The Significant Other's Dilemma free porn video

THE SIGNIFICANT OTHER'S DILEMMA by enduringshades I found a parking place near the place. The neighbourhood is now familiar as I have been here several times observing the house before finally plucking up the courage to ring the doorbell. The neighbourhood consists of townhouses, once the homes of proud upper middle class Victorian households, but now accommodating multiple occupancy flats and bedsits. I got out of my car and made my way to the house, but when I got to the front door I didn't know which doorbell to ring. There were six to choose from and I didn't know her name. I was apprehensive, I didn't feel safe. I was nervous, I didn't know who would answer any of the doorbells. I was driven, I desperately wanted to find my husband but I was fearful, I didn't know what I would discover. So I retreated to my car to wait. THE LAST THIRTY YEARS I first saw the man who I would marry at one of those 'everyone invited just bring a bottle' parties popular among students three decades ago. I noticed him because he was one of a couple of boys dressed as girls. It was a regular party and it was becoming more common for young transvestites to socialise more openly. They were dressed the same as the regular girls, not flamboyantly or overtly sexually. I wasn't particularly attracted to them, they were just party goers. One did give me the eye, but I hesitated and before we made a connection she returned her attention to her companion. But that was enough, beneath the feminine veneer I saw the boy I was going to marry. A month later I was at a similar party when this boy approached me and asked me for a dance. I heart skipped a beat when I recognised him as the transvestite that had given me the eye, but I didn't let on as I didn't want to embarrass and scare him away. Now dressed as one of the regular guys, he was quite handsome. He introduced himself rather bashfully as Richard. We dated. We got married. We raised a son and daughter. And never at any time did my husband give me any inkling that he was that girl or that he had continued to dress in women's clothes or pursue his interest in any way. Maybe it was just that one time, perhaps a dare, and he never knew that I saw him at that party. THE LAST YEAR It was when our children had flown the nest, they had been awarded their degrees and started their careers elsewhere in the country, that I started to pick up signs that my husband had reawakened his interest in transvestism. He would spend long periods on the computer, typing away, reading, browsing and chatting, but there was never anything to show what he was actually doing. Then he started going out some evenings on his own, we had always done everything together. He said some old friends had got in contact and they were getting together again to catch up and reminisce and that I would be bored as none of the other wives would be there. The gatherings were never entered on the calendar, which was our usual practice, and were always on the first Thursday of the month. Before these evenings he would get quite excited and intense, and afterwards he was more relaxed and content. But when he came home, I was usually in bed by then, he would slip into bed beside me and we would have the most incredible sex. And he never smelt of alcohol. After a while, I started to notice small changes in his appearance. Things only a wife would notice, especially with the knowing of her husband's transvestite past. His eyebrows were trimmed. Not in a femine way, but enough to remove overtly masculine characteristics and to give a hint of a shape. His nails were nicely manicured, a little longer than a man's and again with the hint of an oval shape. And then he started shaving his arms, shoulders and legs. They weren't particularly hairy, but the unshaved hair on his chest and upper thighs drew the eye away from the shaved limbs. Just before his monthly meetings, these small changes would be freshened up and his face given a close shave. And then there were the telltale signs afterwards. The little bit of colour on his nails, some residue of makeup especially around the eyes, a slight hint of scent. I was now convinced that my husband was meeting up with transvestites and taking part himself, well I hope that was the case! Keeping secrets is one thing, cheating is another. I never found any suggestion that he was wearing or touching my things. The disappointing part was that he never let me into his secret, into that side of his life. I think I may have enjoyed coming with him as a supportive wife. As I was not questioning him about these changes or his regular meetings, everything was good between us. Then I started to be somewhat concerned. He has stopped getting his hair cut, other than the occasional tidy up, and it was getting quite long. He was lucky not to have male pattern baldness and I wondered if he wanted to be able to do his hair in a femine style. He was also becoming more emotional. And then came my first shock. One morning when he was having a shower the flowing water was flatting his chest hair and I noticed his breasts were becoming puffy. This I really did not expect. Dressing as a woman was one thing, but if he was taking female hormones that was a whole different level. I thought it was now time to say something. However, I needed to understand more before I broached the subject. I didn't want to push him away, I wanted to keep my husband whatever he looked like. I had to attend a residential training course for work the following week. It was only four days, but the evenings would give me time to do some research online and carefully consider when and how I talk to him about it on my return. THE LAST MONTH It was Sunday, tomorrow I would be leaving for the conference. Richard said he would cook dinner as he knew I would be busy preparing for the week. He does occasionally cook, but I was not expecting the meal he had prepared; three courses of my favourite dishes. He also laid the table formally with wine glasses and candles. He asked me to wear my red lace dress, I know he likes to see me in it. I said I'll be back at the end of the week and he said he knows but he wanted to do something special for his one and only love. The conference was busier than I expected in the evenings, but I did have time to decide what I am going to do. I was due back the evening of one of his meetings. I was looking forward to the best sex of the month, but I knew it was a good time to tell him that I had always known he was a transvestite as he would be on a high. I was going to let him know that I knew he had abstained throughout our marriage and while we raised a family. I wanted to reassure