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Closer Than Ever (DarkofNight x EtherealElvenEmpress)

Rob was certainly impressed. Whether it was her enthusiasm, or simply the fact that his cock was currently inside his little sister's mouth, Rob was currently in a state of absolute rapture. By the same token, he had already been through quite a lot tonight, between his sister's vigorous dry humping and bringing her to multiple orgasms. With her soft lips wrapped around his shaft, slowly working their way further and further down his shaft, he wasn't sure how much longer he could reasonably last.

The sudden increase in suction and her determination to take more and more of him into her mouth made him shudder, his eyes losing focus and rolling into his head just for a moment. "Mmm Ri, getting real close. Keep going." he said breathily, any of his previous caution to take her time now long forgotten.
 
It was hard to get used to something so big past her soft plushy lips. Every deep throat made her gag but Riley didn’t give up. Her feathery touch massaged his heavy balls with his blessing. The sounds of her sucking filled her room. Her bed receiving the first sexual action and with her brother no less!

Hearing Rob’s words he could Riley put more determination behind her first low job. His tip hitting the back of her throat as she finally regulated her breathing through her nose.. Rob said he was close but it fell on deaf ears. She let her tongue flicked and circle his pulsing shaft. Little did she know she was about to unlock a grand eruption of pleasure for her dearest brother.
 
For it being her first, it was still one of the best in Rob's life. Whether it was her enthusiasm and determination to take him down her throat or the fact that it was his own little sister doing the act he couldn't put a finger on. In point of fact must thought at all was escaping him at this point. Her small fingers nearly tickling his balls had them feeling heavy, ready to spill his seed.

He was only vaguely aware of the feeling of his cock hitting the back of her throat as his body shuddered under her efforts. "Ohh God. Mmm Riley." He groaned just before he began unloading shot after prodigious shot into his little sister's mouth.
 
Riley wasn’t ready. Even with the warning and every bit of signaling Rob gave her she wasn’t ready. Suckling heavily he could easily hear her enthusiasm as her saliva dripped down his shaft.

Every time his cock tip hit the back of her throat she gagged, but never backed down. Then it came. Well he came at the most opportune time with his tip at the back of her throat. That prodigious shot went down her throat. Riley had no other option to swallow the first few pumps.

That petite body of hers tensed up and froze and she didn’t mean it but she took hold of his balls and squished them without thinking. The action of her pulling back with him mid shot only meant what was left shot all over her face as she gasped for air. His seed dripping from pink lips. Her black dress would bare the marks of her brother’s seed and leaving a memory Riley would never forget.
 
Despite his warning, she wasn't ready for him, though she also managed not to gag. He spasmed several times down her throat with no problems.

And then there were several very bad problems in a rapid sequence. In her surprise, Riley squeezed. She happened to have a nice grip on his balls at the and so his low groan as he released into his little sister's mouth immediately rose several octaves to be nearly a shriek. He dug his heels into the mattress and pushed his body away trying to escape the clamping pain his testicles had suddenly been subject to. With a wet pop, the head of his cock slipped from her lips. Within the same breath his next shot of seed splattered across her face wetly. A few of the declining arcs of her his last few shots struck her chin or just missed it and landed on her dress instead.

"Ow." He chuckled softly, sitting up on his elbows and rising to a sitting position. "And oops, that's some mess." He chuckled softly, reaching for her nightstand and grabbing a tissue so she could clean herself up. "That was really good though, if that wasn't obvious." He smiled, reaching behind her to undo the zipper on her dress to help her out so she could avoid it getting stained.
 
Riley got frightened and when she heard history she let go of his balls but not before he gave her a few extra spurts. Poor Riley looked modified and she pulled back in her hands move completely away. She looked really shy and more than embarrassed about what she had just done. “Robbie? Are you okay oh my God! I’m so sorry.” She whimpered as she stayed on her knees looking at what she had done and brought her hand up to her lips and felt all of his cream that got there then looked down at her dress.

