Old Feelings free porn video

Old Feelings Jack slowly woke up, sunlight filled the bedroom. He looked over to the other side of the bed and was temporarily confused because it was empty. "Library," he groaned. His wife Debbie had wanted to find something part time to occupy herself. She wasn't happy that she was going to work every other Saturday, but she liked the idea of working at the library so she bit the bullet and took the job. Three days each week from 7:30 until 4:30. Jack was sort of happy with the situation; he got to have a few Saturdays to himself to do whatever he wanted. He crawled out of bed, grabbed his biking outfit, dressed, and then grabbed an energy bar. A vigorous ride was the best way to start out the day. He went to the garage and pulled the bike down off the hooks in the wall. Jack started out the ride slow, letting the muscles in his legs and back stretch out. It didn't take very long before he started picking up the pace and cruised his usual course. An hour and a half later he hoisted the bike back up onto its brackets and went to take a shower. He let the warm water run over his hairless body, an aspect of biking that he really liked. He never had cared for the hair that started covering his body as a teen, and though he considered himself lucky that there wasn't a lot, he used his hobby as a reason to keep himself clean shaved. He dried off, wrapped the towel around his waist and spent some time at the sink brushing his teeth and doing the rest of the morning routine. He enjoyed knowing he didn't need to rush because he wouldn't be interrupted by his wife telling him to get moving because there was something that needed to be taken care of. Once done at the sink he walked into the large walk-in closet and turned to the small section that held his clothes. Easily three quarters of the closet contained Debbie's things. They had the closet redesigned a year ago because of the constant turmoil it seemed to be in. Now they each had a stack of drawers to hold underwear, socks, and whatever other little items needed storing. Shoes also had slots into which they were all placed, though once again this was an area where Debbie's things took up a lot more space than his. He barely looked at the larger part of the closet and went straight to where his things hung. He was thinking he might go hit some balls at the driving range and grab lunch at the club house, so for that he needed one of his golf shirts and some khaki slacks. As he looked he was surprised to find one of Debbie's dresses hanging among his shirts. "How can you keep needing more space?" he called out looking back at the rest of the closet. He pulled the item from between his shirts. It was a summer dress: white, long, spaghetti straps, with an elastic top. He shook his head and turned to hang it among the rest of the dresses. But then he hesitated. He started thinking back at a time when he was a teenager living at home. Of how he snuck into his mother's things when he had the house to himself. Many afternoons he would find himself dressed up in an outfit of hers, sometimes for hours, other times for only a few minutes. He had started out trying on some underwear. Then he added a bra. Pantyhose, slips, dresses, skirts, even her shoes fit him for a short while. It didn't take long for him to progress to doing the whole outfit as often as he could. There were even times he wore pantyhose under his pants when he thought nobody would know. He smiled to himself standing there in his huge closet thinking of how he had managed to go all those years until he left home for college without getting caught. Oh, it had been close a few times but somehow he always managed to get everything put away. Thinking back on it now Jack thought maybe he wasn't as slick as he thought. There were times his mother made some remark that seemed like maybe she knew what he was up to but never enough that he knew for sure. He started to slip the hanger over the bar but hesitated again. He pulled the dress back and laid it against his body looking down. There was a full length mirror on the back of the closet door, he pushed the door closed and stood there looking. His heartrate picked up a bit as he started thinking about putting the dress on. "It's been so long, I thought I was over this," he whispered. In actuality he knew that he hadn't really gotten over it. He still looked at women and wondered about the things they wore and how they might feel. He stopped wearing women's things after he left home because he could never build up enough courage to buy himself any of the things he wanted to wear. He had tried to on several occasions. He would walk into a store and decide it was too crowded, that people would see him and know. Or someone he knew would come in and see him with a dress in his arms and know. Or the place didn't have enough people in it and the cashier would remember him and then if he ran into her somewhere later she would know. His paranoia knew no bounds. After getting married he tried to bury those feelings deep. He had managed for quite a long time. Until today. Alone in the house for most of the day, a dress in his hands. His hands shook a bit as he loosened the towel and let it drop to the floor. He kicked it away and removed the dress from the hanger. He pulled the dress over his head and struggled a bit getting the straps into the correct position relative to his head and arms. He tugged the dress down until the stringy straps bit into his shoulders. The elastic around his chest was snug but not too tight. He looked at himself in the mirror. A problem was immediately evident so he turned and went to Debbie's lingerie drawer. He found a white cotton bikini cut panty. He pulled his dress up and slipped them up his legs. They were tight, which was all the better as far as he was concerned, they would help to keep him a bit more under control. He took position back in front of the mirror again, slowly raising his eyes from his feet to his face. "I looked a lot more like a girl when I was thirteen," he huffed. Overall, though, he was fairly pleased. Between watching his diet, biking and golfing, he was in pretty decent shape. He didn't like doing gyms or lifting weights or anything like that so his build had remained fairly slim. The dress fit him well and was only a little short ending just above his ankles. On Debbie, the dress would almost touch the floor, her feet peeking out as she walked. The thought of her walking along in the dress pressed him to action. He pulled open the closet door and strode out into the bathroom. His first stride almost tripped him as the hem of the dress pulled tight around his calves and prevented him from taking the longer step he intended. He laughed a bit, shortened his steps and proceeded through the bathroom, beyond the bedroom and onto the balcony that ran above the main entry into the house. He nervously looked through the windows to see if any of his neighbors might be out and might spot him wandering about the house in the dress. He wouldn't have