Quick Money

 

Harland was a sissy poster. He wanted one thing, and that was views and attention. He found out that the greatest accounts were either original creators or distributors of great content. People had become too lazy to fact-check whether his postings were legit or created for others. They were simple people, they saw a sissy caption, they liked and sometimes commented something promiscuous under his media. Within weeks, he’d amassed a thousand followers and a thousand more in page views. He was living the dream, setting up his account to begin generating revenue with every page view and post interaction, all while not risking his safety or privacy.

Harland wanted passive income, and seeing the opportunity of smut accounts getting thousands of views, jumped on the wagon. He wasn’t a girl, nor had a reliable source of girl pictures to post, so the next best was sissy captions. He’d spend considerable time browsing various subreddits and Twitter pages, collecting data on what did the best, and forced feminization vastly outperformed other sub-genres. The idea of female domination and being forced to dress as a girl was a popular fantasy for many, it seemed, and Harland took months of preparation, collecting various media to post.

It was simple: he’d post on Fridays once a week with a few captions, let the followers consume his posts for the week, and repeat the next Friday. It was easy, and by following various creators, collecting took no time at all. This side hustle became a big secret for Harland, but smut always sells. It was embarrassing to anyone to his genius money-making operation, because they wouldn’t understand he was solely in it for the money.

Until he wasn’t. The thing about media consumption is that no matter how much you convince yourself it’s for another reason, sooner or later, your brain craves it. Harland convinced himself it was for the money, but a simple 15-minute excursion turned into hour-long sessions, or watching various videos and captions. Then it became, for the research, which took more time. If he found better content, then he’d get more views, he rationalized, spending a whole Saturday afternoon jumping from website to website, grabbing information. He was becoming consumed by the media, craving what was happening in these captions to become true for him. His desires reeked of desperation, as his mind toyed with the thought of forced feminization, how he’d feel, the thrill, excitement, humiliation of being forced to be a girl. His heart hadn’t beat that rapidly ever, but the fantasy that bloomed in his mind created a situation that Harland couldn’t escape.

Perhaps it was desperation, or the rapid heartbeat, or even the lack of blood in his head, but Harland secretly broke down. The way to fast money led him down the path of sissy captions and slowly turned him into a sissy. While his roommates were away for Valentine’s Day dinner, Harland snuck into their room. They all had girlfriends, one of whom was staying the night for Valentine’s Day fun. Finding her duffel bag on the bed, he smiled, carefully unzipping it and looking inside. He moved clothes around until he found a pair of white lace panties.

Feeling the fabric for the first time made Harland’s eyes dilate. He’d never touched a pair before, and he dropped his pants, sliding the pair up his legs. He loved how they felt tightening up his legs, and even more as they were adjusted into place. He looked down, loving the feeling, taking in the moment. Then he heard the door to the apartment unlock. Panic settled in as he hurriedly grabbed his pants and ran for the adjacent bathroom. He shut it quietly as his roommate's voice called out. Seeing the light on, he knocked, telling Harland he’d be gone for the night. Harland, wearing that roommate's girlfriend's white lace panties, grunted in acknowledgement, listening as they left. He breathed a sigh of relief, putting his pants on and returning to the safety of his own room. What he didn’t know was that his laptop was open to his sissy blog, and the girlfriend, who saw inside, was about to put two and two together when she returned, and her panties were missing.

Days passed since the Valentine’s Day incident, and Harland thought nothing of it. He’d slept in the panties, enjoying their feeling for the evening, and decided to wash them and return them to the roommate. Sliding them under the bed, Harland thought it would be a good excuse for their sudden disappearance.

One day, he received a DM from his roommates’ girlfriend. They’d been following each other on social media, occasionally liking posts, but had little interaction besides that. Her message was long, and the length worried Harland, who’d hadn’t read the content. It told Harland she knew he’d taken her panties, and she’d be giving them back to him. She saw his sissy blog on his screen and put two and two together. She’ll be over, without his roommate soon to discuss things further.

Harland began sweating at the thought of what might occur. All those months of reading various captions and posts flood into his mind, ballooning his mind and filling it with “what ifs.” Thoughts and ideas that were not likely to come to fruition, but the idea was beginning to excite him. What if he experienced one of those posts or captions, he’d read about?

Hours passed before a knock at the door brought Harland back down to earth. He was worried about her reaction, slowly opening the door. She barged in with a duffle bag, and before the door closed asked if anyone was home. Harland shook his head, his roommates wouldn’t be back for hours. This was typically his time alone.

