Synopsis: Ronald is a bachelor in his early twenties, has an apartment and a part time job that fits his college schedule. Ever since “dress up play dates” at an early age and “punishments” by his mother as an older child Ron never had a problem in wearing makeup or women’s clothes. He evolved. Discovering his femininity - Questioning his femininity - Repression of his femininity – Acknowledging his femininity – Accepting his femininity – Living his femininity required an Angel -

Ronnie reflects on his past: thoughts, feelings, urges and gender identity began to make sense. (This is part 1 of a 3 part trilogy)

Ronnie reflects on his past: thoughts, feelings, urges and gender identity began to make sense

I was an only child being raised in a single parent environment by my mother. I was an introverted loner that craved inclusion.

Two neighbor kids, Josh and Lucy, allowed me into their inner circle primarily because I lived two houses away; it was convenient for them. Josh and his sister were a couple years older than me. We’d play together after school and on weekends primarily at their house. Lucy was the unspoken Alfa leader of our play group. As was the fashion trend of the day Josh and I had shoulder length hair which would soon work to my advantage.

Our interaction and play at age 12 was varied; watching movies, board games, and general messing around kid stuff. Playing ‘dress up’ was not our only activity; it was just my favorite.

Because of Lucy’s girly interest in being a famous rock star (and her dominant personality) we frequently pretended to be in a rock band; an all girl band. Lucy insisted that we always looked the part. Our costumes were never risqué but were always very “girly-girl”; skirts, dresses, feather boas, stockings, bracelets, hair barrettes, makeup and whatever would make us look girly.

I didn’t object to Lucy’s dress code because it made me part of the group. It also gave me the excuse I needed to do what I had been dreaming about for a long time; dress and act like a girl!

To my great delight Lucy began including cosmetics as part of our play activities; we all became adept at painting our nails and applying lipstick as well as removing it. The smell of makeup and nail polish was erotically intoxicating to me. It was my suggestion that Josh and I, for true authenticity, should also wear panties like Lucy; she eagerly donated two pairs of her “pretties” to each of us.

Josh and I wore her pretty panties even when not playing Rock Star. I enjoyed it all and fell deeply in love with my feminine side. Dressing and the love of feminine clothes was our secret; a secret to keep from our parents; Josh agreed.

The band breaks up

When I was 13 Lucy discovered boys and our rock trio became a duet.

Even though Lucy was gone my play dates with Josh in which we used cosmetics and dressed like girls continued; we never pretended to be in a band because our interests, thanks primarily to Josh, had moved on to other things and activities.

Josh goes to camp

Josh spent a week at summer camp and, like Lucy, he discovered boys. The day after returning from camp Josh “discovered” me.

When we would get together Josh began locking his bedroom door. “Just in case” Josh said. “We don’t want our folks to think we’re sissies.” Ironically we were sitting on Josh’s bed wearing panties, pantyhose, lipstick and nail polish which could only be interpreted as a very sissy or queer activity!

Josh had discovered masturbation and other things at summer camp and was eager to show me how it was done. I was a quick learner. Jerking off in his room, dressed as girls, became our favorite pastime. We learned to have a box of tissues handy.

Towards the end of summer while we were dressed in lingerie and skirts, Josh hugged me and said, “Ronnie, I’ve found something even more pleasurable, pay close attention.”

Josh had me slide my skirt and panties down to my ankles and sit on the edge of his bed. He knelt between my legs and applied fresh lipstick. The warm wetness of Josh’s mouth changed my life forever.

It was shortly after this experience that I began to wear panties and stocking under my boy clothes at every opportunity. Seeing naked boys in PE class created thoughts and urges I’d never felt before Josh had pleasured me.

Abandoned

Josh and Lucy’s parents got a job transfer out of state. After so many months of intimate companionship I felt that Josh was abandoning me and it hurt me deeply; it was like Santa was stopping at everyone’s house but mine.

Time passes – age 15

Except for occasionally wearing panties, lipstick and nail polish months passed before I was able to really get in touch with my feminine side again. As it turned out fully dressing in girl clothes would be a total immersion experience and it would be due to an unplanned fortuitous fluke of good luck.