any explanation for them or for Debbie, and he was certain it would get back to her. Sure that nobody was wandering about he carefully made his way down the stairs to the ground floor. He walked to the kitchen and fetched himself a glass of water. He looked out into the backyard but was certain the eight foot privacy fence would prevent anyone from seeing in. Time to return to the bedroom, though. He didn't want to press his luck for too long. He almost tripped on the stairs as his dress grabbed at his legs as he tried to climb them. But, with a glass of water in one hand, and his dress hiked up held by his other hand, he made it back to the top of the stairs and then back to the closet without incident. Once in the closet he pulled the dress back over his head. It was a struggle for a bit but eventually it came off. He placed it back on the hanger and checked it over to make sure nothing had gotten on it; satisfied he hung it among Debbie's other dresses. He started to turn away but couldn't resist fingering along the dresses hanging there. He thought about trying some others on but fought off the impulse. He turned away and saw his reflection in the mirror, the simple white panties barely holding him in. He quickly peeled the off and carefully put them back in the drawer that he had gotten them from. Grabbing a selection of clothes of his own, he dressed and headed for the golf course to try and forget about his morning adventure. * - * - * Once again Jack stirred. The bedroom was still a bit dark as he opened his eyes. Looking out a window set high in the wall he could see a gray sky turning the day bleak. "It might make for a wet ride this morning," he groaned. He didn't like riding in the rain, but he wouldn't let it stop him from his morning exercise either. He slowly crawled from his bed and followed the normal Saturday routine. Two hours later he returned and went about cleaning up. When he finally finished he went into the closet, this time he left the towel behind hung up to dry. He had been thinking about this moment for the last two weeks. Debbie hadn't said anything about noticing her things being moved about so he figured he had done well putting everything back. He was going to push his luck a bit today. For that reason he was happy for the inclement weather. It would keep his neighbors inside and Debbie wouldn't expect him to go anywhere. He went first to the line of dresses. He looked through them trying to decide which one he was going to try on, once he made that decision he felt he would decide on the lingerie he would wear under it. Debbie had a great selection of dresses. They often went out to nice parties that required they dress up. Plus she preferred to look nice for outings at the mall so she had many casual dresses as well. His hands shook as he tried to decide which direction he wanted to go. At last he found a red dress that buttoned down the front to the waist, below that the skirt flared out. A wide black belt hung from the thread belt loops. "That's the one for today," Jack nodded satisfied with his choice. He turned the dress so that it hung down the outside of the remaining dresses still neatly aligned on the bar. Going to the lingerie drawers he searched through each of the drawers trying to decide what he wanted to wear under it. He found a black bra first. Running his hands over it he found it was soft and stiff at the same time. He fastened it around his waist and pulled it up into place, he slipped the straps up onto his shoulders. He crossed the closet and pulled a couple light t-shirts from his side and balled them up placing them into the cups. They fit well and he was happy with his boobs. Debbie was larger than his mother; he used socks back as a teenager. He returned to the lingerie drawer and found a pair of panties, also black. They were mostly lace and cut high on the hips. He slipped them on and tingled with excitement. He turned to look at himself in the mirror twisting back and forth. Debbie looked amazing in these and he felt he looked pretty good too. The back wasn't quite a thong, but he was certain that after moving around they would likely disappear. The thought excited him a little more. He returned to the clothes and took the dress from the hanger. He pulled it down over his head and turned the sleeves that reached his elbows around so they were right. He buttoned the front up as we returned to the mirror, not all the way to the collar, but high enough that it concealed his false breasts. He buckled the belt around his waist and smoothed everything down. "I wish maybe I'd left my hair long," he spoke to the mirror. "If I don't look at my face I think I look pretty good. Legs definitely work!" he noted looking below the hem which was just above his knees. Feeling satisfied, he left the closet and went about doing things around the house. He cleaned a little, went from area to area, anything he could think of to feel the dress fluttering around his thighs. Standing still, he was so aware of the things he was wearing and of how the loose skirt barely touched him, he felt so exposed and that thrilled him even more. All too soon he saw the clock had reached 4:00. Debbie would be home within the hour. With a bit of disappointment he returned to the closet and began stripping off the outfit he had enjoyed all day. He carefully returned everything back to their original places. The t-shirts were terribly wrinkled but he didn't think that would be a problem. He hung one back up and put the other on. Finally he was back in the den, golf on the television, and looking through e-mails on his laptop. "What have you been up to all day?" Debbie asked as she entered the room. "Oh, you know, did my ride, did a few things around the house. Weather pretty much made me want to stay inside," he told her. "How was your day?" "Fine, library isn't too busy," she walked over and kissed him. "I'm going to go change. I want to get out of this skirt and into some comfy clothes." "OK, then we can have some dinner," he called as she retreated from the room. "What is so uncomfortable about a skirt?" he commented to himself. * - * - * Jack woke up to the sound of Debbie leaving for the library. He was looking forward to these Saturdays he got to spend alone. He was wondering how he had managed to not do this before. The feeling it evoked walking around in her things was exhilarating. He already knew what outfit he wanted to wear today so he wanted to get right to his ride. A short time later he was quickly drying off in anticipation of spending the day in a pretty lime green skirt and top set. He remembered it was made of silk and the skirt was long, about mid-calf, but it was full so it wouldn't trip him up trying to walk around. He rushed into the closet and found a bra and panty, white this time. After preparing his boobs, he sorted through the clothes until he found what he was looking for. He pulled the top on; it was short barely reaching his navel and the sleeves were just long enough to cover his shoulders. The skirt had