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Looking for Love I was on my own for the first time in a while and I decided to indulge myself in my own peculiar hobby. I have been in a few relationships and tried to share with a couple but neither of the girls liked seeing me wearing what is considered female attire. I don't know why I feel this need to wear dresses, panties, pantyhose, and other articles but I do. I feel more relaxed, the cares of the day just seem to melt away. It is my escape. For years I kept it hidden and would subtly feel out my partner trying to decide on the level of acceptance I might receive. The closest I got to acceptance was her not wanting to leave me, but also not wanting to see or hear anything more about it. That lasted for several years but I couldn't stay hidden for long. Eventually she left because she didn't like my secret side and couldn't understand why I just couldn't give it up. How can someone explain something they don't truly understand themselves? I started doing some shopping and building up new wardrobe. I did a lot of it online because I still felt so very embarrassed at the checkout counter at the stores, especially when trying to buy panties. I was certain the cashier knew the items were for me. I had reached the end of a long week and decided to stop off at a local watering hole for a drink. I ordered and tool my drink from the bar and picked out a table where I could see the television. A day like today any sport would do, just wanted to be distracted. The place was pretty empty so I was surprised when a voice asked, "You a Dodgers or a Braves fan?" "Neither, actually," I answered as I turned. "I'm just killing some time and a few brain cells." She was pretty dressed in capris and a top that provided a nice view of her ample cleavage. I always noticed the clothes first, how they fit her, what she chose. "That works," she said. "I don't like the Dodgers. Mind if I share the table?" "Not at all, have a seat. I'm Paul." "Chris," she answered as she stepped around the chair and sat. We talked baseball for a while, migrated on to other sports and other topics of the day. I bought her a few drinks. We had a really good time. "Hey, this has been really terrific," I told her. "but I need to be heading back to the house." "Is someone waiting for you?" "No, just need get back and take care of some things to do with work. I work at home. If you like, you can come with me. I have some wine at the house, planning on cooking up a simple dinner when I get done. It ought to take about a half hour to do what I need for work." "Sure, why not." Chris followed me back to my place. I poured us each a glass of wine and got her settled in the living room. Showed her the remotes and told her I'd be back with her in a few minutes. I made quick work of what had to be done and was back in just 20 minutes. We talked for a little while and then threw together a light dinner. After we ate I grabbed some of the dishes and took them to the kitchen sink. When I turned around Chris was there with the rest of them reaching past me laying them on the counter. I couldn't help myself, I reached around her waist, pulled her close and kissed her. It was tentative waiting to see if she would push me away. Instead it must have been just what she was waiting for because she wrapped her arms around me crushing our bodies together. We were so tight together she couldn't miss my reaction. She leaned back and grinned. "I was hoping you would be up for some fun," she purred. "And you certainly are up. Let's go to your room." I led her to the bedroom; we undressed each other and spent the next couple hours giving each other as much pleasure as we could. First time sex can be the best when two people mesh well. Senses go into overdrive watching and hearing the reaction to each touch, feeling her touches. When it eventually ended I was feeling slightly dizzy and numb. I lay there for a minute collecting myself with Chris lying beside me on my arm. I got up and went into the bathroom to relieve myself. I heard the bed creak as Chris climbed out. "Give me just a minute and I'll be done. I can get you a washcloth if you want to clean up," I called to her. I didn't get an answer. I flushed and walked out of the bathroom. Looking around I saw all the clothes from both of us still on the floor. The closet door stood open. I walked over and stepped inside. Chris was in there looking through the few dresses hanging against one wall. "Do you have someone who comes to visit sometimes?" she asked without turning around. "Not enough here for a live in girlfriend." "No, nobody comes to visit." I took a breath. "Those are mine." "Really?" she turned to look at me, her breasts bouncing side to side with the momentum. It was impossible not to look at them. "Yes, really," I answered. "I sometimes wear them when I want to relax. I like the feel of them." "OK, can't say I've come across this before." She stood there looking at me, evaluating me. "Give me your number. I'm going to think about this and maybe I'll want to come back." I looked at her for a second. "I guess I'll give it to you. At least you already have an idea of what is going on rather than breaking the news later." We left the closet and got dressed. I gave her the number but I didn't expect to hear from her again. I walked her to the door and she was gone. Chapter 2 A week later I was finishing up my day at work when my cell rang. "Hello," I answered. "Hi Paul, its Chris," the voice on the other end said. "Oh, hi! I really didn't expect to hear from you." "Well, I decided I had a really good time with you both in and out of the bed and thought I'd give you another chance to show me a good time." "OK. Want to try and do something tonight?" I asked truly amazed. "Tonight is good for me. What do you have in mind?" "Dinner and a movie, nightcap if things go well. How does that sound?" I asked. "That'll do. How about I meet you at your place and we go from there?" "Fine by me. When do you want to come by?" "I'll see you in about 30 minutes. That ok?" "I can do that. I'll see you then." I hung up the phone. I was still feeling a bit stunned. I pulled it together and finished off my work. I changed out of the shorts and tee into some nice jeans and a polo. About 10 minutes later there came a knock on the door. Chris looked stunning in a summery short dress and heels. "Wow!" I exclaimed, unable to contain myself. "Well, I thought it would get your attention." "You got my attention," I told her. We headed out and caught a movie and then some dinner. Conversation was light and easy and we had a terrific time again. I drove us back to my place and we went in for the nightcap. As I handed her a glass of wine I took her in my arms and kissed her. I ran my hand down her back squeezing her ass a bit. I could tell it was bare beneath the dress. "Hold on there a second," Chris spoke. "Before things get too carried away I have something I want." "Of course, what would you like?" "I want you to go put on one of your dresses." She looked me straight in the eye as she said it. "Why?" I asked immediately wary. "Because it is different," she cooed, "and I like different. Now go be a good boy and put on a dress for me." She rubbed the front of my pants. "Please." I was certain this wasn't going any further until I did so I nodded and stepped back away from her. "If you really want I will, but I'd rather just get you out of your dress." "Nope, nothing is coming off until I see you in a dress." She walked to the couch and sat, sipping her wine. "OK" I wandered back to the bedroom and into the closet. I grabbed a dress that came just above my knee and a pair of panties. It only took a short time to change but I stood there for a couple minutes trying to decide if I really wanted to go back out there. Finally, I made up my mind and went back. I stopped in the kitchen and picked up my glass