The Boy Next Door: The Following Summer free porn video

Chapter 1 Trish was really looking forward to getting her maid back for the summer. Mark was due to return home today, and she was looking forward to picking up where the two of them left off the previous summer. Over the winter she had decided to keep increasing her feminization of the young man, and mentally started ticking off some of the things she had planned for him over the coming months. There were the obvious things such as going lingerie shopping, taking him to her hairdresser and getting him some new piercings and tattoos. She had also given some serious thought to introducing him to her sex toy collection, something she had been reluctant to do the previous summer for fear of scaring him away. Now that their relationship was better established she saw no reason not to proceed with that aspect of their love life, and had many sexy scenarios planned for the next few months. Unfortunately after all of that build up in her own mind Trish ended up disappointed. It was now three days later and although Trish knew Mark had returned home on schedule, he had made absolutely no effort to contact her. Just the previous day Mark's mother had confirmed his arrival, giving Trish positive proof her boy toy was home from college. While disappointed she was not entirely surprised by this turn of events. To her there could only be one explanation for his behaviour, namely Mark was conflicted regarding what he wanted from their relationship. She reasoned if he was absolutely certain he no longer wanted to sleep with her he would have come over to her house and told her that. Similarly if he did still want to sleep with her he would have immediately come by her house and allowed her to start ordering him around once again. This meant that the only logical reason for Mark to not contact her was if he was uncertain about what he wanted to happen between the two of them. In the past Trish had made it very clear that if he refused one of her suggestions their sex life was finished, so Mark must be trying to determine what he really wanted before confronting her. Although she could understand what he was up to, she couldn't allow the current situation to continue indefinitely. The next day she decided to take action by dropping in to Mark's house and pretending to visit with his mother. The two women had only been seated in the living room for a couple of minutes when Mark suddenly appeared, apparently unaware his mother was entertaining their neighbour. "There you are Mark dear. You mom said you returned from college a few days ago but I haven't seen you around. Too busy having fun I suppose! If you have a bit of free time this afternoon why don't you pop over to my place and you can tell me all about your college experiences," Trish offered, using the phrasing she typically employed to make it sound like a suggestion but that Mark would know was really an order. Recognizing that tone of voice and realizing he had just been given a direct order, Mark quickly agreed to come by her place at the required time. "That sounds like a lot of fun. How about two pm today?" he told her, trying to make the best of the situation. "One pm would work better for me if that is alright with you," she stated, happy Mark was toeing the line. "Great, one pm it is," he agreed, knowing he had little choice about the time or place. The chat with Mark's mother only lasted another half hour, which meant Trish was back home in plenty of time for the rendezvous with Mark. "There you are Mark honey. I've missed you so much while you were away," she told him as she pushed her body against his and gave him a deep french kiss. "Did you miss me?" she asked once she finally broke off the kiss. After the unexpected greeting it took Mark a handful of seconds to regain his composure. "Yes, I definitely missed both you and that," he said, the second part clearly in reference to the kiss. "Well if you missed that let's find out how much you missed this next part," she told him as she reached inside his pants and started stroking his penis. Once Mark was nice and hard Trish took his hand and led him to the bedroom. Pushing him down on the bed, she pulled off his pants and underwear and proceeded to engulf his penis with her mouth. Running her tongue up and down his shaft, she slowly brought him to the brink of climax and then let him deflate again. She did this a number of times until he was ready to explode. Suddenly she didn't stop, and he found himself shooting his full load into her mouth and her sucking up every drop of his semen. As he dropped down on the bed exhausted, Mark decided she had definitely given him the best blow job he ever had. Trish gave him a minute or so to recover before taking him into her mouth once again. Being a randy teenager she had Mark rock hard within another minute, and quickly flipped up her skirt and mounted him. With Trish on top she gave him quite the ride, bringing Mark to the brink of orgasm several times before finally letting him spew. His ejaculation seemed to go on even longer than the first time, but finally subsided. Giving him one final kiss Trish patted Mark on the cheek and got off the bed. "I have to dash off to an appointment. You can let yourself out whenever you're ready," she told him as stepped into the en-suite. Popping out refreshed a minute later, she kissed him, grabbed her purse and headed for her front door. Mark really didn't know what to make of what had just happened. They had just had amazing sex without any of the feminization stuff Miss Wilkins had done to him last summer. He started wondering if their relationship had changed now that he had been to college for a year. Shaking his head in mystification, he got off the bed and stepped into the en-suite himself to get cleaned up. Still bemused he let himself out of her house and headed back to his own house as he pondered what might be in store for him next time he saw her. Over the next few days Mark kept thinking he would receive a summons from Miss Wilkins at any time, but that summons never came. Even after a week he still hadn't heard anything from her since that afternoon romp. Worse Mark was starting to get really really horny. While he hadn't been having sex regularly while at college, he suddenly craved sex like an addict now that he had been reminded just how good Miss Wilkins was compared to college girls . Finally after a two weeks with no word Mark couldn't stand the suspense any longer. He decided he would have to be the one to make contact with her. He just couldn't help himself, even though he knew he was giving up some power by being the one making the next move. Chapter 2 Once he decided to make contact Mark also decided to call Miss Wilkins instead of going to her house. The next day he had an opportunity where his mother would be outside for a while working on her flower beds. Mark picked up the phone in his room and dialed, with Miss Wilkins answering her phone after a couple of rings. "Hello Miss Wilkins, it's Mark from next door" "Mark honey. Not to be rude but I'm a little rushed at the moment. What can I do for you?" Hearing such a dismissive response from his lover put Mark into a bit of a panic. He wondered if the sex last weekend was some kind of a farewell romp, and she was no longer interested in him. "Ah, I was kind of hoping we could get together later today, if that's okay with you," he hedged, trying not to sound desperate and failing miserably. "That doesn't sound like a good idea Mark. Last summer I told you I want men I'm dating to fully embrace their feminine side, and you don't seem willing to do that," she told him firmly. "During our love making two weeks ago you didn't wear anything feminine, not even a bra and panties. This despite the fact you were well aware of my expectations of you. Because of your actions I've decided we're not a good fit for each other, so the best thing to do is permanently end our relationship," she