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Jamie answered the door, as I sat watching TV trying not to show any emotion. Ron, her date came in with a wide smile on his face and a quick hello. As she grabbed her purse, she turned to say bye and that she expected to be back by midnight. Ron told me thanks and maybe we'd talk later. I nodded my head and said have a good time. It might seem odd to wish your wife to have a good time on her date, but it was partly my idea. We'd been married just under 4 years after living together for 5. She and I were both fairly liberal and sex was a big part of our lives. When we met, I was a virgin but she was more experienced. As we became settled together I had a longing to explore a little more sexually. Initially that meant trying new stuff, like new positions, extended oral foreplay, and role-playing. That helped, but our kinks weren't quite aligned. Finally we discussed possible sex with others. Our first venture was to swing with a couple who lived in our apartment complex, Gary and Marti. We had known them for quite a while and they seemed to be the exact opposites of us. Gary was muscular, with dark body hair, and an aggressive personality; quite a contrast to my trim frame, light blonde hair, and shy demeanor. Marti was petite, with barely A-cup breasts, but very flexible, with long hair and a scholarly personality. Jamie was the typical curvy hour-glass body, very busty, taller, and liked to flirt. So a switch gave us each a taste of something different. Especially for me; Marti loved oral and was as interested in riding my face as my cock, a decided change from Jamie. It was a saving grace for me, as I often had erection problems the first time with a woman. Gary was a definitely different from me in another way as well; his cock was a good 3 inches longer than mine. But we only swapped with them a few times, as Gary was just a bit too hairy for Jamie's tastes and Marti's small size up top wasn't my preference. Next, we tried meeting people at bars, but we went no further than general groping and kissing. The problem was we could never find a couple that we both found desirable. About that time, a young blonde joined the company that I worked for. She had a very sexy body, but wasn't exactly pretty; we flirted almost immediately. I had the impression that she wanted me and I thought that the fact that she might be average in appearance would give me a better shot at her. I had never considered cheating on Jamie, so I talked to her about it and finally suggested that maybe we might try a bit of an open marriage. That way we could each have sex with someone that really attracted us; but we had to be above board so everyone knew what was happening. I was of course sure I could score with the blonde, but naively thought it might take a while for Jamie to find someone. As it turned out, I was completely wrong. The blonde shot down my first couple of attempts at hitting on her. She finally relented to have a drink with me after work, but it was very awkward and nothing happened. After she left the company, I lost my courage pretty quickly. After being with Jamie I had forgotten how my shy nature kept me from really having much success with women. Jamie on the other hand, found someone right away, Ron, a guy from where she worked. He was pretty much just like Gary, without the hairy body. So when he came to pick her up, I had to be polite and let her go. Inside my stomach was turning, and I was a bit depressed because I wasn't getting anything out of it. This was their second date, and I was pretty sure they screwed the first time out. As with our other sexual diversions, I had started the process, but wasn't sure how long it would go and what would happen. That night alone I was quite anxious, especially when Jamie didn't return until 2 am. The next week, we went on as if everything was normal, but I was trying to think what to do next or how to stop it, when Ron called. I was about to tell Jamie to get the phone, when he told me he had called to talk with me. He asked if I could meet him for drink at a local bar. I was a bit puzzled but agreed to meet him the following night on the way home after work. I got to the bar before him, and not being sure what to do, I sat there waiting. He arrived about 15 minutes later than our scheduled time. He was smiling the same way he did when he came to pick up my wife. "Hello Michael, let's grab a table. That one in the corner looks good, why don't you go get it. I'll get us some drinks." I just nodded my head, and got up. I turned to tell him what I wanted, but he was already ordering. I sat down and he soon strolled over. He was holding a beer for himself and a white wine for me. I usually drank beer or rum and coke, but took the wine anyway. He smiled at me as he sat down. "Thanks for meeting me Michael, you do go by Michael don't you? Not some shortened version, like Mike?" "Michael is fine." "Did your parents call you that, or something else, like Mikie?" I blushed. Either he was a good guesser or Jamie had told him that. "When I was younger they called me Mikie, but that stopped by the time I reached high school." "Makes sense, I could never understand guys who kept using cute nicknames when they were older. I mean Mikie is okay when you are young, but who would want to be called Petey, or Tommy, or little Dickie." I didn't quite know where he was going with this, but his last nickname caused me to worry. He had a bit of smirk on his face when he said it. If Jamie had told him my childhood nickname, maybe she said something about my smaller cock size. It was something that always made me self- conscious. She had not said anything about him, but it was obvious from the bulge in his pants that size was a positive for him. "Well, anyway, I just wanted to touch base with you. I was a bit shocked when Jamie asked if I was interested in a drink after work. I mean I knew she was married, but she quickly explained that you guys were cool with sex outside your marriage. We talked quite a bit about it really and I understood that you were each looking for something beyond what your partner could provide. So far, it's been a blast. She is a really sexy lady. But during our conversations, something came up that I wanted to find out more about. She mentioned before you started swinging, that you tried some new stuff, stuff outside normal vanilla sex. Is that true?" I blushed again. My insecurities made it tough for me to talk about some subjects, like sex, with anyone, especially other guys. My mind was racing, wondering what Jamie might have told him about our experimenting. "Yes, we tried a few things, but I guess it really didn't meet our needs." "I gathered that and it makes sense to a degree. I can tell that Jamie likes to be fucked; I mean she has a high sex desire, but doesn't really want to go beyond that. Even oral is not her cup of tea, let alone role playing or anything kinky. But I sense that is not quite the case with you. She mentioned some of the games you guys played, so I know some of the things you might like. To be honest, I like screwing her. The physical relief is wonderful, she is very attractive, and knowing she is married is a buzz, but I'd be more satisfied if I could quench more of my mental needs as well. You see I have a dominant personality, and I like it in sex as well. She told me you played some D&S games, both with her as a submissive and a domme, but that nothing clicked. But I think that is more on her side than yours. I've been a Dom for quite some time and have a general feel for when someone has a sub personality. Jamie is obviously not tuned into those mind games, but my instincts are that you are submissive. What aspect of that appeals most to you? Do you like bondage, pain, or humiliation? They can all be sexually exciting, but triggers are usually pretty specialized to each person." I was stunned, and quite embarrassed. I didn't really want to answer Ron, I mean it