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Careful 2 (Steve's Story) Please note this is the second part of the story Careful by Miss_Anyonamiss. If you have not already done so, please read Careful first. Meanwhile Jennifer's side of this story is being wonderfully told by another author, Mrs_Anyonamrs. It is recommended that the reader also read her side of this tale. Comments are appreciated. The next day I went to work, but I hardly accomplished anything. The images just kept running through my mind, the package, the note, but most of all, the bracelet and the wistful smile on Jennifer's face when she put it on. I tried to focus on my job, but I went though the day feeling like another person. How could I have let this all happen? Driving home that night, I knew I needed to calm down and find some time for myself to do some thinking. I stopped at a liquor store on my way home and bought a small bottle of bourbon. I was never really much of a drinker, in fact I had given it up years before, but I felt like a needed a stiff drink that night. I can't explain why, but the first two weeks after Jennifer's night with Rob were not so bad. I was shocked, but for some reason I was in some kind of denial. I knew it happened, but it felt like some weird dream that would eventually fade away. The package had changed all that. Now I realized that everything had changed. My wife was no longer only mine. I had allowed another man to sleep with my wife. The bracelet would be a constant reminder of what I had done. I wondered how much she would wear it. She wore it to bed the night we opened the package, but I noticed she did not have it on the following morning. As I walked in the house that night, I was relieved when she did not have the bracelet on. She greeted me in the same friendly, but not loving, way she had treated me since Rob left. It was a Friday night and we had dinner as a family. After dinner we all spent time together. Fortunately, this was the one thing that had not changed in my life. Despite the fact that Jennifer would not allow me to feel close to her as a husband and lover, our family life had not changed. We were still close as a family, and I was grateful. My greatest fear was that this fantasy that I had started would disrupt our family life. So far it had not. That night I told Jennifer that I had some catching up to do on my work and that she should go to bed without me. I waited about a half hour and went back to check on her. She seemed to be sleeping soundly. I headed out to the patio attached to the back of our home. It was a balmy late summer night and I felt the dampness on my skin as I sat in one of our lawn chairs and poured myself a drink for the first time in years. My mind was churning as I watched the half moon emerge from behind a cloud. I listened to a slight breeze rustle some leaves. It was peaceful, and the sounds of the night calmed me. I felt like I had taken a break from the mixed emotions and anxiety I had been feeling for the past few weeks. My first sip of the bourbon was stronger than I remembered. I felt the sizzle of it sliding down my throat, but I smiled when I felt the distantly familiar warmth when it reached my stomach. Despite how surreal I felt at that moment, I knew I was at a turning point. I knew that I was no longer in control of my marriage, but I also I knew that I needed to sort out exactly how I felt and communicate with Jennifer. We had not had a real talk about what had happened, only a defensive inquisition on my part. I tried to make a mental list of all the questions I had to answer for myself. Why had I started all of this? Was dressing up this important to me? Why did I have this longing for women's clothing? Why did I not explore dressing on my own, why was it important to me to share dressing with Jennifer? What did I really want from dressing up? How did I feel about Jennifer now that she had slept with someone else? Why didn't I stop it? Why did I agree to it in the first place? Was it really about dressing up or something else? Finally I realized there was something else, something that had nagged at me from the first time Jennifer told me that she had thought about other men. I couldn't quite put my finger on it but there was something deep in my mind that was driving all of this. As I poured another drink I decided to focus on what started it all; my fascination with women's clothes. It was hard to admit, but I knew that it had started early. I remembered my adolescence, my first crush, the first time I considered a girl sexy. I remembered the girls that appealed to me in high school and college. They were always the girls that dressed in skirts and other decidedly feminine attire. I had never been attracted to the athletic type, rather the demure soft feminine women. I remembered specific clothes that these girls wore and how I fantasized about them in class. Ok, I stopped myself, was it the girls or the clothes? It was the girl, but the clothes made a difference. I realized that clothing could take a woman from average to sexy. The right clothes on the right woman could give her power, sexual power. Was that it? No. I did not want power, certainly not sexual power over men. No, I wanted to feel the sensual feeling that women feel. When a woman is dressed her best, she looks confident, carries herself differently, she even smells different. There was something about a woman who looked great, and knew it, that I wanted to emulate. So I had come to a realization about myself and why I wanted to dress up in women's clothes, but I still needed to figure out what I actually wanted to do. I knew that this desire was only a small part of me, but still a part. It was a part of my sexuality. Did this make me gay? No, I knew I had never felt that way. I took a minute to review my past sexual thoughts; I had never felt even the remotest attraction to any man. There, I had reassured myself, even I was guilty of the fleeting thought that cross-dressing had homosexual implications. Even when I had made my initial request to Jennifer, I did not have a clear idea of what I wanted. No wonder she was shocked. If I didn't know what I wanted, how could she? She must have had all kinds of possibilities running through her mind. I winched at what she might have thought. So, what did I want? There was the nagging feeling again. I wanted to feel the excitement of dressing, but not everyday dressing, dressing for something else. I also wanted something besides the dressing, acceptance. That was it, I wanted the feelings but I wanted to share them. I wanted to share the feeling with Jennifer and I wanted it to not just be about me, I wanted to be something we both shared. I realized I was not getting anywhere so it was time to move on. The bourbon had definitely had the desired effect. I was now alert, thinking. My mind was lubricated and I was no longer held back by my insecurities. I decided to move on to the question of how I felt about Jennifer and the changes that had taken place in our relationship. I took a deep breath. I knew I should be angry, but at who? This was not a simple answer. How could I be angry at Jennifer? I had given her permission and I could have stopped it. I knew I should be angry at myself, but I wasn't. The nagging feeling was there again. Why was I not angry at myself? Why did I not wish to turn back the clock to the night when I agreed to let her “experiment”? I thought back to our sexual history. When we were dating the sex was good, but it was rushed. We were always doing it in secret in different places. I blamed it on the fact that we did not have time to please each other. When we were married, before the kids it was still not mind blowing. By this time I had begun to think that Jennifer was just not a very sexual person. In fact she even told me that it was not that important to her. When the kids came, I blamed it on the pressures