Alison Gives It Up To The Wrong Man

Carl pulled into the parking space, the reserved spot just outside her apartment door and reached over to her. She moved toward him and he quickly invaded her open mouth with his tongue. After months of dating, he was determined to get into her pants. She had stoutly resisted his best efforts but tonight, either here in the car or in her bed; this was going to be the night.

Alison seemed especially compliant. He moved his hand to her breast and enjoyed the softness and size of it. Usually she pulled away after a few minutes but tonight she just moaned and pressed herself harder into his probing hand. He dipped his fingers inside her blouse, popping open the buttons on a top that fit too tight anyway. Shoving the thin bra aside, he began tweaking her nipple and then moved downward to capture it with his mouth. She gasped and thrust her chest forward, making little noises of pleasure.

“So be it,” he thought. “I’m going to do her right here in the car.” It was a chilly night and the windows had fogged over anyway. A passerby couldn’t see in but he would definitely know something was going on.

Carl’s hand reached down to her knee and he began pushing her skirt upwards. His hand was at mid thigh between her legs when she stopped him. Grabbing his hand and clamping her legs shut she whispered, “No, not here, not now.”

He tried to push upwards but she held firm.

“Dammit, you’re driving me nuts! I can’t be leaving every night like this.”

“I know, I know. I’m sorry. I swore I would remain a virgin until my first legal drink. That’s next week. I promise….next week.”

He took her hand and placed it on his cock. “What am I going to do about this?

She squeezed it and watched him open his mouth with pleasure. She wanted him to feel good about their relationship but she was determined to keep her virginity for one more week. A dozen boys and a few men and tried and come close but all had failed. She squeezed again, considering her options.

It caused a sharp intake of breath and he put his hand on the back of her head as he thrust upwards against her hand. He pushed her head down, “Your mouth, help me out with your mouth” he gasped. He needed relief and it had to come from her, orally or vaginally tonight or he was prepared to walk away from this relationship.

After a few seconds of resistance, she let it happen. “He wants a blow job.” She thought. “I’ve never done it but, maybe….”

He pulled his zipper down when her face was just inches away. Alison reached in and pulled his hard cock out of his pants. It was surprising hot to the touch and the tip was already wet as she rubbed the head across her lips. Curious about the taste, she stuck her tongue out and licked the juice. “Ohmigod” he whispered as he bucked his hips upwards, trying to bury his cock into her mouth. He wondered if this was a virgin hole, too.

She wrapped her hand around the base of his cock and began to bob her head up and down. The saltiness of his pre-cum tasted almost pleasant to her. The musky smell was strangely erotic. He wrapped his arm around her head, holding it still as he took over, fucking her face like he planned to fuck her pussy. He could hear her gag when he went to deep but he didn’t care. He had planned on making sweet love to her but right now, in his car, he just wanted to fuck something and her face would do.

It took only a few minutes for him to come and he felt like he discharged a gallon. The white, slimy liquid leaked out of her mouth and she swallowed, not out of any erotic or sexual sense but just to keep from staining her blouse or his car seat.

He let go of her head and fell back into his seat, closing his eyes and savoring the moment of release. She used the back of her hand to wipe off her mouth and stared at him for a moment. He opened his eyes and looked at her, maybe to apologize, maybe not. She stared back for just a second. “Saturday, next Saturday,” she said. Pick me up and we’ll go to your friend’s house for that party and then…I promise.”

She bolted from the car and ran to her apartment. She was in quickly, slamming the door behind her. “My God,” she thought when she realized what she had just done, “if he knocks on the door, I will drag him in and do it right here on the floor.” Her pussy was on fire, her juices were leaking down both thighs. Her clit was starting to throb.

He didn’t get out of the car, though. He watched her disappear, waited until his cock shrank back to normal size, started the car and drove away.