was hard enough to try to get my wife to do such things, let alone discuss this with some guy, even more so with a guy that was fucking my wife. Also, I was really worried about what all she told him. I couldn't just sit there, but I just stared down at my drink long enough that an uncomfortable silence fell on our table. Ron just smiled, and took a drink from his beer. "I know this is hard for you, but I also know it is what you fantasize about too. I know that because I focus a lot on my Dom side. For me, it is the control of another person. Making them bend to my will, expressing my power over them. So any of the dominance tools will do for me, but the markl of a successful Dom is to use the technique that gets right to the soul of your submissive. I understand your reluctance, but I expect to be answered. You will have to learn that your needs are secondary to mine. You will do what I want even if it makes you uncomfortable, so what is your poison?" I looked up at him, shocked, a bit angry, but also scared. I quickly decided I'd answer and then politely end this visit. "Umm, I'm not into pain. Bondage is okay, but I guess being in humiliating situations is something I think more about. However, it isn't a big part of me and something that Jamie and I just tried for spice. It didn't work; so no need to go further. Well, Ron I appreciate you wanting to meet and talk, but Jamie will be expecting me soon, so I better go." "I guessed it would be humiliation. That is a very common trigger, especially for insecure guys and really for guys who like to be fem. I can see that is definitely a turn on for you, so much I didn't even need to ask you, also because Jamie mentioned everything but that. Any couple playing sex games will try some form of play with lingerie and inevitably putting the man in some. But she didn't mention that at all. That told me you have a real desire for it and that you are likely very concerned about someone finding out. Looking at you, it seems obvious. I mean you already lean that way; your long hair, smooth face, pierced ears, all are marginally accepted by society as okay for men, but that are really more appropriate for women. Oh, and don't worry about Jamie waiting on you. She is headed over to my place anyway. I knew I would want to bang her again after talking to you and she wants my big cock enough, she'll agree to any time I want sex. But now, I want to set some rules. I know enough about you to be sure that you need to be controlled and I am the person for that. For starters, I expect you to embrace your femininity more. You hair is long enough, but a woman would do something with it. Talk to Jamie; get some ideas, maybe a girly haircut, maybe blonde highlights, or maybe both. But I want it noticeable. Second, even though your face is smooth, I see you have body hair. Girls and fem submissive boys, don't; so shave. I want you smooth everywhere by the time Jamie comes home tonight. Third, I want you to wear some little signs of your submissiveness and fem desires. Jewelry is always good for that. Start with some girly earrings. Large hoops are nice or long dangly styles, or something with color. Rings, bracelets and anklets are nice touches too and of course a petite, ornate women's watch. These are all telltale signs that I want you to display at all times. Another visible sign is cosmetics. Touches of mascara, a little blush, or lip gloss, all identify you as a fem boy. Finally your clothes need adjusting. My fem boy slaves wear panties all the time and more when I tell them. So you and Jamie go shopping this week. I want you to have a full wardrobe by the weekend. I'll tell her what to get you, but you will go with her when she shops. That is part of the humiliation." I had heard enough; enough to be scared and to realize I needed to stop this, even if it did appeal to me sexually. This wasn't the way I wanted to play. "Ron, if I do have a submissive side and if I was at all interested in fem things, that would be one thing, but in no way would I want to do those with a guy. I'm not gay, I don't find guys sexy or attractive, and I just can't see myself doing those things you described." "Honestly I don't care that you aren't interested in men sexually; I'm not either. But control is what I like, and forcing you to do something that is totally against your nature is in fact one of the things I love about dominating a straight guy. They usually hate doing what I say and you can be guaranteed the humiliation you feel will be far worse because a man is telling you what to do. That humiliation will multiply as I dominate you in front of your wife. But don't even think about refusing me. Jamie has an itch for me; an itch for my size that you can't fill, so even if you want to say no, she won't let you. Not to mention how much I know about you that others, others not tuned into D&S would find very interesting. Even the fact that Jamie is having sex with me could be embarrassing for you if those who know you find out. You can be sure I've snapped a few private photos of your hot wife in bed; I purposely took one nude photo that shows my photo on the night stand. So you make your choice who you will be humiliated in front of me or others like your neighbors, your family and the guys at your office. If you're not smooth, when Jamie comes home, then I guess I will have to drop by to see you at work. You don't want that do you, Michelle?" With that he stood up, finished his beer and left. I sat there feeling like the air had just been sucked out of my lungs. I blinked a couple of times, trying to tell myself that this wasn't real; that our conversation had been a dream. But reality began to sink in, and my breath returned, shallow and rapid at first, as I admitted what had just occurred. As I thought about his requirements, about what he outlined for me, I began to tremble. But all I had to do as think about my work associates or neighbors and how bad it would be if they knew. I could live with them being suspicious; of them looking at me oddly because of my feminized attire. But if they knew I was a sissy and a submissive one at that, and that my wife was going to bed with another guy with my permission, I couldn't bear that humiliation; that was too much, even for me. So by the time I reached my car I knew I had to do as Ron said. At least l had to obey him until Jamie got her fill of his cock, and maybe he had tired of playing with me. I wanted to feel like I was doing what I needed to in order to survive, but I had to be honest. My cock was rock hard, so it was apparent that at some level the idea of finally being a submissive to a real dominant was exciting, even if it was a man. By the time Jamie came home, I had done as Ron had instructed me. My body was smooth, everywhere. I had hesitated about shaving my pubic hair especially from my cock and balls, but only briefly. The last thing I wanted was for him to think I wasn't going to follow his orders. I shaved my genitals, but left a small landing strip of hair, realizing that look was even more feminine than being totally nude. After I finished I could see why this had been a requirement. My legs, underarms, chest, everywhere looked so different. In the mirror I saw prepubescent images, mostly a girl's figure, except my cock and balls now looked like those of an 8-year old boy. I never deluded myself into thinking I was large down there but at least average; without pubic hair, I looked downright tiny. My face was constantly flaring up, as my humiliation at my appearance caused blushes to wash over me. Hearing Jamie enter, I quickly threw on my robe. She entered with a sly grin across her face. I could tell she had been fucking, as her makeup was messed up and her clothes were wrinkled. I was embarrassed so much, that I couldn't look her in the eye, choosing instead to stare at my feet. She walked up to me, and pulled open the robe, revealing my smooth chest and legs. "I see you've done as Ron wanted. That's