I had turned 15 and had made my mother very angry for some trivial transgression of me cursing out a school employee; my selection of curse words had offended her deeply. In a heated moment of indignation at school I had called a teacher’s aide a “fucking cunt”. The school principal, Mr. Logan, called my mom and they agreed I needed to be punished for disparaging a female and being a sexist misogynist. “Those tendencies must be corrected if Ronald is to remain in public school” Mr. Logan said.

Mom assured Mr. Logan that a stern and appropriate punishment would be my fate. The two spoke for a short while and they ended the call.

Petticoat Punishment

"Petticoat punishment" is a form of punishment that refers to when a male is forced to wear female clothing such as a petticoat, dress, skirt, panties, stockings, heels, makeup, nail polish, etc. in lieu of other being subjected to other alternate unpleasant punishments. It can be used as a punishment for bad behavior and/or to change a person’s behavior. PP can involve themes of feminization, sissy maid scenarios, etc.

Lucky me!

Mom was determined to punish me into being a ‘good boy’ via petticoat punishment. “I think you need to dress like a ‘cunt’ and BE a ‘cunt’ for awhile!’ she said. “You, Missy, need to learn what we ‘cunts’ have to deal with; walk a mile in our panties and heels and learn what it’s like!”

Unknown by my mother her petticoat punishment was really ‘petticoat pleasure’ for me; it reawakened my dormant femininity and made me realize who I really was and who I would always be. I just couldn’t let mom know that I loved every moment of it. I played the victim card well.

Please don’t!

“Please mom! Don’t make me dress like a girl! Anything but that! Pleeese don’t do that to me! I’ll be good!” I begged.

“You’ll do as I say as long as you live in MY house, Missy!” Mom retorted. I inwardly smiled at being referred to as Missy.

My little girl “punishment” becomes self exploration

I was to be grounded at home for a ten days and would be “forced” to wear lipstick, panties, camisoles, dresses and black patent leather Mary Jane shoes (with a two inch heel) while at home; I was “forced” to wear panties to school Monday thru Friday. On Saturday and Sunday I was required to be in full femme mode day and night and there would be no computer or internet. My sleep wear for the week would be little girl PJs or a pink satin gown; I got to chose which one. Was it a trap?

I had to convince mom I hated her punishment. I dared not let mom know that all this made me very happy!

Punishment day

On the first day after school on Monday mom had to hold my head as she painted my lips a delicious red and applied mascara to my eye lashes; I pretended to struggle and rebel until the threat of her wide leather belt ‘forced’ me into the panties and dress that she had waiting on my bed; the dress had a zippered back that required mom to zip me in and out of it. Once I was zipped in I was deliciously trapped in the dress until mom unzipped it for bedtime.

At bedtime I found a pair of girl’s pink pajamas, and a pink sleep gown and bra set waiting for me on my pillow. I chose the pink gown and bra to sleep in; the PJs would have to wait. I would later wonder if having the two sleep options was a ‘test’ by mom to see what I truly wanted.

I was thrilled by the entire procedure! “You really make a cute girl Ronnie; sometimes I wish I had a daughter.” Mom made a point to take photos documenting my “punishment”.

From that day forward I ‘reluctantly’ dressed myself and applied my lipstick and mascara without being told. I tried to maintain the outward appearance that my punishment was mean and horrible.

During the school week I was required to change into my girl clothes immediately upon getting home from school and do my homework; on the weekend I was subjected to petticoat punishment from Friday after school until leaving for school on Monday morning. I was allowed to lounge in my girly PJ’s until 10 AM. Mom happily took many photos and threatened to expose me to friends and family if I wasn’t a “good girl”.

Kitchen duty punishment

I was required to help in the kitchen with meal preparation and washing and drying our dishes after eating. Mom mandated that I always wear a frilly pink apron to protect my dress while performing kitchen duties. My apron was always hung on the pantry door as a symbol of me being punished. I mastered walking in the two inch heels easily; I really wanted to add black stockings to my outfit. Mom took more photos.

I was made to always curtsy and reply to my mother with a “Yes, ma’am” or a “No ma’am”; I found a calmness and inner peace by playing the role of being a good girl. On my third day of punishment I added blush to my cheeks in an effort to look pretty. My mother ruefully shook her head and said nothing.

