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The Boy Next Door Chapter 1 Between some family money and her divorce settlement, Trish Wilkins could live fairly comfortably without having to work at a full-time job. Now in her late twenties she knew she was considered quite a hottie by most men, and never hesitated to exploit that advantage to get men to do what she wanted them to do. Ever since she was a teenager she had recognized she was different from other women her own age. If there were ever any doubt of that the details of her divorce would have put those doubts to rest. Attracted to each other at first, she and her husband Phil had soon realized their marriage was a mistake. While the divorce papers cited irreconcilable differences as the cause of the breakup, the truth was sexual differences ultimately triggered the split. She wanted Phil to experiment much more than he was comfortable doing, telling him loosen up at least three or four times a month. If their relationship outside of the bedroom had been stronger it may not have mattered as much, but on a night Trish still remembered with a certain amount of fondness she had pushed him too far and he had finally walked out of the house and out of the marriage. For her viewpoint the boy who lived next door seemed young, even if he was nineteen and of legal age. Trish had noticed Mark working pretty hard in his family's yard on a number of occasions, which is what ultimately prompted her to hire him for some minor renovations she had planned. She didn't have anything really big or scary planned, just some new insulation and new walls in both her living room and dining room. Looking for extra cash he readily agreed to the job once she approached him with the idea, although her being the neighborhood resident hot divorcee probably helped his decision as well. Putting him to work starting one Saturday, he managed to do a lot of living-room demolition over the course of the day. "Mark, why don't you knock off for today?" Trish told him, noticing just how dirty he was from all the demolition work he had been doing. "In fact why don't you hop in my shower while I start up the barbeque? Given all your hard work the least I can do is feed you," she added. "I can just pop over to my own house to have a shower," Mark countered. "Don't be silly. My shower is right here. Let me turn it on for you," she said as she walked into the bathroom and turned on the water. Bowing to the inevitable Mark walked into the bathroom and shut the door. Stripping off his dirty clothes he stepped into the shower and started washing himself. Shortly after that he heard the door open and the tap tap of Trish's heels on the bathrooms tile floor. "Mark, I'm putting out a towel for you to use once you're finished in there," she told him. "Thank you Miss Wilkins," he responded, somewhat excited by the fact he was in the shower naked with nothing but a flimsy shower curtain between him and such a good looking woman. "I like it when you call me Miss Wilkins," she commented as he heard her leave the bathroom. After several more minutes of washing himself he felt clean enough to get out of the shower. Stepping through the shower curtain he immediately spotted the towel left for him but couldn't see the clothes he had left on the floor of the bathroom. Opening the bathroom door a bit he stuck his head out and called out. "Hello! Miss Wilkins! What happened to my clothes?" Not receiving any answer he dried himself off and wrapped the towel around his waist. No longer naked he stepped out of the bathroom and went in search of his host, finally finding her in the kitchen. "There you are. I was wondering what you did with my clothes?" he asked again, this time confident he would get an answer. Unfortunately the answer wasn't the one he expected. "Oh those. I threw them in the wash for you. They were so dirty I couldn't imagine you putting them back on after you had gotten all clean," she told him. "What am I going to do for clothes while mine are in the wash?" he asked in exasperation "I'm sure I can come up with something," she told him as she stepped close to him and pressed her lips against his. Suddenly her tongue darted into his mouth and Mark found himself being thoroughly and expertly french kissed by a very attractive woman. Not surprisingly his growing erection started pushing against the towel he was still wearing. "Why don't you come with me," Trish directed once she ended the kiss. Taking his hand she led him towards the back of the house to what appeared to be her bedroom. "I've got just the thing for you to wear," she told him "I want it to be a surprise though, so just let me put this blindfold on you," she explained as reached up and covered his eyes with a section of cloth she picked up off the dresser, tying it firmly in back of his head. Mark then heard the sound of a drawer opening and Trish sorting through the stuff inside the dresser. "I'm surprised you have men's things in the house," he commented. "Why would you be surprised? I was married until very recently," she commented. "I would have thought Mr Wilkins would have taken all his clothes with him when he left," Mark responded. "Most of his things yes, but with some of the things I bought specifically for him he left them behind. Since he didn't want this particular item I want to see how it looks on you. You're about the same size as he is so it should fit you fairly well," Trish told him. "Now I hope you're not excessively shy because it's time to remove your towel," she told him as she grabbed the towel wrapped around his waist and yanked it off, revealing his fully erect penis. It was obvious all of the touching and the mystery was really getting Mark really horny. "Now lift your left foot for a second and back down again. Very good. Now the same for your right foot. That's great. Now you'll feel me sliding the garment up your legs," Trish instructed him. "Yes, I do feel it but it feels kind of odd," he complained. "Well yes, that's because it's actually a costume I had specially made for my ex-husband. Personally I just loved the way he looked wearing it, however he didn't want it enough to take it with him when he left. Here, let me just gently tuck your penis down and out of the way," she told him as she grasped his penis and pulled it downwards before sliding the costume further up his legs. By this point Trish started working the the garment up his body and it felt even odder than before. It started pressing on his ass, stomach and back and was starting to feel very snug across his entire torso. Strangely there was some kind of pouch built into the costume that trapped his penis and pulled it snugly between his legs. "What exactly is this costume?" he asked nervously, starting to wonder what kind of costume she was putting on him. "I told you, it's a surprise. Just relax and let me finish doing this," she scolded him before pressing her lips against his and giving him another french kiss while rubbing his penis through the material of the costume. The kiss seemed to go on for a long time before Trish broke it off and started pulling Mark's costume into position once more. Suddenly it seemed to be fully in place as Trish started sliding a zipper in the costume up his back. While he initially thought the costume quite snug, it was pulling against his body harder and harder as Trish slid the zipper up his back. Stopping just below his shoulder blades, instead of snug he would now describe the costume as very constricting. Beyond that however in important other ways the costume felt completely wrong. For instance the front of the costume felt like it ended a little below his collar bone, the back of the costume ended under his shoulder blades and he could feel boning built into the costume digging into his skin at various points along his torso. The front of the costume also felt like it had some extra weight at the top, causing his hands to start automatically moving towards