Allison's School Fundraiser - Cover

Allison's School Fundraiser

by Tiny Tommy

Copyright© 2023 by Tiny Tommy

Erotica Sex Story: This is a continuation of Allison Goes Back to School and you may want to read that story for context. Allison continues playing the role of the much younger Christine. Plenty of spanking and a gangbang. If breast and pussy whipping aren't your thing, please don't read this and leave a bad review.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fiction   School   Wife Watching   BDSM   Humiliation   Rough   Spanking   Gang Bang   Anal Sex   Cream Pie   Enema   Exhibitionism   Clergy   Small Breasts   .

Pastor/Principal Clarke asked that Christine and I visit his office during summer break. I thought this was an unusual request, but I wanted to know what he had in mind.

“Thanks for coming in on short notice. The school needs your help. We are facing a serious financial gap this year.”

“I really can’t afford any additional tuition.”

“None of our families can. Fortunately, we have a fundraising opportunity this weekend. A potential benefactor contacted me about a party he is hosting this weekend and is willing to make a large donation to the school if one of our 18-year-old students could provide entertainment.”

“So you would like Allison to pretend she is 18 this weekend?”

“No, I need 15-year-old Christine to pretend that she just turned 18 while convincing people that she is probably younger.”

“A younger girl wouldn’t be legal but would be more valuable for their purposes. So we agreed that I would pick a girl who has ‘wink-wink’ recently turned 18.”

“Why would we agree to this?”

“It isn’t a secret that you both enjoy your wife playing the role of a teenager, being spanked, and even fucked, by other men. This weekend will provide an abundance of that. Unfortunately, Tommy won’t be able to stay with you during the party. He will drop you off at 6 AM on Saturday, and you will take the bus back to the church on Sunday morning.”

“I’m not sure about that. I’m worried about her safety.”

“I think you are more concerned with being able to watch. Fortunately, the host is live streaming the activities for some of his close friends who aren’t able to attend in person. I can arrange a login for you.”

Christine spent the afternoon getting ready. We started with a trip to the lingerie store. Christine picked out a heavily padded black lace bra, matching panties, a garter belt, and stockings. She brought me along and made me pay for everything, which was particularly embarrassing given our apparent age differences.

Christine continued getting ready when we returned home. She used extra-strength denture cream to keep her braces on all weekend. She went a little over-the-top on makeup, trying to capture the look of a girl pretending to be older than she was. It worked; the awkward makeup made her look even younger. She fixed her hair in a single ponytail.

Just before we left, Christine changed into her recently purchased lingerie. She put on her school uniform over the lingerie. The padded bra caused her small shirt to nearly split open at the buttons, revealing glimpses of the black lace peeping out between the buttons. The skirt extended just beyond the tops of the black stockings. The seams down the back of the stockings and the high heels completed the look of a costume rather than an actual school uniform. I believed that Christine had perfectly pulled off the look of a younger girl trying to pretend that she was older. I hoped the party guests reached the same conclusion.

The party was being held at a large, stately home across town. It was already crowded when I dropped off Christine just before 6. I rushed home to turn on the live stream.

“You didn’t drive yourself?”

“I’m not old enough to drive.” Christine slipped up.

“I thought you were 18?”

“I am; I just meant that my parents don’t think anyone is old enough to drive until they graduate high school.”

The host, Jamie, made a knowing smile and invited her inside.

“I’d like to introduce Christine. She is a Senior at Community Christian Church School, and she recently turned 18.” At this point, he made an exaggerated wink to the group. “She will be our entertainment for the weekend. We will begin in the auditorium.”

Jamie had installed a small stage at one end of the family room. Rows of chairs were neatly arranged on the wood floor facing the stage. On the stage were a desk, a sawhorse, and a gymnastics high bar. A red curtain ran the entire back wall, providing the further illusion of a school auditorium.

Jamie and Christine climbed the stairs to the stage. 30 men filled the chairs in the room, anxiously awaiting the weekend’s events.

“I’ve heard comments from teachers and other students that your uniform doesn’t conform to school policy. This isn’t the first time, so I’ve determined that being punished in front of the school might get the message through to you.”

Christine embraced the roleplay without any encouragement.

“Please, sir, the punishment is bad enough. Does it have to be in front of everyone? That is so embarrassing.”

“That is the point, young lady. Perhaps now you will finally get the message. Let’s begin with that shirt. It is clearly too small for you, and it’s causing a distraction. Take it off.”

Christine took her time unbuttoning her top. When she removed it, she folded it carefully and placed it on a nearby chair.

“What does the dress code say about undergarments?”

“It states that all undergarments must be plain white without adornments.”

“Does your bra violate that dress code?”

“Yes, sir. It is black with lace.”

“You will need to remove it.”

Christine removed the padded bra and placed it with the shirt on the chair.

“You have much smaller titties than you wanted everyone to believe. Does the student handbook include any instructions about honesty?”

“Yes, students are expected to always tell the truth.”