him that I loved him and he would not lose me. That our friends and family need never know and if he didn't want me to be part of his other life that was okay. But it was no longer a secret between us and so he does not have to be fearful. I got home on Thursday evening, the house was empty as I expected. I had a bath, put on my short black silk camisole that he always admired me in and went to bed. I lay awake and rehearsed what I was going to say and how I would respond to him, until I finally fell asleep. When I woke in the morning I rolled over to caress him but the bed beside me was empty. My first thought was that he was already up, so I rose and went to find him. He was not in the house and his car was not on the driveway. Perhaps he had left early for work and didn't want to disturb me, and then I realised I needed to get dressed otherwise I would be late for work. I'll see him when I get back, but I had a sinking feeling. When I got home the house was still empty, my husband had not come home. I rang his mobile, but got a message that the number was unavailable. I sent him a text message, a WhatsApp message and an email. If we had a Facebook account I would also have left a message, but we weren't into social media. I kept checking all night, but no response. I did think about trying friends and family, but couldn't face explaining why. I have heard nothing for a week now, so I had to accept he had left me and it was now up to me to find him if I wanted him back. I knew him well enough to know he would contact me if he was in trouble. I was quite sure he wasn't cheating on me or that our marriage hadn't broken down. It was just that he was desperate to dress, and perhaps live, as a woman and couldn't face telling me and hurting me. Every night I would cry myself to sleep. I decided to start looking for him using the internet. Just like the now well-known term 'transgender' had largely displaced 'transsexual' in general use, I soon discovered that 'crossdresser' was now a more frequent term than 'transvestite'. I was somewhat reassured to read that many crossdressers were not necessarily gay or transgender. I tracked down various crossdressing societies within reasonable driving distance, including one that met regularly on the first Thursday of the month. I always got the same responses. They were sympathetic but they could not give out any personal information, for obvious reasons, and any guest had to be sponsored by a member. They could not pass on a message using a member's real name and I had no idea if he had used a woman's name and if so what it would be. Some of them did offer advice and one mentioned what she called their 'significant other' councillor. I took down the details. I then tried looking for open events for crossdressers. I only identified one in our area, a monthly event held in a hotel that was organised by a shop specialising in supplies for crossdressing and transgender customers. I made a note of the place and time. I then drew up a list of LGBT friendly venues. Although I had only seen my love once, as a girl nearly thirty years ago, I was quite sure I would recognise him, unless he was in full drag makeup which I did not think was in his nature. There were more places than I expected, some I knew of, but hadn't realised who their clientele were. They ranged from gay bars and drag shows to restaurants and pubs specifically catering for or welcoming crossdressers. I drew up a rota, to visit at different times, but I decided that for shows and clubs just to watch the comings and goings. I spent every evening visiting or observing the places on my list. At weekends, I went up and down the high street and in and out of the shopping arcades and malls. LAST SATURDAY It was the Saturday three weeks after my husband hadn't come home. I had spent most of the day in the high street and the shops were about to close. I decided to have a coffee before I started my evening round, so I went into Costa Coffee. I was now a regular customer and Richard and I had often visited the place during shopping trips. I was waiting while my coffee was being prepared when I spotted a middle aged woman who looked familiar. It was him, or do I mean her, and I wasn't even looking! She was having coffee with an attractive but well built woman who could well be another crossdresser. I turned away, picked up my coffee and retreated to a table at the back. I decided not to make myself known, despite my desperate urge to rush over and hug and smother her in kisses. I did not know who the other person was and how my love would react. I observed her, like a birdwatcher keeping out of sight. She was accomplished in her movements and behaviour, she was almost like a natural woman. I was impressed. She was dressed mainly in black, wearing a polo neck jumper, knee-length pencil skirt, opaque tights and ankle boots with three inch heels. But she had added some colour with a long patterned red scarf. Her nails were red and her make up appropriate for the daytime and it enhanced her femininity. Her hair was shoulder length with gentle curls and looked as it was her own. Although Richard's hair was getting long I knew she must be wearing extensions to her own hair. To the casual observer she was a woman, but closer study would reveal masculine traits and her body was of a larger more stout woman. Well she was middle-aged. After some time, my husband stood up bent down and gave the woman a kiss on the cheek and left. I jumped up as I decided to follow her. She set off down the high street and then turned down a residential side road. I shied off catching her up, I realised I wasn't ready and wanted to know more of her current circumstances, before making a fool of myself. I followed her for about a half a mile, she was doing very well with heels, and then she entered a house. I noted the address and headed back to the high street car park and home for a much needed early night. What had impressed me, seeing my husband looking and behaving like an accomplished woman, was the time, preparation and effort that must have gone into his transformation and new life. I only wished I had been part of it. But the most amazing thing was that her outfit was identical to one of my favourites and the hair style was a close copy of mine. I was flattered but I wanted to take her under my wing and find a colour and style that better suited her. It was clear she was not getting or taking the advice from someone who had been a girl and woman all her life, like me. LAST SUNDAY I decided to stake out the house Richard had entered, I was taking my cue from those police dramas, to observe the comings and goings of the residents. I wanted to gain some