Watching, Fantasizing, Getting...

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Hilary's mom's boyfriend fucks her friend, then her.
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Big Gunz
Big Gunz
997 Followers

Lying almost naked on her bed, Hilary slid her hand under the waist of her panties and slowly glided her fingers towards her aching pussy. The moment she touched her hot, hard clit she let out a low gasp. She glided her fingers slowly around her clit in a circular motion as she closed her eyes and let her mind wander. Her fingers slipped lower, teasing at the opening to her pussy. She spread her lips and pushed two fingers in, just a little. Sliding her panties out of the way, she pushed deeper into her pussy, slowly moving her fingers back and forth, letting in a little more each time. She squeezed her eyes tight as her head rolled back and her clit began to tingle.

As she cupped her ample c-cup breasts and pulled on her rock hard nipples, a soft moan escaped Hilary's lips as she continued stroking herself. Light, gasping breaths now accompanied her gentle thrusting, and her mind began to focus on the images that had brought her here.

It had been lest than a week ago that she had stumbled upon the scene that now manifested itself as the script for her latest masturbatory fantasy...

*

The previous Saturday night, Hilary had decided to have a few friends over, capitalizing on the fact that her mom would be working a 12-hour overnight shift at the hospital, leaving her new boyfriend as the only "adult" supervision for she and her college friends. Steve had been dating her mother for about six months, during most of which Hilary was off at her freshman year of college. He had moved in about a month ago, just before Hilary returned home for summer break. She looked a lot like her mother - both were good looking, lively blondes with cute smiles and shapely bodies.

She had not had a lot of time to form much of an opinion about her mother's new man, though from the early impression Hilary had gotten of him, he seemed like a decent enough guy. She guessed that Steve was about 40ish, and he looked like he kept himself in pretty good shape. He was definitely better looking than some of the guys her mother had dated - about six feet tall with brown hair accented by hints of grey around his temples and in his goatee. Hilary always found him very polite around her, and she appreciated that, at least thus far, he had never once tried to interject himself into any parental issues she had with her mother. Even though she was only staying with them for a few months until school started again in September, she had no idea what his thoughts were towards his girlfriend's 19-year-old daughter now living with them.

Hilary was hoping that Steve's pleasant demeanour and lack of any parenting attempts towards her would continue as she invited about 15 or 20 friends over for a sort of kick off to summer get-together. As the evening progressed, she was quite happy to find that her optimism towards her mother's boyfriend seemed to be holding true, as he behaved better than she could have hoped, even mingling and drinking with her friends.

As the party began to die down and the crowd began to thin, Hilary found herself in a rather blissful state of semi-intoxication as she playfully escorted that last of her guests to the door and wished them goodnight. She then began busying herself with cleaning up the main floor of the house, where most of the festivities had taken place. As she was straightening up the living room, she thought she heard voices coming from the stairs leading to the basement. Figuring that she must have lost track of some frisky pair who were now down in the den, Hilary headed downstairs to break-up the little private party and send the happy couple on their way so she could finish cleaning up and get to bed.

Soft music overcame the voices as she ventured down the stairs to see what was going on. Arriving at the bottom of the stairway, Hilary paused momentarily and thought about how embarrassing a situation this might be for the couple. Deciding to see who she was dealing with before barging in, she slowly leaned around the corner to catch a glimpse of the duo. What she saw blew her mind...

*

Steve sat on the couch watching the beautiful young woman dance slowly and suggestively in front of him. His eyes were glued to her writhing form as she slowly removed her top and bra, her nipples already erect on her abundant chest. His hand was cradling his crotch as his private dancer continued to disrobe, running her hands over her firm tits and up into her long chestnut brown hair.

Hilary could not believe what she was seeing. As shorts and panties fell into the small pile of clothing on the floor, she recognized who the stripper was - a girl she had graduated high school with, now a 19-year-old freshman like her. She had know this Jennifer since grade nine, and now she was watching her strip for her mother's boyfriend!

