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My Path To Womanhood

“Ohhh… Ron, you’re getting boobies just like mine,” my older sister Lisa squealed. I was mortified when I looked down and two tiny peaks formed a sort of party tent on my T shirt. I had not noticed before, but she was right. She was not the only one to notice. As they became more obvious, the other boys humiliated me by taunting and groping me. The most stinging remark was “You should have been a girl Ron.” Up to now I was just another adolescent boy, but these set me apart from the other boys and made me the object of ridicule. The doctor's assured my parents that I was normal and would grow out of it when the hormones kicked in. It was called gynecomastia, or abnormal enlargement of the male breast. But I didn’t grow out of it. I watched Lisa carefully. When she complained that they felt heavy and her nipples hurt, Mother assured her that was normal. Then one day, mine started to ache too. I was confused and bewildered. Normal, Mother said – for a woman. Was I becoming a woman? My breasts grew very sensitive and my confusion deepened when I found that massaging them gave me erotic pleasure. As they grew bigger, they developed a pronounced jiggle as I walked. I tried to hide them by going about with my arms crossed over my chest. Isn't that bouncing awfully uncomfortable dear?" my mother asked.
"I don’t know what to do about it mom," was all that I could say. "Well I do," she said. With that she left the room returning momentarily with one of my sister's bras. She instructed me in the correct manner of putting it on and noted with some satisfaction I think, that I filled the cups. This was much more comfortable, but of course, it made them project more from my chest
My father would have none of this. He immediately noticed my new profile and ordered the bra removed. He then declared that from now on I couldn't leave the house unless they were tightly bound with an Ace bandage. “I’ve tried since you were a kid to get you involved in sports and normal manly things, and now I come home and find you in a bra. Do you want to be a girl son?” Dad was as old school as they come. A lantern-jawed ex soldier, he had indeed set impossible goals for me to achieve. Once he told me how proud he would be if I tried out for the football team. I actually did show up for tryouts, but when we were told to dress out, I slunk off in the corner. Some kid coming out from the shower shouted “the girl’s lockers are down the hall,” and everybody laughed. I turned down Dad’s offer of swimming lessons, summer camps and hunting trips. He probably thought I just didn’t want to be in his company but the real reason was that I couldn’t undress in front of other boys. I know I deprived him of the satisfaction of seeing his son grow into an image of himself. “No dad, I don’t want to be a girl.” I said. So every day I left for school with my chest bound by Ace bandages. That, plus a combination of loose shirts and layering helped me escape most public notice.

