Tale of a Virgin Babysitter
Introduction:
My first sex story. hehe
âYour father and I recognize that, but weâll be gone for almost a week and you wouldnât be able to take care of yourself that longâ
âWell maybe if I had a goddamn license I could.â
âWell you donât which is why weâre getting an able bodied baby sitter to take care of you those five days weâll be gone. This wouldnât have been a problem if you had decided to come along, but you said no. So this is the alternative.â
âPlease donât tell me itâs a guy.â
âWe would never be so mean. Itâs a girl. A young woman. Sheâs a daughter of one of Cindyâs friends. She needs the college money.â
âFine. So when does she get here?â
Diiing dooong!
âI guess I spoke too soon.â
They walked to the door. Uninterested, Scott, the sixteen year old needing the baby sitter, opened the door. The baby sitter walked in.
âHow are you Mandy?â
âIâm doing very good Mrs. Jay,â Mandy said. âHow are? I hope you enjoy your trip,â she said smiling. Her white teeth peering through her lush full lips.
âI am doing well. Happy to finally get some vacation. I hope you donât mind doing this. Weâll pay you what ever you need.â
âThank you.â
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 wasnât 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 didnât get a look at her ass. He began thinking of how he could get a good look at it.
âSo⊠how old are you?â 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. âIâm 21. So, youâre 16?â
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.
âWant something to drink?â he asked getting up and walking to the fridge.
âIâll just have water. Itâs a nice place you got here. Where will I be staying?â
âOh I can show you. Itâs up stairs.â
The two walked to the stairs and then Scott stopped.
âAfter you,â 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.
âOh! A gentleman!â 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 wouldnât notice or sheâd think he was a total perv.
She stopped. âSo where do I go?â 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.
âThatâs the guest bedroom. Youâll stay there,â he said, then pointed to the door next to it. âAnd thatâs my room. So if thereâs any scary monsters, Iâll be next door if you need me,â 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. âWell Iâll have you check under my bed and my closest before I turn in, ok?â she replied.
Scott was relieved that she seemed to go along with it.
âCan you help me get my stuff up here?â she asked after a brief moment of silence.
âOh yea. Lets go get your stuff.â Scott said turning and began walking out of the room.
The two got Mandyâs 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.
âDamn itâs hot in here,â she said wiping small beads of sweat from her forehead. âHey lets change and then go out for some pizza. Howâs that sound?â
âThat sounds really cool,â Scott said grinning.
âOk, I know this great little Italian place so dress kinda nice ok?â
âOk,â 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 Mandyâs door.
âCome in!â 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. âHow do I look?â she asked as she looked herself up and down in the mirror.
âYou look⊠good,â Scott said not sure what to say since he didnât want to fuck up his chance with her. If he even had a chance, he thought.
âGood,â she said turning to him and smiling. âNow letâs go have us some fun kiddo.â
The two had a great dinner and shared a pizza and a pasta dish. During the dinner, Scott kept staring at Mandyâs large breasts. Heâd never see tits that big in person. Sure heâd 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 wasnât youâre 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 didnât 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.
âSo do you like âem? My breasts? I noticed you were staring at âem ever since we were in your kitchen,â Mandy said chuckling. âItâs ok. Donât worry about it. Iâm so used to guys ogling over my breasts I donât even care anymore. It was kind of annoying when I was younger and my breasts were way bigger than all the other girlâs breasts. Theyâd make fun and shit. I knew it was âcause the were all jealous. All the guys hit on me. Itâs a wonder that Iâve never had a boyfriend given the fact that I can pick up any guy I want.â
âYouâve never had a boyfriend?!â Scott exclaimed in astonishment. âHave you ever kissed a guy?â
âNope,â she said, âI 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, donât you? You must be like a school stud or some thing.â
âM-M-Me?!â Scott managed to stammer as his face turned to the color of a bright red apple.
âYeah, you. You little cutie. Iâm talking about you dumbass,â Mandy said teasingly. âYouâre a little cutie even though youâre like way younger than me.â
Scottâs face was now the brightest red you could imagine. He sat with his mouth open, speechless, as if he brain had been fried.
âDamn I broke another one,â Mandy said laughing loudly as she stated the car. âCâmon. Letâs get back to the house. Itâs getting late.â
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 Mandyâs tits until he grew red in the face, but a girl like her would never do that. Especially since⊠she was a virgin. Scottâs 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.
âWhatchya watchinâ there buddy-pal?â he heard Mandy say from behind him. He jumped and yelped softly, startled by Mandyâs 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.
âUh. Shit. Nothing.â he spat out stupidly.
âNo. No. What is this? Its interesting. Its âwho wants to be an air head?â right?â she said laughing at her own joke. She sat down next to Scott, who instantly covered his hard cock with a pillow. âSee. All those shows are the same man. They donât have showâs about smart girls do they? Smart isnât sexy. And that makes me sad ya know?â
âHuh?â Scott grunted not sure what to say or do. He kept looking up and down Mandyâs 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.
âHey. Eyes up here kiddo,â she said chuckling softly. âWhat do you think of those girls? Theyâll show you their boobs for a beaded necklace that isnât worth five cents. Doesnât that seem kinda stupid?â
âYeah, it kinda is,â Scott said looking into Mandyâs hazel-green eyes. They were for sure the prettiest eyes heâd ever seen, and they were piecing straight into his own.
âYou gotta find yourself a good girl. You cant be chasinâ around floozies, ya know?â Mandy said. Scott nodded. âYou ever do anything with a girl, Scott?â
He blushed and nodded. âYeah, Iâve gone all the way.â
âWow. So whatâs it like, huh? To do that with a girl? Is it fun?â she asked seriously.
âYeah, of course it is.â
Mandy sat there silently. She stared off into space. âIâve 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 getâs kinda lonely when you put up a wall, and you get so focused on your goals that you donât ever just⊠live a little.â 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. âI like you kiddo. Youâre one hell of a kid, and Iâve just met you. Watch out or Iâll fall in love with you.â she said laughing softly. âCâmon. Itâs late. Letâs go to bed, ok?â
Scott nodded and they went up stairs. Before Scott got in his room, Mandy grabbed his hand. âWhere you goinâ kiddo? You gotta check for monsters.â They both smiled at each other as they entered Mandyâs bed room. âHey, Scott,â she said quietly.
âYeah?â
âWhy donât you sleep in here tonight. The bedâs big enough, and I promise I donât bite,â she said holding his hand and looking at him intently with her hazel-green eyes.
âSure. Itâll be my job as a gentleman to protect you,â 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 Scottâs 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.
âYou like that?â 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.
âI like this,â 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. âOh, fuck,â she whispered. âTake my panties off.â 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. âTouch them,â she commanded. Scott unlatched his hand from hers and began squeezing her left breast. âYeah, just like that, Scott,â she moaned as she stroked his cock. âI want you⊠in me,â she whispered in his ear. Scott rolled on top of her and positioned him self.
âItâs gonna hurt.â
âI know. Just make love to me,â she whispered as she licked his neck. Slowly, he took his cock and started pushing it into Mandyâs 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 Scottâs 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 Mandyâs now deflowered pussy.
âShit. I came in you.â
âItâs ok kiddo. Iâm on the pill. Just leave your cock inside me. It feels so right in there.â
In the moon light, the two fell asleep.