of parenthood. But why the change? Our sex lives had improved the day Jennifer told me that she was curious about other men. Now I knew. It wasn't the time, it wasn't Jennifer, it wasn't the kids, it was me. I had never taken the time to be interested in what she wanted. I was only concerned about my perception of the sex. Yes, time for another drink. I looked at my bourbon bottle in the light of the moon. It was more than half empty. I wondered if my epiphany was the result of the liquor or the truth. I thought for one more moment. I knew I was right, but would I have the guts to admit it to Jennifer? I sincerely hoped I would, and I hoped for......acceptance. The next day I awoke with my first hangover in years. I clearly remembered my revelations from the previous evening, but I was lacking the enthusiasm I had the night before. I went through the day wondering how I could express my feelings to Jennifer. That evening I went to our living room to gather my thoughts. I wanted to talk to her, to tell her how I felt, but I needed to come up with just the right words. I sat for a long while, staring blankly at the television running the upcoming conversation through my mind. How could I have this conversation with Jennifer and still retain any of my manhood? I was still deep in my conflicted thoughts when Jennifer entered the room. When I heard her footsteps I glanced in her direction to acknowledge her. I quickly turned to face her when I saw how she was dressed. The same short skirt, blouse, stockings, and red heels that she wore the night I gave her permission to sleep with another man. I would never forget that outfit. It now symbolized her new sexual freedom and my infinite stupidity. The only way I can describe it is to say she strutted into the center of the room and did a twirl in front of me. When she ended up facing me she gave me a withering look deep into my eyes and moved her hand to direct my attention to the fact that she was wearing the bracelet. I was not expecting this. I was hoping to be able to initiate the conversation. I knew I was looking at a different woman than the one I had known for the last fifteen years. She had never made an entrance like that before. In one move she had taken me from determined to communicate my feelings to her, to ready to do anything she said. When she looked at me in that outfit with her slight mocking smile, I felt an odd mixture of incredible sexual desire and complete compliance to her wishes. I don't know if I had ever quite felt that way before. All I could manage to say was "Jennifer, please stop taunting me." I was consumed with desire for her. I still had not had any sexual contact with her since Rob left. Her smile broadened as she said "do you like?" She was teasing me in a way I had never known before. "Why do you have to be so cruel?" I responded, now totally off balance. All of my prepared speeches were now out the window. She was in charge. She glided over and took a seat next to me. She crossed her legs and her stocking brushed up against my leg. A shiver went through me. She looked me in the eye again and said,"I think we should talk about your sexy present." She paused and asked "how do you want to be dressed, and what do you want to happen?" I had no idea what to say. Her stare seemed to go right through me. I had to lower my gaze away from her. "I just want to feel what it is like to dress up like a woman and be treated like one." I realized this was a vague answer, but to be honest I really had not reached any decisions about my fantasy. My focus had been on her and her new found desires and freedom. She seemed irritated when she said' "Ok, that is a lot of help, would you make me a drink please?" The words were a question, but the tone was a command. I immediately got up and headed for the kitchen. As I poured her tequila I had a chance to collect myself. I had been working up my nerve to talk to her all day, but I wanted to talk to her as equals. As strange as it may sound, I knew we would never talk as equals with her dressed the way she was, coupled with the fact that she was wearing the bracelet. At the same time I was glad she was willing to discuss my fantasy. At least she still realized I had made a sacrifice and she wanted to treat me fairly. However, I also knew she was still extremely uncomfortable with the whole idea. I wanted her to plan my fantasy on her terms. Plus I still wasn't really sure what I wanted from the dressing, but I knew I wanted her to call the shots. I took a deep breath to calm down and took her the drinks. We sat and talked for a while as she drank. She questioned me relentlessly as we sat, but I was careful not to set any specific expectations for what she called "my big night". As we talked, I slowly began to feel more comfortable around her. We were talking like we did before all this happened and we were even able to share a few laughs about it. I loved her and I knew I always would, no matter what happened. Finally she asked me if I would like to go look through her clothing to see what styles I would like to wear. As I followed her into our bedroom she glanced at me over her shoulder with a sexy smile. I couldn't believe I was married to this newly created sexual creature. She slowly showed me several of her outfits and asked me what I thought. I really liked several of her dresses and skirts but I made sure not to select anything specific. I wanted her to pick out what I wore. Finally she opened her lingerie drawer. This was the part I was looking forward to. I reached for a pink bra that was on the top of the drawer. "You know that bra does not go with the garter belt and stockings Rob gave you," she said. "You should really pick a black bra and panty set." My stomach jumped into my throat at the mention of my gift from Rob. I still could not believe he had done that to me. As a matter of fact, I still couldn't believe Jennifer had told him about that part of our agreement. I wondered what other intimate details of our lives she had shared with him. "Why does he get a say in what I do," I responded in a low voice. She ignored me and started handing me pairs of black panties and their matching bras. I examined each item as she handed them to me but my mind was fixated on Rob. I knew he had slept with Jennifer and taken her faithfulness from me, but I wondered what possessed him to try to make such a mockery of me. What he had done had taken deliberate effort to embarrass me. He had actually gone out and purchased something for the express purpose of making me feel ridiculous. He had also given Jennifer something to symbolize his new status in our lives. My mind then wandered to the image I had of him caressing Jennifer's body. My penis throbbed at the picture I had in my mind. I was snapped back to reality when Jennifer spoke. "How about the bra I'm wearing now," she said as she moved in close to me. My focus now turned to her. I gazed longingly at her chest. It wasn't the bra but her breasts I longed to touch. It had been a long time since I was permitted to touch them, and I was still unsure if she was willing tonight. "It looks great through your blouse," I responded and moved my hands to remove her outer garment. I became even more excited when she made no move to stop me. "Why don't you take it off to see it better," she said. I needed no further encouragement as my hands moved to her back to unhook the bra. I felt like a teenager removing a bra for the first time. My euphoria was broken when she spoke again. "Rob was the last man to remove this bra from me," she said. It seemed to me that she emphasized the word "man". My stomach turned when she said it. I wondered how she could say such a thing. I tried to say something but I am not sure if it came out or not. I assumed she wanted to reject me again, so I tried to let go of her. I was shocked when she seemed to hold on to me forcefully and began to pull