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Taking Off Belladonna Jack Brown walked through the airport parking lot knowing that it would be the second to last time that he would make the walk. He had finally gotten a job commensurate with his education in accounting and could not be more thrilled by it. It had been two years since he graduated and found no luck in obtaining employment in his chosen field. With no luck finding work as an accountant, Jack had taken a job as a steward. He had, largely, been able to get the job based on his employment in various service jobs that helped pay his way through college and not the education he received. Jack hated working as a steward. While there were many men in the field, the field was still predominated by women and some of the airline's pilots made sure to make fun of him for it. Jack felt that the job was beneath him, given his education level, but he knew that he was lucky to have even gotten the job given his overall over qualifications. The job had at least provided him with steady pay even if it was a dead end job. A gust of wind struck Jack as he continued to walk through the parking lot. The gust forced his low ponytail away from his head before it snapped back and the ends of his hairs brushed against his neck. Jack shook his head for a moment as he bemoaned that his new employer was requiring him to cut off his ponytail prior to his first day at the office. In Jack's mind, however, having to look professional was a small price to pay for a job with a chance of career development in his chosen field. Jack's long hair had also resulted in some of the ribbing he received from the male employees at the airline. Given that many of his fellow stewards were gay, the straight male employees and a few female employees often made homophobic jokes at his expense. Jack took it in stride though as he knew the comments were not malicious. Jack put up with as he had no desire to cut his hair. He had kept his hair long since he was in high school. His parents hated it, and that was certainly a large part of its appeal at the time. It also helped with the image he liked to project at the time as he played as a bassist in garage punk rock bands around his neighborhoods. The girls that hung around the band members seemed to like his long hair at the time as well. Jack knew that part of his life was over, however, and he was soon going to put his two years as a steward behind as well. He only had one more set of flights scheduled. While there would be things he would miss about it, Jack was looking forward to a career change. "Hey, Jack, wait up," Jack heard a voice shout from behind him as he walked through the parking lot. Jack smiled as he saw Samantha Stuart walking towards him. She was one of the things that he was going to miss most about his job. She was dressed in the flattering stewardess uniform that he loved to see the girls he worked with in. Samantha was by far his favorite though. She was his age, 5'3" and busty. Jack adored her and could only wish that the feeling would ever be mutual. Samantha hurried up next to him as she wheeled her suitcase behind her back. Jack looked down at her as she moved next to him and asked, "You haven't told me. Do you plan to do anything special for your last flights?" "I haven't really thought about that," Jack replied honestly. "Really? Isn't your last days the 31st and the 1st?" "Yes." "That's right around the corner." "I know." "You know I'm working that one with you and Gretchen." "I'm aware," Jack replied with a smile as he thought about his last scheduled flights. He loved working with Samantha because of her looks, and he was friendly with Gretchen, although she was ten years older than him and he found her slightly intimidating. "Well, I think you should go out with a bang," Samantha said with a smile. "A bang? You know, I'm trying not to lose the airline as a reference or go to jail." "I don't mean you should throw open the doors to the plane and do some emergency escape stunt. I'm just saying that maybe you should just have a little fun on your last trips." "Like what?" "Well, your last day is All Saints Day, so you know what the day before is." "The company doesn't let us veer away from the uniforms on Halloween, Samantha. You know that." "Who said anything about veering away from the uniform," Samantha responded with a grin. Jack shook his head as he asked, "Well, what do you have in mind?" "Maybe, you could dress up like a stewardess. You'd still be, technically, in uniform..." "Are you crazy?" Jack interjected. "No, I think it'd be cute. It certainly would make it one of our more memorable trips together." "Memorable for you, horrifying for me," Jack countered. "Oh, come on, it'd be a lot of fun. I'd love to do this with you." "You may want me to dress up like a stewardess?" "Yes, in fact, I dare you to let me dress you up like one." "Dare? You dare me?" "Yes, you got the cojones, buddy?" Samantha replied with a smirk. "I'm not doing it," Jack replied as a grinned and shook his head. "What are you chicken?" "Chicken? What are you, five?" Jack responded with a laugh. "Buck, buck, buck, buckha," Samantha retorted. "I'm not chicken. I'm just trying not to be stupid about this," Jack retorted, growing more serious. "What are you concerned about? You got a new job. It's not like you'd screwing up your future with the airline." "Maybe, but there would be the humiliation of being a guy in a skirt walking around a plane while everyone is making fun of him." "That shouldn't be a concern," Samantha replied, shaking her head with a smile. "How could it not be?" Jack inquired as he threw up his hands. Jack was confused by Samantha's suggestion. He had never dressed up like a woman on Halloween, and, in fact, had never even considered dressing up like a woman before at all. Jack could not understand why Samantha was pushing the idea on him. "How can I say this delicately, Jack? You've got the looks for the part." Jack looked at Samantha strangely for a moment before he asked, "What is that supposed to mean?" "You know you're not a big guy. You're 5'8," that's tall for a girl, but not really tall. I mean, Gretchen's going to be the other stewardess on the flight, and she's the same height as you, and it never really attracts much attention to her." "Yes, but that's not what I meant." "Is it your build then? I mean, you're a thin guy. You got those lanky limbs. I wouldn't say you're quite a waif, but you're close. You're definitely no bigger than Gretchen."' "You keep mentioning Gretchen. Does she know about your little plan?" "No, but she would definitely have to be part of it. She's the only stewardess I would want to get on board with this, and you couldn't fit into one of my uniforms anyway." "I think you've lost it," Jack replied. "Oh, what could be the hold up, Jack?" "I think I've already made that clear, Samantha." "What? People are going to think you're a guy? Well, I think I've made it clear too that your body is not going to give that away so the only thing that you think might is that cute little thing that's above your neck." Jack smiled as he heard Samantha call his head cute. Samantha read the smile on his face and knew that she had him where she wanted him. Samantha pressed on, "Your face is really cute. Not in that rugged masculine way, but in that baby faced sort of way that really draws in those girls looking for a sensitive man." Jack was a bit torn by Samantha's complimenting of his appearance by referring to it as cute, but not masculine. As Jack looked at her in silence, Samantha continued, "With a little work, I could really make a decent woman out of you." "I don't know about that," Jack replied, breaking his silence. "I'm pretty sure. I'd love for you to let me try." "When?" "How about now?" "Here?" Jack asked as he looked around the airport parking lot. "No, silly. Why don't you come back to my