Expecting & Expectations Ch. 04

This struck a note inside Kelsey's heart. She didn't know what to make of it. Was she being selfish here? "Janie, I... I wouldn't stop you. I wouldn't be mad."

"'s real tempting, Kels," Jane admitted. "But I don't think I could. If I did, I'd feel like shit after. I dunno, I can't explain it exactly. I'm craving a real cock inside me, but not if you're not there with me and part of it. I'm sorry, I'm not trying to guilt-trip you, I just-"

"Shhhhhh," Kelsey said soothingly, caressing her sister's lips with her fingers. "I know you're not. You're really that hungry for a live cock?"

Jane nodded.

Kelsey smiled. "Y'know, I could probably use some too. Wanna go pop a virgin boy's cherry?"

Jane's face lit up. "For real, Kels? You'll share that Ray kid with me?"

"Against my better judgement, yes," confirmed the older sister. "Let's go shopping and get laid, shall we?"

Within seconds, Jane was hustling her sister up the stairs to get dressed, her face aglow with excitement.

"God, I hope this kid is eighteen..." Kelsey thought to herself wearily.

***

They both watched patiently as Ray, the young man from the high-end grocery store, shuttled loads of bags into their kitchen, smiling at them somewhat shyly as he did so. They had been delighted to find out he was on-duty that night and he was more than willing to follow them home again and bring their purchases in. This didn't surprise Kelsey or Jane, since he'd responded well to the last 'tip' they'd given him, with the promise of more.

It was nearly fifteen minutes before he had completed his task, the girls setting about putting the frozen goods away while he scurried back and forth, but at last it was all finished. Ray wiped his brow and smiled. "That all for you ladies?"

"Depends," Jane lilted, strolling toward him and smiling slyly. "Did you like the tip Kels and I gave you two nights ago?"

He blushed but nodded. "Oh, yeah, I, uh- yeah, I did. A lot. Thank you."

"Well you did even more work this time," pointed out the blonde girl, standing in front of him and walking two fingernails daintily up his chest. "Sissy and I were thinking that maybe your tip should be a little more too."

He swallowed and fidgeted. "O-oh?"

"If you're willing, of course," Kelsey chimed in, coming to stand next to Jane. "Wouldn't want to take your choices away from you. But we were wondering if you might listen to a little proposal."

Ray swallowed again and nodded.

"You're a virgin, right?" Kelsey suggested.

He blushed and nodded, looking at the floor.

"Nothing to be embarrassed about, hun," Jane said soothingly, caressing his arm. "But Kels and I both have an itch and we were hoping you might help us scratch it."

He looked at him somewhat quizzically.

"My sister and I are wondering if you'd let us fuck you." Kelsey said, standing beside Jane and pressing subtly into her. "We're both feeling pretty horny and needing to feel a real dick inside of us. Would you be interested in letting us take your cherry?"

Ray looked like he might faint for a moment. "Are you... serious? With me?"

The two girls nodded.

"Why me?" he asked, bewildered.

"Because you're available and we're both craving cock," Jane answered simply, tracing her finger down his torso and hooking it into the front of his slacks, tugging on them slightly. "Don't worry, we don't think you're some god of sex and we're also not going to tear your head off and eat it after we fuck. Would you be willing to lose your virginity to two pregnant sisters who are in need of some real dick?"

He paused for only a second before he shivered and then nodded. "But, I didn't bring any con-"

"Do you have any communicable diseases?" Kelsey asked. He shook his head. "Good, neither do we, and it's not like you can get us pregnant. If you want, you can fuck us both and even cum in Janie. Still want to?"

He nodded again.

"Can we keep you maybe a half-hour?" Jane queried.

Ray nodded. "I'll... just tell them that I helped you put all the food away because your backs were sore, they won't mind that. Yeah, I can do a half-hour."

"Even though we probably won't need it..." both sisters thought in tandem. "Let's go in the living room." Jane suggested, her finger still hooked in the front of Ray's pants and now pulling him along by it. Kelsey followed, her hand on his lower back.

They reached the plush carpet and began undressing their new toy. Ray's cock was already twitching and swelling by the time it was exposed. Both girls giggled and stripped out of their clothes, knowing his eyes were locked on them both. They stood side-by-side as they pulled off their attire, now naked in front of him. Jane smirked, standing with her hips tilted, one hand on them and a sultry smile.

