Pretty Stacy: Beginnings

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“Hello, my name is Stacy. I used to be known as John Miller. I designed the waitress uniform I’m wearing. I added starched petticoats because I love petticoats. Everyone should have some rustle in their bustle. Besides, having a petticoated sissy as a friend isn’t a bad thing. This story explains my beginning and my evolution to full sissydom. I think it was a matter of good luck; right place at the right time. It could happen to anyone.”

Stacy is definitely cute. She stands five feet seven inches tall in her stocking feet and maybe weighs 120 pounds. Her job as a waitress in the small mountain town of Wrightwood, CA requires Stacy to dress in a ‘mountain café waitress image’ of the Alps. Stacy designed the uniform for the cafe. It’s a blue and white gingham waitress outfit with short puffed sleeved shoulders. Stacy’s uniform includes a starched white linen apron with lace trim and front pockets. A snug, front laced bustier pushes up and emphasizes her pert breasts. It hadn’t taken long for Stacy to discover that a good cleavage meant better tips.

Stacy’s attractively short dress ended about four inches above her knees; a starched, white crinoline petticoat, with ruffled hem, gave her outfit the girly flair that she sought and liked. White knee socks, black patent leather Mary Jane shoes, with one inch platform heels, complete her uniform. Her long platinum blond hair framed her pretty face perfectly. Stacy’s bright blue eyes matched her blue sapphire drop earrings and the blue gingham of her dress. Her long, dark eye lashes added to her illusion. A blue sapphire ring on her slender finger accented everything. Blue nail polish was on her beautifully manicured finger nails. Stacy’s makeup was impeccably perfect as were her classic arched eyebrows. Stacy definitely matched the image of a foxy looking serving wench; or a very sexy Alice in Wonderland.

Occasionally Stacy wore more than one petticoat just for effect. Stacy has a pleasant fetish for petticoats. She loves the swishing sound as she walks; their sound and feel constantly reminds her of the femininity she strives for.

What series of events helped make Stacy the pretty sissy that she is?

There never was any child abuse at any stage of Stacy’s ongoing feminization. Stacy was a willing and eager participant. All parties involved learned, benefited and were rewarded by their mutual arrangements. Stacy’s path into cross-dressing evolved from nail polish as a baby to panties, bras, hose, makeup, hair and vocal training to sound as feminine as possible. A girly attitude and demeanor became ingrained.
So how did John become Pretty Stacy? Some folks would say it was just luck or that it was the ‘perfect storm’. Judge for yourself.

The beginning

John Miller was raised in a single parent home. John’s father was out of his life by the time he was 3 months old. There never was a male role model. There was only mom and his sister Sissy.

Mom

Susan Miller – John was supposed to have been born a girl named Stacy. He wasn’t. Four years old Sister Sissy didn’t get the little sister that mom had promised her. Mom had let her down. Mom and Sissy’s disappointment ran deep. Mom didn’t get the baby girl she yearned for. Both were very disappointed that the baby was a boy… but there are ways around such obstacles! Mom was already calling John ‘Stacy’ and referring to him in the feminine ‘her’, ‘she’ etc. before leaving the hospital. Sissy did the same. It was the norm of John’s childhood.

Mom’s great disappointment in not giving birth to another girl manifested itself by mom going out of her way to make John look as girly as Sissy had looked when Sissy was a toddler.

John’s feminization was never extreme but it was long term, total immersion and unending. It was a series of events that subtly imprinted a female mindset deep into John’s young brain. It was a depressed mother making her second child as pretty and girly as her first child. With all the ‘hand me down’ clothes from her first child (Sissy) dressing Stacy as a girl seemed perfectly normal. Use the clothes you have… save money.

At age 3 mom had John’s ears pierced so they could all have matching ear studs. Strangers would gush about how pretty mom and her 2 little girls were. “They look just like you” mom was repeatedly told. This praise was important to mom. Praise gave her the excuse to insure that both her daughters were always as cute and girly as they could be. Nobody guessed their secret.

Stacy was subjected to wear whatever mom and Sissy wanted and the females always wanted cute and girly. Mother-daughter matching outfits were the norm for John until he was 5. The three of them were a matched set from clothes to hair to earrings. They always wore matching nail polish. John’s long blonde hair always had a beret, ribbon or hair clip and went uncut until age 6. Matching jumpers were mom’s favorite clothing item for them as were petite pearl ear studs. Being so young John didn’t have a clue that anything was wrong or out of the ordinary. He knew many things in his life were to be kept secret.

Susan eventually delegated much of her motherly duties to her eldest daughter Sissy when Stacy was 6.

What series of events helped make Stacy the pretty sissy that she is?

As John aged, and would indulge himself in all sorts of femininity, mom would ignore it or praise him for being such a cutie; there were many ‘you’re such a pretty girl’ moments for John. Being girly was reinforced and rewarded. Being an unkempt rowdy boy was always admonished. Girly behavior traits became embedded in John.

Sissy: the older sister

At first big sister Sissy resented having the chore of caring for the little brother…a brother that should have been a girl named Stacy. Eventually boredom and a certain amount of curiosity caused Sissy to begin playing ‘house’ and experimenting on her compliant brother. It started with nail polish and crinoline petticoats and, over the years, evolved to panties, skirts, cosmetics and hair. Beth would look the other way when Sissy would feminize Stacy. A female attitude took hold.

Stacy would bathe Stacy… and would spend a little too much time than needed washing Stacy’s penis.

From birth and through high school John was his big sister’s living doll. Stacy became Sissy’s makeup canvas, clothes model and playmate. Sissy and Sissy’s playmates would play house and John was always their girl friend. Dressing John in her old clothes, dresses and petticoats was routine. John’s fondness for petticoats took root with this. He loved the way they sounded when he walk. And they felt nice.

Cosmetics and jewelry became part of their routine as it is for all young girls. John took pride that his ears were pierced and his playmates were not. His ear studs made him feel special. Sometimes, while watching mom applying her cosmetics, John would ask for some too. Mom was very willing to do so. Mom may have been first to begin John’s feminization but it was Sissy who was the main facilitator.

Sissy created in Stacy an appreciation for all things feminine. Delicious odor of cosmetics and lotions, sensual feel of silks and nylon materials, a sense of fashion, the smell of nail polish and fine lipsticks, the texture and taste of lipstick, how to use cosmetics and just as important, how to remove makeup. Sissy became a surrogate mother and a full time baby sitter. Sissy was also a mentor, role model and confidant. The desire to wear dresses, panties and ‘pretty things’ became Stacy’s reality. Sissy taught John how to be the best ‘Stacy’ possible.

What series of events made Stacy the pretty sissy that she is?

Halloween

Halloween doesn’t cause cross-dressing but it does let a person experiment with their gender alter ego in public. Halloween gives cross-dressers a chance to feel ‘normal’. At various age levels Stacy was; Raggedy Anne, a fairy, Tinker Bell, Ariel, Cleopatra. Stacy’s Taylor Swift impression was extremely well received! From his first Halloween to his last Halloween Stacy always took a female role.

Condensed background timeline

John’s earliest memories of life were watching mom and Sissy showering, shaving, dressing, applying cosmetics. Breasts, bras, nylons, baby dolls, jewelry, lingerie and attitude were embedded in his psyche. It was a single parent, no male role model situation.

By age 4 Stacy was clomping around the house in ½ inch rhinestone wedge heel sandals, in a pretty jumper or a crinoline skirt. Her pajamas were age appropriate for a young girl. Toys included My Little Pony, Pippa Dolls, Unicorns and Disney movies. It didn’t faze John as this is what was normal to him. And there was always nail polish!

By age 8 it was one inch wedge heels, pink Hello Kitty cotton panties and a skirt or dress of her choosing. Stacy would pick a color and apply her own nail polish. She would also wear her hair in a ponytail. It was all very natural for her.

At age 12 Stacy insisted on nylon panties and camisoles because she was a ‘big girl’ now. At home she wore training bras and hoop earrings. She had bracelets, anklets and rings. Her nail polish collection was impressive. Young Stacy could hook her bra like a woman; from the rear and behind the back.

Stacy eventually began to wonder why she was so flat chested while mom and Sissy were amply endowed. Where were her ‘chest bumps’? Stacy began to yearn for breasts of her own. “They don’t have to be huge… just give me something!” To shut her up they gave her their old falsies and breast enhancers. Sissy felt bad that little Stacy didn’t have anything to fill her bra.

For a 13th birthday present Stacy asked big Sister Sissy to take her, fully dressed as a girl, to an out of the area mall for a second ear piercing just above the ones she’s had for years. Stacy was proud of having double ear studs. Stacy continued to lament about being flat-chested.

Sissy takes pity, has a heart-to-heart talk with her little sister.

Sissy: “I feel sorry that you don’t have breast buds yet. I know that you know there are ways for boys to develop breasts. It involves strong hormones which could have long term and major consequences.”

”Are you aware of what I’m talking about? Do you fully understand what this will do and what road you’ll be going down? After awhile you may not be able to get an erection no matter how much you play with your weenie. Would you be ok with that? ”

Stacy: “Yes. I’ve researched it a lot on the internet and YouTube.”

Sissy: “Stacy, I would be a bad sister if I didn’t watch out for your best interests. You are so girly that I don’t see my brother anymore... I only see pretty Stacy. Are you attracted to boys? Do you want gender reassignment surgery?”

Stacy: “If you’re wondering if I want myself ‘snipped’ in order to look feminine, the answer is no. I love my appendage too much. You gave me so much penis pleasure. I wouldn’t want to miss out on the pleasure it gives me… and others. I’m a real sissy when it comes to surgery.”

Sissy handed Stacy a plain brown paper lunch bag of ‘things’. Sissy: “Here are a few things that will help you grow your tits; Crèmes and pills. This bag has all that you need. See me when you need more. Use the crème and do the exercises as they can’t hurt you. If you abuse the ‘vitamins’ I’ve given you’ll wish that you hadn’t. If you become ill from the ‘vitamins’ tell me immediately. If we need to see a doctor we will. This is serious stuff!”

Stacy was jubilant! She never skipped the exercises, always applied her creams and always took her ‘vitamins’. At year’s end Stay was an A+ cup.

The Web

The Web opened Stacy’s world and expanded her horizons. Research and an inquisitive mind taught her many things. She learned about cross-dressers and alternate lifestyles. She researched: taping, gaffs, voice modulation, how to speak and sound like a female, bisexuals, porn, hormones, how to pass in public techniques, YouTube videos, LGBQT friendly websites, etc. Stacy found others with cross-dressing inclinations and she learns the difference between being a ‘top’ vs. being a ‘bottom’. Most importantly she learned about herself.

