Unsuspecting Husband free porn video

My name is Linda, and my story started when my husband Bill and I recently watched a comedy that featured men cross-dressing. Ever since, I found I had a burning desire to have my husband wear sexy lingerie and makeup. I have to mention there is nothing effeminate about my husband, and he certainly had never expressed any desire to wear lingerie or makeup. Still I couldn't get the idea out of my head. Weeks later I was walking through a mall a little ways from home. Never having visited this mall previously I was doing a lot of wandering and browsing and found myself outside a fairly sizable and somewhat classy lingerie store. Some impulse drew me in to the store, and I soon found myself looking through racks of sexy brassieres that looked like they should fit Bill. It just so happened that I had gotten some suits custom made for my husband a month before, and had a full set of his body measurements tucked away in my purse. Images from the movie we had watched popped into my head, my burning desire resurfaced, and suddenly I was speaking to one of the pretty Sales Associates who staffed the store. "Hi Crystal," I said, reading the name displayed on her store name tag. "I am shopping for some women's lingerie for my husband Bill to wear," I confessed to her, taking the plunge by being upfront and honest with this SA. If knew if my plan was to have any chance of working everything I bought needed to fit Bill properly. She seemed a touch surprised but what I had just told her, but recovered quickly. "Okay, I'm sure we can find some things that will do the job," she replied. "Do you know his measurements?" she asked. "Yes. It so happens that he had some suits made recently, and I still have the measurements the tailor made at the time. My name is Linda by the way," I informed her. "Excellent," she exclaimed. The measurements will help a lot, Linda. What lingerie did you have in mind?" Crystal asked. "I definitely want him to wear a bra and panties, and was also thinking about a garter belt and stockings," I told her. "If you can pull out those measurements we can get started," she assured me. "Out of curiousity does your husband know you are shopping for him?" she asked "No he doesn't. I still have to work that part out," I admitted as I turned slightly red. "This situation is definitely a first for me," Crystal commented "From time to time I have had men come in shopping for themselves, but never a wife shopping for a husband who doesn't know about it," she explained. "Do you have a problem with it?" I asked out of interest, wondering if I should find someelse to help. "Absolutely not," she replied "I'm completely in favour of women fulfilling their fantasies. If that means you want your husband to be the one wearing the pushup bra instead of you, then I'm behind you 100%," Crystal assured me. "Great, let's pick out that pushup bra for him," I commented. "Sure, that will be the best place to start. Let's look at some bras for him first, and then we can see about matching the rest of his lingerie to the bra he'll be wearing," Crystal suggested. "What did you have in mind for the cup size?" she added. "Did you want a bra that will take what he has up top and mold it into convincing cleavage, or were you thinking of a larger bust for Bill, with him using falsies to fill out his bra properly? Crystal queried me. "I actually like the idea of molding what he has. I still have to talk him in to this whole fantasy. Trying to also talk him into wearing falsies might push it too far for him, at least early on. Eventually I can definitely imagine him sporting large breasts on his frame," I explained to Crystal "That makes sense," she responded. "Why don't we look over here at some of our 'miracle' bras," she suggested. "You don't look like you would ever wear them, but these are made for those women who don't have much up top naturally and want to look bustier. If your husband has any loose flesh at all on his chest one of these bras will help give him noticable breasts," Crystal assured me. "That sounds perfect. He does have a fit of extra flesh up top that he has been trying to lose," I admitted to her. "Here are all of Bill's measurements," I added, pulling out the paper the tailor had provided me the previous month. Glancing at the paper Crystal quickly made her choice. "A 40 'A' cup bra should do the trick. You can't actually use the measure and add 5 inches rule when looking to fit a man into a bra." she informed me. "They are built differently than we are, and as a result using that women's fitting rule leaves a man wearing a bra that is way too big to fit him properly," Crystal commented. "This 40A pushup bra has some nice lace detail, should fit Bill properly, and will definitely give him a small set of boobs," she assured me as she made her way to a rack of white bras, all of which seemed to be padded, underwired and have nice lace detailing on the cups and straps. I liked it immediately, thinking it was a