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It was early Saturday morning. Dan Flanagan had slept in late since his wife and daughter were away visiting his Mother-in-law for the weekend. His first big chore of the day was to clean the pool He was on his way to the back when the doorbell rang.
"Is Maureen home" cheerfully asked the young girl at the door that he recognized as Cindy, his daughter's girlfriend. Cindy was wearing an oversize t-shirt covering her bikini, carrying a beach towel and a tote bag.
"She is at her grandmother's this weekend."
"Oh, I forgot!" Cindy lied, a look of disappointment on her face.
"But you can still use the pool if you like. I was just going to run the vacuum out there." Dan couldn't help but feel a chill run up his spine as he spoke with the young girl. At 18, the same age as his daughter, Cindy was one of the most attractive teenagers he had seen. She was also a flirt. He wasn't sure if it was innocent or by design, but she had always managed to arouse him when she had come to dinner or stayed over at their house.
It seemed that every time that she stayed over night, she always managed to be in scanty pajamas when he was around. Once, he was treated to an entire evening trying to watch TV while Cindy sat in the chair across from him. Only to his view were her legs slightly parted, just enough for him to see the crotch of her panties and her smooth, white thighs. On a couple of occasions, she seemed to have caught him looking, but she met his glance with a sexy wink and a smile. He didn't know what to do - he was almost sure that she was doing it on purpose -- flirting with him -- but he couldn't afford to let his wife and daughter find out something was going on, innocent or not.
Now she stood at the door, about to enter the house knowing he was the only one home.
"That's great, Mr. Flanigan. Thanks. I was looking forward to working on my tan!"
Cindy had found out at an early age that she had the power to seduce men. An exceptionally cute little girl, whose mother had entered her in beauty contests since she was old enough to walk, she had managed at age ten to seduce a 17-year-old boy who had been paid to babysit her. The boy had been chosen because his sister was sick and because he was a perfect kid who no one would ever suspect of doing any thing sexual with a young girl - and normally he wouldn't have - but this wasn't an ordinary little girl.
Cindy's tactic was pretty much the same as the one she continued to use: innocent flirting. She lay on the floor in front of the TV wearing only her panties and a long t-shirt over them. Gradually, the t-shirt would climb up her thighs until he had a good view of her crotch. She watched his reactions in the reflection of the TV as he sat in the chair behind her. Then when she got up to use the bathroom, she came back with nothing under her t-shirt. She let the shirt climb up her legs until he got a perfect view of her round little ass. When she was sure he had his eyes glued to her, she raised both legs and moved them apart, giving him a perfect view of her crack.
The boy had told her that she should get some pajama's on, but Cindy convinced him it was okay and even ended up on the chair in his lap, her t-shirt pulled above her waste. The boy had lost his usual discipline and fingered at her bald little pussy. She eventually ended up jacking him off - for the first time seeing a stiff cock erupt its' load all over her bald little pussy.
From there she had continued to expand her knowledge of sex by seducing older men. An uncle had taught her to suck cock and her sixth-grade teacher had been the first to sink his cock deep into her virgin cunt.
It had always been her idea to play around sexually. And now she was gonna do it with her best friend's dad!
Cindy lay on her stomach on the lounge clad only in her string bikini. Her long blonde hair was tied in pony tails on each side of her head so that it wouldn't keep the sun off her shoulders. She watched as Dan Flanagan worked around the pool. He was dressed in tight trunks and wore a Hawaiian shirt, unbuttoned, showing his hairy chest.
"Mr. Flanagan, could you help me with this lotion", she asked with all the sweet innocence she could muster.
Dan sat in the chair beside her and rubbed some of the lotion onto his hands. While he did so, Cindy undid the tie that held the top of her swimsuit on.
"I hate string marks." she exclaimed.
