Henry and Eleanor - Cover

Henry and Eleanor

by Rod O'Steele

Copyright© 2008 by Rod O'Steele

Romantic Sex Story: A modern story, strange but eventually worth it.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/ft   Consensual   First   Anal Sex   .

Part I

Henry couldn't help the way that he was raised. The fourth of four boys, Henry was destined to be shaped by that accident of nature. While some youngest boys in a family are the pampered baby, that wasn't in the cards for Henry. His parents didn't have the time, desire, or the attention to pamper Henry.

Some boys, in that situation adapt. Constant bullying by three older brothers toughens some boys. The constant competition with older brothers forces them to compete and compete with all of their strength. These boys often grow up to be athletes, the kind that coaches love to have on their teams, the kind that get by not on their innate skills, but by sheer determination.

That wasn't to be the way for Henry either. Henry withdrew from the hazing of his older brothers. The three of them didn't understand it. What was wrong with their youngest sibling that he didn't play as they did?

It wasn't any of his brothers that started it. It was the vicious boy down the street, Charlie. He was the first to call Henry a fag. In the way that kids can be extremely cruel, the name stuck. Even his brothers started referring to him as a fag. There were young enough that it didn't carry a specific sexual meaning, just that he was a boy that didn't fit in, meant in a bad way. It didn't bother Henry, since he could hide behind the name. If he was a fag, he didn't have to play kick the can where even the girls could outrun him back to the can. Being a fag saved him untold embarrassment.

It wasn't until the winds of puberty began blowing through his body that things changed. He loved Anne. Her body had recently burst out from childhood to young womanhood. Henry tried to express his love for her one afternoon. He brought her flowers he had gathered. When he gave them to her, she laughed and cried out, "Look, Henry the fag likes flowers." All the rest of the neighborhood children laughed and Henry, retiring shy Henry, knew no way to set it right.

He would never again chance such disappointment with a girl. As he grew, his sexuality demanded an outlet. But he had none. The boys and girls his age scared Henry. Finally, he found it. His school required all students to work on a community project. Henry, because he didn't volunteer, wound up being assigned to help at the local boys home, orphanage to you and me. There, finally, Henry found someone who did look up to him, appreciated him, and most important, liked him. The boys in the home gave him their appreciation and in some cases even adoration and Henry opened his heart to those boys. During his tortured years of puberty, the path to his sexuality was opened to those young boys.


This presented Henry with a problem. The boys he was attracted to weren't attracted to him sexually. They were just too young to yet be interested. On the other hand, there were many men who were attracted to boys like Henry. While Henry was willing to try these experiences, and frankly he did receive pleasure from a man fellating him, it didn't fill the emotional need he had for boys.

Henry had a few boy friends, boys old enough to be sexually interested but physically undeveloped enough to still be hairless and smooth. Henry did have several affairs of the heart. He loved these still almost boys. Especially, he loved their boyish asses and watching his shaft disappear between the soft globes of their boy ass and into their tight little boy bottom until he came. Always, too soon though, they would continue developing and hair would grow, their shoulders would widen and their butts would tighten and the hair would sprout like weeds all over their body.

One boy, his favorite boy, shaved for several years, until his mother found out he was shaving his pubic hair and the hair under his arms. The boy confessed and it was only the shame of it that prevented the mother from calling in the police. Now, Henry was older and it was harder to find boys. Henry no longer looked like a boy himself. A profound sadness had descended over Henry as he began to realize his life would always be one of unfulfilled longing for love.


Eleanor was fourteen when her family moved in next door to Henry's bungalow. With her natural curiosity, she tried to figure out this man next door who seemed to carry sadness around his neck like a yoke. To the young girl, it made him seem a man from the stories she liked to read, the romantic hero never finding love until the beautiful princess comes along to free him from his loveless life. It really was all so obvious to Eleanor she couldn't understand her mother's admonishment to avoid Henry.

Eleanor was certain that what her mother didn't know would never hurt her. So Eleanor began her campaign to master Henry, he of the romantic destiny. Poor Henry had no idea he had become a prize to be won or he would have further retreated. The campaign began surreptitiously. Eleanor was lying in wait outside Henry's house after school, as he arrived home much earlier than her mother and father did. That left her several hours after school to pursue her designs on Henry.

"Hello," she said, quite convincingly surprised to suddenly see him there by the gate of his own house.

"Hello," he answered. He went to get past but Eleanor was blocking most of the gate. Henry pulled back in frustration not wanting to touch the girl.