my clothes off. My mind was in a blur as she quickly pulled my shirt up and undid my pants in a smooth movement. Images of her and Rob naked continued to run through my mind. I wondered about his reaction when he removed her bra. Had he immediately licked her breasts? Had he caressed and squeezed them? He had just looked at them, triumphantly? Each scenario had its own humiliating vision in my mind. Again, my wandering thoughts where broken by her words. "Come on, Rob couldn't wait to get my clothes off," she said. As she said it, I gazed into her eyes. I saw a lust I had never seen before. Was it for me? Or was it the memory of Rob? Her statement seemed to confirm what I had hoped, that her night with Rob had been rough, lustful, and full of passion, but not intimate. She moved my hands back to her bra. As I undid the clasps she told me to continue undressing her. When she was naked I admired her body as if I was seeing it for the first time. I was still very nervous but I felt a lot better when I noticed her removing the bracelet as we moved to the bed. At least I could make love to her without the reminder of Rob. As me made love, I couldn't help but try to give her what Rob had given her. I tried to be aggressive, but she still maintained control of the act. There was a mixture of the familiar and the new in our coupling. The positions were the same but she struggled with me, pulling me in new angles and shifting her body as if trying to get me to touch her in slightly new ways. I knew she was trying to recreate some of the feelings she had with her new lover. When it was done I felt a relief. I had regained some of my former privileges. We held each other close for a while then made love again. There was a closeness and tenderness in our second session that made me feel like I was welcome in her bed again. The following day was like old times. Jennifer and I were playful with each other again. I gave and received several hugs from her throughout the day. We had a wonderful day together and as a family. I could barely contain myself. I felt like together we had weathered the storm and our marriage and love for each other had stayed intact. For two weeks nothing was said about the past. No mention of Rob or my dressing came up. I was relieved. My rational mind hoped we could continue our old relationship and eventually forget everything that had happened. Jennifer was the loving wife I remembered. The only difference from before was the more confident way she carried herself. I had to admit the change. Since her night with Rob she acted just a little more self assured. She continued to dress in more attractive clothing. Nothing over the top, but either consciously or unconsciously she seemed to button one less button on her blouses, and she always seemed to be wearing shoes just a little sexier than before. She also teased me with her body language and facial expressions. When she passed me in the hall or kitchen she would lean into me and look me directly in the eye, always flashing a coy smile. I was also glad to have reaffirmed myself in our bedroom. We had regular sex several times; I even initiated it and was accepted. I was happy. I felt like I had my wife and best friend back in my life again. All that changed one evening when the phone rang. I was in our study, finishing up my work for the evening when I picked up the phone. I had not bothered to look at the caller ID. "Hey, what's going on?" it was Rob. This was the first I had heard from him since his package arrived three weeks earlier. I was very apprehensive about speaking to him. I wondered if he had called to speak to me or Jennifer. "Not much, what are you up to?" I replied, it was my standard response. We talked for a while, mostly about sports and current events. As the conversation proceeded I became more comfortable. My hope was that he was sorry for embarrassing me and was trying to smooth things over. Rob and I had disagreements in the past and we always just let it go. My thought was that if I could get through the conversation without mentioning anything about what had happened that would be the end if it. I know it sounds dumb, but that is the way men deal with things. We continued to talk for a while and I made hints that I needed to get off the phone. Then he pushed the issue. "So tell me, did you get everything you wanted for your birthday?" he asked. I was floored; he was not going to let me off the hook. "Well, it is not for a couple of weeks," I countered, still clinging to the hope he would let me off the hook. "Oh sorry," he said. "Well I hope you enjoy the gift I sent you." I had no idea what to say back. How do you proceed with such a conversation? I tried to change the subject back to sports but he continued. "Do you at least know what else you will be wearing on your birthday? Have you picked out and panties yet? Maybe you should get a thong." he teased. We had always had the kind of friendship were we kidded each other relentlessly, but this was different. He seemed to be making a direct assault on my manhood. The problem was he was right. I had no response as he continued. "You know you should get a bra like Jenn's, her breasts are just the right size." He said and waited for my reply. My temper started to kick in. I responded defensively. "What are you trying to do?" I asked. "I'm just asking you about your birthday, I thought since I had played a part in it I should have some input on your big present." He said. I was surprised he was even willing to bring up the subject of me in women's clothing. "My birthday is between Jennifer and me," I said, still pissed. "Ok, but some of it was between Jennifer and me, if you remember. I have been meaning to thank you for that. It was some of the best sex I have ever had. Jennifer really seemed to need it," he said. "Rob why do you have to act like this, isn't it enough that you had Jenn? Why do you have to be a prick about it? Do you really what to fuck up my marriage? It is not my problem that you have never been able to keep a relationship for long." I said. I was trying to hit a point with him. "Alright fine," he said. "But you need to understand something." "What" I said, my tone laced with sarcasm. "I have never, not satisfied a woman, and it was obvious to me that Jennifer was not a satisfied woman until I had been with her. She told me I had found some very special places within in her that you had never known were there. You need to try harder to satisfy her sexually, and I can promise you she doesn't want to see you dressed up like a girl. She wants a man." He said. I worried that he was right. Had I ever been a good lover to Jennifer? Had she tolerated my inadequate love making until I had pushed her over the edge by asking to cross dress? I was sick at the thought. "Listen, why don't I come for a visit on your birthday, you dress up, and then Jenn and I will have our own celebration, you can watch if you want." he stated. I hoped he wasn't serious, and he just wanted to show me how stupid my fantasies were. I hung up the phone. I had nothing else to say. I sat quietly alone for a few minutes. My heart felt like it would pound out of my chest. I had just had a conversation with a man who had slept with my wife, and on top of it he knew my most secret fantasies. I had no idea what to do. At first I thought I should just forget it and not tell Jennifer, but I knew he might call back and talk to her. After a while I got up and walked slowly to our living room. I knew I had to tell Jennifer about the call, but I was not sure how. I walked in and took a seat on the sofa wondering how to start the conversation. Jennifer looked at me. She could obviously tell something was wrong. "What's the matter?" she asked me. I still couldn't bring myself to answer her. "What is it Steve?" she asked again the concerned tone in her voice sounded more urgent. She moved to the couch and held my