of wine. "Cute," she chuckled. "At least you've got decent legs. You still just look like a guy in a dress though. Now I'm ready to get back to enjoying the evening." I stepped closer and leaned to place my glass on the table. She reached out and ran her hand up the inside of my leg under the dress. "I think I might like this though," she leaned closer. I backed away before she got high enough to touch anything other than my leg. I slowly got to my knees and placed my hands on her legs gently pushing them apart. I slid my hands up pushing her dress out of the way as I moved up exposing a white translucent g-string panty. She slid down on the couch, lifting her hips and I pulled the g-string off her. I slid my hands back under her and pulled her to my mouth. After a while Chris pushed me back, not ready to climax yet. I stood about to sit beside her on the couch but she stopped me, sliding forward to the edge of the couch. She lifted my dress exposing my panties. She used her fingers to trace my cock under the lace, "Ooo, sexy panties, too. A bonus." She pulled the panties down releasing me. She took me into her mouth as she let them slide the rest of their way down my legs to the floor. She licked and sucked for a while but stopped before I could reach my climax. She stood up and dropped my dress back over my hard on. She then wrapped her hand around it within the material of the dress, turned and led me back to the bedroom. We spent the next several hours in bliss. Chris climbed out of bed and went into the bathroom. When she came back out she was completely dressed again (except the panties which were still on the floor in the living room). "I've got to be going," she said. "Oh, I was hoping maybe this time we could have breakfast together." "Not this time. I'll call you this week. I'd like to get together again next Saturday. A night in though, just here at the house." "OK, still liking different?" I got up and put on a pair of shorts. She just looked over her shoulder and grinned as she went out the bedroom door. Chris went to the living room, picked up her underwear and put it in her purse. She turned gave me a kiss and went out the door. Chapter 3 Saturday came and there was a knock on the door again. Chris came in dressed in a long casual dress. She had a bag in her hand which she handed me as she came in. "A surprise for you," she said. "Go put these on before we go any further." "OK," I answered a bit taken back. I started toward the bedroom while I looked in the bag. There was a dress, lace thong, garter and stockings. I stripped down and put everything on but I didn't like the way they fit. The dress was too short and I thought it made the whole outfit look trashy rather than sexy. "Hey, this dress is too short," I called down the hall. "I don't think it really works that well." "Does it fit?" she called back. "Well, yeah, sort of." "Then I am sure it will do. Come on back out." I came back into the living room and the first thing I saw was Chris. She had taken off her dress and was wearing a corset with stockings, g- string panty, the top of the corset was sheer enough to clearly see her nipples. The next thing I saw was a guy sitting on my couch. "Uh, what is going on?" I asked as I tried to make the dress longer. "Paul, this is my boyfriend Alex. Alex, this is Paul." "What are you talking about boyfriend?" I was getting angry now, forgetting about how I was dressed. "Well, sometimes we get bored with each other. We go and pick up different people at bars and tell each other what it was like with them. Usually it is a one night stand but you offered a bit of a different twist. When I told Alex about you he asked that I get together with you again and see if I could get you to wear a dress for me and if you would that I make arrangements to have another date. This time he wanted to be here. He wants to watch us, then he wants to fuck us both." "I changed my mind," Alex spoke for the first time. "I think I'll fuck you Chris and then let Paul lick me clean while you blow him. Or her, however you want to think of it." He leaned back while talking and took his pants down exposing himself. I was disgusted thinking of his bare ass on my couch. Chris moved to straddle Alex pushing her breasts into his face. "Come here, Paul," she cooed. "Let me see that cock of yours in that lace thong." "I don't think so," I said. "First, this is not ok with me. You folks need to leave." I grabbed Chris' dress and tossed it over her shoulder. "Hey," she called. "Be a good little girl and do as you are told." "I like to wear dresses, I am not looking to be dominated or any of that crap. Not my thing. I don't like doing guys ot other guy's girlfriends either. If I had known I would have left you at that bar." "Look," Alex said. "Just shut your mouth unless you're sucking on something and get started. I don't want to have to break your arm to convince you." I walked around to a closet and reached inside for the baseball bat that rested there. I held it as I walked to the couch. "Now," I tried to sound tough, difficult to do in a mini-dress. "I think it is time you leave or I can take some batting practice on your knees." Alex pushed Chris off to the side onto the couch, she looked at me and back to him. I gripped the bat ready to swing. He reached down and pulled his pants back up. "Come on, Chris. Seems this guy isn't as much a pussy as we thought, you can blow me in the car." Chris stood and pulled her dress over her head. "Sorry, Paul. Thought we could have a bit more fun. Keep the dress, something to remember me by." She winked and headed for the door. "Secondly," I called to her. "I don't like lace thongs. The lace on the back makes me itch too much." Chris laughed and walked out the door. Paul walked out right behind her. I closed and locked the door. I returned the bat to its old position in the closet and then went to the bedroom. I stripped off the clothes, found a set of my own male clothes and put them on. I didn't think I'd be wearing any dresses any time soon. I thought about tossing them all in the trash. Then I decided I'd wait until morning before I made any rash decisions. Chapter 4 I spent the next several months embedded back in my old routine. I went to my normal places, hung out with people I knew but didn't spend too much time with them. I worked every day and just plodded on through my life. One day I found myself wandering a downtown mall. It was a weekday and before lunch so there weren't too many folks around. I window shopped a lot of stores looking at many different things. I envied smaller women and the fashions they had to choose from. I wandered into the larger stores going through each department, trying to avoid the eyes of the sales people when I went through the women's sections. Just before coming to another large store I saw a dress shop. It appeared to be filled with formal dresses. Before I realized it I had stopped and was looking through the entry at the many colorful dresses hanging off dozens of racks. From where I stood they all appeared to be floor length but I was certain there were some shorter dresses hanging among the many racks I could see the tops of beyond the entry. One dress just inside the door caught my eye. I looked around and didn't see anyone so I decided I would just check the size and cost. I turned the dress looking for a tag and finally found it, size 6. Well, that might fit one leg. Plus the price tag of $450, more than I wanted to spend for sure. Now I was committed it seemed. I looked at the next dress hanging behind the first. Looking at sizes and costs I looked at each one on that particular rack. "See something you like?" a voice came from behind me. I practically jumped out of my skin. I almost tore the tag I was holding from the dress I was looking at as well as I spun to see who had so suddenly appeared behind me. "I'm so sorry," she said holding a hand out