"You say you've never done any of this before. What do you mean? This is the first time you played with yourself?" she said with a smile.
Charlie met her eyes briefly and said, "No, I've done that before."
"So there are two things. Snooping in my drawer and wearing my undies. You never did either of those things before?"
"No, never, I swear."
"I wonder. Tell me what you thought and how you got from the garage to my panty drawer."
"Well, the blade was dull and I sharpened it and my hands got greasy. So I went into the kitchen to wash and I needed to pee, so I came upstairs..."
"There's a wash room downstairs."
"I didn't know that, I figured there'd be one upstairs. If you don't believe me, there's the greasy rag." He pointed to one corner of Jessica's vanity." I was going to take it back downstairs to the garage."
Jessica grunted, provisionally accepting his story. "Go on."
"After I peed, I realized your room was probably close by. I... I I thought you look so beautiful and sexy when we met, I just wondered, you know, what your underwear looked like. Girls wear such pretty, sexy clothes. That's all it was, and I never did it before and I'll never do it again.
"That's not all you did."
"When I saw how pretty they were, and how different from guys stuff, I wanted to see what they felt like. I had no idea I get so aroused. It just felt so good, so sexy, I couldn't help myself and I started... you know."
"You jerked off in my panties. Say it. Say what you did."
"I sneaked into your room and jerked off in your panties."
"That's right, and I'm going to punish you for it. But I have a few more questions first. How much experience you have with girls?"
"Nothing, really. Nothing to tell about." He avoided eye contact. "You were so busy at school and summer camp that you never even talked to girls?" Charlie managed to laugh a little. "Of course I talk to girls. Sometimes there are dances with other schools or camps, but it's hard to get to know someone that way."
"Been on any dates?"
"Did you have fun?"
"Yeah, I guess so."
"But not a lot of wild making out at the end, I guess."
Charlie smiled ruefully. "No, nothing like that. A couple of good night kisses, that's all." He hung his head.
"Never felt a girl up? Or touched her pussy?"
"No, I think about it all the time."
"So you're a virgin?" Jessica realized.
"I'm probably the least experienced guy in the whole United States."
Jessica sat back a moment and recrossed her legs, drawing Charlie's fascinated eye. "I see. I guess you're telling the truth and you never snooped before. It really was curiosity. "Well, Charlie, there's hope for you yet. You're a good-looking guy. Maybe over the summer I can help you out with your virginity problem." She saw the expression on his face and realized she'd given him a false hope. "Down boy. I didn't mean I was going to do it personally. You're a good-looking guy and I know you have a good penis when it's hard. I can introduce you to some girls. But you'll have to take it from there. "I'm still going to spank you. I wouldn't pass up such an opportunity, but at least I have some understanding of why I found you jerking off in my panties. Let's get started. Pick up the brush."
Charlie sighed. His brief hope died instantly. Wordlessly, he picked up the brush and stood by her chair, clenching his butt cheeks. Jessica sat and crossed her legs. Pointing to the floor in front of her, she said, "On your knees."
Wide-eyed, he obeyed, settling on his knees and toes, torso erect.
"Good. Now tell me what you did wrong and ask me to punish you, then hand me the bath brush."
"Uh... Okay. Jessica, I'm sorry I sneaked into your bedroom and jerked off in your panties. I deserve to be punished."
"I'm glad you acknowledged what you did. You did not ask me to punish you. Tell me again what you did and ask me to punish you."
"I sneaked into your bedroom and jerked off in your panties. Please punish me for this."
"Very well, I will punish you, since you asked so nicely. I get to spank you as long and as hard as I want. You'll take it without struggling or trying to get away. Otherwise..." She paused, and expect an eyebrow raised.
"Or you'll tell."
"That's correct. I'm letting you wear my panties because that will remind you of your offense. There is one rule for the spanking. I'm only going to spank you when your penis is nice and hard." She eyed the bulge in the panties. "Looks like it's only half hard. Touch it. Squeeze it. Make it hard."
"Really? Oh, Jessica, that's so embarrassing."