Alison went straight to her bedroom where she undressed and looked at herself in the mirror. Her lipstick was obscenely smeared, testimony to what had just happened. Her breast was beet red where he had used his teeth to tease her nipple. It was on fire and the other one was crying for equal time. She touched it and felt an immediate electric shock that traveled straight to her clit. She reached down and stroked her clit and the sensation caused her legs to give out. She collapsed backwards onto the bed.

Her trembling hand reached over and opened her nightstand drawer and she drew out her friend, the mechanical toy that had helped her keep her virginity. She held it up in front of her. “Hello, Vibraking, my old friend, she whispered. “Come to help me again?”

She had used it often after it was given to her as a gag gift a year ago, always under her blanket and very quietly. The only sound in the room was the buzzing of her toy and the rustle of her sheets. She didn’t allow herself to moan or gasp, just to come to a small mini-orgasm before she put it away.

Tonight would be different. Lying on top of the bed, she stroked her nipple with it — the one her boyfriend had neglected. She moved it down to her clit and pressed. Her orgasm was immediate and huge. She thrust her hips upwards, trying to imagine his cock penetrating her. What would it feel like? She moaned loudly, finally screaming in ecstasy. IT took her almost 20 minutes to calm down. She was gasping like she had just finished a marathon. She was bathed in sweat. Even after 20 minutes she could still feel little spasms deep inside her pussy. Her legs were still wide apart, she didn’t dare press them back together. She was too raw, too tender and too tired for the sensations she knew it would give her.

She glanced toward the window. The drapes were still open. Anyone walking by could look in and see her, see what she had done to herself. See her lying completely naked on her bed and know that she had just been fucked, even if it was by her own had. She was too exhausted to get up and close them, though, and her legs were still too unsteady to carry her the scant five feet to the window. She fell asleep.

Alison woke up the next morning. It was Sunday so there wasn’t much going on outside. If it had been a weekday, the sidewalk outside her bedroom would have been teeming with people and a few of her neighbors would have a lot to talk about later on. It was a little after 9:00 when, still naked, she staggered over to the window. She looked out as the man from the apartment a few doors down walked by. She caught his eye and he looked at her; furtively, at first and then a frank and obvious stare.

“Nice tits.” He silently mouthed as he leered at her exposed chest

Embarrassed, she quickly closed the drapes as she jumped back from the window. Still, the monetary act of flashing him gave her a cheap thrill; it even excited her a little bit. After a long and very hot shower, she got dressed and had breakfast. She wandered back into her bedroom to get a coat she told herself. Instead, she sat down on the bed and looked at the nightstand. Slowly she opened as if she was afraid of what she would find. She knew there was only one thing in there and she pulled it out.

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“Hello, VibraKing, my old friend,” she whispered as she lay down. With her knees up and legs apart, she took a long and leisurely hour to bring herself off again.

He arrived promptly as 7:00 and knocked on her door. She answered it, wearing a long and warm coat. He looked at it. She smiled as she opened it. She was wearing a very short dress that buttoned down the front. The top two buttons were undone, showing a generous amount of cleavage. It stopped a good 12 inches above her knees, making lady like entrances and exits almost impossible. Very high heels made her already long legs look spectacular.

“It comes off easily,” she whispered. “And you can take it off at midnight.”

He looked down and saw that she was wearing a bra that was pure lace, something that did nothing to hold up her breasts. Not that she needed the support. One jerk had described her on a rest room wall at the beach. “Alison has Western tits, high and mighty bigguns.”

Carl opened the door for her and as she maneuvered to get in. she made it obvious that she was wearing the briefest of thong panties. She looked down at what she had exposed and then up at him. “Tonight, dear, tonight, you’ll get to slide them down.”

He walked around to his side, readjusted himself and then got in. The party was a 40 minute drive and it was in one of the finer old homes on Chicago’s North Shore.

“This is going to be a fun night, she said as they pulled into the driveway, looking at him with an unspoken promise in her eye. He reached over and undid the third button. She playfully slapped his hand and started to button it back.