The next morning, placed by the sink in which I wash my face and brush my teeth, were two hair barrettes, a tube of teenager Peppermint Pink lipstick and a jar of makeup remover with moisturizer.

On every evening Mom came into my room, tucked me in, kissed me and said “You’re a good girl when you want to be. Sleep tight my Princess.” Her comments had a comforting effect on me.

Time passes and I had turned 16

Repeat performance

In the fall I’d be starting my Senior and final year of high school. I had let my hair and fingernails go untrimmed; I began subtly shaping my ‘boy nails’ in anticipation of the pretty polish in my future.

I waited until a week before school would be adjourned for summer vacation and then, on purpose, I called my rather effeminate English teacher a “Sissy cross-dresser in a suit” in the hope that mom would inflict the same penalty on me as before. This was either a devious thought or a great strategy. I hoped that I would be “forced” to spend part of my summer en femme.

The Mr. Logan, the school principal, called my mom like he did last time and they agreed I needed to be punished for being a trans-homophobic bigot. “Those tendencies must be corrected if Ronald is to return to public school.”

Mom explained in embarrassing detail the punishment that she had dealt out to me in the past; she promised to be harder on me for this second offense and that my punishment would be for three weeks and would start on the Friday that school let out for summer vacation. She pleaded with Mr. Logan to let me return to school in the fall and complete high school.

“If Ronald is to return and finish his education here I must have photographic proof that Ronald is being punished like you promise. Every few days send me proof that the punishment you say you will inflict on him was duly applied.”

Mom said that she would do what was required

Mr. Logan continued: “Additionally, as proof that you previously punished Ronald in the same manner, you need to send me 3 or 4 photos of his first punishment as proof. If you follow through like you said and if Ronald promises to be good I will admit Ronald in the fall on a probationary status.”

After receiving assurance that my photos would remain confidential and not be shared Mom agreed. Mom emailed Mr. Logan 6 photos of me during my ‘little girl’ punishment!

Mom and Mr. Logan obviously had no idea how far from being transphobic or homophobic I was in thought, deed and dress! To my delight mom did invoke the same “punishment”!

Mom had well thought out plans

In order to be home and keep me girly and out of trouble Mom had enough seniority at her job to get three weeks off work; 2 weeks would be paid and 1 week would be unpaid. She figured that Mr. Logan would not have any excuse to expel me from my senior year. The time off would also let her teach me things that would help me get though life.

All my friends had been told that I would be gone for a month and to forget about stopping by, calling or texting me. Mom confiscated my cell phone, ID, house key and put a very strong parental lock on my computer, internet and social media. I was in effect marooned at home with little access to the world.

Immediately when I got home from the last day of school it started

“What’s wrong with you Ron?! Didn’t you learn anything? Wasn’t your last punishment outfits embarrassing enough? Do you WANT to be a transsexual or Sissy? Do you want your friends to see you dressed up and swishing around the neighborhood?”

Mother further scolded me with, “I think you need to dress like a Sissy and BE a girl for awhile until you learn what Sissies and women have to deal with; walk a mile in their pumps and panties!”

“Yes, ma’am”! I said.

Without waiting for me to reply she continued with “You’ll do as I say as long as you live in MY house, Sissy!” I outwardly smiled at being referred to as Sissy; I could hardly contain my happiness.

“Yes, ma’am”! I said.

To be harsher on me mom extended my punishment to three week and two days of feminine home confinement. Instead of forcing me into young girls clothes like last time mom substituted the clothing style meant for a young woman or Sissy of my age; I was to “suffer” a more adult Sissy/female image. “Yes, ma’am”! I felt blessed.

In her selection of ‘humiliating’ clothes mom skipped over a training bra and went to a ‘big girl’ push-up bra with silicone breasts enhancers; this was also true for my panties, dresses and kitchen duty clothes. My footwear would be black pumps with a 3 inch heel. My makeup would be more extensive and much bolder; pink lip color became crimson red. Eye shadow, eye liner, facial makeup and foundation were added to my beauty regimen as was a small bottle of Channel #5 perfume. A can of Aqua Net hairspray waited in my bathroom.

