Unsuspecting Husband Part 2 free porn video

I was feeling really guilty at the moment. Having introduced my husband to wearing a bra and panties as part of our love life, I was now having second thoughts. My doubts started once we returned from his bra fitting. Wearing one of his new padded bras home from the lingerie store, Bill had seemed very restless the whole way home. Once we arrived back at our house he had immediately headed for our bedroom and removed the bra he was wearing. At that point I started to wonder whether I had pushed too hard or manipulated the situation too much. Did I have the right to manoeuvre my husband into wearing woman's lingerie? Even though I had arranged the situation so that he initiated some of his own lingerie wearing, I still knew deep down none of it would have happened without me continually pushing the idea. Over the next few months my efforts to get Bill into lingerie ceased. Without that pressure from me and with Bill seemingly embarrassed by his bra fitting experience, the lingerie suddenly stopped being part of our bedroom activities. During this period the bra and panty sets sat unused in Bill's dresser. It soon became obvious to me that the intensity of our lovemaking was suffering. In spite of this neither of us seemed willing to discuss what had happened or why the intensity was suffering. Weeks turned into months and still the two of us continued to pretend Bill had never gone for a bra fitting or worn women's lingerie. We also pretended our love life was as good as it ever was. Unfortunately my subconscious wasn't going to let go that easily. I started having dreams that seemed to show me what I really wanted in the bedroom. The first time it happened I dreamt I was standing in front of our bed, with Bill kneeling in front of me eating me out. His talented tongue was bringing me close to a climax. At that point in my dream I looked down at him. I could see the top of his head bobbing back and forth of course. Looking further down however, I could see a very feminine pink brassiere stretched across his very masculine back In my dream I enjoyed the sight of this bra running across his back, and watched his actions for several minutes, finding the whole thing very erotic. Finally as I started to climax in my dream I noticed he was wearing panties that matched his bra. I suddenly woke up and realized my impending orgasm wasn't confined to my dream. Dashing into our en-suite bathroom, I allowed the sensation to roll over me as I masturbated myself to the best orgasm I had in the last two months. After cleaning myself up I slipped back into bed, my mind racing at the implications of my dream. Eventually I fell back asleep, and by next morning I was telling myself the dream meant nothing and would likely never be repeated. I must have been about a week later that I was proven wrong. This time Bill and I were making love in the missionary position in my dream. As my hand gripped his back I could feel he was wearing a bra once again.. As he extended his body above me I could see this bra was red and heavily padded, making it look like he had small breasts. Enjoying the sight of my husband sporting a set of breasts, I realized he had started thrusting his penis inside me. It was at that point I woke up to discover I was about to have another orgasm triggered by a dream. Another trip to the en-suite to masturbate myself was once again followed by me lying in bed trying to figure out what my dreams were telling me. The thing that was really bothering me about this dream was that Bill and I had sex that night before bed, so I really shouldn't have been having dreams with any serious sexual content so soon after the real thing. As far as I could recall, nothing like this had never happened to me in the past. I half convinced myself none of it meant anything, however I did spend the next few weeks trying to entice Bill into lovemaking more often than usual. I convinced myself that if I drained any sexual energy I had, I wouldn't keep having these exciting but uncomfortable dreams. It was a few week later that I finally recognized the cold facts. Not only weren't these desires of mine going to disappear, but they were getting more insistent the longer I denied them. This was forcefully brought home to me one Friday night by yet another X rated dream. In this dream I was once again standing in front of our bed, with Bill once again kneeling in front of me. This time I seemed to be dressed in some kind of black merry widow type garment, along with the typical black stockings and black high heeled pumps. Looking down it took me a minute to figure out what was going on. Bill was wearing a white bra whose cups looked to contain a pair of good sized breast forms. At least I assumed he was wearing breast forms as his bra was completely filled and had he been a woman I would have described him as 'stacked'. A distant part of my mind noted that Bill's breasts seemed to get more pronounced in every dream, and I started to wonder if at some point his chest would start to look like the chest one of those female porn stars. I could also see he was wearing a white corset, which had been laced up to pull his waist in by at least 4-5 inches. In addition he was wearing a padded white girdle, the hip and butt padding adding several inches to his hips. With the falsies up top, the corset pulling in his waist and the hip padding down below he was sporting quite a feminine looking figure in my dream. His outfit was finished off with pair of white stockings attached to his corset and encasing his legs, and a pair of white high heels on his feet. His outfit was one thing, but what he was actually doing was what had caused me all my confusion. He seemed to be bobbing his head back and forth close to my crotch. After watching for a handful of seconds I suddenly realized in my dream I was wearing a strap-on dildo. Bill had the business end in his mouth and was doing his best to 'service' me, and seemed to be having a great time doing so. In my dream I was getting very excited by his actions, going so far as to start fondling my breasts through the cups of my merry widow, nipples fully erect and showing clearly through the lace material of the garment. Suddenly I was awake and incredibly horny, but in this instance didn't have time to make it to our en-suite. Instead almost immediately I started flooding my side of the bed as my vagina cut loose with a massive orgasm. The other thing was I didn't keep things quiet enough while this was happening. Bill started to wake up as a result of the noises I was making and my thrashing around on the bed, and at that point I realized I had a bit of a problem. I had to finally admit to myself that I really wanted to feminize my husband with more than just the bra and panties I had originally envisioned. Other than these recent dreams featuring Bill all dolled up as a woman, I couldn't ever remember having dreams that actually caused me to orgasm. Besides the guilt I felt around wanting to take Bill even further down that crossdressing path, my other big problem was I wasn't sure whether he would go along with everything I wanted to do with him. While he had of course gone along with wearing a bra and