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Chapter Five A whole month slipped by as Jacob looked for work with little luck. Leon, the owner of the grocery store, did offer him a part time job but Jacob didn't want to take it unless he had to. The kiss with the man made him slightly uncomfortable yet curious but he didn't want his curiosity to get the better of him. Other than finding a little old lady in his apartment building work was scarce. The lady he had met was willing to pay him five dollars a week for getting the mail and newspaper for her, a few dollars more if he got her groceries for her. He didn't mind the work at all, it barely took any time out of his day, even getting her groceries, and he was willing to take any income he could find. It took another week to find a car wash that would hire him for seasonal work. There was only a month or so left in summer, though, so cash would be even more tight in the winter. Looks like I don't have a choice but to accept Leon's offer, Jacob thought while walking home. He was just coming home from the car wash, the sun setting and buildings casting long shadows. It hadn't been a very busy day yet he was exhausted. There was something about trying to keep up his false identity that was just making him tired. And yet he was restless. Ever since that first time he felt pleasure in his new body he could do little else to clear his mind of it. It was enjoyable, to say the least, and made him more curious what more would feel like. It was the restlessness that drove Jacob to leave his apartment after eating dinner to walk the streets. Darkness had set in but the street lights were kind enough to be working, nice and bright. Not much thought went into the direction he wanted to go in, he just wanted to walk around the neighborhood to see if he could find anything worth while. Jacob had already searched the immediate area for work, other than the car wash and grocery store no one was hiring. So, he broadened his walk and ended up finding a night club. It looked young and hip, many men and women were waiting in line while others went to the head, flashed a card and got in right away. A night club was intriguing but Jacob didn't have anyone to go with and in his current state he looked like a scared little girl that was lost. He didn't have the confidence, or the curves, to woo his way past the bouncer. Instead he stayed in the shadows, watching and learning. He noticed that a few couples were coming from up the street where he came from so he turned his attention that way. He was more than surprised when he saw a car stop at the intersection and a woman walked up to it. Whatever she said made the car drive around the corner and a minute later a man walked around the corner, the woman waiting for him. He slipped her some cash very discretely and she put in her purse. They then linked arms and headed towards the club. Did he just see a hooker get paid to accompany a guy to a night club? Sure enough another woman appeared on the street corner and the same thing happened again. Curiosity got the better of Jacob and he walked back up the street, crossed and took a right. The street was lined with cars and on the other side there were still a few women standing around. Most looked like they were going to go on a hot date to an awesome club, probably the one around the corner but, others looked like real hookers and just like you'd expect them to. There were a few skinny blonds with fishnet stalkings, skirts too short riding too low with bikini tops. Every one of them had a purse, no doubt it was their cash register. A few ladies looked like they had been around the block, a cigarette hanging out of the corner of their mouth while they leaned against the building behind them. They all looked content, though. None of them seemed angry or desperate or even sad. A group of them were in a circle talking while one watched the street. Whenever a car came by the ladies paused in their little chat and lined the sidewalk as if they were showing off 'the goods'. All of them were nice, too. None were overly rude or raunchy to any of the cars that paused or stopped. For the most part they looked clean, happy and healthy. I thought hookers were supposed to be drug ridden whores whose pimp abused them, Jacob thought the longer he watched. He had seen other hookers before, none of them looked as nice as the ladies he was watching, even the older, more experienced looking ones were nicer. It was a curious thing, especially when he saw a car pull up, park, and a tall man get out. He was a black man, nicely dressed for the summer weather and all the girls lit up with smiles when they saw him then crowded around him. He was either their favorite customer or their pimp. A few minutes went by and the more he watched them the more he determined the man was their pimp. He seemed nice enough, joking with the ladies, gently scolding them when they had bad news, it was like he was a father to all of them and the girls loved him for it. Shaking his head Jacob went back to his apartment. He couldn't believe what he had seen, were those really hookers and that man their pimp? If it was all true it was the nicest operation he had ever seen. Happy hookers weren't a usual thing for anyone to see. Maybe the guy had found out the secret to maintaining something like that? An idea popped into Jacob's head but after a few seconds it turned into a bad idea. Sure, he could try to sell himself for money but would it really be worth it? How much did the ladies get to keep from their work? He knew that the hookers he had been with weren't terribly expensive, at least, not when he was working his job. He had more than enough money to throw away and it didn't seem like much then. But what didn't seem like much back then was enough to pay for at least a month's rent