The Contest Winner
Copyright© 2025 by Terry
Chapter 1
Erotica Sex Story: Chapter 1 - Judy is a contest junkie. She enters any contest that she could find without knowing anything about the sponsor or even what the prize was. Then, she won a big prize, which surprised her and introduced her to a world that she knew very little about. When she discovered what the prize was, it opened up a whole new whole of pleasure for her.
Caution: This Erotica Sex Story contains strong sexual content, including Fa/Fa Consensual Lesbian Fiction Humiliation Light Bond Spanking Sex Toys Nudism
‘CONGRATULATIONS! You are a finalist in our grand prize contest.’
Judy McKee is a contest junkie. Any contest that she came across, she would enter not knowing or even caring what the prize was. Once in a while, she would win a small prize, a gift card or a meal at a fast food or a causal dining restaurant, but nothing she would consider a major prize.
She couldn’t figure out what contest she had won as she entered so many. The By Her Hand was a company she wasn’t familiar with. When she researched the company, she found out that it was a company that specialized in products for women’s sexual pleasure and health. Judy was a little confused as to why she would enter a contest sponsored by a company like that. Of course, she entered so many contests, she often didn’t remembered what she entered or what was the prize.
Reading over the e-mail, it was requested that she text the company for more information. Judy thought ‘what the hell? Even if it was a small prize, it might be worth the effort.’
Judy picked up her cellphone and sent a text:
This is Judy McKee. I received an e-mail saying that I’m finalist in a contest sponsored by your company. It requested that I text you to set up a time for an interview.
A few minutes later, her cellphone chimed. Looking at her phone, she saw it was a text from the company.
Congratulations! Thank you for texting us. As it was stated in the e-mail, we would like to set up a Zoom meeting to interview to see if you meet our qualifications to win the grand prize. I’ll send you an e-mail with a list of times that I’m available. Please select a convenient date and text me.
Again, congratulations on being a finalist.
A few days later, Judy was at her computer waiting for the Zoom call. She logged onto Zoom and entered the meeting info. A few minutes later, the meeting started.
“Hi, Ms. McKee. I’m Sabrina Wilson. You can call me Sabrina. I’m the district representative for By Her Hand. Congratulations on being a finalist in our contest. We have a great prize package for you, if you meet out qualifications.”
“Thank you. You can call me Judy. I must say I have no idea what the prize is. I’m kind of a contest junkie. I enter every contest I came across, not caring what the prize is. A lot of the time, I forget that I even entered a contest.”
“That is understandable. Let me tell you about the grand prize package. The prize was a week stay in the headquarter’s city at a four star hotel, a very special tour of the headquarter, a $1000 gift card and $1000 in spending money.”
“Wow, that sounds like a pretty nice prize.”
“Yes, it is. However, in order for you to win the prize, we have to ask you some questions. Now, these questions will be personal in nature, but it will see if you’re willing to assist us and so we can tailor your visit to our headquarters.”
Again, Judy thought, ‘What do I have to lose.’ “Go ahead, Sabrina. Ask your questions.”
“First, we will ask you one question. If you answer in the positive, we have some more questions for you. If not, we will give you a $100 prepaid cash card for your trouble. As I stated, this question is of a personal nature. We have already lost one finalist at this point. Do you want to continue?”
Judy was a little concern about what this contest was all about. If she didn’t like the way this was going, she could always just reject the prize. “I’m not sure I want to continue, but I’ll try to answer your questions.”
“Good. You know that By Her Hand deals with items for women of a sexual nature. Part of your prize will be going to our headquarters and help us test and evaluate some of our products.”
Judy was confused at the statement. “You mean the winner of the contest get to try out your sex toys.”
“And evaluate them,” said Sabrina.
“That is intriguing,” said Judy.
“There is one more thing. While you’re evaluating the product, there will be one of our testers and developers with you. That way they can gauge your physical reactions to our products. The best way to gauge your physical reactions is for you to be in the nude. The developer that will be with you while you test our products will also be in the nude. Will this be a problem?
“I don’t know if I’m comfortable with that, but I’ll give it a try.”
“That is great, Judy, said Sabrina. “Since you have passed the first questions, we do have more questions for you. Again, these are of a personal nature. If you decide these questions are too personal for you or you don’t want to continue, you will still get the gift card.
