My First Time

Michael sent in this version of one of my favorite kinds of stories, his first time:

A few neighbor kids and I had a tradition of sleeping out in our backyards. When our parents were asleep we would meet and go to nearby neighborhoods with swimming pools. We called it pool hopping.

One night I went with Dawn and Tony. I was a year older and we hadn’t planned anything special, but in the previous pool hops we teased about skinny dipping.

When we got to the pool and hopped the fence. I  don’t remember what we said, if anything. Soon we were getting naked together. Tony quickly climbed in the pool. I looked over at Dawn, the girl I had done lemonade stands with a few summers ago when we were both skinny and undeveloped kids.

One time a few summers before when were were hanging out all the time, she showed me her privates in my bathroom. She asked me to come in, and asked me to show her how I pee. So I shyly turned and pulled out and went. She laughed when I gave a few shakes before putting it away. I’m not sure what she saw, I didn’t really care. She then pulled her shorts down and showed me how she peed. Seeing her bare privates, I was interested and stared and she quickly got up and pulled her shorts on, as we giggled.

A few years later, there she was that magical summer night, fully developed, watching me as I took off my tighty whiteys at full attention. We quietly giggled as we got in the pool.

She and Tony were sort of dating. I swam around as they stayed close to each other. We three met at the wall under the diving board and talked unembarrassed and strangely free.

I was soon enjoying the pool jets streaming around my un-private parts. I think we all found a jet to enjoy as we were silent for some long energy-filled quiet time.

Dawn got out first in the moonlight. Her naked beauty was amazing as she was wrapping Tony in a towel as he climbed up the ladder. I got out and we dressed and walked home quietly in the warm summer air.

Soon we three were separated back in our own home yards in our sleeping bags under the stars, as the cool air lulled us into wonderful dreams. I slept naked for the first time in my young life.

Since then I have had many wonderful naked experiences, with a few more times naked pool-hopping.  The last time the cops came and called our parents to pick us up in the middle of the night. It was Dawn, me, and one of her friends. The girls went off the diving board a few times and the noise wakened somebody in a nearby house.

When the cops ordered us out, I went and quickly dressed, noticing the flashlights were on the two fully developed young ladies fumbling with their clothes, blinded by the light.

I realized later that I could have jumped the fence and taken off, and the cops wouldn’t have even noticed. Our group of pool hoppers agreed to a sacred code of silence.  I was not a quick thinker then and know it would have saved me the embarrassment of going to court with my my mom to get trespassing charges dropped.

It was mostly innocent fun. Our sexual awakenings were evident, but never got in the way. It was healthy way to see the opposite sex without any of the societal BS.

I overheard my Dad on the phone telling my sister who was away at college. I could hear her laughing and see him smiling. I was often and still occasionally teased by my sister and brother. I never got upset, because I know they are just jealous of me in those magical nights. And I’m sure they know it wasn’t the first or the last time.

I have many are other wonderfully and magically clothing-free stories. I’ll save them for later.

We can’t wait, Michael! Thanks for sharing this childhood memory.

By the way, I’ve added a new tag for stories: pool hopping. Anyone else? (Although I don’t suppose I should condone it! :-))



  1. Sounds like an amazing child hood and you and your friends where comfy skinny dipping and being nude around each other.

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