if not two. If those ladies even got to keep half of what they made each week he was more than sure enough it would be able to sustain him. Something nagged at him, though. He couldn't be just a hooker, it didn't seem right. He needed something else to do, something normal to make the rest of his life seem normal, being a 'lady of the night' would just spice things up enough, give him just enough excitement to be content. The plan started to formulate for Jacob, he would keep his day jobs, even taking the offered position at the grocery store and if he could, if the pimp was 'hiring', he would also work the street. If he was going to take the grocery store job and possibly take the street job he would need more clothes. He had enough money left for a month or two of groceries but if he started working it would be of little consequence how much he spent. He certainly couldn't go to the Macy's where Miley worked to get clothes to work the street, they didn't sell those kinds of clothes. Maybe I'm getting ahead of myself, Jacob thought as he lied in bed. I haven't even figured out how to get this guy's attention let alone make a deal to work for him. The thought nagged at him until he fell asleep. Restful was the worst word to describe how Jacob slept. It was hard not to think of the opportunity to make some cash, the idea was sounding better and better to him the more he thought about it. He could bring in money hand over fist if he worked for Leon and did the street job. His initial reservations about having intimate relationships with other men went out the window when he thought of how much money he could bring in for it. He wanted to be sure, though, that the girls were really happy and healthy and enjoyed their work and their employer. The only way he could do that was through observation; it would look strange if a young Asian girl walked up to one of the hookers and started asking them about their work. It would also be rude, he might even look condescending to them and that was the last thing he wanted. For the next week Jacob scouted the girls, they were always on the same street but the clients were different each night. He did find out that work was light during the week but when the weekend rolled around the clientele tripled, and so did the amount of ladies. Most of them worked at least one or two nights a week, he started to recognize most of them and was surprised when he finally figured out there were about thirty girls. During the week only five or six of them would be working, at least where he could see them and on the weekend they practically lined the street. Thankfully he went unnoticed, as far as he could tell, the entire time he watched them. He did try to stay out of sight, wearing dark clothes and waiting until it was fully dark outside before venturing out. He didn't want to get caught, someone might think he was working for the police since he had been watching them every night for a week. No, he wanted to stay unseen, in the shadows, until he got a better grasp of the situation the ladies had. As far as Jacob could tell it was safe work. None of the ladies got in a car with a stranger, unless he stayed parked. Other customers were either led into the alley between two buildings or into one of the actual buildings. For all he could tell they either lived or worked out of that building. It was nice, clean, and looked completely normal. During the day no one would know that it was run by prostitutes. What do they do during the day? he thought while walking home. It was still early in the evening and after seeing the usual set of girls he decided to head to the grocery store. Did any of the girls work during the day or was it only at night? He did have the next day off of the car wash, maybe he would check it out. Ah, Leon, he thought as his feet took him closer to the store. The cute man was coming up in his thoughts more every time he thought about the job. Curiosity finally was getting the better of him and overriding any uncertainties he may have had. He was a female now, even if it was a disguise, no one needed to know any different. As far as anyone was concerned, he was Rita, the little Asian girl that lived down the street. Feeling better about himself, and his decision to try and get into the hooker business, he walked with confidence into the store. Leon wasn't that hard to find, he was behind one of the few cash registers and waved to Rita when she came in. Leon was more than happy when his female friend came into the store. He hadn't really seen her since the night that they had kissed. He was partially afraid that he had scared her off after rushing to a kiss but the mood was just right and it wasn't malicious. In fact, it seemed like she had enjoyed it. "Hi," Leon said after getting away from his work. It was late, close to closing time and he met her in the bakery section. She looked like she wanted to talk and waited for him until he wasn't busy, maybe she had thought about the job he offered? He did need another person to stock things during the day, even if it was for just a few hours. "Hi," Rita said and she blushed. To Leon she seemed nervous, as if she wasn't sure how to go about talking to him. "Have you thought about the job offer?" He was trying to give her the leeway she needed to ease into a conversation. He knew money was an issue for a lot of people, it was why he created the tab system in the first place. All of his regular customers needed it at some point or another and all of them had always paid up on it when the time came. His business was doing well enough now that he could take on another employee and he was hoping it was Rita. "I did, and I'd like to take it...if it's still there," she replied. At first she was strong, like she remembered why she had come there but she finished as if she was too shy to