“Well, I have gone this far so I might as well continue.” Sabrina started to ask Judy the questions:
‘Are you a virgin? – No. ‘Do you masturbate? – Once in awhile. ‘Do you use toys when you masturbate?’ – I only have a dildo and a vibrator, but I guess I don’t really know how to use them. Mainly I just use my fingers. ‘Are you masturbatory sessions satisfying?’ – I usually get myself off, but they aren’t anything to write home about ‘Have you done any anal?’ – No, but sometimes I’ll stick my finger up my butt. I kind of like that feeling. ‘How about girl-girl action?’ – When I was younger, I fooled around with some of my girl friends. In college, I had a brief affair with a classmate. ‘Have you experienced any bondage?’ – No, but I’m a little intrigued about it. ‘This is a tough question, but please answer this one honestly. No matter how you answer it, you will still get your prizes.’ – Okay. – Some of our products are designed to cause pain. Would you be willing to test and evaluate them? I can promise you, while they will be painful, but nothing too intense or permanent. – Judy wanted to fulfill the requirements of the contest. – I’m not sure about the pain part. Would I be able to stop at anytime? – We really want you to help us, but we don’t want to make it too uncomfortable for you – If you promise I could stop at any time, I’ll give it a try.
That part of the interview was done. “Can I ask you a question?” Sabrina said sure. “Why are you asking all these questions?”
“We have all kinds of products. Some are for regular masturbation, some for anal play, some bondage products and some designed for girl-girl action. If you aren’t interested in a certain activity, we won’t show you those type of products. If you accept our conditions, we want you to be as comfortable as possible.”
It wasn’t too long until Judy was on a plane, heading toward the headquarter city of By Her Hand. This was the first time she had ever flown first class and she was enjoying it. She was reading information about the company that they had sent to her. As she looked through the catalog, she hoped they would explain some of the products to her. Most of their products, she could figure out how they would be used, but there were some she didn’t have a clue.
After she landed at the airport and had gotten her luggage, she saw a woman holding a sign with her name on it. She walked over to her and said, “Hi. I’m Judy McKee.”
“Pleased to meet you,” said the woman. “I am Sylvia from By Her Hand. I’m here to drive you to your hotel.”
“Thank you.”
It wasn’t too long before they were in the car, heading toward the hotel. “Ms. McKee, Bev Rogers, the head of the company, is going to take you out for dinner at 7:00. You will have plenty of time to relax and get ready for dinner, which will be at one of the best restaurants in town. I hope you brought some nice clothes as requested.”
“Yes, I did,” said Judy.
“Good. Ms. Rogers will call you before she arrives at the hotel. If you have any questions or concerns, please talk to the Concierge at the hotel. If needed, they will put you touch with Ms. Rogers.”
They arrived at the hotel. Sylvia took Judy’s luggage to the front desk. “I hope you enjoy your stay and your prize.”
“I hope so, too, Sylvia. Thank you.” Sylvia left and Judy turned to the front desk agent. “I’m Judy McKee. I believe you have a reservation for me.”
The agent checked the computer and said, “Yes, Ms. McKee. Welcome. Your room is ready. Here is your keycard.” Judy signed the receipt and picked up the keycard. “I have a note from a Ms. Rogers. She requested that you call her upon your arrival. I hope you will enjoy your stay with us.”
That evening, Judy and Bev Rogers were having dinner at one of the best restaurants in town. As they ate, they made small talk, but Judy was dying to find out more about the prize she had won. After they were done, Bev asked if they could go back to the hotel to talk about what going to be happening in the next couple days.
“Thank you so much for taking me to dinner at the restaurant. I have never been in such a fancy restaurant and having such a delicious meal.”
“We always treat our special guests to the best. I’m glad you enjoyed it. While you’re here, you are welcome to go to other restaurants or activities in the area. On the desk is a list that you can choose from. If there is something you would like to do, just contact the Concierge and they will make all the arrangements.”
“I still can’t believe how nice you’re being to me.”
“It is our pleasure,” said Bev, smiling. “We are hoping you will ‘pay’ us back by helping us out.”
“I still can’t believe what I have to do, but I accept the conditions to win the prize,” replied Judy. “While I think I can help you, I think I’ll be embarrassed.”
