Lessons to Be Passed Along
Copyright© 2025 by rlfj
Chapter 1: Meeting and Dating
Romance Sex Story: Chapter 1: Meeting and Dating - Multiple generations of women marry and pass along their wisdom.
Caution: This Romance Sex Story contains strong sexual content, including Ma/Fa mt/ft Consensual Anal Sex First Oral Sex
1964
“Well, aren’t you a little cutie!” said the cashier.
Tommy Caparelli smiled at the young woman. She wasn’t talking to him, but to his infant son. Herschel was sitting in the child seat of Tommy’s shopping cart, kept upright by a few baby blankets, and was looking around at the world. When he heard the cashier talking to him, he turned to face her and gave her a big smile. He flapped his arms and made some happy gurgles back at her.
“I am guessing you are talking to him and not to me,” said Tommy.
“Nothing personal, but I’ll get in trouble if I start flirting with Daddy. Better that I stick with him,” she laughed.
Tommy smiled. “Thanks ... I think.” He began putting items on the belt. It was Saturday afternoon, and he was grocery shopping at the Grand Union with his son.
Tommy looked closer at the girl and realized just how pretty she was. She was very short and wearing a not very flattering grocery store uniform of pants and a shirt, but she seemed to be quite curvy underneath it. She had wavy auburn hair and brown eyes but what really set her off was when she was smiling. That transformed her from pretty to breathtaking.
“What’s your name?” asked the cashier.
Tommy looked at the girl, who was wearing a nametag that said she was ‘Mary T.’ “Tommy,” he replied.
Mary giggled. “I was talking to the cute guy.”
“Now that hurts!” protested Tommy. Mary giggled again, and he added. “Oh, you mean the short, cute guy, not the tall, cute guy. His name is Joey.”
“Thank you.” Mary kept ringing up the groceries and talking to Joey, though some of her comments seemed aimed at his father. When she finished, she bagged the groceries and took a lollipop from a container next to the cash register. “Can I give him this?” she asked. Some people got picky about giving their children sweets.
“Sure, but I think I’d better hold this for him, otherwise he’s going to fuss when he can’t get it open.”
“Hmmm ... sounds fishy.” She looked at Joey and said, “I think Daddy is going to take your lollipop! I’d better give him one, too.” She pulled out a second candy and handed both to Tommy.
Tommy laughed as he loaded the grocery bags back into the shopping cart. “So wise, so wise.” The lollipops went into his shirt pocket.
“Bye!” Mary waved her fingers at Joey, and he gurgled and flapped his arms.
“Bye,” replied his father. Tommy pushed the shopping cart to the exit.
Over the next three weeks, Thomas Caparelli went grocery shopping three times at the Grand Union. On the first try, he missed Mary, but casually asked another cashier when she worked. The next two times, he made sure he went through Mary’s line. On the third week, he stopped shopping halfway through his list and followed her to the lunch area, where he found her buying a piece of pizza and a Coke. When she saw him, she smiled and asked, “Where’s your little helper?”
Tommy smiled back. “He’s at home with my mom.” He pointed at the chair across from her. “May I?”
She looked at him curiously. “Okay.”
Tommy sat down. “Feel free to tell me to buzz off, but I think you are ... well ... uh ... I feel so stupid.” He moved to stand up.
“What’s going on, Mister Caparelli?” The week before he had worn a work uniform while shopping. It had ‘Tommy’ embroidered above the left breast pocket and ‘Caparelli Construction’ on a patch above the right breast pocket. She had asked him about it, and he admitted that his last name was Caparelli, and he worked for his father as a carpenter.
He sat back down. “I thought I might ask you out,” came rushing out.
“I don’t date married men.”
Tommy said the first thing that came to mind. “Neither do I.”
“What about that cute little fellow? You’re divorced?” she asked.
He didn’t smile. “I’m widowed.”
Mary’s eyes popped open. “Oh, my God! I am so sorry! I ... I mean...”
Tommy shook his head. “You had no way of knowing. Don’t worry about it.” He paused a moment and added, “I’m not trying to make you uncomfortable. It’s just so hard to meet people at times. If you want, I’ll leave you alone. You’ll never see me again.”
“No, it’s just you surprised me.”
“I was just figuring something simple, maybe dinner, or even just a lunch. It would have to be on a weekend, though, for a lunch.”
Mary looked at Tommy, but then looked away. “I don’t think so,” she said quietly.
“Well, okay. I’ll leave you alone.” He stood up.
“That might be best.”
