Next Time I'll Wear The Dress free porn video

Next Time I'll Wear the Dress I was shoving paper around on my desk keeping half an eye on the clock waiting for lunch to come around. I had a date that I was really looking forward to. Doris and I had been friends a long time ago but hadn't been in touch for a while. We ran into each other over the weekend and decided it was time to meet up for some long lost conversation. Beep! Beep! Beep! The phone on my desk alerted me to an incoming call. I snatched the receiver from the cradle. "This is George," I answered in my most professional tone. "Ah, good, I caught you before you left," Doris' voice came through. My heart dropped, she was cancelling. "Yeah, I was hoping to get out of here in about ten minutes," I let my voice carry the disappointment I was feeling. "Something go wrong?" "Oh, no," she laughed. "Something is very right. I'm out front of your building. I just felt like the weather was too nice for a stuffy, crowded restaurant. Come on out and we'll discuss a new plan." "I'll be right there!" I dropped the phone back onto the base and practically sprinted from my office. I squinted into the bright sunlight as I emerged from the building and scanned for her car. I spotted it, trotted over, opened the passenger door and dropped into the seat. "Hi!" I leaned over and gave her a kiss. I didn't think about it, just did it because I've always had a strong attraction to her and was relieved when she returned it without hesitation. "Hi," Doris grinned. "So is this weather just incredible or what? I was thinking it might be just a perfect day for a picnic. I have a blanket I keep in the trunk; we could hit the drive-thru of a sandwich shop on the way to the park. Enjoy lunch by the creek. What do you think?" "I think that sounds great!" I grinned. "I'll buy lunch since you are driving." "Deal," Doris shifted into drive and we took off. She started talking about her day at work and explaining she felt she would have some extra time and not feel rushed to get back to the office. I told her I was in the same boat. As she went on talking about her day I looked her over. She was wearing a white dress with little green flowers adorning it. The skirt was loose and hung at her knees down between her legs as she drove. Tan wedge sandals on her feet. Fifteen minutes later I was spreading the blanket on a patch of grass and held the drinks as she carefully folded herself down onto the blanket tucking her dress around her. We talked about our lives and what was going on, or not going on, neither of us was dating anyone. Both of us going out on occasion with friends or doing a first date that never became a second date. "I would love it if we could go out again," I offered. "Been a few years since we tried it, things are a lot different now." "Oh," Doris started picking at her dress, checking the collar, making sure her skirt hadn't come loose, "I've thought about that too. You were always a nice guy. I just still wonder about us in a real relationship." She checked her collar again. "Is there something wrong?" I asked. She leaned toward me a little giving me a view down the front of her dress. "There is a guy over there staring at me, I just feel like something is exposed." "Well, until you leaned toward me I couldn't see anything," I assured her. "But thanks for the peek." "You've seen it all before," she answered and pressed the front of her dress back against her chest. "I just don't want some scum looking." I snickered. "There was a time you didn't care, hell you wore some skirts so short it was almost impossible not to see everything. You were quite adventurous back then." "I'm still adventurous," she defended herself. "I just prefer to share more with fewer people these days. You want another kiss? I'll even let you give my boob a squeeze as long as your hands are clean. I don't want any mustard stains on my dress." I was shocked. There were a lot of ways I had wanted this lunch to go but that was not anything I had expected. I picked up a napkin and made sure my hands were clean of any foreign substances. "You just proving how adventurous you are?" I scooted a little closer. "Yes," she grinned and leaned toward me, "and I've been thinking about you some. You were always good in bed before and I've just decided we ought to go out again. This will be a little preview." I leaned back a little. I was feeling outside myself and thought of a story I had heard back at a bar we both used to hang out at together. "How adventurous do you dare to be?" I couldn't help but lick my lips a bit. "Bet I can guess how much you weigh?" Doris frowned for a moment then the light went on. "You can't be serious." "I'll give you a kiss that will distract you all afternoon, you won't risk any stains on your dress, nobody will see anything, except me of course." She hesitated, her eyes darted over to where the man was still sitting, watching. She looked at me again. "I am wearing underwear." "Spanx?" "Do I look like I need Spanx?" "Not in the least, but a lot of women wear them these days," I grinned. "Been spending a lot of time with women in their Spanx?" she giggled. "Nope, but I do look around a lot," I ran a couple fingers under the edge of her dress against her knee. I could see her nipple getting hard through her dress. I couldn't believe she was going to accept the dare. "Fine, do it," she looked around. I lay down on the blanket. She looked around again then in one quick move and a swirl of her dress she was over me and the sunlight dimmed, filtered by the dress that now covered my upper body. I saw the lacy white panty that covered her and gently reached up and slipped my finger inside it. "Pretty panties, I like them." "Just get on with it before someone comes along," she urged me. I leaned up and let my tongue make first contact. I heard her suck in her breath, I don't think she expected me to go through with it. I sucked on her and a moment later she was pressed down on my face. I don't know whether it was my talent or being in public but it didn't take long before she let out a little scream. She started to move away from my face and I quickly reached up and got her panty back in place. She held her dress and collapsed onto the blanket. "Oh my God," she shuddered. "I can't believe you did that, that I let you do it." "So, regrets?" I asked as I wiped my face with one of the napkins. "Well, I'm grateful the guy over there didn't start jerking off," she looked like she just ate something bad. "But he certainly got a show. I bet he comes to the park every day for the next couple weeks hoping for another one." I laughed, "Well, next time I'll have to wear the dress and you can tell me how much I weigh." "That would be something," Doris looked at her watch. "I do need to go back to the office today. I think it is time we go." "Yeah, not much else we can accomplish here," I stood up and offered her a hand. She gracefully got to her