informed him. Desperately searching for a way to salvage the situation Mark started grasping at straws. "I could come over to your place right now and put on something frilly for you," he offered lamely. "I'm sorry but you're still missing the point. After last week I would need a major gesture from you to show you're willing to fully embrace your feminine side. Think harder," Miss Wilkins ordered him, offering at least a tiny ray of hope. Suddenly Mark realized what kind of gesture might satisfy Miss Wilkins. "While I was at college I bought myself a new dress and matching high heels, plus the lingerie to go with it. I could bring that over to your house and model all of it for you," he suggested desperately. "No, still not good enough. Now if you were to put everything on at your house and then walk to my house dressed as a woman, then it's barely possible I would reconsider our future together. That would at least show me you are serious about your feminization and are willing to do whatever it takes to please me. I'll leave it up to you. I have to leave my house in less than an hour, so you'll need to decide quickly. It really depends on whether you are willing to make a serious effort to salvage our relationship or not," she told him before hanging up the phone. Mark knew an ultimatum when he heard one, and realized if he didn't do this now Miss Wilkins would never give him another chance to sleep with her. Peeking out of his bedroom window Mark could see his mother was still working away in her garden. As their backyard was out of sight of Miss Wilkins front door he reasoned he just might be able to get away with this if he hurried. Stripping off his clothes he dug into the back of his closet where he had been hiding his feminine things and pulled out the necessary items. Quickly donning the bra, panties, garter belt, stocking, dress and high heels he had purchased while at college, he looked at himself in the mirror to verify he was ready. Checking on his mother one last time he hurried as much as he could in three inch heels up the basement steps, went through the kitchen and out the front door. The tapping of his high heels sounded incredibly loud to him as he rushed between the houses. Making it to Miss Wilkins house undetected by his mother, Mark had an anxious few seconds as he waited for Trish to answer his knock. He felt very awkward standing at his neighbours front door wearing high heels and a dress, causing him to almost fall over when she finally did open her door. "Mark, I'm glad you are willing to make such a serious effort to be feminine for me. I also have to say I quite like that dress on you. In fact I would like to see you in dresses much more often, particularly that one," Miss Wilkins commented loudly as Mark continued to stand on her front step. As he shifted nervously from foot to foot he was hoping none of his neighbours was within earshot of this monologue from Miss Wilkins. "For the next month I want you to come to my front door every Saturday morning at 10 am in that pretty dress, high heels and full makeup. I'm sometimes in the middle of doing something on Saturday mornings, so be prepared to wait at my door until at least 10:15 each time before you even think about giving up and going home," she added as Mark cringed inside. The idea of standing on his own street every Saturday morning for up to fifteen minutes wearing a dress and high heels was so daunting he did his best to shut it out of his mind. "Getting back to today, while the way you are dressed is a good start there are a few improvements we need to make to your overall appearance to really make you feel feminine," Miss Wilkins explained as she finally brought him inside and closed the door behind him. Leading him upstairs to her bedroom she sat him down at her vanity, picked up a pair of tweezers and without another word started plucking his eyebrows. Of course by this point he knew better than to object or provide any kind of comment on what she was doing to him. "I'm tired of your eyebrows looking so masculine. A pretty girl like you definitely needs feminine eyebrows," she commented as she plucked away. "To be honest since last summer I've been looking forward to shaping your eyebrows like this, actually ever since that salon only did a partial job on you. I know you are going to look and feel so sexy once I've made those furry caterpillars of yours more ladylike," she mused as she continued to remove hairs. "You may want to come up with a something to explain the way your eyebrows look when you're presenting yourself as a male. It's up to you of course, however I suspect a lot of people will be wondering why such a normal looking man would choose to have his eyebrows done in such an obviously feminine shape. My personal suggestion is you tell anyone who asks that you've always admired the way women groom their eyebrows, and finally had the courage to tell the salon to groom yours the same way," Trish suggested as she continued to pluck away. Mark started feeling a bit queasy inside at having such an obvious change made to his appearance, however given the stakes he still made no move to stop her. "While I'm making your eyebrows all nice and pretty I'd like to hear about the shopping trips you made to buy this outfit," she told him. "I spoke with the sales associates you dealt with months ago of course, once you provided those details to me as we agreed. However I would like to hear you describe what happened in your own words," Miss Wilkins added as she finally put the tweezers down and picked up an eye makeup brush. Although distracted by the work she was doing on his face, Mark turned his mind to the dress shopping he had done while away at college. "You can see the dress I bought so obviously I don't need to describe that to you. Exactly what details did you want to know about my shopping trips," he asked as Miss Wilkins applied brown eye shadow to his eye lids. "This brown shadow will really highlight your blue eyes," she commented "Between that and the mascara I'll use next your eyes will be quite noticeable by the time I'm done. Of course it will be obvious to anyone who sees you that you are wearing a lot of eye makeup, but that is all part of the fun after all. Your feminine new eyebrow shape really cries out for sexy eye makeup, so shortly you get to see how having both done to you will dramatically change the way you look. Regarding the shopping, I certainly don't need to hear a blow by blow account of the trip. Just describe some of the highlights from your trip, including some of the more memorable things that were said by the saleswomen helping you," she told him. "Well I ended up going to three different stores to find this dress I'm wearing. The first two stores stocked dresses women wear on an every day basis, the third one had those as well as a selection of gowns," he finally told her after a short pause to gather his thoughts. "What else? How did the saleswomen react to having a male shop in their stores," Miss Wilkins asked as she put down the eye shadow and picked up a bottle of mascara. "The saleswomen in the first two stores weren't all that interested," Mark told her as Trish started applying mascara to his lashes. "The owner of the third shop however seemed to get a real kick out of a guy being willing to try on dresses, and I even ended up trying on some gowns I had no intention of buying. In the end the owner Jessica took a bunch of pictures of me all dressed up and insisted I work in the back of her shop every Saturday. She told me she would have me do things like counting inventory and ordering new stock if I didn't want her to publish the photos of me all dolled up," he told her. "I'll hoping she had you dress appropriately for your job," Trish stated as she stopped working on his face and looked him right in the eyes. "To be honest the whole thing was pretty embarrassing for me. Jessica insisted I wear a bra and panties, high heels and a dress all