“Strip.” She said bluntly. Harland was confused by the request until she gestured for him to quickly do it. In the living room, Harland dropped his pants and took off his shirt. The roommate’s girlfriend giggled at his appearance, making comments that he was on the right path, he’d be better off as a girl. This both angered and excited Harland. He was beginning to live out the fantasies of the captions he’d read about.

She tossed him a pair of panties, the same white lace ones he stole. “Don’t worry, you can keep those perverts.” Harland put them on as she watched and smiled, continuing to emasculate him. She proceeded to toss him a matching white bra and a thin white floral dress. Slowly, Harland put it on as she took out her phone and snapped a picture.

“What was that?’ Harland asked, his voice trembling with embarrassment.

“Collateral,” she smiled. “See, I’ve always wanted to have a sissy pet. And I want to make sure this stays between us. You tell anyone about this arrangement; these pictures get sent to everyone on campus, and you get exposed as the sissy you are. Don’t worry, they won’t be seen by anyone but me.” She smiled. “Now pull up your skirt and show off those panties of yours.”

Harland shook his head. Being feminized was enough, but posing for photos was where he drew the line.

“Let me reframe this,” she said coldly, stepping closer. “Pull up your skirt and show off those panties, or I'll send this picture to my boyfriend and explain that you took my panties. How is that going to look?” Harland was stuck, and he was slowly realizing it.  

Harland lifted the dress to cover his face, hoping his bulge wasn’t showing too much. It was embarrassing enough. She laughed, taking numerous pictures, front and back.

“So I did some research,” she continued, sitting Harland down and pulling out some instruments from her bag. “I know you like quick and easy money. I mean, that’s why you made your blog, right?”

Harland didn’t answer. She began working on putting on a dirty blonde wig. “Well, I know a place where sissies can make a few extra dollars, and I thought if you liked sharing that content, I’m sure you’ll be interested in going.” Harland didn’t say anything. He didn’t know what she was alluding to, and he was scared to ask for clarification.

For the next hour, she delicately did Harland’s makeup, did his nails, and fixed his wig. Finishing by putting him into some knee-high white boots to finish the look. She smiled, excitedly taking a picture before pulling him outside. Harland felt nervous walking down the hall. What if his peers recognized him? What if his roommates came back early? They stopped outside as the roommate's girlfriend took a step back.

“Pose, girl!” she smiled, and Harland struck the only pose he could; dolled up, worried, and confused.

They then drove over to the other side of campus, Harland trying to catch as many landmarks as possible and street names in case he had to walk back home. He didn’t have his phone or wallet, spelling trouble if he had to get back to the apartment after she was done tormenting him. They pulled up outside a brick building that Harland never knew existed. There were stores adjacent to this building, and they were generic businesses, a laundry, and a bookstore. She got out and opened his door.

“Come on,” she gestured, and uneasily, Harland left the car. She knocked on the business whose windows and door were taped up. After a few moments, it opened, and they were ushered inside. The interior did not match the uninviting exterior.

The inside was darkly lit, but the lights they did have were bright pink and blue. They were in the process of setting up for an event, bartenders cleaning the bar, servers setting tables, and dancers on the stage. Not any dancers, erotic dancers, wearing various outfits, talking to each other while others worked around them. The man who granted them access hugged the roommate’s girlfriend and began whispering to her. She nodded, and he took out some cash before handing it to her.

“You always know how to find them,” he laughed. She tucked the money away.

“Please don’t break him,” she laughed, pulling Harland closer to the man. “He’s fragile and hasn’t had this experience yet.” The man smiled widely, looking Harland up and down.

“Well, he has the looks of a good addition,” he said. “I’m sure the girls will love meeting him.” The man started guiding Harland towards the stage.

“I’ll be back after the lunch rush to pick you up!” she called back walking towards the door. “Just remember not to lose all your masculinity.”

Unwanted Territory

 

Swap Class - Crosby

 

StitchFix Order

 

Aunt’s Birthday Present

 

Supportive Friend's - Extended Cap

 

Dawes recently got dumped by his girlfriend. He thought everything had been going well until one night he got a call that ended with “we need to go our separate ways.” While initially upset and hurt by the decision, a new sense of clarity and strength emerged from the loss. An opportunity to be a better, more fulfilled version of himself became apparent. He realized that for years, he never allowed full exploration or self-expression to be apparent, instead allowing himself to conform to those around him. Today was the day it stopped.

