Fantasies of a Babysitter
Hi, my name is Cindy. I'm a twenty-year-old college student living
One of my best jobs is to house sit. No kids to take care of just stay at someone’s house for a couple of days. And these are not just ordinary homes, most are multi-million dollar homes at the beach. Last week I was house sitting one of my favorite places.
Let's just call him Bill; I won't use his real name. Bill used to be a movie star about ten years ago. Very famous. He did quite well and just retired from entertainment, having been very successful in the entertainment business. He travels a lot for his investments, so I often get to house sit for him. He pays well and I get to work on my tan.
By the way, Bill is the most gorgeous man I have ever seen. He's only about mid forties, a deep tan, works out in his own gym and takes great care of himself. I've seen him with a lot of women, sports stars, movie stars, socialites, all gorgeous. But Bill is still single, not sure why. I would let him in my panties in a second! Okay, maybe I wouldn't. I told you, I don't date much, but masturbate a lot. Shy thing I guess. But back to the story.
I stay in one of his guest rooms. It's a massive room the size of my parent’s
whole house, one glass wall overlooking the
Bill walked quietly into the house, noticed that all the lights were out, and hoped that she was asleep. While Cindy wasn't as beautiful or sophisticated as the women he usually dated, there was just something about her that always drew her to him. He had finally figured it out. It was her lips. His cock seemed to spring to life each time she opened her mouth. The only thought that raced through his head was what it would be like to feel her hot breath blowing on his cock, her wet tongue racing over the head or her silky lips wrapped tightly around the head of his cock. He could hardly think of anything else when he saw her. He had seen the way she looked at him, hoping that he was right, hoping that she would do anything for him. His cock throbbed at the thought of her sucking his cock. He crept toward the guest room, quietly opening the door. The room was partly lit by the full moon, the drapes open. He could see neatly tucked under the comforter as he moved closer towards her.
His cock jumped in his pants when he saw her. Her head was on the pillow, her mouth open slightly as she slept quietly. He could hear her gentle breathing, her lips slightly moistened. He watched her for about ten minutes, seeing her tongue come out and swipe at her lips, her lips glistening in the moonlight. He couldn't wait any longer. He slowly slipped out of his clothes, his breath ragged as he indulged in his fantasy. His hand went down to his cock, gripping it tightly as he stroked it up and down. God, he had to have her mouth soon, before he came all over the bed. His naked body moved quietly to the bed, kneeling on the edge, holding his breath as he waited to see if her body moved. She didn't stir, so he slid over towards her.
He moved his hand closed to her face, only inches from her moist lips. He held his breath as his finger lightly ran over her lower lip, her eyes seem to flutter but they didn’t open. His cock jerked in excitement as he felt her soft lips for the first time, the thought of them touching his cock exciting him. He ran his finger around her lips, and then pushed into her open mouth, her tongue touching his finger in reflex. He let his finger slide inside her mouth, Cindy still soundly sleeping as he moved deeper into the hot recesses of her mouth. God, he couldn't wait much longer. She still didn't stir. He moved next to her head, kneeling only inches from it. He stroked his cock as he lowered his throbbing member until he felt her lips touch his cock. "GGODDD," he moaned too loudly as he felt her lips touching his cock. He saw the head of his cock leak out pre-cum, eager to pump his cock in her mouth and fill it to overfilling. His cum glistened in the light on her lips as if it were a lipstick. His cock jerked in pleasure, her head turning slightly as it bounced on her lips.
Cindy was having one of her erotic dreams. This one even more vivid than the others. She was dreaming of the time when she was younger and had sex with two older boys. It was one of her most reoccurring dreams. The difference in this one was that one of the boys was trying to get her to suck his cock. One was between her legs, his hard cock sliding in and out of her recently violated pussy, the other was rubbing his slippery cock all over her face, a trail of his cum clinging to her skin as he moved it back and forth. Hands tilted her head back, Cindy submissively opening her mouth in response to the strong hands urging her to perform the task. She had always been afraid of perform such a loathsome act, needing to be forced to accommodate the act that she thought was so degrading. The dream was so real, licking her lips, the salty taste quickly basting her mouth.