talk. Leon had seen it a few times from other women who didn't know the boundaries of their relationship. The kiss probably had thrown her off and she didn't know if they were dating or just friends. "It's still there, I could use a part time person to stock during the day. If you have time we can hash out a schedule and the next time you come in just bring the paperwork, I'll get you signed up." He finished with a smile and Rita nodded to him. He took it as a sign that she did have the time and led her to his office in the back. Jacob was slightly apprehensive of Leon wanting to get started right away, he could have waited until the next day but if the timing was right it was right. There was little he could do as he was led to the office then sat down across the desk from Leon. He brought up the schedule and asked for when he was available, after telling him the schedule was done and an awkward silence ensued. They both just looked at each other, Leon enjoying the view and Jacob wondering if he should bring up the kiss. He wanted to clear the air, or make sure there were boundaries, he wanted to know where he stood, he needed solid footing. "About the other night, when you came over?" Jacob started. He didn't like the sound of his own voice, it almost sounded like he about to accuse Leon of something but the man stayed calm. "I apologize, I shouldn't have done that, it was inappropriate," Leon responded smoothly and Jacob immediately felt like he was about lose an opportunity. "No, no, it's okay," he said somewhat shyly. "It wasn't unwelcome," Jacob explained and it was mostly true. He was curious, they kissed, end of story. Now that he knew Leon was more of a gentleman Jacob felt more comfortable with him but, he didn't know what to say next. "If you work for me I don't want you to feel pressured," Leon explained. "I treat all my employees the same, regardless of relationships." "I understand," Jacob nodded and smiled. Fuck buddies, popped into his head and he liked the idea that he didn't like before. He wasn't looking for a serious relationship, it was the last thing he wanted but, if he could get a fuck buddy out of Leon then he would okay with it. Hell, it would even help prep him for the street job if he could get it. "Maybe you could come over for a beer and you can explain what I'll be doing at the store?" Jacob offered and Leon smiled warmly at him. "Sounds good, I have to close up, though, I'll meet you back at your place?" "Sure," Jacob said and he couldn't contain his smile. Leon nodded to him then walked him to the front of the store. Jacob almost skipped back home. If he was lucky he would be able to get a 'friend with benefits' out of Leon and possibly have his first intimate encounter that very night. Waiting for Leon seemed to take a lifetime. Jacob straightened everything in the house several times, even made sure the bed was made and the bathtub clean. Nothing made him more nervous than trying to get his first time being with a man out of the way. It's not really getting it out of the way, he thought, feet pacing. He was nervous because inside Jacob was still a man. He wasn't a homophobe macho man like a few that he knew, he was more laid back than that. The thought of two men, or women, together didn't make him uncomfortable, he had just never looked at the same sex the same way he did the opposite. Now was his chance to explore that aspect, even if he was a female on the outside. The mental barrier of getting intimate with a man would come down and he would hopefully come away from the experience a little wiser, maybe even a little more sensitive to what gay men were like. I don't think I'd be strictly gay, though, he thought, feet still pacing. He liked women, no, he loved women and all the things they could do and the things he could do. He couldn't do most of those things now but there were still a few options. Maybe I could try a threesome, he thought before there was a knock on the door. Jacob's heart flew and for a moment he stood frozen in his bedroom. Leon was at his apartment, store finally closed. Trying to keep calm Jacob answered the door with a smile and led Leon into the kitchen to get a few beers. The beers were really a crutch for the whole thing Jacob wanted to do. He wouldn't feel so bad if he was completely drunk and had sex but...it wouldn't be the same as being completely aware of the situation. "Let's cut to the chase," Jacob said getting a spurt of confidence. Leon looked at him like he didn't know what was going on and truthfully, he didn't. "I want to work for you," Jacob started then paused. He had no idea how to propose the next idea without sounding...like a girl. "I also want to...be..." the beer went to the new coffee table and his hands made the back and forth motion between him and Leon. "Be...what?" Leon asked. At this point he got a slight inkling of what Rita wanted from him but he wasn't sure. Had she spent all this time thinking about it? "Not together," she said then her brow scrunched. It was cute and endearing to see, Leon wondered if he should throw her a rope or let her struggle with the subject. If he was wrong, though, it would be really embarrassing and would definitely upset her. "Fuck buddies," she suddenly blurted out and Leon was caught off guard. He hadn't expected her to just come out and say it, he was prepared for a few more minutes of cute struggling. "I see and..." "And I want you to treat me the same at work. I don't want to influence or be influenced by this. I don't want to have sex to get special treatment," she finished and nodded. She looked very determined, which was also cute, and Leon couldn't agree more. "Agreed," he said and took a sip of his beer. "I also want," Rita started and took the beer from Leon's hands, "the first time to be clear, unhindered," she said and leaned forward. Jacob