insight into what my husband was doing. I hired a car, as she would recognise our own car, and parked a little way down the road. I never saw her leave or enter the house. Other residents left and returned, they all had keys, but nobody seemed to have any visitors and only one delivery. I surmised that she was living alone and had few friends, unless they were busy on a Sunday. YESTERDAY I had to go into the office the following day, but I arranged to take the next day off. On Tuesday, I returned to watch the house. I arrived in time to see her leave. She was dressed smartly in a royal blue skirt suit worn over a white blouse. She wore court shoes and carried a shoulder bag. She must be going to work, I was surprised she had a job, but there had been no withdrawals from our joint account and Richard's regular income had recently been paid in on time. I decided to follow her. She walked down the road to the high street and entered an office block. There was a sign board listing the companies and organisations, but I didn't recognise any. As I was in the high street I decided to do some shopping and come back before lunchtime. When I got back, I saw fortunately that there was a bench free with a view of the main entrance of the office block. I settled down and watched. It was not long before she came out in the company of the woman I saw her with in Costa Coffee. I was about to follow when they entered a nearby cafe. The cafe was quite small and I decided not to go in myself, despite being desperate as well as hungry. They came out after about half an hour and headed back to the office building. I went home for a rest. I was quite sure she was at work, so I returned at the end of the day in time to see her leave and go straight home. That night I decided I couldn't wait any longer. I planned to return to her place after work. I was a little disappointed that what she wore suited her perfectly, perhaps she didn't need my guidance after all, or there was another woman. But her gait needed improvement, she see-sawed from walking with masculine tendencies to an overexaggerated femine style, as if she was trying to remember to walk like a natural woman. Maybe I was needed after all. TODAY After my indecision over all those doorbell pushes, I am sitting in the hire car wondering what to do next. Then I saw her in the car's door mirror. She was coming home later than yesterday. As she passed, I impulsively jumped out of the car. If I had hesitated I would still be sitting in the car. I caught up with her while she was unlocking the front door. I put my arm through hers and said with a huge smile. "Hello, darling! Are you going to invite me in?" Richard looked shocked and then relieved. She didn't say anything. She opened the front door and led me up the stairs to a second floor flat. She opened the door, we entered, she turned towards me, hugged me and burst into tears and I started crying too. "Rachel, I'm so so sorry," she said, "I have behaved abominably towards you and I regret what I have done very much. You must really hate me. But it is solely my fault so I will accept any settlement you want." "Richard, my Richard," I said with the most loving and reassuring smile I could do, "then we're good, I want you and I want to be with you". She was taken back and looked surprised. "And I don't care if you are Richard or, oh what's your name now." She was overjoyed. "It's officially Caroline, I am Caroline to everyone I now know, but I like to keep it to Richard between ourselves, after all I that is who I am really. But otherwise I prefer it if you treat and refer to me as Caroline and as a woman." "Richard, you will always be Richard to me. But I need to tell you something." I paused to see a look of concern cross her face. "I have always known about you, about your dressing as a girl." "How can that be? I've been so careful to hide Caroline from you," she said. "A month before we first met and you chatted me up, if you remember, I saw you at another party dressed as a girl. You looked at me briefly and then turned away," I replied, "but I had watched you and, so, I easily recognised you again as the girl I had seen." "When I first saw you at that party I was smitten and I had to seek you out, but as myself. I never dressed as a girl again, I did want to ruin my chances and our relationship. Then once we were married I had no strong desire to dress until a year ago," Richard explained. "Why, what happened to cause you to change?" I asked. Richard seemed relieved I had asked. "Our company was bought out and I discovered that the new owner was Sue, she was the other girl at that party. Sue was my best mate Steve. We spent a lot of time together doing mates' things, when not with our girlfriends. Then one day we discovered we both had a secret, a common interest. We were both crossdressers. From that day on not only was Steve my best mate, as Sue she was my best girl friend, we were like 'sisters'." "When I started going out with you, Steve and I agreed not to stay in contact, to safeguard my relationship, and later marriage, to you," Richard continued. "What I didn't know was, while my crossdressing was fallow, hers blossomed. Sue now lives openly as a woman. And with my role at work we were in regular contact. After quite some urging, my curiosity was piqued and I agreed to attend a meeting of a society she was heavily involved in. I make no excuses, but she was an old friend and my boss, the children had left home and our marriage was rock solid so I thought 'what was the harm'?" Richard paused to wipe a tear from his eye and I was starting to swell up with tears. "Attending the meeting had an unintended and profound effect on me and I wanted to experience again what it was like to be dressed as a girl or rather now as a woman. Later in the office, Sue asked me if I enjoyed the evening and I admitted that I did. She suggested that I go should again, but this time en femme. I was to come to her place first and she would lend me some clothes. I was now hooked, or rather hooked again. But I was sure that if it went too far, or there was a risk it would come between us, I would stop; just as I did before." Richard got up and went to fetch a bottle of wine, she didn't ask me, she knew me. I looked around, she was plainly renting a furnished flat, the furniture was of reasonably quality, but still with an air of universality. It was clear that a woman was living here, but it didn't have a woman's touch, poor Richard not quite a view she would have liked. "Before I continue I thought we could have some wine," she said as she handed me a glass. "After about six months I fell in with a clique of girls who took their dressing seriously. Everything