Bill could see her eyes beginning to flutter as she moved. Her mouth seemed to be opening, Bill didn’t waste any time, and took advantage of the situation to let his cock rub around her lips, his cock jerking in pleasure as he did. He saw her stir, knowing that she was wakening, the moment of truth upon him.
"Don't open your eyes," he instructed in a deep, demanding voice.
Cindy was suddenly brought back to reality by the familiar voice of Bill. She was awake, her eyes still shut, quickly realizing that the dream of hot, hard flesh on her lips wasn’t a dream, she could feel it sitting on her lips. She heard his command, not wanting to open them, afraid of confronting the reality of the situation. Did he really have his cock on her lips? She squeezed her eyes tighter, her only response to his command.
"Do you know what I want you to do?" He moved his cock from her lips, letting it rest on her cheek, the cock jerking against her silky skin.
"I've never done that before," was the only thing she could answer.
His cock leaped in joy at her response. It wasn't a denial, more of a statement of her intentions to perform.
"I'll teach you."
"Yes Sir," she muttered.
Bill picked up the black mask that he brought. "I'm going to put a mask to cover your eyes so you don't have to squeeze your eyes tight. Lean your head forward so I can put it around your head." It was an order, not a request.
So he'd planned it, the mask ready. How did he know she would submit? She shivered when his fingers touched her neck, sliding the mask down until it covered her eyes. She opened her eyes, confronted by the darkness of the mask. She waited, not sure what to do. She felt the hot flesh touch her cheek again, his hand pushing her face softly towards it. She could feel it throbbing against her skin, almost feeling as if it were burning her flesh. She kept her lips closed as he slid it across her lips, her tongue instinctively coming out, startling her as she suddenly came in contact with it.
"No, don't stop. Open your mouth and stick out your tongue. Your lips are so inviting, my cock is throbbing in lust. It wants to feel your lips wrapped tightly around my hot flesh."
She couldn't believe that Bill desired her. He had often looked at her, but not like she looked at him. She had even imagined him taking her body one night, but the thought of him taking her in her mouth was something she could never have fathomed. She was always disgusted by the thought of taking someone's cock in her mouth. Even worse the thought of having it fill her mouth with cum and being forced to swallow it.
"Are you going to cum in my mouth?" She had to know.
"Yes. And you're going to swallow it."
"Yes Sir." She didn't know if she could do it with choking, but she knew she wouldn’t have a choice.
"You're going to have to take my cock deep in your mouth. Once you get use to it, I going to push it into your throat where your throat muscles will give me a very enjoyable fuck."
"I'm afraid I'll choke and gag if you do that?"
"I'm counting on you doing that. That's what makes it so enjoyable. If you are a good girl, I'll let you masturbate while I fuck your mouth."
The thought of him making her take it in her throat sent a shiver down between her legs. The thought of his hands on her head, forcing his cock into her throat while she gagged and choked excited her. Now he wanted her to masturbate while he fucked her mouth. "Under the covers Sir?"
"No, I want to see your naked body and watch your fingers play with your pussy. The thought of watching you cum is appealing to me, to see the expression on your face as you orgasm for me, your mouth filled with my cock. Hopefully I can cum at the same time, see your cheeks bulge out as I fill your mouth with my cum."
"I don't know if I can do that Sir." Her mind quickly filled with pictures of her legs spread, her pussy wet as her fingers played up and down her slit, Bill instructing her what to do as she sucked his cock eagerly, holding her breath as she waited for the inevitable time when he would cum in her mouth.
"It wasn't a question, Cindy. You will masturbate your pretty little pussy while you suck my cock. I won't tell you again."
She felt his hand tighter on her head. She could only murmur, "Yes Sir". She opened her mouth; her tongue slowly began to stick out, almost afraid of what she would find. Suddenly she felt it, the hard, rubbery head of a cock. She pulled her tongue back, then pushed it out again. She could already taste the salty flavor, knowing that it was his cum.
He liked the way her tongue moved tentatively, barely touching his cock, his throbbing member jumping in appreciation at her wet tongue finally reached out and touched it, then shooting back into her mouth. "Yes, good girl," he complimented her as her tongue moved back out again.
