Chapter 5

Jen and I only really had one full day left and, although it was fun, there was an element of sadness there too. We had been practically glued together for years, so a forced separation, even for only a week felt troubling. At least she would be able to explain everything to my parents, not a conversation that I was looking forward to. It's not that I expected them to be unaccepting or anything. It just feels awkward to turn up looking like a complete stranger and give them the love and hugs that I would want to.

The next day was spent packing and then a tearful farewell. Not exactly how I was expecting it, since Amy and I went on the bus back to the airport with the others who were leaving. In our case it was to relocate to a more shopping appropriate area. It gave me a bit more time to spend with Jen and the farewell happened at the airport rather than the resort, but it was still tearful. I was a bit more weepy than normal which could have been the female hormones that had not been suppressed for a few days, psychological, since culturally boys are told that they can't cry, but girls are allowed, or even driven by stress, considering my week.

We checked in to a nice spa type resort. Amy was very considerate and consulted with me about her plans to make sure I was OK with them. There were various treatments available as well as a pool, spa and sauna. Before we could enjoy any of the amenities, I desperately needed new clothes. Again being almost excessively careful to not upset me, Amy went through a list of clothing that she suggested we buy. Making sure that we could discuss the reasoning in private and come to a unanimous decision before entering any shops. We did this over dinner and relaxing in our room afterwards.

We were sharing a room with two single beds in it and she was not shy about taking her clothes off in front of me, but turned away strategically to not rub my nose in her nakedness. I tried to do the same but felt embarrassed and uncomfortable. I knew it was something that I would have to work on. Even why I felt that way was not clear to me, but it was what it was and I would have to deal with it. I slept well and readied myself for the day.

Most of what Amy was suggesting was pretty unobjectionable. A whole set of new panties, various styles so that I could experience the differences and find what I liked. A few pairs of jeans, leggings, slacks, more colourful tops, jumpers and jackets. She suggested a few pairs of tights, so that I could try them, telling me that they were very useful in the winter to keep warm. She also explained that I needed a bra. I was completely flat chested since my body had been on hormone suppressants since it was eight, however, a fifteen year old girl would normally wear a bra even if there was nothing filling it. Likewise my swimming costume needed to be a female version that would cover my chest. I couldn't disagree with anything that she had said, so the shopping marathon began.

I decided that I had a choice with regards to my attitude. I could try and hang on to my boyhood and just choose what I would have happily worn as Dillan. The thing is, that would not serve me in the long run. Instead, I decided that I would try on anything that Amy suggested and try and be as honest as I could about how I looked in it and whether I would be willing to wear it. I was not a complete novice at this, since I had accompanied Jen on lots of trips and I knew what I thought looked good on women in general. I just had to apply it to myself.

I tried my best to go with what I thought looked cute or nice. I did wonder if there was no cultural bias whether I would have chosen similar colours as a boy. I have always liked certain colours that Jen wore that are considered feminine. Baby pink, lilac and various shades of purple, but as a boy it never even occurred to me that I should look for something in those colours for myself. I don't know if that meant I had changed by switching to this body or I was just more free to express myself.

I surprised myself and definitely surprised Amy with my choices. There were a few moments that really stuck out. We didn't go for a bra fitting as there really was nothing to measure, but trying on these starter bras and sports bras, really brought home to me my change in circumstances. Having seen me try on relatively feminine colours and styles, Amy felt comfortable enough to try and push me a little. Some of it, I agreed with and went along and some was just too much.

A more female type haircut sounded great, but, when you have pretty short hair there is not much you can do. In the end we went with using clippers on either side and brushing the front back straight. That seemed the best of the options available. She tried to convince me to get a nightie in addition to some PJ's. I think part of it was because I liked a baby pink PJ set with red hearts on it that was so soft, just touching it made me smile. Some of the nighties were just as soft, but I wasn't ready to go that far yet. She got one anyway, in case I changed my mind.

We almost had an argument about shoes, but I refused to even consider anything that was not comfortable. Over lunch she tried to get me to agree to have my ears pierced, with her main argument being that all girls have pierced ears and I would stick out if I didn't. For me, that was not reason enough, so I managed to keep my ears unblemished. When Amy suggested we have a Mani Pedi together, I was torn. Most of me wanted to say no, but two elements made me agree. I had always loved Jen's fingers after she had put polish on them and the eagerness on Amy's face when she was asking. My nails were short and I refused extensions but I can't deny, I did like how they looked with a light pink coating. The joy Amy seemed to get out of it made it worth any squeamishness I felt at pushing my boundaries.

Despite these discussions, which I wouldn't call arguments because Amy never pushed me too far, we had a great time. A lot of money was spent. I was quite happy to pay it back but Amy said that the amount we were spending was tiny when considering all the clothes that Richard had not wanted growing up. I would have stressed about it more if I didn't have the money to easily cover it, if needed, and I liked all the clothes we had bought. Apart from the nightie that is.

When we got back to the spa resort, Amy helped me pick out a nice outfit for dinner. With a small smile she offered to help me by lending me a necklace that would enhance the top I was wearing and tried to convince me to wear a little bit of makeup. She gracefully accepted my declination.

We had an lovely dinner and I have to say I was really warming up to Amy. She was a beautiful person inside and out. She encouraged rather than forced, explained anything and everything if I had any questions, without ridicule or making me feel bad in any way. After dinner we relaxed in our room and watched a movie. It was a chick flick and we both cried and laughed together. A real bonding moment.

Amy had a cleansing and moisturising routine that she suggested I follow. She also showed me how she put her hair in a sleep braid. Obviously my hair was way too short to do anything like that, but Amy had a chance to show her daughter something she didn't know and was revelling in it. I could see that Amy was a great mother. I had a great childhood growing up as a boy in my family, but Amy was showing me that I would have had a wonderful time growing up as a girl in her family.

The next morning we had a light breakfast and then went for a swim. Richard couldn't swim. He had refused to wear a girls swimming costume from a young age and so never learned. The fact that I could swim was clear evidence that I was not Richard, not that Amy needed it. It was quite an experience for me as well. To start with I felt very self conscious wearing a swimming costume and in the water, swimming felt a completely different experience. I think my skin was more sensitive and I was more flexible. Feeling the water caress me was a very sensual sensation. Not erotic, but quite pleasant. I loved pushing off with my feet strongly and just gliding under water until I slowed down.

As nice as that was, it was nothing compared to the hour and a half massage that Amy had organised. That was all we had time for since we had to pack up and get back on a bus to take us back to the ski resort. Amy promised sometime in the near future we would spend a weekend in a spa resort in England and have a whole two days being properly pampered.