place, and we'll see what I can do with that wonderful face and great hair," Samantha replied as she pulled on Jack's low ponytail. Jack blushed as he thought about going back to Samantha's apartment. He had never been there, but he had long wanted to. As Samantha rubbed his arm and asked, "What do you say?," Jack stood in silence as he daydreamed about the chance to take her to bed. He had caught himself fantasizing about her many times before and was sure that she had to know that he thought that she was attractive, but he figured that she was more than aware that most straight guys probably did as well. As he looked down at Samantha's smiling face and eager eyes, Jack relented and said, "What do you I have to lose." "That's the spirit," Samantha said as she slapped his arm. Jack nodded before Samantha told him how to get to her apartment, but she then instructed him to follow her car to the apartment. Jack nodded again and agreed to follow her. Jack got into his car and followed Samantha out of the parking lot. He tailed her home as she instructed and felt a bit strange about the whole thing. The doubts in his mind about Samantha's intentions crept up periodically, making him think about veering off and heading home. Jack's mind kept warning him that letting Samantha feminize him was probably not the way to her heart. The small sliver of a chance that things could go his way, however, made him continue on behind her. Jack saw Samantha's car turn into the parking lot of a suburban apartment complex. Jack followed her into the lot and parked a few spaces away from her. Jack walked over to her and followed her into the apartment's lobby before they walked up the stairs to her second floor apartment. As Jack followed her up the staircase, he could not take his eyes off her shapely rear that was hugged by the tight pencil skirt of her uniform. Jack walked behind her as she approached her apartment door. She fiddled with the key in the lock before she pushed the door open. Jack walked into Samantha's apartment and looked around. Much like his own apartment, the place was not large, however, Samantha's apartment was far more intricately decorated than his own. The decorations and furnishings struck Jack as being almost girly girl in style, but they were not over as the top as some girls' places he had been in. Samantha turned towards Jack and said, "Take a seat on the couch and make yourself at home. I want to get out of this uniform and into something a little more comfortable." "Sure thing," Jack replied as he sat down on her beige colored couch. He fantasized about what she would come out wearing, even though he knew that it was foolish to think that she would be wearing only her lingerie or nothing at all as she was in his imagination. Samantha came out a few minutes later dressed in a form hugging t-shirt that barely covered her midriff and a pair of brown leggings. Jack leered at her legs and her shapely rear as she walked towards him in her tight fitting clothing. Samantha caught the look on Jack's face and figured she knew all the things Jack must have wanted to do to her at that moment. She smiled as she asked, "Are you ready?" Jack nodded at her as Samantha walked over to him and took him by the hand. She led him into the bathroom and sat him upon the closed lid of the toilet. Samantha smiled at him as she said, "First off, let's do something about that hair." Jack felt a sense of arousal as Samantha took his hair out of its low ponytail and ran her fingers through it before she tied it back up in high ponytail. "There, more feminine looking already," Samantha replied with a smirk while she took out her makeup bag. Jack shook his head before Samantha took hold of her mascara and went to work on Jack's eyes. She placed the mascara down and picked up her eyelash curler. Jack closed his left eye as Samantha approached it with the curler. He felt it clamp down almost upon his eyelid before she pressed down on it. Jack sensed a little pressure for a few second before she released the curler and moved it up his eyelashes and repeated the process. She then did the same for his other eye. Samantha put down the eyelash curler and took hold of the mascara once again. Jack listened to Samantha tell him what she was doing as she put the mascara onto his bottom eyelashes first before she told him to look straight ahead as she used a back-and-forth motion while she moved the mascara wand up Jack's lashes in an upward sweep, to help give his lashes a curled effect. Jack waited patiently as Samantha repeated the process two more times to put three coats of mascara onto his lashes. With his eyelashes done, Samantha took to applying eye shadow to Jack's eyelids. Samantha smiled as she looked down at Jack and said, "I'm dusting a medium color on your eyelids. It really works when you've got light skin like yours and almond shaped eyes." "Glad to hear it," Jack said, unsure of what she wanted him to say. "Okay, I'm going to work the darkest tone into your top and bottom lash lines, the crease and outer corners and then we're going to blend it." Jack sat still and silent afraid that any further comments or movements would result in him getting poked in the eye by the brush in Samantha's hand. Samantha smiled as she put away the eye shadow and said, "Your bone structure and skin are great so you don't need any foundation or really any rouge." "Is that good?" "Is that good," Samantha repeated Jack's words back to him, "Girlfriend, you can't take a compliment." "Very funny," Jack said with a scowl and blushed as he heard the girl he fancied so much call him 'girlfriend.' "Oh, I'm just teasing you. Don't take it so personally." "I know. I'm sorry," Jack replied as he rubbed his arm. "Good, now, I'm to do a little work on your lips to help give them that kissable look that guys love, you little slut," Samantha said with a laugh as she put her hand on his shoulder. "Really not helping," Jack replied with a faint smile. "Oh, I'm just having a little fun, babe. I don't get to do this too often." "Often, don't you mean ever?" Jack retorted. "Well, I used to do it with my little brother." "He let you..." "Oh, no, not him. Me and my sisters used to tackle him, tie him up and take turns making him over as our baby sister." "And what did your parents say?" "They usually chided us, but we could tell they found it almost as funny as we did since they never gave us much of a punishment for it." "Sounds like a lucky boy," Jack replied as he rolled his eyes. "Luckier than most, I'd say," Samantha retorted with a grin before she took out her lip liner and lipstick. Samantha smiled at Jack as she outlined his lips from the center to the edges with the lip liner before she took hold of the lipstick. Samantha then told Jack how to apply the lipstick as she swiped it across his lips. She then showed Jack how to blot the lipstick with a tissue before she turned her attention to his nails. Jack gave Samantha a curious look as she took out a box of press on nails with a French manicure design. Jack asked, "When did you get those?" As Jack wondered if this was part of some larger plan by Samantha, she replied, "I've had them for a few years. I got them to be part of a Halloween costume I decided to never wear." "Why not?" "My girlfriend's decided to go as a group as something else that didn't quite go with the nails." Jack nodded as Samantha began to apply the glue to his fingertips. She smiled at Jack's hands and said, "It's good that your hands are so small. It will make your appearance a lot more believable." "Thanks," Jack replied as he blushed. He knew that he had small hands for a guy. That was one of the reasons that he played bass. His hands were not large enough to spread his fingers to play the guitar with the effectiveness of other guys, even though as a punk rock band, such musicianship was sort of frowned down upon. Samantha smiled and kept talking