That evening, Mary told her mother about what had happened at the store. “What’s he like?” asked Angela Tomasino.
Mary shrugged. “Well, he’s tall, like really tall.”
Angela snorted and said, “Mary, you’re all of about five foot nothing. Everybody on the planet is really tall next to you.”
“Mom!” Mary gave Angela a Bronx cheer.
“What else?”
“He’s older than me, but not like really old, like you and Dad.”
Angela said, “You are pushing your luck.”
“And he has this little boy. So cute! He’s about one, I think. He says he’s a widower, but it can’t have happened all that long ago, right?” She continued telling her mother about Tommy.
Angela was curious about what her daughter was up to. She seemed to know an awful lot about this guy, much more than she would know about any other customer. “So, why didn’t you say you would go out with him?”
“Mom, you know why. I can’t date...”
“Mary, what makes you any different than this Tommy fellow. He has a baby boy? So what? So do you!” She looked at the small bundle wrapped in a blanket next to her. “And yours needs changing.”
Mary rolled her eyes and grabbed a disposable diaper.
The next week, Mary Tomasino saw Tommy Caparelli shopping in the Grand Union. She quickly called for somebody to fill in and then went searching for him. She found him pushing a shopping cart through the bread aisle. His eyes lit up when he saw her approaching. “Mister Caparelli.”
“Tommy.”
“Tommy, were you serious about going out?” she asked.
“Yes.”
“Okay.”
Dinner Saturday night was at a restaurant on Broadway in Saratoga Springs. Mary asked Tommy to pick her up at the grocery store. She was nervous about meeting him at her home; her mother knew she was going out on a date, but neither had told her father.
It was raining lightly, so Mary was wearing a trench coat and hat that she had borrowed from her mother. She drove to the Grand Union in her mother’s VW Beetle and parked near the entrance, instead of the side where the employees parked. She looked around nervously. What if he didn’t show up or something? Then she saw a tall man walking to the store entrance and looking around. He, too, was wearing a trench coat but didn’t have a hat. She flashed her lights, and when he turned in her direction, she grabbed her purse and got out of the car, locking it behind her.
Tommy walked towards her and met her in the parking lot. “I was worried you might change your mind.”
“I was worried about you not showing up,” she admitted.
“And miss that incredible smile? I don’t think so!” She smiled at that, which simply reinforced his belief that she was gorgeous. “Yes, that smile.” That earned him a blush.
He led her to a pickup truck with Caparelli Construction on the side. She eyed him curiously but noticed the truck looked immaculate. Tommy blushed and said, “Mom’s got a car, but only Mom is allowed to drive it. Dad and I make do with pickups for work and whatever. I made sure to clean it earlier.” He opened the door and held her hand while she climbed in.
Mary said, “That’s fine. Dad drives a pickup, too. Mom and I use her car.”
They made small talk as they drove into town. The grocery store was just a few blocks from Route 9, called Broadway in Saratoga Springs. Broadway was the main drag in town and was where most of the restaurants and hotels were. The rain was keeping traffic down and they found a parking spot near a group of restaurants and bars. Tommy said, “I made a reservation here, but if you don’t like it, we can go elsewhere.” They were parked in front of a place called The Golden Pony.
“I’ve never been here, but I’m willing to give it a go,” said Mary. She smiled at him and his heart began racing again. He led her inside.
The hostess pointed them towards the coat room, where they took off their coats. She grinned at Tommy and said, “You clean up nice.”
Tommy laughed. “You mean something other than work jeans and shirts with my name on them? Thanks. You look fantastic!” Mary was wearing a fitted short sleeved white blouse, a slim knee-length skirt, and pumps with a two-inch heel. Her work clothes, shapeless blue trousers, and a blue and gray striped loose-fitting shirt, completely hid a gorgeous hourglass figure.
“Thank you. This is very nice,” she said, looking around the room. It was very upscale, with lots of race and horse related decor, and had both tables and booths. They were seated at a table near the bar.
Tommy grinned. “Yes, it is. Be glad it’s not the season. They have separate menus for then, with all the prices doubled.”
Mary’s breath caught when he said that. She quietly said, “I know.”
Saratoga Springs summer events revolved around the horse racing season. Saratoga was one of the oldest racetracks in America and the race season ran from the end of July to the beginning of September. Saratoga was old money, and that money flowed during the racing season. The wealthy would fly in from around the world, to see and be seen, and the sums involved could be staggering. Some residents reportedly rented out their homes for the season and moved elsewhere; the rental supposedly paid for the residents’ vacation elsewhere as well as the home’s mortgage for the year.
