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My Life Began at 50 Chapter 1 Reunion It had been six months since I relocated back to Sacramento and a year since my divorce had finalized. My work day was finishing up, the weekend was here and I was really excited about the evening. I hadn't seen my friend Jeanie in a couple years. I had been making efforts to connect with all my old friends since returning, but as usual, Jeanie and I always seemed to be unable to connect. Tonight we have a date. This would be our first date ever though we have known each other for fifteen years. We spent so much time together for the first eight years working at the same place that we knew each other really well. That didn't change the fact that I was actually quite nervous. I drove up the hill to her house and went to the door. We had agreed it would be a casual evening so I was dressed in jeans and a polo shirt with brown loafers. I went to the front door and knocked. When the door opened she was standing there in a summer dress with low heels, casual but looking so great. She stepped toward me and we hugged telling each other hello and how good each other looked (I know I meant it) and how good it was to see each other. I stepped inside briefly while she gathered her things and then we went off to dinner. We went to a local restaurant that offered good wines (easy to find in the Sierra foothills) and excellent food. We discussed all of the events in our lives over the past couple years while finishing off a bottle of wine. Conversation flowed easily as it always had with us. It seemed like moments had passed but we lost more than two hours. "It's still pretty early, want to find someplace to have another drink before calling it a night?" I asked. "I really don't know of a place that we can talk without being drowned out by loud music" Jeanie answered. "How about we head back to the house, I have some wine there we can open." I paid the check and we made it back to the house. I watched her as she checked through the bottles and found one that she deemed appropriate. I took the corkscrew and proceeded to open the bottle. As I was removing the foil she said, "Mind if change clothes?" Actually I did, I always loved seeing her in a dress and she knew it. But I told her to go ahead and get comfortable. I finished opening the bottle and poured a couple glasses. She returned as I was bringing them into the living room, she was now in a sweater and pants with socks. We settled on the couch and I handed her a glass while kicking off my shoes. Conversation kicked right off where we left off and hours disappeared from the clock, as well as wine from the glasses. "I had such a great time tonight. I don't want to wait too long before we get together again," I told her as I walked toward the front door. "I have a party to go to next weekend, perhaps you would like to be my date?" "Absolutely! Anyone I know?" "Yeah, Amy and Gary. They'll be happy to see you again. I told Amy we were going out tonight and she remembered you." "Yeah, they are good folks. Now I have something to look forward to." I opened the door and turned to face her. She stepped forward a bit closer and I closed the distance between us and took her into my arms for a hug. We stood like that for a minute until I leaned back a bit and kissed her lips. It was an easy kiss but it felt like more. I started to end it before it became obvious how the kiss had affected me but I felt her arms tighten a bit as I moved. I renewed the kiss and her lips parted in response. Suddenly it felt as if a furnace had been ignited inside me. I let my hands slide down her back and then back up again. The second time I was under the sweater, my hands on the bare skin of her back. I held her again, relishing all the touch of hands, lips, and tongue. Her hands gripping my back, she took a step backward without letting go bringing me back into the house. Without stopping the kiss she pushed the door closed. The kiss ended as we needed more air but the embrace did not. I leaned and kissed her neck as she tugged at my shirt getting her own hands on the bare skin of my back. I couldn't wait any longer; I pushed her away and pulled my shirt off, dropping it on the floor. I knew this was the moment where it could end, a break to allow the senses to realign and let reality back in. I stepped forward again and took hold of the bottom of her sweater; she raised her arms over her head and I pulled it up and off. I took her in my arms once again and pulled her close feeling her warm skin against mine, her lips once more against mine. She reached behind herself and unclasped her bra, though it stayed trapped between our bodies. After a moment she stepped back and I made sure the bra came off and fell to the floor. Our hands explored the body of the other, breathing accelerated. Finally she took my hand and led me toward the bedroom. More time was lost as we pleasured each other until we eventually dropped off into an exhausted, pleasant sleep. * * * * I awoke the next morning to an empty bed and the smell of coffee. I climbed out of bed and found my pants on the floor; I assumed my shirt was still in the hallway by the front door. I walked toward the kitchen passing a few articles of clothing along the way. Jeanie was standing there stirring her coffee. She was wearing a different sweater, one long enough to cover her bottom. I couldn't tell what, if anything, she was wearing under it. Last night's activity hadn't completely drained me and I responded immediately to seeing her standing there like that. I was glad I took the time to put on my pants. "I didn't make you a cup because I don't remember you drinking coffee. There is orange juice, milk or water if you like" she said without looking around. "You remember right, milk will do" I answered. "Are we ok? I didn't expect last night to go the way it did. I'm very happy with it, but I won't be if it is going to be a problem. You've been my best friend for a long time, even though we were apart for all those years; I don't want that to be in jeopardy." She looked me in the eye as she handed me my milk. "I am very happy about last night. I also didn't plan it to go that way. I guess that means you will still want to be my date next weekend?" "Absolutely! Never a doubt." I reached for the milk and she moved it forward at the same time, the result was me wearing most of the milk as it splashed off my chest and ran down into my pants and onto the floor. For a moment both of us just stood there staring at the floor and the running milk. Jeanie turned and grabbed a towel and started wiping me off. I stood there looking for something to wipe the floor and saw nothing that would help. "You need a shower," she said with a bit of a laugh. "If you wanted me in the shower all you had to do was ask," I answered. "Oh no, not together, not now. I'm going to clean up this mess and your clothes need to be washed now. Looks like we will be spending at least part of today together. Hope you didn't have any serious plans." "Nothing in particular. I guess I'll get in the shower." "I'll finish cleaning up and find something you can wear until your clothes are ready." I reached out and pulled her close, I could feel she was wearing nothing under the sweater. I kissed her, briefly, I hadn't brushed my teeth and neither had she. "By the way, do you have an extra toothbrush? I'd like to give you a proper good morning kiss." "Yes, under the bathroom sink there is a new one. You can use that." I walked off toward the shower collecting the clothes from last night and peeling the damp clothes from my body. I left them in a pile with the wet clothes on top and went for my shower. Feeling refreshed I left the bathroom for the bedroom. The pile of clothes was gone and there were clothes sitting on the corner of the bed: bra, panties, and a sundress. "Hey