Stacy was trying to resolve deep inner conflicts and trying to figure out where she fits in and why she was different. Stacy accepted and embraced her feminine side and willingly went further down the path to femininity and outright sissy-dom. Stacy eventually concluded that she is a bisexual cross-dresser with a petticoat fetish. She could live with that!

By age 14 Stacy was a B cup and began routinely sleeping in baby dolls, camisoles and satin PJs. Wearing pantyhose and tights became normal especially under her boy pants. Shaving her legs and arm pits, like Sissy and mom, was the norm. She continued doing her breast enhancement exercises and taking her ‘vitamins’.

At 15 Stacy, thanks to Sissy’s help, was compelled to begin wearing a sports bra and to bind her chest for physical activities like running or jumping. Stacy’s ‘bumps’ were pleasantly apparent. Her nipples would tingle when she rubbed them on a blouse rubbed or when she played with them. Stacy found that camisoles protect nipples.

A compression T-shirt was all she needed to make her B cup chest flat enough to stop the stares and questions while out in public. When wearing boy clothes Stacy always wore panties, pettipants and nylons underneath. Fittingly enough, when Stacy competed in the Womanless Beauty Pageant during her senior year in high school, she was the only contestant that didn’t need to stuff their bra.

Stacy was 13 when 17 year old Sissy began a two year Cosmetology program

If Stacy allows herself to be Sissy’s cosmetology practice model then Sissy would reward her by stroking her penis to ejaculation. “I’ve given you baths and I’ve washed your weenie since you were born. Every time that you do something for me I’ll masturbate you. Stroking your penis now is no different than what I did when I bathed you except now there’s no water. You loved what I did then and you’ll love even more what I’ll do to you now. Oh, and by now you’re probably squirting sperm.”

Sissy explains things

“I need a practice model for my cosmetology class and you’re it. As young kids we always dressed you up and made you up with no complaints from you. Hell, you started using cosmetics on your own! Let me work on you, for my classes, and maybe you’ll learn a job skill that will get you a job. We’ll help each other. Besides you’ll get to look pretty and learn more about makeup. You’ll also attract boyfriends. Sounds like a good deal to me.”

“You have been raised and immersed in femininity since birth; your girly manners and traits come much too easy for a real boy. Inwardly you are one of us. Accept your fate. We all know you should have been born a girl… the little sister that mom promised me. You are Stacy.”

“You wear girl clothes and makeup, your ears are double pierced and your eyebrows are perfectly shaped. I stopped shaping them a year ago so you obviously pluck them yourself. What boy does that? You also have more colors of nail polish and lipstick than me and mom combined.”

“Another thing, your favorite ‘around the house’ clothing is a pink jumper, panties, bra and one inch heeled rhinestone sandals. Your favorite shoes have a 1 ½ inch heel. By choice you always wear nylon panties, pettipants and a bra. You even have a favorite mascara and lipstick. Sometimes the only “boy” I see in you are the ‘Boy Short’ panties you wear. Need I say more? Do you disagree?”

Stacy hesitates awhile and then replies: “OK big sister, I’ll help you out. I want to learn all I can about cosmetology, makeup and how to look prettier. Having you play with my weenie will be an added benefit.”

More than makeup

Sissy is also curious about the male anatomy. Specifically she is curious about penises and she’s curious about oral sex. She’s tired of only reading about blowjobs and is anxious for some hands on and mouth on experience.

Sissy decides to practice fellatio on Stacy before she tries it on her boyfriend Randy. Stacy was happy to be there for her sister. While sucking Stacy off Sissy would always ask Stacy to tell her what made her feel good and what did not. Knowing that Stacy is a virgin without STDs Sissy is also curious about what sperm tastes like. With Stacy there seems to be an unlimited supply of pristine cum which Stacy is very happy to provide. When Sissy would suck the sperm out of Stacy’s cock she would always kiss Stacy and share Stacy’s fresh cum with her. “Every girl should know what sperm tastes like.” Stacy never complained and began to look forward to the sharing. In fact Stacy began sampling her own cum whenever she pleasured herself. Sissy had watched Stacy do this on several occasions.

Stacy too is curious about oral sex and Sissy happily instructs Stacy on how to orally please a woman as well as how to orally please a man. Stacy decides that sperm tastes better than pussy.

Stacy has first sex

During her 15th year Stacy had sex with a 17 year old neighbor boy that was in the schools LBGQT group. The boy seduced Stacy and sucked Stacy to an earth shaking orgasm. For the first time Stacy has a finger inserted in her rectum as part of sex. Actually it was more than a simple finger insertion; it was a true and proper finger fucking. Afterwards Stacy showed the boy blow job techniques that better pleasure a penis by using her tongue, lips and hands in imaginative ways that Sissy had taught her. Like Sissy had taught her Stacy swallowed his sperm, which is something Kenny did not do.

Stacy needs a big sister talk

“Sissy, we need to have a talk. I had sex with a man and I need to sort things out. He sucked me and I sucked him and I liked it. He fingered my butt hole and I liked it. It felt nice. Does that make me a sissy?” Sissy assumed a nurturing big sister role and listened as Stacy explained about her first sexual encounter with a man. Sissy let Stacy vent without cutting her off or passing judgment.

“I met a cute boy in our LGBQT group. I went over to Kenny’s house because he was going to show me how to make my own gaff out of an old pair of jockey shorts. All you need is scissors. I thought I’d be safe with Kenny. I thought he was like me. Once we had made one gaff I needed to try it on to make sure it worked. I was wearing my panties and bra. I took off my panties and pulled the newly made gaff on making sure I was properly tucked.”

“I was having difficulty getting the gaff to fit right. Kenny offered to help me with the gaff. He stood close behind me. I could feel his breath and body heat on my neck. And he may have nuzzled my ear a bit. I don’t know why but I began to get an erection. Kenny reached between my legs to make sure I was properly tucked and his hand gently cupped me. The pressure and warmth of the palm of his hand was pleasant. He pressed his hand up and held me. I knew he felt my penis begin to grow. He kissed me softly on the back of my neck and I tightened my legs together to keep him from moving his hand away from my cock. I had never been touched there by a man.”

“While holding my crotch he used his fingers to rub my penis. I made no attempt to get away. Instead I flexed my legs and trapped his hand again. I hoped he’d rub me more…smear my precum and rub the tip of my dick like you do. It was so exciting! It made me swell down there. My breathing became rapid. Kenny slowly withdrew his hand from between my legs, making sure to stroke my growing hardness, as he continued kissing my neck and ear; my dick was leaking a lot. Kenny slowly turned me around and he was naked. His penis was pointing at me. It was longer than mine. I reached out and felt it. It was warm, firm and beautiful. I could feel his pulse in it. I gently stroked it a couple of times and then released it. He isn’t circumcised! What a turn on!”

“Kenny began kissing me on the lips and he slipped his hand under my bra. He circled my nipple with his thumb. It made me feel light headed. So I kissed him back and took hold of his stiff penis. I rolled back his foreskin and lightly stroked his cock like I do to myself. He let go of my tit and moved his hand to my dick. I was so aroused that I didn’t protest. I was eager for whatever would happen. He gripped my dick like I was grabbing his dick. He stroked me and I stroked him. It felt wicked but thrilling at the same time.”

“As if we were dancing Kenny waltzed me backwards to his bed. He put his hands on my shoulders and gently pushed me down into a sitting position on the edge of his bed. He spread my legs and knelt between them. He had my dick in his hand.”

“Kenny leaned forward and kissed and then licked the tip of my penis. He swirled his tongue around the glans and the corona. It was so exciting! He began pumping my penis. He tongued my shaft from the bottom to the tip before guiding my penis into his mouth. It felt so warm and pleasant! He sucked my dick into his mouth like big spaghetti. It felt divine! It felt different than when you pleasure me. I was moaning and my dick was harder than ever before. And then it got better!”

“Kenny stopped sucking me long enough to find a tube of lipstick. I was panting as I watched him slowly apply Crimson Red lipstick to his lips. I had no idea what he was doing but it looked erotic to me. He put the lipstick away, knelt and then grabbed my shaft with one hand and used his lips to grip my dick just below my cock head. He pressed his lips snug and deliberately left a red ring! You’ve never done that to me! He even left a mark at the base of my dick! And then he began milking me with his lips and mouth, dragging his pressed lips and tongue from the bottom to the top. I could feel the texture of his tongue.”

“I was close to an orgasm when he slowed the pace for a moment. I felt him take a deep breath and then to my surprise he inserted a finger deep into my rectum while still sucking me! I felt an electric shock and my cock got rigid as a crow bar. Kenny kept sucking me while slowly sliding his finger in and out of me. It was fantastic! Kenny then began finger-fucking me in earnest! I muffled a scream; it was a feeling I never had before. What in God’s name will a real cock feel like in my ass? I’m getting hard just thinking about what he did.”

“After he blew me I willingly and slowly sucked Kenny to orgasm. It seemed fair to me. His penis felt firm yet soft in my mouth. I used my tongue to lubricate, tickle and explore; just like you taught me! It was my first cock and I took my time. Based on what you’ve done to me I knew what to do to him. Because wore lipstick while sucking me I did too! I left rings up and down his shaft. Seeing my lipstick rings on a man’s cock was so freaking erotic... it added to my hardness and pleasure. I felt naughty and very, very horny! And then Kenny came. The force of his cumming surprised me.”

“A throbbing in his cock told me that he was about to cum and then he did. I savored the taste of him. He was surprised when I swallowed his load! Kenny was more surprised when I kissed him and slipped him a full dose of his own sperm like you do with me! Based upon the sperm that you’ve shared with me I definitely taste better than he does.”

Well sweetie, I think that’s a very telling reaction. We need to talk and help get you sorted out.”

“What I didn’t like was when, just before he exploded in my mouth, Kenny forced my head down to the bottom of his shaft… he wouldn’t let me move! And then he squirted down my throat. The feel of him pulsating in me was nice but I thought I was going to gag when he held my head in place. At first I couldn’t taste much of what he pumped into the back of my throat; his sperm sort of went down all by itself. That’s mean of him on several levels.”

“Kenny and I lay in his bed for awhile enjoying our post orgasm glow. Eventually we started kissing and I was hoping for another suck. Kenny likes my puffy titties. He licked and sucked both of them while he fondled my dick with a free hand. My nipples got hard, large and sensitive. Kenny rolled me onto my side facing away from him. He moved into a spooning position and began probing, wetting and rimming my sphincter with his tongue! It was wet, warm and totally wonderful! I thought I was going to explode! It’s an amazing sensation to have someone tongue your backside.”

