Allison's School Fundraiser by Tiny Tommy Copyright© 2023 by Tiny Tommy 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. The crowd cheered as the next man eagerly prepared for his turn. None of the men fucked Christine’s needy pussy for more than a few strokes. They didn’t want to risk missing the rest of the weekend, so they quickly switched to fucking her ass. The itch in Christine’s pussy was never satisfied. If anything, she was hornier after the ten men fucked her than before. Cum leaked from her asshole and ran down her thigh. “Time for another faculty vote. All in favor of cleaning out that messy bottom say, ‘aye.’” The crowd responded in unison with a loud agreement. “The enema is prepared especially for extra naughty students. The oil helps it spread deep into her intestines. The ginger shavings add a burning sensation. The nozzle inflates to form a plug.” Jamie held up a nozzle that looked more like a long dildo than any enema nozzle. He inflated the bladder until it looked like a dog’s knotted penis. The nozzle slid easily into Christine’s well-lubed ass. The 5-quart bag hung well above Christine’s hips. Jamie released the clip, allowing the mixture to flow into Christine. The bag was only half empty when Christine started begging him to stop. “Consider your request carefully. If you can’t accept one type of punishment, I will double up on several others. This will be uncomfortable. The amount of fluid will stretch your intestines. You will feel like you are going to burst. I promise that you won’t. The pressure will slowly force the fluid even deeper inside you, cleaning out your body like never before. Do you still want me to stop?” “No sir, I will accept any punishment you deem necessary. I apologize for my outburst.” “Your apology is noted. You will receive ten additional swats with the strap for the outburst. The good news is that the strap may help distract you from the enema.” Jamie drew another name and handed him the strap. It looked like a wide belt with a handle, except the leather was much thicker than any belt I’ve seen. The selected gentleman swung the strap across the center of Christine’s ass, hitting both cheeks. The strap produced a distinct crack. He waited after the first stroke as the white rectangles turned bright red before repeating the next stroke. The enema bag was empty by the 7th stroke. Jamie pumped the bladder even larger, making sure that nothing would leak. He pulled her stockings down to the knots securing her ankles. “This young lady still needs to be punished for her uniform violations. Since she is a repeat offender, the punishment will be increased to 50 strokes. Each classmate who hasn’t already spanked her will have two swats with the small paddle.” Jamie held a leather paddle roughly the size of a paint-stirring stick. The 25 men who hadn’t already spanked her lined up. Christine remained tied to the sawhorse with her legs spread wide. Her ass cheeks were bright red from the strap. Her pussy lips were still swollen with excitement. The pressure and burning in her abdomen hurt more than her bottom, at least until the spankings restarted. Each man favored a different approach. Some liked adding the red on her butt. Most enjoyed finding white space on her thighs so they could leave their own mark. Finding unmarked skin meant some of the swats had to focus on her inner thighs. It wasn’t prearranged, but the last three men decided to spank her directly on the pussy. Christine’s shrieks of pain from the first swat on her sensitive cunt likely motivated the last two men to spank her there as well. “Are you ready to empty those bowels, young lady?” “Please.” Jamie placed a collar around her neck and attached a leash. He untied her from the saw horse. Christine removed the hose bunched at her ankles and began to run her butt. “There will be none of that, young lady. Crawl like a dog and follow me.” Christine hesitated when they reached the back door. “What if a neighbor sees me?” “It could happen. Do you want to wait until dark to empty yourself?” Moving around had made the bloating and burning worse. Christine couldn’t tolerate choosing to keep feeling this way. “No. I need to go too badly to wait. Please let me poop outside.” Christine crawled out to the yard and squatted over a pail. Jamie released air from the plug, yanking it out before it was completely empty. Brown water gushed from Christine’s ass. “May I have some toilet paper?” “You’ve made too big of a mess to use toilet paper. I’ll rinse you off. Sort of like an outdoor bidet.” Jamie retrieved a hose with an attached spray nozzle. “Kneel and spread your ass wide. Head on the ground.” He sprayed cold water on Christine’s ass cheeks and thighs. She found the cold water relatively soothing on her freshly spanked skin until Jamie changed the nozzle to produce more concentrated, forceful streams. He aimed these directly at Christine’s asshole and pussy. “Reach back and pull those cheeks wide apart so you can get a thorough cleaning.” Christine was noticeably shivering when Jamie finally stopped. “Let’s walk you around the yard to dry off.” She understood that meant crawling like a dog while