good; I didn't want to fight with you about it. I can tell you're embarrassed, maybe even ashamed, but don't' be. This will be a good thing. We wanted to be open with our relationship, so we could still love each other without denying ourselves any pleasures. You know I couldn't be the dominant person you'd fantasized about and you have to admit you can't give me the feeling that a large cock can. Luckily for us, Ron can do both. He was very specific about what we need to do for you this week; you know that already. But he was equally specific about my needs. He said he expects that we will fuck whenever possible and wants me to be available for him, which fits my desires as well. That doesn't mean we won't still have sex, but that I won't get any more of his large cock until you are ready. So that means, we are going to get your requirements out of the way as soon as possible. I want you to see if you can take tomorrow afternoon off; if you can I'll make an appointment with Becky to do your hair. After that we can go shopping; just us girls and get you some new stuff. Ron was clear about what you needed to have, so it should be pretty easy. Since it's already late, I think we should get ready for bed. I need a shower, first, so just look through my dresser. You can borrow one of my nightgowns to sleep in, okay? Ron said we should be like girl friends for a while until he tells us otherwise. Once you have fully submitted to him, become his little girl then he will allow us to have sex again." With that she leaned in and kissed my cheek before heading to the shower. I was petrified, because I could see no resistance from her to his plan. Defeated, I went to her dresser and picked out a plain, light pink, knee length gown. I choose it partly because I knew it had matching panties and I didn't want my small bare genitals to be uncovered. I slid beneath the covers and waited for Jamie to come to bed. I must not have realized how drained I was by the evening's events as they next thing I heard was our alarm. It took me a minute to get oriented but everything soon came crashing back into my mind. As we got up to get dressed, Jamie calmly put a pair of her panties on the bed. "Here use these today; we'll get your own stuff after we finish at the salon." We dressed in mostly silence and soon were off to work. The morning was agony. Every time I looked at one of my co-workers, I imagined what they would say if they knew my hidden secrets. My boss said I could have the afternoon off, so after some phone calls with Jamie, I had my hair appointment set for 12:30. I was to meet her at the salon. As time drew near for me to leave, I began to panic. In the abstract, it was easy for me to think that being feminized was better than Ron telling them directly, but now that I was to get changes made, I saw how humiliating it was going to be. As I was getting my stuff together to leave, Leah asked what I had planned. She was one of the young, single secretaries that worked for our company. Although we spoke at work, we were not close. After the blonde had left, I briefly considered trying to hit on her, but I never got any kind of sexual interest from her when we talked, so I hadn't pressed it. Now I decided I would be proactive, so I told her that I was going to try a new look for my hair and do some shopping with Jamie. She smiled and told me that it sounded like fun; her boyfriend would never do anything like that with her. I forced a smile back. Leaving, I just prayed that my appearance when I returned tomorrow would not be too bad. Jamie arrived at the salon just as I did and we entered together. The receptionist checked our appointment and rang Jamie's usual hair dresser. In few moments, Becky came to the front. She was a stylish dressed woman our age or slightly older. "Jamie you look good. How are you? In your call you mentioned that you needed a favor for your husband, Michael. What's up?" "Hi Becky, we want to try something different. He's kept his hair the same for so long, we just wanted to go a bit wilder, you know? Something wavy, maybe some color or highlights something with some pizazz." As Jamie was talking, Becky smiled at me and gave me a quick look, I'm sure checking out what my hair looked like now. I had never been here before, so she probably had no idea what it looked like. Finally, Jamie looked over at a poster on the wall. It showed a woman with long wavy hair, past her shoulders, with curls at the lower ends. Pointing to it, she said. "We want something like that, you know with some body or style." Becky glanced at the poster and then back at us. "That style is real popular now, but it's a woman's hair style. Is that what you want?" "Well, something similar to that; I mean, maybe something with a side part, and some waves." Becky nodded her head, and then reached for a book showing some men's hair styles. They looked through it a while, but after Jamie refused her suggestions, she picked up a book of women's hair styles. She flipped it open to a page showing something similar to the poster. The model's hair was about my length. She looked at Jamie again. "I can certainly do some highlights for him. His base hair color is nice, a warm blonde, but if I put in some lighter streaks, all over, it will give it much more depth and pop. And I can cut his hair so it sweeps over his face from a side part like the style in the book. But to get waves, we have to either give him a perm, use rollers, or a curling iron. Are you talking about a perm? That usually gives much more curl and with his thick hair, I'm not sure it will do what you are showing me here." "Definitely give him highlights and restyle it for a side part, but I agree a perm is probably too much. We just want to punch it up. If you roll his hair, can you just give him some waves to frame his face?" "Oh, I can do that, as long as he is okay with using rollers. Most men tend to shy away from them. But I can show you how to set his hair so you will be able to repeat the look later. You guys have anything else in mind?" "Yes, his brows are so thick and unruly. Can you shape them a bit; make them a bit thinner, so they look much neater?" "Sure. Kathy can do those in a jiffy. Is that it?" "Just one more thing, how about we get his nails done? His look terrible, and I'm due for my regular manicure and pedicure this weekend, but I was hoping you could work me in to save a trip. Could we have them done together if possible?" "I think that can be done. Talk with Regina at the front desk, but our nail techs are pretty open today. If that's it, I'll go ahead and start on his color work. You like what we talked about Michael?" I had sat there, mortified at what all was being discussed. Now that it was happening I was getting scared. But I nodded my head yes and let Becky do as she had outlined. Jamie lined up the nail appointments and then left to shop some, so I was all alone. The color, cut, and then rolling my hair took over an hour and I felt humiliated as she did the work. I kept getting smirks and odd looks from the women in the salon as she worked away, especially as she set my hair. Just as Becky finished rolling my hair and sitting me under a big hood dryer, Jamie returned. Kathy came over to do my brow shaping. At first, she looked them over and used scissors to trim the hair so it wasn't so long. But then she applied some wax to the upper edge of my left brow. I almost squealed when she ripped it off, but I kept my composure. She followed by doing the lower edge. When it was off, she looked at Jamie, who nodded but said something I couldn't hear because of the dryer. Kathy then re-applied some wax taking more off both the upper and lower edges of my left brow. This time when she was finished, Jamie smiled and nodded her approval. Kathy then repeated the work on my right brow, taking more off with the wax applications on the first try this time. After she was done, I sat under the dryer for another 10 minutes or so, until it was time