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The Introduction:
It was August 4th, 2000. Still under the influence of summer, the skies were clear, the suburb was quiet, and many of the people Leslie knew were on vacation. But Leslie, a boy turned man as he ventured into his 20s, decided to stay back with his parents to attend a prestigious university within his own city: North Marlow University of Science and Technology, or as some would say, NMU.
“Thank you for taking care of him, Jane,” Leslie’s mother spoke. It was only fair for both parents to take a vacation a little before Leslie’s first term began at NMU. However, Linda was not very confident in Leslie’s ability to take care of himself without burning the house down. While he could take care of himself, she did not want him staying completely alone, and so her neighbor was someone she could rely on, perhaps a trusted friend, one could say.
“Sweetie, Jane will come to check on you often. Please be respectful, understood?” Those were the words spoken with softness and kindness as she left her son for a short week of vacation with Leslie’s father, David.
“Sure, whatever…” Such reluctance. With the way he behaved, he wanted them to leave. Unbothered, he continued to spend time reading or listening to music. Silence followed as they left, and Linda went over to Jane’s house to thank her, leaving them behind as Linda and David departed for a well-deserved vacation.
But to know Leslie, one must understand the kind of young man he was. To truly know him, one must recognize the influences he had had, kept secret for decades. Until today, he found himself in moments of serenity, no judgment, and a life of peace. For once, as he breezed through the world of science, he would find a way to embrace who he was through the art of self-expression.
As he looked over at his window, he saw his parents departing from his neighbor’s door, walking across her lawn to their car, bags packed and ready for a break. He sighed, a gentle sign of relief, picked up his cassette, the record by Twisted Sister, Love Is for Suckers, and played “Hot Love.” He moved around, finally letting himself be a little free. He headbanged, his body jerking in directions odd for a man his age, his hips bouncing as his legs gently jumped in the air to the beat of the music. He sang at the top of his lungs and, for the first time in several years, he was finally able to learn what being fulfilled in his own desires felt like.
But for Leslie to partake in his own comfort, he hid himself in the old makeup of his mother to look and feel like the “rockstar” he had envisioned. He sang and lay in front of the mirror, pulling out a secret compartment of lipstick, a deep pink color that ran over his lips. He felt so true to who he was, unknown to what kind of person anyone would describe him as. He found comfort in the coloration of makeup, products intended for women, but somehow suited to him too.
He ran downstairs as he continued singing while he grabbed himself a cold beer. He noticed Jane tapping on his kitchen window from the other side, pointing to the front side of the house, his door. Leslie was startled, his drink almost slipping from his already sweaty hands. He placed the drink on the kitchen counter and rushed to the door. The music was faint but still audible from his room, especially when the door opened.
Jane spoke, “Oh my goodness, Leslie, the music can be heard all the way in my room. Please turn it down.” Her eyes squinted around his face and reached down to his lips. “D-did you… is that lipstick?”
But Leslie ignored her. “I’ll put the music down. Sorry about that.” He instantly scrubbed off the lipstick from his lips, and his eyebrows turned into frustration and anger, wondering why she would even ask or care about it.
As he closed the door, Jane stopped it. Firm in her voice, she continued, “Your mother said you have something to eat for lunch. However, she asked me to call you in for dinner. She’s afraid you’ll burn her kitchen down, so from this evening onwards, until they come back, I’ll be cooking and you will have to join me.” She paused for a reply from Leslie, her eyes widening, carefully looking at him and his reaction.
He replied softly, “S-sure, whatever. I’m going to, like, relax for a bit. See ya.” He left her as he closed the door on her, but somehow, she could not forget the color of his lips, the deep pink, the music. What was he on? What did he want to pursue, or what kind of thoughts did he venture toward? These questions, unanswered, had Jane puzzled, but she was curious. Once a noisy neighbor, always a noisy neighbor.