day while working in her store every Saturday. Thankfully she did let me change at the shop, so I wasn't wandering around the city dressed like that," he told Trish as she got back to work. "I was mostly on my own in the back of the store, however the odd Saturdays she would bring customers into the back and introduce me as her sissy stock boy. She would then tell those women that I didn't want a salary for my work, but instead insisted on receiving womens clothes in exchange for all of my work efforts. Jessica would usually finish the interaction by showing them whatever dress I was working towards buying on that particular day, holding it in front of me so the customer would see how it would look on me once it was mine. More often than not the customer would ask me to model my new dress, which Jessica would always have me agree to if requested by her customer. At first it was pretty difficult stripping down to my bra and panties in front of women I didn't know, but eventually I got somewhat used to the feeling," Mark admitted as Trish finished applying makeup and started applying nail polish to his fingernails. "I'll definitely have to contact Jessica and ask her what she enjoyed most about feminizing a young man such as yourself," she commented as she worked on each nail. Once she was finished his nails Trish grabbed his arm and pulled him towards the door, not even allowing him a chance to see himself in the mirror. "I really have to run now Mark. We'll see you later," Miss Wilkins told him as she hustled him towards the front door. "Just one last thing before you leave. When you were at the age when most girls start wearing a training bra, say eleven or twelve years old, your mother unfortunately didn't put you in one. If you do the math it means by the time those girls become your age most of them have had at least eight years to get used to wearing a bra full time. We can't go back and fix your mother's mistake now, however we can compensate for it. Because your mother didn't take care of this critical experience when you were a young girl, I've decided I now want you to start wearing a bra all day every day so you can make up for lost time and get used to the feeling of wearing them. I'm aiming to very quickly get you to the point where you tend to forget you are wearing a bra, at which point we'll have achieved our goal," she told the stunned young man. Before he could react to the latest assault on his masculinity he found himself outside of the safety of her house. Miss Wilkins immediately walked to her car, started the engine and pulled out of her driveway. It was obvious she expected Mark to go back to his own house in the middle of the day, makeup, plucked eyebrows and all. The alternative would be to walk around his neighbourhood in 3 inch heels until it got dark out. Even should he do that his mother might lock the door on him, not knowing where he had gone and thinking he had house keys with him. Deciding sooner was safer than later Mark decided to take his chances and headed for his house. Miss Wilkins had kept him at her house long enough that Mark could no longer be sure his mother was still gardening in the backyard. He decided to gamble that his mother had likely gone inside while he was at the Wilkins house, so he snuck around to the back of his own house. Peering around the corner it did indeed look like his mother had gone inside. Mark had to hope she wasn't looking out one of the windows facing the backyard as he strode along the path in his dress and high heels. Once at his back door he listened for a second for sounds of movement, before cautiously opening the door while trying to minimize any noise it made. Stepping out of the high heels he picked them up in one hand and carefully slid through the doorway. He suddenly heard a couple of kitchen type noises. Taking that as his cue he glided down the steps leading downstairs and tiptoed towards his bedroom. Once in the safety of his own room he breathed a small sigh of relief, even if he wasn't out of the woods quite yet. He still needed to put his appearance back to normal before his mother came looking for him, and decided to start by looking in a mirror to see what Miss Wilkins had done to him. His first reaction was 'holy crap', after which he kind of wished he hadn't looked in the mirror. While he could still easily recognize the image in the mirror as himself, he was amazed at how feminine Miss Wilkins had made him look in such a short amount of time. The mascara and eyeshadow drew a lot of attention to his eyes, but it was his eyebrows that had the most impact on the way he looked. While Miss Wilkins hadn't given him the ultra thin brows some women favoured, there was absolutely no doubt his eyebrows had been plucked and shaped to fit a female beauty ideal. His eyebrows were now noticeably thinner than they had been before he went to her house, plus she had given them that distinctly high feminine arch and thin tapered tail that he personally found so sexy on a beautiful woman. Seeing those same brows on himself was incredibly disconcerting, and he was quite surprised his eyebrows could look as feminine as they did. Just as Miss Wilkins had promised Mark knew anyone looking closely at him would instantly realize his eyebrows had been intentionally shaped in a feminine style. So much so that anyone seeing him might even wonder whether other parts of him had been similarly feminized. Certainly if he himself saw a guy sporting those eyebrows he would wonder why the guy wasn't in a dress and high heels as well. Looking at himself in the mirror once more, to his utter surprise he found his new look was turning him on more than a little. Reaching up with his index finger, he traced the sensuous new line of his eyebrow as his penis gave a few little twitches. Mark examined his eye makeup closely, starting to wonder whether he could recreate the look himself. As soon as he admitted to himself he liked some of what Miss Wilkins had done to him his penis started twitching like crazy, and within seconds he was well on his way to a full blown erection. Thankfully the thought of masturbating while looking so feminine was too much for him to handle at the moment, causing him to quickly calm down and lose his erection. With his erection gone he was disconcerted that being all dolled up and looking like a woman had gotten him so close to orgasm. He realized Miss Wilkins really had changed him over the past year, or at least had completely tapped into some kinky part of him that liked the idea of being feminized and had been waiting to get out. Once the sensations from his crotch had died out completely Mark put aside the disturbing thoughts looking like a woman were causing him and instead turned his thoughts to removing all traces of what Miss Wilkins had done to him. Taking a deep breath he started the process by stripping off all of the incriminating clothing. Once that was done he went to work on his face. It took Mark a good ten minutes but he finally managed to remove all traces of the eye makeup and lipstick, all the while trying to come up with some way to deal with his eyebrows. The last thing he wanted was for his mother to see what his eyebrows looked like and decide he had either done this to himself or paid someone else to pluck them. By the time all of his makeup was off he had come up with a tentative plan. Taking a pair of scissors he kept in the bathroom, Mark carefully trimmed some hair from the back of his head and placed it on the counter. Trimming the hair a little more to match the length of his eyebrow hair, he retrieved a glue stick from his dresser and started carefully gluing strands of hair around the small amount of eyebrows Miss Wilkins had left him. It took him close to an hour, but by the time he was finished Mark looked almost normal. The eyebrows looked a little odd, almost as if they were having a bad hair day, but they were masculine eyebrows once again. While not a long term