"You don't have to do it if you want me to tell. Besides, I've already seen you stroking it when it was very aroused indeed."
Blushing, Charlie reluctantly moved his right hand to his cock and squeezed lightly. Jessica uncrossed her legs, keeping her knees together. She spoke softly. "If it helps, you can look up my dress." Charlie's eyes opened wide. Jessica's mini dress allowed him to see all the way to the lace tops of her stockings and a tiny hint of white lace with her legs met. He squeezed himself harder and his penis responded. In a few moments, he slightly adjusted himself and the tip rose above the skimpy garment's waistband. Released, it exuberantly pointed straight to his bellybutton, barely above the flaring tip.
"There it is," Jessica exclaimed in delight. "It looks very cute peering out of the top of my panties. Now hand me the hairbrush." Jessica leaned forward, far more forward and she needed to, watching Charlie's eyes. They widened anew as her dress fell away from her cleavage.
"Oh, Jessica, you're so beautiful."
"It's okay to look, but you know you're not allowed to touch."
"Yes, I understand. I'm being punished."
Jessica took the bath brush from his hand and placed it on the floor by the chair. She sat up and patted her thighs. "Bend over with your head to my left."
"Okay," he said nervously as he bent over her lap.
As the boy bent over her in submission, Jessica drew in her breath sharply and she felt her pussy go damn. Smiling broadly, she rubbed Charlie's cheeks with a swirling motion. "You do look cute in my panties. I see your pale skin through the lace." She gave him his first, light tap. "Pretty soon, though, I'll see pink there." She smacked him lightly, with a steady rhythm. She felt his stiff cock pressing against her left thigh. Oh, this is fun she said to herself. She slapped harder and faster. Charlie squirmed a bit, but did not struggle or protest. Jessica, paused, again rubbing his cheeks. "Wow, you're already getting red under there. You sure look pretty."
"I'm not pretty. I'm a boy."
Jessica stepped up her speed and force. "Yes, a creepy boy who sneaks into my bedroom and wears my panties to jerk off!"
"I'm sorry, Jessica, really I am. I'll never do it again."
Jessica paused. She no longer felt the head of his prick against her leg. "You're getting soft already, aren't you?"
"I... I guess so."
"Stand up." Charlie obeyed, crossing his hands in front of his limp dick. "Take your hands away. You are not to hide yourself from me. I won't tell you again. Now I can't continue your spanking until you're hard again, that's the rule. Go ahead, make yourself stiff." With a loud sigh, almost a sob, Charlie fondled the tip of his cock where it flopped over the waistband. Jessica crossed her legs, right leg on top. She turned up the hem of her skirt and stretched out her leg, tugging at the elastic top.
"Oh, my God," groaned Charlie, staring avidly at her brazen display. His cock popped right up.
"I thought that would get you stiff," Jessica said with a confident smile. She uncrossed her legs and patted her thighs. "Back you go for more spanking."
"Wasn't that enough? It sure stings, Jessica, and I've learned my lesson. I know I have." "Don't be silly. Stop arguing. Get over here now. I'll decide when you've learned your lesson. Besides, I haven't even begun with the hairbrush. If you think it stings now, just you wait."
"Okay," muttered the boy, resigned. Without further protest, he lay across her lap. Jessica squeezed each cheek, then resumed spanking. She lit right into him. Pretty soon she noticed his cock was not as hard as before. Yet she did not wish to stop spanking. She kept it up a few more smacks, until her hand began to hurt.
"You're losing your boner again. Stand up."
"I suppose you want me to do this again," Charlie mumbled, eyes averted as he squeezed his limp cock.
"Yes, of course. I'm glad to see you get with the program." She paused, watching him squeeze. "But it's not very effective this time. Why might that be?" "My bum really hurts, Jessica. You spank hard. Isn't that enough? I already said I'll never do it again and I'm sorry."
"The point isn't whether you've learned your lesson. For one thing only time will tell. Maybe you'll turn into a real panty freak. The important thing is for me to take out my anger on you and I'm just getting started." She frowned, looking at his limp dick. "You can't even get it up. Must I do everything?" Exhaling sharply, she said, "Take your hand away." When he let go, Jessica took his cock head between her thumb and two fingers, twirling it gently.
"Oh, oh, wow!" gasped Charlie, mouth open, eyes wide. "Oh, that feels good." Charlie achieved a full erection in record time. Immediately, Jessica let go. "Quick, back over my lap." "Aww..." Charlie began to protest, but a glimpse of Jessica's snapping eyes persuaded him otherwise. He lay across her lap. Jessica smacked him a few times, then reached down to her side and picked up the hairbrush. She pressed it into his cheeks, rotating it around her target. As with her hand, she started with light swats, gauging his reaction as she increased the force. Soon, Charlie grunted with each blow. Breathing hard, Jessica controlled her inclination to strike harder and harder. I want to make this last, she told herself. Only a few really hard swats made his penis wilt again. "All soft and tiny again. Stand up."
Charlie jumped up, glad for that relief, however temporary. He jogged from one foot to another, standing in place. "Oh, Jessica, the hairbrush really stings. It hurts. Please, I learned my lesson." "Remember, it's not your promise, but my anger that makes the difference here. I'm still angry. Stand still." She leaned forward, peering at his limp cock. "You do have a nice one, Charlie, but right now it looks forlorn, hanging down over my panties." With her open palm, she lifted the exposed portion. "Charlie, I want your cooperation in what I'm going to do. Now I'm going to make you very hard, like I did last time but I'm not going to stop until you tell me to. Tell me to stop before I make you cum. When I'm ready, I will let you come. Promise. But if you come before I let you, your punishment stops. Do you understand?"
"Uh... I guess so. Maybe."
"I'm going to keep you hard and excited while I spank you until I'm done. I need you to cooperate with your punishment. Let me know when to stop playing with you so that you won't come. If you take your spanking well, I will let you come. Now do you understand?" "Oh, wow, now I get it." Charlie shook his head, grappling with the pleasure/pain principle. "I thought you'd figure it out eventually," said Jessica sweetly wrapping her hand around his penis. One squeeze in the lab became fully erect. She slowly stroked him, tugging the panties below his scrotum with her other hand.
"Stop or I'll come!" gasped Charlie, twisting away from her.
Jessica let go. "Stand still, take a deep breath, Charlie. Calm down. That's it, regain control. You see if you can't last longer this time." She held his cock and stroked it, but avoided the sensitive tip. Nevertheless, pre-come coated him. "Oh, good. Pre-come. You like this part of your punishment don't you?"
"Oh, yes, Jessica! It's the best thing that ever happened to me!"
"See how long you can last and let me know before you're going to come."
Charlie stood still, breathing hard. His cockhead flared as more pre-come lubricated his tip. He gasped and grunted, trying to avoid ejaculating. Jessica let go. "Take a break, you'll last longer. Oh, look at it twitch." Charlie's cock and hips bobbed and thrust. He panted. When his breathing slowed again, Jessica gently wrapped her hand around the bottom of the shaft. "It must be hard for you, Charlie, so strong and handsome with a nice dick like this and no experience. No wonder you're curious about my panties. If you take your spanking well, I'll give you a lesson about panties. " She looked up at him sympathetically. "Oh, I hope so." Charlie, reveling in the sensations grunted and curled his toes to control his urged to spray. "Stop, or I'll come."
Jessica immediately let go. "Well, you're certainly hard enough that I can spank you again. Back over my lap you go, my boy."
Charlie bent over instantly. "Okay!"
Jessica grinned. He wants it now. He's sure learning some sort of lesson. She smacked him with the hairbrush on alternate cheeks. Charlie grunted and gasped. "Ow!" He kicked his legs. "Oh, that hurts, Jessica." Jessica grinned, thrilled by the sounds he admitted in his kicking legs. "I was right, Charlie. Your red bum shows through the lace very nicely. Whoops, you went all soft again. Stand up."