feet, I picked up the trash and handed her the blanket. She folded it as she strolled toward her car; I detoured to a trash can and then joined her for the ride back to my office. When we arrived I wasn't sure what to do next. Kiss her? Ask her out? Just wait and call her later? "What would you think of coming over this weekend?" she asked before I could decide. "Yeah, sure, love to," I blurted. "OK," she laughed. "I'll call you later when I have a plan." She leaned over and kissed my cheek. "You ought to wash you face as soon as you can before someone notices that you might have been up to something at lunch." "Oh, yeah, good idea," I could feel my face getting warm. I was probably blushing all the way to my toenails. I got inside, went to the restroom and washed up, then went to my desk. It took a long time before I was able to get focused on my work and later that afternoon my phone rang again. "This is George," I immediately answered. "Hey," Doris answered. "Saturday morning, around 11? You good for that?" "Sure, no problem," I told her. "What are we going to be doing? How should I dress?" "Be casual," he told me. "See you Saturday." The line went dead. "Casual?" I asked my office wall. "Shorts and a t-shirt? Or Khakis and a polo?" I went back to trying to clear work from my desk. I walked up the stairs to the door with 1425 on it and knocked. I decided on blue jean shorts, concert tee and sandals. But, just in case, I had stashed khaki slacks, polo and shoes in the car in case I guessed wrong. I heard the lock turn and the door open. Doris was there in very short denim shorts and a white blouse knotted beneath her breasts baring her stomach. She looked incredible, and I felt I had guessed right on casual. Good start for me. "Hey, come on in!" she turned away from the door and started walking away before I could give her a hug, kiss, or anything. I walked in and closed the door. "I mixed up some chicken salad and have some crackers. You hungry for some lunch?" "Sure, sounds good." I met her in the kitchen. We ate and chatted. I didn't bring up the lunch date, though I was dying to find out how she was still feeling about it. After about 45 minutes I helped clean up. "So, you ready to get naked?" she grinned. "Huh?" I was caught totally off guard. "Oh, sure, with you any time." I tried to regain my composure. "Come with me," she took my hand and led me to the bedroom. Once there she told me, "Go ahead and get your clothes off, I'll be right back." I watched her disappear into her closet and quickly got undressed. Before I could decide whether to lie down on the bed or remain standing she came out and threw something at me. I caught it and held it out. It was a red knit dress. "Try that on," she moved to her dresser. "Huh?" I just stood there. "You said next time you'd wear the dress," she pulled open a drawer and started searching through it without looking back at me. "So I thought about that and the more I thought, the more I liked the idea. Ah, these should work." She walked to me and took the dress from my hands and handed me the other item. I examined it and discovered it was panties. I wondered if I was being punished for what I did at lunch but decided to go along with her for now; I was feeling pretty horny. I examined the panties, they looked like a regular pair, plenty of coverage except a lot of lace on the front as well as a little black satin bow. I carefully stepped into them, I was feeling a little shaky, and pulled them up my legs. Once I got them in place I realized the front didn't actually come up as high as the back but instead had a look more of a V that left me very exposed. "Hmm, I think this can work," Doris draped the dress over her arm and took hold of me, tucked me in to the lace. "How does that feel? I think they are tight enough to keep you in place." She ran her fingers along the lace that covered me. "Oh," I shuddered. The feeling was intense, unlike anything I had felt before. "Don't be getting ahead of the game here," Doris started adjusting the dress getting it ready to pull down over my head. "Arms up." I obeyed, shaking from the intensity of the feelings going on. The dress descended down my body and my head squeezed through the neck opening. It was sleeveless but the collar was a mock turtle neck. The rest of the dress was tight as well and Doris pulled it down to about halfway down my thighs. "Well, I don't think this will work," Doris looked me over. "You definitely can't do sleeveless, your shoulders are too muscly, and you can't do a dress this tight because the panties obviously can't hide you completely." She caressed the bulge in the dress sending more shivers through me. "Go ahead and take off the dress, I'll look for something else." I pulled the dress up and as it slid across the lace it practically drove me insane. I laid the dress on the bed and couldn't help but touch myself. I avoided the lace, I was afraid I wouldn't be able to stop. I ran my hand across the smooth material that covered my backside. It felt so nice. Was it silk? Satin? Nylon? I didn't know and didn't care. "OK, another dress," Doris emerged from the closet. "It seems you like those." "Yeah," my voice was shaking as much as my hands. "I guess so." "Good, because I think this dress will be great and you will have to wear a bra, probably would have anyway but I hadn't thought about it. So, hold onto this," she handed me a dress, "and I'll get you one." "Why are you doing this?" I finally asked. "Adventure," Doris answered. "I can see how excited you are about this, and believe me I am every bit as excited as you are. I would take you to bed right now except I got so excited by this idea that I don't want to take a chance of getting side tracked. Lay the dress on the bed and give me your arms again." She held out the bra. I looked at the lacy bands that hung from her hands and reached out toward her. She slipped the straps up my arms and turned me around. I felt it tighten as she stretched the ends together and hooked it. I pressed against the satiny cup and could feel my nipple behind it. "I'll find something to stuff the bra in a bit," she told me. "But let's get the dress on." I recognized the style as a shirt dress but this one seemed very dressy. The material felt as silky as the panties, and it shimmered shades of yellow and burnt orange. I slipped it on, the sleeves stopped at my elbows and were cuffed. I started buttoning the dress, a lapelled collar started just above my bra, I closed the dress down past my waist and was pulling it up to do more buttons. "Leave a couple at the bottom undone," Doris instructed me, "and here's the belt." I let the dress drop, it was several inches below my knee, but it gapped open to just above my knee before closing again. I found a couple string loops and fed the belt through them as I wrapped the belt around my waist and fastened it. When I pulled it tight it helped the skirt to fill out a bit more. "This is perfect," Doris clapped her hands. "We are going to have so much fun tonight. We do need to do a little touch up. Take the dress off again and we'll get everything done." I was confused. Tonight? I was still in a heightened state of excitement so I just did as I was told and after hanging the dress back up I followed Doris to the bathroom wearing just my panties and bra. I let Doris shave my legs and chest, then she sat me down and put make-up on my face. She styled my hair. She tried several things to create my boobs and finally decided on flour in sealed baggies. I dutifully put the dress back on. "Oh, my," Doris sighed. "You make a good girl. You look great!" I turned and look at myself in her mirror. I saw me in a dress and makeup. But that was what I expected to see. I looked to see what it was that made me so sure and couldn't identify anything. I closed my eyes and then looked again. I saw a young lady. She is attractive. I was beginning to understand about the magic of makeup. I looked at the front of my dress but it was too full to betray my secret. "OK," Doris broke in, "I'd like you to go wait in the living room while I get myself ready. Don't get anything on your dress, be careful how you sit to not get too wrinkly." I turned and went to the other room. I have been watching the way women move for a long time so when I got to the couch I knew to gather my dress to avoid sitting on it and wrinkling it. I sat there not knowing what to do with myself. I was also becoming aware of how warm I was feeling. My face felt warm from the makeup, I could feel sweat gathering around my bra and panties. I stood up and just walked around for a while. I liked the feeling of the dress caressing my legs, the lace still kept me extra sensitive and the dress would slide along the panty as I moved making me so aware of what all I had on. I reached up and gave my breast a squeeze, not too hard, I didn't want to rupture the baggie and get flour everywhere. But it was odd to feel this lump on my chest and I could feel pressure against my own skin and some weight on my shoulders from the straps. "Ready?" Doris called. "For what?" I answered nervously. "A night out," she responded and came into the room. If I had been holding something I would have dropped it. Doris was in a skin-tight deep blue dress. It had long sleeves which made the fact that it was as short as it could possibly be even more noticeable. She also had on high-heeled thigh-high tan suede boots that left just a few inches of bare skin visible. Makeup and hair were exceptional. "I'm afraid there is one more thing we are going to need, well you are," she stared down at my feet. "Your sandals are completely wrong. That dress really needs to be worn with heels and my shoes won't fit you so we will have to make a stop at a shoe store before dinner." "Wait," I was starting to realize she was planning on actually going somewhere. I had been fooling myself that this was going to be an indoor thing just between us. "We are going out?" My voice squeaked. "Oh, yes," Doris smiled. "I thought we would go out to dinner and then maybe some dancing depending on how that went. Midtown. I figured nobody would care down there if they figured anything out." Midtown did make sense, lots of gay and lesbian bars down there. Restaurants wouldn't be an issue since a large part of their clientele would be regulars from that area. It didn't make me feel any more at ease. "Adventure," Doris whispered. "The other day you made me realize how much of a rut I have allowed myself to get into. Every once in a while the envelope needs to be pushed. I was quite the recipient of that at lunch the other day and believe me, you will be tonight." With that we were out the door. I walked down the stairs and to the space where her car was parked. I was nervous as hell but couldn't take my eyes off Doris. So many thoughts around how long we had been apart, how we suddenly seemed to jump into a relationship again. What led me to offer to do that at lunch? Has she changed so much that she is going to try and humiliate me somehow tonight? She never seemed cruel before and why would she now? All these things rolled through my head during the short walk. I got into the car in the passenger seat. I looked over and stared down at Doris' legs. "It has been a very long time since I dared wear anything as short as this," she informed me as she started the car. "But, I felt like if I was going to put you out of your comfort zone in a dress, the least I could so it push my own comfort zone, and hopefully give you something to enjoy while I was at it. I can still pull this off, can't I?" "Oh my God, yes," I immediately spilled. "I am just confused about why you felt you had to dress me up like this. I was wondering if you were upset with me about something from the other day." "Simple," she watched the road carefully as she piloted the car toward our destination. "I was a complete wreck that afternoon after our lunch. Not so much in a bad way though I questioned myself in that I so readily accepted your offer. Granted, we had a past history but it has been a few years. I was never in the habit of engaging in that sort of behavior with anyone that quickly. As I said before I realized I was in a rut. "So, I am sitting at my desk, and I kept thinking about it. And I'd find myself fingering myself. Thank God there wasn't anyone around to see. But that is why I wanted you in lace, you know how sexy it can feel and how good. But you said next time you'd wear the dress and I started thinking about what that could be like. When I called you I didn't have any kind of a plan. Just come to my place and dress you up for a laugh. But the more I thought about it the more I wanted more than that. So, here we are. And here we are." I looked up and realized we were parked in a shopping area. I spotted a shoe store close by. "We are going in there?" I gulped. "Don't worry," Doris reached down and laid a hand on my thigh. "Don't talk, you haven't got the right voice yet but otherwise nobody will have a clue. Oh, your name. I can't call you George, Georgia?" I could feel my heart beating a mile a minute. "Uh, no, I don't really like that," I tried to think of something. Girls names all flowed around my brain, Doris waited patiently. Something generic like Pat? Terry? No. "Gia," I whispered. "Gia?" Doris answered. "Yeah, I like it. It fits you. Let's get you some shoes." "Wait," I suddenly realized my wallet was in my shorts back at her apartment. "I don't have any money." "I know," Doris nodded. "I should have thought to give you a purse. No worries though, tonight it on me: shoes, dinner, drinks. Now let's go." She pushed her door open and stepped out. I watched her go first unable to look away. She did it gracefully and gave her dress a tug back down once standing. I extracted myself from the car, made sure my dress was hanging right and not clinging to