Sara: Princess for a Day - Queen for Life

Before and after photos confirm that clothes make the man; while cosmetics and clothes can make the man a woman.

Uncle Stevie Before
Aunt Linda After

If Uncle Stevie can be a girl why can’t I?

The back story: Mike’s dad and Uncle Stevie were brothers that grew up in Southern California. Stevie was the smaller and lither of the two and he had no interest in athletics. Stevie preferred more gentile activities like creative writing, fashion and drama class. Drama class introduced Stevie to the use of make-up and an excuse to let his hair grow long in case a role would require it. Through high school it was plausible justification to look feminine.

During his senior year of high school Stevie had both of his ears pierced. Family and teachers graciously referred to Stevie as being “sensitive” and “delicate.”

Uncle Stevie had been married briefly before divorcing. Shortly after his divorce Stevie began sharing a house with a “roommate” named Carl. Carl rarely came to family functions.

It’s all about nephew Mike

From his earliest memories Mike had silently struggled with an inner feeling that something was drastically wrong with him; that he should have been born a girl. From Kindergarten thru 2nd grade Mike had used crayons and colored pencils to make his fingernails pretty. For recess activities Mike played jump rope and jacks with the girls rather than baseball or football with the boys.

Girls and girl activities were fun and safe while boys were aggressive and their activities could get you hurt. A pattern of non-traditional gender identification was on display.

As to be expected with a ‘delicate and sensitive’ youngster like Mike he took every opportunity to dress and look as girly as possible. This need spilled over into his childhood games and playing house; if there was a remote opportunity to wear a skirt, dress, makeup or be the mother figure in playing house he took it. Halloweens always allowed him to fulfill and enjoy his budding femininity.

At a Halloween party, when Mike was 11 years old, he saw his Uncle Stevie decked out as a beautiful and believable woman for the first time. Mike became enthralled with Uncle Steve’s subtle yet obvious feminine aura. There was no ‘drag’ element to Stevie’s very believable womanly appearance. Whether in skirts, dresses or casual wear Aunt Linda’s wardrobe and selection of accessories were always perfectly feminine.

Even when not dressed as a woman Stevie’s innate femininity and mannerisms were obvious; his shoulder length hairstyle was more of a long Pixie cut shag than a man’s hairstyle; his nails, although not painted (except for a clear top coat) were always perfectly shaped and well maintained. The term ‘androgynous’ defined him perfectly.

On one occasion Mike asked Uncle Stevie why his fingernails were always so pretty.

“Manicures are one of life’s simple pleasures” he told Mike. “The shiny top coat gloss is to prevent my nails from chipping or breaking.” If Uncle Stevie can be a girl why couldn’t he? Mike wondered. He began using clear coat just like Uncle Stevie.

While en femme Stevie asked to be called Linda or Aunt Linda. Through the years Aunt Linda’s warm hugs, feminine scents and demeanor were comforting to Mike; he hoped to be just like Aunt Linda someday. Gender fluidity was a concept that Mike would need to deal with eventually.

When Stevie would visit on holidays or special occasions he didn’t always arrive as Linda. However any time Aunt Linda was present Mike always made a point to hug his Aunty and tell her how beautiful she was. The subtle scent of her perfume was deliciously mesmerizing to Mike.

By age 12 Mike was asking Auntie about cosmetics, fashion and what ‘chick flicks’ she liked. These were very unusual questions for a young boy to be wondering about. In accord with the fashion of the day Mike had let his hair grow to shoulder length. Around home he often sported a ponytail and perhaps a barrette. His parents thought nothing of it and made no comments. As long as Mike maintained good grades and stayed out of trouble they left him alone.

On more than one Christmas Mike gifted his Aunty a tube of lipstick, a perfume sample, bottle of nail polish, etc. The family thought it was a cute gesture. Mike’s family began to accept that he too was “sensitive” and “delicate.”

Aunt Linda knew that Mike’s interest in cosmetics and hemlines foretold many things. On several occasions Aunt Linda had seen the missed flecks of nail polish that his nephew had failed to completely remove; lightly stained lips and the unmistakable aroma of makeup were other interesting “tells”.

“Be careful Princess. I want my niece to have a pleasant childhood; some people don’t approve of girls like us.” Mike was alarmed that he had been ‘outed’ by Uncle Stevie.