for Jamie and me to get our nails done. We sat next to each other with two young nail technicians working on us. Jamie outlined what we wanted. "I'll have my regular work with that nice Fire Red color you guys have. Since this is Michael's first time, you'll probably need to do his cuticles, shape the nail, and do any callouses. I know some guys just get the nail surfaced buffed, but I think a clear polish will look closer to what we had in mind and eventually he wants a nice elongated oval shape to his fingernails so keep that in mind too.' Smiling she looked at me, reached over, and lightly squeezed my arm. The nail work took about 30 minutes, as both girls were really good. Jamie's long nails sparkled. Looking at mine, they seemed so visible, even though the polish was clear. It was just that they sparkled when I moved my hands. I could already see that it would be quite humiliating for me and hard to keep from being noticed. As we were finished, Becky came to get me and sitting in her chair, she removed the rollers to comb out my hair. She worked quickly, occasionally teasing out a curl with her fingertips. Finally she seemed pleased with how it looked, so she covered it heavily with hair spray. I could see from Jamie's reaction that what Becky had done pleased her. Spinning the chair around, so that I faced the mirror, Becky spoke up, looking at me but talking as much to Jamie. "What do you think? I hope this is what you had in mind. When you described it, I wasn't sure it was a good idea. But seeing how it turned out, I kind of like it. The color is a definite improvement and the style both fits his facial shape and his delicate features. I mean a guy with a big nose or rough skin would look mismatched with such a pretty hair style. Luckily, Michael has a cute button nose, high cheekbones, and the full lips that compliment such a soft, sexy hairstyle. Styling his brows was a good idea too; they complement his overall look now. Michael, it may take you a bit to adjust too, but I think once you get over your initial shock, you'll see how cute it looks.' "Becky, it is perfect! That is just what I wanted for him. I mean it is soft, pretty, sexy, and so unusual for a guy. I was so tired of him looking like every other guy with long hair; their hair just hanging down, straight, from a center part, with no personality or interest. I love long hair but Michael's just didn't seem to live up to its potential; now it does and how. " As they chatted on, I sat staring at my new image. The hair was cetainly different. The color would have been radical enough, but my new cut was definitely a feminine look. It now swept across my forehead left to right, with soft waves, falling to about half-way down my neck. The style produced a sort of bangs look and as I moved my head it would drop down partly over my right eye. Below the part, the hair was curled in soft waves. The part itself only went back about half-way on my head; the remaining hair was combed up and then backwards down to my neck. All around the bottom the hair was curled under with loose waves. Overall my hair had a lot more body and appeared bigger. Although Becky had sprayed it all, when I moved my head the waves bounced. Below my hair, my new eyebrows were thick near my nose, but were thin and arched going outward. They were markedly different than the solid looking caterpillars that sat up there before. Luckily, they were light blonde and were never highly noticeable. Alone they might not have been too radical, but with my wavy hairdo and polished nails, I would have to endure lots of stares and probably questions and jokes at work. As I rolled this around in my head, I noticed both women staring at me and realized that Becky had just asked what I thought. "It certainly is a new look for me. You did a great job of changing things up and I can see this is much more stylish. The woman's style influence is noticeable, but I can see where you've toned it down a bit from what we looked at in the book. I'm pretty excited about my new look and really appreciate your help." I added the last part, just so Becky wouldn't feel bad or be suspicious of our explanation. I could see that Jamie was happy too, which meant in reality the look was more feminine than any man would normally wear and just what Ron had ordered for me. I could see I would get little support from her, as she was entranced by him. The ladies continued to talk, making a follow-up nail appointment for both of us in 3 weeks. I knew that Jamie was also interested in completing our shopping so after I paid we headed out to the car. She told me had picked up some cosmetics and hosiery while I was at the salon, so that should make our trip shorter. We needed some lingerie, jewelry, shoes, and a dress; all of which we could get at the mall. The first store was Belk, a large department store where Jamie headed straight to the lingerie department. I immediately felt awkward, but she wasted little time as she started looking at panties. She held up a hipster style, with a lace front and small bows on each side. "What colors do you like, pink or the pale blue?" "I guess the pale blue." "Good, I like the pink so we can get them both. Judging from how my panties looked on you this morning, I'd say you are a size smaller than me. A size 5 should do just fine. Ron wanted you to have some cute sexy styles and some with matching bras. I think this cute little print pair will do and so will this leopard print bikini. Let's choose your bras and then we can find some panties to match that." She handed me the panties and we headed over to the bra area. We had just begun to look at styles, when a young saleslady approached us. I already was a bit anxious standing there holding my panties in my new feminized hair style, but her approach heightened it. "Hello, welcome to Belk, can I help you find anything?" She was cute and petite with a pixie hair style and fashionably dressed. Her face was practically beaming although she did have a puzzled look when she glanced my way and saw my hair. Jamie smiled back, as she held up a white lace bra. "Yes, we could use a little help. We need some smaller size bras, A- cup, probably, but I'm obviously not really familiar with what styles or designs work best for a smaller bust. " The saleslady smiled at her comment, because Jamie was easily a C- or D-cup. Glancing again my way, she looked me over a bit more and I could see a flash of understanding of what might be happening here. "Well, there are a couple of styles that most small busted women like and I'd be glad to show you some choices. We have a nice sale on our lingerie this week, and I think we can find something you'll like. But first, what band size are you looking for?" Jamie smiled wider at her question, and almost started to giggle, but answered her that we didn't quite know. Glancing at me again, the saleslady smiled back at Jamie. "I'd be glad to do a bra fitting. We can go back to the dressing rooms, where it is private. If you're not sure of the band size, it makes it almost impossible to get a proper fit without measuring. Come on back honey and let me see what we need." As she talked, my face began to flush. This was exactly the kind of humiliation that I craved and feared the most. Someone seeing me for what I was inside, I knew it couldn't be avoided but it was just like the hair salon, frightening. Seeing that the saleslady now understood, Jamie nodded her head and we followed her back to a small booth, off the main dressing rooms. The saleslady looked at me and could tell I wasn't wearing a bra. "Normally, you do a fitting over the existing bra, but in this case I think I can just measure over his chest. Take off your shirt and I'll get started." She just calmly stood there, smiling, as if this was a regular occurrence. Jamie was right outside the room. I put the panties on the bench and quickly unbuttoned my shirt, hanging it on the hook next to the curtain. Peeling the shirt off and exposing