had to be as realistic as practical, some of them had undergone feminisation to various degrees and I found myself being drawn in deeper than ever before. Then about three months ago, with much urging from them, I came round to the idea that I would like to live as a woman full time, but I didn't know if and how. Then Sue made an offer I found very difficult to refuse." "Sue must have heard about my aspiration, because she offered me a promotion to be her personal executive, her deputy. But with conditions. I was to move closer to her office so I was more readily available; I was to present myself at work as a woman and to change my name to Caroline and my declared gender to female, to make it official." Richard looked uneasy as she told me, she must have recognised that it was this offer that was the trigger that sent her on the path to leaving me. I didn't respond as I didn't know what to say, but it was clear that Richard had accepted Susan's offer with all the conditions. Richard then continued. "I was over the moon, I yearned so much to spend more time as a woman. And to be and dress as a business woman was a dream come true. When the girls at the society heard, to them it was a foregone conclusion, all the talk was all about my future as Caroline and the wardrobe that I would need and where I would live. And of course Sue only ever talked about her future plans for me. To be honest, as old friends she wanted me to follow in her footsteps." She continued her story. "I would earn enough money to live a separate life and still contribute to our household. I could see no downsides. I was blind to the consequences to our relationship and your feelings. I was swayed by the encouragement by those around me and the argument that I should be myself and not be held back by my past and society's expectations. They were all committed crossdressers and most of them lived as women. It all seemed so natural." "I had already decided I wanted to live as a woman so when Sue made me the offer I was very excited. But I took some time before I gave her an answer. I decided to formally accept the offer including the conditions. I would be able to afford to live two lives, contributing to our household and maintaining a place near the office for me as Caroline. But I made it clear to Sue, but perhaps more importantly clarified my own thoughts and desires, that I had no intention to transition or to embark on new relationships with either men or women. I would remain a married man. Name changes and any feminisation would be reversible or acceptable when living as a man. At that time I had every intention of remaining at home as Richard." "I agreed to a date with Sue to start work with her. It turned out to be the first day of your conference. I was planning to prepare a special dinner the evening before and after we finished and we had settled down I was going to break the news. But sitting there enjoying our meal I realised I had made a horrible mistake in not discussing my desires and plans with you earlier. I had no idea how you would respond, I was so selfish that I assumed, like many of crossdressers, that you would accept Caroline and be happy for me. I had no intention to leave you and I expected to enjoy your company on weekends and holidays, or whenever, as my new weekday accommodation would not be that far away. I was keeping my manhood and expected to continue our intimacy and keep my place in our marital bed. I had fallen for all reassuring talk from my crossdressing so-called friends. But instead of opening up to you I froze". "As you discovered, I took the unexpected opportunity to spend the four days you were away to move to my new accommodation and start my new job and new life as a woman. The decisions had already been made and everything was in place. Sue had rented for me this flat, using the company account, for the time being while I looked for a new place, and as she later admitted to me, in case I changed my mind. I also had my hair and nails done." "I was then going to welcome you home as Caroline, believing naively that you would better understand and accept me if you saw me as Caroline and I didn't look like a man in a dress or a flamboyant drag queen. But I chickened out, again." Richard paused and looked at me expectantly, but I silently signalled for him to continue. "I had quickly settled into my new life, those first few days were heady and my new colleagues and crossdressing friends made me feel very welcome. I became more frightened of facing you, of upsetting or disgusting you. Of you not accepting me. I didn't want our marriage to end or indeed change, but I had gone too far and the longer I left it the more difficult it became to confront you or indeed contact you. Sue arranged to pay part of my new salary, equivalent to my former income, into our joint account. So you would not go without and would also know I was okay. The plan was to continue to do so." "You may not believe me, but it is my intention to go back to being Richard fulltime and to my old job if you could not accept me as Caroline and my new life. I believed this conviction was a barrier to me contacting you. I am enjoying living and working as a woman. But I do really miss you and our life together; my new job and meeting up with crossdressing friends is not enough." We sat next to each other on the sofa in silence, but not together. I started to cry and it wasn't long before tears started running down Richard's cheeks. He never used to cry, but it was endearing seeing this side of her. I broke the silence. "I need to go home now and think about this. I knew you were a crossdresser and suspected you had started again. But I hadn't realised how deep you were into this new life of yours until I saw you in town last Saturday. Before I make any decisions I might later regret, I would like very much to meet Sue." "Of course, I'll speak to her tomorrow in the office," said Richard standing up holding his arms out to me. I got up and we had a long close hug. I could feel it was Richard, despite Caroline's padding and narrower waist, and perfume! I pulled away and said goodnight. I wasn't the time for more talking. THE NEXT DAY I returned to work the following day with mixed feelings and my emotions all over the place. I was elated I had made contact with my missing husband, but confused whether I wanted him back or not; if it meant he would not be able fulfill his desires. Which, perhaps, now were more of a compulsion. Would he resent me? It was about mid-morning when my mobile buzzed, it was an unfamiliar number but I answered hoping it was my Richard. "Hello," my heart leapt when I heard Richard's voice, "it's Richard." I thought 'I