In 1955, I was approximately twelve years old. One afternoon in the fall of that year, I remember joining my parents who were visiting some friends in the neighborhood. These friends had an older teenage daughter. She was very pretty, and I had a crush on her. Furthermore, she always wore the ubiquitous penny loafers that were the rage of teenage girls and young women at the time.
On this particular day, as my parents and their friends were talking, I walked through the house and entered the daughter's bedroom. Her closet door was open and I noticed a pair of penny loafers by the door. My curiosity drove me to sit down and pick them up. They were beautifully crafted and glove soft. I put them up to my nose and gave them a sniff. They smelled pleasantly of roasted nuts. All of a sudden, my twelve year old penis got very hard. While caressing them, I noticed a worn logo on the inside of one of the loafers. It read Old Maine Trotters.
Then, I decided to try them on. The owner was not only pretty but very tall. Consequently, her loafers would fit me! Ripping off my sneakers, I slipped into the loafers. The experience was exhilarating. Continually looking at my feet, I walked around the bedroom. My penis was very hard, and my stomach ached I was so aroused. I sat down again, removed the loafers and started kissing them. At the same time, I feverishly grabbed my penis and masturbated.
Even at twelve, my discharge was immense. It showered all over my shorts and the loafers. Fearful of being discovered, I quickly grabbed a bedspread and wiped the cum off myself and the loafers. Then, I carefully replaced them in the girl's closet. What an experience! I had lost my virginity not to a teenage girl but to her Old Maine Trotters. It was very excitlng.
I joined my parents who had not missed me. My girlfriend, years later, wore only loafers. Not just loafers but...Old Maine Trotters. She was sexy and her loafers were sexy. She owned four pairs, two brown, one red and one black. It was the summer of 1961, and we were sitting by her parent's pool. Around noon, she had to leave and visit her college counsellor. She left her old brown Trotters by the pool and wore the new pair for her visit. When she drove off, I stayed by the pool. I kept staring at her loafers and finally picked them up. They were smelly and soft and damp from her sweaty feet. She had not been wearing socks, and the smell was a strong leathery pungent odor.
I got very hard immediately. Squeezing them with both hands, I moved to the pool house. Overcome with desire, I masturbated and smeared the cum all over the loafers. I returned poolside and replaced the Trotters in the sun. The cum dried quickly, and because the counsellor was nearby, my girlfriend returned within the hour. She changed into a little sun dress, and barefooted, she came back to the pool. She wiggled into her loafers and sat down next to me. Then, she noticed the faint lines of semen on her Trotters. I had done this before, and she liked it. She grabbed my hand and led me into the poolhouse. Inside, she took off her sun dress and stood naked in front me. She whispered she was very horny, and we made love. Like many times before, she kept her Old Maine Trotters on. Over the years I have never been attracted to men's loafers or even to all women's loafers. However the fantasy of a beautiful woman with long legs, thin ankles and her feet tucked into a pair of Old Maine Trotters is a huge turn on. I still masturbate frequently with these thoughts.