hand. The warmth of her touch made me feel better, somehow secure. "Tell me." She said with a worried look. "That was Rob on the phone," I replied as I looked her in the eyes looking for some sympathy. My heart sank as I saw Jennifer's face turn from worried to somewhat amused. A small smile crept over her face and she visibly relaxed. "Did he give you a message for me or ask to speak to me?" she asked, I could hear the hopefulness in her voice. I could only shake my head no. "Well, what did he say?" her tone now had and edge. I was not sure if she was angry at me for not elaborating, or angry at Rob for not calling to talk to her. My voice was trembling as I replied. "He said he just called to talk. So we started talking about sports, but then he asked if I had my birthday. When I told him it was still a few weeks away, he told me he hoped I enjoyed wearing his present." "Go on," she said. The slight smile had returned to her lips, and her eyes were locked on mine. I tried to go back to discussing sports but he kept slipping in remarks about what I should wear, like panties or a thong and that I should have breasts like yours because they were just right to hold." I stopped to take a breath. I need to collect myself. I could not believe I was sitting here telling my wife about my conversation with her lover. As I resumed my voice quivered with embarrassment. "After a while he thanked me for letting you spend the night with him and he told me that he was sure you enjoyed it as much as he did." I looked at her face as she turned her head and blushed. I continued, "I tried to turn the conversation back to sports but then he asked if you had told me about the special places he had found that night." She returned her gaze to me. Her face was flushed. I could tell she was fondly remembering her time with Rob. I could feel my heart pounding in my chest. "Well my girly man, what did you say to that?" she replied. "I told him I did not know anything about what happened that night," I paused before continuing. "He laughed at me, and then said he was sorry but I probably had not been allowed to have sex with you yet." I stopped for a moment. I did not know if I could tell her anymore. My mind was going in so many directions. Part of me wanted to just beg for forgiveness, but another part wanted to give Jennifer some space to see where she wanted this to go. Finally I told her the last of it. "He also asked if he could come over on my birthday and see me dressed, then the two of you could celebrate my birthday together." My voice trailed off, but Jennifer sensed there was more. "And?" she said glaring at me. I took a deep breath. "He said I could watch if I wanted to." I was struggling for air as I said the last sentence. "I hung up the phone while he was laughing." Jennifer continued to glare at me, "Well what did you expect, did you want to watch instead of listening outside the door?" How could she have known that? I was taken aback. "You did give me to him as a present; maybe I should call Rob back to discuss this." she said in a very aggressive tone. "No please don't" I pleaded. "Why not? I am sure he wanted to talk to me before you hung up, why don't I call him back. I will put him on speaker so you can hear." She said as she looked at me. "I think I will have a drink first," she said as I looked her, she raised her eyebrows which was my queue to go get it for her. I was glad for the chance to retreat and try to catch my breath and get my pulse down. As I made her drink, I tired to take deep breaths to calm myself. I thought about what Rob had said and tried to sort out my own feelings before returning to Jennifer. Rob's comment about letting me watch stirred something in me. The image of Rob and Jennifer on our sofa, locked in a passionate embrace burned itself into my mind. I am not sure why but I became extremely aroused. I immediately got a strong erection. I tried to turn my thoughts away so as not to let Jennifer know my arousal. I tried for several minutes but I could not get the thoughts of the two of them together out of my head. I realized I could not stall any longer so I took Jenn her drink and hoped she would not notice the bulge in my trousers. I give Jennifer her drink and took a seat next to her as quickly as possible to hide my embarrassment. "Go ahead, call him," I said as calmly as I could manage. "Do you want me to?" she replied. "You want to humiliate me so go ahead, it does not matter what I want," I tried to sound sympathetic. I was hoping she would tell me she would not call him. "Its getting late now and I know we have a lot to talk about," she said. I breathed a sigh of relief, but she continued, "perhaps I will call him tomorrow." "Oh no," I realized she would not let this go easily. She reached over and put her hand on my leg. I was hoping it was a gesture of sympathy. "Its ok sweetie, when I call him you can listen," she said. This was not the sympathy I was looking for. I wondered how I could have let all this happen. I had no idea what to say. "Did you want Rob to tell you what happened?" she said. I was still speechless. The truth was I wanted to hear it from Jennifer, but how could I admit that to her. "Never mind, perhaps you will hear it when I call him," she added, twisting the knife. "Do you want to tell me what you think happened?" I buried my face in my hands and said no. "Perhaps you prefer to imagine what happened when Rob undressed me?" her voice had taken on a low lustful tone. I imagined Rob slowly unbuttoning the red silk blouse she wore the night she slept with him. I wondered what thoughts went through Jennifer's mind when another man saw her naked. I could not stop my own arousal at the thoughts. She paused for a moment, "and imagine his hands moving over my body?" I had never heard Jennifer say anything that way before. My thought shifted to an image of Rob's hand cupping and squeezing her breasts. I wondered if he had been gentle or forceful. I could not take it anymore; my brain seemed to be on overload with the erotic images of their love making. I turned to look Jen in the eyes and tried to muster some words. "Stop, please don't Jen," I begged her for some mercy, some show of affection. She reached for my crotch. My complete arousal was obvious to her. "Are those just words or do you really want me to stop?" I knew I didn't, but at the same time I was not sure if I was ready to hear every detail. There was a pain that accompanied the lust I felt. The pain of losing the woman I thought I knew so well because of my own stupidity. I had no answer. She put her drink down and drew her body close to me. She whispered in my ear, "did you like watching Rob and I making out on this settee?" My body stiffened, "I didn't know you saw me," I said. She gave me a sexy giggle, but a withering glare. "Its time I went to bed," she said. I grabbed her hand. I wanted to hold her and tell her that I loved her but how could I after what I had done? We looked into each others eyes for a few moments before I got up to lock the house for the night. As I headed for the bedroom my sexual arousal subsided, but I still longed for Jennifer's affection. I wanted to climb into bed and hold her. I wanted her to know how much I loved her despite what had happened and what I had allowed. My hopes were dashed, when she was obviously angry at me for being so passive to Rob. She made some snide comments to me before kissing me goodnight and rolling over. The following few days were some of the most insecure of my life. I realized Jennifer knew my most secret thoughts and fantasies. I wondered if she still thought of me as a real man. I wanted to hug her all the time and I even asked her to hold me as we went to sleep one night. A few days after the phone call,after we put the kids to bed Jennifer literally attacked me in our living room. It felt like she devoured me. She was aggressive and demanding as we made