very pretty looking bra and definitely something I would like to see Bill wearing. "Looks like we have a winner," I commented after inspecting the bra. "How about a matching panty and garter belt next?" I asked. "We should have something in Bill's size that will match his bra nicely," Crystal assured me. "We just have to go to the next aisle over," she added. Following her as she changed aisles, we quickly found panties and a garter belt both in a large size, and both with the same lace detail as the bra. "We can get his stockings at the front counter," Crystal told me. "While you are here is there any other lingerie you want to buy for him?" she asked me. "Better if I don't," I replied. Once he sees the stuff he may ask me if that is all I bought for him, and I want to be able to honestly tell him yes. If he thinks I've bought him an entire feminine wardrobe it could scare him off," I explained to Crystal. "If I were to buy something else in future for him, what would you suggest?" I asked curiously. "A merry widow, a corset or both. And high heels of course. Men always want us to wear a pair of sexy high heels. It's about time some of them did the same for us," she told me. I started to imagine Bill in a corset and pair of heels and really liked the mental image I was getting. If I could talk him into the things I had just picked out, putting him into a corset and heels would be next on my to do list. "Thanks for the advice," I told Crystal as I broke out of my daydream. "My pleasure," she replied. "You should also think about bringing Bill in for a proper bra fitting at some point. I would be more than happy to give him one, and that way you can be certain all of his bras wll fit they way they should," she told me. "It would also definitely reinforce the whole feminization thing you are trying to do. Once a man has been in for a bra fitting I doubt he will ever get that big macho feeling most men have. Having a strange woman putting bras on a man should kill that feeling within him for good," she observed, to which I had to agree. I did have serious doubts whether Bill would go for something like a bra fitting, but adopted a wait and see attitude. Talking him in to doing something in the privacy of our house was one thing. What Crystal was talking about was a pretty big next step, but I filed it away for future thought anyway as I was somewhat intrigued by the idea. I suddenly started to think about my own reactions in all of this. I was a little surprised that I watched this one movie and was now contemplating involving an outside party in a bra fitting for my husband. Shaking my head to clear it, I brought my thought back to the matter at hand. "I guess we are pretty much done here," I commented to Crystal. "If you come with me to the front counter I'll ring up your purchases," Crystal replied as she headed for the front of the store carrying the bra, panties and garter belt. She snagged a package of sheer white stockings on the way and then moved behind the counter to ring up my purchases. "Best of luck getting Bill in his new lingerie," she commented as she totalled my bill. "I'm not sure I would want to do that with my man, but I do admire you for having a desire and then pursuing it like this. I really do hope you get Bill into his bra and panties. Also please let me know if I can give you further help. And even if you don't end up shopping in my store again, I would still like to hear how this whole thing turns out for you," she told me as I paid her and she handed me the bag containing Bill's lingerie. "Thanks for all your help Crystal. I suspect I will be back in your store at some point, however regardless of that I will definitely keep you updated on how successful I am getting Bill to do this. After all your help and encouragement I think you deserve to know," I promised her. "Have a nice day Linda. I look foward to hearing from you again," she told me as I left the store. While uneventful, the trip home gave me lots of time to think about the future. Why this sudden urge to crossdress my husband? Did I really and truly want to have Bill do this for me? If I did talk him into doing it what would happen afterwards? I had no good answers to my questions other than the realization from somewhere deep inside me that yes, I would be trying to get him into the lingerie at some point soon. I didn't know how and when, but was certain I would make the attempt. I didn't really understand why I wanted it, but I realized I did want to femininze my husband a little, and was determined to have it happen one way or another. It was at that point that I started planning the when and how details, with a tentative plan of raising the topic during or after lovemaking. I had arrived home by this point, and soon had Bill's new outfit stashed away in one of my dresser drawers. Weeks had passed and while there had been a few lovemaking sessions during that time, I had balked at raising the issue with Bill during any of those sessions. I could feel