West Valley High Day 121: Cupid

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Susan is a delivery girl.
1.8k words
4.32
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Part 33 of the 130 part series

Updated 10/17/2023
Created 09/21/2016
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Valentine's Day used to be one of Susan Mitchell's favorite holidays. That was typical for popular girls like Susan, who always had a boyfriend who knew they had to spend some serious money on such an important romantic holiday. Somewhere there was a box full of jewelry gifted to her by boyfriends past, trinkets and baubles given freely knowing they would lead to sex with the trim, popular blonde cheerleader. This year, however, Susan knew it was just going to be another day in a long string of painful days for her. There would be no flowers or chocolates and no fancy dinners. She wasn't even sure if she would be attending West Valley Academy's annual Valentines' dance and she wasn't sure she would want to, considering how she would likely be treated by Headmaster Krutz and her friend, Kylie.

It wasn't long before Susan found out how she would be celebrating Valentine's Day. Kylie opened the door, carrying Susan's breakfast tray as well as a long cardboard box. She handed Susan the tray and told her to eat breakfast and take a shower. She took a seat on the floor across from Susan as the girl picked up a piece of toast. "Any chance you plan to tell me what fresh hell you and Krutz have in store for me today?" Susan asked in between bites.

"Nah," Kylie said. "You will see soon enough. So please hurry up and eat and get cleaned up. You have a long day ahead of you." Susan rolled her eyes and finished off her toast and picked through the bowl of oatmeal. She got to her feet and headed over to the shower stall. Even though she had showered in front of, and even with, Kylie a few times as cheerleaders, it still felt odd for her friend to be sitting there cross-legged on the floor watching Susan bathe. The woman took her time under the hot water until Kylie finally yelled at her to wrap it up.

Susan grabbed a towel from a small pile next to the shower stall and spent some time thoroughly drying off her nude body, knowing she was just delaying the inevitable. She wrapped her blonde hair up in the towel and walked back over to Kylie. Her friend opened the box and Susan could see what looked like a pair of long feathered wings. Kylie pulled them out of the box and spread them out on the floor.

Then she tossed Susan a small white stick vibrator and instructed the girl to insert it inside her. Susan did as she was told and then was handed a tiny G-string and told her to put it on. It was a thong that covered virtually nothing, but served the purpose of holding the vibrator in place. In the small triangular patch in the front was a big red heart.

There were a pair of tall, spiked heels in the box and Susan was handed those next. She slipped them on and Kylie assisted her in tying the white ribbons on them. The ribbons wrapped around Susan's ankles and up her shins to just below the knee, where Kylie tied them off in a neat bow. Susan got to her feet and teetered on the six-inch heels. She hadn't worn heels in a while, and it had been quite a while since she had worn ones this tall, so they took some getting used to.

The wings were connected with a metal loop which Kylie passed around Susan's neck and clasped together in the front. The wings were relatively lightweight, but still pulled Susan's head back. Kylie grabbed the strap attached to the base of each wing and brought it around and tied it just under Susan's breasts. While she was still standing in front of Susan, she reached out and placed her hand around Susan's left breast, holding it in the air. She positioned a large red heart over Susan's nipple and pressed the sticker against the girl's breast until the glue set. Then she did the same to Susan's right breast. "That adhesive is made from the same stuff as super glue," Kylie commented, "so good luck getting it off." Susan sneered at her friend but also mentally prepared herself for the pain of trying to get the glue off her nipple later tonight.

Kylie reached back into the box and pulled out a tube of bright red lipstick. She had Susan lean down and she slowly applied the red hue to Susan's lips. Above Susan's eyes, Kylie painted a dark red shade on her eyelids and then placed small red heart stickers on the woman's cheeks. A pair of long white lace gloves that stretched to Susan's elbows completed the ensemble..

Two more items were handed to Susan. One was a plastic bow and arrow and Susan got the idea she was supposed to be some highly-sexualized BDSM version of Cupid. The second item was a white mailbag, which she slung over Susan's neck and left shoulder. "In that bag are valentines that the senior students have purchased for their boyfriends and girlfriends. All you have to do is deliver each of those valentines to the appropriate students this morning." While Susan thought her outfit was ridiculous, she didn't think the task was very daunting, at least by Krutz' standards.

