Benjamin, more or less fondly, looked through the candlelight at Harriet, his part-time lover for the past couple of decades. Both had decided this would be their last dinner together, though neither had shared this tidbit with the other yet.
Harriet, at 59, was still beautiful. Benjamin was biased because older blondes had always turned him on, but Harriet was still trim, firm, tanned and gorgeous, and, importantly, still liked the young cock. Fortunately for her, and for Benjamin from time to time, she had the money to indulge this desire. They were not married. Well, Harriet was, but not to Benjamin. They had met years ago when Benjamin was 21 and Harriet 39, when Benjamin was dating Harriet’s daughter Brenda, whom he had met at college. The fact he was dating Harriet’s daughter didn’t really bother either of them.
At the time, Benjamin presumed he had too much good sense to fuck his girlfriend’s mother.
He presumed wrong.
———
Two decades earlier Benjamin had been standing in the large, lush garden of Brenda’s family’s estate, his role as Brenda’s current flame required his attendance at a large gathering. Benjamin was taller than average, trim and blessed with good looks that included a shock of black hair that was somewhere between wavy and curly. He was somewhat quiet, especially around strangers, polite to a fault and had a dry sense of humor and was wrapping up an average middle-class upbringing. He was wearing khakis and a purple polo shirt and had been abandoned by Brenda, whom he went to college with and had been dating for a few months. Brenda’s abandonment had left Benjamin to feign interest in a conversation that interested him not at all between two people he didn’t know.
“Excuse me, sir?”
Benjamin looked behind him. A servant, a short, trim Filipino man of indeterminate age, was at his elbow.
“Yes?”
“Will you come with me, please?”
“Sure,” Benjamin said. “Any place in particular?”
“Yes, sir. If you will follow me, please,” the servant said.
They walked out of the garden, past the pool house and behind the main house of the estate. When they were out of view of the other guests the servant addressed Benjamin.
“Joan has requested an audience.”
Benjamin’s stomach froze. Brenda’s grandmother and Harriet’s mom, Joan was the matriarch of the family. Benjamin had been presented to her earlier in the day. Very wealthy, she maintained a fabulous form: firm, and trim, with frosted blonde hair in a bob that drove Benjamin wild. When Joan had warmly taken his hand, kissed his cheek and told him how very nice it was to meet him, Benjamin found himself sporting wood.
Benjamin followed the servant. He got the impression they were taking a back route to wherever they were going and soon enough they entered a back door, walked down a wood-paneled hallway and came to two large wooden doors. The servant opened them and they walked to another set of double wooden doors. The servant opened those, too, and they entered what was obviously a library. It, too, was wood-paneled, had a variety of comfortable chairs and a desk and had inlaid bookcases.
“Right in here, sir. Joan will be with you presently.”
Benjamin didn’t have to wait long. Within a minute another door opened and Joan entered the library.
“Hello, Benjamin.”
Benjamin now understood why they had taken a circuitous route to a far corner of the estate: Joan was wearing a white bikini, a sheer, purely for adornment cover and come-fuck-me heels.
Slowly and deliberately, Joan walked towards Benjamin and removed the sheer, purely for adornment cover. While not to the manor born, Benjamin did know which fork to use, however he was unclear exactly what etiquette dictated when being seduced by your girlfriend’s grandmother.
After meeting his eyes, Joan looked down.
“You’re hard again,” she said.
Instinctively, Benjamin looked down. When he looked up he gave Joan a shy smile.
“Again?”
“You were hard when we met, young man.” It was neither query nor indictment. Joan was merely stating the fact her granddaughter’s boyfriend had achieved sexual arousal upon meeting her. “That gives us something in common because you made me wet, young man. Very, very wet.”
Benjamin was speechless. He could smell Joan’s perfume.
“I was wondering if you wanted me as much as I wanted you,” Joan said. She paused and then nodded in the direction of Benjamin’s hard cock. “But I am not wondering that anymore.”
Benjamin smiled and shrugged. Joan was in command. When she wanted Benjamin to do something, like speak, she would direct it. For example, if Joan wanted Benjamin to undress, he would undress. If Joan was desirous of sucking Benjamin’s dick Benjamin would let her do that. If she wanted Benjamin to eat her out, Benjamin would do that, too.
Joan walked up to Benjamin and placed her arms around his neck and kissed him. It was a warm, tender kiss, as if they were in love. Then she pressed her body against his cock.
“My beautiful, beautiful boy,” she whispered. “There are some things I want to do to you. And then there are some things you are going to do to me.”
Joan kissed again, tenderly and with an open mouth, her granddaughter’s boyfriend
“First, I am going to suck that large, hard cock of yours.”
Joan’s tongue tickled one of Benjamin’s ears.
