As Bill waited for Cindy to exit the shower, he had a moment’s doubt about the day’s chore. He wondered what he would say and how this Katherine woman would respond to it. He was ostensibly going to find out if the dress was going to be permissible. In point of fact, he was counting on it not being allowed. But, either way, how do you ask, “Would it be alright for my wife to wear this dress; she’s agreed to be the prom date for our next door neighbor?” On it’s own, the statement was beyond awkward. Throw in the fact that the dress couldn’t be any sluttier, and his wife was built like a pin-up model, and it just got more embarrassing. Then there was the fact that unlike approximately half the kids attending the prom, Paul was legally an adult; in fact a full year into adulthood, at the age of nineteen,
Bill decided that Paul’s age was the fact that he’d play up. Not his age directly; but the reason a nineteen year old was still in high school. Everyone knew Paul’s tragic story; the car wreck that had taken his parents, and cost him two years of school. Mill would emphasize that it was this story that had brought out his and Cindy’s empathy, and had convinced them to agree to his request that Cindy be his guest. It was the truth, wasn’t it?, Bill thought. But more and more of late, he doubted his own motives. Had prurient interests played a role? Had all that wife-watching porn gotten to him, twisting his thoughts and desires? Did some small part of him want Cindy to wear the dress for Paul? And more?
Even as he wondered, Cindy finally exited the bathroom. Bill glanced over, and Cindy gave him a shy smile and averted her eyes. There’s the cindy I know, he thought ruefully. All wrapped up in that big terry cloth towel, and finally embarrassed about last night. Oh, well, even if she is embarrassed, what happened once can surely happen again, can’t it? Little did he know just how right he would be.
He gave it little thought though as he went to take his own shower. No matter how hard he tried, his mind wandered from last night to the coming appointment with the high school vice principal. He imagined that though the vice principal was a woman, that would change little in the way of the stereotypical demeanor. Vice principals were the enforcers, the stern taskmasters. He imagined that no matter what reasoning he gave, she wouldn’t be approving of Paul bringing a married woman to the prom. And, she would not be pleased with the dress at all. But, that was the point, wasn’t it? To have the dress disallowed? Nevertheless, Bill was nervous. He was always embarrassed being in situations where people might judge him. He realized suddenly that this wasn’t going to be as easy as he had envisioned.
But the situation became infinitely more difficult when he arrived at the school to find that Vice Principal Katherine Sabbatino was none other that Kate O’Brien, the last woman he had dated before meeting and eventually marrying Cindy. His relationship with Kate had been intense, and kinky, and he had sought to put it behind him. She hadn’t taken the breakup well, and he’d done all he could to distance himself from her. He had no idea she’d married and become the high school vice principal. His earlier characterization of vice principals sprang immediately to mind as he thought, Stern taskmaster, indeed.
Still, as she came around the desk to greet him, smiling, he hoped she had forgotten all her past animosity. And as she greeted him with a kiss on the cheek, he thought perhaps it was so. But, something seemed amiss. After kissing his cheek, she reached past him and locked her office door. Then, she stood too close and she seemed to have prepared for this, as she asked sweetly, but unprofessionally, “So, the Snow Queen, Miss Purity, wants to go to the prom with Paul does she? But you’re concerned about….the dress?’
Bill stammered in shock, “Wwwwell, it’s….it’s a little risqué.”
Before he could say more, Kate pulled the dress box from his arm, and had it open. She held the dress up and whistled, “Oh my. This isn’t a little risqué, Little Bill. This is downright, absolutely, no holds barred slutty.”
Bill’s face went scarlet with embarrassment as she spoke her nickname for him. Though he hadn’t known it had a label back then, SPH, small penis humiliation, had been a central theme of their sex life, when they’d been together. Despite the embarrassment, he felt a twinge of arousal. But he chose to ignore both the embarrassment and arousal, as he asked, “So, it’s too much, right? There’s no way that’s going to be permissible, is there?”
Kate didn’t answer him though, instead asking her own question, “She can’t wear a bra or panties with this, can she?”
“Nnnno, no she can’t,” Bill again stammered, before asking again, ”So, she definitely can’t wear it, can she?”
Kate laid the dress back in the box, closed it and returned it to Bill. She handed it to him and then half-whispered, “This is just an extension of the other thing, you know? When you used to love me to tease you about your teeny tiny cock?”
She then reached out and cupped him, and Bill was stunned to find he was rock hard, and that he couldn’t find it in himself to resist, as she continued, “Mmmm. You still get so hard, Little Bill. But it’s even smaller than I remember. I’ve had quite a few since then; I guess the experience made it a little hard to remember something this little.Still, it’s nice to know that the teasing I introduced you to still affects you so strongly”
Bill squirmed in embarrassment, even as he throbbed to her touch. Kate wasn’t as tiny as Cindy, but he could have easily pushed her away. Only, she’d always had this hold over him. “somehow, he found the strength to say, “That was a long time ago, Kate. That’s not a part of my life anymore. You need to tell me the dress is barred, and then I need to leave.”
Kate smiled wickedly, as she began to slowly pump his cock through his pants, “Little Bill, stop kidding yourself. Aside from your cock, you’re as big as a house. If you didn’t like this, you’d stop me. But you like it and miss it, that’s why you’re in this predicament. It’s too small for her, isn’t it? You don’t get her off, do you? Has she ever come on your cock?”
Bill didn’t answer, but Kate’s eyes went wide at his expression, and she continued to stroke and torment. “She’s never come at all, with you? Oh. Little Bill, you must love and hate that. Love the confirmation the you’re just too small. But hate that you can’t bring sexual pleasure to the woman you adore.”
Without meaning to, Bill blurted, “She won’t let me.” Then catching himself, he asked once more, “The dress?”
“Oh, Billy, Billy, Billy. I like that, that’s a little boy’s name. In any event, this isn’t the farm country we grew up in Little Bill. Sub-divisions filled with high tech workers have replaced those fields. And those workers are far more liberal than the farmers they replaced. There’s no dress code for the prom.”
Bill gasped, his last hope shattered. But Kate wasn’t done, talking or stroking. “Have you heard about it?” she asked, and again her eyes went wide at his expression, and she continued, “Oh. You seen it, haven’t you? It’s all you can think of, isn’t it? Sweet little Cindy going to the prom in that oh so slutty dress? Her big titties all but spilling out of it? And him getting hard?. Eventually, he’ll show it to her, Little Bill. And then the Snow Queen is going to melt. She’s going to be dripping wet, Billy. And she’s going to need to be, to stuff that colossal cock up inside that unused pussy.”
Bill wanted to protest. But as he shuddered in orgasm, as Kate laughed, there were no words to say, no way to justify hs reaction. She stroked, and he filled his underwear with cum Then, he let her kiss him full on the mouth before he turned and left as she opened the door. Her final words were, “Don’t worry Bill. You, Paul and Cindy are all going to love it.”
That just can’t be true, he thought. But the sticky mess in his pants suggested very much that it was true.
My other stories are here:
Naïve Wives Turn Naughty, Amazon (5 Volumes): http://www.amazon.com/Jake-Wittol/e/B009O3BZWG/ref=ntt_athr_dp_pel_1