that part of the costume to figure out what was causing the weight. Before his hands could start exploring Trish grabbed his hands and held them tightly. It was at this point Mark started thinking to himself that he had never heard of a man's costume using boning and certainly couldn't imagine one that should feel this way. It was then the first doubts began to enter his mind. Because Trish had told him she had bought the costume for her ex husband Mark had been assuming all along it had to be a man's costume she was putting on him. Suddenly he had a dark suspicion Miss Wilkins had bought Mr Wilkins a woman's costume and had now tricked him into putting it on. "I really need to see what I'm wearing," he told her as firmly as he could manage under the circumstances. "Okay honey, it's time for the unveiling. Stand up and step over this way so you can see yourself in the full length mirror," she told him as she guided him a handful of steps across the bedroom. "That's perfect, time to remove your blindfold," she told him as grabbed the front part of the cloth and pulled it off over his head. Mark almost fell over when he saw his own reflection staring back at him. Trish had just put him into a Playboy bunny costume complete with built in falsies, padded hips and a bunny tail. Reaching between his legs Trish started stroking his penis vigorously through the material of the costume, making sure Mark got rock hard while dressed in one of the sexiest womens costumes imaginable. Turning slightly sideways he could see in the mirror that the costume immediately drew the eye to his tits and ass, to the point where he couldn't pull his eyes from them even though he knew they were mostly fake. "Why have you done this to me Miss Wilkins?" he asked her as his hips started to thrust forward in response to her stroking. "I wanted you all nice and feminine for me," she admitted as she continued to masturbate him. "Phil was occasionally willing to wear a bra and panties for me, but when I bought him this costume and asked him to put it on and serve me drinks he balked and asked for a divorce. Since then I've been looking for a man who is secure enough in his masculinity to really embrace his feminine side like this. I thought a young and uninhibited guy like you would be willing to be playful without getting all bent out of shape about masculine and feminine clothes," Trish explained as she continued stroking him. By this time his penis was pushing hard against against the costume and Marks hips were thrusting back and forth. "Oh honey, you are just so sexy like this!" Trish exclaimed as his orgasm started to build. "Don't you just love the feeling of having breasts filling out the top of your costume, straining the cups of the built in bra as they add that extra weight to your chest. The feeling of extra padding in the hips so the costume draws the eye to your ass. Dressed the way you are anyone seeing you will definitely be checking out your tits and ass Mark. How does that make you feel? People not only looking at you as a sexual object, but as a female sexual object." Between the way she was masturbating him and the way she was talking to him it was all too much for a sexually inexperienced teenager. Mark started to ejaculate inside the crotch of the costume, spurting for a good twenty seconds before falling down on Trish's bed exhausted. Removing her hand she let him lay there for a few minutes while she went to attend to other things. Finally she returned with a wet wash cloth. Helping him to sit up on the bed, she stripped him out of the bunny costume and started cleaning up his crotch with the wash cloth. "Your clothes are finished being washed but are in the dryer at the moment. I'll just lend you some panties, shorts and a top while you are waiting," she told him as she slid a pair of panties up his legs. This was followed by a pair of shorts that were a little on the girly side of unisex and a top that also looked a little feminine. Once dressed she led him into her fully fenced backyard and where she handed him a beer while she started to barbeque some food for the two of them. Being outside dressed as he was Mark was pretty self conscious at first, however a few beers later he was feeling a lot more mellow about it. Once he calmed down and forgot about the clothes he quite enjoyed himself chatting with Trish. "So Mark, can you come back next weekend to do some more renovation work?" Trish asked him an hour later. "Sure Trish, how about next Saturday?" he replied. "Mark honey, no matter what happens between us I want you to always call me Miss Wilkins instead of Trish. That will help keep our respective statuses in this relationship perfectly clear. Getting back to the original question, you coming over next Saturday works for me. Here is the money you earned today, and here are your clothes fresh from the dryer," she told him handing him his money and the shirt and pants he had worked in. "Also here is a bra and panty set that Mr Wilkins used to wear for me when I was feeling particularly horny," she added handing him a plastic bag containing the underwear. "I want you to have your own bra and panty set at home just in case you suddenly feel the need to be more feminine. With the lingerie handy you can put them on and pretend you're a woman," she told him. Before he could protest she guided him over to the gate in her fence and sent him towards his own house. As it was dark by this time she had apparently decided there was no need for him to change out of the slightly girly outfit he was wearing, especially walking only one house over. Keeping to the shadows just in case someone was looking out a window, he snuck in the backdoor to his house and tiptoed down the basement steps towards his room at the back of the house. Thankfully no one in his family spotted him and he was able to change into his normal clothes without incident. Chapter 2 The following week passed uneventfully, except for the cheerful wave from Miss Wilkins when she spotted him mid week. The package she had given him along with the clothes he had worn home stayed hidden at the back of one of his drawers all week, although he did think about both occasionally. Finally on Friday he pulled out the package and examined the bra she had given him. It was a plain white bra with smooth cups and no real lace, so other than the fact it was a bra he couldn't complain it was overly feminine. After staring at it for ten minutes or so he finally decided to try it on. It wasn't so much that he had a major urge to cross-dress. It was more because he suspected if he wanted to continue his sexual relationship with Miss Wilkins she would insist he wear things like the bra, and he wanted to determine whether he could go through with it. Picking the bra up he fumbled around for a few minutes but finally managed to get his hands to line the fasteners up at the back of the bra and hook himself into the garment. It definitely felt odd to be wearing something like that on his chest, but it didn't feel as 'wrong' as he thought it would. It really just felt like an odd piece of clothing to him and nothing else. He found himself getting a little aroused not so much from the garment itself but more from the sense of what Miss Wilkins would do to him once he was dressed like this. Out of curiosity he donned the panties, shorts and top he had worn home the previous weekend. Again it didn't feel that odd but he did get a little more aroused thinking of how his neighbour would react to seeing him dressed like this. Dressed as he was he didn't want to masturbate, so Mark started stripping off the clothes. He struggled a little to undo the bra but finally managed to unhook himself and let the bra drop to the floor. Finally naked, he lay down on his bed and started stroking his penis as he thought about Miss Wilkins. It wasn't long before he started ejaculating for what certainly felt like as long as he had ever done it before. His knees were so