Dan rubbed lotion until he had covered her back and sides. An occasional finger would make contact with a half-bare breast. She didn't flinch or complain. He wondered if maybe he was letting himself in for a lot of trouble. As he questioned his ideas about this girl, she reached back and untied the stings that held her bottom on. She folded down the back of her bikini bottom and looked back at Dan with her most flirting smile said, "I don't want to be a cotton-tail, either."
Dan was speechless as he sat their viewing what had to be the most perfect teenage ass in the world. His hands rubbed in a circular motion as he covered her buns with the lotion, and then her thighs. He allowed his hands to slip occasionally between them and Cindy accommodated him by moving her legs slightly apart. Soon he found himself with his fingers buried in her crack.
"Is this something that your boyfriend usually takes care of", he asked.
"No, I don't have one, Mr. Flanigan.", she responded as he continued fingering her hole. Her beautiful body was second only to her flirty personality. She looked at him with her beautiful eyes and sly, sexy smile and asked, "Do you know why I don't have a boyfriend"
He knew she was flirting with him. The temptation was great but He knew he had already gone to far with an underage girl and didn't want to risk ending up on the wrong side of the law. He knew he had already gone way too far.
"No, seriously, do you know why I don't have a boyfriend"
"Why Cindy", he asked, patronizing the girl.
She reached over and gently rubbed his crotch, "Because, all the boys my age don't have this much cock!" She giggled. "Like, they stick it in, cum two seconds later, and then tell all their friends how they drilled you to the madras." she explained. I like older men.
He felt his rod start to harden. Cindy started to stretch out completely with her legs now spread obscenely. Talking to him with her mouth just inches away from his cock she said, "I want you to fuck me, Mr. Flanigan."
"Come with me into the house." he said, "We sure don't need someone seeing us together like this."
"This is it!", she thought to herself. She was on the verge of getting fucked by Maureen's dad. She had dreamed of it for so long, now it was going to happen!
"You know," she said as she got up and lead the way in the house, "I've been thinking about this for a long time."
He couldn't believe this was really happening. She gathered her bikini and headed indoors at a rapid trot. She had the most beautifully shaped butt he had ever seen. Dan got up and followed her indoors. He just caught a glimpse of her as she headed up the stairs to the bedrooms. He decided he would take a minute and lock the downstairs doors - just in case. This would be the worst time for someone to walk in.
Dan first looked in the master bedroom for Cindy, but didn't find her there. He looked in the guest room -- no luck either. Then he went in his daughter's room to find that she had dropped her bikini on the floor and closed the bathroom door. He sat on the bed and waited for her to come out. When she did, Dan got a shock. She looked just like his daughter.
Both girls did look something alike anyway, same color hair and eyes, same size and build. Maureen liked to wear her hair in pony tails on either side and this is how Cindy had her's fixed. She was Maureen's flannel nightshirt that had her name on it.
"Did I scare you, Mr. Flanigan", she asked.
"I wasn't expecting that," he replied. "How come you're dressed like Maureen"
"Like I thought that when we did it you could pretend that I was her. Don't you ever fantasize about doing it with your daughter"
"Uh, well, not really," he replied. But the small note of hesitancy carried across in his voice and Cindy picked up on it.
"Like, I've heard all Daddys think about doing it with their daughters. Not all do, or would even do it if they had the chance. But I think that at one time or another they think about it. You can tell me anything because now we are gonna have a lot of deep secrets between each other anyway."
"You seem wise beyond your years, young lady," he replied in an advisory tone.
"So have you thought about what it would be like to do it with Maureen" she continued. Now she was sitting on the bed beside Dan, her knees drawn up to her chest, her arms around them. Dan could see that there was nothing underneath the nightshirt. He reached beneath it and sent his hand between her thighs.
She spread her legs slightly to accommodate him, now leaning back and bracing herself on her hands behind her. Dan fondled the teenager's mound, once again sinking a finger into her hole. This didn't distract the young girl from her line of questioning. "Well" She persisted.
"Since you're THAT interested," Dan submitted, "Uh, I haven't really thought about doing it with Maureen but I have thought about watching her do it with a boy." He stopped for a minute, then quickly added, "When she is old enough to do it. And I wouldn't want her to know I was watching."