It felt strange, his cock so hot. It was hard, yet rubbery, a different texture then she had expected. Her tongue moved again, this time not pulling back, lightly rubbing along the thick head. She felt it jerk as her tongue moved in a circle, feeling the hole in the center, resting the tip of her tongue on it. She could taste the fluids that her tongue had coaxed out, a thick texture, salty, not all together unpleasant but just a small amount seemed to spread quickly inside her mouth. She let her tongue run down the side until she felt the ridge around the head, imagining the large red helmet that was the head, running her tongue all around the edge, the tip of the cock rubbing against her cheeks as she did.
He enjoyed the way she seemed to be exploring his cock with her tongue. Would she be so willing once she started sucking his cock, taking it in her mouth? "While I am enjoying your tongue Cindy, it is time for you to wrap your lips around my cock as well."
She opened her mouth wide, his hand under her chin, lifting her head up until she felt his cock touch her lips again. She waited until she felt it, his cock sliding along her lips, slowly and sensuously entering her mouth.
"What a lovely hot mouth Cindy, your hot breath is making me want to cum." He pulled her forward more, eager to feel her lips around his cock. "Close your lips on my cock. Make it nice and tight, just like your pussy would be."
She let her lips close, grasping the hard cock in her mouth, her lips capturing it just below the rim, the thick helmet of his cock inside her mouth. It felt strange and exciting, being forced to take his cock in her mouth. Not as she thought it would be like, not as distasteful as she remembered. Maybe it was the slow buildup, his teasing her as she lay there, the darkness of the blindfold making it as if she had no choice but to submit to him, laying there unable to know what he was doing until she felt it. She let her tongue run over the head, feeling it jerk, her lips tightening on it, holding it firm. Her tongue continued to explore the hot flesh, running over the head, feeling it leak out when she ran across the slit, tasting his juices. The taste seemed to grow on her, the thought of it filling her mouth exciting her. Would she be able to swallow it all?
"Oh yes Cindy. You have a God given talent for sucking cock. You just needed lessons on how to perform. OHHH GGGGODDDD," he screamed, sliding his cock forward into her mouth, fighting the urge to cum.
She felt it, the jerking of his cock, his body pushing his thick cock through her tightly clenched lips and then his body grew rigid. She felt the jet of cum shoot from his cock into her waiting mouth, her tongue suddenly bathed with the thick, salty fluid. She froze, not sure of what to do, afraid she had made him cum too soon.
His hands gripped her head hard, holding her still as he fought the urge to cum, unloading a short ropey burst of cum into her mouth before he could control himself, pleased that she stopped moving her tongue. "Sorry Cindy, but your mouth is just too good. Don't worry; it was just a little shot. My cock is still hard. There is so much more for you. You still have to take my cock in your throat. Now hold the cum in your mouth, don't swallow it until I tell you. Tongue my cock again."
She felt the thick cum sitting on her tongue. It slowly spread, filling her mouth, the salty taste permeating her taste buds. It was no longer unpleasant, just different. She held it inside her mouth, using her tongue to coat his cock with his cum, taking the thick crème and lathering his head with it.
He began to slide his hips back and forth in a gentle fucking motion, holding her head firmly as he used her mouth. He had to fight the urge to cum. "Let me see your tits Cindy. Slip the comforter down to your waist."
He wanted to see her naked body, or at least half of it. But she knew that it was only the beginning, he had already told her that he wanted to watch her masturbate until she came. At least she was blindfolded; she wouldn't have to see his eyes raping her naked body. Her hands trembled as she gripped the top of the comforter, his cock beginning to slide in and out of her mouth, aided by the cum that coated the thick member. She felt her nipples harden suddenly when the comforter slid over the tips, the cool air seemed to rush over them, signaling to her that she was half-naked.
"What a lovely set of tits Cindy. Big, pink nipples, nice dark areolas, nice firm flesh. Arch your back and stick out your tits for me Cindy." He teased her.
She thought the darkness would prevent the embarrassment, but he enjoyed describing her naked body, making her pose for him as she arched her back, a mental image in her mind of how she must look posing her naked body for him. "GGGODDD," she cried out when she felt a wet finger touch her nipple, feeling the tip almost burst in pleasure. She felt the finger return, this time slapping one hard tip back and forth until she felt a strange stinging in the end of her nipple. It felt as if it would explode. His hips continued to rock back and forth, shoving his cock in and out of her mouth.