my shaved chest and underarms made my face begin to blush. The saleslady ignored my discomfort and expertly wrapped a cloth measuring tape around my chest, measuring below my breasts, across the nipples, and then just under my armpits. Her touch was electrifying and my nipples quickly hardened, but she didn't seem to be phased. Glancing at the panties on the bench, she dropped the tape down to quickly measure my waist and hips. Finally she looked up at me and then out to Jamie. "His measurements indicate 35 inches, and we normally round up to an even number. I think his best fit will be a 36 band. Now his cup size is just slightly below a full A, so I'd recommend he use a contour cup or a balconette style bra. Contours generally have some foam lining and maintain their own shape, which will help his projection and smooth out any irregularities from his smaller size. A balconette has some padding below with wide set straps, both of which help push the breast inward and upward to give a little d?collet?. Both of these styles are real popular with smaller women and I think you two will be pleased with the result. The other choice would be to opt for a padded style or use inserts which would give a larger bust. If you want to remain with the natural looks, the best brand for those are Wacoal and they are on sale today. By the way, based on his narrow waist, he would take a 5 panty. Is that you guys picked out?" "Yes, I had him figured for a five. For the bra, I definitely want a natural look for him, so maybe we can find a couple of each style. He does want a matching panty. Does Wacoal offer that?" "Of course, they have some lovely styles and with his petite frame they will look good on him. Why don't we go out and find some for him to try on?" The women left me there, blushing and feeling like I wanted to die. In my fantasies this was the kind of humiliating situation I would be forced into by my wife. Now I was having mixed feelings between the arousal from the humiliation tempered by the shame of knowing my wife's lover was the one controlling me. The women were gone about 10 minutes, but returned with 4 bras. Three were contour styles in beige, white, and a salmon color, all trimmed with white lace around the band. The balconette style was sheer lace in black. Each bra had a matching panty. Jamie had brought two panties for the balconette, one a thong and the other a garter panty. The saleslady wasted no time in slipping the beige contour onto me. It fit nicely, although I was a bit distressed by how the formed cup gave me more breast than I normally had. The balconette had less projection, but the cup shape formed a slight cleavage. Jamie was thrilled with both and as I dressed they took the lingerie to pay. I was relieved partially because it was over and I had been afraid, Jamie would insist I wear one out of the store. I joined them at the counter, as she was finishing up processing the sale. The saleslady smiled as she looked up at me and handed me the bag with my bras and panties. "I'm sure you'll love these. Wacoal is a great brand and they fit you perfectly. If you ever need any other accessories, Wacoal has some lovely camisole and shape wear options that will match your new lingerie, so just come back. By the way, I love your hair style. It looks so current and unusual for a guy. Thank you for your purchase and have a lovely day." We headed out of the lingerie department and I felt pretty awkward holding the bag of underwear. Jamie headed straight for the misses department. We made quick work there; she said I only needed a white dress, we found a cute lace shift, and a skirt outfit, pink pleated with a matching flowery blouse. I was relieved since she didn't feel I needed to try anything on. From there we breezed through the shoe section. A pair of simple tan pumps with a 3-inch heel would be all we needed; again she knew my size so we just bought without trying them on. After finishing our clothes selections, Jamie led me out of Belk into the mall. We stopped at a small jewelry kiosk where we found a variety of items that Jamie said we needed. These pieces included a watch in gold and silver with glittery trim, a set of matching necklace, dangle earrings, and multiple bangle bracelets in aqua and silver, several silver rings, a silver anklet with a heart locket, large silver hoop earrings, and a bracelet made of originality beads. The beads featured sayings, like love to shop, or charms shaped like high heels, hearts and flowers in silver and black. After we paid the girl at the kiosk, we decided to get something to eat at a restaurant in the mall. The whole time I was shopping, walking and now eating, I could see people glance my way. My fem hairstyle was attracting a fair amount of attention, although most people seemed only intrigued by my look. The waitress did refer to us as ladies when she first came up to the table, but after a closer look seemed puzzled and started to apologize. I figured that would make more of an issue of it, so I just laughed it off and she smiled. At the end of the meal she brought the check and I could see she was dying to talk. "I can take the check anytime you're ready, no rush. But I do have one question if you don't mind. I love your hair; it's so different and stylish. Have your worn it this way long and where did you get it done?" "I just got it styled today, although we've talked about a look like this for a while. I liked to keep my hair long, but felt I was in a rut for my look. I'm glad you like it. My stylist is Becky at the Sheer Locks salon." The girl seemed pleased with the answer and we paid and left soon after. Although I felt a bit exposed walking around with my new look, the fact that I had gotten a couple of positive comments made me feel a bit better. I just worried about going to work tomorrow. At home Jamie had me try on the new dress and skirt outfit. Both fit well, so she was pleased. We then did a few chores, paid some bills, and went to bed early. I tried to sleep but the fear of what awaited me at work kept flashing though my mind. It was not going to be an easy next step. The next morning, I woke up dreading my first day at work. I washed up and shaved quickly. My hair had not been too rumpled by sleeping on it, so all Jamie had to do was add back some curl using her curling iron. I dressed normally otherwise, except for the pink lace hipster panties and my ladies watch. Jamie told me Ron preferred I transition slowly to my new appearance. I was relieved at that, it was going to be bad enough with my hair, brows, and polished nails. I got to work a bit earlier than normal and went right to my office. I plunged into work, trying to delay an interaction. That was short lived, as Leah came by first thing. When she knocked on my door and entered, I had to turn to face her. "Michael, what a change! Your hair looks so cute; I love the color and the way it frames your face is so attractive. Did you pick the style or did Jamie? I really like the soft waves; they make the most of your longer hair. Your old style just sat there. How do you feel about your new look?" Her bubbly outburst was a bit unexpected, but I was happy she thought it looked good. I answered her questions and as we talked I could see her glance at my nails and notice my shaped brows. I decided to be proactive again, representing that I didn't think this changes were unusual for a man. "I'm glad you think it looks good. I love it and so does Jamie; we looked at some choices and agreed on this one. She was also tired of how bland my hair looks. Her stylist was so helpful, she also persuaded us to neaten up my eyebrows and get a manicure. She was pretty convincing about how small details can make a big difference. I must admit I was a little nervous about it all; I mean it was such a change. Jamie loved it so much she even bought me a new watch. She felt my old one was too big and bulky anyway. You don't think it is too much do you?" "Well, it is very