It had gotten easier after that first time when she felt that his cock was going to rip open her poor butt. One day every week, she’d wear the hat and Henry knew. She would be Robert on those days. It was always Eleanor who decided which days. Henry never asked her when she would become Robert. When she did come dressed as a boy, they’d go to his bedroom and Robert would flop down on his knees, take out Henry’s dick, and suck him till he was hard. Some days, Robert wouldn’t stop and Henry would empty himself into the boy’s mouth.
Some days, Robert would get him hard, then he would take off his pants and lay face down on the bed, his tight little butt there for Henry to admire. Eleanor never removed her shirt for the sight of her tits threw Henry off. She’d wear the hat and her shirt and she’d keep her legs together not to expose her pussy to him.
Henry was repulsed by her pussy. Once, when he was still a boy, he had heard older kids taking of sex, how the boy stuck his thing into the girl. When he asked, his brothers had told him that a girl’s pussy had teeth and if he put his dickie in it, the teeth would bite it off. That image had never left him, even though later he knew it was foolish. When he swore off girls it just seemed a confirmation of the earlier fears. Girls emasculated boys.
He was only interested in her boyish butt. Robert would pull her cheeks apart and Henry would glop the lube over his cock and spread it down between the boy’s cheeks. Eleanor had learned how to relax her tight muscles and it no longer felt like it was ripping her apart.
Once they were done, they would clean up and go out into the front room. Eleanor would put the hat aside and she was a girl again. They’d read or talk about the books. They never discussed what happened in the bedroom. It was as if there really were two different people, Robert there for sex and Eleanor there for friendship. This made it easy for Henry to keep the two separate. He didn’t want the two things getting all mixed up, friendship and sex.
For Eleanor, the feelings were bleeding over one to the other. She liked the sex even though she didn’t enjoy it. She liked knowing she was pleasuring Henry, that she was saving him with her romantic gesture. But she wished he could also please her. After a day when they had sex, Eleanor would go home, take a bath, and relieve the tension while in the bath. She did this so often she began to worry that she’d have a climax every time she went swimming.
They were talking about love in Nineteenth century English novels. Henry, always a bit of a skeptic, thought that Victorian love was overblown. Never having been in love himself, he couldn’t see how it could be so all encompassing. Henry was more apt to be in the Henry James camp that these things were caused by hidden emotions, or he would claim that when Dickens had Scrooge claim the ghosts were just bits of undigested beef, Dickens was speaking of all such nonsense. Twain, the great debunker, was his favorite author.
Eleanor knew love as all encompassing, for she was in love with Henry. Her tastes ran to Thackeray, Alger, and Surtees. Henry abhorred Surtees as an emblem of everything wrong with 19th century culture. They both adored the poetry of Poe, Tennyson and Scott, though Henry for the majesty of the poetry and Eleanor for its romantic doomed loves. Those were interesting conversations.
Since love is a recurring theme in literature, and love was foremost in the mind of one participant, it was a frequent topic in their conversations. Henry usually pooh-poohed whatever position Eleanor took. He was quick to attack romantic love in whatever form the author presented it. It was a constant consternation for Eleanor that she couldn’t pin Henry down about love.
One day, in frustration, she changed tactics in their on-going verbal sparring matches. “Well, then Henry. You are always so fast to put down whatever I say love is. So, now it’s your turn. What is love? And don’t give me some snippy comment from Twain. I want you to actually answer my question. For you, what is love?”
Henry was about to give her one of his snippy answers when he saw the look on her face. She was serious in a way he seldom saw. But when he saw it, he knew the conversation was important to her. He bit back the comment and set his book down. “Well then, yourself.” He steepled his fingers as he looked at her. “Love, hey. If you mean the sort of romantic drivel in literature, I don’t think it exists.”
“Of course it exists. Why else would everyone write about it?” Eleanor asked.
“People write about Golden Mountains,” Henry argued.
“But not as though they themselves have seen them. But all great writers write of love as though they have experienced it. Henry, saying love doesn’t exist is like saying the plague doesn’t exist, simply because you haven’t experienced it,” she said.
For poor Henry, that last line struck home like a lance through his breast, for it was true. Henry hid behind his skepticism. But even he was aware, maybe too aware of the lack in his own life, that love did exist and that he had none. Usually he could ignore the gaping hole where the lance of thwarted love that Annie had thrust once into his adolescent heart. Sitting across from Eleanor, forced to look honestly, he could not ignore it. The pain of it tore at his soul.