to him as she affixed each fake nail onto his fingertips before she turned her attention to his hair. She let his hair down from his high ponytail and began running her fingers through the strands of his hair again. Jack loved the feeling of Samantha's hands moving through his hair. She then took out a brush and began to brush out his naturally straight, thick hair. When Samantha finished brushing out Jack's hair, she said, "Since your hair isn't layered, there's really only so much I can do with your hair, but it will certainly do." "Do any girls not have layered hair?" Jack asked feeling a bit nervous. "Of course, plenty of girls do. Why, even Kate Middleton does." "Is that the English girl?" "Yes, the princess." "She's pretty." "She sure is, and I'm going to style your hair just like that. Just think, you'll have hair like a princess," Samantha said with a straight face. "Just great," Jack replied without any emotion. Samantha laughed and said, "Cheer up. A lot of girls would love to look like you." "Still, not helping," Jack replied. Samantha put on a curling iron and asked Jack if he wanted anything to drink. He took her up on her offer and followed her into the kitchen to get a soda. Samantha was careful to keep him away from the darkened window so that he could not get a good look at his feminized self while they waited for the curling iron to heat up. After a few minutes, Samantha took the drink from Jack's hand and brought him back into the bathroom. She sat him back down on the toilet lid and began to work some dry shampoo through his hair before she took hold of the curling iron. Samantha smiled as she used the two inch curling iron to clamp down on the ends of Jack's hair. She then rolled the curler up, holding the iron horizontally to create big curls at the ends of his hair. Samantha was careful to mist the curls with hairspray after each curl to make sure she did it right. Once Samantha finished with Jack's hair she unplugged the curling iron and said with a smile, "Do you want to see the finished product?" "Sure," Jack replied with some hesitation, sure that he would look like one of the transvestites he had seen periodically on the Jerry Springer and Ricki Lake shows during his high school afternoons. Jack pushed his hands against his knees as he stood up and turned towards the mirror. Jack froze as he stared at his reflection. "Oh, my god," Jack exclaimed. "I know right," Samantha said, unable to hide the giddiness in her voice. "How did you do this?" "I'm a magician," Samantha replied with a smile as she hugged Jack before she continued, "It was all you, baby. I told you that you've got the perfect bone structure for this." Jack touched his cheek as he gazed vacantly at his reflection. He could not believe how feminine his face was with a little makeup on. He had sometimes been teased for looking boyish or girlish, but he had never realized just how feminine the features of his face naturally were. "What do you think?" Samantha asked. "I look like a chick," Jack exclaimed. "See, I told you, no one will be able to figure it out. Do you believe me, now?" "No. I can't do it. I must be seeing things," Jack said as gazed at his reflection, still refusing to believe his eyes. "Oh, don't be such a scared little girl," Samantha replied as she slapped him on the arm and laughed. "I'm not. I'm going to embarrass myself..." "How?" Samantha interjected. "Someone will see through this," Jack said as he pointed to his face. "I don't see how. Look at that pretty face in the mirror, baby. No one's going to see anything, but a cute little girl like me." "Well, that's fine for you because you're a girl, but I'm..." "A scared little girl," she interjected with a giggle. "Would you stop calling me that?" "Oh, come on. What else can I call you? You're afraid of being called out on being a man in a dress even though you have to admit you make a convincing girl and, on top of that, it'll be Halloween. We can play it off as a lost bet on the perfect day for it if you're caught." "I don't know." "Come on, it's one day, baby. Don't you want to do something special for once? This will be a memory that will last a lifetime." "Yes, humiliation is the kind of thing that tends to stay with you." "You won't be humiliated. No one will know, but us and, well, of course, Gretchen." "Why her?" "Because we have to get the uniform from someone, and she's the only girl on the flights who's your size. Gretchen's the only person on that flight who could figure out who you are too, so she'd have to know anyway." "I'm still not sure about this." Samantha shook her head and took his face between her hands and turned it towards the mirror and asked, "Do you see a man in this bathroom?" "Kind of," Jack answered. Samantha shook her head once more and said, "No. It's just two cute girls," before she placed a kiss on his cheek. "You're sure about this?" Jack asked. Samantha nodded as she took out her cell phone and told Jack she was calling Gretchen. Jack nodded and relented, "Okay." Jack sat back down on the toilet lid and nervously tapped on his knees with the fingertips that were still covered by the French manicure style press on nails. Jack listened as Samantha said hello to Gretchen before she got to why she called. As Samantha explained what she and Jack agreed to, Jack cringed. He heard Gretchen exclaim before he heard her laughing. Samantha smiled as she kept talking to Gretchen who Jack realized was more than on board with the idea as he, mostly, only heard Gretchen talking. Samantha looked at Jack and put her hand over the phone and asked, "What size shoe are you?" "I wear an eight." Samantha nodded and told Gretchen. Samantha smiled and then told Jack, "She's going to bring two pairs of shoes for you too. She wears a nine so you're in luck." "Won't that be too big..." Samantha laughed as interjected, "No girls' shoes run smaller than men's. You'll be fine." Jack nodded as he nervously ran his fingers through his hair. Samantha finished speaking with Gretchen and said goodbye to her before she hung up. Samantha turned her attention to Jack as she put the phone down and said, "You're lucky you such little feet. Now, we don't have to buy you new shoes." "Well, I do great stunts with my little feet," Jack replied. "Stunts?" Samantha countered. "It's from a Mel Brooks movie." "Mel Brooks? Oh, stop being such a boy, quoting Mel Brooks movies. Keep it to chick flick stuff so you don't give yourself away," Samantha said with a laugh. Jack squirmed as he sat before her. Samantha smiled down at him and said, "Okay, let's clean you up." Jack nodded before he let Samantha use her makeup remover on him to clean away most of the makeup that she had put on his face. She then took off his fake nails and retied his hair in a low ponytail. When she finished, she led Jack to her door and said, "I can't wait to do this next time." Jack lied as he looked into her eager eyes and said, "Me neither." ----------------------------------------------------------------------- Jack waited the few days prior to his last scheduled flights as a steward with an uneasy feeling in his stomach. He feared what those he would counter en femme would say to him and figured that someone would have to see through the ruse. As Jack drove towards the airport that Halloween, he hoped that Samantha was just fooling with him and had no intent of making him go through with what he agreed to do. The memory of the look in her eye, however, made Jack realize that such hopes were probably in vain. Jack pulled into the airport and drove to where he always parked. He took his suitcase out of the trunk of his car and wheeled it towards the terminal. Jack showed his identification card to security and walked to where the other stewards and stewardesses in his airline waited before they went on board the planes to prepare for their flights. Samantha saw Jack walk in and approached him with