Leslie immediately went to close the window in the kitchen and rushed to his bedroom to wipe any lipstick off his lips with a tissue. He was unable to see himself so vulnerable in front of someone he barely knew, yet cared enough about their opinion. He lowered the music and decided to lie on his bed until lunch.
After several hours of reading and watching television, he finally found himself at her doorstep at 6 pm that evening. He rang the doorbell, and Jane welcomed him with a smile. “Oh hi! You came. Glad you decided to come.”
He replied softly, “Mmhmm, I was pretty hungry. I wasn’t a fan of what Mom made anyway.” He welcomed himself in as Jane turned her body to create space between her and the door. The elaborate gesture of showing her place with the extension of her hand made him feel like she had something planned. However, he didn’t mind, as he was there to eat.
“You’ll be glad to know I made your favorite, lasagna. I know your mother doesn’t make it often, so feel free to have as much as you like.” She smiled. Underneath her character, she truly did care about Leslie as a human being, in a way that he could express himself in ways other boys or men his age couldn’t.
As they sat for dinner, Leslie took the chair on the edge of the table while Jane sat in the middle like the queen she was. As Leslie indulged in the sweet, nectar-like dinner that quenched his hunger, Jane did not hesitate as she placed her fork down. “So, you like makeup, huh?” Leslie choked, drinking water while clearing his throat.
“Careful now.” She said in a slightly sing-song manner, placing the tissue box to his side. Leslie did not take it. Instead, he looked at his plate and softly said, “Th-they were for Halloween.” His lips closed, unable to digest anything further.
“Halloween is a while away. What kind of costume requires a boy like you to wear...” Jane paused, “makeup?” Leslie didn’t reply. She found his silence quite intriguing. She felt his body warm up. “Come on! Finish what is on your plate.” Leslie continued to eat politely. His naivety was catching up to him. Why didn’t he have anything to say? What if she caught on?
“Do you enjoy dressing up like those 80s hair metal bands?” Jane asked curiously. Her directness was to be studied with intensity, as she was piercing every needle into Leslie’s aching self. “I… I guess. I don’t know. I never tried it.” He paused. He was truthful, but not all the way true. “I have different shades of lipstick that might suit you.” Leslie’s voice hitched. “I… I don’t k–.”
“Don’t worry. Your mother doesn’t need to know. It can be our little secret.” Jane cut him off as she replied with firmness. She was curious how far he was willing to submit to her dominance, to turn him into a little doll.
“Maybe, if you’re interested, you can come a little early for lunch tomorrow and I can show you.” Leslie was once again quiet, but Jane wanted to know. “So? What do you say?” she followed up. “I’ll…” he paused, waiting for the tension in his bones to release for a second. “Think about it.” Jane replied with a soft hum. “Hmm.”
That very night, Leslie stared at himself in front of the mirror. He found himself with makeup: an old worn-out blush, an eyeliner that no longer had its integrity at the nib, and lipstick. The lipstick was the only thing he found comfortable with, the only piece of color he enjoyed against his body. He picked it up again and, elaborately and gracefully, ran it over his lips, smacking them and pouting. He loved it. He loved himself so much.
But his body yearned for more. His soft erections and gentle arousal were something he did not enjoy, since a woman did not find the stiffness of a cock placed between her legs. It was only with fire that she elaborated her sense into maddening moans and a cascading climax.
Leslie slept with his lipstick on, placing his cock between his legs and pretending that he had a flower, a pretty pussy.
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The Unravelling:
The morning was around 11:30 a.m. Leslie had knocked on Jane’s door, a soft knock, enough for her to notice but soft enough for him to wish she hadn’t. She came over and opened the door. “Oh!? You’re a bit early. I’m still making some chicken and rice, your mom’s recipe, but don’t worry, I’m adding my own spin to it.” She smiled as she continued to talk while going back to the kitchen for Leslie to close the door. “Close the door, honey.”
