Lessons to Be Passed Along
Copyright© 2025 by rlfj
Chapter 2: Dating and Meeting
Romance Sex Story: Chapter 2: Dating and Meeting - 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
“So, how did the date go?” asked Angela Tomasino.
“Okay, I guess,” replied Mary.
“Did you have fun?”
“I guess so.”
“This is like pulling teeth! Was he nice? Was he polite? Where’d you go?” Angela asked a bunch of questions.
“Mom!” protested her daughter. “Yes, okay, he was very nice, and the restaurant was nice and all that.” Then she became quiet. “I told him about Herschel and, well, you know.”
“And what did he do? Did he leave you there at the table while waving a cross in your direction?”
“No! My God, of course not!”
Angela asked, “So, it didn’t bother him?”
“I guess not. He asked me out on a second date. I guess that’s good.”
Angela rolled her eyes. “Of course, it’s good. It’s better than not asking you out again. What did you say to him?”
Mary answered, “I said I would think about it, and he said he would call me.”
Her mother sighed. “Mary, you need to start dating again. If you don’t like this guy, fine, but you can’t stay in the house and hide the rest of your life.”
“I don’t know, Mom. I mean, I like him, but still ... he’s a really nice guy. He isn’t the type of guy who wants to date a girl like me.”
Angela was on the verge of answering when the phone rang. She went into the kitchen and pulled it off the wall. “Hello.”
It was a pleasant baritone. “Hello. Is Mary Tomasino available?”
“Can I say who’s calling?”
“This is Thomas Caparelli. Can I speak to her?”
“Of course. Let me get her.” Mary set the phone on the counter and went into the living room. “Okay, Juliet. Romeo is on the line.”
Mary got a sudden look of fear in her eyes. “What do I say?”
“Start with hello.” She took her daughter’s hand and pulled her upright. “Go!” She nudged her towards the kitchen and then sat down on the couch. She didn’t even fake any sense of privacy; she listened intently to Mary’s side of the conversation.
Half an hour later, Mary came back into the living room, smiling. “Well?” asked her mother.
“He asked me out again.”
“I thought as much. And?”
“He wanted to know what I wanted to do?”
Angela nodded. “Smart guy. Put it on you. What did you say?”
Mary shrugged. “I said I didn’t know. I’d have to think about it.”
“Lord, save me! Well, if nothing else, this gives you a chance to call him back.” She thought for a second. “Listen, you need to introduce him to Herschel.” Mary looked nervous and began to protest, but Angela overrode her. “No, I’m serious. You’ve met his son, and you’ve told him you have a son. He needs to meet Hersch. Face it, the two of you are a package deal. Buy one, get one free.”
“Mom! Well, maybe, but I don’t want him coming here to pick me up,” answered Mary.
“Why not?”
“Because when Tommy shows up Daddy’s going to give him the third degree! I won’t be the one scaring him off! It will be Daddy!”
Angela laughed. “You let me worry about your father. Maybe the weather will be nice this weekend. Go on a picnic. See how the boys get along.”
It was Mary’s turn to roll her eyes. “They’re not even a year old yet. What are they going to say?”
“Hey, I raised two boys before you came along, and Herschel is number three. They can be very different!”
“I’ll call him back.
“Tomorrow. Build up the anticipation.”
“Mom!”
If their first date was scary and tentative, their second was an unqualified success. Tommy quickly agreed to a picnic date with the boys, and they divvied up the tasks. Mary would prepare a picnic basket, and he would bring a cooler of Cokes. They would both drive, since they each had only one car seat, and that way they wouldn’t have to try moving them around. Tommy would bring some blankets to lay on the ground, and each would bring the appropriate food for their individual son. Herschel was still on formula, but Joey had graduated to Gerber gruel.
The picnic was at Saratoga Spa State Park, a large and sprawling complex a few minutes west of the racetrack. They met at one of the entrances and then Mary followed Tommy to a picnic area. When she parked next to his truck and got out, he smiled and gave her a hug, and then kissed her warmly. He had kissed her at the end of their first date, but this seemed much more tender and unforced, and she returned the kiss happily.
Then it was time to have a picnic. The weather was perfect for a lovely fall day. It was warm, dry, and sunny, but not too breezy. It was mid-September, but unless they stayed after dark, it wouldn’t cool off unreasonably.
They got the boys out of their car seats, which were nothing like what they would evolve into. They were nothing more than lightly padded metal frames that hung over the back of the car seat and kept a baby upright after you tucked him in with some blankets. Tommy had a stroller in the back of the truck and they put the boys in the stroller together, where they were pushed towards a grassy meadow with a scenic view. A blanket was laid out, the boys were deposited on the blanket, and then Tommy was sent back for everything else while Mary supervised a pair of pre-toddlers.