noticeable. But it looks good, so that is what counts. I can see what she meant by your brows and nails; I think way too many men just blow off personal grooming like that. I'm glad to see you feel it is important too. I understand what Jamie means too about your watch. You don't have that big, bruising look of most guys. A smaller style watch is more appropriate for you, especially with these new looks." Just as we were finishing our chat, her friend Sammie came by, so I recapped it all again. She was not quite as enthusiastic; I could tell that she saw it as too feminine for a guy, but she didn't say anything directly. That was the response I got from the majority of my co- workers that day. Most were polite, but still looked at me oddly. The men especially seemed puzzled by the change; one even asked if that didn't mean more work keeping it looking that way. I could tell they just didn't see why a guy would go to all that trouble for his hair. The implication was that women would do that, but guys had better stuff to do. I found talking with the women about it a little easier. With the men, it was just humiliating. I even blushed when my boss first saw me and I tried to explain. He finally said it didn't matter to him, as long as I did my job. I realized then, that the path of humiliation that Ron had chosen to use on me was effective, very effective. By the end of the day, I was emotionally spent. At home, Jamie was full of questions. She pumped me for information as we got dinner together and ate. That evening, we relaxed watching television, but she told me I need to roll my hair because my hairstyle would not survive another night's sleep. After I washed it, she showed me how to put in rollers and what pattern to use. Sleeping on them was another story; it took me twice as long to fall asleep. The next day, it took a lot longer to get ready. Combing out my hair and spraying it in place was nerve wracking. The last thing I wanted was for it to look bad. Jamie also insisted I use women's brands of deodorant, shaving cr?me, and that I apply body lotion to my shaved legs. All in all, it took an extra hour of prep. At work, the initial excitement about my new look was over, but I still got funny looks from most of the guys, usually a longer stare, a whisper to someone, or a puzzled shake of their heads. I just smiled and tried to act like nothing was really different. The morning went by quickly as I was buried in work, but Jamie called and said she wanted to meet me for lunch. I arrived at the restaurant and saw her at a table, but she was not alone. Ron sat next to her. As I approached, I could see the smile spread across his face. He stood up, and actually pulled out my chair for me. I couldn't help but blush. "Very well done, Michelle; Jamie told me you had fully embraced your submissive, feminine role. I like that your hair style, both the color and cut, screams girl. I guess you've turned some heads at work. Well you need to get used to it. I have no intentions of stopping at this. I will however, allow you to gradually expose your inner girl. Once they see and accept the tract you're on, then we can be sure you won't lose your job. You will of course be humiliated at it, but I don't want to threaten your livelihood. Jamie's told me you are complying with my orders, but I want to see for myself. Please undo your pants. I want to see what pretty panties you have and make sure you are smooth as ordered." I blushed further, but unbuttoned my pants as discreetly as I could and pulled down my zipper. Laying back my fly, I exposed the blue lace panties that Jamie had told me to wear this morning and pulled up my shirt, so he could see my smooth, hairless belly. Jamie pointed out that I picked out the panties as ones I liked. He laughed and seemed satisfied. The rest of the meal was awkward for me. They sat close together, with lots of touching and intimate chatter, and Ron had insisted that I only eat a small salad. That was going to be my lunch menu from now on. At the end of the meal, as we were about to leave, Jamie reached in her purse and handed me a small bag. I opened it to look in, and saw a two-piece swimsuit. The top was a strapless bandeau style and the bottom was a small bikini. I looked up at them puzzled. "Michelle, I decided to reward your good behavior. I noticed when we met at the bar the other night, that your skin is decidedly pale. Most women would choose to tan themselves, so they would look better in the skimpy outfits that you will progress to. I took the liberty of calling a friend of mine; she runs Suntan Holiday, a tanning spa on Beaumont Avenue. I told her Michelle would be coming by so she is expecting you. You are to sign up for the two week vacation special. Wear this suit when you tan; I want you to have definite tan lines indicating your feminine preferences. Start today after work. Jamie and I are going to take the rest of the afternoon off, and she won't be home till later. She needs to see that when you obey my commands, she gets the rewards she wants. Understand? Also, I want you to slowly increase your feminine signature. Start by wearing your girly earrings tomorrow, and then add something more each work day afterwards. Since tomorrow is Friday, I'll come by your place to be with Jamie on Saturday. You can show me how you look in your new dress then." They rose and left, leaving me to pay the bill. I was angry, a bit hurt, but didn't know what to do. I felt trapped. It was obvious he was going to ratchet up my feminization and that Jamie had no problems with it as long as she was getting the sex she wanted. The rest of the day dragged on and I stayed a bit late, just to delay going to the tanning salon. Finally I left and headed there. It was a small place and not particularly busy. I approached the front desk where a middle aged woman sporting a rich tan and a name tag, Teresa, was behind a computer. "Hello Teresa, a friend of mine suggested I come by here to get some color. He suggested I try the vacation special. Ron said he knew you." "Oh yes, Ron did call. You must be Michelle. I see what he means, you certainly need some tanning. The vacation special will bring you up to speed gradually but continually over 10 visits. It's real popular with girls who want some color before spring break or other beach holidays. I can work you in now, and then you will come every other day. I'll set the timer so you get slightly more exposure each time. That way you get a chance to build up some without getting burned. Just sign here and pay the fee up front." I nodded and did as she asked. It was embarrassing for someone else to call me by the feminine name Ron had christened me with, but I just acted as if it was nothing. Entering the tanning room, it felt awkward to disrobe and put on the swimsuit. I felt silly, but lay down in the bed following the suggested positioning of arms and legs. It was only about 20 minutes and I soon was dressed ready to leave. She gave me my appointment schedule and I headed back home. The rest of the evening was dreadful, knowing Jamie was with him. She didn't come home until nearly midnight and I had purposely gone to bed so I wouldn't have to face her. Friday was the first day I increased my feminine look; the hoops were a big hit with Leah. I used the excuse that Jamie wanted me to accelerate my fashion upgrade. As he indicated, Ron came by on Saturday. It was horrible for me. Jamie insisted I shave everywhere again, so I would be totally smooth. I wore a matching bra and panty, some pantyhose, my dress and heels. She did my makeup, using mascara, blush, and lipstick. Along with my curled hair, I had to admit I looked a lot like a girl. The evening was awkward. He had brought over Chinese food and after eating, they sat on the couch watching a movie. The day ended with them fucking in our bed. I slept in the guest room, even after he left around 1 am. The rest of the weekend I spent doing chores with Jamie, dressed like I used