Lessons to Be Passed Along
Copyright© 2025 by rlfj
Chapter 5: A New Generation
Romance Sex Story: Chapter 5: A New Generation - 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
1960s & 1970s
After the reception Tommy and Mary left the children with Tommy’s parents; the Tomasinos would rescue the Caparellis midway through the week. At the reception, Sarah practiced flirting with her new brothers-in-law, who responded in kind. Billy apologized but said, “Sorry, sweetheart, but my fiancée is on the other side of the room, and she wouldn’t be happy about that.”
“I’m available, though,” laughed Jake.
“Yeah, but you’re queer, so that’s no help to Sarah.”
Jake kept laughing. “No, I’m not, and if I could have brought Inge or Maria, they would have been happy to tell you!” He winked at Sarah and said, “Why tie myself down when there are so many German girls who know a good thing when they see it.” Both Sarah and Billy just laughed at him.
The honeymoon went as perfectly as Mary and Tommy could have asked for, in that they spent almost the entire time screwing their brains out. Even when they weren’t fucking, they were resting up from fucking. As Mary had teased Tommy, she hadn’t packed any bras or panties, just some skirts, blouses, and sundresses, all small and light. It didn’t take much more than a lewd wink to get him to help her get naked.
Tommy was ecstatic when he discovered what Mary had been hiding under her wedding dress. “Your mother bought that for you?” he gasped.
“Better than that! She bought one for herself! She said she was going to see if Daddy liked it.”
“Wow! When we get home, you’ll have to talk to her. I mean, your dad’s so much older than I am. What if he had a heart attack?”
Mary giggled and asked, “Do you think I should ask Mom to talk to your mom? Maybe she could buy them in a three-pack.”
“I don’t even want to think about that!” Tommy protested. Then Mary grabbed his cock, and he stopped thinking completely.
The craziest thing happened early in the honeymoon. It was mid-afternoon and they took a waterfront walk and went into town for lunch. That simply gave them what Mary called ‘fuel for sex’ and when they got back to their room, she pulled off her skirt and top and stripped Tommy down. A quick session of sixty-nine took the edge off before she had knelt on their bed and Tommy moved up behind her. He put his stiff cock into her doggy style, and Mary sighed happily. Tommy slowly pumped his cock into her as his hands roamed across her back and bottom.
Then his fingers moved down the crack of his wife’s ass and she moaned loudly. It was something he had done before and he had heard her moan appreciatively before, but this was the first doggy-style fuck they had enjoyed as man and wife. Chuckling to himself, he rubbed her asshole a second time and asked, “You like that, huh?”
Mary pushed back, burying his cock in her pussy. “Oh, God, don’t stop! Don’t stop!”
Tommy began hammering his cock into her from behind and brought his hands together, to separate her beautiful buttcheeks and tease her asshole with his thumbs. “Like that?”
“Oh God! Oh God! Fuck me! Fuck me!”
It was like music to Tommy, hearing his gorgeous wife demand he fuck her. Then he gently pushed a thumb tip into her asshole, and she went nuts. He’d never seen her so turned on before. She was moving like she was going to break his cock off, all the while demanding he fuck her. No man could hold out against that; thirty seconds later he was blasting a heavy load of cum into her spasming pussy.
Breathing hard, Tommy collapsed onto Mary’s back and then rolled off to the side. “Wow!”
Mary roused herself enough to roll against him and drape an arm and leg across her husband. “Oh, Tommy, that was wonderful!”
“Yeah, it was,” he agreed.
“What you were doing there, it was so ... so... erotic!” That was a word she had only learned recently, and it seemed appropriate.
“Erotic, huh. Happy to help.”
Mary looked at him nervously, and asked, “Can I ask you something?”
“After what we just did, you can ask me anything,” he laughed.
“I’m serious!”
“So am I!” Then he looked at her and saw a nervous expression. “What?”
“Tommy, that thing you did with your thumb, when you put it in my, well, you know,” she looked very embarrassed.
“Your bottom. Sorry about that. I won’t do it again.”
Mary looked at him and hugged him, but she said, “No, I mean...”