solution, Mark was hoping his temporary repair job would at least fool his mother for today while he figured out a more permanent solution to the problem. Next it was time to do something about his nails. While he didn't have any nail polish remover himself, Mark knew his mother kept some in the house. Now to try and find it. Carefully making his way upstairs Mark managed to slip into the upstairs bathroom without being spotted by his mother. Thankfully he found a bottle of nail polish remover under the sink. Quickly slipping it into his pocket he headed back towards his room. He breathed a sigh of relief once he was safely back in his room without being spotted by his mother. Ten minutes later with the aid of the polish remover he had managed to strip off all the nail polish Miss Wilkins had applied and was starting to feel much more normal once again. He spent an uneventful night thinking about fixing his eyebrows a little more permanently. Ultimately he decided a wig store might be able to help him with his problem. Early next morning he found himself putting on one of his bras right after his shower in obedience to the latest edict from Miss Wilkins, and then once fully dressed he headed to a local wig store. He managed to arrive shortly after it opened for the day. "Can I help you sir?" the pretty sales woman greeted him, looking slightly puzzled as to why Mark was in the store. "I certainly hope so," Mark replied firmly. "I want to make my eyebrows look more masculine than they are at the moment. "They look a little shaggy and out of proportion, but they don't look too bad," she commented, still seeming puzzled "No, you don't understand. A woman I'm dating decided it would be fun if she plucked my eyebrows into a very feminine shape. Because what she did to me was so obvious, I spent an hour last night gluing little bits of my hair onto my eyebrows to fill them out and make them look normal again. I was looking for you to do something similar, but hopefully do a better and more permanent job of it. It would be nice if I didn't have to worry about how my eyebrows look until they grow out again," Mark told her. "That is too funny!" she exclaimed. "You must have been drunk and passed out when she did that to you" "No, not exactly," Mark replied sheepishly. "To be honest I was awake and completely sober while it was happening" "I don't understand. If you were awake and fully in control and didn't want your eyebrows changed, why didn't you just walk away? Or is it at the time you really did want her to do it, but are now having second thoughts?" she suggested. "It's a little complicated, but essentially letting her pluck my eyebrows like that was the only way she would keep sleeping with me," he confessed in a low voice. "Really. Your girlfriend insisted on giving you feminine eyebrows or she wouldn't go to bed with you? First time I've ever heard that one. If that's the case how will she feel about you coming in here and asking me to undo all her hard work?" she questioned Mark. "She might be pretty unhappy with you if you show up with your eyebrows looking like they always do" After only getting a sickly smile in reply she continued to talk. "Well, since you want to do this let's see what's going on under your patch job," she told him "My name is Angela by the way," she added as she opened a bottle of liquid and soaked a cloth with the contents. Approaching him she started dabbing it on his eyebrows. "Nice to meet you Angela, I'm Mark. What's that stuff your using?" "It just a mild solvent that should remove whatever glue you used for your quick patch job" After she had wiped for a few seconds clumps of hair started coming off. In less than a minute it felt like his eyebrows were back to the way Miss Wilkins had left them, a conclusion quickly confirmed by Angela. "Damn, that woman you're dating did a wonderful job on your eyebrows. The way she did them really makes your face look much more pretty and feminine. Considering how well it compliments your facial structure it seems such a shame to hide all of her hard work. Are positive you don't want to keep the look she gave you? We could put some eye makeup on you to really highlight that whole part of your face, and then find a wig to finish off your new look. I already have a couple of male customers who love it when I make them all girly. I'd be happy to take you on as a new client and do the same with you," Angela told him. "No thanks. I had all of that done to me yesterday, and to be honest looking so much like a woman made me really uncomfortable. I just want to go back to looking like a normal guy. Can you fix this for me?" "It seems a shame, but I'll see what I can do on one condition. You have to buy a really sexy womens wig from me as well," Angela informed him. Once Mark nodded she got to work. He had to sit quietly for the next hour as Angela worked away at her task. Finally she was done and swung him around so he could see the final result in the mirror. He had to admit her work looked pretty good. While his eyebrows looked slightly different then they did previously, she had definitely made them look masculine again. "I used glue that is not water soluble, which means the hair won't come off in the shower. It does however mean once your eyebrows start growing back in you'll have to wait until the fake hair falls out on its own, or alternatively come back in here so I can remove it for you." "That works for me," Mark told her enthusiastically, pleased none of the people around him would know what Miss Wilkins had done to him. "Now, let's find a wig that makes you look really pretty," Angela told him as Mark realized she hadn't forgotten that part of the agreement. For the next half hour Mark found himself trying on a number of different womens wigs, none of which could be considered the least bit masculine. Angela finally talked him into getting a particularly pretty blonde wig that gave him hair down to his shoulders. After paying Angela for her efforts and his new wig he quickly left the shop and headed home. Running into his mother as soon as he stepped through the front door, she gave him a slightly odd look as if she knew something about him was different, but couldn't quite put her finger on it. He reasoned if that was the worst thing that was going to happen to him over this eyebrow thing he was way ahead of the game. Chapter 3 The following week Mark cut through the kitchen on his way to the front of the house while his mother and Miss Wilkins were having coffee. Before he could make it all the way through Trish brought him up short. "Mark honey, I remembered it is your birthday tomorrow and got you a present," Trish told him as Mark's mother looked on in surprise. It seemed obvious from her reaction that Mrs. Morgan didn't expect her neighbour to remember her sons birthday. "Here you go sweetie, I got you a gift certificate from Romantic Interlude Lingerie," Trish told the surprised young man. Meanwhile the look on Mrs. Morgans face went from surprised to incredulous. "You got my son a gift certificate for a high end lingerie store as a birthday present?" she asked Trish in astonishment. "Absolutely. I figured he's old enough now that he likely has some special friend to buy lingerie for, however being a student he might not have the money to do so. So what do you think Mark, is that gift certificate something you can use? Did you want to buy lingerie for that special someone?" Trish asked with a wide grin. Of course Mark immediately knew Trish expected him to buy lingerie for himself. He had to admit he was embarrassed Miss Wilkins was doing this in the presence of his mother. While she was being clever about it by implying it was for some mystery girlfriend of Mark's, he was still very concerned that his mother would begin to suspect something if this continued. It was especially worrisome after that somewhat feminine haircut he had come home with the previous summer. "I'm sure I can make use of the certificate," he