In utter shock, Hilary found herself unable to move as she watched Steve remove his shirt and loosen his belt. Jennifer, standing naked in front of him, pulled him from the couch and up against her body. Hilary watched, anxiously, as her lips parted and she took his tongue in her mouth. They kissed passionately, his hands roaming over her smooth skin, digging into her ass and pulling her tight against him. Her skilled hands worked quickly to unfasten his jeans, and she abruptly broke their lip-lock, sinking slowly down to her knees, pulling his pants down with her.

Jennifer grabbed his cock and stuffed it through her lips in one fluid suck. Steve let of a low growl as she began working her mouth back and forth over his dick. She grabbed at his ass and pulled him towards her face as his hands found their way to the back of her head, tangling in her coiled locks. Slowly, his hips began to thrust forward as she continued to pleasure him with her capable oral skills.

Hilary could not take her eyes off of the sight in front of her. 'How could he do this to my mother?' she thought. At the same time, she found herself feeling flush in the face and could feel that her panties had begun to dampen as she watched the scene playing out before her. They turned slightly and she could now see his glistening penis sliding in and out of her mouth. She sucked him down to his root, working him over feverishly for several more minutes, until she pulled away from him suddenly.

Jennifer pushed him back onto the couch and placed her knees on either side of his hips, straddling him and hovering her pussy over his wet manhood. As Steve held his pulsing erection at her opening, Hilary could not help but stare. It was not too long, but it was very, very thick.

As Jennifer slid herself onto his slick shaft, Hilary suddenly realized that her right hand was suddenly down the front of her pants and she was now pushing two fingers into her own body. Unable to stop herself, she shook slightly as she parted her labia and slid her digits in. As she watched one of her high school friends impale herself on the throbbing cock of her mother's boyfriend, she slid her fingers into her now dripping pussy.

Steve drilled his dick up into Jennifer's hot hole and her eyes glazed as she quickly started in with moans, gasps and cries as she began fucking him with slow and steady thrusts up and down. He grasped her hips as she quickly pulled him forward and kissed his ravenously, his cock pumping back and forth, and her cunt driving up and down to suck him in. Placing her hands on his shoulders for support, she cried out, "Fuck me! Fuck me!"

Captivated by the sight, Hilary almost forgot where she was. Her jeans were completely undone and she was now matching the couple's thrusts, driving her fingers deep each time Jennifer rode down Steve's penis. Wetness was running down her legs as the scene in front of her quickened.

Steve pulled Jennifer off of him and tossed her down onto the couch on her back. He swiftly positioned himself between her legs, and without hesitation, slid his cock back into her pussy. He lifted her legs up onto his shoulders and grabbed onto her hips, pulling her back and forth on his cock. She was gasping and moaning, her hands alternating between rubbing her clit as fast as she could, and squeezing and grabbing at her big tits as the shook wildly from the pounding she was taking.

Hilary watched as a shudder passed through Jennifer's entire body and she squealed repeatedly as the throes of her orgasm swept over her. Close to cumming herself, Hilary continued pumping her cunt as she watched the girl get off. Right then, she thought she saw Steve look right at her, almost stealing a glance in her direction and pausing to give a little half-smile before he resumed pumping into his young lover.

Her legs high in the air as he pounded into her pussy, Jennifer continued her squealing as his brisk fucking motion was unrelenting. "Yes! Fuck me!" she almost screamed as she thrust back hard to meet his rapid pace.

"Here I cum, baby!" Steve gasped, as he suddenly pulled his cock from Jennifer's pussy and scrambled off the couch and stood beside her. He stroked his cock hard three or four times and erupted all over her chest and neck. He laid about four long, white strands of cum all over her tits and hair. Still rubbing her clit, she grabbed his cock and milked whatever was left in his balls over her open mouth and hanging tongue, covering her mouth with cum that she let roll down her chin and onto her chest.