"Play with your tits for me Cindy. Show me how hard you can make them. And keep your tongue running over my cock. I'm going to fuck your face now." He watched as her hands moved to her breasts, cupping the twin globes, her fingers plucking at her hard nipples. He heard her moan, not sure if it was because of her fingers or his cock as he began to take deep thrusts into her willing mouth. "Yes, suck hard Cindy," he moaned in pleasure as his cock banged against the back of her throat, his hips driving his cock with pounding thrusts, her sweet lips wrapped so tightly around his cock. He gripped her head tighter, enjoying her lips as they pressed tightly around his cock as if it were her pussy encasing his cock.
His cock drove in and out of her mouth, his balls slapping hard against her chin as he fucked her face, his hands holding her head firmly, her hands plucking at her nipples, deriving so much pleasure as she pinched them hard. She felt so degraded, yet so excited as he used her mouth as if it were her vagina, fucking her with deep strokes that each time threatened to race down her throat at the same time, forcing her to play with her body as she imagined him watching her. It seemed that she was deriving as much pleasure from the oral copulation as he was. She decided to get brave, her hands sliding down from her breasts, over the flat plane of her stomach to push the comforter off her abdomen. His cock slowed down, Cindy imagining him gazing down at her.
"Yes, I like that. Show me how you can play with your pussy. Masturbate for me." Bill began to slow his thrusts in her mouth, his cock feeling as if he would cum soon. He wanted to wait as long as possible; he wanted to get her aroused so she would cum when he did. "All the way down, kick the comforter off of you. Then spread those lovely legs for me. Show me that sweet pussy."
She sucked hard on the cock in her mouth, dragging it deep into the hot confines, her tongue running back and forth over the shaft, feeling the bumps and ridges, wanting to please him. She felt the cool air on her naked body, slowly spreading her legs, feeling her wet pussy lips separate, the cool air of the morning blowing on her wet sex. She could only imagine how she must look, Bill poised over her naked body, the bright morning light shining on her naked body as she sucked his cock. She let her hands move down to her spread legs, pulling her pussy lips back even farther, realizing how brazenly she was revealing her inner sex, her inner pink pussy dripping wet with desire.
"What a lovely pussy Cindy. So nice and pink. Pull your lips apart more, until they hurt a bit. You'd been surprised that a bit of pain feels good." He watched as her fingertips gripped her lips, digging into the slick lips, pulling them, stretching them wide, a moan on his cock that she was pulling them hard. "Yes, now bring your legs up and bow your knees out. Show me all of your treasures." He gave his hips a powerful thrust, driving his cock forcefully to the back of her throat. But he didn’t stop until her heard her choke, his cockhead banging against her tonsils.
"GGGHH," she gagged as his cock pushed farther then it had ever, slamming into her mouth until she almost swallowed it, the thick head making her choke, his cock taking advantage of the situation and push deeper, deeper into her opened throat. She felt his hands tighten on her head, knowing that he was getting to the point where he would drive his cock into her throat. She didn't know where she would be able to stand it, but she wasn't sure she had much choice. She began to rub her clit, hoping the increased arousal would somehow make the inevitable throat fucking more pleasurable.
"Yes, play with that big clit. Look how aroused you are. Stick two fingers in your pussy. Fingerfuck yourself. Imagine my cock driving between your legs." Her mouth seemed to take a renewed interest, her lips so tight that it was getting difficult to drive it back and forth. And her tongue seemed to be everywhere, lathering up his cock from the tip down the shaft, the raspy surface of her tongue bringing such pleasures to his cock. He couldn't help himself any longer, his cock continually leaked into her hot mouth, his balls tingling as they banged against her chin with each thrust.
She was going crazy with lust, finger fucking herself brazenly as he fucked her face, his hands pinning her head to the pillow, driving his hips back and forth. She had never been taken so ruthlessly before, her mouth serving to please him, her hands having to derive her own pleasure. She took a deep breath as he drove into her mouth, gagging as he breached her throat. She knew it was time as he held his cock in the breach, his hands gripping her head until Cindy felt like it was in a vice. "GGGHH," she gagged again, her throat opening as she choked her stomach turning as she fought the urge to vomit. He yanked off the blindfold, tears streaming from her eyes, but she knew that there would be no turning back. He was determined to force her to take his cock in her throat and she was unwilling to stop him. She jammed three fingers in her pussy, two fingers twisting her clit harshly, hoping the pain in her loins would take away the fear she felt.