When he returned after the second trip, Tommy asked, “Whose idea was a picnic? Remind me!”
Mary just laughed. Then she whirled around. “Hold on, buster!” Joey at eleven months wasn’t quite walking, but he had mastered crawling, and he had taken off, moving at high speed into the far distance. She scooted after him and picked him up, depositing him back on the blanket. He laughed and flapped his arms and looked around for another horizon to conquer, which led his father to grab a few blankets and pile them up around the edge of the blanket.
“We are going to have to corral these two somehow,” he said.
“Maybe we can tie a rope around their ankles and tie them to a tree,” said Mary.
“You’re lucky. Herschel can’t move as fast.”
Mary smiled and shook her head. “He’s still working on rolling over.”
“Who did you name him after?”, asked Tommy. “Or is that indelicate?”
Mary shrugged. “I certainly wasn’t going to name him after his father.” She paused and said, “I picked my grandfathers’ middle names. I forget which was which, but one was Herschel and the other was Walker.”
“Herschel Walker Tomasino.” He smiled. “It’s a good name. Did he ever meet them?”
“No, they died when I was a baby. What about Joey? Where did that come from?”
“It’s my father’s middle name. Joseph George Caparelli. George was my mother’s father’s middle name.” He looked over at little Herschel. “Does he get outside much? Joey often plays outside when he’s with my mother,” said Tommy.
Mary nodded. “I live with my parents, and they have a big old farmhouse out west of Saratoga. This is pretty normal for him, but I don’t know how much longer. November is only a couple of months away, and it will be snowing at some point.” Tommy snorted out a laugh at that. Saratoga was in the middle of the Adirondacks, which meant it snowed six months of the year.
Mary sat next to Tommy at one end of the blanket, and they watched their sons. Herschel found it all quite fascinating and kept looking around and squirming to face different directions and trying to roll over. Joey was more animated and kept trying to crawl to freedom, though the blanket barrier at the edge of his domain tended to slow him down. After a bit, Mary opened the picnic basket. She had raided the family refrigerator and had packed some cold fried chicken, egg salad, and homemade dill pickles. Tommy stood and went back to his pickup truck, retrieving a cooler of sodas, along with a large baby bag.
He reached into the baby bag and pulled out a big Thermos, along with an empty baby bottle and a little jar of Gerber mashed peas. “I liked your idea of making some warm formula and putting it in a Thermos bottle.” He opened the Thermos and poured some into the baby bottle and then grabbed his son. It was lunch time. Mary did the same a few seconds later with Herschel. Then he fed some of the green pea gruel to Joey.
“That stuff looks awful!” Mary commented.
“It smells even worse,” Tommy replied. “Let’s just say that when it hits his diaper later today, you won’t be able to tell the difference.”
“Yuck!”
Tommy nodded.
Once the boys had been fed, burped, and cleaned up, they were put down on the blanket to get into trouble while their parents had their own lunch. Tommy was very appreciative of their picnic lunch. “This is pretty good! Your cooking?”
“Some. Mom did the chicken, but I did the egg salad and the pickles.”
“I didn’t know you could make pickles, I mean, at home.”
Mary nodded. “It’s pretty easy, but they need to be refrigerated. They can’t be put on a shelf in the pantry. It’s just cucumbers in a brine solution with some garlic and dill. We don’t can them at high temperature.”
“I follow you, I think. Tell your mother I like her chicken.”
Once they finished eating, Tommy lay back on the blanket and held a hand out to Mary. She curled up next to him, kissing him gently and resting against him. She began dozing in his arms and Tommy kissed her forehead and watched as the boys fell asleep at the other end of the blanket. After a few minutes, his eyes closed as well.
An hour later Mary stirred awake and that roused Tommy. The two infants were just starting to wake, and Mary knew that her son needed a diaper change. The parents went through the routine of changing the boys and feeding them some more formula before letting them loose again. As before, Joey tried to head for parts unknown and Herschel concentrated on rolling over and squirming around.
Late in the afternoon, Mary said, “This has been a lot of fun. Thank you.”
“No, thank you. It was your idea to take the boys to the park for a picnic. I wasn’t too sure how they would get along.”
Mary shrugged. “I don’t think either of them is quite up to mischief or mayhem yet.”
Tommy smiled. “Give them time. Once they’re both walking, Joey might be the ringleader, and Herschel might be the loyal minion!”
“Yikes!”
“So, does this count as a successful second date?” he asked.
Mary pushed him back on the blanket and put her head on his chest. “Very.”
Tommy thoroughly enjoyed the kiss she gave him.
“How did your picnic go?” asked Angela.
Mary blushed. “It was very nice.” Angela gave her a look indicating she wanted more information, and her daughter added, “He wants to keep seeing me.”