Tommy asked, “What?”
“It felt good. It didn’t hurt! I mean, I liked it. I know it’s dirty and wrong, but I liked it. I’m sorry if you think I’m a slut or a whore.”
“Mary, I have never thought that about you. What are you talking about?” Mary looked away but Tommy gently turned her head back to look at him. “Talk to me,” he said.
“It felt good. I enjoyed your thumb up my ass. It made me wonder, you know...”
“What?”
Mary answered, “What would your cock feel like there? I mean, I’ve heard girls say things about their boyfriends. I know that sort of thing happens. Women can suck cocks and fuck cocks and they can take them up the butt. Whenever you’ve touched my bottom, I’ve always loved it. I just feel so wrong about it.”
“Mary, you’re nuts. I don’t think you’re wrong or bad or whatever,” he said in exasperation.
“I promise, I’ll never talk about this again with you.”
“Mary, talk about what? Did you enjoy it or not? Did you want me to keep touching you there? What if I were to touch you there more? Would you like that?”
Mary didn’t answer but nodded, even as she cried. This was so embarrassing. It felt so good when he touched her there, but it was so wrong and dirty. Some of the girls she had talked to had said they would break up with a boyfriend or divorce a husband or something if he even thought about asking for butt sex.
Tommy didn’t know why this was so upsetting to his bride. He had told her that he was willing to do anything she wanted at least once. Playing with her butthole and maybe even fucking it ... well, he’d give it a try. Mary seemed to like it, so maybe he would too. “No big deal. Give me a chance to recuperate and we can give it a go.”
“You mean it?”
“Sure, why not? I’ll try anything once. We might want something to get things slippery back there.”
Before he could say anything more, Mary was draped over him, kissing him and telling him how much she loved him. That led to another round, followed by a nap. That evening, when they went out to dinner, they stopped by a drug store and bought a small bottle of Johnson’s baby oil and a tube of Vaseline. When they got back to the room, Mary insisted they both take a shower, since things might get messy. Afterwards, she turned down the sheets and got on the bed. Tommy lay down with her. They started out normally, kissing and licking and petting each other, a process that brought Mary to orgasm easily. Then she rolled face down and said, “Let’s try this, Tommy. I’ll understand if you don’t want to.”
“Will you stop worrying. Put a pillow underneath. Maybe that will lift you up some.”
Mary took one of the big pillows and pulled it under her pussy and then lay down with her butt lifted. Tommy knelt between her legs and slipped his cock inside her pussy. It felt like an iron bar, he was so turned on. Then, as he slowly pushed in and pulled out, he ran his thumbs down the crack of her ass and teased her anus. Mary groaned, “Oh my God! That feels so good!”
“Pass me the baby oil,” he asked.
Mary reached over to the nightstand and grabbed the bottle and passed it back. Next, she felt something oily trickling down the crack of her ass. Then it got wild. Tommy oiled up his fingers and began teasing her asshole. At first it was only around the edge, but then a thumb went in, and not just the tip. Tommy slipped it in up to the first joint, and then further, until it couldn’t go any further. “Are you okay?” he asked.
“Oh, God! More! More!” Mary was orgasming constantly by that point and her pussy was pulsing around her husband.
Tommy was enjoying himself thoroughly, so he brought his other hand down and slipped in his other thumb beside his first. That spread her wide, which was not something he had ever expected to witness, but it really made his wife crazy. She was humping up off the pillow, driving his cock into her. “Don’t stop! Don’t stop! Fuck me! Fuck me!”
Tommy moved his thumbs around, using them to tease and fuck her. He waited another minute, while she came loudly, and then pulled his cock from her pussy. Carefully lining it up with her bottom, he slid it in slowly, even as he withdrew his thumbs. The effect was electrifying. Mary begged him to fuck her even harder, and he couldn’t believe how hot and tight it felt. Tommy leaned down, laying over her back, and began pounding his cock into her. Mary moaned happily. It was more than she had ever expected. A few minutes later, as another orgasm swept through her, Tommy gave up the effort to hold back and exploded into her. It was the most amazing feeling.