“No, leave it that way. I want to show you off tonight.”

“I look like a pole dancer.”

“No, you look gorgeous and every man in the house will agree.”

She left it unbuttoned. “Every woman in the house will hate me.” She thought. But her heart raced when she thought back to Sunday morning and her neighbor. “Showing off a little more might be fun.”

She did make a well-noticed interest and they were both right. Every man in the house ogled her and every woman looked at her as a threat. Ted, the owner and the host of the party took special notice. Shortly after they arrived, he walked over and handed them both their first drinks of the evening.

“Carl, Here is your Bud Lite,” he said, “and for Alison, a Black Russian.”

“What’s a Black Russian?” she asked.

“An old school drink,” he replied, trying not to be too obvious that he was staring at her breasts. He could see the delicate lace of her bra and he desperately wanted to see more. “Take a sip,” he urged.

“Mmmm, tastes a bit like chocolate milk,” she said.

“It does, indeed, drink that one and I’ll bring you another.

The high alcohol drink quickly loosened her up. The thought of what she was going to let her boyfriend do to her tonight made her even more flirtatious. She danced with several men, careful to be with just those who were single. No reason to piss off any wives she thought.

Ted watched her like a hawk, waiting for an opportunity to separate her from the crowd. Long legs, great tits, perfect ass; she was the woman of his dreams and he was a sexual predator. He had gone through three wives because he couldn’t resist the challenge of bedding another woman. His wife’s best friend, her sister, another man’s wife or girl friend? It didn’t matter. The thrill of sliding between a woman’s legs for the first time and fucking her senseless was one of his greatest pleasures.

Jack, one of his ‘wing men’ when he went out looking for what he called a little sport fucking, noticed Ted’s point of interest. “That’s his girl,” he said pointing toward Carl. You gonna take a run at that cute little piece, you’ll have to get rid of him first.”

“It can be done,” said Ted. “I don’t plan on sleeping alone tonight so it might as well be here in my bed.”

He watch as the band he had hired played something slow and sensuous. Alison grabbed Carl and they danced something that looked more like vertical sex. Hands playing over each other’s body, mouth-to-mouth breathing — it was viciously erotic and left them both panting with desire. It was only 10:00 PM, though; two more hours before she would let him finish unbuttoning the dress and devouring every inch of her body.

Ted brought them another drink. He handed Alison her fourth Black Russian of the night and said, “Look guys, if you need a room, go upstairs.” He smiled to show he was just joking.

It took about 15 minutes for the doped beer to hit Carl and he sat down and passed out. Ted walked over and said, “Don’t worry. He’ll be ok in the morning.”

“But . . but…we were going to…” Alison caught herself and let the thought trail off. “I don’t think I feel so good myself,” she said.

“No throwing up on my new carpet,” said Ted. “Let’s get you into a back room and let you sleep it off.”

He hooked her around her waist and led her to the master bedroom, the office where he did some of his best work, he thought. He took her into the bath and bathed her forehead with a cold cloth. She was still unsteady on her feet. He laid her down very gently on his bed. “I’ll be in later to check on you” he whispered into her ear, “Just relax for now.”

He walked out to join the party. Jack had noticed what had happened. “Doped him, gonna screw her in his absence?”

“She’s sleeping it off on my bed. I’ll have her tonight or let her take care of my morning wood.” He smiled and patted jack on the shoulder. “Maybe you could bat clean up tonight? She was hotter than a five dollar pistol before her boyfriend ‘passed out’ tonight.”

“I hate sloppy seconds. Leave one hole unfucked for me.”

Ted ushered his guests out shortly after 1:00. Jack went into the kitchen and began preparing an early breakfast. “I’ll be here for about another hour,” he told Ted. If you’re done by then, I expect a ‘blow-by-blow description.”

They both looked at Carl, still slumped over in the chair. “How long do you suppose he’ll be out?” asked Jack.