Dawes was a straight man; he loved women, and the only sex he’d had any interest in was women. Despite his masculinity, Dawes had a secret side to him, which only a few people knew; he liked cross-dressing. In his teens, he’d enjoy frequent cross-dressing sessions, wearing his sister’s clothes when home alone, but as he grew up, the thrill of wearing women's clothes morphed into wearing panties and wearing women’s shorts. Rhett knew that much, and for the last few years, he’d been wearing exclusively women’s panties. Some were flashy, with various styles, designs, and fabrics, and others were more basic with solid colors. Either way, he’d stopped wearing boxers years ago and only wore panties. One of his ex-girlfriends knew that, and they didn’t particularly care, to his relief, as long as he didn’t try to wear their panties or wear thongs, which Dawes had no desire to do.

Dawes, now single, began questioning and exploring his feminine side. He was wearing shorter shorts in public, both as a boost for his confidence and to catch some sun. Dawes was focusing on being himself and not caring about others’ opinions. What he was wearing wasn’t wrong, nor inappropriate, so what did their opinions matter? He began reading and even writing various crossdressing and feminization captions as an outlet to explore this previously ignored femininity. As part of his progress, Dawes wanted to be more open about his feminine side and not lock it behind his mask of masculinity. He can be both masculine and feminine, keeping himself authentic and attracting people who are like him.

Colette was a close friend of Dawes. They’d known each other for years, and while there were no romantic feelings between them besides friendship, they often discussed intimate and personal details about themselves. There was no filter or judgment between the two as they joked. Following the breakup, Colette was the only person Dawes could seemingly be authentic to, so while planning a Christmas week adventure to the mall, Dawes took a deep breath and asked if they could visit Victoria’s Secret. Colette, without missing a beat, jumped at the idea and agreed.

When they arrived at the packed mall, they wandered through various stores as Dawes disclosed more of his feminine personality. Colette didn’t need the outright admittance, since she thought something was up when Dawes’s eyes lingered too long on the display lingerie at Victoria’s Secret. No judgment, as Dawes confessed his likings to women’s underwear, and his desire to be feminized.

Colette asked if they wanted to venture deeper into the store to see more lingerie, to which Dawes excitedly agreed. They wandered through various displays, discussing various styles and preferences. To Colett’s surprise, Dawes knew a fair bit about women’s lingerie, too much not be an enjoyer. Dawes confessed he liked lingerie; he’d bought a few sets for his exes who never wore them for various reasons. While he disliked that, Dawes expressed interest in owning a set himself that he could wear when he wanted to and not be reliant on another to dress for him. Dawes felt comfortable in his masculinity to wear a lingerie set, and why should women be the only ones to dress sexy?

Their day at the mall came to an end, as Colette and Dawes set up a date to exchange gifts before Dawes left to see family out of town. A few days later, Dawes, gift in hand, knocked at Colette’s apartment door. With a smile, she opened it, expressing surprise at Dawe’s wrapping and inviting him inside. Eagerly, Colette opened up her present and hugged Dawes for his gift. Dawes didn’t expect anything big in return, so when she handed him a box, Dawes eagerly opened it.

When the tape on the box split, Dawe’s life would change. Inside, he pulled out a plastic bag containing the red lingerie set he’d been gawking at a few days previously. Dawe’s stomach dropped, his breath shallow, his heart beating rapidly. This was the test to see if all those words he’d said about being comfortable with his masculinity were true, or if they were merely lies.

Dawes held up the lingerie set, taking it out of the plastic bag, his eyes getting wider as he looked at the beautiful set. He ran his fingers through the lace, the soft, textured fabric giving him goosebumps as he took it in. For years, he always gifted, never received lingerie, and now Colette had fulfilled a secret wish for him. Dawes felt conflicted, he really wanted to wear it to feel feminine and have a slight taste of the feminine experience. But he was nervous about the outward appearance of accepting and knowingly wearing lingerie. What would Colette think? What would future girlfriends think? Would they like it too, or would they judge him? Dawes took a deep breath, taking in the whirlwind of emotions. Why give their opinions weight?

“Go try it on,” Colette said, happily. She pointed to the bathroom.