didn't even know how to seduce Leon in a feminine way, being coy or seductive wasn't in his repertoire but he didn't need it, not tonight. Leon was already leaning in, gently cupping the soft jaw line that defined his Asian features. "We can do that," Leon said and pressed his lips against Rita's, the softness making him ease into it and relax. She was still a bit stiff but he contributed that to moving so quickly; he hadn't thought she was interested at all after the first kiss but now...now she wanted a fuck buddy and he couldn't agree more. The kiss was stiff to Jacob, it was still odd, he just said that he wanted to have sex with another man, it was more than confusing to him the more he thought about it. So don't think about it, he thought to himself and he finally just relaxed and leaned into the kiss. Leon took the relaxation of his female friend as a good sign so he moved in closer, kissing her more deeply with a little more passion. Having a fuck buddy wasn't about passion, though, it was primal and only to get the primal urges out of their systems. That primal urge led Leon to take the lead and he wrapped an arm around Rita loosely so as not to make her feel trapped. She didn't seemed to mind, in fact, she moved into him more, letting him wrap his other arm around her a little tighter. The make out session was getting intense, they could both feel it and soon fires were burning in both of them. Jacob didn't know what to do or how to transition to anything else but Leon did. He broke the kiss only for a moment to scoop up the little Asian girl and carry her into the bedroom where he set her on the bed and climbed on top of her. Kissing continued until the heat was radiating from the two bodies and Jacob got so caught up that he reached for Leon's belt, Leon leaned back and sat up on his knees to take off his shirt and let Rita get his belt undone. He smiled down at her before scooting back and taking his pants and socks off. He didn't take his boxers off just yet, he wasn't sure if she would be comfortable with getting naked so quickly. Leon wasn't right about that, Jacob didn't hesitate to take his shirt off, he needed no bra and didn't wear one. It was when Leon almost lovingly started to unbutton Jacob's jeans that he started to get uncomfortable. He thought that his manhood would spill out of his pants and pitch a tent so large that the entire world would see it; he almost didn't let Leon take his pants away. They came off nonetheless and were tossed aside, soon forgotten as Leon went back to his position and started kissing the Asian girl again. She was so soft, so warm, so inviting, it was hard not to rip her panties off and take her at that moment but he held back. Not having sex for the last...he didn't know how long, was no excuse to practically rape a girl. A sudden moan almost startled Jacob but when he realized it had come from him he went with it, his hands started to roam Leon's back, he felt the muscles and the difference in skin texture. He had no idea that a man's skin was so much rougher than a woman's. He also didn't know how annoying it was to get poked by a clothed erection until Leon pushed into him a little too much. With slight hesitation Jacob gently ran a hand down Leon's chest towards his boxers, he didn't want to get poked anymore and he was sure Leon would appreciate being free of the restrictive clothing. The only thing Jacob wasn't too sure of was sex itself, he wanted to warm up with something else first, if he could manage it. Leon had to have gotten the hint because he pushed his boxers down then kicked them off with ease. He was looking forward to the moment when he could feel a woman's warmth surround him again. The only problem was that Rita didn't seem ready just yet. She was moaning into the kisses, her hands were timid but exploring; the only thing missing was that she wasn't turned on very much. Leon confirmed it when he brushed a hand against her clothed sex and she gasped. She was warm but not excessively, he wondered if he wasn't doing it for her. Was there something he was missing? Good old oral should do the trick, he thought and gently pulled on her underwear. She reluctantly let it go and watched it as it sailed away over the edge of the bed. Her doe eyes turned back on him and she looked apprehensive at best. "It's been a while," she said knitting her brows together. Leon smiled down at her and nodded. "For me too," he said and leaned back over her. For a few moments they looked into each other's eyes, even though they had just met there was a slight connection of trust between them. They were going to work together, after all, and would see each other on a regular basis. There was no time for animosity to breed itself and drive them apart. "Can I..." Leon started and glanced down before looking into Rita's eyes again. She didn't understand him and he could tell, "warm you up?" he finished and she smiled then nodded after biting her lower lip. Leon was only too happy to kiss a trail down her stomach then position himself between her legs. She wasn't fully relaxed so he took his time wandering around her legs with his lips and hands before slowly moving closer to his goal. Jacob was more than thankful that Leon was letting him get used to the feelings and sensation he was feeling through being touched. It was all so...delicate to him. Everything was new and shivers continuously wracked his small frame every time he felt Leon's breath on his skin. Even as the dark haired man went closer and closer to the female sex of his person Jacob was getting more and more used to the idea that he was going to be intimate with another man. Not knowing there was a man in the mind of his partner Leon finally made it to his goal, first kissing the outer lips of her womanhood then gently using his tongue to lick her as he