Dear Sister, Here's Some Advice

After my eyes grazed the time on the digital clock, I turned onto my other side so I was facing Jack. It was eight in the morning and Jack was still sleeping soundly on his back. The bed was so comfortable, and if it had been any other day, I would have curled up next to Jack to continue to sleep. But that wasn’t the case. Though it officially wasn’t a ‘special’ day, and Jack had no reason to believe it was, there was something I had planned.

I softly placed my left hand on his left cheek (which was furthest away from me) and used it to keep up steady as I kissed his other cheek, trying to wake him up calmly and slowly. While he definitely did notice me, which I could tell from his closed eyes flickering just a little, he decided to ignore me. I repeated my action to show him it wasn’t just me kissing him before falling asleep again. However, he still refused to acknowledge me. So, I swung my leg over and sat up so I was straddling him and kissed his neck instead. Using the sensitive spot to my advantage definitely did tell him I wanted his attention. After kissing his jaw, I finally got a reaction.

He groaned loudly in protest and rolled his head to the side, peaking open one eye before closing his eyes and ‘looking’ back in my direction. “Isle, it’s eight-fucking-am. Go back to sleep.”

“There’s no time for that, we have to be somewhere!” I grinned in excitement and put my hands on his chest.

“No, we don’t, fuck off,” he grumbled and let out a deep breath, trying to get comfortable again.

“Oh, but we do,” I corrected him and leaned forward to catch him off guard and go for his lips this time, kissing him fairly deeply.

“Ugh, Isle, we can do this later. Just… sleep,” he continued to complain and tried pushing me off with the little strength he had.

I didn’t get off, though, and continued to let my chest press onto his so I could whisper in his ear. “You see, I have a little surprise,” I told him and pecked him underneath his ear. “I missed two of your birthdays, it’s only right to make it up. So, I actually made plans for us.”

“Fuck,” he dragged out the word and brought his hands up to rub his face once I started to part from him. Eventually, he dropped his hands to his sides, right next to my knees, opened his eyes, and breathed out shortly to try and wake himself up. “Okay, what do you have planned?”

“Well, I’m not telling you where we’re going, but we have to leave latest at ten-thirty,” I explained.

“Isle! That’s ages away! Why the fuck did you wake me up now?!”

“You don’t think all I’m doing is taking you out somewhere to make up for missing two birthdays? There’s other stuff!” I scoffed and shook my head. “I know for a fact it is something you would have loved. Something you missed on your actual birthday.”

“You?” he grinned tiredly and cheesily.

“Exactly.” I bit my lip and stared down at him. “You get to choose anything you’ve always wanted to do, whether that is something completely new, something we’ve done before, or something you’ve done before.”

“What? You mean like eating a humongous stack of blueberry pancakes?” he asked in confusion.

“Well, if that’s what you really want. But… I was thinking more something along the lines of…” I let my actions to the rest of the talking and pulled off the shirt I was sleeping in, leaving me completely topless.

“Oh.” His eyes widened and I could feel his heartbeat pick up in pace. “Anything?”

“Anything.”

His eyes flickered around as he thought. He was really thinking about it. I could see the cogs in his head turning. It was like he wanted to make sure he hadn’t forgotten about a fantasy he always had. Right now, this was his one opportunity, and he didn’t want to choose wrong.

“Too many choices?” I laughed, knowing about some of the things he’d suggest out of the blue that didn’t even seem possible. Often they were jokes, or at least I perceived them that way.

“No, I just don’t want to choose something you’re uncomfortable with,” he worried, looking me in the eyes and biting his lip in temporary stress.

“Then you tell me what you want, and I’ll say if I’m comfortable with it or not. I won’t judge you for anything--but you know that--no matter if it’s some secret kink or something dark. Maybe I won’t do it, but I know you have many other options if that is the case.”

“Okay, okay…” he continued to rack his brain. “Just let me think a little longer.”

“Maybe getting you in the mood might help a little,” I suggested and resumed my position of leaning into him.

I started kissing his neck sensually and let my hand slip to the back of his head, tugging where his hair started getting longer. While he continued going over his options, his arousal grew. There was only a thin barrier still between us consisting of his boxers and my panties. Although it was taking Jack some time to come with an answer, I wasn’t going to stop.

“Blowjob,” he blurted out of nowhere.

I broke away from him in shock and stared down at him. “That’s all?”

“Do you not feel comfortable doing that?”

“No, I’m down,” I assured him and sealed the deal by finally kissing his lips again. “You just need to guide me a little. I have no idea what I’m doing.”

He nodded without saying a word and pulled me back down to resume the kiss. His hand was on the back of my head, tangled in my hair, giving us more pressure between our lips. I let my hands start at his collarbones and trailed them down his bare chest. He shivered underneath my touch. Although I technically wasn’t going to get anything from this act, I was more than happy to do it for Jack.

Eventually, his hands went down to my neck, grazed softly over the sides of my breasts and underneath my arms, all the way until they were on my waist. It caused us to be pressed up against each other even more. Everything felt great. But then I noticed something. Everything seemed a little too familiar still.

I pulled away just a little, just enough so I could look him in the eyes. “Wait, hang on. I’m going to have to go… down there… but how do I transition to that?”