Jeanie! Did you find something for me to wear?" "Yup, they are right there on the bed." "Uh, ok," I answered wondering what was up. I had figured sweatpants or a robe or something. I set the bra aside, I didn't feel I needed one and picked up the panties. Plain white and satiny I put them on. They were a little tight but fit. Even erect they kept me somewhat flattened out. I got the dress on after a brief struggle. It was pretty tight under the arms but pretty loose the rest of the way. It wasn't much longer that the sweater Jeanie was wearing. I walked out into the kitchen feeling more naked than if I really were. Jeanie looked and gave a quick laugh as she eyed me up and down. "Nice legs," she offered. "Do you mind telling me what is up? Is this really all you could find for me to wear?" She moved and put her arms around me running them up from my ass to my shoulders. "You didn't put the bra on," she said as she leaned away from me. "I really didn't think I needed one. Besides, I may have some man-boobs but nowhere close enough to fill your bra." She ran her hands around to my chest lightly running her fingertips over my nipples. "OK, it also helps to hide these though." She dropped her hand down tracing my hard-on with her fingers. "You do seem to be enjoying this" I smiled and slipped my hand under her sweater and between her legs. She was so warm and moist I reacted under her fingers even more than I thought possible. "You seem to like this too" I moved to kiss her but she pushed me back. "I need a shower as well. Make yourself comfortable while I clean up and then we'll have some breakfast" As she moved past me toward the bedroom I snagged the hem of the sweater flipping it to expose her naked rear for a second as she walked away. I turned on the television and found the news but I couldn't pay attention to it thinking about the last 12 hours. So much had changed in such a short time, not the least of which was me sitting in Jeanie's living room in a dress. I went back to the bedroom and struggled out of the dress. I decided I'd gone that far I'd play the rest of the game. I put the bra on and slid the dress back on. I heard the shower cut off as I went back to the living room. A few minutes later Jeanie entered the room wearing another sundress, short but not as short as mine due to me being taller. I went to her and gave her the good morning kiss I had wanted to give all morning. At the same time I took inventory of all she was wearing. By touch we seemed to be dressed exactly the same now. "You put the bra on," she said and smiled. "I figured I had gone this far, I might as well go with all you provided. Now, do you want to tell be why?" "Not quite yet. Breakfast first." We went to the kitchen together, Jeanie pulled out some eggs, potatoes and bread. We divided up the tasks and put together a nice breakfast. We talked but I didn't press for information. I knew she would tell me when she was ready. We sat down to eat, the seat cold against my bare legs. I put a napkin in my lap in part because the dress was so short I felt I could almost see my own panties. "Do you remember back when you, Kari and I went to lunch and I made that comment about forgetting you are a guy sometimes? There were times I felt you were as much a girl friend of mine as anything. It seemed safer since we were both married then as a way to keep our distance and still be close." "Yeah, I remember that. I wasn't at all put off by it, maybe because I felt the same way, maybe for other things. Is that why you gave me this dress to wear this morning? You telling me you want me to be one of your girl friends?" "Well, yes and no. I don't want to lose any of the friendship that we have. I would like to be able to talk to you like a girlfriend. But I also want to continue to see if what started between us last night can work. The fact that you actually put on those clothes instead of walking out in a towel and insisting on something else or your own clothes back said something about how much you trust me. Did it occur to you that I might have been angry about last night and looking for a way to embarrass you? I could have had camera waiting or just pushed you out the door and let you drive home in that dress." "You know, that didn't occur to me at all. I expected you would have told me before the shower. We've been honest with each other in discussing things, no reason to believe you would do something like that. However, since you seem to have thought those things out, were you thinking of doing that?" "No, just trying to think of what your reaction might be, trying to have a response if you were totally freaked out by the request. I did it the way I did because I thought you would go for it. And I'm glad you did." I stood up, smoothed my dress back down, and picked up the plates taking them to the sink. I rinsed them in the sink letting everything sink in, judging what I wanted to say next. "When did you concoct this little plan to get me into a dress? Did you spill the milk on me on purpose?" "Actually, no, but the idea came along pretty quick when I realized your clothes would have to be cleaned and you would need to wear something during that time. Which reminds me, I probably ought to get them started." "You haven't started them yet? How long are you planning on me hanging out here today? Not that I am complaining, I'll stay all day if you like." "Well, I was waiting on your reaction. You might have just decided to go home in milky pants. So, since you aren't in a rush, I'll get to them soon, just don't let me forget." "Oh, trust me, I won't. If it'll make you feel better, why not let's get them started and I promise I won't change as soon as they come out of the dryer." Jeanie smiled and went to the laundry room. I heard the washer start and I headed for the living room. I sat on the couch and tried to tuck a bit of the front of the dress down between my legs. Jeanie came back and sat across from me on the loveseat. I watched as she sat exposing nothing, and she knew I was watching. "So" she started again, "the thought I had for the costume party was a bride and groom. I get to be the groom. You can be the bride." I just blinked and stared at her. "This is going to take me a minute. First, I don't think you mentioned this would be a costume party. Secondly, it is one thing for me to sit here like this with you right now, going to someone else's house in a wedding dress. I need to process." She got up from the love seat, not as carefully as I saw a flash of white beneath the edge of her dress. My body reacted immediately and I was reminded of how short my own dress was. She walked back to the kitchen and I could hear her moving around. I knew she was honoring my request for time. Thing is, I knew right away that I was going to do it. I just didn't want to appear too anxious. She came back and sat down on the couch with me. Her legs were positioned slightly away from me so I didn't see anything again. I wondered if the panties she wore were the same as what I was wearing, though I wanted hers to be sexier, lacier, something. "OK, first I want you to know that I will do it." Her face lit up and she grabbed me around the neck and kissed me before I could say anything more. I savored the taste of her mouth, moved and felt the bare skin of our legs come together. With an effort I separated us. "Wait, I will do it, but I have some things to tell you." She sat back, concern clouded her eyes. "I want honesty in all things between us. The way this has come down, I feel like I can do that for the first time ever. This isn't the first dress I've worn, or the tenth. I'm not sure how many for that matter. I will say you are only the second person ever to see me wearing one. The other was a friend from long before I got married. Long story short I let her convince me into trying on a dress and pantyhose. We