Becoming his Woman

Becoming his Woman

Christine and Doug were the best neighbours you could wish for. After my rather messy divorce, they were so supportive, checking on me regularly, helping out with various things and inviting me around for the occasional meal. What little confidence I possessed had been drained from me and, although my friends and family were very supportive, they were mostly too far away to be much help when I needed them. Christine and Doug had no children of their own and kept themselves to themselves. It was as if they almost adopted me!

I may as well confess now. My wife had left me because she found out that I cross-dressed occasionally and, being somewhat neurotic at the best of times, it was something that she simply couldn't handle. The counselling sessions were a waste of money in terms of saving our marriage, but they were helpful for me to come to terms with myself. I saw the therapist a few times alone and she was very sympathetic to what she called my gender dysphoria. Unfortunately she had no real answers for me other than to not feel ashamed and to embrace my inner femininity and see where it went.

Christine became my role model. It was a natural choice as she was the woman that I saw the most. But it was more than that. She had a natural sense of style and, although she was not a great beauty, she was very attractive with the loveliest smile. I got a wig that matched her hairstyle and bought similar clothes. I would observe her mannerisms and her makeup and copy her in my private time at home. I realised that I had a dreadful crush on her, and loved looking in the full-length mirror when I had transformed myself into her twin sister.

Women are so much more observant and perceptive than men, and one Sunday afternoon I was chatting with Christine in the kitchen while helping wash up. We had just finished a particularly filling roast dinner and Doug was in the living room where the log fire, football and filling food, had sent him to sleep. As I washed up, wearing Christine's apron, I felt her pull at the back of my trousers. I looked around in surprise.

"We need to have a chat Chris," she said in a soft voice with a warm and smiling face. I realised at once that she has seen that I was wearing panties and my heart began to race. She held my hand and squeezed it, causing tears to flood down my face. She hugged me and soothed me, whispering over and over: "It's all fine Chris, it's all fine!"

We sat down at the kitchen table and she poured us a coffee. She told me how she had noticed signs of makeup on my face occasionally and how, earlier that day when I had bent over to pick something up, she had caught a flash of my panties. I was not sure how I felt. Dreadfully embarrassed in part, but also relieved that someone knew my secret and did not seem to care.

"I'm sorry!" I said and immediately wondered why we feel it necessary to apologise so much!

"Don't be silly, there is nothing to apologise for," Christine replied, taking hold of my hand, "one of my nephews is transgender, so it's no shock to me, but I just wanted to warn you to be much more careful if you want to keep your secret a secret."

Over the next hour, I poured out my soul to her: how I loved the dressing; what the therapist had said; how I was beginning to love being more feminine and how natural it felt for me. To my absolute delight, she offered to help me, to be my teacher. She only worked three days a week and Doug was often at the Golf course, so I invited her round to meet my other self. We heard Doug stirring and she dried my eyes and we carried on clearing up as if nothing had happened.

Dressing on your own is fabulous, but dressing for a friend is ten times better, especially for a friend that you have a crush on. That first day I remember the look of shock on Christine's face when I opened the door. Her smile showed it was a good sort of shock, but there was a light element of puzzlement too.

"I have to ask, but are you modelling yourself on me?" She said, once I had closed the door. I blushed deeply in answer. It was quite obvious.

"Well I am more than flattered and I have to say you really do make a rather striking woman!"

I was unsure if that was a compliment until she explained. "Striking is a good thing, my dear, it's what a girl would say about another girl. You are very pretty and have a fabulous presence!" She held her arms open and I hugged her. Although I felt a strong sense of sexual arousal, something I am sure she must have noticed, it was a very loving and caring hug and made me feel more relaxed and happy than I had done for many many months.

Over the next few months, she taught me so many things. She explained the finer points of makeup, and how I could grow my hair so that I could style it in both a masculine and feminine way. She taught me about daily routines, creams, conditioners and subtle uses of scents. She taught me to cook and enjoy all sorts of vegetarian dishes as well as how to look after my clothes and keep my house clean and tidy. All the time it became easier and more natural for me to be this new woman that she had christened, Cristal. I liked that name!