love. Actually it did not feel like love making, but it was passionate. During the act she was driving me for more. She was pulling me into new positions and new angles while urging me on to satisfy her. After a while I was exhausted but the memory of her taunting whispers from a few nights before kept my passion fueled. When we were done, I asked her what had gotten into her. She gave me a very coy reply, which I knew meant it was none of my business. As I drifted of to sleep I worried that it was not me that had aroused her but the memory of Rob. However I was comforted by the fact that I could satisfy her, no matter what turned her on in the first place. I slept soundly that night. After that night we seemed to return to our normal selves and I was happy. I realized that though things had changed we still loved each other. In fact, now we even had a very exciting sex life to go with our deep friendship and love. Around the same time, I started to experience some problems with my work. I managed a team of employees and we had a group project that required everyone to put in extra hours and effort. We had a deadline which put everyone in my office on edge. I normally try to be a very supportive boss and not put a lot of pressure on my people, but this project was different, I had to take the lead and I could not stand for anyone wasting time. Several times I was forced to take a hard line with my team in order to get their best efforts. This put a great deal of stress on me and I know I took some of it home with me at night. One evening after a really tough day, Jennifer told me she was planning on having her hair cut short. I put up a bit of an argument because I loved the way she looked with her shoulder length hair. After a little back and forth, Jennifer walked over to where I was sitting and glared at me. She told me her mind was made up. Then she gave me the same raised eyebrows that she gave to me the night she slid into the booth with Rob. I immediately realized that she would do as she pleased and that I had no say. Strangely enough, as she walked away I breathed a sigh of relief. It was great to have her showing so much confidence. Her attitude stirred feelings of arousal. When I arrived home the next night I was shocked. I thought she would just have a little cut, but she looked like a different person. Her hair was really short and it conformed to the shape of her head. I guess I was so accustomed to the old style that this style looked very severe to me. I avoided the question when she asked me how I liked it and sat down in a chair. She strode over to me in her now familiar swagger. I could tell she wanted to make a point. "You look like you intend to be in charge," I said, feeling defensive. She reached down and lifted my chin as she planted a very aggressive kiss on my mouth. "You will soon get used to it," she said in a very firm voice. "I am sure I will, you look great," I said. I think my mouth hung open as she walked away from me toward our dining room. The day before my birthday, my team finished its work project. It had gone well and it was a tremendous relief for all of us to have finished. In retrospect, I was glad the project had come up. While it had created a lot of stress for me, it had allowed me to get past the last few weeks without constantly thinking about my birthday and about Rob. Thankfully he had not been mentioned in our house since the night of the phone call. In fact the only mention of the subject had been when Jennifer had told me we would wait for the weekend for my present. Driving home that evening I reflected on the past few weeks. I was actually surprised that I had been able to keep my mind off of the upcoming event. I thought back on my history again. I realized it had always been this way. Don't get me wrong, I had always been interested in women's clothes, but there were times when I thought about it all the time, I burned to feel them, but there we other times when it hardly entered my mind. I was in one of those periods now, and I questioned whether I should go through with dressing up at all. Maybe it was something I could control. Rob's words rang in my mind; "Jennifer does not want to see you dressed as a woman." For the next day I wrestled with the thought of calling off my big night. I thought if I told Jennifer I had changed my mind about it, we could eventually forget everything that had happened. I even planned my conversation with her, hopeful that I could find a way to permanently bring back all of the love and affection that was once a constant in our lives. Finally my birthday came. It fell on a Thursday night. That day at work I continued to turn over the possibilities in my mind. Would giving up my fantasy bring the old Jennifer back? Did I even want to go back? I realized that even though she seemed to have me constantly off balance, I had never been more attracted to her than I was now. Every time I saw her now I wanted to touch her and hold her. I was still waffling as I arrived home the night of my birthday. I immediately made up my mind when I saw Jennifer. She was wearing a long black skirt, black stockings, and a matching black turtleneck. The turtleneck clung to her curves and while it was not revealing, it certainly showed her assets. She looked incredibly sophisticated and sexy. She must have spent some time considering her outfit, because it seemed so perfect. To the kids and our family members it appeared as if Mommy had dressed up for Daddies birthday. However from my perspective it was the promise of excitement, the promise of more to come. We had a nice party with the kids. My mom stopped by after dinner to drop off a gift and have some cake with the kids. I noticed she seemed rather cool toward Jennifer. It struck me as odd because they had always seemed to get along very well in the past. As well as a mother in law and a wife can, I guess. After dinner Jennifer and I sat together for a while. I couldn't help myself and I asked her what would be happening this weekend. All she would tell me was that I would be dropping the kids off at my mothers on Saturday. I was beginning to get nervous about what might happen. I had no idea how far Jennifer would go with my present. My nervousness was abated when she allowed me to caress her body and eventually make love to her. That Friday at work was a very relaxed day. We had finished our project and we had the weekend coming on. I allowed my staff to spend extra time at the water cooler and even allowed several of them to leave early. I spent most of the day thinking about the coming weekend. I was nervous and excited at the same time. What would Jennifer have me wear? Was her outfit the night of my birthday a preview? As the day wound down I found myself getting more nervous and my mind more preoccupied with my fantasy. I told my assistant it was ok if she left an hour early. She was a fairly attractive young woman about twenty five years old. Despite her youth she had great work ethic and had been a huge asset to me from the day I hired her two years before. One of her best qualities was that she could normally read me like a book. She could tell when I was angry and trying not to show it. She could also tell when I was not angry, but was trying to act that way to make a point. As she was packing up I was walking past her desk. "So any big plans for the weekend?" she asked. My mind was turning and I was not ready for the question. "Uh, no, not at all, why?" I stammered my response. "Oh, no reason, you just seem to be in a great mood today," she replied and smiled at me. I relaxed a little. I paused a moment to watch her to see if she had noticed my uncomfortable response. She was just smiling the way she always does. "No, I think I am just relaxed because we finished the project on time, you guys did great," I made sure I threw in a compliment. "Yeah it does feel good to have it done, Ok, see