the pressure to act building inside me however, and decided it would be better to do this while I could still do it skillfully rather than waiting until I said something in the heat of the moment. It was Saturday and I knew I could likely entice Bill into another session later that day. I determined my best bet was to do this in stages, with part one being to make use of panties in the heat of passion. As predicted Bill was ready and willing to go, and by mid afternoon we were engaged in foreplay. Once he was somewhat aroused I told him 'I want to try something new'. Although distracted, he didn't object so I went to the dresser drawer and pulled out one of my pairs of satin panties. Moving back to the bed I started rubbing the panties up and down his penis. This turned out to be an instant success, as within a less than a minute he was ejaculating into the panties before sinking back onto the bed exhausted. "Wow, that was intense," he told me once he got his wind back. "You liked that, did you?" I replied, playing it really coy. "Yes, I wouldn't mind doing that again in future," he confessed, muuch to my delight. We chatted as I gave him some time to recover. After giving him ten minutes or so I started masturbating him once again. At the appropriate time I told him to 'stay where you are' while I once again went to my dresser drawer. This time pulling out the panties I bought for Bill, I once again moved in. I started by rubbing the panties up and down his shaft as I had done last time, with similar results. Just before he was about to lose it I stopped, and gave him thirty seconds to calm down before starting up again. Once again I stopped before he could climax, and once again gave him a bit of time to calm down. Finally I started rubbing the panties against his penis for a third time. Then, just as he was about to climax I stopped, took the panties, moved down his body and slipped his feet into the leg holes of the panties. He was a little confused and seemed about to questions me so I quickly pulled the panties up his legs and settled them around his hips. Then I started rubbing his penis through the satin material of the panties, bringing him to the point of climax yet again. Once he was ready I stopped rubbing, pulled his panties down away from his cock and guided it inside my waiting vagina. He automatically started thrusting, and we came to a mutual climax in under a minute. I then pulled the panties the rest of the way off him before sinking down on the bed exhausted. Inside I was elated. I had done it! I had taken the first step and pulled it off successfully. I knew Bill would question me once he could talk again, but I was prepared. "That was wonderful honey. Thank you," I told him, and promptly pretended to fall asleep without giving him any chance to talk about the panties. Within a few minutes I could tell he had fallen asleep for real. With everything under control, I did fell asleep as well. I woke a few hours later with my stomach growling. Glancing at the clock I realized it was suppertime. Throwing on a robe I headed to the kitchen to prepare a meal. The food was almost ready when Bill appeared. Likely he had woken up in response to his stomach, and seeing I wasn't in the bedroom had come in search of me. "That was a lot of fun dear," he told me grinning. "I enjoyed it. I'm glad you did as well," I replied, waiting for him to bring up the panties. "Yes, well, what was the thing with the panties?" he asked, not quite asking the real question he had in mind. "You mean rubbing you with them? You seemed to really enjoy that. I don't have to do that again if you didn't like it," I replied, intentionally misunderstanding his question. "Yes I did like it, and I do want you to do that in future," he told me quickly backtracking. "It was the part where you put the panties on me that is throwing me off," he explained, finally coming out with the real issue. "Oh, that!" I responded, pretending to suddenly understand his issue. "It was a lot easier for me to do that than to keep holding the panties, and I was getting a little worn out at that point. I didn't think you would mind me making things easier for myself considering your reaction at the time," I explained. After considering my explanation for a short space he seemed ready to back down. "No, I don't mind you doing something to make it easier for you when we're having so much fun. It's just that wearing a pair of panties seemed really odd to me," he confessed, not wanting to spoil future lovemaking but also not wanting to let what happened pass without comment. "It was just the two of us involved honey, and what we did doesn't bother me at all. We were just having some fun in the bedroom," I told him. "Nothing happened to get upset about," I assured him. He seemed to accept that to a point, and I knew that while I still had some work ahead of me, I had won round one. I didn't initiate anything for a few days, deciding it was better for the idea of wearing panties during