A hug and a kiss from Uncle Stevie let Mike know his secret was safe with her. Mike smiled and relaxed at Stevie’s feminine reference to him. “Aunt Linda knows I’m a Princess!”

For his 14th birthday, and with his parent’s permission, Aunt Linda treated Mike to getting his ears pierced at a local mall; earrings on males were quite the rage. Celebrities and famous athletes had made them acceptable.

Although his folks would only allow Mike to wear discrete gold ball studs in public Aunt Linda gifted him a set of 2 inch gold hoops and a set of inexpensive Cubic Zirconium studs ‘for special occasions.’ Mike was very appreciative.

Linda knew that when they got home Mike’s folks would be gone for the entire day; Aunt Linda could not contain herself. With no objection from Mike Auntie removed Mike’s studs and carefully installed the hoops in his ears; Mike was smiling from ear to ear with excitement. Linda took a brush from her purse and, with a little teasing, easily created a feminine look to Mike’s long hair. Linda insisted that Mike join her at a full length mirror so they could stand side by side for a selfie photo on her cell phone.

Mike looked very pleased with his earrings and image yet Linda looked perplexed. “There’s something missing Princess” she said. Retrieving her lipstick she twisted it out exposing the lovely color that it was. Without a word Linda held it up for Mike to see. Mike gulped and his eyes enlarged; he knew what was next.

“This shade is much too stark and red for a young lady with your skin tone but it sure is pretty.” Linda gently held Mike’s chin; Mike made his lips firm and held very still. Linda applied the cosmetic to Mike and smiled. “My, what a pretty niece you have become.” Mike heart was racing and he felt he might faint. Linda took him by the hand and returned to the mirror.

“There’s still something missing Precious.” Aunty led her niece to the couch and had her sit down. “Watch and learn Princess; this is an easy fix that every girl your age learns early in life. Look straight ahead and stay still” she admonished.

Linda used her lipstick and put two small dots of color on Mike’s cheekbones and began rubbing and blending it in. In mere moments Mike had a pretty blush glow that added greatly to his feminine look. Linda looked a moment, smiled and said, “There’s one more item that every woman needs: mascara!” she gleefully exclaimed.

From out of nowhere Linda produced her mascara wand and deftly coated Mike’s lashes several times. Then she used her eyelash curler to further feminize Mike. His crimped lashes looked longer and exceptionally pretty; the mascara dramatically enhanced Mike’s feminine image.

Still not satisfied Aunty used her tweezers and took time to pluck a few stray eyebrow hairs to reduce the masculinity of her nieces face. Mike held very still.

“Look and learn Precious. The traditional method to shape brows is to line up the inner corner of your eyes as a reference point and cautiously pluck one hair at a time and one brow at a time making sure no hairs are in between those reference points. At your age you should not over pluck to extreme or everyone will notice and call you a Sissy; you can do that when you’re older.”

“Thank you Aunty.” Sara was the closest to having a daughter that she would ever have and she wistfully vowed to take every opportunity to indulge her niece. Perhaps it was her hormones because Linda was suddenly feeling very motherly. Linda regretted not having had anyone to guide her in such matters when she was a young girl.

Back at the mirror Linda let Mike absorb the moment. He was awestruck with his very girlish appearance! His eyes and eyebrows were amazingly feminine; he couldn’t be giddier! More selfies were taken. It was clear that Mike was very pleased with his look.

“What the heck. As long as we’ve gone this far we may as well complete what we’ve started.” Mike looked puzzled. Linda took her purse, walked to the kitchen table and beckoned Mike to have a seat. Reaching into her purse Linda retrieved nail polish and began to paint Mike’s fingernails a beautiful red that matched his lipstick. “I see that you are already shaping your nails, Princess do your parents object?”

“No Aunty. As long as I don’t let them get too long or color them they don’t care.”

“Just so you know it’s always a good idea to match the color of your lipstick with the color of your nails.” Linda was enjoying being a nurturing aunt.

By the time Linda was finished Mike was over-the-rainbow with girly joy. He was gently blowing on them to make the polish dry when Linda said “Look and learn.” From her purse Linda removed a bottle of clear quick-dry and proceeded to apply a coat to Mike’s freshly painted nails.