"Happy you're not saving yourself for anyone, sport?" she asked, enjoying how wide his eyes were. The boy swallowed and nodded, his cock now rigid and begging for attention. Kelsey walked over and knelt beside him, pressing her finger down on top of the erect shaft and then releasing it to wobble up and down. Jane joined her, kneeling on his other side across from her sister. They both began kissing his cock, flickering their tongues against it. Ray's legs trembled and he groaned.

"C'mon, Kels" Jane giggled, smirking at her sister. "Let's lie him down before he collapses."

The sisters eased the young man down and returned their attentions to his twitching cock, kissing it together and sliding their tongue up and down its length. They took turns holding it and giving it gentle strokes.

"Hah... uhhhh..." Ray gasped.

"Oh no you don't..." Jane purred, squeezing at the base of his shaft and interrupting his imminent orgasm. There was no way in Hell she was letting that happen before she fucked him. "You're nowhere near sufficiently tipped yet, big man."

Jane stroked his base carefully while Kelsey slipped her mouth down over his throbbing head and began bobbing up and down, the shaft glistening behind her lips. She swirled her tongue around the sensitive skin, counting on her sister to keep him from busting too soon. She had no doubt Janie knew how to keep him aroused until they were ready. She was already wet and one of her hands snaked back between her legs and began fingering her pussy. She heard Jane sigh and knew she was doing the same.

They knew they didn't have the time available to let Ray cum in them both, but Kelsey had generously agreed that Jane should be given that gift, as long as Kelsey was allowed to ride him for a few moments, just to feel a live cock inside herself. That was their agreement- Kelsey would be the first one he fucked, the one to actually take his cherry, while it would be Jane that he came inside, his very first. It suited them both just fine and they were certain he would have no objections.

Kelsey pulled up now and let Jane suck his cock ardently for a few moments, until he almost came again, his climax interrupted by a skillful fingernail against the base of his member. It was a trick she'd learned a long time ago in high school, to make sure teenage boys didn't just get their jollies and leave her in the lurch. She'd used it more times than she could remember, always to her satisfaction.

The sisters both began kissing around his cock, their tongues flicking and tangling playfully with one another. Ray squirmed and moaned, his toes curling, but Jane dutifully kept him from cumming too soon. Their hands caressed his torso or fondled his balls, teasing him until he didn't know which way was up. By now, Kelsey had herself really worked up, her sopping pussy begging for attention.

"Saddle up, sis," Jane cooed. "I'll keep him ready to ride."

Kelsey nodded lustily, more eager to get this cock inside her than she would have admitted to earlier, before Jane had hatched this insane scheme. The blonde girl held Ray's pulsing dick steady while Kelsey straddled him, shivering as the mushroom head tickled her clit. She hissed almost in frustration as her sister teased the head back and forth along her pussylips, but then took matters into her own hands (figuratively) when she simply pushed down, sinking him deep inside her.

Ray moaned and Kelsey exhaled, delighting in the feel of a warm, pulsing member inside her once again, the first in months, and it felt like a thousand years. Ray arched his back reflexively, pushing deeper inside. His hands reached up and began groping her tits. He was unskilled, but at this point, Kelsey didn't care, it just felt so good to have a man's hands on her. Ray didn't seem to notice or care as her nipples leaked profusely, covering his palms in her milk. She could feel Jane's fingers, still at the base of his cock and now pressing against her lips, but knew that the hand was required, to keep him from busting too soon. She concentrated on the feel of his shaft inside her instead.

Slowly, gently, she began to move up and down, her eyes closed. This was a singular Heaven she had missed so much. True, he wasn't the biggest cock she'd ever had, nor was he as big as the dildos she was sharing with Jane, but he was larger than her ex and large enough to play his part in making her cum, if Janie could keep him from blasting off early.

Kelsey and Ray fucked, the young man looking absolutely transported by this new and wonderful experience. Kelsey undulated on him slowly, never going too fast, knowing that sometimes a slow boil was best. She could make herself cum on this dick, even if she'd promised his essence to her sister. She leaned forward, resting her hands on his shoulders, while he continued to roughly molest her tits, massaging them in circles and squeezing.

She changed the angle of penetration by lowering herself down, also changing the rhythm and prolonging his use. She was laying almost flat against him, his hands trapped against her tits while she pushed back and forth on him, his cock sinking into her wanton pussy. Her hands went to his cheeks and she smiled down at him, her eyes glinting with delight.

"It feels wonderful, Ray..." she whispered, meaning it. "Are you enjoying fucking me?"