panties a few times, that would only be the tip of the iceberg if my libido got it's way. I started considering foundation garments for him, dresses, shoes, makeup sessions, maybe even some sexy costumes. With pretty much anything I had ever done to make myself more sexually appealing, I started to think of Bill wearing or doing the same. I knew it was time to stop hiding it and start being somewhat honest with him about my desires. While I wouldn't tell him absolutely everything because I was afraid it would scare him off, I nevertheless knew I had to at least tell him the broad strokes of what I would like to happen in future. Selling him on wearing panties as being his own idea had been possible, but convincing him wearing a bra was his own idea had already been stretching the limits of credibility. Once we moved him to foundation garments, high heels and the like it would no longer be feasible to act as if it was all in response to what Bill wanted. I would have to confess my own desires if I wanted to have any credibility left with my husband. As he was now awake and likely wondering what had just happened, I felt now was as good a time as any to start talking to Bill about taking his dressing to the next level. "Did you just have an orgasm honey?" he asked, sounding surprised. "Yes I actually did," I answered honestly, something I wanted to do for the most part going forward as I still felt somewhat embarrassed about subtly manipulating Bill into lingerie. "Where you lying beside me masturbating?" he responded. "No, no exactly," I replied. "I was having a very erotic dream, and suddenly woke up beside you ready to explode. Suddenly I orgasmed before I could do anything else," I explained. "Do you remember what were you dreaming about?" he asked, bringing the conversation to the moment of truth. "Yes I do. You were fully dressed in women's clothes and eating me out" I told him, figuring that answer was honest enough as far as it went, without getting into those details that would likely freak him out. "I think it's about time I talked about some things with you dear," I continued, deciding to take the lead in this conversation. "I was really enjoying our bedroom play time, especially when you put on a bra and panties. Then when we got home from our bra shopping trip I suddenly started to really worry about whether I was pushing you too much into wearing lingerie. If you were completely comfortable with the idea that's one thing, but if you were uncomfortable and were really only doing it to please me I didn't feel that was a good enough reason for it to continue. Of course after our shopping excursion you completely stopped wearing the lingerie, which lead me to believe I really had been pushing you into it and had gone too far. That's why I haven't mentioned it since, even though I would really love to see you back in your lingerie. To be completely honest seeing you in a bra and panties gets me incredibly horny," I explained to Bill. "Oh, okay," he responded. "I assumed the reason you hadn't talked about it ever since our shopping trip was you were starting to regret seeing me in woman's underwear, and would be just as happy if I stopped doing it." he told me "To be honest though, the main reason I stopped wearing the stuff was because I felt guilty," he explained. "Part of me loved it, and another part felt really guilty for loving it. A little voice in my head kept telling me that men shouldn't wear women's underwear, even if it is reserved for the bedroom. The little voice had a lot more to say about men who enjoy wearing women's underwear, none of it good. In the end I convinced myself the whole thing was just a silly experiment and was best forgotten, especially as you no longer seemed interested," he told me. "It's good we got that out in the open," I commented. "Why don't you go put on a bra and panties and we can talk about it some more," I told him, waiting to see what his response would be. Somewhat to my surprise he stripped naked and walked over to his dresser. Opening the drawer containing his lingerie, he pulled out a nice pink bra and panty set. Stepping into the panties, he then spent a minute or so slipping his arms into the bra and getting it fastened properly on his chest, before looking at me for instructions. I patted the bed beside me, indicating he should sit down close to me, which he did. I have to say I enjoyed the sight of Bill walking across out bedroom wearing nothing but a bra and panties. I found the experience very erotic, and it definitely got me in the mood for my next actions. Once he was seated I reached inside his panties and started stroking his penis. "I told you about my naughty dream. Have you been having any naughty dreams I need to know about?" I asked him, wondering if his subconscious had been sending him messages over the last few months just as mine had. After a slight hesitation he responded. "I did have one particular dream a few times, where I was dressed as I am now and we were fooling around in the bedroom similar to what we are doing now," he confessed. "Were you wearing anything else in this dream of yours?" I prompted him "A nice pair of high heels perhaps?" I added, waiting for his reply. "One time I was, yes," he told me in a small voice. "What colour were these high heels you were wearing in your dream?" I probed "Do we need to go shopping to see if we can find the same pair in your size? I would find it incredibly sexy to see you like that," I added before he could respond to my questions. While he didn't answer my questions, I could tell from the way his penis was reacting that he was very turned on by what I was saying to him. By this point my other hand was inside his bra, playing with his nipples as we talked. "I love playing with your breasts like this," I told him as my fingers continued to roam around inside his bra fondling his nipples. "I promise to play with your breasts if you wear high heels for me," I promised him as he continued to squirm. Not getting anything from him other than little noises of pleasure I continued my monologue. "We'll put shopping for high heels for you on our to do list," I informed him "Was there any other girly stuff you were wearing in these dreams of yours?" I prompted Bill as he got more and more aroused. "Earrings," he gasped as he seemed barely able to talk anymore. "Oh, I like that as well. We'll get your ears pierced and find some nice dangly earrings for you to wear," I promised. "One thing I wanted to mention however. I will of course help you get the high heels and earrings you want, but in return for my help there are some things I want to pick out for you," I informed him. "If you are going to be my girl sometimes, I want you to dress properly for the occasion. For starters I would like to see you laced into a nice corset to improve your figure. Once you have that nice womanly figure we can then pick out a pretty gown for you. Seeing you in a sexy ballgown with it's tight fitting bodice and big poofy skirts would really get me hot," I assured him as he started ejaculating across the front of his panties. This went on for a good ten to fifteen seconds before Bill sank down exhausted. Once Bill had spent a few minutes recovering and