know who it is silly, we haven't been apart that long'. "I've had a chat with Sue and she would be delighted to meet you. She suggested here in the office after work. Are you okay with that?" "Yes, of course, thanks," I gabbled. "Great, I'll text you the address and this number is my direct line in case there is a problem or you have second thoughts. Come anytime you want, we will both be here. I have to go now, see you later." Richard always said 'I have to go now' if he didn't want to talk anymore. It was six o'clock when I pushed open the door to the office and entered the reception area. There was nobody there so I rang the bell on the desk. Almost immediately, Richard appeared with a grin on her face. "I'm so pleased you came, to be honest I thought you may cry off, but I know you are made of sterner stuff than me! Would like to see my office first?" I wasn't sure but I said yes. I followed Richard down the corridor from reception. She was wearing the same outfit in black as last Saturday: the polo neck jumper, knee-length pencil skirt, opaque tights and ankle boots with three inch heels. She hadn't realised I had already seen her wearing it, and knowing him, she would have carefully chosen what she was going to wear knowing that I would be meeting her in these unusual circumstances. I am looking at her closely. Her outfit certainly flattered her and was perfect for business, smarter than my usual office wear. I also had time to notice how well she could handle heels and her gait had no hint of masculinity or indeed exaggerated femininity. Had she been practising? I think it was because she was in familiar surroundings and not in the public realm and subconsciously being natural. A sign that being a woman is natural for her? We entered an open office with a number of desks and rooms leading off. "This is our main office where the head office support staff work." She pointed to a desk outside a windowed office "and this is where my secretary sits." I was surprised. At first, I thought she was showing me her desk especially as she told me she was a personal executive! She opened the door to the office and announced with a grin "and this is my office". It was roomy with a good view over the rooftops of the old town. In addition to a desk there was a meeting table, cabinets and bookcases. I noticed a picture frame on her desk, I took a peek and my heart flipped, it was me wearing my red lace dress during our last meal together. I didn't remember it being taken and I don't think she necessarily put it there for me to see. The office had a feminine touch including a vase with fresh flowers. "Susan's office is next door, she is expecting us". Susan's office wasn't much bigger than Richard's and had more personal items and pictures on display. So Richard was truly an executive and Susan's deputy. Sitting behind her desk was the attractive, but well built woman I saw in Costa Coffee. She got up and walked towards me with her arm out, "Hello, you must be Rachel, I'm Susan. You probably don't remember me but I was at your wedding. I only dressed as a girl occasionally at that time, I was, well I still am, Stephen Hutchins, but please call me Susan, or Sue as my friends do." I replied "Hello Sue, I do remember Steve. You were Richard's best man at the wedding!" I stretched out both of my arms, Susan read my signal and we embraced, after all I did remember Stephen. Richard was pleased that I had remembered him and that we were still on friendly terms. "We have a small office cafe, the staff have gone home so we will be alone and can relax." We went across the open office to a recreational area with armchairs and sofas and a small open kitchen. "Please sit down, the two of you. Would like tea or coffee? Or perhaps some bottled water?" asked Susan. "A latte please, if it is not too much trouble," I replied. "It is no trouble, I had a bean-to-cup espresso machine installed as I like decent coffee. And you Richard?" I noticed Susan called her Richard, clearly to put me at ease. "Same for me please, thanks," he said to Susan while smiling at me. As Susan prepared three lattes she said. "Richard told me this morning that you tracked him down last night, which did surprise me because I assumed you two were still together. It is not just a matter for me as Richard's old friend and new boss, but I hope I can help you both. I would like to renew our friendship. I did admire you back in the day, and of course for anything I can do, I will do my best. But I am not going to act as a mediator, well not tonight, but Richard said you would like to meet me." "Yes, I did, but I am not sure why. But you were clearly a major influence and helped facilitate Richard's new life as Caroline. And thought it might help me either accept the inevitable if I cannot resolve my dilemma," I replied. Richard looked at me quizzically and with some disquiet. "We have spent most of the day discussing Richard's situation, his relationship with you and your son and daughter, the opportunities from his new job and most salient of all his failure to tell you about his dreams and desires and the distress his poorly handled disappearance has caused both of you; Richard agrees with that view. If I have understood from Richard that you are considering your future and your relationship with him and have yet to decide." "Yes, that's right. I did know Richard crossdressed before we first met. I don't know if he told you, but first I saw Richard at a party dressed as a girl with another girl. Richard told me last night that the other girl was you." I looked over at Richard and smiled. She was sitting demurely with her hands clasped resting on her lap and her legs together and at angle. The hemline of her dress had risen to expose her knees and lower thighs. I had always thought he had shapely legs, and that was as a man, but now shaved of hair and encased in 10 denier black tights, as a woman they were certainly one of her strong features. Too bad she was of the wrong age and shape to wear miniskirts. "I remember that party because Richard turned to me and said he had just seen the girl he was going to marry," recalled Susan. From that the day on he never dressed again as he was hoping to find you and didn't want to put you off. He gave me all his girl things the following day. Richard really enjoyed his crossdressing and treated his presenting as a girl seriously, so I knew he was being earnest. And to make sure there were going to be no slip ups or sliding back, we agreed during your wedding reception that we would go our separate ways but remain 'sisters' in our hearts. That is why you never saw Steve, and indeed Sue, until now." "I do feel terrible about what has happened," said