you on Monday," she said as she picked up her purse and headed for the exit. I noticed a small smile as she left. "Bye," I said. I thought about what she would think if she only knew my plans for the weekend. Saturday finally came. I was on edge all morning. My mind was turning over all the possibilities that Jennifer might have in store for me. I was also nervous about what her reaction would be after I was dressed. I feared she might be so disgusted that she would stop the whole thing. She had already told me that she thought of me differently since I had confessed my desire to dress. Would seeing me dressed make it even worse? Thoughts of calling the night off started to resurface. That afternoon I dropped off our children at my mothers. She asked if I wanted to stay for a bit, but I told her I had some errands to run. The truth was I wanted a little time alone to think before I went home. On my way home I stopped at a shopping mall. I wanted to just walk for a while. As I did, I ran everything through my mind again. Should I decide not to go through with the dressing? After a while, I passed an attractive woman about my age. She was dressed very nicely, not sexy, but smart. She seemed so confident, so self assured as she noticed me looking at her. She gave me a smile when she noticed my gaze. She was not self conscious at all. She seemed to enjoy the unspoken attention I gave her. I looked away after returning the smile. What was it about her that made her that way? I knew on a conscious level it wasn't the clothes, but my mind wanted to feel the way she felt, or at least the way I thought she felt. I made up my mind at that point that I would have to experience the feeling of being a woman, even if it was just for a little while. As I arrived home I had no idea what Jennifer had in store for me. I took a deep breath and opened the front door. Jennifer was waiting for me. She was dressed in her casual around the house clothes. I felt better when she seemed to be as nervous as I was. "Are you sure you want to go through with this?" she asked me. "Yes, I think I have to," I replied as I hugged her. She seemed to hold the hug a little longer than normal. It was as if she was hugging me for the last time as I was. I tried to push this thought out of my head. "Ok, from now on you must do everything I say," she said. I nodded my head in agreement. She seemed to smile a little and relax once she had my consent. She told me to go shave and I headed for our bathroom. I took my time and tried to shave as close as possible. When I was finished she lovingly caressed my face. She told me she still felt some stubble and told me to shave again. This time I put in a new blade and shaved even slower. I felt my face and it felt smooth to me. This time it passed inspection. Jennifer then told me to go get a shower. She had been quiet so far and was not giving me any clues as to what was still to come. As I showered the warm water help relax me as I wondered what outfit she had picked for me. She was waiting with a towel when I finished. She had me dry off but did not tell me to get out of the shower. When I was dry she began spreading a lotion all over my body. I was looking forward to her touching me, but her motions were not sensual. She was applying a thick layer over every part of my body from my neck down. The only area she skipped was very conspicuous. The lotion was cold going on and after a while I noticed it had a terrible smell. I was starting to get the idea that it was not a skin moisturizer as I had originally thought. After what seemed like fifteen minutes I felt my skin beginning to tingle. I called out to Jennifer to let her know it was getting uncomfortable. My fear was confirmed when she called back that it was removing all my body hair. My nerves came back as I immediately realized I would be dealing with this for some time to come. I tried to figure out in my mind how long it would take to grow back. I was glad it was early fall and cool weather was coming on. It would make long sleeve shirts less noticeable. For the next five minutes I tried to relax and accept what was happening. That all went out the window when Jennifer turned on the shower. The first blast of cool water shocked me, but not nearly as much as when I saw all of my hair just rinsing off my body. Jennifer made a coy comment about no pain no gain when she saw the scared look on my face. When she was confident all of my body hair was gone she led me to our bathtub. She had drawn me a bubble bath and the feminine scent of the water was a welcome change from the smell of the hair removal lotion. I was glad to have a few moments to relax as I slid into the warm water. While in the bath it dawned on me just how different my body felt without hair. First I ran my hands over my arms and felt the strange smoothness. Then my hands slowly moved down the rest of my body until I ran my hands over my now smooth legs. The sensations relaxed me further. I made up my mind at that point to just try to relax and enjoy my night for what it was, and worry about the consequences later. I relaxed in the bath for another ten minutes or so before Jennifer came in with another towel. I dried off and she led me to our guest room. She had laid out my clothes on the bed and placed a chair near our full length mirror that she had covered with a sheet. I took a quick inventory of the items on the bed as we entered the room. A white silk blouse, a black skirt, a black bra and panty set, and a pair of black strappy sandals were all arranged on the bed. In the center was the gift box from Rob. The sight of the clothes set my mind racing and my arousal level increased significantly. Jennifer noticed my arousal and immediately handed me the panties to put on. She smiled as she handed them to me and took a quick glance at my crotch. The panties were silky but seemed to have a lot of elastic in the material. I experienced yet another new sensation as I pulled the panties up my hairless legs. The material seemed to mold itself to me as I pulled them in place and tucked myself off to the side to make myself more comfortable. I glanced up quickly at Jenn, her eyes were still lingering on my now constricted manhood. She quickly looked up and handed me one of her silk dressing gowns. I put it on as she led me to the chair. The material felt cool on my skin. I sat down as she began working on my hair. When she had finished putting curlers on my head she pulled out a cosmetic bag and began to work on me. There was very little conversation as Jennifer proceeded to do my nails and applied make up to my face. When she glued false nails on my fingers I had to remind my self to just enjoy the experience and to worry about how to get them off later. She had selected a soft pink shade of nail polish, and from what I could tell applied a matching lipstick. I found the makeup had a faint but pleasant smell and I smiled softly when I pursed my lips. There was a new silky feeling from the lipstick. Finally Jennifer stepped back and admired her work. She had even polished my toenails. A strange feeling swept over me as I felt like I was being evaluated. She turned around and pulled something out of a drawer behind me. She paused for a few moments before coming around the front of me with two artificial breasts. My eyes widened. I wondered were she got them. I was shocked she was planning to go this far with my dressing. I tried to relax as she held them to my chest. She spent a few minutes trying to make sure they were in the right position, and then she pressed them onto my chest and held them against me for what seemed like two minutes or so. When she removed her hands I immediately felt the weight of them pull against the skin on my chest. I looked down and then quickly back at Jennifer when I realized she had glued them in place. "When will they come off?" I said, I knew my voiced sounded petrified. She