The Lucky Day

He was unaware of Caitlin's romantic endeavours, so he couldn't do that if he tried. Besides, showing up in person just for that would be gratuitously cruel, even for their embittered relationship. "No, no, I would never do that," he found himself saying. He had made a plan in his head for how to approach this, but her behaviour was already throwing him off.

"Well, it doesn't matter, cause now that you're here, you're not going anywhere." She grabbed him by the collar and pulled him into the doorway. She was no match for him physically, but he hadn't been expecting to resist such a yank. "You're gonna help me cope by fucking my brains out. No ifs or buts. Got that?"

Ivan couldn't suppress a chuckle of sheer astonishment. "Yes, ma'am. Should I-"

He couldn't finish his sentence before Caitlin threw her arms around his waist and kissed him. After a moment of surprise, he returned the embrace and leaned into the kiss. Her tongue was forceful and aggressive, more inclined to battering than caressing, but he didn't mind a bit of roughness. His lust was inflamed in mere seconds by the prospect that the sixth pussy of the day was waiting for him.

He blindly fumbled around to close the door behind himself, before the two of them shuffled clumsily into the living room, their hands wandering across each other's bodies. Ivan slipped his hands beneath her hoodie and made a run for the clip of her bra right away. He had mostly gotten over missing Caitlin as a person some time ago, but he had never quite stopped dreaming about her breasts. Such a huge rack on such a slender girl was hard to replace.

Once he had undone the clip, Caitlin broke the kiss and shoved him away before he could do any more. "Sit on the couch. And take your pants off," she commanded while pulling her hoodie up over her head.

Ivan felt no need to resist her bossy streak today. He struggled out of his shoes, jeans, and boxers, then plopped down on the couch, his hard cock swaying. Caitlin had taken off her hoodie and bra in the meantime, and now her heavy breasts were bouncing hypnotically as she peeled off her jeans and panties, revealing her smooth pussy.

Once naked, she moved up and straddled him, then promptly pressed her breasts against his face. "Did you miss these?" she said mockingly while placing one hand on the back of his head and caressing his hair.

Ivan only hummed approvingly as he locked his lips around her stiff pink nipple and ran his tongue around it in circles, enjoying the salty taste of her smooth skin. With one hand, he reached up to grab and kneed her other breast. With the other, he blindly trailed down across her side, over her stomach, to her pussy, where he wasted no time in pushing two fingers inside.

Caitlin moaned softly as she arched her back. "So impatient," she mumbled while groping around with her free hand and taking hold of his cock.

She started slowly jerking him off while he continued fingering her snug pussy and devouring her lovely breasts, switching from one nipple to the other multiple times. Her pussy had been slick when he first touched it, but it quickly ramped up to dripping wet.

Soon enough, it turned out that Caitlin wasn't much for patience either. She swatted at the hand inside her pussy, causing Ivan to withdraw it. Then she shuffled forward and lined up his cock with her entrance. She had to lower her body to do so, pulling her breasts away from his face and planting them against his chest. She then looked at him with a familiar red-faced expression as she lowered herself further upon his cock, pushing it all the way inside.

"You haven't lost your touch," she panted as she started a riding motion, repeatedly plunging his cock inside to kiss the mouth of her womb.

"Did you think I would?" Ivan answered with a grin while caressing her hips with both hands.

"Shut up," she mumbled before leaning in and kissing him again.

Her riding motions quickly sped up, in accordance with the aggressive stirring of her tongue. Despite his increased stamina, the excitement of feeling Caitlin's body again had him building up quickly. Thankfully, Caitlin seemed to have the same experience. He could feel her orgasm coming well in advance, from her wavering moans and her shaky knees. When it arrived, the clench of her pussy pushed him over the edge as well. Blast after blast of cum were once again coaxed from his cock, filling up her womb as she released her own warm fluids across his crotch and the couch below.

Caitlin slowed down but kept up her riding motion for a while, until the full extent of Ivan's sperm had been milked from his cock. Then she broke the kiss, pulled his cock free from her slit, and plopped down on the couch next to him, breathing heavily. They lay side by side for a few moments before she broke the silence. "Alright, you can leave now."

Ivan chuckled sluggishly. "That's cold."

"Yeah, well, you've cleared my mind and now I need time to think." She ran her fingers through her hair, tucking back some rogue strands.

He reached out and caressed her thigh. "Well, if you ever need more mind-clearing, feel free to call. No strings attached this time."

She waved away his touch. "Yeah, yeah, we'll see."