an apologetic Susan, "I didn't expect to meet Richard again, but short of firing him reconnecting was inevitable. He told me your children had left home and the two of you were as close as you had ever been. We very easily took the view that Caroline could emerge again without risking your relationship. What we didn't expect was the influence on Richard of a group at our regular crossdressing meetings." "But I don't want to dwell on matters that should be private between the two of you. But I do want to be more honest with you about Richard's new job working with me here. First I want to make it clear that I promoted Richard on his merits, although it did help that we were old friends, but I did lay down some conditions that quite frankly were to help him fulfill his dreams." "While working with Richard, after I took over the company he worked for, I quickly picked up on his managerial style. He worked well with his staff, encouraging and rewarding them or helping out if they were in difficulties. He was not aggressive or demanding. His office had the highest ratings in staff satisfaction and attendance as well as productivity and quality among all my companies. I recognised the potential to be a very successful business woman, and in that I mean his style was more that of a woman than a man. I knew he would fit it at the head office. If he had been younger than me then I would have groomed him to take over when I retire. "Firstly, I told Richard it would be Caroline who would be offered the job. All the staff in my office here are women, or present as women. I find it creates a good atmosphere and we thrive. One of my staff is a trans woman and I am a crossdresser as you know. My son is gender fluid, he chooses almost on a day-by-day basis whether he is going to be a girl or a boy, and she works here during the school holidays. She is most captivating and my colleagues love her. And one of Richard and my old crossdressing friends from back in the day, also works for me now. She loves to dress and work as a woman in an office, but spends most of his own time in his male personna, only presenting as a woman at the odd social event and occasional shopping trips with his wife." "I implied it was a condition of employment in this office to be or present as a woman. That is not strictly true. It is what my staff and I prefer, but I am an equal opportunities employer and if any member of the staff, man or woman, want to present as a man then they are welcome to do so. So Richard could come to work as Richard or Caroline. I didn't tell Richard as I was selfishly encouraging him to be Caroline. I hadn't given any thought to the possibility that your marriage may be threatened." "It is true that I like my senior staff to live close to the office, for a number of reasons, but to be honest the travelling time from your home is quite acceptable. Again I used the excuse to give Richard a place that would be Caroline's, where he could fully immerse himself into living as a woman and distancing himself from his male life, his clothes and male- orientated belongings. Mind you being able to walk to and from work is a bonus in my view" "And finally the name change to Caroline. That just seemed a logical step in Richard's new life as well as being administratively convenient. But it hasn't happened yet, I intended to offer the services of my company lawyer but it is not a requirement." "I promoted Richard to being my deputy because I was impressed with him, as indeed were the former employers, and I knew him. That he had the same interests than me was the icing on the cake. Although they do say managers tend to promote people in their own image!" "Thank you both for listening to me patiently. I wanted to make it clear that if you decide the only way you can get back together, which I really wish and hope you do, then Richard would not lose out on his promotion or his future with my company. So unless there are any questions I will now go back to my office and leave you two to talk," said Susan. I had listened to Susan in thoughtful silence. I didn't want to interrupt in case she lost her thread and forgot to mention something important. I also couldn't think what to say. I expect Richard thought it best to say nothing although it was clear from his expression, he tried to keep a calm face but I knew him too well, it was all new to him. "Before you go, thank you for your explanations and reassurance about Richard's future," I answered, "it does open up in my mind other ways to possibly solve my dilemma and I am grateful for that. I have a lot to consider and after a quick chat with Richard I will go home. Thank you for agreeing to see me, I don't really know why I asked but I am glad I did. It was nice meeting you again after all these years and I must say you make a fine woman!" "You are welcome to contact me at any time, with or without Richard," offered Susan, "my door will also be open and I will answer my phone. I will now say good evening and really hope to see you again soon." After Susan left the room I turned to Richard. "Thank you for arranging for me to meet Sue. I am still confused why you were so accommodating and readily took this path. Although I do understand the attraction of the promotion and for you to crossdress, what I don't understand is why you never divulged your desires and plans and then left me while I was away from home without at least leaving a message, you even disconnected your phone. You say you did not want to lose me, but then you acted in the worst possible way. I need to think seriously about my future so in the meantime enjoy your new life. When I am ready to talk to you I'll call you, now I have your number. Just remember that I knew you were a crossdresser in the past and had started again. That is how I found you. I looked for you because I missed you, that feeling has not changed. I am going home now." Richard looked crestfallen. "I'll show you out, I need to unlock the front door." I followed her, she didn't have that bounce in her walk she showed when she showed me in. When she opened the door I stepped through, lifted my head up and gave her a kiss on the lips, the first as Caroline. I wanted to assure her that all is not lost. I said "Good Night, Caroline," and as I left I wondered why I had just called Richard, Caroline. When I got home I sat down in our sitting room, it was still our sitting room, with a glass of wine and thought about Susan, what Susan had told me and about Richard. I did truly remember Stephen at our wedding, despite the constant interruptions from my family and friends; I was the bride after all and he was the best man, we sat and talked. I found him very personable. I