Sissy Caught: First Time Feminization, Crossdressing (A New Woman (Transgender Women and Feminized Men Romance Stories))

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I tried to calm myself down and then went to open the door. I was still nervous if she would suspect something but with a smile I opened the door and welcomed her. She looked exhausted from her trip and said she wanted to take a shower to freshen up. When she was out, I would then take out my secret stash of feminine items and get dressed and enjoy myself. One day, I finally decided to step out of the house dressed as a woman in the evening because I started to get bored just dressing up inside the house. Ben thought that she was just being young and dramatic and that he could make it up to her somehow over the weekend. No you are not. We all wanted to find out what was going on and this is the only way. Now we will give you a few minutes. then we are off to the mall for a shopping trip.”

With that comment , dad sprayed his drink all over the table with the classic goldfish look on his face. Borrowed one, silly boy. There's plenty lying around in her room. Just go grab one of those." She smiled again and James felt a nauseous feeling grow into his stomach.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! We agreed on a time, and he wanted me waiting inside the house, where he would come fully dressed up as well. We would simply both enjoy the moment as pretty women. The next two days dragged on and on… It all started innocently enough. I never meant to do it, it just sort of happened. I got home from school, when I was in the 10th grade. I put my bag down on my desk, and noticed that mom had left the laundry basket on my bed. This was her signal that I was supposed to put the clothes away in my drawers, and bring down any dirty clothes I had. While you were sort of unconscious, we decided to get you dressed. Why don’t you get up if you can and look into the mirror?”

As he pulled up in the van, he could see his sister standing alone against the wall near the gymnasium.

I must have taken like thousand of photos and videos of me going around the house. I was too scared to go out in public but I did step out in the balcony at night fully dressed from head to toe. It was an exhilarating feeling. I dressed everyday for the whole week my wife was away and when it was time for her to return. I just got rid of all the stuffs that I brought and promised to never dress up again. Right then. I do not know what happened; I think I fainted cos the next thing I know is I was coming around. But time and again, I would really feel bad about my crossdressing and then throw out all the clothes and feminine stuffs that I had brought and try to live a normal life. I crossdressed on and off for quite some time and after college, when I started working, I completely stopped to crossdress. 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.

After that incident, we had a long conversation and I had to convince her that I wasn’t interested in men but I did like to dress feminine once in a while. She was very understanding. I was sure she would leave me but she didn’t and now she is okay with me dressing up sometimes but only inside the house. Now, when I think of it, it was better that I was caught because after that I felt really relieved and accept myself for who I am. 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. 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.

I tried really hard to resist the urge to dress up but every time I was alone in the house, I just wanted to sneak into my sister’s room and try one of her outfits. Few times when I had the opportunity, I would wear one of my sister’s dress and roam around the house. It felt so wonderful. But I felt guilty every time after I had crossdressed. So, I decided to put a stop to it. Too bad. I had a couple of outfits now. I loved the one yellow floral dress, because it was such a soft material, and when I whirled around, it would swish against the pantyhose, and send shivers up and down my spine. I just loved it! It turned me on so much! But one day, even in full dress, it didn’t seem like enough. I wanted more! Nobody was home, so for the first time, I left my room dressed as a girl. I was *so* afraid that someone would look in the windows and see me! Yeah well they are in the middle of moving to Bessemer, and were looking after Nicola here for a few weeks; we’ve sent Nic there to help unload.” So, I decided to dress up when one time, my wife told me she was going to be away for a whole week. After she was gone, I brought few dresses, hair wig and heels online. It was so thrilling to be dressed again. I felt like I was reborn again. I got dolled up from head to toe and couldn’t stop admiring my own looks in the mirror.

Hey no fair. We have been after him for ages, NICOLA here has been a girl all of what? And she has already caught his eye. This isn’t fair, but well talk later ok, by the way MISS are you going to buy that?” I had to act fast and get rid of everything. I had heavy makeup on and even had nail polish in my hands and toes. So, I went straight to the bathroom, got undressed and started to remove my makeup and the nail polish as fast as I could. Then, I took all the clothes, makeup and shoes and put it in a bag and hide it in the store room. The look mom got from dad was a classic also; I thought it was my day for being looked at in a very angry way. I tell you this day was getting better and better, well apart from being caught that is. And then the front door opened! My heart raced. I looked around the room and there was literally no escape apart from breaking the window and jumping out. I could tell from the footsteps that it was my dad and he was on his way in. Come on, we’re late. We’re taking your father out to dinner tonight for his birthday. Don’t you remember?”I don't know if she ever told anyone, but I never heard anything about it from anyone. I was scared to death for months afterwards. I would see Jan from time to time and she would wink at me, giving me a knowing smile, but she never brought it up again. It was one of the most intense experiences of my life... I ran to get tissues to clean it all up. That was stupid of me! But for some reason, thinking of myself as a girl made me really turned on, and made me climax so easily! I wanted to be with a girl so much, but this was exciting too. I would just do both. If I could get Lynn, my crush, to go out with me, I’d still do this in my spare time. Perhaps, I could get some of her panties too. Then I’d be wearing *her* clothes. Now *that* sounded really exciting to me! Over the next few weeks, I kept dressing up. Sometimes with just the panties, but sometimes in full outfit. I stole a pair of pantyhose from the laundry room, and started wearing those too. She then realized that I was not Geni, although there was a hint of recognition in her face. She broke into a wide grin and I had tears streaming down my face. She knew exactly who I was now and I was petrified! She tried to calm me down and asked me my name, although she knew damn well who I was. I replied Tiffanie, and she told me that it was a very sweet name. She said I looked cute in my apron and asked me if I was the new house cleaner, to which I replied yes. She was actually playing along with me, trying to put my mind at ease.