to steady me. "I didn't mean to scare you like that. She was pretty, but not overly so, very girl next door pretty. She had long dark hair, dressed in a skirt and blouse with a name tag that read "Brenda". The skirt short enough to allow me to appreciate her legs, the blouse fitted nicely showing her figure, she was not overly buxom but wouldn't be mistaken for a boy by any means. "Oh, um, I, ah," I stumbled looking for words, an excuse for why I was looking at the dresses. "It's ok. There hasn't been anyone in all morning. I'm glad to have someone to say hi to," she answered trying to give me an out. "Oh, well, I'm sorry you are so bored. Afraid I'm not going to be much company for you either. I just stopped to look out of curiosity at this first dress and got caught looking at the others. I don't know why, but I ought to be heading on." I started to step around her and leave. "Oh, OK. Would you just tell me why you were looking? Is it for someone else or for you? We get a lot of guys in here that do the drag shows so it's no big deal." "No, like I said, I don't know why I stopped. There isn't anyone else and I don't do drag shows." A bit of an edge had crept into my voice. "I'm sorry. I didn't mean to pry. I hope you have a nice day and maybe come back again." She smiled but there was a bit of sadness to it. I nodded. "Have a nice day," and I left the store. I walked through the big store at the end of the hall, moving quicker than I had previously trying to avoid another face to face, I was certain my face was a bright scarlet. I reached the electronics section where I finally stopped. At least here I could easily put off any annoying salesperson without any anxiety. I looked through DVDs, watched some television, finally I made a decision and left the store. I walked down the hall on the opposite side as I passed the dress shop looking through the windows as I passed. The store still appeared to be empty of customers. I continued a few feet passed the shop and crossed the hall turning back to the store's entrance. I took a breath and went back in. This time I went deeper into the store past several racks of dresses. Any number of people could be wandering the maze of clothes; I listened for any conversation but heard nothing at first. Then I heard the rustle of material as someone was working their way towards me. I turned to face the noise as Brenda emerged. "So, you decided to come back," she said. "Any particular reason this time or are you just lost." She smiled as she said it and she had a very nice smile. "No, I'm not lost. And yes, I have a reason this time," I confided. "Everything I told you before was true except not knowing why I was in here. The dress looked interesting to me and I wanted to check the size and price. Both were wrong for me so I meant to just leave but got caught looking at other dresses." "You know, there's no crime in looking." "Yeah, I understand that. But, it seems to be socially unacceptable for a guy to be dress shopping for himself. I find it a bit embarrassing. I just finally decided to try this time and be open and honest with you." "I'm honored. By the way, I've heard that something like 1 in 10 men cross-dress and oddly enough over 90% of those are believed to be straight so don't be so you don't need to be uptight about it." "That's easy for you to say. Cashiers always seem to have something to say or some look to give whenever I try and buy something so I just don't do it very often. Actually, almost never. The fact that I am even in here now is completely out of the norm. The reason I came back was because I felt like you were looking more for company and something to do than judging why I was here. I decided to come back and give it a try." I had watched her eyes through my whole speech looking for the slightest reproachful look. Instead she seemed to be happier. I relaxed a bit, but only a little bit. The specter of Chris still haunted me. "Good enough. So, do you know what size you are? Style you are interested in?" she asked as she eyed me up and down. "The size seems to depend on the dress, 18 sometimes, 20, XL or 2XL. That's what makes shopping online so tough, it's a hassle trying to return things that don't fit. So, I don't have a lot. Best I know is from sneaking into some closets here and there when no one was around." I could feel my face heating up again as I talked. "OK, we'll just have you try on a few different sizes of the same dress to get an idea of where to start. Then we can probably get close as we go through some dresses." She turned to one of the racks. "What do you think of this here?" "Wait, wait, just wait a second. I barely had the nerve to come in and now you think I can just start trying on dresses in a mall store where anyone can walk in, not to mention the fact that you are here. Plus, I don't run around wearing the appropriate underwear for doing this. I don't want the dress looking ugly because of that. Perhaps I can drop by another time when I can be more prepared. Now that I have met you, maybe I'll feel I can come in and not be so reluctant." Brenda just looked at me for several seconds. "Look," she started, "have you ever decided you have the nerve to do something and then put it off swearing the next time you'll do it but you never go back? Well, that is where we are now. You walk out that door and I'll bet I never see you again. Stay and do this and at least if you never come back you'll have done it and might be brave enough to try it again elsewhere someday. "Frankly, it doesn't matter to me. You seem like a nice guy and if possible I would like to sell you a dress because it might be the only thing I get to do today other than sit on my ass or wander around trying not to watch the clock. And even if you don't buy one I still get to spend a little time doing something. So, what's it going to be?" she hesitated for a couple seconds. "Well, staying or going?" She waited patiently while I fought a war within myself. Part of me wanted to cut and run while a voice in the back of my head pleaded to believe her. Finally I spoke, "OK, how about we look through the dresses. Maybe find a few that look interesting. I can then decide if there still isn't anyone else in the store whether I will try one on." "Well, it's a start. A good start," she smiled. There had to be hundreds of dresses in the store. Some looked ridiculous to me, others didn't look like they would work on me. Some I loved but didn't come in sizes large enough for me. Brenda and I spent an hour sorting through and chatting. Eventually I didn't even think about the oddness of what I was doing. "Could you watch the store for just a minute?" Brenda asked. "If someone comes in just tell them I will be back in less than 5 minutes." "Yeah, sure," I answered. I saw her scamper out the door and down the hall. She returned without anyone else having come into the store. She came up to me and stuck something in my hands. "Here, you owe me $10." I looked down at a package of sheer nude pantyhose and then back at her. "We've been pulling dresses for over an hour now and I found one I would for sure like to see you try on. Put those on and we'll see how things look. That should remove the last concern you had." I frowned for a second again warring with myself. Finally I nodded and turned to go to the dressing room. I grabbed a dress off the rack we had been storing our choices on and entered the dressing room. I did a quick check for cameras. I knew there were some watching the store but there shouldn't be any in here. Satisfied of my privacy I stripped down and put on the hose and dress. This dress was a deep blue with a full floor-length skirt and it almost reached the floor on me which was a plus because I was pretty tall. The top was sleeveless with a V-neck. I grabbed the empty package, a $10 bill and opened the dressing room door. Hearing no extra voices I walked out. I tried to