The Rest Of William's Day To Remember free porn video

The Rest of William's Day to Remember Author's Note: Sequels seem to not go over as well. I intended to leave the story up to the reader's imagination, but this wouldn't stop running through my mind. I hope someone enjoys it. I thought it was going to be a short story when it started but there was apparently a lot to tell, but this is the end. William glanced back at the clock and saw it was just about time to meet the ladies to head out for lunch. He was looking forward to it but also was starting to feel a bit worried. He knew how terrific the women were from his brief time as Doreen, but would they act the same with him? Only one way to find out. He locked his terminal, got up and headed for the building lobby. He got there and nobody was waiting. He had just enough time to wonder if they had gone on without him having changed their minds when they entered the lobby together. "William!" Brianna called. "So great of you to join us!" "I appreciate the invitation," William grinned. "I can't believe you, uh, girls? Ladies? Women? Oh, what do I call you without sounding condescending?" They all laughed. "Girls, ladies, either works," Evelyn told him. "OK, ladies," William snickered. He held the door as they filed out. "Seems like sometimes you hear people in a group call each other something, but if someone outside the group tries to use the same term people get offended. We live in turbulent times." "That is the truth," Jenny answered. They walked to a restaurant that was nearby, not the one he had lunch with Michael in. They got a table and ordered quickly. The place was busy, but tables were turning over as many were finishing their early lunch and rushing back to their respective offices. "So, William, why the sudden awakening?" Evelyn asked. "I don't mean to pry but of all the people in the office that was to suddenly stand up for equality I didn't expect it to be you. Not that I think you don't care, or anything. It's just you do your work and seem to fade into the background." He looked around and saw all three women waiting on what he had to say. Could he tell them about his stint as Doreen? No, how could they believe it when he was still unsure of what that was. "Well, I, um, don't know really." He tried to find something plausible to tell them. "I was sitting there at my desk and wanted coffee and at first I thought I would wait, and then decided I should just go. Maybe someone would have made it but if not, it wasn't that tough a task. Then in the meeting I thought about what you said about making coffee and realized there was more than just coffee going on, so I decided to support Evelyn's idea." The women looked at him for a moment or two weighing his words. "Bullshit," Brianna stated and took another forkful of salad. "Not entirely," Jenny added, "but there is something more you are not telling us." William felt a sheen of sweat form on his body, a touch of panic setting in. These women were more intuitive than he was ready for. And lying was not his strong suit, even half-truths were a struggle for him to pull off. "OK," William admitted, "maybe there is more to it, but you won't believe me so can we just leave it that I had a sudden clarity of vision?" "So, there is more to the story," Evelyn grinned. "What will it take to get the whole enchilada? Don't you trust us?" "Oh, I trust you plenty," William blurted. "I just think you'll think I'm crazy and I know how wonderful you three are and I don't want this new friendship to end as quick as it started. I mean, if this is a new friendship." "William," Jenny put down her fork, "we haven't spent hardly any time together. The conversation in the breakroom this morning was probably the longest casual conversation we've had. You always come in, do your work and leave keeping to yourself the whole time. Evelyn was more shocked that you spoke up in the meeting than the fact that you did it to support her idea. I think, well, we think that if something has changed you this much, and it is a change we all really like, that we'd be interested in knowing what drove it. If you don't want to tell us, fine. Just tell us it isn't any of our business and we'll drop it. But don't try and make it some big mysterious thing." William looked at each of them and at his watch. Lunch was almost over, and they would need to be heading back to the office. Not enough time to tell the story in any case. "OK," he told them, "I'll tell you the whole story but not now. There isn't enough time. Perhaps next week we can do lunch again and I'll tell you. Maybe we can find somewhere a bit less crowded." The girls all looked at each other, no words were exchanged. After a moment Evelyn nodded, Brianna shrugged and then nodded. Jenny turned back to William. "Tonight, after work, we are going to stop for drinks," she told him. "Perhaps you would like to join us? There will be plenty of time for your story and perhaps the drinks will help loosen you up to tell it." "The bar on Elm by the drug store?" William asked. "Yeah, how did you know?" Jenny sat back. "It's part of the story," William answered knowing he had committed himself to telling the tale. They each pulled out some money and paid the bill along with a generous tip. They paraded out of the restaurant and back to the office. "I don't suppose you can tell us a little of the story," Evelyn pressed. "No," William shrugged, "I'm afraid it seems like it needs to be told all at once." They went into the building and back to their cubicles to finish off the workweek. Later that afternoon Jenny poked her head into William's cubicle. "We are heading down to the bar. You will be coming by, right? We are all very curious about this story." "Yes," William turned from his terminal to face her. "As soon as I finish this one up, I'll head out. Take me about another ten or fifteen minutes." "OK, we'll see you there." She disappeared. William finished off the work, logged off his terminal and proceeded to head for the bar. This time he knew he was going to stop and marched straight to the door. He was still far from confident in sharing his tale but felt he had committed himself to the path. He walked in the door and though temporarily blinded by the change in lighting turned immediately toward the table he knew the ladies would be gathered around. "William! Just in time," Jenny called. "What's your poison? First drink is on me." "Fine, but next round is on me," William answered. "I think I'll have a bourbon and water." He remembered the marguerita wasn't all that special. "That's a deal," Jenny headed for the bar. "How did you know we were coming here?" Brianna asked. "We do different places each Friday." "I'll explain once Jenny gets back," William noted the extra undone buttons on Brianna's blouse. "Here you go," Jenny set the drink in front of him. "Now, how about the story?" "Mind if I give it a few more minutes? Perhaps I could start when I get the next round," William begged. "I need a little liquid courage." "I don't like being teased," Evelyn told him. "This story had better be worth it." "Fine, next drink," Jenny acquiesced. They stood and drank and chatted about things at the office. The girls were surprised at the knowledge William had of things going on in the office. They didn't believe he was aware of many things outside his cubicle. "I am ready for another drink," Brianne put down her empty glass. "Same here," Evelyn swirled the ice in her glass. "Seems like the time has come," Jenny grinned at William. "Indeed, it has," William nodded. "Everyone wants the same I assume?" The girls all nodded. "What about a shot? Anyone want one? I think I need one to get over the hump. Peppermint Schnapps for me. Anyone else?" "Same," Jenny answered. Evelyn nodded. "Tequila gold," Brianna grinned. William got the shots, delivered them to the table and went back to the bar for the rest of the drinks. "To William's tale," Jenny lifted her shot glass. They all clinked the shots together and tossed them back. "OK, William," Brianna leaned on the table toward him. "Time to spill." William looked at her and then, unable to control himself, he looked down the front of her blouse. He could see her breasts resting in the cups of her bra. He forced himself to look away. "OK, so I was on my way to work this morning on the train and there was a girl," he began after looking to be sure he would not be overheard, "well, not a girl, a woman, a young woman. I don't want you to think she was too young, like a teenager or something." He was becoming flustered. "I think we got it," Evelyn assured him. "Probably a twenty-something? Close to our age?" "Yeah, that sounds good," William exhaled and wiped at his forehead. "Anyway, she was sitting across from me reading a book. She had on a white blouse and black skirt." "And she caught you trying to look up her skirt, right?" Brianna asked. "Well, yeah," William could feel his face redden. "I mean I couldn't see anything; her skirt wasn't that short, and she had her knees together, but I couldn't help but try and take a peek." "What is it with guys doing that?" Evelyn asked. "Who wants to look at someone's underwear?" "Really?" Brianna answered. "You should see some of the underwear I wear. There have been some guys who have