For as long as I can remember I was infatuated with my Auntie Celeste. Who wouldn't be? She was a gorgeous, sophisticated lady who always looked perfect--long, wavy auburn hair matched by long, shapely legs, an hour-glass figure, dark smoldering eyes enhanced by mascara and eye shadow, and ruby red lips. I was often alone with her, even as a child, and when it was just the two of us, she would always lounge around her apartment, wearing full make up and spectacularly sexy lingerie from baby doll negligees with hemlines right at that most delicious spot where the buttock meets the leg, or long, satiny gowns with slits up to her womanly hip.
My family lived on a farm in the country. I could never imagine how my mother and Auntie Celeste could be sisters because they were complete opposites. Whereas Aunt Celeste was the very picture of confidence, success, beauty, and sophistication, my mother was mousy, plain, shy, and socially and physically awkward. Unlike other boys who went to summer camp and family vacations, I spent all my time when not in school with Aunt Celeste.
My parents labored all the time on the farm and never took vacations. I think everyone in the family recognized from an early age that I had a special affinity with Aunt Celeste and was happiest in her presence and that I really didn't belong on the farm. I was not like the other farm boys, big strapping lads who liked to rough-house and get sweaty and dirty.
I was small and timid and preferred being indoors. When the other boys were out playing or working, I stayed in the house longing for Aunt Celeste. I would spend hours gazing at the framed photos of her I had in my bedroom and counted the days when I could join her on spring break and summer vacations. I was sort of a cross between Mom and Aunt Celeste.
Although I was a boy, I was beautiful like Aunt Celeste downright pretty, long lashes, full lips, a cute face, but like my mother, I was shy and submissive.
Auntie Celeste had a bossy streak and when I was with her I quickly fell into the role of house-boy servant. We made a great pair. She really would not lift a finger when I was there. She might be sitting on her bed within easy reach of a nail file on her bedside table, but she would call me to hand it to her. And, wherever I was, whatever I was doing, I would run to her, thrilled to be able to serve her.
In time, she would extend her long, tapered fingers without a word and curl her index finger in a "Come to Aunt Celeste" signal, and I would come to her, hold her graceful hand, and file and buff her nails. I would give her manicures and pedicures as well, being very, very careful to paint her nails with the little brush, so not the tiniest wisp would blemish the flesh of her perfect toes and fingers, and blowing on her finger and toe nails to dry them. Aunt Celeste would not even pick out her own panties and bras, but would direct me to her underwear drawer to select her intimates.
This, of course, allowed me to feel all the silky and lacy sensations, to enjoy the perfumed aroma of her panties, and to grow envious that ladies could wear such lovely things next to their skin but that boys were supposed to be denied that pleasure. As summer vacations passed and I grew older, my feelings for Auntie Celeste only grew and deepened.
Aunt Celeste was not married, but had an active social life and frequently went on dates and sometimes entertained her lovers back in her flat, even when I was staying with her. Aunt Celeste always let me help her get ready for her dates, allowing me to help roll silk stockings up her long, shapely legs and to fasten the tops to her garters resting on her soft thighs.
I would kneel at her feet and slip her feet into her high heels. As she sat at her vanity in bra, panties, garter belt, stockings, and heels, she would apply her make up and allow me to brush her long, thick, auburn hair. She also allowed me to spritz her with perfume and when she was feeling playful, she would spritz me with her perfume as well.
Left alone for hours while she was on her dates, I would sit at Aunt Celeste's vanity and apply eye shadow, mascara, rouge, and lipstick to my face. I would look at my pretty face in the mirror, seeing what a cute girl I would be and then I would practice making sexy faces, pouting my lips, licking my lips, batting my long eye lashes.
I would lavish Aunt Celeste's perfume on my neck, slip Aunt Celeste's camisoles and thongs over my slim body, put my feet in her high heels and walk around the flat, practicing how to sway my hips like Aunt Celeste. It didn't take long for Auntie Celeste to discover my activities.
On my birthday, Aunt Celeste gave me my very own make up kit. She taught me how to apply eye shadow and mascara and took a real interest in my use of cosmetics. From then on, I always wore make up when I was with Aunt Celeste, glossy lip stick, nail polish, rouge, and eye shadow.
Also, when she grew bored of her panties or lingerie she would "hand them down" to me. It gave me such a thrill to wear panties that I knew had graced Aunt Celeste's most private silken moist treasures. It would always make my little willie grow hard whenever I slipped on her panties. She even let me wear her bras, which I stuffed with her silky underthings to give me a womanly figure. Aunt Celeste was bossy, but she was also affectionate.
She would let me cuddle with her to feel her warmth, to breathe the heady aroma of her perfume, to feel the softness of her skin. I grew my hair to shoulder length, and Aunt Celeste and I would brush each others' hair.
My parents realized that I was unhappy on the farm and repressed in terms of the person I wanted to be. After much discussion, my parents and Aunt Celeste agreed that I would move in with her when I turned 18.