gotten to where he could speak full sentences once more we picked up the conversation where we had left off. "I don't think I'm ready for to go that far," he replied in response to my corset and gown suggestions. "I'm not sure I'll ever be ready for something like that," he added. "Wearing some bits of lingerie in the heat of passion is one thing, but you're talking about spending a couple of hours getting fully done up in women's clothes," he observed. "As I keep telling you, we'll only do things you are comfortable with. Don't be surprised though, if I keep trying to expand your comfort range," I assured him. "I'm starting to have fun with this, and as it's really not hurting anyone I figure why not continue?" I explained for his benefit. "I don't disagree with you in theory, but I can't really promise anything at this point," he answered. The status quo held for the next few weeks, Bill's lingerie making the occasional appearance in the bedroom but never outside the bedroom, with nothing new added to his wardrobe. I had to admit I was getting a little restless with the way things were going. I had these visions with Bill being like a giant Barbie doll I dress however I wanted, and it wasn't working out quite as planned. Figuring that deep down Bill wanted to take it further but was still being overwhelmed with guilt, I decided a new plan was in order. Since shoes were the first thing he had mentioned when we had talked about new additions to his wardrobe, I determined that would be the best place to start. To minimize the guilt factor I thought it best if I went to a women's shoe store shopping for myself, and arranged it so Bill would tag along. Once in the store I had a few ideas on how to get him looking for shoes for himself. A perfect opportunity came along on a Monday. Both of us were at work, and we were talking on the phone to each other as we usually did once or twice a day during the work week. It worked out that neither of us had any plans for that night. As it had been weeks since we had gone out to dinner, going out after work seemed to make a lot of sense to both of us. I mentioned to Bill there was a shoe store close to the restaurant, and I wanted to quickly pop by before dinner as I needed to look for a new pair of shoes. I suggested we meet up at the store, and then head to the restaurant from there. I promised Bill I would make my visit to the store very quick as we would both be very hungry by then. He agreed, we made the arrangements, and both of us hung up our phones and went back to work. The rest of the day sailed by, and it was soon five o'clock and to meet up with Bill. I made it to the store first, and started browsing through some of the sexy high heeled sandals the store carried in my size. Through my research I also knew the store carried many of the same shoes in Bill's size, and double checked this by moving over to the larger sizes and looking through the current selection. There were five or six different styles I could image Bill wearing, and as the store did carry all of them in the larger sizes that part of the plan was working out perfectly. Moving back to shelves displaying my size, I settled down to wait for Bill's arrival. He showed up ten minutes later mumbling something about bad traffic. I ignored his complaint and started asking his opinion about some of the shoes. Essentially I was trying to get a sense of what he himself might like to wear by asking him what he would like to see on me. After ten minutes or so I had established that of the six or so pairs I had identified earlier, Bill pointed out three of them as pairs he liked. Focusing on those three pairs, I located all three in my size. Slipping off the shoes I wore into the store, I started trying the new shoes on. Buckling on the first pair, I strutted back in forth in front of Bill to let him get a really good look at how they looked on my feet. I did the same with the second and third pairs, looking for Bill's feedback the entire time. By this time he looked to be getting somewhat agitated. This caused me to suspect he might be imaging himself in some of the shoes, and was then scolding himself silently for imaging such a thing. Feeling this was a good time to ease off, I suggested we head to dinner. I made sure however, we had an understanding that I would be thinking about the different shoe options over dinner and might want to quickly stop by the store on the way home to buy one of the pairs of shoes. Bill readily agreed, and we headed off to the restaurant to enjoy our meal. It was a couple of hours later, and Bill and I were enjoying the after effects of some good food and better wine. We were both very relaxed, exactly the mood I wanted him in for the next part of my plan. Leading him into the store, we were advised it was only twenty minutes till closing. Looking around I could not see any other customers, not very surprising given what time it was on a Monday night. We arrived back at the side of the store containing the shoes I was considering. Picking up the pair that Bill seemed to favour most, I handed a pair in my size to him. "I'm seriously thinking about getting these," I commented on what were a very sexy looking pair of black 3" heels. "What do you think?" "Of the ones you tried on, those are my favourites," he confessed. "I just want to try them on once more and see how they feel," I told him. Slipping off my own shoes I soon had the new pair on and buckled. "If you don't mind follow me and tell me how well I'm walking in this pair," I requested. "Sometimes a pair of shoes feels fine when you're wearing them but someone watching you can tell they don't fit properly," I explained. Bill followed me as I headed down the aisle towards the same shoe in the larger sizes. Stopping strategically right in front of the ones in Bill's size, I appeared to be pondering the shoes I was wearing. Meanwhile Bill was looking around, and had soon spotted the same shoes sitting on the shelf. His eyes seemed to be glued to those shoes. Once I looked up it was easy to pretend I was following his gaze and had spotted the shoes in his size for the first time. The whole thing was a bit staged on my part, but I wasn't looking to harm Bill so figured my little white lie was okay. "Look, they have exactly the same shoes in the larger sizes," I exclaimed. "You know, a few weeks back you mentioned you were wearing high heels in one of your dreams," I commented, dropping my voice to a whisper. "Did the shoes in your dream look something like that pair?" I asked him in the same whisper. He appeared unable to speak, so I continued to take the initiative. "There is no one else in the store, and we're so close to closing time the woman on the counter won't be letting anyone else into the store," I told him in a low voice. "I think it would be a lot of fun for us to have matching high heels. Why don't you go ahead and try them on," I suggested. He still wasn't saying anything so I guided him to a nearby bench and started to unlace his shoes. As he didn't make any move to stop me I had both shoes off in thirty seconds. Grabbing a pair of the nylon socks all women's shoe areas keep handy, I stepped over the shelf with the size I thought would fit Bill and grabbed