Hilary's body could not take it as she watched the lovers finish. She felt the tightening of her stomach, the heat flowing through her thighs, and her pussy contracting around her pumping fingers. She came like a waterfall. Gushing cum all over her hand, she stifled her moan as best she could as she watched Steve shooting his load on Jennifer's tits.

Again, Hilary swore she caught Steve stealing a look at her. Glancing over his shoulder, he stared for a second or two, with a little smile on his face, then rolled his eyes back and turned his head back to watch his lover clean his cock...

*

Lying on her bed naked, save for a little pair of panties, Hilary had become incredibly wet as she rehashed the events of the previous weekend in her mind. Her left hand was massaging her breasts and pinching her hard nipples, her right hand worked on her dripping wet vagina, both in rhythm with her gyrating hips and soft moans.

She increased the speed of her fingers in her pussy and continued to fondle her tits with her other hand as she replayed watching her mother's boyfriend cumming all over her high school friend's heaving chest. Her eyes were squeezed shut in ecstasy and her moist lips opened slightly as she began whispering softly.

"Fuck me." she sighed. "Fuck me." Over and over again she moaned.

A few minutes later, her face flushed and her hand pumping fanatically, her body shook with orgasm and she whispered again.

"Yes. Yes. Cum on my tits. Shoot your hot cum all over my tits."

Suddenly, her bedroom door opened and she jumped in surprise. It was Steve...

*

There she was, legs spread, only wearing a skimpy pair of soaked panties, and caught in the act. Her face flushed, her nipples hard, her pussy dripping, Steve shook his head and walked towards her bed.

Hilary tried to cover her breasts with her arms as she stammered to say something. "What are you doing... how long have you been out there?"

"Oh, long enough." he said with a smirk. "Just what are you doing in here?"

"Get out!" she screamed as he moved closer to her bed. She was certain she saw the beginning of a bulge in his jeans.

"I think your mother would be very interested to know what you do in here." he chuckled as he looked her up and down.

"I think you should leave right now and we won't say a thing about it." she replied, increasingly aware of his eyes on her uncovered body.

"Just like we didn't say anything about what you saw last weekend?"

Hilary could not believe what she was hearing. She tried to speak but her lips would not move. She began to tremble.

"Were you masturbating as you watched Hilary?" he asked.

"I... I..." she still could not but together a response.

"I know you were. Did you cum watching me fuck her?"

Flushed, her mind was swimming as she searched for words. "I... I..."

"Were you picturing it just now, while you masturbated?"

"I... I..." she dropped her head, unable to look at him. "Yes." she replied, squeezing her eyes shut.

"Did you like it?"

"Yes." she sighed.

"Show me Hilary." he whispered. "Show me what you were doing."

In an almost trancelike state, her eyes still closed, she slowly slid her arm off of her breasts and began to roll her nipples between her finger tips. Her other hand quickly found its way back down to her wet crotch and she began rubbing her pussy through the damp fabric.

"Tell me what you're seeing Hilary" he ordered.

Moistening her lips with her tongue, she moved her right hand underneath her panties and began stroking her clit. "You fucking her." she moaned. "You cumming on her tits."

"Yeah? Does that turn you on?"

"Yes." she whispered, fingers pulling at her nipples.

"Does that get you off."

"Mmm hmm." she moaned, her fingers now pumping into her pussy.

"C'mon Hilary... tell me what you're really picturing. Tell me what makes you cum."

"I... I can't." she whispered, short of breath.

"Say it Hilary... tell me what you're imagining."

Nearing a second climax, she could take no more. "You fucking me!" she blurted out. "Oh God, you fucking me like you fucked her! Cumming on my tits!" With that her orgasm hit, sending her body into a shudder as she moaned uncontrollably.

Her eyes still shut tightly in the aftermath of cumming, Hilary was barely aware that Steve was now on the bed with her. And she definitely had not noticed that he had taken off clothes...