a wide, soft elastic waist. He stepped into it and pulled it up to his waist, just barely under the hem of the top. He left the closet marveling at the feeling of the wispy fabric as it slid across and between his legs as he walked through the house. He watched it billow as he quickly descended the staircase. "Oh, yes," he muttered. "I wish I could dress like this all the time. I wouldn't be in any hurry to change into something comfy." It was well after four when he realized the time and hurried back to the closet to change into his own clothes. He looked at himself in the mirror as he was leaving, now clad in jeans and a slightly wrinkled t- shirt, and sighed. * - * - * Jack fell into a regular routine every two weeks while Debbie was working at the library. Go for a ride, shower, pick out a different outfit to spend his day in, and then change right before Debbie was due home. He found it was having a beneficial effect on him in other ways he didn't expect. He was in a better mood during the week and he believed it was entirely due to how he was spending his Saturdays. What else could it possibly be? Nothing else was different except Debbie working. And that couldn't be it because they weren't having any problems at all. In fact, if he were to admit to any feelings of frustration it would be that he didn't feel he could wear some of the blouses or dresses because they were too sheer, or cut too low. He wished he had something that would allow him to have what appeared to be natural breasts. Then there was his head. He enjoyed everything so much but when he saw his face in a mirror atop one of the outfits, it depressed him a little. Today he decided to try and resolve that. After his shower he wrapped his towel around him and sat in a chair Debbie kept in the bathroom for the very purpose of putting on make-up. He positioned his laptop nearby. He had watched a few videos on applying make-up and had one ready now. He punched play and watched intently. When the first step was completed he paused the video and searched the drawer for what he needed. He spent a long time first putting on the base then washing it off again to be sure he could get it all off. Step by step he went about trying to make up his face only to clean it off again to be sure he could. It was more than two hours later when he had decided he was done he went to the closet and got dressed. He chose a white blouse with a black miniskirt. The skirt was tight for a change, he hadn't worn too many tight skirts, but today was going to be totally different. When he finished dressing, he found a colorful silk scarf. He placed it over the top of his head and carefully knotted it in the back so that it covered all of his hair. He finally went to the mirror. "Well," he eyed himself critically. "I look like a cancer patient who had trouble getting her make-up on this morning. But, I think I at least look like a female cancer patient!" He spent the day as usual puttering about the house. This time he didn't avoid looking in any of the mirrors. He would look and try and decide if there was anything more he could do to look more feminine. He could tell the make-up job was amateurish but he felt that would improve over time. Unfortunately all of Debbie's earrings were for pierced ears and his weren't. Maybe some other jewelry would help though. He kept a closer eye on the time and at 3:30 went to clean up. He wanted to be sure he could get all the make-up off before Debbie returned. After closely inspecting his face he decided he had done as well as he possibly could and went to sit in the den again. * - * - * Weather was now getting a bit cooler and so was the temperature in the house. Jack selected a deep blue knit dress with a cowl neck and long sleeves. It was sort of long, just below the knee, but he found a wide belt that he wrapped around his waist and allowed him to pull the dress up to just above his knee and draped the extra over the belt. The best part for this day was it was cool enough that he added sheer black pantyhose. He had gotten better at doing his make-up. Maybe not as good as a real girl, but a lot better. He also felt he had developed a good eye for accessorizing. Fortunately, Debbie had a great selection of things to choose from and he was naturally conservative feeling less was more. He went about the house and took care of the few things he needed to handle, then went to the den. He was in the mood for a movie so he turned on the surround sound and the flat screen and leaned back to enjoy the show. "Who are you and what are you doing in my house!" came Debbie's voice from the doorway. Jack jumped to his feet, facing her, his eyes wide with horror. "Jack? Is that you?" she asked as she advanced into the room. "What the hell is going on here?" "Uh, um," he fumbled trying to speak. His mind racing in circles trying to figure out what to do, what to say. "That's my dress! And my necklace!" she was now just a foot away. "Are you going to answer me or just stand there opening and closing your mouth like a fish?" "Oh, um," Jack swallowed and licked his lips reminding himself it wasn't just the clothes. "I've, uh, well, I've been experimenting with, uh, your clothes." "No kidding," she sneered. "You know what? I can't handle this right now. I'm leaving and I'll be back at dinner time. I would appreciate it if I could talk with my husband at that time." "Yeah, sure," Jack dropped his head, his stomach was flipping. "Um, what are you doing home so early?" "A pipe burst early this morning at the library. We've been cleaning up all day. The library had to be closed until it gets fixed Monday. Once we were done we left," she answered as she left the room. Jack stood there for several minutes just staring at the open doorway. Finally he found the ability to move and turned off all the electronics. Then he trudged his way to the bathroom where he went to work cleaning off his make-up and putting the things he was wearing away. He wasn't as concerned about putting things back exactly as they were this time, though he was still careful to put them back where they belonged. Back in his own clothes he returned to the den but he didn't bother with the television. He just sat there in the quiet trying to decide what he was going to tell Debbie when she returned. "If she returns," he corrected himself. In the quiet he heard her come in the house several hours later. She went straight into the kitchen. "Come get some pizza," she called out. "I didn't think anyone would feel like cooking tonight so I picked one up. Grab a plate and we'll talk." Jack walked into the kitchen to see Debbie pouring herself a glass of wine with a plate full of pizza in the other hand. Without a word he picked up a plate of his own and dropped several slices onto it. He wasn't sure he felt like he could eat any of it, but he thought he could chew on a piece if he needed time to think. He waited and when Debbie finished pouring her wine he took a glass for himself and filled it. Debbie went back to the den, unusual as she normally