[ENF] Valentine's Disaster

[theoneandonly27]

(Everyone is 18+ years old)

Cara was extremely excited about her first real Valentine’s Day date. She wasn’t popular and instead was more like your average geeky girl. Cara had shoulder length brunette hair that she normally wore in a ponytail and black rimmed glasses over her green eyes. She had a slender body with a small chest and rounder than average behind, which she always hid beneath wavy skirts or baggy pants. Cara was definitely cute but her social status kept many boys from her. Out of the blue, one of the popular football players, Jason, asked her out for Valentine’s Day. Of course Cara said yes! Cara had a huge crush on Jason that she didn’t hide really well. A crush that Sasha, who was the head cheerleader, and her cronies knew about. Sasha didn’t like Cara. She didn’t like that Cara always stared at Jason, or that she would always offer to do his homework. Sasha secretly wanted to date Jason and when he asked Cara out instead of her, it made her lose her cool and contemplate doing something truly devious. Sasha made a plan with a few of her cheerleader friends to ruin Cara’s big date with Jason. She had one of her friends ask Jason his plans in a very friendly manner even pitching some ideas.

The plan for the date was for Jason to pick Cara up at her house and then go to a restaurant for some food and then go to the minigolf course. It was a simple date, but Cara couldn’t wait. She has been glowing all day and even caught herself humming a happy tune from time to time. Cara took a shower and then wrapped herself in a big fluffy white towel and went back to her room. She contemplated her choice of clothes for the date. She obviously didn’t want to wear fancy dress but also didn’t want to look like a bum. But before clothes she opened up her underwear drawer and went through it. Cara blushed a bit moving aside some of her more dorky/childish pairs of panties that were adorned with ponies or kitties and stuff of the like. She pulled out the 2 thongs she owned that she practically never wore. One was a gag gift from one of her friends that was completely transparent and tiny with red borders, the other was black and had ‘Bad Girl’ written across the front. Cara felt her face get red as she imagined Jason seeing her in either. “Oh, you like my thong? Haha, oh Jason, I wore it for you…” She shook the dream from her head and placed them both back in the drawer. Cara instead pulled out a cute pink and black striped bikini style pair that fit her ass very snuggly. She then found a black pushup bra that would make it seem as if she at least had a Bcup. After putting on her underwear choice, she admired herself in the mirror. Her panties accentuated her round behind in a very nice manner. Cara’s alarm on her phone suddenly brought her back and she began to panic that Jason was going to be here any minute. Cara scanned her closet for a nice poutfit and happily settled on black leggings with a small grey skirt over them and a white button up blouse. Instead of putting her hair in a ponytail, Cara put a pink headband in. She stepped back and judged her outfit and really liked what she was seeing. Cara left her room and waited by the door for Jason to pull up and when he did, she went to his car and got in.

Jason complimented her look as he clearly saw a change from the normally geeky looking girl. The two talked as he drove and it was going really well. Jason told her he was always very appreciative of her willingness to help with his work and just for being very sweet. Cara’s cheeks flushed red a bit listening to her crush talk about her. The night was going perfect so far. But then Cara saw them drive past the restaurant they were supposed to eat at. She began to question Jason, but he calmly told her that he couldn’t pass up a suggestion for this new diner he got from Becky, a cheerleader. He could see that Cara was a little taken aback from the change of plans so he told her they didn’t have to go there if she didn’t want. Cara, playing cool, said she didn’t mind and would like to try the new place too. Besides, what could go wrong by going to this diner?

Jason and Cara entered the new diner and found it half full. A few older couples and random people from their town were sitting and eating. Cara scanned the room and was surprised how nice the place actually was. She feared a ‘diner’ would take some romance from this date, but the inside was really welcoming. That is until Cara spotted a cluster of Cheerleaders sitting in a booth in street wear, Sasha among them. Sasha was wearing a blue belly shirt that showed off her abs and a low riding blue jean skirt. Cara was about to motion to Jason to leave, since she knew Sasha was always rude to her and she didn’t want this night to be ruined, but the hostess started to lead them to a table and he was already following her. Cara followed meekly behind trying to not be seen by the group. Sasha instantly spotted them and grinned and followed them with her eyes to their booth across the diner. Phase 1 can now begin.