Without hesitation, and perhaps too quickly, Dawes bolted to the bathroom with the box, locking the door behind him. He looked at himself in the mirror, heart still beating against his chest, like a part of him wanting to be free from the expectations and opinions of others. Dawes knew what he had to do. He threw off his shirt, unbuckled his belt, and dropped his pants, casting his masculine clothes aside. He was going to do it. And if he looked ridiculous at least, he could say he tried something he always wanted to.

First, he slid the red lacey panties up his legs. The lace seductively rubbed against the inside of his thighs, causing chills through his body and a bit of excitement. He pulled the pair up to above his waist, adjusting his junk, and tucking them between his thighs. Dawes admired himself in the mirror, running his hands on the lace, and enjoying the feeling against his body and hands.

Next, he unwrapped the bra and placed it against his chest. Dawes hadn’t worn a bra since his teenage cross-dressing years and didn’t remember how to put one on. He brought them back to the front of his chest, fumbling to connect the hooks as excitement coursed through his body. Finally, locking the clasps in place, Dawes pulled the bra around and put his arms through the straps, sliding into place. He liked the way it hugged his chest, and Dawes admired himself in the mirror, spinning around to see every angle his neck would allow him to turn and see. He felt undoubtedly feminine, sexy, and excited.

When he moved the box from the counter, he heard a rattling sound. Confused, he looked inside and saw a red collar. With Dawes' confidence sky high, his face turned a matching red to the lingerie as he looked at it. It matched the set, and why not? Adjusting the side, he put the collar around his neck, enjoying the restrictive and submissive feeling it provided as the leash fell down his chest.

Dawes smiled at the person he saw in the mirror, confident, sexy, embracing parts of him he never thought existed until recently. He was comfortable with himself and admitted he was a straight man who liked wearing lingerie. It was rare to have supportive friends like this, and Dawes was blessed and grateful for Colette. Taking a deep breath, he unlocked the door, stepping into the living room to hear her reaction, feeling more confident and sexier than he had ever felt before in his life.

 

A Friend’s Snap

 

Must Be A Phase, Right

 

New Years Shift

 

All I Want For Christmas Is a Girlfriend

 

A Sissy’s Christmas Gift

 

Coworker's Carpool

 

Secret Cabin - The Expanded Cap

 

Jenson cut the engine, staring at his cabin. A lot of trees stood to the side of the house, surrounded by fluffy snow. He took a deep breath, the cold November air beginning its invasion into the car. What he was doing wasn’t wrong. It wasn’t cheating. It was pure pleasure within the comfortable and communicative confines of his relationship. If that was true, why was he so nervous to enter his cabin?

Logic fell to the wayside as the cold got to him, turning the warm, heavy air into sharp glass that nipped at his exposed flesh. Taking the key out of the ignition, he opened the car door and got out into the cold, quickly closing and entering his house. The house stood with that familiar oak smell and the same lukewarm air as when he left a month ago. On the chair was a black dress he’d left for his next trip, and he smiled. Slowly, he walked around, verifying no intruders had entered during his hiatus. Jenson’s boots clicked on the wooden floors as he flicked on the lights and checked the corners. Both floors were clear of anything but Jenson’s activity, so he opened the first-floor drapes, pulling back the blinds slightly to bring in light.

He walked over to the black dress he had left for himself; it was oddly caring and thoughtful for him to leave something so romantic and elegant for him to return to. He unbuttoned his shirt and cast it aside, unlacing his boots and undoing his pants in the same fashion. This weekend, those clothes would sit on the same chair as a reminder of what he’d be going back to, until his next trip up to the cabin. Underneath was a pair of red panties and a white lace bra. A choice of undergarments to wear under his black dress, but Jenson knew he was alone and didn’t have to conform to society’s dress standards alone and far away from civilization.

Slowly, he raised the red panties in his left hand, allowing the satin to rub against his leg. Years later, the feel of satin on his inner thigh aroused Jenson, and the flood of pleasure filled his brain. He was no longer worried about anything but enjoying the vacation. He slipped the bra over his head and pulled it into place, groping his chest as he admitted himself in the full-length mirror. Finally, he unzipped and stepped into the black dress. It was new, not worn, so another sense of excitement flooded over him. Zipping it up, he smiled in the mirror. He looked fantastic; he couldn’t see any sense of masculinity as he patted down the tight dress. His mind wandered, wondering who he could cosplay as on this trip? Perhaps a woman meeting her man for a romantic getaway? Or a lonely woman escaping the city life for time to herself? It didn’t matter; he was too enamored with his reflection to think too deeply. So much so, Jenson didn’t hear the tires disrupting the gravel outside from an unexpected visitor.

