Harold's First Time Part I - Sex Stories

Harold's First Time Part I

There is one thing in this world that will always be consistent, the sexual desires of a teenage boy for older women who are clearly out of their league. Having been a teenage boy and knowing how much truth there is to it I decided a little story about a young G.I. and a barber might be something worth sharing… Harold was 17 years old when he enlisted into the military. He was about 6 foot tall, 160 to 175 lbs, medium build, black, and in pretty good shape due to high school athletics. He was a decent student in high school but could not afford college. Enlisting in the military was a quick decision but in the long run would turn out to be one of the best decisions he had ever made. His first duty assignment was Lakeside Air f***e Base in California close to San Francisco and only a few hours from San Jose. Harold had kept to himself in high school deciding that concentrating on his studies and graduating on time were more important than girls or sex (funny how many teenage boys really don’t think that way). This was mostly due to his shyness around girls and inability to talk to the opposite sex without looking like a complete idiot. It was time for the weekly military style haircut. The barbershop was always busy so Harold had to take a number and wait. When they finally called his number he was surprised to see his barber was female…a very, very attractive female. He did not know how his hair would look later but by the end of this story you will see it really doesn’t ...

... matter. The name on her name tag was Jeanne and she did not look to be much older than Harold. She was a very attractive lady with medium length black hair, brown skin, she look like she weigh about 110 to 115 pounds, and about 5 feet 3 inches in height. Let’s finish describing her by saying she was the most attractive woman Harold had ever seen. For the first time in his life he was looking forward to getting a haircut. So far their conversation was absolutely boring until dummy finally noticed that each time she moved her breast were in his face or somewhere close. He even noticed how hard her nipples were because he could see them through her shirt. Being a teenager he had absolutely no control over anything so as soon as he started breathing a little heavy he noticed his little buddy wanted to make an appearance (thank goodness the aprons the barber use to cover their customers are so large). Jeanne was no fool and she knew exactly what was happening, Harold was getting an erection. This had happened before with other young men but this customer didn’t ask for her phone number, flirt with her or anything he was just nice. “How often do you get your hair cut?” she asked. “Once or twice or month, how long have you been a barber, do you enjoy it?” “Not really. I am good at it but for right now it is just helping me pay to get my training and license to become a realtor. But, it has been a good job and the tips I receive are really good. What about you, how long have you been ...