Tale of a Virgin Babysitter
Introduction:
My first sex story. hehe
“Your father and I recognize that, but we’ll be gone for almost a week and you wouldn’t be able to take care of yourself that long”
“Well maybe if I had a goddamn license I could.”
“Well you don’t which is why we’re getting an able bodied baby sitter to take care of you those five days we’ll be gone. This wouldn’t have been a problem if you had decided to come along, but you said no. So this is the alternative.”
“Please don’t tell me it’s a guy.”
“We would never be so mean. It’s a girl. A young woman. She’s a daughter of one of Cindy’s friends. She needs the college money.”
“Fine. So when does she get here?”
Diiing dooong!
“I guess I spoke too soon.”
They walked to the door. Uninterested, Scott, the sixteen year old needing the baby sitter, opened the door. The baby sitter walked in.
“How are you Mandy?”
“I’m doing very good Mrs. Jay,” Mandy said. “How are? I hope you enjoy your trip,” she said smiling. Her white teeth peering through her lush full lips.
“I am doing well. Happy to finally get some vacation. I hope you don’t mind doing this. We’ll pay you what ever you need.”
“Thank you.”
The three moved to the kitchen began discussing details. After the details are taken care of, the parents leave and the baby sitting has commenced.
Scott and Mandy walked back to the kitchen. Silently they sat at the counter. When Mandy wasn’t looking, Scott silently began to steal glances at her. Examining her features. Her jet black hair went down to about where her breasts were. Her fair skin looked like silk in the sunlight. Her breasts were at least a DD. She wore no make up, but had little, black glasses. She had on a black and white stripped sweater with a black spaghetti-strap shirt under it. Scott could see she was wearing jeans but didn’t get a look at her ass. He began thinking of how he could get a good look at it.
“So… how old are you?” he asked as casually as he could but still his voice cracked under the pressure of talking to the hottie five feet from him.
She glanced at him and blushed. Her checks flushing and becoming rosy pink. “I’m 21. So, you’re 16?”
Scott nervously nodded. At school he was a total smooth operator. A true ladies man, but this was with girls his age. Ones that were easy to get, but this girl was in a different class. She was a college girl. If he could pull this shit off, he would be one of the few crowned as high schoolers at his school that nailed a college chick.
“Want something to drink?” he asked getting up and walking to the fridge.
“I’ll just have water. It’s a nice place you got here. Where will I be staying?”
“Oh I can show you. It’s up stairs.”
The two walked to the stairs and then Scott stopped.
“After you,” he said coolly. He grinned and showed his white teeth through his lips. His blue eyes looked at Mandy who was just slightly shorter than him.
“Oh! A gentleman!” Mandy said smiling. Her hazel-green eyes meeting his deep blue eyes.
Scott felt blood rushing to his cock as Mandy looked in his eyes and began walking up the stairs ahead of him, and as he wanted, he got a full view of her gorgeous ass. Her jeans tightly hugged her ass and held them firm. All he could think was that he wanted to hold her ass firm in his hands. His cock was getting hard now. It may not be noticeable at the moment, but anymore blood that went in, would make it noticeable. He saw that on the left ass cheek of her jeans that there was a little, red lace heart woven in the pattern. He stared at it as her ass bounced as she walked up the stairs. When they got to the top his cock was fully hard and he prayed that she wouldn’t notice or she’d think he was a total perv.
She stopped. “So where do I go?” she asked as she stood at the top and peered down the left hall way then to the right.
Scott pointed to the right and Mandy kept walking in front of him. When they got to the end of the hall way, there were three rooms. To the left was a restroom. Then in the middle were two doors side by side. Scott pointed to the door to the right.
“That’s the guest bedroom. You’ll stay there,” he said, then pointed to the door next to it. “And that’s my room. So if there’s any scary monsters, I’ll be next door if you need me,” he said laughing a little and giving Mandy a wide grin. He felt like a total dumbfuck but he hoped the even more stupid grin would charm her.
Mandy laughed and returned the smile. Her lush lips curling up into a beautiful smile unmatched by any girl Scott had ever met. “Well I’ll have you check under my bed and my closest before I turn in, ok?” she replied.
Scott was relieved that she seemed to go along with it.
“Can you help me get my stuff up here?” she asked after a brief moment of silence.
“Oh yea. Lets go get your stuff.” Scott said turning and began walking out of the room.
The two got Mandy’s large suitcase and Scott, like a gentleman, carried it for her up the stairs, of course she led the way. He was a gentleman as she had clearly stated. Once all her things were in order, and unpacked and in the drawers, Mandy took off her sweater, exposing her large DD breasts. Now it was way more noticeable when the bounced as Mandy walked.