**

“There he is!” Lora yelled as Noelle pulled up. “Slow down, we don’t want him to hear us!”

“I think he’s just here to hunt,” Noelle assured, stopping the far a bit further down the path from Jenson’s truck. “Maybe he’s a bad shot?”

“Lies,” Lora dismissed, sitting back. “He can shoot. You’re telling me that over two years for his monthly hunting trip, he never hit anything? It’s either extremely bad luck or something is up. I can tell.”

Lora and Jenson have been together for two years. Everything so far was perfect for the two of them, but what bugged Lora was Jenson’s monthly hunting trips. The act of hunting didn’t bother her; it was the suspicion that ate at her. For two years, Jenson never brought her up with him, nor any friends. It was always solo, and he never caught anything. When asked, he provided various excuses, but the odd bad luck was beginning to create a scary illusion in Lora’s eyes; Jenson is cheating on her. She noticed he wasn’t as active in the bedroom, which didn’t matter too much to her, but she found it odd. Most men would be foaming at the mouth, and Jenson was content. The vibes were off, and there were suspicions. She knew roughly where the cabins were but never went out to see them until now. Bringing her best friend, Noelle, she was going to put all these suspicions and unproven thoughts to rest. What was Jenson really doing?

Noelle pulled off onto the side of the path, concealed behind some brush. Jenson wouldn’t be able to see her, but they could see her. Plus, if another car pulled up, they’d see who was visiting. Noelle killed the engine as the friends sat in silence, Noelle looking at the slowly decaying winter surroundings and Lora looking through a pair of binoculars. There was no activity.

“What if we do see something?” Noelle asked. “Then what?”

“Then we confront that cheater in the act,” Lora replied sharply. “But I hope it doesn’t come to that.”

Suddenly, the curtains to the second floor opened, and the blinds opened to show a feminine figure in the window looking out; a blonde woman, with a black dress. She looked out briefly before turning away from the window.

“Oh my God,” Lora cried, putting down the binoculars. “There is a woman there.” Lora peeked through them again and saw that the blinds were pulled back a bit further, blocking the view outside. “Drive slowly up.”

Lora was confused, hurt, and angry. How could Jenson do this to her? After all these years, he was a cheater, and she believed him to be faithful? Lora was going to make this cheater pay! Noelle pulled up behind Jenson’s recognizable truck. When the engine stopped, they carefully opened and closed the car doors. Lora didn’t have a key, but she did have a sneaking suspicion where a spare could be found. Digging around the back door, she found a hollow rock that rattled when she shook it. Opening the hatch in the back, a key revealed itself. Here comes the moment of truth.

Lora’s hands trembled as she slid the key into the lock before slowly turning it, listening intently to the sound of the lock sliding open. Once it was unlocked, Lora looked back at Noelle. Noelle nodded with confidence and assurance, and together the two girls made their way into the cabin.

The same stagnant air hit the girls as they quickly entered and quietly shut the door behind them. The windows let in the harsh winter light, and to Lora’s horror, she saw Jenson’s clothes on the chair. Her heart sank, and a part of her wanted to leave. She couldn’t deal with this heartbreak and betrayal, but footsteps above confirmed someone was here.

A faint sound of pop music followed down the stairs as the girls looked up. Whoever it was was singing off tune to the lyrics and moving around to the sound of the beat. Noelle and Lora exchanged confused looks because the voice was masculine, rather than feminine, which confused what Lora saw in the window. Slowly, they climbed the stairs, confusion intensifying as they began to hear Jensn’s voice singing. He wasn’t a pop music enjoyer, at least not as long as Lora knew him.

When they reached the top, the girls stopped in shock; it wasn’t a woman at the window, it was Jenson. His back was turned to them, an array of panties on the bed as he carefully folded them while singing the song. Lora’s jaw hung open in shock, and like a sixth sense, Jenson snapped his head towards them and, startled at the sight, fell to the bed.

“What is this?” Lora asked, stepping forward, taking in the room. The closet was full of feminine clothing, and the open dresser drawer contained neatly folded panties of various styles and colors.

“Lora, I didn’t want you to find out like this,” Jenson stammered, covering himself. “It’s just harmless indulgence.”

Lora looked at him, perplexed. “What?”