Mom didn’t overlook a thing; she provided all the accessories, breast forms and ‘bling’ that a girl could want; bracelets, rings, anklets, feminine gold chains and even a few pairs of clip-on earrings; one earring set proclaimed “Sissy”.

It started with the basics

Before the day was over I had showered, washed my hair (Mom put my hair in curlers), and was wearing panties and a prosthetic filled push-up bra; my eyebrows had been femininely arched, eye shadow and liner applied and my face, lips and eyes were perfectly made up. I had shaved my legs and armpits twice because mom insisted I needed the practice.

I was to repeat the process of plucking my eyebrows and shaving my legs every 3 days as part of my punishment; I was told that curling my hair would be my duty every third day throughout my punishment. I became adept at using curlers and sleeping in them if needed. The results were worth the effort especially when mom brushed out my hair afterwards. I was learning what mothers teach their daughters and I was learning how to be a daughter.

Mom took a photo of me sitting on the bath tub shaving my legs, with pink curlers in my hair as part of her agreement with the Mr. Logan. I was told to smile for the camera and “show Mr. Logan your lipstick and pretty bra”. He also would see my pretty red nails holding the razor, my perfectly made-up face and the ‘Sissy’ clip-on earrings that I was wearing. I was a bit embarrassed but enthralled with this very feminine experience. I hoped Mr. Logan would appreciate my feminine appearance.

Mom held out an open purse and commanded “Put your ID, house key and cell phone into YOUR purse.” I did as I was told. I noticed that inside the purse there was already a tube of lipstick and four Pearl Lite Day tampons. I didn’t dare question moms decisions on the purse contents. Mom replied, “Some Sissies like you sometimes need a tampon. Let’s see if you’re one of those!” Her comment made me curious.

Mom made sure I had 2 dresses and a maid’s uniform (all with zippered backs), 2 sets of PJs and a clean panty for every day of the week. I kept all my ‘pretty clothes’ neatly folded in my dresser drawer or hanging in my closet. My cosmetics were neatly organized on my vanity.

Girly boot camp training

Mom had a daily routine that I was to adhere to. Without saying so she was instructing me on how to be a pretty young woman or perhaps a daughter.

In general my duties were:
Mornings: remove hair curlers, dress, makeup and nail polish application
Kitchen duties: French Maid uniform for lunch and dinner
Midday: hand wash lingerie and silicon breast forms
Evenings: makeup removal, shower, shave legs, curl hair, facial cream, nails

There were times we simply sat on the sofa in the living room and watched a movie or read a book. Sometimes I’d sit on the sofa painting my nails, curlers in my hair, waiting for my hair to dry. When dry I’d remove my curlers and mom would brush out my hair. When I painted my nails I’d then do the same for mom. I felt us bonding in a very special way; a way that Ronald would never have experienced.

Other duties

On specific days I had to hand wash my mom’s panties, bras and stockings along with my own and hang them to dry on a clothesline hung in my bedroom. Little did she know that seeing and feeling ladies “dainties” was not punishment. I began to wonder if mom DID know about Ronnie.

Trapped in drag

I was again required to help in the kitchen for lunch and dinner. This time Mom mandated that I change out of my dress, into the frilly French Maid Sissy dress and refresh my makeup before beginning my duties. Like my dresses the maid uniform also had a zippered back that I could not undo by myself; I was always trapped in drag.

After seeing me fully made up, dressed in my maid uniform and wearing my Sissy earrings mom shook her head, left the room and returned with a lovely pair of black stay up stockings that she “made” me wear with my outfit. The stockings really completed my image and made me feel very pretty. She also substituted a pretty tiara instead of the traditional French Maid white cap; she said I was her Princess! In reality I think mom was becoming fond of Princess Ronnie. This was another photo opportunity of proof for Mr. Logan.

My Sissy Maid outfit was always hung on the pantry door as a symbol of punishment. Being the epitome of femininity I remained in my maid outfit as long as possible afterwards; I mastered walking in the three inch heels easily.

I found out much later that mom had compiled a substantial quantity of photos of me en femme and had organized the photos of both my petticoat punishments into a lovely photo book entitled “My Princess”.