“It is an embarrassing subject, but we don’t want to really embarrass you. We want you to be as relaxed as possible and to enjoy the experience.”
“I appreciate that.”
“Here is more information. Think of it this way. We are hiring you as a temporary independent contractor. You will come to our headquarters and tryout some of our products. Your pay is the prizes that we offered to the contest winner. Not bad pay a few days work, which we are hopeful you will get a lot of enjoyment.” Bev could tell Judy was thinking about what she had just learned. “Just from talking to you, while it could be a little embarrassing for you, I think you could get a lot out of this experience.”
Bev continued saying, “When we get to the headquarters, you will get a tour of the headquarters. One part of the tour is of the model store. We use this store to figure out how to display our products and to train employees,” explained Bev. “Then you can try out any of our products and give us your opinion of them.”
“How long should it take to do the evaluation?”
“We think four days should be enough time, but that is flexible. We will give you the weekend off. The way we have it planned out is this way. We have several different lines of products, dildos, vibrators, erotica jewelry and bondage items. We will block off time for each product line. We would like you to test many different items as you can in that time.”
“I have a feeling my libido and my pussy will get a real workout.”
Bev smiled as she said, “We hope so.”
‘Ring ... ring ... ring.’ Judy woke up from a sound sleep and reached for the phone. “Hello.”
“Good morning, Ms. McKee. This is the Concierge with your wake up call and a message.”
“Thank you. What is the message.”
“Ms. Rogers left the message. She will be sending a car for you to take you to the headquarters at 9:00. Would you like to have breakfast in your room or in our dining room?”
“I think I’ll eat in the dining room.”
At 9:00, Judy stepped out of the hotel on to the street. As promised, a car was waiting for her. The driver got out of the car and came around to where Judy was standing. “Good morning, Ms. McKee. How are you?”
“Good morning Sylvia.” Judy recognized the driver as Sylvia, her driver when she arrived. “Please call me Judy.”
“Okay, Judy,” said Sylvia as she opened the door to the car for her. Then, Sylvia got in the car and she pulled out of the parking spot. As they drove down the street, Sylvia said, “Ms. Rogers will be meeting with you when we arrive.”
“Are we far away from the headquarters?”
“It is close, but Ms. Rogers has an assignment for you.”
“An assignment? What is it?”
“I’ll explain it to you in a few minutes.”
A few minutes later, Sylvia pulled into parking spot. She said, “Our local By Her Hands store is around the corner.” Sylvia handed Judy a credit card. “Ms. Rogers would like you to go into the store and buy, at least, $150 of anything in the store. The card I gave you is a $250 prepaid debit card. It doesn’t matter what you buy, but it has to total at least $150. Also, she would like you to spend at least 20 minutes in the store. She would like you to get an idea of what the store is all about.”
Judy was going to tell Sylvia that she didn’t want to do it, but it seemed like it is was a requirement of the prize. She got out of the car, walked around the corner and entered the store. First thing she notice was the store was clean and modern looking. It looked nothing like the store she had been in. It wasn’t long before Judy felt completely at ease and comfortable in the store. One thing that made her a little uncomfortable was the first thing she saw was a display of dildos and vibrators.
She walked around the display cases, trying to process everything that has happened to her. She was so overwhelmed by the products she was looking at, she completely forgot about looking at the prices. After being in the store for about 10 minutes, a clerk came up to Judy.
“Hi, welcome to By Her Hand. Can I help you find something?”
Unlike the other adult stores she had been in, the clerk was a professional dressed young woman. At first, she didn’t know what to tell the clerk. Then, she had an idea. “I would like to buy something for a friend who doesn’t have much experience with products like you sell here. It is for a party, but a little more than a gag gift. I ... I mean we have to spend $150.”
It was about fifteen, twenty minutes later when Judy returned to the car. She got in and Sylvia pulled out of the parking spot and headed toward the headquarters. “Did you have a good time in the store?”
Judy hoped Sylvia couldn’t see her face because she was sure she was blushing. “Well, it certainly an eye opening experience. The store was nothing like I thought it would be. I have only been in two other adult stores, but I was really uncomfortable in those stores. I enjoyed being in there.”
“That is the philosophy of By Her Hand. We want women to be comfortable exploring their sexuality.”
