A Journey of Crossdressing Support and Friendship

Ok. Here goes. I'm writing this with the consent of the wonderful girl I met. I used to crossdress when I was a lot younger and a lot lighter. Its been years since I did, and since then I've had an attraction for other crossdressers. So when I saw her ad, a guy new to crossdressing, wanting some assistance in getting started, I decided to reply. We chatted via email, and she had been experiencing similar issues I'd had. Being in a relationship, and only getting to dress infrequently, when an opportunity came for some free time. Finding a safe guy to dress up for. Not feeling fem enough. I told her I'd help her with some beauty tips, and we emailed back and forth about makeup, makeup application, preparing for a date, etc. She had experienced several disheartening no shows, and felt like giving up. So I was surprised when she emailed wanting me to help her with this date she'd made, and had even got a motel room. I agreed, and got the room number and evening to arrive. I knocked, and she opened the door, hiding out of view so nobody but I could see her. I smiled at her, and told her she was stunningly beautiful. She asked me in. She was in a matching bra and panty and sheer teddy, and her wig was on. We small talked and drank a beer, sitting at this little motel room table. She was very shy, but I kept complimenting her, and she began to relax. I asked if I could do her nails, and she began to talk and laugh more as I filed, buffed, and coated her finger nails. Then she really became comfortable when I did her toenails. I had her do a slow spin, and she blushed as she modeled in front of me. Her excitement showed in her panty, and I wasn't surprised when she kissed me to thank me. I asked if she wanted me apply her makeup and she happily agreed. I led her to the bathroom and removed her wig. Then I explained each step as I did her eyebrows, eyes, and lipstick. She loved my work. We had another drink, and she told me about her date, still not due for an hour. An online guy, married, but seemingly sincere about wanting to meet her. She had his pic, and he was attractive. I asked if she'd had a fantasy about their meeting, did she meet him at the door in lingerie, or in a dress? A dress. We went to her closet, and compared her two dresses. She had a skirt and blouse, also. I said close your eyes, think about how you'd like to meet him? Have him see you the first time, as a beautiful woman, opening the door, inviting him in. She frowned. What'd I like? I said the skirt and white blouse. She smiled and took out the skirt and blouse. I buttoned her top, pulled her skirt up, helped her zip her skirt. Then we returned to the bathroom to put her wig on. I brushed it good, and told her she was beautiful. She turned, hugged me, then reached up to kiss me. I decided I'd better go, as it was 30 minutes before date time, and told her to be herself. And enjoy. She let me out, but this time she kissed and hugged me in the doorway. Good girl, I whispered to her. She closed the door, and I went to my car. But I decided to stay. Make sure this guy at least looked like his picture. Or more than one guy show up to rob her, or worse. Well, his time came and went. I waited fifteen minutes. Asshole! I emailed her. Could I come back? I replied I was in the parking lot. Her door burst open and she stood there in the doorway holding her phone. I added Your beautiful! Got out, and walked to her. She met me halfwat, and kissed. I held her hand and we went back inside. She slammed the door and locked it, then led me to her bed. I told her I was too old, too heavy, but she shushed me. She unbuttoned her blouse, doing a nice slow striptease. I laid back and watched. She said she was glad the guy didn't show. She said she had wanted me to stay before I had left. She unzipped her skirt and let it fall. I undressed, picked her up, and laid her in the bed. It was her first time making love. Shes mine now.