“Eleanor, I’m tired today. Maybe we can finish the conversation later,” he said.
She saw the sadness, his great sadness welling up in him again. “Henry?”
Mastering himself as he had so long trained his mind to do, he said, “No, it is all right. I’m just tired.”
Eleanor left, the concern for him in her face. Henry couldn’t help but see it. After the girl had left, Henry went into his room and fell on his bed, great sobs of a lost life wracking his body. 'Annie,' his mind screamed as the agony tore his soul.
Henry was ashamed of himself the next day. But inside, he feared that seeing Eleanor would again awaken those feelings. Henry stayed late at work, convincing himself that this project had to be done, and taking a later bus so that Eleanor would have to be home before he arrived. As he walked up the street he saw the girl was nowhere around. He ducked into his house.
The scene was repeated the next day and the next. Finally, it was Saturday. Henry had arisen and made breakfast. He wasn’t prepared for a knock so early for Eleanor never came when her parents were home. Henry opened the door and stared. A visibly distraught Eleanor was there. She launched herself through the door nearly knocking Henry down as she wrapped her arms around him.
“Henry,” she cried. He could feel her sobs.
“Now, now. What’s this all about?”
Eleanor looked up. “You haven’t been home. I thought you never wanted to see me again.”
Henry heard the agony in her voice and it hurt him, first because he hated hearing pain in her voice and second because he recognized his own complicity. There are times for blunt truth. This wasn’t such a time. “I had to work late is all,” he said.
Eleanor wiped her eyes, “What?”
“I had to work late at the office. I’m sorry if it worried you,” he said.
“So you don’t hate me?” she asked, her voice aquiver.
“Why would I hate you?” he asked, genuinely perplexed. He had avoided her but he didn’t hate her.
“The other day, when I asked about…” she broke down again.
Henry was surprised once again at how perceptive she could be. He knew what she had seen. “Eleanor, I was just tired. It happens to old folks like me.”
Furiously, Eleanor answered, “You aren’t old.”
“All right. Didn’t mean to set you off,” Henry answered, somewhat unsure now. “Listen, aren’t you concerned that your parents will find you here?”
“Yes,” she said. “But I was so worried.”
“Don’t worry. I’ll be back on schedule on Monday,” making a promise that surprised him.
Eleanor let go, then as if struggling inside, turned and left, calling out goodbye as she ran down his walk.
‘What did that all mean?’ Henry would spend the next two days rolling that question over in his mind. There were many possible answers. Why did he get along so well with Eleanor anyway? After all, he liked boys. It was only Eleanor’s resemblance to the boys he liked that made this whole relationship work.
But as he mulled it over he began to realize he did like Eleanor for herself, for her quick wit, for her humor, and for her cheer. She made him feel good when she came over.
He just wasn’t attracted to her. He was attracted to Robert – Robert of the nice boy butt. Henry never thought of Eleanor and Robert together. One was different than the other, at least as much as he could separate them in his mind. Eleanor was for pleasures of the mind, Robert for sins of the flesh.
But several scenes kept replaying themselves in his mind. One in particular emerged and kept coming back: the last one, where she had thrown herself on him and sobbed. Why? It wasn’t difficult really. Henry simply shied away from the answer. About the fifth time the scene played out in his mind, it was as if one part of his mind grabbed the other and shaking it violently said, ‘See! You can’t ignore it any longer! Eleanor loves you, you simpleton.’ Henry was surprised since no woman had ever loved him. And here, this little cutie seemed to be doing just that. She loved him?
Henry was struck by the irony. If only Eleanor had been Annie… How his life would have been different. Now he liked boys, not girls. That choice had been made long ago.
Not that it mattered since it was impossible. There were the practical implications of their respective ages if there were nothing else. Silly girl. On the other hand, Henry knew he would have to be careful. He didn’t want to do to Eleanor what Annie had done to him. Best if he kept it on the same path it had been before. Henry emerged from the weekend with a new understanding of Eleanor and a new resolve not to hurt her.
Monday, Robert was already waiting at the door. Henry smiled and Eleanor nearly melted. She had worried that Henry was done with her. She determined to give him exactly what he wanted come Monday. His smile as he came up the walk made the whole world come alight again. Eleanor bounced up and put on her Robert persona. “Hello,” she said in a slightly deeper voice.