lovemaking to become firmly lodged in his head as opposed to trying to repeat the experience right away. The next time we did start something in the bedroom I left any sort of panty play out of the mix. As I had hoped the session was good but not nearly as intense as the previous one. I could sense that Bill felt the same way, and expected him to talk himself into a repeat of the Saturday afternoon experience. Sure enough the weekend rolled around and from the feeling in the air we seemed destined for a Friday night romp. We started kissing in the bedroom, with one thing leading to another until we got to the point of starting to remove various articles of our clothing. "I would like you to use the panties on me again," he told me as things heated up. "I'm sorry honey, I'm a little tired from working all week," I told him, waiting for him to commit himself. After a short pause he said in a small voice, "I could wear them," and I knew I had won round two. "I thought that was throwing you off," I replied, not wanting to look over anxious for him to wear the panties. I wanted to make sure the whole thing appeared to originate from him, not me. "As you said, it's only the two of us in the privacy of our bedroom. I'm okay with it if it makes it easier for you," Bill told me. "Okay, we'll do that then," I finally agreed. Walking over to the dresser drawer I pulled out his panties once again. Moving back to the bed I had him step into them and helped him pull them into place. Inside I was jumping up and down as he was know wearing the panties I had bought for him, and more importantly wearing them at his own request. I made sure the ensuing action was intense as I wanted Bill to associate the panties with having amazing sex. Weeks passed with Bill's panties generally playing an important role in our bedroom antics. Now that they were firmly established and accepted as part of our lovemaking I knew it was time to up the ante. The question was whether I should try to get Bill to wear the bra or the garterbelt and stockings? After a bit of thought I settled on the bra, deciding if I could pull that off the rest would be easy. The question of course was how would I pull it off? After a little more thought I had a tentative plan, which I put into action a few months after I had first purchased the lingerie. Launching my plan on a Saturday afternoon once again, we had started some foreplay and Bill was soon wearing his panties as usual. I also made sure he was more or less sitting up while this was happening, in anticipation of putting the bra on him quickly when the time came. After some of our usual activity he was at the point where he was almost ready to climax. I then stopped my stroking. I did the same thing a second time and stopped. In cases like this it was usually third time lucky for Bill but in this instance I stroked him and once again stopped before he could climax. By this time he was almost going wild with the pent up urge to ejaculate and I used that to move my plan along. As I started stroking his penis through his panties for the fourth time I started talking. "You know honey, I've just had the weirdest thought," I told him, and then stopped talking while continuing to rub. "No, it's just a heat of passion thing, not something we should try," I told him as I stopped stroking him. After pausing for 10 seconds or so my hands got busy once more. Once I could feel his body's reaction start to build again I started talking once more. "It might be kind of silly and playful though," I commented as I kept him at a fever pitch. "No, you might be embarrassed and I would never do that to you," I commented as once again my hands stopped moving. Another 10 second pause to let him calm down and I started stroking once more. "Still it might be a fun little experiment kind of thing," I mused, paused as if thinking and then said, "No, it's a crazy idea," as yet again my hands stopped pleasuring him. By this point he was going absolutely nuts, and I was concerned Bill would grab his penis himself and finish off what I had started. He didn't do that quite yet, and after the standard quick pause I started in again. "It wouldn't really hurt to ask you, you can just say no," I pondered out loud as I continued bringing him towards a climax. Then, "No, I shouldn't even ask," I said in a quiet voice. This time, instead of stopping altogether, I simply slowed down as if to suggest I was about to stop stroking him altogether. As I went slower still I was trying to give Bill the impression I was distracted and would likely stop my hand job before he could finish his orgasm. Still on the edge of ejaculating but not quite there, he finally burst out "What is it? What do you want to ask me?" he gasped, before contining to talk when I didn't answer right away. "I'm sure whatever you have in mind is fine. I'll do it." I acted as if I still wasn't sure I should ask him, while all the while keeping him at the point where he wasn't thinking clearly about anything other