“Kenny got off the bed, pulled me around and put my legs over his shoulders. I thought he was going to lean in and suck me off again. He had a lustful look in his eyes. He was holding his dick and began circling my wet sphincter with his leaking cock head. I felt my love hole being stretched as he tried to slide his penis in me! Kenny was going to fuck me!”

“I think he got his dick part way in! I panicked. He was trying to rush me so I told him to stop and I rolled over. If he would have let me relax and gradually accept his dick I would have gone through with it because I was so aroused. The thought of it… the thought of him sliding in and out of me, the thought of what I missed out on makes me so horny!”

“Well sweetie, that’s a very telling reaction. We need to talk and help get you sorted out.”

“Since that day with Kenny I find myself staring at guy’s crotches and wondering what they taste like or how it would feel with their cock in my ass. Now I want to suck a circumcised cock. I want the feel and taste of a penis in my mouth again. I can’t stop wondering what a penis in my ass will feel like. Sex with a man was so amazing! It’s as if someone flipped a switch in my brain.”

Stacy confides, “No offense to you but I love sucking cock more than sucking your clitoris. A penis is more sensual and fulfilling. I can grab, hold and stroke a penis but I can’t do that to a clit. Why is it that when I’m sucking cock I get a tremendous erection and when I’m licking pussy I don’t? I guess that makes us both Sissies. These thoughts give me erections.”

Sissy listened intently until Stacy had let it all out. “My gosh, little sister, you’ve been a busy girl. I can’t believe how quickly you’ve grown up. I didn’t see this situation coming up until a few years from now. I’m glad we’re having this talk. Hold on a minute I want to go get a few things. I’ll be right back.”

When Sissy returned she handed Stacy a pink paper bag that contained 2 tampons, 2 panty shields, 2 condoms, a travel size personal lubricant, breath mints and a pack of baby wipes. “You need to learn how to use all these things. Most are self explanatory. You will need to deal with pre-sex pecker tracks to avoid spotting your panties. Panty liners are the solution.”

“The tampons are for the post sex leakage that you’ll always have. Tampons are cheaper than dry cleaning or a new mattress. If you need help with learning how to insert a tampon I’ll give you a hand. There is a technique that makes it easier. With a boy it’s a matter of depth.” Stacy was inspecting all the items but seemed mystified about the breath mints. Seeing Stacy’s quizzical look Sissy admonished, “No one wants to smell sperm on your breath.”

Stacy advises Sissy

Stacy: “Oh Sis, if you want to surprise and pleasure your boyfriend you need to slip a finger into his ass! There’s so much more to it than just ‘sticking it in’. You need to tickle his rosebud, move it around and then slide it in. Then slide it out and slide it in again…and again. Finger fuck him… and there’s a prostate gland that will send him waves of pleasure… he won’t be able to control himself and he may just grip your finger… he’ll love it! Poke him when you’re sucking him.”

Stacy: “All this talk has given me an urgent hard on. Look at the erection I have … just talking about Kenny with you makes me want to have sex. Do you feel like helping your little sister out?” Stacy stopped talking and paused a moment to consider what she had just asked her sister to do. Continuing Stacy pleaded, “And would you use a finger on me like Kenny did? Please? I’ll do anything for you!”

Pondering what Stacy had just confided Sissy said, “Little sister you are quite the cocksucker it seems; a real fellatrix. You need to suck more cocks in order to become more proficient. If I help you out now with your obvious need for sexual relief will you suck my boyfriends cock? His birthday is next week and he would appreciate some variety. I’d like you and your mouth to be my present to him.”

Taken aback by her sister’s bold request Stacy took a moment to weigh her immediate and very pressing need for sexual relief vs. the opportunity to taste another penis. Stacy reclined back on Sissy’s bed with her penis pointing towards the ceiling; a drop of precum was dribbling down her shaft.

Stacy smiled and replied, “OK, I’ll suck your boyfriend but I won’t stick my finger up his rectum… my long nails would hurt him.” Sissy nodded that it was a deal. She moved closer to her little sister, knelt and grabbed Stay’s penis at the base like she had so many times before.

Sissy: “OK, but there are a few requirements; I get to watch and when he cums you need to share some with him before you swallow. I want him to swallow some of you, OK? Hell, now I’m horny too.”

Using her thumb Sissy smeared Stacy’s abundance of precum lubricant in a circular motion around and down Stacy’s cock head. Stacy moaned in delight. Stacy watched as Sissy momentarily stopped her efforts. Sissy reached over to the night stand and retrieved a tube of lipstick. Applying a thick coat of red to her lips Sissy leaned over and reclaimed her throbbing prize. Sissy resumed Stacy’s blowjob and ‘marked territory’ on Stacy’s dick.

After a few minutes of putting lipstick rings on Stacy’s cock Sissy stopped her head bobbing, Sissy firmly sealed her lips on Stacy’s shaft and slowly milked her way up and off her penis making sure she collected as much precum and saliva in her mouth as possible. Sissy loudly popped off of Stacy. Stacy at first was disappointed at Sissy interrupting the sweet relief she needed.

Making sure that Stacy was watching Sissy inserted her middle finger into her mouth and used her tongue to fully lubricate her longest finger. For Stacy’s benefit Sissy moved her finger in and out of her mouth in a very sensual way. Stacy looked startled at first until she understood Sissy’s intentions; Stacy relaxed, laid back and spread her legs to allow Sissy easy access to her love hole.

Sissy resumed her cock sucking and slowly wiggled her longest finger deep into Stacy. Sissy smiled as Stacy gripped her probing finger with her rectal muscles. “Maybe there’s something to be said about finger fucking,” Sissy thought. “And there is something erotic about leaving lipstick rings on a cock.” To Stacy’s delight Sissy got busy with Stacy’s finger fucking. Stacy squealed when she came. Sissy slurped up Stacy’s sperm and kissed Stacy on the lips. Stacy sipped her sperm from Sissy’s mouth. It was part of their routine.

Stacy rested and day dreamed awhile before getting up. She pulled up her panties. “Thank you Sissy for taking care of me so well just now.” Stacy was about to leave Sissy’s room when she turned to Sissy and asked “Is your boyfriend circumcised?”

Time to re-pay her debt

It was about a week after Stacy’s sex confessions and their ‘mutual relief’ agreement when Sissy asked, “Remember our agreement from last week?” Stacy said “yes”. “You need to be in my bedroom tomorrow by 3 PM. Randy is coming over and is expecting a very good time. If you play your cards right your curiosity about what a dick feels like in your ass could be solved. By tomorrow night you will have another taste of man to compare things too. Be sure to wear your Taylor Swift Red lipstick, use your girl voice, leave ‘love rings’ on his dick and don’t wear a gaff. I want you dangling in easy reach for him.”

Sissy: “There are a couple more things. Sometime while you are sucking Randy off I’m going to do as you recommend; I’m going to slide my finger into his ass. I’ve even trimmed 2 of my fingernails. I want you to tell me afterwards if he twitches in your mouth when I poke him? I’ll let you know if his ass grips my finger like you did.”

Sissy: “After you’re done with him, be sure to show him your stiff penis. Don’t tuck it away too soon as I want to see if tries to suck on your bone. I think he may have cock sucking tendencies.”

Stacy: “You make it sound like there’s something wrong about being a cocksucker. For my sake I hope he is a cocksucker. That would work quite well for me!”

New discoveries, new delights, questions answered: Stacy sucks Randy

In accord with the birthday sex agreement Stacy sucked Randy dry. Randy had just finished gushing into Stacy’s mouth when Stacy leaned forward and kissed him on his lips. With practiced ease Stacy transferred a mouthful of sperm into Randy’s mouth. She made sure to coat Randy’s lips. Stacy immediately pinned Randy to the bed and clamped a firm hand over his mouth and pinched his nose. Randy’s resistance and head shaking only resulted in coating his mouth and teeth with sperm. It didn’t prevent the inevitable. Randy swallowed and let his head fall back onto a pillow in surrender. Randy laid there a moment with his eyes closed. He slowly licked his lips clean and swallowed again. He opened his eyes but remained in bed.

Stacy: “I did that because you need to know what my sister has tasted over the last few months! It’s not too bad is it?”

Randy was about to get angry but relaxed and laid back. Rather than make a scene, and to prove he was unfazed, Randy looked over to Sissy and softly said “I’ve tasted worse.” Sissy began laughing. Looking at Stacy Sissy said “Way to go sis!”

Randy lay in bed recovering from his orgasm; recovering from swallowing sperm. He was quiet and deep in thought. He opened his eyes and stared intently at Stacy’s crotch. Maybe it was being finger fucked or maybe it was the taste of his own sperm; the combination of the two events brought out long suppressed desires. Randy was lustful in a way that Sissy had never experienced before.

Randy sucks Stacy

It wasn’t very long before Randy began cuddling Stacy. “Thank you for my birthday blowjob. It was perfect.” Cuddling became kissing. Randy groped Stacy’s breast; he obviously wanted something more.

Stacy: “It appears that you want something extra special for your birthday. After the blowjob I just gave you what could be more special than that?” ‘Maybe I’m about to get fucked!’ Stacy thought.

As Sissy had predicted, Randy tentatively touched Stacy’s penis and began stroking it to hardness. Randy’s eyes and concentration were on Stacy’s dick.

Sissy: “So what’s your special request?”

Feeling Stacy’s dick begin to swell Randy licked his lips and looked pleadingly into Stacy’s eyes. “May I suck you cock?” Momentarily startled Stacy said nothing. Sissy said nothing. Randy’s eyes darted over to Sissy before asking again, “Please, may I suck your penis Miss Stacy?” Stacy winked at Sissy as she ordered Randy, “Use the lipstick.”

Randy immediately grabbed the gold colored tube and began frantically looking for a mirror. Out of frustration Sissy took the lipstick from Randy’s hand, firmly grabbed his chin and applied the lipstick to Randy’s lips. “Press your lips together to even it out.” Handing the tube back Sissy continued, “You better learn how to put on your own lipstick, missy!”

Sissy took Stacy’s erection and held it level for Randy. She felt Stacy throb at her touch. Looking at Randy Sissy asked, “Is this you want? Don’t make my sister wait. Come and get it!” Sissy maintained her hold on Stacy’s prick until Randy was gripping it with his lips. As she let go Sissy said, “And you damn well better swallow every drop of her cum. Is that understood?”

Finding it difficult to speak with a mouthful of cock Randy bobbed his head up and down Stacy’s stiffness indicating ‘yes’. Randy worshipped Stacy’s penis with his mouth and tongue. He also made a point to explore Stacy’s ‘rosebud’ too. His tongue made Stacy’s toes curl up in response.

Randy proudly put red lipstick rings on Stacy’s cock. He also left lipstick marks and tongue tracks around Stacy’s anus. Randy’s probing tongue was an unexpected but enjoyable new experience for Stacy. Randy’s tongue went deep. ‘Sissy never taught me about this!’