weak when he was finally done he had to spend a few minutes laying on the bed before he could stand up. Even though he was working at her house the next day Mark still ended up masturbating twice more just thinking about the next encounter with her. He was quite happy he was scheduled to arrive at her house by 8 am the next day, meaning he would wake up, shower and head directly there. She greeted him sweetly when he arrived, but quickly got down to business. "Mark, before you start doing more construction I want you to really understand the situation here. If you only want to make some extra money working for me that's perfectly fine. You do the work, I'll pay you, you'll go home. On the other hand if you are interested in exploring our sexual relationship even further than we did last weekend that comes with some conditions. I determined years ago I am completely straight. However I also came to realize that even though I have no desire to sleep with women, I do want my male partners to display a very strong feminine side. At first Mr Wilkins played along with my desires, letting me put him into nightgowns and womens lingerie. He finally balked at being feminized when he realized I would keep expecting more and more from him as time went on. Deep down he felt being married to me entitled him to sleep with me, however I decided there was no way I was going to let him sleep with me unless he allowed himself to be increasingly feminized. I'll insist on the same thing from you, continually pushing the boundaries of your own feminization. If that's going to be a problem for you we should end things right here and now. To be blunt if you want to keep sleeping with me you have to do exactly what I say, no exceptions. If you ever say no to one of my suggestions our sexual relationship is finished forever. On the other hand if you say yes eventually I will do things like bringing you into a lingerie store for a bra fitting and telling you to wear a dress and high heels in public. Now I'm sure all of this is a little overwhelming at the moment, so why don't you get to work right now and think about what I've said. You can give me your final decision later today," Trish told him. Eight hours later Mark still wasn't sure he had sorted things out to his own satisfaction. He knew he definitely wanted to keep sleeping with his sexy neighbour, but the thought of being increasingly feminized by her was pretty daunting. He had always considered himself your typical red blooded guy and what Miss Wilkins was proposing flew directly in the face of that belief. Miss Wilkins came and got him around dinnertime and he once again allowed himself to be talked into having a shower at her house. Once his shower was done he dried himself off and wrapped a towel around his waist before allowing Trish to guide him to the kitchen. "Well honey, have you decided yet?" Miss Wilkins asked him as the two of them sat across the kitchen table from one another. "No, I still can't decide. The whole thought of wearing womens clothes for you makes me uncomfortable, even if I don't hate the idea. It's just so contrary to the way I was brought up. I was always being taught that boys dressed liked boys and anything else was just plain wrong," he explained. "I suspected you might feel like that. Most boys in this country have been raised that way. However in spite of your upbringing it doesn't mean what I want you to do is wrong. After all we're only talking about some clothes. It doesn't change who you are inside or even affect your sexual orientation. People have been wearing clothes for thousands of years. You really believe if you put on a dress it will have some great impact on civilization, considering half the population already wears them?" Trish asked him. "No of course not. I can see what you're saying from a logical standpoint, however emotionally it still feels very odd," he told her. He could feel that deep down he wanted her so badly he might be willing to ignore any feelings of wrongness he might have about the clothes. Still not sure what to tell her he finally decided to tell her what he had done yesterday. "Before I give you an answer I have a confession to make. Yesterday I tried on the bra you gave me last weekend," Mark admitted as his face went red. "Well isn't that interesting!" Trish exclaimed. "How did you put it on? Did you put it on backwards and then spin it around forwards and slide your arms through the bra straps? Trish asked curiously. "Ah, no. I slipped the straps up my arms and then reached around behind me and hooked the bra up," he admitted, his eyes staring at the floor. "Oh honey, that's wonderful. Show me!" Trish exclaimed. "What do you mean?" he asked puzzled. "I want to see you put on a bra just as you did yesterday, just as a woman would do it. Stay there while I go get you one," she told him as she headed to her bedroom. Returning about a minute later, she was carrying a lacy pink padded bra. "Here you go. This should fit you," she told him as she handed him the bra. "This is another one of the bras I bought for Phil that he left behind when he divorced me. It's your bra now," she told him. Taking her ex husbands bra from her, he stared at it for a minute. With a sigh he put his arms through the straps, pulled the bra up until it was pressing against his chest and then reached behind his back to hook it in place. It took him thirty seconds and a couple of tries before he succeeded but eventually there he was, Trish's young lover standing in front of her wearing a heavily padded bra. She had bought this particular bra for Phil because it promised to add two cup sizes to the wearer, which meant Mark was suddenly sporting a B cup sized chest. "I didn't think you would be ready to go for your bra fitting appointment anytime soon Mark, but I'm obviously wrong. Phil never got to the point were he could put his bras on that way, so if you're able to do it in your first week it's obvious you have a lot more feminine potential than he ever did. Still, even though I'm very tempted I'm not going to take you for a fitting today or even this week. First I'll give you a bit of time to get used to the whole idea of trying on bras in a store," she assured him. "Instead of the lingerie store, today I am going to do some work on a dress for you. Earlier this week I started putting together the basic pieces of your first dress, and now I need you to try it on so I can start adjusting it to your body. It will take a bit of time to finish, however once it's done I'll take you out somewhere in public wearing your new dress," she informed him. "Leave your bra on and put on some panties and we'll get started," she added as she went over to the closet and pulled out a partially finished dress. After he donned the panties Trish had Mark step into the dress and then pinned it in place on his body. She then started making other adjustments, putting pins in the various places she would need to take it in or let it out. Mark couldn't believe the odd feelings running through his body at the thought that Miss Wilkins was making a dress for him. What normal young man would stand there and let this happen to him he wondered. Then he started thinking a lot of his horny teenage buddies might just do this if it meant sleeping with Miss Wilkins. After that thought occurred to him he felt a little better, so in spite of any misgivings he allowed the dress adjustments to continue. After ten minutes of adjustments and pining Miss Wilkins finally took the dress off him. "I'll make the adjustments this week and next weekend have you try it on again. After I do your second dress fitting I should have the dress ready for you to wear within a week or so, which means something like two weeks from today. I have to tell you this is just so exciting! I get to be part of both your very first dress and your very first bra," she said as she put away the dress. Leaving him in the padded bra and panties, she led him to the bedroom