A Break Up Cuckolding (Patreon)

“This isn’t working out,” Ava said.

Leo laughed.

“I’m serious,” Ava said. “This isn’t working. This relationship. It’s not working. Which means it’s over.”

Leo felt as though he’d been punched in the gut. It was Saturday night. Ava was wearing a remarkably sexy lace dress that showed off her spectacular breasts and her long, lovely legs. She was dressed for a date – or a particularly pleasurable seduction – not for a break up.

“I…but…I feel like it’s working,” Leo said. “Tell me what’s not working for you. I can work on it, whatever I’m doing wrong, I can work on it.” He knew he sounded desperate, but it was all he had in the moment.

“It’s nice that you feel like it’s working, but there are two of us in this relationship, Leo, and it’s not working for me. I know this sucks, but I’ve come up with an idea that I think will make this a little easier for you,” Ava said.

“Easier for me? What are you talking about?” he asked.

Ava’s phone buzzed and she glanced at the screen before smiling at Leo. “You know that fantasy of yours?” she asked. “The one where I fuck other people?”

All Leo could think was that Ava had the most perfect smile he’d ever seen.

“Leo, pay attention,” Ava said.

“Yes, sorry,” Leo replied. “My fantasy. Yes, I know what fantasy you’re talking about. Why are you bringing that up? It seemed pretty clear that you weren’t interested.”

“Have you ever heard of break up sex?” Ava asked.

Leo nodded. He’d heard of it, though he’d never experienced it. He’d never really understood how someone could have sex in an emotionally devastated state.

“Well, think of this like that. It’s a break up cuckolding. I’ve invited a guy over and I’m going to fuck him while you watch,” Ava explained.

Suddenly the dress made sense. It wasn’t for Leo, it was for the man she was replacing him with.

“You’re already seeing someone else?” Leo asked. “You’ve been cheating on me?”

Ava shook her head. “No, he’s an ex. He was a crappy boyfriend, but the sex was out of this world and the one thing I could use right now is a really good fuck and he’s guaranteed to give me that, plus there won’t be any messy emotional stuff as he knows we’re not going to start dating again. He’s just going to fuck my brains out and head home. I’m sure I’ll find someone else soon enough, but I’ve been faithful.”

“You could really use a good fuck?” Leo asked. “Did I not…I mean, was I not good enough?”

Ava offered a sympathetic smile and said, “No, you weren’t. You’re not bad. I probably could have made it work – that’s what toys are for, right? – but our sex never reached the heights of pleasure that I’ve experienced with other men, so I think it’s fair to say that you’re not good enough.”

“Oh,” was all Leo could say.

“Sorry,” Ava said. “I know that’s harsh, but I’m not your girlfriend anymore so I figure I might as well be honest. Maybe it will help you the next time you date someone.”

“What could I have done better?” Leo asked. “Not just with the sex, I mean.”

Ava reached over and put a hand on his knee. She leaned a little closer and he thought for a moment she might kiss him, especially when he caught a whiff of her intoxicatingly sexy perfume. “Leo, I’m not your girlfriend anymore. I don’t owe you anything and I’m certainly not going to hash out what went wrong with our relationship. Plus, there’s no time for that. Gavin will be here soon. You need to decide if you want to experience your break up cuckolding. If not, you need to leave.”

Leo was going to leave. He really was. Then Ava’s hand moved up his leg. The arousal was instantaneous. She leaned closer and he felt her breath against his neck. Her lips brushed against his skin and she unleashed a soft, sensual moan.

“Don’t you want me to cuckold you?” Ava whispered. “Don’t you want to live out your fantasy? Don’t you want to watch another man fuck me?”

“Yes,” Leo said as Ava’s fingers found his newly-erect cock.

She stroked him gently and kissed his neck. She moaned, a little louder this time. Leo closed his eyes and imagined someone else fucking her. It wasn’t the first time he’d done it. It wasn’t even the hundredth time he’d done it. Of course he wanted her to cuckold him, especially if their relationship was over. Why not go out with a bang?

Ava released his cock and stood. “Good. I’d like you to go to my bedroom and take your clothes off. I want to see you on your knees by the door when Gavin and I come in. Do you understand?”

Leo nodded.

“What are you waiting for?” Ava asked.

Leo hopped to his feet and rushed towards Ava’s bedroom. He stepped inside and was hit with an unexpected wave of emotion at the idea that he’d no longer get to spend the night in her bed. It was over between them. It was truly over. Leo leaned against the wall and asked himself if he really wanted to do this. His cock was still hard. Desire still coursed through him. There was a healthy dose of anxiety in there too, of course, but he wanted to do it. He wanted to live his fantasy.

Leo stripped, folded his clothes, and got on his knees by the door. He reached down and stroked his cock to help build his desire. Leo closed his eyes and imagined Ava in her bed with another man between her legs. It was enough to make him moan.