When Stacy did ejaculate Randy swallowed it all and then sucked Stacy’s shaft vigorously in an effort to get more. Randy was a very willing cocksucker. ‘Yes, he’ll be back for more’, Stacy thought.

Stacy: “You did a fine job. You can blow me anytime that Sissy says you can. You swallowed like a pro. From now on, between us three sissy’s, your new name is Rhonda.”

Rhonda and Sissy both smiled and nodded their heads.

After sucking Stacy Rhonda fucks Stacy

Stacy: “Ok, Rhonda I think Sissy and I gave you a memorable birthday. If you to do me a favor your birthday will get even more memorable. You have no idea how lucky you are.”

Sissy: “What?”

Rhonda: “How could it get any better?”

Stacy: “With Sissy’s permission I want you to fulfill a fantasy that I’ve had for a long time. I want you to fuck me!”

A dream comes true: Stacy gets boned

Randy fucks Stacy Same day. Rhonda lusts for more.

In an effort to keep her ‘boyfriend’ Sissy sucked Rhonda into hardness to get her ready for Stacy. Sissy put ‘love rings’ onto Rhonda’s rigid shaft. Being the ‘good sister’ that she is Sissy also lubed and stroked Rhonda’s shaft while wondering, ‘I sure hope Stacy appreciates what I do for her’.

Stacy removed her bra, laid back ion Sissy’s bed with her feet on the floor and waited. Rhonda stepped between Stacy’s legs with cock in hand. Sissy hooked Stacy’s legs over Rhonda’s shoulders.

Sissy was so anxious for Stacy to have her first fucking that she grabbed Rhonda’s cock and helped insert the first 2 inches into Stacy’s ass. Rhonda held still for a few moments and then slowly slid a third of her cock into Stacy’s rectum. Stacy relaxed and let her ‘love hole’ stretch. Rhonda withdrew completely and then shoved two-thirds of her shaft inside of Stacy. Upon gaining full entry Rhonda began slowly giving Stacy everything she had fantasized about.

The fucking lasted for about 15 minutes. Stacy felt Rhonda cum insider her! It felt warm and wet. By reflex Stacy came immediately. Her sperm blast hit her breast and neck. Still embedded deep in Stacy’s ass, Rhonda leaned forward and eagerly sucked the sperm off her tit. It was only after Rhonda had licked the last puddle of sperm from Stacy’s neck that she slowly backed out of Stacy’s rectum. Rhonda obviously likes Stacy’s sperm. Stacy was pleased with the experience.

All traces of the red “love rings” that Sissy’s lips had placed on Rhonda’s cock were wiped off by Rhoda’s thrusting and Stacy’s tight sphincter. Stacy learned what ‘bareback’ means when it comes to sex. Enjoying her post sex glow Stacy felt a cum dribble seeping from her hole. Sissy came to the rescue.

Stacy’s need to use a tampon was a new experience. It took Sissy 2 attempts and 2 tampons to achieve one successful insertion. Rhonda refused to watch. Sissy handed Stacy a mirror so Stacy could see the tell tale dangling tampon string hanging from her recently ravaged sphincter. Sissy gave the string a playful tug. As promised there was no leakage.

End of the day: What did Stacy learn? She’d sucked, been sucked and was fucked. Now what?

Stacy determined that she definitely prefers sucking circumcised cocks and that she still prefers the taste of her own cum over any of the other cum she’s tasted so far. She also discovered that a cock in her ass is more thrilling than having a finger in her ass; Stacy enjoyed being fucked and wants to experience mounting and fucking a man. Stacy wants to have experienced anal sex from both ends; she wants a break from always being the ‘bottom’ in a sexual encounter. Stacy thinks that fucking Rhonda would feel great and be empowering at the same time.

The birthday sex session was over and Rhonda was taking a shower.

“You queered my boyfriend!”

Sissy: “So what do you think about today’s activities?”

Stacy: “She is the cocksucker that you thought she was. She begged for dick. Thanks for putting the lipstick on her. She liked it.”

Sissy: “Anything else standout?”

Stacy: “Yeah, I want to have a go at Rhonda’s ass with my penis. I don’t think she’d resist.”

Sissy: “Why do you say that; because she sucked you off?”

Stacy: “It’s not because she blew me, it’s the way that she blew me, and it’s the way she screwed me. She was too eager to get my penis in her mouth. She begged to blow me! She wanted more! I’m sure she’s just as eager to get a penis in her ass as I was. She’d take it, she’d like it and she’ll beg for more. Tell Rhonda that you have one more birthday surprise for her. Be sure to call ‘him’ Rhonda, OK?”

Sissy: “There’s no way that she’d allow that.”

Stacy: “She sure liked your finger deep in her ass, right? She liked blowing me, right? She really likes sperm in her mouth. Tell Rhonda that it will be our secret. Tell her that I’ll be gentle with her but that I can’t fuck her until a week from now.”

Sissy left the bedroom and went to where Randy was showering. She was gone for about ten minutes. Reentering the bedroom Sissy sat on the foot of the bed and patted Stacy on the leg.

Sissy: “You were right. Rhonda wants to get fucked. I think you queered my boyfriend!”

Stacy: “It wasn’t that difficult. I sensed that she’d be back for more. There was the no hesitation when she swallowed my load or when she tongued my ass the way she did. I knew. She was thinking of me fucking her ass while she was busy doing me.”

Sissy: “A week from now will be fine.”

Stacy: “If Rhonda wants my stud services, tell her she needs to come to me wearing pantyhose, a bra and lipstick. Tell her that she needs to have a hole cut in the backside of her pantyhose before she gets here. It might be fun having my own sissy.”

Sissy: “Don’t forget that Rhonda is my boyfriend!”

A week later: Sissy meets Stacy in her bedroom.

While Rhonda was in the bathroom applying her lipstick, and adding eye shadow to her eyelids, Sissy took the time to update Stacy.

Sissy: “Rhonda wants me to tell you that she’s wearing a bra and that her pantyhose are ready for you. She agonized on which style bra to buy so she bought two: a black lace sleep bra and the exact flesh tone pushup bra that you wear. When she bought the bras, pantyhose and lipstick she also picked up a package of Pearl Lite tampons. She’s really gotten into this. She shaved herself without me asking. Like I said I think you queered my boyfriend!”

Stacy: “She shaved herself?”

Sissy: “Yes. Shaved her legs, arm pits and her butt! That’s dedication. In preparation for you Rhonda tried to glam herself up. I loaned her my mascara and did her eyeliner. Be sure to compliment her.”

Stacy: “Good girl! I knew she was eager but not this eager. She has a promising sissy future. Is there anything else of interest with her?”

Sissy: “For foreplay Randy… er, Rhonda wants to suck your cock again in order to get in the mood. I think she likes your sperm!”

Stacy: “That works for me. You need to hand her a tampon before she comes into the room. I’m trying to create some psychological anticipation in her. I want her holding it when she enters. If I needed a tampon then Rhonda will need one too. Tell Rhonda that before the hour is up that she will be wearing it.”

Sissy: “Remember, Rhonda wants to be taken doggie style at first.” Sissy took the Pearl Lite tampon from Stacy and left to get Rhonda.

After the fucking; Stacy and Rhonda liked it

Two hours later Rhonda was happily waddling towards the shower. A tell tale string of her own dangled from her backside through the hole in her pantyhose. As a favor Sissy inserted the tampon into her deflowered boyfriend’s ass. There would be no leakage, no crème pie.

Serendipity and a feeling of empowerment

Stacy was happy. She had fucked a man! After her final deep thrust Stacy climaxed and held tight to Rhonda’s hips, holding her motionless while enjoying her last few squirts. In a subconscious show of dominance Stacy remained deep in Rhonda until her penis deflated.

Stacy felt virile: alive, vibrant and in charge of her life! Her curiosity, but not her interest in anal sex, was gone. Being the ‘top’ in anal sex was a new sensation. The sex act felt better than she had hoped. Ravaging Rhonda’s rear passage was one of those experiences that are a landmark in a sissy’s life. It was a landmark for Rhonda too.

Sissy: “So what do you think, little sis? Was Rhonda a good fuck?”

Stacy: “I think that Rhonda has been fucked before. Did she ever go to summer camp or was an altar boy? She has the makings of a real slut. Did you see the way she kept backing deeper onto my prick and moving her ass around and around? She definitely wanted it deep. The milking of my penis with her anal muscles was not an amateur move; she removed all the red love rings that she had put on my prick.”

“Rhonda may have said she wanted to be screwed doggie style but before she was satisfied she had wrapped her legs around my waist and also had her legs over my shoulders. She couldn’t get enough dick. She was searching for what would feel best! I wonder what a ribbed condom would do for her. In fact I wonder what a ribbed rubber would do for me!”

Sissy: “Yeah. I saw her making sissy quivers on your dick; very sluttish! I was there, remember?”

Stacy: “You jacking her off from time to time while we fucked made things interesting for everyone.”

Sissy: “If this goes where I think it’s going our group will have three sissies; you, me and Rhonda.”

She’s my boyfriend! A request for the next time

Sissy returned from speaking with Rhonda who was still in the bathroom. Sissy walked over to Stacy and handed her $25. “Rhonda says ‘thank you’. She’s very appreciative. There will be another $25 next time. She can afford it.”

Stacy: “I want you to have this money; she is your boyfriend. We’ll split the money next time.”

Sissy: “Rhonda wants to know if she could wear a garter belt and nylons for her next fucking. I’d prefer she wore a garter belt as it give me access to her penis; you’ll probably be busy with her other end anyway. I can’t believe that she is MY boyfriend… my slutty boyfriend.”

Stacy: “No problem sis. A garter belt and nylons will be fine. It’s a fine idea! I may wear my garter belt and nylons, without panties, the next time I fuck her. Did you tell her that I want her ass squeaky clean?

Sissy: “Yes. When Rhonda is buying her enema I’ll also have her buy us a box of deep ribbed condoms. Like I said, I have to get something out of this.”

Stacy: “Have her buy new sheets too. We need them.”

The two hugged. Months pass.

Serendipity: a fortunate unplanned, life changing event or discovery

Stacy’s fucking of Rhonda had ripple effects in Stacy’s life; it was an empowering moment. The sex act elevated Stacy from being the demure, subservient, soft spoken ‘bottom’ to being a confident, in charge, person that would speak up and assert herself. Deflowering Rhonda aided Stacy in being more prepared for life, less accepting of being taken advantage of... assuming a take charge, speak up attitude. Her new attitude would do her well as she goes through life. Stacy would never be a door mat. Stacy’s new confidence could win a beauty contest, get her a job, and… help her in many unknown ways. At age 16 it was a profound moment of self discovery.