“Well, I’ve kept the chicken for a few minutes of simmering. It’s on low heat, so it should take another 15 minutes,” she said, looking at him. Leslie was quiet. He walked around her living quarters that merged with the dining hall seamlessly, with no wall separation. There was silence. Just then Jane started going upstairs, and she turned around. “So, are you going to come upstairs?” Leslie looked with curiosity, his eyebrows flaring up. He walked quietly and slowly, following Jane as she had already made it up to her bedroom.
As Leslie entered the room, he noticed her waiting for him on the bed. “Come on, sit.” She patted her bed, got up, and went to her dressing table. She picked a few things up and showed them to him. “So, I’m a bit of a nerdy girly when it comes to makeup, umm…” she paused, trying to look at the brands and discuss them. “So, this is M.A.C. It’s my favorite lipstick, a deep cherry color.” She looked at him. Her eyes followed his face, but her head stayed where it was, facing the lipstick. “I think you’ll find this to your liking.” She smiled slyly.
She continued, “The blush is from Sephora. The lip gloss, I believe, is from CoverGirl.” She went back to her dressing table and found another lipstick she liked. “This is slightly similar to yours. It’s from Lancôme, bubble gum pink. I like it. Guys tend to like it often too, haha.” She giggled while finally discussing the final piece of her arsenal. “And this is my eyeliner from L'Oréal Paris. I love this. It’s my second one. I use it often.”
Jane went back to place all of them in her pouch on her dressing table. She turned around. “So, anything that caught your interest?” Leslie was blushing, his cheeks flushed red. He was so shy yet so glittered with excitement that he wanted to try them all, but he ached, softly whispering, “I like the… pink one.” His face pouted. His eyes fluttered left to right and right to left. He rarely looked at her.
“Hmmm, I think I might use the lip gloss and the cherry-colored one. You’ll look… pretty.” She smiled, noticing his expression was all she wanted to know about what kind of boy he was. For Leslie, his hands clenched the sheets. “Aww,” she thought to herself. “He likes to feel pretty like a girl.” She sighed. Just then the alarm bell rang. “Well, maybe another time,” she said.
While she left her room, she continued, “Leslie, come on…” Jane paused for a few seconds. “I was thinking of going out this evening. Do you want to come out? It’ll be good to get some fresh air.” She said this while looking down at the steps she took to reach the kitchen.
Leslie was quiet. He barely made any sound. He knew how thrilling it felt to try putting on some makeup. He was close, and he yearned to have his body dressed in the same beautiful colors as a woman, or as a pretty young lady would. For it was this very decision that would reinforce the idea for Leslie that Jane was truly the person he could let his guard down with.
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The Purchase:
As the evening unraveled and the sun began to set slowly and steadily, Jane honked from her car, a slight brush-up on the paint job, but a beautiful Nissan 300ZX colored in teal green. It was a gift from her ex-husband post-divorce.
"Sweety?" she rolled the windows down to let the heat escape and the fresh air in. Leslie left his home, closing the door behind him and taking the keys with him. He was dressed normally: a regular pair of jeans and a t-shirt of his favorite band. It was no surprise that Leslie didn’t think much of this short trip to the mall; he even brought his cassette player just in case it got boring.
"Sit in front," Jane smiled, patting the seat next to her. Leslie invited himself and sat in the front as they drove to the nearest mall. Leslie was not very excited, but Jane, oh Jane, was thrilled beyond recognition. She even looked at him gently and bit her lips.
"You are doing great, you know that?" she tried to make small talk. "What makes you say that?" he replied. "I know you tend to be hard on yourself, the way you try to be and people don’t see it. But with me, you can be whoever you want, no judgment," she responded gently. She was vague on purpose; she knew anything more could short-circuit the young man into reclusion.