anything. I followed her into the store. There were a few other customers there. A few women gave Doris a nasty look. They could never pull off the same look and I wrote it up to jealousy. I followed her down one aisle. "Best guess," she spoke low enough to not be overheard, "is that you should be somewhere in these sizes. I want a sandal with a pretty good heel on it. Wide, but not too high. You'd likely break an ankle if you tried to wear a heel like this." She lifted one foot. "Take a seat on that bench, I'll pick out some shoes." I tried on a couple before we determined the right size. Then a couple styles before Doris was satisfied. I stood up and took a few steps. It seemed odd being up on my toes so much but the heel was stable enough that I didn't wobble too badly. Doris stashed my own sandals in the box and we went to the counter. The bored clerk rang them up, Doris swiped her card, scribbled her signature and we were back in the car. "Now I think that was the finishing piece," Doris told me as she backed out. "You look fabulous. Feeling any better after your first encounter with other people, Gia?" Goosebumps travelled up and down my body. "Well, one thing I was appreciative of was that everyone seemed to be more interested in you than me. It helped me get through." "That may change as we go through the evening," she warned me. "The places we are going they'll be checking everyone out." That made my stomach turn over. She drove us into Midtown, the streets were crowded with people. There were groups, couples, and singles all wandering past restaurants, clubs and stores. I was starting to get sweaty again worried about mixing in with all these people. Then I spotted three women, though they were obviously not female. There had to be a drag show nearby that they were going to be attending. Oddly enough it made me feel better for some reason. I picked at my dress as I waited for Doris to find a place to park. She pulled into a public lot, found a place and got the car parked. We got out and began a long walk to the restaurant. We talked, or more she talked about things, I kept my mouth shut as much as possible. I couldn't help but take inventory of how I was feeling. The light material of the dress sliding along my legs, my knees appearing and disappearing through the slit in the front of the dress, the way my bra fit, my panties, the way my feet felt and how I could feel the shift in the way I was walking, I had added a little wiggle to my walk. A couple blocks later we came to the restaurant. A nice place, not a four- star place, but it looked nice. Doris spoke to the maitre'D and we were told a table would be ready soon. I took a seat in the waiting area, my feet were already a little sore from the walk. Doris sat beside me crossing her legs in one smooth motion. I was still enraptured by how short her dress was. Ten minutes later we were shown to a table. Doris insisted on sitting on the bench side next to me so we could look out at the restaurant together. She ordered water and a bottle of wine which I was extremely grateful for because I seriously needed alcohol. My first glass disappeared before the appetizer made it to the table. Doris poured another glass and reached over with a hand on my thigh. "Slow down, I don't want you so drunk you can't stand and you'll break an ankle on those heels." I nodded, started to reach for the freshly poured glass, and withdrew my hand paying heed to the warning. It was then that I noticed the lipstick stain on the glass. The realization that I had left it there sent a tingle through me. And I was aware that Doris' hand was still resting on my thigh. And that led to a different response which made me even more aware of my lace panties. And that got me to sweating again. I was grateful when the salads arrived and it allowed me to focus on something else. The restaurant was crowded and I was certain people would be staring at me but whenever I scanned the crowded tables all I saw were people consumed with their own company and the food or drink in front of them. Doris and I were able to talk since she was sitting so close and the place was so noisy that I knew nobody could overhear us. I became a little less worried again and oddly comfortable with my situation. I crossed my legs under the table and adjusted my dress without really thinking about it. Dinner came and went along with a second bottle of wine. I was feeling a bit tipsy but not sloppy drunk; I could still manage walking in the heels. Doris paid the check and we left the restaurant. The cooler air outside felt good as she led the way to the next stop and we entered a club filled with women. As crowded as it was I was certain someone would figure me out for what I was and cause a problem. Doris found a small table, ordered a couple of drinks and paid for them when they arrived. "Come on, let's dance." She grabbed my hand before I had a chance to answer and pulled me to the dance floor. It was body to body, strobe lights, lasers, colored spots flashed the mass of women as it ebbed and flowed with the music. I got bumped and maybe even groped as we danced. I found I liked dancing as a woman. I liked making my dress swirl and would take handfuls and swing it back and forth. I even tried shaking my boobs at Doris which elicited a laugh. I was starting to get to a point where I needed a break and Doris seemed to reach it at the same time. She grabbed my hand and led me off the floor. But instead of heading to our table, she pulled me through a door marked "W". We waited for a moment looking for an open stall. I spent the time trying not to stare at two girls making out; one had her hand down the front of the other's pants. At last a door opened and Doris pulled me into the stall and pushed the door closed. I watched as she pulled her dress up to her waist and sat on the toilet. A small patch of blue fabric that matched the color of her dress still maintained some form of modesty. I was confused, I thought she needed to pee and that was why we were here. Instead she reached out and up my dress. "Hold this up, please. Time to weigh you." I was stunned, and immediately excited. I lifted my dress higher exposing my black lacy underwear to her. She didn't rush into it as I did in the park that day. She stroked me through the lace, slid her fingers along the satiny parts. I was aching for her to do more and fortunately didn't tease me too long. She pulled me free of the panty, then lowered it enough to expose all of me to her. My hands shook trying to hold my dress up. My knees wobbled trying to maintain balance on the heels. The bra seemed to get tighter when I tried to take a deeper breath as her mouth performed its magic on me. While I felt like it lasted forever, I was done in what was probably minutes. Doris put me back together, took my dress from my hands smoothing it out then finally stood and pulled her dress back down. "Do you need to go while we're