One morning Christine turned up wearing her coat and boots and carrying a bag. No sooner had I invited her in than she told me to put on the coat which was one of hers and step into some ankle boots that she had specially bought for me. Much to my horror, she announced that she was taking me to the local mall for some shopping, coffee and cake. She quickly adjusted my makeup and got me to tone down my lipstick before brushing my hair. She got me to transfer everything to the handbag she had brought for me and pushed me out of the door and into her waiting car.

That day will live with me forever. It felt like it would never end, but at the same time, it seemed to be all over far too quickly. I was so nervous walking into the mall, head down, avoiding eye contact, but Christine forced me to walk tall. She made me buy her a coffee and I had to put everything she had taught me into practice. My quiet voice, my shoulders back, getting out my purse and card. All the time I was waiting for some comment, some reaction. All I got was a beautiful smile and 'thank you' from the girl who served me.

After that I felt much more confident. Christine and Cristal walked arm in arm. We laughed in shops as we tried on things that really didn't suit us. We had a lovely salad at a bistro with a very flirty waiter. I bought some more sandals, a blouse and a lovely long dress. I helped Christine choose some sexy lingerie that she wanted to surprise Doug with. It was absolutely to die for, but far too expensive for me to treat myself to a matching set!

I was so tired when we got home, but invited Christine in as she wanted to try on her lingerie properly. I said she could use the spare bedroom, but she was happy getting changed in the living room and said I should try on my dress and sandals. We undressed and I was quite embarrassed, embarrassed that Christine was undressing in front of me, and embarrassed about the effect it was having on me. I tried to avoid looking at her, but I couldn't help myself, and had to think of all the household chores I had to do to try and keep myself under control. I was soon in the dress and sandals, while she was barely dressed at all.

'Oh my, you look absolutely adorable!" Christine smiled, swivelling her bra around under her ample bosom and pulling the straps over her shoulders before settling her breasts into the cups.

"What about me? How do I look?"

It was a three-piece in bright blue satin. Brazilian lace panties, suspender belt and balcony bra. She looked so sexy I could barely contain myself and just let my eyes wander over her body.

"Well?" She asked, "do I look so awful that you're speeechless?"

"Oh no, you look absolutely gorgeous, Doug won't be able to keep his hands off you."

"Come over here and give me a hug. I've absolutely loved today and can't wait to go out again with my new girlfriend!"

I slowly approached her and gave her a very tentative hug. She, however, almost crushed me against her, pressing her breasts into my chest. She kissed me on the left cheek, then the right. Then she kissed me gently on the lips. My body was on fire, and I kissed her back, forcing my lips on hers, my tongue in her mouth. My cock was tenting my dress and rubbing against her thigh. She pushed me away.

"Cristal, that's not how girl's do it. Let me show you." She leaned in and kissed me gently. I responded likewise. Soon our lips were roaming across each other, pulling, caressing, squeezing while our tongues gently played. It was so erotic and felt absolutely amazing. I have no idea how long we kissed, but however long it was, it was not long enough, but eventually Christine pulled back from me and asked me to take her to my bedroom.

"Oh!" I exclaimed, "but Doug, what about Doug?" I was feeling dreadfully guilty that I had even kissed Christine.

"What about Christine, what about Cristal, what about making you a woman," she replied, taking my hand and leading me upstairs.

Our passion was unhurried and beautiful. She sucked my nipples, and I sucked hers, breaking for passionate kisses in between exploring all our other erogenous zones. My tongue lapped at her pussy while she gently kissed and sucked my cock. Eventually, she rolled me onto my back and slipped me into her, riding me, her breasts rubbing across my chest, our nipples tormenting each other. She climaxed and shook and I came too, pushing deep inside her and groaning. I sighed. I loved this more feminine and sensual love-making, it simply filled me with so much joy!

The next month was a roller-coaster of new experiences. The trip to the mall had been just the jump into the deep end that I needed and was completely convinced that I wanted to live as a woman. I had changed my diet more and was taking some pills to make me softer. Christine continued to take me out and show me the ways of love. We went to a sex shop and bought all sorts of toys with a lot of girly giggling.