insisted on eating at the table. She took a seat in a chair across the room and set her glass on the small end table beside it. Jack sat at the end of the couch. "So, how long have you been doing this?" she asked him. "Well, that's difficult to answer," Jack responded nervously. "I think I need to tell you a lot of things." He took a big bite of a slice of pizza and worked up the nerve to tell his wife his story. He started off slowly telling her about how he started experimenting with his mother's things. Told her how he progressed to wearing full outfits and how it made him feel free and happy. Then he explained why he stopped and how he was afraid to buy anything for himself so he just couldn't do it any longer. He admitted he still thought about it from time to time, but hadn't succumbed to the desire. Not until that day he found her dress hanging among his clothes. "At first I was just going to move it back to your side of the closet," he smiled weakly at her. "But then I thought about being at home alone, and that it looked like it would fit, and I wondered if it would feel the same as when I was a teenager." He looked down and was surprised to see his plate was empty. He set it down and picked up the wine glass. One more sip and that would be empty too. "Actually, I think it felt better," he admitted. "The next time I went with a whole outfit. A few weeks later I decided to try make-up. Shortly after that I added the accessories. Would you like some more wine?" Debbie just nodded and held her glass out. Jack took his empty plate and glass, added Debbie's glass and went to the kitchen. "Any more pizza?" he called from the kitchen as he poured the wine. "No," was all that came back from the den. Jack sighed and picked up the full glasses. He handed her a glass and returned to his spot on the couch. "That is everything," Jack told her. "Is it?" she asked, a tear threatened to spill down her cheek. "I have noticed you have been in a better mood lately and I wondered what it was that put you there. Then I started worrying that you might be having an affair while I was working. I walk into my house today and find a woman sitting in my den! Then I see it isn't a woman but my very own husband. So I leave to get my head around what I've seen and I start thinking perhaps you are having an affair, only you are having it with another man. I don't think that it is everything at all. I need to know not just what you have been doing but where this is leading." "Oh, my," Jack gasped. "An affair? No, my dear, no, never. I love you so much. The idea of having an affair with another woman hadn't even occurred to me. And with a guy, no thank you. I have no desire to touch a man. That isn't part of this at all. Any fantasies I might entertain involve you." "You sure?" she visibly relaxed a little. "Yes, positive," Jack assured her. "I think that after this afternoon lying about anything now would be a huge mistake. If there were anything else to this, I would prefer to clear it out now. Even with my total honesty I don't know what you are going to do." "Well, I don't know either," Debbie told him. "But I'm not going anywhere. It's a lot to digest and I am going to need some time. Can we talk more later?" "Absolutely, whatever and whenever you want," Jack dared to feel a little happier. "OK," Debbie stood up. "I am going to bed. I'd appreciate it if you would give me an hour or so before you come in." "Would you prefer I stay in the guest room tonight?" Jack offered. "No, I don't think that would be necessary," she stood and headed toward the kitchen. "I just want some quiet to think about this for a while. I might be asleep by the time you come in." "OK," Jack stayed where he was. He waited about fifteen minutes before going to the kitchen and emptying the wine bottle into his glass. The leftover pizza got put in the refrigerator and the dishes were rinsed in the sink. He took his wine back to the den, turned on the TV and half-watched the images on the screen for a couple hours before he turned it off and went to the bedroom. He crept into the room and heard the soft heavy breathing of his wife. She had managed to get to sleep. He stripped down and climbed gingerly into bed. It was some time before he was able to get to sleep. The next morning he woke and found the bed empty. He dressed and went downstairs where he found Debbie sitting still in her nightgown, legs pulled up under her sipping at a cup of coffee. "Good morning," he offered not certain whether he would get a response. "Good morning," she replied. "Why don't you get some juice and let's talk some more." Jack went and found a glass and poured himself some orange juice. He had no idea how much more he could tell her. The feelings were there, like many other things in life this was something he liked. He couldn't help it and after these past few months, he didn't really want to help it. He enjoyed his Saturdays. He turned and went back to the den. Jack hesitated when he entered the room uncertain of where he wanted to sit. He wasn't sure if he should take the couch beside Debbie, or retreat to one of the other chairs in the room. After a moment he decided to sit in a chair that was close to the couch. "I've done a lot of thinking about this," Debbie started, "and I can't really say I understand it. But I've grown up all my life being able to pretty much wear whatever I wanted. There are women who absolutely hate wearing dresses, some who won't wear anything else. I like them enough to wear them most of the time. All that being said I haven't come across a lot of straight men that want to dress up like you were yesterday. You say you aren't interested in men and I guess I can accept that. It's not like I caught you here with another guy, but you need to understand that I have a lifetime of being taught and believing what I have. For now, I am going to accept that this is just something you like doing on your day off when I am working." "I'm not sure I understand," Jack was confused. "Are you saying that it's ok if I continue dressing up on Saturdays when you are at work?" "Yes," Debbie nodded. "For now, I would still appreciate it if you would still clean up and change before I get home. I don't think I am ready to watch you around the house that way yet." "I can do that," Jack nodded vigorously. "That was a neat trick with the scarf," Debbie grinned. "But I think you really ought to have a wig if you are going to try and look female." "I told you, I'm too nervous and embarrassed to buy anything for myself," Jack complained. "I know you don't feel like you can go to the stores, but you can order things online," she explained. "I won't open any packages that come addressed to you, ok? It'll spare you some anxiety. But, you may find going to a store is easier in some circumstances. Halloween is coming. You could just explain you are dressing up for a party." Jack was stunned. It was a simple solution that he had never considered. He nodded at her numbly. "Babe, I love you," Debbie smiled at him. "And I'm not