My first time buying condoms, at age 16, I went to the pharmacy. The hot cashier at the counter could see that I was new at it and gave me the pack asking if I knew how to use one. I said, "No, it's my first time."
She took one out, put it on her thumb, and told me to make sure it was on tight.
I still looked confused.
She looked around the store to see if it was empty and it was.
"Just a minute." she said and locked the door.
She led me to the back room, took off her shirt and bra.
"You like these?"
I could only nod my head.
She said to put the condom on.
As I was putting it on, she dropped her skirt, removed her panties and laid down.
"Come on." she said. "We don't have much time."
So I climbed on her.
It was so amazing that I couldn't hold back and KAPOW! I was done in two minutes!
She looked at me concerned and asked, "Did you put the condom on?"
I said, "I sure did!"
...and held up my thumb to show her.
That reminds me of a true story that happened to me the week before I started middle school. My mother had bought the required things that I would need for gym class but forgot to get me a jock strap. She gave me some money and told me to go down to the local men's store and buy one.
All the way there I was nervous because I had never bought one before and what if a woman waited on me? My worst fear came true. A woman waited on me. I told her that I needed an athletic supporter. And then came the dreaded "what size?" I guss she could see terror in my eyes and she told me that it goes by your waist size. Phew!!!