really appreciated it." They all stared at Brianna for a moment. "William, go on," Jenny turned back to him. "Well, then something happened," William took another big swallow of his drink, "and this is the part where it gets weird." The girls were all leaning in closer. "The lights flickered for a station, and I was a woman named Doreen," he blurted. The girls looked at each other for a second as if to confirm they all heard the same thing. "Come again?" Brianna asked. "I found myself sitting in the same place but instead of being dressed like this I had on a yellow blouse, brown skirt and heels. I came to work, found a badge with Doreen's name and picture, my picture as a woman. I knew everything I was supposed to do, remembered getting dressed in the morning, including shaving my legs and picking out some fancy lingerie because I had a lunch date." "And we were all friends in this alternate life?" Jenny pressed. "No, I was as much a loner as Doreen as I have been as William," he told them. Then he went on to tell them the story of the rest of the day concluding with running into the same woman in the subway station after the bar and returning to his current state. "Well, that was quite a story," Jenny answered. "We need another round," Brianna opined. "And I want to get off my feet. That table over there opened up, let's grab it." William, Jenny and Evelyn walked over to the booth while Brianna went to the bar for the next round. Jenny slid in one side and over to the wall; Evelyn took the other side sliding over as well. William chose to sit beside Jenny leaving a space for Brianna beside Evelyn. William picked up his drink and worked it waiting for the reaction from the ladies. "So, why the big mystery?" Brianna asked. "You didn't think we'd believe you were suddenly a woman for the day?" Jenny and Evelyn both laughed. "That is a rather hard story to swallow," Evelyn added. "I mean, aside from knowing that we were coming to this bar tonight, which I haven't forgotten about, what else could you say to prove it?" William thought about the conversation they had when he was Doreen, then looked around the bar. He spotted a guy laughing a little too loud. "See that guy? He's the one that you threatened to knee. I don't know if he will still try and join us since it isn't four women instead of a guy with three. Plus, we never sat down before. Frankly, my feet were aching in those heels, I was surprised we didn't find a seat earlier. You three must have been just as sore." "Actually, my feet are just a dull throb until I get off them," Brianna explained. "Then, once I take the shoes off, that is when it becomes a combination of pain and relief. At least for a little while." They talked more trying to decide what it would take for William to provide more proof about his adventure when a shadow fell across the table. "Good evening," the lush swayed at the edge of the table. "I thought this guy here," he slapped William on the shoulder, "was burdened with too many riches and thought I would come over and help him out. Mind if I pull up a chair and join in? I'll even buy a round." "Yes, we mind, please go away," Jenny answered quickly before he could pull a chair close. "Oh, come on, I'm a funny guy and there hasn't been enough laughter at this table," he went on. "Get lost," Evelyn sternly addressed him. "If I have to get up to get rid of you, I will not be happy." She glanced at William. "I will knee you so hard you will choke on your balls." The grin disappeared from his face. "Shit, why do you have to be such bitches when a guy wants to have some fun too?" "To put up with assholes like you," Jenny answered. The guy stumbled away. Evelyn just stared at William. "You just mouthed the exact words that ass and Jenny said. You knew exactly what they were going to say." "I thought that was what was going to be said," William answered. "Except we were all standing by that table over there and Jenny had her arm around me after I escaped his grasp." "You really believe it happened," Brianna whispered. "I don't know," William sighed. "It felt so real, the things that seemed to go just the way it would if I were Doreen. The you all were trying to be my friend and then today, well, here we are. I have had such an incredible day. I hope it doesn't end. I wish maybe I could be Doreen because it might be easier for all of you to be a friend to her." "William," Jenny laid a hand on his arm, "you are a nice guy. We didn't know you before because you kept so much to yourself. It is easier for girls to approach other girls, but now that we have gotten to know you, I feel like we will still be friends. I've enjoyed lunch and our happy hour." She glanced around the table. "I think we all will want to include you going forward." The other girls nodded. They enjoyed one more round of drinks and decided to call it a night. "So, this has been really fun," Brianna announced once outside. "I hope we do this more often." She hugged Jenny and William. "I second that," Evelyn answered and hugged Jenny and William as well. They turned and walked away. "Are they, um, together?" William asked. "Oh, no," Jenny laughed. "They live near each other and ride into town together. They park in a city garage about a block over." "Oh, I feel stupid," William looked down at the sidewalk. "You could have been right," Jenny told him. "At least you didn't try and prove how accepting you are of a situation that didn't exist and say something really stupid." "I guess," he nodded. "So, do you ride the train? Take a cab? How do you get home?" "Actually, I walk," she told him. "I have a condo a few blocks from here. Saves time. And I don't even own a car since the subway gets me most places I need to go. If I need a longer trip, I rent a car for the day, or however long." "That sounds really convenient," William agreed. "Well, I guess I ought to go catch my train. I'll see you Monday?" "Actually," Jenny began, "would you be interested in another drink?" William looked back at the door of the bar, "Well, if you really want to, I suppose I could have another." "Not here," Jenny looked around, "I mean at my place." "Oh," William was startled. "First, let me be clear," Jenny told him. "No sex! I am not inviting you in for that." "Oh, right, of course not," William nodded furiously. "Look, I am making a mess of this," Jenny took William's hand. "I would like you to come back for a drink. I do like you. It's odd but the longer the day went on from our first conversation about the coffee making until now I have felt like I really like you more each minute. I'd like to talk to you a little longer if you'd like." "I'd like that," William answered. "And I have no problem with no sex." They walked together to her building. William looked up at the high- rise building. They walked in past a security guard in the lobby and took the elevators up to the seventh floor. Jenny led him to the door with 709 on it, unlocked it and walked in. William followed her in. "Do you mind if I get comfortable?" she asked as she pulled the shoes off her feet. "No, not at all," William answered still taking in the room around him. "It is your place after all." "Thanks, I'll be right back," she padded off barefooted carrying her shoes. William looked around while he waited. The main area was a combination kitchen/dining/living room with a small balcony off the living area. He stared out through the large windows that made up the wall between the balcony and living room at the panoramic view of the city outside. "Oh, I feel so much better," Jenny called as she came back into the room. "Bourbon and water still good for you?" "Yes, that's fine," William answered without turning around. "This is quite a view! I don't mean to pry but I think they must be paying you a lot more than they are paying me." "Inheritance," she answered drawing closer. "Was able to buy this and the monthly fees aren't any worse than what I would pay for rent somewhere else. Plus, I told you how much I save in other ways living so close. Here's your drink." William turned to accept the drink and froze. Jenny was standing there, his drink in one hand, hers in the other. She had changed into a pink silky nightgown that just reached the top of her thighs. The V neck didn't go so low as to show any cleavage, but her nipples dimpled the fabric. William forced his eyes away and accepted his drink. "No sex," he reminded himself. Out loud he said, "Thank you." Jenny turned and sat on a plush chair, carefully crossing her legs as she did, giving William no view to what lie beneath the nightgown. William moved to her couch and sat. He crossed his legs trying to hide the problem that had arisen in his pants. "OK," Jenny began, "what I am most curious about is the time you spent as Doreen. Listening to your story I was most intrigued by the fact that you didn't seem too freaked out that you were suddenly a woman. And, to tell the truth, it seemed to me that at the end of the day you weren't in a huge hurry to get back to being a man again. I think you told us about how the day went, but I want to know how you felt about things." William took a big sip of his drink and looked to put it down on the coffee table but there wasn't a coaster, and he was certain he shouldn't just set it down. "Oh, shoot," Jenny