here?" she grinned. I just shook my head no. The toilet flushed automatically. We exited the stall and went to the mirror. Doris pulled a lipstick from her purse and handed it to me. She took another and began touching up her lips. I did the same. We went back to the table, drank some water, and then after a little rest went back to the dance floor. Suddenly the lights came up, it was closing time. We flowed out the door with the rest of the crowd. We were making our way back toward the car when we heard some idiot yelling out obscenities as they drove by. These are the very same fools that had me scared most of this night. Now, walking along with Doris, feeling the breeze pull at my dress I wonder how I would have reacted if something had happened. We got in the car and went back to her place. "I can't believe I did that," I exclaimed as soon as the door was closed. "I can't believe you did that. What I did to you was over in a couple minutes. We've been preparing, doing, whatevering for fifteen hours now. Why?" "I've told you why a couple times," she shook her head. "Don't you believe me? Now, do you want to spend the night? Ready to go to bed?" "Yeah, I'd love to stay," I moved toward her and wrapped my arms around her. We kissed for several moments. "OK," she broke it off, "we both need to get this makeup off. Not good to sleep in it. That will take a bit." She led me to the bathroom. We each stripped off our dresses and proceeded to clean up, me taking instruction from her. Once clean we walked back to the bedroom, helped each other remove our bras, pushed our panties to the floor and climbed onto the bed. By the time I laid back I could see the daylight starting to brighten the curtains. I fell asleep a moment later. We woke up later that afternoon. I showered first at her insistence. Then dressed in the clothes that I had worn only a short time the day before when I arrived. "So, I guess I ought to be heading back to my place," I told her. I didn't want to but I knew I needed to. "I really had a great time with you, the whole time." "I did too," Doris grinned, came to me and wrapped her arms around my neck. "So, what's next?" "More lunches, more dinners, more whatever to spend time together," I pulled her close to me. "I would like to make a real go of it with you this time. If you want to know the next adventure, I couldn't say. Opportunity led to the first one. You created the second one." "Truth be told, yesterday was a lot of fun," she kissed me, "I didn't know what it would be like compared to what I imagined but I wasn't disappointed. Would it freak you out a lot if I told you I might want to do it again? You don't have to if you don't want. It was way out there on the weird scale for you I'm sure. Have you ever worn a dress before? Ever get into your mother's things growing up?" "Um, first, no, never worn a dress before, never got into my mom's stuff, never had that desire I guess," I confessed. "However, it was a lot of fun and if you had a plan to want to try something again, I think I could be game." "Really?" she beamed. "I think it might be something I want to do once in a while. If you've never done anything with girl's clothes I think we could have a real adventure trying things." "Sounds like you really are excited by the idea," I laughed. "But I'm game if you are." "I can't believe I really want to do this," she giggled. "So, lunch this week?" I asked. "I'll have to call you once my schedule gets set," she moved away from me and toward the door. I followed close behind. "Sounds good," I kissed her long and deep. "I'll be waiting on your call." I walked down to my car, got in and began the drive home. I thought about the day and night before and wondered what more she might come up with. I knew it didn't matter; I'd do it with her. I was surprised at how much I enjoyed wearing her clothes, and it wasn't just the culmination in the stall of that bathroom. I knew next time I'd be able to relax and enjoy being with Doris as her girlfriend the next time she wanted to do it. Beep! Beep! Beep! I snagged the phone, "This is George." "Hey, Sweetie," Doris cooed at me. "Hi, Babe, how are you doing today?" "Missing you," she complained. "I haven't seen you in almost a week. Wanted to see of you would like to meet after work for a drink." "I'd love to," I perked right up. "Good," I could practically hear her grinning. She gave me the name of the bar and we hung up the phones. We've been going out for three months now and we've kept it kinda light getting started again. Oh, we spend plenty of time together over the weekends, and an occasional dinner date during the week. The clock finally ticked over to allow my release. I cleaned up my desk and made a brisk walk to the car then sped off to meet my sweetheart. I got to the bar, parked and walked inside. At first I was blind due to changing from light to dark but eventually my eyes adjusted and I spotted Doris over at a table. She already had a drink so I went to the bar, ordered a beer, and then joined her. "Hi," I slipped in beside her and we kissed. "Great idea meeting up today." "Well, for some reason I just couldn't get you of my mind today," she teased. I knew when I saw her why, she was wearing the dress I had worn on our dinner date back when we were just starting again, and that made me think of the picnic. Both adventures that took me outside my comfort zone, but I thoroughly enjoyed both. "I am wearing the same bra, too," she whispered in my ear. "But I couldn't find the panties you wore. Have you stolen my panties?" My mouth went dry. I realized I was caught. "Oh, yeah." I coughed, drank my beer to try and clear my throat. "It was a couple weekends ago, I saw them sitting on some laundry that you hadn't put away yet. I don't know what came over me. I picked them up, just to feel them and then I stuck them in my pocket. I keep meaning to return them." Suddenly I was aware of her hand rubbing against my crotch. "Are you wearing them now?" "No!" I said too loud, then softer, "no. I have worn them around the house a couple times. I'm sorry, I shouldn't have taken them." "No, you shouldn't have," Doris withdrew her hand and sipped her drink. "You should have asked me first." "You haven't mentioned anything about that evening. I thought maybe it was just a one-time deal," I tried to explain. "After that though, I couldn't stop thinking about how it felt. Are you mad?" "Possibly," she stared out at the bar. Then a grin broke across her face. "Mad about you. But since you've confirmed what I suspected when I couldn't find them I've decided it is time for a new adventure because I have thought about it a lot since that day but I was afraid you might get weirded out if I asked you to do it again too soon. Today at work I was given two tickets to a formal charity event. Gia and I are going to attend." I was stunned. I had been secretly hoping Doris would suggest another outing with Gia, but a charity