Judy arrived at the headquarters of By Her Hand. Bev greeted Judy and they went to Bev’s office and talked more about the company and what was going to transpire. As they talked, Judy was getting more nervous, but excited.
“Did you enjoy your shopping assignment?” asked Bev.
“Yes, I did,” replied Judy. “I have only been in two adult stores and I didn’t enjoy them. I enjoyed being in your store.”
Bev and Judy talked for a few more moments and then Bev asked, “What did you buy in the store?” Judy picked up her bag and took out her purchases. “Mmm, a rechargeable panty vibrator. Nice choice. A rabbit vibrator and a lesbian porn DVD set. Interesting choice.”
Judy blushed as she said, “Well, I picked the DVDs just to get it over the amount you wanted me to spend.”
As they were talking, there was a knock on the door and a lady entered the office.
“Hi, Brandi,” said Bev. “This is Judy McKee, the winner of our contest. Judy, this is Brandi. She is one of our testers/developers. She will be your guide while you’re here.”
Judy and Brandi exchanged greeting. Brandi continued to explain what they would do. Brandi was quite thorough with her description. Judy was still nervous, but listening to Brandi made her feel a little bit more comfortable.
Judy followed Brandi as they went to the display store. It look a lot like the store she had just been in. Again, Judy had a hard time figuring out what some of the products did, but she was willing to learn. When Judy asked questions, Brandi answered her questions.
“Are all your stores like this?”
“They are bigger, but basically the same layout. We use this store to test layouts and to train employees.”
“I have been in a couple adult stores, but they were so creepy, I didn’t want to spend much time in them. The stores I was just in made me feel comfortable,” said Judy. “I like the idea of being able to see and feel the toys before I would purchase one.”
Brandi smiled as she said, “I will let you in on a little secret. What you’re going to experience can be experienced by anyone. We don’t make it widely known, but our special clients can do it. It cost $500 dollars.”
“Wow.” Judy was surprised that the store offered such a tour, but if she wasn’t getting this VIP tour from the store, she might have been interested in doing a tour.
“Those clients only get to sample a selected group of our products. You will have the ability to sample any of our products.”
Judy and Brandi continued the tour of the facility. They went into the shipping area. It was small, but seemed to be very busy. Part of the room was the call center. One of the phone rang and one of the employees picked it up.
Brandi tapped the operator on the shoulder. “Ann, would you turn on the speaker.” Ann did as she was requested. “Most of our orders are done online, but there are people who like to talk to a person in case they have any questions.”
They listened to the call. Judy was surprised at how ordinary the call sounded. To Judy, it sounded like someone was ordering a pizza. Judy and Brandi listened to a couple calls before moving on.
Brandi said, “Let’s go to the cafeteria. We can get something to eat and talk. We will be starting the invasive part of the tour soon and you will need the energy.”
In the cafeteria, Judy and Brandi got some food and sat down. Brandi said, “Just to repeat what we are going to be doing, we would like you to sample any of the products that you’re interested in and maybe some you aren’t really interested in, so you can tell us what you like or don’t like about the product.”
The two women talked more about what was going to happen. “Okay, Judy, let’s get started, but first we need to go back to Bev’s office to do some paperwork.”
In Bev’s office, she explained the papers she needed to sign. One was a NDA and another one was a waiver for any injuries. “Am I in danger of being injured?”
Bev replied, “There is always a possibility, but we will do our best to prevent any injuries. If you’re injured, the company will take care of any expenses. If there is a long term injury, that will be taken care of to. It states so in the wavier.”
After reading the wavier and seeing that it did say that, Judy said, “Okay,” and signed the wavier.
“Thank you, Judy. Now, you can get to the fun part of your visit. Brandi, she is all yours.”
Brandi leaded Judy back to a private area. Brandi went over to the door, locked it and pulled down the shade. “Now, we are in a private area and no one can see us or interrupt us.” Brandi started to take off her clothes.
After a few moments, Judy hesitantly started to take off her clothes. After Judy finished taking off her clothes, Brandi took a good look at her, but didn’t make a comment. Brandi didn’t know it, but she was being checked out by Judy.
Brandi walked over to a display stand, indicating that Judy should join her. The stand was full of dildos of all sizes, colors and shapes. Brandi could tell Judy was surprised at the variety of the fake penises in front of her. “These are samples of the dildos that we sale. Bev said that you had a dildo.”
