Ashley's babysitting goes wrong (18 year old +)

Started by Allison · 0 Replies


2 yrs

Posted: 2 yrs
One of the things I like to do is post fantasy stories about some of my girl friends that I know. So here's my first one.. Along with pictures attached of my friend Ashley om my profile.

Mr. Freeman was on the prowl again. He was at a high school football game and he was looking for a hot cheerleader to lure to his house and have his way with her. Of course he needed to make sure she was 18 and of legal age. Mr. Freeman was a 91 year old man that was very powerful physically and with his status because he was a billionaire. He had multiple surgeries to make his sexual life extraordinary. He was pretending like he came to watch his grandson play although he didn't have any grandsons he just wanted to take a cheerleader home. As soon as he saw her he wanted her right away. "Hello, I'm here watching my grandson play, and you seem like a sweet girl I needed someone to help babysit my other grandson" he lied, making up a story. The hot young cheerleader blushed "oh thank you.. I don't know.." she said nervously as it seemed weird a random old man was asking her. He opened a briefcase offering a lot of money. "I'll pay a lot it's not a problem" he said. "we can arrange a meet up somewhere public so you can get comfortable with me and my grandson before you come babysit him. I'm Richard. What's your name and how old are you?" he asked. " Ashley, I just turned 18 last week" she said smiling. 'perfect' Mr. Freeman thought. They talked for a while until she finally decided to meet with the old man and his fake grandson in a local Starbucks to go through the details of the babysitting. Mr. Freeman had her lured, now he just needed to bring the hot barely legal 18 year old cheerleader inside his home. Mr. Freeman had a friend that let him borrow his son to hang out with in exchange for a lot of money. The friend and son had no idea the old man was using his son as an excuse and what nasty plans the 91 year old man was planning on with an 18 year old cheerleader. They met with Ashley at a local Starbucks and after a while she agreed on babysitting him. It seemed like a lot of money she could use to fund her college and the old man seemed like a sweet person. Mr. Freeman smiled, knowing the young beautiful teen was all his. The first day of babysitting Ashley showed up wearing a long sleeve gray shirt tied around her waist, showing off her sexy tight waist, and blue short shorts sowing off her fresh clean teen legs. Mr. Freeman was caught off guard when she showed up to babysit dressed like that, he wished he could grab her right then and force his way with her but he had to control himself and wait for the right opportunity. He only wished she was wearing flip flops, as she was wearing sneakers. He wanted a good idea at how the sexy teen looked like from head to toe. They went over everything and finally Mr. Freeman left her to babysit. The only thing that made her a little nervous was how the old man kept eyeing her up and down, really pausing at her legs multiple times. She brushed it off. She had no idea how old Mr. Freeman was and what he had planned for the innocent vulnerable young teen. It was the second week of babysitting and Mr. Freeman couldn't take it anymore he had to have Ashley one way or another. He didn't realize the day would come quicker than he thought and unexpectedly. Ashley had put his "grandson" to sleep. Her phone had died, she didn't bring a charger, and Mr. Freeman wouldn't be home for a few more hours. The teen was bored and started looking around the house. Mr. Freeman really wasn't working or anything, he was out and about either on business meetings or scoping out other hot Girls he wanted for himself. Ashley opened a drawer and gasped. She found a bunch of pornography DVDs inside. 'Gross' she thought thinking about how the old man still watched that stuff. Ashley was an innocent 18 year old virgin teen. Not only because was a shy young teen but she was saving herself for that special someone, but since she was bored and lonely, curiosity and horniness got the best of her. She grabbed some of the DVDs and headed upstairs to one of the rooms, locking the door. Mr. Freemans grandson was asleep and he wouldn't be home for a few hours so she had the place to herself. She popped in one of the DVDs and layed down on the bed. Mr. Freeman had cameras installed all around the house and with a live update to his phone. When he saw this, it caught his eye. He watched intently. The DVD was of a blonde teen getting double penetrated by two old men. Ashley started rubbing her pussy through her shorts as she moaned softly. As the scene grew more intense, her other hand slipped under her shirt and bra and started rubbing her tiny young teen tits as she continued rubbing her teen pussy. Mr. Freeman was excited, this was his opportunity! He could use this footage and whatever else Ashley did of playing with herself as blackmail to force the teen to be all his. He quickly got himself together and started driving home, an excitement in him so bad knowing the little 18 year old barely legal cheerleader teen was finally gonna be his. As he pulled into his driveway, the scene on the movie had grown more intense and Ashley was now completely naked, her gray shirt, blue shorts, blue bra, blue panties, and her shoes laying piled on ground all messy. The teen had grown so horny that she started stripping off her clothes and threw it on the ground, eager to play with herself. She now had both of her sexy legs in mid air, pointing and curling her pretty fresh painted pink toes and feet as she fingered her beautiful perfect pink teen virgin pussy and rubbed her clit at the same time, moaning softly as she was feeling so good and building up an orgasm. "oohhh... Ohhhh yes... Ohhhh!.. Mmmm, mmmm, mmmm harder..." Ashley moaned as she played with her tight teen body. Mr. Freeman watched the live feed on his phone from his car parked outside his home. He couldn't believe it! He was waiting for the right moment to make the cheerleader all his and it came so soon and so unexpectedly. He was not expecting the sexy cheerleader to be laying naked on his bed watching one of his porn DVDs with her legs spread in mid air fingering herself and moaning. He wasted no time, as he went inside though one of the back entrances. He snuck into the room with his fake grandson and told him if he left though the backdoor quietly and went to wait for him in his car, he would give him extra money. He quickly agreed as he left the house. Perfect, he thought. Just me and 18 year old Ashley in the house alone, he smirked. He made his way quietly upstairs, standing next to the door Ashley had locked herself in. He could hear her moans through the door as she was growing hornier and closer to her orgasm. He wasted no time, taking off all his clothes and started stroking his abnormally huge 14 inch cock. With the surgeries he had, he was able to get an enormously big and thick cock, he loved it because since it was so abnormally huge, it drove all the girls wild when he fucked them, even if he forced them and they didn't want it, it made their bodies go wild because of how huge and thick it was. He started recording on his phone from outside. Poor little Ashley had no clue what was about to happen to her.