Gretchen in toe. They pulled Jack aside and brought him into a private bathroom. Jack felt uneasy being in there with the two girls as Gretchen took out the extra uniform she had brought for him. Jack looked at the familiar uniform with a queasy feeling in his stomach. Samantha told him to strip and put on the pair of control top tights first. Jack asked the girls how to put them on, prompting Samantha to demonstrate how to roll them down and put them on. Jack followed their directions as he took the tights from them after he stripped down to his briefs. He slowly unrolled the opaque navy blue tights up his legs and felt his member start to stiffen from the silky feeling climbing his leg. His evident arousal caused Jack to blush around the two girls who appeared mercifully oblivious to it. Once he finished putting on the tights Samantha helped him put on a bra and stuffed it for him before she handed Jack the standard powder blue blouse the stewardesses at the airline wore. Jack put his arms through the sleeves before he fumbled with the buttons he believed were on the wrong side. After he finished putting on the blouse, Samantha handed him Gretchen's uniform dress. Jack stepped into the navy blue dress with a button up top. Jack fastened the silver buttons over his false bust. When he finished Samantha straightened the dress out to show the blue collar of the shirt that peeked out from beneath the dress. With the outfit finished, the girls handed him a pair of navy blue two inch heeled pumps. Samantha smiled and assured Jack that the low heel would be easy to walk in as he stared warily at the shoes in his hands before he put them on. Samantha then turned her attention to doing her makeup. Jack sat still and followed Samantha's instructions as she gave him the same makeover that she did in her apartment a few days earlier. Gretchen shook her head as she saw the face that emerged as Samantha continued to put makeup on Jack. She laughed as Samantha finished and turned her attention to his nails. "What's so funny?" Jack asked he squirmed nervously in his seat. "You look like a girl." "Isn't that the point?" Jack asked while his heart continued to race. "Yes, but I can't believe you look this much like one. I would never think that you were a guy." "Thanks I guess," Jack replied as he rubbed his hands. Samantha then told him to stay still as she began to apply adhesive to his nails and covered them with fake French Manicured tips. After she finished with his nails, Samantha turned her attention to his hair. She styled it as she previously did in her apartment. Gretchen shook her head as Samantha did it and complimented Jack about his hair. Given that her own hair was dry and damaged because of repeated colorings and straightening, Gretchen was envious of his long, silky and healthy hair. Samantha smiled at Jack as she stopped fussing with his hair and said, "Are you ready?" "As ready as I'll ever be," Jack answered. Jack stood up and immediately felt off balance in his heels. He steadied himself and looked at the girls. "Don't worry. I've got a pair of flats for you for take off and any turbulence. We won't have you walking the cabin in flight with those on if there are any problems." Jack nodded at Gretchen's reassuring words as he approached the door. "Oh, I almost forgot," Samantha said before she took a perfume bottle and sprayed Jack. Jack breathed in the flowery aroma that immediately excited him. He shook his head and asked, "What did you do that for?" "It'll throw people off a little more. People will smell that scent and think that you could never be a man smelling that pretty." Jack nodded in response before he followed her to the door. He took a deep breath as he walked through the doorway. He breathed a sigh of relief as the room was empty since the other flight attendants had left to get on their planes. Jack looked at the board in the room and saw that the plane they were supposed to be relieving the flight attendants on had just landed. Jack's attention was drawn away from the board as he took hold of a pocketbook handed to him by Samantha. Samantha opened the pocketbook up to show him that they had put his wallet and keys inside of it before they put his clothes away in his suitcase. Jack thanked her before he took hold of his suitcase and made his way towards the door leading towards the main terminal for the airline. As Jack walked towards it while wheeling his luggage behind him, he felt the pencil skirt of the dress starting to restrict his gait. He had not noticed it as he walked out of the bathroom with the girls as his steps then had been small and hesitant for fear of what he would see beyond the door. While Jack was still nervous, he was trying to present himself as calm and steady to avoid any unnecessary attention. The strangeness that accompanied each skirt shortened step Jack took was amplified by the uneven weight distribution on his feet and the stretching feeling of the nylon tights that moved along his legs. As Jack took a deep breath and walked through the doorway to the main corridor of the terminal, he felt the straps of his stuffed bra starting to dig into his shoulders. Jack whispered a compliant about it to Samantha. Samantha laughed and said, "You'd better get used to it," before she explained to Gretchen what Jack had said, causing Gretchen to laugh as well. Jack looked around as they walked through the terminal. They received a few looks as they walked by others, but Jack was relatively sure that it was only their uniforms that attracted attention. Jack did not notice anyone looking at him oddly, which was reassuring to him even as it made him wonder just how feminine he naturally was if he could so easily pass himself off as a woman in public. They reached their gate and saw the ground crew who manned the gate to let fliers onto the plane. Jack and the girls smiled as they walked past them and onto the plane. They put their bags away in the overhead compartment and awaited the pilots to enter the cabin. Gretchen walked down the aisles of the plane while they waited and ordered Jack and Samantha to do a little cleaning up before the pilots and passengers came on board. Jack and Samantha followed Gretchen's orders. As she was the Cabin Service Manager, they knew they had no choice but to do as she told them to. Jack was happy that he would soon be ordered about mostly by men. Some part of his male psyche found being ordered by females, as he so often was as a steward, to be degrading even as he knew that it was part of the modern world. Soon after Samantha and Jack finished tidying up, the pilots came on board. Jack instantly recognized them from the many briefings he had over the two prior years, they were Brad Winthrop, the pilot, and Ray Winsley his copilot. Jack stood behind Samantha and Gretchen as Brad said hello to them. Their unfamiliarity with the feminized Jack prompted them to inquire about his name. Jack responded with the name that Samantha had told him to use. "I'm Gabriella Baker, sir," Jack said in a higher voice than he normally used, hoping to disguise his true gender. The men shook his hand and thought that there was nothing strange about Jack given Samantha and Gretchen's easygoing interactions with him. With the introductions finished, Jack took a step behind Samantha and Gretchen again, hoping to minimize the opportunity for the men to connect the contours of his face with the steward the men had met many times before. Brad then began to remind them about the safety procedures on the plane as the company policy forced him to do before each flight. Jack listened to the briefing on emergency equipment and checklists that he had heard hundreds of times before. After they finished discussing emergency procedures, Brad informed his flight attendants of the anticipated turbulence during the flight and when they should expect to experience it during the flights. Jack