event? That was a different type of crowd than what I was hoping for. "It is this Saturday," she went on. "Fortunately, I have a dress I bought a year ago that I never got to wear. And I have another that you can wear; I think you'll like it. We are going to have a great time! How about you show up early Saturday morning? It starts at four with a dinner, then music, silent auction and other things." "OK," I muttered too stunned to say anything more. I wondered if I hadn't stolen her panties if she would still have decided it had to be Gia she wanted to go along. Saturday morning I showed up at Doris's apartment again. She let me in wearing a long robe. "You ready?" she asked. "Do we need to do any shaving before we start?" "No, I got up early and shaved everything," I told her. I was in a strange combination of excitement and fear once again. "Oh, these are clean." I pulled her panties from my pocket and handed them to her. "Thanks," she put them in a pocket of her robe. "You'll wear something different tonight. You should experience as much as possible I think. And I think you'll like what I have planned. Come on, let's get you into your lingerie." I followed her into her bedroom. She pulled the panties from her pocket, tossed them into a drawer, and then with her back tome she peeled her rob off and let it drop to the floor. I was instantly excited. "It's called a bustier, if you didn't know," she said and began to slowly turn around. It fit her from about her hips to her breasts, her rear was naked except a small black strip that disappeared into the crack of her ass. The bustier was almost sheer black. She turned completely, I could not see her nipples, the cups were the densest part. And the panty was no larger than a playing card, also not transparent. Garters connected the bustier to the black stockings that encased her legs attached to the wide lace band at the top of them. "Oh, wow," I sighed. "Thank you," she wiggled her way over to me. "I'm sure we'll have a lot of fun tonight when we get home. I just hope you like me in my dress as much as this. But first, a surprise." "A surprise?" I gulped. I didn't know if I wanted a surprise. She reached into a bag beside her dresser. "Look what I found!" she held up a strip of something. As it turned I saw nipples and realized it was fake boobs. She slipped it around my chest like a strapless bra. "Oh, yes, that will work. A little makeup around the edges and it will blend right in. The skin tone is almost perfect." I looked down at my breasts. It was a great improvement from what we tried the first time. They were bigger but not too big. I reached up and felt myself up a bit. "I hope you don't get more interested in them than me," Doris teased. "Too bad you can't really feel them. Now, let's get you into your bustier." She wrapped the black satiny material around me and began fastening the back. "Reach into the bra and adjust your boobs. Make sure they fit right." I did as I was told and getting hornier by the minute. At the same time I noticed it was getting harder to breath. I stood a bit straighter and felt the last of the hooks getting put together. The garters tickled my thighs as the dangled there. "Not only do you get to enjoy the feeling of all these wonderful clothes," Doris stepped back around me, "but you'll understand the pains we go through to look as good as we do. Stockings next." She pulled two wispy black ribbons from a drawer. "Sit down, and do like this." I watched as she gathered the stocking onto her fingers. I stretched my leg out and she pulled the stocking over my toes then gently worked it up my leg until she had me stand again. She demonstrated how to connect them to the garter. I accepted the other one and tried to duplicate the effort. I was pretty successful except I had issues trying to connect the garter on the back of my leg. After giggling a bit she helped me out then said," it takes practice, now shoes." I gasped when I saw them. "There is no way I can do that." There wasn't really a whole lot to the shoe: a toe box, the sole, a small heel guard with an ankle strap, and the heel itself. The heel was the issue. It looked like it was ten inches tall and thin as a hair. "You can do it," Doris insisted. "I've worn taller than these, these are only three inches. They are narrow compared to what you wore the other night but a little practice and you'll be strutting them like a pro." She put them on my feet and strapped me in. "One last thing." She turned and fetched a pair of panties from the drawer and tossed them to me. I looked at them. This time no lace and it seemed a lot more material. I slipped them on with a slight problem of getting them hung on my heels. Once they were halfway up my thighs I stood for the first time. I felt a little dizzy, like I was suddenly towering over everything. One of my ankles tried to turn but I shifted and caught myself. I pulled the panties up to just below the edge of the bustier. They were cut high to the hips and front and back provided complete coverage, sort of. They were very sheer. I saw myself in the mirror and really could see everything in the mirror. I carefully turned around to look at the back, just as sheer. Doris joined me, wrapped an arm around my waist and looked into the mirror with me. "Both all in black but still quite different, huh?" she whispered. "Our dresses will be a lot different. And we still have some things to do. I need to paint your fingernails. Don't worry, we'll be able to clean it off before you go back to work. I'll do that, then work on your make-up. After I do mine we'll slip into our dresses and be on our way." We chatted while I watched her brush my nails with a dark red color. Then she instructed me not to allow them to get smudged while she did my make- up. It was the second time I found myself sitting in a chair in lingerie getting makeup applied to my face. Last time I was scared and didn't know what was coming: a night out on the town. This time I know what I am in for, and oddly enough, I feel more at peace. The fear I felt when I first heard the plan has passed. I'm actually looking forward to it and I am stunned at that revelation. "Go practice walking," Doris instructed, "while I get myself ready. If you need a robe, there is one hanging on the back of the bedroom door. Help yourself." I stood and wobbled out toward the living room. Short of someone knocking on the door I didn't feel I needed a robe. I was actually feeling pretty sexy and wanted to strut my stuff. Needless to say I nearly broke my ankle a couple times while strutting my stuff, but by the time Doris called me back to the bedroom to put on my dress I was walking fairly well. As long as I didn't have to run I felt like I could get through the night. When I came in Doris was standing there in a burgundy dress. The top was lace, the sleeve was just a touch of lace that lay halfway down her arm leaving her shoulders and upper