“Always apply several thin coats of polish to prevent smudging; thin coats dry faster. And always have a bottle of quick-dry handy. It save’s a girl a lot of time.” Mike was absorbing everything his aunt was saying.

“You need to be more careful when cleaning your nails” she instructed. “I’ve seen what you’ve missed. Use enough remover and cotton balls to remove all the color around you cuticles. Put the used cotton balls in a plastic bag; tie it in a knot and dispose of it in the outside trash cans. This keeps the odor of the acetone away from your mom and dad. For the same reason always thoroughly wash your hands afterwards. When you remove your lipstick be sure to flush the tell tale tissues down the toilet.”

“I’ll be more careful Aunty.”

Linda let Mike appreciate the beauty of his freshly painted nails. When they finally stood up they embraced. Linda insisted in taking a few commemorative photos and selfies of her niece with her cell phone.

Aunt Linda took a firm hold of Mike’s shoulders and shook him once to underscore what she was about to say. “Young lady, you are to never tell your mom and dad what WE did today. All I did was add a little nutrient to the budding flower that is you. The rest is up to you.”

The awakening

Mike quivered and began to softly cry. “I love you Aunty, I love you more than you can imagine.” Linda hugged him lovingly and let Mike finish his tears of joy; she passed him a tissue from her purse so he could blow his nose.

To evaluate how immersed and committed Mike was to his girly side Linda asked, “What’s your dress size Missy?”

“I’m an 8/10 Aunty.”

“Do you wear panties or briefs?”

“It depends on where I’m going or what I’m doing. I never wear panties to school; I’m afraid people will notice and call me a Sissy.”

“There’s nothing wrong with being a Sissy if that is what you want; you’re too young to know what life has in store for you.” This statement was quizzical to Mike and he made a mental note to explore this topic further. ‘Am I a Sissy’ he wondered? ‘Perhaps I am.’

Linda continued her questions.

“Tell me what name has my pretty niece chosen when you are feeling girly.” Looking a little embarrassed Mike smiled warmly and softly said “Sara, Aunty Linda; I want to be known as Sara.”

Linda beamed her delight, embraced her new niece and said, “Nice to finally meet you sweet Sara. I wondered when you’d finally confide in your Aunt Linda that you wished to be a girl. All of the signs have been there for many years.”

“You have about two hours until your folks are due home; be a good girl and cleanup with great care. I know your mom has cold crème and mascara remover; be sure you use them and toss out the soiled cleansing pads and tissues like I taught you.”

“I promise I’ll be the good girl you want and be very thorough. Someday soon I’d like to ask you about bras, breasts and boys.” Linda winced at the mention of the “3 Bs” but smiled.

Linda pinched and pulled Sara’s shirt out to simulate what titties would look like while saying “The day will come my Princess when I’ll be happy to have that conversation with you but not now. You can keep the mascara and lash curler. Remember to swap your hoops for the gold ball studs that your mom expects; sometimes it’s the simple things that will trip you up.” Linda opened the door and left.

Sara spent the remainder of her time happily staring into the mirror and posing for personal photos; she had fallen in love with her own feminine image. Sara retreated to the privacy of her room, donned her hidden bra and lay on her bed contemplating the femininity that simmered within. She made time to pleasantly resolve her urgent erection before cleaning her face and nails. ‘Boy, I sure wish I had a boyfriend’ she thought.

Sara had already acquired a few panties, a pair of pantyhose (Sara’s very favorite article of clothing!), a few basic cosmetics and a Sable Grey ‘A’ cup training bra. Sara added Aunt Linda’s gifts to her collection. She also had acquired several well worn CD/TG magazines all of which she kept well hidden.

When the opportunity or urge arose Sara would lock her bedroom door, don her panties and bra, apply her cosmetics and read her magazines. She was very fortunate to have her own bathroom attached to her room. When she was in her room with her girly things and reading materials Sara would become very aroused.

Sara’s ‘library’ had expanded to include gay themes, fantasies and photos. Her first wet orgasm occurred while masturbating to photos of boys and men dressed like girls having oral and anal sex.

Gay Times, Dream Boys, Teen Queens and Twinks were particularly interesting magazines and very arousing to Sara; her mind and desires wandered deliciously as she read them. Her ejaculations were always more powerful when she read her magazines, often landing on her chest and pillow while reading them.

And then one day while reading Dream Boys one of her forceful creamy spurts hit her face and lips.