“Just do what I always do,” he whispered back.

Something told me that he was going to have to instruct me more than he was initially expecting. “Just as you do? But the first time you didn’t tell me what you were going to do and just hid underneath the covers. And going down slowly doesn’t seem right either. You don’t have the boobs to spend time on! And there’s too much space.”

“Too much space?” Jack raised an eyebrow and laughed.

“Yes! You’re too tall. Your whole upper body is too long, it would take ages at the rate you always use.”

“Maybe it’ll be easier if I sit up,” he suggested. After I got up, he pushed himself up against the headboard before reaching out for me. “Come here.”

I sat on his lap as we resumed kissing. Although I still hadn’t figured out exactly what I could do to smoothly transition, the distance I had to move already seemed a lot easier to cross. Now it was more like a dip-down instead of a whole journey.

“Just take your time,” Jack breathed out, probably noticing that I was trying to plan it in my head. “There’s no need to rush. If it’s too much, you don’t have to do it.”

“But I want to,” I promised.

“Okay, then, if you decide to just go ‘time for blowjob’ and just go down, that’s cool.” He decided to take another approach to show that he didn’t care if I was having trouble. “If you want to do it any other way, that’s cool too. Do whatever’s easiest.”

“Okay… I think I’ve got this,” I said as an idea popped into my head.

It started with just another kiss continued at the pace from before. Because of the new position, I could easily sneak my hand down to the waistband of his boxers. I was going to start with something I knew. So, I teased a little, not going in completely, more like trying to find an ‘opening’ to left my hand creep inside. I inched it down lower and lower until I was touching him. Jack reacted positively, pushing a bit further into the headboard and moaning softly and shortly. At first I stroked him inside his boxers, but I then later used my other hand to hook around the waistband and pull down the fabric constraining him. He was no longer as focused on kissing me, and often opted to pant a little instead. This was still the easy part. Eventually, I had to move on before it was too late.

“Okay, give me some quick tips,” I told Jack as I broke away from him and planned on actually doing what he wanted.

He nodded, trying to make sure the pleasure didn’t take over his ability to speak just yet. “No to teeth… yes-- yes to tongue. Don’t f-heel the need to make yourself gag. And I’ll try to warn you bef-hore I… I… before I cum.”

“Okay, got it.” I gave one single nod and shifted down the bed.

It was intimidating. I don’t think I had ever been so close before. Well, close as in my head being that close. I just didn’t want to screw up, even though I knew Jack would completely understand if I did. If things went wrong and nothing was traumatizing, we could always try again. If things went well, then we could definitely try again and again. But I needed to go for it if I wanted to know which possibility was going to happen.

I took him into my mouth, focusing more on the sounds Jack made than anything else. I didn’t think about the way it felt in my mouth or the way it tasted. All that really matter was that whatever I was doing, Jack was enjoying it. And his slight whimpering did sound like immense pleasure, not like pain. When his hands pulled at my hair, I for sure knew I was doing it right, and continued to bob my head like I would do with my hand.

I don’t know whether time slowed down or sped up, but I suddenly got a different response from Jack.

“Isle,” he panted heavily, his body tense, “I’m--oh, fuck--I’m going to cum soon.”

Although he meant for me to then stop and either continue with my hand or something else, I figured I could push it just a little further before it was really necessary. I knew the signs that told me that he really was that far. So, I kept going despite his warning.

“Isle!” he warned again, now also tugging on my hair to get me to come up. “Isle! Off, off, off! Off!”

All of a sudden he twitched, his entire body went rigid before relaxing. His eyes were screwed shut and there was no point in trying to get me to stop anymore. I could feel warm liquid both pouring and shooting into my mouth. My eyes went wide with shock, but I let him ride out his high. Everything happened way quicker than usual. He really must have wanted to do this for a while.

Eventually, I sat back-up while Jack was catching his breath.

“Oh, shit, are you okay?” he checked, worried about me and how it ended.

I stared at him with my lips pursed shut for a while, unsure what to do next. There was a slight panic that I could feel, never having prepared for this in the short time I got to figure it all out. I just quickly nodded and suddenly sprinted into the bathroom. The door slammed shut behind me. I couldn’t spit it out into the sink fast enough, washing my mouth out with water.

“Isle, are you okay?” Jack asked from the bedroom, knocking on the door.

I turned off the tap, wiped my mouth dry, and quickly opened the door for him despite it being unlocked. “Yeah, all good.”

“Are you sure? You probably hated that.”

“No, it was fun,” I ensured him, leaning against the doorframe. “It wasn’t ruined for me. I just should have listened to you at the end.”

“Woah, I never would have imagined you ever say that,” he gasped. “You should have listened to me?”

“Oh, shut up,” I rolled my eyes.

He smiled back and pulled me into a hug, kissing the top of my head. “It was pretty fun, though. It makes me wonder what else you have planned for today.”

“You know, just some sightseeing in Baltimore.”

“Oh, sounds fun.” He nodded, acting excited. He obviously was expecting something awesome after the first thing I had planned.

“From the sky,” I added, looking up at him, “in a helicopter.”

“Now, that is badass.”

Notes