played around like that for about a week with me wearing different dresses. What she didn't know was that I have wanted to wear dresses since I was very little. I think I was five the first time when a girl in my kindergarten class showed up in a red velvet dress. I wanted to wear it. "When I was 9 I was playing hide and seek in the house, I hid in my mother's closet. While standing there I decided to step inside a dress that was hanging there wondering if that was what it was like to wear one. A couple years later I was baby-sitting and the woman had left several pairs of panties drying on a radiator, I tried them on. "It accelerated from there. I was trying on everything I could to see what it was like, constantly trying to keep it secret. Once I was on my own I would buy a dress or a nightgown, I never had the nerve to buy underwear, and would end up throwing them away a month or so later in fear that someone would discover my secret. "I told Sherrie before we were married. She didn't like the idea at all. So, I continued to hide things. I did eventually buy my own panties, some hosiery and would borrow dresses. I frequently put on a dress and would go to work, since my office was in my home, while she was off at work. Since the divorce I have picked up a couple things to wear around the house. "So, are you totally freaked out?" She sat there looking at me for a moment. I was relieved she didn't just tell me to get my clothes and go. I think I was programmed to believe that would be the response from all my years of secrecy but once I thought about it, that shouldn't be the response considering I was sitting here in her dress at her offering. She leaned in again and kissed me gently, then laid her head on my shoulder, adjusting so that our bodies aligned. She draped her arm across my waist and gave me a small squeeze. "I'm disappointed," she started. "Through all our talks I had a feeling that something like that was there for you. I had hoped that I would be the first to get you to share this with me. Considering our age, that was unlikely, but I had hoped." "Well, you are the first to get the whole story," I said, barely above a whisper. Her hand dropped down and started tracing lines up and down my thigh. I was aching for her to travel just a bit higher under the edge of my dress. Instead she went on talking, still tracing her fingers on my leg. "So, it's all out there now. I'm happy you've told me, I like this. I think we have a good start going." "OK, so I don't suppose you have a wedding dress you want me to wear next weekend, do you?" I asked. "Actually, no. You are going to have to go shopping for one." "Um, do we have a backup plan? In case I am unable to find one?" "Not really, no. Worst case we could go over to the City Friday night. Party doesn't start until 7:30 Saturday so we could find something in time. You ok financially to do this? I could help." "No, I'm good. I'll work on figuring out how I'm going to do this a little later. Tell you what, don't tell me too much about what you are going to do. I'd like to be surprised." "Haven't had enough surprises yet?" she grinned. She leaned up to kiss me again and her hand slid up under my dress. I gasped in surprise and reached around sliding my hand under her dress as well. Within moments panties were on the floor and she was sitting atop me, my hands raising her dress to get to her breasts. I had been too worked up most of the morning and didn't last as long as I wanted but right after I exploded into her she collapsed against me, both of us exhausted. After a few moments she leaned back, "I need to move the laundry." "OK," was all I could muster. She slid off me and padded barefoot to the laundry room. I gathered my senses and picked up both pairs of panties from the floor. They were both the same. "Gee," I teased. "I don't know whose panties are whose." "Mine are probably wetter than yours" she called back. "I have been hyper-excited since you came into the kitchen after the shower." I checked and sure enough one pair was quite a bit damper. "Would you like some fresh ones? I'll get you some if you tell me where." "No, I'll do it. I need to clean up a bit first anyway. We need to discuss some rules here as well," she said as she walked through. I fell in line, panties in hand, my dress sporting an unnatural bulge. I also became aware of sweat around my bra. She went into the bathroom; I chose not to follow but instead dropped her panties on the bed and put mine back on. "First, I'd rather you not go digging through my clothes or wearing things without my giving them to you." "I can do that. Frankly I'm surprised you found something to fit me." "Well, that is probably the only one. Maybe one other, but it is too warm, a maxi-dress. Maybe another time." "The blue one? You still have that? I remember you wearing it to work." "Yeah, that's the one. I'm surprised you remember it. It wasn't particularly sexy or anything. It practically floated on me." "As I told you before, I loved seeing you in a dress. Any dress. "What other rules?" "Not much, I don't want this to be an every time we are together thing. It has been fun - a lot of fun" she giggled, "but that doesn't mean I want it every time." "Do you wear a dress to work every day?" I asked. "Of course not, you know I don't" she responded. "Right, because some days you feel like wearing a dress, other days you don't. It is the same with me. Just because I could wear a dress when I was alone didn't mean I always did. Some days I feel like it, other days I don't." "Great. I like that" she said as she came back into the bedroom. She went to the dresser and grabbed a fresh pair of panties. She turned her back to me as she pulled them on. I got a brief glance at her bare bottom and then her dress fell back into place. We returned to the living room. "I'll make a deal with you," I began. "If you have something you want me to wear, just ask. If I am just not in the mood for it I'll tell you. If you are not in the mood to see me dressed that way, you tell me and I'll change." "Deal, and you get to do the same with me." "But I'm always in the mood to see you in a dress," I said, turned and started my hand under her dress again. She grabbed my hand before it got too far, pressing it down against her thigh. "I can't believe you are trying to go again. I'm drained." I laughed. "Actually, I'm not ready either. I'm just feeling so good right now I forgot I haven't that kind of stamina any longer." We ate lunch and dinner and spent the afternoon talking and enjoying each other's company. Finally the time came I needed to head back home. I changed clothes and with a lusty kiss good night proceeded to head for home. I had until Thursday to figure out what I was going to do about the party the next weekend. Chapter 2 The Search and Preparation I spent the week going to thrift stores all over town. There were bridal shops around but I really didn't want to spend that much money, or garner that much attention, going to one of them. I walked a couple of the malls as well looking for things other than the dress. After many stops over a couple days I finally found the dress in my size Wednesday night, the last place on my list. It was a style I felt I could wear, lace over a corset top, the skirt was floor-length and full, it had lace sleeves as well. It was a good deal and I bought it. I found a veil and also an underskirt to fluff it up. Now I was starting to get a bit braver. I went and bought bridal lingerie: a corset with garters, lace-topped white stockings and a string bikini lace panty. I also had a garter for my thigh for my groom to remove when we got back home. This ought to make for a nice surprise. While at the mall I took a seat on a bench just a bit outside one of the big stores. Just inside was the perfume, make-up and jewelry department. I watched as the ladies working the