His fantasy was interrupted by a loud knocking at the front door. Leo’s eyes shot open and he listened to the muffled sound of Ava welcoming her guest.

It was the deep sound of Gavin’s voice that sent a wave of panic rushing through Leo. He’d fantasized about being cuckolded countless times, but it was happening without warning and the idea that a man Leo had never met would soon walk into the bedroom and see him stark naked and waiting on his knees freaked Leo out.

“So he really wants this?” Gavin said as he and Ava approached.

“He does,” Ava replied.

Leo felt lightheaded. He looked down at his cock. He was still hard as a rock. Gavin and Ava were a few steps away. Leo considered grabbing his clothes and running out of the room. He wasn’t sure he could actually handle actually being cuckolded.

Then Ava stepped into the room and smiled at Leo. “Are you ready to be my little cuckold?” she asked.

Leo nodded. He wasn’t even remotely certain that he was ready, but Ava looked so perfect and the fact that she was willing to cuckold him made Leo want to do it. If she was the one to guide him through it he felt confident it wouldn’t be a scarring experience.

“Prove it,” Ava said. “Tell Gavin that you want to watch him fuck me.”

Leo looked at Gavin and said, “I want to watch you fuck Ava.”

“Your ex-girlfriend,” Ava added.

“Yes, I want to watch you fuck my ex-girlfriend,” Leo said.

Gavin laughed. “Wait, you broke up with him?”

“I did,” Ava replied. “The relationship wasn’t working for me. Leo’s a good guy, but he’s not the guy I need. I wanted to give him something nice, though, and I know he wants to be a cuckold. I don’t want that to be a part of my life, but I figure that as long as we’re breaking up I might as well give him a treat. There’s no harm in letting him watch you fuck me, after all.”

“Plus, who knows, he might learn something,” Gavin added.

Ava laughed. “I doubt that. You can’t teach a guy to fuck, at least not in the way that you fuck, Gavin.”

Gavin looked at Leo and flashed a confident grin, though he had every reason to do so. Ava had just told him he was better.

“Have you missed what I used to give you?” Gavin asked.

Ava looked at him and nodded.

Gavin stepped closer and put a hand on her waist. “Has dating Leo made you yearn for the days where I would fuck you so hard you screamed when you came all over my cock?”

Gavin pulled her body against his and Ava nodded a moment before they kissed. It wasn’t the sort of slow, sensual kiss that Leo favored. It was a feverish, open-mouthed kiss with a healthy dose of tongue. It was animalistic, even, and when Gavin grabbed Ava’s ass with both hands and squeezed hard, she moaned into his mouth like he was already inside her.

“I’ve missed you,” she said breathlessly. “I can’t believe how much I’ve missed you.” Ava pulled his shirt off and tossed it aside before kissing him again. This time she was the aggressor and her hand moved between Gavin’s leg to stroke his cock through his jeans as she sucked on his tongue.

“I’ve missed you too,” he said.

Ava laughed. “I know, I can feel how much you’ve missed me.”

Leo looked down to see that Ava’s fingers had found Gavin’s thick, erect shaft. She was stroking him vigorously through his pants and she had him moaning, no doubt from the intense pleasure.

“Leo, unzip my dress,” Ava said.

Leo stood, gently tugged on Ava’s zipper, and slowly pulled it down. He couldn’t help but note that it was probably the last time he’d see his ex-girlfriend in her underwear. As always, she looked splendid.

Ava stepped back, pushed the dress off her shoulders, and it fell to the floor as Gavin’s eyes moved over her body.

“I forgot how fucking sexy you are,” he said.

“Do you remember now?” Ava asked.

Gavin nodded and Ava moved towards him. She reached out and removed his pants with remarkable swiftness. It was an act of desire that Leo couldn’t remember her ever doing for him. She’d taken his pants off, of course, but not with that sort of need driving her behavior.

They kissed again as Ava dropped his pants and underwear. Leo groaned as he watched Ava wrap her fingers around Gavin’s thick cock and stroke him. His fantasy was coming to life and it was so much hotter than he’d ever imagined.

“Take my panties off, Leo,” Ava said.

Leo moved behind her and dropped to his knees to pull Ava’s panties down her long, lovely legs. He stared at her perfect ass until Gavin’s hands grasped her flesh and squeezed it tight. He spread her lovely ass cheeks and Ava looked over her shoulder, smiled at Leo, and said, “Eat my ass.”

Leo looked up at her and smiled. He crawled forward and pressed his face between Ava’s ass cheeks. He licked her perfect asshole and Gavin released her flesh. It closed around his face and he moaned at the sheer pleasure of getting to run his tongue over her wrinkled hole while she kissed the man that would soon be fucking her.

“It sounds like he’s really going at it,” Gavin said.