“I didn’t want to tell you, but I like crossdressing,” Jenson admitted, looking away. “I figured you’d get the ick and break up. So, this is a cabin I spend once a month, crossdressing and indulging my feminine side.” Noelle laughed, stopping when she met the sharp eyes of Lora.

“This is certainly an experience,” Lora admitted, looking around.

“I’ve always wanted to feel feminine. But only for a short amount of time. I found out before we started dating that a trip once a month fulfilled that desire, so I made it a monthly habit.” Jenson continued. “I didn’t expect you to find out like this.”

Lora began exploring the closet, running her hands through the various blouses and dresses that hung. “All you do is cross-dress?” she asked, bewildered at her findings.

“Yes,” Jenson replied. “I act like a girl, and I live out a safe fantasy. It’s only me and no one else. No one, but you two, knows about this.”

Lora looked at Jenson, who sat on the bed looking back at her. There was a little bit of fear in his eyes as she made eye contact.  The situation was unexpected, and Lora didn’t know how to feel about this revelation.

“So do you play a character?” Noelle asked.

“Yeah, I make up one and act like her for the weekend. Sometimes I’m bratty or lonely. Sometimes it’s just a girl stepping into her feminine side.” Jenson explained.

“What are you doing this weekend?” Noelle pried, looking at Lora, who shot her a confused look.

“I haven’t decided,” Jenson admitted. “I was thinking about being here for a romantic getaway with a guy.” Lora’s stomach dropped. This was getting weird, and she couldn’t look at her boyfriend wearing these undergarments.

“Well, maybe we can help you with that,” Noelle smiled, stepping forward. She leaned into Lora’s ear and whispered, “I can tell you’ve got the ick, and once you get that, there is no going back. Might as well send him off properly and maybe get some blackmail photos. If we’re the only ones who know, he might be willing to pay to keep this a secret from others, and you can afford to go to Europe.” Lora looked at her friend in shock. That was deceitful but seeing Jenson wearing satin red panties and a white lace bra, she didn’t know if she could view him the same way again.

“If you’d like to stay and you’re okay with this?” Jenson said, hopefully. Lora was not okay with this; in fact, when they left, she was breaking up with him, but she might be able to have some last bits of fun humiliating him.  

“Okay, we’ll stay,” Lora confirmed. “But you’re going to be playing my submissive wife.” Jenson’s face flushed, but he nodded. Lora couldn’t tell if he liked this idea or was scared of the idea.

Noelle removed her phone from her pocket as Lora stepped towards Jenson. He tensed up as she pushed him back gently and grabbed a thin piece of fabric on the bed. With her other hand, she grabbed a thong. “Open up.”

Jenson did as instructed, and Lora stuffed the thong into his mouth, placing a finger over his lips and hushing him. A multicolored zebra print pair lay next to Jenson’s head. Lora grabbed it and placed it over his face like a mask, using the white fabric to gag Jenson, who was enjoying the act.

Noelle took time snapping pictures of Jenson, who sat on the bed, enamored with Lora’s feminization domination. She positioned him onto his knees, kneeling in the many pairs of panties. Lora slipped off her pants, wearing nothing but a pair of purple printed polkadotted panties with mint green lace and her tank top. The idea of seeing her boyfriend feminized was still awkward, but she was going to make sure the pleasure he felt this weekend was unlike any other he’d ever experienced again.

With one hand, she slipped it down his shirt and began twisting his nipples as he moaned into the gag. This could be fun, being the dominant one for once. And maybe she can invite some other people over to give Jenson the true feminized experience. But right now, she was going to have her fun with her sissy of an ex-boyfriend.

First Girl Date

 

Thankful For The Boys

 I know I post on Fridays, but I wanted to post another Thanksgiving-themed caption today. So this is also my Friday post. See y'all in December :)

Roommate's Thanksgiving

 

9-9-9 Challenge

 

Old Memories

Harlan parked his car outside his childhood home, shutting off the engine, staring at the warmly lit house. The exterior hadn’t changed in a year since his time away at college, and both a sense of familiarity and pity filled his chest. Familiarity with a sight he’d grown up seeing for 18 years, and pity that accompanied his parents' inability to evolve or change. They remained stuck in the past, not bothering to change anything; they were too stuck in their ways. His father said they’d change the exterior siding when he was away, and by his next visit, it would be a different color, but like most ideas, it remained only an idea. 