Cara sat across from Jason and must have looked a bit uneasy, because Jason asked if she was alright. Before Cara could answer though, she was interrupted by their waitress who had a voice she knew. Cara looked at the girl and saw that it was Tina, a friend of Sasha’s and fellow cheerleader. Cara shifted in her seat and watched Tina flirt with Jason a bit and touch his shoulder. The two talked about the coincidence of being here. Tina paid Cara no attention which really irked her. She cleared her throat loud enough to break their conversation where Jason then proudly announced that he was on a date with Cara. Tina’s facial expression changed to disgust and faked a ‘hi’. Cara was happy that Jason stuck with her. Tina got their drink orders and left. Cara was watching her leave but was interrupted by Jason starting a conversation, which she happily participated in. Unfortunately, if she kept watching Tina she would have seen her stop at Sasha’s booth and talk with the group and giggle and leave. Cara and Jason were in deep talk about all types of things when a shadow of a figure approached them again. Cara turned to see who it was but was shocked when her body was drenched with ice cold water. Almost half a pitcher of water fell onto her head and white blouse. Cara shrieked and stood up as Tina righted the tipped pitcher. Cara grabbed at napkins to dry herself while Jason also sprang to his feet too and began to grab napkins and started to help pat Cara down. Jason wasn’t really aware of what he was doing as he was just trying to help, but he was patting onto Cara’s chest. Cara blushed and stepped out of the booth away from Jason’s helpful hands. Tina began to ‘apologize’ to the dripping wet Cara. Cara looked Tina in the face and saw that between her half hearted apology she was staring at Car’s chest. Cara looked down and saw that her black bra was very visible through her wet white shirt. She threw her arms over her chest and let out an “EEEkk” before running to the bathroom. She had to run past the booth of cheerleaders who were sitting right outside the door and they were giggling at her. She tried to pay them no attention, but if she did, she may have noticed that Sasha was not with them.

Cara entered the bathroom and did a quick check to see if anyone else was in there but all the stall doors were slightly opened, meaning no one was inside them. She then turned and locked the bathroom door. Cara went to the sink and looked at herself. Her white blouse was practically see through so the black pushup bra was clearly visible. She stared at her heaving chest as she breathed very hard. She was on the verge of tears. Cara made a decision and removed her blouse. She grabbed paper towels and went to work trying to dry her shirt. She felt exposed being in her bra, but the bathroom was locked so no one else could come in and see her. Cara d****d her shirt over a sink and patted it down with handfuls of paper towels. It finally looked like she was drying it. The sound of something falling on to the tile under the sink area, made Cara jump in fright. Curious as to what made the noise she bent down and looked under the sink. She saw a quarter still spinning before finally falling over. Sh cooped up the quarter and stood back up and placed it on the sink next to her……Wait, her shirt was missing! Cara looked at the sinks and back to the floor. Where did it go? She was startled when she heard a voice from behind her.

“Looking for this?” The evil voice of Sasha came from behind her. Cara turned slowly covering her bra with one arm. She saw Sasha smiling and holding the damp shirt out to her.

“Wha..what are you doing in here? How did you get in here? Were you waiting for me?!” Cara’s last question made me mind race and scared her a bit. “Gimme my shirt back” Cara reached for her shirt with her free arm.

“Oh, no please?” Sasha whisked the shirt back out of Cara’s reach. “I can’t give you this shirt back, its ruined and wet. I should just throw it in the trash.” Sasha mockingly walked toward the wastebin.

“Wait! No! I need my shirt. Please, Give it back!” Sasha stopped her walk and turned back grinning at Cara.

“Hmmm, well how about a trade? I’ll give you your shirt back, so you can cover up your pushup bra..” Cara went to protest that last statement but Sasha continued, “..Yes I said that right, pushup bra. Please I know one when I see it. So I’ll give it back only if I get something from you in return.”

Cara didn’t like hearing what Sasha said, but she shoved her free hand in her pocket and found a crumpled up 5 dollar bill. She reached it out toward Sasha. “Here, this is all I have on me. My purse is at the table, I’ll give you more if you let me go back out there with my shirt.”

“$5?! I don’t want any of your money. I was thinking more along the lines of your skirt.”

“What? No way. I’m not giving you my skirt!”

“Ok, well then I guess I’ll just keep your shirt and leave. You can go back out with your pushup bra on and face Jason. I bet he’d like to see that.”

“Wait! Stop. Ok. Ok, I’ll give you my skirt. I have leggings on so its not that bad. I’ll just tell him my skirt was wet too.”