counters would do samples and occasionally some customer would take a seat and they would do make-up stuff for them. I decided to take a chance and walked into the store over to the make-up counter. As I got closer one of the young ladies working the area looked up. She gave me a smile and came toward me, her badge said Denise. "Let me guess, Halloween Party?" she asked. "Uh, yes. How did you know?" "Every year about this time we get about a half dozen guys who want make-up tips or advice for their costumes. Some are real theatrical, others are doing the girl thing. Which is it for you?" She was very professional about it, didn't seem to be judging at all. Any thoughts I had of trying to hide my intentions had gone out the window. "Well," I started, kind of looking around to be sure I wasn't overheard, "I am going to be a bride." She kind of smirked a bit but recovered her composure. "OK, I can help with that. Just out of curiosity, is there a groom?" "Oh, yes, this was her idea." "OK, why don't you get her to do your make-up for you? You are obviously a bit edgy about being here talking about this." "Long story, but for now let me go with it'll be our second date and I want to surprise her." "Second date? And you are doing bride and groom?" She had a look of something I couldn't identify. Was it concern or disbelief? I wasn't sure. "Whatever works for you, I guess," she went on. "So, do you want me to show you things you will need? How to use them? Or would you like to come in before your party and one of the girls can do your make-up for you?" "The party is Saturday. Would you be here? I'm afraid it will be real busy." "No, I am off on Saturday. But, like I said, there are lots of guys who do this so you have nothing to be embarrassed about." "Well, let me ask another question. Would you be interested in coming to my house to do the make-up? I would be happy to pay you for your time. Would $50 cover it? I would expect that it would take less than an hour." Denise just stood and looked at me for a moment. She appeared to be trying to decide if I was legitimate or some kind of dangerous pervert. "Sure, I can do that. Do you have any of the things you'll need at home already?" "I have nothing," I answered. "OK. Well, come over here and I'll get you set up with stuff." We went over all sorts of things, some I knew, some I had no idea about. I gave her my address and phone number as I paid for everything and we agreed she would come to the house about 1:00 Saturday. After I left the store I walked back through the mall to the other end where my car was parked. I passed one store that had manikins and noticed the hair on one. A wig. I almost forgot I was going to need one. I did a quick search and found a place nearby. The folks at that store must also be accustomed to guys needing wigs for Halloween because no one batted an eye when I walked in. I spotted one I thought would do and asked about it. A quick fitting and some care instructions and I was on my way again. I called Jeanie and told her I was all set. I would be arriving at her house about 4:00 Saturday ready to go. She said she was impressed and looking forward to seeing me. * * * * * Saturday arrived and I got up and ate breakfast. I couldn't eat much because I was very nervous. I was nervous about Denise coming by. I was nervous about the party. I was nervous about Jeanie. I was very nervous about driving to Jeanie's house all made up and in a wedding dress. So many what if's running through my mind I was making myself sick with worry. I finally decided to take a shower and get the day started. I knew I wasn't going to back out so I just had to bite the bullet. It was the longest shower I had taken in my life I think. Besides making sure I washed thoroughly, I also shaved every part of my body. Some of it was a struggle, but I managed. After toweling off, I shaved my face as close as possible, brushed my teeth and took a good long look in the mirror. Taking a deep breath I went on to the next step. I put on the corset, stockings and panty then grabbed a robe to put on over it. Denise would most likely run from the house if I opened the door without the robe. I was now ready for her to arrive. I checked my watch, it was 10:30. I had some time to kill. I picked up and cleaned up while I waited. Surfed the net, watched some television. Sometimes the clock seemed to be standing still. Finally the doorbell rang. I did a quick check out the window to be sure it was Denise, though I laughed a bit as I thought "What if it is Jehovah's Witness, wouldn't that be fun!" "Hi there," I said to Denise as I opened the door. "Hi," she answered and looked at me in my robe with my white legs and feet. "Looks like you've started getting ready." "Well, I've seen enough movies to know that you don't get totally dressed before you put on make-up nor do you want to take off something that will smudge the make-up. Is this not good?" "No, you're fine." She stepped in through the door and I pushed it closed behind her. "Terrific. Where would you like to do this? What do you need for space and light?" "How about we check out the kitchen first? I assume you have a table in there and hopefully the light will be sufficient. I'd rather not be in a stuffy bathroom and I definitely don't want to be in your bedroom." I smiled at that and led her to the kitchen. "How will this do?" She looked around for a second. "This will be fine," she judged and started putting a few things she had brought on the table. "Good, I'll be right back." I went and grabbed the make-up and other things and went back to the kitchen. "First," I handed her the $50 "just to get this business out of the way." "Thank you, I really appreciate that," she dropped the money into her purse without counting it. "Take a seat here." She had moved a chair into position. "What sort of lighting are you expecting?" "Lighting? I haven't been to the house before. I assume regular house lighting as well as something out on the patio. Why?" She draped a cloth around my neck. "Just trying to make sure the coloring is right. Don't want you looking too orange or pale or something. Now, if you don't mind, why don't you tell me the story about you and your groom while I work. I'll explain some things that I'm doing so if you decide to do this again you'll have an idea of what to do. Otherwise, I can listen while I work." I told her the story of Jeanie and I while she worked. She listened while I recounted everything except I did not tell her about the details of the morning after our first date. The story didn't take as long as I thought it would and the make-up job was taking longer than I thought. We chatted about a few other things. Finally she finished by painting my lips. She stepped back and looked at my face with a critical eye. "I think that is it," she announced. "You look pretty good." I took a hand mirror and looked at myself. She had done an amazing job. I wasn't any kind of beauty queen, but I wasn't hideous either. Definitely a better job than I could have done myself. "Look, I've enjoyed this little session," she stated while I was admiring the job she did. "I'm guessing you are plAmying on wearing the dress out there since you're already partially dressed. Nice lingerie, by the way." I looked down and saw the robe had fallen open exposing the top of my thigh showing the lace top of the stockings and the garter attached to it. "Oops," I said pulling the robe back over. "Glad it didn't open further than that. Not something you were looking to see." "No worries. I figure if you were trying to get weird with me you'd have made your move before now. So, that is why I am offering to help you finish up. Go put the dress on and I'll help you with the wig and veil as well." "Hey, great. Thank you." I headed for the bedroom. I put the shoes on because I needed the extra couple inches to not trip