He had state of the art keyless entry doors, that were quiet if opened without a key. He scanned his finger and made his way in the room quietly, locking the door behind all in one swift motion. He kept recording as Ashley was more into the movie now, spreading her sexy legs as wide as she could, pointing and flexing her sexy teen toes, and arching and squirming her back as she was feeling amazing fingering herself and close to having an orgasm. "ohhh yeas.. Ohhh fuck.. Ohhhh my God.. Ughhh yes!, harder.., harder!.. Ughhh!" Ashley moaned. Mr. Freeman had the whole scenario recorded. Ashley had no clue as her back was turned to him and she was laying on the bed playing with herself. He wasted no time as he ran and jumped in between Ashley's legs, grabbing them forcefully and holding them open. "Hello Ashley!" he said. Ashley gasped, her heart racing a million times an hour as she didn't expect to see Richard, much less get caught. She tried to speak, caught off guard and so scared. "U-u-uh.."

"shut up slut!" Mr. Freeman interrupted the vulnerable teen. "you see this?" he said showing her the video of her playing with herself. "unless you want your family, friends, and the whole school to see little 18 year old Ashley naked with her legs spread in mid air fingering herself to porno, you will shut up and not do anything stupid. Don't try to run or yell" he explained. "I've wanted you since I layed my eyes on you Ashley.. And your finally all mine" the old man said. Ashleys heart pounded out of hr chest as she couldn't believe who she thought was a sweet old man was now blackmailing her and had her legs held open forcefully. She tired to cover her tits and pussy with her hands as she tried to speak again but was so scared and shook no words came out. "n-n-n-no.. Pl-p-pl-plea... I-i-.. Do-do-don't.." she couldn't speak at all to save her life. Mr Freeman smiled as he moved his enormous nasty 91 year old cock right in front of Ashleys 18 year old pink tight virgin pussy. Ashley gasped her eyeballs becoming wide with terror. She was so shook by how fast everything had happened she hadn't seen the old man had a not-normal **** cock. There was no way she wanted that nasty old thing anywhere near her. This is not how she was expecting to lose her virginity, to a random nasty old man, much less to a humongous cock. There was no way that huge thing would fit inside her barely legal tight teen body! Poor little Ashley tried putting her small hands on the old man's chest as if to push him back but little Ashley was no size and strength for the old man. Mr. Freeman was 6'1", broad and a little fat. He had a lot of size on him and since he was pumped on a lot of drugs he had a lot of strength for his age. Ashley was no match for him. He shoved his nasty old cock inside of Ashleys tight teen virgin pussy. It wouldn't go in at first because of how huge his cock was and because she was a virgin, however slowly but surely as the old man kept forcing and jamming his cock against her pink pussy, it slowly pried open and her 18 year old virgin pussy was broken and forced by the old man's 91 year old cock. Blood came pouring out as the old man kept forcing more and more of his cock inside of the helpless teen. Ashley screamed and tears came pouring out of her eyes as her eyes bulged out in pain. Not only did her virginity being taken hurt but the sheer size of the old man's cock forcing its way into her tight teen body hurt so bad. Ashley couldn't belive what was happening. She just wanted to make extra money babysitting for a sweet old man and everything happened so fast. She had her virginity stolen from her and was now being forced by a nasty old man, tears of sadness started mixing with tears of pain as Mr. Freeman forced more and more of his huge cock inside of the helpless teen, picking up his pace and thrusting harder and faster. Only about five inches of the old man's cock were going inside of the teen for now because of how tight she was and how huge Mr. Freemans cock was, but he didn't care. For now, it felt amazing and he was in heaven, feeling even better knowing little Ashley was a virgin and that he was the first man to be inside of her. "ohhh Ashley.., Ashley yes!!, Ashley!, Ashley!, you feel so good Ashley!, how does it feel to have a 91 year old cock take your virginity!, Ashley!!" the old man moaned. Ashley couldn't believe what she has just heard. It was so hard to process anything with so much pain, but she didn't truly know the old man's age until now. 91!? How nasty, she thought as her stomach turned. A 91 year old man had really taken her just turned 18 year old virginity. She couldn't believe it. The pain started mixing with pleasure as her teen body started turning against her. She couldn't believe it, she didn't want it, not one bit especially not from this nasty old man! But her pussy couldn't help it, the feeling of the old man's huge cock rubbing up against her gspot over and over was starting to build up an orgasm in her. "Ughhh.. Ughhh!!, ughhhh!, ahhh!!, ahhh no!!, no!!!, no!!, aghhhh!!"