It was time, his cock poised in her throat, her body clenched and tight. He shoved, feeling her choke, the muscles of her throat opening up and then clenching down on his rigid cockhead as he began the gradual ascent into her throat. It felt like a warm gloved hand gripping his cock. "God, your throat is eating my cock alive." He pushed deeper, another gag coming from her muffled mouth, tears running down from her wide-open eyes, searching for some relief. "Take it deep Cindy. Take my cock in your throat." He gave her a couple of staccotto jerks of his cock, harshly pushing in and out of her throat, her muscles beginning to spasm on his hard flesh. He placed a hand under her chin, pulling her head up so he could see the look on her face as he throat fucked her. The mask no longer hid her from what was happening her eyes only inches from his stomach, feeling his balls on her chin, as she was slowly pulled onto the hard cock, the thick member sliding deeper and deeper into her clenching throat.
"Such a good cocksucker. Can you cum for me Cindy? Play with that sweet pussy and cum for me. If you do, I'll pull my cock from your throat. Then I'm going to empty my balls in your mouth, filling you with my cum."
He was using her throat as if it were her pussy, pulling her on and off his raging cock. She felt her throat rubbed raw, the choking making her stomach turn. She rubbed her pussy faster, running three fingers in and out, spreading her fingers when they were inside her, feeling her insides stretching. Her other hand pinched her clit, her ass raising up from the bed, the pain and pleasure mixing together, Cindy not even able to comprehend what was happening. All she knew was she had an urgent need to cum. Even worse, she was looking forward to Bill cumming in her mouth, wanting to experience the complete surrender of her body to him. It came on her quickly, her pussy clenching uncontrollably on her fingers, yanking hard on her clit, stretching it out. It hit her like a freight train, her body shuddering and shaking as she came, her fingers drenched in her own juices. She took a deep breath, long enough to fill her lungs before Bill blasted a thick load of cum into her mouth. It wasn't anything like the last one. This one seemed to make her cheeks bulge out with the thick crème as he unloaded gallons of cum into her willing mouth. It seemed like gallons, cum dripping from the corner of her mouth as she attempted to swallow the thick cum. She coughed, choking on the thick crème as she tried to swallow the abundant crème bulging out her cheeks. As soon as she swallowed, a second load spilled from his cock into her waiting mouth, his hips pumping in and out of her tightly clenched lips, her tongue lapping at the head like a cat.
Bill couldn't wait any longer. He saw her cumming, her fingers moving so fast as she fingerfucked herself into an orgasmic frenzy, her hips moving up and down as her fingers raced over her pussy. He pulled his cock from her throat, her eyes open in relief at being able to breathe. He let her tongue run over the head as he felt the tingling race up from his balls to shoot a load of cum into her waiting mouth. Her eyes opened wide in surprise as she scrambled to contain the copious fluid that bulged her cheeks out. He let his hand rest on her neck, feeling her beginning to swallow, another load of cum shooting out before she could finish, her choking exciting him. One more load filled her mouth as he watched her hand slow down her masturbation, her fingers glistening from her juices, her throat swallowing, a river of cum dripping from the corner of her mouth.
She almost hated for his cock to leave, tightening her lips on his shrinking cock as he pulled it out, her body exhausted from the orgasm that raced through her body. She had never been so completely taken by one individual, her body used solely for the purpose of pleasuring him, her mouth taken as a substitute for her pussy, forced to orally satisfy him until he discharged his semen deep into her stomach. He pushed her hair from her face as he got up.
"Go back to sleep. I have to go to work. There is no hurry for you to leave. I hope to see you again soon. I enjoyed taking you so completely." He looked down at her naked body. "And a beautiful creature you are." He got up and left, but not before he left some money on the table.
"I've never been so sexually overcome by one person before,” she responded. “You saw that I enjoyed it," looking down at her naked body, not even ashamed of him seeing her that way.
She sat up on the bed when she heard the door close. She leaned over the table and counted the money he left. She smiled, pleased. It was exactly the same amount that he always paid her. She was glad.