hadn't met Stephen while Richard and I were courting, perhaps they were truly worried they would let the cat out of the bag, and I always wondered why we never saw him again. I recognised the same good-natured person in Susan tonight, despite the years. Her revelation that she had been, shall I say mischievous, in the way she promoted and encouraged Richard should have been enough for me to walk away, but I saw it as a genuine admission that she had messed things up in assuming that Richard was talking to me. And her revelation that her conditions weren't conditions after all, just nudges to push Richard down the path she thought he wanted to go. Yesterday after my intrusion into Richard's new life, welcome or not, I could only see two options. I give up the last three decades of happily married and family life and let Richard go to follow his dream. Or I could take him up on his offer to come back as Richard and we pick up where we left off a month ago. I never went to bed that night, I just sat there. I ranged from doing rational actions, like making pro and con lists, to aimless wandering of thoughts and reminiscences. If I let Richard go, it would have to be a permanent separation. I didn't want another partner and therefore I didn't want a divorce, other than to free Caroline to marry someone else. But I don't think I could have an active friendship with Caroline, she would just be a girlfriend and not my husband. I don't think I could face the constant reminders of what I had lost. I may have come round, but what if I hadn't deep inside? On the other hand, we couldn't really return to our old life. The memory of this last month and Richard's, what I have to call, selfish behaviour, could not be something I could forgive easily, even if he was being indoctrinated by those 'hardline' crossdressers and was worried about my revulsion of his new lifestyle and my rejection of him. Of course, he didn't know I already knew and he had put family first. But now the genie is back out of the bottle, Richard yearning to be Caroline may become uncontrollable and living through it may be worse for our relationship than now. I thought about the offer I had of advice from one of the society's representatives to meet their 'significant other' councillor. I had taken down the details. But I also read quite a lot of 'advice' and 'opinions' on the internet. It also seemed to boil down to my dilemma. The 'significant other' should either let her husband be herself and accept it by joining in, which may be acceptable for an occasional crossdresser, or the crossdresser to suppress his yearnings and not be selfish and think of his loved ones. But it was also clear that the yearning would never go away even if under control. Some even advocated keeping on dressing, but at times and in ways the wife would never know. Talking to a counselor may help, provided they didn't have preconceived positions and beliefs. But a common thread was that the man should be who he wants to be and his partner to accept it. The irony was it was a classic case of male superiority, not the behaviour of a self-declared woman! So I decided not to seek help from someone who may have an unconscious bias. But in the early hours of the morning a possible approach was starting to take shape. Richard should continue in his new job, what wife wouldn't want her husband to be successful in his career? I would accept him dressing as Caroline to fit into the office culture and more importantly provide an outlet for his desires, and I was rather taken with her appearance in her smart office attire. But I did want him to come home, that had never changed, and for that to happen I had to accept Caroline. Richard could hardly transform himself before and after work. But what about feminisation? I would have to accept hair, brows and nails and maybe electrolysis, otherwise she would not look convincing at work, but breasts or loss of manhood? That seemed a step too far for me. So I decided that it would be conditional that any feminisation had to be easily reversible or acceptable. He could not take hormones and had to spend time as Richard. I wasn't sure of the balance of his life between Caroline and Richard that I could live with, but I was sure we could work something out that was acceptable to both of us. He was my husband. After all, I loved him and wanted him to be happy. I wanted to bring the children on board, they were modern adults. But if they rejected Caroline then so be it and we would have to find a way to keep in touch and enjoy family events. So I arrived at a package of acceptances and conditions, I wrote them down so I could be sure they were rational and with no contradictions and to avoid any misunderstandings. I then fell asleep, my mind no longer restless. THE DAY AFTER I woke up late. I rang the office and said I would not be into today due to a family crisis. They were understanding and after a breakfast, during which I went through my notes to ensure my reasoning had survived to the new day. And then I made a call I wasn't expecting to make so soon. "Hello Sue, it's Rachel," I said, "thank you for your time last night. I was wondering if I could see you without Richard knowing?" "Of course, Rachel," replied Susan, "I wanted to have a chat, but did want to encroach until you were ready. Last night, after you left, Richard and I had a heart-to-heart conversation. He was distraught, he didn't really understand how he allowed himself to end up in such a terrible place. I told him not to come in today, but I expect he will do so when he's ready, to take his mind on things while waiting for you to get back. Can we meet in Costa Coffee, say in an hour?" "Thank you, I will see you there," I replied with some relief. I needed to run my thoughts past somebody and quite frankly Susan was an obvious choice. Susan was there when I arrived waiting with two coffees. "Hi Sue," I said as she stood up to greet me, I gave her a kiss on her cheek and she returned it. "This is the table I was sitting at when I first saw you and Richard. I was having a break from searching for him and there you were!" "Well let's hope this table plays another important part in you getting Richard back. I won't say anything more, well other to say that Richard is devastated and will do anything to get you two back together again. Now I will shut up". I decided to start from the very beginning when I saw Richard dressed as a girl. It was the only way I thought Susan could fully understand both the positive and negative. I finished off by describing what I intended to discuss with Richard. "In the light of what I have told you, what do you think? Will it work? Is there something I don't know