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Dear Sister, Here's Some Advice

Taking Forever and Lasting Long

SMUT WARNING

We were in a hotel lobby waiting to get our rooms. Our people were practically infesting the place. And with ‘our people’ I meant me, my boys, Jack, the other guys from All Time Low, including their tour manager as well. This was our only night in a hotel and everybody was looking forward to the extra space, whether it be a larger bed, more space to walk around, a proper bathroom, or just some distance from each other. The latter had to be taken lightly, we were still all sharing a room with another person. I was just glad we got to stay at the same place as All Time Low, because the other support bands didn’t and neither did all the crew. My main reason to be happy was that I got to share a proper bed with Jack. Although I had been getting sleep again, a bed seemed like heaven. Technically, I was sharing with Charlie, but let’s be honest here. This was a once in a tour opportunity. I was looking forward to it with all of my body.

Literally.

Usually Jack was the one to show that kind of affection towards me in public, and usually I’d always tell him to stop or tone it down. This time, I couldn’t keep my hands off of him. I wasn’t making it too explicit, but I did make it clear to him what my intentions were. We were sitting on a sofa with Rian. However, I was practically sitting on top of Jack, with my legs draped over his lap, my feet still hanging off the sofa, and Rian was sitting by himself on the other side, trying to ignore us. He was the only one who could see the subtle gestures if he wanted to.

My hand was on Jack’s thigh, just a tad too close to his crotch to make it a normal more general touch. It started out more natural, since my hand did just lay there. However, I had slowly inched it inwards more and was rubbing in soft motions. Jack didn’t stop me except for the time he thought I got a bit too close. I wanted to see how far I could go and went even closer until my little finger was on top of his jean’s zipper. He had picked up my hand and shifted his position a little before laying it back down on his thigh.

I was also giving him looks that I knew could make his heart beat a little faster. The trick was to look at him lowly, a bit through my eyelashes, and then bite my lips a little. Not obviously, but more like tugging on the skin on the inside on the right side of my bottom lip. He was actually trying to look anywhere but at me. Whenever he happened to make eye contact with me, the lust just poured out. He would breathe in a little more and exhale just a bit louder.

“Keys!” Both tour managers announced as they approached the group. They handed out the right keys to everybody, keeping to the agreed on pairings we had all made before. I got a key to the room I was supposed to share with Charlie ‘just in case I got enough of Jack’.

While I was totally horny and didn’t want to do anything but Jack anymore that day, there was just one small obstacle. We didn’t just share a room together. Either Rian or Charlie were in the way. It wasn’t like we could just finally have sex like we wanted. They were in the rooms as well. There was no way to go at it without sending one of them away. And with one of them, I meant Rian. Charlie had already made it clear to me that he was going to be catching up on sleep and refused to leave just so Jack and I could ‘fuck each other’s brains out’.

“Okay, here’s how it’s going to work.” Rian turned to us while everybody started to collect the belongings they had brought with them for the night. “I’m going to bring my belongings upstairs. Then, I’m going to be going out for coffee with a few of the others. So, I’m going to be gone for a bit. You guys… behave.”

Both Jack and I knew exactly what he was implying, and we were more than grateful. We all went up together, bringing our own bags. Rian dropped off his small duffle bag on one of the beds, claiming it as his before grabbing all the stuff he needed for his coffee outing. Once the door closed behind him, Jack and I were on each other immediately.

Our lips were pressed together tightly, my arms around his neck trying to close more space between us while he pressed on the small of my back to do exactly the same. The kiss was anything but sweet and loving. It was fast paced, pretty sloppy, and full of lust. Honestly, it was just pure physical attraction. Yes, I loved Jack, and yes we had some good love making sessions, but I just wanted him to fuck me this time.

When I thought we were close enough, my hands travelled down his chest and stopped at the hem of his t-shirt. I took a fistfull of the fabric and started pulling it up. Once I had gotten to about halfway up his chest, he put his arms up and pulled away from the kiss to give me space.