“That is correct,” replied Judy. “I don’t know if I’m using it wrong or what, but it doesn’t seem to do much for me.”
“If you would like, I could give you some instructions on how to use a dildo.”
“I would appreciate that,” said Judy, “especially if I’m going to be walking out of here with a boat load of sex toys.” Both ladies laughed at her comment.”
“What does your dildo look like?” Judy looked at the samples and picked one out. “That is a pretty run of the mill dildo.” Brandi looked over the selection and picked out a dildo. “Give this one a try and see how it feels.”
Judy took the offered dildo and looked at it. It was shaped like a penis, but had ridges on it. “Where should I go to try it?” asked Judy.
Brandi pointed to what kind of looked like a gyno chair. Judy looked at the chair and said, “You want me to do it right in front of you?” Other than a few times when she was younger and at a slumber party and in front of a boyfriend, she had never played with herself in front of anyone.
Brandi didn’t say anything, but picked up another dildo, walked over to the chair, sat down, inserted the dildo and started to masturbate with it. Judy was shocked to see someone exposing themselves to her like that.
She really didn’t want to play with herself in front of Brandi, but she did agree to trying out some of their products. After Brandi got out of the chair, Judy sat down and put her feet into the stirrups. She knew she was wide open, but somehow, she wasn’t embarrassed. She inserted the dildo and started to move it in and out.
As she used the dildo, Brandi watched with a clinical eye and giving suggestions on how to use the dildo. After hearing her suggestions, Judy knew if she used a dildo in the future, it would feel better. After a couple minutes, Brandi asked her to stop, which Judy didn’t want to do.
“I liked that dildo,” said Judy. “I could feel the ridges as I moved it around and in and out.”
“Even though I have to test them, I’m really not into dildos,” said Brandi. “I would rather use a vibrator, but if I used a dildo, I would like something like this one.” Brandi walked to the display and picked out another one. It looked like a regular dildo, but it had bumps all over it. She gave it to Judy.
Judy inserted the dildo and moved it in and out of her. Brandi could see a smile on Judy’s face. “I really like this one. Those bumps feel good.” After using the dildo for a little bit more, Judy pulled the dildo out.
For the next hour, Judy tested a bunch of dildos. Some of the dildos looked like regular dildos and some she wouldn’t have thought they were dildos. Some of them looked like they wouldn’t comfortably go into a vagina, but they did. She gave her honest opinion of each of the toys. Judy was getting pretty worked up, but she didn’t climax.
Brandi picked up another dildo. “Here is a dildo to that you can use hands free.” To Judy, it looked like a penis, but with a suction cup. “You can stick this on any smooth surface and then mount it. Do you want to give it a try?”
“Sure,” said Judy.
“Come over here and get down on your hands and knees.” After Judy did what she requested, Brandi put some lube on the dildo, knowing that she probably didn’t have to. She positioned the suction cup dildo at Judy’s pussy level. After making sure it was positioned, she said, “Okay, Judy, the dildo is at the entrance to your pussy. Go ahead and push your butt back.”
Judy did as Brandi requested. Brandi could see that the dildo was entering Judy. “The dildo is in your pussy. Now, gently, move you butt forward and back.”
Judy did as Brandi requested for a little bit. As she watched, Brandi could tell that Judy was enjoying the dildo. Other than testing a few dildos herself, Brandi hadn’t used many of these dildos. Maybe she was missing out on something by not using one of these toys.
After a couple more minutes, Brandi suggested she stop. “What did you think of that dildo?”
“It felt very good,” said Judy. “However, I think it is too much work to get ready. If I’m going to use a toy, I want to be able to get going right away.”
“Putting the dildo on the floor would speed things up,” said Brandi, “but I understand how you feel.”
“Still sounds like too much work,” said Judy, but she still gave it a try. She stuck the dildo to the floor, making sure it was securely attached. She got down on the floor and squatted over the dildo. It didn’t take long for her to get the dildo into her pussy. Judy started to move up and down on the dildo. She did it for a couple minutes and then got off the dildo.
“What did you think about using it that way?” asked Brandi as she handed Judy a wet wipe.
“That felt pretty good. I liked it,” said Judy, “but again, it seems like too much work to get it ready.”