on the dress. Then I stepped into it and pulled it up into place. I wasn't able to finish closing the back. I went back into the kitchen. "Would you mind?" I asked as I turned away from Denise. "Sure." She quickly did up the couple buttons I couldn't reach. I sat back down and she placed the wig and after fussing with it a bit she placed the veil as well. "There you go. I think you make a very nice bride," she smiled. "Thank you for all your work. It took longer than I expected. Please, take this for your trouble." I handed her an extra $20. "You know what? If I didn't need this I wouldn't take it. I feel like I've had as much fun as I could possibly want in doing this. I hope you have a great time and everything works out." I walked her to the door and she was on her way. I decided I was not going to be able to drive with the underskirt, just too much stuff by my feet so I dropped it in the back seat of my car. I was glad to have it parked in a garage so I wouldn't be walking around outside for all my neighbors to see. Chapter 3 Halloween Party I showed up at Jeanie's right at 3:30. I felt fairly proud of myself for getting to the house without any problems considering it was the first time I drove in heals. And I had so much dress piled in my lap to keep my feet free. I grabbed the underskirt from the back seat and debated trying to put it on before going to the door but decided not to try it. I closed up the car, flipped my veil down and headed for the door. I took a deep breath, well deep as possible in the corset, and proceeded to knock on the door. I could hear footsteps approaching and the door opened. Jeanie stood there staring for a minute. She had found a tux with tails, black with a red vest, black slacks, white shirt and black glossy shoes. Red bowtie and hanky completed the look. The short-haired wig was amazing but not as amazing as the fake mustache she had, it looked better than the one I had before this morning. "I love the dress" she finally said. "I love everything, you look great." "You look absolutely amazing. I have to say, though, I have never kissed someone with a mustache so this is going to be a little odd." "Well, come on in. Looks like you aren't completely ready yet." "Just this one last detail," I said. "There wasn't any way I could drive with this on. If you will excuse me for a moment." I went back to the bedroom and closed the door. It was a bit of a struggle keeping the dress out of the way while I got the underskirt on and zipped. I smoothed the dress down and checked myself in the mirror. The whole outfit together looked pretty good. I went back to join Jeanie. I sat down and Jeanie lifted my veil. She smiled at me, her eyes so familiar while the mustache made everything seem surreal. She examined my face. "Your make-up is incredible. How did you do all this?" "Well, actually, I didn't." I answered. I proceeded to tell her about my week of shopping, meeting Denise and her coming to my place to do the make-up. "I see," she said when I finally finished. "So, do I have competition to deal with now?" "Of course not. I told her all about us and how much I was hoping to get something long term between us." I wrapped my arms around her and kissed her lightly. "I need to ask one more question," she said quietly. "Are you having second thoughts about this?" I asked fearing she wanted to back out after all I had done. "No. I'm fine with it, but I've had all week to think on what you told me and I need to know if you ever thought about wanting to be with another man when you dress up." "There have been times that I wondered for the sheer sake of curiosity what it would be like, what you might feel like. But the actual idea of trying to go through with it doesn't appeal to me at all. I like the clothes, I like being with women. I would love it if I could find someone who can accept that part of me and not be threatened by it or feel it means more than what it is. And I would love it if it turns out you are that person. "Now, I hope saying all that while we are dressed for a wedding doesn't freak you out too bad!" She laughed a little bit. "No, not freaked out. And thanks, I suspected as much but wanted to hear it from you." "You seem to suspect a lot about what I thought were my little secrets. I wonder if you know more than I do about what I'm thinking." I bent down and kissed my groom. After a second she backed up. "Hey, don't smudge your lipstick. I want you perfect until we at least get there. Speaking of which, did you get a purse or clutch or something since you don't have pockets?" "Add another to the list of overlooked items" I frowned. "I could try and stick it in my garter but it might be too big to stay put." "You have a garter?" "I raised my skirts just high enough to show the garter above my knee." "What else have you got going on under there?" she smiled. I dropped my skirts. "Later, what do I do about my wallet and keys?" "I have something you can use." She went to the closet and came out with a small white clutch handing it to me. "Put what you need into this and we'll get a few things from the dining room. Don't get your whole wallet, there won't be enough room." "Um. Speaking of which, I think you will have to drive tonight. I've only driven in heels just this time and I doubt I could drive in all this dress now." "Yeah, you're right. Last thing I want to do is end up in an emergency room dressed like this." I collected some cash, credit cards, keys and license. Jeanie added some makeup I had brought and we headed out the car. Getting into the car was funny. I hadn't anticipated trying to get all that dress into the passenger seat. We both pushed and pulled and piled the material until Jeanie was able to close the door. I pressed down on the front of the dress so it was clear to see through all the windows. As I looked down another realization hit me. "What happened to your boobs?" I asked as Jeanie settled behind the wheel. She glanced down like she hadn't realized they weren't as prominent as normal. "Oh, I found a camisole that fit tight enough to make it seem like I was a bit over weight. I left the shirt and vest loose so you can't see that the stomach is smaller." We headed off down the road. I was so nervous about being out looking how I did. "Are you nervous?" I asked. "Yes, a bit. I am looking forward to this. It's going to be a lot of fun. Why, are you?" "Absolutely. I've never been much of a costume partier and I've never gone out in a dress, nor worn make-up, and I am going to meet a bunch of people I have never seen before. So, again, yeah I'm nervous. And that makes me more nervous about making this dress look terrible." Jeanie reached over and switched on the a/c, turned up the fan so that it blew cold air right at me. "Thanks, that helps." She just smiled and continued along down the road. We arrived at the party, there were already several cars out front and we could hear music drifting through the air. "Before we go in I have one question. What if someone asks why we chose this as our costumes?" I was a little unsure of myself at this last moment. "If asked, we say it just the way it happened, just leave out the details of the morning. I asked you to the party, suggested the costumes, we agreed it would be a great laugh and here we are." She smiled. Reached over and moved my veil down over my face. "Let's play it that we are just arriving at the church. You are still the bride to be." I smiled. I couldn't kiss her through the veil without smudging it so I reached over and fished around for the door handle letting myself out. We walked hand in hand to the door, I carried my little purse and she carried a couple bottles of wine that we were contributing. The door opened just as she was reaching for the doorbell. Amy was dressed as a 1920's flapper. She looked fabulous in silk and fringe. She stared for a moment at us