“I am so fucking horny,” I confessed while taking the chance to desperately catch my breath again as I threw Jack’s shirt on the floor.

“I can tell.” He nodded, panting heavily as well.

“You make it sound like a bad thing.” I crossed my arms and grabbed the bottom of my own shirt before pulling that off as well, letting it join Jack’s on the floor.

“Oh, no, it definitely isn’t.” He shook his head, taking my body in now that I was topless. “I’m going to make sweet hot-and-steamy love to you.”

“I’m counting on it.” I breathed out and reconnected our lips.

His hands traveled down my body before going back to my back again. One was resting closer to my hip while the other went to my bra strap. He pinched the fabric together, unclasping it. I quickly took it off, tossing it away. Once I pressed my breasts up against him, I could finally feel his jeans getting tighter. There was something pressing up against my leg and my need for him increased.

“Take off your pants and I’ll take off mine,” I whispered against his lips.

He gave one single nod in agreement and we both started unbuttoning and unzipping our jeans at the same time. I got mine off a little quicker, but that was only because I wasn’t wearing a belt while Jack was. When he finally kicked his jeans off his feet, he started walking back to me. He was wearing tight red boxers that didn’t allow him to tent, but I could definitely see his arousal. I wanted to go and kiss him again, maybe touch him and tease him a little, but he just lightly pushed on my shoulders, which I caught on was the sign for me to fall onto the bed. So, I did. I shuffled all the way up until my head was on the pillows after my back had hit the mattress.

Jack climbed on top of me, grinning down at me as his eyes scanned my entire body. He stopped when he had one knee in between my legs and one on the side of my legs, and dipped down to resume our kiss. I put my hands on his jawline and deepened it, heat coursing through my body knowing that contact was only so far away. His knee was literal inches away from what I wanted touching. And while that wasn’t the optimal contact, it made me anticipate what was coming.

Jack didn’t want to keep me waiting much longer either. He moved his kisses from my lips down my jaw, down my neck, over my collarbone, between my breasts, and all the way down my stomach. His fingers hooked onto my panties, which did not match at all with my bra, and pulled them down far enough for me to kick them off the rest of the way. As I waited for his next move, he smirked up at me and pushed himself further down my body a little more until he got comfortable. I watched in anticipation as he used his hands to part my thighs a little further and his head went in between them.

A shiver ran through me as his tongue passed over me. I tangled my fingers in his hair and tugged a little on it to express my pleasure. He continued to move his tongue in different directions, making me arch my back and causing my eyes to occasionally slip shut. I had no idea how I had ever lived without knowing what pleasure Jack could give me just through doing this. He had gotten me off so many times with nothing but this. It made me feel euphoric. His tongue just managed to send tingling sensations up my entire body with just a few swipes.

Unfortunately, he stopped and looked up at me as he took a small break. “You still okay up there?”

“Uh-huh.” I nodded, so he went back to what he was doing before.

I felt so close to having an orgasm. But then my eyes fell on the digital clock on the bedside table between the two beds. It had been just over forty-five minutes since we originally came up to the hotel room. I frowned, wondering what had happened with the time. Jack must have been getting bored by now.

So, I tugged on his hair softly to get him to stop. “Come up here.”

He did as I said and crawled back up my body, kissing me deeply with either hand on one side of my body. I could taste myself, which didn’t come as a surprise to me. He had been down there for so long, I had no idea how he kept it up.

“Can you flip us over?” I asked, wanting to do my bit as well, especially since he had been pleasuring just me for that long.

He nodded and let himself fall beside me. I got on top of him and straddled him in one swift motion. I continued our kiss and cupped his bulge through his boxers, moving my hand up and down slowly and occasionally rubbing over the head. Having had this hard-on for so long must have started getting painful for him, and I wanted to change that.