sure how things are going to go from here except that I am willing to try and see how I feel about it over some time and you can help me by doing just like you have been. If I get off early, I'll call and warn you I am on my way. Will that work for now?" "Oh, absolutely," Jack smiled. "But one question: If I do start picking up things like wigs, will it be a problem if you see things start accumulating in the closet?" "No," Debbie answered after a slight hesitation. "I think it will help me continue to deal with this. If it becomes a problem, we'll talk about it again." "Thank you," Jack got up from the chair. "I love you so much and appreciate the effort you are putting forth." He went to the couch and leaned down to kiss her. To his relief she kissed him back. * - * - * Jack and Debbie didn't discuss it any further over the next two weeks. Jack was happy for that because as much as he thought he would like knowing that he didn't have to sneak around, he also wasn't sure how he felt about walking into a room all dressed up with Debbie there. The next Saturday that Debbie left for work Jack went about his normal activities. That included going for his ride, showering, and putting on make-up and a nice outfit for the day until Debbie was due. On this particular day he chose a belted knee-length red and white striped dress. Once he was ready he went down to the den and grabbed his laptop. He started searching online for wigs. He soon realized there was a lot he didn't know about them. He went to site after site looking at the various styles and the prices. "Good Lord!" he called out as he saw one site that had wigs with prices in the thousands. One site led to another and he eventually stumbled onto one that was specifically for cross-dressers. He looked over the selection and saw several he liked. They were mostly less than $100, which was good, though he had hoped for less. "You get what you pay for," he told the empty room. As he dug deeper he found out how to measure his head for a good fit and after hunting the house for a tape measure, was pleased to see he was Regular, so he had planty of good choices. His fingers trembled as he made a selection and then clicked the Add to Cart symbol. Before he left he searched the rest of the site and saw many things that interested him. He realized that it wouldn't take long to spend a lot of money doing shopping like this. He needed to be careful. Before he went to the checkout he decided to look at one other tab: breast forms. He looked them over and decided he wanted to add the realistic ones. They were expensive, but they would be better than the balled up t-shirt that he was using all the time. He checked out and put the laptop away. He could hardly wait for the next Saturday, certain his order would arrive before then. What a difference he believed they would make. He saw the clock had reached the 4:00 hour and went upstairs to change. He scrubbed his face clean, carefully put away all Debbie's things and returned to the den. He just sat down when Debbie returned. She smiled, gave him a kiss, and went on to the kitchen to start dinner. "Hey, dear?" Jack called. "Yes?" "Why is it that you always make dinner except when I get take out or we go out? When did I stop doing any cooking?" "Shortly after we got married," she appeared at the door. "You did fine with the few things you cooked, but I prefer to do the cooking. Has this got something to do with what you are doing on your days alone?" "No, I don't think so," Jack frowned trying to decide why he suddenly was thinking about this after all this time. "I just realized that after working all day, maybe it would be easier for me to fix something while you were heading home." "That is really nice of you to think of me like that," she smiled. "But I don't mind. I just plan something easy on these nights." "OK," Jack settled back on the couch. "I just thought I'd ask." Debbie lingered in the doorway for a few moments before she returned to the kitchen. * - * - * Jack finished his ride in record time and had trouble not rushing through the shower, but he wanted to be sure he was exceptionally clean. His box had arrived earlier in the week and he immediately placed it in his corner of the closet. He didn't know if Debbie had noticed it, she hadn't said anything. He walked into the closet and grabbed a pair black satin and lace panties and put them on. Then he took his box and opened it. He pulled the wig out and looked it over. His heart raced at the idea of having long hair. He took a brush and fixed it up. Though he was certain he should do his makeup first, he couldn't wait any longer, he pulled it on. He looked himself over in the mirror and adjusted it here and there. He shivered from the feeling of the hair brushing his shoulders and back. Next he removed the breast forms. They looked quite real; the color was close to his skin tone, the pink nipple protruded just a bit. He held them against his chest and looked in the mirror. More shivers. He found the last item in the box, adhesive. He went through the instructions and carefully attached them. The weight felt strange and good. He returned to the closet and pulled out a black strapless long- line bra. He put it on and adjusted his breasts in it. He returned to bathroom and sat to do his make-up again. It was so different fixing his face with the long hair and the breasts felt different as he moved and reached. He used darker colors than he did before because he was going formal today. Before he had always chosen dresses that suited going to work, or daytime outings, though he never left the house, now he was going for a formal evening look. With the dress he chose he was going to be showing off his new cleavage. He applied some makeup to the edges of his breasts to camouflage the edges. Satisfied with the look he removed the black strapless dress from the hanger. He held it against himself and looked in the mirror. It was going to look splendid! But he decided he needed something more. He carefully set the dress aside and searched the lingerie drawer. He was so familiar with things it only took a moment to find what he desired: garter belt and stockings. He fastened the belt around his waist, then slid the shear stockings up his legs and attached them. Once again he took the dress, though this time he stepped into it without hesitation. He pulled the side zipper closed and then adjusted it so that it sat properly on his body. He turned to the mirror. The tops of his breasts were visible above the top of the dress; it fit him tight through the waist and accented his hips nicely. His legs looked sleek in the black hose beneath the hem which hovered about mid-calf. He stepped forward with his right leg and the split opened exposing his leg to mid-thigh. Then he saddened a bit as he realized what was missing. He needed shoes. The outfit just wasn't complete without them. He sighed. Then he took a breath and held his head up. He wouldn't let this one setback ruin his day. He went about the rest of his day sometimes