nodded and made a mental note of it before Brad finished with the preflight briefing. Jack and the two girls then began to do their preflight safety check. They checked the life-vests and other safety equipment to make sure that the proper number required was in place before they verified that the flashlights and firefighting equipment were fully operational. As Jack did his familiar preflight routine, everything felt different to him, which helped him maintain the presence of mind to keep acting feminine. With every skirt restricted movement, uneven step or bending of his back that caused the straps of his bra to pull against his skin, he was reminded of what he was supposed to be presenting him as. After they finished, Samantha and Gretchen walked out of the plane and towards the gate to help the disabled board the plane first. As she did so, Jack began to fear what the airline's customers would think when they boarded the plane and saw him. Even though the pilots he knew as a man did not see through his ruse, he knew that there was a chance that one of the fliers would be astute enough to notice the little cues that he was sure would give away his masculinity. He tried to think of ways to excuse it all. Some of the excuses he thought of were simple, such as for his occasional awkward steps in heels, he could blame movement on the plane. He knew, however, that he was going to have to stretch for others. He figured that some one would notice his faint Adam's apple. Jack believed the best comeback was to tell them he had "Ann Coulter syndrome". Jack watched as Samantha wheeled a man in on a wheelchair. Jack helped her seat the man before he placed the man and his elderly wife's luggage into an overhead compartment. Gretchen then brought in another special needs flier, and they repeated what they had done for the first. Once they finished seating the special needs passengers, those with small children were permitted to board. Jack helped them put away their bags, which proved more difficult than he expected with his heels as the kids and other passengers tried to force themselves by him while he lifted the heavy bags into the overhead compartment. Jack lost his balance, but one of the passengers caught him at his waist and helped him rebalance himself. Jack blushed as he thanked the man before the remainder of the passengers were permitted to board the plane. Jack assisted the remaining passengers with the loading of their carryon baggage into the overhead compartments as others forced themselves past him. Jack felt relieved that he did not lose his balance as he did it, unlike before. After everyone was seated, Samantha walked over to those sitting in the emergency exit rows to make sure they were willing and able to assist in an emergency situation. Jack was happy to let her do it since he did not want to do any unnecessary speaking while en femme. Jack then made a safety check with Samantha of the plane's passengers while Gretchen checked in pilots. Jack and Samantha made sure that all tray tables were properly stored, that the seats were in the upright position and that the armrests were down and that the baggage compartments were fully closed. Gretchen then came out and began to go through the safety demonstration. She advised the passengers that a pamphlet regarding proper safety procedures was in the pocket of the seat in front of them before she advised of what to do in the case of sudden drop in cabin's pressure and other emergency situations. Jack then took hold of the flotation device and demonstrated to the fliers how to put it on and where to blow as Gretchen explained what Jack was doing. Jack was careful to not actually touch his lips to it as he knew that it would leave lipstick traces on it. After the safety demonstration finished and Gretchen reminded the passengers not to try to disable the smoke detector in the bathroom and to shut off all electronics, Jack and Samantha walked down the aisles. They made sure that all passengers were properly secured with their seatbelts and that all other safety precautions had been taken. As Jack walked down the aisle to ensure that all safety precautions were being followed, he felt the pain in his feet growing more intense. He grimaced at the thought that he had another ten hours on his shift and knew that there was going to be at least another four hours he was expected to wear heels to maintain the proper presentation the airline expected from its stewardesses. Jack smiled as he finished making the final preflight safety check of the passengers. Jack breathed a sigh of relief as took hold of his flats from his pocketbook. Jack was happy to be getting out of his heels as they were already causing his feet to hurt after wearing them for little more than two hours. Jack and Samantha then changed out of their heels and put them away before the plane began to make its initial ascent. As Jack and Samantha sat next to each other at the rear of the plane behind the bathroom, while Samantha sat in the front of the plane, Jack whispered to her, "I always thought girls exaggerated the pain caused by their shoes." Samantha shook her head and said, "Now you know better, and by the end of the day, I think you'll have a better understanding of all the girls you worked with." "I can't see how I wouldn't," Jack said with a smile. Jack and Samantha waited for the plane to finish its ascent before they took off their seatbelts and began moving about the cabin. They then began to take orders for drinks. Jack was nervous about this task since it would involve him speaking to the passengers about what they wanted. Samantha and Gretchen put those fears to bed for him by doing it themselves and having him prepare the drinks while they continued taking orders. As they continued, Jack brought the drinks to the passengers. He kept his verbal interaction to a minimum as he did so, only announcing the drink and saying your welcome if a person thanked him for handing them their drink. As Jack walked through the cabin with the drinks, he did feel eyes upon him as he caught men on the aisle seats staring at his legs beneath the knee length hem of the skirt of his dress. Jack felt exposed and degraded by the occasional lustful leers he caught from the men, but he knew that it was better than getting inquiring looks regarding what his real gender was. After they finished handing out the drinks, Jack took hold of a basket of snacks and carried it down the aisle from the back, while Samantha started from the front of the plane. Jack asked the flier if they would like a bag of nuts, cookies or chips that were complementary on the flight. As Jack carried the basket, he felt his bra straps readjusting themselves as he bent to hand out the snacks while one strap was partially pinned and stretching beneath the basket pressed into his shoulder and false bust. Most took the free bag before Jack and the girls inquired about the prepackaged food they also sold on the flight. A handful was sold, and Jack had to come back with the credit card machine to process their orders before he handed them out. Once they finished handing out the food, Jack and Samantha sat down for a few minutes before they were scheduled to do their periodic cabin checks. They talked a bit about Jack's new job before they got up and conducted the cabin check. While Samantha checked on the passengers, Jack made sure that the smoke detectors in the lavatories were not deactivated. Jack and Samantha then took out garbage bags and collected the waste from the passengers that had accumulated after the initial snacks and drinks were brought out. Jack smiled as he held out the bag and took peoples garbage from them as he was required to do. They then put the garbage away in a compartment in the rear of the plane while Gretchen checked with the pilots to make sure that they were having no difficulties. Jack and Samantha sat back down and