and rubbing his nipples through the bra and his penis through the panties. She kept going until he started spurting all over the inside of the panties, stopping when he finally sank back onto the bed exhausted. "That was a lot of fun!" Trish exclaimed "Dressing a guy in womens underwear and masturbating him to climax is always so much fun. I always loved doing it to Phil while we were married. Also as I mentioned earlier you just have so much feminine potential it's wonderful. I'm really looking forward to finishing my sewing project so you'll have a dress of your own you can wear whenever you're feeling particularly girly," she told him. "I think I already know the answer, however have you decided you will accept any suggestions I make and continue our sexual relationship?" she asked, looking for an answer to the question she had put to him earlier that day. Mentally Mark kept asking himself whether the amazing sex was really worth what she was doing to him, and kept coming up with the answer that yes, it was worth it whatever she had him do. After all, he reasoned he could always get out later if she started taking the whole thing too far. "Yes, I want to continue our relationship. I will do whatever you tell me to do," he told her, finally committing to letting her cross-dress him whenever she wanted to. "That's great. I'll see you here around 9am tomorrow then," she ordered. Chapter 3 Showing up first thing in the morning the next day, Mark was a little surprised she didn't put him to work immediately. Instead she pulled him out the door and into her car. Once they were driving the two of them soon arrived in front of a mall Mark had never been to, given it was a little distant from their neighbourhood. Trish explained she wanted to do a little shopping and would enjoy having his company on the trip. Mark was a little preoccupied with the idea Trish would expect him to wear a dress in public sometime soon. That's why at first he wasn't paying much attention when the two of them stopped by an jewelry kiosk in the local mall. "My boyfriend Mark would like to get both his ears pierced twice, and then we'll pick out some nice earrings to go in his new piercings," Trish informed the teenage girl working the kiosk, whose name tag identified her as Bonny. "Not a problem. I'll do the piercings first and then we can discuss what earrings he's interested in," she said. Mark soon had both ears pierced, at which point Bonny started talking about the earrings themselves. "Most men are interested in either the tiny hoops or the small diamond solitaires. With two piercings you might like one of each," she suggested. "Actually I think those inch and a half silver hoops will look good in the lower piercings, and that single pearl in the upper," Trish pipped up. "Okay. You may not be aware that both of the earrings you picked out are generally considered womens earrings. To be honest I don't remember ever having a man buy either of the sets for himself. Are you sure those are the ones you really wanted for your boyfriend?" Bonny asked Trish, apparently decided she was making all the decisions in this case. "Thanks for pointing that out, however the whole point of this is for Mark to start wearing womens earrings. He has started to let me gradually feminize him. Over the past few weeks he has worn a bra and panties plus a Playboy bunny suit, and at the moment I am sewing him his first dress. Having him put on womens earrings is an excellent next step while he waits for me to finish his first dress," Trish explained. "Okay, the large hoops and pearls it is," Bonny responded, proceeding to insert the indicated earrings into Mark's new piercings. "Anything else you ladies are looking for today?" she asked. "Oh, I like you referring to him as a lady. Yes there is something else I'd like to look at. Do you have any cute bracelets that will go with his new earrings?" Trish responded. "Yes, we have a few. Let me show you," Bonny replied, pulling out a few different possibilities, all of which were quite pretty and clearly designed for women. "You may also be interested in a pretty ankle bracelet for Mark. They are all the rage with teenage girls at the moment," she commented, pulling out a chain with several small hearts between the chain links. Taking her cue from Miss Wilkins, Bonny was obviously only suggesting jewelry from the womens collections. "Oh, a few of those look about right. I think he will look just darling in one of those silver pieces," Trish replied, pointing to a few of the prettier bracelets. A typical man would never be caught dead wearing something like that, which in Trish's mind is what made it perfect. "We will also take that ankle bracelet for him. I like the idea of him wearing a pretty ankle bracelet even when he isn't wearing his other jewelry. A kind of constant reminder of his new status," Trish commented. Mark soon had the chain wrapped around his ankle, and found himself trying on several different bracelets before Trish settled on one he would have never purchased for himself, indicating she wanted him to wear it now. During the entire time he kept looking around nervously, afraid someone he knew would spot him shopping for womens jewelry for himself. "You know putting him in such pretty jewelry but nothing else seems a shame," Bonny commented. "I don't know whether you have thought about having his nails done all nice and pretty, however there is this darling little place down at the end of the mall that can do the job if you are interested. They'll do tips, french manicure, little heart shapes, all of the popular looks for teenage girls," Bonny commented. "That is interesting!" Trish exclaimed as she paid for the earrings, bracelets and ankle chain. "I had only been planning on some jewelry purchases for today but I quite like the idea of Mark getting his nails done as well. In fact we could both get our nails done at the same time," she added as Mark looked slightly green. Grabbing his hand she pulled him towards the part of the mall indicated by Bonny. "Here's the deal Mark. I've introduced you to womens earrings today so I normally wouldn't ask you to do anything else new for the rest of the week. However if you have your nails done today as well, sometime in the future I'll give you a complete pass where I won't ask you to do anything new for the entire week. What do you think?" Trish inquired. "Just to clarify if I don't do this we won't be sleeping together anymore?" he commented. "Yes, of course. That's the agreement," Trish responded firmly. "Okay then, sure," he finally responded after realizing that by doing this today he might delay appearing in public in a dress for a least a few weeks. He reasoned to himself that before the dress was ready he might be finally willing to give up the sex and break off things with Miss Wilkins for good. Once he had agreed the two of them walked away from the kiosk and soon arrived in front of the nail salon. "What can I help you with today?" the pretty blonde receptionist inquired, giving Mark's feminine looking earrings and bracelets an extra long look. Not surprisingly Mark was too tongue tied to respond. "My boyfriend Mark and I would each like a manicure and pedicure, nail extensions and a cherry red polish to finish," Trish informed the young woman. "You want the extensions and nail polish for both of you?" the woman verified, raising her eyebrows in a small show of surprise. "Absolutely. I can't wait to see how Mark will look with really pretty nails. While it's being done we'd like to sit side by side if possible. Part of the fun will be to watch while the work is happening," Trish commented. "Well then you're in luck. A couple of our consultants are available right this moment. We can take both of you immediately and give you the side by side stations you want." she told us. "Wonderful. Let's do it," Trish exclaimed. They were escourted to adjoining workstations by the receptionist. A pretty Asian girl appeared