a pair. A couple of strides put me in front of Bill with both nylons and shoes in hand. Bending down, I slipped the nylon sock on his right foot and followed it with the high heeled sandal. Buckling it in place I did the same for the left foot. The fit seemed good, with his feet slipping into the shoes without undue difficulty. "Stand up and walk around a bit to see how they feel," I suggested. "Don't worry, we have a few minutes before the store will be closing," I assured him. Helping him to his feet, I watched as he tottered a little in the heels. He wasn't used to being up so high, and you could tell he was struggling a bit. After walking back and forth three or four times I could tell he was getting much better at navigating in heels. He was also starting to get aroused, made obvious by the fact his pants were starting to tent out in front. Stepping up to him in my matching heels, I placed my hand on his growing bulge and informed him, "This part of you really likes the shoes. I vote we both buy them. Do you agree?" I asked. He nodded once to show he agreed with my suggestion. "Great, why don't you take those off and put your other shoes back on. I'll walk back to where I left my shoes and do the same. Once we're both ready we can meet at the front counter. Be sure to put your new shoes back in the box and bring the box to the front with you," I reminded him as I turned and walked back down the aisle. I knew I would have my new shoes off and my old shoes back on before Bill could do the same, so decided to be a bit naughty. Once my new high heel sandals were in their box I immediately headed for the front counter of the store. Arriving at the front I spoke with the salesperson, whose name tag read Jessica. "Hi Jessica, I'm Linda. My husband Bill and I will be buying two pairs of shoes tonight. Here's the first pair," I told her. "Okay, I may as well wait for Bill to bring the other pair up here before I ring yours up. Will he be very long? It's getting late and I'd like to close up the store," she told me as she opened my shoe box and double checked the shoes to make sure there were two of them and they were in good shape. "No, he will be along any time now," I assured her. "He has already finished trying on the shoes he wants to buy, and just had to take them off and put them back in their box," I told her. "So, what's it like working in this store? Does it get very busy usually?" I asked her while we waited for Bill to appear. "It isn't too bad. We have our really busy times of course, but those are not that frequent.. Normally there are just enough customers in here to keep us busy without going crazy," she told me. "Ah, here comes Bill now!" she exclaimed. Turning I caught sight of him heading for the counter carrying the shoe box. "Hi there Bill. If you just hand me the box I'll ring up your shoes and your wife's shoes on the same bill," she told him as she extended her hand towards the box Bill was carrying. He gave her the shoe box, which she promptly put down on the counter and opened up to check. There was a momentary pause as Jessica suddenly realized the shoes were the same women's high heel dress sandal as I had picked out, but in a larger size.. She was also probably remembering I had told her Bill was trying on the shoes he was going to buy, making it very obvious he would be the one wearing the high heels he had just handed her. When she looked up she had her expression under control, although the corners of her mouth kept trying to twitch upwards. She replaced the lid and ran the bar code scanner across both boxes, causing the cash register to beep and display the total amount we owed. Pulling out my debit card I swiped it through the debit card machine and paid the bill. "I hope you like your new shoes," Jessica said to no one in particular. "Please come again," she added as we headed for the door. While she didn't seem disapproving, Jessica certainly seemed a bit uncertain as to how to speak to Bill once she realized he wore women's shoes. Likely she was wondering whether he was currently wearing anything else not considered typical male attire. "Did she know the shoes were for me," Bill asked once we were outside the store. "No, I don't think so," I lied. "I was definitely getting this weird feeling from her," he persisted. "No, you're imagining things," I assured him. "She didn't suspect a thing," I added as we got in our separate cars and started home. After an uneventful ride to our house I convinced Bill to slip into one of his bra and panty sets and add his new high heels into the mix. A very pleasant and exhausting hour followed this, during which I once again tried to prove to Bill how much better the sex was when he dressed in a more feminine way in the bedroom. Based on his reaction to those activities I think I succeeded in getting my point across. At this point, as had happened in the past, there was a bit of a lull in Bill's crossdressing. It was some three weeks later that I walked into our bedroom to find Bill facing away from me, wearing panties and high heels, and in the process of putting on a matching bra. From the mood in our house earlier I could sense both of us had sex on our minds, and apparently Bill wanted to spice things up a little. "Why don't you let me help you with that?" I offered as I stepped up behind him. At this point the bra straps were already positioned on his shoulders, however he hadn't yet fastened the back of his bra. "Sure," he replied, let go of the bra band he had been about to fasten. Reaching around to the front of his body, my hands soon found his nipples. I started playing with them, running my fingers in little circles over the bud and then pinching them every so often. As I caressed his chest I could feel his hips start to move around. Reaching downwards with one hand, I could feel his erection straining inside his panties. I started stroking his penis with the one hand while cupping his breast with the other hand. "Do you like it when I fondle your breasts?" I whispered in his ear. "You probably wish they were bigger though," I added. "Would you like that, having bigger boobs? Oh yes, I can see you would like that, having full size breasts like a woman, with large feminine nipples," I told him as I continued to masturbate him and his penis continued to grow. I could tell he was getting incredibly aroused by this point, so I eased off a little as I didn't want him to orgasm just yet. Releasing his penis, I finished fastening his bra and then used both hands to stroke his nipples through his bra cups. "Leave your lingerie on, but take your high heels off," I instructed him after a few minutes of caressing. "And put some clothes on over top. We need to go shopping tonight," I informed him as I stepped away from him. "How about sex?" he asked, clearly desperate to climax. "We will get to that later, I promise. For now I have a little surprise in store for you," I told him. In spite of his objects Bill was soon dressed and ready to go. Scooping up his high heels, I put them in a bag and brought them with us. As I drove I reached over every so often to stroke his penis or nipples. The fact he was still wearing a bra and panties seemed to cause my attentions to arouse him