Over the course of the next two weeks, we used them all. I loved the butt plug, and she showed me how to make myself cum by just using a vibrator on my hole while she sucked my nipples. She made love to me with a strap-on and it was the longest and best orgasm I had ever had. It went on and on, filling me with a special tingling pleasure and a desperate sort of happiness, unlike any of the orgasms I had ever had as a man.

I had not been oblivious to the fact that she was losing a lot of weight. My new feminine sensitivity had also noticed a subtle atmosphere when I was with Doug and Christine. I feared that our secret was out, that everything was going to end. I was right, but for the wrong reasons. I was inconsolable when Christine and Doug broke the news to me. Christine had been diagnosed with stage four breast cancer. She had only weeks to live.

Later she told me that she could not bear to tell me because she feared I would react the way I did and that it would give the whole game away if Doug was not there at the same time. She apologised, but I understood that she had to maintain Doug's belief in her, and told her she had done exactly the right thing. After that, she declined quite quickly. We made love a few times, slow, lingering, sensual love that was about saying farewell as much as anything else. We were both very tearful.

After the funeral, where I wept a river, Doug took me to one side at the wake and my heart began to race. He had a very serious look on his face.

"Chris, I know that you and Christine really got on well, and she loved spending time with you, and she has been very honest with me and told me everything."

I was waiting for the bombshell. I wanted the earth to swallow me whole, to join Christine! He continued, his words barely discernible from the noise in my head.

"She said you loved going out shopping, that there was another you, and that she wanted me to accept that you and look after you."

My heart slowed, I lifted my head and looked Doug in the eyes,

"You know?"

"Yes, Christine told me about Cristal, and how much she means to you."

"What else did Christine say?" I asked.

"She told me that you are quite fragile, and that she was your rock. I will be that rock for you now. That is what she wanted."

"I see, but are you OK with that?"

"I am, but I'm not saying it will be easy. We've always been friends, and I guess I've never been the most open-minded of people, so I can understand why you didn't want to tell me, but I do want to help, so let's see how it goes."

"OK, give me a call when you are ready. I'm relieved you know. Christine loved you so much!"

Doug's eyes welled up. "I know. I was a bit jealous of her relationship with you, even thought that you might be having an affair, so it was a huge relief when she told me about Cristal."

"I'm sure it was," I replied with great relief of my own that he had no idea. I gave him a hug. I could feel how uncomfortable it made him as he was tense and rigid.

I really wasn't expecting Doug to call me, he needed time to grieve and, as he had said himself, he was not the most open-minded person in the world. When he did call, I was pleased, but expected him to invite me round as Chris, so it was a real shock when he said he would like to meet Cristal. I suggested he come round to mine that evening and I would cook him dinner. He loved lasagna, so I got myself dressed, made a lasagna and then spruced myself up. I wanted to look my very best for Christine's sake.

I can still see Doug's throat gulping as I opened the door and he caught sight of me for the first time. I was wearing that long dress and sandals that I had bought with Christine that very first day at the mall. I was wearing my favourite wig because, although my hair had grown, it still did not look right when I styled it. I knew I looked good. I knew I looked just a little like Christine as I had copied all her makeup techniques and my hair was exactly the same as hers.

"Come in Doug," I said, smiling broadly and stepping aside. Doug was still unable to say anything. His head was coming to terms with the fact that this beautiful woman was his neighbour, but more with the fact that the moment he had seen her he had felt sexually aroused despite knowing that this she was a he.

"Is that for me?" I said, taking the flowers and prosecco from him.

"Oh, yes, sorry!"

"Not what you were expecting?" I asked, quietly.

"No, no, not at all. You are very beautiful, err." He paused, dealt with how flustered he felt, and started again. "I didn't know what to expect, but yes, you are really very beautiful, and I have to be honest, I was not expecting that."

"Well thank you, Doug. So you can see that Christine was not that daring taking me out to the shops after all." I laughed at my own joke, but I could see he was still confused and unsure. Not really clear what he could or should say. I offered him a seat at the table and poured him his favourite beer. Of course, I knew what he liked. I knew everything about him.