“Hello, Robert,” Henry said. He could feel his staff responding to the thought of Robert soon to be in his bed. Robert led him down his hall. As soon as they entered, Robert went over to the bed. Lying face down Robert pulled down his pants so that just his cute butt showed.
Eleanor was always careful when she was playing Robert to try not to let Henry see her tits or pussy. Her pussy sometimes caused him to lose his erection entirely. She’d have to start over, sucking him hard when that happened.
Henry looked at the cute bare butt and smiled. He started removing his suit when it happened again. That same observant part of his mind slapped him across both cheeks. ‘Listen up; I’m not going to let you ignore it any longer. You love Eleanor. She’s Annie, you ass, only this time she loves you.’ Henry nearly gasped out loud as that thought echoed in his mind. The voice continued, ‘And you love her. That’s right, you do, you knobby headed twit. And you love her two ways. You love her mind and she’s the one giving you physical pleasure. Quit pretending and look at Eleanor. That’s her white ass waiting for you to give you anything you want because she loves you.’
Eleanor looked back to see Henry standing stock still looking off into the distance. She worried that something had gone wrong, just like the week before. “Henry?” she said tentatively, the worry coming back.
Henry shook his head and looked towards the voice. Henry saw Eleanor in boy’s clothes. Suddenly, Henry was struck by just how utterly foolish this pretending was; a beautiful, young, sexy woman in boys clothes. “Eleanor, why don’t you join me in getting naked? You know, I’ve never seen you that way.” He continued taking off his suit.
Eleanor had no idea what to do. This wasn’t like Henry at all. She couldn’t move, so unsure of the outcome if she did.
Henry saw that and smiled, “Come on, don’t be a chicken. I’m taking off my clothes.”
It was with a sense of unreality that Eleanor got off the bed and began to undress. It was probably a good thing since she had never undressed in front of a man before. If she weren’t so shocked by the change in Henry, she probably would have been petrified at getting naked in front of him.
Henry smiled. It was all so clear now that the filters had fallen from his eyes, those filters put there to protect him from getting hurt so long ago. Eleanor wasn’t Anne. Eleanor wasn’t going to hurt him as Anne had done. She was Eleanor and she looked sexy. That surprised him more than the voice had. I love her, he said to himself an affirmation of knowing that he had suppressed for too long. ‘I love her!’ he screamed defiantly to the other part of his mind. Henry nearly burst out in joyous laughter as the ridiculousness of life filled him. What was to be feared when a lovely young woman loved him?
Eleanor crawled back onto the bed, naked for the first time, and laid face down. She felt better now, her nakedness against the bed. When the bed creaked, Eleanor cringed. Was Henry going to find her body repulsive?
Henry got behind Eleanor. He pulled her cute butt up in the air just for him. Now that he had realized that he loved Eleanor for herself, making love seemed wildly different. The realization of love changed something inside Henry. He wasn’t seeing Robert. He was seeing Eleanor, the girl he loved - the girl who loved him. It was her cute butt and it turned him on. How strange; a girl was sexually turning him on.
He looked down, something he usually avoided since he didn’t like to see her sex, only her butt. There it was, her pussy flowered open. Instead of revulsion, Henry felt desire. His love made him desire Eleanor just as she was.
Henry felt his cock pulse with desire, each beat causing it to grow and get hard. He leaned forward.
Eleanor was waiting for the lube, but as Henry leaned forward his cock touched against her pink rosebud. She trembled. No, he couldn’t. His cock was uncomfortable even when she was well lubed. Dry, he’d tear her apart. She was about to say something when she felt him slide his cock down and in between her pussy lips. Was he planning to use her natural lubricant to fuck her ass? He never did that.
Henry felt the heat and wetness of Eleanor’s pussy. It felt surprisingly good. He rubbed the head of his cock up and down getting it thoroughly wet. He slid down and the head of his cock found her opening. He paused.
Eleanor was confused. Henry never acted this way. His cock slid around, then caught in the opening of her vagina. She felt him push and the never before breached muscles around her opening slowly flexed and gave way. Then she felt the skin guarding her entrance tear and she squeaked in surprise. The pressure continued as his cock opened her and the head slipped inside, filling her as she had never been before. In her butt, his girth always hurt. Here, in its natural place, it felt wonderful. Henry was taking her as a woman.