“Wouldn’t you agree that your padded bra was a deliberate attempt to deceive?”

“I guess so.”

“These are three serious infractions and need to be appropriately punished. Stand under the high bar and raise your arms.”

Jamie tied Christine’s arms overhead stretched out to the sides of the high bar. Her small breasts nearly disappeared in this position, but her thick, pokie nipples seemed to stand out even more.

“I think that anyone who feels they have been deceived should have the opportunity to inspect those tiny titties more closely.”

All 30 men stood in line, waiting their turn for inspection. For the next 45 minutes, Christine’s tits and nipples received considerable attention. Some men were more interested in caressing and sucking on those breasts, proving that those tits were well less than a handful or mouthful. Her nipples received even more attention. While some men were gentle, others preferred to pinch, pull, twist, and bite.

“Now that the inspection is complete, we can proceed to the punishment for the infractions. For lying about your tiny titties, you will receive 20 swats with a ruler on each tit. We will draw names for the two men who will have this honor.”

Each of the men in attendance had paid for chances in the drawings. Jamie drew two tickets, and the lucky winners came forward.

“There is one firm rule for this weekend. We will not permanently damage this young lady’s perfect skin. If you draw blood, you will be asked to leave immediately. Contain your enthusiasm.”

The first man chose to swing the ruler forehand, striking Christine’s right tit. The first few swats were slightly tentative as he judged the effect on her skin. Soon, the strokes were leaving deep red, overlapping marks. Christine was flinching and starting to cry.

The second man was also right-handed, so he swung backhanded at her left tit. Unlike his predecessor, he aimed all 20 strokes at Christine’s nipple. Christine’s light tears turned into heavy sobs.

“Christine’s titties may be too small to take any more swats right now, but there are still plenty of ways for her to receive the rest of her punishment.”

Jamie untied Christine’s arms, and she returned to standing next to him on the stage.

“Time to remove your skirt.”

Christine stepped out of her skirt, folded it, and placed it on the chair with her other clothes.

“Those undergarments don’t follow the dress code either. Take off the panties. Our policy doesn’t address the garter belt and stockings. I will need to call for a faculty vote on that.”

Christine removed her panties.

The assembled group voted in favor of allowing Christine to keep the garter belt and stockings.

“We still have the punishment for the two previous uniform violations, plus the new ones. Stand in front of the sawhorse.”

Jamie tied her legs to the sawhorse and her hands behind her back. He attached clips to each nipple with wires leading to a control box.

“This box will send an electric current to your nipples. Sometimes the sensation will be delightful” Jamie adjusted the knob slightly, creating a pleasant vibration for Christine.

“Other times, the pain will be worse than having your breasts spanked.” Jamie adjusted the knob until Christine writhed in pain.

“You will receive 30 swats with the crop on the front of your thighs while the box teases and torments your titties.”

Jamie drew names again, reminding both new men about the restrictions. Christine’s legs were spread a little over shoulder width apart, providing a nice view of her bald pussy for the spanking. The first man was very skilled with the crop. He began at the top of the stocking, using three strokes of the crop to work around to the inside of Christine’s thigh. None of the marks overlapped, but there was only a thin white line between them. He moved slightly higher on her thigh and repeated the sequence. The final swats barely missed her cunt.

The second man violently attacked the other thigh, not caring whether the swats overlapped. He had finished 12 swats when an excruciating shock started pulsing through Christine’s nipples. He made three hard smacks in rapid sequence directly on Christine’s pussy.

Jamie rubbed his finger between the lips of Christine’s recently spanked pussy.

“This little slut is enjoying all the attention.”

Jamie’s finger returned to Christine’s pussy, rubbing her clit.

“I have decided to include a bonus auction. I never expected that a Christian girl would be such a slut. The winners of this bid will have the chance to fuck her needy pussy and cum in her ass. Only the top 10 bids will be allowed to participate. If you cum before you are fucking her ass, you will be asked to leave this event without any refund of what you have already spent.”

The men watching were horny, excited to fuck that teenage cunt. Men were bidding against each other for the chance to be the first cock inside that young cunt and the chance to cum. The bids raised over $10,000 additional dollars for the school. The ten winners lined up along the side of the stage.

Christine was still tied to the sawhorse. Jamie tied her arms to the other side; the highest bidder stepped forward, lowering his pants to his knees. His cock was at least 8” long, although the length made it appear skinny. He slid the head of his cock between Christine’s wet pussy lips until the tip was barely entering her cunt. He slammed his hips forward and buried his cock inside her body. Christine gasped in some combination of surprise, pain, and pleasure. He took his time, sliding his cock in and out slowly after that first deep stroke. After about a dozen strokes, the man pulled out. Christine pushed her hips towards him as much as she could, begging to have her needy cunt filled while he lubed his dick in preparation for taking her other hole. He took her tight asshole with vigor, stroking his cock deep in a steady, fast rhythm. He only lasted a few minutes before dumping his load deep in her bowels.

 
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