Cindy giggled. "Old enough Well, I think you missed the date if you're waiting for her to get old enough."
"You mean she is already doing it with boys" Dan felt a little short of breath and wasn't sure if it was shock or excitement. Cindy was now laying back, resting on her elbows, her legs apart, as Dan continued to sink his finger into her tight little cunt. He could feel her cunt tighten when she giggled and he knew when he got his cock in her it was going to be heaven.
"I shouldn't tell on Maureen.", Cindy said, giggling again.
"Listen, little girl," Dan said in a lecturing tone, "I told you my secret... this is no time to be holding out."
"Okay. I guess we both will have a secret then. Well, um, like what you want to do I have already done!" Cindy said, her indirectness coming across in a tone of embarrassment.
"What do you mean You have done what", Dan asked.
"Well, um, I have watched Maureen do it with a boy.", she replied.
"When Who was she with Tell me the details. Were you on a double date or what", Dan questioned the girl eagerly, now more aggressively fingering her cunt.
"Well", she replied, "she was staying overnight a couple of months ago when my brother was home from school. He 19 and goes to college. After she thought I was asleep, she got up and snuck into his room. I knew something was up 'cuz she had been flirting with him all night -- the same kind of stuff I do to you when I stay over."
Well, our bathroom connects our two rooms." She continued "At first I went into the bathroom and just listened. After a while, I could hear the bed squeaking so I opened the door a little bit. I watched until my brother got off and Maureen started moaning. Then I went back to my room and pretended to be asleep when Maureen came back into bed. I couldn't sleep.
"I was so excited -- I had actually seen my brother's beautiful buns as he pumped the living shit out of my best friend -- I couldn't sleep. So when I was sure that she was asleep, I felt up under her shirt -- the same one I have on now -- and felt her up. I wanted to see if my brother had came in her. Boy, had he ever! She was drenched with it. Like I am not into other girls or anything but knowing Jason's, uh, that's my brother's cum was in her made me do it. I got it all over my hand and then fingered myself, getting his cum up my cunt too. I figured it was the only time that I would ever get my brother's cum in my hole."
Dan was beyond control now. He had never been this excited. His fingering of Cindy had gotten her pumping her teen little ass as she told him about his daughters' exploits. Now his rod was stiff as a lead pipe beneath the swimsuit he still had on. He stood and pulled the suit off, exposing himself to the girl for the first time. As if in reciprocation, she removed the nightshirt, exposing her budding little breasts.
They were small and firm. As she wriggled the shirt over her head, he felt the saliva in his mouth accumulate and he had to swallow. She still looked a lot like his daughter and the sight sent spastic shock waves to his cock, as if it couldn't finish hardening fast enough. He noticed the a faded tan line right above her small triangular island of pubic hair. He felt the blood rush to his head. She was smiling as she jumped up and wrapped her legs around his waist. She flung her arms around his neck and stuck her tongue deep into his mouth. She seemed so light and small.
Her breathing got incredibly heavy. He layed her back down on the bed as she buried her face in the hair on his chest.
His cock was standing straight up. He felt Cindy's juices on his leg as she rubbed her pussy on his thigh. "I want you to fuck me, Mr. Flanigan, oooh, I want you fuck me deep, please." His shaft was harder than he could remember. He knew he couldn't contain himself much longer. He swallowed one of her luscious little tits whole.
"Daddy!", she gasped, still pretending to be his daughter. She reached down and felt his rock hard tool. She continued to talk in breathy whispers, "Oh, God", she breathed. She grabbed his tool with her hand, her fingers just barely making it all the way around.
"Oh please, oh please, oh please, Mr. Flanigan," she continued. "Mmmmmm, she sighed, "God it's so big, it's so hard." She began to stroke his cock up and down with both hands. When he couldn't take it any more, he grabbed one leg in each hand and spread her wide.