than getting his rocks off. Finally I sounded like I had warmed up to the idea. "As long as you are okay with it, why not," I told him, kept stroking with one hand while reaching beside the bed with the other. Earlier I had strategically positioned Bill's new bra beside the bed in anticpation of this moment. Now I quickly grabbed it, told him, "Please hold your arms out honey," and as he complied I stopped stroking him, took the bra in both hands and slid it up his arms. I then gave his penis a few more quick rubs through the panties to distract him and then asked him to "lean forward". As he did that I reached around behind him and fastened his bra. Once the bra was fastened securely I yanked his panties down and mounted him. I built up a good rhythm as my hands massaged his nipples through his bra cups. As the pace intensified my hands slid inside his bra and started tweaking his nipples, something he seemed to be enjoying immensely. Suddenly he was fully aroused, and proceeded to have a massive shuddering orgasm that seemed to go on for at least 15 seconds before he finally sank back on the bed exhausted. Happily he seemed to be drifting off to sleep. I kept completely still and silent and was rewarded within the next few minutes when he did in fact fall asleep. After giving him 10 minutes to move deeper into sleep I carefully reached behind him and undid his bra, before removing it from him. I stripped his panties all the way off and tossed both pieces in the laundry basket. I felt it was very important he not be wearing the gear when he woke up. That way he would remember what happened, but would have no real evidence of it happening and would presumably not have to explain it or discuss it with me. Short term my goal was for him to associate incredible sex with him wearing lingerie. My ultimate goal was to have him initiate wearing lingerie without my prompting, which is why I didn't want him to wake up in a bra and panties and think I had done it to him. It had to be something he wanted for himself if this was to work long term. Bill slept for a few hours while I went about my normal Saturday routine. When he appeared a few hours later nothing was said about our lovemaking session other than a "that was incredible" from Bill which received a "yes, yes it was" response from me. A few weeks passed during which we made love a couple of times a week. The first time after our Saturday afternoon romp didn't include any lingerie, and I tried to make sure the experience was only average. The sessions after that all involved Bill wearing panties. For those I believe I made it so Bill would have classified them as 'great'. At this point I was very happy at how my plan was working out in practice. For Bill him wearing no lingerie of any kind should translate in his mind into having average sex, him wearing panties translated into great sex, and him in a bra and panties meant amazing sex. Having established this connection in his brain I sat back and let his male ego fight it out with his male libido. I was betting that the libido would win in the end, his desire for incredible sex outweighing any shame he might feel over wearing a bra to get that sex. I knew I was very close to success when he started a discussion with me. "Honey, you remember that amazing sex we had a couple of weeks back on that Saturday afternoon?" Bill asked me on a Sunday evening two weeks after the incident in question. "Yes. That was something," I replied, not wanting to be too coy about it. "I've noticed we've had some very good sex since then, but not quite as good as that time, if you know what I mean," he observed. "Yes I had noticed that," I answered, guiding him towards the conclusion I wanted from him. "Any idea why that is?" he asked me. That was the question I was waiting for. I knew he had the answer already, but was unwilling to voice it because he felt it would threaten his masculinity. I suspected in his own mind having me verbalize the reason would let him off the hook in some weird way. "Yes, I do have an theory on why that is," I told him before deflecting him with my next statement. "What we share on a regular basis is really good. I'm happy with our love life as it is now. We don't have to do amazing to be happy," I told him. "But isn't amazing better?" he replied. "Well yes, of course it is. I just don't think what we did that afternoon to make the lovemaking amazing is really your thing. I have absolutely no problems with anything we did that day, but since you have never talked about it I assumed you were uncomfortable with the 'garments' we used. I believe those garments were the key to the intensity you felt, however I don't want you to do anything that makes you uncomfortable," I told him. "You really have no problem with any of what happened that time or anything we 'used' to make it happen?" he asked me, still unwilling to fully commit. "Absolutely not. I love you just the way you are. Why would anything we did change that?" I told him. "You're 