Part One

A Young Man's Self-discovery

 

Chapter One

 

The young man was somewhat miffed on his last summer home from prep school to learn that his parents had hired a guardian to oversee his well-being during their prolonged trip abroad. His visions of unsupervised partying melted into oblivion as they introduced him to Miss Laura, a trim, petite brunette with a slight British accent whom he guessed to be a well-preserved 40. She greeted him with an ironic dignity, and promised in private to give him as much leeway as possible within the fairly stringent limits his parents had defined. Over the first few weeks of their summer, the older woman and younger man developed a tentative friendship, with Miss Laura treating him as an adult in a natural way. He appreciated that her attitude towards him was notably devoid of the patronization that had characterized some of his parents' other hired caregivers who had tried to get chummy with him before.

They settled into an amiable rhythm of sharing most meals over pleasant conversation, with the young man working out in the home gym and pool most mornings and spending afternoons and evenings socializing with his friends. He had no idea how Miss Laura spent her days, though subtle signs indicated that she made dedicated use of the exercise facilities in his absence. He found himself entertaining some erotic fantasies about her at odd moments when he would notice her lean, athletic physique, but she seemed far beyond his reach, and certainly gave him no reason to hope otherwise.

One evening over dinner he noticed a subtle change in the atmosphere, with her already defined air of irony exaggerated a bit as she questioned him more deeply about his life at prep school. When they finished eating and the cook came in to clear the table, he rose and started to leave to join his friends for his evening plans. He was surprised to hear her state firmly, "I'm afraid you'll have to cancel your outing this evening, as you and I have an issue to settle."

He reacted with surprise, asking what the matter was. Glancing over at the retreating form of the cook and raising an eyebrow suggestively, she said that the issue would be better addressed privately. Miss Laura then instructed him to phone his friends to cancel his plans and meet her in his room where all would be made clear. Feeling a surprising sense of foreboding about what was ahead in the hands of this suddenly very authoritative woman half his size, he complied.

Within a few moments, he answered a firm knock at his door and Miss Laura entered and stood before him, fixing him with her direct, brown-eyed gaze. She said that she had become aware of a serious violation of conduct on his part, and that the consequences would depend on how frank he was in his responses to her. He colored and stammered that he had no idea what she meant. She responded that so far he was only worsening his predicament, but he remained genuinely bewildered. She then inquired, "Where do you store your erotica?" He blushed fiercely, and stammered that he had no idea what she was talking about. "Even worse," she said, as she strode to a bedside table and opened a bottom drawer, from which she removed a book that had been hidden underneath some others.

Miss Laura went on with her usual sense of faintly humorous irony, "Now are you going to make things even worse for yourself by denying you know anything about this?" She held in her hands a copy of Beauty, Anne Rice's erotic fantasy about submissive young men and women, termed 'Princes' and 'Princesses'. In this book, these attractive young people were willingly subjected to all manner of sadomasochistic sexual experiences at the hands of their jaded mistresses and masters. He stammered his renunciation of further denials, and admitted that he had filched the volume from his parents' bedroom.

Miss Laura stood before him, clearly in complete command of the situation, and went on: "So you have violated your parents' privacy in the service of your own sexual gratification by stealing a dirty book about boys and girls whose naughty bottoms are violated in all sorts of ways. If the punishment is to fit the crime, I think that you should have the chance to find out exactly how they felt, don't you?" He muttered that he guessed so, and she took his arm gently but firmly and guided him through the now-empty household to the guest suite in which she was staying.

The young man was led into the spacious bathroom of the suite, and told to stand and watch while she prepared for his punishment. He was filled with conflicting feelings of fear and excitement as he watched Miss Laura methodically move an armless vanity chair to stand with its back to the sink and counter. She reached into a bathroom drawer and removed a large wooden hairbrush and placed it on the counter, glancing significantly at him as he did so. From another drawer she took a shoebox, from which she took what he vaguely recognized to be enema apparatus, as well as a large jar of Vaseline, which she uncapped and placed on the counter. She then took a container of liquid soap from beside the sink, and squirted a generous quantity into the enema bag.