even more. By the time we arrived at the mall across town he seemed almost ready to ejaculate once again. Despite Bill's arousal I exited the car on my side, before going around to Bill's door to drag him with me. Once he stepped out of the car he suddenly realized where we were. "Why are we back at Crystal's store? Did you need something?" he asked me. "No, actually you do. We need to fix your shape," I informed him. "You are flat up top, too thick in the waist, and too narrow in the hips. Luckily there are products women can buy to fix all three problems. I've already spoken to Crystal about it and she should be able to fix you up still tonight," I told him as I guided him into the store. As during our previous trip the store was fairly deserted. I tended to try and hit times where I knew there wouldn't be a lot of other customers around, and it looked like I had nailed it again. "Linda, Bill, how nice to see you again," Crystal greeted us enthusiastically as soon as she spotted us. "I hope it's Bill you're shopping for tonight. I had so much fun picking out things for him last visit kit would be nice to do it again," she added. A few days previous she and I had a discussion about altering Bill's shape, so I knew she would be fully prepared for all the things I wanted to do during this visit. "Yes, Bill does need a few more things," I told her. "We've decided to try and improve his shape. Normally I love his masculine shape, however when we're fooling around in the bedroom and he wears some of his feminine things, it would be nice if he could shows off a more feminine shape," I explained. "Can you help us with that?" I asked. "Certainly. Customers come into the store all the time with those issues. Some breasts forms to increase his bust-line, a corset to reduce his waist, and a padded girdle to increase his hips should do the trick. Give me half and hour and Bill will have a lovely feminine shape, and of course once he removes the 'helpers' he will easily get his masculine shape back," she assured us."Why don't we start with the breast forms and work from there," Crystal told Bill. I wasn't positive he would go through with it, so stepping up to him I gave his nipples and penis a quick rub and whispered, "I promise to make this worth your while," before french kissing him. He seemed a bit shell shocked as Crystal guided him to the change rooms and asked him to take off his shirt, bra and pants. Within a minute he was standing in the change room wearing only a pair of panties. Meanwhile Crystal had returned with a pair of pink boxes. Placing the boxes on a shelf in the change room she opened the first one. Nestled inside was a very realistic looking breast. Removing it from the box, Crystal moved towards Bill, peeling a piece of plastic off the back of the form as she walked. "This form has a built in adhesive on the back," Crystal explained. "You simply wash the form after every use to keep the adhesive working properly," she added. Bill was looking extremely nervous and jittery, but Crystal ignored that. Measuring by eye, she positioned the form on Bill's chest and pressed the form against his skin. It stuck there, giving him a fairly good sized breast. Walking back to the boxes she removed the second form and repeated the procedure. I was surprised Bill hadn't balked at taking his dressing this far, but there it was. Bill now had a very womanly chest. He was kind of staring down at his chest looking a little scared and confused. I figured the fact they were 'naked' was really throwing him off so decided it was time to cover them up. Picking up the bra he had taken off. Handing the bra to him I said, "Why don't you put your bra back on and give your chest some proper support?" He looked a little confused as to how to proceed, never having worn a bra for support purposes. He just stood there with the bra dangling from his hands. Crystal stepped in at this point. "Let me help you with that Bill," she offered, taking the bra out of his hands. "Arms through the straps and then lean forward," she instructed. Once Bill had done as requested she continued. "Let your breasts flow into the cups of your bra. Once they are sitting comfortably you can straighten up and fasten the back of your bra," she coached him as he performed the required motions. "Finally check and make sure nothing shifted or needs adjustment," she said as he straightened up. Placing her hands underneath his falsies she hefted them a couple of times, watching how the bra was reacting to the motion. "That looks perfect Bill. The girls are ready for a night on the town," she told him. "The girls?" he said, finally speaking. "Yes, that's what a lot of women call their breasts when they're feeling playful," Crystal told him. "Now that you're no longer flat chested let's see what we can do about your waist. You could get a bit of help from a panty girdle," she commented. "But for really serious waist control we need to lace you into a corset. We will be able to take a good 3 inches off your waist today, and even more if you wear the corset regularly," she explained to both of us. "I'll quickly measure Bill's waist, and then go see what I we have in his size," Crystal told us. She soon had Bill's waist measurement and left the change room, only to reappear within minutes carrying a formidable looking black corset with built in garters. I didn't wear them myself, but recognized the corset Crystal was carrying as the real deal. Once Bill was wearing it I knew we would easily be able to reduce his waist be the promised 3 inches, and I was hopeful we could lace Bill's waist even further and take 4-5 inches off today. Now that Bill had a proper bust-line I was anxious to give him a feminine waistline to match. I realized I really wanted to see a classic hourglass figure on my husband. While I had been musing Crystal had wrapped the corset around Bill's waist. She now grabbed the laces and started pulling. "I know this seems like a lot of effort Bill," she commented as she continued to lace him in"but it will be completely worth it once you see how feminine your body looks once we're done," she assured him. The lacing continued for a few minutes with nothing from Bill other than the occasional grunt. Crystal finally seemed satisfied with her efforts and stopped pulling the laces tighter, instead tying them around Bill's waist and knotting them securely. I have to say I was amazed. When Crystal pulled out her measuring tape again and indicated we had reduced Bill's waist by four inches I was ecstatic. If you blocked out his face and only looked at him from the neck down he now really had a woman's shape. I absolutely loved it, and right then decided I wanted to take Bill dress shopping this very night. "We'll just let you get used to your new corset for a minute, honey," I told him "I just want a quick word with Crystal," I added as I motioned her outside the change room. She followed me as I put a bit of distance between the two of us and Bill, as I didn't want him to overhear what I was about to say. "I just love his new shape," I confided in Crystal. "You've made me so happy. In fact I've decided with him looking like that it would be the perfect time to take him dress shopping," I advised