be very nonchalant as I spoke, "Here's the $10 I owe you. Is there a trashcan where I can throw this out?" Brenda looked me up and down. "Very nice. That fits you well. There is a trash can behind the counter, and then come over here to the mirrors." I dropped the trash and went to the mirrors, five of them angled to provide some perspectives other than just head on. Brenda stood behind me giving the dress and me a once over with a critical eye. I was so nervous I started worrying that I would start to sweat despite the coolness of the shop. Brenda smoothed down the top above my hips where it was tight against my skin, then crouched down giving the hem a tug to straighten it some. "Give us a spin," she ordered. I complied doing a complete 360 while trying to watch myself in the mirror. "Yes, very nice. I think that works really well on you, a good fit so the size is perfect," she offered. "OK, next one." She took my hand and ushered me back to the dressing room. I grabbed the next dress off the rack as I passed. Though I thought I might only try one on, im all I tried on 15 different dresses of all sorts and sizes. I had the last one in the dressing room with me. I was doubtful though the dress was beautiful. It was a one- shoulder, floor length column style with a back slit that had to be at least half way up the thigh. It was white with sequins that added just a slight hint of color to it. I got it on and got the zipper almost all the way up, most of the others had a side zipper which I liked, but this one was a back zip. I walked out to the mirrors and a waiting Brenda. "I need zipper help," I told her as I went to take my place in front of the mirrors. "No problem," she said as she stepped behind me. She placed one hand near the base of my spine as she pulled the zipped up into place. In the mirror I saw a small bulge begin to grow under the dress. I felt my face redden once again. "Well," she started, "this was the one I wanted to see you in. You've got a pretty decent figure for it and the back slit is great for your legs. Obviously the pantyhose aren't enough though to resolve every issue." The fact she noticed didn't help as the bulge continued to grow. Eventually the various clothes prevented me from going too far but I was pretty uncomfortable and trying to think of anything to reduce the erection. "You know the drill, give me a spin," she ordered. I did the turn, I saw how high the slit in the back was and it appeared to just barely cover what needed to be covered. I reached back fingering the top of it touching my leg only an inch or two below my rear. "Yeah, it does come up a bit too high. I could alter it to lower it by a couple inches and then you would still be able to move around ok." She offered. "No, I don't think this is for me." I said. I crossed my hands in front of me hiding the lump. "Are you sure? I think you look hot in it." I could tell from the way she was looking she actually meant it. "OK," she said, "which one or ones are your favorites?" I walked back over to the rack and started sorting through the dresses one at a time resorting them with my favorites to the left. I chose three: the first blue dress, a red cocktail length that had black tulle peeking out from under the hem, and a short black dress sprinkled with a gold fleck that had half-sleeves. "Do you really like this one?" I asked. "Well, the three you've picked are good. I liked them all as well but the one you are wearing is my favorite." I heard a noise at the front of the store and realized someone had come in. I turned and quickly went into the dressing room. Outside I could hear a woman talking to Brenda about needing a dress for a formal party. Their voices faded as they moved into the store. I decided to try to change and sneak out the door before I could be seen. I would come back later and talk to Brenda when the store was empty again. One problem, try as I may I could not get out of the dress. I finally gave up and sat on the bench of the dressing room. About 10 minutes later I heard the door to the next dressing room close. I cracked the door open on my room and peeked out. Brenda was standing there looking into the store. "Psst," I called. "Oh, there you are!" she answered as she turned. "Shhh, come here. I need you to unzip me." She came and opened the door further as I turned around. I felt the zipper drop and the top of the dress loosen. "Thanks." I pulled the door shut. I quickly took the dress off and put on my own clothes sticking my underwear in my pocket not wanting to take the time to remove the pantyhose while listening for the other customer to come out. Finally ready I practically ran from the room and put the dress back on the rack. "Are we going to discuss a purchase?" Brenda asked. "There is someone else here," I said, thinking that was explanation enough. "Yes, and I am hoping she will buy a dress too," she answered. At that moment the lady came out of her dressing room. I stepped away from Brenda and pretended to be interested in something at the other end of the store. Brenda went to the mirrors with the customer doing as she had done with me. Eventually the woman went back to the dressing room and I went back to Benda. "OK," she started, "have you made a decision?" "Let's start with the 3 I like and the 1 you like," I practically whispered. "What's the damage?" She checked the tags on each of the dresses and quoted a price of $840. "Ouch!" I squeeked. "I can't do that. Perhaps two of them. Maybe the blue and the black. How does that look?" "Well, those two come to $370. But I'll make you a deal. Give me $550 and I'll throw in all 4." "Can you do that?" I asked. "Won't you get into trouble?" "Well, no. It's my shop. That will be a break even deal for me. You'll need to come back later in the week to pick up the white dress after I make the alterations I suggested." I heard the door to the dressing room and quickly said "Deal." I waited again while she dealt with her other customer and then gave her my credit card. Toting the 3 dresses with me I headed for the car and then home. I couldn't believe what I had just done. * * * * A few days later I went back up to the mall. This time I walked straight to the store and entered without trepidation. I looked around a bit but Brenda wasn't anywhere I could see her so I just waited. A couple minutes passed and Brenda stepped out from a back room. "Oh, Paul, I didn't hear anyone come in. How are you doing?" "I'm doing ok, how about you?" "Things are going well." She looked around the counter a bit, looked to be checking things in the area. "Well, I expected to see the other dresses on the counter or hanging nearby. Since I don't see them can I assume you are keeping them? Or do you have them in the car just waiting to bring them in?" "No, they are still at my house; I'm not bringing them back. I have yet to figure out what I am going to do with 4 formal dresses, but I'm sure something will occur to me. Have you finished the alterations on the last one?" "Well, I am surprised, and pleased," she smiled. "I just finished up with the white one. Would you care to try it on so I can check to be sure it is good?" I looked around. Once again the store was empty except for the two of us and the hall outside had little traffic. "OK, might as well." Brenda disappeared into the back and emerged with the dress draped across her arm. She escorted me to the dressing room handing me the dress and pushing the door closed. I stripped down, this time I was prepared wearing a tight pair of no- line panties. I slipped the dress on and zipped it as far as I could. Holding it in place I stepped slowly out of the dressing room, hearing no one else I walked over to the mirrors where Brenda stood waiting. "How are you planning to zip it at home," she asked, "if you can't do it here?" "Oh, I'll figure something out. Or maybe I'll just have to have you come by and zip it any time I