Cara unzipped her skirt and let it fall to her ankles. Even though she had black leggings on, she felt incredibly exposed. Sasha was surprised that Cara was complying this easily. She must really like Jason. Cara bent over and grabbed her skirt and walked it to Sasha and the two traded items of clothes. When Cara turned around and walked back to the sink area, Sasha saw her bubble butt for the first time perfectly framed by the leggings and her jaw dropped in jealousy. She had no idea Cara had such a nice ass and she knew that if she was confident enough and Jason saw it, that Cara could easily have him wrapped around her finger. Sasha needed to go a step further right now. Cara was busy trying to put her damp shirt back on when Sasha snuck behind her. She shoved her hands down the back of Cara’s leggings and grabbed her panties. Cara yelped as Sasha pulled her panties up into a fierce wedgie. She was trapped in her wet shirt and couldn’t get her arms free. Sasha laughed as she pulled and tugged harder and harder. The pink and black striped panties were at mid back now and Cara was standing on her tippie toes to relieve the pressure and pain. She screamed for Sasha to stop but it wasn’t any use. Sasha gave one more hard pull and held the panties up with one hand. With her other she reached under the back of Cara’s shirt and unclasped her bra. Cara felt her bra go loose and was able to grab the front of her cups thinking Sasha was trying to remove it. Instead she felt Sasha pull her panties up more and then she felt her bra get reclapsed. Sasha shoved Cara forward and stepped back to admire her work. Cara was stuck in a bra connection wedgie. Her Panties were pulled up from the back of her leggings and held up by her bra. Cara finally got her shirt on but waddled around with the wedgie. She tried to figure out what was causing it and finally realized what predicament she was in. She went to free herself but Sasha stopped her.

“Oh no no no. That’s gotta stay like that, sweetie. If you remove it, I’ll take your shirt and pants and send you out to Jason in your undies. I’ll be watching your every move too, so don’t think about trying it during dinner. So go out there and try to have a good time, darling.”

Cara was about to protest when she heard Jason’s voice coming from the other side of the door.

“Cara? Are you ok in there? Want me to take you home?”

Sasha looked at Cara and walked up to her and whispered to her, “tell him you’re fine and go eat or I’ll strip you right now and shove you out.”

Cara was too scared to think anything through so she obeyed,” I’m…fine. Coming out now.”
Cara went to the door and unlocked it and saw Jason leaning against it. His expression made her blush when he looked her up and down, noticing her skirt was missing and her shirt was partially see through. Jason led the way back to the booth, turning and asking if she was ok like a gentleman during the short walk back. And it’s a good thing he walked first, because if he trailed Cara he would definitely see that she was in a bra connection wedgie, because the back of her shirt was still very much see through. Cara scooted into her seat that was now dry. Sitting down made her wedgie seem worse for some reason. But Jason was very kind to her and her pretended everything was ok and normal and started joking and talking with her again. Cara moved her terrible feelings to the back of her mind and tried to make the best of this dinner. Every time she shifted though she was reminded of the constant pain and pressure in her ass and pussy.

Sasha watched like a hawk at the couple talk and smile and joke around. She was fuming. This isn’t supposed to be how this goes. Cara was supposed to be humiliated and act like a little bullied nerd. Sasha needed to do something else to ruin this night for Cara so her and her cheerleader friends all started thinking. Maybe they could sprinkle some colon-blow in their desert….but they didn’t have anything like that on them, maybe they could have Tina drop the desert on Cara so she would remove her shirt….but if that happened she would probably just leave instead of remove her shirt. Damn, what could they do? In the meantime, Cara and Jason finished their meal and decided to opt out of desert altogether. Cara asked Jason if they could leave, clearly not wanting to be near Sasha. The two got up and headed for the door. Sasha jumped to her feet and watched them exit the diner. She looked at her friends and simply yelled “after them!” with no plan in mind. On the way to Jason’s car, Cara asked to be brought home. Jason looked extremely disappointed. He wanted to go mini-golfing still and hang out more. It seems he’s actually fallen for Cara. He agreed of course, but Cara then said, “Well, if you have a jacket I can wear then, I guess I’ll go mini-golfing still.” Jason’s face lit up, and he responded by saying “heck yea!”

Jason dug through his car to find a jacket for Cara and while he was distracted Cara unhooked her bra which set her panties free. With one hand she rehooked her bra, and the other she stuffed her stretched panties back into her leggings. Jason would glance back at her while sifting through his back seat and see her awkwardly shift around but thought nothing of it other than she was cold. When in actuality, Cara was picking the wedgie from her ass and smoothing out her stretched panties so they didn’t look weird if Jason were to see her backside. But unbeknownst to Cara, Sasha watched her undo the wedgie. She and her cronies slowly began to exit the diner and cross the parking lot toward Cara. They stopped however and saw that Jason handed Cara his letterman jacket. Jealousy and rage filled Sasha while glee and warmth filled Cara. Cara put the jacket on over her damp semi-transparent shirt and did a small twirl. Jason smiled and laughed, and when Cara twirled he got a glimpse of her bubble butt in the leggings and his smile grew wider. The two got in his car and off they went to the mini-golf course no too far away. Sasha and her crew scrambled to her car and quickly took off following them from a distance. Becky, one of Sasha’s friends nervously asked what they were gonna do if Jason is just dropping Cara off at home. Sasha turned to her and made it very clear, no matter where that b*tch was headed she was going to be humiliated in front of Jason.