immediately, and once she knew what was requested started working on Mark's nails. While Mark was tempted several times to get up and leave, given the alternative he continued to put up with the odd sensation of having his nails worked. He watched in fascination as the woman glued extensions onto his existing fingernails, applied a special goop to blend everything together, and used a nail file to shape his nails into the oval shape women favoured. This was followed by her applying a bright red polish on both his fingernails and toenails, with the end result being his nails looked identical to what you would see on a stylish young woman. As the work progressed Mark started to feel a stirring in his loins, until he finally had to acknowledge something was getting him aroused. Whether it was caused by the work he was getting or the fact that Miss Wilkins was so thoroughly in charge he wasn't completely sure, but it was undeniable something was doing the trick. Although he really didn't want Miss Wilkins to realize something was getting him sexually excited, unfortunately he wasn't subtle enough in his movements and was quickly spotted by the nail technician. "I think your boyfriend is getting turned on by having his nails done all nice and pretty," the woman working on Mark's nails commented to Trish as she continued to apply the polish to his nails. "Really! Is that right Mark? Are the earrings and the nail polish doing giving you an erection?" she asked him. Instead of replying Mark blushed a bright red, to Trish's mind confirming exactly what she said. "Oh yes, I've had guys like him come in here before," the nail technician commented. "They try and play it cool, but you can tell getting their nails or makeup done as if they were a woman gets them so horny that can't control themselves. I have to admit though, I'm a bit surprised he didn't come in dressed in at least some items of womens clothing. Guys like him almost always are partially or fully cross- dressed while I work on them," she added. "If you're interested I know of this wonderful lingerie shop over on Main Street that is a bit edgy. I'm fairly certain they would do a bra fitting for a guy if asked. I've got a friend who works there, so I could find out for you if you're interested," she offered. "Yes that is definitely something I want to know. I had already planned on putting him through a full bra fitting appointment sometime soon. Can you call the shop right now and see whether they deal with male clients?" Trish requested. "Sure, why not," she responded, putting down the nail polish and picking up her phone. It sounded like someone answered the other end almost immediately. "Hey there Gloria, it's Sun Li. Just a quick question for you. Does your shop do bra fittings for guys?" she asked before pausing for a response from her friend. "No, no, not for anyone I know. I'm working on a guy's nails at the moment, giving him the works but he's dressed completely in men's clothes. I think I mentioned to you before how unusual that is for guys like him who have their nails done. Anyway I asked his girlfriend if he's had a bra fitting yet. She told me not so far but it is definitely going to happen eventually. That's why I wanted to know if your shop has any problem with guys trying on bras in the store?" she asked, loud enough for the entire salon to hear. Several of the other customer turned towards Sun Li and seemed to be waiting to hear the answer she got. "That wonderful. I didn't think it would be a problem. Their names are Mark and Trish, and I'm sure both of them will be happy your store is so open minded about that kind of thing. I believe they will be interested in looking at both bras and breast forms for Mark when they come in. That's right, the forms you can glue in place for a few weeks at a time. I'll give them the good news along with your location," she said before hanging up the phone and turning back to the two of them. "It's all set whenever you want to go. Here's the address, and you can ask for Gloria if you want to when you shop there," Sun Li told them as she wrote the address on a piece of paper. "Thanks a lot Sun Li. We're a little busy today, however I'll definitely take Mark there sooner or later," Trish commented. By this point Mark wanted to sink through the floor of the salon, but somehow endured until his nails were done and dry. Sun Li had done a nice job, making them as pretty as any nails he had ever admired on a woman. Mark started wondering both how he was going to change him nails back to normal, plus how he could avoid going bra and breast form shopping with Miss Wilkins. He had no desire to shop for either item, and was dismayed by the whole idea of doing something like that in as public a place as a lingerie store. Somehow he endured the rest of the appointment, and even made his thanks to Sun Li sound sincere. He was very thankful when he and Miss Wilkins finally left the salon and headed home. Once they got back to her house the two had a quickie in the bedroom before Trish put him to work for the rest of the day. It felt odd to Mark doing construction work while wearing nail polish, earrings and bracelets, but after hours of work he was gradually getting used to the feeling. Finally Miss Wilkins came up to him, gave him a very long and deep French kiss and told him he was done for the day. "Here you go Mark. I want you to leave the nail polish on your toenails, however if you really want to take it off your finger nails you can use this polish remover once you get home. The remover will also work on those extensions Sun Li glued on," she told him as she handed him a bottle of nail polish remover. "Thank you Miss Wilkins. I will definitely want to do that," he told her as he accepted the bottle. "Okay then, we'll see you later. You can plan on working here next Saturday again unless I contact you during the week and make other arrangements. Until then enjoy yourself," she told him Chapter 4 It turned out Miss Wilkins didn't need him during that week as she didn't contact him, so first thing Saturday morning he showed up at her house once again. "I need you to try on your dress again," Trish informed him as soon as he arrived. "I've done some work on it this past week and need to note any final adjustments it will require before it's ready for you to wear. Why don't you put on a bra and panties and we can get started," she ordered him. This dress Miss Wilkins was making was still causing Mark a lot of concern. Walking through a mall for ten minutes wearing earrings was one thing, while wearing a dress in public all day was something else entirely. Even though he had bought himself a few weeks by wearing the nail polish, that time would soon be up. Thankfully the dress wasn't quite ready, which meant he might be able to avoid wearing it for an extra week or two if he was lucky. He still wasn't sure he could go through with wearing a dress in public, but was still unwilling to terminate a sexual relationship with a hot divorcee. Even though the dress wasn't quite finished, spending fifteen minutes wearing even a partially finished dress felt odd to Mark. He was thankful when Miss Wilkins finally allowed him to take off both the dress and the padded bra and change back into his regular clothes. "Great. Why don't we get going," Trish told Mark once he had finished changing. Guiding him to her car they soon drove off towards downtown. Mark wasn't paying that much attention to where they were going so didn't realize the significance when Trish turned onto Main Street. Once they pulled into the parking lot of a store with a large window display of bra wearing mannequins he started to understand the purpose of this trip. Thinking back to the phone call in nail salon he suddenly realized he would be trying on bras within the next few minutes. As he had earned that one week pass for getting his nails done he had been assuming Miss Wilkins would use the pass this weekend, but apparently