"My name is Eleanor. What's yours?" she asked.

Ignoring her question Henry told her in his most authoritative voice, "You are blocking..."

She interrupted, "I live right next door. How long have you lived here? We just moved in."

Flustered, Henry answered, "Well, I don't know. I've been here many years. Now, if you don't mind."

"I don't mind at all how long you've lived here. In fact, I'm glad you live here as I don't have any one else to talk to. I suspect we are going to become very good friends," she said.

Henry was quite taken aback. He hadn't had anyone talk to him in such a fashion for as long as he could remember. Poor Henry lacked social skills from his reticent youth, and had never cared to add to them, these unneeded social graces, as he aged. It did leave him in a poor position when caught like this. He felt he couldn't just barge past the girl. And it was apparent she wasn't taking his hints to move. Worst, she had the temerity to suggest they would be friends. He didn't want any friends, especially girls.

"I'm not sure about that," Henry answered hoping she'd take the cue and leave.

His hopes were quickly dashed. "Oh, I am sure. Yes, we will be very good friends." She smiled up at him still blocking his entrance. "What's your name?" she asked, as if she hadn't noticed her last attempt went nowhere.

Henry was nearly shaking at the injustice of her intrusion into his life. Indignant, he answered, "My name is Henry Smith, for whatever you need it."

"Henry! Oh, how lovely, Henry," she said clasping her hands.

Henry's eyes widened now. What was wrong with this girl?

"That is perfect since my name is Eleanor. You know, like Queen Eleanor of Aquitaine. She married Henry the Second, King of England, France and Ireland," she said.

Henry said, "I'm not sure that is historically accurate..."

Eleanor interrupted him, "Of course it is. Eleanor married Henry the Second."

"Yes, yes," Henry agreed. "That part is true."

"So, there it is," Eleanor said soothingly. "a wonderful royal wedding."

Throwing up his hands, Henry tried a flanking movement hoping to slide round the girl and into his gate. In a burst, he was past the girl and heading up his walk.

"Bye, Henry," she shouted.

Truly afraid to look back that the girl might be following, Henry quickly opened his door and rushed inside.


The dread started for Henry as he walked the two blocks from his bus stop to his house. Before he rounded the corner, he leaned out and looked ahead. No girl outside his gate. He quickened his pace while continuing to look around. As he reached his gate he breathed a sigh of relief. Henry quickly paced up his walk. As his hand was fumbling for his keys he heard her voice. "Hello, Henry Smith."

He spun around to see her bouncing up his walk. The sight caused him to drop his keys. Eleanor quickly bounced up to him, bent over, and grabbed his keys. "Which is it?"

Recovering a bit, Henry asked, "What?"

"Which is it? Which key opens the door?" Eleanor asked.

Just as had happened the previous day, her manner threw poor Henry completely off stride. He had no idea how to cope with a girl like this. He stayed away from girls. Eleanor was thumbing his keys. "This one?" she asked holding up his door key.

"Yes," he said. Had he known what was about to happen he would have said no. But it was beyond Henry's comprehension that Eleanor would do what she was about to do.

She put the key in the lock and pushed open the door ... his door ... his protection ... his sanctuary. His mouth dropped open.

Eleanor bounced into his house, "Come on, then."

This was intolerable. Henry felt the rage building inside. He huffed and followed the girl only to find her still for once, staring at his bookshelf. Like many of the disaffected, Henry had retreated into books, for the fantasy of books was better than the reality of his life. To see the girl staring in wonderment at his bookshelves, and he had many, stopped Henry. It was so unexpected.

"I love books," Eleanor said. Henry could feel the sincerity of her words. For the first time, he felt some affinity for the girl, someone else who loved books. The girl went over and touched several of them like they were precious relics. Henry was amazed, for he often felt exactly like the girl was behaving. For the first time since Anne, he felt close to a girl, though not as a girl, but as a fellow traveler in fiction.

She turned back to Henry, "May I?" her face full of light. He nodded. She slid one book from the shelf. "Orlando, I've wanted to read this but mum said I was too young, too young to read a book."

"Rubbish," Henry said, uttering his first real communication to the girl. "There's nothing pornographic in that book. It's almost Victorian as a matter of fact. But it is a fascinating little read."

Eleanor clutched it against her chest. "May I ... read it?"

Eleanor didn't notice but Henry smiled. "Certainly. Just don't spill on it."

"Oh, I shan't," she said. She fell into one of his chairs and was instantly engulfed by the words.