I took hold of the waistband and pulled down the boxers, letting him be free. Much like I had done, he pushed them off his own feet. When he was done shuffling around, I started to move myself down his legs so I could bend over and give him a blow job. But Jack grabbed my arm and stopped me.

He was shaking his head, beckoning me to stay where I was. “I don’t need that, just get on me.”

I looked at how desperate he was, and nodded in quick agreement. Before I could tend to his request, though. I got off him and scrambled to his backpack. I took two condoms from the front pocket and rushed back over to him, putting one on the bedside table and tearing open the other one. After rolling it on him, I got into position. I took hold of the base and lined myself up before lowering myself down. We both moaned quite loudly when he was sliding inside me. Jack, because he was waiting for the sensation, and me because I was already so close to that orgasm happening.

I started using my legs to bounce up and down. The room filled with skin slapping on skin. My hands were holding onto Jack’s shoulders as I sat up while his hands were digging into my legs. His fingerprints were probably going to leave bruises, but everything felt too good to care.

“Babe,” Jack groaned after a few minutes, but I didn’t acknowledge it. He repeated, “babe. Isle. I’m really close.”

“No, not yet,” I breathed out heavily, actually speeding up my pace despite it doing the opposite of helping Jack last longer. “I’m so close. Just a bit longer.”

So, Jack tried his best to hold on. He threw his head back in the pillows and his fingers dug even deeper. I really felt like I was just on the edge of losing it all, but it just wouldn’t come. I just wouldn’t come. But even Jack didn’t get the opportunity to come before I heard the door open and close.

I looked at the entrance and saw Rian. Out of surprise and fear, I yelped loudly and couldn’t get off Jack any faster. In the process, I had managed to fall in between the beds; I smacked onto the floor, but at least I was hidden from Rian seeing me naked for any longer.

“Oh, shit!” Jack shouted out himself. “Isle, are you okay?” But I didn’t say a word, too afraid to do anything with Rian still in the room.

Rian seemed just as shocked, quickly sputtering out an excuse. “I’m sorry! It’s been an hour and fifteen minutes. I thought you’d be done by now!”

Instead of getting mad, Jack told Rian in the most serious and calm voice, “dude, don’t just stand there, get out.”

Rian left immediately. Why he didn’t do so in the first place, I did not know. Maybe it was the shock that made him freeze up. Either way, I was still on the floor.

“Isle? You okay?” Jack asked me again, this time leaning over to look at me.

“Yeah,” I replied, getting up slowly and lying down on the bed next to Jack. My legs were shaking like crazy, but that wasn’t from my entire body slamming on the floor at a weird angle.

“Do you want to stop?” he hesitantly suggested. He knew full well that I usually would have been too embarrassed to continue. This time, however, I was determined to get off.

“No, leaving us hot and bothered isn’t going to do either of us any good.”

Jack seemed more than happy with my answer. He got on top of me and slid back in, kissing me deeply. To get back to the level we were at before, he rocked back and forth at a fast pace, he even gave a helping hand. Trusting himself to hold himself up with just one arm, he used the other to rub circled around my clit. In no time, I felt like I was close to being pushed off the edge yet again. This time, however, I didn’t get to because Jack did it first. He groaned deeply and twiched, his pace slowing and coming to a halt.

It was obvious he was exhausted. He collapsed on me for a few seconds, but he didn’t want to leave me hanging. Being the good guy he was, he mustered up the energy to get back up and finish me off. He continued to rub me, sucking softly on my neck. And it felt great. Once again, I felt like bliss was just a second away, but it just didn’t come.

“Isle, tell me how to help you,” Jack eventually sighed, deflating a little since he couldn’t get me to orgasm. Usually him touching me for a bit longer was all that I needed, but it wasn’t working.

“I don’t know,” I whined.

“Just tell me what feels good. Even if it’s something you’ve done yourself. You know your own body better than me by now.”

“It all feels good, I just can’t seem to– It just won’t– I’ve been so close for so long. Please help, Jack!” I begged, tears threatening to fall.