it was being saved for future use. Unfortunately as per their agreement he had absolutely no say in the matter when it came to such things, and allowed her to guide him inside. "This place is just perfect," Trish commented as the two of them stepped into the store. Admittedly there was a lot of lingerie on display, from the sexy to the naughty, and all of it was very pretty. Before Mark could respond to her comment a saleswoman approached the two of them. "I'm Gloria. How can I help the two of you today?" the woman greeted them. Sandwiched between a hot divorcee and a pretty twenty something saleswoman Mark was in heaven. "Hi there Gloria. You must be Sun Li's friend," Trish replied. "I'm Trish and this is my boyfriend Mark. Today we're actually here to buy some things for Mark, unfortunately we're not really positive about his sizes in women's lingerie. Lately he's been wearing a couple of bras that belonged to my ex husband, but has never gone through a proper fitting to establish his own bra size. If he is going to start wearing women's underwear regularly and present himself as a woman I wanted him to go through a proper fitting. I understand your shop can help us with that," she explained as Mark blushed a deep red. He knew it would have happened eventually but was pretty embarrassed Miss Wilkins had revealed his secret as soon as they entered the shop. "No problem at all. I'm free right now to give Mark a bra fitting," Gloria exclaimed. "For starters I'll walk him through what we in the store call Lingerie 101. It's a bit of a process we've put together over the last few years to introduce teenage girls to the world of lingerie. While it was designed with young girls in mind, the few times we've used it on males like him we've found it works equally well. Please come with me Mark," she finished, grabbing his arm and leading him deeper into the store. "First let's talk about your bras. It's a basic piece of underwear for a girl, but of course feminine guys like yourself need to understand the ins and outs of a bra as well." "What do you mean by feminine guy? I don't consider myself that at all!" Mark told her. "Come on sweetie, get real. You're a teenage boy who's come in for a bra fitting. I don't think calling you feminine is out of line. Now getting back to the matter at hand, from what Trish said bras haven't become a part of your everyday wardrobe as yet, however once she wants you to wear a bra everyday trust me when I say you really don't want them riding up on you, the straps falling off your shoulder or the cups puckering out from your chest. After you've been wearing a bra all day you'll really start to appreciate the difference between a properly fitting bra and a poorly fitting bra. If you'll just step over here to this rack of bras here I can start explaining some of the difference types of bras you might want to wear," she told him. Picking a bra off the rack she stepped towards him and started rubbing the bra cup along Mark's cheek. "Feel the fabric this bra is made from," she commented before picking up a second bra. "And now this one," Gloria added as she stopped rubbing his cheek with the first one and now started rubbing the second one along his cheek. "You can really feel the difference can't you? The first one is very soft while the second one is a bit rougher but feels much sturdier. Think how each bra cup would feel against your skin if you put it on. It isn't quite as important for you because you are so flat chested, however for a lot of women they have to decide if they want to buy a bra that feels better against their skin or one that will last them longer and provide better support to their breasts," she explained. "You should also be aware of what under-wires do, and decide if you want your bras to have under-wires or not," she continued as she gathered up a handful of bras and handed him an under-wired bra to examine. "You likely already know an underwire is semi circular wire that runs below each cup of a bra, but you may not realize the under- wires are there to give the bra better overall structure. Of course there are some women and even men who complain the under-wires of their bra dig into their skin, but I've generally found that only happens if the person is wearing the wrong size bra. If your bra fits you properly there is no reason the under-wires should be uncomfortable or dig into your skin," she explained as she helped Mark trace the under-wires running through each bra cup. "Certainly today I'll make sure you only buy bras that fit you properly. Personally I think you should have under-wires in all your bras and take advantage of the better structure they provide, but that choice will ultimately be up to you," Gloria told him. "Next you need to decide if you want padding in your bras. The padding helps to both hide the nipple and make your breasts look bigger," she explained as she removed the foam pads from the underwire bra he was holding and showed them to him. "Because you are so flat chested I'll assume you want all the help you can get to make your breasts look fuller, which means I'll be bringing mostly you heavily padded bras to try on. I should mention if you are planning on stuffing your bras with breast enhancers or breast forms most of the time then the padding becomes much less important," she added. "Finally you have to decide on the shape of the bra cups. The most common choices are pushup bras, full cup bras and balconette bras. Here is a pushup bra," Gloria said, picking up a bra from the pile and pressing the cups against his chest while leaving the bra straps and bra band dangling down. Even though she didn't actually put the bra on him, Mark felt very odd having a bra positioned on him as if he were about to wear it. "The cups are designed to encase the breasts but push them upwards and towards each other, drastically increasing the amount of cleavage you have. The purpose of the full cup bra is little different," she commented, dropping the pushup bra and replacing it with a full cup bra in the same color scheme. "This is designed to cover the entire breast, and provide good overall support for the wearer. If you want to be a fairly busty girl Mark, and start wearing sizable breast forms regularly you may want to wear a full cup bra to support them properly. Even if you glue the forms to your chest you'll still want the support a good bra provides you. On the other hand if you stick to smaller forms you'll be able to get away with wearing something like the pushup bra instead." "Finally there is the balconette bra," she told him as she removed the full cup bra and positioned a new bra on his chest. It was at that moment that a couple of teenage girls appeared, staring at Mark as Gloria continued to press the bra against his chest. "You likely won't be wearing one of these anytime soon as they only have partial cups to support the breasts," Gloria continued speaking, to all appearances unaware of the attention of the two girls. "They are not really designed for the breast forms you'll be wearing to fill out your bras, this style being much better suited to real breasts. I'll have you try on a few of balconette bras in case you are interested, however they may not be too practical for you unless you decide to get breast implants or decide to wear bras regularly without your breast forms," she explained as the teenage girls were overcome with a giggling fit. Turning to the girls Gloria addressed the two of them. "I can help you ladies once I determine Mark's bra size and select the first few bras for him to try on," Gloria told them. "Do you mind waiting for a few minutes for me to finish with him?" she added, continuing to ignore their giggles. "No, not at all. Please get Mark all set up first. We'll look around the store while we're waiting," the taller dark haired one said when she finally managed to say something coherent, and promptly broke down in giggles once again. "Great. I'll find you once I'm