Ivan got up to put his clothes back on. Then he gave her breasts another playful squeeze, evoking a slap of Caitlin's hand, before heading out the door. Once it was closed behind him, he let out a deep sigh. He didn't know if digging up old emotions like that was healthy, but it sure was enjoyable in the moment. More importantly, his strange lucky streak had continued even in the face of overwhelming adversity. He wasn't sure yet what to do with that information.

"Ivan, is that you?" said a feminine voice nearby.

He turned to see that the door to an adjacent apartment had opened. Standing in the doorway was a young woman with red hair tied back into a bun, big green eyes, and oval glasses. She wore a grey blazer over a red shirt, a pencil skirt, and dark pantyhose. She had her arms crossed in a shy posture, which enticingly pressed her large breasts together between her upper arms.

Ivan recognised her right away, but had to think for a moment to remember her name. She had lived here during his entire relationship with Caitlin, so they had interacted plenty of times, but never in a very close capacity. "Yeah, it's me. Uhm... Ashley, is it?"

She smiled demurely. "That's right. What brings you here all of a sudden? Are you and Caitlin, uhm, getting back together?"

"No, no, I... was just checking up on her." Whatever else might happen, a renewed relationship wasn't in the cards for them.

"Ah, good. I mean, not good. I mean-" Her cheeks rapidly flushed with red. "She's a nice girl and all, usually, but I've always thought you two weren't quite right together."

"Oh, you're right about that," he said while approaching her. The neckline of her shirt showed a generous hint of cleavage, appealingly presented by the way her breasts were propped up. It was hard not to look. How could his mind still be drawn to that, after all that had happened? "How have you been doing in the meantime?"

"Pretty good. I thought it was kind of a shame when you didn't visit anymore though." She looked away into the distance, clearly contemplating something, then back to him. "Hey, can I tell you something embarrassing? It's okay to say no."

"Yeah, you can tell me. I'm not afraid of a little embarrassment if you aren't." He leaned against the side of the doorframe to show that he wasn't going anywhere.

"Ok, well..." She looked up at him with big frightened eyes. "I, uhm, while you and Caitlin were dating, I... I kinda had a big crush on you. I dunno why, I mean, it's kinda sad, since we didn't interact that much, but you were so nice to me any time we met and you made me feel seen even though I'm kind of a dweeb and-"

"Hey, hey, it's alright, you don't have to justify yourself," Ivan interrupted her nervous rant with a gentle hand on her shoulder. "Having crushes is totally natural."

She blinked at his hand, then raised her own and placed it onto his, caressing his fingers. "Yeah, that's true," she said with a bashful smile.

Ivan felt for the timid girl - looking into her sweet eyes made him want to cheer her up. On top of that, his agitated sex drive gnawed at the back of his head, even minutes after his previous orgasm. "Was it frustrating for you, seeing me with Caitlin all that time?"

Ashley pursed her lips. "Yeah. It's the only reason why I now have the courage to admit it, frankly."

"How would you feel about relieving some of that frustration? Right now?" He straightened up to stand in front of her, and placed his free hand on her hip.

Her face lit up with wide eyes. "Really? You mean you want to... with me?"

Ivan showed her a quiet smile, then leaned in for a kiss. Ashley froze up for a moment, then melted into it, hesitantly wrapping her arms around his waist. He embraced her as well, holding her slender, curvy body against him as their tongues emerged and danced against each other. He nudged her backwards and together they shuffled into her apartment, where he blindly closed the door behind them.

After a few more stirs of the tongue, Ashley broke away from the kiss to show him a nervous smile. "Oh god, I can't believe we're doing this. Uhm... bedroom?"

"Yeah, that'll be most comfortable," he answered while caressing the small of her waist.

"Okay, let's do that." She timidly took his hand to guide him into her living room, then through into her bedroom. Her bed was a bit small for the two of them, but it would do. Once inside, she unbuttoned her blazer and shrugged it off, revealing the way her large chest strained against the fabric of her shirt. "I hope my body doesn't disappoint."

"Oh, you don't have to worry about that," he said truthfully while taking off his own shirt in turn.

The two of them undressed in tandem. As Ivan dropped his boxers, he realised that his half-erect cock was still faintly sticky with Caitlin's fluids. He would just have to hope that Ashley wouldn't notice. His worries about that were quickly blotted out when he looked up at Ashley's naked body. Such a lovely figure on such a shy girl brought his thoroughly-drained cock back to full mast very quickly.

"You look great." He wrapped his arms around her and initiated another kiss.