replied graciously, trying desperately to downplay the whole situation. Unfortunately Miss Wilkins had other plans. "That wonderful. It would make me very happy if you could do your lingerie shopping by tomorrow afternoon and let us see what you purchased. Your mother and I are having coffee again at 2 pm tomorrow so that would be the perfect opportunity to show off what you picked out for that special friend," Trish told him. "Oh, and in case you are a little stuck for ideas I have included a list of suggestions in the envelope," As soon as said that Mark knew what was on the list were not actually suggestions, but was really what he was expected to buy for himself while at the store. He also realized he would have to try all of the things on while in the store to make sure everything fit properly if he didn't want to be sent back to the store later to fix any mistakes. "I have time tomorrow morning. I'm sure I can fit in some shopping," Mark replied with an internal sigh. "I'll look forward to it," Trish responded as she turned back to her conversation with Mark's mother. The next twenty four hours was a blur for Mark. Even though it seemed like only minutes, it was soon 2 pm the next day. He found himself bringing the bag from Romantic Interludes into his living room for the approval of Miss Wilkins. "Mark, I'm so happy this worked out. I can't wait to see what you're purchased with that gift certificate!" Trish exclaimed while Mark's mother looked on curiously. Reaching into the bag he pulled out the first item, holding it by the straps as he nervously displayed it to the two women. It was a very sexy black merry widow with red lace trim, and seeing it once again caused Mark's mind to flash back to that morning. Explaining to the sales woman that he was shopping for a merry widow had been embarrassing enough, however he wanted to sink through the floor right then and there once he admitted to the saleswoman he was actually shopping for himself and would want to try on all of his lingerie selections. The only thing that kept him going was the fear of having to wear a garment like that on a regular basis and it not fitting properly. He suspected wearing a badly fitting merry widow for hours on end would be nothing short of torture, but he also knew that is exactly what Miss Wilkins would insist upon if he took the easy way out and didn't try things on before buying. "That is just so sexy!" Trish gushed as she took the pretty garment out of Mark's hands and held it up by it's bra straps. "Your special friend is going to just love it! There is one odd thing though," she continued, sounding puzzled. "This merry widow looks like it would fit someone exactly your size," she said with a gleam in her eye. "Tell me Mark, is this mystery girlfriend of yours exactly the same size as you are? Or is there maybe something you're not telling us about yourself?" Trish said with a grin as she stepped over in front of Mark and held the garment against his chest as if sizing it up to fit him. "It is just too sexy, the way a Merry Widow like this molds the body of the person wearing it, pulling in the waist and emphasizing the breasts and hips. It is just such a wonderful garment that I'll bet even someone like you would look and feel sexy wearing one," Miss Wilkins mused as she continued to press the garment against Mark's body. With the garment pressed against him it was obvious to both women that this sexy item of womens lingerie would in fact fit Mark perfectly. Mark started getting a massive erection while his brain suddenly flashed back to earlier that morning, remembering how the saleswoman had hooked him into the garment and had him stand in front of her for minutes while she adjusted the fit on him. At the time he had been surprised how horny he had gotten having a woman put him into such a sexy garment. He wondered how his mother would react if he admitted not only was the merry widow for him, but he had already tried it on in front of a sales person. He turned bright red thinking about trying it on as well as the current situation he was in. "No, I've told you everything. Jennifer is just a bit of a big girl, but I'm sure she'll like what I got her," Mark replied making up an imaginary girlfriend on the spot. Putting down the merry widow Trish started rooting through the other items in the lingerie store shopping bag. "Well, well, what have we here!" Trish exclaimed as she extracted the heavily padded pushup bra her note had ordered Mark to buy. "How on earth did you know this Jennifer's bra size?" Trish commented as she held the bra by either strap, stepped over to Mark once again and positioned the bra in front of him just as she had done with the merry widow. Being from the same collection as the merry widow the bra used the same black and red color scheme as the other piece. "If this Jennifer or yours is a bit of a big girl as you claim, why would she need such heavy padding in her bra cups," Trish commented as she continued to hold the bra against Mark and looked him straight in the eye. Mark couldn't believe Miss Wilkins was still planting all these seeds of doubt with his mother, implying her son was secretly a cross- dresser who had just this morning gone lingerie shopping for himself. "The bra you bought looks like it would add at least two cup sizes to the person wearing it, which would mean this Jennifer of yours must be as flat-chested as a boy," Trish suggested with a smile as she examined the padding, knowing full well she had been the one who ordered him to buy a heavily padded bra. "Also how can you be certain the bra will fit properly if no one tried it on in the store?" Trish asked, driving the knife in a bit deeper. "You may not be aware that no two brands of bras fit quite the same, so the only real way to ensure a bra fits someone properly is for them to try it on before buying it," she commented, trying to embarrass him even further. "I could be wrong, maybe you do already know that about bras," she added with a grin. "Of course I could be completely wrong about what happened at the lingerie store this morning," Trish continued "I can think of one person who would not only fit nicely into this bra, but would also want heavily padded bra cups. The person I'm thinking of could certainly have already tried on both the bra and the merry widow in the store this morning, and found both fit him perfectly," she added with an evil smile. "Now why don't you stop pretending you have an imaginary girlfriend, put on your new merry widow and model it for your mum and me," she suggested with an evil grin. Miss Wilkins seemed so tickled by putting him the spot like this that it made Mark that much more flustered. "I'm sure if you didn't have a problem trying it on this morning in the store you should have no problem showing us how it fits you," she added with a wink. "Don't worry, I won't be made if that special someone you bought lingerie for is yourself. In fact I think it's cute you want to get in touch with your feminine side" "I may have made a mistake with the padding, but it is removable," Mark shot back, ignoring his lovers suggestion that he wear his purchases in front of his mother."I admit I did decide to take my chances and buy the items without Jennifer trying them on. If not she can always exchange them," He added, sighing with relief when Miss Wilkins finally stopped holding the bra to his chest and dropped it in his lap. Rooting through the bag once more Trish held up a pair of regular panties and then with a quirk of her eyebrows towards Mark held up a pair of thong panties and matching garter-belt, all from the same collection as the previous pieces. "This is quite a sexy set you've bought. The person wearing these things couldn't help but feel incredibly feminine. I'm sure you can't wait to put them all to some good use," Trish commented as she intentionally avoided referring to Mark's imaginary girlfriend. Trish was making it obvious to Mark's mother that