pretending he was at some formal event wandering about among the crowd, being admired by men and women alike for the sophisticated look he had achieved. He stopped on occasion to rise up on his toes trying to imagine how he would look with the right shoes on his feet. The end of the day seemed to come too soon for him once again. He reminded himself that he was fortunate that he had rediscovered this wonderful side of himself, and that his wife was at least tolerant enough that he could continue it at least for these few hours. He strutted off to the bathroom to clean up. He stored the wig on a head stand back on a shelf in the corner by his clothes, his breasts he made room in one of his drawers. After he dressed he went to the den and pulled out his computer. He searched women's shoes until his wife returned home. * - * - * Jack came into the house after getting off work. He threw his jacket over a chair just as Debbie came into the room. "Hi, honey," she smiled. "How was your day?" "Pretty good, I guess," he turned to face her. "Nothing exciting. How did yours go?" "Really good I think," she grinned. "I have a surprise for you. Come on to the bedroom, I want to show you something." Jack frowned worried about what he was about to find. They hadn't talked about his Saturdays since the day he'd been discovered but he hadn't been making any effort to hide it either. He followed her through the bedroom, bath and into the closet. Debbie stepped through the door and then back out of the way facing Jack's corner. With a big smile she held out her arms like one of the models on a game show displaying the prize. "What do you think?" she begged for approval. Jack looked and saw that some space had been cleared of her clothes. Beyond that there were more drawers built into the corner and cubbyholes for shoes. He looked back at Debbie slightly confused. "I brought the carpenter in that helped with the closet and told him I needed some extra space," she explained. "I felt it was time to get rid of some of my older clothes and boxed them up to be donated. I've seen some of the things you've been buying and I decided you ought to have more room for them. "As a matter of fact," she blushed slightly, "I think you really need to buy more of your own things. Lately I've gone to wear something and they need to be cleaned or at least ironed, or they have been stretched a bit out of shape, or you've gotten some make-up on them. You are just slightly larger than I am so nothing is too bad. But I think it better if you have your own stuff, and that means its own space. Unless you are deciding you are done with it, in which case I can make use of this space, believe me." "I think you can tell," Jack went to her, "from the things I've bought that I'm not done with it." He kissed her. "Thank you, very much. I can't believe you've done this for me." "Well," Debbie wrapped her arms around him keeping him from moving away, "I have something else I'd like to ask you." "Sure, anything," he stared into her eyes looking for a hint. "I'd like to have a nice dinner, just the two of us, here at home after I get home from the library next Saturday. And I don't want you to change before I get home. I want to see how things go this time with both of us prepared. Will a week and a half be long enough to get something of your own together? I'd like to see what you come up with that isn't mine this time." Jack swallowed. He was thrilled and scared at the same time. "Yes, I can do that. I probably need to do some shopping tonight to be sure." "I understand," Debbie smiled at the shakiness she heard in his voice. "That is why I decided to wait to do the grocery shopping I had planned for today until after dinner. That ought to give you about an hour and a half alone. Can you work with that?" Jack smiled, nodded, and kissed her again. *- * - * After his shower, Jack put on his lingerie. "My lingerie," he grinned as he sat down to do his make-up. He had tried on all the things that came in the mail to be sure they would fit properly. "I can't believe I am going to be eating dinner with my wife like this," he had to stop for a moment because his hand started shaking. His plan was to dress casually, a skirt and blouse, for most of the day. But when he usually would be cleaning up in preparation for Debbie's arrival, he would instead change into the dress he bought for their date. He went to the kitchen and put on a roast with sliced up vegetables in a crock pot. Once it was set to go there wasn't much left for him to do so he went to the den. All day long he had trouble sitting still. While most Saturdays he felt the clock spun its hands far too fast, today they seemed to be dragging around the clock. After an interminable amount of time he finally decided he could change. Back to the bathroom he went. He stripped off the blouse and skirt and hung them back up in his corner of the closet. He fingered the dress he was going to wear for dinner, but first he returned to the bath to put on his make-up. He had done a light daytime job but he decided to do a more dramatic touch for the date. He watched his image reflected in the mirror as he approached the table. He liked the look of the bra and panty he bought. Both were light beige, almost the same tone as his own skin, which would work well with his dress. The panty was a bikini cut with strings at the hip. It was a style he decided he liked a lot. He'd also bought some with lace and a bit more material, but this was his favorite. His hands finally calmed down so he returned to applying his make-up. He wanted it to be perfect this time since he wouldn't be the only one to see it. He sat back and studied his face. He nodded his satisfaction. His hair would need a little brushing out but that would wait until after he got his dress on. Jack returned to the closet and removed the dress from its hanger. After undoing the small button that closed the collar he pulled it carefully over his head. A short dark green sheath covered him. The hem fell just about mid- thigh, the top scooped low allowing a generous view of the cleavage his breasts provided. He adjusted the thin straps so that they aligned with his bra straps making them even more camouflaged. Then he adjusted the dark green lace dress over the top letting it fall to his knees. He reached back behind his neck fishing through his long hair, to find the button and loop that would close the collar. A pair of black sling-back heels, a simple gold chain around his neck, a couple simple clip-on earrings and a gold bracelet completed the look. He stood at the mirror and fussed at himself for several moments before he decided he was really ready. With a deep breath he left to return to the kitchen. He grabbed an apron to be sure he didn't get anything on his dress. Then he removed the roast and let it set. Then he pulled out a bottle of wine and opened it. He set the table, placed the wine bottle on a coaster in the middle after pouring two glasses. Then prepared the roast and vegetables in a covered dish and set