Frozen there as well I’ve had to help her get out of that dress leaving her only in a bra as it fell around her thighs leaving her only covered with just the bra and her upper half. “Robbie… I think I did that right…you taste a little sweet..”. Her last compliment may have broken attention as she said they’re mostly nude covered and her brothers gift.
 
He took a few long deep breaths calming himself down a bit. "That felt amazing until right at the very end." He grinned widely. "And you do look pretty hot with me splattered all over your face." His eyes roamed over his sister's mostly naked body. "If I let you try again sometime, you're gonna promise to try not to literally tug it off, ok? He grinned, shrugging off his own shirt, gathering up all their clothes and standing up.

"I'm going to get these in the wash quick like while you're getting cleaned up, ok? He grinned stepping out of his sister's room and giving her some time to get herself sorted out.
 
The look on her face was more worried for him that herself. Riley looked mortified but hearing her sweet brother’s kind words and constructive criticism helped. Seeing his grin reassured her that she didn’t do too horribly as she nodded. “I’ll do better next time. I promise. Next date I’ll do so much better. I’ll even watch extra…you know.” He already knew she watched porn but it was still hard to say it.

It was then Rob took her dress to get it in the was asap or that stain would set and that would be hard to explain away. Riley took the initiative and took off her bra leaving her mute as she handed it to him. “I’ll be quick.” She said making her way to the bathroom and opting for a shower since after that left her winded but she couldn’t even explain how good it felt. Showering she couldn’t explain the high she had but when she was finished and all wrapped up in a towel and went to change her bedsheets since she did cause this mess. Hopefully she’d finish before her brother caught her still dripping from the shower.
 
Rob practically floated to the little laundry room, feeling extremely relaxed after the big load his little sister had taken from him. He smiled to himself as he loaded up the washing machine. He and his little sister had just gone down on each other. She'd basically admitted to having had feelings for him for years. It all seemed too good to be true. Not only that, but she seemed enthusiastic to go down on him again. How quickly would that happen? Knowing Riley, probably tomorrow night. With the laundry sorted, he returned to her room.

He found Riley wrapped in a towel, leaned over her bed and changing the sheets. Quietly, he crept up behind her, reaching under her and undoing the towel she had wrapped around herself, letting it fall to the floor as he chuckled. "When does date night end anyway?" he grinned as he checked out his little sister, her pale skin still glistening from the shower. "Snuggling up together and going to bed sounds like a nice way to finish out the date. Your bed or mine, assuming you're interested?" he grinned.
 
Rob knew his little sister better than she knew herself. That little minx was an overachiever and he knew that she would try this again tomorrow night or even in the morning. He saw how she got with her studies and she loved keeping a 4.0 GPA. If she treated Rob like her studies he was going to get this treatment every day!

She was pent up and hormonal with no chance to have relief for years. all of that pent-up sexual attention focused on Rob would either make him happy or extremely tired. She did not hear him when he came into the room she was changing the sheets. Those very dirty sheets.

He managed to catch her off guard and doing her towel and letting it fall leaving her nude and glistening from the shower. “ROBBIE!” She squeaked and playfully hit him that she turned around giving him a full frontal shot. Those beautiful b cup breast perky pink nipples. She was not very top-heavy at all but she was very proportional.

It didn’t phase her embarrass her that she was nude in front of him he’d already seen her naked and licked her in unspeakable places and she had had his lower region in her mouth. There is no coming back from that.

“Your bed. My bed is kind of damp because of you know…what we just did…” his petite little sister said sheepishly. She looked down embarrassed thinking of what they did but more of the fact that her bed was practically soaked in her juices. It was new to her that she could produce so much. Her bed would need to dry off and she would leave the air conditioner on for a few hours to help. “I’m still interested you goofball behave I’m gonna make your bed wet too. If we do that we are both sleeping on the couch.” Giving him a playful punch on his arm not enough to hurt but enough to sting. Most siblings would be modified after the fact but here Riley was treating him like he was a date. The fact that he was not mortified made her more comfortable. Either way this is the start of Riley sleeping in his bed more than her own.
 
He gave a broad smile as he looked her up and down. For being not very top heavy, she certainly had her brother's interest there. His hand reached out to cup one of her bare breasts softly as she spoke.