she wasn't really buying the whole girlfriend story her son was telling the two of them, and half expected Mark to head downstairs and don the sexy lingerie himself as soon as he was alone. "Mark, why don't you bring this Jennifer around to the house this week. I would really love to meet her," Mrs. Mason pipped up, obviously at least partially driven by Trish's insinuations to confirm the existence of this girlfriend Mark was talking about. "Well, Jennifer is pretty busy this week, but I'll do my best to arrange something," Mark replied, frantically trying to think of a way out of this. "That's great. You could even give her these presents at the same time," his mother added, apparently trying to verify her son really had purchased the items for a girlfriend and was not planning on wearing the lingerie himself. Mark quickly gathered all of the lingerie together and shoved them back into the shopping bag. "You know Mark, I could take you dress shopping sometime if that would make you happy. There are lots of cute flirty dresses that would look great on someone your age, especially if you wore your new padded bra and we laced you into a nice corset to help your figure," Trish commented, still doing her best to embarrass him. "You could look like quite a dish by the time I finish with you," she added. "Trish please stop this. My son is not a cross-dresser! He doesn't want to dress as a woman!" Mrs Morgan exclaimed, finally confronting the whole cross-dressing notion directly and coming to her son's defense. "If he was, would that be a problem for you?" Trish asked, turning to the other woman and confronting the central issue. "I don't know. I've never it any thought," Mrs Morgan replied, sounding distracted. "Well it really isn't an issue as I'm not one," Mark spoke up, trying to end the speculation even if he was lying to his mother. Getting no response from either of the women, he said a polite good bye and headed to his room with all possible speed. Once safely in his room he racked his brain trying to come up with a plan for not only producing a girlfriend named Jennifer in the next week, but also making sure she would be the correct size for the lingerie he had purchased. 'No wait' he thought to himself. 'I can hire a stand-in to pretend to be my girlfriend for the afternoon, and go back to the store to buy the identical lingerie set in whatever size she is. As long as it's close to the size I've already bought, my mom shouldn't notice the difference'. Mark decided this changed this whole problem from impossible to merely difficult. Mark just had to hope Miss Wilkins wouldn't give the whole thing away on him. He didn't think she would as that would mean admitting her own involvement in Mark's cross-dressing, however he still was never quite sure what his lover would do in any given situation. Certainly the incidents yesterday and today were complete surprises to Mark, who never imagined the divorcee would first entice him into cross-dressing and then relentlessly hint at that cross-dressing to his mother. He was just glad she hadn't come right out and asked him whether he had tried on the garments as he would have to either lie about that or tell the truth, both of which would have been potentially disastrous Somewhat surprisingly Mark did manage to arrange the whole girlfriend meeting, and the following week had an actress posing as Jennifer spent more than an hour at the Morgan house receiving the lingerie gifts and chatting with both Mark's mother and Trish. While thankfully Trish didn't expose his deception to his mother, there was still a downside for Mark as it cost him much more money than anticipated. While Mark had already budgeted to pay the actress for her time, he had planned on returning the unused gift lingerie to the store for a refund. That plan failed when Trish insisted the actress try on all of the gifts while at the Morgan house and then removed the tags once it was obvious everything fit her perfectly. Once that happened Mark had little choice but to give the actress the lingerie as an added bonus for her performance. Despite the financial cost Mark was quite glad he got away with it, even though Trish had looked on in amusement the entire time the farce was going on. Apparently while Trish was willing to have his mother become suspicious about Marks activities and love life, she wasn't determined to out him just yet. He had to hope things would remain that way as he was still not willing to give up his relationship with his neighbour or have his mother find out about the terms of that relationship. To him he felt like the status quo was his only option. Chapter 4 As ordered the previous week, at 10am the following Saturday Mark showed up at Miss Wilkins front door in a dress and high heels. To make it over to her house without being spotted by his mother had been touch and go, but he somehow managed to sneak between the two houses across undetected. It would have been a real shame for him to successfully convince his mother he was buying the lingerie for his girlfriend and then get spotted by his mother wearing a dress. Thankfully on this particular Saturday once he knocked Miss Wilkins answered the door immediately and escorted him inside. "Mark Honey. You'll remember I brought you to a hair salon last summer. Today I want you to go through the whole process of setting up a salon appointment for yourself. Specifically I want you to experience the fun and embarrassment of informing the salon receptionist that you want a service normally only requested by women. I am willing to make one concession in all of this in that as long as you cancel the appointment before the appropriate deadline, you don't have to keep the appointment," Trish informed him once they were settled in her living room. "Here is the phone number and your set of instructions," she added as she handed him a piece of paper and her cordless phone. Considering the look in her eyes Mark decided he had better not be tardy with this particular call and immediately started dialing. "Beautiful New You Salon. How can I help you?" a youngish sounding woman answered after a few rings. "Oh, hi.....er, yes, I.... would like an appointment.....umm, you know, for myself," Mark finally managed to get out. It was at that point that Miss Wilkins reached under his dress and started stroking his penis through his panties. Within seconds his erection was straining the fabric, trying to escape. "Okay, I have an opening for tomorrow morning. Is this for a haircut?" she asked as Miss Wilkins continued to stroke him, causing Mark to worry he would orgasm while on the telephone. Although the woman on the other end of the phone had phrased it as a question, from her tone of voice Mark could tell she meant it as more of a statement. Trying to focus his attention, Mark read down his instructions to see what he was supposed to say next. He didn't quite understand the next part, but read from his script anyway. "Er, no..........I would like a roller set," he told her, wondering why he was getting an appointment for something that sounded like it belonged at a hardware store. "A roller set? You mean a wet set young man?" she asked, a note of surprise in her voice. Miss Wilkins was close enough to the phone to hear what the woman was saying, and nodded her head firmly. Apparently he had asked for the service correctly, whatever it was. "Yes, that's right," he replied as Trish continued her work under his skirt and whispered 'good girl'. "Young man, have you ever had a wet set before?" the salon receptionist on the phone asked, a note of surprise creeping into her voice. "No, I haven't," Mark replied as he struggled to concentrate. The task suddenly got even harder as Miss Wilkins ducked her head under his dress and started sucking on his penis. "I assume you are aware that particular service involves me first shampooing your hair, then putting your hair in curlers, and finally putting you under the dryer for close to an