She embraced him in return and they quietly made out for some time, with her soft breasts and stiff nipples pushing against his chest, and his hard cock throbbing against her belly. He gently caressed her slender waist and rounded butt while she ran her hands across his toned back.

"Thanks," she whispered when their lips finally parted. "You do too."

"How about you sit down on the bed and I'll show you something fun," he proposed, figuring the girl might need some direction.

"Okay," she said with a big smile, before sitting down on the edge, making her breasts bounce with the motion.

Ivan got down on his knees on the floor and spread her thighs apart, revealing a good view at the plump lips of her pussy, decorated by a patch of soft red pubes. He carefully spread out her outer lips with his thumb, revealing the shiny pink folds inside, before leaning in and running his tongue across her sensitive slit.

"Ooh! That's nice..." Ashley purred as her thighs quivered. She leaned back onto her elbows, spreading her legs further for easy access.

Ivan spent some time eating out her eager pussy, running his tongue across her slick folds and stiff clit, occasionally dipping into her snug tunnel. He caressed her soft thighs with his hands as he enjoyed the taste of her increasingly wet pussy, and in return she ran her hands through his hair encouragingly. He wanted her to feel good, but this was also a way to give his cock a little more time before going in again. Soon enough, however, the scent and flavour of her pussy had him throbbing wildly with anticipation.

He pulled his mouth away from it, then took a moment to wipe the excess fluids from his face. Ashley looked down at him with a red face and breasts that heaved alluringly with her heavy breathing. "Is it time?" she said, while crawling backwards to the middle of the bed, making space for Ivan to crawl between her legs.

"Yup." He did precisely that, crawling on top of her so that his raging cock loomed over her eager pussy. On a hunch, he took hold of her wrists and pinned them to the mattress above her head, so that her large breasts rested freely atop her chest. A sultry look from Ashley confirmed that she quite enjoyed the touch of dominance.

He pulled back and took extra care to line up his cock hands-free. When it was neatly nestled against her entrance, he gently pushed it inside the tight embrace of her pussy, until it could go no deeper. "Were you a virgin?" he whispered while stirring his hips to get a good fit inside of her. The possibility had occurred to him a bit too late.

She looked up at him with a guilty expression. "Yeah. Pathetic, huh?"

"Not at all," he assured her, before kissing her once again. As their tongues danced together, he picked up a gentle thrusting motion. When she seemed comfortable with receiving his cock, aided by the abundant lubrication, he gradually increased the speed and force of his thrusts, making her breasts bounce and sway atop her chest.

The reduced sensation in his cock drove him to fuck her increasingly more vigorously. At first he was afraid of being too rough on her, but her moans and shivers only became more frantic as he picked up the pace, filling the room with the wet slapping sounds of their embrace.

The grip of Ashley's thighs around his waist gradually become tighter and the movements of her tongue more frantic, until soon enough Ivan felt the delightful clench of her pussy around his aching cock. She released a long muffled moan into the kiss as the warm fluids surged out from her slit to soak his crotch, but Ivan kept riding her pussy, thrusting forcefully against her womb even as her walls pulsed down on his shaft.

Just as Ashley's orgasm was dying down, Ivan achieved his own release, forcefully shooting what little sperm he had built up deep inside of her body. The orgasm was no less powerful, with his cock and balls working their hardest to provide whatever they could, but he simply had little to give right after his encounter with Caitlin. He let his orgasm wind down as usual, then broke the kiss while carefully pulling his cock free from her pussy.

She looked up at him with red cheeks and a big loving smile. "That was great. Thank you."

"The feeling is mutual," Ivan chuckled while letting go of her wrists and lying down beside her.

Ashley promptly snuggled up against him, resting her head on his shoulder and smushing her breasts against his side. "Can we do this again sometime?"

"Of course," he answered thoughtlessly.

"Awesome." She reached behind her head to undo her hairclip, letting her long red hair fall loose across his shoulder. "Do you have anywhere to be tonight?"

"I suppose not. Do you want me to spend the night?"

"I'd really like that," she purred happily.

"Then I will." He wrapped both arms around her to hold her close.

All sexual urges aside, Ivan couldn't help but feel an affinity for the sweet girl. That could prove to be a problem, as she was the second girl today that he had made a more-than-casual connection with. That fact may bite him in the ass later, but for now he couldn't worry about that. For now, he was satisfied and thoroughly exhausted, eager to get some rest after the Herculean task of satisfying seven women. He would consider his next move in the morning. Perhaps this strange lucky streak would have ended by then, letting him think straight again. Or perhaps not.