hands were shaking as I opened

the box and gently removed one of the breasts. They felt so amazingly real

- it was hard not to put them on immediately but, given the magnitude of the

event, I couldn’t do it without my Mistress.

These breast forms are designed to adhere to the chest without

additional adhesive. They also can be worn bra-less which, as it turned out,

is how we tried them first. Attaching the breast is a matter of cradling and

positioning it prior to pressing it against the skin. It sticks… and strong

enough to bounce on one’s toes without it becoming dislodged. In a matter

of moments I went from being flat-chested to having a voluptuous D-cup

bosom. Dressed in pink panties, black hose and heels, and my breasts

attached, I don’t think I ever felt more feminine or that excited.

Mistress Sara made it clear as she gave me permission to remove my

chastity device, whenever I have my breasts in place I no longer have a

penis or pee-pee, it is now a clit or clitty. By then it was getting quite hard.

 

The level of excitement continued to grow; it was as though I was losing my

virginity again only this time as a woman. My Mistress used an eight inch

dildo on me; giving me the gift of an orgasm so intense it left me crying

tears of joy. This journey we began when my Mistress decided to feminize

me isn’t over; I am very much a work in-progress and in truth, I hope the

adventure never ends."