100% sure?" he asked me, still trying to get comfortable with the idea. "Positive," I told him, waiting for him to take the plunge and ask what was really on his mind. After pondering what I had told him for a few minutes he finally seemed willing to move it forward, however indirect his words were. "I'd like to do that again," he confessed. "You know, the great sex and the other stuff," he added. While he didn't seem willing to say out loud he would wear a bra, he did seem willing to do it, which at this point was good enough for me. Sometime soon however, I would have to get him to actually say the words out loud. It was essential for my future plans that he be comfortable with both the words and actions. "Okay then," I told him. "Relax and I guarantee this will be a lot of fun," I enthusiastically informed him. We started in on the foreplay, and both started get worked up. After some minutes I stopped and walked over to the dresser. Pulling out Bill's bra, panties, garter belt and stockings I moved back to the bed and dropped them beside him. He was staring at the garments so I quickly moved in and worked at getting him more excited than he already was. My ministrations worked well, and after a few minutes I knew I could stop and take the time to get him dressed in his lingerie. "You're sure you want to do this?" I questionned him, not wanting him to be able to deny anything later. "Let's get you dressed then, shall we," I told him, to which he nodded. Sliding the panties up his legs was easy. Next I had him stand up as I slid the bra up his arms and fastened it on him. Next came the garter belt, which I postioned on his waist and hooked. Finally I had him sit down as I worked the stockings up his legs and used the garters to secure them. He looked exactly as I had mentally pictured he would, and it was getting me incredibly excited. I practically overwhelmed him, rubbing his nylon covered legs, stroking his bra cup covered nipples, fondling his satin panty covered penis. Soon both of us were going absolutely wild, and after a good ten minutes of increasing arousal on both our parts he was inside me and we shuddered to a mutual orgasm. This time as we both sank back on the bed completely spent I left all of the lingerie on him. I wanted him to wake up dressed like that, remember how good it had been and realize how he was dressed was a big part of the experience. I also wanted him to see how cool I was with him dressed in lingerie even when we weren't in the middle of intercourse. One thing I did do before falling asleep was to pull his panties back in place. I woke up many hours later. Glancing at the clock I realized it was now early Monday morning. Looking around I realized Bill was asleep beside me, looking so sweet still fully dressed in his new lingerie. When I first had the desire to dress my husband like this I had my doubts whether I really would want it once he was wearing the underwear. Turns out I was concerned over nothing, as at this moment I knew I wanted Bill in a bra and panties every day from now on. I could imagine that every morning when I put my undergarments on, he would be beside me putting on a matching set. With this vision dancing in my head I reached over and started running my hands over Bill's brassiere. Rubbing along his bra straps to the bra cups, playing with his nipples through the material of the cups, reaching inside his bra cups to stroke his nipples directly. After a minute or so of my light touching I noticed two things. Bill was starting to wake up, and an erection was growing in his panties. I continued to play with his bra and pretend he had breasts as he gradually woke up. Although he seemed somewhat awake at this point, he wasn't doing anything to stop my hands from stroking him. I decided to play the situation for all it was worth, shifting on the bed so I was behind Bill, playing with the back of his bra before reaching around to cup his breasts through his padded bra cups. I couldn't believe it as his hips started thrusting, apparently turned on by me treating him as a girl. "Do you want to be my naughty girl?" I whispered in his ear, continuing to stroke everything except his penis. "Do we need to put a pretty dress and sexy high heels on you to help you feel more feminine?" I asked him as he seemed to get more and more excited. Reaching over to the night stand I grabbed the lube and squirted some on two of my fingers. Pulling down his panties with one hand, I positioned one lubed finger against his anus and started pressing while the other hand continued to play with his bra and breasts. It didn't take long for me to thrust my finger inside him, and which point he really went wild. "You're my girl now," I told him as he started humping my finger, getting more and more excited "my pretty, sexy, feminine girl who loves her lingerie," I added as he finally exploding all over the front of his panties. Once he was fully spent I withdrew my finger and then moved off the bed, starting my getting