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Breaking Up Is Hard To Do

"She had left him before but gone back each time. Now, she had an incentive and a plan to make it final."

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Competition Entry: Anti Valentine

Author's Notes

"A tragedy in three (sex) acts. Any similarity to medieval legend is purely intentional."

It had been a week—a week of reliving their last encounter and anticipating this one. Lately, while her live-together boyfriend Art played poker with the boys, Gwyn had been skipping chick flicks with the girls to meet Lance.

She lost a button as his urgent thick fingers opened her blouse, then gasped when they reached under her skirt to push aside her damp panties. Distracting him with a tongue-filled kiss allowed her to remove her other clothes without damage. Kneeling in front of him, she pulled down his pants and wrapped her lips around the longest cock she had ever tasted. She had practiced with a dildo to take him deeper, but as he reached his full size, she still gagged a little.

He grinned down at her when she looked up. Holding her head, he guided her mouth up and down his cock. As she sucked, his deep moans resonated in her pussy. She would have happily continued, but he decided he was ready and lifted her to her feet.

Without negotiation or discussion, Lance arranged Gwyn on her elbows and knees on the bed. Standing behind her, he slowly drilled his cock into her hungry cunt. Savoring every millimeter, she squirmed back to ensure she had it all.

His first thrusts were slow but grew faster and harder. From time to time, he would seize her hips and grind in her depths, or withdraw completely and use his meat to slap her ass or tease her folds before plunging back in.

Lance shoved her face to the mattress, making her upraised ass a steady target for the jolts that made it ripple. His sporadic sharp spanks made her clench with bolts of forepleasure. He liked to push her limits; being pushed thrilled her. When he surprised her by jamming his thumb into her asshole, she squealed as the ecstasy overtook her. Gwyn was still twitching when he grunted his eruption inside her.

He collapsed on top of her, pinning her to the bed. Skin against warm, damp skin, they lay until he slipped out and rolled next to her. She rotated into his arms to intertwine and kiss.

“How much longer?” Lance asked as he did each time.

“Next week,” Gwyn promised. “Valentine’s Day. He’s going to propose.”

Laughing at the shocked look on his face, she mashed her lips against his, provoking his tongue with hers.

When she broke the kiss, she explained, “He thinks he’ll surprise me, but I know him too well. I’ll say ‘no’ and tell him about us. That should do it.”

For over a year, Gwyn had tried to end her four-year relationship with Art. Each time, he talked her into reconciling. After all, there was nothing wrong with him. He was a kind, supportive partner, and a good lover. She didn’t realize what was missing until she met Lance. He awoke passion within her that Art never did.

“That’s nasty!” Lance mused, seeing an unexpected side of her.

“I know,” she admitted. “But I need to hurt him enough so he won’t want to forgive me and convince me to get back together.”

Taking Lance’s still-slimy staff in her hand, she began to resuscitate it.

“After that, we won’t be limited to sneaking around once a week.”

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Sunday morning was Art and Gwyn’s scheduled time for sex. They would also do it other times when the mood struck, but a non-work day after a night’s sleep provided their most enjoyable opportunity. The regularity provided reliable time for intimacy and also allowed for planning adventures like bondage or role-playing.

With Valentine’s Day—and his proposal—coming on Tuesday, Art’s heady anticipation led him to do something goofy. When they woke, Gwyn got out of bed first to refresh herself in the bathroom. When he took his turn, he returned wearing something that made them both laugh. Strapped to his chin was a dildo!

With hard-ons projecting from both face and crotch, Art announced, “Let me show you how we make love on my planet!”

Gwyn hadn’t expected anything like this but had no reason to object. They discovered the gizmo interfered with their usual preliminary kissing, but she humored him by sucking it a bit. He did his best to find interesting places to poke it as he licked and caressed his way around and down her body.

Between her legs, he let it bump teasingly as he addressed her pussy with his mouth. Knowing her preferences, he soon had her moaning softly despite the distraction. When her juices were flowing, he eased it inside her.

Many sex toys look good on paper but fail to deliver; this one seemed to fulfill its promise. While his mouth worked on her clit and the surrounding folds, his chin-cock churned her channel. He could thrust with it, too, although that was hard to sustain with his neck and jaw muscles.