Harlan grabbed his bags from the trunk, pulling his sweater hood up to cover his ears. The temperature had dropped sharply since the sun went down, and Harlan failed to dress according to his situation. It didn’t matter as he searched towards the doors and rang the doorbell. The clinging and clanging of pans and pots being put away ceased before a hurried figure made its way to the door. Wiping their hands on themselves, they opened the door. His mother smiled, opening her arms for a hug, which Harlan reciprocated. 

“It’s nice to see you, honey,” she said as they unembraced. “Your father is out getting some things for Thanksgiving. Take your stuff upstairs and get settled in. He should be back shortly.” 

Halan walked up the stairs as his mother closed the door and returned to her task. The familiar creeks accompanied the photographs on the wall of their family. Even a few solo pictures of Harlan and his sister, who would be coming back tomorrow from college. He walked down the narrow hallway past the shared bathroom, his sister's room, and finally his room. Harlan opened the door, and a whiff of musty, stagnant air hit him. His room was just as he had left it a year ago. It was oddly calming walking in, seeing everything as it was, nothing moved or touched since he’d last touched it. 

Harlan dropped his bags on the bed and went to change. He closed the door as he rifled through old drawers of clothing for something to sleep in. He found some old gym shorts and put on a tee. Before he left, he truly wanted to know if everything had been left alone. He walked over to his TV, which sat on a broken dresser. He opened the middle drawer and pushed some boxers to the side. Buried in the corner were a pair of PINK panties, balled up and shoved with other panties. They looked untouched. 

Visions of his mother discovering his panty stash came to mind. She’d be looking for something, and where would someone guilty of a crime hide evidence? Their underwear drawers. She’d be going through it and see various panties in various styles in the corner. More than what a boy should have, especially a boy who hadn’t had a girlfriend yet, should. He imagined her shock when she would discover it, growing confused, then concerned over the drawer's contents. Luckily, they’d remained untouched until now. 

Harlan grabbed a pair and took them out, letting the fabric unball itself into a purple fabric, and a bikini style. He remembered this pair; it was the first he’d ever try on. In high school, Harlan knew he wasn’t like other kids. He was obsessed with panties. It started young when he saw a panty slip on a YouTube video, and to this mind, this was golf. He’d never seen something so intimate, so forbidden as a child. He began seeking out other forms of media that had panties but not adult content. He eventually found a blog of feminized men, men who would be in varying scenarios where they’d be forced to cross-dress. 

Harlan is a straight man; he has no desire to be with a man, but those stories brought him hours of fun and pleasure. Sometimes during school, he’d think of various situations like the captions he’d read. That helped with his panty obsession from desperately looking around for any classmate panty slips. Eventually, the reading didn’t bring the same satisfaction as it once did, so he decided to elevate it; touch some panties. 

His sister had extracurriculars, so when Harlan was alone, he snuck into her room. He knew his sister wasn’t neat but knew if anything was out of line, she’d know. He opened drawer after drawer before finding her panty drawer. Dozens of panties lay in there from varying styles, colors, and manufacturers. Harlan’s heart throbbed in his chest as he carefully pushed pairs to the side, enjoying the feeling of the various fabrics running between his hands. The smooth, enchanting feeling of lace. The soft, cool feel of cotton. The cold, sleek feel of satin, he was in heaven. He went towards the bottom, figuring if he took anything off the top, he’d be discovered. From the pit of his sister’s panty drawer, he withdrew a deep purple cotton bikini. He was mesmerized by the look, the feel, and the rush of excitement to try it on. Harlan figured that since it was at the bottom, it must be a pair she didn’t wear often, so if he tried it on, then she wouldn’t know. 

Harlan scurried to the connected shared bathroom and dropped his pants. His heart was still beating rapidly, and he slid the pair up his leg, the smooth cotton rubbing up his legs as they lifted into place. He adjusted his crotch in the tight-fitting panties, admiring himself in the bathroom mirror. The cotton felt weird; they weren’t the same as the rough interior of his boxer briefs. They were soft, but firm. He felt everything contained and secure. They felt better than his male underwear. Harlan slipped on his shorts over the panties, secretly wearing them for the rest of the night. That became his nightly pair to wear, going as far as to do his own laundry so no one would know. Unfortunately, it didn’t stop there. 

Harlan smiled, putting the pair back and going to his closet. Buried in the back was a container, and when it was opened, it contained various articles of women’s clothing. He’d secretly bought them from various vendors, and when he was home alone, he’d put them on. He’d spend hours trying on various outfits and admiring himself in the mirror. He’d imagine he was a girl, and how a girl would react to what he was wearing. It oddly gave him confidence, and he felt sexy wearing women’s clothing, even if a slight sense of disgust was lingering in the background, with worry that this would balloon into something more. 

