Pokesex Chapter 1: May's dismay by lilsweetbaby

May screamed and squirmed all over. She was stuck in the water with thousands of tentacles around her. The tentacles were wrapping around her making her unable to move. They were ripping off her clothes and cupping her breasts. She continued to scream until one of the tentacles shoved it self down her throat. She was completely defenceless and one tentacle was twisting around her pussy making her cringe. The tentacle drew back and then forced it’s way into her pussy.May woke up with a jolt. She was pouring with sweat and panting like mad. She had been having the same dream for years but it had never had gotten so far before. Never had a tentacle actually gotten inside of her. May reached down and felt her pussy it was very wet. The excitement of being touched like that must have sparked her interest. She sighed a sigh of relief after all it was just a dream. She looked around the room and saw her Warturtle was still sleeping in it’s bed. It must have been early in the morning and no one else was up yet. She got out of bed and decided to start her day.

She went over to her closet and put on her traditional red shirt and blue shorts with her red headband. She went downstairs and began making her breakfast of fried egg noodles. She finished making her breakfast and sat it on the table. She decided to get some juice from the fridge and when she got back to the table Ash and Dawn were coming down the stairs. May gave them a strange look because they always seemed to get up at the same time despite being in different rooms. The four of them had been sharing a home for a while now well they trained their pokemon.

Ash and Dawn sat down next to May and began taking some of the noodles. May’s face turned to anger as she stared the two of them down, she didn’t like people taking her food. She sighed and went to get a bowl of cereal. “So how did you both sleep last night?” May asked as she chewed on her soggy cereal. Ash and Dawn look at each other sort of nervously. “Oh we slept ok no bad dreams or anything.” Ash said quickly. May sighed she couldn’t say the same.

A carrier Piggy came to the window carrying a letter in it’s beak. Ash went over to the window and got the letter. “Hey it’s for you May.” May took the letter and opened it. It was from a pokemon coordinator judge who wanted to see her pokemon in action before putting them in a contest. “Wow finally, I haven’t been in a contest in over a month. This is excellent.” Dawn smiled “Awesome May where is the audition being held?” “It’s in a small theatre in town but I have to leave now it’s in an hour.” May got up and went to her room to gather her pokemon. She grabbed her Warturtle, Venusaur and Glaceon. She waved bye to Ash and Dawn and then left for the audition.

May walked though the woods with a big smile on her face. It was a beautiful day and she was on her way to a pokemon contest audition. May finally got to the address written on the letter but something seemed wrong. The building didn’t have any signs or markers saying it was a theatre. She went to the door and went inside. She looked around, something was definitely wrong, the building looked nothing like a theatre but more like an abandoned warehouse. She started walking backwards in fear when she backed into something hard. She looked up to see a large Blastoise staring down at her. Before she could even scream the beast smashed her on the head knocking her out cold.

May awoke slowly, her head hurting and her vision blurry. Her recent memories came back to her, the letter, the warehouse and the Blastoise. Her vision cleared and she franticly looked around. She was sat down, tied up to a post with strong rope. She squirmed around trying to reach for her pokeballs but they were all gone. “Looking for these?” a mocking voice asked. May turned and saw a figure cloaked in shadows holding her pokeball belt. She squirmed more and tried to free herself and grab her pokemon but it was useless. The mysterious man laughed and threw the belt away.

May grew scared because she was tied up and now her pokemon were gone. The man in the shadows continued to stare at her. “What did you want?” she asked the man. He laughed and stepped into the light. May braced herself expecting a large ugly and ferocious man however the man that stepped out was much less intimidating. He was fairly young about Ash’s age. He had brown spiky hair and a blue t shirt with brown pants. He was truthfully quite handsome. “Who are you?” May asked. The boy laughed “I’m Gary.” He said with great pride. May was shocked, she had heard of Gary but had never met him. He was supposed to be Ash’s great rival but he was not an overall bad guy. “Why are you doing this?” she asked with panic. He smiled “I want to battle Ash one last time but I want to face him at his very best. In order to do that I have to put on of his friends in danger and I found out about you and your contests so I set this little trap.”