But not all. One day as I walked home from school, I was assaulted by 3 boys from school. They taunted me and groped me. I tried to run, but they caught me and surrounded me. My face burned with embarrassment and I felt tears welling up in my eyes. They finally succeeded in tearing off my shirt and the Ace bandages. This delighted them and they soon had me on the ground with my arms pinned down. My humiliation now turned to pure terror as I felt my pants being pulled down. "Oh God, help me" I screamed as I realized they were going to rape me. I was totally powerless to resist as my fragile manhood was about to be torn from me. I felt the biggest boy tried to penetrate me from behind as the other two screamed their encouragement. I struggled desperately to free myself, but it was the intervention of a passing stranger who broke up my ordeal. I ran home crying with my arms folded over my chest. My Father was working in the driveway, and I flew into his arms. I felt dirty and violated. I only wanted my Father’s strength and comfort. Sobbing breathlessly, I told him what had happened.
“Well they probably thought you were a girl” he said biting off each word in ridicule. I was electrified at this remark. That could he excuse the fact that I had nearly been raped as a mistake in gender recognition was beyond anything I could grasp. My shame could seek no comfort from him. I realized at this moment that I had lost my father forever. His stern countenance revealed no trace of compassion. I found this only in my mother’s arms.
From time to time Mother brought up the issue of a bra for me. And my father’s response was usually some variation of, “Hell no, I won’t have a son of mine wearing women’s underwear. He’s caused me enough embarrassment already.” On one such occasion my mother reached over and pulled up the front of my sweatshirt.
“For God’s sake John, will you face the facts? Look at him- he’s my size.”
By now they were indeed the size and shape of a girl of equivalent age. My father’s eyes bugged. “I guess you’re right” he replied weakly. As I slipped into one of Mother’s bras,
I was surprised to find her scent still lingering. This was much more comfortable for me at least at home.
During this time my mother and I became closer than we had ever been. I keenly felt her compassion as much as I felt my father’s rejection. One Saturday morning when my Father was gone, she said we were going to the shopping center. I started for my room to bind myself as usual, but she said that wouldn’t be necessary today. We went directly to the foundation department of a large department store. She found a sales lady and announced “I want my daughter professionally fitted in a support bra.” Wow! I was dumbfounded! ‘My daughter.’ This was the first time she had used the feminine noun for me and a thrill ran through me. “Certainly, follow me ladies.” the sales lady said.
As if in a dream I followed them into the fitting room where I removed my jacket and blouse as instructed. I was vaguely aware of the sales lady stretching the tape over my bra. What was this woman thinking? This was the first time that anyone outside the family had seen me without my Ace bandages. Did she take me for a boy with breasts or just an awkward gangly girl? My beardless face and unisex hair offered no clue.
“38 C cup should do it,” and the sales lady went to select several models. Mother picked one and held it out to me. Now I was grateful that she had showed me the proper way to put on a bra. I was distantly aware of their conversation about uplift and separation that this model provided. It did feel wonderful and it completely controlled the jiggle. Mother finally selected the two that she thought offered the most support and added a frilly pink sleep bra. Almost as an after thought she sent the saleslady back for a black lace push up bra. When I wiggled into this I was amazed that I appeared to be at least a D cup and I had more cleavage than I had ever had. The sales lady even showed us that the lace lining the top of the cups could be folded under revealing even more.
“I don’t know when you will wear it dear, but every girl ought to have one.” my mother said smiling her approval.
It was only in the car going home that the full enormity of what had just happened settled on me. Mother has pronounced me her ‘daughter’, thereby validating my innermost suspicion that I should have been a girl. Those boys had been right years ago when they taunted me. Mother knew it and now I know it. She was also openly defying my father and ending forever his intention to make a man of me. And if further proof was required, I had successfully passed the scrutiny of another woman in the most personal circumstances. I felt that which I had been fighting all my life beginning to slip away, replaced by the warm glow of reassurance. If I could not have my father's approval, I would at least have my mother's.

Mother now took every opportunity to encourage my feelings of femininity. She brought me pretty frilly things to wear in the privacy of my bedroom or under a robe. We spent hours at her dressing table styling my hair. She taught me about skin care and moisturizers. She brought home my first pair of heels- bone white pumps with three inch heels and patiently taught me to walk with confidence and grace- lessons I never forgot.
All this attention was appealing to my very core. Being pretty was much nicer than being drab
One time my sister had a sleep-over for 3 of her friends. Some time in the night, the four girls entered my bedroom and aroused me. It seems that Lisa had told them about my secret and they wanted to see for themselves. I was agreeable, but said,
“Only if we all do it.” So giggling like school girls, we all unbuttoned our pajama tops. I was very proud to show my perky boobs to the other girls and there was much feeling and comparing. I noted too that only one girl was larger than me, and she was already sagging.
There were further opportunities to bond with my mother. On one such occasion there was to be a designer fashion show in town and it happened that my father would be out of town. Mother had two tickets for us. But first she declared,
“We have to do something about that awful mop of hair.” This occasioned a trip to the hair salon where they created a sort of pixie cut that could be styled girly or boyish as the occasion demanded. At home we selected what we would wear for the event. Mother a charcoal skirt and blazer outfit with burgundy alligator sling back pumps. We were delighted to find that I could wear most of her clothes in a size 14. I selected a white satin blouse paired with a light grey pencil skirt. We decided that red leather heels and a belt would make that outfit pop. But since my mother wore a size 9 and I wore an 11, this necessitated a trip to the shoe store.
“How do I go Mother?” “Girl mode definitely dear. We can’t have boys trying on heels in public”. We came home with a beautiful pair of red leather ankle strap sandals with a 3 ½ inch heels. As I stood looking at myself in the mirror, Mother observed that I was over 6 feet tall. “Tall women make the best models dear,” she concluded.

On the morning of the event, Mother and I spent hours getting ready. We found that my still youthful skin needed only a light foundation with some rouge highlights over the cheekbones .She plucked my eyebrows into as feminine a shape as we thought we could get away with. She instructed me carefully in the application of mascara and eyeliner, having me do it over until I got it right. Lipstick and gloss were a snap. As she worked she observed,
“I knew you could be prettier than your sister. She never cared about her looks and never let me teach her anything. She’s was always more a boy than you were.”
“So, I’ve not been a disappointment to you Mother?”
“No Hon, you’ve been the daughter I’ve never had with Lisa.”
Mother had her own little grown-up Barbie doll now and she loved it.