They lay there like that for several minutes until Tommy’s limp cock slipped out of Mary. She giggled and said, “I really think we need to get up and take a shower.”
“Together?”
“Together.”
They climbed off the bed, noticing the pillowcase was stained. Well, what did you expect after what they just did? Tommy stripped off the pillowcase and tossed it aside and followed Mary into the bathroom. As they washed up, he put his arms around her and asked, “How are you feeling?”
“A little sore, but it’s a good sore. Are you okay? I mean, are you disgusted or angry with me?”
“Never,” he laughed. “Mary, I enjoyed it. I always enjoy putting my cock inside you, no matter how we do it. You are my hot and horny wife, and I love having sex with you. If you enjoyed it, then I enjoyed it. Is it something you would want to try again?”
She blushed but nodded and said, “Yes, but not for a few days.” Then she giggled and reached between them to grab his cock, now clean. “This guy is pretty big and I’m pretty small, but I love him so much.”
“That’s convenient, since he loves you, too.”
Mary giggled and kissed her husband. Then she grabbed the soap and began washing him again. It was still early, and she was sure that Tommy was good for another screw before they went to sleep.
Honeymoons were great! They needed to take a lot more!
Shortly after coming home, Tommy and Mary met with a family law lawyer in Schenectady that Father Frank found for them. He agreed that cross-adoption would be a good idea and relatively simple. He took down the critical information, made copies of all their birth certificates, and said he would get back to them in a few weeks. Three weeks later, he called and had them come in to sign some paperwork. Then they went home for another month, before being told to come to the Saratoga County Courthouse. They met with a smiling older judge who asked a few questions and made sure that they wanted to make the adoptions. After that, he signed a few papers and smiled again and congratulated them on officially being a family. That night Mary made sure to thank her husband repeatedly!
They kept living in their apartment for another couple of years, but when Tommy asked Mary if she was interested in growing their family further, she looked around. “Not here,” she said. “This place is too small as it is.”
“No, we’ll have to do something else,” Tommy agreed.
“Get a larger apartment?” she asked.
He shook his head. “And pay somebody else’s mortgage? I don’t think so. We need to pay our own mortgage.”
“Yeah. Buy or build?”
Tommy thought about that. Yes, his father owned a construction company but that was a big ask. “Let me think about it.”
“Okay. Now take your pants off. We need to practice knocking me up. I wouldn’t want to do it wrong,” Mary told him.
Tommy laughed and they got undressed. “Yeah, so far the results on both sides have been questionable at best!”
They ended up buying an old farmhouse in West Milton, just a few miles south of Rock City Falls. It was in the Ballston Spa school district, which is where all the Caparellis had gone to school. The farmhouse needed some work, but it was a lot cheaper to get Tommy’s father and brothers to come over and do repairs and remodeling, and what they couldn’t do, Tommy could. It seemed to take forever, but it looked great when they were finished.
By the time that happened, Tommy and Mary’s practice sessions had paid off. Four years after the wedding, she tossed her birth control pills in the trash and went to work on getting pregnant again. She took to the job with real fervor, often requiring multiple treatments that left Tommy gasping and complaining about heart attacks, but she was ultimately successful. By November of 1969, Mary was once again pregnant. If Tommy thought that he was going to get some rest from his wife’s excessive amorous inclinations, she quickly disabused him of the notion. If anything, pregnancy made her even hornier than she was normally, and that was already pretty horny.
Tommy did get some rest in May 1970 when Mary delivered twin boys, Samuel and Daniel. Mary was out of romantic action for eight weeks. By then Joey was in first grade and Herschel was in kindergarten. Janice and Angela came over and helped frequently. Both sets of grandparents were empty nesters by then, and two boys were never so doted over until then.
Vietnam screwed things up for everybody. Billy liked the Coast Guard and planned to make it a career; he and Teresa married in late 1966. As Vietnam heated up, he thought he had made a safe choice. Then, Squadron One was created and sent to Vietnam; Billy was assigned to a cutter and did two consecutive tours doing interdiction duty. Teresa was not amused and divorced him in 1968. It was worse for Jake. He had decided that Vietnam didn’t sound anywhere near as enjoyable as advertised and planned to get out when his hitch was up. Unfortunately, his unit was deployed to Da Nang in late 1966. He died in a VC attack eight months later. That almost killed his mother.
