Yes I started a week ago. I help after school and on weekends. My mom seemed to think if I didn’t start working, then I’d end up getting in trouble with my friends.” He swam a few laps before hearing the garage door open around the side of the house. He thought this was weird as Megan usually just parked in the driveway but thought it must be easier to get the groceries in through there. I said I was really sorry and I didn’t know why I wanted to but I just felt like trying. I wasn’t a kid anymore and that made me feel more embarrassed. My mom then asked me how long I have been dressing up in her clothes and I lied saying it was my first time. The good thing was she wasn’t very angry and tried to be understanding. As soon as the zipper was down, I rushed to my room to take of the dress and pantyhose.

We go inside and sit on the chair. We start our conversation by telling each other a bit about ourselves. He tells me her feminine name is Samantha and he has been cross-dressing for the past 10 years. It was really exciting to have another crossdresser to talk with. I was really enjoying the moment and I had a lot in my mind about what to do next. But then, all of sudden, he comes really close to me and kiss my lips. The look on dads face after that little chat was great, talk about eyes popping out of his head . probably wondering how he goes to work in the morning, gets a phone call about his son dressing and can they meet at the mall. Then he finds out he is being setup for dates by his sister while dressed as Nicola. I tell you it was the best thing to happen all day. I returned the clothes to my mom and she said if I wanted to talk about it. I said I was sorry and just wanted to know how it felt to wear a dress. She agreed to not tell dad and after that moment I made sure to never get caught like that. My mom didn’t asked me about it again and I think I feel more comfortable like that.

Discussions (52)

I don’t know what got over me. I am really sorry Jody. I promise.. I will never do this again.” I answered, almost about to cry. Yep me and mom. As I said, we knew someone was. And we were waiting for the right time to either catch you at it or talk to you without you denying it.” No mom I’ll be ok. Where did the dress and heels come from? I don’t remember seeing this in Dawn’s closet before.”

About an hour later, aunt, telling me, as I was reading a woman’s magazine of hers, that she just be over the road, to chat to her friend for awhile. 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.Once puberty hit, crossdressing took on a whole new aspect. I started to realize that I wished I could dress in girl's clothes all the time and that I preferred the way girl's dresses fit my body and how they looked at me. I also began to feel trapped in the wrong body and that I should have been born a girl. These realizations were confusing and scary for me, and I wasn't sure what to do with them. 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. Right , first things first, one you look very nice, a younger version of your sister but very nice indeed, and two lets eat and Nicola?” Okay, I won’t tell them but from now on you have to do as I say.” She said. “Fine, just don’t tell them. I will do anything Jody, please.” I said hopelessly. “You better get changed now. Mom’s going to be home soon.” Jody said with a smile, knowing that I was completely under her control. By now even Michelle was aggravated and just wanted to go home and hang out with her friends. "Are you coming or not?"

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.”After that day, my wife allowed me to crossdress inside the house. I couldn’t believe how supportive she was to me and I felt so grateful to have her in my life. Slowly as time passed, she accepted my crossdressing more openly and sometimes helped me get dressed and also teased me on how cute I looked. It was really wonderful to have the weight of my shoulders about keeping my crossdressing a secret. My family once noticed my sister's panties in our guest room closet, her one piece in my sink, her compression shorts 3 times in my closet, once confronted with my mom and sis finding a two piece in my closet as I was in the room, I said as a complete lie "Well I chafe down there, and use the bottom half to stop that, and my dad caught me wearing a sports-bra once when I was 9(Which I could have gotten away with, had I not told him I was ) So I guess they basically know, and would tell them, but I dont think I could go on full time(Even though I really want to) and just the way people think of you, my friends who id loose alot of, basically telling them I have lied constantly and that I feel so wronged and cheated. Plus, I want to make my parents to feel proud when people know Im their son, and be to proud of 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.” She was silent for a while. I could understand her reaction. I apologized to her for keeping such a secret from her. After that, she went to bedroom and we didn’t speak that whole night. I felt so bad about myself and I sat in the living room feeling so upset and embarrassed about my actions. I had no confidence to face her so I slept on the couch in the living room.