looked around. "Oh, here." She leaned over the arm of the chair and William saw the narrow strip of white lace on her cheek with sheer white between giving him a good view of her butt. She had a nice one. She leaned back and placed two coasters on the coffee table. He put his glass down. "Um, well I think at the beginning I was in shock and couldn't freak out. Next thing I am walking along to work feeling my panties crawl up my butt." The image of the white panties he just glimpsed tightly hugging her butt flashed in his mind. "I wondered why I was wearing underwear that would do that when another part of my mind told me why. As the day went on, I got more and more comfortable with being Doreen. A lot of it was you trying to draw me out of my shell." "What about sitting around the office in a skirt all day?" she pressed. "You indicated it was short, not too short, but above the knee. I mean you are used to wearing pants all the time. How did you like wearing the skirt." William shifted around a bit. He didn't want to admit his feelings on the matter, especially after just starting a friendship with this woman. Why was she being so eager about this. He took another long sip. "I bet you are wondering if you should say anything," Jenny interrupted the silence. "I think if you didn't like it, you would have jumped right in and said so. I think you really enjoyed being dressed up in sexy lingerie, skirt and blouse." William felt his face heat up and knew he would not be able to deny it. Would she also figure out that he was thinking of buying something to try at home? Jenny stood up tugging at her nightgown at the same time apparently unaware that she had flashed her butt at him moments ago. "Would you like to get comfortable, too? I have another nightgown like this I would be happy to lend you. Even a pair of panties I think you'd like." William was frozen in place. Now he was totally in shock. He wanted to say something, but his mouth wouldn't work. Jenny turned and left. A few moments later she returned and had a red nightgown of the same style she wore. "Here," she handed it to William. "And," she held up a pair of red lacy, sheer panties. Then handed them over to William as well. She sat back down in her seat and waited patiently. William fingered the items and wanted to give them back to her and tell her she was mistaken. He had enjoyed his day as Doreen, but he was William again. But, while that was what his brain was telling him his heart was begging him to put on the panties and nightgown. He looked back at Jenny but held on to the clothes. "There is a bathroom just down that hall," she smiled. "You can change in there." William stood up and went down the hall, he closed the door and removed all his clothes. He slipped the panties up his legs; they had a high waist and were cut high to the hip. The front was all lacy and hid almost nothing. He turned and looked at his butt in the mirror and saw the same panty in red that he had seen on Jenny. He slipped the nightgown over his head, and it reached just to the top of his thigh. Like Jenny, he knew he had no room for error. One thing that bothered him was his legs had too much hair. He considered this would be a good excuse for not wearing the nightgown, but he let his fingers trail along the nightgown and touched the panty. He liked the feeling too much to let it go. He remembered the smooth legs Doreen had as well. The drinks he had up to this point also helped cement his resolve. He gathered up his other clothes and folded them neatly and set them on the counter. He went to go back and join Jenny but before he entered the living room he leaned around the door. "Jenny?" he called. "Yes," she smiled as she saw the red nightgown covering what little she could see of him. "Come on in! Show me!" "Well," William hesitated. "My legs, they are too hairy. I was wondering if maybe you had a razor that I could use first. I think they look too horrible." "Really? You want to shave your legs?" she smiled even more. "In the bottom drawer of the vanity. Shaving cream and new razors. Take your time and don't cut yourself. Would you like me to bring you your drink?" "No, I think I'd better wait before drinking anything more," he turned and started back to the bathroom. "I'll try and hurry." "We have all night," she called back. William went back into the bathroom, found the razor and cream, then inspected the tub. She had a shower head that could be detached from the holder and be used by hand. He peeled off the nightgown to keep it from getting wet, sat on the edge of the tub in the panties and spread the cream across both legs up close to the panties. He then took the razor and began scraping the hair from his body. He sprayed off and felt how smooth his legs now were. He pulled the panty out and thought about shaving off the pubic hair but in the end opted to leave it alone. He did decide to take them off and shave his chest while he was at it reasoning that if his legs felt that good, then imagine how good his body would feel in that nightgown without the hair. He dried off and got dressed again. He walked back confidently into the living room, turned and carefully sat on the couch, holding his nightgown to prevent it riding up. He picked up his drink and sipped at it waiting to see what Jenny would say. Instead, she reached over and glided her fingers up his leg. She looked up at him, "I thought so. Do you like the nightgown and panties?" "Yes, very much," he admitted. "I was afraid to tell you that after I was back to being William that I was thinking about maybe getting a skirt to try for myself." "There was something that told me you wanted to express that part of you again," she leaned back and sipped at her drink. "I think that woman, whoever she was, whatever she was, saw the Doreen in you and let you live a day as someone you've kept repressed for a long time." "Then you believe me?" A tear leaked from the corner of William's eye. He wasn't sure if it was being believed or understood that had him feeling so emotional. He had been denying this desire for a long time. But what now? Will Jenny be a friend? Or will this turn into something else that will make his life miserable. "Yes, I do believe you. Oh, it is getting late, and I am getting tired," Jenny stood up. "Would you like to spend the night? We can sleep together but still.." "No sex," William finished. "Right," Jenny nodded. "Just Jenny and Doreen spending a night together and maybe trying on some dresses in the morning. I have a couple dresses that I think you might really like." William nodded. Jenny took his hand and led him to the bedroom. They crawled into bed together, Jenny wished him good night and turned to go to sleep. William was still too hyper to sleep. The feeling of the lace panties, silky nightgown, the woman sleeping beside him in the same style pink nightgown and white panties. He heard Jenny's breath deepen as she slid off to sleep. It took him a lot longer but eventually darkness took him. He woke the next morning, the room light muted by the shade and curtains on the window. Jenny was lying with her head on his shoulder, her arm across his chest and a leg laying across his leg. He became aware that his nightgown had ridden up and her leg was actually brushing against his panty. He spent a couple minutes trying to wake up completely, reviewing the events of the past day (or was it two days), and trying to decide if he should try and disentangle himself from Jenny when she stirred. She squeezed him with the arm on his chest and raised her leg a bit sliding her thigh along the front of his panty. "Oh, good morning," she mumbled. "I'd say you are still liking the feel of the panties." She slowly let her leg slide back down the panty but left it on his leg. "I'm sorry," she said after a couple seconds and pulled back away from him. "That is a terrible tease. I didn't mean to do that. I just liked feeling you in that nightgown and the panty felt really sexy. I'm still not ready for us to have sex but if you want to go in the bathroom and relieve yourself that's fine. If you come to the kitchen for breakfast still in your nightgown, I'll know I haven't offended you too badly." She turned to leave the bed and as she pulled the covers back William caught a glimpse of the front of her panties as she started to roll over. The dark shadow of pubic hair that lay beneath the panty plainly seen. He got up and pulled his nightgown down and went into the bathroom. He headed for the kitchen a short time later, the edge of his nightgown slipping again his smooth thighs. Jenny fried some eggs and sausage and poured them orange juice. "So," she sat down and began eating, "are you still up for trying on some dresses today?" "I guess so," William answered and took another bite of sausage. "Can you tell me, why are you doing this?" Jenny took another bite and thought about it for a minute. "Honestly, I'm not sure. It just felt like something I wanted to do when we left the bar and felt like it was something you wanted to do. I liked waking up with you like that. And if you wanted to try on a dress or two then I think I would like to help you do that too. Believe it or not, I feel like we are going to have a fantastic friendship." "OK," William agreed. "That sounds great. I'd like a friend, a true friend that I can really trust. You are discovering things about me at the same time I am discovering them. I mean that. I haven't done anything like this," he slid his hand down the front of his nightgown, "before. Nor, I think, anything like what we may do after breakfast." "Well, let's not waste time," Jenny stood up. "Help me clean up and we'll start exploring." The two of them went about cleaning up the kitchen washing and drying and putting away the dishes. Jenny was a very neat and orderly person. She did not like leaving things undone. They went back to her bedroom and Jenny went to the closet. "Hmm," she muttered as she stood looking over her clothes. "I think maybe this one, and this, and yup this one too. Oh, and I want to see what this looks like on you, but I am keeping it. I just think it will look good on you and you will like it." She emerged from the closet carrying a dress. She laid it on the bed. "What do you think? Do you want a bra? We can stuff the cups with something for now. Or do you just want to go without one and a flat chest?" "Oh, are you sure you want to be lending me more of your underwear and all?" William was feeling a little anxious. Both afraid of doing this and wanting to do it. "Sure, it is just clothes," she walked back into the closet. When she came out, she was carrying another dress, but she had taken off the nightgown. Naked except for the lacy panties she laid the dress on the bed and went to the dresser. She pulled a bra out of a drawer and proceeded to put it on. "Want one? Help yourself." She went back to the bed and picked up the dress she had just taken from the closet and pulled it on. "Do you mind zipping me up?" She turned her back to William. William still shocked at how easily she was walking around naked only a moment before reached over and ran the zipper up the back of the dress. It was a simple blue sleeveless dress, just above the knee. It followed her curves nicely. He took a breath and pulled the nightgown off and tossed it on the bed. He looked in the dresser drawer and saw several bras. He decided to take a red one to match the panties he had on. He slipped it up his arms and began to try and reach back but his arms just wouldn't make it. "Let me help you," Jenny came behind and fastened his bra for him. "Let's see," she turned him back around and looked at how the bra sat. She tugged and adjusted the straps. Satisfied she turned back to the dresser, opened another drawer and pulled out a couple balls of brown nylon. "Pantyhose should do fine for now," she put one into the left cup, pulled it out and added a second, molding them together to be not as lumpy. Back in it went and she gave his new breast a good feel. Deciding it worked she duplicated her work on the other breast. "Alright, let's see how the dress fits!" She handed him the first dress; it was gray, sleeveless with a full pleated skirt. She helped him get it on, zipped it up and led him to a mirror in the bathroom. William was enjoying the feeling of the bra, and the dress as it swirled around his legs as they went to the bathroom to get a look. It felt a lot different than the skirt he had worn as Doreen. "You look cute!" Jenny grinned. "I think we could both use some make- up but before we do that, let's decide on a dress for the day." "For the day?" William asked. "Don't worry," Jenny patted his arm. "We aren't going anywhere. I just thought that it would be nice to spend the day together, just Jenny and Doreen. I'm sorry, I didn't think to ask if you already had plans for today." "Um, no, no plans," William answered still looking at himself in the mirror. "That dress is nice, just above the knee, not too short and it is good that you have nice legs," Jenny commented. "I'm glad you decided to shave them. I can't imagine what it might have looked like if you hadn't. Let's try another." They went back to the bedroom and Jenny helped William out of the dress. The next one she pulled from the closet was a minidress, much shorter than the first dress and tight. Not as short as the nightgown but only about hallway down his thigh. "Well, everything looks great except for this suspicious lump here. It looks pretty good on you as well," Jenny rated him. Another dress, this one a bit longer. "OK," Jenny pressed. "Which one do you want to wear today?" "Actually, I liked the first one the best," William answered. "I liked the way it felt on me." "Sounds good," Jenny nodded. "They are all yours if you want them, I am done with them and I think you would get good use out of them. I tend to like my dresses to be form-fitting as I am sure you can tell. But, before we get you set for the day, I want to see you try on this other dress. We are going to change everything, including your underwear for this one." She helped him out of the dress, unfastened his bra, and flicked her finger at him indicating the panties had to go too. She went to a different drawer and pulled a special black bra with a little black stringy thing she handed to William. He looked at it skeptically. There was a long black triangle, silky smooth attached to another smaller black triangle joined by three strings. "Go on, slip it on," Jenny instructed him. "We are going formal for the next dress." William slipped the stringy thing up his legs and got it settled. One string slipped in his butt and the smaller triangle settled just above the crack of his butt. In front there was just enough material to keep him in place. Jenny placed the new bra against him and clasped it around his waist. "This is a special bra for a backless dress," she explained. She fixed his breasts and went to the closet. She returned with a long black sequined dress. "I've worn this a couple times; I think you would look really cute." She got the dress over his head and pulled it down to his waist. She lifted the top and fastened the choker style neck. A triangle of black descended around his breasts to the small of his back, just above the bra strap. She moved and pulled the dress down his legs, a slit to mid-thigh on the front of his left leg. She zipped it up. "What do you think?" William took a couple steps and almost tripped over the dress. He pulled up the front a bit and went and looked in the mirror. He liked the way the light reflected off the sequins, the way it fit him, the feeling of material against his bare bottom. "Wow," he turned back and forth, pushed his leg forward through the slit. "I really like it." "Yes," she placed her hand against his bare back. "Sorry about the length, I mean it is nice that we are about the same height and build but your feet are bigger than mine. I can pad your chest to make up for boobs, but I don't think we can chop off your toes," she giggled. "I usually wear heels with that dress to keep it from dragging." "I would have loved to see you in this dress," William still eyed himself in the mirror. "I bet you were gorgeous." "Thanks," Jenny hugged him, "you are sweet. Make-up goes a long way to making that happen." She hesitated. "Let's go for it! You want to?" "Go for what?" William finally looked away from the mirror. "Unzip me," she told him. "I am going to pull out my other formal dress and we are going to do our makeup and spend the day pretending we are doing some really fancy soiree." "Um, ok, if you want to," William followed her back to the bedroom. He watched as she peeled out of all her clothes. Put on a black g-string panty, even smaller than the one he had on, and disappear into the closet. She came out carrying a short black dress. "This one is short, and while that might work better for you so you don't trip, you really need your own boobs to make it work, you'll see." She started tossing the dress around trying to locate the way to get it on and finally pulled it on. "It has a built in bustier, so I don't need a separate bra, one of the things I like about it. Zip please?" William stepped behind her and ran the zipper a short distance up her back. The dress was strapless and when she turned back to face him, he could see what she meant by needing his own boobs, hers seemed to be ready to fall out. She was fluffing out a multi-layered short skirt. "Like it?" she led them back to the bathroom. Once in front of the mirror she reached into the front of the dress and adjusted her breasts. "No, they won't fall out," she explained as if reading him mind, "I am held in place pretty well. So, let's do make-up!" She led William back to a small vanity in the bedroom, sat him down and went to work doing his make-up. He sat there patiently waiting, following instructions and trying not to stare at her breasts as they jiggled with her movements. He was amazed that he had so much trouble looking away when he had seen her naked already. The power of women's clothing was really starting to make an impression on him. "OK," Jenny grinned, "I think that will work. I wish your hair was longer, and I had some bigger shoes that would fit you, but for what we are doing today, I think we are good. Turn around and tell me what you think." William turned to face the mirror. He was astounded. He could only see from the tops of his shoulders and up, and the hair was totally wrong, but she had transformed his face completely. He pursed his lips, now a deep red. Closed