took a moment to read the tube of glue she had in her hands before responding, "It says they should hold for about a week." She had a satisfied smile on her face, the same one she had as she watched my body hair wash away. "I can't wear these for a week, everyone will see," I pleaded, hoping she would tell me there was something that would get them off quicker. She just giggled at me. "Well you will have to behave then, or maybe wear a sports bra to flatten them," she said as she handed be the black lacy bra. I lowered my eyes as I put the bra on. My new "breasts" filled the cups perfectly. As Jennifer adjusted the straps for me, the tugging I felt on my chest lessened. When it was on, my hands instinctively cupped my chest. As I felt the bra a feeling washed over me. It was one of contentment. I knew then I would do whatever else Jennifer demanded. My worries seemed to fade away. I proceeded to put on the garter belt, blouse and skirt with the help of Jennifer. She gave me some instructions and I followed them. I loved the feel of the skirt, it had a silky lining that gave me a wonderful sensation as I pulled it up my hairless legs and it rubbed against the panties I had put on earlier. Finally Jennifer said "Stand up, hands by your side, and let me look at you." It seemed like and order to me. I did as I was told and Jennifer gave me the once over. My eyes were downcast but I heard another of her satisfied giggles. "Now for the stockings," she said. I glanced at her and she smiled and raised her eyebrows at me. I excitedly reached for the packet and started to open it, but Jennifer stopped me. "Careful, don't snag them with your new nails," she said as she opened them and handed me the first stocking. I sat down and placed the stocking over my foot. I was conscious of my nails and was very careful to try to grip the material with the pads of my fingers instead of the tips as I would have normally done. I took a long time putting the stockings on, both because I was careful and because I was really enjoying the feeling of the flimsy material as it stretched and conformed to my legs. When I was done Jennifer told me to stand and lift my skirt. It felt very strange standing there holding up my skirt while she adjusted the stockings and reattached them the garter belt. Her hands felt wonderful as she adjusted the fabric and smoothed out the stockings. Finally she handed me the shoes and I put them on. There was a small heel which seemed to make standing just slightly awkward. I noticed that the breasts and the heel of the shoes gave me an ever so slightly different posture. At last Jennifer pulled the sheet off of our full length mirror. I was immediately transfixed by what I saw. While I did not think I would pass a close inspection, I definitely looked like a reasonably attractive woman. The clothes gave me a very soft, feminine appearance. I looked a little flat in the chest from the front, but when I turned to the side, I could see the outline of my breasts. I was really pleased that I did not look totally ridiculous. I even noticed how good my legs looked in the stockings which were very visible since the skirt only came down a few inches below the ends of the garter. I stood and admired Jennifer's work for a few moments and even struck a few poses for myself in the mirror. In was jolted back to reality when Jennifer asked, "Do you like?" "Yes very much," I replied and I moved toward her and kissed her cheek. "Thank you, Jenn." "It's ok my girly man," she said. Her tone had softened. She smiled a soft reluctant smile, which I returned. "Now go sit on the settee and look at the magazines I've left while I get ready," she said. I walked out of the room and towards the living area. I enjoyed the many sensations I felt as I walked. The skirt swishing around my stocking covered thighs, the new bounce in my chest, and most of all my legs slightly brushing up against each other. As I sat down on the couch my mind began to churn again. It was incredibly exciting to finally be dressed as a woman, but I could not shake a feeling that I needed something more. I wondered what else Jennifer might have in store for me that evening. Would we simply spend the evening talking or did she have other plans? I am not sure why but I thought back to the night Rob called, and how she taunted me for not standing up to him. Would she do more of that tonight? Worse yet, would she call him to tell him I finally got my wish and was wearing his present? My rational mind feared these things but as I imagined them I felt that strange feeling of serenity creeping over me again. What did I really want from all of this? I realized I still wasn't sure, but at the same time I knew whatever did happen, it was up to Jennifer. I made up my mind I would do whatever she said and hope for the best. After a while, she entered the lounge carrying some drinks. She was dressed in a simple black outfit with some high heeled sandals. The mono colored clothes made her appear taller and more confident. She looked like she was in charge of the situation as she sat down with me and we began talking. We talked for awhile about nothing in particular, but the way she talked to me was odd. She was talking to me as if I wasn't dressed as I was, just innocent chatting. Finally we went into the kitchen to have dinner together. Over dinner she finally brought up my outfit. She questioned me for some time about how I liked my clothes and how I felt about her choices for me. I found it difficult to talk about my feelings. I was still embarrassed about why I would like to be dressed like this. I tried to avoid most of the questions; I worried if I told her how great everything felt she would think less of me than she did already. When we finished our meal, Jennifer stood and took my hand. As she lead me away from the table she said, "Let's go for a walk in the garden." I froze. Even though it was dark outside it was easy to see into our garden area from the neighbors houses. I was petrified that anyone would see me. I made a weak protest. "Don't be silly, it's dark and I will turn off the outside lighting," she said and paused for a moment before continuing, "all anyone will see is two women walking together," she added with a smile and raised eyebrows. I was still frozen. I felt like I should stand my ground. That was before Jennifer's smile turned to a scowl. "Outside now," she commanded, and smacked me square on the ass. I was surprised at the force of the blow. I could not remember ever seeing her hit anything before. I immediately went through the door, but I cowered just outside the entrance. Jennifer took my hand when she emerged. The warmth of her touch made me feel better for a moment but then she pulled me out into the open. I looked up at the night sky. Unfortunately, it was a clear early autumn evening. There was a nearly full moon that gave a pale light to our garden. Jennifer and I walked toward a group of trees at the far end of our garden. It was only twenty five yards away but it felt like a mile from the security of the house. When we reached the trees Jennifer pulled me close and kissed me. Her lips felt wonderful against mine, and it felt strange as her hands traveled down to my bottom and pulled me into her. I really wasn't sure how I was supposed to react. Jennifer broke the kiss and began to lead me back to the house. I was happy to be getting out of sight, but about halfway to the house our neighbors outside lights came on. I immediately tried to hide behind Jennifer and hurry into the house. Jennifer however, turned and called a greeting to our neighbor before casually walking back to the house. I felt like my heart would explode out of my chest when I finally reached the safety of out living room. I was short of breath as I said, "How could you?" She simply laughed at me. "Its all right, no one would recognize you anyway," she said. "Please don't