Stacy goes public via Womanless Beauty Pageant – senior year, age 17

Stacy’s high school promoted a Womanless Beauty Pageant as a fund raising effort on behalf of the on campus LGBQT club. In her junior year of high school, when she was 16, Stacy saw her first public celebration of cross dressing; A Womanless Beauty Pageant.

Two seniors, Bob (Bonnie) and Conner (Connie), took first and second prize. Stacy envied the way they carried themselves and she admired their courage to be so open. Stacy knew that Bonnie’s and Connie’s involvement with the pageant, and femininity in general, ran much deeper than a casual onetime dress up event. These ‘girls’ were obviously very committed to being pretty; and committed to each other in a way that extended beyond casual friendship. Stacy felt compelled to speak to them.

“Hello, my name is John but friends call me Stacy. You girls are different than the other contestants. I can tell that you truly enjoy being feminine. I know because it takes one to know one. You inspire me with your courage to let your girly side show. It’s very brave of you.”

Bonnie smiled. “Thank you. Your voice is girly, your nails look pretty and your eyebrows are perfect. I can tell you have a bit of a bosom too. You’ll do fine. We are all sisters in a way. Good luck.” Shuffling nervously Stacy continued, “Next year I’ll be a finalist.” Connie reached over and shook Stacy’s hand. “You are very pretty. I see you have several ear piercings but I only see two ear studs. Why aren’t you wearing your other earrings? I don’t want to push you but always be true to yourself. Good luck.”

The next year, at age 17, Stacy was one of eight beautiful contestants in the Womanless Beauty Pageant.

Stacy wins

The pageant went well. Sissy’s entire cosmetology class helped Stacy look stunning. Stacy was their class special project. Nothing was overlooked. Stacy’s hair was amazing. It was also more platinum than usual. Stacy ‘cheated’ by adding hips pads to achieve a perfect figure. Long acrylic nails were added. Stacy wouldn’t remove them for over a week as she enjoyed their girly-girl look. Stacy’s ‘slit-to-the-hip’ white dress showed off her legs when she walked as did her 3 inch heels. The illusion was perfect. Stacy won the pageant. Her photo would be added to the Pageant Wall of Fame. Sissy was very proud.

Stacy’s win wasn’t all smoke and mirrors. Her win was due to her attitude and the way she deported herself. Her win was yet another experience that led Stacy to become Pretty Stacy.

Stacy gets a job: a waitress at age 17

Stacy’s goals after graduation were to get a job, study cosmetology (like big sister Sissy) and then get a better job. With all of the beauty sessions Sissy had given her, combined with all the information she had learned by reading Sissy’s school books, etc., it made sense to get the cosmetology degree and then get a real job.

After graduation Stacy went to work at a local eatery where the family had frequented as far back as she could remember: Benny’s Diner. Benny and his wife Jan knew the entire family. Benny and Jan also knew that John was a bit different than most 17 year old boys.

John was built like an androgynous Russian ballerina; thin and waif looking. The word ‘delicate’ comes to mind. John blended in so well with his sister and mom that it was only two years ago that Benny and Jan learned that John was a boy; mother and sister always called him Stacy. John’s shoulder length blonde hair was always in a low ponytail or under a cap when he was in the diner.

In terms of size Benny and Stacy were close with Benny being 1 inch taller and maybe 20 pounds heavier. For a guy in his early 30’s Benny looked physically fit. Stacy and Benny shared the same light complexion. They could wear each other’s makeup.

Stacy approached diner owner, and long time family acquaintance, Benny Johnson. Benny was sitting in a café booth reviewing invoices. Initiating a handshake Stacy extended her hand toward Benny. Looking up from his work Benny paused. Seeing that it was John Miller Benny politely shook his hand.

John’s weak hand clasp caused Ben to look closely at their grip. Soft palm, weak grip, girly fingers and shaped nails were noted. Conversely Stacy observed that Ben had a firm but gently grip and obvious traces of maroon nail polish in his cuticles. Looking directly at Ben’s face Stacy made a mental note of the pierced earring holes in each of Benny’s ears. Thinking about Benny’s nail polish residue Stacy inwardly smirked. ‘I used to be that careless too’ she thought.

“Mr. Johnson” began Stacy, “I’m applying for the dishwasher busboy job that’s posted in the diner window. “I just graduated high school and need a job that will help me pay my way through college. You’ve known me for over 10 years and I live nearby. I’ll never be late. You need a dishwasher and I need a job. I won’t let you down.”

Benny Johnson replied, “Yes, John, Jan and I have known you and your family for a very long time. We’ve watched you and Sissy grow up. You are steady customers. You always leave a tip.”

Benny paused and took time to inspect Stacy from floor to ceiling. There was more than just a little bit of ‘girl’ oozing from John’s demeanor. Delicate facial features, beautiful complexion and he had pretty hands. He also had double piercings in his ears. Benny was fascinated. Benny let out a low “hmmm” as he continued his thinking.

Benny: “John, do you realize how physical the job is? It gets fast and sweaty. By your looks and size the job may not be right for you. You seem almost too delicate for such a rough job. Our trash cans are about ½ your weight. You might get hurt. Have you thought this through?”

Stacy smiled about being called delicate. It pleased her. ‘If Mr. Johnson knew I was wearing panties and nylons under my pants he’d really think that I was delicate!’

Stacy: “Mr. Johnson, my determination will amaze you. Besides, is there room to advance in such a small place?”

Benny: “Please, call me Benny. It’s good to have goals but here the only option for more money is to promote to waitress. They earn a couple dollars more than busboy and they get tips. Waitress’s need people skills and a good memory. No sweating involved. You’ve seen what it takes to be a waitress.”

Stacy: “Benny, while I’m in school I can give you 25 - 30 hours a week. I can work weekends. Occasionally I’ll need time off for final exams. I can start tomorrow if you need me.”

Benny “OK. I’ll give you a chance. You can start in 2 days. Complete the hiring paperwork and bring it with you on your first day. Be prepared to work hard and long. Don’t wear your good shoes. If you start to feel faint or ill come see me.”

In an attempt at making a smug reference to John’s ears Benny added “You can wear your ear studs on the job if you like.”

Stacy: “Thanks Benny! You won’t be disappointed. I’ll see you the day after tomorrow.” Before leaving Stacy got in a flip comment too: “I’ll wear my studs if you wear yours!”

By reflex Benny touched one of his earlobes.

Benny: “Report at 10 AM for the first few days. Your regular shift will start at 7 AM.”

Weeks later

What events aided Stacy in becoming the pretty sissy that she is?

Stacy had been on the job for just over 3 weeks. Benny and Stacy were both sporting ear studs. Stacy’s were shiny cubic zirconium that looked like diamonds. Benny’s weren’t.

The bus boy/dishwasher job was definitely hard, hot and sweaty but school and work balanced very well for Stacy. As she worked Stacy always observed what was going on around her in the diner. One of the things Stacy observed was that Benny routinely wore panties to work. Benny would stoop to stack supplies or reach high for something and Benny’s panties would show themselves. ‘Maybe he wears thongs’ mused Stacy.

During Stacy’s short tenure Benny had gone through three waitresses. Waitresses were in demand. At least they were at Benny’s Diner.

Time for a change

It was a Sunday morning around 9 AM. John-Stacy had been working relentlessly since her shift began. Diana, the ‘new’ waitress, quit mid-shift during a very busy Sunday morning breakfast. People were lined up and waiting outside. Diner owner Benny exclaimed, “What’s it going to take to keep a good waitress?”

Stacy pulled the stainless steel door of the industrial dishwasher closed and pushed the start button. She had clearly heard Benny’s comments. Just as clearly Stacy decided it was time for a change. She was done bussing tables and washing dishes.

Stepping into the employee break room, Stacy grabbed a spare pink waitress uniform in her size from a linen closet. She grabbed her purse from her locker and stepped into the employee unisex bathroom. Stacy locked the door.

Hanging the uniform on a hook Stacy removed her rubber work apron, shirt and pants and laid them on a bench. She pulled off the compression t-shirt that hid her 34B breasts. Wearing only her panties Stacy took a few moments to rub and dry under her tits. ‘Damn, it feels so good to let them free! I need a job that would accept that.’ Stacy placed the t-shirt in her bag. Always prepared she was disappointed that a spare bra was not in her bag.

Taking a few cosmetics and a hair brush from her bag Stacy leaned closer to a convenient mirror and quickly darkened her eye lashes with mascara and also blended eye shadow onto her eyelids and applied a coat of ‘Taylor Swift Red’ lipstick to her pouty lips. Stacy made for a nice image.

Stacy deftly brushed the boy-cut hair style out of her shoulder length blonde hair. Pulling her hair into a perky high pony tail she locked it in place with a dark blue scrunchie hair tie. She made sure to add bangs. Reaching deep into her bag Stacy pulled out a small pull-string ‘poke’ purse. Opening the poke Stacy reached a finger inside and withdrew a set of two inch round gold hoop earrings. Without the need for a mirror she tilted her head and expertly inserted and clicked them in place. Returning the cosmetics to her bag, Stacy blew a kiss to the image in the mirror and reached for the pink uniform.

The uniform was a ‘button in the front’ classic style diner waitress uniform. It had pink short sleeves with white cuffs and a white collar. Stacy tried to shake the wrinkles out of the uniform and then stepped into the dress and buttoned it up. Bending at the waist Stacy made sure her breasts fell into the darted chest area of the dress. Standing upright Stacy lifted her B cup breasts and let them settle in place; bra-less. Walking over to her locker she placed her busboy pants, shirt and purse inside. Stacy grabbed an order pad and started towards the dining room.

Stacy exits the back area of the diner.

In the alcove before entering the dining area Stacy pushed past her boss Benny; she stopped and turned around to face Benny so customers could not hear. Shifting her voice into the well practiced ‘girl’ vocal tone that she was so familiar with, Stacy put her hands on her hips and spoke to Benny: “Whatever the girl that just quit was making add $2.00 per hour and I’ll be your new waitress. I get Mondays and Tuesdays off, the hem on all waitress uniforms goes up three inches as I want a fighting chance at earning some decent tips. By Friday I want a name tag that says ‘Stacy’.”

As an afterthought Stacy, in an exasperated tone, added: “Get some uniforms that look pretty. Heck, I could design nicer looking uniforms!”

Benny stared with his mouth open. Who is this waitress? Was she his busboy? The reality of the moment befuddled Benny. Shaking off the strangeness of what he was seeing Benny said, “John? Is that you? It doesn’t sound like you! What’s going on? Why are you dressed like that? What’s going on!?”