"I was just discussing sleeping arrangements..." He grinned mischievously as he gave her breast a squeeze. "Are you really such a hornball that we need to worry about you soaking my bed just cuddling with me?" He chuckled softly and kissed her forehead. "Maybe you're just worried you won't be able to keep your hands to yourself?"

Without waiting for an answer he leaned in and tossed her slender frame over his shoulder. "If it needs to dry, it can do that without your help." He smiled before turning and carrying her out to the hall and down to his bedroom, dropping her on to his bed with a gentle toss.
 
When her brother took the chance to cup her small breast Riley quickly shushed and blushed. He could easily see why the boys and even girls were eying his sister like a snack. Speaking of sleeping arrangements for her to keep silent and him calling her a hornball got her to huff in a cute, angry tone.

“It’s your fault I can’t keep my hands to myself. You can’t blame me. I never got to touch myself at home with mom or dad being the virginity police. Maybe we need a practice room just for this. It’ll keep out beds dry…ROBBIE!” His tiny sister yelped as he easily picked her up and carried her to his room tossing her to the bed gently. “You weren’t complaining either and I think you like my wet spot…” she teased.
 
He chuckled softly. "It's my fault Mom and Dad wouldn't even let you touch yourself? Not sure I follow you there..." he laughed as he carried her down the hall. "A practice room? I know Mom and Dad aren't exactly around day to day, but I think you should realize they do like to drop in with very little notice. I think they'd start asking questions if we had a room just for our little 'dates', don't you?"

"Of course I like your wet spot." He grinned, looking down at her sprawled on his bed. "After all, I spent quite a while with my tongue in your little wet spot tonight, didn't I?" he smiled, turning down his blankets and sliding into bed, patting the spot next to him for her to crawl in and join him. "Come on, you were super cuddly last night, I bet it's even better without clothes getting in the way." he grinned at her.
 
Riley nodded sheepishly. “You are not the problem mom and dad are just over protective Robbie.” She said offering him the sweetest of smiles. “I guess in that case I’ll just use your room instead.” The fact that he was going to keep date nights made her ecstatic. when he said he liked her wet spot it sent her into a fit of giggled as she forgot that she was literally as naked as a day she was born. “ what do you think if when we’re together I don’t wear clothes. I mean I like being naked with you and it’s not like you haven’t seen me or had your tongue in my wet spot I like it down there. Is that such a bad thing?” She said turning closer right cuddle you against her brother wearing nothing at all.
 
Rob reached out to the nightstand and turned off the light, casting his bedroom into darkness. His arms wrapped around Riley, feeling her bare skin pressed against his. His hands roamed over her curves, cupping her breast, grazing her narrow waist, squeezing her ass.

"I won't say I don't like the idea of seeing more of you around the house." He chuckled softly. "But that had better not be a distraction that gets in the way of our studies and housework." He gave her another squeeze. "Last thing we need is to start failing classes because we can't keep our mouths off of each other."

Holding her close, he made himself comfortable and quickly fell asleep. The next thing he knew, early morning sun had filtered through his bedroom window awakening him. They had gone to bed fairly early so this was hardly a surprise. The surprise was rather the position he awoke in. Riley had her back turned to him, pressed against his chest. His morning wood had worked it's way between her thighs, held in place with the top edge of his cock held along her pussy lips.

With a grin Rob leaned over and kissed her temple, giving her bare breast a squeeze as well. "Good morning." He whispered as his hips began to move, dragging his length across her lips.
 
Rob turned off the light as she got comfortable and curled up next to his nude body with her out. This was new but she didn’t mind it. She really liked us but who could she brag to? Not her friends they think she’s crazy. Besides most of her friends had crushes on Rob anyways. They wouldn’t believe her if she told them that they fooled around.

“ I won’t let us mess up our studies you know how I am about grades. I graduated at the top of my class you know. And do the same here and I’ll help you as well. I’m already placing at sophomore and Junior levels for science and math. Come to think of it I might be in one of your classes or three.” She couldn’t help but brag about her achievements since she was proud of them and she knew Rob would not call her snobby or bratty at least not with studies.