"Oh, one more thing," Kylie said. "Sewn into that bag is a transmitter with a timer. You have one minute to deliver each letter. The timer is reset each time a letter is removed from the mailbag."

"So what does the timer do?" Susan asked, although she already had an idea based upon the device she was told to place inside herself."

"Just what you expect," Kylie said with a grin. "It controls that little toy. And don't get any ideas about removing more than one letter at a time from the bag. Each letter has a tag in it so the timer will sense if more than one is removed at once."

Susan thought for a moment and replied. "How am I supposed to know where to deliver the letters?" Kylie explained that each letter had a note on it with the recipient's name and their class schedule for the morning so all she had to do was find the classroom. Susan quickly realized that she had to pull the letter out of the bag first to read it which meant the timer would start and she would only have a minute to race across the Senior House on those ridiculous heels.

The young woman pondered just not opening the bag at all, figuring that would cause the timer to never be activated but she knew Krutz wouldn't let her off so easy. So she opened the satchel and pulled out the first letter, which was addressed to Mindy Lee, who was currently in a classroom in the C wing. Susan started moving as fast as she could, but a minute was a short time and she had barely made it to the atrium before the she felt the vibrator. For such a tiny little cylinder, the device was quite powerful, causing deep vibrations which made it even more difficult for Susan to walk. She hustled as fast as she could with the letter and knocked on the classroom door. The teacher who opened the door had apparently been briefed by Krutz as he let her in wordlessly and Susan handed the letter to Mindy as the classroom gawked at her costume.

Susan quickly reached into the bag and pulled out another letter and the vibrator stopped. She had gotten lucky and the next recipient was in the same classroom! She handed the second letter to David Miller and then walked out of the room. She decided to wait until she felt the vibrator start again before reaching into the bag.

She wasn't as lucky this time as the next letter was in the A wing, back near where she had started. She decided she couldn't keep going back to the atrium and down the wings so she would have to use the access paths. That meant going outside through the courtyard. The weather had turned decidedly colder last night and a strong arctic chill hit her naked body as soon as she opened the door. She was halfway across the courtyard to the A wing door when the vibrator started again. But this time it wasn't a strong buzzing but more like a sharp sting. Apparently the thing had a small electric shocker and it was currently sparking against her clit. She winced in pain and moved as fast as she could to the door.

The young woman's breasts were starting to burn as well and when she placed her hand over them, they felt warm. She thought at first she was having a reaction to the adhesive and then realized the stickers had been coated in some sort of balm like that used for treating aching muscles. She moved even faster to the third student and then drew the next envelope, which would send her back to the C wing. The first orgasm struck her as she passed near the atrium and she had to lean against the wall as the vibrator sent her into ecstasy. Since it wasn't going to stop, she hustled to the next classroom. Her feet were aching from the heels and the vibrator was alternating between pleasurable pulses and painful shocks now.

Luck was on Susan's side once again and she pulled out four letters in a row, all in the C wing, which gave her a respite from the tremors and shocks. But the next three letters had her crisscrossing the atrium or courtyard and the second orgasm struck as she tottered across the cold sidewalk, the combination of the chilly air on her naked body and the vibrator conspiring to betray her.

The third orgasm occurred as she delivered the last four letters to the B wing. She handed off the last letter to Brian Taub and thought that was the end, but then the vibrator came to life once more. With no more letters in the bag, she opened and closed it, hoping it would stop, but it just kept going. She made her way back to her cell where she would feel comfortable removing the device. She found Kylie waiting there with a wicked grin on her face. Her friend reached through the panties and shut off the torture device after watching Susan orgasm one final time and then helped her out of the wings, heels and panties. True to her word, the heart stickers on her chest proved to be almost impossible to peel off, but since the pain from the balm had subsided, Susan decided to just leave them there and lay down on her thin mattress and tried not to think of tomorrow and Valentine's Day.

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