May couldn’t believe her ears. Why would Gary go to such lengths just to battle Ash? May turned to him “Why do you want to battle Ash so much?” Gary grew annoyed. “You ask way to many questions here!” He pulled out a piece of cloth and wrapped it around her mouth stopping her from talking. “Now it’s time to tell your friend to come and join us.” Gary went over to a small pc on the railing. He pressed a few buttons and called up Ash on the screen. Ash’s face appeared on the screen. “Who is it and what do you want?” Ash asked sounding quite annoyed. Gary smiled and laughed. “Hey Ash long time no see. Now listen I’m a busy man so I’ll get straight to the point. I want to battle you so we can finally decide who is the best trainer from Pallet Town.” Ash grew angry “Listen Gary you know I love to battle but I’m way to busy at the moment!” Gary smiled some more “I thought you might say that so I decided to provide you with some incentive.” He moved out of the way of the camera and pointed it at May. Ash’s eyes widened and he stared at May. “If you don’t come to battle me at the abandoned warehouse in town then she will become a meal for my pokemon.” Ash couldn’t believe what he was hearing. Gary smiled and turned off the pc.

May grew scared, he was going to kill her and feed her to his pokemon. Gary went over to her and knelt down in front of her. He reached out and caressed her face. “You really are beautiful I would hate to have to kill you.” Gary moved his finger down her neck and chest and felt around her breast. May cringed at the sensation, his finger felt like a tentacle. Gary smiled “You don’t like that do you? I can’t say I blame you. If I went through what you had gone through I wouldn’t like to be touched either.” May’s eyes widened in horror for he knew her terrifying secret. “Oh that’s right May I know, I know all about your little day at the beach.”

(It was a beautiful day with the sun shining and a gentle breeze swept over the sandy beach. May lay down on a blanket enjoying the sun. She was 6 years old wearing a blue bathing suit with a blue headband. Her parents were on beach chairs holding hands. Her father was listening to music and her mother was lost in her book. May stood up “I’m going for a swim ok?” Neither of her parents so much as turned to acknowledge her. She frowned and went for a swim in the ocean. The water was cool and fresh and the waves massaged her back as she lied back and enjoyed the sensation. She smiled for it was a perfect day and it would seem like nothing could spoil it.

Suddenly something knocked into her arm. She looked over and saw a tentacool swimming beside her. She smiled at seeing a real pokemon up close. Suddenly more tenacools came over her way. She laughed and reached out to pet one when it snapped it’s tentacle at her. She screamed in pain as one from behind came up snapped a tentacle across her back. She screamed and more tentacles started slapping her and wrapping around her. She began calling for help but one of the tentacles went down her throat gagging her. All the tenacools started wrapping around her body and began wiggling their way down every hole in her body. She was trapped and couldn’t scream for help. Her parents found her almost an hour later half dead and scarred for life. It was years before she got over her fear of pokemon and she still has her fear of being touched.)

May had lost herself in memory and was oblivious to the fact that Gary was undressing her and fondling her body. He began massaging her pussy and wrapping her finger around her clit. The sensation bought her back to reality. She tried to tell him to stop but she was still gagged. Gary loved the sound of her struggling and began slapping her bare ass. She screamed in pain which just made Gary hornier. He gently pushed his fingers inside of her. She winced and closed her eyes trying to pretend this wasn’t happening. Gary fingered her faster and faster causing May to blush and pussy juices to flow from her vagina. Gary smiled and removed his fingers. He licked them up and sucked off all the juices. “Umm you taste really good baby. I should let my cock have a taste.” May screamed and closed her legs. Gary laughed and shoved his fingers in her pussy causing it to gush more. “Your telling me no but your body is screaming yes.”

Gary pulled her legs apart and put himself in between them. He pulled down his pants and underwear to reveal an erect 9 inch penis. May was scared and a little intrigued because she had never seen a penis before. Gary smiled “Don’t worry I’ll be gentle….to start.” Gary placed the tip of his penis at the lips of her vagina and pushed in as much as it would go. May’s whole body quaked and tears flowed from her eyes. The tentacles had penetrated her before but they couldn’t match the width of a penis. Gary slowly began to hump her slowly but increased his speed with every pump. May half screamed and half moaned. This may not how she would have liked to been fucked but she had to try and make the best of the situation.