A twist in punishment; “public outings are for your own good”

Mom thought that if she took me out into public that it would accomplish several things.

1 - Embarrass me so I didn’t repeat my bad behavior
2 - Allow me to get accustomed to being a young woman
3 - Understand that life for girls like me is not easy and is fraught with dangers

When I was older and reflecting back on my situation I realized that mom’s “punishments” had very little to do with punishment but were actually centered on her concern for me and my future. She was prepping me to survive in a hostile world; in effect I had gone through ‘girly boot camp’ training that gave me self confidence in my femininity and the ability for Ronnie to go out into the world that I did not have before!

Mom decided that on Tuesday’s and Saturday’s after becoming my prettiest we would take a one hour ride around town and the surrounding area. On Thursday’s while in my maid’s uniform we would take another one hour drive. We always drove thru fast food places where my dress, legs and I were on full display. At first this was very awkward. At stop lights I would hunker down in an effort to not be seen; I felt very exposed and vulnerable wearing a dress.

By the second week I had relaxed into my situation and sat tall and proud in my dress on every outing. As we drove I began using the sun visor mirror to apply my lipstick and check my hair; my barrettes, earrings and faux tits were on full display and I didn’t care; I felt perfectly normal and at ease.

During our outings Mom and I enjoyed taking selfies with our cell phones; some photos were for Mr. Logan. I loved feeling that I was mom’s teenage daughter.

Mom would stop at local parks and we’d go for a walk; I’m sure the fact that I did not stumble in my heels surprised her. I was not in my French Maid attire and felt comfortable as mom played photographer. She would have me pose multiple times as she took photos for herself and Mr. Logan. We laughed when I managed to get a run in one of my stockings after mom had me sitting on a low hanging tree limb for a photo.

A learning moment

In an ‘end of the day’ inspiration Mom drove down the interstate highway to a very large ‘Flying J’ truck stop; she drove to where big rig trucks were permitted to park or spend the night. Mom parked the car in an out of the way spot that faced the idled trucks. She turned off the engine and we unbuckled our seat belts. “Be mindful of what life holds for some special girls like you, Princess.” I sensed sadness in her voice. We sat in silence and just watched the activities unfolding in front of us.

After awhile Mom broke the silence and began pointing out the ‘lot lizard’ trannies with five o’clock shadow, soiled dresses and cheap looking wigs as they walked from truck to truck offering their special services to lonely or randy truckers; a few of the ‘lot lizards’ looked very manly.

“Those are working “girls” and horny Sissies in desperate need of sex, money or drugs; for some it’s a combination of all three. They are in a dangerous business where horrible diseases, HIV, physical abuse and rape are common place; their risks are many and their reward is small.”

Mom pointed out that what sparkled on the ground and looked like wet leaves next to the trucks were in reality used condoms, hypodermic syringes and an occasional wad of discarded soiled panties.

After we’d been observing for about 45 minutes I said, “Mom, I noticed that those girls were in and out of a truck in 15 to 20 minutes.” Mom put her hand on my stocking covered knee and replied, “Those “ladies” aren’t here for love Princess; they need to move on to the next paying customer. Some are so desperate and broke that they sell themselves for a burger and fries or a warm place to sleep. Promise me Princess that you won’t let yourself slip so low as to become a ‘lot lizard.”

I turned to face her, smiled and tenderly said, “I promise.” I leaned over and kissed her on her cheek. I left a small smudge of a red lip print that I teased her about. She insisted that we take a commemorative selfie of this mother-daughter milestone. At that moment I felt content and warm inside.

The following days were a beautiful slow motion dream of being a young woman. I was sad to see it end. Before it ended, in typical mom reasoning, she had me doing the driving while in my 2 inch heels from my first punishment! She was right; the practice made me a better woman driver.

My “punishment” was over and I loved every day and night of it!

My punishment may have been over but my desire and NEED to look pretty had grown stronger. Mom must have sensed this aspect of my life a long time ago. She told me to keep all my feminine finery and makeup from both of my punishments. The only item she wanted was the MK purse which I reluctantly surrendered. Looking inside to be sure I had removed my ID and house key mom looked at me and said, “There’s only two tampons left, Princess; where are the rest?” she asked.