only got up to answer call lights from the passengers seeking special orders and requests for pillows and blankets. Jack processed the purchases with Samantha and helped keep the passengers as comfortable as possible before he felt the need to go to the bathroom. Jack approached the vacant stall hesitantly. Samantha called for his attention before he stepped into the stall. She handed him his pocketbook and whispered to him to make sure he brought in every time he used the bathroom so as to draw any inquiring looks. Jack nodded as he took the pocketbook and opened the bathroom door. He locked it behind him and began wonder how he was going to use the toilet. He knew that he would have to pull his tights down, but he wondered how he would go with the dress on. Thoughts about taking off the dress crossed his mind, but he knew that there had to be an easier way. He pulled down his tights and underwear and stood in front of the toilet, still mulling over the idea before he tried to pull the tight dress up. Jack struggled to do so, but he got up high enough that he was able to get the skirt of his dress over his member, but he could not hold it there long enough to go. Jack clutched the dress again and yanked it up as he sat down on the seat and forced his member below the seat and let out a sigh of relief as he relieved himself. Jack finished, got up and pulled his tights back up and made sure that his dress was properly situated in the mirror before he washed his hands. Jack exited the bathroom and saw a call light on. He assisted the man and then took a seat next to Samantha again. More than midway through the flight, a period of turbulence was expected. Gretchen made the announcement and the passengers were told to buckle their seatbelts. Jack and the stewardess then made their way through the aisle to make sure that each flier was properly secured in their seats before they sat down in their own seats. As the plane started to shake from the turbulence, he saw the usual displeasure on many of the passengers faces. He had seen it more times than he could remember before Samantha broke his concentration and began speaking to him again. The fasten seatbelt sign was removed shortly before they were scheduled to land, permitting the passengers one last chance to use the bathroom before Jack, Samantha and Gretchen made the final pre-landing sweep of the plane to get the passengers ready for the final descent. Jack and the other stewardess walked down the aisles with new garbage bags to collect the additional waste that had accumulated on the plane. They made sure to collect all hot liquids and disposed of them prior to landing. As the fasten seatbelt sign came on again, Gretchen announced that they were about to begin to make their final descent. The flight attendants walked down the aisles again to make sure that all seatbelts were fastened and that all tray tables were up and collected any last bits of garbage the passengers wanted to throw out. Jack and the stewardess then took their seats until the plane landed. Shortly after the plane finished its final descent, Jack and Samantha took off their seat belts and slipped their heels back onto their feet. Jack could see that he dreaded it more than Samantha who was used to the constant pain in her feet. After they put their heels back on, they helped Gretchen collect more garbage from the passengers as the plane taxied to the gate. Jack could see the evident relief on some of the fliers faces that the plane had landed as he walked down the aisles. He smiled at their expressions as he also realized that no one had given him a strange look throughout the entire flight. He could only wish that the passengers on the next flight would not think there was anything strange about him either. The plane reached its gate and Jack began to assist the special needs passengers off the plane first before the remainder of the passengers were permitted to exit the cabin. Jack stood by the cabin exit with Samantha and Gretchen and thanked the passengers for flying with the airline as he continued to look down the aisles to make sure that no one needed any assistance taking out their bags from the overhead storage compartments. When the final passengers exited the plane, Jack and Samantha made one last check of the plane to verify what was consumed and cleaned up any remaining garbage left by the passengers, while Gretchen filled out the proper paperwork required to complete the flight from the stewardesses' perspective. After they finished, Jack looked to Samantha and asked, "Can we take off our heels while we get something to eat?" Samantha and Gretchen both shook their heads and noted that they were expected to maintain a certain image as they walked around the terminal. Jack shook his head and frowned, but he knew they were right. Jack helped the girls take down their luggage before they exited the plane and headed through the terminal to get something to eat before their next scheduled flight. Jack ate with Samantha and Gretchen as he had many times between flights with them before. They chatted about the usual things going on at the airline and memorable flights, mostly caused by aggravating fliers they loved to complain about. When they finished, Jack and the girls went to the restroom, where Samantha refreshened Jack's makeup. They then returned to their plane and put their bags away before they repeated the same preflight process as they had with the first flight. The shorter flight was without incident and Jack and the girls relaxed as they thanked the passengers for flying with their airline on their way out. After the passengers finished departing the plane, Jack and the girls cleaned up the plane and noted the overall condition of the plane. When they finished, they took hold of their luggage exited the plane again. They headed for the terminal exit as Samantha called a local taxi company to pick them up to drive them to their nearby hotel. With each step towards the exit, Jack felt like his heels were driving nails into his feet. He made a compliant about it to Gretchen while Samantha continued to make her call. She only laughed at him and told him to "Toughen up, sister." Jack and the girls exited the terminal and chatted as they waited for the cab that picked them up 20 minutes after Samantha's call was made. Jack placed his luggage in the trunk of the cab, while the girls chose to keep theirs on their laps as they sat in the rear of the cab and forced Jack into the middle seat with only his pocketbook on his lap. Jack and the girls began to chat as the cab made its short trip to the hotel. They talked about their flight and how Jack was holding up in veiled terms so as not to draw any unwanted attention from the driver. The cab pulled up in front of the hotel ten minutes after they entered the vehicle. As Samantha and Gretchen got out of the cab, Jack opened his purse and paid the cabbie his fare. He turned away from the driver to get his luggage from the trunk, but the cabbie pulled away from the curb and sped off for his next fare. Jack ran after the cab in a desperate attempt to flag it down. As he hurried towards it flailing his arms and shouting, Jack tripped in his heels and fell into a car parked next to the curb. Jack let out a sigh as the cab turned a corner and left his view. Samantha and Gretchen ran over towards Jack to see if he was okay. They realized what had happened as they looked Jack over as he told them that he was fine. Jack rested against the car and asked, "Did anyone get the cab number or the driver's name?" Samantha and Gretchen shook their heads before Jack exclaimed, "I'm screwed." "No. It'll be all right. We can..." Samantha began to speak but stopped as Jack interjected, "We can't. I don't have enough to buy myself new clothes. Money's tight right now, and even if I could, we couldn't get a uniform on this short of notice and all the stores are closed