Stacy:”I’m going out to wait your tables. Your customers will get fed and the diner will make money. I’ll make some tips. By the way my shift started 2 hours hour ago and you need to hire a new busboy immediately. And you better start treating your waitresses better; you seem to go through them rather quickly. Stop it! Play nice.” Grabbing her order pad Stacy made for her customers.

Stacy: “You’re to call me Stacy from now on.”

Benny remained motionless staring at his new waitress. Reaching over to an empty table Stacy pulled a flower from a small table vase and expertly pinned it behind her left ear with a bobby pin.

Benny: “John… eh, Stacy… come to my office when you’re shift is over. I really need to know what’s going on. I’ll try to work with you but I need to know what’s happening.”

End of shift talk

Stacy refreshed her lipstick and brushed her hair before knocking on Benny’s closed office door. Benny immediately answered with, “Enter”. Entering the office Stacy saw that Benny’s wife Jan was sitting in a chair near her husband. Benny and Jan had obviously been discussing the situation.

Stacy: “Hello, Mrs. Johnson.”

Jan: “Hello, eh… Stacy? You sure look different from when I last saw you and your sister. You look very… pretty. Please come in and sit down. Benny and I are a little confused. By the way the uniform looks very nice on you. You fill it out surprisingly well. Your ponytail looks cute as does the flower in your hair. Combine that with your hoop earrings and the pink uniform and you present an attractive waitress image. That is part of our confusion. Who are you? I’m sure you can clear things up. And please call me Jan.”

Stacy walked to a chair, smoothed the uniform under her, and sat down. She crossed her legs in a most un-masculine way.

Jan: “The way you cross your legs seems to be second nature to you. You just did the Sharon Stone, ‘Basic Instinct’, leg crossing move!”

Stacy smiles and re-crosses her legs the opposite way. “My legs look much nicer when I’m wearing stockings” Stacy offered as an ice breaker. Stacy noted that Benny’s eyes were focused on her crotch as if he was looking for something.

Benny: “How do you think you did today? Is waitressing something you like? My customers had only good things to say about you. I asked them. I notice that since we spoke this morning that you found time to paint your nails. Painted nails are not how I remember you… Stacy. At least the color matches your uniform.”

Staring directly at Benny’s hands Stacy said: “Many boys wear nail polish. Getting it all off is the hard part.”

Stacy reached into the front pocket of her uniform, brought out a wad of money and placed it on the desk in front of her before speaking further.

Stacy: “I like the job. I made $75 in tips over a six hour shift and never scalded my hands or broke into a sweat. Once we raise the hemline of our uniforms I’ll do better and so will the diner. I may even be able to accelerate my electrolysis. I think we should completely change the uniform into a style that our guests and we girls would like. I’ve been able to come up with a couple of ideas for improvements since I started working here. I’m very observant.” Stacy was staring at Benny’s fingers and cuticles. Benny noticed. So did Jan.

Benny: “So you’ve have suggestions on how to improve on what we’ve spent 20 years putting together?”

Stacy: “Yes, I have a few thoughts that could help out the diner. I’ll keep them to myself unless you ask me to explain them.”

Jan: “Stacy, on a more pressing matter please explain to Benny and me about your new look and choice of clothing. It’s a pretty major transformation. You’re voice…”

Stacy: “Jan, it’s not so much a transformation; it’s an acceptance by me of who I really am. Working at the diner gives me the money and flexibility to finish my degree. It may not be much of a surprise but I’m following in my sisters high heels and will get an AS degree in cosmetology and a minor in Business Management. “

The three of them talked for about a quarter hour more. At the conclusion of the meeting it was agreed that Stacy would report to work in two days and at the salary Stacy suggested. She would have Mondays and Tuesdays off. There would be properly fitting uniforms for her with ‘Stacy’ stitched on it. The following week the hemline of all uniforms will be 4 inches higher. By mutual agreement pink would no longer be the color of uniforms. The uniforms needed to be upgraded but at a later date.

Stacy as a waitress worked out very well. She was able to save more money and work towards her cosmetology degree. Benny mentioned there was an ‘uptick’ in diner revenue since Stacy started. Stacy was an asset.

Another meeting: 2 months later

Benny sought out Stacy in the break area after her shift. She had already changed out of her uniform and into a comfortable looking green sundress. Stacy was sitting on a bench and was just buckling her white sandals when Benny sat down next to her. Benny began with, “So how are things going? You still like the job? How are things at home? Is everything good?”

Stacy: “Yes, I like the job. It’s actually become less stressful as I find easier ways of doing routine things. The customers and the cooks like me and so do the delivery men. In fact Mr. Tracy, the pharmacist, asked me to move in with him. He claims he’ll treat me like a princess and I’ll never have to work again.”

Benny: “That’s pretty bold talk from an old man!”

Stacy: “Ms. Lebronski also wants me to move in with her. She’s a retired gym teacher. She promises to take me hiking in the Alps and fuck my brains out in the mountain meadows! That’s pretty bold for an old lady.” Stacy noticed that Benny was fixated on her red lips as she spoke. So Stacy slowly licked them for Benny’s delight.

Benny: “I have a work related thing that I need some help with. You said that you had suggestions for the diner, right? Here’s what I want your input with. Our diner is a bit dated and if were to do a business refresh we’d need to update our waitress uniforms. I’m not saying Jan and I would actually adopt your ideas but we would like to hear your thoughts… get a few ideas.”

While Benny was speaking Stacy reached into her purse and retrieved a tube of lipstick and a mirror. Stacy made a show of painting her lips while Benny talked and watched. When she was finished with her lips Stacy fully extended the lipstick and held it under Benny’s nose. “What do you think of the scent of this?” Stacy was gently probing for information or reaction. That unexpected question took Benny aback. He licked his lips.

Benny: “Does it taste as good as it smells? It smells very nice and looks pretty.” was his only comment. He was careful to not take the bait and comment more about lipstick. Lipstick was a subject that he should know nothing about. Yet he did.

Stacy pulled the tube back and put the cap on. “This color works well for fair skinned people.” Stacy made a point to include Benny with her “fair skinned people” comment. The term didn’t go unnoticed by Benny.

Stacy:”So you only want uniform ideas? I could suggest how to clean up your eyebrows; nothing too drastic. I can suggest what colors accent our skin tone and which nail polish remover you should use.” Benny again did not go through the door that Stacy had opened.

Benny replied with a tone of exasperation in his voice. “Yes. Just uniform ideas for now. We have a couple of other concerns that may need some thought later. You’ll need to focus. We’re considering going with a country-mountain concept for the diner. Like a ‘mom and pop’ operation would be in a Colorado ski town. We envision a pot belly stove, ski lift seats as outdoor seating and fake icicles hanging from the roof. We want to exude casual comfort in our menus, atmosphere and uniforms. Do you think that you might be able to generate some ideas, some sketches within two weeks?”

Stacy: “Yes, I will bring you a few suggestions.”

Benny: “Great! In two weeks I want you to show Jan and I what you’ve come up with. No guarantees that we’ll make any changes as we’re looking at what our options are. That is a scheduled work day for you. For your time and trouble you can report to us at 10 AM and when we’re done you can have the rest of the day off with full pay.”

Stacy: “OK, I’ll be there.” Stacy grabbed her purse, put on a nice pair of Audrey Hepburn sunglasses and ‘model walked’ out the door for Benny’s benefit.

Benny stared as Stacy left. ‘Damn! She looks so fine. If I could look half as pretty I’d be pleased’ he thought to himself.

Two weeks later

Stacy sat in the break area wearing a large sized mans beige overcoat that was fully buttoned. She sipped coffee and waited. At the appointed time Stacy picked up a manila folder and went to the office and paused in the open doorway. Jan and Benny were sitting at a meeting table and were in midst of a discussion. Seeing Stacy they stopped and beckoned her in.

Jan: “Hello Stacy, please come in and have a seat. We’re anxious to see what ideas you have.”

Stacy placed the file folder on the table and took a seat in a lady like manner.

Benny: “We want to see the designs you brought us. You may want to take off that hot overcoat before we get started.”

“Stacy: “I think you’re right.” Stacy made short work with the buttons on the overcoat. She opened it but did not take it off.

Stacy began: “A motif reset will call for an extreme change if you want maximum results. You’ll need to be bold.” Picking up the folder she continued, “I did research and I did drawings. They’re pretty good. But as the old saying goes “a picture is worth a thousand words.” With that in mind here is your new mountain meadow motif uniform.” Stacy stood up and let the overcoat fall to the floor, exposing the new uniform.

Stacy remained still to allow Jan and Benny to take in the full effect of the proposed new uniform. Stacy turned a quarter turn left and then right. Doing a 360 turn around Stacy made sure to flutter and rustle her petticoat.

Stacy was wearing a blue and white gingham waitress outfit with short puffed sleeved shoulders. It included a starched white linen apron with lace trim and front pockets. A snug, front laced bustier pushed up and emphasized her pert breasts.

“A good cleavage means good tips” Stacy volunteered.

The attractively short dress ended about four inches above her knees; a starched, white crinoline petticoat, with ruffled hem, gave the uniform the girly flair that Stacy envisioned. White knee socks, black patent leather Mary Jane shoes with a one inch platform heel completed the uniform. Stacy’s long platinum blond hair framed her pretty face perfectly. Stacy’s bright blue eyes matched the blue sapphire drop earrings and the blue gingham of her dress. Her long, dark eye lashes added to the illusion. A blue sapphire ring on her slender finger accented everything. Blue nail polish was on her beautifully manicured finger nails. Stacy’s makeup was impeccably perfect as were her classic arched eyebrows. Stacy definitely matched the image of a foxy looking serving wench; or a very sexy Alice in Wonderland. All these details helped “sell” her idea.

Stacy: “You want mountains, you want change and you want customers. This outfit will do all that.” Reaching into her apron pocket Stacy took out a pen and an order pad. “May I start you off with some coffee or beverages?” as she pretended to take an order.

Jan and Benny were staring at Stacy. In unison they both said “Wow!”

Stacy did another slow turnaround, fluffed her petticoats and curtseyed. “Hear that sound? Hear that rustle? So will our customers. We’ve got the visual image AND now we have the audio reinforcement to go with it.

Jan: “My god, you look perfect! This is the exact look that we could go with. Don’t you think so dear?”

Benny: “It’s spot on! You look so… so…, eh…” Benny was almost drooling. His interest in Stacy’s costume is apparently more than a passing interest. Ben was envisioning how he would look in it. He felt a bulge of approval begin to rise in his pants.

Stacy: “Sexy, right?” Stacy noticed Ben’s eyes move between her bodice, her crotch and the top of her thighs.

Jan: “Yes, sexy.”