do that to me Jennifer," I pleaded. Even though I was enjoying my outfit my greatest fear was that everyone would find out about my present. Rob knew already, that was bad enough. I wondered if she had shared it with anyone else. She gave me hug and flippantly said, "Do what?" I tried to calm down as we moved to our sofa. I did not even have time to catch my breath before Jennifer moved into me. She placed her hand on the calf of my leg which was crossed toward her. The feeling was electric as her hand slowly slid up my stocking until she reached the hem of my skirt. She then lifted her hand to my face and turned it so I was looking into her eyes as she moved in to kiss me. She had kissed me outside but it was nothing like this. Her mouth covered mine and her tongue pressed into my mouth. This kiss was gentle but firm at the same time. Her hand remained on my jaw as if she was thought I would try to break the kiss. After a short time her hand left my face and began caressing my body. She slowly began unbuttoning my blouse. Eventually her hand found its way inside my bra. She gently squeezed my breast form and although she was not touching me directly, I felt her movements as the breast form pulled and tugged at the skin it was adhered to. I was surprised at how good it felt. Despite all the good feelings I was experiencing as we made out, I noticed a strange feeling inside of me. On a conscious level I was experiencing everything I had fantasized about for years. However I could not shake the feeling that something was missing. There was the same nagging feeling I had felt several times since the night Jennifer had slept with Rob. It was as if her new aggressive attitude had awakened feelings that had been sleeping deep with in me. Despite the fact that I was definitely enjoying the feeling of Jennifer fondling and kissing me, my self doubts were manifesting themselves below my waist. I noticed that I had not yet achieved an erection. After a while Jennifer's hands began to move under my skirt. My first reaction was to open up to her and allow access but I did not want her to feel my limp penis which was still trapped in my panties. My anxiety built as her hands reached the tops of my stockings. I shifted positions trying to evade her caressing, probing fingers. Finally despite my struggles her hand cupped my flaccid manhood. She continued to kiss me for a few more minutes before breaking the kiss and moving away from me. I could hear the frustration in her voice. "It's time we went to bed," she said as she got up and took my hand. We walked toward our bedroom. I was hoping a change of venue would help me relax and enjoy the experience. Unfortunately my penis still felt as unresponsive as ever. Halfway down our hall she stopped. We were right in front of our guest room. She turned to me and gave me a soft kiss on the check. I looked into her eyes. There was sadness in them. "Goodnight, girly man," she said to me softly. "What?" I pleaded, "Aren't we sleeping together?" "I don't sleep with women, and I only invite men like Rob into my bedroom," she replied in a manner of fact voice. I looked down. How could I argue with her? I was standing before her in a blouse and skirt. I remembered the night I slept in our guest room while she and Rob slept together in our bed. I felt like I had given up my masculinity. I had no idea what to say next but I knew I could not spend the night alone in the guest room. Instinctively I grabbed her arm. "Please Jenn sleep with me," I begged. I held on to her arm as if I were hanging on to our marriage. "Why," she shot back. "You aren't interested and I am not into rape," she almost shouted at me. She looked at me with a piercing stare, "let go of me." I released her arm. I knew I was in no position to make any demands of her. After all that had happened, I knew that whatever happened from here would be up to her. I was in her hands. Our marriage was in her hands. "I'm sorry Jennifer, please forgive me," was all I could say. I knew I was asking for more than forgiveness for grabbing her. I was asking for everything. I moved forward to embrace her. She avoided me and pushed me toward our bedroom. "Go in and we will get you ready for bed," she said. "Please Jennifer," was all I could manage. I was terrified of what she thought of me, dressed as a woman, begging to sleep with her. "Go touch up your lipstick," she told me. "I don't know how," I asked. I wondered why. "Just do what you have seen me do many times," she said. Her voice had changed back to a soft encouraging tone. I went to her vanity and picked up the lipstick I found there. It took me a minute, but I tried to put it on as evenly as possible. I looked at my reflection in the mirror. I still looked like a woman, but I was not sure what I felt like at that moment. Suddenly my thoughts were shattered as I saw the flash of our camera. I immediately spun around to face her. "What are you doing?" I screamed, even though I knew. I had dreaded that she might do this. She was taking my picture for Rob. The image of his condescending smile flashed through my mind. "I thought we should have a picture of girly," she said with an innocent smile. "Stand up and let me see you properly," "No," I begged her to stop. She simply smiled at me. Her demeanor had changed. The uncertainty has left her. I could tell she knew exactly what she wanted. "Yes Steve, I want us both to remember this," she said coolly. Her tone sent a shiver through me. I rose slowly. For what ever reason I knew I had to. My eyes were downcast as she again spoke to me. "Now tidy yourself up," she commanded. I just stood there not knowing how. She moved toward me and rubbed a tissue over my face. She stood back and admired her work when she was finished. "Now button up your blouse and look presentable," she said. I slowly turned and looked at myself in the mirror as I buttoned my blouse. It was strange trying to adjust myself in the mirror. I actually wanted to look nice for my picture. It was the moment I dreaded most but for some reason I was taking a small amount of pride in my feminine appearance. I wanted the picture to at least be respectable. I turned back to Jennifer and asked if I looked ok, my eyes were still glued to the floor at her feet. "Better," she said. "Now look at the camera." I slowly looked up. I thought she would give me a chance to smile or do something, but she snapped the shot just as I looked at the lens. "Good," she said. "Now shall we have one showing off your figure?" Her tone was lighthearted but slightly mocking. "Take your blouse off," she commanded. "Oh no," I stammered. I started to unbutton the blouse and remove it. She took the next picture as it fell from my body. I realized my new breasts would be clearly visible in the shot. When it fell away Jennifer told me to take off my skirt. I begged her not to take any more pictures. "I need one for Rob showing his present," she told me. I am not sure how to describe my feelings at that moment, but I will try. I knew that Rob had slept with my wife. I knew Rob had already been told of my desire to wear women's clothes and I knew that he probably knew what was happening to me that night, but at the same time I could not bring myself to pose for a picture for him. It was as if Jennifer was stripping away my last shred of dignity. My eyes began to fill with tears. I felt like I had given up everything, just for the feel of women's clothes. My voice came out in a raspy whisper. "Oh no, you can't do that," I said feebly. She repeated herself, "Steve, take off your skirt." I just stood there frozen. She quickly moved toward me and in one motion, unzipped my skirt. As it fell, I grabbed for it, it felt like my last chance. Then I felt the slap of Jennifer's hand on my upper thighs. She smacked me hard twice. I let the skirt drop. I felt the cold fabric pool around my feet. My hands moved to cover the exposed are