“Damn it’s hot in here,” she said wiping small beads of sweat from her forehead. “Hey lets change and then go out for some pizza. How’s that sound?”
“That sounds really cool,” Scott said grinning.
“Ok, I know this great little Italian place so dress kinda nice ok?”
“Ok,” he said walking to his room. Scott changed into a nice pair of jeans and a nice long sleeve black shirt. He walked over to his dresser and pulled out his best cologne. A couple squirts for good luck and he was set. He walked out and knocked on Mandy’s door.
“Come in!” she said.
Scott opened the door. Mandy now had her hair up and changed into a pair of black dress jeans. She still had on the spaghetti strap shirt and was fitting a black long sleeved jacket over it. “How do I look?” she asked as she looked herself up and down in the mirror.
“You look… good,” Scott said not sure what to say since he didn’t want to fuck up his chance with her. If he even had a chance, he thought.
“Good,” she said turning to him and smiling. “Now let’s go have us some fun kiddo.”
The two had a great dinner and shared a pizza and a pasta dish. During the dinner, Scott kept staring at Mandy’s large breasts. He’d never see tits that big in person. Sure he’d seen at least G-cup tits in different pornos but he was used to seeing the teenaged B and C cup tits at school.
After they were done, they left the restaurant and went for some ice cream. They sat in the car and ate and talked. Mandy wasn’t you’re average college girl as Scott was finding out. She had brains. She was in her third year in med school and was at the top of her class for all three years so far. She also knew different languages. She studied Spanish in high school and could speak it well. She also knew some Korean and Japanese. Then came the big shocker. Mandy was a major geek. Scott was kind of clued in when she said she was a med student, but then she revealed that she was very much into the Japanese comics and cartoons. She didn’t care much for the American comics though. Mandy talked bout how she went to a couple conventions before dressed up a character from one of the comics she liked. She said it was funny because all the guys kept looking at her breasts. Then Scott froze after what Mandy said next.
“So do you like ‘em? My breasts? I noticed you were staring at ‘em ever since we were in your kitchen,” Mandy said chuckling. “It’s ok. Don’t worry about it. I’m so used to guys ogling over my breasts I don’t even care anymore. It was kind of annoying when I was younger and my breasts were way bigger than all the other girl’s breasts. They’d make fun and shit. I knew it was ‘cause the were all jealous. All the guys hit on me. It’s a wonder that I’ve never had a boyfriend given the fact that I can pick up any guy I want.”
“You’ve never had a boyfriend?!” Scott exclaimed in astonishment. “Have you ever kissed a guy?”
“Nope,” she said, “I guess I never really cared about all that shit. I was always way to busy with my school work. So I never gave it any thought. I bet you get a lot of girls hitting on you, don’t you? You must be like a school stud or some thing.”
“M-M-Me?!” Scott managed to stammer as his face turned to the color of a bright red apple.
“Yeah, you. You little cutie. I’m talking about you dumbass,” Mandy said teasingly. “You’re a little cutie even though you’re like way younger than me.”
Scott’s face was now the brightest red you could imagine. He sat with his mouth open, speechless, as if he brain had been fried.
“Damn I broke another one,” Mandy said laughing loudly as she stated the car. “C’mon. Let’s get back to the house. It’s getting late.”
Once they got back Scott began watching TV and Mandy went up to change and read one of her manga. Scott flipped through the channels. His mind filled with little devious thoughts. He really wanted to squeeze Mandy’s tits until he grew red in the face, but a girl like her would never do that. Especially since… she was a virgin. Scott’s mind stopped. He just realized that the big-titted hottie that was going to be staying with him for the next five days was… a virgin.
Scott began thinking. He began fantasizing about having sex with Mandy and instantly his cock began to harden. His cock was about six and a half inches long and about two and a half inches wide. A good size for his age. Though he had seen some guys in the locker room with dicks that were about eight inches. Even so, his cock was noticeably larger than most of his classmates. He kept fantasizing about Mandy as he stared off into space.
“Whatchya watchin’ there buddy-pal?” he heard Mandy say from behind him. He jumped and yelped softly, startled by Mandy’s unheard entrance. He looked at the TV and noticed he had accidentally left it on one of those provocative model shows where they have to blur something out every five seconds.
“Uh. Shit. Nothing.” he spat out stupidly.
“No. No. What is this? Its interesting. Its ‘who wants to be an air head?’ right?” she said laughing at her own joke. She sat down next to Scott, who instantly covered his hard cock with a pillow. “See. All those shows are the same man. They don’t have show’s about smart girls do they? Smart isn’t sexy. And that makes me sad ya know?”