one eye to try and see the effect of the dark colors there. "I wish my hair was longer, you've performed some real magic here." "Thank you," she executed a little curtsy behind him. "Now, why don't you go to the living room and let me do my own face up. I'll join you in a little while." William stood up, picked up his skirt and walked back to the living room reveling in the feeling of the dress on his body. He moved about nervously, tried sitting on the couch and adjusting the dress considering how much leg he wanted displayed with the slit. He was nervous and excited and confused and a myriad of feeling he couldn't identify. He was about to get up and pace around the room again when Jenny came in. She had done a similar make-up job on herself and styled her hair. She was drop-dead gorgeous. "Wow," William whispered. She gave him a smile and did a twirl. "So, you like?" "You look amazing," he stood up and went to her. "You look like the type of girl I would be too nervous to ever approach. Way out of my league." "Well, you look like just the type of girl I want to have for my friend," Jenny reached out and took his hands. "I'm glad you are here, and I'm thrilled to be doing this with you. Now, next thing, we are going to paint each other's fingernails and toenails." William just nodded. He didn't care what they did at this point, he just wanted to do it with Jenny. She started painting William's toes in the same shade as his lipstick. While he watched her carefully apply the color a question came to mind. "Have you ever done anything like this before? Play dress up, I mean." "Well," she paused and then resumed, "my sister and I used to play dress-up in some of my mother's things when we were younger. We had a lot of fun clomping around in over-sized shoes and dresses and smearing make-up on our faces. We looked like total messes, but we thought we looked all so elegant." She blew lightly on his toes. "And now me?" he wiggled his toes admiring her handiwork. "Yes, and now with you. Be careful not to smudge them," she warned and shifted positions laying her feet in his lap. "Your turn." She watched him carefully applying the color on her toes. She liked thinking about playing dress-up with Doreen but also wanted to keep it in mind that it was William sitting there in her dress. "Truth be told, I am enjoying this so much more. Brianna and Evelyn and I are friends, we enjoy hanging out and bashing people at the office, but we haven't hung out like this. They might, I haven't ever asked them, but there was always something that kept me from wanting more. Then you told us that wild story about being a woman for the day. It sounded ludicrous but the longer you told it, the more I could see you believed it happened. And then I started wanting to know more, to feel more about what happened. I could see the other girls were still more skeptical, but I decided this was the you I wanted to know. I pushed a little to see how far you would go and you surprised me by leaping into it." "It felt like I struggled the whole time," William answered and then blew lightly on her toes. He was rewarded with a giggle. "But I really wanted to do this. Let me do your fingers, your nails look nice, mine will take a bit of work I think." He waited while Jenny shifted around, and he took her hand and started painting her nails again. "I was wondering, though. Will this be the only time we do this?" "I guess that depends," Jenny answered. "I think I would like to do it again if you still want to." She watched him work for a couple minutes. "What about the no sex thing? Isn't that going to be a problem for you? I could see how excited you get about wearing these things." "True, there isn't any hiding that," he sighed. "But, like this morning, I can at least take care of things." "OK, it's going to take a little bit for these to dry," Jenny waved her hands, "so why don't you make us some lunch. There are things in the fridge for a salad, some leftover chicken that could be cut up and added to it. You don't mind, do you?" "Not at all," William stood and strutted over to the kitchen. "Shall I just poke around? Or do you want to direct me to where things are?" "Explore," she answered and leaned back against the couch. William opened and closed cabinets working around the small kitchen occasionally having to pull the hem of his dress out from under his feet. After a short while he set two salads and two glasses of water on the dining table. Jenny got up from the couch and took a seat. "This looks wonderful," she complimented. "Thanks, it was all your stuff," William swept his dress around as he sat and pulled the dress over his legs closing the slit. "I think we should open a bottle of wine after lunch," Jenny told him. "A nice light chardonnay sounds perfect. And then, I'll get your nails done. Following that, I'd like to pull out my laptop and see if we can find some shoes that will fit you. We have decided we are going to do this again, right?" William's eyes lit up. He had hoped but it was still unconfirmed, easy to cancel. Shopping online meant she really was serious. "That sounds great!" The afternoon slipped by, wine bottle emptied, William nearly tripped over his dress trying to hurry to retrieve his wallet from the bedroom when they found several pairs of shoes that would work. They looked at wigs as well. They found themselves laughing and hugging as they carried on through the day. "Oh, it is getting late," Jenny sighed. "I think we should have dinner delivered. There is a fine restaurant down around the corner with an excellent menu. More wine, and we watch the sunset from the patio. How's that sound to you? My treat since I had you spend all that money online today." "That sounds good, as long as I don't have to answer the door," William answered. "Can't hide this hair." "You can hide in the bedroom if you like, or just stay out on the patio when it comes," Jenny assured him. They ordered the dinner online, opened the next bottle of wine and proceeded out onto the patio. The sun was an orange ball still a bit above the city's skyline. William felt the cooler air caressing his back and slipping through the slit in his dress. "Are you too cold?" he asked. "Um, no," Jenny answered. "This feels really nice to me. Are you cold?" "Not at all," he adjusted his dress again as he sat. "I just wanted to be sure you were ok. Your dress doesn't cover as much as mine does." "You might be surprised how warm this dress can be," she explained. "All the layers in the skirt can really get warm. At least the top allows me to let go of the heat." They watched as the sun slid down between the buildings. The doorbell rang. Jenny went inside and retrieved dinner from the delivery person. William resisted the urge to look inside. It would be impossible to tell who was out on the patio and how they were dressed from inside if he didn't get up. "Come on inside and grab a plate," Jenny told him. "We can still eat on the patio." They set up their dinners, refilled their glasses and went back outside. William was being extra careful not to trip on the dress. "I think after dinner it will be time to get out of these dresses, and wash off the make-up," Jenny decided. "Are you ready to get out of that dress?" William considered it, "Yes, I think so. I've had a wonderful day and actually I think I will miss wearing it, but it is time." They finished eating, went back inside and cleaned up the kitchen. Jenny led them back to the bedroom and proceeded to undo the back to William's dress. They turned and he unzipped hers. She stepped out of her dress and peeled the little panty off while William undid his bra. He hesitated before removing his panty still not wanting to expose himself too brashly to Jenny. "I think after being in these dresses all day they need to go to the dry cleaners," Jenny collected them both and put them in a bag in the closet. Still naked she walked over to her dresser and pulled a pair of panties out and slipped them on. From another drawer she grabbed a green silky nightshirt and slipped it over her head. She turned to head for the bathroom. "I am going to clean off my makeup," she spoke as she walked through the door. "Pick out whatever panties you like and something to sleep in. Just poke around and find something you like." William peeled off the little panty he wore and went to the dresser. He opened the drawer he had seen Jenny pull a panty from and stared in at the collection of panties there. He selected a silky string bikini panty that had a swirl of colors and slipped it on. The other drawer had several things for sleeping. He pulled out several and decided on a white silky nightshirt. It wasn't as short as the one he had worn the night before but had notches cut up on the side. His panties weren't visible through the sides either and he liked that. He went to join Jenny in the bathroom. "Good choice," she commented as she dried off her face. "Let me help you get that stuff off your face." By the time she was done he felt like he had lost a couple layers of skin. But, all traces of the afternoon were gone, except for his nails. "We'll take care of that tomorrow before you go home," Jenny assured him. "For now, let's get into bed." They crawled into bed and Jenny curled up beside him draping an arm