The warm impact of her viscous emissions hitting her face was so thrilling that Sara spontaneously ejaculated several more times! By reflex her tongue automatically lapped her warm goo from her lipstick coated lips; the taste was not unpleasant. Just like the characters in her magazines Sara had tasted sperm; her life was forever changed.

Having her ejaculate hit her face and mouth became a routine part of Sara’s masturbation sessions; off- target puddles of sperm on her stomach and chin were now scooped up and devoured. The experience was sensationally erotic. Sara wondered what being intimate with a man would be like. Her wondering soon evolved into a burning desire; she needed to find a boyfriend soon.

Since her conversation with Aunt Linda Sara’s androgynous manner of dressing and judicious use of light makeup had became routine. Sara concluded that lip-gloss is not the same as lipstick even though they could smell and taste the same.

The Road Not Taken: “Two roads diverged in a yellow wood, and sorry I could not travel both…”

One day after school, when the library was almost empty, Mike was sitting at an out of the way table reading Teen Girl fashion magazine; a gender neutral clutch bag lay next to his magazine. He was in full Sara mode wearing True Religion skinny jeans, gold hoop earrings, a colorful print shirt/blouse and a white scoop neck camisole. For underwear she was wearing her usual nylon tricot girly tap pants. To show off her earrings and her below the shoulder hair Sara had tucked her hair neatly but femininely behind her ears. She held her hair in place with matching tortoise shell barrettes. Sara had also used Aunty Linda’s blush fashion trick on her cheek bones like she had been shown.

Mike became startled when an upper classmate named Paul suddenly appeared and sat next to him. Paul started an innocent conversation about nothing in particular and then unexpectantly changed the topic to how long and pretty Mike’s hair was and that her hoops looked sexy. And then he said: “I’ve been checking you out for over a week and wanted to say hello.”

“I noticed right away that there was something special about you; I can spot a cute twink a mile away. Your long hair, ear studs and skinny jeans first caught my attention. Then I noticed clear polish on your nicely shaped fingernails and ultimately your demeanor added to your already feminine mystique. I had to meet you to confirm my suspicions.” Mike became un-nerved by Paul’s comments.

Mike quickly closed the obviously girly magazine fearful that Paul would notice he was reading an article about the proper way to shave your legs. As luck would have it the magazine cover was more femme and revealing than the article he had been reading: “Who is the cutest boy band heart throb.” Paul noticed both details. “By the way your hoops look great! I guess that’s more of your feminine mystique.” Mike blushed at Paul’s words. “What a flirt” Mike thought. Paul’s overtures were titillating to naïve Sara.

Paul scooted closer to Mike and whispered in his ear, “I see we both have the same taste in magazines.” Mike squirmed in his seat and struggled to find a proper replay. The warmth of Paul’s breath on his ear made Mike squirm in a pleasant way. He remained motionless and maintained his gaze on the closed magazine. Most importantly Mike didn’t pull away. Paul took notice of that too.

“You should really read the article on what lip color goes best with different skin tones” Paul suggested. Mike swallowed hard and turned his head to face Paul; they were mere inches apart. Paul continued to whisper: “The article is on page 28…” Paul placed his hand under the table and on Mike’s upper thigh; he leaned over and with his free hand opened the magazine to the page 28.

As they stared together at the now open magazine Paul volunteered, “A reddish coral would look nice on you. I prefer more of crimson. What shade do you prefer?” Paul placed his open palm onto the elongated lump of Mike’s crotch; his fingers rubbed Mike in a very salacious way. Mike spread his legs further apart and boldly placed his hand on Paul’s thigh. Mike turned his head and made eye contact with Paul.

Paul smiled handsomely, looked around to see if anyone was near, leaned in the final two inches and kissed Mike firmly on the lips; it was not a brief peck. “Your lip gloss tastes nice” Paul said. “Is it strawberry?”

Mike’s hand found and rubbed Paul’s zipper line. They caressed and explored each other’s hardness under the table in silence. Not a word was said. Time passed. Their breathing became labored with young lust as their passions and needs increased; lustful urgency is a powerful thing.

Paul was cupping and sexually kneading Mike’s ‘package’ with his hand and Mike courageously did the same for Paul. “You are quite a handful Sweetie; I sense you have special needs” Paul softly said. Mike was beginning to softly moan as their mutual stimulation continued.