so I'd be stuck wearing Gretchen's flats anyway." Jack clutched his head as he finished stating the obvious to the girls. Samantha put her arm around his shoulder and said, "It's okay. Everything is going to be all right. You can wear Gretchen's uniform on the way back too." Jack groaned as he fought off the urge to cry as he responded, "I'll have to go through security like this though. You don't think security might have something to say if I walk in with an identification reading Jack Brown, looking like this?" "It won't be that bad..." "How do you figure?" Jack interjected. "I..." Samantha went to respond before Jack continued, "It won't even be Halloween tomorrow. I can't even play this off as a costume after tonight. They'll just think I'm a dumb tranny." "It's okay. You'll never see them again," Samantha said in effort to console Jack. "You'll be off to a new job next week and this will only be a memory you can look back on and shake your head at," Samantha then continued with a smile after a pause. "Yes, it'll be all right," Gretchen added. Jack nodded before he clutched the purse that he was happy contained his identification and money and smiled at the two girls. The girls helped Jack to his feet and walked towards the hotel lobby. They checked in and headed for their rooms. After they settled in, Jack heard a knock on his door. Still dressed in his stewardess uniform, Jack answered the door and saw Samantha standing before it. She invited him to the room she was staying in with Gretchen. Having nothing better to do, Jack put on his flats and walked down to their room. Jack walked in and saw that they had ordered room service. "What's this?" Jack asked. "Well, we figured that we'd give you a little gift since you do not seem to want to go out to eat tonight, right?" Samantha said. "No way," Jack replied with a smile. "I don't know why. It's still Halloween, and you could play it off if you were caught," Gretchen countered. "I'd rather not go that route. Not after today and what my feet and legs feel like after working in your damn shoes." The girls shared a brief laugh at his expense before they began to eat. They chatted about various little things as they ate with the television playing in the background. They finished and threw away their garbage before Samantha looked at the coffee maker and said, "Do you think we should have coffee?" "It's a little late and we have to get up tomorrow," Gretchen countered. "I know, but I'm kind of feeling it. Gabriella, do you think you can make me a cup?" Samantha asked. "Gabriella?" Jack asked. "Well, what else I'm going to call you when you're looking so fine, girl. Damn girl, why do you look so fine," Samantha replied with a smirk, prompting Gretchen and Jack to laugh a little. Jack smiled and was sure to sway his hips as he approached the coffee maker. The girls laughed at his overly feminine gait as he walked towards it. Jack laughed along with them as he made Samantha a cup of coffee. Jack brought the cup of coffee over to Samantha and asked, "Miss, Coffee, tea or me?" Samantha grinned as she took the cup from him and said, "Well, seeing as we don't have any tea, I'll settle for the other two." Gretchen rolled her eyes and said, "You two get a room." "I think we have one," Samantha countered. "Just don't let me see or hear anything," Gretchen replied. Jack and the girls continued to talk while Samantha drank her coffee before Gretchen said, "I'm turning in." "Yes, it's about that time," Jack said as he went to leave the room. Samantha smiled at Jack and said, "Why don't you stay with us tonight, girlfriend." "With you?" Jack asked. "Yes." "Won't that be a little odd?" Samantha shook her head and said with a smirk, "There's nothing odd about two girls sharing a bed, sweetie." Gretchen laughed as she said, "Again, I don't want to hear any Lesbo business tonight." Samantha giggled and said, "I'm sure that Gabriella will be a good girl. Right?" Jack nodded before he said, "I don't have anything to sleep in besides my underwear." "I can help you," Gretchen said as she reached for her luggage and handed Jack a nightgown. Jack looked at Gretchen oddly before she said, "I always keep spare underwear and nightgown's on me. You never know what's going to happen." Jack shrugged and nodded as he understood her point. He walked into the bathroom and changed into the nightgown. He came out of the bathroom and saw the girls underneath their covers. Jack walked towards Samantha who lifted up the covers to let him in. Jack laid next to her before Samantha rolled onto his body and said, "Wow. I love how this silky nightgown feels, don't you?" Sensing his own member stiffen, Jack nodded and said, "It feels great." Samantha kissed Jack's cheek and said, "Goodnight, Gabriella." ----------------------------------------------------------------------- The next morning, Jack rose early to the sound of the beeping alarm clock. He felt Samantha's head squirming on his silk nightgown covered chest and smiled as he hit the alarm. "It's too early," Samantha replied. "Usually is," Jack replied before Samantha pushed off of him and brushed his erect member with her thigh and hand. Jack blushed and hoped that Samantha did not realize what she had touched but the coy smile on her face told Jack that she was well aware. He was happy that she seemed to take it well even though he wondered what she thought was the reason behind his erection. Jack waited for his arousal to temper before he slipped on his uniform dress and blouse and hurried back to his room with the rest of his uniform in hand. Jack got into the shower and carefully washed his body, remembering Samantha's admonishment, on the way out of her hotel room, to not get his hair wet. Jack dried himself off and redressed in the uniform, following the instructions the girls gave him the day before. He put on his tights and underwear before he slipped on his bra and stuffed it as he had seen the girls do it. Jack then covered his bra with his blouse and stepped into his dress. It was not long after Jack slid his feet into Gretchen's flats that he heard a knock on his door. Jack stared through the peephole and saw Samantha standing before the door fully dressed. Jack let her in and she explained that Gretchen let her get ready first so that she could help Jack finish preparing for his second feminized day. Jack was happy that she was she was there to help as he stared down at her. Samantha did his makeup as she did the day before. She then worked on his hair a little to give it a more orderly appearance and to eliminate the bed head look Jack was sporting. Shortly before she finished fixing his hair, they heard another knock on the door. Samantha opened it to let in Gretchen, who wheeled her bag and Samantha's bag behind her. Samantha then finished getting Jack ready before Jack collected his pocketbook and headed for the lobby with the girls. Jack felt sick as he walked through the hotel still dressed as a stewardess. While he knew that no one in the hotel thought there was anything strange about him, he was aware that the people he met at the airport certainly would once they saw his employee identification card. They checked out of the hotel without incident and Jack carried his purse towards the curb as Gretchen hailed a cab for them. They got into the cab and made their way back to the airport. As the cab made its way to the airport, Jack continued to dread the reactions he was going to get from security. While the cab drove alongside a street abutting the airport, the sight of descending plane flying over the car reinforced the reality of Jack's situation. The cab pulled up in front of the airport terminal, and they split the fare between them before they walked towards the door after they changed into their heels. Jack nervously took out his identification as he walked beside Gretchen and Samantha taking his careful and straight, skirt