The dress that my mom wore the night before was lying on the bed. It immediately caught my eyes. It was a burgundy bodycon dress with a cut on the front side. I also found her bra, pantyhose and heels lying in one corner of the room. It was already making me tingle with excitement just thinking about putting them on . Yes I was, we all know someone has been trying on your sisters and mothers clothes for quite a while now. It was just a matter of time before we caught you at it .” With plenty of time to plan and wait, I crafted an ad online. I had always fantasized to spend some time with other crossdresser. Having a place to host, in this case the empty house, while not glamorous, gives me a much better chance than I would otherwise have had. So as you might imagine, I got quite a few more replies than usual…of course, that means nothing if they’re all flakes who just want dirty talk and pictures to get them off.

I arrived home, from work, on the Bank Holiday weekend, of Easter. The following week, I was taking days off that were owing to me, so the forecasts were good, and I was happy. As I entered the house, I heard chatter, and recognized my mom and aunt Marilyn’s voice. I had no other option but to tell her everything and I was surprised how calm and supportive she was. She patiently listened to me and told me it was all-right. She did mentioned that it would have been better if I had told her about my crossdressing before. Then I went to change clothes and she stopped me and said ” You do make a beautiful girl”. I blushed and she kissed me.

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The first time was while I was still living at my parents house and I actually got caught. They were out of town on business (they owned a small electronics company) and my sister was at work. I push Samantha to go and he leaves immediately. Now, I had to face Bob and explain everything to him. I was never so embarrassed in my life. Bob had calmed down a bit. Then, I sit down on the chair and with a deep breath, I start explaining everything to Bob about me being a crossdresser and what I had planned to do this evening. Bob then comes a bit closer. So. You think that just because I may or may not be here, it gives you the right to slander one of my children?”

My parents were quite strict so I was extra careful every time I got dressed in my sister’s clothes. Usually all her dresses fit me well and soon I also started to try out some of her bra. It was usually for a very short amount of time. I just put them on wanting to know how they felt and then take it off immediately because I was really scared someone would catch me like that. But this really made me feel so excited. Then, I got the pantyhose. I had never worn them before but always wanted to wear one. This was my best chance. So, slowly I put them on. I struggled to get it on because the alignment always got wrong. With quite a bit of effort, I finally got the pantyhose on. It was an intense feeling that I had never experienced before. I completely fell in love with how it felt on my legs. Lastly, I put on my mom’s heels and my feet could fit in them. It felt amazing. Same thing as earlier I wake up on the bed again. I do not know if my poor brain can handle this. First I am caught. Then Dawn says she and mom know. Then I faint. Then they dress me up while I am out of it. Then I see mom, Dawn and what could only have been me in the reflection, and what do I do. I faint again charming just charming. No way! I won’t.” I said angrily. “Fine, if you won’t then I will tell mom and dad what you were doing with my stuffs!” She said and turned around marching to the door. I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn’t easily wear under my man clothes. With that all done, all I had to do was wait…for two more days! That’s like two MONTHS for my level of excitement and anticipation. I wasn’t simply planning on dressing up and prancing around an empty house at night…I wasn’t planning on being the only one to enjoy what I would be wearing!

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When I went to college I did not have the opportunity to dress until I was able to get an apartment with one of my sisters friends who was living in the same city. When my sister found out who my roommate was she sent pictures and video to both of us and said to have fun. And fun we did have. We took things to the next level. Dressing up and going out together to parties and bars. Staying in makeup and women’s clothes whenever I was at home. She even took me to her salon for pampering, hair removal, eye brows and acrylic nails Because it makes you look more like a girl your age. If you’ll just look in the mirror you will see for yourself.” What are you doing? I can’t believe this. Are you doing a prank on me or something?”, she asked me. Due to my crossdressing habit, I was quite an introvert and shy to interact with other people. I loved spending time alone and just dressing up and trying to look as feminine as I could. I even went out in public few times dressed as a girl and it was so amazing to me. I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger.