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Wingate Chronicles: The Virgin's Bribe

Sandy discovers a talent for acting the virgin.
This story continues where “Oral Quickie Class” ended.

In the future, sexual repression will be considered especially heinous. Enlightened parents will enroll their 16 year olds in sexual schools, which include rigorous college preparation. In the United States, female graduates of the Wingate school are members of an elite squad known as the Wingate Girls. These are their stories.

Robert returned to his hotel to eat and recuperate. Sandy and Elena later met him to plan the fantasy role play.

By the end of the meeting, Sandy was very impressed. As Robert described his fantasy, both girls took notes, but Elena’s were much more detailed. After Robert finished, Elena asked many questions, clarifying Robert’s fantasy for him. “You say she’s wearing ‘cute’ panties. Describe them.” After a series of questions, they knew Robert liked very tight white cotton hiphuggers or bikinis for this particular schoolgirl fantasy.

Telling Robert they’d return after preparing Sandy, the pair went to the wardrobe room. “One of the things you learn in Fantasy Fulfillment is to get the man to be as specific as possible about what he wants. Once you have that, you think of ways to make it more realistic for him. Then he thinks you’re great and pays big money to act out other fantasies. Do a good job with Robert, as I’m sure you will, and he’ll be back.”

Elena had Sandy lie on her back on a padded table and fitted something into her slit, then gave it a kiss, briefly sucking the girl’s clit, much to Sandy’s enjoyment.

Sandy tried on several panties before she found a pair so tight her pussylips filled the front and the back clung to the contours of her cheeks. “What every schoolgirl should wear to her spanking,” Elena teased.

She fit Sandy with a red pleated skirt that came halfway down her thighs. It was decorated with a couple of short belts on one hip and a small pocket on the other. A white underwired demi-bra, white blouse with a tie at the neck, white knee-highs, black Mary Janes and a touch-up to Sandy’s make-up completed the outfit of a blushing miscreant.

Carrying a wooden paddle and a short rattan cane, Sandy knocked timidly on Robert’s door. “It’s Sandy, Mr. Robert, sir.”

“Come in, Sandy,” said Robert as she opened the door. He took the paddle and cane from her. “I see you brought the proper punishment tools as I told you. Now then, the sooner we get started, the sooner your ordeal will be over.” He sat on a straight-backed wooden chair and placed the implements on the floor at his side. He spread his legs and said, “Come stand in front of me.” Sandy, hands clasped behind her back stood a yard away, eyes downcast. “Closer, girl, stand between my legs.”

Hesitantly, Sandy moved up and stood before him, nervously clenching her skirt. “Please, Sir Robert, I’m truly sorry. I know I deserve to be punished, but do you have to use the paddle and the cane? I promise I’ll never do it again.”

“Of course you won’t because the punishment will be effective. Let’s have no more of that nonesense. On your knees, hands behind your back, tell me what you did to deserve punishment and ask me to punish you.”

Sandy got into position obediently. “Sir Robert, I borrowed Rachel’s blouse without permission and got ink all over it. I promise to pay her back for the blouse right after punishment. Could I please not get the paddle and the cane, since I’m going to pay for the blouse?”


“Oh, you’re right, sir. Borrowing without permission truly is stealing. Thank you for correcting me, sir. Must I be paddled and caned?”

“Of course you must, silly Sandy. You tried to conceal your theft and lied. No mercy for you, my dear. You haven’t even asked me to spank you, only tried to beg off. What do you say, Sandy?”

“I’m truly sorry for stealing Rachel’s blouse and ruining it. I promise to pay it back and never steal again. Please p...punish me, sir, so I’ll remember.”

“That’s much better. I consent to spanking you until I’m certain you learned your lesson. Now, I’m going to check that you’re properly dressed. Stand and lift up your skirt.”

“Oh, sir, must I? I’m wearing panties. I always do, and you’ll see them while you spank me anyway.”

“Stop this useless protesting. If you’re not properly attired, your punishment will be increased. If you are, there is no penalty. Up!”