I counted the days until my 18th birthday, and dreamed and fantasized about my life with Aunt Celeste. When I moved in with Auntie Celeste, she had already prepared a bedroom for me. The walls were pink, and it had a frilly pink canopy bed, and I now had my very own vanity with a mirror and fully stocked make up kit. I opened the most lovely presents: silky lingerie, the tiniest, sexiest little thongs, and high heels in my size.
Aunt Celeste also started me right away on "ladies vitamins," pills that I later found out were not vitamins at all but female hormones that would prevent me from growing hair on my face and body and which made my breasts start to grow and swell and my skin to be soft and supple as I developed a sheen of feminine body softness at a time when other boys were developing hard muscles. After moving in with Aunt Celeste, I changed my name from Jimmy to Kimmy.
Auntie Celeste insisted that I always wear high heels because she said they made my legs and bottom look beautiful. She taught me how to do the runway strut of fashion models to maximize the swish of my hips as I walked. I noticed that when I walked outside with a tight mini skirt that men would turn their heads and stair at my cute bottom as I walked by. It made me feel so sexy and desirable. But I rarely went out.
I mostly stayed at home to serve Aunt Celeste. Aunt Celeste and I had an amazing bonding experience. She was beginning to feel her aging and decided that she wanted a boob job. Aunt Celeste schedule me to have breast implants at the same time. We went into surgery together and helped each other through the painful recovery period. We both now proudly possess beautiful, full, perky breasts topped with ever erect, ultra sensitive nipples.
With my set of beautiful breasts, I enjoyed the extra attention of men and I loved flirting with them, and how girly I felt when men were attracted to me. But I remained attracted to women as well. Aunt Celeste got very jealous whenever she noticed me "checking out" a pretty girl or caught me flirting--or even talking--with a female.
She wouldn't hesitate to break into a conversation and order me to follow her away immediately, even though it was rather embarrassing. But I always obeyed her because more than anyone else, I was hopelessly infatuated with Aunt Celeste and could not resist her beauty and her dominant strength.
Aunt Celeste and I both found that we liked it best when I was at my most obedient. She would wiggle her finger in a beckoning motion, and I would crawl on my hands and knees to her. When she was in the mood for being pleasured, I learned to follow her silent commands; a snapped finger, an arched eyebrow, was all I needed to start servicing her with my tongue.
I would lick her clitoris until my tongue would ache so much I thought it would fall off, but I would stick with it until Aunt Celeste would reach orgasm, push my head away, and close her beautiful legs. Auntie Celeste never touched my penis or over showed any interest in having me make love to her as a man to a woman, or even in giving me sexual pleasure.
I learned to subjugate my own pleasure, realizing that giving her pleasure was all that mattered. I would have plenty of time, later, alone, to fantasize about Aunt Celeste and to satisfy my personal needs. Before long, Aunt Celeste and I engaged in more cosmetic surgery, narrowing and feminizing my nose, getting lip augmentation implants so my lips would be full, juicy, and lush, as well as electrolysis to permanently remove my body hair.
Aunt Celeste also encouraged me to dress in sexy clothing.I loved dressing up in a French Maid's outfit when I cooked and cleaned for Aunt Celeste.
I did all the housework wearing stiletto heels, black nylon stockings over my perfectly shaved legs, a frilly mini skirt that showed off my pretty round girly bottom, especially when I was on my hands and knees scrubbing and polishing the floor.
The maid's uniform would be cinched tight at the waist and had a built-in push up bra that made the most of my luscious breasts. My creamy soft feminine shoulders were bare and my long hair swayed across my shoulders as I dusted. Even when I was alone in the house cooking and cleaning I always wore full make up, blue eye shadow, mascara, rouge, and lipstick. I had to be ready in case Aunt Celeste brought home one of her boyfriends, so I could be ready to serve them wine, hors d'oeuvres, and dinner.
I had to be ready when Aunt Celeste snapped her fingers.
My obligation was to anticipate her every desire so she need not articulate a command because I had already met her need, whether it was to fill her glass or make her date feel more comfortable by kneeling in front of him and taking off his shoes and putting a pair of slippers on his feet.
Although Aunt Celeste was intensely jealous of any interest I showed in other women or them in me, she encouraged me to flirt with her man friends and showed no jealousy at all with respect to their attentions.
I learned how to bat my long eyelashes at them when I served them drinks, to make little curtsies, the better for them to enjoy the sight of my cleavage, and I always gave my hips a special extra wiggle when I knew they were watching me from behind. I took every opportunity to lightly touch their arms or to brush against them.
Her dates invariably asked about me, and Aunt Celeste would tell them the story of how she inherited her farm-boy nephew and turned me into her beautiful young niece. Her boyfriends were usually initially shocked, but also intrigued and I would notice for the rest of the evening that they would keep stealing glances at me. It made me feel so sexy to see their eyes devour me and I tingled as I sensed their desire for me. The evenings would progress in any number of ways. If the date was not up to Aunt Celeste's standards, often because they failed the "Kimmy" test by being uptight about me, she would summarily dismiss them and Aunt Celeste and I would finish the evening together (more about that later), but if the man was one who Aunt Celeste was attracted to, he would likely spend the night enjoying her charms.