that might ruin it all?" It was an answer to my last question that I was most worried about. "Well after talking with Richard last night when it emerged that Richard's new life wasn't as clear as I thought. Although over the last month has been as a fulltime woman it was not what he realised he really wanted. He never wished to give up being Richard, he is a crossdresser after all and not transgender. Seeing you again reignited his real feelings and the realisation that he had been bamboozled by a clique of crossdressers and had been blind to his love for you and your feelings. And I didn't help my making offers he couldn't refuse and guiding him down the wrong path. Although to be fair to you, I did misread the situation but I should have been more circumspect. I thought he was drawn to the clique and their dogma and not that they were indoctrinating a gullible man." I was uplifted by what Susan had just told me. "As for your conditions, that would not be a problem. One of the more zealous members of the clique encouraged Richard to take some vitamin pills to help soften his skin. It was when he was changing at my place that I noticed the puffiness of his breasts. Oh I should mention that it is not unusual for crossdressers to help each other when changing, I was lacing up his waist cincher. Otherwise we are quite modest! I discovered what had happened and Richard disposed of the so-called vitamins." "Given what you have in mind for Richard's future, it may be timely to tell a little of myself," said Susan. "I'm a crossdresser. I am not trans or wish to live as a woman full time. I mentioned my son yesterday, well I am happily married and we have two more children, both adults now. I have never taken hormones and these," he waved at his breasts, "are the best breast forms money can buy. Other than the obvious beauty treatments, like my hair, nails and brows, the only procedure I have had is the removal of my beard. As a working business woman it was difficult to get through the day. Even my earrings are clip on." "Looking at you that does surprise me!" I giggled, "as you have described just what I have in mind for Richard." "Even more than you think, I spend my time at home as Steve. However, I usually go out as Sue, it is just more convenient and I do enjoy dressing up and down, I am a crossdresser after all! But I also socialise as Steve, I go on holiday with no Sue in sight." "Oh that is relief, I had noticed the puffiness of his breasts. I was shocked that Richard was prepared to go that far and it was a major difficulty for me," I said, "it just goes to show that not saying anything just makes matters worse. If I told Richard that I had seen as a girl all those years ago, things may have been completely different and not necessarily for the better. As he never said anything I didn't tell him I knew. I fell in love with him, or should I say her, at first sight." "I think you know what to do now. There is nothing more I can add other than you have my complete blessing. We would just go round and round in circles and you should strike while the iron is hot!" advised Susan. "I would just be happy with both Richard and Caroline as colleagues and friends. I still remember the pleasure of our chat at your wedding and look forward to a long friendship. If it all works out, of course. I'll keep my fingers crossed." We hugged each other and when I back out on the street I called Richard, Susan had given me his new mobile number. It was a company phone, that was why his old number was disconnected; it wasn't needed anymore, but then Richard didn't let me know. "Hello," I said when he answered, "I'm ready to talk, can you come home tonight?" "Yes, of course, where are you?" he replied. "I'm outside Costa," wondering why he asked. "I can be there in ten minutes, can we go home together?" he asked with a suggestion of pleading. "Yes, I would like that," I said in a comforting manner, "even if you are dressed as Caroline!" "'Fraid so," he giggled, "see you in a mo." Well we had our own heart-to-heart chat following on from both our individual chats with Susan. I had shown Richard my notes, in case I had forgotten something. Needless to say, he thought my suggestion was perfect, so much so I decided to believe it would be a good way to spice up our life now the children had left home, and I got quite excited. But I was truly relieved that Richard did not want to let go of his male persona and life, or to grow breasts. I made one more request, that when en femme, especially at work, he used the title Mrs, after all he was married, married to me. "Are you going home," I asked coyly, "or do you want to stay over?" "I am home," he smirked. "Good," I said with a grin, "you owe me a night of passion from a month ago!" We made our way upstairs to our bedroom. I must say it was both strange and tantalising to see Richard remove his dress and lingerie, and the falsies and padding that gave him such a shape any woman would be proud off. And then go through the same night routine I go through. Now he was looking more like his normal self, albeit with long hair, I now had a chance to properly take in his appearance. He was a handsome man, but when dressed he did present as an attractive plus-sized middle- aged woman. I now wanted to take him under my wing with my life-long experience as a girl, and now also a middle-aged woman, to make Caroline the perfect woman, a woman that both Richard and I could be proud of. But one thing I am going to do something about is that I have been having a go at him to lose some weight. I am definitely going to put him on a regime to go down at least one dress size, he can't procrastinate now! I have always loved Richard and still do despite what has happened, it was what drove me to find him. I know he wasn't cheating and I knew he was dressing again. But I could not forgive and I could not forget. He had hurt me, disappearing without the courage to say anything. I knew he did not want to distress me and it wasn't his intention, he just lost control of events. I can put it all behind me and over time the wound would heal and we can get on with our lives. After all, I first fell in love with Richard when he was being Caroline. I just hope he has learnt his lesson and has nothing to fear from me and knows he has my support. That's what lovers do. THAT NIGHT "Do you want to wear one of my nightdresses?" I asked Richard anticipating the joy it would bring him. Richard looked surprised and then smiled. "Oh no, I have continued to wear my T-shirt and shorts at night. I've never really wanted to go far as dressing as a woman at all times, only when I am presenting as one. We consummated our marriage again that night.