Tommy missed the haunted look on Mary’s face. “I told Joey I was going to see you tonight and he thought the idea was great. He grinned and babbled and waved his arms all around.”
She smiled. “He does that a lot. You could have told him you were taking the Hunchback of Notre Dame to dinner, and he’d have done the same.”
“Probably,” he agreed, with a smile.
“How old is Joey?”
“He’s almost a year old. He was born last June, so it’s just over eleven months. Karen died in August.”
“What happened?”
“She died in a car crash. She was hit by a drunk driver.” Tommy paused in remembrance. “We were visiting my parents and Karen had to go out and buy some formula. She never came back, and I ended up calling the police. That’s when we found out.”
“Wow.” What a godawful way to find out, she thought. “How old are you?” she asked. Thomas Caparelli didn’t seem old enough to have married, have a child, and lose his wife.
“Twenty-four.” He saw her trying to work out the details and explained, “I met Karen our senior year in high school, and we fell in love. We stayed together after graduation, which a lot of high schoolers don’t manage. I went to work full time for my father, and she went to work as a waitress in town. She wanted to save some money to go to college.” He shrugged and smiled. “That didn’t work out so well. We got married a year later and moved into an apartment. A year later she... we ... got pregnant. You know the rest.”
“Oh.”
“So, tell me about you. What are your deepest and darkest secrets?” Tommy was laughing as he asked. What he wasn’t expecting was for Mary’s face to turn ashen as she stared back at him. “Mary?”
“I shouldn’t be here,” she whispered.
“Mary?”
“This was a mistake. I shouldn’t be here.” She moved to stand up.
Tommy reached out and took her hand. “What is going on, Mary? What have I done?”
She tried to pull away and said, “It’s not you. It’s me.”
“Sit down and tell me. I won’t bite.” Mary was crying but she sat down. A waitress noticed and came over, but Tommy waved her away. It took her a couple of minutes to calm down. “Now, what is the problem? I must have done something.”
Mary shook her head. “It’s not you, Tommy. It’s me. I was listening to you talking about your son and your wife and it hit me. It really hit me.”
“What?” he asked.
“You’re a good person, Tommy. You’re just a good person.”
“So?”
Mary sniffled and began crying again. “I’m not a good person. I shouldn’t be with you.”
“Mary, what in the world are you talking about?”
“I have a son, too. He’s seven months old.”
Tommy nodded. “Okay. So, what’s the problem? I am guessing your husband didn’t die since you would have mentioned that. Divorce?” That was unusual but not illegal.
Mary cried and shook her head. “We weren’t married,” she whispered.
Tommy’s eyes opened somewhat, but it wasn’t as if he hadn’t heard of that happening. Usually, the child was given up for adoption, but some women got abortions. They were illegal, but you heard about such things. “Talk to me.”
1962
Mary Tomasino looked around the restaurant and wondered what being a waitress involved. It didn’t sound all that difficult, but she was smart enough to know that there was more to it than she imagined. She had just graduated from Saratoga Springs High School and needed a job. Her parents weren’t all that rich, so she would need to earn some money to go to college. At least her older brothers would get some help from Uncle Sam. Jake was four years older and was in Germany with the Army, and Billy was two years older and in the Coast Guard. Both would qualify under the GI Bill when they finished serving.
She had dressed nicely for the job interview and sat nervously when the manager looked over the job application. He looked up at her from time to time, but then just looked back at the application. After a bit he put the application down and looked at her again. He nodded. “Have you ever done anything like this before?”
“No sir. I mean, I’ve helped out at St. Elizabeth’s during church dinners and that sort of thing.”
The manager smiled. “This is a little different.” With that he explained the hours and the pay. There was a flat amount paid for the night, but the real money was in the tips, from which a cut was given to the busboys and dishwashers. The dress code was a nice white blouse and a black knee-length skirt, and dark shoes with low heels. Mary accepted and was turned over to an older woman. At least she seemed a lot older to Mary. In reality, she was in her late twenties. Her first shift would start the next night.
With that, Mary Tomasino entered the world of restaurant service. Mary had led a very sheltered life, with her father and older brothers watching over her like a hawk. A fancy restaurant like The Aspen Grove was very different from the parish hall at St. Elizabeth’s. Mary had a sunny disposition and meshed well with the other waitresses. They had a tiny bathroom-slash-changing room in the back. The older girls passed along the secrets of waitressing.
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