Caught in a Compromising Situation


Troy Miller was a bit naïve for his age, growing up in a sheltered environment. His parents were devout Southern Baptists and they were determined to see that he made it through to adulthood with his innocence intact. Hoping to shield him from the everyday perils that teenagers faced these days, they strove to control virtually every aspect of his environment.
Being wealthy, they could afford to enroll him in a private academy, a very exclusive school with a limited number of students, all of whom came from families like the Millers. Families who were of a conservative nature, serving God and the church, donating a portion of their wealth and time to charitable causes, striving to preserve morality in America.
They kept close tabs on the company he kept, always keeping him close to home, even chaperoning him during social events. They limited the television he watched, allowing him only to view educational programs, never decadent sit-coms or (God forbid) movies portraying violence and nudity, allowing instead only family movies carefully censored for language or other inappropriate content.
Despite this, at fifteen, Troy was your all-American teenage boy. His young body showed the promise of the man he would become, being active in sports and an avid swimmer; he had all the cuts and tone a boy his age could possibly have. He also had a deep bronze tan from head to toe, that came from spending all his time at the pool in his backyard.
Troy aspired to be an Olympic swimmer one day. He currently was captain of the swim team at the academy, showing an unusual talent that far exceeded any other swimmer on what was considered possibly the best team in the state. He knew he had a good chance at making it if he practiced hard and this is what he did, everyday, all day long.
His idol was Mark Phelps, the 2009 Olympic champion, and Troy studied everything Phelps had ever done. He copied his diet, his practice routine; he even had the same Speedo bikini brief swimsuit, which he wore all summer long, rarely seen wearing anything else while at the pool, thus the excellent tan.
Troy was a good boy, and everyone knew it.

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   His work ethic was high, his willingness to always help without being asked ever noticeable, his moral fiber of the highest caliber. He worked hard while practicing daily and he was determined always to do his best at any task he undertook. His parents were proud to see their efforts rewarded and never missed an opportunity to brag him up to family and friends alike. Troy enjoyed the constant praise and strove to live up to their standards.
Troy had a secret though.
Troy sometimes did something dirty.
When home alone, every so often he took off all of his clothes and masturbated.
Not realizing that this was perfectly normal behavior, even considered healthy in fact, Troy was convinced he was a pervert of some kind.
His father, described in some circles as a religious zealot, had once told Troy that sex was sinful in nature, that only under the sacrament of marriage and strictly as a means of procreation was such a necessary evil to be to be undertaken.
Troy knew that his father was a bit of an extremist when it came to religion, so he was not sure he swallowed this in its entirety. He planned to ask his mother sometime, knowing that she did not share his father’s view in all things, trusting her judgment on matters of importance far more. When the opportunity did come to do so however, he realized he was far too embarrassed to broach such a subject to her and never brought it up.
Had Troy felt just a little more comfortable, speaking to Regina Miller would have saved him several years of guilt and self-loathing. She would told him he was normal and not to worry.
Regina Miller was what some would describe as a true Southern Belle.

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   Hailing originally from South Carolina, she had risen above her humble roots, and married into the richest family in the county. Self educated, Regina was well spoken, thoroughly versed in social etiquette and when the way she carried herself bespoke noble heritage and a cultured upbringing. She encouraged this impression.
The truth was, Regina did not share her husband’s beliefs and merely played along because it was required of her. Ever a dutiful wife, she respected her husband’s wishes and never argued. Her reward was living the life of a wealthy wife, never having to work for a living, having all the free time in the world to pursue her hobbies. It was a good life, and though sometimes she craved sex, her carefully hidden vibrator seemed to take care of most of her needs.
Troy did not have that talk though and carried around his guilt. It did not deter him from doing it, however. In fact, if anything, he was masturbating more frequently. That and his comfort level was up as well. Previously, he was exceedingly careful. He was terrified of the thought of one of his parents walking in on him, finding out what kind of person he really was. Lately, his urges seemed to be affecting his judgment. He sensed that he was taking risks, doing these things at times when he was uncertain how much time he had.

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One day in particular, he took such a chance. He knew his father was at work but was unsure where his mother was. He tried to resist the urge, but his hard dick prevailed. He decided and play it safe and take it to the downstairs family room. He was sure he would hear the garage door opening from there.
Originally, Troy planned on just opening his pants and rubbing one out, and started out doing just that. As he progressed though, he started feeling freaky and throwing caution to the wind, he removed his clothes and lay naked on the couch and lost himself in fantasy.
This was how Regina found him. Upon arriving home, she wondered where Troy could be and checked upstairs for him. Then she thought to check the family room downstairs. The basement steps being covered in thick carpet, she did not make any noise coming down the stairs. Not intending to be stealthy, she walked all the way into the room not registering at first what was before her eyes.
Troy, lost in fantasy still was unaware of her presence.
Standing in the middle of the room, Regina’s eyes widened in surprise as she comprehended the sight before her. Troy lay naked as jaybird, pumping a rather large erection furiously, clearly getting close to his intended goal.

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Involuntarily, her eyes locked onto his penis and she marveled at the impressive organ. Pushing the thought out of her head, she spoke up.
“Uh, Troy do you think you could do that in private?”
It was as if a jolt of electricity hit him. His eyes flew open wide and he sprang to his feet. He attempted to cover himself and was only partially successful. Panic and fear showed on his face and his eyes darted left and right frantically like a trapped animal searching for escape.
Then he let out a loud mournful wail and ran out of the room, she could hear him still wailing all the way up to the second floor, followed by the sound of his bedroom door slamming.
Clearly, the kid was mortified. Sympathy filled Regina and she decided she had better go speak to him. His father would be home in several hours and Regina knew that this one of those things that he simply would not understand. Knowing Harvey, he would probably suspect demonic possession and demand an exorcism.
Fucking nut.
When Regina reached his bedroom door, she her loud sobs on the other side. She tapped lightly.
“Troy honey, can I please come in?” The sobbing got louder and she tried again.

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   “Troy, really, we can talk about this, its okay baby, there’s no need to be embarrassed. ”
The sobs continued. Regina pushed the door open and entered the room, closing it behind her. Troy was under the covers, a pillow over his head, and he was crying uncontrollably. She sat on the edge of his bed and rubbed his back through the blankets soothingly.
“Troy, I’m sorry if I embarrassed you. You weren’t doing anything wrong, it’s natural for a boy your age to. . Uh…to do things like that. ”
His sobs subsided and from under the pillow, she heard his muffled voice, quavering with remorse.
“I’m sorry Muh-muhu-mum…” a new set of sobs wracked him.
    She shushed him like a baby, rubbing his back more and giving him a chance to calm down. Once he seemed quiet, she went on.
    “Troy, really it’s no big deal. Everyone does it, it’s perfectly normal”.

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    He lifted his pillow and an eye peeked out. “Really?” he asked not believing. Regina pulled the pillow away and pulled him up into a sitting position.
    “Alright, enough of this nonsense. You’re a big boy now, almost a man; let’s talk about this like adults. ”
    Troy seemed better now. “You mean I’m not a sick pervert?”
    Regina laughed, “What in the world would make you ever think that?” and then thought of her husband. Anger flashed through her. “Did your dad ever say anything like that to you?”
    “Not exactly, but you know how he is. One time he talked to me about sex and Satan was in the same sentence. ”
    Regina knew she should have spoken to her son about this before. She assumed a kid his age already knew the ropes, between sex education at school and what they learned on the streets, he should have been better versed.
    She realized just how sheltered Troy really was, thinking he was a demented pervert for masturbating, and she became concerned. Not wanting her son to grow up maladjusted sexually she decided to take the matter into her own hands.
    “Troy, we really need to talk, I’m under the impression you have the wrong idea about a lot of things.

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    She proceeded to tell him the facts of life, starting with the basics and proceeding to other forms of sexuality. She talked of masturbation and peoples sexual needs. He did not ask any questions until she got to that point. Then his curiosity out weighed his nervousness enough for him to ask.
    “You keep saying everyone does it, is that really true?”
    “Of course honey, at least everyone with normal sexuality” she threw in the last with his father in mind.
    “Even you?” Troy never looked at his mother as a woman before, let alone a sexual being. Looking at her now, he wondered how he never noticed how nice looking she actually was.
    It was Regina’s turn to get slightly embarrassed. “Yes honey, especially me. I probably shouldn’t tell you this, but you know how your father is…” Troy knew what she meant. “Well as a woman, I have needs and your father doesn’t exactly meet them in that department. Your father is a good and I love him, so I overlook this failing and compensate by taking care of my needs myself. It’s not as good, but it keeps me sane. ”
    Troy thought about this. His mom got horny too? She played with herself and got off? He wondered what kind of dirty thoughts might stimulate her when she masturbated.

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    He felt himself getting horny thinking about it and his dick began to harden under the covers. Feeling liberated he decided to ask another question.
    “You say it’s not bad for me to get…to get horny?” Regina smiled warmly. “Of course not dear, it’s normal like I said.
    Troy continued. “And it’s okay for my. . . my penis to become erect? That doesn’t make me bad?” Again, Regina smiled. “Honey, it would be bad if you didn’t get erections. ”
    Troy was delighted to hear this. He liked that he could speak openly to his mom about this now.
    “So like, what if I told you talking about this stuff is getting me kind of horny and that I was erect right now? Would you be mad?”
    Regina was not expecting this. Not wanting to contradict herself she decided to offer her assurances.
    “I suppose that’s normal too…are you really erect right now?” she asked curious.

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    Troy lifted his covers away, and Regina looked down to see a very healthy looking erection pointing in her direction. Have not have seen a hard cock in years, a pretty un-motherly thought crossed her mind. She felt her heat rise and she flushed. Troy spoke again, “does it make you horny to then, us talking about sex stuff like this?”
    Regina could not lie, “now it does. You have to understand I haven’t seen a hard co-. . ” She caught herself”an erect penis in a very long time. You have an awfully big one for your age…hell, for any age!”
    “Girls like that…a lot”, she added.
    Troy giggled and to her surprised he stroked himself. “You can look at mine all you want”, he offered.
    Regina wanted to do more than look at it. She had a thought.
    “Troy, can I tell you a secret?” her excitement built as he assured her that she could. “Do you know what I think about when I masturbate?” she saw his eyes light up as he shook his head clearly wanting to know.
    “Well, there’s something I really like to think about doing.

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      ” She hesitated wondering if she should really be doing this. “Troy, I want to suck one. . . ” There, she said it aloud to her son.
    “A co-. . . ” his turn to almost slip. “I mean a penis, mom? You want to suck on a penis; really?”
    They both looked down at his swollen member. They looked up at each other simultaneously.
    Regina spoke first. “If you promise to never ever tell anyone, I’d love to suck yours…. ” She watched her son’s expression carefully and went on. “I’ll be honest, Troy.


       Mothers are not supposed to do that to their sons, I know and I could get in a lot of trouble for even suggesting it. I am really horny right now though and I know you are too. . . ” she let her hand creep towards his cock. They both watched as she made contact, she wrapped her hand around it and gently worked it up and down.
    Nothing more was said. Troy sighed and leaned back on his pillows. Regina lowered her head to his waiting cock, taking him into her mouth. He let out a soft moan and she got busy, starting out slow, soon gobbling his meat hungrily.
    The poor kid did not last three minutes.
    Regina was treated to a man-sized load, delivered by a boy. She savored the taste of his young cum and knew that there was no way she could stop here.



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