trying to place us. Finally in a lower voice she asked "Jeanie?" Her voice rising as she asked "Brian?" "Hi!" Jeanie called out and gave her a hug. Amy gave a little squeal and hugged her then looked over Jeanie's shoulder at me. She started to reach toward the veil but I reached up first and lifted it a bit so she could see my face clearly. "Hi, it's been a while." "Oh, my God! You look amazing" she cried. "Come in! Come in!" We went in and mingled. There were costumes of many different designs, couples and singles. Nobody seemed overly concerned about our choice of costumes. Everyone complimented others. I wandered about straying not too far from my groom since I didn't know too many folks to start with. Suddenly I realized I had a problem. We had been there several hours and I needed to go to the bathroom. Put another check on the list of things I hadn't thought about. Wrestling the dress out of the way in the car was bad enough, now I needed to move it and not get it wet. Oh joy. I got to the bathroom and the door was locked. I patiently waited for whoever it was to finish. Finally the door opened and the flapper emerged. "Brian! I hope you are enjoying yourself" "Oh, absolutely. Having a terrific time. Quite a crowd you have here." "It is a wonderful group. I hope you and Jeanie become a regular part of it. I was talking with her this week and she is real excited about having you back." "I am just as excited and happy to be with her again. We are going to be spending some time together and see how it goes. But for right now, if you will excuse me, I need to get in there." "That's a lot of dress there. Are you going to be ok?" "I think I'll manage. It may take a while though." I closed the door and started trying to figure out how to accomplish my task. I tried a few different things and finally decided that I would have to remove the underskirt. Once I had that off I was able to drop my panties and gather enough of the dress to allow me to sit and take care of business. Once done it took another several minutes to get everything back in place again. I raised the veil and inspected my make-up. I decided to reapply the lipstick but otherwise Denise's artwork was intact. Another quick look in the mirror and I felt I could head back out. I opened the door and Amy was standing there. "Was I in there so long you need to go again?" I asked. "No, came back to get you. Jeanie would like a word." I followed Amy back out to the crowd and we found Jeanie chatting away with several folks. Even with a mustache and short hair I found her so pretty. When we got closer she suddenly turned so serious. I glanced around at the others but got no clue as to what was coming next. "I am tired of trying to see your face behind that veil," she started, "so we talked and decided there needs to be a wedding." She then dropped to one knee. "Will you marry me?" I was dumb-founded. I looked all around me trying to figure out what was going on. After a minute I realized I had stopped breathing. I looked back down and Jeanie was still there. Doubt was creeping into her eyes. "Oh, of course, yes! Sorry, I...I'm just so shocked." Everyone started laughing as a huge smile crossed her face. "Gary has agreed to perform the ceremony and I've asked my friend George here to be best man." "Well, this is just so sudden. Guess I'm lucky I'm dressed for the occasion." My senses were starting to realign again, taking longer as the wine was slowing things down a bit. I looked around at all the folks. "Amy, would you be my Matron of Honor?" "I would love it," she was bouncing up and down sending the fringe in a myriad of directions as she answered. We decided the ceremony would be outside where a light breeze had come up. I was grateful for it as I was getting very warm buried inside all the material. Gary was already dressed as the pope and the rest of the wedding party was made up of a bride, groom, flapper and zombie. It was perfect. Amy had gathered a couple flowers and tied them together for my bouquet. Someone else had fashioned together a couple rings out of twist ties. Gary kept the ceremony short and sweet. Finally reaching the "you may kiss the bride". Jeanie reached up to remove my veil, I had such a huge smile I wasn't sure I would be able to kiss her properly. It wasn't a problem and the crowd cheered and fresh drinks were poured. I tossed my bouquet to a crowd of women (though some were as female as I). I sat so Jeanie could remove my garter.The breeze felt good as she lifted my dress above my knees and slowly pushed it higher to get to the garter. I saw her eyes widen as she looked up under the dress and saw more than I had anticipated. She quickly dropped it back to my thighs and I pressed my hand down while scAmying the crowd, fortunately I think the light was dim enough that nobody except Jeanie got a view. She eyed me as she took hold of the garter and began sliding it down my leg, a slight smile playing at the corners of her mouth. She turned and fired it off to a bunch of guys (also not all male) while I rearranged my dress. The party seemed to be recharged. I looked at Amy and asked if I could use her bedroom for a moment. "You're not planning on consummating the marriage right now are you?" "Oh, no. I just think I need to get rid of some of the fluff under this dress." With permission I wandered back into the house. I pulled off the underskirt and left it lying on the bed. The dress, still fairly heavy, collapsed against my legs. The fabric felt cool and I was happy for the relief. I migrated back outside. I went to Jeanie, wine in hand, and put an arm around my new husband giving her a gentle squeeze. She looked me over and slid her arm around me, giving my butt a feel as she did. "Hm, we will be going home soon. I'm curious about what I am feeling," she whispered as she explored more of my behind. I looked down to be certain the front of the dress wasn't showing more. Fortunately there was still enough material to hide everything. About an hour later we headed for the door. I gathered my discarded underskirt and bid all good night. Jeanie drove us back home. "I know it's supposed to be your job but shall I carry you over the threshold?" I asked. I swept her up in my arms without giving her a chance to respond. She reached out and opened the door and I carried us in and straight to the bedroom. I set her on the bed pushing her back lying down. "Stay there," I whispered. I stepped back and removed the dress, it wasn't a nice smooth reveal, but I got there. Then I moved onto the bed straddling Jeanie. I started unbuttoning the vest as I watched her eyes checking me out. Her hands came up cupping my butt feeling the lace, lightly caressing me. I slid back off her and pulled her up so I could remove the jacket, vest, shirt and the camisole that was keeping her contained. She let out a sigh as pulled it off over her head. As she brought down her arms she reached out and lightly rubbed my cock through the lace. The feeling so intense I let my head drop back. I felt the parties sliding off releasing me. She took hold and I felt the warmth of her mouth on me. It felt so good I almost let her go on but I wanted to do this my way. I gently laid my hands on her shoulders and pushed her back down on the bed. She reluctantly released me. I knelt down and removed her shoes and socks and moved up to undo her belt and pants. I laughed a bit as I removed her pants exposing a pair of plaid boxers. I leaned up and gave her a small kiss on the mouth, then a little kiss on each nipple, then moved down and pulled her boxers off. I buried my face between her thighs and proceeded to pleasure her to the best of my ability. I believe I did a good job as it didn't take long before she locked her legs behind my back, arching her own back forcing my mouth harder against her and suddenly relaxed. I waited as her legs slowly