Monday evening, after I’d cooked dinner and cleared up my girlfriend tells me that my training will be stepped up further tonight. I’m told to have a shower and to ensure that my legs and body are freshly shaved. When I enter the bedroom half hour later my girlfriend is laying on the bed and Amy’s long wig is next to her. My girlfriend tells me that I’ve spent enough time in the house dressed as Amy. Tonight I will be going outside and walking whilst dressed as a female. My girlfriend tells me that I can choose whatever I want to wear and that I’m to be ready to go out at 9pm. I look at her and she reads my mind “yes it will still be light, and the chances of you being seen by people whilst dressed in female clothes is very high”. She heads downstairs leaving me to dress and do my makeup. I sit on the bed for no other reason than I need to. What time does it actually get dark now? Is it 9.30 or more closer to 10? My obvious thought is which of my miniskirts can I wear and should I wear hold ups or suspenders. But no, this is going to require more thought than my previous outings as Amy back in February. It won’t be dark when I step outside. I look at my finger and toe nails which are painted bright pink. They will need to be changed for starters. Nail vanish remover quickly takes the pink off. Opening the drawer where I now keep my makeup I select a dark brown nail vanish and sit down to apply it. 15 minutes later I’m painted and dried. Next I select a matching burgundy bra and knicker set. The bra isn’t that padded so once I’ve added my silicon inserts I have a small B cup going. Next I select a pair of plain black tights. The desire to wear stockings is really strong, but I’m so conscious that it will still be light and I don’t want to draw to much attention to myself. As the weather tonight is still very windy and cold so I’m going to avoid wearing any clothes that could be easily lifted by the wind. So I put on a black long sleeve top with a round neck so I won’t be showing any cleavage. Finally a black and mauve pinafore dress that’s a couple of inches above my knees. Looking at myself in the mirror I’m very pleased with my outfit. It’s definitely female but not over sexy. Time for makeup to be done. I choose a lighter shade of foundation than I usually wear as Amy and apply it to my face and neck. Then the eyebrow pen is used to darken my eyebrows and make them look feminine. I apply three different dark shades of eyeliner to my eyelids and around my eyes which make them look a lot softer. For lipstick I choose a shade of brown to go with my nails. I smile at myself in the mirror. Every time I apply makeup I getting better at it and becoming more female. The wind is definitely going to be a factor with my hair tonight. My girlfriend has chosen a long wig for tonight, so I going to have to do a ponytail otherwise it will be going everywhere and I will be noticed. Once the wig is on and brushed, I pull it into a ponytail and add a hair scrunchie to hold it on place. I’ve left to long strands out of the ponytail and these hang either side of my face. Lastly I add a pair of small hoop clip on earrings and a spray of my own perfume completes Amy. Looking at the clock it’s 8.50 so I pick up my ankle boots and head downstairs to find my girlfriend. When I walk into the lounge she whistles at me and says “Amy I’m very impressed with the outfit and I can see you’ve thought about what you’re wearing tonight. You are going to be such a good sissy”. I ask if I can borrow one of her jackets as that’s something Amy doesn’t yet own, and she tells me to go and help myself. 9 o’clock and I’m ready to go outside. All I have to do is to make it to her car without being seen. I ask my girlfriend to go first to make sure no one is walking past, but she refuses telling me I’m a sissy and as a sissy I need to be seen by people. We leave the house together and I’m relieved that the road is quite and I make it to the car unseen. We only drive a few minutes to a large park that’s near the house. There’s a large lake and lots of different paths to walk along. Parking in one of the smaller car parks I’m happy to see that there’s not many cars or people I can see, but it’s only 9.10 and the sky is still light. “Come on Amy get out of the car were going for a walk and remember don’t hold my hand where not a lesbian couple” my girlfriend tells me. We open the doors together and step out of the car. My girlfriend leads the way chatting about this and that. She’s not taking any notice that her boyfriend is dressed fully as a female and is walking next to her. I can see people walking on other paths but so far no one has come close to us. Then that changes. My girlfriend says “I can hear a jogger coming behind us”. So can I now and 10 seconds later he goes past us. He gets about 5 meters ahead of us then he turns his head and looks back then he’s gone. “Ooh Amy you just got checked out by your first man you lucky girl” she tells me. “He was probably looking at you is all I can reply with”. “No don’t think so” says my girlfriend “he was definitely getting a good look at you”. We walk on and fortunately it’s starting to get darker. We are passed by a couple walking their dog who don’t seem to give us any attention. Another couple of joggers go by without incident. Then two other females are approaching us. As they get level one of them says “hi” to us and without thinking I say “hi” back. Why did I do that? They must now know I’m a bloke dressed as a female. My girlfriend starts laughing which doesn’t help. It’s nearly dark now and luckily we have made our way back towards the car so she says we can go home now. Once we are home I pour us glasses of wine, my first glass doesn’t last long. Sitting in the lounge my girlfriend asks me how I’d enjoyed the walk. Fortified by the wine I told her it was scary and I didn’t like going out in daylight dressed as a female, that I’m more comfortable at home. Her reply which I’ve tried to remember the best I can gave me a clearer insight in to what I’d agreed to become. She told me “you wanted to wear female clothes. Initially you were happily wearing underwear around the house and sometimes a skirt or dress. Then you was the one who wanted to go outside in February dressed as Amy. I’m just building on what you obviously want to be. So if you now think that being a sissy is just going to mean putting on a dress every now and then, you are so wrong. You are going to be trained by me to be a complete sissy. So you can stop thinking you have any say or control with what’s happening to you, you don’t. You said you wanted to be a sissy so that’s what’s going to happen to you. How I choose to do this is completely up to me. Your job is to do as your told and not to question me. Have I made myself clear sissy?” I look at her quite shocked by what’s been said and say “yes I understand”. “Good” she says “no go refill my wine glass”. I walk towards the door and that’s when she tells me that tomorrow night I be going out as Amy again, only this time I will be walking alone. Amy xx