her. "I was hoping you might have some suggestions as to where I can take him," I asked. "Actually, I know of the perfect place. This may be too much of a jump for you and Bill, however a friend of mine works close by in a shop that sells women's formal wear. I know she'll be willing to help the two of you assuming you are willing to buy something from her. Is that too much of a leap, going right to gowns instead of trying everyday dresses first?" Crystal asked me. "Actually that sounds perfect. Bill has been so docile tonight it feels like the perfect time to try something like this. Can you arrange it with your friend?" I requested. "Sure, I'll just give her a quick call," Crystal assured me as she pulled out her cell phone and started dialling. "Hi Darlene, it's Crystal," she said into her phone once she appeared to have a connection. "Just working the end of my shift," she said after a short pause "Listen, at the moment there is a couple shopping in my store who are around our age. They've been my customers for the last few months, and for this recent visit I've just finished putting some falsies on the husband and lacing him into a corset," she said before pausing again. "Yes, that's right, bra, panties the works. The two of them have been exploring the husband's feminine side for the last little while and want to take it even further. Linda the wife wants her husband Bill to try on some dresses tonight, and I told her you might be able to help them," she explained into the phone. "You can! That's great!" she exclaimed. "I'll send them right over. Yes, I'll make sure the husband doesn't remove any of things he's wearing. I'll explain to Linda he'll need the keep the shape I've given him to fit into the gowns you have."she assured her friend "Thanks a bunch. Talk to you later," Crystal said into the phone before hanging up. "You heard all that? Darlene is expecting you, however Bill needs to wear his new things over to Darlene's store if you want this to work properly," she informed me. "No problem. Thanks a lot by the way. I really appreciate this." I told her "This is just perfect," I added. "My pleasure," she responded. "We should probably get back to Bill and see how he is doing," Crystal suggested. Bill seemed to be doing okay. As we entered the change room I could see Bill examining his new chest and waist in the change room mirror, turning this way and that to see them from all angles. "Hi honey, how does your corset feel? Can you breathe okay? And your bra. Is it supporting your breasts without digging into your skin?" I asked him as he spotted the two of us. "I have to take really shallow breaths," he complained in response to my question. "That's perfectly normal," Crystal assured him. "That's the price you have to pay to get that wonderful shape the corset is giving you," she told him. "I can feel extra weight on my bra straps, but it seems comfortable enough at the moment," Bill replied in answer to the second part of my question. "It sounds like we're ready to release you into the world," Crystal commented. "If you'll just step into this padded panty girdle, it will give you a better shape in your hips and butt. After that you can then put the rest of your clothes back on. Meanwhile I'll head to the front and start ringing up your purchases," she added as she left the change room. "You want me to wear all this stuff underneath my regular clothes?" he protested. "Yes. Actually honey, I have a surprise for you, and it requires you to wear your new things. Crystal has spoken with a friend of hers and arranged for us to visit the Friends store tonight. This is going to be so much fun!" I assured him "Now please finish getting dressed," I asked him. He grumbled a bit but continued to put on his normal clothes over top of his new figure. Even with his men's clothes on you could really see the womanly shape underneath, and it was starting to get me very horny once again. "What's the surprise," he questioned me as he continued to get ready. "If I told you it wouldn't be a surprise anymore, would it?" I shot back. While on the surface he was moaning and grumbling over what I had him wearing, deep down I knew he was starting to get off on this whole thing. At this point I doubted I would be able to stop him wearing bras and panties if I tried. While he did stop for short periods, he always seemed to end up wearing them again in the long run. I was determined to have the same thing apply to him with dresses and high heels before we were done. By this point he was fully dressed so we exited the change room and headed up front to pay. Crystal was ready for us, and efficiently took the payment from me while handing me directions to the friends store. "Thanks for your business. Hopefully you'll come back soon," Crystal exclaimed. "Thanks Crystal, you've been a huge help," I told her. "Bill, be polite, thank Crystal for giving you such a nice figure," I scolded my husband. "Yes, thanks Crystal. We'll see you later," he told her as we left. Within a few minutes we on our driving towards Darlene's store. As promised it was fairly close, and we arrived within minutes. Pulling up outside the store we were greeted by the sight of at least twenty exquisite gowns arranged on mannequins in the front display window. Upon entering the store we were soon overwhelmed with even more beautiful gowns in every style and color imaginable. Both of us were so busy admiring the gowns we didn't notice the young woman over behind the counter until she spoke to us. "I'm Darlene. You must be Bill and Linda. Crystal told me to expect you," she said by way of introduction. "Yes, that's right. Very nice to meet you Darlene," I responded. "Nice to meet both of you. It's only ten minutes until closing time, and there are no other customers in the store at the moment, so I've decided I may as well close right now so we can get started on Bill immediately," Darlene told us as she headed for the door and engaged the heavy deadbolt mounted into the door. "That's very nice of you," I commented to her once she had finished locking the door. "My pleasure. I'm good friends with Crystal and she explained your situation to me," Darlene told us "I understand Bill has already been laced into a corset and is wearing a convertible bra and breast forms," she continued. "Yes, once Crystal had given Bill the proper shape for these kinds of dresses we headed straight here from her store," I confirmed to Darlene. "That's great. It makes it so much easier to fit men with the right gown when they have the proper shape to start with," she told us. "Now Bill, don't worry about a thing. You can keep trying on pretty gowns until we find the one that makes you feel like a princess," Darlene assured Bill. "As the store is completely empty aside from us, and no one outside can see in, Bill I am going to suggest you strip down to your lingerie and come out onto the sales floor. It will make the whole process much quicker and easier if you don't have to constantly run into the change room each time you try on a new gown. And don't worry, I've put a number of men into our gowns in the past, so you aren't doing anything I haven't dealt with before," she explained to us. "That sounds good," I told Bill, supporting