At the least I would be close at hand, to attend to any needs they might have, which I daresay, also provided me with a voyeuristic thrill. If Aunt Celeste's date took an interest in me, she had various ways of introducing me into the evening's more exciting activities. One of my favorite ways she did this was by having her date help "get Kimmy ready for bedtime." Aunt Celeste would announce that it was getting late and that it was way past Kimmy's bedtime.
She would ask her date to unzip my French maid's outfit and to unhook my bra, then she would tell me to go get ready for bed and to come down for a good night kiss.
While I was upstairs changing, Aunt Celeste would usually be necking with her date and getting him good and hot.
I would change into a pink see-through baby doll nightie with a pink tie-at-the-side string bikini showing underneath. My breasts topped with my delectable nipples were visible under the translucent material. I wore clear high heeled slippers topped with pink fuzzies.
I put on high gloss pink lipstick and my neck and chest shimmered with sparkling pink lotion. I would come down the stairs and say, "Goodnight Auntie Celeste." With her boyfriend sitting next to her, I leaned over her to give her a kiss, which I knew would cause my nightie to fall forward, exposing my gorgeous breasts for anyone who might be wanting to sneak a peak.
I always lost my balance when leaning over to smooch my aunt, and my hand lands would on her man friend's thigh.
The man's natural reaction would be to catch me and I often managed to squirm in a way that would make his hand touch or even grab one or both of my breasts. If was not too obvious I would fall into his lap. At which point Aunt Celeste always said, "Maybe Daddy would like to give Kimmy a good night kiss, too." In my experience, very, very few "Daddies" passed up the invitation to kiss me. Realizing there was a good chance this was the first time most of these guys had ever kissed a girly boy, I made sure it was a really warm, sensual, delicious, kiss and did my utmost to melt in the gentleman's arms as his tongue explored the seductive warm wetness of my mouth.
If the kiss continued--and it usually did--I would run my fingers through his hair, to wiggle closer, and to moan.
Meanwhile, Aunt Celeste would sit close by, cooing, her eyes sparkling, clapping and encouraging the kisses to continue. Before long, she would join the kissing, and we would have three tongues and mouths playing with each other and we would never miss the chance to sandwich her boyfriend's face between our two sets of oversized breasts.
Before long, inevitably, boyfriend would be sucking my breasts like a man dying of thirst. Aunt Celeste would whisper encouragements in his ear while she played with his cock.I would be pressing against him panting and moaning. As his cock would get big and hard, Aunt Celeste would take over the kissing as I would slide down and start the cock sucking. This way the man would lose track of me as me, only feeling the sensation of my expert, sensual mouth on his dick while his conscious mind would be engaged with Aunt Celeste's tongue in his mouth, her beautiful face, his hands on her magnificent breasts When it's clear her boyfriends are totally aroused and close to coming, Aunt Celeste says, "It's really way past Kimmy's bedtime.
Let's go tuck her in bed and give her a good night kiss." I would walk up the stairs swaying my pretty butt highlighted by my tiny pink string bikini showing through the translucent baby doll negligee. Aunt Celeste would position a big bolster pillow across my bed and instead of putting it under my neck, she would have me lay face down with the bolster under my tummy causing my pretty, young, round butt to stick deliciously up high.
Then she would whisper the invitation, "Would Daddy like to fuck baby Kimmy's pretty little ass?" I would wiggle my butt in anticipation. She would whisper, "Kimmy needs a big strong daddy to make her his little baby doll." And, "Show me what a big,strong may you are." With rare exceptions, these macho, straight men would start fucking me with wild abandon.
I would make little squeals as Aunt Celeste would urge them on. Of course, I would feel gloriously hot and sexy, but, again, with impeccable timing Aunt Celeste would interrupt Daddy just before he would climax, cooing in his ear, "Save some for me, Daddy." Aunt Celeste would extricate her man from my tight buns and take him into her bedroom. I would be left to relive the evening as I would play myself to orgasm and drift into blissful sleep.
Other scenarios take place, of course. Sometimes, when her date does not meet her standards or gets cold feet, Aunt Celeste will put me to bed herself. She has a quite impressive strap-on dildo. When she's in the mood, Aunt Celeste can really give my tight little boy pussy quite a pounding.
However an evening goes, I remain completely devoted to Aunt Celeste. Although my boy pussy and my mouth are as experienced as any courtesan, I am still a virgin as far as my penis is concerned.
Don't get me wrong, I love bringing myself to orgasm as I fantasize about my Aunt Celeste, and someday I would love to make love to a real girl, but I know that my true fulfillment comes from making and keeping Aunt Celeste happy as her little girly boy slut.
When I do make her happy, I feel like the luckiest sissy on earth. Proudly signed, Willing Wimp