decide to wear it." I laughed a bit. "Well, I might not always be available," she answered while examining her handy work. "But, maybe once in a while I could be persuaded." I just stood there staring at her in the mirror. She looked up and said, "Going to spin for me?" "Uh, yeah, sorry." I slowly turned looking alternately at her and my reflection. She had shortened the slit so it didn't feel like it was exposing my rear and lengthened the skirt a little so it almost touched the floor. "OK, that looks good to me. You didn't mention if you wear heals or not so I left it a bit short. I hope you are happy with it." "Oh, I don't own any shoes. I do think it looks wonderful. I really appreciate it." I turned to face her. "Would you consider coming over to my house for a formal dinner?" "Foreseeing zipper trouble already?" she asked. "No, not at all. I haven't even decided on which dress I'll wear. I just decided I want to have you over for dinner. And it seems like a great reason to wear one of my new dresses." She studied my face for a moment and smiled. "I'd be delighted. I close the store early on Sunday." I told her where I lived and she figured she could be there around 6:30. "That would be perfect." I turned away from her. "So, a little zipper help again please. I need to go plan a dinner." She unzipped the dress and I went back to the dressing room to change. After I came back out she wrapped the dress in plastic while I asked about food likes and dislikes. I finally took the dress and went home. Chapter 5 Sunday came around. I had found two very nice rib-eyes, a couple potatoes for baking (with all the fixings), some asparagus, plus salad and a cake for dessert. I found the challenge was scheduling. I wanted dinner to be almost ready when Brenda showed up, but I also wanted to be dressed and ready. But I didn't want to take a chance that I would get anything on the dress. This was more of a challenge than I expected. I found myself running around the kitchen in just a pair of panties and black silk stockings, checking the clock about every two minutes. The steaks were just about done, I had removed them from the broiler and placed them in the oven to finish cooking and stay warm. The asparagus was also on the verge of finishing, suated in a little butter, still very crisp. I cheated with the potatoes nuking them in the microwave then wrapping them in towels to finish cooking. At last I ran back to the bedroom and grabbed the red dress from the closet door. I slipped it on and checked myself in the mirror before dashing back to the kitchen, the sound of the tulle and satin sounding loud to my ears. I checked the steaks and then pulled the salad from the refrigerator. I checked the table and made sure everything looked in place. At last I grabbed a good Cabernet Sauvignon, opened it and decanted it into a crystal carafe to breathe. Just as I set it on the table there came a knock at the door. I brushed out the front of my dress as I went to the door, took a breath and pulled it open. Brenda was standing there looking amazing in a long green dress, her hair was done up and her make-up was evident but not overdone. I was envious of her at once. "Wow, you look amazing," I offered. "Please, come in." "Thank you," she beamed. "I wasn't sure what to expect from you. No makeup, wig or even shoes." "Well, I said I haven't any shoes. Now that I have nice clothes I'll take a look. But makeup and wigs, I just really like wearing the clothes; I'm not trying to pass as a girl." "OK, guess we'll go with that." I closed the door and led her to the dining room. "Can I pour you some wine? Dinner is just about ready but it won't hurt to wait a bit if you like." "I'm ready to eat if you are. Between rushing around today and getting ready for tonight I haven't had much of a chance to eat today. If I am going to have wine I better get something in my stomach." I poured us both glasses of wine, got her seated and went to fetch the salads from the kitchen. We worked out way through dinner. I was fortunate that everything came out perfect, not a usual occurrence for me. We chatted about a lot of different things from childhood to politics. We were able to discuss and disagree without any problems. I refilled the wine glasses and we moved to the living room where I had some music playing softly. We sat together on the couch, my dress spilling over the top of her legs as I sat. I tried to gather it over to the other side. She reached down and took my hand. "Don't worry about it, it's fine," she offered. "Where do you think this is going tonight?" "I don't know," I answered. "I thought I would just let it go and see what happened. We made it through dinner so that was a good thing. I figure we chat some more, drink some more, and maybe I try and kiss you at some point. If you go along with all that, then we see what happens next. If you don't then you'll likely tell me you need to leave at some point." "Well, I'll make it a bit easier for you. I'm enjoying the chat and the wine, but when this glass is empty I am going to head home. I will let you give me a kiss good night when I leave. How's that strike you?" "Strikes me just fine." So we chatted, and finished our wine. When she set her glass down I offered to see her to the door. She stepped out the door and turned to face me. I took a quick glance and saw the street was empty and focused on her again. "Thank you for coming over. I had a wonderful time," I told her. "I think I should be the one thanking you for having me in your home, for preparing a wonderful meal, and for making it such a wonderful evening." I reached and put my arm around her pulled her close. She looked me straight in the eyes. I leaned in pressing my lips to hers. The kiss started slow but became deeper. After a little time passed she pulled back and I let her. "Thank you again," she said "I hope to see you again soon." With that she went to her car while I watched. I went back inside the house closing and locking the door. I went to the dining room and began cleaning up. After about another hour I was ready to head to bed. I stripped off the dress and stockings, hung the dress back in the closet and threw the stockings in the laundry. I grabbed a nightgown, turned off the lights and went to sleep. Chapter 6 The week was passing with nothing much exciting happening. I had been thinking a lot about the dinner from the previous weekend trying to decide when I should go up to the mall and visit Brenda. I wanted to ask her out again, perhaps something of a more normal date. I was going through my daily routine and had gotten the mail. Among the typical bills and junk I found an envelope which I did not recognize the hand writing of. There was no return address and the postmark indicated it was mailed from nearby. I went into the house and opened it. Within the envelope I found an invitation: You are invited to dinner Business casual dress with shoes! Saturday 7:00 pm RSVP Brenda There was a phone number listed. I wondered about the business casual dress line. I figured it meant I was supposed to wear a dress with shoes this time rather than casual business guy clothes. But I would be sure before I showed up to a party with a dozen guests in the wrong clothes. I took out my cell and dialed the number. "Hello?" came Brenda's voice. "Hi there, it's Paul," I began. "I was just thinking of coming by the shop to say hi when I found your invitation in the mail." "Oh, good, it got to you. I was afraid it wouldn't get there in time for you to get things together for Saturday." "Yeah, I had a question about that. Are we talking a dress or something like khaki slacks and a polo?" "Oh, I expect you to wear a dress. The ones you bought from me are too formal though so you need something more casual. And I expect you to have the correct shoes to go with it. Can you do that?" "I'll see what I can do. As a matter of fact I'll get to work on