“He’ll come to around 9 or 10 in the morning but he’ll have a nasty little hangover for at least another 24 hours. Now, if you’ll excuse me,” he said while adjusting himself,” I have a job to do.”

“You are one noble, self-sacrificing son-of-a-bitch.”

The smiled at each other and Ted walked down the hallway.

Alison was still where he left her, sprawled out across the bed in the darkened bedroom. Her legs were in full view and the dress had hiked almost up to her crotch. Her hand was between her legs. The light from the hallway reflected nicely off her pure white thong. It was obvious she had pleasured herself.

Ted stood there at the foot of the bed, enjoying this voyeuristic view of her fantastic body. He watched her breasts rise and fall as she breathed. His hands itched to feel their coolness. He slowly disrobed, savoring the moment and what was about to happen. He walked over to the bed and sat down beside her. He placed his hand on her knee and urged to closer to him, spreading her legs even wider.

Her hand still covered her crotch which was still wet. His hand drifted up, nudging her legs farther apart. Twice, she seemed to stir so he stooped until she settled down again. When he reached the top of her thighs, at that warmest and most delicious spot, he slipped his hand under hers and felt the wetness of her pussy.

“She made herself come once tonight,” he thought as he smiled to himself. “I’m going to make her come at least two more times.”

He reached over to her other leg and slowly bent her knee up and away, creating a wide space traversed for now by just the thin crotch of her panties. He moved in on his target from the foot of the bed. Reaching under her legs, he pulled her pussy to his face and began running his tongue gently up and down along the silk strip of her thong. It didn’t take long for her to revive and she grabbed his head and began flexing her hips.

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“Oh….Oh…God that feels so good” she whispered.

“It would feel better if nothing was in the way,” he replied in a similar low whisper.

She reached down and pulled the crotch of her panties aside, giving him unrestricted access to a virgin site. He reached up, pulled the dress open and slid his hands under that flimsy excuse for a bra. Squeezing her breasts as he increased his oral assault on her pussy he could tell he was bringing her to the brink. Not so quick, he thought. She needs to feel it build up.

He slowed down for a moment and then picked up the pace. Her hands covered his and pressed hard as she drove her hips upwards, fucking what she thought was Carl’s face. Her actions became more and more intense as she felt an orgasm building. Her hands squeezed harder and her hips were moving in a frenzy. She was extremely vocal, urging him on.

When it came, it was earth shattering. Her orgasm exploded throughout her body, leaving her shaking and trembling. She howled in ecstasy and was left quivering on the bed as she slowly came down from complete rapture.

While she was still panting from the exertion, he moved up, covering her body with his. Reaching between them, he positioned his cock at the entrance to her pussy. Her juices were running, creating a large wet spot under her ass. Her pussy lips were wide open, needing something to grasp. He pushed forward, feeling his cock head slip inside. With just the tip, he began a slow rhythm. He wanted to take some time to enjoy this and he knew if he penetrated her completely, how would never last.

“Oh, Carl,” she whispered as she wrapped her legs around him, “Don’t tease, do it now?’ She opened her eyes for the first time and realized it was Ted who was about to fuck her.

“My God, what are you doing?” She gasped.

“I’m doing you, babe,” Ted smiled as he continued his slow pace. “Don’t you want me to do it? He whispered into her ear. His breath made her shiver. She could feel the slow in and out motion and it was bringing her to a slow boil.

It was too late for her. She wrapped her arms around him and pushed up, taking almost half his cock. “I’m a virgin.” She whispered.

“Yeah, sure,” he thought. He pushed into her a little more and bumped into her cherry. “Well. I’ll be damned, she really is!”

He backed almost all the way out and with a grunt, slammed all the way in, tearing through her maiden head and coming to a rest with his balls tight against her ass. It hurt her like hell and she shrieked out pain but Ted wasn’t about to stop. He began pistoning in and out of her pussy, changing the pain to pleasure and quickly building into another major orgasm. She moaned and thrashed through the pleasure, coming at least half a dozen times before Ted unloaded. He growled like a wounded bear as he pumped load after load deep into her. She passed out.