I blushed and hesitated too long before sheepishly saying, “I think they got used.” Mom shook her head like she does and handed me back the two remaining tampons. “I guess you needed the experience and the practice will do you good” she said. I took them in hand, smiled, curtsied and said “Thank you.”

Mom confesses

Mom hugged me tightly and softly said, “I know you’ll be a beautiful woman someday Princess but for god sakes buy your own damn tampons and stay out of my cosmetics and panty drawer.” We kissed lovingly like mothers and daughters do.

“I never said anything to you Ronnie but there were signs since you were young that you were going to drift in the feminine direction that you are obviously headed… after your play dates and visits to Lucy and Josh as a young boy I noticed tell tale signs of your fondness for nail polish and lipstick; stained lips and remnants of polish in your cuticles gave you away; I was impressed with the way you washed and hid your panties when your first punishment was over.”

We broke our embrace and mom told me “You can get pretty at home anytime you want Princess.”

Long after the punishment was over I took frequent comfort in dressing as the girl I felt I was; I always slept in something femininely sexy. I continued to keep my legs and armpits hair free and had expanded my shaving to include my pubic areas. In public I reluctantly repressed my femininity in order to conform to what mom and society expected of me.

My total immersion punishment into femininity boosted my confidence Ronnie would be able to survive and thrive in life; it became obvious that womanhood was my destiny. Thanks to mom I had a nice wardrobe at my disposal.

High school blackmail

Summer was over and there was a mandatory conference call between Principle Logan, mom and myself in order for me to return to school. Mom and I spoke from our living room.

I listened intently and said the right things when I needed to. I promised to behave the entire school year. The principle agreed to allow my return but emphasized that if I messed up again there would be severe consequences. I was wondering what this could involve when mom’s and my cell phone dinged multiple times as messages came in. “Check your phones ladies” said Mr. Logan.

He had forwarded many of my punishment photos that showed me in very feminine activities and clothes.

He continued: “If Miss Ronda screws up her glamour shots will be shared with others including the school newspaper; it would make for an interesting story. Certain web sites would pay good money for shots of your pretty Princess. Do you understand?”

I smiled at being called Ronda. I liked the name, it sounded so nicely femme.

“Tell Miss Ronda that she better ‘butch it up’ a bit long before school starts. Stop plucking her eyebrows and no mascara either. The school doesn’t need male lesbian Sissies causing problems.”

We made it clear that not only did we know what he was saying we made it equally clear that we knew exactly what he was implying.

Almost done

Ten days before graduation a classmate named Dan asked if I would like to be taken out for dinner as a graduation celebration. I knew Dan from seeing him nude in the showers after PE for the last three years. He was on the track team and was in great shape and physically attractive.

I thought for a moment and tried to remember if Dan had ever had a girlfriend. “Will your girlfriend be joining us?” I coyly asked. Dan cocked his head, took a deep breath and quietly replied, “I don’t have girlfriends.” That is exactly what I was wondering about. “What time will you pick me up? I smiled. I had over a week to shape my eyebrows and finger nails and get ready.

I graduated! - It took a lot of effort and self control but I made it thru high school

Mom watched my graduation ceremony and had tears of happiness when I received my diploma and exited the stage; I wore my hair in a low pony tail. We hugged, embraced and took a couple of photos. As we were making our way to the parking lot Mr. Logan approached and handed me a graduation card, said “Take care of yourself, Missy.” and left; it was a brief encounter.

The envelope was addressed to Ronda. Inside was a $25 gift card to “All About Eve” ladies boutique! The card was signed “Jack” and oddly enough he had written his email address at the bottom. I think “Jack” must have really liked my photos.

I went to All About Eve and used my allowance and gift card to buy a few things; Skinny Jeans, a blouse, black ballet flats with 1 inch heels, knee high stockings; a pair in tan and a pair of black.