"So Doug, how are you coping? I was a bit worried about you, and that maybe you no longer felt you could turn to me, knowing about my alter-ego"

"I'm OK, and I'm sorry it's taken me so long to arrange this. I wish now I'd not reflected on it so much. I do miss her so much. It's the silence and the emptiness that really gets to me, it just reminds me of everything I've lost. I miss her so much."

"Me too. It's not fair that she has been taken from us." I added.

We talked while I served up the lasagna. Extra meaty with a cheese sauce, just how Doug liked it. I gave him a big portion and a little salad, while I had a thin slice and a large pile of green leaves

For dessert we had Tiramisu, but that was shop bought and another of his favourites. Over coffee, we talked about the next steps. I knew what I wanted and suggested that it would be nice if he got to know me as Cristal rather than Chris. He seemed very positive about the idea and we even agreed to go for a walk the next day. He would treat me to a pub lunch.

Over the next few months things settled down and Doug and Cristal became best friends. He would take me shopping, we would go to the cinema, and he even took me out to an expensive restaurant. But my favourite thing was just spending time with him. In fact, I was spending a lot of time in his house, looking after him, even washing and ironing his clothes. We would relax in the evening with a little alcohol and watch television before I made my way home. He always escorted me to my front door.

We were getting on so well that my feminine intuition detected a slight element of sexual tension between us. It was nice, and I encouraged it with some very basic flirting. I began to kiss him on the cheek when we met. I would occasionally reach out and hold his hand when we were walking. I would make little compliments about how clever he was. He began to flirt back.

One evening he told me that he wanted to take me on holiday. He showed me the tickets. It was true. We were going on a cruise from Aberdeen to the Norwegian fjords. We had had a bit to drink and I simply couldn't believe it. I kissed him on the lips and was pleasantly surprised when he kissed me back. We stopped there. Somehow, that was enough. Something that could be passed off as a quick drunken moment, but we both knew it meant more. I rang the cruise company and modified the booking from two single cabins to one luxury double as I wanted to contribute. They had one cabin left and were happy to oblige for a few extra thousand.

The preparation for the cruise was amazing. I had to get several new outfits and spent ages selecting the right ones. Doug insisted on paying for all of them despite my protestations. Instead, I bought the same lingerie set that Christine had bought, the one she had worn the first time we had made love. I wanted to lose my virginity to Doug wearing it. It would be my tribute and thanks to Christine. I so wanted to complete the inevitable seduction. I had fallen in love with Doug and I needed him to love me.

When we got on board, I had to reveal my deception. Doug was a quite angry and adopted a real moody persona, making quite a few comments about me going behind his back. When we got to the cabin, I was so distraught I began to cry. Buckets. Enough to sink the ship. Suddenly he changed. He held me and said he was so, so sorry. He told me over and over that he was sorry and that he was only angry because he should have done it, that he felt like a bit of a cheap skate! I was inconsolable until he finally said that the worst thing of all was that by booking two single cabins he had been far too safe and that he should have booked what he wanted, what he now knew I wanted. I looked at his face, misty through my tears. I saw the sparkle and loging in he eyes and kissed him right on the lips.

"I love you!" I said, smiling broadly, my hands wrapped around his neck. I kissed him again. I kissed him with that kiss Christine had taught me. I felt him melt into me and I fumbled for the door handle to let him push me into our room. We were immediately distracted by how fabulous it was. There was a large bed, an amazing window, a balcony, and chairs and a table. Doug smiled at me, a smile that said that he loved me. I know how hard it is for men to admit it!

"Can you ever forgive me for being such an ungrateful, rude and stupid idiot!" He said, his trembling voice showing how heartfelt his apology was.

"Oh yes Doug, I should have told you! Of course I forgive you!"

I kissed him again, but with more urgency. I wrapped one arm round his neck while the other hand slid down his side and I neatly undid the belt of his trousers. I kept him held in place, distracting him with my tongue, preventing him from stopping me freeing his cock. I took it in my hand. It felt so hot, so big and so sexy. I began to stroke it and he moaned. I worried that I was now taking things too fast, but I also knew that we had taken months to get here, that our pent-up frustrations were overdue for release, and that now really was the time.