Jack was standing at the foot of the bed when Ted finally pulled out and rolled over.

“How long you been there?” He asked.

“Since I heard her scream. Watched as you fucked the shit out of her.”

Ted reached between her still wide spread legs and began fingering her clit. Between her natural juices, his sperm load and some virgin blood, there was a lot of liquid running down her ass.

“A virgin,” he said holding up his finger and showing the pinkish fluid. “I took care of that but I suspect her back door is still untouched.”

Alison was still struggling to catch her breath and regain her awareness. She heard a second voice but it seemed to be very far away. Ted was doing some pleasant things between her legs and she rolled toward him, lifting her knee to give him better access. He was strumming her clit and pushing the fluids back toward her ass. She felt him push a finger into her anal opening while his thumb kept gently stroking her clit.

“Not back there,” she gasped. “I’ve never done that.”

“I know he said as he kept up the twin assaults on both opening. He pulled her mouth to his and kissed her hard, leaving her breathless. When he broke the kiss, his middle finger was planted all the way in her ass. His thumb was doing incredibly pleasurable things to her pussy, though, and she felt another orgasm building. She wanted to come again so she leaned into it, urging another explosion within her loins.
Jack had stripped while watching this foreplay. It was a technique they had perfected over the last few years. They found most women won’t consent to anal sex or a three way unless they’re about to come anyway. Alison sensed more than felt someone sliding into bed behind her. She started to turn to look but Ted had her leg in a tight grip, keeping her facing him.

Ted was already rock hard from watching the action so he was ready. He pressed his cock against her anal sphincter. She looked at Ted in shock. He smiled and said, “Relax, we’re about to take you to places you’ve never been before. He slipped his cock back in, coming in high so that it rubbed across her engorged clit. She gasped at the sensation.

Jack pushed in harder until his cockhead popped through her ass muscle. Even with all the lubricant Ted had spread back there it was incredibly painful, more than losing her virginity. She jerked her pelvis forward, impaling herself completely on Ted’s cock. He pushed back, slowly but firmly which served to drive Jack’s cock deeper into her has. Alison, caught in a sandwich, was unable to move. She was trapped between indescribable pain at her back door and incredible pleasure in front. Tears streamed down her face as she said, “He’s in my ass, he’s all the way in my ass.” A half hour ago, she was a virgin, now she was pinned between two men penetrated completely in both holes.

“Shhh, my little slut, concentrate on what’s happening with your pussy,” said Ted as he began a slow, lazy fuck. Jack held still. Even with a strange cock in her ass, the pleasure of fucking began to take over. When she began that strange irregular breathing that signals a soon-to-come orgasm, Jack reached around front to cup her breasts and began fucking her ass.

What Ted was doing had caused her to relax and stop tensing her ass muscles. She was still concentrating on what he was doing to her but Jack’s cock had moved from causing pain to creating a different kind of pleasure. It still hurt but in a strangely good way. She was a whore, their own little fuck toy now so a little punishment was OK. The orgasm hit as soon as she accepted that thought. It exploded again, this time starting with her ass and surging upwards. She was rapidly moving her hips, driving first Ted cock deep within her pussy and then Jack’s cock all the way up her ass.

“My God, I’m coming,” she shrieked. The intense clenching of her pussy and ass caused both men to come, too. Ted slid his cock out first and rolled over, trying to catch his breath. The tighter back door grip Alison has on Jack’s cock took almost a full minute for him to withdraw. Alison was gasping for breath; the intensity of the act had completely exhausted her. She rolled over to see who had taken her from behind. She looked down at his cock and wondered what he would feel like if he fucked her missionary style.

Updated: April 16, 2018 — 3:49 AM

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