Not caring if anyone was watching Mike planted a passionate and lingering kiss on Paul’s lips. Paul added to Mike’s arousal with a French kiss that almost sent Mike into a spontaneous orgasm. Mike was so hopped up that he automatically reciprocated and began to squirm with a carnal urgency.

Paul took a deep breath and broke the moment by bringing his hands above the table. “We need to take a walk and sort things out. I’d love to show you the back seat of my dad’s Ford Explorer SUV. All of the rear windows are tinted black.”

Mike was in complete agreement. It was like dream coming true! Paul stood first and pulled Mike’s chair out like a man would do for a woman; it was a subtle but meaningful gesture that Mike liked. Paul was sending Mike a subtle message of who the man was in their budding relationship.

“Before we go follow me to the men’s room so I can get some paper towels.” Mike led the way with Paul naughtily fingering the perineum crevice of Mike’s butt as they walked. Mike giggled and made a point to wantonly gyrate his butt and walk more slowly; Mike was thoroughly enjoying Paul’s lascivious touches.

While Paul got the towels Mike removed his barrettes and used the bathroom mirror to deftly tease and brush his hair into a more fitting hairstyle; he also applied a strawberry pink lipstick over his depleted lip gloss. When finished Mike put his lipstick, barrettes and brush into his clutch bag. The bags short gold chain confirmed what Paul already knew. They exited the library.

Upon reaching the car Paul made a point of opening the passenger door for his cute date, patting Mike’s butt suggestively and helping him step up and into the SUV; it was another sign that Paul was to be the man. Paul drove to the furthermost part of the library parking lot and backed into a spot under a large shade tree. The forward facing windshield would alert them to any approaching people or cars. The two got busy.

After 45 minutes and multiple orgasms they exited the car and straightened, buttoned and zipped their pants. Mike’s lipstick was obliterated. Even though the paper towels had been put to good use they still managed to soil their panties. This session only involved kissing and mutual masturbation which was more than Mike could have hoped for when he woke up this morning. Mike apologized to Paul for the wet spots he had shot onto Paul’s sport shirt and neck.

A hyper aroused young virgin will do almost anything when their rutting urges kicks in; Mike was no exception. To Paul’s delight his young twink sensuously kissed and sucked his wetness from Paul’s neck while continuing to stroke his very rigid and needy shaft. When Mike used his tongue to thoroughly clean Paul’s juicy emissions from his hands Paul knew he had found his perfect date. These erotic acts did not go un-noticed by ‘daddy’ Paul; to his carnal delight Mike’s actions screamed Sissy.

Be grateful for what you have received

Mike was happy about what had transpired in the back seat of Paul’s car. Paul’s smoothly shaven pubic area was a delightfully erotic turn on; Mike made a mental note to do the same. He also had held, explored and jerked off a man’s engorged penis; discovered that kissing a male was a significant turn on; discovered he liked his private parts caressed and manipulated by another. Most exciting is when Paul touched him in a place that no one had ever probed before; it was a thrilling experience and Mike wanted more. He was also pleased that he had sampled another person’s sperm.

Paul was grateful that a cute ‘earring-and-panty-wearing-sperm-eating-virgin-fairy-twink-that-liked-to-wear-lipstick’ had jacked him to multiple orgasms. He was doubly grateful in the way that Mike had removed wayward sperm from his neck; pleased that his new Sissy had allowed him to tickle and probe his pussy; disappointed that he was unable to determine the tightness of the rubbery ring surrounding Mike’s boy-pussy.

Could Mike handle what Paul had in store for him on Saturday? Paul made a mental note to bring condoms. And lube. The prospect of fucking a virgin Sissy was more arousing than getting Sissy ‘love-rings’ on his penis; it would be a win-win situation.

“On Saturday we’ll take a ride up Azusa Canyon Road to Chantry Flats. It’s a nice area with secluded pullouts and grassy meadows that overlook the valley. Maybe we’ll go to a drive thru with you all dolled up, get hamburgers and drive around town with you looking pretty before we go to Chantry.” I’ll bring a blanket and a box of tissues.” Mike was uncertain about driving around en femme; what if they got pulled over by the police?