We slipped into our clothes giggling more like best girlfriends than mother and son. Mother chose a garter belt and hose, but offered me pantyhose as all the younger women were them wearing them these days. The white satin blouse, cinched by the belt, molded perfectly over my bosom. Mother’s efforts had produced a striking change. I was lovely. I was ready to meet the world as the woman I should have been. As we walked from the car, our heels clicking on the pavement, she repeated her instructions for the
100th time. “Walk with your hips leading, take shorter steps, relax your upper body, let your arms swing naturally, stick your chest out, and remember to adjust your skirt when you sit.”
The room was buzzing with the titter of high-pitched girly laughter and the clink of wine glasses. A long spotlighted runway dominated the room with clusters of folding chairs surrounding it. We left our purses on our chairs and joined the other ladies in a glass of wine. Mother immediately engaged a clutch of women in conversation, but I was a little self-conscious about my voice and preferred to limit my interaction. There was no question about being accepted as a young woman and one woman even commented,
“Your daughter has such lovely long legs. She should be on the runway.” Mother beamed with satisfaction at the compliment.

The show was delightful and as each new outfit was modeled, we eagerly imagined how we would look in it. One tall elegant model appeared in a stunning royal blue gown with a high empire waist and a décolletage trimmed in rhinestones.
“I want to wear a gown like that someday,” I whispered into my mother’s ear.
In the car going home, Mother asked,
“Wouldn’t be much nicer if you had a handsome young man to whirl you around the dance floor in that lovely blue gown that you admired?” she said. “A man… I don’t know,” I answered.
“Do you like men?” she asked.
“I like being around girls, but still I watch men, and wonder what it would feel like to be in their arms. And besides, I’m not exactly like the other girls you know.”
“There’s a man for every girl dear,” she concluded.
“And besides, I don’t even know if men would find me attractive.”
During this time I enjoyed cross dressing whenever my parents were away. It was wonderful to release the inner woman. On one such occasion, I met a young man in a movie theater. We talked, held hands which soon led to petting. I shamelessly allowed him to unbutton my blouse. I thrilled as he caressed my breasts. We were both fully aroused by now and he had a very large bulge in his pants. It was a hormone-laced voyage of discovery for both of us, he being as inexperienced as I was. He soon had an enormous climax, and I was amazed and pleased that I could produce such an effect on a man. But I had my answer. Men could be attracted to me sexually, and apparently I was to them.
And so I entered my adult life, working in male mode and hiding my bosom as best I could. I worked in an office of 4 women and 8 men who never suspected that I had a secret in my shirt. Cross dressing after work allowed me to unleash the woman inside for shopping, clubbing, and once, for love.
Hunter actually thought I was a good looking woman. He was 25 with a model’s good looks, and I was over 30. I never would have approached him first. He simply would not be on my radar screen. We met on one of those rate/ me/date/me sites where I
foolishly posted my picture in a little black dress and heels. But his emails were so sweet and respectful. He was very complimentary and asked only if we could chat. I couldn’t resist. I’ll admit that I took it as quite a compliment and I was as giddy as a schoolgirl anticipating a prom night.
He was a culinary arts student in New York City and since I made routine trips there, my fantasy world blossomed with the possibility that we might actually meet. In my heart I knew that this should never happen. .
Hunter was so dynamic. Exciting things were happening in his life and he was eager to share them with me. He freely emailed me about his course work, his career plans, and even some relationship issues with girls. He dated quite a few young women but always he came back to me. I listened and gave him my best advice and like conspirators we plotted his next move.
We finally met in the spring at Tavern on the Green in Central Park. I wore a tweedy jacket and skirt with brown leather boots. His good looks were breath-taking in person. He was tall and slender with steel grey eyes and curly blond hair. We had a long lunch under the greens of the Tavern, and at the end he asked if he could see me again.
“Hunter dear, I’m not like any other woman you’ve met,” I said. I know, that’s why I want to see you again” he replied. I took a long swallow of wine and confessed that I had been born a man. He stared at me unbelievingly, his eyes wide in wonder. “I don’t care,” he finally stammered, “I want to see you again.”
The next few months were deliriously happy ones as we explored and deepened our feelings for each other. Our intimate moments were natural and joyous. Nevertheless, Hunter had some rough edges. He was naïve in many ways. He had never been to a symphony or an opera, never owned a suit or ordered wine in a restaurant. I happily addressed and remedied these deficiencies in his experience.