it right now. I'll bet I can find something online that can deliver by Saturday," I offered. We talked for a few more minutes both saying how much of a good time we had. She gave me her address and we said good-bye until Saturday. I grabbed my computer and started searching for shoes. I was surprised at how many sites had larger sized women's shoes. Once I saw I had choices I went to my closet to look through my dresses. I pushed the formals out of the way and looked at the others. Forget the red mini- dress, not going there, it served as a reminder that I needed to be careful. I only had a couple other dresses and I checked them each over. I decided I didn't really like any of them. It is different picking out a dress to wear around someone else than what I wore just for me. I went back to the computer and opened another window to search for dresses. It took me a while to decide but I finally decided on a short green shirt dress, it appeared to be a nice mid-thigh length. It looked like it would be casual enough for the dinner. I swapped back over to the other window and found a nice sandal with a low heals. Both ordered and should be delivered in time for the dinner. I went back to doing my regular work week. Of course I couldn't keep my mind entirely on work. I was thinking on what I had chosen to wear as well as going to her place and not knowing what I was going to be walking into. I was thrilled and terrified at the same time. * * * Saturday came and I threw on some nice clothes, khaki slacks and a nice polo. I packed the clothes I would be wearing later in a bag and went out the door. I was prepared for whatever direction this date would take. No surprises this time. The drive over was not exciting and I found the address without a problem. I grabbed the bag off the passenger seat and proceeded to the front door. I looked around as I headed up the walk; it was a nice quiet neighborhood, aside from someone walking a dog down the opposite sidewalk there was nobody in sight. I stepped up to the door and rang the doorbell. I could hear the noise of someone coming to the door and my heart started racing a bit as the door started to open. "Um, what is this?" Brenda asked as she looked at me. "I thought I was clear as to the dress code." "Very clear," I answered. "But I couldn't just drive over here in a dress. Something could happen, someone might see me." I held the bag up. "I did come prepared though if you will give me just a couple minutes." She seemed to be considering sending me away for a moment or two. Finally she let me in. "You can use the room on the right down that hall." She pointed in the direction I was to go. "I'll be right back," I promised. I found the room which appeared to be an office. The window looked out on a nice backyard with a gazebo out toward the center. I quickly stripped my clothes off and redressed in the clothes I bought. I found a mirror on the inside of the closet door and checked myself before I went out. "Better?" I asked as I entered the living room again. Brenda was sitting on a couch sipping a drink. She looked up and looked me over. "Yes, much better. I like the shoes too." She was wearing a tube dress. It was short but had a nearly transparent skirt that was mid-thigh length in the front and just longer than knee length in the back, a liner a bit shorter in the front visible underneath. Very sexy. "Would you be interested in something to drink?" she asked as she got up from the couch. "Yes, please. Whatever you are having will be fine with me." I watched her leave the room then looked around the room I was standing in. It felt odd to be standing in a strange place in a dress, not to mention the shoes. I could hear Brenda in the other room making the drinks. After a minute she returned. "Here you go." She handed me the drink. Before I could say thank you the doorbell rang. Panic struck me. I looked around trying to decide which way to go. "Relax, it's just the pizza," she offered. "You can go to the kitchen if you like and wait." She headed for the door. I headed for the kitchen and hid by the door listening. I heard her thank the guy and pay him. The door closed and she came to the kitchen carrying the pizza. "Are you ok?" she asked. "I thought after that day in the store you might be able to handle at least a little bit of public." "Well, right now, you are the little bit of public that I can handle. I've never been particularly brave but a few months ago something happened that made me even more jumpy. I'll tell you about it while we eat." We grabbed a couple slices of pizza and our drinks and sat down at the dining table. I proceeded to tell her about Chris and her showing up with Alex on our 3rd date. "So, while showing up here and changing into this outfit did demonstrate a lot of trust on my part, I was still worried about what might happen when I showed up." She thought on it a while. Then said, "Come on, help me clean this up and we'll make another drink and talk some more. I hope you've decided you can trust me not to pull something like that on you." We cleaned up what little there was to clean. Most of it just went to the garbage can. A couple of fresh drinks were prepared and we started out of the kitchen. Brenda headed for the back door. "Let's sit outside. Sun's down and it should be real nice out. Don't worry, no lights and a high fence. Nobody should be able to see in." She reached back, took my hand and led me out to the patio. "I did notice your gazebo out back earlier through the window." "Well, it actually houses a hot tub, but we aren't going there tonight. "So tell me, why the dresses? I know some men enjoy wearing women's clothes, but why you?" "For me it always just seemed to be a part of me. I started wanting to wear them as early as I can remember. Even though I knew boys don't wear dresses, as my mother would tell me, I couldn't help myself. I wanted to try everything, every style, all the different underwear, etc. Once I got older I started narrowing things down to what I liked and didn't like. I've bought clothes and thrown them away a couple months later in fear that someone would find out. I finally reached an age where I decided I needed to be happy in who I was and everyone else be damned. "Now I know that seems to fly in the face of what I said before about being worried about being seen but it is one thing to accept someone might become part of my life and know about it and another to go flaunting about and, in my mind, asking for trouble. "I think there is something about me and my manor. I don't think I act effeminate or anything, well, except like now where I am wearing a dress, but all through school I seemed to attract the bullies. I often wondered if there was something that some people just sensed about me in that regard." "That is all quite interesting," she mused. "First, though, when you came into the shop I felt you were looking for a dress for yourself. It was the way you were looking at them. There is a difference in the way a guy looks at a dress for a woman and looks for themself. First of all, very few men look for their wives or girlfriends, but it is just different. If we could watch different men shop for dresses, I think I could tell which were which. When you took off after I approached you the first time I was certain the dress was for you but I didn't expect to see you return. When you did I was impressed, and as we went through the fittings I really started to like you." "I'm glad you like me. I like you too but you know, you don't have to keep asking me to wear dresses. I like going out and wearing guy stuff too." "For now I've decided I like you. I haven't decided if I want to date you. I like doing this because I sort of have the best of both worlds, girlfriend/boyfriend in one. I'm not put off by the dresses, I make my living in dresses and I don't care who wears them, but I'm not certain I want to date someone