He had worn her out and she fell right asleep next to him not long after she was chatting she really could not stay awake long anyways.

Night came and went and she slept so well but she also woke up at first light. Laying in bed and she felt Rob give her a kiss and she broke her fake pretend sleeping by giggling. “Not awake yet ten more minutes.” Riley said knowing that her brother would probably say no and she didn’t mind. Her joking would stop when she felt how his length of dragged across her lower lips making her moan and push back without thinking. If he kept teasing her like that she would not stay a virgin very long with him in bed. “Oh that feels so good…” murmuring as she wiggled her hips making sure to get his bulbous tip wet with her own morning juice. If Rakuten her like this she might wanna feel just the tip one more time. It was still practice and the tip really wasn’t sex anyways.
 
Rob chuckled at her request. "I don't mind if you lay here for a while longer." he told her before he moved his hips. One hand had slipped under her neck and he could just reach her breast to give it a squeeze as he slid between her thighs. Her wetness helped him move a little easier as it coated his member.

"Mhmm, feels real nice." he murmured as his other hand moved to her hip, the better to hold her as thrust against her. "This angle feels a little safer than last night too." he chuckled. "I almost accidentally popped your cherry, that still kind of freaks me out." he chuckled.
 
Rob’s voice was met with silence as he felt Riley pushed back and rub against him. Her breathing quickened as she let her body take over. Whatever he was doing felt good. It was like the night before when he said they had to be careful. They were always careful as he trusted her brother to a fault. He would never hurt her or do anything against her. She loved him with all her heart and maybe more. “Almost but didn’t Robbie. You know I trust you and even if you had popped my cherry I wouldn’t hate you. Do you know I love you? You should. You’re the best brother any girl could ask for. Even if he actually popped my cherry I wouldn’t care. At least my first time would be with someone I truly love.” He could take that in anyway he chose but she loved him in a sibling way but also in a way she probably should never love her brother. But right now they were alone and she could speak her mind especially since she was nude and rubbing against her brothers forbidden zone.
 
Rob sped up little by little, letting his pleasure guide his motions. "I love you so much Ri." He gasped softly as his cock rubbed against her lips. "It's frustrating though. If you weren't my little sister I doubt I'd even hesitate to pop your cherry and make a woman out of you." He let out a low moan, squeezing her against him as his pleasure grew and grew. "But by the same token, if you weren't my little sister, these last two nights probably wouldn't have been the best dates I've had in years." He told her honestly.
 
Riley had soft sweet moans that only got louder the more Rob rubbed against her lower lips. “ you’ve been my best date I’ve ever had to. What if I said I didn’t mind if you do you know where we…ummm… you’d say no anyways…” Riley figured that he had his mind made up and he was right. They were brother and sister so thinking of that was really wrong. “I’m being so selfish right now…. let’s just enjoy it…” resigning too heavy flirting and grinding which didn’t bother her if she knew her body was talking mostly. Either way she was happy to have her brother and she knew he’d eventually find a girlfriend so why not enjoy this precious moment right now. “ should I put on my panties to make sure we don’t accidentally…pop my cherry?” She asked wondering if that would help her brother not feel so conflicted but she did like the feeling of his tip rubbing against her lower lips.
 
Rob groaned softly. His brow furrowed. She was making this worse for him, telling him she wouldn't mind. He wanted to, badly, but he couldn't. It wouldn't be right. He was supposed to be protecting her, keeping her safe. Even this was wrong but he couldn't help himself now. "Yeah..." he grunted. "We'll enjoy it." He started thrusting faster. "No, let's not stop. Just... Don't move around too much. It'll be ok." He was feeling himself getting closer. He let out a low groan, squeezing her tight. "I'm getting close Riley..." he panted, thrusting harder and harder. "So close. Are you feeling it too?" his speech was a breathy gasp as he asked. "Cum with me sis." He nearly begged.
 
Even though Rob told her to stop moving around so much Riley kept squirming. Did he have any idea how this felt especially to her? Perhaps he did since she was rubbing against his tip and shaft slowly grinding herself back letting the tip slide into her but not all the way.