“Huh?” Scott grunted not sure what to say or do. He kept looking up and down Mandy’s delectable body. She was now clad in the same damn black shirt and blue athletic shorts. The really short kind that all the cheerleaders wear.
“Hey. Eyes up here kiddo,” she said chuckling softly. “What do you think of those girls? They’ll show you their boobs for a beaded necklace that isn’t worth five cents. Doesn’t that seem kinda stupid?”
“Yeah, it kinda is,” Scott said looking into Mandy’s hazel-green eyes. They were for sure the prettiest eyes he’d ever seen, and they were piecing straight into his own.
“You gotta find yourself a good girl. You cant be chasin’ around floozies, ya know?” Mandy said. Scott nodded. “You ever do anything with a girl, Scott?”
He blushed and nodded. “Yeah, I’ve gone all the way.”
“Wow. So what’s it like, huh? To do that with a girl? Is it fun?” she asked seriously.
“Yeah, of course it is.”
Mandy sat there silently. She stared off into space. “I’ve always wondered what its like. To have some one inside me. Making love to me. You know. I lied. I do think about that shit. It get’s kinda lonely when you put up a wall, and you get so focused on your goals that you don’t ever just… live a little.” Mandy said softly. Her words were so soft and quiet that is there was a gust of wind they would have been carried away and would have not been heard. She looked back at Scott. Her eyes were a little wet but she was smiling and a depressed kind of way. She leaned in and kissed Scott on the cheek. “I like you kiddo. You’re one hell of a kid, and I’ve just met you. Watch out or I’ll fall in love with you.” she said laughing softly. “C’mon. It’s late. Let’s go to bed, ok?”
Scott nodded and they went up stairs. Before Scott got in his room, Mandy grabbed his hand. “Where you goin’ kiddo? You gotta check for monsters.” They both smiled at each other as they entered Mandy’s bed room. “Hey, Scott,” she said quietly.
“Yeah?”
“Why don’t you sleep in here tonight. The bed’s big enough, and I promise I don’t bite,” she said holding his hand and looking at him intently with her hazel-green eyes.
“Sure. It’ll be my job as a gentleman to protect you,” he said as they both quietly laughed. They got in bed together and Mandy turned out the light. As they lay in the darkness Mandy reached out and touched Scott’s hand. She laced their fingers together and held it tightly. She moved in closer to him and began licking at his neck. He moaned and squirmed.
“You like that?” she whispered in his ear. He nodded. She continued to lick. She reached with her free hand to his cock. It was already rock hard. Her inexperienced fingers pulled his cock out of his boxers. She began to stroke it to the best of her ability as she licked his neck. Moonlight sifted through the window so that they could see enough in the darkness.
“I like this,” Mandy whispered as she stroked Scotts fully hard cock. He turned to face her and they began to kiss. His tongue slide into her mouth like a sly snake. It danced around her tongue and massaged it. He reached a hand down her shorts and massaged her untouched, virgin pussy through her panties. Mandy instantly moaned. “Oh, fuck,” she whispered. “Take my panties off.” Scott did as she commanded. Her virgin pussy was so hot and wet that her panties were soaked with her sweet nectar. Scott began rubbing her pussy again, and she began moaning instantly once again.
Mandy took her shirt off exposing her large breasts in the soft moonlight. Scott stopped massaging her pussy and stared are her beautiful breasts. Her nipples were so hard you could cut glass, and she had large areola surrounding her nipples. “Touch them,” she commanded. Scott unlatched his hand from hers and began squeezing her left breast. “Yeah, just like that, Scott,” she moaned as she stroked his cock. “I want you… in me,” she whispered in his ear. Scott rolled on top of her and positioned him self.
“It’s gonna hurt.”
“I know. Just make love to me,” she whispered as she licked his neck. Slowly, he took his cock and started pushing it into Mandy’s sweet, virgin pussy. She let out her loudest moan yet as his cock began to rip her hymen and enter her fully. He slowly pumped his cock in and out of her pussy. Her moaning was increasing in volume. Scott thrust faster inside Mandy. She moaned with every one and grit her teeth in pain. Her pussy was so tight it was numbing Scott’s cock. It felt so good to have his cock inside her, and finally, he came. Scott moaned along with Mandy as cum shot out of his cock and filled Mandy’s now deflowered pussy.
“Shit. I came in you.”
“It’s ok kiddo. I’m on the pill. Just leave your cock inside me. It feels so right in there.”
In the moon light, the two fell asleep.