that on the table as well. He looked things over and took a sip of his wine. Satisfied that everything was in order he looked at the clock. Debbie should be home any moment. As he put his glass down he noticed he had left a bit of lipstick on the rim. He used his thumb to erase it. The apron was removed and hung back in the pantry. Before he could decide what else might need to be done, he heard the clicking of Debbie's heels coming toward the kitchen. Jack quickly returned to the table and lit the candles he had placed there. When he turned around Debbie was standing in the doorway. She looked lovely. She was wearing a red sleeveless dress that fit her body well. It was short, just a couple inches above the knee, and had a simple thin black belt around her waist. She had obviously taken time to fix her hair and adjust her make-up for the date tonight as it wouldn't have been suitable for working at the library. He thought it was funny that he noticed that, he wouldn't have before. "Wow," Debbie whispered. "You've set up quite a spread. It looks very nice." After a moment's hesitation she added, "And so do you. That is a very nice dress." "Thank you," Jack answered fidgeting at the dress smoothing it and checking himself over. "You look terrific, too. And I'm not just saying that." "Thank you," Debbie moved toward the table. Jack could see she was eying him over as she approached. He remained still letting her take in all in. His heart was pounding in his chest and he was beginning to feel very warm under the make-up. He waited, though, letting Debbie take it all at her own pace. She stopped a couple feet away; he could see she was studying his chest, looking at the cleavage visible beneath the lace. "Would you like to have a seat?" he finally had to ask. "Dinner came out just a few minutes ago and should still be warm." "Oh, yes, of course," Debbie answered, clearly flustered at having been caught staring at Jack's breasts. They both sat, Debbie immediately took a large sip of her wine and recomposed herself. They filled their plates and started eating without any more conversation. Jack wasn't sure how to proceed. This was his first meal with his wife dressed in his own things. He wanted to get her reaction but was afraid to press the issue. "I have to say you have come quite a long way since I walked in on you that day," Debbie finally broke the silence as she refilled her wine glass. "Your make-up tonight is impeccable; I think the wig is amazing I wouldn't know it wasn't your own hair. Your dress is great, tasteful and sexy at the same time." "Thank you," Jack set down his fork. "I tried real hard to get everything right for you tonight." "Well, you succeeded," she flicked her eyes down for a moment. "I'm still not certain about your breasts, though. They look real and, well, uh. Damn, Jack, you're my husband and I am very confused at the moment. I thought I might come in tonight and find you looking like a guy in drag, obvious overdone make-up, obvious wig, some dress that was totally inappropriate. Now I feel like I'm at a dinner with a girlfriend of mine. But don't get too over-confident with that. You have some masculine features that I can still see the man in you. I think you could probably walk down the street without anyone really being sure, but if you stand around people for a few minutes they will begin to wonder." Jack dropped his head down disappointed. "Now I am confused. You don't like this, but you do like this. I look really good but not good enough?" he asked calmly. "Please understand, this is really confusing for me!" she pleaded. "I never thought I would come home to find my husband wearing my clothes, let alone my make-up. But you have been so happy. I thought I could ignore what you were doing while I was at work. But the more time passed, the more I found myself thinking about what you were doing here at the house while I was away. Again, you were so happy all the time. You seemed less stressed. So, I decided I needed to see if I could be a part of it, to maybe allow myself to be with you for dinner or something. Now, I see just how good you can look and I am dealing with feelings I never imagined. I want to touch your breasts to see how they feel; I want to look under your dress to see what type of lingerie you've chosen to wear. I haven't ever thought that way when looking at a woman. I've never been interested in being with a woman and I know you aren't a woman but you do look like a woman, this doesn't make sense. And I am babbling." "It's ok," Jack soothed. "I understand how much these things don't make sense. When I first discovered I wanted to wear things that are women's I was concerned that maybe I was gay. But like I told you before the idea of being with a man has no appeal to me. I am still wildly attracted to women, specifically you. Once you gave me permission to do things while you were at work, it freed me to experiment more. I was able to perfect things and buy things that helped. I think it isn't so much that I want to be a woman as that most things don't look right with a male shape. So I've taken steps to improve my shape, temporary steps. I love how I feel when I do this. I understand if you don't want to do this again. I appreciate that you've come this far with me. I feel the best I have in all my life." They sat there for a few moments more each letting the other soak in the information they traded. "Let me help you clean up," Debbie finally offered. "And open another bottle of wine." Jack nodded understanding she still needed more time to process. They got up from the table and went about the kitchen putting leftovers away, cleaning off plates and storing them in the dishwasher. At one point Debbie leaned past Jack and he felt her hand press against his left cheek just below his hip. It lasted only a moment but he smiled. They moved to the den, Jack put some soft music on the sound system and they sat on the couch together. They talked more while they drank the wine. This time it consisted of their work lives, what needed to be done around the house, other things that didn't deal with how Jack looked at the moment. After a few moments of silence Debbie spoke again quietly, "Can I touch your breast?" Jack's eyes widened momentarily, but he recovered and turned toward her. "Of course." Debbie tentatively reached out and laid her hand against his breast. She slipped her fingers outside, her thumb opposite. Jack could feel the pressure from her testing; he began getting a little turned on by it. "They're firm, but pliable," Debbie remarked. "They have some weight to them. How are they done? Does it have a nipple? I can't feel it through the lace and bra and all." "It's a prosthetic that I attach with an adhesive so they are supposed to feel and look real," Jack explained and reached for Debbie's breast. "Not ever actually having my own I can hardly say if they do or not, but they feel a bit like the real thing to me. And they look pretty good." He began to rub her breast. Debbie looked Jack in the eye but continued