Cara and Jason already started to play when Sasha and her friends got to the place. From what Sasha could see the two were basically in love and having a wonderful time. It was only a 13 hole course but it was filled with all sorts of hazards and windmills to make it a fun challenging time. Sasha examined a course and put together a plan. On hole 8, that’s when they strike.

Cara was on cloud nine. The mishap at the diner was far from her mind. Jason was a genuine great guy and they seemed to be completely into each other. She feigned that she didn’t know the proper stance to putt and had Jason show her. He leaned over her shoulder and placed his hands on hers and put them on the putter. Then he had her spread her stance a bit and move their hips together as she hit the ball. Cara felt Jason’s body press against her lower back and butt when they moved together and she blushed a bit and if she saw his face, so did he. Everything was going great. They had just both sunk their putt on hole 7, and started along the path to hole 8. Hole 8 was in a more secluded area that had a giant windmill at the end around a giant blind curve that was in a cave you had to walk through, in other words you can’t see the end from the start. On the way to the starting of hole 8, a ‘stranger’ bumped into Cara pretty hard and caused her to drop her ball. The stranger mumbled an apology when Jason turned to yelled at them but he couldn’t see who did it since the start of hole 8 had more foot traffic because there was a refreshment stand near by. Like a gentleman he told Cara he would go get the ball, but found it a more difficult task because it seemed like someone was ‘accidentally’ kicking it further and further away. Cara sat on the wait bench at the start and grabbed out her phone. She wanted to text her friends about how well the date was going. She was in mid text when 4 hands grabbed her from behind and began to drag her into the cave and out of sight. A hand was plastered over her mouth so she couldn’t be heard, but that didn’t stop Cara from trying to yell as loud as she could. She looked around her surroundings and saw that she was dragged to the end of the cave and could see the giant windmill. Then she felt duct tape placed on her mouth and her hands taped together. Cara was then shoved to the ground and she looked at her assailants and began to panic seeing Sasha and 2 other cheerleaders standing over her.

“Hey b*tch! I saw you take out the wedgie. You shouldn’t have done that. Now you’re going to get really humiliated.”

Sasha was interrupted by the sound of Jason echoing through the cave, “Cara? Hello? Cara? Where did you go?”

Sasha immediately grabbed Cara’s phone and scrolled through her contacts and sent Jason a text…”Sorry, ran to the bathroom, be right back.”

They heard Jason walk back away from the cave to the start of the hole. “Whoa, ok, that was close. We don’t have much time I guess. Damn, in my head I really wanted to drag this along and prolong your humiliation, but I guess I’m going to have to speed it up.”

Cara had tears in her eyes and fear in her heart. What was this crazy b*tch and her cronies gonna do? And Why? Why her? Cara tried to inch worm away but Sasha’s 2 friends grabbed her shoulders and lifted her up. Sasha pulled out pair of scissors and cut Cara’s hands free. Cara thought that maybe they were letting her go, but the girls behind her stripped her of Jason’s letter man jacket and then retaped her hand behind her back. Sasha then approached Cara’s front and slid the scissors along the bottom of her shirt and began to snip it upwards. Cara began to panic and move when Sasha started cutting her shirt off her, but the 2 girls held her in place. The cool metal of the scissors was an unwelcome feeling against her warm skin. Sasha easily finished cutting the shirt open and without hesitation cut the sleeves and completely removed the ruined shirt. Cara was now only in her black pushup bra again and leggings. Sasha didn’t stop though, she placed the scissors down the side of Cara’s leggings and snipped them to her shoe. The material split open and revealed Cara’s left pale leg and left panty clad ass cheek. Sasha went to the other side and did the same thing. Cara’s tattered leggings lay around each ankle like a peeled banana peel. She now stood in her underwear. Cara was crying now. Tears ran down her cheeks leaving a trail of dark mascara they took with them. Sasha put the scissors down and started to remove Cara’s shoes. She got the right shoe off and when she started on the left Cara kicked her in the nose. Sasha fell on her ass and clutched her hurt face. Cara tried to wiggle away from the two girls and almost got free until she felt Sasha grab the back of her panties and pull her back to the girls.