Paul reached into his front pocket and produced a gold colored tube of lipstick which he handed to Mike. Mike was momentarily taken aback. Not about wearing lipstick, it was the bright Taylor Swift red color that took him by surprise; it was the same shade that Aunt Linda had put on her.

“I like my Sissy’s to wear this color! I like seeing their lipstick rings on my cock; it pleases me. I want YOUR lipstick rings up and down my shaft! Is that understood?” Paul noted that Mike did not flinch or object to being called a Sissy.

Mike nodded and submissively said “Yes Paul, I understand.”

“Does my pretty Sissy want to please me?” asked Paul.

Mike nodded again and softly said, “I promise I will please you.”

“I want my Sissy twink to wear her best panties, put her hair into a pony tail and wear the lipstick I gave you. Maybe we’ll look at the stars… or maybe we’ll make stars of our own.”

“Yes, I will wear and do whatever you want; I’ll even wear my French Cut panties for you” Mike demurely confessed. “I will please you in any way I can.” The implications of what Mike said opened a wide variety of possibilities. Mike’s heart was racing and his penis was becoming engorged again.

Paul’s comments and flirtatious manner made Mike feel delightfully submissive and feminine. These feelings and the earlier activities in Paul’s SUV underscored that Mike’s life was forever changed. Today’s activities were also an acknowledgement that he was destined to become a femininely submissive and willing cocksucker; dare we say Sissy? Only time and Paul would tell.

Unexpectantly Mike assertively announced. “Paul, let’s get this understood right now. Any time we’re together or I’m in girl mode you WILL call me Sara. Is THAT clear?”

“Crystal” and a head nod was Paul’s reply. Paul was surprised but impressed with Sara’s assertiveness. “Yes, Princess that will be no problem; you’ll be my Princess Sara… you are destined to be a lovely Fairy Queen.”

The two embraced, exchanged gropes and kissed goodbye. “I’ll pick you up this Saturday at the library at 4 pm.” Sara floated home on a cloud of bliss and with a throbbing bulge in her panties. She resisted the urge to reapply her lipstick.

Sara was already mentally planning what items to include in the MK cross-body purse that Aunt Linda had gifted her; makeup, makeup remover pads, nail polish and remover, cotton balls, baby-wipes, spare panties and travel size bottle of mouth wash. She also decided to wear her wispy Sable Grey training bra for effect and personal arousal. Sara smiled and decided to included condoms and lube in her purse. “In case I “get lucky” this Saturday.” She vowed that she would ‘see stars’ one way or another.

At home Sara continued to marvel about what she had done. Wrapping her hand around Paul’s hardness was more thrilling than anything she had ever done; it fit the palm of her hand perfectly. Its length and girth were longer and larger than she expected; her hand had slid nicely up and down Paul’s wet shaft; Sara fondly recalled the throbbing warning of Paul’s pending ejaculation as she pumped him to orgasm.

The days that followed

Sara had recurring wet dreams about performing fellatio on young teens and adult men; she dreamt about stroking penises. Her boy-pussy became an object of intense curiosity. She wondered how to safely lose her virginity. Would sex hurt? She was desperate to have her pussy filled by someone or something…‘just like the photos and characters in my magazines’.

Not knowing how her Saturday date would work out Sara’s impatient bi-curiosity led her to wonder what consummation of sex between her and Auntie Linda would be like. Maybe Linda would take pity and do her a favor. Such an experience would be safer with Auntie than with a stranger. Aunt Linda would be the safest option to quell her pressing carnal needs. Maybe Uncle Stevie would volunteer.

With that in mind Sara wrote her Aunt a poignant letter outlining her concerns that she would mail on Monday.

Dear Aunty Linda,

Sara

When the sun came up Sunday morning, the day after her date with Paul, there was no longer a need to mail the letter.

Is this end for Sara or just the true beginning?

Dear reader: I have several stories posted on this site. I even have another Sara story posted that is also very exciting. You can do a ‘Search by Author’ for Donna T. - Take a look.

Adventures of Sara: Evolving Deeper into Femininity – “What does summer camp, college library, the Caribbean and cross-dressing have in common? Sara! On vacation: "There are 'women' here but there are no females." "You, Princess, brought attention on yourself starting at the airport. You made yourself the perfect fall 'girl' for their needs."

https://bigclosetr.us/topshelf/fiction/90121/adventures-sara-evolving-into-femininity