Charlie stood up with alacrity and reached around for his cheeks. "Oh no, no rubbing your buns during punishment. Not till I tell you. Hands at your sides." Charlie obeyed instantly, waiting expectantly. Sure enough, with a smile, Jessica grasped him around the base of his cock, which instantly stirred, swelling. With a lilt in her voice, Jessica said, "You like wearing panties, don't you Charlie? You like the way they feel." She slowly stroked his cock with a loose grip.
Embarrassed, hanging his head, Charlie mumbled, "I dunno."
"Oh, I think you should admit it. When I came in here, your hard dick was sticking out of my panties and you almost ready to come, weren't you?"
Charlie, fully erect, involuntarily thrust his hips back and forth as Jessica stroked him. "Yes, I guess so."
"Then say it, sweetie. I think it's nice that you like my panties."
"Say, 'I like wearing girls panties because they feel so good.'"
Hips thrusting, biting his lip, with a sob Charlie gasped, "I like wearing girls panties they feel so good. Please stop, or I'll come, Jessica!" Before he finished speaking, Jessica released his cock. "Deep breaths, Charlie. Hold still. Relax. That's good." Their eyes met and she smiled at him as he regained control. "Ready to try again? Remember, don't come." Charlie took a deep breath. "Okay, but I don't think I can last long. You are so sexy!"
"Thank you. I'll make it easy for you to control yourself." She ran the tip of her forefinger up and down the front of his shaft, stopping below his frenulum. She looked up at him smiling to gauge the result. Charlie closed his eyes and panted. With her free hand, Jessica tugged the panties from his hips, down to above his knees. "You're kicking threw off my aim a bit, so these panties will keep you under control." Continuing the delicate finger massage, she rolled his dripping cockhead between her thumb and fingers.
Almost instantly, Charlie's hips thrust and he cried out desperately, "Stop, or I'll come!"
Jessica released him and a smile played across her lips as she watched him breathe to regain control. "I'm going to spank you quite hard this time, Charlie. If you take it well, I'll give you a reward. Over you go, my boy." Again, she patted her thighs. Fully docile by now, Charlie draped himself over her again. Jessica felt his pre-come soak her left stocking.
"Wait, stand up again."
Puzzled, Charlie obeyed. "What?"
"Look," said Jessica, pointing to the damp spot. "You get so much pre-come, it's getting all over my stocking. Very hot, very sexy. You have a very nice cock." "Wow, I'm glad you think so, Jessica. You are the sexiest and most beautiful girl in the world." Jessica smacked him again and again, sometimes on alternate cheeks, sometimes concentrating on one for a time, only to switch to the other. Charlie, beyond words, gripped the chair to stay in place and kicked his legs wildly, as far as the stretched panties allowed. He grunted and cried, finally gasping out, "Oh, please, Jessica!"
Jessica stopped. "Don't get up yet, Charlie I want to enjoy the view. You are so red! I love it." She rested her hand on his cheek. "Oh, that's so hot! You're being very good about it, taking your punishment very well. You can put your hand on your bum to feel your heat, but don't rub yourself."
"Oh, wow, that is hot. You're really blistering my ass, Jessica." "Okay, hands off. Stand up. Good, nice and obedient. Look at that limp dick. I bet your bum hurts, doesn't it?" "It sure does, Jessica." He caught her eye with a sly smile. "But I hope my punishments not over yet." Jessica laughed. "Now you've got it! You learned a lesson you never thought of before, didn't you?" "I learned a lot from you today, Jessica."
Jessica crossed her legs "Well, Charlie, you earned your reward and you're about to learn something new. On your knees in front of me, hands behind your back." Charlie obeyed, eyeing her expectantly. "Do you think I have nice legs, Charlie?"
"Oh, my God yes! Everything about you is beautiful."
"Isn't the lace at the top of my stockings pretty?"
Charlie's breathing grew audible. "Really pretty."
"Take a good look at the lace. Notice the pattern. Take a close look. Oh, I see you like the lace. Your cock's beginning to rise. Do you have the pattern memorized?"
"I guess so," said Charlie uncertainly.
"Does it match my lace panties?" Jessica uncrossed and opened her legs.