Nonetheless, his enthusiastic lips and tongue soon had Gwyn approaching a peak. From her viewpoint, she didn’t see the fake dick but felt pleasantly more filled than when he finger-fucked her while he ate her.

“I’m close,” she groaned, which usually would encourage Art to keep doing what he had been doing but this time made him stop.

“Sorry, my love,” he apologized. “I’ll get back to work if you want, but there is another way to use this that I think you might prefer.”

He flipped onto his back and gestured for her to move above him. Art’s grinning anticipation more than the plastic penis persuaded her to kneel astride his head and lower herself onto it. His swirling tongue immediately demonstrated the value of the device. The combined sensations of riding a cock and riding a face soon had her dancing the hula.

“I don’t know what galaxy you’re from,” she sang, “but you’re sending me to the moon!”

His mouth was too busy to smile, but he reveled in the view, looking up her torso between her wobbling boobs to see her intense face looking down at him. From behind, he raised his arms to massage her breasts and tug her nipples.

The sight of his worshipful eyes looking up at her added to all the stimulation and ignited her euphoria. Art helped keep her upright as the spasms of pleasure overwhelmed her. He kept licking until she slumped forward and tumbled off him.

He crawled next to her, the dangling dick tickling her neck and making her giggle as he kissed her lips. She sucked it briefly, tasting herself, but decided it had served its purpose and yanked it off over his head so she could kiss him properly.

“I hope you don’t ever do that to a real alien,” Art quipped. “They might destroy the world!”

“Fortunately, you have a backup,” she cackled, her hand grabbing his swollen cock.

A few determined pumps got him rigid and she urged him on top of her. His cock slipped inside her flowing cunt with a squish. He fucked her slowly, enjoying the grip of her hot slippery flesh.

Gwyn wrapped her arms and legs around him, holding him tight. She wanted their last time together to be memorable for more than the sex toy. Art was a good man; she had chosen to go back with him after their previous breakups. But Lance had made her promise that that wouldn’t happen this time.

Ironically, knowing that she would soon be free from Art stirred her excitement with him. She loosened her hug to let him take control, cooing, “Let’s cum together.”

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He interpreted her resurgent ardor according to his secret agenda and applied his best techniques. Bursts of rapid shallow thrusts alternated with respites of slow, deep ones as they built to new heights of anticipation. When she pulled her legs wider, her half-closed eyes told him to keep going. He did.

Gwyn’s thighs closed as she quivered beneath him. Her lilting sigh unleashed the geyser Art had been holding back and he gushed deep within her. Together they experienced the rapture that each separately desired. They cuddled in the afterglow until other appetites beckoned, then shared a shower and breakfast and continued an otherwise ordinary Sunday.

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Valentine’s night, after the debacle, when the bartender cut him off and ordered him a taxi, Art had no idea where he should go. He ended up at Morgan’s place, perhaps because she was the only one who knew about the proposal. An old friend of his, she also was friends with Gwyn, but not so close that he worried she would divulge his plan. She had been helpful, providing a female perspective and advice on the ring and the proposal plan.

When she opened the door, Morgan’s face immediately mirrored his despondent expression. His presence told her all she needed to know about what had happened earlier that evening.

“I can’t go home,” he blubbered, tears starting to flow.

“You can stay here,” she reassured. Her consoling embrace triggered him to hug her back, too tight and too long, but she didn’t mind.

“I’ll make some tea,” she said, extracting herself from his arms.

They sipped it mostly in silence; Art’s muttering to himself was all that disturbed the calming music she had put on. When he yawned, she led him to her spare bedroom. Closing the door, she listened as he used the bathroom and then became silent before retiring herself.

It wasn’t yet dawn when she woke to the sound of his incoherent laments and noisy movement. She rushed to his room.

Seeing his hungover disorientation in unexpected surroundings, she reassured him, “It’s okay, Art, you’re with me.”

He sat on the bed in his boxers. Morgan hadn’t grabbed a robe, so just wore her bra and panties. He was quietly ranting, not making much sense besides expressing his discomfort and dismay. She sat next to him, putting her arm around him, finding herself enjoying the feel of his skin against hers.