Caparelli Construction did well over the years. Tommy began running crews of carpenters and other trades as a foreman and manager. His two brothers stayed with the company, too, but it was obvious that Tommy was going to take over when their father retired. Andy became a master electrician and took over that side of the business. Jack, on the other hand, decided he didn’t like plumbing, so he got a degree in accounting and handled that part of the company as well as any contracts. Even Joey and Hersch got in on the action. Once they were old enough, even before they turned fourteen and got their working papers, they worked as gofers and trainees for their grandfather, father, and uncles.
Sarah, however, wanted nothing to do with construction. She was as smart as she was beautiful. She managed a full scholarship to Sarah Lawrence in Yonkers where she got a degree in English literature. She also earned an MRS degree, meeting a pre-med student at Fordham. They waited until he finished medical school before getting married, but unlike so many TV movies, he didn’t cheat on her after she put him through college. They were happily married and living on Long Island with their three children; he was a cardiologist, and she was a schoolteacher. She stayed in close touch with the family, and every year they traveled to Saratoga to visit family. She frequently compared notes with Mary about their husband’s bedroom abilities. She seemed quite content with Doctor Goldstein’s cardiac workouts.
Mary kept working part-time at Grand Union as a cashier. She also spent several hours each week working at St. Joe’s as a secretary, filling in when Mrs. Jenkins needed time off. Mary liked being a housewife for Tommy. She could see the boys off to school every morning and was usually home in time to greet them when they got home. Living outside of town kept them from getting in too much trouble, though they tried, but she had an eagle eye out for them, and didn’t mind chewing on them as needed.
It was a good life, but most importantly, it was a life that Mary had once despaired of ever having. Every night when they went to bed, she thanked Tommy for loving her and marrying her, and then usually proved it by slipping a hand inside his boxers. She made it her mission to make sure he went to sleep with a smile on his face, and she usually had a smile on hers, too. Their sons frequently told them they were embarrassed by the way they held hands in public, but Mary and Tommy just smiled and ignored them. Worse, they sometimes even kissed each other! It was so embarrassing!
1978
The school bus stopped at the corner and a girl got on. Both Joey and Hersch Caparelli smiled and nodded to each other. She was very pretty, slim but very curvy, with long dark brown hair and blue eyes. They smiled at her, and she smiled back, but then sat down on the seat behind the bus driver. She was new to Ballston Spa and to Ballston Spa High, and didn’t know if she should sit any closer to the two boys several seats back. It didn’t help when the larger of the two called out, “We don’t bite. Usually. I mean, we’re actually quite harmless, well, Hersch is anyway. If you like bad boys, you should sit near me instead.”
That worried the girl, but the bus driver laughed. “Don’t mind him,” he said quietly. “He’s all talk.”
She looked back over her shoulder and smiled. It was a beautiful smile, and both boys smiled back. “Maybe some other time.” She turned back and heard the boy who had been talking say to the one called Hersch, ‘I’m in love! Oh my God! I’m in love!’ She smiled to herself, especially after the one called Hersch said, ‘You have zero chance. She is way out of your league!’ She wondered what kind of name Hersch was.
After that the bus began making more frequent stops, and a bunch more kids climbed on, and she stopped thinking about the two boys behind her. Bus 51’s route started out in the boonies and then worked its way into Ballston Spa. Judy Roswell’s parents had bought a rancher just outside of town, and after picking up the Caparelli boys it stopped at her house before going into a trailer park and then picking up a few more students in a suburban area. When the bus got to the high school, she was one of the first off, but she looked around in confusion. She had been with her mother when she registered her daughter at school, but with everybody around, she was simply lost. She moved towards the front door, where a woman looked at a list in her hand and then pointed the girl inside and gave her a room number to look for. She also had a list of locker numbers and said it was right outside her home room. Judy Roswell was a sophomore.