As they reached the mall and led themselves into an empty parking lot, they both walked. Obviously, Leslie followed and Jane moved further ahead. “Right, first things first, I need to collect something from a store, umm, just stay out for a bit.” She paused so as not to hint anything further, but while they walked in a surprisingly less crowded mall at the start of the evening, she made it to floor two: Victoria’s Secret.
“Stay here, I’ll be back, need to collect something.” She was firm in her words, so Leslie hung around a small cafe, imagining what was going on inside as he could see Jane pack a specific lingerie item he could not make out from afar.
Jane arrived in approximately seven minutes. “Come on,” she smiled as she walked over to another store. This time, Leslie was allowed in, a place for finding any accessories pertaining to women: clips, hairbands, wings, etc.
Jane looked around and smiled at one item she saw that was perfect for Leslie. As she picked it up, Leslie browsed other things like earrings and hair clips. She held the wig in suspension, aiming it at his head with her one eye closed, imagining how it would look on him, and it was perfect. She smiled. “Perfect.” She whispered, paying for it without Leslie noticing. Leslie was very quiet during much of these short endeavors. He observed and cherished knowing that someday he could simply buy them without letting anyone know his true desires.
“You want anything, anything to eat or drink?” she asked softly, her tone warm and giving. After all, she did have a beautiful surprise for him at her place. “N-no, it’s fine.” He looked away, trying to pretend that the places she had been were something he wished so badly to visit.
“I have one more stop, but it’s somewhere else, fifteen minutes away. After that, we can head home. I made your favorite again this evening. I know how much you love shrimps, so I was able to make you some shrimp pasta.” She smiled, excited for him to come home with her and try the many amazing goodies she had just gotten for him.
A deep breath sighed from Leslie’s face. His body burned in tension for reasons unknown. He was aware of what he truly wanted to get from the stores around him, and so, badly wanted to stay home and just dress up with clothes he had carved out with scissors, making his pants short, his shirts cut in half, and using some old lipstick. He wanted to feel the freedom, the worry-free look on his face, away from the judgments or ideas of others, especially now, especially this week.
As Jane and Leslie got in her car and drove, she made a stop a few minutes away at a store, a store that sold sex merchandise or peripherals. It didn’t take too long for Jane to come back. “Wait here, I’ll be back soon, sweety.” Around fifteen minutes in and out, she got herself a few items that might be the most revealing for Leslie.
“I hope I didn’t take too long,” she said, to which Leslie smiled, “I-it’s fine, you actually came a bit early, thirteen minutes to be precise.” She chuckled, “Look at you keeping time on me.” She winked at him and drove off to her home.
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The Dress-Up:
An hour passed. Leslie and Jane had arrived home. It was only a matter of time before Leslie would be softly decked in tones of beauty by Jane herself. It was natural that Jane realized how this was going to play out, especially for Leslie. She went upstairs by herself, placed things in an orderly fashion, then came down the stairs and halfway down spoke up, “Leslie, honey, could you come upstairs?” Leslie was sitting on the couch watching television to pass the time.
As he stepped on each stair, each pound felt like an unsolvable mystery about to be revealed to him. He was, and would be, getting into a persona that he could truly wear and be proud of. He entered the room unannounced and noticed Jane in just her underwear. His breath hitched, his body shivered. “I… I’m sorry!” He closed the door as his first instinctive motion. It was not right. This was not right!
“It’s okay! Come in.” She rushed to the door and opened it. “Come in, Leslie.” She held his hand and allured him into her room. “Sit.” Placing him on the bed, she noticed his cheeks flushed the color of red, like freshly plucked cherries. How perfect she was, and how shaken he was underneath the clothes he had on. He was quiet, not a peep, not a sound. His eyes wandered everywhere but in her general direction.
“I’ve got a few things for you.” She smiled as she announced the pleasures, she had gone through to get things for Leslie. She opened her first bag, and in it was beautiful pink lingerie. “I think you’ll like this a lot. Want to give it a try?” She did not hesitate in announcing what Leslie liked and didn’t like. She just knew, an intuitive feeling that was precisely hitting the right spot.