Harlan managed to find some bits of clothing his sister didn’t wear frequently that still fit him. He’d spend time on those weekdays alone trying on her clothes, and he liked the way it felt and looked. Crossdressing gave him confidence he’d carry forward, but it also gave him thrills beyond his wildest comprehension. The rush to go against societal views, mixed with the risk of being caught in an intimate and vulnerable position, made these cross-dressing adventures highly pleasurable. He felt guilty for loving this so much, even guiltier hiding this from his current girlfriend. He didn’t know how she’d react if she found out, but Harlan could only guess and not accept. 

He took off his shorts and put the purple panties into his hand. Harlan’s heartbeat was rapid as he did what he knew would happen. He slipped the pair up his leg, getting the same rush from all those times before. The smooth cotton dragged up his leg and into place, the same crotch adjustment to make sure everything fit properly. He admired himself in the mirror again, the feeling of déjà vu. Harlan felt bliss looking at himself in the mirror, wearing the panties, as he slid up his shorts to cover them. 

His phone vibrated, and a message notification from his girlfriend appeared. 

“How’s it going?”

“Good, reliving old memories.” Harlan texted back, sitting on the bed. He knew his grandparents would be at dinner later this week, and they always gave $20 to him and his sister. The sudden nostalgia, and maybe a bit of blood loss to the head, made Harlan wonder if he could pick up some pairs for college? To wear when he is alone or sleeping at night. While waiting for his girlfriend to reply, Harlan jumped from website to website for Black Friday deals on panties. Could we go in and get them this week? 

“Awe, that’s nice,” she wrote back. “Any cute stories?” 

Harlan didn’t know how to reply. They’d only been dating for six months, and she was unable to go to Thanksgiving with him this year. She hadn’t met the family yet. He didn’t know how to reply, so he decided to test the water on his new, resurged obsession. 

Harlan wrote about a story when he was younger, his mother washed their clothes together and misplaced his sister’s pants in his pile. So, he confidently went downstairs wearing them, to the surprise of his parents and the giggling of his sister. While the story is partially true, he did borrow a pair of her pants; no one else was home, but the mailman who Harlan opened the door did get a little giggle out of him wearing bright pink pants, so it was partially true. Not really, but the vision of a young, innocent Harlan doing this seemed cute. 

“That is funny,” she texted back. “Wish I could have been there to see it.” 

“Maybe one day you’ll be able to,” Harlan thought. Being home made him excited, and part of him wanted to crossdress again secretly. It would be harder with the family around, but currently, it’s only him and his family around. Unless it was right now. 

Harlan quietly opened the door and sneaked down the hall to his sister’s room. Her car wasn’t in the driveway yet, so she’s not home yet. Opening the door gave the same odor as his, with the stagnant and musty air. He knew his sister, over the years, had been very deliberate with her placement of stuff and would know if things were moved. But she might chalk up minor misplacements to their mother cleaning. Being in her room for years, he knew exactly where her discarded clothes were. In the corner of her closet.

Harlan opened the doors quietly, seeing various hanging dresses and tops. In the corner, in a depressing garbage bag, there were various tops, bottoms, and dresses. Harlan, feeling the rush of adrenaline, grabbed an orange dress from the bag and closed the closet door. He couldn’t wait anymore, trying to throw on the dress as quickly as possible, but becoming entangled in it. Taking a deep breath, he adjusted the straps, put them properly into place, and pushed them down. 

Harlan admired himself in the mirror, striking various poses to see himself from different angles. He smiled at what he saw, reliving those glorious memories, one more time. He imagined someone seeing him wearing those purple panties with the orange dress and snickering about the absurdity of color choices. The fleeting thought of a boy seeing him wearing that, all with female anatomy, made him blush at how confused the boy may be. Or even how turned on he’d be at the sight of a feminized Harlan wearing purple panties and an orange dress. 

The sudden sound of a cheerful voice downstairs and the hurried sounds of footsteps calling after him broke Harlan from his fantasy. 

“Harlan, are you up there?” as the sound of heavy footsteps climbed up the stairs. What to do now?

Camp Sissywalka – Gideon

 

An Exes Halloween Costume

Listen Halloween is on a Friday, I'm obligated to post today! Nothing more until next Friday, I swear.