"Naughty bottoms need a thorough cleaning as part of their punishment, I'm sure you'll agree. A good hot soapy enema should just do the trick, I think!" Her humorously matter-of-fact attitude and language and behavior left him paralyzed in red-faced silence. She allowed the water to become steaming hot after clamping the enema hose, and carefully filled the bag. The small woman stretched to her full height to hang the apparatus from one of the ornate clamps securing the mirror above the sink, revealing an expanse of firm thighs beneath her dress. She then reached into the shoebox and produced a white plastic nozzle with a knob the size of a large olive at its end. She screwed this onto the end of the enema hose, and carefully twirled it in the Vaseline, leaving it in the open jar. He watched with serious trepidation from across the room as she then turned and seated herself on the chair facing him.

"So, young man, here we both are in the predicament you've created for yourself. As you can see, you're to receive a thorough enema and spanking on your bottom. Here are the rules under which we shall proceed. You are to do exactly as I tell you, no more and no less. Any violations of this simple principle will increase your punishment, which I'm sure you will be most anxious to avoid. You can begin by removing your clothing and placing it on the counter next to you."

"But Miss Laura," the young man pleaded, suffused with embarrassment as he thought of revealing the raging erection he was harboring under his shorts. Her rich laughter rang out, and she went on, "Silly boy, did you think I was going to just lower your pants in order to save you some embarrassment? I intend to punish you, not your clothing. Embarrassment is a key element of your well-deserved consequences, since I think we both know that it would embarrass your parents seriously to know that you had violated their sexual privacy. So it seems quite appropriate that we will be thoroughly violating yours. A humiliating display of just how exciting you find the proceedings until this point is only the barest, so to speak, beginning of your embarrassment!"

As the young man haltingly removed his polo shirt, shorts, and boxers, Miss Laura watched him with apparent amusement and enjoyment as she went on, "I'm sure you enjoyed the view of my bottom while I was hanging the enema bag. Correct?" He remained silent until she prompted, "How much worse do you want to make things for that poor bottom of yours by any lack of cooperation?" He admitted that he had in fact enjoyed looking at her trim backside. By that point, his muscular young body was fully revealed, including a spectacular erection. The older woman went on, "Well, it seems only fair that I will get a very long and detailed opportunity to observe your bottom at very close range, then, don't you think?" The young man nodded in miserable agreement.

Miss Laura then commanded the young man to stand directly in front of her. He did so, his erection bobbing with each step, and stood 2 feet in front of her as she had directed him. She then surprised him by reaching put and firmly grasping his penis in her right hand. He gasped as she watched his face closely. Then, with her left hand she reached forward and took his testicles firmly in her left hand, holding their root encircled by her thumb and forefinger. She went on, "So here is how things will go. Since boys and girls cannot help but wriggle as extremely uncomfortable things are happening to their naughty bottoms, there must be some means of holding them in place. Boys like your self have a convenient handle with which to accomplish this, namely their oh-so-sensitive little balls. So, after you have obediently bent yourself over my lap with that penis lodged firmly between my thighs for additional control, I will reach around your waist and resume this hold on your little ball-sac. This will sharply limit any wiggling you will want to do for obvious reasons," she stated matter-of-factly while giving his balls a slight squeeze for emphasis, producing another unconscious gasp.

Miss Laura went on further with her humorously delivered instructions to the thoroughly cowed young man, "In addition, having a firm hold on your family jewels also enables me to overcome another little problem that arises in these situations. While I am punishing you, I am going to be asking you to do a number of things that are, shall we say, quite challenging. First of all, in order to give me the greatest possible access to those extremely sensitive areas I am going to be making very uncomfortable, I will instruct you to open your legs as wide as possible and keep them that way. This is going to seem very counterintuitive to you, and you will experience a strong impulse to close them in order to protect those delicate parts from my not-so-tender ministrations. This would be an impediment to my purposes, and would not be tolerated. "

The older woman went on, looking steadily up into the frightened eyes of the young man whose genitals she so firmly grasped in both her hands, "Second, you will experience a strong impulse to plead with me for mercy, which I find so unappealing in a young person. While I expect you to cry out, and would indeed be disappointed if you didn't do so, since it would mean that I was not having a sufficient effect, I will not tolerate undignified begging. Throughout your punishment, the only words I will expect to hear from your lips other than wordless cries will be my name. Both of these purposes will be enforced by the other purpose of my grip on your balls, which is to deliver chastisement beyond that which I plan for your bottom. If you should give in to impulses to close your legs or speak beyond the limits I have prescribed, I will remind you of them like this!"