free," Gloria promised before turning back to speak with Mark. "Now let's start you trying on some bras," she commented, ignoring the deep red color he had turned as a result of the interaction with the teenagers. Guiding him to a change room she helped him remove his shirt and pulled out her measuring tape. "I am going to try you in a 38 band size for starters," she informed him once her measuring was complete. "Personally I think a C cup will work best for you in proportion to your body size. With that cup size you can start wearing a pair of larger size breast forms and really fill out your bras well, and of course the size and weight of the forms will be a constant reminder of your new look. Unfortunately the store doesn't carry breast forms, but instead we carry a product called enhancers or fillets. I mentioned those to you earlier without explaining them. Essentially it's a product designed to add or enhance breast volume for the wearer, not really create an entire bust for someone who is flat chested. What I'll do for the moment is put you in some 38B bras with heavy padding and add the enhancers as well. That should let you fill out a B cup bra nicely, and if we find your bust should be bigger I can then put you in some C cup bras in the same style. That way once you get some breast forms you won't have to go bra shopping for new bras. Of course you may find you enjoy bra shopping for yourself so much that you end up going every so often just for the sake of getting some new bras. Some of my male customers come in every few months to shop for new intimates," Gloria added to a speechless Mark. "Stay put and I'll be right back with the first batch for you to try on. And leave your shirt off. You'll need to try the bras on over bare skin or we won't be certain they fit you properly," she added as she headed out of the cubicle to gather bras for him to try. Mark started getting that same feeling of embarrassment and arousal he had while getting his nails done. Part of him wanted to flee, part of him was intrigued by what he was going through however the biggest part of him by far didn't want to give up sex with Miss Wilkins. Gloria soon reappeared carrying a handful of bras, quickly dropped all but one on a convenient chair and started threading the one she held up his arms. "I thought I would try a nice under-wired, full cup bra on you first," she commented as she stepped behind him and hooked his bra closed. "With my male customers I typically try this style first and have usually had very good results." Reaching into the pile of bras she produced a couple of odd jelly like objects and promptly inserted one into each of his bra cups. "These are your enhancers. As I mentioned before they will fill out a padded B cup very nicely, but at some point you should still consider getting proper breast forms to give you a bust-line properly proportional to your size. I mean what's the point in you wearing a bra unless you're going to have a proper bust. The enhancers will at least start getting you used to having something filling out your bra cups," she commented as she started adjusting his bra straps. "There all done, what do you think? How do you like the feeling of having breasts," Gloria asked as she stepped back to admire her work. Mark was tongue tied and didn't reply. "Oh my. I can see part of you really likes having boobs," she commented as she glanced at his crotch. Being put into a well filled full cup bra had really excited him on some level, that arousal evident by the way the front of his jeans were being pushed outwards. "Why don't I leave you alone for a minute to calm down. Once you're ready feel free to try on some of these other bras I've brought you. Meanwhile I'll go attend to those two women who are waiting," Gloria commented as she exited the change room. The embarrassment of being caught like that caused his erection to subside. Not knowing what else to do Mark then attempted to remove the bra he was wearing and put on the next bra close at hand. It was a bit of a struggle, and he had just managed to switch bras when Trish suddenly appeared in the change room. Unfortunately putting a bra on himself had gotten him aroused once more, even more-so than when Gloria had helped him. As she stepped through the curtain Trish immediately spotted his reaction to the situation. "Gloria mentioned trying on bras was getting you horny, and she wasn't kidding," Trish commented as she slid her hand down the front of his jeans and started rubbing his penis. "Do you want me to take you home wearing your new bra and finish dressing you up completely as a woman?" she asked as she continued to stroke him vigorously. "Or would you prefer appearing in public dressed as a woman instead?" she asked as Mark got to the point where he was about to explode. "I could finish that dress for you and put you in a nice pair of high heels before taking you out to dinner or something," Trish suggested as she continued to stroke him. "I'm definitely going to dress you head to toe in woman's clothes very very soon. Just tell me if you want it to be public or private. You don't even have to tell me verbally which choice you want. Just nod at the correct choice. So am I cross dressing you in private? I don't see you nodding. Than it must be you want to publicly cross-dress," she concluded. "Now that we have that sorted out let's just calm you down a little so you don't make a mess inside your panties," Trish commented, finally releasing his penis. It took a minute or so of quietly standing in the change room, however Mark's penis finally became limp once again. "There, that's much better," Trish commented once his erection subsided. "What's all that noise," she added as they heard a man's voice just outside their cubicle. "Hold on honey, I'll get that one in the next size up," could be heard plainly through the curtain. At that point Trish stepped through to see what was going on. Mark heard, "Here you go, put this on and let me see how it looks," followed by a short pause and then, "I like the way that looks," before Trish came back through the curtain. "Two cubicles over is a girl trying on bras, and her boyfriend is running back and forth bringing her different bras to try on," Trish explained in a voice low enough that the couple being discussed wouldn't be able to hear her. "Actually that looks like a lot of fun. Let's do that ourselves, although you will obviously be to one trying on the different bras while I fetch them for you. Does that sound like as much fun to you as it does to me?" she asked, once again bringing a look of panic to Mark's face. "Great let's get started then," she told him when he didn't respond. "Because you're so flat chested to begin with, that bra you have on just doesn't give you the cleavage we're looking for. Let's try you in a nice padded pushup bra and see how that works on you," Trish said in a voice loud enough to be heard by anyone in the change area, including the couple two cubicles over. Stepping through the curtain, Trish left it part way open as she went to locate a suitable pushup bra for him to try on. Mark went to move the curtains closed but stepped back in shame as the boyfriend walked past the cubicle, apparently off to find yet another bra for his girlfriend. Glancing over as he walked past, Mark thought he detected a double take from the guy as he walked out of sight. He wasn't positive, but had the impression the boyfriend had suddenly realized it was a guy trying on bras in the cubicle, not a girl as he likely assumed. Stepping timidly forward once more Mark pulled the curtains closed while he waited for Trish to return. Suddenly Trish reappeared, stepping through the curtain and leaving it wide open behind her. "Here you go. This bra should give you some really nice cleavage," she told him in that loud voice as she handed him a pushup bra for him to try. "Let me help you remove that other bra," she added as she stepped behind him and