"Yes..." he breathed, lost in sensation. The sisters were in total control and he didn't mind one bit. "Uhhhnnnn, God..."

"Let Janie and I do the driving, you'll enjoy it," she cooed, stroking his face. "You're gonna make me cum, you know? Your first time fucking and you'll make two girls cum. How about that?"

Ray didn't seem capable of speech, just moaning as he felt her pussy clasping his cock like a wet, warm vise. Clearly he had no objections. She rocked back and forth more, panting and hissing. She felt him trembling, but then moan as Janie did her thing and interrupted his orgasm again. This must have been some exquisite torture for the boy, but how many young men his age could truthfully say this is how they lost their virginity?

"Mmmmm, I'm ready to cum, Janie," she said huskily, squirming on Ray's cock and feeling herself gripping him tightly. "Keep him from busting, baby..."

She pushed herself upright, rocking her hips and her head falling back, eyes closed. She could feel Jane's fingers moving beneath her, incidentally stimulating her while her sister worked on Ray. A tingling, wet heat blossomed through her until she pressed down on him and moaned loudly, her orgasm sending her soul soaring.

Jane grinned, pleased that Ray had not cum when her sister had, meaning that she would get his spunk in her. She waited for Kelsey to enjoy the last tendrils of her orgasm before they moved on to the next phase of their plan. Kelsey slowly, almost lethargically, pulled herself off Ray's cock and began to shift herself around to straddle his face and look down his body.

"Now Ray, honey," Jane remarked as she watched her sister hover over his face. "While you fuck me, you're going to get a crash course in licking and eating pussy, courtesy of my sister, okay? You should know how to do it, and if you're concentrating on pleasing her, you'll last longer with me, okay?"

She could see him nod and his hands came to rest on Kelsey's thighs. Kelsey giggled and teased her pussy against his lips, which he awkwardly licked and nibbled at. Jane smirked, pumping his cock slowly but steadily, keeping him hard and stimulated, but letting him concentrate on his oral ministrations to Kelsey. Kelsey pursed her lips, enjoying whatever it was Ray was managing to do to her. She settled down a little more, allowing him better access to her sopping cunt. Jane leaned down and took his member into her mouth again, bobbing up and down slowly, enjoying the feel and taste of a cock in her mouth. God, how she'd missed this...

Kelsey watched her sister suck Ray's cock, shivering in taboo pleasure. It turned her on so much to see her sister performing sexual acts, and if she dared admit it to herself, it probably always had, ever since they were young. The sigh of her sister's full, pouty lips wrapped around that glistening, silken shaft, her dainty hand pumping up and down behind her mouth, it was so enthralling. If she timed it right, she'd probably have another orgasm. The thought thrilled her.

Janie now clambered over Ray's hips, lining her pussy up with his pulsing cock and teasing the head along her slippery lips and clit before inserting it inside her. She exhaled loudly as she sank down on him, sitting against his hips now.

"Oh, shit, yeah," she whispered to no one in particular, her eyes closed as she enjoyed the sensation. "That's the stuff..."

She eventually opened her eyes and smiled at her sister, sitting opposite her on Ray's face. "Still think I'm crazy for wanting some real cock, sis?"

"Mmmmm, you're crazy, you just happened to be right about wanting cock," Kelsey breathed, squirming over their shared toy. "You were definitely right, slut..."

The feeling of a warm, throbbing cock inside her was making Jane wild, like she wanted to ride it in a frenzy and cum as quickly as possible, but she reigned herself in, waiting for Kelsey to reach a second orgasm, hopefully with her. She pushed herself up and down only slowly, regulating the tempo, making sure Ray didn't blow too early.

The sisters both leaned forward and pressed their lips together, kissing heatedly. They couldn't get any closer over the length of his body, and if they tried to fondle one another, they would need to lean back slowly to keep their balance, and then couldn't kiss.

Ray's hands moved to hold Kelsey by her ass cheeks while she was leaning forward, leaning his head up slightly so he could nibble and lick at her. Kelsey moaned into Jane's mouth in response while she squirmed back against Ray's mouth. His tongue fluttered against her clit and pushed inside her, making her shudder.

Jane writhed up and down, enjoying the liquid heat of her pussy wrapped around Ray's cock, all the while kissing her sister and paying attention to how her body reacted- she really wanted, no, needed Kelsey to cum with her. She'd keep Ray going until Kels was ready.