"Oh Daddy, ram it in, ram it in", she practically screamed. He positioned himself over her and just touched her drenched little island of hair. "Ohhhhhh, yes, yes, please, yes." She sounded as if she was crying. The tip of his shaft rubbed her soft mound, but He couldn't yet feel the opening.
She lifted her legs straight back to her shoulders as she pulled on his cock with both hands toward her cunt, the teenager was definitely experienced in helping a cock find it's mark. "Uoooh, Mr. Flanigan, put it in!"
But Dan had other ideas. Before he fucked this little girl he wanted to taste her and see her. He moved down so that his face was between her thighs. He gazed at her cuntal hole. She didn't have that much hair so it was easy to see. Her lips were together much like a virgin. With his tongue flat He licked her hot little box from the beginning of her asshole all the way up to her budding little clitoris. "Mmmmmmm" she moaned while biting her upper lip. Cindy started rotating her hips as his licking increased in tempo. He gave her a deep stab with his tongue.
"OOOOOHHHHH!!!" she exclaimed, "Again, please, again" she said as she grabbed his hair and tried to shove his face inside. He began to eat her furiously. "Oh, yes, put your tongue inside" Her pussy tightened around his tongue as He opened his mouth wider and stuck his tongue in deeper. She began to fuck his face with surprising power.
He knew she was close to orgasm. She stood up as he repositioned himself on the bed with her above him. She turned around and straddled him, placing her cunt over his throbbing tool. She braced herself on one arm, reached back with the other and guided the head of his cock to her opening and inserted just the tip of it into her slippery box.
"I want you... no matter what it takes, I'm getting that monster all of the way inside of me". She said as she positioned herself straight up over him. He felt his head start to slip in deeper as Cindy pushed. "God, it's so big," she said as she manuvered on his member hunching down to get it in. Then with a long grunt she forced his rock hard head in. "Ooooh mmmyyyyyy gooooddddddd!!!"she breathed as she began to move up and down very slowly.
Her pussy was so tight. "When did you lose your virginity" he asked. Oblivious to his question she just rocked gently up and down, and even though most of his tool was still outside of her, she seemed to enjoy herself just fine. "Cindy, I'm talking to you, when did you lose your virginity"
She barely replied between breaths, "...three years ago... Sixth grade."
Squatted over him, she used her body weight to push his gleaming wet cock back inside of her. "Oh yeah, I love it Mr. Flanigan.", she said. She started moving up and down as another half inch disappeared into her sweet canal. She felt herself starting to com and the extra lubrication enabled her to sink another inch.
"Ooooooooooo yeah, this is what I needed, a real man." Even though three quarters of his rock hard shaft remained she began to slide up and down with a steadily increasing tempo. "It's going in all the way!", she cried out. "Oh yes, it's going in," she said. Supporting part of her body weight with her hands on his chest she began to make slow circles as his cock began to disappear inside of her.
She began to rock back and forth on his cock. "Oh yes, Mr. Flanigan, let me fuck you, just like Maureen fucked my brother.", she said as she began to pick up speed, "Don't move, oh it feels really incredible." Her eyes rolled back and her mouth opened as she continued to hammer away at his rock hard shaft.
Alternating from a quick succession of quick strokes and slow long strokes he began to feel an eruption coming on and all he could think of was getting ALL of his cock up inside of Cindy. Coming up on one of her long strokes she pulled his cock out of her cunt just enough to maintain his head just outside as she began to rub the slippery knob back and forth between her asshole and her pussy hole. Then she slowly slid it back into her succulent young cunt. Penetrating her again felt like breaking new ground for the second time. Going in, he felt his foreskin pulled all the way back exposing his head inside of her. The sensation was unreal. Then she stopped. He wondered if anything was wrong but she just stood there motionless with her eyes closed.
He looked at her, she was beautiful, I mean a really beautiful girl blooming into womanhood. She looked so much like his own daughter. Then slowly she opened her eyes and looked at me and said, "I want you to get on top of me and fuck me until it hurts, fuck me like a whore."