across his waist. "I've had a wonderful day today; I am pretty sure you did too." "I have," William patted her arm. "Thank you for everything." Jenny turned and drifted off to sleep. William had no trouble getting to sleep this night. He woke the next morning unsurprised to find Jenny once again with her head on his shoulder, arm around him, and leg draped over his. He didn't move not wanting to disturb her, wasn't worried about needing to leave. But other thoughts invaded his mind." A short time later, Jenny began stirring. "Oh, good morning," she purred. "I slept so well last night, and I seem to keep latching on to you at some point. I hope I didn't disturb you too much." "Not at all," William stroked her arm. "I woke up just a few minutes ago. I have no idea how long we have been in this position." "Should we get up?" she asked without making any move to try and leave. "Only if you feel you need to," William answered. "I'm pretty comfortable. I have been thinking though. Can we talk some?" "We can talk and lie here all morning if you like," she adjusted herself a little to get more comfortable but didn't move much. "We ordered all that stuff yesterday and it is being delivered here," William started. "And we did say we were wanting to do this again. I just wanted to be sure you still wanted to. I know we didn't drink a lot of wine yesterday, but maybe you might feel differently this morning." "I had a wonderful time yesterday," she answered. "And I hoped you wouldn't feel differently this morning. So, no, I don't feel differently, yes I want to do this again." "Good," William hugged her close. "But there is something else on my mind. Tomorrow we go back to work. Are you going to want to share what we did this weekend with Brianna and Evelyn? I mean if word gets around the office about this, I can't imagine what my life would be like." "I understand your concern," Jenny replied. "But be assured that I have no intention of telling anyone. As a matter of fact, I am not ready to have anyone know that you spent the weekend here, or even that I invited you to my place. I'm just funny about people knowing too much about my private life. Understand, I am not embarrassed about spending time with you, I just don't want to be the subject of office gossip." "Well, I don't have anyone to tell," William answered. "Though I guess I might actually say hello to the other girls this time. My lips are sealed." "Thank you," Jenny sighed. They laid there together without speaking for another fifteen minutes before Jenny decided she needed to get out of bed. "How long before you want to go home?" Jenny called from the bathroom. "If you'd like me to stay a bit, I could go home after lunch," William answered. "I'd like that," she flushed the toilet and came back out. "Would you like you put on that gray dress? One last little bit of time with Doreen before you need to go." "If you'd like me too," William climbed out of bed. "Help me get a bra on?" He peeled off his nightgown and went to the dresser. He selected a white bra, found his breasts from the day before, and slipped it on. Jenny fastened it for him, and he created his breasts. While he did that Jenny handed him the dress from the closet. He slipped it over his head and Jenny zipped him into it. "Thanks," William adjusted his dress getting it settled. "What about you?" "Not sure yet," she moved back to the closet. "I have some waffles in the freezer. You want to toast them while I change?" "Sure, I can do that," William headed for the kitchen. He moved about feeling like he belonged there after acquainting himself with where everything was the day before. He liked the feeling of this dress on him, the way it slid around his legs, and especially liked not having to worry about tripping over it. The waffles popped up and he put them on a couple plates. He put butter and syrup on the table, along with silverware and the plates. He just finished pouring a couple glasses of apple juice when Jenny came into the kitchen. He stared at her for a second. "Wow!" he stammered. "I thought since I don't go out much except after work," she did a slow turn around, "I couldn't wear this to work, and I had someone here to appreciate it, I would try it out. I've had it for more than a year and never worn it." She had on a black minidress. Long sleeves, turtleneck but very short. It was sheer above the spaghetti strap liner that scooped down showing her cleavage through the black fabric. "You look amazing," William told her. They sat down and ate breakfast. William had a difficult time not staring at Jenny. They finished breakfast, cleaned up the kitchen together and then sat down where Jenny went to work removing the nail polish from William's fingernails. "OK, let's clean your toes now," she put her hand out to lift his foot. "No," William answered, "I think I'd like to leave them." "Really?" Jenny grinned. "Yes, I'll have shoes on, and nobody will see them," William grinned, "but I'll know, and so will you." "I like that," Jenny put the remover down. They talked the morning away and had lunch when it came time. "I'm afraid it is time for me to go home," William groaned. "I wish tomorrow was a holiday so I could stay longer." "Me too," Jenny stood up and reached out. "Come on, let's get you changed." She led them back to the bedroom and helped William get out of the dress and bra. "Do you want to wear the panties home? No one will know under your pants." William thought for a minute then slipped the panties off. "No, I think the toenail polish is enough for now." He dressed in the clothes he had arrived in. "Well, I guess I'll see you tomorrow morning," he told Jenny while opening the door to leave. "Absolutely," Jenny pulled him into a hug. "It'll be nice having a new friend at work. And Doreen will stay just between us. If you don't mind, I think I am going to start calling you Doreen whenever you are here dressed up." "I don't mind," William squeezed her. "Doreen is the reason we are friends now." The week was different for William. He joined the girls for lunch a couple times and was invited to join them for drinks Friday once again. They asked about any more encounters with the mystery woman, but he told them he felt she had done what she set out to do: awakening him to a world of diversity and acceptance. After drinks Friday, he and Jenny walked to her place. "I have something for you," she pointed to a collection of boxes in the corner of her dining area. "It looks like everything is here. I got you something else." She led him back to the bedroom. "I thought you might like trying a longer nightgown." She handed him a yellow silky nightgown and a pair of panties. She turned and began undressing while William quickly started stripping off his own clothes. He slipped the yellow panties up his legs and adjusted himself. They were cut high on the hip, nearly sheer with lacy accents. He took the nightgown and worked it around over his head. He struggled a bit because the straps were all very long and thin. Once he finally figured out which holes he needed to get his head and arms through the slinky fabric slithered down his body. He looked in the mirror and saw the back was mostly made up of those strings, the fabric starting just above his butt. He turned to Jenny. She was watching him admire the gown she had gotten for him. "We'll see if you like sleeping in it," she stood there in a short, light blue nightie. "I still prefer mine very short." She picked at the hem lifting it a bit exposing a pair of sheer blue panties underneath. "Shall we have another drink before bed? Like last week." "Sounds good to me," William followed her back to the living room loving the feeling of the gown slipping around his legs as he walked. He was also aware of his bare back, which brought him back to thinking about the dress he wore the previous weekend. "To another weekend of Jenny and Doreen," she toasted. William clinked her glass and drank. They talked a bit more and finished their drink. "Well, I don't know about you, but I am exhausted after this week," Jenny got up and took the glasses to the sink. "Are you ready to call it a night?" "Sure," William stood and pulled the gown free from where it stuck to his body. They crawled into bed and drifted off to sleep. The next morning William wasn't surprised at all to wake up and find Jenny snuggled up to him. He needed to work his legs a bit, gently in order not to wake Jenny, because they were wrapped in his nightgown. Jenny stirred. "Good morning," she muttered. "Good morning," William answered. "Sorry, I didn't mean to wake you, but my legs were tangled in my gown." "So, did you like the long gown, or do you want to go back to short ones?" Jenny ran her fingers across his stomach. "I liked both," William confessed. "Probably prefer one over the other at some times but thank you so much for the gift." "Totally my pleasure," she purred. After a minute she asked, "how are you feeling about the no sex thing?" "I'm ok with it," he admitted. "I am enjoying this relationship too much to want to do something to destroy it." "So, you don't want to have sex?" she pressed. "Well, I wouldn't go that far," William sighed. "I don't want to do anything to make you uncomfortable. I've taken several cold showers this week thinking