He looked down at me, a concerned look spread across his face. He knew exactly what it felt like being edged on, and he also knew what it felt like when the edging went on for too long. The pressure was built up so much, it wanted to be released. But it just wouldn’t. I felt like a coke can being shaken, just not able to burst open.

“Okay, okay, we’ll figure this out. I promise, Isle.” But he got up instead of helping me. “Just give me a second.”

I sat up to watch him run into the bathroom. He took off the used condom and wrapped it in some toilet paper before throwing it into the bin. Once he came back into the room, he stood at the end of the bed and beckoned me over. I pushed myself down until my legs were over the edge. He took another second to think of a game plan.

“What do you want to do?” he asked me when he was unsure of which approach to take.

“I don’t know,” I sighed, almost ready to give up and just take a shower.

“Okay… what do you enjoy when you’re by yourself?” He took a different approach.

I looked at him and raised an eyebrow. “I don’t do anything by myself.”

“Fuck it.” He shrugged and leaned over to kiss me.

He used his hand again to try and get me to finish, only this time he was using more pressure and a quicker pace. The position couldn’t have been the most comfortable for him, bending over like that, but it didn’t matter to me. If anything, this position gave him a lot more access, making it feel great for me. Over time, the feeling started building up again after the short break we had. Still, it took a very long time, so long that Jack even managed to get aroused again.

While I felt like we were just going to have to call it a day, a switch suddenly flipped. It was like the dam that was holding everything back was finally starting to crack open. Jack must have noticed as well, because he took his fingers out of me, only keeping his thumb in place, and thrust into me. It wasn’t long until I finally got to my climax. This was the strongest wave that had ever come over me. I couldn’t hold back the loudest moan, I was just a few decibels away from screaming, and my nails dug into Jack’s skin. He released for the second time shortly after. After we had ridden out our highs, he pulled out and lied down next to me, his legs also hanging over the edge.

“Oh, man,” he whistled.

I was about to comment as well to show my satisfaction, but a familiar feeling between my legs stopped me, making me squeeze my thighs together. “Ugh, shit, Jack, you came inside me.”

“Shit.” He reciprocated the feeling. “I forgot, I got caught up in the moment.”

“It’s okay,” I brushed it off. The only reason it was bad was because I had stopped taking birth control since I always managed to forget to take it anyway on tour, making my life a living hell. We could easily fix this with a trip to the pharmacy. “But I’m going to have to run to the shower before we gross out Rian even more.”

“I’ll join you.” Jack nodded, also knowing the trip to the pharmacy was going to happen right after.

We laid there for a bit longer before I had to do the all too familiar waddle to the bathroom.

Notes

Comments

@settle for me.
I usually just post a chapter a day or every other day. Sometimes less, sometimes more frequently. No need to force it in a short amount of time.
Well, two stories are close to finishing, so a new one will arise. It's based on an idea I got years ago, but I made it a bit more sophisticated. If a story about an age gap intrigues you, keep your eye out for it.

@aweirdkindofyellow
I remember you saying and I did say I was going to do the same but I just honestly never got around to it.
I have been told nothing about any of your new ones, just that you have lots on the go.

@settle for me.
I've been transferring everything to Wattpad and AO3 for quite a while now. Given up on Mibba though. Never liked that interface and layout, so couldn't be bothered.
I'm going to start another story soon (after I finish some that I am currently writing). And I'll still post it here, but you'll just have to actively search for it yourself if you want to read it. I don't know if you've been told anything about it yet, but you might like it or hate it.

@aweirdkindofyellow
Same! No one else updates anymore and I need to start on another site but I just... don't have the energy?
I'm going to be absolutely lost when you finish the ones I'm subscribed to. I honestly won't have anything to do.

@settle for me.
I've also really been missing reading other people's new stories. Seriously, the only story I still read right now is yours. I just can't find anything else.
I've actually been trying to figure out a way how to change the sequel to this story so it's not as long and officially ends there as well.