chest bare. The skirt was layered and ended just above her knees. She looked amazing. "Wow!" I complimented her with the only word that came to mind. "Thank you," she turned a complete circle making the skirt flair out as she spun. "I hope you like your dress just as much." She helped me step into my dress. It was black and once in place I found the dress was layered, the top layer was sheer and the back reached down to mid-calf, the front just above my knee. Under was a dress that fit tighter to mid-thigh. The top was lace with an underlay that covered up to the top of the bustier and lace covered my upper chest, shoulders, and back with sleeves that reached halfway down to my elbows. "OK, now a necklace, a couple earrings," she narrated as she adorned me. "I had to get some clip-ons since your ears aren't pierced. And let's take a look." We stood side by side looking at ourselves in the mirror. I was thrilled with my look. And over the moon about her's. I let my fingers rove over the bare skin on her back while we stood there. "I thought the gold jewelry would help but you have just too much black. I think we need to change your stockings, nude will help. Take your stockings off." I sat on the bed and pulled my dress up. I was able to quickly undo the garters, remove my shoes and the stockings. Doris handed me a beige puff of nylon. "You'll notice there is a seam on those," she told me as she retrieved the black stockings and went to put them away in a drawer. "Take your time and try and keep the seam straight as you pull them up your legs." It took some effort and some twisting around to see around my dress piled around me as I pulled them up. But I did finally manage to get them on, felt they were straight enough and got the front garters attached again. I struggled a lot trying to so the back ones again, especially while trying to hold my dress up out of the way. "Let me help," Doris said as she sat on the bed. "This is easier without a dress on, or a dress you can pull up over your hips. I held my dress up and felt her hooking the garters to the stockings. She pinched at them a bit straightening the seam in a couple places. Then I felt her hand caressing my rear, then she reached around to the front. It felt great and I wobbled a little on my heels. "Hmmph, sorry," she pulled her hand away. "Pull your dress down before we start something and miss the whole evening." "I can be quick," I offered. "Later," she brushed my dress down as I let it loose. "Now, that's much better. You don't look like you are going to a funeral now." I laughed. "I don't know how many funerals I'd attend in a dress." "Before three months ago how many dinners or charity events did you expect to go to in a dress?" "Good point," I conceded. She handed me a small clutch with some things I might need during the evening and we went out the door. Once again she drove. We talked about how excited we were to be going on another adventure. I admitted that I was excited to be going out with her again as Gia and how much I appreciated her help. We worked on me trying to find a voice that I could use while we talked around other people. "I can't believe how much I am enjoying being with Gia again," she told me while waiting in line for the valet. "I am glad we've discovered this part of ourselves. I'm happy we discovered each other again. The hall was huge with large round tables. Buffet stations were in each corner of the room each with its own cuisine: American, Mexican, Italian, and desserts. We wandered around looking then prepared our plates. Hungry as I felt I didn't think I could eat a lot in the clothes I was wearing. That turned out to be correct. Even after a few bites I felt like my dress was getting tighter. Once dinner was over we were told the dessert bar would be moved to the hall outside. The inside would be converted into a dance floor with a live band. So we left and took an escalator down to another hall that had the silent auction at one end, casino games at the other. We toured the auction looking at the various items: sports memorabilia, art, gift cards to various restaurant, spas, and stores. We wandered over to the casino games and decided to play some blackjack. I pulled $20 from my purse to buy chips and we played for about an hour. Doris was ready to go back up to the dancing, we could hear the steady thump of the beat reverberating from upstairs so we gave the chips we had to the others at the table and turned to leave. "Doris?" a lady's voice called. We both turned. "Sandy? Really!" Doris hugged a woman in a tight gold strapless dress. "What are you doing here?" "Probably same as you, just looking to have a good time, support a decent charity. It's been what? Five years?" Sandy stepped back to look Doris over again. "You look amazing." "At least five," Doris answered, "and you look pretty awesome yourself. Not many could pull off that dress but your coloring you look great as always. Oh, I'm sorry, I need you to meet Gia, my date for tonight." "Your date?" Sandy cocked an eyebrow. "Hi Gia, I'm Sandy." "Hi," I answered unsure of what else to say. "Yes, we've become great friends," Doris answered. "I'm seeing a man named George before you go off spreading some rumor." "Oh, you are such a tease. I thought I had something really juicy," Sandy laughed. "Let's get together and catch up soon." "I'd like that," Doris answered. "How about brunch tomorrow? Gia and I are needing to do a little shopping. Was thinking about heading to that little open-air mall outside town. They have some good shops and a restaurant that does an exceptional brunch." "That sounds like a great idea!" Sandy clapped her hands. "Around eleven? Great." She hugged Doris and blew an air kiss. "Nice meeting you, Gia! See you both tomorrow." I watched Sandy disappear into the crowd and turned to Doris. "What the Hell? Shopping with Gia tomorrow? I can't do that!" "Of course you can," Doris assured me. "You've been amazing both times we've gone out and you are getting better. This will just be a little different. Now, let's go dance." I followed her back up to the ballroom and we went to the dance floor. It took me a few minutes to clear my head of the challenge that I felt tomorrow would bring but once I convinced myself that I didn't need to worry until the next day, I started having a good time. And I could see once I did Doris immediately brightened up and did as well. I danced until my feet required a rest, found a drink and a little table off to the side. Doris joined me of course. "This has been a fabulous night," Doris leaned in and hugged my arm. "You've got to be exhausted, and your feet must be killing you not being used to those shoes." "Not exhausted, a little tired, a little sweaty," I laughed. "But my feet are the reason I had to sit down." "If you can handle it," Doris suggested, "fifteen minutes rest, one more dance, then we can go home. Are you up for that?" I gave her a big smile