Ashley moaned in pain and as her orgasm started building up. The other thing about the old man and his surgeries and being on drugs was that he would last as long as he wanted until he truly wanted to cum, no matter how hot or tight the girl was. He loved it. Plus he loved making girls bodies go crazy against their will because of his massive cock. He grabbed Ashley and forcefully layed her on her side with her back turned against him as he grabbed her leg and held it up in mid air as he rammed his cock inside the barely legal teen as he started fucking her sideways. He reached around and grabbed her teen tits with one hand while he held her leg up with the other, slamming his **** cock inside the helpless teen. Ashley couldn't take it, she was about to orgasm. She threw her eyes to the back of her head, clutching the bed sheets tight, squirming her back, and pointing and curling her toes as her little body exploded, having an out of this world level 7 orgasm. "Ughhh!!, ugh!!, ahhh!!, aghhh!!, no!, Ughhh fuck!!, uhhhhahhhh!!!" she yelled as she exploded her teen juices all over the old man's cock and her virgin blood. Mr. Freeman smiled, knowing the teen cheerleader was all his. Ashleys body trembled as she was panting like a dog trying to recover from the extraordinary orgasm while her beautiful face was filled with tears. Mr. Freeman wasted no time, grabbing Ashleys helpless body and forcing her on her back again as he grabbed her legs and stuck her pretty pink teen toes in his mouth, slobbering all over them, taking his time with both of her feet as he licked, sucked, kissed and sniffed every inch of her feet, soles, and toes. Ashley gasped as her stomach turned in disgust. The old man was really having his way with every inch of her body, from head to toe! She had no time to react as the old man forced his massive cock inside her tight teen pussy again. Mr. Freeman started fucking little Ashley while he sucked and slobbered on her toes. "ohh Ashley!!, Ashley!!, Ashley these toes!, they taste amazing!, Ashley yes!, all mine Ashley!, your all mine my little teen cheerleader slut!" he said as continued fucking Ashley harder and faster. Ashley couldn't believe it the feeling was coming again, much faster this time. Her body was building up an orgasm against her will. Her eyes shot to the back of her head again as she grabbed the bed sheets as tight as she could, arching and twisting her back in mid air off the bed, and pointing, flexing and curling her toes inside the old man's mouth as she exploded, having another level 7 orgasm. "Ughhh!!!, aghhh!!, aghhh fuck!!, fuck!, fuck!!!, Ughhh noooooooh my God!!!" she yelled as she exploded more of her teen juices on the old man's cock. Mr. Freeman was in ecstasy, not only fucking and taking the just turned 18 year Olds virginity, but being able to suck and taste her beautiful teen toes as well. Poor Ashley now had her pretty teen toes wet and covered all over in the 91 year old man's spit and saliva. Her body was trembling like crazy now as she was catching her breath, twitching at times as her body didn't know how to reach to the out of this world extraordinary orgasms. Mr. Freeman didn't care the state she was in, he wanted more and more of her. He grabbed her forcefully, bringing her teen ass up in mid air, forcing Ashley in doggy style position. Ashley was so out of it as the orgasms drained her little body and made her exhausted as her head slouched on the bed but Mr. Freeman held her up from her hips and ass as he wasted no time and rammed his cock once more inside of Ashley, fucking her doggy style this time. He grabbed her hair as he pulled it and used it as leverage to fucking Ashley harder and faster. This position allowed him to force more of his giant cock inside of Ashley, as now 7 inches of old cock were going inside of Ashleys tight teen body. Ashley was so out of it but she could feel another orgasm building up. She couldn't believe it. She had her virginity stolen by a nasty 91 year old man and he had made her cum twice now against her will and now he was doing it again. But before she could react she felt the sharpest pain ever. Mr. Freeman had now forced his huge cock inside of Ashleys tight virgin teen ass. Like he did with her perfect teen pussy he slowly but surely forced his cock until it went inside. Ashley yelled in pain as her eyes bulged out, snapping her out of her state of exhaustion and confusion. She couldn't believe it! Not only had the old man stole her virginity but he had taken her virginity from her asshole as well! Mr. Freeman moaned in ecstacy as picked up his pace, slamming Ashleys teen virgin ass. "ohhh Ashley!!, Ashley your ass feels so good!!, Ashley your all mine!!, my little teen slut!!, Ashley yes!!!" he moaned. Ashley felt the orgasm about to happen, she couldn't believe it, the nasty old man was forcing her body to orgasm even from fucking her in the ass! Her eyeballs turned white as she threw her eyes to the back of her head, biting the sheets as much as could, clutching and scratching the bed sheets, twisting and arching her back uncontrollably as her body exploded again.