Stacy: “Jan, I have all of your measurements and I brought a perfectly fitting uniform for you to try on. Do Ben a favor and put it on. He’ll thank you. With your legs and that starched petticoat you can’t go wrong! Add the bustier and smile. After you put it on I’d really like you to come with me and wait on a few customers. The experience will help you… and Ben… decide.”

Jan: “An extra uniform? What a great opportunity. I would be stupid if I didn’t give it a try.” Jan quickly left to fetch the uniform.

With Jan out of the room Stacy said, “Ben, give me a week and I can have a uniform that would fit you perfectly. You have to start sometime. I see a look in your eye that I recognize.”

Benny blushed. “No, I don’t think so. Not right now.”

Stacy: “If I was a betting girl I’d guess that you’ve worn your share of panties before. I’ve seen them on you here at work when you’ve bent over, knelt or reached high. Your pierced ears are no secret. I’d also bet that you have a stash of girl clothes and cosmetics at home and that Jan helps you with your makeup. It’s good to have a hobby.”

Benny: “What are you talking about? Of course I appreciate nice clothes but that doesn’t mean that I’m a …a cross-dresser… a transvestite!”

Stacy: “That’s true but the left over nail polish at the base of your cuticles on your well shaped finger nails leads me to believe you at least have a more than a passing interest in girly things. You also need to get a better eyeliner and mascara remover. I’ve noticed that you usually leave subtle traces. You worry about cross-dressers? I think there’s a little sissy in most people. Don’t you agree?”

Stacy: “Let me know when you’re ready for your uniform. It’s waiting for you. You’ll look cute! I’ll toss in an extra petticoat or two. I’ll even give you a makeover if Jan will let me. You’d look fantastically girly. Would you like that Ben? Would you like to look sexy?”

Benny looked like someone had hit him in the stomach.

Jan’s return interrupted their conversation. She had opted to add a bright red lipstick before re-entering the office. She too looked amazing in the new uniform.

Benny: “That outfit looks so hot! The petticoat was John’s idea… I mean Stacy’s idea.”

Stacy: “Jan, let’s test the uniform. Let’s wait tables for the lunch hour. You check the customer response and the functionality of the uniform.”

Jan: “This dress is so fun. I feel young and decadent. It gives me such a thrill that I’m wearing it home! Benny, you’ll love the way the bodice fits and the petticoats flare!”

Stacy: “I was just telling Benny the same thing; that she should have her own uniform. She definitely has the legs for it.”

There was no reply to Stacy’s comment or to her mixing of gender terms. Ben returned to his office and the 2 girls went to wait tables and put the uniforms to a real life test.

45 minutes later… after waiting tables

Jan: “I have to admit that our new uniform with the shorter hemline and other enhancements definitely look sexy. The crinoline petticoat creates a cuter image. Stacy loves her petticoats! Pockets in the apron are convenient. The other waitresses will like it and so will the customers. And it’s fun to wear.”

With Ben still in his office Stacy leans forward and speaks quietly to Jan.

Stacy: “I’m glad you like it. I built it from the bra outward. It took me awhile to conceive the look and then a few days to make it really happen. Benny likes it too. I sense that he would like to try it on. I know that he indulges in wearing female clothing and makeup. I saw a blue pair of panties on him when he bent down to get some supplies in the stockroom shortly after I started and I’ve seen other tell tale signs.”

Jan looked startled at Stacy’s revelation. Jan shuffled her feet and looked around avoiding eye contact with Stacy. There was no denial.

Stacy: “Don’t worry about Benny being outed by me for being a cross-dresser; it takes one to know one. There’s nothing wrong with men liking petticoats and pretty things. I think there’s a little sissy in most people. Don’t you agree?”

Jan stared at Stacy. It looked like Jan was going to say something but didn’t. Again there was no denial.

Stacy: “It’s just a matter of time before either you or Ben asks for a uniform for him. I think you should make it happen for him. Take the initiative. Imagine how excited he’ll be to see our new waitress uniform waiting for him on his side of the bed. Be sure to place a new tube of lipstick on top of his uniform. It will show him your support. Think of how happy she’ll be to wear the dress and flutter her petticoats. And there may be a reward for you by making it happen.”

Jan: “I’m afraid he’ll freak out.”

Stacy: “There’s something to be said about a nice fetish to keep the winter nights a bit warmer.”

Stacy: “When you place your order I’ll add a couple of starched petticoats purely for added arousal reasons. Neither of you will regret them. Everyone should have some rustle in their bustle, right?” Stacy quipped.

Benny called Stacy and his wife back into the office. They all took a seat.

Benny: “Jan and I agree that showing us the real thing like you did was much better than just looking at drawings and photos. It was a great idea. It took a lot of confidence to wear your presentation. You brought the uniform to life and, in a way; you brought me to life too.”

Jan: “We’re definitely committing to the new uniform.”

Stacy provides more suggestions

Stacy: We given customers an audio experience with the petticoats, we’ve provided them a visual treat with the uniform, so why not give them olfactory stimulation too? There needs to a subtle pleasant smell, like cinnamon buns in the oven. You can pump it in, light a candle or actual bake things. It can’t hurt you and it will make us unique! You and Jan need to pick a very subtle scent.”

Stacy: “If you want to increase money streams for the diner consider opening ‘by appointment only’ cosmetology services. Do it on site or offsite. It would set us apart from others. I think we could make it work. My big sister has her cosmetology certification and I’ll have mine soon.”

Leaning forward as if confiding to them Stacy expanded on the idea of a beauty operation. “We could add offsite special services and makeovers for cross-dressers and trans people. It could become a retreat and day spa. If you offer a safe, nonjudgmental haven for those in need people will come. No one is offering such a thing within 50 miles of Wrightwood. There IS a market for these services, wouldn’t you agree Benny? I think that ‘sissy’ can be a harmless lifestyle, don’t you? My sister and I could put our cosmetology certifications to good use.”

Jan: “I’m so excited about the possibilities. Ben and I need to do some deep thinking. We’ll meet again soon, clarify a few things and see where we go from here.”

Stacy did her ‘Fatal Instinct’ leg crossing maneuver, leaned back in her chair and said: “I have one question. What is Benny’s femme name?” There was no reply.

Jan: “You presented interesting things to consider. We’ll get back to you in a while.”

Stacy: “No problem. I’m easy to find.”

Stacy picked up her purse and left.

Four hours later Stacy’s cell phone alerted her to a text message. It was a one word message from Jan’s phone. It simply said “Bethany”. A moment later another message buzzed in. “Order Beth a uniform”. Stacy smiled and hit the ‘save’ button. ‘You never know when this information might come in handy.

Another meeting: 2 weeks later

Benny gave Stacy a one week advance notice about another important meeting. Benny said that he and Jan wanted to discuss a few more things with her but did not elaborate further. She was asked to be there at 10 AM on a day that she was not scheduled to work. It seemed a bit odd to Stacy. Was she going to be fired?

Vowing to make the best of it Stacy wants to make a good impression. She also vowed that she would not cry if she was terminated. Stacy arrived 20 minutes early and waited in the employee break area until it was time. She was dressed for success.

Stacy’s makeup, as always, was impeccably perfect. She sported long dark eye lashes, classic thin arched eyebrows and tasteful eye makeup. Taylor Swift Red lipstick brought attention to her pouty lips. Stacy always wore a subtle musk perfume. Her long platinum blond hair style framed her face perfectly.

Stacy made the choice to show Ben and Jan a different side to her fashion sense. She selected a pretty, form fitting, yellow pencil dress that ended 5 inches above her nylon clad knees. A yellow garter belt held her shear ‘Suntan Beige’ stockings up. French nails from her favorite salon were a perfect accent for her outfit.

Pearl studs dressed her ears. Stacy wore the blue sapphire ring and necklace set that accented her blue eyes. Nylon stockings made her legs look smooth and tanned. Yellow open toed pumps with a 2 inch kitten heel were perfect for her ensemble. Stacy carried a yellow clutch purse and tortoise shell ‘movie star’ sunglasses. A Victoria’s Secret pushup bra emphasized her chest.

The office door was open when Stacy arrived at the requested time. Benny and Jan greeted her and asked her to be seated. Stacy made a point of taking her time in walking to the chair so Benny and Jan could absorb her professional woman look. The three exchanged pleasantries and Stacy sat down, again smoothing her dress beneath her.

Jan: “I want to tell you how beautiful and attractive you are. Your makeup is always perfect. You carry yourself well. You have a ‘presence’.”

Stacy: “Thanks, Jan. I always do my own makeup but my big sister helps me out with some things. A girl can’t do it all by herself all the time.”

Jan: “I have to admit that our new uniform with the shorter hemline and everything else you suggested definitely looks nicer. We are going to go with it. Adding a crinoline petticoat creates a cute image; a very nice touch. The other waitresses like it, I like and so do the customers.”

Stacy: “I’m glad you like yours. I’m sure Bethany likes hers too.” Jan blushed.

Benny: “Stacy you have done well over the months. You have solid ideas and Jan and I respect your work ethic. And our profits have gone up too.” Benny stood up and closed the office door. Benny sat down nearer to Stacy and Jan.

‘Oh, god… am I about to be fired? Why the secrecy?’ Stacy wondered.

Benny:”Stacy, I have good news and bad news. We are NOT going to re-brand our diner. Instead Jan and I have bought a second restaurant. It’s called the Grizzly Café and is located in Wrightwood about an hour away from here. It has all the elements we’ve talked and dreamed about.”

Stacy: “Wrightwood? That’s in the mountains, right?”

Benny: “It’s small mountain community at a 6,000 foot elevation. There are lots of pines trees and fresh air. It snows in the winter. In the spring and summer there’s camping, fishing and hiking. The Pacific Crest Trail runs through town. What’s not to like? It’s a lifestyle that Jan and I are looking forward to. It’s secluded enough that a person could walk around nude and nobody would know or care.”

Stacy: “It also sounds like a person could even walk around in a waitress uniform and no one would know or care, right Beth?” Benny shifted his gaze and said nothing. Everyone knew that Bethany had had her uniform for a month already.

Jan: “The Grizzly will have the mountain theme we spoke of. There will be lots of pine cones, deer antlers, sleds and skis on the wall; a mountain village theme. Besides selling food we’ll also sell rustic items and art. There will be old skis, sleds, bear themed salt & pepper shakers, gingham aprons, rusty saws with paintings on them, post cards, etc. This is a great opportunity for everyone!”

Stacy: “So it’s like a Cracker Barrel restaurant?”

Jan: Yes, it’s like a bit like Cracker Barrel but with a Mom & Pop local’s eatery vibe.

Stacy: “Have you considered changing the name of the place?”

Benny: “Why would we do that?”