about you." "Oh, really!" she laughed. "Well, the reason I asked is because if you are interested, I want to have sex." "Oh?!" William felt his heart begin to race at the thought. "Can you be honest with me and tell me how you really feel about me?" Jenny pressed. "Absolutely," William answered. "I was afraid of saying too much, of scaring you. I think I started falling for you when we went to bed Saturday night. Sex not being a part of it I wasn't distracted by it, just my feelings of wanting to be there with you, of wanting to make you happy, of feeling like I was going to be leaving a piece of myself behind when I left the next day. I was afraid you'd freak out that I was going too fast. I actually still am." "Don't be," Jenny assured him. "When I woke up Saturday morning and found myself rubbing on you, I thought I was just horny from seeing you in that nightie and panties and sleeping with you. But as the day went on, I was feeling more and more that I might actually love you. I didn't want to admit it to myself, let alone tell you. I kept thinking 'What sort of a ditz falls in love with a guy because he makes coffee one morning and thinks he was a woman for the day?' But I guess I am. I missed you all week long. I even bought that nightgown and slept with it laid out on the bed pretending you were here with me. So, now are you ready to head for the hills to get away from this wacko?" William laughed. Instead of answering he turned and kissed her for the first time. An hour later William climbed out of bed and pulled his nightgown off, his panties had disappeared long before. He smiled at Jenny lying naked on the bed, a huge smile on her face. "I believe I need a shower," he put the nightgown on the bed. "Do you want to pick out a dress for me to wear today? Or at least my lingerie? And if you want me to scrub your back, you can certainly join me." "Go get in the shower," Jenny grinned even more. "As soon as I get the feeling back in my legs, I'll grab panties and bras for us both and join you. Don't clean up too fast." William stepped out of the shower and grabbed a pair of white panties. He slipped them on and grabbed the bra. Jenny peeked around the curtain. "Fasten it around your waist where you can reach it and then pull it up." She watched as he got it on. "Now, there is a small package beside the dresser. I wasn't sure if I was going to do this or not but now I am sure. I got you breasts! They just slip into your bra." William turned and left the bathroom. He found the package and opened it. Inside he found two breasts complete with nipples. He slipped them into his bra and felt the weight tug on his shoulders. He walked back into the bathroom to look in the mirror. "They look good," Jenny had pulled back the shower curtain and was reaching for her towel. "Yours look better," he grinned. "Can't have everything," she giggled and started drying off. "Go put a dress on." William went to the closet. He turned on the light and saw for the first time how organized it was. Skirts lined one area, dresses another. Blouses and slacks. Shoes neatly lined along the floor. He went to the dresses and worked through them trying to decide what he would like to wear, and what Jenny would like to see him in. He could tell most of the dresses were going to fit him tight because that is how she liked them. He thought for a moment, then reached into his panty and tucked himself between his legs. It wasn't particularly comfortable, but he ran his hand over the smooth front of his panty and felt it would work. He selected a dress and pulled it down over his head. It felt odd pulling it down over his breasts but worked it down to just an inch above his knees. He wondered how difficult it would be to walk in it but found the material was stretchy enough to allow him to move. He walked back into the bedroom thinking about one of the packages in the living room had shoes that ought to fit. "Wow, nice fit, Doreen," Jenny came out of the bathroom in her bra and panty. "Hard to believe I had fabulous sex with you not that long ago." "I thought I would try one of my pairs of shoes," Doreen answered. "Good idea. You go find them, and your wig, and I'll pick a dress for myself. When you get back, we'll do make-up." Doreen went and opened several boxes, located the shoes and put them on, then found the wig. She carried that back. She wobbled a bit at first on the heels, but they weren't that high nor that hard to navigate. They definitely made her legs look better. "Oh, yes!" Jenny called when Doreen entered. "Love everything. Let's finish the rest and see just how good you look." Doreen grinned and took a seat at the vanity. "I am going to take my time and tell you what I am doing this time," Jenny explained. "I want you to be able to do this yourself one day." She fixed Doreen's face and brushed out the wig, placed the blond wig on her head and styled it a bit more. "Well, there you are Doreen. Is that the woman you saw in the mirror before?" Doreen turned and looked. She did see a similarity to that woman who suddenly changed William's life. She could still see flaws in the fa?ade, but overall was very impressed. The makeup wasn't as dramatic as the job Jenny had done last week for the formal dresses. "Now, scoot and let me see if I can make myself as pretty as you," Jenny teased. Doreen left and went to the living room. After a moment she decided to stroll out on the patio to enjoy the open air. She was standing there looking at the city when Jenny joined her. "You look beautiful," Doreen told her. "I like that dress, but it might be a bit short for me." "I think with a little practice you could do a short dress like this," Jenny assured her. "Since I wouldn't wear something this short to work, I like to wear them whenever I have an excuse. And spending my day with my girlfriend Doreen is just the excuse I need." They spent the day talking, playing games, eating and just enjoying each other's company. They watched the sun set together. "This has been a wonderful day," Jenny sighed. "It seems to be getting better every time we get to spend time together," Doreen agreed. "I'd like some dessert," Jenny announced. "Sure, what have we got?" Doreen started toward the kitchen. "Nothing, I'm afraid," Jenny hedged. "We'll need to go out." "What?" Doreen stopped. "Listen to me," Jenny went and took Doreen's hands. "We've spent the whole day together. You act just like any other woman. In that dress nobody would think there is actually a William inside, sometimes I even forget about it. There is a gelato shop a short walk from here. We go, get our dessert, and eat it on the walk back. We won't stay anywhere so nobody will even have a chance to question you. Please!!" Doreen was scared. It was one thing to spend the days and nights in the security of Jenny's place but to risk going out in public. She turned away from Jenny and saw her reflection in the windows leading to the patio. She took a couple steps and thought about what Jenny had said about loving William, about what William admitted to her. There was no way she would put him in harm's way. Right? It would be the ultimate trust fall in a way. "Do you have a purse I can borrow that goes with this dress?" Doreen asked. Jenny clapped her hands. "Absolutely!" She disappeared but returned a couple moments later carrying two purses. "I put your wallet in here," she handed Doreen the purse. "You need to have some id on you just in case. Nothing will happen, we are going to enjoy a nice walk." "What about building security?" Doreen asked. "Won't they be suspicious that William came in with you and now Doreen is going for a walk?" "I doubt they pay that much attention," Jenny assured him. "Plus, shift changes. There will likely be a different person at the desk." Doreen gave in and they went to the elevator. The ride to the lobby was uneventful as was the walk to the gelato store. They got their treats and walked back to Jenny's building. By the time they reached the lobby Doreen was totally at ease. They marched together through the lobby and got on the elevator. As the doors were closing a hand reached through forcing them to open again. Two men stepped into the car and punched the button for the 5th floor. Doreen stepped back into the corner and concentrated on her dessert. Jenny stepped back beside Doreen. One of the men turned to them. "Ladies! You look like you've been having a nice evening. Would you be interested in having a drink with us? Looks like you are heading to seven, short distance from five!" "Thank you," Jenny answered. "But we are just going to head home. But you guys have a good rest of the night." "OK," the guy turned back. "Maybe another time." The doors opened and they left. When the doors closed Doreen fell back against the wall. "Well, that was exciting," Jenny told her. "You did great. Those guys never had a clue. The light in this car is bright too." The doors opened. She reached and took Doreen's free hand and pulled her out of the car. "We can go anywhere we like: dinner, theater, shopping! Wouldn't you like that? Wouldn't it be great going into someplace together to have a nice dinner? Or to try on dresses?" "Is that what you want?" Doreen asked as they entered the apartment. "You want me to go with you as your girlfriend