Darlene "after all it's just us girls here," I added, watching him squirm as he did every-time I called him a girl. Helping him remove his shirt, pants and shoes, he was soon standing in the middle of the sales floor wearing his stuffed bra, panties, corset and stockings. "Crystal mentioned you've brought the high heels Bill will be wearing with his gown," Darlene stated to us. "Yes, that's right," I responded. "Bill, if you can please put on your high heels, and then we'll get an ankle length petticoat on you. We need to see how the skirts of the various gowns are going to look, and the only way we can see that is if you are wearing the proper petticoats," she explained to Bill. Pulling out the shoes, I placed them on the floor in front of Bill. With my help he stepped into them, after which I bent down to fasten each buckle. Meanwhile Darlene had produced a very full set of petticoats, which she had Bill step into. Once both of his high heel clad feet were in the opening of the petticoats she pulled them up his legs and settled them on his hips before fastening them snugly around his waist. I was getting a serious rush seeing Bill standing in the middle of dress store, stripped to his lingerie and wearing high heels and a substantial set of petticoats. I couldn't believe I had gotten him to do this, but was loving every minute of the experience. Darlene quickly took his key measurements, Hips, Waist, Bust, and started picking out gowns he might like. The first one was a dazzling ankle length gown in an aquamarine color. It had a tight fitting bodice and was heavily sequined across the entire gown. Slipping it over Bill's head, Darlene soon had him zipped into this first gown. I had this overwhelming urge to take Bill for a complete makeover. His head was still very masculine looking, but from the neck down he looked incredibly feminine. The tight fitting bodice really emphasized his corseted waist and prominent bust, while the big flaring skirt brought attention his his womanly looking hips. As he stood there you could just catch a glimpse of the black 3" heels he was wearing, although it would have been more appropriate if the color of his shoes matched the color of his dress. He would have looked absolutely perfect if his face was made up with mascara, eyeshadow, lipstick etc. "You look amazing dear," I told him as I felt myself getting so horny I was at risk of losing control right in the middle of the store. "Is there a washroom I can use?" I asked Darlene. "Sure, over in the back corner," she replied pointing towards one end of the store. I almost sprinted towards the washroom, although no so fast as to miss seeing a number of gowns I would like to see Bill try on. Arriving at the washroom I splashed some water on my face and sat while I tried to calm down. It took several minutes but I managed to control my sexual excitement. Standing up with a sigh, I headed back to where Darlene was helping Bill try on more gowns. Once back in earshot I was greeted by Darlene. "Bill tried on two other gowns while you were gone, but neither of us liked how they looked on him. I think this one could be a possibility though," she said stepping away from Bill. This time he was wearing a bright red strapless gown with intricate detailing across the bust. The effect was spoiled somewhat due to Bill's bra straps being visible, however Darlene immediately acted to fix that. "I'll just detach Bill's bra straps so we can get the full effect," she said as she stepped up to Bill and detached the straps from the back of his bra, before stepping in front of him and detaching each strap from cups of Bill's bra. She then moved back out of the way so I could get a better look. Part of me couldn't believe I was looking at my husband wearing a strapless ballgown and loving the way he looked in it. The rest of me however, was too busy enjoying the whole experience to pay any attention to the disapproving part. While I loved the way the gowns looked on Bill, I also enjoyed the part where he removed the gowns and was standing in the middle of a store wearing nothing but high heels and women's lingerie. If Darlene wouldn't have been there, I swear in no time flat Bill and I would have been going at it like a couple of bunnies, right there in the middle of the sales floor. The red strapless gown was followed by a very pretty green colored gown, with the final ankle length gown he tried on being a pink gown taken right out of a fairy tale. I couldn't believe the amount of frills and lace on this dress, or the fullness of the skirt. It was one of those gowns where the person in it couldn't do much of anything except wear it and look pretty, as doing anything besides that would be close to impossible. At one point I mentioned to Darlene I wanted Bill to try on some cocktail dresses, and this seemed like a good time for the switch. While Bill manoeuvred his way out of the pink gown Darlene and I headed through the display racks looking for a few likely candidates for Bill to try. Within a couple of minutes we had located two dresses that both of us thought would look good on Bill. Darlene and I then each carried one of the dresses back to where Bill was waiting for us, having managed to free himself from the final gown. "We'll have to change your petticoat Bill, as the one you're wearing will be too long for theses next couple of dresses," Darlene informed him. The first cocktail dress had a full skirt that fell just above the knee, with the entire dress made of a satin material. It was a vibrant red, with spaghetti straps and a sweetheart neckline. I would have liked to wear it myself, and thought it would look just darling on Bill. Darlene helped him step into the dress, and soon had everything positioned properly and had zipped him into the dress. Bill's shoes should have been the same color as the dress, and he should have been properly made up, but the overall effect was worked well. After modeling the red dress for a minute or so I helped Bill take it off while Darlene picked up the black dress we had found. Although it had a skirt similar to the red dress, the second cocktail dress had a lot more material in the shoulders, cap sleeves and more of a V neckline than a sweetheart neckline. "That's enough for tonight," I told Bill and Darlene once we had viewed that final dress. "I really liked the way the blue ballgown and the red cocktail dress looked on you honey. I think you should get both," I said to Bill. After a brief pause Bill said, "Okay, whatever you want is fine with me" "That's great," Darlene exclaimed "I'll just pop up to the front to ring up your purchases for you, including both the short and the full length petticoats," she informed us before heading to the front of the store. "It would make me happy if you would be willing to wear your new cocktail dress home," I told Bill in my best bedroom voice, once Darlene was out of earshot. At first I was positive he would refuse, but then a funny look went across his face and he finally told me, "I will if you really want me to." "Okay, it's settled then. I'll unzip you from that dress and help you put the red one back on," I directed. It only took seconds before the black dress was down around his ankles. I