She looked back over her shoulder to see Henry concentrating on entering her slowly. Eleanor relaxed knowing he wasn’t going to hurt her. As she relaxed, Henry pushed and slid deeply into her. “Oh,” she gasped as she felt his shaft slide deep into her. Oh my God, she thought. That was immediately followed by a burst of pleasure as Henry reached bottom pressing against her clitoris. “Henry?” Eleanor asked, her confusion prevented her from even finding words to the questions.
Henry answered from his heart. “I love you Eleanor.” He had said it.
Henry said it! Eleanor’s heart soared. Henry loved her. Henry began slowly moving in the girl, and the physical pleasure, combined with her soaring spirit lifted Eleanor. She was experiencing the heights of love in both ways for the very first time. Henry was moving faster and Eleanor was taken. Playing with herself never felt like this… little mewling sounds came from her throat.
Henry had never felt anything like this. His cock was being massaged by the muscles in her tight wet warm vagina. Henry quickly realized that the woman was designed for taking a man and pleasing him. This was better. Henry nearly laughed with the release, but he was too close now to his own climax. There wasn’t breath to be wasted as his hips pistoned back and forth, sending his cock deeply into the girl below him again and again.
Eleanor felt the waves of pleasure washing through her body, cresting higher and higher until she knew it couldn’t go any higher… Her climax tore through her, crying out in pleasure, “Oh God, Oh God, Goddddd…”
When Henry felt the girl’s pussy pulsing on his cock, it was too much, and his own climax exploded in his loins. He shoved his cock deeply into Eleanor and felt the spasm in his balls as the first great blast of cum exploded down his cock and into her. Again and again he shoved his cock hard into the girl to feel another great blast of cum filling her pussy. Sated, Henry slowed as a last few small spasms wracked his loins and dribbled into the girl. His cock was awash in their combined cums. He looked down as he slid his cock from the girl to see her pussy flooded with his seed. It filled Henry with a satisfaction that he had never experienced before.
Eleanor’s climax had exploded in her body when she felt Henry slam hard against her ass and his cock pulse inside her. She felt the warmth of his cum filling her with his seed and a second climax exploded in her. ‘He’s cumming in me,’ Eleanor shouted in her mind. She wasn’t a boy anymore, but a woman being taken by a man as a woman should. It filled Eleanor with a satisfaction that she had never experienced before. Eleanor felt Henry slid from her leaving her empty. She fell to the bed, happy.
Henry lay down beside the girl. His heart was overflowing with new emotions, new sentiments that he had locked out of his heart from the time when he was a young boy. He had come alive again and more, he knew it. He looked at Eleanor, lying on the bed, her face a mask of satiated lust, and he knew he was in love, real love, true love, for he wanted nothing except the good of his beloved. He was happy in a deep way he never even knew existed. Now, Henry knew what the poets meant by love.
Eleanor looked up to see Henry smiling at her. His face was transformed, soft and glowing. She wasn’t quite sure what to make of it.
“I love you,” he said clearly, softly and plainly as if it was the most obvious thing in the world.
Eleanor was stunned for a moment. The power of his declaration sped like an arrow fired by Eros straight to her heart. She stared at him for a moment, then her heart, filled by his love for her and hers for him, overflowed. “I love you,” she cried as she threw herself into his arms.
Nothing else mattered to either one now; not the lost love of earlier lives, not the age difference, not the pain, not the uncertainty, and not even the sacrifices. They held onto each other knowing that nothing else would ever matter as long as they had each other. And come Hell or high water, they would have each other.
We’ll leave them there, these two actors in our strange love story, in his bed, holding each other fast to their breasts, joy, true joy, filling them both.
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Henry smiled. It was all so clear now that the filters had fallen from his eyes, those filters put there to protect him from getting hurt so long ago. Eleanor wasn’t Anne. Eleanor wasn’t going to hurt him as Anne had done. She was Eleanor and she looked sexy. That surprised him more than the voice had. I love her, he said to himself an affirmation of knowing that he had suppressed for too long. ‘I love her!’ he screamed defiantly to the other part of his mind. Henry nearly burst out in joyous laughter as the ridiculousness of life filled him. What was to be feared when a lovely young woman loved him?