Jamie held her leash. Christine was sure that she saw curtains moving in nearby houses but also thought that it could just be her paranoia. When Christine finally returned inside, the sawhorse had been replaced with a Y-shaped contraption. The two sides that formed the top of the Y were heavily padded with thick leather straps hanging next to each pad. The center bar of the Y contained only a ring with a hook. The young student knelt on the pads and leaned forward to have her collar clipped into the hook. She could feel the straps being secured to her legs. “I’ll bet this little slut has left many of you frustrated and horny with her blatant disregard for our uniform policy. I think it would be an appropriate punishment for her and recompense for each of you if anyone who needed relief after all of her teasing behavior had the opportunity to release their load in her vagina. Please raise your hands if you are interested.” Every person in the room played along and raised their hand. “Under your chair is an envelope with a number. That will be your order.” Jamie rubbed her pussy. Christine was so aroused by the public humiliation that he could quickly slide two fingers inside her. “Each of you deserves a chance to use her fresh pussy. In the first round, you will have 15 seconds to fuck her before the man has his turn. The next round will extend that to 30 seconds, increasing by 30 seconds each round until everyone has emptied a load inside her pussy.” Christine had multiple orgasms in the first 30 minutes. It was over 90 minutes before the first man came in her pussy. She had a cock filling her pussy for over 5 hours straight before every man finished. Cum ran down her legs to the floor. Her pussy was so abused that it made no attempt to close. It wouldn’t have mattered because Jamie shoved a baseball bat into her sloppy cunt and secured it in place with athletic tape. The men broke for supper. Supper, and perhaps some medication, helped all of the men recover. They were eager to take a turn with Christine’s ass. The men reversed the order and repeated the same process with Christine’s backdoor hole. Christine endured six hours of having her ass pounded by these 30 men. More cum leaked down her legs. It was after midnight. “Christine has earned one final punishment. The student handbook prohibits sexual activity. She has clearly broken this rule and will be whipped for her infraction.” Jamie had a single-tail whip with a flapper tip. The wider tip made a satisfying noise and painful strike with much less chance of cutting the skin. He delivered blow after blow with practiced accuracy and intensity. He worked both thighs and butt cheeks, leaving distinct marks everywhere he hit. He finished with five strikes directly between Christine’s spread legs. The welts he left, particularly on the tender flesh around Christine’s pussy, would take days to heal. Christine was left tied on the Y-frame all night. The 30 men wanted to get their money’s worth. At least one man was with her at every point during the night. Her nipples were pinched, pulled, and twisted. Her pussy and tits were slapped with the ruler. Her cunt and ass were attacked repeatedly with enormous dildos. Christine gave numerous blow jobs. Some men came in her mouth, but plenty opted to cum on her face. Sunrise triggered the end of Christine’s punishment. Many of the whip marks were still visible. Cum had dried on her face, chest, legs, and hair. Jamie untied her from Y-frame and handed her a thin, tiny sundress to wear home. The thin material clung to Christine’s body, making it clear she wasn’t wearing anything underneath. Christine was allowed to use the bathroom but not clean anything from her body. Not even wiping herself with toilet paper after peeing. It had already been arranged that Christine would take the bus to the church. Pastor Clarke and I would meet her there before church. Christine walked four blocks to the nearest bus stop. She passed multiple dog walkers and joggers. Riding the bus was even worse. Christine was sure that the stench of sex and cum had to be overpowering in a closed space. She was right. It felt like everyone was staring at her. She was mostly right about this as well. Christine arrived at the church about an hour before Sunday School started. We met in the pastor’s office. Pastor Clarke took command. “Undress so I can inspect the results and confirm that Jamie and his friends abided by our agreement.” Christine removed her sundress, folded it, and placed it on a visitor chair. “Stand on the coffee table so I can get a better look.” The welts on Christine’s thighs and around her cunt were still clearly visible. No other marks remained. The dried cum seemed to cover most of her body, although that certainly wasn’t truly the case. Our pastor began rubbing his finger gently on her clit hood. Her clit popped out almost instantly. Christine’s pussy lips quickly swelled, revealing a pussy opening that was still gaping open at least as wide as my thumb. “It looks like you enjoyed this punishment more than a young lady should. Perhaps I should have several of the elders join me while we continue your punishment.”