held the dress ready as Bill stepped out of the black dress and into his new cocktail dress. I zipped him up and stepped back to admire how he looked. I decided we would definitely be going shoe shopping at some point to find red high heels to match this dress. I also had hopes I could get Bill to wear his new dress in public sometimes. Maybe get him to go out to dinner dressed like this. "Time to pay for your dresses and head home," I told him as I gathered up the pants, shirt and shoes he had worn into the store. We held hands as I guided him to the front cash where Darlene was waiting. "You're wearing the red dress," she exclaimed as we came into her sight "Have you decided to wear it home?" she asked Bill. "Yes, Linda talked me into it," Bill responded. "How cute. You look pretty in that dress," she complimented him. "It really suits you," she added, much to Bill's embarrassment as he turned red. I assume as a man being told a dress looks good on you isn't necessarily what you want to hear from a pretty young woman. I handed Darlene my credit card and within a minute had completed payment and were ready to leave. "Thank you so much for everything Darlene," I told her. "You were wonderful" "My pleasure. Please feel free to come back when Bill needs more dresses. The two he has won't be enough if he starts regularly going out dressed," she suggested. "Next time you might want to consider one of those strapless numbers he tried on. With the right makeup and jewelry he can pull off that look no problem," Darlene assured us. "Thanks Darlene. We'll give that suggestion some serious thought," I responded as she handed me the package containing Bill's blue gown and petticoats. Stepping up to Darlene we exchanged a cheek kiss. Once I stepped back I indicated to Bill he should do the same. When he was dressed as he was now I wanted him to think like a woman. It occurred to me I needed to teach him to curtsy, which I resolved to do within the next few weeks. Bill stepped demurely up to Darlene and copied my cheek kiss. I loved the way he balanced on his high heels as he did it. We exited the building and I could hear Darlene locking the door behind us. It was fairly dark out, however the lights in the parking lot allowed us to easily locate our car. "Let's get in the back seat," I suggested as I used to key-less remote to open the car. Bill looked at me quizzically but slid into the back seat without speaking.. Following him into the car, I shut the door behind me, triggered the remote to lock the doors and then jumped on Bill. I lifting up his skirt, pulled down his panties and started giving him a blow job right there in the back of our car. He started thrashing around and within thirty seconds did something I that surprised and delighted me. He grabbed his breasts and started stroking them just like a woman in the throes of passion. Stopping the blow job I was giving him I asked him "Does that get you horny, playing with your boobs like that?" before continuing where I left off, causing his hips to move faster and faster. "You didn't answer my question"I scolded him as I stopped once more "Does pretending you have breasts like a woman get you excited?" I demanded, waiting for him to respond. Finally he gasped out, "Oh yes." I made use of the slight pause to move us into the sixty-nine position. I chuckled inside thinking to anyone glancing into our car we would look like a couple of lesbians giving each other oral sex. Our mutual passion built up steadily, and I went wild feeling his tongue on my clitoris. In the end our timing was excellent as we managed to have an almost simultaneous orgasm. During the drive home both of us were very quiet. Now that our passion had cooled Bill seemed a little uncomfortable riding in a car while wearing a dress and high heels. As for myself, my lack of conversation was intentional. By this time I was familiar with the pattern Bill tended to follow. Namely tonight I had pushed him further into dressing in women's clothes than he had gone previously. While he had been a willing participant and had obviously enjoyed the whole thing, by now he was feeling guilty because of the fact he had enjoyed it.. If he followed his usual pattern his next step would be to pull back, store the dresses out of sight and then go on with his life pretending tonight had never happened. That phase would last for anywhere from a couple of weeks to a couple of months, at which point he would start to miss the intense arousal brought on by the clothes and awesome sex that followed. When he reached that point the clothes would come out of storage, and with the right incentive I could then entice Bill to wear them once again and likely go even further than he had previously. I knew Bill would need to progress through the entire sequence, so I thought it best to give him a bit of time to ease into that by not reminding him how he was dressed currently. I did make a couple of comments regarding traffic and how long it would take us to get home, but other than that I focused on my driving and left Bill to his guilty thoughts. The one thing that did concern me was whether I had moved him too far too fast. It might have worked better to get him into everyday type dresses first before introducing the more formal gowns he had tried on tonight. On the other hand my gut feeling was a dress was a dress as far as Bill's reactions were concerned, and the type of dress would likely have very little impact on the length of his 'guilty' phase. All in all I felt tonight had worked out very well. If we hadn't done it this way, Bill likely would have gone through a guilt phase when I introduced him to dresses and a second guilt phase when I later introduced him to gowns. This way seemed much more efficient all things considered. Arriving home I made sure Bill got out of the car first so I could watch him navigate up the stairs in his high heels, the skirt of his dress swinging with his steps. I could understand why men liked to watch women in high heels. The whole thing was very sensual, and I looked forward to Bill in future spending many hours dressed like he was now. As we headed into the house I offered him my assistance. "Did you need help with anything honey?" I said in a helpful and non sexual way. "No, I should be able to do everything myself," Bill answered as he continued to head towards our bedroom. "I'll start dinner then," I informed him and detoured towards the kitchen. Bill appeared some ten minutes later, dressed in a shirt and pants as he typically did, all evidence of his feminine attire gone. I was a little sad but not surprised. "Did you need any help with dinner?" he asked as he came up behind me. "No, why don't you relax. You're the one who tried on all the clothes. I know from experience that can be exhausting. Go sit in the living room and I'll call you when everything is ready," I told him as I worked at making everything tonight conform to our typical routine. We ate dinner once I had it ready, however the dinner conversation never strayed towards discussing our just completed shopping trip. That night I drifted off to sleep, happy at the progress we had made and enjoying thinking about ways to move Bill's crossdressing to the next level.