He needed a little help with his appearance. He appeared one night to take me to the Symphony, followed by dinner. He had three days worth of beard, and rumpled jeans paired with a shabby sport coat. I was in a black sheath, Manolo Blahnik stilettos and
black Donna Karan hose. The next day I bought him a suit and several shirts and ties. I had to show him how to tie the tie.
Young men, I discovered were often shy and unsure of themselves. Hunter was likely to blow the slightest mishap all out of proportion. I suppose this was a consequence of having less life experience to draw upon. If his soufflé didn’t rise that morning he would despair that his culinary career was over. So I guess chefs begin to develop their emotional volatility early on. I’d always put my arm around him and soon his perspective would be adjusted. I never understood what he saw in me.
“Hunter, why did you pick me on that website? You could have had any of the beautiful 20 or 30 year old girls,” I asked him one day.
“Because you’ve got it all together,” he said with a wry look on his face.
“Meaning what?” I asked.
“You’re calm, cool, and comely. Besides I like how you look in a dress, hose and heels and I like how you smell and feel.”
“But Hunter, most women my age dress that way.” “Yes, I know,” he said with a twinkle in his eye
Hunter was as generous as his situation would allow. But he had no appreciation of age-appropriate gifts. He once gave me a beautiful black lace bustier that he bought from Victoria’s Secret. I tried it on and said, “Oh God Hunter, I look like the front bumper of a 1950 Buick”. “No you don’t. You’ll look like Lady Gaga when we go out clubbing.” What was this man thinking about me?
Another gift was a tartan miniskirt and it was really short. So I found myself prancing all over midtown with cold January winds caressing my bottom but from the look in his eyes, he approved.
In the end, I had to let my little cub find his own way. His studies were taking more of his time and my trips to New York were getting fewer and fewer.
In male mode, I occasionally dated women, who were either delighted when I revealed myself, or repulsed, saying “it would be like having sex with another woman.” I never wore a T shirt, learned to swim, or exposed myself in any way. I could have had them surgically removed of course, but they were beautiful part of me that gave me much pleasure.
It finally occurred to me that if I looked a little more female I might appear in public without benefit of binding. I started laser beard removal, and had my hair cut to a little more girly style. A little color on my lips and maybe some earrings pretty much insured that I would be taken as woman. I found however that I had to patronize two sets of shops and stores- one male mode, one female. Inevitably there were the slipups when I’d open the door for a delivery man in male mode but with a perfectly obvious bosom.
“So when are you going to do it?” my friend Kay asked. Kay was my age and lived in the same apartment building. She was deeply interested in my gender conundrum and we found that we could share some of our clothes. Kay helped me with a thousand little details that come naturally to women. She filled the vacuum left by the death of my mother.
“Do what?”
“You know, transgender. How long can you keep up this charade of changing your gender to fit the occasion? And that breast binding of yours is positively medieval.”
“Well it’s kept me from sagging,” I responded. “Every woman your age is entitled to sag a little.” She replied.
She was right. By age 50, I had grown impatient with this lifestyle. I was aware that life was passing me by without ever releasing the inner woman that lurked within my skin. I decided I would transgender. We found a clinic in Cleveland that specialized in such matters. After 3 days of tests and interviews with a half dozen specialists, it was determined that I was a good candidate and could expect optimal results.
Although the clinic required that I live full time for a year in my desired sex, I was not entirely convinced I’d have the ultimate procedure. They did start me immediately on hormone treatment and very soon after I noticed a softening of my skin and my hair grew more luxuriantly. I also experienced an inner contentment that was never there before. I was convinced I was on the right track.
That same year my trachea was shaved to eliminate the Adam’s apple and I began professional voice instruction to help me develop the pitch, lilt and expression of a female voice. My experience was that I could pass as a female in person, but on the telephone I’d be ‘sired’.
During this time they added progesterone to my hormone cocktail and before long my areola’s and nipples enlarged to womanly proportions. My figure however needed a bit more work. I still had the straight boy hips I was born with. Had I been younger, the hormones might have corrected this, but for me there was no option but surgery. Fortunately there was a procedure that implanted silicon sacks over each hip bone and buttock, which could then be filled with injected saline. This was offered by a luxurious spa-hospital in India. Ultimately Kay and I booked a flight to India.
The hospital was indeed luxurious and we were soon installed in side by side rooms. The doctor I was assigned, filled me with confidence and it was decided that 500 ml of saline would be injected into each hip and buttock. That would add about 2 inches to my contours, bringing my lower body into proportion with my upper.
The procedure went smoothly. And after a few days of pampered luxury, we were ready to fly home. I was shocked however to find that I couldn’t get my pants over my hips. I had foolishly forgotten that little detail. Kay had to make an emergency pants-buying spree downtown before we could fly home. It was an uncomfortable flight home for me, and I discovered that I was now a 16 dress size.
These changes were now impossible to hide and I undertook to tell my friends and relatives. The clinic had warned me that most such patients can expect to loose some friends and even family. It was indeed so- my father never spoke to me again.
I was greatly vexed at how to tell the dozen or so people at the graphic design center where I worked. I decided I’d introduce my new self slowly, a little at a time to get them used to the changes. Of course, now that I had to wear women’s pants. I couldn’t very well hide that. I did however add clear polish on my nails.
Not many noticed when I went back to work on Monday. “Packing on a little extras weight Ron?” my obnoxious co-worker Walter asked. But the four women in the office said nothing. After a week of so, I added earrings, very small but perfectly visible. Next I took to wearing women’s shoes- flats of course, and boyish ones at that. Still no one noticed. A little color on my lips brought no reaction.
Finally I had only one card left to play. I would wear an every day bra and forgo the binding. To lessen the impact, I chose to wear a big bulky sweater. I had to walk through the outer office past the three secretaries, then down an office-lined passage to my own office. I had hardly closed the door when Alice, the office spinster, and Megan the office tart, pushed their way in and closed the door.
“What’s going on with you?” hissed Alice. Before I could answer, Megan piped up,
“You’ve got boobs! Did you get implants?”
“No, I got them the same way you got yours. I’ve just been keeping them under wraps,” I said. “Could we see?” asked Megan. I raised my sweater to reveal my bosom in a crisp pink bra. “ohhhh, they are real!” squealed Megan and she reached out to cup them. Alice was a bit more restrained. “Are you changing your sex Ron?” She asked. “Yes girls, after a lifetime I’m finally being honest with myself and adjusting my body to fit the inner soul. So please, from now on call me Rhonda.”
“We knew something was going on when we noticed you were wearing nail polish” said Megan. Oh fine- I walk into the office with 44 inch hips in women’s pants, and they notice I’m wearing clear nail polish I thought to myself.
The cat was out of the bag now. I had to assume that everyone in the office knew. That afternoon, one of the guys passing me in the hall murmured “Still got your balls Ron?” Another asked “Care if I cop a feel Ron?”