That was all he needed to hear. As He rolled on top of her little teenage body he wondered how it must have been for the guys fucking his daughter. He got on top and positioned his hands on her ass cheeks. She whispered in his ear, "Don't be afraid, do what you want." With that she began to lick his mouth. He started to fuck with only a fraction of his strength. Her snatch felt so good He didn't want to turn her off by hurting her. "What are you waiting for", she asked, "Put it all the way in. Fuck me like you would that slut daughter of yours."
He started to fuck her like he knew he always wanted to fuck his little girl. "Oh, oh,oooh, yes, oooooooh, that's the way, that's the way, yes, yes, fuck me.", she moaned.
He began to pound her letting most of his weight crash her but He still couldn't get his whole cock inside of her. "Oh please, fuck me just like that, please don't stop, God it feels so good, break me in half." He grabbed her ass cheeks tighter and with all of his strength He pushed the FULL length of his shaft inside of her. It sounded like the muffle sound of knuckles cracking.
"Ahh, ahh, oh God, hold it right there", Cindy said, trying to catch her breath. He looked down to her love hole and He couldn't believe that all of his meat was inside such a small opening. "Hold it right there, it hurts but it feels so good. Is it all the way in" she asked.
He looked down to make sure, there was absolutely no space between them whatsoever. "It's all the way in Cindy."
"Good," she said, "Now we can take care of business." He began to ram her with reckless abandon.
"Uh, uh, uh ,uh, uh, oooh, uh, uh," said Cindy with each pelvic crash."Oh, God, Oh, God, Oh, Yes, I, Feel, It, Oh, F, Fu, Fuck, Me, Fuck, Fuck, Fuck, Fuck, Me," she continued between each forceful thrust. She now had her legs wrapped around him tightly, her feet touching over the small of his back.
He knew he was about to explode in her. He wondered whether he should. Was she on birth control he started to ram her even harder. She couldn't move anywhere, he had her pinned down and she loved it. As his eruption got nearer he wondered, should if he should pull out. It felt so good. "I'm coming," he said.
"Oh yeah," Cindy replied, "Come baby, flood me with your love cream. Give me the same cum that started Maureen!" Those very words were what did it. He exploded inside of her. "Ooooooo, give it to me all, empty yourself inside of me!", she cried. He wanted to go even deeper inside of her as his balls quivered with each burst. "Oh God, I think I'm coming," moaned Cindy, "Oh yes, I think I'm coming, oh, oh yes, oh please don't stop, please don't stop, fuck me, please fuck me."
His hot scum made her cunt feel even better than before. "OH, OH, YES!, OOOH, AAAH, FUCK ME!", Cindy screamed as she drew closer to her blissful ecstacy. She began to thrust him obscenely, and her cunt made wet farting noises as It grabbed his creaming cock. "AAAAH, OOOOOH!, OH GOD!, OH GOD!, OH YES!, AH, AH, AH, OOOOOOOOOOOOOOOOOOOOOHHHHHHHHHHHHH!", she screamed as her love box opened up and her juices flowed.
By now, Dans' sperm had been churned to a white frothy foam that covered the young girl's crotch like a slippery lather. As they stopped and she lay back on the bed, her legs still wide open and bent at the knees, dan's sperm literally flowed from her wide-open cunt, down the crack of her ass and onto his daughter's bed.
"It feels good opened up this way" , Cindy said as she drifted off to sleep. He looked at her thinking how lucky He was to have been given this opportunity. She was so beautiful.
Dan watched the naked girl sleep, admiring her 18 year old body. He knew that he wouldn't stop with this first fuck. He also knew that he was probably going to use this opportunity to hear the details of his daughter's sexual experiences from her best friend and to realize a long time fantasy -- watching his own teenage daughter get fucked by a young boy.
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- Cindy's Friends Father
- Published: Sep 27, 2005
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