to, only with panties. Ron made it clear that I didn't have to be fully feminized unless he said so. I was a bit surprised on Sunday when we went to bed. Jamie cuddled up to me and eventually we had sex. It was good for me, but I could tell it didn't quite have the same effect on her. Afterwards, she told me that Ron had told her I deserved a reward as I had been a 'good girl' that week. It stung a bit to know that my only time to be a man with my wife was when her lover thought I was being a proper girl. The next two weeks I settled into a routine, slowly expanding my feminine appearance. After the hoop earrings I wore on Friday, I added the silver rings, the anklet which was basically hidden, a bracelet, a necklace, and finally a bra. Ron also had me use a clear shiny, lip gloss and a touch of mascara. Generally, I wore most of the jewelry every day but alternated on the makeup. Each item raised my feminine profile at work. I didn't try to hide the change or avoid talking about them. In fact, I usually showed them to Leah and Sammie, using a cover story about how Jamie wanted me to show more fashion touches. Of course the bra was different and it gave me the most anxiety, but I felt it was hidden fairly well by my jacket. I had started wearing those constantly in preparation for this change. I also went to all my tanning appointments, and I could see my skin taking on a golden hue. That color was beginning to offer a clear contrast to the pale bands of white where my swim suit was. The result was that my feminization was always documented on me at all times. Weekends I dressed fully on Saturday, even if Ron and Jamie went out. I also was assigned more chores. Ron also wanted my feminization at work to extend to my behavior. He quizzed me about everything: how the office was setup, my work assignments, my boss, other co-workers, and especially my girlfriends, Leah and Sammie. He was thrilled about Sammie, it turns out she was one of his brother's wife's friends and they had met once before at a summer picnic. He made it clear that if he felt I wasn't doing as he told me, it wouldn't be hard for him to check with her. That's all I needed was a possible spy for him. Once he understood the office dynamics, he outlined some requirements for me. First, he wanted me to associate more with Leah and Sammie, since they were secretaries for most of the group. I was to take breaks with them, eat lunch with them, and if possible help them with chores as well. He liked the idea that my branch of the office was only me and my boss, Mr. Jim Anderson. We handled specialty energy issues, while the main branch, which had more staff, covered the oil energy, our primary business. He suggested I start functioning as a secretary to my boss. To emphasize the shift in my roles, he said I could continue to refer to all my women associates by their first names, but men should be only addressed by Mr. and their last name. I reluctantly started doing as he asked; I got more than a few odd looks from the other men when I first addressed them that way, but after a couple of times it was routine. Similarly, my boss seemed a bit puzzled when I offered to screen his calls - our phone lines were linked to a main unit designed for a secretary to use in a larger group - and get his mail. I think he was just baffled by my recent changes and didn't want any more aggravation. But after a few days, I could see he liked the change, as I handled the less demanding tasks, and he would appear elevated to his clients as I had them hold while I transferred their calls. I think he had always felt slighted by the other managers since they had not allowed him to hire a secretary for us. Our coffee routine was another activity that Ron wanted me to change. Generally a mid-morning coffee run would be made to Starbucks for the people in our immediate office, which included me, my boss, the secretaries, their direct supervisor Mr. Tom Garrett, and an occasional intern. The women took turns doing this. So, on Monday Ron told me to offer to make the run. Leah was surprised, and at first refused. I could tell she felt odd having a higher-grade position doing one of her more demeaning tasks. But I insisted and finally she allowed me to do it. I had to go ask everyone what they wanted, go out of our office, and down the street to the shop. It easily took 30 minutes. I hadn't realized it, but the women paid for this out of their own salary. Initially the guys had chipped in, but it was a hassle and eventually, it was assumed that it was a secretaries' job requirement. On Tuesday I repeated it, again only after another protest by her and Sammie. Their protests were shorter on Wednesday and by the end of the week they went along with the idea that the coffee run was now my responsibility. For me, it remained humiliating as I asked the men what they wanted, paid for their drinks, and delivered it to them. As with my other actions, the men at first thanked me, but soon they took it as if I owed them this chore. It was especially humiliating because two young interns came and asked if I would get their coffee. I said of course, called them Mister and generally acted as if they were doing me a favor by allowing me to get their coffee. Generally, the women had not included them because they were so new at the company and were seen as even lower on the office hierarchy than secretaries. But my taking the coffee run did put me much closer with Leah and Sammie. Because of these shifts in my work assignments along with my fashion changes, they were beginning to see me as one of the girls. I know our conversations became different; more office gossip, talk about clothes and fashion, or household issues. I even was included in their talk about men and any dating recaps they would give about their previous night's activities. I think the finally step in my becoming accepted was my offer to cover the phones for them at lunch. Mr. Garret insisted that one of them stay over lunch so the phones would be answered. That meant they could never go out to eat together. Since Ron insisted I bring a small salad for lunch, I offered to handle the phones for them. The first time they again were very reluctant to allow me to sub for them, but I convinced them it was no problem for me. The next day, they tried to refuse but I insisted. As with the coffee run, within a week covering the phones became my job. Of course Ron would not let it just go with me sitting there; he had me start bringing a women's magazine to read while I sat at their desks. Generally, it was a fashion or celebrity gossip magazine. The first time the women returned and saw me reading one, they both grinned broadly. Soon they just accepted it as one of my new 'fashion' changes. Ron also required that I touch up my makeup before leaving their desk area. I had started carrying some in my coat pocket or lunch bag. The first time I pulled out a compact mirror and ran the gloss over my lips I felt like dying; the women had just returned and both glanced at each other with big smiles, although nothing was said to me. The fact that their desks were in open cubicles along the main corridor where others in the office walked, and positioned in front of the supervisors made my transition obvious to just about everyone in the branch. I was now being thought of as part of the administrative support; that was made easier because most of my own work was directly with clients rather than with other people in our branch. I hadn't really realized it before, but my regular work load was quite light. The interaction with my client list was pretty infrequent, so even with my new secretarial duties I could cover my old assignments. I could tell that Ron's plan to force me into a more feminine life was on tract and I was not finding a way to derail it. Plus, Jamie had become used to having sex with a bigger man. We still fucked occasionally, but her response was pretty minimal. My conversion to a fem boy accelerated at the end