and nodded. An hour later we were trudging up the stairs to her apartment. Once inside we helped each other out of our dresses, shoes were discarded, and before we could go much further we were in each other's arms. Quite some time later, a lot more disheveled, we stripped off the remainder of our lingerie, I removed my boobs, washed our faces and crawled into bed naked. We were asleep in seconds. I felt like I'd just gotten to sleep when I felt Doris kissing me on my neck. It was a pleasant way to wake up even if I didn't want to. I wrapped an arm around her and pulled her close. "We need to get busy," she whispered. "Big day of shopping ahead." That woke me up. I'd forgotten about that. "Couldn't you just say I couldn't make it and you can go meet your friend and do whatever shopping you need." "But the shopping is for you," Doris explained. "I don't mind sharing my clothes with Gia when I decide we should go out, but I don't want you stealing my panties any more. Or anything else for that matter, so we are going to be getting you a few things." I thought of reassuring her I wouldn't be doing that. That getting caught once was enough but I had a feeling that wouldn't last long. Another few months would pass and if Gia hadn't made an appearance I would likely be tempted to pilfer something. I slipped out of bed and went to the shower. A couple hours later Doris and I headed out the door. This time I was in a red t-shirt and denim miniskirt. I thought the skirt was too short, Doris assured me it was just right. She was in a flowy layered mini with a white blouse. She'd also been real careful with my makeup doing it just so for a daytime excursion. On the drive there Doris gave me the sizes of the dresses I had worn, the panties, my shoes, and my bra size. It wouldn't do well for me to be shopping for clothes and not know my size. We got to the restaurant, got seated without any second looks, and ordered a couple mimosas. We chatted for about ten minutes when Sandy rushed up to the table. "Hi, sorry I'm late, so much trouble getting started after last night but so excited to get to see you today," she ran on without taking a breath. Then turned to the waitress, "Bloody Mary, please." She sat down. We ordered, drank, and they talked through most of the next hour. Occasionally I got pulled in to the conversation but I actually enjoyed listening to them girl talk when at least Sandy didn't think any men were around. "So," Sandy started to push away the dishes in front of her, "what are you shopping for today?" "Gia needed a few things. The weather has been rather exceptional lately so I thought this would be a great way to spend the day," Doris explained. "Happen to be looking for anything formal?" Sandy pressed. "Not really, last night was a lucky break for the tickets, why?" Doris pressed. "Well, there is a dress shop here, opened a few years ago. Really quite nice," Sandy went on to explain. "It is a bit unusual though. The owner is very customer oriented, does most of the selling at the store herself. Provides a really nice atmosphere to everyone. She has a place for the husbands to relax while they wait on their wives and even caters to men who want to shop there! Can you imagine! But that isn't even the best part. Her husband is there quite often and is said to have impeccable taste in women's clothes. He even wears some of the dresses around the shop himself!" I drank what was left in my glass and nervously shot a glance at Doris. "Well, that is something," Doris answered. "If I need to shop for another formal I think I'll have to go there. I like the idea of an open-minded shop owner. And someone who takes enough pride in their work to do some of it themselves instead of just hiring others to do it for her. And her husband, well, he must be something exceptional to do things for her like that. I bet they have quite a story." "I've only gotten things second hand," Sandy went on, "but I hear they are quite friendly and open to talk about it. I can't imagine having a husband running around in a dress all day. I wonder if he sleeps in a nightgown too? That would just be too much." "Sandy," Doris challenged, "are you saying that if you met a man who seemed perfect in every way: good looks, good job, great personality. Then you discovered he likes wearing a dress on occasion you would just break it off?" "I'm afraid I would," Sandy huffed, "and I bet you would too. I mean, how could you trust him? One day you might discover him running around midtown hooking up with the boys down there." Doris laughed before she could stop herself. "Dear, I don't think it works that way, at least not for everyone." "Well, I don't think I could take any chances like that," Sandy answered. She pulled some money from her purse. "I'm afraid I don't have time to do any shopping today, but I had a wonderful time catching up. Let's do it again sometime soon. Gia, good to see you again." She turned and left. "What was that about?" I asked. "Sandy is a bit of a prude and quite a gossiper," Doris explained. "She just was dying to spread some dirt about that shop and expects everyone to relish in someone else's issues. Sometimes though, what she perceives as someone's issues isn't one at all and if you don't play her game she gets huffy. I'd forgotten how petty she can be, I think that is why we lost contact all those years ago. I got tired of it. So, let's go get you a few things. And maybe, one day, we can find something where we can go to that shop and do some shopping for a couple formal dresses. Now that I know a bit about it I think I'd like to go there. But for now, let's get you a couple complete outfits just for you. And you know what else? I think we ought to pick up a couple nightgowns. Ever sleep in a nightgown?" I just shook my head. Of course I hadn't and I knew she knew that. "Well we'll just have to try it out and see how we like it," she put out some money and I added to it. We strolled out of the restaurant and began our day of shopping. After a few stops I decided I needed to ask a question I had on my mind. "What would you think of finding a place to live together?" "You would still need your own clothes," Doris answered like it was an everyday question. "Who would I see more of? George or Gia?" "George, I think. Does it matter?" I answered because I wasn't sure at the moment. I felt really nice walking along in my miniskirt. "No," Doris answered after a moment. "Not really. I think we'll be happy either way. Unless you decide Gia is going to be a permanent change, then we'll need to talk." "I don't think so," I answered, "but I never thought I'd be buying my first bra at any time in my life either." We wandered around, spent too much money on my clothes, and discussed the sort of place we would like to live in. I briefly thought back to a picnic lunch and saying "next time I'll wear the dress". Six little words that unintentionally changed my life. For the better.