“You need to sleep it off,” she urged. “You can talk to Gwyn tomorrow and sort things out.”

“No,” he wailed. “She has been cheating on me with another guy! She laughed when she said ‘no’ and showed me pictures of them fucking!”

“Oh shit!” Morgan exclaimed. “Well, she’s a fool if she thinks she’s found someone better than you!”

She hugged him closer, crushing her breasts against his chest, rubbing her cheek against his as she stroked his hair.

“Let me help you relax so you can get some rest,” she soothed, easing him backward and rolling him onto his stomach.

Kneeling next to him, she began massaging his arms, shoulders, neck, and back. She continued down to his waist and then worked from his feet to his thighs, kneading his butt through his underwear. Lifting his leg, she turned him onto his back and proceeded to rub his face, chest, and belly.

Art had kept his eyes closed until her hand slipped under his waistband and fondled the pole that had raised a tent. Abruptly opening them, he was surprised to see that she had somehow removed her lingerie. Seeing dark nipples on her full breasts and the hairless divide of her pussy caused his cock to throb in her hand. Still emotionally numb, he was not inclined to object when she dragged his boxers off and settled between his legs.

Morgan had wetly dreamed about this possibility, but Gwyn and Art had always seemed like the perfect couple; she never imagined she would have the chance. Despite his passivity, sucking the cock of the star of her fingered fantasies fueled her growing excitement. She judged his arousal by the stiffening organ between her lips.

Moving up over him, she dangled her boobs in his face. He sucked instinctively when she fed him her swollen nipples. Another involuntary reaction caused his cockhead to poke against her dampening pussy as she wiggled atop him. When she shifted lower to take it inside her, his anguished expression eased with the relief she offered.

Morgan rode him slowly, pressing her warmth against him like a soft snuggly quilt. His motionlessness made her think he wouldn’t cum, but she was happy just to share the tingling between them. At some point, his faraway focus changed and his eyes met hers, seeming to see her for the first time.

“Thank you, Morgan,” he sighed. “You’re too good to me.”

Almost automatically, his hands slowly stroked her from head to butt. Increasingly persuasive sensations led his hips to match her rhythm.

His caresses and his cock moving inside her made her itching clit demand attention. Not wanting to lose the moment, she wriggled and bounced and ground herself to a sweet explosion. Reflexively, he gripped her ass and whimpered as he followed her lead and garnered a dose of solace. Spooning, they drifted off to sleep.

The whole evening had seemed a crazy dream to Art. It was late morning when he awoke alone hearing a voice from the other room. Despite his headache, when he recognized it as Morgan’s, he smiled, self-consciously grateful for the degree of her willingness to comfort him in his desolation. As the fog of sleep dissipated, he cracked open the bedroom door and was able to overhear her animated conversation.

“You agreed that I would pay in full when the job was done. You’ll get your money in a month,” she said. There was no response, so he assumed she was on the phone. “You have to keep stringing her along so they don’t start thinking about getting back together.” There was another pause. “Come on, Lance, I know it’ll be more than once a week now, but she can’t be that bad a fuck!”

The blinding explosion in Art’s skull chased him to the shower to relieve the throbbing. Under the steamy downpour, he had time to clear his mind and understand what had happened. Despite his discovery of Morgan’s involvement, there was no way to undo Gwyn’s betrayal and cruelty.

When he was dressed, he strode to leave but was intercepted by a smiling Morgan.

“I’ll make us breakfast,” she offered.

“I suppose I should thank you for exposing Gwyn’s heartlessness,” he said, bitterly.

Aghast at his sudden awareness of her machinations, she tried to recover.

“Art, dear sweet Art, I watched Gwyn hurt you again and again. I just wanted you to see how she really is so you could find someone who truly cares for you!” she pleaded.

“After what you did, there’s no way I would ever be with you.” His words landed like blows. “You might as well cancel your deal with Lance, which will break Gwyn’s heart sooner rather than later.”

“But Art, I love you. I’ve always loved you!” she sobbed.

As he stepped through the door, Art turned and said those famous parting words, “Frankly, my dear, I don’t give a damn!”

Published 
Written by Trousseau
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