Gina Loses Her Virginity While Babysitting

by mysteria27

Copyright© 2015 by mysteria27

Erotica Sex Story: An eighteen year old loses her virginity while doing an overnight babysitting job.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   First   Oral Sex   Anal Sex   .

I've been babysitting for the longest time. Every weekend, I have a job and have made enough money to buy a car. I've been babysitting for the Jackson's for about two years now. They hired me overnight and will be paying me three hundred dollars.

I'm so excited to go over there tonight. The best part of babysitting over there, is their gorgeous son named Jack. I wasn't sure if he'd be home, but I was hoping he might be. I've had a crush on him for the longest time. He's so incredibly handsome.

I kind of get nervous being around him. I'm going to make sure that I look really nice, if he happens to be home. A few times, Jack has flirted with me. I think he might like me, but I mean he's twenty-one.

I'm eighteen and just a little girl in his eyes. You could say, that I've dreamed about being with him. I know that must sound so silly, but a girl has to have a dream crush, right?

The Jackson's needed me very short notice. But, they're paying me three-hundred dollars. That's the highest amount I've ever been paid. The usual babysitting jobs are like fifty dollars. I'm really excited to be doing this job. My parents are also home, in case I need them to help me in anyway.

Ding, Dong

"Gina, come in. How are you? We're so happy you could do this for us tonight. We're sorry, it's a little short notice. We would have asked you sooner, if we had known earlier."

"Don't be silly! I love to babysit Allyson. Everything is really good. I'm doing really well in school this year. Things are going really well."

"I'm so happy you're doing well in school. I have fed Allyson and she's already sleeping. She should be out for the night. Occasionally, she wakes up with nightmares, however, I doubt that will happen tonight. I stocked the refrigerator and you can help yourself. We'll be home around noon tomorrow. I really think it should be a very easy job for you. Jack will probably be out for the evening, so you don't have to worry about him."

"Okay, I'm sure everything will be fine."

"If you need us, our cellphones are on the refrigerator. Jack's cell is also there, if you need him to come home."


"Will see you tomorrow. Make yourself at home and enjoy yourself!

The Jackson's took their luggage and left. I walked upstairs and put my overnight bag into the guest room. I then opened Allyson's door and peeked in. She was sleeping just like Mrs. Jackson had said. I noticed the monitor was on. I knew that Mrs. Jackson had monitors set up all over the house.

I walked back downstairs and went into the kitchen. I was a bit famished and wanted to see if there was anything good to eat. I noticed there was some Chinese food. I made a plate and then put it into the microwave to get heated.

I heard the front door open and then Jack appeared in the kitchen.

"Gina, how are you doing?"

"I'm great Jack. How are you?"

"I'm doing really well. I thought I'd hang around with you tonight."

"Oh, You don't have to do that. You're mom said you'd be out."

"I think I'll be staying home tonight. Do you want a beer?"

"I don't think I should be drinking. I'm babysitting and I'm only eighteen. The drinking age is twenty-one."

"I won't tell if you won't tell. Come on live a little."

"Okay, I guess one beer would be okay."

"I'm glad you agree. Let's have some fun."

Jack went to the refrigerator and pulled out two beers. He opened them both up and handed me one. I wondered what he meant by having fun. I was amazed he was talking to me.

"You're looking very pretty tonight. You must drive all the boys in your high school crazy."

"No, I'm just focusing on my school work. I don't have a boyfriend."

I took several sips of the beer. Jack was just staring at me. I was really excited he was going to be staying home with me. I wondered what he had on his mind. He looked so hot just sitting there.

He was wearing a guinea tee shirt and a pair of bootleg jeans. He was tan and looked amazing. Jack is 5'10" and about one hundred and seventy five pounds. He's got brown short hair and blue eyes. He's really dreamy looking. I was pretty sure he must have a bunch of girlfriends. I wondered why he'd want to spend the evening with me.

I'm 5'4" and kind of on the thin side. I have blonde hair and blue eyes. I have small and perky breasts. I have had a few boyfriends, but nobody serious. I'm still a virgin, but really want to have sex. I watch porn to see all the moves that the women do in the movies. I really want to have sex, but the opportunity has never come up. I masturbate a lot of the time. I have a few vibrators that I play with.

"I'm really surprised you don't have a boyfriend. You're a very nice looking girl."

"Thank you! You're so nice to say that."

"If you were in my grade, I would have dated you."

I could feel myself starting to blush. I drank the beer down quickly, because I was starting to feel a bit nervous. I was also wondering why Jack would want to hang around with me for the evening. I mean the guy could have any girl he wanted.

"Have another beer. I promise not to tell."

"I better only have the one. I'm babysitting and need to be alert."