“And do you want to keep seeing him?”
Mary blushed again and nodded. “Uh huh.”
“Enough to incur the wrath of your father for taking the last jar of pickles?” Angela teased.
Mary laughed. “I’ll have to take my chances.”
“You are going to have to bring him over, you know. Your father is going to want to talk to him at some point.”
“Talk? Or torture and interrogate?”
It was Angela’s turn to blush. She shrugged and said, “That’s his job.”
Mary smiled. “Great. Listen, give me another week or two. I still don’t know what is going to happen, but I want to wait before I subject Tommy to Daddy.”
“Your father’s not that bad. He just worries about you.”
“Did he worry about Jake or Billy, too?”
“Maybe not.”
Mary nodded and smiled. “I’ll warn him. Well, eventually. Maybe after our next date. We’re going out to dinner Wednesday night.”
“Just let me know.”
The third date was relatively mild. It was basically dinner at a small family place off Broadway, so the rents and subsequent prices were much more reasonable. Mary enjoyed being with Tommy and told him that a ‘command performance’ was in his future. That got them both laughing, and he said he would put on his armor before arriving. They didn’t dawdle over coffee, though, since they both had to work the next day. Instead, they spent quite a bit of time hugging and kissing while standing between their cars. Mary was more than a little flustered when they broke apart.
Her father was in the living room when she came in. “How was your date?” he asked.
“It was very nice. We went to Angelo’s for dinner.”
“Honey, I think we need to talk.”
“No, we don’t,” said Angela, coming in from the kitchen.
“Angela...”
“Go to bed, Harry. Your daughter and I need to talk about sex.” Angela winked at her daughter.
“WHAT!” he protested.
“Go to bed, dear. It’s time for some girl talk.”
Mary giggled and kissed her father on the cheek, standing on her tiptoes to reach. “Bye, Daddy.”
Harry Tomasino harrumphed and headed up the stairs. The two women smiled at each other, and Angela pointed at the couch. They sat down.
“How’s Hersch?” asked Mary.
“He’s fine. I gave him a bottle of formula right after you left and another just before you came home. He’ll be out till morning,” said Angela. “So, how was the date. The truth, not what you said to your father.”
Mary smiled at that. “Actually, that was the truth. It was very nice. We went to Angelo’s and shared a pepperoni pizza and a couple of beers.”
“And?”
“And not much more. We kissed some in the parking lot and then split. He asked me out Friday night and...”, she paused at that.
“And?” repeated Angela.
“And I think Tommy wants to move things forward. He didn’t say anything, not specifically, but I got the idea that he wanted to move ahead.”
“You mean sex.”
Mary nodded. “I think so. I mean it wasn’t like he told me he was expecting it, but he wanted it. I think, anyway. Maybe I’m wrong.”
Her mother made a wry face. “No, you’re probably not wrong. Things move faster these days than when I was your age. You girls have more choices than I did when I was dating.”
“You mean, the pill.”
“I do. If you’re smart and responsible, a girl won’t get pregnant. That doesn’t mean you can’t still get a reputation, but that’s not really an issue anymore for you, is it?”
Mary gasped. “Mom!”
“Honey, I’m not trying to be mean or rude. It’s just that the damage has already been done, so to speak. I know you’re not the kind of girl who hops from bed to bed. It’s just that some girls will do that and get a reputation. Now, let me ask you a question,” Angela said.
Mary wasn’t smiling at the reminder of what had happened to her, but she said, “What?”
“If Tommy is expecting something more than just kissing in the parking lot, what are you thinking. Do you want more than that, too?”
Mary looked down but silently nodded. “Is that bad? When he puts his arms around me, it just drives me nuts! Am I wrong to feel like that?”
“No. It’s sort of the way biology works, I guess.” Then she smiled and said, “I still feel like that when your father puts his arms around me.”
“Daddy?”
Angela laughed. “What? You kids think you invented sex? Where do you think you and your brothers came from? Hah!”
“Oh my God!”
“Give me a break! Listen, when you go out on Friday, pack a little bag with a change of clothes, makeup, whatever. Something casual, so if anybody sees you the next morning, they won’t think you’ve been spending the night with a hunky guy. He is hunky, isn’t he?”
Mary smiled. “So hunky! He’s big and strong and muscular and so good looking! He looks like a cowboy in an ad for cigarettes, though without the cowboy hat. Or the cigarettes.”
“Well, if you don’t want him, maybe I’ll trade your father in.” Mary giggled at that, and Angela continued. “Seriously, if this is what you want, don’t play coy with him. Again, not to be rude, but it’s not like you have to protect your virginity. And don’t do it in the back seat of his car. You’re both grownups. Get a motel room and a real bed.”