*

Steve tugged her panties down to her ankles and slid them off of her. He ran his hands over her breasts, the nipples hard and erect. He reached for her hand and put it on his bulging hardon. He felt her hand close around his cock and she could feel it throbbing against her touch. He rose to his knees and slid his hands into her mess of blonde hair. Without a word, Hilary leaned forward and slid his manhood into her mouth.

He shuddered as her lips closed around the head of his dick. She sucked him in and out of her mouth as his hip moved back and forth in time with her pace. She slid her tongue up and down his cock as it glided deeper into her mouth. He slowly pumped in and out of her mouth as her lips slid up and down his cock, her tongue swirling around it.

Pulling back on her blonde mane, Steve forced her off his dick and he dropped back down onto the bed, positioning himself with his back against the headboard. Again, with no word of encouragement, Hilary manoeuvred herself into place, straddling his crotch and placing her wet pussy against his cock.

"Pleasure yourself again Hilary." he ordered.

Without hesitation, she began massaging her breasts and running her hand over her cunt. It was not long before her hand rubbing her pussy was alternating between playing with herself and stoking Steve's cock. She soon gave up on pulling on her nipples and let him take over, moaning in approval.

"Tell me what you want Hilary." he commanded.

Forgoing her focus on her pussy, she grabbed his dick and began slowly pumping it. "Oh, God..." she sighed. "Fuck me. Fuck me like you fucked Jennifer!"

As soon as he got the tip of his cock inside her she plunged down quickly on his manhood.

"Fuck me!" she cried out, riding him, bouncing her pussy onto him hard and fast. It was all Steve could do to keep from cumming when she slammed her wet cunt onto his rock hard meat. He established a rhythm of his own, picking up Hilary's hips and fucking her slow, long, hard thrusts deep into her pussy by lifting her up and then pulling her down onto his cock. It only took a dozen or so of his hard plunges for her to start groaning and biting her lip.

He reached up and grabbed her tits, leaning forward to suck her rock hard nipples into his mouth. She was bucking on his penis at a feverish pace, matching his hard a powerful thrusts. His cock was starting to throb and he feared he would not last much longer.

Steve quickly pulled her off of him and repositioned her on her back. Her back arched and her eyes squeezed shut as he drove his dick into her again. He slowly pulled out of her almost entirely and then thrust it all the way back in. As they fucked Hilary began to buck wildly, forcing him reach down and squeeze her tits, almost pinning her down to keep from slipping out of her thrashing body. He tried to slow his pace, but she was driving back against him at an incredible pace.

Sensing his climax was imminent, he started plunging his cock into her faster. "Tell me what you want slut!" he screamed.

"Fuck me!" she yelled. "Fuck me like the whore I am! Make me your dirty whore!"

Her words increased his intensity, as he furiously pile-drove into her. Steve knew he was seconds away from orgasm. "Say it whore!" he ordered. "Tell me what gets you off!"

"Cum on my tits!" she screamed at the top of her lungs.

In one quick movement he pulled out of her pussy and moved up to her chest. He aimed his pulsating dick at her breasts and pumped his fist frantically around it. He let go with several hard blasts of cum that reached all the way up to her chin and covered her tits and half of her stomach.

Steve shuddered as the final drops of cum fell onto her tits, and he wiped the tip of his cock over one of her drenched nipples. Exhausted, he collapsed on top of Hilary as she moaned softly, a new fantasy now forming in her mind...

Big Gunz
Big Gunz
997 Followers
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4 Comments
AnonymousAnonymousabout 15 years ago
Great start!

Great start... now we need Hilary's mom to join in with them!

AnonymousAnonymousover 16 years ago
NICE STUFF!!!!!!!!!!!

First story of the night, and I'm unzipping already..........Thanks

AnonymousAnonymousover 17 years ago
holy shit

jeez that made me so wet i gotta go get my dildo now and get off that was amazing ive read all ur stories write more please

AnonymousAnonymousalmost 18 years ago
superb

really great; very hot; very real; wonderful detail

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