to massage the breast in her hand. Her eyes took on a bit of a dreamy look as Jack continued to rub his thumb over the nub he found becoming stiffer under his touch. He felt Debbie's other hand land on his thigh atop the lace but below the hem of the liner beneath the dress. She leaned in and kissed him. "Let's go to bed," Debbie whispered. "Absolutely," Jack grinned. "It takes me a while to clean up though, but I guess you need to get your make-up off too." "No," Debbie stood, "I don't want to wait. I want us to undress each other and make love. Make-up can wait til morning if we don't get it off tonight." Jack took her hand and she led him to the bedroom. True to her desire they spent no small amount of time exploring each other as they removed the other's clothes. Eventually they dropped onto the bed and made love. * - * - * Jack woke up the next morning and saw his wig lying on the nightstand. He looked over his shoulder and saw Debbie still there, naked, a sheet covering only a part of her. He smiled as he remembered the evening. It hadn't gone exactly as he had thought it would, but it ended better than he could possibly have dreamed. He crept from the bed, picked up his wig and went to the bathroom. He saw a real mess when he looked at his reflection. He turned on the shower before he brushed out the wig and placed it back on the stand. He returned to the shower and proceeded to wash off as best as possible. Upon leaving the shower he went to the mirror and finished removing any stray make-up still clinging to his face. Dressed in denim shorts and a t-shirt he walked back into the bedroom. Debbie was awake and had pulled the sheet around her. "Good morning," Jack went to the bed and kissed her. "How are you feeling?" "I feel wonderful," she grinned and stretched. "You were wonderful last night." "I can't be wonderful without an exceptional partner," he answered as he began picking up the spent lingerie from the floor. "I was happily surprised by how the evening went. It was better than I could hope for. You surprised me." "I surprised myself," Debbie answered. "Those will probably both need to go to the dry cleaners," she informed Jack as he picked up their dresses. "OK, be right back." Jack disappeared into the bathroom to dump the used clothes and returned a moment later. "Even through dinner I didn't think the evening would go the way it did," Debbie began explaining as Jack entered. "Then, I don't know, maybe the wine loosened me up some, but my curiosity of how you achieved the transformation started pushing me to know more. And then as I learned more I found I wanted you more." "I'm glad you did," Jack sat on the side of the bed and took her hand. "If you want to go back to the original deal, I'm ok with that. I know I can't stop. Even if I promised I would, in some time I would be back to doing it again. And you would know because of all the changes in your clothes that you saw this time that moved you to change the closet again. I'd rather not lie about it. I'll just tell you I am going to be doing it." "Dear Jack, I don't want you to stop," she placed her other hand atop his. "As a matter of fact, if you would be up for it, I would like to have these Saturday evening dates more often. While you were showering I was thinking a lot about last night. Knowing it was you, despite what my eyes were telling me, made it ok for me. And once I convinced myself of that, I had an amazing time. I know you did a lot of work putting that dinner together, but if you would be up for doing it again, I would like it." Jack leaned and kissed her again. "Baby, I haven't brushed my teeth yet," Debbie laughed. "I don't care," Jack grinned. "I love you so much more than you can imagine right now. I would be happy to cook for our dinner dates. What's the big deal, all I have to do is cook once every other week?" "Actually," Debbie took on a mischievous look, "they asked me if I could work every Saturday for the next couple months. A couple people are taking vacation and one is quitting. I told them I'd let them know when I came in next week. So, if you are up for it, you could be cooking every Saturday." Jack sat there for a moment trying to absorb what he had heard. "You want to have a date night like last night every Saturday for at least the next few months? Where I get to dress up?" "Yes," she smiled. "And the extra money I will be making will help to pay for the new clothes we are both going to need." "Both?" "You don't expect me to keep wearing the same dresses of mine that you were wearing while you get new things do you? I am getting some fine new dresses out of this as well." "That sound reasonable to me," Jack laughed. "Then we are agreed," Debbie smiled. "One thing," Jack prompted. "What?" "I think we should plan on one of these evenings being a really formal affair, long dresses like a high dollar charity event," Jack explained. "I can't exactly go to the library dressed like that now, can I?" "I can plan to start dinner late so you can come home and change." Debbie waited a moment. "Well, I guess we have a deal. Now, let me get to the shower. I need to get cleaned up, I probably look a mess." "You look wonderful to me," Jack stepped out of the way. "One more thing," Debbie added standing naked in the bathroom door, looking back over her shoulder. "Have you ever thought about wearing a nightgown to bed?" "Uh," was all Jack could manage. "You ought to," Debbie giggled. "I think you would like to have something slinky to slip into after our date nights." * - * - * Three months of date nights later Debbie was off for the first time on a Saturday. She and Jack sat side by side at the mirror in the bath applying their make-up. They talked about what they were going to do with the day. The would spend it at the house doing things, but they both liked dressing up for the day as though they were going to be out and about. This day Debbie chose a short white lace skirt with a light blue silk blouse. Jackie, a name that just seemed to appear over one Saturday night, chose a black leather miniskirt with a red silk blouse. Both left the blouse unbuttoned enough to tease the other. Jackie appeared most every Saturday morning now and stayed until Sunday morning, unless there was something that required they go out, then they just moved it to Sunday. He thought it funny that Debbie now occasionally borrowed his clothes. Some of his skirts and dresses fit her very nicely despite his being a bit larger. Since he had gotten his breasts to fit her bras, everything was pretty close, except shoes. Debbie admitted that it excited her to wear his dresses sometimes. She told him she tried wearing one of his bras and panties once but they felt just a little loose and she was afraid the panties would fall to her ankles. So, she kept to his outer wear. Life was good for Jack and Debbie. Six days a week Jack went about the normal business that his friends and neighbors new of him. And one day each weekend Debbie and Jackie would do things around the house and have a girls day in.