who wears them either. Jury is still out." "Interesting. But, this is exactly the sort of thing I want. This is why I am trying to be more open, at least privately, that sounds like an oxymoron if ever I heard one. What if you and I got into a serious relationship and a few months or even years down the road you found out about this. Better you decide on your own without all the other pressures whether it is something you want to be a part of. Because, as I've told you, it is a part of me." We sat in silence for a couple minutes. "Would you like another drink?" I asked. "I can go make us a couple more." "Sure, last one." She handed me her glass. I went inside and mixed the drinks. I could see her sitting there staring up at the night sky. I picked up the drinks and went back. "Here you go." I handed her the drink and sat down. "OK, so how do you decide on a dress you want?" she asked. "Probably the same way you do," I reached down and took the sheer fabric of her dress in my fingers. "For example, I love this material, what is the dress under it like? Is it just a liner or is it another kind of fabric?" She pulled the cover out of the way and lifted the hem of the skirt. "Look," I took the edge of the skirt in my hand and felt the fabric. "Oh, this is nice. See, I like this but I don't think I would buy it because tube top dresses just don't work for me. But the material is great." I dropped the skirt and she smoothed everything back over her legs again. "Makes sense. OK, what about underwear, panties and bras, etc.?" "We are getting a bit personal now, aren't we?" "I am just trying to understand," she offered taking a drink. "Well, I like the same kind of materials in panties: silk, satin, lace. Not cotton, too bland I can wear regular underwear if I want that. Also, I prefer high cut, nothing like boy shorts or anything like that. "What about you? What do you like to wear?" I asked back. She looked stunned at first and then her face cleared. "I guess it is only fair you ask since we are talking this way. I have a little bit of everything, I guess. Only a couple pair of what I would call really sexy panties. Same goes for bras, mostly functional stuff. You didn't mention bras." "I don't have any. I haven't seen the need. I have one casual summer dress, long, spaghetti straps with a padded bra top built in. But other than that I don't have anything. I've played with the idea of getting a corset with garters just for the sexiness of it but I haven't yet." Brenda turned her glass up finishing her drink. "It's after midnight, I think I've taken in as much as I can tonight." "OK, I know I dumped a lot on you. And it's time I head home. Mind if I call you later this week?" "Make it later in the week, ok? I'm going to be pretty busy early on." She got up and headed for the house. I followed. Once inside she went back to the office and came back with my clothes in the bag. "I think you need to get a little braver. If it truly is a part of you then you should start accepting it and worrying less about what others think. You aren't a kid any longer." I took the bag from her and immediately started breaking into a sweat. I took a breath and headed for the door. "Fine," I said pretending a level of bravery I didn't feel, "I'm heading straight home anyway." I turned at the door and she hugged me and gave me a friendly kiss on the mouth, too quick to let it turn into anything more. I smiled back at her as we separated, then I turned and walked to my car. Right as I got to the car I realized my keys were in the pocket of my pants in the bag. I placed the bag on the trunk lid and started rummaging through trying to find them. A car turned onto the street heading my way. I started rushing trying to get in the car before it reached me, finally got my hands on them and dropped them on the ground before I could press the button to unlock the doors. I looked up and Brenda was still standing in the door watching. The car turned out to be a pick-up truck and it sped past me making my dress blow. I grabbed at it to prevent it flying up, then squatted down and picked up my keys. I unlocked and opened the door, tossing the bag onto the passenger seat, and then I waved to Brenda. She waved back and I carefully got into the car. After another deep breath I started it up and drove home. I got home without any other incidents and once inside I collapsed on the couch for about half an hour waiting for the adrenaline to drain from my body. Finally, I went off to bed. Chapter 7 Over the next several weeks Brenda and I saw each other off and on; more often we talked on the phone. We talked about just about everything there was to talk about and became truly best friends. A day wouldn't go by that we didn't talk for at least a little while. One day I needed to go to the store for some things and decided to stop by the mall. I walked toward Brenda's store but as I got closer I saw that it was very crowded. I assumed it was a wedding party looking for bridesmaid's dresses. Whatever it was I knew she wouldn't have time to chat so I walked on by. I took a stroll around the mall and as I passed one shop I saw a beautiful white blouse on a manikin. I decided to go inside and check it out. It was a light silk and felt wonderful. I checked the rack and found one in my size. I took it and after searching a bit found a camisole with lace borders that would look terrific when paired with it. I went to the cashier and placed the items on the counter trying to act as nonchalant as possible. Other than asking if I wanted to open a store credit card and where I wanted my receipt she didn't give any indication of me being anything other than a normal customer. I left the store feeling really good, very confident. I decided I needed a skirt to go with it and I was going to find one that very day. I walked through a couple stores checking out the selections but either didn't like the material, the price, or the length. I was about to give up. I was heading back down the last hall when I noticed a leather shop with a sale sign. I stopped in to look and see if they had any wallets, mine was starting to wear out. They had a good selection and I picked one out that I thought would be good. I turned around and saw hanging on the opposite wall a leather skirt. Crossing the store I found a rack full of skirts and started looking through them. A nice mini in my size caught my eye and I decided it would look great with the blouse I just bought. Without a second thought I went to the counter to check out. The guy there rang up both items, gave me a look, and then seemed to decide not to say anything other than "Thank you" as he handed me the bag. I went back to my car and then headed home. Once there I got on the internet for a little more shopping. I suddenly had an image in my mind and I wanted to get it done. I can find clothes easily enough, but finding footwear is difficult because of the size I require limits the style available. After almost an hour of searching I found what I wanted and placed my order. I went and put my new clothes away. *** A few days later I was working at my desk when there was a knock at the door. By the time I got there I could see someone walking away and realized it was a delivery. I opened the door and saw the box sitting there. I picked it up and took it inside; my heart was racing with excitement. Once I checked out my order I decided I had to see the whole look together. I stripped off my clothes and started dressing again. First, I put on some sheer black pantyhose, the kind with a silk finish, then the camisole, blouse and finally the leather mini. It came to about mid- thigh on me which I thought was perfect. Finally, black high-heeled boots, just short of knee height made everything look terrific. The heels were about 3" and tapered so it took me a bit of practice to walk in them without feeling like I was going to roll an ankle. It made