“Nobody in this family sucks dick like I do. Nobody. Not that child you’re seeing now,” Joan hissed dismissively “and certainly not her mother. Nobody.”
“Really?”
“Young man, when you marry this rich it ain’t for love. You’ve got to earn it. Head is a good way to do that.”
Benjamin smiled.
“Then you are going to eat me out. Then you are going to fuck me. Do you understand that?”
Benjamin nodded softly.
Joan took Benjamin’s hand and led him to a wall. She moved a framed picture of her, Harriet and Brenda and pushed a button.
The wall moved silently. It revealed a short hallway with soft lighting.
Joan took Benjamin’s hand and led him to the end of the hall, where she pushed another button.
Another door slid open, revealing a small bedroom. There was a king-sized bed, nightstands on each side and another door that led to a washroom.
“Make all the noise you want. The library is not only remote, it’s soundproofed. Trust me.”
Benjamin still maintained silence. He was going to fuck this beautiful older woman. There was nothing to say.
“Get naked, young man.”
Benjamin complied.
Joan took off her bikini. There were some signs of age. 59 is 59, after all, but the wrinkles were few and Joan didn’t look a whole lot older than her daughter, Harriet.
Both naked, she told Benjamin to get on the bed, preferably on his back. Benjamin complied and in short order, Joan joined Benjamin and began sucking Benjamin’s dick. Joan did this with enthusiasm. She enjoyed sucking dick, and she especially enjoyed sucking 21-year-old dick. Sadly, however, Joan had seen her opportunities to suck 21-year-old dick diminish over the years.
But not end entirely. Though the number of young men in their 20’s that were attracted to Joan had declined as she got older, Joan had a great deal of experience fucking younger men. It began when her beloved daughter Harriet was in high school and began throwing parties, which were attended by a variety of young, strapping boys. Most of these boys were not attracted to women her age, but some were, and it wasn’t particularly difficult to find which boys these were. They were the ones with tents in their swim trunks when Joan happened to run into them in the kitchen. They were ones who stared at her and tried to drum up lame conversation with her and who enjoyed it when a foxy older broad grabbed their cocks while they were alone in the kitchen, even though anyone, like Harriet – or their girlfriends – for instance, could walk in at any time. It took some planning so innocent, precious Harriet didn’t find out, but Joan got her share of young cock.
Nobody would know. The estate was large and the party was well on the other side and she wasn’t going to tell her guests she had just fucked her granddaughter’s boyfriend. Also, Benjamin could probably be trusted not to go around blabbing about what a great lay Joan was, either. As long as they weren’t gone too long and didn’t waltz back to the party holding hands it was likely no one would miss them. The library, and the servant, had been doing their duty for years.
Joan really did not want to stop sucking Benjamin’s dick. It was insanely hard and thick and long and young, but they didn’t have all day, and Joan desperately wanted the 21-year-old cock in her pussy.
So she rolled over and Benjamin was on top of her before Joan could order it. Her perfume was intoxicating. He kissed her and sucked on her tongue and worked his way down Joan’s neck and before he knew it he was working on Joan’s breasts. They were nice breasts, still firm, still more or less real. The surgery to keep them looking young had been as discreet as it had been expert.
Benjamin worked his way down Joan’s stomach and soon was eating 59-year-old pussy. He liked it, too. Benjamin tried to explain his older woman tendencies to a buddy once but he didn’t see it. Too bad for him, Benjamin thought, because nobody fucks like an older broad getting young cock. Nobody. And Joan’s pussy tasted just like her granddaughter Brenda’s pussy tasted.
Joan, though, had more patience than her granddaughter. Where Brenda got really worked up really quick, Joan was willing to let Benjamin do his work. It wasn’t expert work, by any means. Benjamin, after all, was a younger man and while in possession of the raw materials required for pleasing a hot older blond, his pussy eating technique, tragically, was more useful for eating corn on the cob. But Joan’s guiding hand provided expert instruction, however and in no time at all Joan had Benjamin eating her out so well she lost count of the number of times she had come.
Benjamin found he had zero moral issues with eating out his girlfriend’s grandmother. None at all. It was rather easy, actually. 38 years was a lot of age difference, but Joan wasn’t Benjamin’s first older blonde. Two, he and Brenda weren’t exactly Couple of the Year and Benjamin thought they probably would be broken up before the holidays.
Joan certainly didn’t care. Her life, while certainly luxurious and not too difficult, had not been particularly satisfying. Like most women, she liked the cock and her late husband had been a dutiful provider, but her husband had been her age.
On Joan’s orders, Benjamin stopped eating her pussy and started fucking her.
———-
Harriet: It’s A Family Affair, Part II
The Benjamin Chronicles