ready for work routine. I decided to not say anything about what had just happened, leaving Bill to come to terms with his own reactions. Nothing was really said as we both got ready for work. Obviously at some point Bill had stripped off the lingerie, however I didn't actual see him do it as next time I saw him he was naked and heading for the shower. I ended up being ready for work slightly sooner than Bill, so giving him a "have a nice day, dear" I headed off. The entire day I was thinking about Bill and how he would react that night. At this point it was a question of whether he would want to do what we had done again, or would he try and forget about the whole thing and never talk about it again. My money was on the first reaction. He seemed to have enjoyed himself too much to never do it again, however his sense of embarrassment might mean it would take a while for him to admit he enjoyed it and ask for more. I was a little surprised then, when he started to discuss it after work. He had gotten home before me, and almost as soon as I walked in the door he raised the issue. "Ah, Linda, about last night and this morning," he started off. "That was fun wasn't it?" I responded, not wanting him to thinlk I disapproved in any way of what we had done. I wanted this discussion to be about him being comfortable with wearing lingerie, and not about my reaction to it. "Yes, it was fun, but I'm very uncomfortable with what we did," he replied. "Okay dear. It worked out so well I thought we should do it again, however we don't have to if you don't want to," I told him, deciding to back him into a corner and see how he responded. "No, I don't mean that," he told me and then stopped talking. "Well what do you mean? You're not being very clear on what you want," I observed, trying to move him forward. "Well, I liked what happened," Bill started saying "You mean how excited you got while wearing a bra and panties and me calling you my girl?" I interrupted. "Yes, that. The problem is I'm really uncomfortable and embarrassed by the fact I enjoyed all of it," he confessed. "You will have to deal with that part yourself. My only question is whether you still want me to dress you up as my girl again?" I said, laying it out for him very clearly "I have to admit I didn't give it much thought at first, but personally I'm having fun dressing you up," I told Bill, the part where I claimed not to have thought about it being a small fib of course. After a short pause Bill responded. "Yes, I still want to include lingerie in our lovemaking evn if it does embarrass me somewhat," he stated. "Okay, if that's how you feel the next step is for you a have a bra fitting," I informed him. He was caught completely by surprise by this, and it took him a minute or two to recover. "Why do I have to do that?" he asked, still looking surprised. "If you are going to keep wearing bras you can't be stretching out mine. We need to figure out your bra size and then buy you some bras that will fit you properly. The best way to do that is for you to have a bra fitting," I told him in a matter-of-fact voice. "In fact why don't we go right now," I suggested, grabbing his hand and pulling him towards the door. He didn't seem able to resist as he let me lead him from the house and into my car. Within half an hour we had arrived at the mall where I bought previously bought lingerie for Bill. Leading him to the lingerie store, I was happy to see that Crystal was working at the store tonight. "Hi Linda," she greeted me as Bill and I entered the store. "Hi Crystal, how have you been?" I responded. "Very good thanks. I'm glad you came back to do some more lingerie shopping in our store. What can i help you with tonight?" she asked me. "You were so wonderful last time I shopped here, I'm hoping you will help me with a slightly unusual request," I prompted her, figuring she would take my cue and play along. "I'll see what I can do. What did you have in mind?" she replied even though I suspected she already knew what I was up to. "My husband Bill and I have been experimenting in the bedroom lately," I told her, indicating Bill "Bill wore one of my bras last night, and liked it so much we've decided he'll be wearing bras regularly from now on. I don't want him stretching out my regular lingerie so I want him to have a proper bra fitting. Once we know his proper bra size we can buy him a number of bra and panty sets he can wear whenever the mood takes him," I added as out of the corner of my eye I could see Bill turning red. "Oh, that sound like a lot of fun," Crystal responded "I've done a lot of bra fittings for male customers. I'm sure we can get Bill fixed up in a jiffy," she assured us as she motioned for us to walk with her to the change room area. "So Bill, will you just be wearing your new bras in the bedroom, or were you also planning on wearing them under you regular clothes when you go out for the day?" she asked "I hadn't really thought that far," he replied, sounding surprised Crystal