all the time?" "No, not all the time," Jenny assured her. "Sometimes it would be nice though." "I need time to think about this," Doreen answered. "I didn't expect it to go this far. Actually, I didn't expect it to go this far with the wig, the heels, the breasts. I'm not sorry about that, about any of it. But being in public, especially if guys are going to be hitting on us? I'm not sure I'm ready for that." "I understand," Jenny nodded. "I think I'd like to let dessert settle for a bit before going to bed. You are going to stay, aren't you?" Doreen looked at her confused, then understood. "Of course, I'm staying. I told you last week that you are learning things about me at the same time I am learning them. And now, I think I understand that you are learning some new things about yourself as well." "I guess so," Jenny answered. "I never thought about a situation like this. I started liking you and thought maybe I could help last week by giving you an opportunity to try out this new person. Then I started really liking you like I told you this morning. And I've also started to really like Doreen. I like spending time with her. But I know that at night I will crawl into bed with William, who happens to enjoy panties and nightgowns." She smiled. "OK," Doreen turned and sat on the couch. "I think we understand each other. Come sit with me?" Jenny quickly stepped around and sat on the couch beside Doreen. She pulled the hem of her dress down a bit and snuggled in close. "I hope we solve all our issues that easily." "I'm sure some will take a bit longer one day," Doreen told her. "But getting them solved is the important part." They sat together for a while holding each other. After a while they went to bed, made love for the second time that day and fell asleep in each other's arms enjoying the warmth of their bodies and silkiness of their nightgowns. Two months later William moved into Jenny's condo permanently. They had a lot of rearranging to do, and it took a lot of work, but they managed to find a way to get William's clothes for work in, and they mixed the dresses and skirts he had accumulated in with Jenny's since they were the same size agreeing there was no need to divide them. William joked that Jenny was free to wear his clothes any time she wanted. Another dresser was added to the room and William stored his regular things as well as some lingerie in it. The people at the office became aware of the new relationship and the girls were thrilled, the men confused. How could a girl as hot as Jenny be attached to someone as plain as William? Of course, they didn't care what anyone else thought. Another couple of months went by and things had settled into a comfortable pace. William surprised Jenny with a request. "Are you sure about this?" Jenny asked for the fifth time. "Yes," William answered as they went through the lobby at work. "I need to push myself a little more. And I think it is time and this is the way to do it." "OK," Jenny kissed him before they went through the doors into the office. A short time later, William was in the breakroom making coffee when Jenny came in. "This is where it all started," she put an arm around him but heard someone coming so backed away. They had decided to keep it professional at work, well, just as long as anyone else was around. Brianna walked in. "Hope I didn't interrupt," she grinned. "Not at all," William answered. "I smell coffee!" Evelyn came in. "Well, the gangs all here!" Jenny answered. "Got a question for you. How would you like to come to our place for dinner Friday?" "Really?" Brianna exclaimed. "You've never asked us up before. Looks like William is having a positive influence on you." "I never thought you would be interested," Jenny admitted. "You two always seemed to be ready to just head home after drinks." "I smell coffee!" Alan walked into the breakroom. Before he could get the carafe William pulled it out. He poured Evelyn's, Brianna's, Jenny's and his own before handing the pot over to Alan. "Good thing there was enough left," Alan huffed. "Yeah," William answered. "You might have actually had to make some yourself." Alan gave him an evil stare and marched out of the breakroom. They all waited a minute before bursting out laughing. "I have to say," Evelyn said between laughs, "you two are definitely good for each other. Now about dinner." "Yes," Jenny picked back up. "I thought we could all have a drink nearby before going up to our place. William has some preparations to do first and that will give him time. Sound good?" "Sounds great to me," Brianna answered. Evelyn nodded her agreement. Friday rolled around and the girls laughed and giggled on the ride up the elevator to 709. Jenny opened the door and walked in, Brianna and Evelyn followed and stopped dead in their tracks and stared. Doreen came from the kitchen in a long tan print dress. It had short puffy sleeves and a round neck with a touch of ruffle. It was perfect as a casual dress for entertaining. She carried a tray of appetizers. "Good evening," she greeted their guests. "I hope you had a nice time so far, dinner will be ready in a few more minutes but these crab puffs ought to hold off the stomach rumbles til then." "Thank you, dear," Jenny took the tray and kissed her lightly so as not to mess up her lipstick or her own. "William?" Brianna asked and squinted at her. "Doreen, please," she answered. "And please, close the door. We don't want any unexpected guests." "Sorry," Evelyn answered and pushed the door closed that she had been holding. "What's going on? Jenny?" Brianna still hadn't moved. "Why don't I get you both something to drink and we'll sit out on the patio while Doreen finishes getting dinner ready," Jenny pushed them toward the patio. She poured drinks and looked at Doreen. "Well, at least they didn't run right away." She went out onto the patio. An hour later Doreen appeared at the patio door just in time to hear Jenny say, "and rather than start going out doing things, except for an occasional walk at night to the gelato shop, she thought she would rather have you both see her. I tried to say it might be better if we went places where nobody knew us, but she trusts you to be honest with her." "Dinner is ready," Doreen told them softly. "Great," Evelyn answered. "I'm starved." "Yeah, I'm ready," Jenny answered. They all gathered at the dining table. Doreen finished putting the food down then swept her long skirt under her as she took her seat. "So, Will..., um, I mean Doreen," Brianna started. "Is this something you are considering full time?" "No, this is just something I enjoy doing," she answered. "Jenny helped me discover a lot about myself after that weird day I told you about. The more we did, the more I liked. But Jenny wants to do more now. We are best friends both as in a boyfriend-girlfriend relationship, and as girlfriends. I am still scared and uncertain. But I trust you both to tell me if I should be able to go out like this somewhere that people would be around." "You want the truth?" Evelyn asked. "Of course," Doreen braced himself for whatever was coming. "How long did it take you to get ready tonight?" Evelyn pressed. "Oh, about an hour," Doreen answered confused. "OK, because I was just wondering how long after work we would need to give you to get ready for a real girl's night out!" Evelyn crowed. "I think you look fabulous and if I didn't already know William, then I would never have guessed Doreen was anything but Doreen. Is this what you looked like when you were changed into a woman?" "Yeah, pretty much," Doreen sighed feeling better. "That is why we picked this wig; it is how my hair was then." "I am impressed," Brianna finally spoke. "Look, we aren't all Chrissy Teigen or Heidi Klum, and I think it is even better that we aren't. You look amazing. And I agree, we need to do a real girl's night out. We can have a drink at a bar while you get ready, join us when you can and then we go find someplace really nice. Have some dinner, do some dancing." "See, I told you," Jenny reached over and took Doreen's hand. "I know, and I wanted to believe you, but something just held me back," Doreen told her. "I'm ready now." "Great, we'll make plans for the great girl's night out," Jenny answered. "And we should go dress shopping for something special to wear that night." "That is another question," Brianna started. "Do you just like long dresses? Or will you do something short too?" "Oh, you don't have to worry about that," Jenny spoke before Doreen could answer. "She has terrific legs. She isn't quite comfortable with skirts as short as you like them, but she wears them short enough." "Would it be too forward to ask you to change after dinner?" Evelyn pressed. "I'd like to see you in something short. I mean I think you chose the perfect dress for entertaining; I'd like to know where you got it. I might find something I could wear at home when I have people over." "No," Doreen answered. "I don't mind changing. You all can clean up the kitchen while I do!" "Seems like a fair trade," Jenny laughed. "I have a feeling that adding William to our little group," Brianna smiled at them all at the table, "may have enriched all our lives more than we initially thought. He brought us our new sister. Welcome, Doreen!" They all toasted.