Urban legend says: A high ponytail exudes a youthful, energetic vibe, ideal for sporty settings or for a girl on the prowl! A low ponytail is associated with being demure, elegance and sophistication and is NOT typically for girls or cougars on the prowl

First date

Dan arrived at 5 PM and waited in his car for me to come out. I had told mom I was going to get a burger with a friend so she would be expecting me leave. I grabbed my black clutch purse that held my ID, money, house key, lipstick and lots of tissues; I kissed mom on the cheek and scampered out the door. I was wearing a bulky sweater and denim jeans; my hair was in a low pony tail and I wore no cosmetics except for a dash of mascara and a very small amount of Channel #5 perfume behind both ears.

Dan was driving an older Chevrolet Impala that had bench seats. He opened the car door for me and closed it after I was seated; I placed my purse on the floor by my feet. Dan told me that I looked pretty! Once we were a couple blocks from home I removed my sweater to expose my new long sleeve blouse. “What a beautiful blouse, it goes with your skinny jeans perfectly” he said. I undid my pony tail and shook out my hair to give him a better understanding of who I was. I smiled at him.

“Damn, you are really gorgeous Ron; and your shoes are very pretty.” Dan had noticed my ballet flats! I can hardly wait until he sees me in real heels.

We ate at a cozy restaurant he frequented called Bette’s Place that would allow us to relax while we ate. Colorful rainbows were prominently displayed on all of their signage and menus. Over dinner Dan said he had been attracted to me for a long time but dared not say or do anything until school was out. He said I looked like a fun person and that I was pretty. He said he was uncomfortable calling me Ron and asked, “How should I call a pretty boy like you?” I reached across the table and touched his hand before replying and said “Call me Ronnie when I’m pretty.” It was pleasant time for us both.

When finished Dan paid the bill and as we went to his car I felt him feeling for my bra band; without objecting I asked, “My, aren’t you frisky tonight!” I thought Dan’s back rub was a cute moment of a teenage virgin’s first-date curiosity and exploration. Like before he opened and closed my door; I was feeling very ladylike.

Before Dan pulled away I opened my clutch purse, retrieved my lipstick and used his sun visor vanity mirror to do my lips. Dan watched in rapt attention as I made myself prettier. With my tube still out I playfully turned to face him and asked, “Would you like to borrow my lipstick?” Dan shook his head back and forth indicating no. I leaned over, grabbed him, pulled him close and pressed my lips to his.

After being sure to have transferred color to his lips I made it a real kiss before pulling away. Dan looked surprised but not mad. Before he could say anything I said, “Boys can look pretty too if they want.” Dan paused and slowly looked me up and down. “Yes, they most certainly can!” We broke into shared laughter. I made a mental note that Dan did not try to wipe “his” lip color off.

We drove into the hills for about 20 minutes making idle chatter; Dan seemed to know where we were going and I didn’t care. He pulled to a stop at a roadside turnout with a beach view overlook and parked. Dan tentatively put his arm around me and softly said, “Your perfume makes a lovely statement of the femininity that is you.” I reflexively leaned my head against his chest a moment before rising up and kissing him on his cheek. It was like I had flipped a switch that turned Dan on! The bench seat was very convenient.

Issues that require tissues

After an hour or so of sightseeing Dan began slowly driving me home; all the tissues in my purse were gone. His arm held me snuggly against his body and I liked it; I felt like I was glowing. We held hands as Dan slowly walked me to my front door; he kissed me goodnight and I kissed him back… several times. It was 11:30 PM and I was late.

I entered the house to find mom sitting in a chair and staring at me sternly; “Listen to me young lady! Don’t play with fire and lead a man on like that. I assume he knows that you’re a male?”

“Yes mom, he knows. I’ll be a good girl.”

“Now go to bed!”

“Good night, mom. No truck stops for me!” I curtsied cutely for her benefit. I dared not tell her that Dan was planning to visit me for a few days once I got settled in at college; he wouldn’t need a motel if I had my way.

I washed up and slipped into a new 2 piece black sleep set; it made me feel pretty. I floated to my bed with thoughts of Dan and Josh and the moments of young passion I’d had with them both. As I laid there I sought out and attained the orgasmic release that I had just experienced; I fell into a delicious sleep.

Next stop College - I was accepted at Evanston College which was too far away to be able to live at home. I was going to study Interior Design. To be more comfortable I planned to arrive a month before classes began.