"Nnnn, he's not bad at this..." Kelsey breathed, leaning back now and sitting over Ray's face. Jane likewise sat up straight, gazing at her sister hungrily. They both rode up and down, lost in one another's gaze and almost forgetting the boy pinned beneath them. "He's legit gonna make me cum with that tongue of his."

"Let him, Kels," Jane panted, sinking up and down on his cock, squeezing rhythmically. She couldn't wait to feel his creamy spunk inside her, blissfully free of consequences, at least for now. "Let him make you cum, I wanna see it..."

"Gnnnnn, fuck..." the older girl rasped, her face going flush, skin slick with sweat while she writhed on Ray's surprisingly limber tongue. She felt like her eyes were going to cross and switch sockets. She'd been eaten before, why was this so intense? Ray wasn't that good.

Was it because Jane was right here, watching? Because they were sharing this boy? Because they were going to cum together again?

"Uh!" Janie gasped as his cock hit a sweet spot inside her on a thrust down. She was trembling too, her body glistening with a sensual sheen of sweat. Kelsey wanted to kiss her sister's skin, to taste the salty exertions, to soothe the exquisite heat Janie was feeling. She wanted it to be her who gave her sister bliss and then cooled her down.

"Oh, yes, here were go," Kelsey grunted, her hands gripping her breasts and squeezing them while she tried to control her hips as she ground on Ray's mouth. "Uhhhhnnnnnn, gonna cum, soon."

"Jesus, Kels," Jane breathed. "Me too! Gnnnnn, he's gonna cum in me, I can feel his dick throbbing in me!"

"He's gonna cum in you?" Kelsey murmured, eyes still locked with her sister's. "He's gonna cum in my little sister?"

"Uh-huh!" Jane whimpered, her heavily-lidded eyes glazing as she approached her orgasm. "Gonna feel so good!"

"Make him cum, Janie!" Kelsey hissed, feeling her own body begin to shake almost uncontrollably. Beneath them, Ray was squirming and pumping his hips, his hands flexing and gripping Kelsey's ass cheeks. All three of them were writhing and undulating now, no longer trying to prolong the inevitable.

Kels!" Janie cried out as she was wracked by pleasure and began to thrash around. She jammed her hips down onto Ray, taking his cock as deep inside her as possible. Her back arched and she clenched her teeth, snarling, a noise her sister found so unbelievably sensual that she seized up, unreal pleasure lacing through her. She let out a scream, bucking lustily.

Jane shuddered and squealed, flexing her pussy greedily around Ray's cock, milking the cum from it, pulling it inside herself. The unreal thrill of the three of them cumming together filled her, a rapturous joy that sent her soaring. Pleasure touched every nerve in her body, lighting her up like a beacon. She couldn't really see Kelsey at this moment, but she could feel her sister, equally lost in shared orgasmic bliss.

Some time later, they all relaxed, breathing heavily as they started to come down from their climax. Ray was still throbbing inside Jane, although he was so beyond functioning now that he'd stopped licking and sucking on Kelsey's pussy, which was no doubt okay with the older girl.

The sisters were panting, still looking into one another's eyes, leaning forward to support themselves in their exquisite exhaustion. Their heads came together and they kissed wearily, needing the intimacy of kissing. Tongues tangled slowly, keeping them centered while their bodies came down from the dizzying heights they'd reached.

"God, I love you, Kels..." Jane whispered through the kiss.

"Love you too, whore." Kelsey murmured, making her sister smile and giggle. "Did it feel good to get some cum in you again?"

"Oh my God, yes!" Jane replied, leaning back now and seeming rather energized, beaming a smile at her sister. "Nothing like a protein injection to give a girl an energy boost, y'know?"

Kelsey smiled and shook her head, climbing off Ray's face. She had barely accomplished this when she heard Jane snickering. She looked at her sister in confusion but then saw her staring at something, eyes welling over with tears of mirth. She followed her sister's gaze and realized she was looking at Ray's face. The boy was looked positively dazed, staring at the ceiling. His face was glistening with Kelsey's cum, from forehead to chin. She smirked in spite of herself. He did look pretty funny.

"Did we kill you, stud?" she cooed, leaning over him and smiling down into his eyes.

"Al... almost..." he said finally.

"Well, you've done your part, and you've done it well," she said, patting his cheek. "Now all that's left is for Janie and I to clean you up, okay? Just lay there and let us take care of it."

Kelsey now turned to look at her sister, who was still impaled on Ray's cock and showing no particular signs of wanting to vacate her perch.