dropped off me to the bed, gently kissing her thighs. I kissed her nipples again as I climbed back up on the bed, on top of her. My own erection was now screaming for attention. I kissed her neck and then whispered, "Can you take me now?" She took a breath and nodded. I repositioned myself and slowly entered her. I slid in easily since she was so wet. Slowly sliding in and out I waited for a response. Soon I felt her hips come up to meet my thrust. I pushed harder, trying to give all I had. The pace quickened, her legs wrapping around me again. Soon I pushed, she lifted rotating her hips taking me as deep as possible, I stopped and exploded. I squeezed her against me hard as I could, her arms wrapped around my shoulders just above the corset. I was spent and everything went limp. I could feel all her muscles relaxing as well but she still held me with her arms. After a few moments my brain started functioning again. "I think I need to get all this makeup off." "I'll help you. Get the rest of those clothes off. I'm ready to have the male you back. I've had enough girl-friend you for a while" I stripped off the remaining clothes and went into the bathroom where we scrubbed away the remaining evidence of my blushing bride. Then we went back to bed and snuggled up together, falling asleep in moments. She woke me the next morning by finishing what I stopped her from doing the night before. Before I could recover she went off to take a shower. After a few moments I joined her there and helped her wash. Then I cleaned up after she left. I dressed in my regular clothes and headed for the kitchen. She was putting together a light breakfast dressed in jeans and top. "Next weekend let's go do something. Wine tasting, hiking, something," she offered. "Sounds good to me" I answered. "Let's see what the weather looks like about mid-week before we decide." I gathered up all my things and headed for the door. I stopped and gave her a kiss I intended to carry her through the week. She returned it in kind and I headed out to the car. I waved and headed away realizing at that moment we were both still wearing the twist tie rings. Chapter 4 The Next Year Most weeks we stayed at our respective residences giving each other time and space. But the weekends, we took full advantage of the time we spent together. We would run off for wine tastings, or shows in the Bay Area or up to Tahoe. Sometimes we would hang out at her place or mine. Another thing we enjoyed doing together was playing golf. I got her a couple nice outfits to wear on the course, always with a skort. Though I knew it was shorts that looked like a skirt I couldn't help staring at her. One weekend we went to play and as she retrieved her ball on the first green she flashed her panties to me showing that she was wearing a skirt instead. I couldn't take my eyes off her all that day. Played the worst round I had played in years, and had the best time all the same. That night I showed her just how much I appreciated it. One weekend we were hanging out at my place. We were both wearing casual everyday dresses while enjoying a bottle of wine and music when suddenly the conversation changed. "Brian," she stood up and started pacing, "I love the time we are spending together and all the things we do, but I am starting to have a problem with the dresses, and the lingerie and all." "You want me to stop?" I asked as I looked at the dress I had on, a green shirt dress that was mid-shin in length. It was very comfortable and I liked wearing it a lot. "Or are you saying you want to stop wearing them?" "Don't try to be funny, I am serious," she chided. "We spend a lot of the week apart still and sometimes I feel the need to take care of business on my own. I have fallen so in love with you that you are the center of my fantasies." "And my wearing these things is interfering with those fantasies," I told her. "No," she exclaimed, "exactly the opposite! I close my eyes and I see you in lace panties, or pantyhose with no panties, or a short skirt and, Bam! I am done." "I'm confused, this is a bad thing?" I frowned trying to puzzle out what was bothering her. "Before we started this I had a wonderful little fantasy life. A normal fantasy life, if there is such a thing," she shook her head trying to make it clear what she was getting at. "I'd picture some nameless guy going down on me, or a naked stud pounding away, never a cock in lace!" "Baby," I tried to soothe her, "there isn't anything wrong with any kind of fantasy, you have found what works to trigger you best. I'm flattered." "What about you? What do you fantasize about?" "Well, I like to picture things that have already happened and maybe alter them a little. One favorite is when you removed my garter at the party. After you look up my dress and see the lace panty, instead of covering it with the dress, you reach up and pull it loose and give me a blow job right then and there with everyone watching. I cum in seconds." "So, public sex is a turn-on for you?" "No, I think the idea that I am so irresistible to you that you couldn't wait is the turn on." She sat back and thought about it for a while. "What else do you fantasize about?" "I'd rather not say," I explained. "These are things that I like to have for myself. You center in most of them, and I like that I have so many images in my mind of us together that I can make them seem so real." "OK, I guess I can appreciate that," she turned and dropped back down onto the couch, her dress flipping up a bit to mid-thigh. She didn't miss me watching. I leaned back, reached down and pulled my dress all the way up exposing my sparkly yellow panties. "What to help fuel more fantasies?" She grinned and reached over sliding her fingers under the edge of the panty forcing it to the side releasing me. As she leaned over to take me in her mouth I reached up under her dress slipping my finger into her panties and into her. That lasted only a couple moments before positions shifted and we were eye to eye with her riding me. * - * - * After a few months we decided we had enough of our own space and didn't need any more time on our own. We started looking for property and planning what our new home would look like. A bit of luck landed us a terrific couple acres in the foothills and we were able to start construction. Six months later inspections were completed and we were free to move in. It took us another couple weeks to sort everything out and get settled in but we finally popped the cork on a nice bottle of wine and settled down together beside the pool. We toasted as we watched the light fade from the tops of the mountains in the distance. It was still warm for late September and I decided to take advantage of remoteness of our new home. I went and got the bottle and refilled both our glasses. Instead of sitting down, I proceeded to strip off all my clothes. Jeanie sat and watched. I turned and jumped into the pool. As I surfaced I floated back away from the edge watching her. Finally she stood and stripped as she moved to the pool's edge. Rather than jumping in, she went to the stairs and slowly entered the water. I silently paddled my way toward her as she moved toward me. We met, kissed, and wrapped arms and legs around each other. Soon, we left the pool and made love on the patio. "I think I'm really going to like this place," I mused and I lay there holding her in the star-lit night. "Me, too" she murmured. "By the way, I got a call from Amy about another costume party next month. Want to go?" "Sure, I had a really good time last year. What do we do this year?" "Not sure. I want to change it up though." We talked for a while, moving inside when the air grew too cool. We went to the bedroom and I grabbed panties and a long silk nightgown. After slipping them on I turned and saw Jeanie in a sweatshirt preparing to pull on the sweatpants. "Is that new?" she