Later in the afternoon, Mary Alice and Grace came into my office asking for a peek. The girls were genuinely curious and I suppose if I was to be one of them, I could reveal a little of myself. “How did you manage to hide those from us?” Mary Alice asked. I let them in on my secret binding ritual.
I hoped that day would be the hard part. Next Monday and from now on, I’m going to walk in as 100%woman. That weekend I had my hair cut into the layered bob I wear today. I had my nails done and I even made a stop at the spa for exfoliation.
Monday morning I selected a calf-length plaid wool skirt, a black turtleneck sweater, belted at the waist, black leather high heeled boots and gold hoop earrings completed the outfit. I swept into the office with as much drama as I could muster, I did a little pirouette
for the girls before they surrounded me saying,
“Rhonda you look marvelous”, and” I love your style,” and “where did you find that lovely skirt?” It was like welcoming a long lost traveler.
But, it was the reaction from the boys that surprised me the most. They immediately offered me the deference they accorded to other females in the office. They held doors, they brought coffee, there was the occasional flirtatious glance, and best of all, they called me Rhonda.
It’s been 5 years now and I have fully transitioned. It is wonderful to be so proud of what I had kept hidden perfectly for so many years. I thank science that some of natures mistakes can occasionally be fixed.
rhnd rhnd 51-55 4 Responses Aug 9, 2012

Your Response


I so much enjoyed your story and I am so glad it has worked so well for you in many ways. It gives so hope for me that someday I may have the same results and acceptance.

Go Rhonda!

Well thank you so much. Telling this story required a great deal of emotion from me. But I feel better when I get compliments from strangers who read it. Many thanks

what a terrific story!

wonderful story