Leslie gasped, not in awe but in shock. “I… umm…” He was speechless, rightfully so. He was mesmerized by many aspects of the confrontation he was being faced with: the pretty pink lingerie, the fact that Jane knew about his true identity, the desires he wished to explore despite the uncomfortable nature of today’s world, and yet she was able to stir past them all and provide the most resilient hues of comfort for him.
“Go on, you can change in my closet if you’d like.” Jane was quite accommodating to Leslie. A small room with all her clothes was simply too good of an offer for Leslie to miss out on. He wanted to try it. He was given a chance. Despite his breathing getting heavier, the air gushing in and out of his nostrils, he got up from the edge of the bed, took the bag, and rushed into the closet. Leslie knew, he knew how this worked. He understood how every formation of the lingerie would be around him, and luckily everything captured his body perfectly.
He looked at himself in front of the mirror. “Wow,” he whispered. He loved every aspect of it. He finally felt at home in his own body for the first time in many years. It was finally happening. “Come out!” she exclaimed as Leslie took his sweet time admiring his own body. But as he did, as he entered the room with the soft white light, Jane smiled gracefully. “Oh, you look perfect. But we have a few things still to do, a few things you might enjoy. Come! Sit.”
Leslie walked back to the edge of the bed, and he looked gorgeous. The stockings covering his soft, tender legs, the balcony bra covering his chest, oh, it was perfect indeed. “Now to have you put this on.” She smiled, taking a wig out, blonde-colored hair that was softly placed over Leslie’s head. “Perfect!” His face glowed. Jane was impressed at how well everything was placed on him, especially the wig.
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The Cage:
Jane noticed something. As he got decked up, Leslie had invited something else too. A part of his body aroused in absolute ecstasy, his cock poking through the fabric below his waist. “I… didn’t know you’d get so excited.” Leslie blushed and looked away. “I’m sorry, it’s… I…” he stuttered. He didn’t know what to say as he thought of other moments that might stir him away from the excitement he was feeling at this very instance.
“It’s okay, but I don’t think a beautiful girl like you should have a boner, right?” Jane grew a little wicked with the thought. Her body heated up against Leslie’s, but as Leslie opened his eyes, he looked straight into hers. Those words, the idea of not having a boner, all of it felt perfect to the senses in his body. The crescendo to reaching peak excitement was not about having a hard-on, but about being a pulchritudinous woman. He whispered back to her, “I… I don’t like having a boner.” A confession masked in a plea for help?
“Don’t worry, we can fix that.” She went to the chair that harbored another item. In fact, it had two. She picked out one and placed it in the palm of her hands. Walking slowly, Leslie’s eyes followed, his breathing continuing to be elevated. “W-what’s that?” His eyes grew wider.
“Oh, this is a chastity cage. It helps control boners. Well, it prevents you from having one. I got this just in case. I figured you’d like it. A tiny cage around your dick, to finally feel like you don’t have an erection. After all, women don’t have erections, do they?” She paused. “Well, some do, but most women…” She smiled, biting her lips, “don’t.”
“May I?” Jane requested Leslie’s permission to touch him. He nodded obediently, like any good girl would. Jane noticed that his cock wasn’t very impressive. In fact, it wasn’t even that big to begin with. She ran her soft hands over his balls. “Mmhmm, you don’t have any girth or length. Kinda fits the whole persona you’re going for.”
Leslie’s body shivered. He wasn’t aware of the kind of power words could have. “I… I always wanted to be a girl.” Another confession! “You want a pussy, huh?” she asked dominantly. “Yes, yes, I want a pussy. I wish I could finger myself instead of stroking.” Leslie let loose, his mind becoming softer with the euphoric pleasures of Jane’s hands over his gentle length.