asked. "I picked it up a couple months ago along with a few others, some are short and a couple of them are long. I decided to go long tonight since it is a little cool." "Well, I can see I am going to have to upgrade my wardrobe for times like this. I cannot let you be dressed better than I am." "Would you like to borrow one for tonight? I think I might have something you will like." She hesitated for a few seconds and then dropped the pants on the floor. "OK, just for tonight though." She pulled the sweatshirt off and walked over to me naked once again. She placed her hand against my chest running her fingers against the material. I saw her nipples tighten and felt mine doing the same under her touch. Her other hand slid around and down my back sliding down across the curve of my butt. "Thong?" she asked. It sounded like a note of disapproval in her voice. Disappointed, I quietly replied "Yes. I like the feel of the silk so much I decided to wear one. Not bad really, I wasn't sure I'd like it." "That's fine, and I understand. I'm going to need more than nightgowns it looks like." Her fingers traced the crack of my ass. "I think I might like it too. Now, give me something to put on, I want to finish this discussion before I get too distracted." I gave her another of the long silk nightgowns and she slipped it over her head. An adjustment for her breasts and I wasn't sure I could avoid being distracted. I reached over and ran my hand over the material giving her breast a squeeze as I did. "Doesn't this just feel so incredible?" "Yes, I have to agree, it most certainly does. Now, let's get back to Halloween and then I think we'll be ready for each other." "Well, I'm ready now, as you can tell, but what about going as Daphne and Shaggy from Scooby-Doo?" I asked. "Who gets to be Daphne?" she asked. "You, that changes it up. Besides, I'd like to spend the night looking at you in that short dress." I grinned and winked. "OK. It'll be a lot more comfortable than what you wore last year, and you get to drive this time! But, I'm not certain I want you to be Shaggy. Velma was short and wore a pleated skirt, right?" "Yeah, turtle neck sweater, pleated skirt, knee socks. Do you want to be her instead?" "I think so, and I want you to be Daphne." "Really, two years in a row with me in a dress, aren't you afraid people will start asking questions?" "To be honest, I don't care. I never thought I would be enjoying this as much as I do. And I like the effort you put out for me." "Well, I'd do almost anything for you. I am so happy with my life right now." "Good, then it's settled. Let's do some shopping this weekend. Perhaps we can find what we need and improve my wardrobe." It didn't take long before the nightgowns were pulled up and we were pleasuring each other until we stumbled onto bed and collapsed in a pile of silk covered bodies. We slept peacefully until late the next morning. * * * * * After a quick breakfast we jumped in the car and went off on our shopping spree. We bounced from store to store buying a couple things in each place. Most of the clothes were for her but I found a few things for myself. Her outfit was fairly easy to find but we couldn't find the purple sweater dress for me. We stopped for lunch, hunted some more, stopped for dinner. I was getting tired of all the getting in and out. We agreed to one more stop and then back to the house. It is always in the last place you look, they say. We found the dress, it wasn't perfect, but it was close enough. We bought it, congratulated each other with a kiss, and headed back home. Once there we put all the clothes away and settled in to watch a movie. I slept late the next day and woke to Velma standing at the end of the bed watching me. "I wanted to be sure it worked. I think you should check yours out as well," she said. "Good morning," I answered, still a bit groggy. "Good morning," she smiled. "Now get up and get ready." I fell out of bed and stumbled into the shower. It took a couple hours, I wanted to do it right since she seemed to be so intent on getting this right, but at last I looked in the mirror to finish touching up the make-up and decided this was as good as I could make it. "Well, it's about time. But I have to say, you look terrific! That dress fits you nice; you don't usually wear tight dresses." "Well between a particularly tight pair of panties and the tights I think I will be able to pull it off." "Terrific, let's go." "Go? Go where?" "We are going to spend the day in the City, lunch, shopping, dinner, whatever." "When did you decide this? You know I like the party idea, some friends and a theme, and being at home, and especially with you at home, but out in public? I don't know about this." "In answer to your first question, yesterday while we were shopping I was having such a good time and thinking how much fun I have going shopping with my girl-friends. Then I thought it was pretty much the same with you except yesterday you were my boy-friend helping me shop. "So, let's go, let's have a good day out together. We don't have to shop, we can go to a movie or museum, or whatever. In the City nobody will even recognize either one of us. And there, nobody will even care." I looked at her eyes and knew I couldn't deny her. I nodded, "Let me go get my purse." Her face lit up in a huge smile and she gave me a light kiss. "Thank you." To say I forgot about my situation that day would be completely untrue, I was hyperaware of it all day, but I decided I wouldn't let it prevent us from having a great day together. We got there just in time for a late lunch and then we covered the city museums, tourist sites, and the whole ball of wax. Finally it was getting late and we decided to have a late dinner and head for home. We got back in the car and began the long drive back. Jeanie was quiet watching the scenery pass by. "Are you ok?" I asked. She looked over at me then reached over and placed her hand on my leg just below the hem of the dress. "Did you have a good time today?" "Yes, I did. I was a bit tense at the beginning but I decided I wanted to be spending time with you. Within the first hour I saw you were right, nobody cared. I had a great time." "Good," she rubbed my leg a bit, "I'm glad. I started feeling guilty about pushing you into it. Next time we'll plan it together. That is if you want to do a next time." "I think I can handle it again." I reached over and laid my hand on the bare skin of her thigh and gave her a smile. We got home and went inside, cleaned ourselves' up and got into bed, too tired to do more than drop off to sleep. A few weeks later we reprised our roles as Daphne and Velma and were quite a hit again. We mingled and drank and joked about Scooby snacks. After a couple hours Jeanie turned to me, "I'd like to do a New Year's party at our house and I want it to be another costume party." "Costumes again?" I asked. "You sure everyone will be up for that?" "Sure, you wait and see" She wandered off to talk to Amy and then I heard Amy's voice over the crowd. "Listen up everyone! Jeanie has an announcement!" "Brian and I have decided to have a New Year's Eve party at our new home. Everyone here is invited because we know you like costume parties and this is going to be another costume party!" Everyone let out a cheer and I gave her a big smile. We spent another hour and said good night to everyone. During the drive home I asked, "so, do you have an idea of what you want to do for costumes?" "Of course, that is why I suggested it. How about the witches from 'Wizard of Oz'?" I thought about it for a moment. "OK. But you get to be Glenda the Good. I don't want to have to wear all that dress again. Besides, you make a prettier girl even though I think I'm getting pretty good at putting make-up on this face." "Agreed. It's the way I wanted it anyway. I want to do the sparkly dress for you." Chapter 5