constricted steps. Gretchen and Samantha tried their best to temper his fears, but they knew that they could not do anything to fully allay them. Samantha went through security first. She was let in without issue before Jack showed the man his identification. The man stared down at the name and photograph before he stared up at Jack's nervous face. He repeated his action three more times prompting Samantha to giggle. Samantha's response caused Jack to glare at her for a moment before the man looked Jack over and confirmed his bone structure against the male face in the photograph. The man shook his head at Jack and said, "If you're going that route, you need to update your photo, missy girl." Jack blushed and put his head down as he nodded at the man who let him through. Gretchen followed behind them. While they moved farther away from the man, they could hear him laughing and joking with another man not far from him. Jack cringed as he knew that their laughter was at his expense. Samantha smiled at Jack while she put her arm around Jack's waist, hugged him closely and said, "It's not that bad. You won't ever see him again after today anyway." "Yes, I guess," Jack replied in a solemn tone as his cheeks continued to burn red. Jack and the two girls waited to board the plane that was already at the airport when they arrived. They got on board and greeted the pilot and co-pilot. Before they began to be briefed, the pilot and co-pilot from the day before began to laugh as they realized that what they had heard from security on the way in was true. They had not given Jack much attention the day before, but they knew that he really was there in drag that day and had been so the day before as well. Jack squirmed as the two men broke out into laughing as he stood beside them. Jack blushed as they teased him while Gretchen and Samantha gave him sympathetic looks and reassuring touches. "Bergie, did you know that he was this way?" Brad then asked Gretchen, calling her by the nickname he and several other pilots used based on her last name. "It was just a Halloween prank that got out of hand," she countered as Jack squirmed behind her. "Halloween's over, Bergie," Ray added. "We know," Jack interjected in a low, quiet voice, unable to meet the men's gaze. "Don't be so uptight, Gabriella. I'm sure your boyfriend will like the new you when you get home," Ray responded, using the name that Jack had introduced himself with the day before. Jack shook his head. He hated when the pilots insinuated that he was gay because he was a steward, but he had to admit that he was making it easy for them as he stood before Ray and Brad in a stewardess dress, tights and heels. The pilots continued to laugh amongst themselves while Jack, Samantha and Gretchen alternatively pouted and gave the pilots scornful looks. The pilots then collected themselves to brief Jack and the girls. They then began to get the airplane ready for the passengers to board as Jack and Samantha went about their preflight routines under Gretchen's guidance. They helped the passengers aboard and put away their luggage before takeoff. The flights that day were similar to those of the day before. Jack walked about doing what he was expected to do with the constant reminders of his feminine appearance making itself known with the pain in his feet, pulling of the bra and the restrictions on his legs. As usual, Jack grew tired during the second flight that was taking them to their home base. He could not wait to go home, but he had to put up a chipper front around the passengers despite his weariness and the occasional snide remarks from the passengers who viewed themselves as above stewardesses. One of the drunken passengers even walked up to him and asked if he wanted to join the Mile High Club. Samantha glared at the man before Jack responded in a calm voice with a grin, "I don't know. Do you want to join the kicked in the balls club?" Samantha laughed and the man smiled before he continued his blustering comments prior to entering the bathroom by himself. Jack and Samantha shook their heads with smiles on their faces as the man finished and retreated to his seat. Samantha grabbed Jack's arm and said, "I think you should have let him try to join the club with you. It would have been priceless to see his reaction." Jack shook his head and replied, "Based on that guy's behavior, I think we'd have to make an emergency landing so they could take me to the hospital." Samantha shrugged and said, "Yes, I guess it would have been too dangerous." Jack nodded as he turned the page in the magazine he was reading prior to making their final check of the airplane before landing. Jack was happy when the plane landed and the passengers departed. He made his last post flight cleanup of his career as a flight attendant. He was happy it was his last shift at the airline, but as he looked back at Samantha and Gretchen, he knew that he would miss them as he moved forward with his life. Jack and the girls exited the plane with their bags. They then headed for the exit leading to the parking lot. As they walked towards it, Jack slapped his forehead, lightly scratching it with the edge of one of his fake nails. The girls stared at him oddly and asked, "What's wrong?" "I can't go home like this," Jack replied as realized how he was dressed. While the clothing and shoes made it clear to him how he was dressed, Jack had grown comfortable enough with what he was wearing to not even realize that he would look entirely out of place entering his apartment dressed as a stewardess. The girls nodded as he explained that it would be humiliating if his neighbors saw him dressed a stewardess. Jack told them that he could never live it down. Jack's concerns were not lost on the girls. Samantha and Gretchen nodded in response before Gretchen offered to give him something to wear home. Jack agreed to go to her home to get a change of clothes, and Samantha told them that she was going to go too. Jack was happy to hear that Samantha was going there as well as he still enjoyed looking at her despite his feminized appearance and what she had put him through with her dare. Still, Jack knew he could not blame her as he was the one who agreed to the dare after a little pressing by Samantha. Jack also could not get his fantasies about her out of his head even though he knew that there was likely no way that she could ever consider him boyfriend material after the experiences they had shared over the prior two days. Jack sighed as he got into his car before he headed down the road, trailing Gretchen and Samantha. He pulled up in front of the house that Gretchen had kept after her divorce a few years earlier. Jack did not hesitate to get out of the car in his stewardess uniform as he was sure that none of the strangers in Gretchen's neighborhood that night could tell that he was a man. He hurried beside them and followed the girls into the home. Jack looked around the home before Gretchen directed Jack and Samantha to her den. Jack and Samantha sat next to each other on the couch, waiting for Gretchen to bring out a change of clothes for Jack. Samantha smiled at Jack as she clasped his hand and said, "You did great." Jack smiled at the feeling of Samantha's soft hand upon his. The words that she spoke, however, did not make total sense to him. Jack gazed at her oddly as he shrugged and replied, "I suppose." "Do you think you'll do it again?" Samantha inquired with a smile. Jack shook his head and stared at her in stunned silence before he replied, "Are you..." Jack's response was cut short as Gretchen interjected when she entered the room with some clothing in her hands and said, "This is the best I can do for you." Jack nodded as he looked over the clothing he took from Gretchen's hands. Gretchen explained as Jack looked it over, "That shirt was one of my ex-boyfriend's. The sneakers are the least girly thing I've got, I'm