Ava laughed. “He is, and it actually feels pretty good.”

Leo heard the unmistakable sound of a finger entering Ava’s pussy. She moaned as that finger found her wetness and pushed deeper inside. It had to be Gavin getting her all wet for the sex they’d soon be having.

“Does that feel good?” he asked.

“You know it does,” Ava replied. “You always knew how to make me feel good. You always made me cum harder than any guy I’ve ever been with.”

“Even Leo?” Gavin asked.

“Especially Leo,” Ava answered.

Gavin laughed. “Is that why you’re breaking up with him, Ava? Is that why the relationship wasn’t working for you? Is it because Leo’s a fucking failure in the bedroom?”

Ava moaned in pleasure as Leo waited to hear her answer. He didn’t think he was particularly bad in bed. It wouldn’t have surprised him to know he wasn’t great, but he’d always thought he was decent when it came to offering sexual pleasure to his girlfriends.

“Yes,” Ava answered before unleashing a long, low groan as Leo heard Gavin finger her with a deeper sense of vigor.

Suddenly Ava stepped away from Leo and spun around. He looked up to see Gavin’s hands move to her perky breasts and gently pull on her nipples.

“Did you hear that, Leo?” Gavin asked. “Ava called me in because you weren’t getting the job done. She dumped you and called me because you can’t fuck her worth a damn.”

Leo looked at Ava, though he couldn’t bring himself to ask the question that waited on the tip of his tongue.

“Eat her pussy,” Gavin said. “Eat her pussy while she thinks about my cock inside her.”

Leo followed his lust between Ava’s legs. He ate her pussy as Gavin instructed. He heard them kissing as his tongue danced over Ava’s clit and pushed between her labia to taste her wetness. He was the cuckold. He was on his knees preparing her pussy for another man to fuck her. He was the kind of cuckold he’d been in his fantasies.

“Is this what you wanted?” Ava asked. “Is this your fantasy?”

Leo nodded without pulling his tongue from her pussy.

Ava smiled, reached down to grab a handful of Leo’s hair, and pulled hard. His head snapped back from between her legs and she bent over and her lips hovered achingly close to his. “Beg him to fuck me,” she said. “Beg him to fuck your ex-girlfriend. Beg him to fuck me like you couldn’t. Beg him to satisfy me in a way I haven’t been satisfied in the three months we’ve been dating.”

“Please, Gavin, fuck her,” Leo said. “Satisfy Ava like I couldn’t. Please, fuck her and cuckold me. Cuckold me just once before I never see her again.”

Ava closed her eyes and moaned. Leo studied the pleasure on her face. Gavin must have slipped his cock inside her from behind. They were having standing doggystyle sex in the middle of the bedroom. Gavin was fucking her in a position Leo had never fucked her in.

“God damn I missed this pussy,” Gavin said as he began to fuck Ava in earnest.

Ava smiled and opened her eyes. She put her hands on Leo’s shoulders and said, “I missed your cock so much more than I thought. Fuck, I fucking missed your cock so much, Gavin. Pound me. Pound my pussy while this little cuckold bitch watches.”

Leo’s gaze drifted from watching the pleasure on Ava’s face to gazing at her breasts as they bounced with every thrust Gavin delivered. The longer he went, the harder he fucked her, which amazed Leo. He seemed to be building energy instead of dissipating it.

“He deserves a better view,” Gavin said as he pulled out. “Get on your back in the bed, cuckold.”

“Do it,” Ava said when Leo hesitated for a moment.

Leo got to his feet and got on his back in the bed. His heart pounded as Ava crawled on top of him in a 69. Her hair brushed against his chest, stomach, and upper thighs before she came to rest with her pussy just above his mouth.

“How’s the view?” Ava asked.

“It’s perfect,” Leo said. “Your pussy looks perfect.”

Gavin laughed and moved into the bed behind her. He rubbed the head of his cock over Ava’s pussy lips and it came perilously close to brushing against Leo’s face. He felt a mild desire to have Gavin do it, to push him right over the edge and into the deep end of cuckolding, and yet Leo wasn’t sure he could actually handle it.

After a little bit of teasing Gavin slowly filled Ava as she grabbed Leo’s balls and squeezed them tight while her moans filled the bedroom.

“That’s what it looks like when Ava takes a real cock,” Gavin said.

Leo was certain he’d never seen anything so beautiful. He’d never taken the time to study Ava’s pussy when he’d been that close to it before. He’d simply eaten her out with vigor in the past. Now he studied her labia. He studied her clit. He studied the cock sliding in and out of her. He listened to the beautiful, wet sounds of sex. He felt the little droplets of juice hitting his nose and cheeks. A few even got in his eyes. All of it stood as a beautiful reminder that Leo was experiencing so much of what he’d fantasized about.