started to unhook him. Unfortunately that meant she was no longer blocking the view of the inside of their cubicle. It was right then the boyfriend came back from his mission, carrying a new bra for his girlfriend to try on. This time he looked fully into the cubicle and was treated to the sight of Mark standing there in a bra, with Trish standing behind him undoing it for him. The boyfriend took all of it in as he walked past, managing to make full eye contact with Mark before passing out of sight. Mark had absolutely no idea how to react to something like that, caught red handed by another guy while trying on bras. "You will never believe what's happening two cubicles over," the boyfriend exclaimed, obviously not caring whether Trish and Mark heard him. "There is a man and a woman doing what we're doing, except the guy is the one trying on the bras and the woman is the one helping. I can't believe some guy would let a woman put him into bras like that! Not only that but she's obviously older than he is so I can't say whether they are boyfriend-girlfriend or it's his mother," the boyfriend said excitedly. "I've got to see this!" they heard the girlfriend exclaim loud enough for them to hear. Mark attempted to move forward and close the curtain on the cubicle. Unfortunately by this point Trish had the first bra off him and was in the process of hooking him into his second bra. Given the firm grip Trish had on his bra band Mark had a lot of resistance to overcome to make it to the curtain quickly. He ended up moving far too slowly, giving ample time for the couple to appear in the doorway of his cubicle before he could close the curtains. For the first few seconds Mark was mesmerized. The girlfriend was still wearing the most recent bra she had been trying on, and hadn't bothered to put her top back on before coming over for a look. A shock ran through his body as soon as he realized the woman was wearing the exact same make of bra as he was wearing. He had to admit not only did the girl looked quite good wearing that particular bra, she had a very nice body in general. He could feel his penis getting fully erect at the thought that he was wearing the same bra as this sexy woman. Meanwhile the couple were being treated to the sight of Trish hooking Mark's bra on him and then adjusting his bra straps when they didn't fit quite right. "Mark what do you think?" Trish asked as she stepped out from behind him. "Do you like the way this bra shows off your bust-line?" she added before looking over to the couple standing in the doorway of the cubicle. "If I buy it for you I'll want you to wear it whenever we go out on a date, so make sure it's the right bra for you," she added with a grin. When he didn't respond immediately Trish turned her attention to the other couple "How about you two? I admit this style of pushup bra looks much better on you than on my boyfriend, however do the two of you think this bra looks good enough on him for him to wear it a few times a week?" Trish said as she made eye contact with the two strangers. "I've recently decided Mark needs to start wearing a bra fairly regularly from now, so I think it's only fair to make sure his new bras are both pretty and will fit him comfortably for hours at a time," she explained to them. After a bit of a pause the girlfriend finally spoke. "That bra is very pretty on you Mark," she commented. "Have you been wearing bras for very long?" she added when he didn't respond to her comment. While the question was directed at Mark, it was Trish who ended up answering her question. "Actually we've only been exploring Mark's feminine side for the past few weeks. To the best of my knowledge he had never worn any womens clothing before that. For me it was just recently I realized I really liked the idea of cross-dressing a hot young guy, and putting Mark into his first bra is one of the key steps in achieving my goal. How about you? Has your boyfriend been wearing bras for very long?" Trish asked the girl mischievously. "No, I've never done that with Todd, although I did once it a few years ago with a previous boyfriend. At the time I thought it would be a playful thing to do, however once he was wearing my bra that boyfriend got really embarrassed about the whole thing. It mat have even caused our breakup, although there were a few other problems as well. Because of his reaction I've never explored that kind of thing any further with any of my boyfriends," the girl explained. "How about it Todd, are you willing to try on a bra for your girlfriend?" Trish asked the boyfriend, looking him full in the face. "You can't be serious," Todd replied, a shocked look on his face. "That's never going to happen Darlene," he told his girlfriend. "I'm nothing like your sissy boyfriend!" he exclaimed to Trish and abruptly stomped off. "Well, well, well, isn't that interesting," Trish commented. "How about it honey, how do you feel about playing dress-up with Todd there?" she said to Darlene in a low voice. "You heard him. He doesn't want any part of it," the Darlene replied, dodging the question as she continued to gaze at the pushup bra Mark was wearing instead of his face. There was a very definite feeling in the air that she really liked the idea of putting a guy into lingerie. "Yes I heard what Todd said, but I don't believe him. I guarantee your boyfriend is willing to wear womens underwear for you but is too embarrassed to admit it," Trish explained in a quiet voice. "I don't see that," the Darlene replied. "It's quite simple. He reacted too strongly when I suggested it to him. If wearing womens underwear had no interest whatsoever for him, Todd would have laughed about it or looked at me in disbelief when I first suggested it. Instead he made a dramatic show of rejecting the idea and then an even bigger show of stomping off in disgust. In my experience the ones that make that much of a fuss about something are exactly the ones who secretly interested in doing that something, but don't want to admit it even to themselves. I've never experimented with cross- dressing before, however I have asked some of my previous boyfriends to do some pretty kinky things and that is how it always played out with them. I found the bigger the reaction my boyfriend had up front when I asked him to try something new, the more likely it was I could talk him into it eventually. I found it was always the ones who gave me a simple no who would never budge later," Trish explained. "Um, okay. Supposing you're right and I want to pursue this I'll have to think about what to do about it," Darlene commented as she headed back to her cubicle, seemingly unconvinced. Turning back to Mark once more Trish could tell all of the activity had gotten him really really horny. Putting one hand inside his jeans and the other hand inside his bra she started stroking both Mark's penis and his nipple at the same time. "You liked standing there in your bra in front of strangers didn't you?" she prodded him as she continued stroking. "You especially like the fact both you and Darlene are wearing the exact same bra. Standing in front of a good looking woman, wearing the same underwear as she is really got you all hot and bothered didn't it? Personally I think you got excited because it made you feel like one of the girls, and you want to feel like a girl don't you?" Trish commented as she continued to stroke him. Between her words and her actions it didn't take long for before Mark couldn't contain himself any longer and started ejaculating all over her hand and inside his jeans. It took approximately thirty seconds for him to wind down and another minute for him to realize he couldn't go out in public as he was. He knew at a minimum he would need a new pair of jeans and a new pair of underwear. He turned to Trish with a pleading look in his eyes. "Yes, I know. You can't leave this dressing room looking like that. Don't worry, I'll take care of everything," Trish informed him as she wiped