hour while your new curls dry properly. You're positive you want an appointment at a womens hair salon and shouldn't be shopping at the hardware store instead?" she asked, echoing his own earlier thoughts on his request. He heard the same note of surprise creeping back into her tone as she clarified his request with him. "Y..Yes. What you said is exactly what I want," he finally blurted out as Trish let his penis drop from her mouth and sat back with a big grin on her face and cooed 'good girl' again. The girl on the phone giggled and said. "Okay, sure. If you don't mind me asking, why do you want us to put pink rollers in your hair in the middle of a busy salon? I'm curious as most guys would find that kind of service and that kind of situation far too girly for their taste. I was wondering why you don't feel the same way about having your hair done on curlers in front of a salon full of women," she asked. Mark had to take a deep breath before he could speak once more. He was suddenly getting a sense of what Miss Wilkins had gotten him into, although thankfully she had promised he would still be able to cancel the appointment before it happened. "It isn't the work itself, I'm really just curious about how I'll look with curls," he told her, going with the first thing that popped into his head. Once he blurted out such a lame excuse Mark was even more happy he wouldn't have to go through with the appointment. "Okay...sure, if you say so we'll give you some really pretty curls. As this is the first time I've ever had a male request a wet set I just wanted to make certain you understood what you will be getting during the appointment. Sunday morning is one of our busiest times of the week, and there will be lots and lots of women in here having their hair done like yours. To be honest the only reason I can fit you in is because I just had a cancellation 10 minutes ago, and you are the first person to phone in since the cancellation came in . Ten minutes later and I likely wouldn't have anything available for you," she told him. "If you're positive you want to go through with this I'll mark you down in my appointment book for 10am tomorrow. My name is Colleen by the way. Just ask for me when you arrive and I'll get you sorted out," she told him "If for some reason you have to cancel the appointment please do so before 6pm tonight so we'll have a chance to give the time slot to someone else. "One last thing. You might want to consider wearing a cute top or even a dress to your appointment. Either would certainly help you fit in much better with our normal clientele," she added as she hung up on the other end before he could respond. "Boy I am so glad I don't have to go through with that appointment," Mark said with a sigh of relief, echoing his thoughts from a minute earlier. Imagine her suggesting he show up in a womens top or worse, a dress! Almost against his will Mark started imagining what it would have been like to have his hair put up in rollers and sit there in the middle of a bunch of chattering women for a couple of hours. The mere thought of it caused his hands to start shaking. With the phone call done he promptly changed into the French Maid outfit Miss Wilkins kept for him and spent much of the rest of the day thoroughly cleaning her house. Throughout the day he would occasionally imagine what it would be like to show up for the appointment dressed as he was now, but quickly dismissed the idea as completely crazy. He was kept busy all day by Miss Wilkins, so much so that it was much later in the day when his thoughts turned towards canceling the appointment. "Miss Wilkins. It is getting towards supper time. I really should call to cancel that salon appointment. Colleen requested I cancel before 6pm if I wasn't going to go through with it," Mark commented as he starting changing out of his French Maid outfit and back into the dress he had worn to her house. "Go ahead and call then," she told him, dismissing the issue with a wave of her hand. Unfortunately when he called the number he got an answering machine telling him Beautiful New You was closed for the day, but he could leave a message after the beep. He finally managed to stammer out his cancellation before hanging up the phone. "Uh, Miss Wilkins," He said hesitantly "I'm afraid the salon had closed by the time I called. I think Colleen gave me the wrong closing time, however I did leave a cancellation message on the salons answering machine," He explained. It was at this point that Miss Wilkins dropped another bombshell on him. "Sorry but that's not good enough Mark. Since you didn't give the salon time to rebook the appointment you'll just have to go through with it. Otherwise it wouldn't be fair to their business or Colleen," she informed him in that no nonsense tone she used when she expected him to do something with no back talk. "If it makes you feel better you can put all of the salon services on my tab. I had you call that particular salon because I'm a regular there, and once they've finished with you tell them to bill everything they've done to my account," Trish told him firmly. "I also want you to wear a cute top as Colleen suggested, however if you keep arguing about this I'll be tempted to send you there in that dress she mentioned. Now let's end this discussion before I decide to send you to the salon in a dress," she told him, causing Mark's mouth to snap closed. "Mark dear, just one last thing before you head back to your house. I've notice how long your hair is getting, so I decided it would be fun if you to start wearing a hair bow. To help you along I've bought you basic ones in blue, red, yellow and pink. Start with the blue one to give you a chance to get used to the feeling of wearing one, and once you're more comfortable wearing your hair bows we could try the more girly colors on you like the yellow or even the pink," she told the surprised young man. "When would you expect me to wear a bow?" Mark asked, assuming she would tell him when he was over at her house. He was really hoping she wouldn't expect him to wear the bow when they were on a date outside the house. "Why all the time of course, silly. You can take it off at night and then put it back after you've had your shower in the morning," she told a stunned Mark as she pulled out the blue hair ribbon. She then proceeded to pull what hair he had into something of a high ponytail and secured the whole thing with the blue ribbon. Looking in the mirror he couldn't believe he was a guy wearing a hair bow. To his eyes the whole thing looked very feminine, and he couldn't imagine a normal guy doing it. Instead of taking the ribbon out he found himself taking the remaining ribbons from Miss Wilkins and storing them in his pocket. With nothing else to say Mark slunk out of her front door and tried to make his way back inside his own house without being spotted. He was already months overdo for a haircut, which meant his hair was fairly long at the moment. He speculated the salon could do a lot more girly things with hair his current length than if he had a haircut when he should have, and was worried his hair would look a lot more feminine than just a hair bow by the time Colleen was finally done with him. With Mark gone Trish picked up the phone and dialed Colleen's cellphone number. As soon as Colleen answered her phone Trish started talking. "I can't thank you enough for doing this Colleen. I'm very excited to see what you'll end up doing to Mark tomorrow, but whatever it is I'm sure it will be great. Please put the cost of any work on him on my tab, and add a $100 tip for yourself to the bill." "That tip is way too generous Trish. Besides, it's me who should be thanking you. Making that guy Brad you sent me a few years back girly was so much fun, plus I've had a lot of time since then to think about all of the things I should of tried with him at the time. Incidentally, what ever happened to old Brad?" Colleen asked. "Actually the things I