Stacy: “There are several advantages to changing the café’s name. Add one word. Call it ‘Beth’s Grizzly Café’. Beside the most obvious reason to change the name is that by adding a woman’s name at the beginning it softens the name AND implies home cooking.”

Jan and Benny looked at each other as if a deep secret had been revealed to them.

Ben: “That’s a concept that would cost very little and could work to our advantage. Let us consider our options.”

Jan: “Beth and I want to back away from the business a little and start enjoying life. Beth’s brother will run ‘Benny’s Diner’. We’ll run the new place. We’ve been slaves to the business and we think that you could pick up some of the duties we do. We can use help. It will be a challenge.”

Benny: “We want you to help us get it up and running. This will mean a raise. You’ll need to move to the area like we are. You need to live local. Bethany and I bought a nearby four bedroom house on a 1/2 acre of land surrounded by towering pines. We have a 3 car garage. There’s also a cozy two bedroom rental house in the rear. It’s on Blue Bird Lane. It snows in the winter and there’s a ski resort a few miles away. Skiers like to eat.”

Benny: You know our menu, you know our goals and we know your work ethic. We also want you to hire and train the wait staff. Reduce turnover. Make the place run smoothly and make us all money.”

Stacy: “That sounds very nice but how does this impact me?”

Benny: “If you agree to join us we’ll give you a raise, give you a percentage of profits and let you live in the guest house at a reduced rent. You could walk to work!”

They reached mutually beneficial arrangements on everything to do with the new diner. Stacy became part owner, had a comfortable salary and a cheap place to live. On a similar note Bethany, Jan and Stacy made a similar mutually agreed upon arrangements regarding other things.

The meeting ended and Stacy said that she had another, non-business, suggestion. Jan and Beth listened intently.

Facing Bethany Stacy quietly said, “For some variety Beth should change out the white knee high stockings of her waitress outfit and experiment with black or white nylons. Maybe add a cute garter belt for special occasions…maybe have the garter straps visible for an erotic touch. I like the look and feel of hose on my legs.” Pulling up her sundress enough Stacy exposed a yellow garter strap attached to her shear ‘Suntan Beige’ stockings.

Jan, Benny and Beth smiled in approval. By reflex Beth reached out and fingered Stacy’s nylons. Beth gave a gentle tug to check the tautness of the strap. “Your garter strap has cute bows where they clip to your stocking!” Beth blurted out.

Stacy: “I like the way straps tug when I walk… they remind me of… of an old boyfriend.”

Stacy took a moment to visualize Bethany in a lacy red garter belt with her engorged cock sticking out and framed by the petticoat of her waitress uniform; framed as if Beth was offering her cock to Stacy. She smiled at the mental image. A stirring began in Stacy’s panties as she envisioned herself kneeling and taking Bethany deep into her mouth. Stacy fantasized that she could feel the heat of Beth’s cock as it neared her lips. She imagined a penis texture on her tongue. Stacy wanted to leave red rings all over Beth’s shaft. Shaking those thoughts out of her brain Stacy made mental notes: no sex with management and she must have sex soon. Maybe Rhonda would be at home. Maybe Kenny would answer his phone.

Benny looked at Jan and made a subtle affirmative nod indicating that garter belts and stockings were a good idea. Their meeting ended.

Weeks later they had all moved to the mountains and made the diner operational. Time passed.

“Beth’s Grizzly Café” had been open for almost six months – the story goes full circle

Rhonda and Sissy had only visited a couple of times. Rhonda came up one time by herself and spent the night. Stacy was feeling lonely and needful.

Stacy reunites with Bonnie and Connie

Stacy watched the dusty blue SUV pull into Beth’s Grizzly Café parking lot. She watched as the passenger and driver kissed. ‘How sweet,’ Stacy thought. ‘What a nice couple’ Stacy thought. The short one was wearing a cute jumper. It was the taller of the two that Stacy fixated on. She was pretty in a handsome way; she looked fit, athletic and attractive.

As the two got closer to the café entrance Stacy’s heart skipped a beat. It appeared the couples were two women! Or were they? ‘I bet the taller one is the “top” in their relationship,’ Stacy mused. ‘Very intriguing,’ Stacy thought. Were two kindred souls about to walk into her work place?

Stacy quickly walked over to the café’s hostess and said, “Linda, we have two customers about to come in and I want to wait on them. Put them in my section in the big booth by the front window. I’ll be right there.” Linda just smirked and nodded her head. She gave Stacy the thumbs up signal.

Stacy dashed into the restroom, took her lipstick from her apron pocket and touched up her burgundy lips. Peering into the bathroom mirror Stacy fluffed her hair and her petticoats. Stacy’s pulse increased as she pondered how to best handle the moment. “Dang, the tall one sure is cute” she said lamented.

Hostess Linda greeted Bonnie and Connie and walked them to the large booth that Stacy had specified. The couple slid into the booth. Their matching Raven Red Maroon nail polish glistened. It appeared that their lipstick matched their nail color. Bonnie took off her sun hat and ran her fingers through her shaggy blonde hair, exposing forgotten pearl ear studs. Connie shifted her sunglasses to the top of her head. Linda handed them menus. “Your waitress will be with you shortly.” Linda sort of smirked and added, “I think you will find her very pleasant.” Linda returned to her hostess station.

As Stacy exited the bathroom Linda motioned her over and softly said, “You’re in luck. Your customers are not women…yet.” Stacy’s smile broadened.

Stacy returned and sat the girl’s drinks down. She was just about to write down their food order when she hesitated. Bonnie and Connie looked up. Stacy said, “I was thinking that I may have seen you two before… maybe a few years ago. You look familiar. Did you or your girlfriend attend South Hills High?” Bonnie nudged Connie under the table and in a mocking tone said, “Nobody will recognize us, right?”

“Yes, we both went to South Hills High. Why do you ask?” Smiling broadly Stacy replied,“My name was John Miller. I saw you win the beauty pageant in your senior year! I spoke to you afterwards. You told me I should be true to myself so entered the contest the next year and I won first place!” Doing a 360 degree turn around Stay fluttered her petticoats and said, “Look at me now: my name is Stacy and I’m part owner of this place!”

This is how Stacy was reunited with Bonnie and Connie whom had won the Womanless Beauty Pageant the year before Stacy won. It was random happenstance that brought the three together at Beth’s Grizzly Café in Wrightwood, CA.

Before Bonnie and Connie left Beth’s Grizzly Café Stacy extended an invite. “Did I mention that I live in town on Blue Bird Lane? It’s a two bedroom house. I’m off work in 45 minutes. Maybe you would like to stop by? My walk-in shower can easily hold three people. I have a petticoat collection that I think you’d both love to see… or try on. Having a sissy as a friend isn’t a bad thing. Everyone should have some rustle in their bustle, right?”

PS - Does Randy Rhoda rate a spin off story? Does Stacy?

PPS - “Pretty Stacy” is the work place safe story where Bonnie and Connie accept Stacy’s invitation to stop by her house. “Pretty Stacy” is ‘work place safe’. Give it a read. “Pretty Stacy” was posted 4/25/2019.

Stacy, the waitress character mentioned here, was introduced in the last few pages of ‘High School Reunion: Bromance on Pacific Crest Trail – Chapter 3’. Reading those last few pages will add to your understanding of Stacy in general. ‘Bromance’ spawned a second story called “Pretty Stacy”. There was enough interest and curiosity about Stacy that caused THIS story, “Pretty Stacy: Beginnings” to be written.

Below is a concept image of what Stacy’s uniform looks like. They are similar but the actual version is better! Some would say it has more flair. Ask Bethany.

85409-rebel-alice-wonderland-costume-dress-900x900.jpg

Who is Stacy?

Stacy’s first appearance was in the last few pages of High School Reunion: Bromance on Pacific Crest Trail – Chapter 3 of 3 where she was working as a very cute waitress in a small mountain town. Stacy was such an interesting character that she deserved her own story called Pretty Stacy. That story necessitated Pretty Stacy: Beginnings to explain how Stacy evolved to being Pretty Stacy; it shows her becoming empowered and confident. She is referenced in “Girls” for the Summer Club next. Which brings us to Stacy’s most recent story (“Girls” for the Summer Club 2 – A sister’s revenge).

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Comments

A sissy with balls

laika's picture

Even though Stacy calls herself a sissy she's nobody's doormat. She knows what she
wants and doesn't want in life, and in sex, where she's not just some passive plaything,
more like an eager play-partner with people she likes. The girl definitely has a healthy libido. and a knack for finding others like herself and bringing out the girl inside them ("You queered my boyfriend!" LOL!)

I liked her character in Bonnie & Connie's Pacific Trail Bromance and in Pretty Stacy,
so I waded through the few parts of this I didn't like so much and was glad I did; Learning her whole
backstory and how she wound up working at the Grizzly Bear Cafe in that adorable outifit...

What parts of this didn't I like? I liked the mentorship her sister provided
and the love between them, but some of what Sissy + Stacy did
together sexually was way too incestuous for my taste.
But hey it's only a story, I'll survive...
~hugs, Veronica

My longest posting

Donna T's picture

I struggled with the incest part too but then Sissy asked a favor... and Stacy asked for a favor in return... and I went to the darker side of things. The length of the story kept growing & I didn't want to break it into a multi-part. Stacy's 'self liberation' & confidence, based on a sexual awakening, was interesting to explore. Getting her to reunite with Bonnie & Connie was key. I was trying to tie in a couple stories. It was a real process for me!

Some characters in any story standout & are memorable... you wonder 'what if'. Beth & Randy in this story intrigue me. Retiree Lindsey/Lyle in "Rose Bud", Wiley/Wanda in "Cam-eo Performance" are all interesting to me as is Maddie in "Acceptance". A skiing/hiking excursion with Connie, Bonnie, Stacy could also be interesting.

You have substantial tenure with BC. Thank you for your ideas, comments and private messages are appreciated.

Regards,

Donna

Never Had A Chance

joannebarbarella's picture

John was destined from birth to become Stacy. Ignatius Loyola reputedly said " give me a child until they are seven and I will show you the (wo)man". John was Stacy forever after. She is much more than a sissy. Even though she has male appendages she is actually all woman.
I can only wish that I had been raised as she was.

Thanks for the comment

Donna T's picture

JB, Sorry about my slow reply! I appreciate you taking the time to comment.

I Googled " give me a child until they are seven and I will show you the (wo)man" Aristotle gets one credit for the comment but Ignatius Loyola got more credit!

Thanx again,

Dee

Donna

Stacy

Donna T's picture

Stacy pops up in a few of my stories; toward the end of Bromance, again in Girls for Summer stories and the Stacy stories. She's a most memorable cutie!

Donna