"My parents are away. My sister is sleeping. Have a little fun."

"Okay, One more beer."

Jack went and pulled out a few more beers. He opened them up. I finished up my food and washed the dishes. I was starting to feel a little tipsy, but pretended that I was okay.

"Why don't we go into the living room? I could put on some music or we could watch a movie."


We both walked into the living room and Jack put on some music and we sat on the couch. Jack sat very close to me and was looking at me very strangely. I really didn't know what he was planning on. We both continued to drink our beers. He was chugging his beer down very fast. I did whatever he did, because I didn't want to seem like a novice.

"I can't believe how pretty you are. Are you sure you don't have a boyfriend? Is a pretty girl like you a virgin or are you a bad girl?"

"What? Why are you asking me that?"

"I'm just curious if you've had sex. I think you're very attractive."

I knew I was blushing and couldn't believe he was asking me these things. He was smiling and giggling to himself.

"Is Miss Gina a hot and wild girl or is she a nice and sweet virgin?"

"No. I just don't have a boyfriend right now. I wouldn't say that I'm wild. I'm just a very nice girl."

Jack got up and grabbed a few more beers from the kitchen. He opened his up and took a swig out of the bottle. He seemed like he wanted me to be his next conquest.

"Do you want another beer?"

"No. I think I've had enough. I'm babysitting your sister and cannot have anymore beer. But, you can drink."

"I sure would like to kiss you. Would you allow me to kiss you, Gina?"

"Sure! I'd like that."

I was amazed that his gorgeous guy would want to kiss me. Jack leaned in and put his arm around me and put his lips onto mine. We kissed passionately on the mouth. He then pushed his tongue into my mouth and we shared a passionate kiss. I had kissed boys before, but never had such a passionate kiss before.

"You kiss really nice, Gina."

"I'd really like to be with you. Do you want to be with me?"


Jack was kissing me and then put his hands over my dress and was rubbing at my breasts. I could feel my nipples getting hard in my bra. I couldn't believe I was making out with Jack. He moved my dress up my thighs and put his hand over my panties. I was getting excited that this might be my chance to not be a virgin anymore. I was hoping that Jack would want to go all the way with me.

"You're really warm down there. You're making me really horny. I really like you."

"I like you too."

I was getting really turned on that Jack had his hand on my panties. I kind of lied to him and told him I wasn't a virgin. I didn't want him to think I was a prude. I had never been with anybody ever. I had watched pornography with friends and knew the general idea on how to have sex. I really wanted to have sex with Jack.

Jack then pulled my panties to the side and started to play with my pussy. He was rubbing his fingers all over my cunt. His fingers felt amazing while he explored my vagina. I had only masturbated with my fingers and vibrator. I never let another person touch my pussy. I wanted Jack to be my first time lover. I wanted my dreams and fantasies to come true tonight. My heart was beating very fast.

Jack's kisses were so deep and he had pushed his fingers into my vagina. He started to move his fingers in and out of my pussy. I was so turned on and feeling very horny. My pussy was starting to drip onto his fingers.

Jack stopped kissing me and put his creamed fingers into his mouth. Then he stuck his fingers back into my pussy and then put his fingers into my mouth to taste myself. I had never tasted my pussy juices before. I was amazed how sweet my pussy tasted. I was just wanting Jack to lick my pussy. I wanted to be like those women in the porn movies screaming in pleasure.

"Let me take off your dress. I want to show you some things."

I stood up and Jack helped me take off my dress. He unhooked my bra and released my small and perky breasts. He pulled down my panties and helped me to lay down on the couch. He then opened my thighs and dove into my pussy. I had seen this in movies and always wondered how it would feel.

"You have a very pretty pussy, but it would look so much better shaved. Would you let me do that for you?"


"Take my hand and we'll go into my bedroom. I'll shave your pussy in there. Grab my sister's monitor so you can listen if she needs you."

I grabbed the monitor and followed Jack into his bedroom. Jack took the monitor and plugged it in. He then motioned to me to lie down on his bed. I went over to his bed and got comfortable.

Jack then went and got all the supplies. He came back over to the bed with some shaving cream, a razor, and a washcloth. He took the washcloth and rubbed it all over my pussy and then pumped the shaving cream into his hand and put it all over me. Then, he carefully took the razor and shaved my pussy. It didn't take very long, but he shaved my pussy bald.

"Go to the mirror and look at yourself."

I walked over to the mirror and looked at what he had done. He shaved all my pussy hair off. It looked just like the women in the porn movies. I noticed that Jack had taken off all his clothes. He looked amazing just standing there naked.

"Come back to the bed. I want to lick that gorgeous pussy."

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