Slowly, Sandy got up and raised her short, pleated skirt. “All the way up, girl,” commanded Robert.

“Oh,” sighed Sandy as she obeyed.

Robert stared at her tight, white panties with the cute heart pattern of tiny holes, the lace waistband and the outlined cuntlips. He encircled her hips with one arm, grasping one cheek to hold her in place, then gently rubbed a finger over Sandy’s slit.

Sandy tried to flinch away, but was held by Robert’s arm. “Oh, sir, are you allowed to do that? No one’s ever touched me there.”

“I have to see if you’re properly attired, Sandy. You know that.” He held her lips between his thumb and forefinger and rubbed her up and down, feeling her dampen and filling his nose with the odor of her arousal.

“Oh, Sir Robert. I’m sure I’m wearing the right panties.”

“Yes, you are, dear, so over my lap you go.”

Sandy let her skirt back down and positioned herself over Robert’s lap. He began spanking her, quickly building up to some rather hard swats. Sandy started gasping, but held her position. Soon, Robert raised her skirt. “This cute skirt and the pleats give you too much protection, so up it goes.” “

Sandy sighed, but made no protest. She cried out, “OH!” after each strike because they now hurt more. Before she knew it, Robert paused again. “Raise your hips, girl,” he said, grasping panty waistband.

Sandy locked her legs together, attempted to tug her panties up and wailed, “Oh, no, Sir. Please! No one’s ever seen me down there.”

“There’s a first time for everything, Sandy. I’m going to spank, paddle, and cane you on your bare bum, so separate your legs and raise up so I can remove these panties. You’re so pretty, lots of guys will want to look between your legs, so you might as well get used to it. I’m just lucky to be the first.”

“Oh, I’m so embarrassed!” But she obediently spread and raised. Robert slowly drew the panties over her tender bum and down her thighs. He was treated to the sight of a very pretty bum and slit indeed. Sandy sobbed, “Oh, the shame.”

Robert resumed spanking immediately, striking her with both hands.“Oh, please, sir, it hurts so much! Please stop. Please!”

“Do you really think you’ve learned your lesson?”

“Oh, yes, sir, I’ll never steal or lie again. I mean it. Oh, it hurts!”

“A spanking’s a punishment, you naughty girl. It’s supposed to hurt. Your pretty bumcheeks are getting red, but the real pain won’t start until I use the paddle and after that comes the cane, which hurts the most. So we’re just getting started, my girl.

“Oh, please, sir. It hurts. My poor bum hurts. Let me do something for you instead. Let me do what I do for my boyfriend.”

That sounded intriguing. Robert paused with his hand upraised. “And what do you do for your boyfriend?”


“ know.”

“I’m afraid I don’t unless you tell me. Do you hold his hand? Write his essays?”

“No, sir, I use my mouth for him.”

“Oh, you mean you suck his cock?” Sandy nodded. “Say it. Say what you do.”

“I s...suck his cock, sir.”

“That’s a very good thing for a girl your age to do for her boyfriend. I’m sure he loves it when you do it for him. Do you like sucking? Do you like how it feels in your mouth? And how it tastes when he comes?”

“Yes, Sir Robert, I do. I like all of it. Please let me do it for you so I don’t have to be punished more.”

“So you’re offering me a sexual bribe.”

“Yes, sir.”

“All right, that’s possible, Sandy. Back on your knees facing me and we’ll talk about it.”

Sandy quickly scrambled into position and looked up hopefully.

“Tell me exactly what you’re offering for a bribe and what you expect in return, Sandy.”

“I’ve really, really learned my lesson, sir. My bum sure stings and if you won’t hurt me any more, I’ll suck you as long as you want, just like I do for my boyfriend.”

“And swallow every drop when I shoot off in you?”

“Oh, yes sir.”

“Have you sucked anyone else besides your boyfriend?”

“No, sir, just him.”

“And you’re a virgin?”

“Oh, yes, Sir Robert. I’ve never gone all the way.”

Robert pondered a moment. “Well, Sandy, that’s a very tempting offer. I wish you’d sucked a few other guys off, that gives a girl experience and teaches her a variety of techniques. Also, I get my cock sucked lots of times. My wife does it whenever I want and my secretary does it almost every day. More important, I really like punishing a girl. I love paddling and caning and I don’t get many chances to do this, especially to a pretty schoolgirl like you. No, Sandy, I think you need to offer me a better bribe than simply a blowjob.”

“W...what do you mean?” quavered Sandy.

“Just think, sweetie. I’ll enjoy your very first fuck and you’ll...”

“Oh, sir! Not that! Please! I’m not ready!”

“Of course you are, Sandy. You’re maturing fast, you’re very pretty so guys want to fuck you, and I saw and smelled how aroused you got when I touched your panties. A virgin who gets that excited is ready for her first fuck. So the choice is clear. Perhaps a bit of pain as as I first enter you and then pure pleasure while we finish our fuck or a lot more pain from the cane. Just think. You’ll be prepared to give your boyfriend the best surprise of his life, his first fuck, the next time you see him. Which is it to be, dear?”

Sandy reached in her pocket and retrieved a handkercheif. She dabbed her eyes with it. Tears flowed down her cheeks. “Oh, please, sir, not that. Let me use my mouth. I don’t want my first time to be like that. Please!”

Robert, charmed and excited by the tears, remained adamant. “Sandy, I already told you a blowjob isn’t enough for me to give up the pleasure of caning you, watching you jump around, squealing and begging. If you weren’t a virgin, I wouldn’t be interested at all. Now I’m running out of patience. Which is it to be, the cane or the cock? If you choose the cane, come back over my knees. If the cock, move to the bed and undress. I’ll have you suck me to get started, and I expect you to let me do whatever I like with you. In exchange, no more spanking”

“Oh, what a cruel choice,” Sandy moaned, but she moved to the bed and slipped out of her skirt and top, looking sidelong at Robert.

Robert, grinning, came onto the bed to claim his bargain. He pushed one of her breasts out her its bracup and kissed and sucked it.

Sandy arched her back, pushing her breast into his mouth. “Oh, sir. this is much nicer than a spanking. You make me feel good now.”

Robert nibbled her nipple until the cute girl sighed. Then he slipped down her body to look at her cunt with the thick, developing outer lips.

He had her get on all fours and rubbed her cuntlips, commenting on how wet she was becoming and breathing deeply of the aroma.

“Oh, sir, it feels good, but I wanted my first time to be different. With my boyfriend.”

“You don’t have to tell him I fucked you, Sandy, and with your new experience, you’ll give him a better fuck than two fumbling virgins can do. I suggest you relax and enjoy it.” He probed her cunt with his finger.

Sandy clamped her muscles together as well as she could. “Oh, sir, I think you found my cherry,” she said, her voice rising with apprehension.

“Well, I don’t want to break it with my finger but with my cock. Let’s see if I can’t make this pretty cunt feel better.” With that, he licked her pouting lips and sent his tongue up and down Sandy’s slit.

“Oh! Sir Robert! Oh! I never.... Oh, that feels good. Please! Yes!”

“Roll over and spread your legs, Sandy.” The girl complied quickly. Robert flicked his finger over Sandy’s clit.She flinched and gasped. “Oh, my, that’s wonderful. My boyfriend must learn to to this.”

“You’ll have fun teaching him. See, this isn’t so bad, is it?”

“This part’s very nice, I must admit.”

Robert lay between her spread legs, licking as the sweet, young girl gasped and moaned. Her girl noises rose in volume as the man kept licking and sucking her wet lips.

Sandy was genuinely excited to be playing a virgin. She remembered how good it felt her first few times and really got into it, soon climaxing loudly. “Oh! Yes, yes, that feels sooo goood!” She thrashed her head from side to side and kicked her ankles into Robert’s back.

When she calmed down, Robert looked up at her and grinned. “You sure sound like you’re ready for your first fucking.” He rolled over and pointed to his cock. “My turn.”

With a grin, Sandy moved to his side, and grasped his thick cock in both hands.

She licked the tip, then took the whole cock in her mouth,

She bobbed her head up and down, giving strong suction with her mouth, rubbing her tongue over the cockhead. Robert groaned and cried out. Sandy tasted his precum and sucked harder, bouncing her head faster.

“Allright, cutie, you’re very good for a beginner, but I want you to stop and get ready for the big event.”

Sandy tried once more. With the cock still in her mouth she mumbled, “Pleash, sir, let me finis wis my mous. I’m sure you’ll like it.”

“Sandy, I’m getting tired of your begging. Now quit stalling and climb up on top of me and put my cock inside you or I’ll cane you and fuck you as well.”

“You want me on top?”

“Yes, I want you to put your first cock in your cunt all by yourself.”

“Do you have to use those nasty words?”

“No, but I like to. Now get on top of me and put my cock in your cunt. It’s time for your first fuck.”

Wiping her eyes with the bunched up handkerchief once more, Sandy cried as she straddled Robert. “Oh, I don’t want to,” she moaned.

“Hold still right there,” said Robert when she was poised right over his tip. He held the base of his cock and rubbed it over her cuntlips, pushing it against her clit. “That’s not so bad, is it?”

“No, but...Oh, well,” Sandy sighed. The cockhead was poised at her entrance.

“Good girl. Now just push down.That’s it. Let me fill your sweet cunt.” Sandy bore down and with a cry, let the cock all the way in.

The invading shaft broke the seal on the capsule nestled in Sandy’s recesses, and red “blood” flowed out, completing the deflowering. Sandy sobbed most convincingly. “Oh, that’s it. It didn’t hurt as much as I thought it might. I guess we might as well have fun.”

She bounced up and down on Robert, getting into a rhythm, sobbing and grimmacing, then finally breaking into a smile. “I like it, having you deep inside me.”

“Girls make too much of virginity. They’re much better off being fucked and giving pleasure to themselves and the guys who like them.” Robert thrust his hips up, driving himself into the girl again and again, with Sandy sliding up and down the pole.

“I think you’re right. I like doing it and my boyfriend will love it.”

“Here, I want to show you another way to do it, Sandy. Climb off me and get on all fours again.” She complied eagerly and climbed off and got in position. Robert was quick to slide back into her warm, damp cunt. He tightly grasped her ass, still slightly red from the spanking. He was tempted to resume the spanking, but stayed in the bounds of their bargain.” This is called doggy style, ‘cause you’re on all fours and I’m behind you like this. How do you like it?”

“I like it a lot, I like it both ways. I didn’t want to, but I’m glad we made the deal.”

“Me, too. I like fucking you and I’m sure your boyfriend will also. Let me hear you say it.”

“Say what?”

“Say what you like doing, fucking.”

“I like fucking, I like fucking you, and I want to fuck my boyfriend.”

Robert sped up, slamming his hips into Sandy’s bottom. “I like fucking you a lot, girl, and I’m going to shoot my hot cum into your wet cunt!” Spasming and grunting inarticulately, Robert pressed himself into her, pulling her hips back and filling her with his fluid.

Sandy tossed her head from side to side, moaning louder and louder, not slowing down until Robert, spent, relaxed.

The pair lay side by side, rubbing each other. Robert told her she’d done a wonderful job, and she kissed him impulsively.

“While I was fucking you from behind, I really wanted to spank you some more. I also love caning, but that role play was really something. You’re a talented girl, Sandy.”

“Well, why don’t we make another appointment, may be for tomorrow, and you can spank and cane me and fuck me again, too?”

“Well, I wasn’t planning to, but...Sure, what the hell?”

“OK, we’ll make the arrangements after I get dressed and ready to leave. How about we make it an extension of this fantasy?”

“Wow, that would be great, Sandy!”

Later, Elena reviewed a secret tape of the session with Sandy. She complimented her on how she used her clothes, the onion in the handkerchief, and how convincing the capsule made everything look. “But your acting was really good for an untrained girl and the way you got him to agree to a new session and suggested continuing the same fantasy, that was the real trick. You’ll go far, Sandy. Like he says, you’re talented.

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