of my third week. My last tanning visit was set for a Friday and I went in as usually at the end of the day. I assumed this was going to be a more extended tanning bed session and went in to see Teresa to see what cubicle I was in. "Hi Michelle, your tan is looking really nice. It's time for the final boost to bring you to a nice rich color. You've created a base that we want to highlight, so this session we are going to apply a spray-on color. It's a stain that will be a bit darker and last a couple of weeks. After that, you will just need a weekly tanning session and then a spray every few weeks to maintain your look. So, just head into the cubicle to your left and get prepared as if you were using the bed." I immediately panicked because I knew she would see me in my women's swimsuit. I wasn't ready for that. "How about we just skip that part, and stay with the tanning bed. I don't know if I like the sound of a spray on stain. It might be messy or affect my clothes." "Don't worry honey; it won't stain clothes. We use a precise air-brush technique and dries in just a few minutes. I couldn't skip it and feel good about it with Ron. Are you nervous about me seeing you? If you've been going totally nude that is okay, because I've seen guys before." "Um, no I've been wearing a suit, but I'm just not convinced I need it. Can't we skip it?" Teresa wouldn't take no for an answer and I was soon standing in my two-piece bikini waiting in the spray room. She was chatting as she entered, but stopped mid-sentence when she saw me. She had to stifle a giggle, but regained her composure quickly. The spray application was quick and added a lot to my overall color. She had me stand in front of a bank of small fans to dry off. After 5 minutes, she said I could get dressed. Teresa had been talking with me the whole time. As she said I was dry, she offered to help me remove my top. I started to refuse, but she reached out and quickly unhooked it, holding it in her left hand as it fell free. I was amazed and very humiliated by how much contrast there was from my exposed skin and the bra pattern highlighted by my white skin. Even without the top, my breasts looked more pronounced and feminine; a result of the optical illusion created by the white bra pattern. "Michelle, I had forgotten how light your skin was before you started your sessions. But now your skin looks really good. I think you made a good choice wearing a top, too. I know a lot of girls go topless, so their breasts are tan but with girls who are petite on top, the white pattern actually gives you a size boost. I'm sure Ron and your wife will be pleased with this look." I felt totally humiliated and began to get dressed; the fact that she had seen me topless, and knew my swimsuit secret was bad enough, but she obviously knew about my wife and Ron too. I just wanted to go home and hide, but I was supposed to meet Jamie at the hair stylist. It was time for us to get our nails done. I dressed and was soon at the shop, where Jamie was waiting. The process was much quicker this time, as my nails were still in good shape. They removed the old polish, shaped them a bit and asked us what new color we wanted. I said clear polish was fine, but Jamie over-ruled me, suggesting that I get a bit of color. Looking at the choices, she selected a pearly polish with a hint of pink color. It wasn't much compared to her color, but for me it seemed a lot. When we left, she insisted we pick up some more makeup. We spent the next 30 minutes or so looking at lots of choices; when we left I had some lip gloss with some pink color to coordinate with my nails, eye liner, eye shadow, eyebrow color, and a light foundation. She told me I needed to practice that night, so I would know how to use my new treats. The rest of the weekend only got worse. She had a date with Ron on Saturday and we were to meet him at his house. I had to dress in my skirt, blouse, heels, a matching bra and panty and white thigh-high stockings. Of course, I was fully made up featuring what she said was to soon be my signature look. Once we got to his house, he ordered me around and lined up several chores for me. They planned on going out to a movie and dinner and then return, to have sex obviously. Ron decided it was time for me to step up in my transition. First, he said I needed to learn some humility and he told me to go to the bathroom and strip down to my heels and stockings. Taking off my clothes was embarrassing; I hadn't really shown him my tan lines. Walking back into the living room, I wanted to die. My cock and balls were shriveled up from cold and embarrassment, so they stuck out only an inch or so. They stood out anyway because of the white contrast with the rest of my tan skin. My little boobs seemed to be flashing at everyone, again because of the high contrast. As I approached them, Ron smirked and Jamie giggled softly. I felt my face flush red-hot as Ron told me to kneel in front of him. "Michelle, I think it is time you start to learn some new sexual skills more appropriate for your sissy appearance. It's pretty obvious that you don't have what it takes equipment wise as a man, but you do have the feminine potential and Jamie said you loved oral. So let's get you started." With that he reached into a small gym bag, took out a wide leather collar, and locked it in place around my neck. A short 3-inch chain hung from the front and was connected to a pair of thumb cuffs. My hands were soon immobilized in front of me by the chained cuffs. He then brought out a gag. It was shaped like a penis, about 3 inches in length but wide, with a locking strap. I opened my mouth, and Ron filled it with the penis gag, locking it in place. The size of the gag caused me to have to keep my mouth stretched open and I could feel spit staring to fill my mouth. "This should help you appreciate what a cock means for a girl like you. I can tell you're starting to drool over it already; you must have wanted this for some time. But you need to start sucking, or you'll get drool everywhere. Don't be shy; it's natural for fem boys to want to suck a big cock when they get the chance. While we're gone you will have lots of time to get comfortable with this new feeling in your mouth. But I think it is important that you pay for this sexy opportunity. So I expect you to clean my toilets and bathroom floor while we are out. I want it spotless when we return or you will suffer." With that, he handed me a small toothbrush. Jamie couldn't contain herself any longer, and laughed softly before leaning in to kiss Ron. As I started toward the bath, they kissed again and went out on their date. The next few hours were pure torture. I had to constantly suck on the penis gag to keep from drooling and the feel of the true to life form in my mouth and the loud slurp sounds forced me to admit I was practicing my blow job skills. Cleaning was almost worse. Because of the short chain and small toothbrush, I had to practically put my head in his toilet bowls to be able to scrub them. They were pretty nasty, lots of piss stains, pubic hair, and a crusty ring at the water level. Each one took an hour. Scrubbing the floors wasn't much better. All this was complicated by having to kneel on the hard tile floor; my knees ached by the time I was done. The only thing worse was when I saw myself in the mirror. My tan body contrasted with my pale white pubic area and shriveled cock made we wonder what a woman would ever see in me as a man; I knew Jamie didn't see me as very masculine any more, at least compared to Ron. By the time they returned I was broken; I had finished my cleaning, but all I wanted was to get this rubber cock out of my mouth and put on some clothes. Despite how I felt about myself and the fact I knew they would soon have sex, I was glad to see them. When they saw me standing there, both kind of chuckled. Ron asked if I was done and as I nodded he went to look at my work. He finally took out the gag. "Very good, Michelle,