This story is a mixture of real life events and events that could have happened. At the time I'm glad they didn't, but now I kinda wish they had.
*****
It was the late 1970's and a young man name Jack had been an 18 year old for less than six months. He was thin, only about 135 pounds, with dark brown wavy hair that fell just below his shoulders and a natural medium tan complexion. Since his birthday his life had changed dramatically and it seemed like, to him anyway, that he was finally experiencing sexual things he had only read and masturbated about. Since the internet and social media had not been invented yet, the only advice and information he had about sexuality and orientations came from the adult magazines he often read, so his thoughts were a little confused and unsure.
Less than a month after his 18th birthday Jack finally lost his virginity. He was in a relationship that was fun, but nothing beyond 'second base', so for his present he practically begged for his girlfriend Diane to have sex with him to which she had eventually agreed. Having sex the first time was everything he had hoped it would be. When he slid inside her warm wet pussy, he knew that the stories he had been reading in magazines had not exaggerated the joy of sex. He knew it wasn't a grand performance and probably not long enough for her, but he figured any short comings would surely be forgiven under the circumstances.
Over the next few months they had sex regularly about once or twice a week. Usually the encounter was a two orgasm experience for him, but because of his lack of knowledge and experience, he wasn't sure if she had ever came. She seemed to like it, but he really didn't know how to please her and certainly didn't know how to recognize a real female orgasm.
On one occasion Jack and Diane were in his room on the couch drinking some wine and smoking a little pot when things heated up and they began to get passionate. Eager to be naked, Jack stood up and slid his pants and underwear off revealing his cock and as it instantly grew harder...Diane watched. Feeling sexy and lustful, he straddled her lap and began kissing her passionately. She grabbed his cock firmly and began stroking it as they kissed and she too was became excited. Suddenly she sensed he was breathing faster and deeper and his hips pumped his cock hard against her hand. It was the first time she ever gave a guy a handjob in this position and she thought it was strange, but exciting. She ran her free hand up his exposed thigh and grabbed his ass and a moment later she felt warm fluid spray onto her forearm and ooze across her hand and palm.
"OMG Jack! You Came?" She asked surprised after he all but finished his orgasm. He had been extremely excited by what was happening and he couldn't hold back. Now it was over, he was feeling a little embarrassed.
"Yes, I guess I did" He answered meekly, "I'm sorry, I just..."
"Oh don't worry, I thought it was exciting too. It felt like our roles were reversed, you sitting on my lap and me getting you off, kind of like you were my girlfriend!" She kidded. That really embarrassed him and was blushing red as that was exactly how he had felt...like a girl, or more precise... a feminine character of some sort. He was confused and uneasy with the situation and tried to shrug it off as it being the pot they had smoked.
"Oh? Well must have been the weed Diane" He reasoned, "Guess I got a little carried away."
"You must have been pretty excited" She smiled, "Come on, your turn to do me now!"
They played most of the afternoon, but in the back of Jack's mind he kept wondering why feeling feminine had gotten him so excited.
Weeks passed and the events of that afternoon soon faded and life continued as normal. His relationship with Diane stayed about the same, a lighthearted sexual affair with neither of them growing too serious about it. School had come to and end and he had graduated with his class, but not without a lot of hard work juggling his dishwashing job at night and having extra classes to make up credits. He had been lazy and failed several courses his first two years in high school.
Thankfully the stress of passing his heavy workload of classes was over and he had his diploma in hand. His night shift job was now the only thing he had to do besides partying with his friends. The job was at a hotel restaurant and he had been one of the dishwashers there for almost a year and a half. It wasn't a bad job, not too busy most of the time and when he wasn't helping the cooks cutting lettuce or something, he could just kind of hang out. It was during the slow times that he had explored around the hotel and found he could access the seldom used banquet rooms from a service hallway that ran off the back of the kitchen area. As luck would have it, the hotel didn't turn off the drink dispensers and he found in the kitchenette there was a multi-button tap that dispensed not only soft drinks but liqueur as well! More than once he had snuck back to the banquet room and made himself a rum and coke to make the evening of dishwashing more enjoyable.
Everything was going well and Jack's only worries seemed to be what he would do if he had to work on a night when there was a really good concert he wanted to see. But that changed when the restaurant hired a new dishwasher. They wanted back up in case someone decided to go on vacation or decided to quit and move on. It was Thursday night when Jack met Rick for the first time. He seemed alright, he was older, around 45 and ruggedly handsome and on first impression he was someone you might like and not fear.
That evening Jack was tasked with showing Rick the dishwasher duties and later there was plenty of time to talk and get to know one another. It turned out that Rick had been in the Navy for a few years and had some interesting stories to tell of his travels around the world in one ship or another. To Jack it seemed strange that he had such a career and was now doing a minimum wage 'Kids' dishwasher job, but Rick explained it away saying he was just bored and wanted some extra spending money.
During one point in the evening Jack was showing Rick where to stack the clean plates when Rick leaned in close and put his hand on his shoulder to see back into the shelving. Jack thought it was a little too touchy for his liking, but didn't really think much of it since Rick seemed ok. Later though, while Jack was sorting silverware, Rick came up from behind and stood next to him and once again placed his hand on Jack's shoulder and said, "So Jack, you graduated High School recently?"
Jack responded after eyeballing Rick's hand but pretending not to be bothered by the contact, "Yeah it was real pain...I had to make up several classes I failed earlier".
"Oh, guess you were too busy chasing those young girls around to go to class?!" Rick kidding and casually let his hand slide down across Jack's thin shoulders and to his lower back. "Ah Yeah" Jack responded wiggling away from Rick's touch and looking at his smiling face, "You know how it is." Rick crossed his arms and played it off, "Yes I know how it is, I like the young ones myself."