“YOU b*tch!! I can’t believe you did that. I think you broke my nose! That’s it, we’re going all the way”

Sasha grabbed the back of Cara’s bra and unhooked it. But because Cara’s arms are behind her the bra didn’t fall off, it just became loose. The cups laid atop each tit, threatening to fall down. Cara didn’t move for fear but it didn’t matter. Sasha grabbed the scissors and 2 snips later, Cara’s bra was on the ground and her tiny Acup tits were free in the night air.

“Oh my! Look at how small they are! Ahhhahaha! Oh look at her rosy nipples. They are so hard and pointy. Don’t get too close girls, they’ll poke your eye out.” Sasha’s taunts sent Cara into hysterics. “Save you’re crying for what comes next sl*t.”

Sasha grabbed the waistband of Cara’s pink and black striped panties and yanked them to her ankles and then off her feet. She twirled the panties around her finger. “OH MY GOD. Look at her fuzzy pussy! Oh Cara dear, I love your trim job. A perfect triangle of brown hair. It really is the only thing on you that screams adulthood, well that and your ass. I want you to know, if I had time I would shave you bare and take your sign of adulthood and leave you looking like a baby b*tch.”

Cara was now completely naked and being taunted. Her tiny tits and small trimmed pubes were completely exposed to Sasha and the outside world. Cara’s tears fell down her cheeks. She wanted to wake from this nightmare. Instead she was pulled toward the windmill. She was shoved against the wooden spokes and heard the noise of duct tape…

ZZZT ZZZZT Jason’s phone vibrated and he got a text message. He looked at it and it was from Cara, “Come to the windmill, I have a surprise for you that you don’t want to miss. Xoxo” Jason grinned. He was wondering what was taking her so long, but now he got his hopes up. “What is she doing? Is she gonna be naked under my letterman jacket and pull me in close and then we would bang in the windmill?!” His mind ran wild like any horny man’s would. Jason ran through the cave and what he saw was nothing he had in mind.

Cara was duct taped completely naked spread eagle upside down on the wind mill. Her pink and black striped panties covered her face , but her eyes were visible through the leg holes. Her small naked tits were capped with sharpied in black nipples with the words ‘Tiny Tits’ above them. Across her stomach the word ‘sl*t’ was sharpied in. Her small patch of pubes led to her wide open pussy which contained about 4 inches of her putter handle. On top of the putter hung his letterman jacket which was bowing in the slight wind, which slightly shook the handle that was penetrating her. Jason dropped his putter in shock. Cara opened her eyes and saw Jason staring at her and she began to freak and go into hysterical crying. Jason ran up to her and didn’t know where to help first. He grabbed the putter and slowly pulled it from her wet pussy. Cara’s body reacted on its own and she humped at the air and moaned a bit, much to her shame. Jason then slowly spun the windmill until she was right side up. He removed her panties from her head then slowly undid the tape on her mouth. Cara had her eyes closed and quietly mouthed ”J..Jason”. He undid the tape on her arms and legs and helped her down. Cara got down in the fetal position and Jason wrapped his letterman jacket around her. “Jason…please look away..now” He did as was asked and he heard her fidget about, then he heard a golf ball fall and roll toward his feet. He knew where her attackers must have shoved that. He turned back to Cara and removed his own jeans. He motioned for her to put them on and she did. Then he scooped her up and carried her to his car in his boxer briefs. When they got to his car he went to call the cops but Cara stopped him.

“It was Sasha and her friends. This whole night…they wanted to ruin it and they did. I…I can’t look at you. You’ve seen…everything.”

“What? Those b*tches. Cara, listen to me. I like you, like really like you. Don’t worry about what I saw. Let me call the cops on them. Let me go after them. Please, what can I do?”

“No. They would get away with it. Her step dad works for the police. I really like you too Jason. The only thing we can do…is get revenge. They ruined something so important to me. I want to take something from them. Will you help?”

“Cara, I’ll do anything for you.”

Jason drove Cara home and the two stayed in his car in the driveway. They cuddled next to each other. Cara wasn’t physically hurt at all, but she was emotionally hurt and full of shame. She kept thinking about what Jason saw, but she felt comforted that he was still with her. Once she was sure that her parents were asleep she left and went inside. Over the next few days Jason and Cara feigned being sick to avoid school and instead were plotting revenge. Revenge that the couple will bring to Sasha and her friends soon.

END

[todd_cheese]

This was good. Looking forward to the revenge.