would ask something like that. "It seems a shame to only wear bras when you are fooling around in the bedroom with your wife. I'll assume you will want to start wearing a bra fairly reglarly and fix you up accordingly," she informed him, as he seemed to turn a little red. "Remove your shirt please," she then requested of him. Not wanting to give Bill time to think or back out of this, I moved over to him and helped him remove his shirt. Once his shirt was off Crystal approached him with a measuring tape. Having once gone through a fitting myself, I wasn't surprised when she proceeded to measure under his lower chest, across his nipples and across his upper chest. "I'll be right back with some selections in your size," Crystal commented as she exited the change room. She returned with a couple of minutes carrying what looked like at least ten different bras. Bill looked a little stunned at the number of bras he was expected to try on in front of two women, but this hadn't actually caused him to flee as yet, which I took to be a very good sign. "Arms out please, and we'll try this first bra on you," Crystal mentioned to Bill. He turned red but didn't reply, however he did as ordered, holding out his arms as Crystal threaded a pretty black bra up his arms before stepping behind him to fasten it. "That looks pretty close size wise," she commented as she started checking the fit on him. First she examined the way the bra band was sitting across his back before stepping in front of him to check the underwires. Pulling on the underwires she told him "That is sitting nicely on your chest Bill. Notice the way the underwires are flat against your body?" she pointed out, taking his hands and pressing them against the underwires in his bra cups to demonstrate. "Because the underwires are flat against your skin it means you are wearing the right size bra. Also if you turn slightly and look at your back in the mirror you will notice how the bra band is level across your back and snug against your skin." she told him, turning him slightly so he could have a good view of how the bra fit across his back. "See how level the back of the bra is sitting on you and nicely below your shoulder blades, without being too tight," she commented, running her finger across the lower band of his bra to emphasize this fact. Bill nodded his head to indicate he understood what she was saying. "Also your bra straps are sitting against your skin without digging in. Taking all of those different things into account means you are both wearing the right bra size and your bra straps are adjusted to the right length. If you end up wearing a bra for the entire day you really want it to fit you correctly. If it doesn't fit properly the bra will start to become uncomfortable as the day goes on and you will really want to take it off, which we don't want you to do," she commented to him. "We now know this bra fits you well and will give good support to your falsies if you start wearing breast forms. Why don't we try some of the other ones on you to see what else might work for you," she told him "I brought some pretty padded bras for you to wear in the bedroom, as well as some seamless unpadded bras you can wear under your normal clothes without anyone knowing you have them on," she informed him. At one point Crystal left to bring back more bras, so in the end Bill spent the next hour trying on at least fifteen different bras, getting running commentary from Crystal on most of them. By the time he was finished trying on all the different bras Crystal brought him Bill seemed to have gotten used to the situation and appeared a lot more comfortable wearing a bra in public. He didn't appear to think twice when Linda handed him his shirt and suggested he put it on over the last bra he had tried on. In effect she was asking him to wear a bra home even though the bra in question was very heavily padded and would show clearly through his shirt. To my surprise he did donned his shirt without question. In the end I picked out a total of six bras for him, with three being 'bedroom' bras and the other three everyday bras I would be encouraging him to wear regularly as part of his day to day clothes. Going to the front counter to pay for all of Bill's new lingerie, I kept glancing with approval at his padded chest. If I didn't know better I would have sworn he had a perky pair of breasts under his shirt, and couldn't stop imaging how he would look in a nice sexy dress and high heels. I also started to think about Bill's reaction to me thrusting my finger in his rear end the other night. I knew I would be experimenting in future with my finger again, and was considering buying some sex toys at some point soon. I looked forward to exploring our new sex life in which Bill took on an increasing feminine role in the bedroom. The thought of Bill dressed as a girl and me using a sex toy on him put a smile on my face, as I found I had a new burning desire now that the first one was completely fulfilled.