would a candy. She cooed softly and a small hand found his hair to twirl it in her fingers as he continued his ministrations. She moaned and gasped which only encouraged him and he was soon ravaging her with his tongue far too consumed by his lust and need to even noticed that she orgasmed several times. That need and hunger drove him to move without thinking and soon he was on top of her again, member out from his boxers and pushing against her entrance. He barely had enough will power to stop and look her in the eyes to see if she was ready. When she nodded he pushed in slowly, savoring the tightness and the heat that surrounded him until he was buried up to the hilt. He stayed there, paused, head back and eyes closed, it had been too long since he had been with a woman. It seemed like a miracle that he had a cute one beneath him squirming slightly as he let his member hold still yet throb. When he looked at her again her cheeks were flushed and she was breathing a little heavier. Instead of just pumping away he eased down to his elbows so he could hug her beneath him. "Protection?" he whispered. Even though he was inside of her, ready to pound away he was still considerate, and worried, about needing protection. When she shook her head and smiled he took it that she was on the pill or something similar. With a green light Leon eased back and gently slid back in. She was slick, so slick and so warm; his even rhythm soon started to pick up pace. He wasn't the only one moving, though, Rita's hips started to buck up to meet him and he soon found himself rubbing against a certain spot in her that made him feel is own orgasm come on too quickly. He paused for a few moments and felt her walls clenching around him, had she made it already? Did she want him to keep going? Slightly worried eyes looked down at Jacob but he smiled back. Even though he had just had another orgasm he was more than willing to have a few more. He nodded and once again Leon started to thrust deep inside his new body making him feel pleasure from places he didn't even know he had. The pace picked up quickly, though not as deep, as Leon turned to a fast then hard and fast rhythm. The change in pace was exhilarating to Jacob and he bucked his feminine hips to meet Leon every time until another orgasm exploded leaving him light headed. Leon felt another round of twitching from Rita and decided to change things up a bit. With him still inside her he leaned back but took her with him. She was light enough that he was able to pick her up and keep her around him as he carefully walked to the bathroom. There the giggling Rita hung on tightly as Leon turned on the water for the shower, waited for it to get warm then stepped in. He pinned her against the broad wall so that warm water hit both of them and continued to thrust into her. She held onto his neck and that allowed him to brace a hand against the wall and let the other grip her thigh so he had leverage. Jacob had more control in this position, which made him explore more movements with his new body. When Leon was deep inside of him he found a certain place inside the female body that made Jacob tingle all over and he just wanted the man to stay buried in there rubbing against that spot. He suspected that Leon knew this and was intentionally avoiding it with long hard thrusts. That spot had to effect Leon the same way it did Jacob and he wanted to last longer than that, dragging forth more orgasms from Jacob. Suddenly without any warning Leon pulled out of Rita entirely and set her down but before she could even protest he turned her around and bent her over. Leon was getting too close to his release and he wanted the pleasure to last longer, if he could. But thrusting into Rita from behind just made him lose that much more control and they were soon on their hands and knees, Rita's peach high in the air as Leon grabbed her hips and pulled her to him. He tried to slow down his pace and soon stopped deep inside of her where he rocked for a few moments. He was catching his breath and letting Rita do the same. He was damned if this jaunt was going to be so short lived. Rita looked back at him and smiled slightly. She wiggled from side to side a little bit then tried to push back into him. She had a twinkle in her eyes that Leon was sure he liked but didn't want to give in to. "Hard and fast," she said and pushed back again to emphasize what she wanted. Leon had to smile then nodded before giving her a light tap on one cheek. He steeled himself and started off slow but hard, gripping her hips tightly and thrusting with as much power as he could as such a slow speed. The speed increased quickly, much to Leon's dismay and he was soon pounding into the womanhood he had been longing for, hard, fast and quickly getting closer to his release. Jacob savored the rough pounding and he added to the pleasure by lifting his hips every time Leon pulled out. His goal was to hit that first g- spot on himself and catch Leon's on the way out then in. He knew he was successful when he felt himself orgasm and heard Leon start to grunt. It came on too quickly for Leon and he soon found himself shoving into Rita harder but in a jagged rhythm. His manhood throbbed with exploding seed and he soon just buried himself in her, panting hard and feeling light headed. The two slowly caught their breath and when they did they showered together. Both wore smiles and cleaned silently. Contentment was in the air and words didn't need to be said. Even after they got dressed again silence filled the room but each glowed. Jacob didn't know he could feel so happy and content and Leon was just happy he didn't have to give up on women. He was thankful for Rita and appreciated the fact that they were going to be 'friends with benefits'. Jacob, for once in what felt like his entire life, was happy.