Hearing robs voice egging her on she lowered one hand between her legs wrapping her date to hand around the shaft as she used it to rub his tip up and down her soaking wet slit. This was a move she saw an erotic videos figuring that would feel good to her brother as much as it felt good for her. He wouldn’t be able to penetrate her but she was letting him only go tip deep as she grinded and wiggled against him. “Let’s cum together…. I really want to cum together…” The way she was rubbing and letting his cock tip dip into her he would have to be careful because if he exploded in the right way he easily come all over her inviting pussy.
 
Feeling the tip of his cock entering her again, even just a little sent shivers up his spine. He fought to keep his thrusts shallow, not to let himself enjoy it too much even as he rocked against her roughly. He groaned loudly as he felt her hand pressing him against her and grit his teeth. It was good, too good, and he knew he would be finished soon. He kept thrusting, still fighting the urge to thrust harder, go farther, take her for his own. It would be terrible. He'd be going against his own decision, but not only that, he could only last a few thrusts at this rate and surely Riley deserved more than that her first time, right? If he was going to do it, he was going to do it right. And that thought echoed through his mind over and over. He was going to do it, and he was going to do it right.

"Together. Yes. Together." he groaned between his swift shallow thrusting, feeling himself edging ever closer. His body spasmed, muscles tightening as his orgasm washed over him. No, his tip was still inside her. He pulled back a bit, even though it took all his will, as shot after shot splattered over her fingers and innocent little entrance. "Mmm, Riley... So good." he murmured as he held her close, feeling waves of shivers moving up and down his spine, hoping he had pulled out in time, hoping that little depth wouldn't matter even if he didn't.
 
His younger sister wasn’t thinking straight. This amazing feeling took over as she felt his shell thrust slowly sliding in and out of her. She couldn’t rub two brain cells together and get out any words. She could hear her soft and shallow breaths. The way her body quivered he could tell she was close without her saying a word.

The way she moaned he could tell she was very close to exploding herself. Rubbing his tip against her at slowly penetrated her but it never went too deep. Rob did a damn good job especially when he started irrupt Ing he pulled out enough to spurt all over her lower lips and her hands as she still rubbed him and held on. Riley dreamed of having a way to come back but she couldn’t even talk at her own nectar flowed over his mixing with his cum. He came all over her but luckily nothing made it inside.

He was so good at holding back and even though Riley wanted to go all the way her brother was a gentleman and wasn’t going to take her virginity in such a simple way. Panting as she laid there rubbing the tip of his cock with her thumb feeling all that came out of him and using it to wet her fingers. “Did I make you do that?” Oh her voice was so innocent. With how cute she was it sounded very dirty. “Don’t worry I’ll do the laundry today.” She managed to say especially since she thought she caused him to explode that much and now his bed was the wet one.
 
His cock was extremely sensitive having just cum. Feeling his sister's thumb moving against his head nearly hurt, but by the same token he could also feel her rubbing as if mixing their fluids together, smearing it further over her pussy lips. In some small way it almost felt like claiming her, marking her as his own. This was all just for fun. Until he got himself another girlfriend. Until she got a boyfriend. He didn't want that though. His sister dating anyone else. On some level though, he knew that sooner or later he was going to have to accept it, and he was going to have to do his due diligence to make sure that guy was right for her. And part of him hated that thought.

He grinned widely. "You certainly helped. I think it was a shared effort." His hand drifted around her hip, meeting with her fingers and helping to spread their shared mess over her lips and mound. It was easy to relax and let those thoughts out of his mind. He'd just cum and was curled up against a beautiful woman. For the moment at least all was right with the world even if this couldn't last. "A guy could get spoiled waking up like this." he chuckled softly. His hand continued to paw and squeeze at her soft breast even though he was spent. For the moment he could just let himself bask in the afterglow.

After a few minutes he gave a stretch. "Thank you. Laundry would be good. We should get up and get moving here soon though." he told her, not actually liking the idea. "It is your first day of class, and I should make sure you know where you're going at the very least." he smiled.
 
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