Henry shook his head and went off about his business. He looked in an hour later to see Eleanor still engrossed. He took up his latest read, and joined her sitting across the room and soon he too was lost ... but not completely. He realized that it was a companionable silence, knowing he was sharing this wonderful moment with the girl. It had been so long since he had felt such a feeling.

Some time later, Eleanor looked up. "Oh, mum will be home soon. I've got to go. Henry, can I leave the book here?"

He looked up from his book. "What? Oh, of course. There are bookmarks there," he said pointing.

Eleanor rushed over and grabbed one, put it in the book and closed it, leaving it on the top of the bookcase. "Thank you. I've got to rush," and she was out the door.

Henry looked at the book sitting there, out of place. He wasn't used to having things out of place. Yet, he didn't feel like he wanted to move it. It felt right to have it there. Ah well, he'd finish this chapter and go fix some dinner.


Eleanor was waiting for Henry, sitting on his front step when he arrived home. She jumped up, "Hello, Henry."

Henry smiled, this time at himself. He had tried to not admit it but he had wondered all day if she would be there when he got home. He found he was glad. Silly him, he thought, to be glad that a girl was sitting on his front step. "Hello, Eleanor." He tossed her the keys. She looked surprised. "Well, you seem better at finding the right key than I," he said to her surprised face.

She pouted, "You're making fun of me." Then a radiant smile burst through the pout. "But it's all right. I can open a door." She opened the door and ran into his place, grabbed the book from the shelf, and flopped down into 'her' chair. "Thank you, Henry. I really love this book."

Henry went off to change out of his suit. She was again entranced when he returned. He smiled and sat down with his book.

Some time later, Henry stretched and looked at the clock. "Eleanor, the time."

She glanced up. "Oh pooh." She carefully closed the book and took it back to the shelf. "I've got to go. Tomorrow?" she asked.

"I'm sure I'll be too busy," Henry said. "Probably the president will be calling me in to consult."

Eleanor stuck out her tongue at him, turned, and sped out the door.

Henry chuckled. He sat back in his chair and stared off into the distance, seeing nothing. Just what was happening? Should he stop it before ... before what? What could possibly happen between him and a girl? The obvious answer was nothing. He set down his book and went off to prepare dinner.


So began a strange friendship.

Henry was an intelligent man with a curious intellect. He read voraciously. He was also socially inept. He had a whole world locked inside and had never had the opportunity to let it out for others to share.

Eleanor was an intelligent young woman with a romantic streak and a curious intellect. She wanted to see the whole new world that was opening up to her at this time in her life. It truly was a match made in Heaven.

It worked for Henry because she was a girl. Had she been a boy, then lust would have interfered. Had she been a woman, fear would have interfered. But since she was neither, she was deemed harmless, though Henry was wrong there. This allowed him to open up to Eleanor. He quickly saw how much she could learn from him and he blossomed, feeling of worth for the first time since he had been adored by the boys at the home.

What started as simply shared reading, grew into long discussions. Each discussion of some book would inevitably bring discussions of others. Eleanor's reading list grew apace, not that she minded.

Each new book meant more time spent with Henry. She never forgot her mission, to save the sad Henry in some romantic act of courage.


"Henry, I have been wondering. How come you don't like me?"

"Don't be silly, Eleanor. I do like you," he said.

"No, you don't."

"Yes, I do," he said.

"I don't ever see you looking at me like a girl, you know," she said. "You think I'm too young to appreciate, don't you?" she accused him.

"Appreciate?" Henry asked with a smile.

Eleanor pouted. "All right, I'll be blunt. You think I'm too young to be appreciated as a woman."

Henry smiled, "Believe me, dear Eleanor, I don't think you are too young," he said. He wasn't about to say it but he loved looking at her cute young butt, so much like a boy's. If she just wasn't a girl. She was still shaped like a boy. He would love to ... well, if she were just a boy.

"Well, then, I'm not too young. I think I'm okay looking," she said. "I mean, I know I'm no model and my breasts aren't very big, but..."

Henry flopped down on a chair. He had agonized, fearing this moment would come, hoping it never would. He knew what he had to say. He didn't want to say this but he knew no other way, "Eleanor, it's that I don't like girls."

"Women?" she asked.

He shook his head.

"Men?" she asked.

He shook his head again.

Frustrated, Eleanor said, "Well who do you, well, you know, do it with?"

"Eleanor, what would you mother say with you asking such questions?"

"She'd be as confused as I am, that's what," she said.

