Double Dared

Double Dared

I was 15 the summer of 1950 when I was persuaded to perform a dare. It was embarrassing at first but it was fun at the same time. Several of my friends, all about 15 years old, met a neighbors house for a cook-out one evening. When I arrived Adele said she really liked my shirt. I was wearing a striped polo shirt and she was wearing a similar one I said, "I like yours too. Wanna swap?" To my surprise she started to take off her shirt and someone yelled, "Hey, Adele and Jack are going to swap clothes!"

Joe yelled, "I dare you!" Adele said she thought it would be fun and then Frank double dared us to switch all our clothes. I said, "Oh! No!" But Adel said, "Let's do it! You are a yellow coward if you don't!" What choice did I have?

Adele was wearing the blue polo shirt and white shorts and was bare foot. I was wearing a blue and white striped polo shirt, levis, Converse basketball shoes, white socks, and jockey shorts. I figured it wouldn't be so bad to dress in Adele's clothes since she wasn't wearing a skirt and we were almost the same size. So I agreed to the cheers of the others.

We went into the rec room, which opened onto the patio and Adele shut the door and suggested we turn our backs while we removed our clothes. I took off my clothes and laid them on a chair without peeking at Adele. Just as I took off my briefs she said we will just have to face one another to get to the clothes. This was the first time I had seen a naked female in the flesh and I suppose it was the first time one had seen me nude. I immediately turned my back again to hide my erection. I grabbed her panties and slipped them on and then her shorts. They fit OK but a little tight in the waist. I was surprised to find the zipper on the side instead of the front. I turned again just as she was pulling up my levis. She actually had on my jockeys! I started to put on her shirt when she said I would have to wear her bra because we agreed to exchange everything. It was uncomfortably tight but she helped me fasten it all the while she was topless. I couldn't keep my eyes off of her and she seemed in no hurry to put on my shirt. She was topless as she sat on a chair to put on my shoes and socks. When she put on my shirt we were completely dressed as each other. I was amazed we could wear each other's clothes.

We returned to the patio to the applause of our friends. Everyone thought Adele looked really sexy and I looked kind of silly. Adele commented that she had never worn boy's clothes before and was surprised at how heavy they were and it felt funny to have things in the pockets especially the billfold. I added that I didn't like the feel of the thin fabric of her clothes. Even her polo shirt, though similar to mine, was a much lighter weight.

We had performed the dare and I suggested we change back. But Adele said, "No. I want to wear these the rest of the day. We'll switch back before we go home. I agreed if they would allow me to take off the bra since it was uncomfortable. Everyone agreed so I did. Adele commented she thought it would be fun if the others switched too. Frank suggested Adele and I go to school Monday dressed as each other. Adele thought it would be fun but I didn’t like the idea. I said I would do it if the others switched too. The girls all agreed but the boys declined. When it was time to go home Adele said she wanted to keep my clothes for weekend.

I wish we had taken some photographs!

After the others had left Adele and I helped Frank clean up and wash the dishes. Frank’s parents were expected back at 11 PM and it was already 10:30 so I asked Adele to switch clothes with me because I didn’t want them to see me in girl’s clothes. Adele said she would really like to wear my clothes home. I said I couldn’t walk to my house barefoot it was a couple of miles. Frank said, “I’ll lend you something to wear and Adele can take her clothes home.” I agreed if Frank would lend me some of his to wear home. I couldn’t walk home bare foot wearing girls’ clothes. Frank and I were about the same size so he agreed. The others were leaving so I told Adele to wait while I went in to change so I give her clothes back to her. Frank and I went to his bedroom where he supplied me with some male clothes. Now I felt more comfortable. When we came back to the patio Adele said, “By golly, you look just like Frank.” Frank said, “Yeah, and you look just like Jack.” “I guess,” I said, “if we walked down the street people would say there goes Frank and Jack. And they would be only half right.”

Adele picked up her stuff and started to leave. “Wait,” I said, “I’ll walk you home.” “OK,” she said and we said goodbye to Frank who asked me to come back later.

When we got to Adele’s house, it was just three houses up the street, she invited me to sit on the porch swing with her for a few minutes. She told me how much she enjoyed our evening and hoped we could get together again—just the two of us. “Wow!” I thought. I said, “I can’t wait.” Just then Adele’s mother came out on the porch. She looked surprised to see how Adele was dressed. “Whose clothes are you wearing,” she asked. “Jack’s,” Adele answered.

“Why are you wearing Jack’s clothes”

“Somebody dared me to do it. So I did. Jack is wearing Frank’s.”

“Oh,” her mom said and went into the house.

I thought she might figure out what we did but if she did she didn’t say anything.

I got up to leave saying, “I’d better get moving. It’s dark and I have to walk a couple of miles. Adele came to me and gave me a kiss on the mouth! This was the first time I received a kiss like that! She said goodbye and went into the house. I walked on air all the way home.