The Betting Dress

My name is Patrick and I am going on a trip to visit my cousins for the week. I woke up in the morning has my mom was yellinng for me. I looked at the time and we were suppose to be leaving, so I jump out of bed and got dressed. I didn't care about going because I had only girl cousins. So, I packed some stuff in my suitcase and ran out the door to the car. I put my suitcase in the back and got in the car. Before I knew it we were off to my cousin's house. My cousins live in a cottage by the lake. That's why I loved visiting them. It had never rained there before, so we could always go swimming.

When we got there, it turned out to raining for the first time?? I grabbed an umbrella and went inside. I saw my cousins in the living room before they ran over to hug me. I put down my umbrella and took my shoes off. They brought me to the living room to sit down while they played truth or dare. They asked me if i would like to play and I agreed and sat on the floor. When it came to my turn, I dared one of cousins to go outside in the rain for 2 minutes. She agreed and went outside. I watched her all wet as I was laughing. When she came back in, she was dripping on the floor and went to get changed as we continued to play. When my wet cousin came back out she was in a pink dress. My mouth dropped open at the sight, I never knew she wore dresses shes my age but the others were older. After that my oldest cousin suggested we play bets on eachother. That's when they looked at me. My cousin in the dress wanted me to make a bet with her and I agreed. The bet was to see who could stay in the rain longer. She agreed to it and asked what happenes if one of us wins or loses? I said that she would have to sleep in a bathing suit. She laughed at it and said that if she won I would have to dress as a girl for the whole week.

My eyes opened wide as I agreed and me and my cousin walked outside into the rain. We both stood in the rain for 5 minutes and didn't run inside. After about 10 minutes I ran inside all wet as my cousin had won. I dind't care, I just wanted to be dry. They laughed at me that I lost to a girl, I ignored them and grabbed a towel. I was dry after about an hour and that was when the bet started. A bet is a bet so they brought me to my cousin's room. They told me to ***** nude as they grab a pair of panties and closed their eyes as they told me to put the on. After that they brought me to the bath room. They held me down on the toilet and they shaved my legs hairless like a girls body. After that theey brought me back to her room and gave me a pair of red tights to put on and I did. It felt nice without hair on my legs as they pulled out a bra and strapped it on me and then stuffed it. It felt nice, but I didn't want to get noticed liking it. Next, they put a full slip on me, then they put some black heels on me and then made me put a dark blue dress on over the slip. Theybrush my long blond hair in a girly way and curled it. Then applied make up. I looked in the mirror and there wasn't a boy there was a girl. They called me Patricia and brought me out for my aunt to see me. She smiled and said how pretty I was and that the girls did a good job. I thanked her and then out of no where I smiled and the girls noticed I had enjoyed being dressed up. They smiled at me and brought me back to there room. They pushed me onto the bed and talked to me about if I liked it. I said yes and they took the clothes. I was left on the bed in panties. I got up and they put a nightie on me. They took off my make up and made me where a nightie for the rest of the night. After wearing it for about an hour I really enjoyed wearing it. I smiled and hugged my cousins. I thank them and then we played girly games.

When it came to going to bed, they brought me to the spair room and got me into bed. They gave me a pillow that said I love dresses and I hugged it. I then fell into my sleep. I had an amazing dream about being dresses at my house and not just at my cousin's. It felt like a five minute dream but it turned out to be the whole night and my cousins woke me up in the morning. They said it wasn't raining and that they planned to go to the public park. So thye got me out of bed and gave me a blue play dress, white knee socks, and mary janes. We had breakfast and then left for the park. No one was there at first but about 30 minutes later people showed up and didn't even notice I was a boy. I had a great time playing there. I met up with some other boys that were wearing dresses and played with them. We were at the park until lunch time when we had PB and J sandwiches that were amazing. I made so many new friends and played with a lot of great people. We talked about girly things and how so much better it is to be a girl than a boy.

I was dressing for the whole week and really enjoyed the experience.

This story is fictional and doesn't relate to someone or something.
Jacklyn13 Jacklyn13
61-65, M
7 Responses May 1, 2012

add me sweetie

add me sweetie

Wow, My female cousins did dress me up

add me sweetie

That happened to me before

I WISH!!!!!!

Damn, until the disclaimer I was enjoying the story and the fact that this had actually happened. Wish it had actually happened to me.

no need for the disclaimer (wink) it was a very nice story.