She got to the room and found her locker, and after putting her jacket in it, she locked it with the combination lock her mother had bought for her. Then she went into the class, where Mrs. Hadley checked her name off a list and pointed her to a seat two rows back and one row away from the window. She sat down and was surprised to be seated next to one of the boys who had greeted her on the bus. “Hi,” he said.
“Hi. You were on the bus.”
He smiled. “Yeah. I’m Hersch Caparelli. The mouthy guy is my older brother, Joey - he’s a junior - but don’t worry, he’s harmless. Just tell him you’re my girlfriend and he’ll leave you alone.”
Judy laughed at that. “Thanks, but no thanks.”
“Well, at least think about it. What’s your name?”
“Judy. Judy Roswell.”
“Hi, Judy. Tell me all about yourself. By the way, do tell Joey you’re my girlfriend, even if you’re not. It will drive him crazy!”
Judy laughed again but that was the end of the conversation as the classroom filled and home room started. After calling the class to order and saying the Pledge of Allegiance, there was a welcome message over the intercom, and then Mrs. Hadley explained the school and class system to any new students. She handed out school maps to those who were new, answered some routine questions, and when the bell rang, she sent them off to their destinies.
Hersch followed Judy down the hall to Room 216 and followed her inside. She looked at him curiously. “English 10, right?” he asked.
“English 10,” she agreed. They compared schedules and found they had four classes together, English 10, Science 10, World History, and Algebra 1. They had different language options; Judy had Spanish 2 and Hersch had French 1. The other difference was that Judy was taking Junior Band with a clarinet and Hersch took Chorus. Then they took seats near each other and class started.
So it went the rest of the day. At the end of the day, when they boarded the bus to go home and Joey got on the bus, he found his regular seat next to his brother taken by the beautiful girl he had teased that morning. Laughing, he sat a few seats back with some of the older kids he was in class with.
“That’s Joey?” asked Judy.
Hersch smiled. “That’s my brother Joey. He’s actually only about six months older than me, but that actually puts him in the tenth grade. He’s harmless.”
Judy was about to say something, but then her face screwed up. Hersch knew exactly what she was thinking, and she proved it when she asked, “How are you only six months younger than him. Last I heard, babies take nine months.”
Hersch grinned. “Yeah, I heard that, too. His birth mom died when I was a baby, and Dad met Mom, and here I am.”
“Oh.”
Hersch just laughed. He wondered why he had explained it to Judy. Most of the time he just said he was younger than Joey and left it at that. There was just something about her that made him want to keep talking.
After Judy got off the bus, Joey moved up to sit next to his brother. “So, what’s with the hot chick?”
“She’s Judy Roswell. She and her family just moved here.”
“From where?”
Hersch shrugged. “I haven’t found out yet.”
Joey grinned. “You planning to share your toys?”
“You planning to eat soup for a month?” A buddy of theirs got into a beef the previous year and got his jaw busted. Eating soup for a month was a reference to what Ray Buxley had to go through while his jaw was wired together.
Joey simply laughed.
The next morning Joey moved as soon as Judy got on the bus. She smiled and sat next to Hersch. The weather was a bit warmer, and she had skipped out on the jacket, and was now wearing tight blue jeans and a white blouse. If anything, she looked even better than the first day, because she had worn a sweater then, Now Hersch could see that Judy had what looked like really nice tits! Really nice! He couldn’t say that of course, and if his brother said anything to him, he’d have to say something about eating soup, but Judy Roswell was very hot! He was fifteen and Herschel Caparelli was very interested in girls, and Judy was a prime catch. He knew Joey was already seeing a girl in the eleventh grade, though he didn’t think he had gotten anywhere with her yet.
That afternoon, after school, Judy sat next to Hersch on the bus again. He was struck by just how beautiful she was, and he could feel he was getting a hardon. He knew she’d be disgusted by it and put his books in his lap. Once he got home, he headed out to the barn and jerked off while thinking about her. He wasn’t sure if that would actually help, though. By the time he got back to the house he had another hardon. Jerking off felt great, but it seemed as if it was going to be a permanent problem with Judy around.
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