was putting him through were too much for his male ego and he fled shortly after his visit to you," Trish confessed. "Oh, now I feel bad about driving him away from you!" Colleen exclaimed. "No, it absolutely wasn't your fault. It was all my fault for pushing him too much far too quickly. I learned my lesson from working with Brad, and have been much more careful with Mark as a result. I find it's a very delicate balance to continually feminize a male while not moving so quickly that they run away. After my experience with Brad I've gotten much better at maintaining that balance," Trish explained. "So you don't need me to play this low key?" "Not at all. In fact quite the opposite. I want you to give him whatever your imagination can come up with. At this point I have Mark hooked really bad, and I'm sure he'll accept whatever you decide. In fact lately I've noticed subtle signs he starting to enjoy his increasing feminization. For instance tonight I told him to start wearing a hair ribbon and ponytail at all times and he seems willing to do it. Also I've been careful to associate all of these things I make him do with fabulous sex, and it looks like he's getting to the point where the two things are becoming indistinguishable for him. If he keeps progressing like this by next summer he won't be able to get an erection unless he looks like a woman" "Really! Wow! That is so cool. You'll have to tell everything I would need to do to a guy to get him to that point. Ever since the thing with Brad I've been thinking about doing something similar to a guy myself. Men are just so cute and docile when you make them all nice and girly, aren't they?" she exclaimed. "Absolutely. I've decided I wouldn't want my guys any other way. The whole lesbian thing isn't really for me, but any time give me a nicely feminized guy who knows I'm in completely in charge over those macho jerks that are far too numerous," Trish agreed. "I agree. After our little chat I know I need to start my own project to do just that. There is a guy I've been on a couple of dates with over the last few weeks that might be a good candidate. I'll let you know in a few weeks how that works out. Meanwhile I have some really great ideas on what to do with Mark tomorrow. By the way, that was such a great idea you had of booking an appointment for yourself for tomorrow morning and then have me give it to Mark when he called in. Otherwise there was no way he would have gotten an appointment on such a busy morning," Colleen told Trish "I have to say it was a pretty good idea, but doing that seemed so obvious once it occurred to me" "Did you want to hear some of the things I have planned for your little femme boy toy?" "No, I want you to surprise me. I'd like to see the results of what you've done on Mark first hand, and then I will talk to him about it. I would prefer if the last step in all this is where you and I talk about it. I have to tell you I am so looking forward to seeing the results of your work when he walks through my front door tomorrow night, that you telling me any of the details in advance would just spoil it for me. Just so you know, I will make him follow that great suggestion of yours, and send him to you in that cute top you mentioned," Trish told her. "Great. The idea just came to me as I was speaking with him so I'm glad you like it. Don't worry, I'll give him a complete feminine salon experience and then send him home to you all nice and pretty," Colleen summarized as she hung up. Chapter 5 The next morning was something of a trial for Mark as his mother immediately spotted his hair ribbon. "Mark honey. Why are you wearing a ribbon in your hair?" his mother asked with a very puzzled note in her voice. "It's all the rage for guys my age," he lied, hoping she would accept it as one of those odd teenage behaviours and let it go at that. "Really? Teenage boys are wearing bows in their hair? Are you sure about that? I don't remember seeing any of the boys around town with those in their hair," she told him. "Thankfully it hasn't got to the point where every guy is doing it. By the time that happens it isn't cool anymore. No, it's still just a minority of guys into this. Once the style goes too mainstream I plan on stopping," Mark lied, tying desperately to convince his mother that this latest change was just him being a typical teenage boy. "Okay honey. I guess I'll keep a lookout for other boys wearing hair ribbons," his mother told him with a sigh, apparently not completely sold on his story but not quite ready to reject his explanation out of hand. With a sigh of his own Mark headed out the door so he could make his appointment on time. "You must be Mark. Well Mark, I have to say that is a very pretty hair ribbon you are wearing. Please take your coat off and have a seat in the waiting area," Colleen greeted Mark as he walked through the door of the salon. "I'll start doing your wet set as soon as I'm done with Mrs. Ambrose here," she promised before continuing. "Meanwhile you will have to outline what else you wanted done today. If you want I could give your hair some soft curls, some highlights and then tease it out a little to increase the volume and make it really quite sexy," she suggested "To be honest I'm don't really know. I've never done anything like this to my hair before. Whatever you do, can you make sure it looks very masculine," Mark said faintly as he removed his coat, revealing the blue vaguely feminine top Trish had made him wear to his appointment. With it's neckline and fancy detailing the top was definitely a bit girly looking for a typical guy, and Mark was visibly uncomfortable wearing it. "Um, okay," she replied as she continued working on Mrs. Ambrose. Colleen finished with the customer a few minutes later, quickly ringing her bill through the cash register. As Mrs. Ambrose left the salon Colleen turned towards Mark. "Have a seat please and we can get started," she told him, indicating the chair at the front of the salon, facing the big plate glass window with 'Beautiful New You Salon' engraved on it. "Does it have to be the chair in front of the window?" Mark asked. "That's where my station is," Colleen said innocently, not telling Mark she had moved her station there just for today in order to place Mark in front of the window while she worked on him. She wanted anyone walking by the salon to spot what was happening to this young male customer. "Besides even if I wanted to move you, it's a very busy morning and there are no other stations available right now," she added. "But it's so public!" he exclaimed, not ready to give up quite yet. "Don't be such a baby. Everything will be fine," she assured him as she pushed him into the chair and wrapped a pink cape around him. "That's a very pretty top you're wearing. It matches that pretty hair ribbon of your so nicely," she added "although you may want to consider wearing a nice padded bra under it next time. Having a proper bust-line would make you feel so much more girly," she commented with a grin, saying it loudly enough for most of the salon to hear. Colleen's banter was disconcerting for Mark, especially as he was actually wearing a bra under his top, just not a padded one. As instructed by Miss Wilkins he had started wearing a bra every day and was getting a little more comfortable with their presence in his life. He had finally gotten to the point where he would refer to 'his' bra and 'his' panties instead of pretending the lingerie in his dresser drawers belonged to a girlfriend and he was just storing it for her. He was also used to the routine of having his shower and then immediately donning a bra and panties as he prepared for the day. What he was not really used to as yet was the feeling of wearing a bra all day. The way his bra band and bra straps would flex and shift as he moved still threw him off, and he would find himself fussing with his bra quite a bit as a result. Tilting Marks chair backwards over the sink while turnin