Again Gavin seemed to build energy as he fucked Ava. He pounded her with such vigor that the sound of flesh meeting flesh was all Leo could hear. With each thrust Gavin pulled out until just the tip was inside her before slamming inside once more. Ava squeezed his balls harder the harder Gavin fucked her, and though it was a little bit painful, the pleasure of witnessing the sex in close up overwhelmed everything else.

At one point Gavin pulled out a little too far and his cock slipped out of Ava’s pussy. He was moving so fast that he pushed forward without getting back inside her. Instead, his cock rubbed over Leo’s nose, lips, and chin. He instinctively opened his mouth and licked Gavin’s shaft. He tasted Ava’s juices.

“Holy shit,” Gavin said.

“Oh my god,” Ava added. “Look at him go. Look at that little fucking cuckold go.”

“Open up,” Gavin said as he rubbed the head of his cock over Leo’s lips.

Leo opened his mouth as instructed. The thick head of Gavin’s cock pushed into his mouth. He closed his lips around it and sucked as Gavin’s balls settled over his eyes. Arousal ripped through Leo’s body as he indulged in his fantasy.

“Your ex boyfriend is a fucking cocksucker,” Gavin said. “He didn’t even hesitate. He ate my cock like a fucking street whore.”

Ava laughed and wrapped her fingers around Leo’s cock. She stroked him and Leo moaned around the dick in his mouth. “It’s kind of hot,” she said. “But I need you inside me. I need to cum, Gavin. I don’t care if Leo wants to suck your cock until you flood his mouth with your load. You need to give me what I want.”

“You heard the woman, cocksucker,” Gavin said as he pulled his dick from Leo’s mouth and pushed it into Ava’s pussy.

“If you need to use your tongue, you can lick my clit, cuckold,” Ava said.

Leo put his tongue to work without hesitation. He licked Ava’s clit as Gavin resumed fucking her. The sounds of sex once again filled his ears. Ava stroked Leo’s cock slowly and with a tight grip and every time her hand neared the head he moaned in pleasure.

“Harder,” Ava said. “Fuck me harder, Gavin. Fuck me harder while that little bitch licks my clit.”

Gavin fucked her harder. Eva moaned louder. Leo felt her thighs tremble. Her pleasure was building. She was getting closer.

“Oh, fuck, Gavin, I’m close. Keep fucking me. Keep fucking me!” Ava screamed.

Gavin gave Ava exactly what she needed. He pounded her to a loud, lusty orgasm that left her legs shaking. He kept fucking her, too, and it wasn’t until a few moments later that Leo realized that Gavin was close too. He sped up and then buried his cock in her pussy and Leo watched his balls pulse as he emptied his load inside her.

Ava moaned like it was exactly what she wanted and she squeezed the head of Leo’s cock in a way he found utterly delightful.

Gavin pulled out slowly and Leo prepared to roll away. Ava had other plans, though. Instead of giving Leo a chance to roll away, she sat on his face. Her pussy opened up and cum spilled out. She gave Leo a facial, of sorts. She made a sticky, salty mess of his face and slapped his stiff cock a few times for good measure.

When Ava finally lifted her pussy Leo could feel the semen all over it. He heard Ava laugh and reached up to wipe the cum off his eyelids before looking at her.

“You deserve an orgasm before I officially dump you,” she said. “So put your legs behind your head and I’ll jerk you off onto your face.”

“What?” Leo asked.

“Do it or you can go home and jerk off all alone,” she said. “It’s your choice.”

Leo looked down at his stiff cock and decided that a humiliating handjob from Ava would be better than jerking off alone. He flipped his legs back over his head until the head of his cock was just a few inches from his face.

Ava wrapped her fingers around his stiff shaft and stroked Leo vigorously. The position was uncomfortable, but her touch was blissful and he knew he’d cum quickly.

“Oh fuck,” Leo said. “Oh, fuck.”

A moment later cum erupted from the tip of his cock. It sprayed all over his face, making a massive, sticky, salty mess as Ava laughed in pure delight. She released his cock when Leo was finished cumming and he let his legs fall to the bed.

“It’s been fun, Leo,” Ava said. “But it’s time for you to go. I hope you enjoyed your cuckolding, though.”

“I did,” he replied. “Thank you, Ava. I’m sorry I wasn’t better. In bed, I mean.”

“I am too,” Ava said. “But you weren’t, and now you’re single and wearing two loads of cum on your face. Why don’t you wear the cum home? You’d like that, wouldn’t you? Maybe you can keep it on your face until you’re ready to jerk off again. You can think about Gavin fucking me, which he’ll almost certainly be doing by the time you get home. You can jerk off and think about what you just watched.”

“Okay,” Leo said softly.

“Good. Now it’s time to go,” Ava replied.

Leo got out of bed, got dressed, and left with two loads of cum on his face.