“Come and look at these,” said Brandi as she walked over to another display. Judy did as she requested. “I like the looks of these,” said Brandi as she handled Judy a colorful glass dildo.
Judy took the offered dildo and said, “This is really pretty,” as she rubbed her hand up and down the dildo. “This is really smooth, too.”
“Why don’t you give it a try,” suggested Brandi.
Judy took the offered dildo and gently forced into her pussy. It felt pretty good. It was really smooth which help with moving in and out of her pussy.
After Judy used it for a little bit, Brandi said, “There is a trick you can use with these dildos.” She took a similar looking dildo out of a bowl, wiped it off and gave it to Judy, who quickly slipped in her.
“Oh, that feels nice and warm,” said Judy as she moved the dildo in and out of her pussy. “I never felt anything like that in my pussy.”
Brandi smiled as she said, “Give this one a try, but put it in quickly,” and handed Judy another glass dildo.
Judy did as Brandi asked and quickly inserted the dildo. “Oh,” said Judy as she took a deep breath as she felt the chilled dildo in her pussy. “That is cold, but it feels ... strange ... but in a way, nice. I have heard of ice play, but I have never tried it.”
Judy kept moving the dildo in and out of her pussy. It didn’t take too long for her hot pussy to warm up the dildo. She took it out and gave it back to Brandi.
“The good thing about a glass dildo is that you can heat it up or cool it down, depending on your mood. It’s a good way to give your pussy a different sensation.”
“I like both the warm and cold feeling of those dildos,” said Judy. “I should include one of those when I use the gift certificate.”
“Another feature of these dildos is they are pretty enough to leave out in the open,” said Brandi, “if you don’t mind explaining to people who see it what it actually is.”
“It might be a little embarrassing to tell people that is actually a dildo,” said Judy, laughing.
“Since you kind of liked the chilled dildo, check this one. I’ll be right back.” Brandi walked out and came back in with another dildo. “This is a dildo that had a chill-able center. You cool this down in a refrigerator. It doesn’t get real cold, but if you use one, you shouldn’t leave it in for too long.”
Judy took the dildo and felt it. “This is a lot colder than the glass dildo you put into the cold water.” After a few moments, she walked over to the chair, got her legs in the stirrups and slipped the dildo into her pussy. “Ooh! That is an interesting feeling.” Judy pumped the dildo in and out of her pussy. “I kind of like the sensation of a cold object in my hot little pussy.” Judy continued to use the dildo.
Brandi had another dildo in her hand that looked similar to the one that was in Judy. “Try this one, Judy.”
“There is another type of dildo that you should try out.” Brandi picked up a long sausage shaped object. “This is called a double dong. With this, two girls can penetrate each other at the same time. Want to give it a try?” Judy said sure. “Get on your hands and knees. I’ll have to touch your pussy, okay?” Brandi felt Judy’s vagina and found it plenty wet. She slipped one end of the dildo into Judy. “How does that feel?”
“It bigger than the other toys I have tried, but it feels nice,” replied Judy.
Then, Brandi got on her hands and knees and slipped the other end of the dildo into her. “Okay, Judy, I’ll push it into you and then you push it into me.”
Judy said okay. The two women started to move back and forth. It didn’t take long for them to get a rhythm. Judy was enjoying this. After about five minutes, Brandi asked if she wanted to stop. Judy said no.
After a few more minutes, Judy climaxed. “Oh, I’m cumming. It feels so good.” After a few more moments, Judy came down from her climax. She was still on her hands and knees, panting.
Brandi pulled her end of the dildo out of her. Then, she gently pulled the other end of the dildo out of Judy.
“I’m sorry that I climaxed,” said Judy, “but it just feel too good.” This was the first time that Judy could remember cumming in front of anyone other than a boyfriend.
Brandi helped Judy up and sat her on a chair. “You don’t have to apologize for cumming. The idea of our products is to give pleasure. From what I saw, your climax looked like a pretty good one.”
“It was,” said Judy. “I would love to have someone that I could share that with.”
“Maybe you will,” said Brandi.
They went to another display stand. There were more dildos, but they were oddly shaped. Judy couldn’t imagine they would fit comfortably in a vagina. She picked up a couple of them to get a closer look. “Brandi, what are these?”
“Strange looking aren’t they?” Judy agreed. “There are from our Monster collection.”