"AGHHH!!!, AGHHH!!!, IT HURTS!!, FUCK!!, AGHHHHHHHHH!!!" poor little helpless Ashley yelled as she had a third intense orgasm. Mr. Freeman felt like he was about to finish also. He wasted no time, knowing the three level 7 orgasms would leave Ashley unconscious soon. He turned her back to her back as he moved to her head, pulling her hair causing her to open her mouth and yell. He jammed his huge old cock inside her pretty teen mouth as he grabbed her hair and head and started sliding his cock in and out of her soft teen lips. Ashley was so out of it she didn't know how to process anything, she just knew that the old man literally had his way with every inch of her body, her virgin pussy, virgin ass, her teen toes, and now her mouth. She felt so disgusted, not only knowing that a 91 year old cock had been inside of her 18 year old body, but inside her mouth as well. Mr. Freeman picked up the pace, feeling Ashleys warm soft lips slide up and down his cock. He couldn't take it anymore. "Ashley!!, Ashley yes!!, fuck Ashley!!, you feel so good!!, Ashley YES!!!!" he said as he exploded, shooting wads of thick old cum inside Ashleys mouth, as he quickly took his cock out knowing Ashley was turning unconscious and would throw up, continuing to unload his cum on her beautiful face and hair, making his way onto her tits and tight waist, as he continued pumping load after load onto her legs, pretty teen toes, feet, and soles, then jamming his cock into her pussy to pump load after load inside of the helpless barely legal teens pussy, and finally sticking his cock inside the teens tight asshole, unloading the last of his cum inside of Ashleys tight asshole. That's the other thing with Mr. Freeman and his surgeries and drugs he was on, that he would cum bucket loads of cum. He loved it because he loved unloading and covering every inch possible of the girls body he was fucking and taking advantage of. Ashley was unconscious at this point. Her body caving in to the three intense orgasms, unaware the nasty old man had just unloaded his old cum all over her helpless teen body. He took some pictures as he laughed. "Make sure you come dressed with a mini skirt, no panties underneath, and stripper high heels tomorrow for daddy okay? Your my little teen cheerleader slut and you do as I say!" he said laughing as he left the room.
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