Henry took a deep breath, "Oh my. I expect I am about to lose a friend, but you asked. Remember, you asked. I like boys." Henry waited for the explosion, but none came.

"Boys? But that's illegal," she said.

"Yes, and that's why you don't see me with anyone," Henry said.

In a flash it all came clear to Eleanor. No wonder Henry was so sad and lonely. "But you like me."

"Yes, I do like you. But I like your mind first of all," he said.

"That's all right. I like yours too. But don't you ever notice my body?" she asked.

Henry looked down. "Well, dear. Sometimes, when you are turned away and I can't see your long hair, and you are wearing jeans, you look like a boy."

Instead of being repulsed, Eleanor was fascinated. "Really? If I was a boy would you..."

Henry looked up surprised with the question. "Eleanor."

"Oh, don't Eleanor me. You're the one said you like boys and you've already admitted I'm not too young. So, if I were a boy, would you?" she asked.

Poor Henry blushed wildly for he had that thought many times, if Eleanor were just a boy. He had sometimes fantasized that he would bring her into his confidence. She could seduce some boy her own age and bring him round so that Henry could have a go at him. He was sure there were boys who would gladly spread their ass cheeks for him if they thought it would give them a chance at a girl like Eleanor. They could both be happy, sharing some cute boy.

She saw the blush although she misread why, "Henry! You would."

"Now Eleanor. Do you know how men do it?" he asked. "It's not the same at all."

"You mean in the butt?" she asked. "Yes, I know that. If my hair was short and I dressed like a boy, would you?"

Henry didn't have to answer, for the truth of it was writ large on his face. Eleanor finally had her answer about Henry. Now the question was, what to do about it, her romantic act of courage.


That night, Henry lay awake and worried. Now that his secret was out in the open, would Eleanor decide he was a silly old fag and never come back? The thought of that was painful. He fully realized how much he had come to like having Eleanor around. He was shut of loneliness for the first time in decades and the thought of going back ... He couldn't do that.

That settled, his thoughts turned to setting it right with Eleanor. Somehow, he had to get her to forget today. He'd give up his fantasies of her bringing round boys for him. That would never happen. He had to convince her that they should continue as it had been, reading and talking in the afternoons.

With a plan how things could be put right, Henry was finally able to get to sleep. Ah, how easily our plans are derailed.


Eleanor arrived early. She was waiting for Henry on his doorstep. He turned in the gate and stopped. He could have sworn it was a boy, for Eleanor had cut her beautiful long hair and she was wearing a boy's hat. "I'm Robert," she said. "Can we go in?"

Henry nodded. He opened the door and led him/her inside. Inside, Henry saw how much she looked like a young boy, thin and small as she was. She could be a boy. "Eleanor, what is this all about?"

"Please, call me Robert. My name is Robert," she said. Henry nodded, still perplexed. Robert continued, "I want you to take me to bed. I want you to do me like a boy does to another boy."

Henry was shaking his head.

Robert turned round and showed Henry his cute butt. Turned away as she was, Eleanor looked just like a boy. Then Eleanor took a chance but she thought it would work. She pulled down her pants to expose her cute ass. Henry almost couldn't breathe. Her thin little butt looked just like a boys, two soft globes all creamy white. "Robert," he said quietly.

Eleanor smiled. It had worked. Once again, in a deeper voice, but still boyish, she said "Please Henry. Show me."

The years of denial burst out and Henry lost himself in this cute little boy butt. He paced across the room, bent down, and kissed those lovely cheeks. "Follow me," he said.

Robert pulled up his pants and followed Henry down his hall and into his bedroom. For Henry everything in the world had stopped except his desire to fuck this boy. "Get on the bed, face down and pull down your pants."

Eleanor had second thoughts. What exactly was she doing? But she knew this was the sacrifice she needed to make to save Henry. She crawled up onto his bed, pulled her pants down to her knees, and pushed her butt up in the air.

Henry had gone into his bath and gotten the lubricant he always kept. He dropped his pants on the floor and came over to the bed. Robert reached back and pulled open his cheeks, displaying his rosebud for Henry. Henry ran his hands over the boy's soft white butt. It had been so long ... His cock was throbbing in longing. He squeezed the lube along his cock sliding his hand up and down until it was covered. Then, he squeezed a glob onto Robert's ass.

Eleanor felt the cold lube and almost giggled. Henry began rubbing it around her hole, then his finger pushed inside her, spreading the lube inside her. It felt strange but it wasn't especially painful and Eleanor started to relax.

 
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