“Can’t put you in the cage when you’re so aroused,” she said. “I can’t help it. I feel so… it feels so good right now. I…” He lost his words as he closed his eyes. “Go on,” she replied, trying to help him finish his words as she stroked him slowly. “I feel so complete wearing this.” He breathed heavily, his nostrils letting the air in and out, fueling his body with the urgency of an orgasm if Jane continued.
She continued to stroke, her nails digging into his balls, tugging them, grazing them up and down. It was all too sensitive; it all felt good. Leslie’s hands parted, resting on the bed as his fingers expanded, his back arched to give Jane signals to continue pleasuring him. “You’re doing amazing, that’s how I like it. It’s okay, you can moan.” Leslie whimpered, his throat burning with the resistance of not making any noise, but with the permission, he made tender sounds, “ngh… mmm… nnh~”.
“Who’s a good girl?” Jane whispered flirtatiously. “I’m a good girl; I’m a good girl~.” Leslie ached, biting his lips, not completely, just a bit. His eyes closed; he was in pure jubilation of what was happening. “Oh, I’m, I’m so close!” he moaned between each of his words. His perineum and pelvic muscles contracted. He was holding it in to let a huge load out, to squirt cum. “C-can I cum, please?” he asked permission, his chest rising up and down while his heart continued to race. It felt like being underneath a blanket during the harsh cold winter nights. To him, to Leslie, this was the pinnacle of recognition, to finally be who he wanted to be, a girl, a woman.
“You mayyyy~,” Jane smiled softly, whispering, and just a split second later, Leslie squirted a rope of cum right into Jane’s hands. “Oh!” her eyes widened as she felt the warm load dripping in the palm of her hands, heat with passion. “Quite a load.” She looked at it, completely licking it off. “Mmh.” She paused in awe of how delicious it was. “I think keeping you locked up until you can finally fill those balls up to let out a huge load again is something I am quite interested in.” She giggled as Leslie’s cock finally became limp from the excitement, from what he witnessed, his inner brows flared up as he finally took a deep breath to be locked up.
“Let’s lock it up for some time, hmm?” “I’m a bit nervous,” Leslie softly whispered, “It’s going to be okay, it’ll feel a bit tight, but you’ll get used to it.” As she finally took the cage, unlocking it and covering his cock up, chastising him with the percussive sound click from the lock, she smiled, “Perfect!” taking the key away and placing it in her secret makeup box. “It should be safe from you here.” Leslie whimpered at the cold plastic of the cage, “Nghn! No… no more boners.” Jane nodded, “Nuh-uh!”
She paused, her eyes squinting. “Hmm.” She moved closer to him, noticing how pretty Leslie looked, that the weight of the cage underneath the panties was the kind of bulge that both excited him and Jane. Now, to do the final touches, to doll up Leslie. “Let’s put on some blush. Perk you up for something else I have planned.” Leslie smiled, “please?”
Jane put some eyelashes on Leslie, a little blush on his cheeks. “Let’s see.” She picked up her cherry red lipstick and softly traced the outline of his lips. “Mmh.” He closed his eyes as she placed it, the softness of the wax against his peach-colored lips accentuating the colors against the pale skin he wore. “Love this, quite the dainty lady you are.” She smiled sentimentally, knowing how much Leslie was enjoying this moment. “I do have one more surprise for you,” she paused, unsure if Leslie would like it or not. “Would you like it if I wore a strap-on?”
Leslie’s eyes opened, the shock, the chills up his spine, the hair underneath the wig standing up straight, his fingers pulling the sheets. He was lifted to seventh heaven with the idea of it. “I… you… you’ll fuck me?” he asked, to which she replied, “Would you like me to?” In that very moment Leslie nodded. “I want you to fuck my little asshole, please. I promise to be a good girl.”
And Jane smiled, knowing they had a very adventurous weekend ahead of them, while the final artifact was still yet to be revealed, placed securely behind the bag she took the cage out of.
Fin.
Thank you for reading :)