me think about taking up ice skating again. I went back to work and after an hour I took a break and called Brenda. "Hey, Paul," she answered. "What's up with you?" "Not much. I walked by the store earlier this week and it looked like you were getting slammed so I didn't stop. Still busy?" "I'm working on alterations. Have been all week and I need to finish them by Saturday morning." "Sounds like you've got no time. I was hoping I'd get a chance to see you. Have you been eating?" "I catch a bite when I can," she confessed. "Look, I was going to turn over the store close to my help tonight so I can work on these dresses at home. If you want to come by about 7:00 I think I can take a break for a while. I could probably use it by then." "Sounds great. How about I order a pizza to be delivered and I'll grab some wine to bring along." I couldn't wait for the clock to spin its hands into the correct position and when it finally did I placed a call to the pizza delivery, placed the order and gave them Brenda's address. I grabbed a couple bottles of wine, my wallet and my keys and jumped into my car. There was a lot of traffic but I ignored everyone else. Trucks up high enough to see I was wearing a skirt couldn't see my head. Others could see my head but probably wouldn't notice the blouse unless they really stared. Driving in the boots was a bit different at first but I managed to get everything under control pretty quickly so the drive over went without incident. I arrived at Brenda's and walked up to her door. I rang the bell and waited. It took only a couple seconds before the door opened. "Hell...," Brenda started and stopped just staring. "Well? Do you love it?" I asked, too excited. "I found the boots online and the rest at the mall. What do you think?" "I'm dumb-founded," she began. "You look good, the outfit is great. I just can't believe you are standing on my doorstep in broad daylight dressed like that. I didn't expect this kind of openness this fast." "Well, now that you mention it, would you invite me in? I'd rather not make too much of a spectacle of myself standing here too long." "Oh, of course, come in." She stepped back allowing me in and closed the door behind me. "Besides, what has it been, something like 6 weeks since our first dinner date? And you were sending me home in a dress after our second dinner telling me to get braver and accept who I am," I stated. I pulled a $20 from my wallet and handed it to her. "If you don't mind paying for the pizza, it ought to be here in a minute to two. I'll open one of these bottles." I turned and went to the kitchen. Just as I started with the cork-screw I heard a knock at the door. Shortly after Brenda came to the kitchen with the pizza box. "That smells good," I said. "I hope you're hungry." "I am, and I appreciate the break," she began, "but would you mind explaining all this?" "What's to explain? I put together an outfit that I was really excited about. It was the first time I really went shopping for myself in stores, well except for the time I let you talk me into shopping in your store. It was a huge step for me and when I saw it in the mirror I couldn't think of anyone I could, or wanted to, share it with except you. You're my best friend and I've been sharing a lot with you these past few weeks. I thought you'd be proud of the step I've taken. I was able to do this because of you." I had stopped working on the wine cork and laid the corkscrew down. I was disappointed with her reaction and was not feeling all that great any longer. "I'm sorry, I'm just in shock. So much has changed since the last time you were here in a dress. We've been talking a lot and the few times we have seen each other you've been dressed in your regular clothes. I almost forgot what it's like seeing you in a dress. I really didn't expect to see you out in daylight. You just caught me by surprise. "Are you going to pour that wine?" she asked. "I think I'm ready for dinner if you are." "Yeah, sure." I poured a couple glasses. "Come on, let's eat outside. I could use some sunshine and you don't seem to be too adverse to it either." We talked while we ate and I realized pizza might not have been the best choice for dinner. I spent most of the time trying to be very careful not to get anything on my new white blouse. "I think I'd like another glass of wine," Brenda started. "Would you mind getting us some more? As a matter of fact why don't you just bring the bottle out? I think I'm done with work for tonight. If I push it tomorrow I should have everything done for the clients on time." "Absolutely, no problem at all." I picked up the empty glasses as well as the dirty dishes and brought them all into the kitchen. Once there I drained the remaining wine from the bottle into the glasses and proceeded to open the other bottle. Everything ready I went back out to the backyard to Brenda. The sun had finished setting and it was perfectly comfortable outside. As I walked out the door I heard a low hum. I looked around for the source and noticed the gazebo had been opened. "I thought it might be a nice evening to do a little hot tubbing," she told me as I handed her the glass of wine. "Um, I didn't bring anything to wear in a hot tub. Hell, I'm not even wearing panties tonight." "Really," Brenda smiled as she looked down at the front of my skirt. "That's ok." She took the bottle from me and headed across the yard. She placed her glass and the bottle in a couple holders on the side of the tub, then facing away from me she pulled her top off over her head, she wasn't wearing anything under it. Next she removed her shorts by letting them drop to the ground and stepping out of them. She was now completely naked. I just stood there staring at her, my body reacting of its own accord. "Well, are you getting in?" she called as she climbed over the edge and into the water. I sat down and removed the boots and set them aside. Finally I decided I didn't want these nice new clothes getting wet or dirty so I would have to leave them here. So I stripped off the skirt and folded it neatly over the back of the chair, then the blouse and camisole draped over the top. Finally I pealed the pantyhose off and dropped them in a lump on the seat of the chair. I picked up my glass and walked across the yard completely naked, my excitement quite evident leading the way. I reached the tub and placed the glass in another holder and climbed into the water opposite of her. I looked Brenda in the eyes as I got in but her eyes were focused much lower. "It would appear to me," Brenda began, "that you were honest with me about how you feel about women. I hope I can take that hard-on as a compliment? A reaction that you find me attractive?" "Oh, you can absolutely take it that way." I answered. Several things went through my mind but all sounded stupid so I didn't say anything for a moment. "Is this payback for the shock earlier? Are you getting me back for not warning you I was coming over dressed up?" "No, nothing like that at all," she answered. She picked up her glass and moved next to me. "I've actually been thinking about how things have been the last couple weeks with us. Tonight when you showed up I was still looking for some sign that we ought to be together. I still was dealing with some doubts, but when I opened the door and saw you standing there so happy, not caring about anything other than showing me your creation, I thought this was the sign I've been wanting." She reached over and grasped my cock. "I want all of you and I hope I am right that you want all of me too." I set my glass of wine down and in answer I turned toward her and kissed her full on the mouth. I took her breast in my hand while our tongues tangled. I let her nipple slide between my fingerf pinching it lightly. All the while I was so aware of her hand caressing my cock and balls. We broke the kiss, both of us panting. "Stand up," she comman