Principle Jack pulled some strings and was able to find me a very affordable one bedroom ‘mother-in-law’ apartment behind a school administrator’s house just 10 blocks from college. It was small but much better than a dorm. I wondered if Jack Logan would turn up at my door someday looking for a personal lip-to-lip form of “thank you”. Perhaps he would be holding a stack of Ronnie ‘punishment’ photos as an added ‘incentive’ for me to invite him into my apartment! I’d deal with that if it happened.

Leaving the nest

It was sad to leave mom and the safe environment that was home but she was happy that I was trying to get ahead in the world. Her savings allowed me to attend college.

As a parting gift a week before I left for college mom took me to get my ears pierced at a department store’s jewelry counter; it was a big deal for a young girl like me; like a coming of age (or acceptance) landmark. While there Mom gifted me a set of gold pierced ear hoop earrings, a fine gold chain necklace that proclaimed ‘Princess’, a three pack of pretty panties and a box of condoms. “You’ll need all of these someday Princess” she said. I kissed her sweetly, curtsied to be cute and said “Thanks you.”

“Be a good girl; keep away from truck stops!” mom said. I nodded, climbed into my car and drove to where my future waited. Gently tears of farewell rolled down our cheeks. Except for my skinny jeans I wore my boy clothes.

College

As planned I arrived a month before school was to start. Within a few days I had enrolled at college, confirmed my classes and moved into my new place. As a struggling student I was always on the outlook for ways to earn additional income. I would pick up odd jobs whenever I could. I knew that I would need some income ‘eventually’; I planned to get a job ‘someday’. I needed to set priorities and I did.

My Breast friends!

I had wanted to have my own titties for a long while so the first thing I did once I got settled was to buy and start taking low dose female hormones. There was nothing wrong with the silicon breast inserts that mom had given me but it was time for this girl to grow her own. I had tried a breast pump with little results. It was very ironic that I found my source for my hormones from a girl at a local truck stop; her name was Bob. I knew the dangers associated with taking hormones.

Before my first semester had ended I had been taking my hormones for six months and breast buds had formed. My breasts were very puffy, my areolas had increased noticeably in diameter and had gotten darker; my nipples had grown to the diameter of a pencil and stood ¼ inch in height without stimulation. There was definitely a heightened sensitivity and soreness in my breasts. I was proud of my cleavage but oddly enough my bra size remained 36B. It would be another 11 months or so before my new titties would be “ripe.”

Body fat at my hips had slightly increased. I was aware that this is typically Stage 2 of female puberty. I considered a tracheal shave to make my voice sound feminine but I definitely did not have an extra $3,000. I will look into male to female voice training.

In need of income

I took a few temporary jobs that fit my college schedule as they presented themselves. The end of my first semester was near and I knew I needed something more steady or more lucrative; I stayed alert for opportunities. Eventually I found a lead that would fit my immediate needs.

What’s more fun than having titties and more lucrative than a traditional job? A Womanless Beauty Pagaent with a $1000 first place prize!

End of part one

Follow Ronnie on her next adventure; she enters a Womanless Beauty Pageant and meets an Angel

Part two prologue

Yes, I entered a Womanless Beauty Pageant.

As a struggling student I was always looking for ways to earn additional income. I picked up odd jobs whenever I could. I was ecstatic when I found an opportunity to make a quick $1000. It was also an opportunity for me to indulge in socially acceptable cross-dressing! All I had to do was win the Womanless Beauty Pageant that was to be held in about 4 weeks! The ‘job’ would also allow my alter ego, Ronnie, to emerge from a long period of seclusion; I was excited and apprehensive at the same time. Third place paid $500.

Preparation for the Pageant brought back memories and dormant desires from years ago; memories of my life altering “punishments” and memories of the years between age 11 and 16 years in which “Ronnie” was ‘born’. The Pageant would give me the excuse to be pretty in public.

I already had a tiara that mom had given me but I wanted to win one for being femininely pretty. I wanted to send her a photo of her Princess as a beauty pageant queen; she’d be so proud of me!

(This is part 1 of a 3 part trilogy)

(This story is 100% adult fiction with a liberal helping of literary license... a fantasy for some.)
For a 'feel good' stories read my "Yuletide Acceptance" and "Accidental Acceptance".