Miss Laura gave a sharp squeeze to the young man's scrotum, digging her nails into his testicles. He gave an unwitting shout and bucked in her grasp. She quickly relented, and his pain subsided as he swayed above, obviously controlling an impulse to protect himself with his hands, which he conceivably could have done with a woman literally half his weight, though perhaps at great risk given how she had a hold of him. She observed his face intently throughout this exchange, and once he had started breathing normally went on, "So, do you understand me clearly?" He stammered out on agreement, and then she spoke once more before she released her hold on his genitals, "As far as this firm young fellow is concerned," giving his penis a significant squeeze, "We'll see about him later. This part of a man always thinks everything is about him!" He then clumsily draped himself over her lap, as she guided his erection between her thighs. Her bare skin felt so delicious against his penis that he experienced a moment of fear that he would climax in an instant.

Miss Laura extended her left arm around the young man's waist as she had promised, asking him to raise up to accommodate her resumption of her grip around his balls, which he did with a sinking sense that all was now truly lost. They both settled back down into position, which required her to bend only slightly forward because of the trimness of his waist, placing her head directly above his exposed bottom. She instructed him to spread his legs as wide as possible, which he did, though the left one was limited in its range by the counter behind them. He gasped again as she began stroking his muscular young buttocks, which quivered involuntarily under the unfamiliar intimate touch. She spoke softly as though talking to herself, "Such a pretty young bottom, and so vulnerable like this. Such a pity that this innocent young bottom has to suffer so terribly because of the naughtiness of its owner."

The young man's awareness had fled from his entrapped penis to reside in the contact between the older woman's stroking fingers and his obscenely quartered backside. He gasped again as her stroking left his outer cheeks and began to drift inexorably toward his bottom cleavage and the puckering rosebud of his anus, so rudely exposed to whatever she intended for it. Miss Laura continued in her crooning, almost sedative tone, "And here we have this virginal little bottom-hole! I am correct that no one has been here before me, am I not?" He admitted this was so. "I'm so glad!" she exclaimed, as though somehow he should be as pleased with this fact as she was. He continued to twitch involuntarily as she played with the tiny hairs surrounding this ultimately vulnerable part of his anatomy, while she laughed softly at his discomfiture.

"Such a sensitive place," she murmured, "and especially so when it knows it's in for such a difficult time!" Miss Laura was clearly enjoying every instant of this opportunity to punish the young man, and he knew it as well as she did. This heightened the intensity of the situation for both of them as she toyed with him like a cruel cat with a helpless mouse. Suddenly, he flinched again as her right hand left his behind, and he heard the sound of her reaching into the Vaseline jar behind them. She resumed speaking, "Well, the time has come to venture inside this tight little virgin rosebud and make it ready for the trials ahead. Her lubricated index finger returned to rest lightly on his anus itself, languidly circling it as she began to probe. He gasped as her finger firmly pushed past his helpless musculature, entering him for the first time in his life. He moaned as she continued her twirling invasion of his bottom, and she moved her finger in and out a few times, gently fucking him, provoking a deeper moan.

After a minute of this rhythmic penetration of the young man with her finger, Miss Laura began to speak as she probed more deeply, "Such a tight little bottom hole, I think we'll be needing to loosen it up so that its coming trials don't cause it any harm. No sign of anything nasty in there so far, though we'd be taking care of that soon enough if there were." Her finger twirled around as she reached forward to contact his prostate. He gasped in surprise as even more unexpected waves of unfamiliar sensation washed over him, this time clearly pleasurable and sending a jolt to his still-erect penis clasped between her thighs. She spoke with a laugh, "What have we here! This, young man, is your prostate gland, and in my opinion, is the best evidence that God intended boys' bottoms to be fucked, which we are just about to do quite thoroughly!"