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Chapter 59 by caitlynmasked caitlynmasked

What's next for Sadie and Louis dating?

Sadie learns more about pleasing Louis

Like a deer in headlights, I’m completely frozen and don’t know what to do. The strong flavor of Louis’ cum overwhelms all my actions, all my thoughts. The donut cream while a good representation of the warmth of cum, doesn’t match the consistency or flavor at all. The cum on my palm feels stickier. On my tongue it has an oddly runny texture almost like raw eggs or oysters. The taste is sour but there’s a sweetness underlying it with a metallic scent. And all I can do is hold my palm to my open mouth, to my tongue, as Louis stares at me with his eyes wide.

What finally gets me moving again, gets me to breath and almost relax, is Louis’ reverent shaky voice saying, “That is so fucking HOT!”

Just like that, it’s like I have permission to continue. It doesn’t necessarily make it easier as I had absolutely NO intent of doing this tonight, but just as watching Louis cum gave me pleasure, seeing how much he enjoys this gives me another wave of pleasure and makes licking up his cum almost okay.

It takes a frustratingly long amount of time to lick both of my hands clean. Realistically I can’t even call them clean, but they’re at least clean enough that I can work on putting Louis back to rights. I try wiping him clean with the napkins… they may as well not go to waste at this point… but they just stick to him and his shrinking member. I have to lean over to the other side and use my water to wet the napkins down and then try again, finally getting Louis clean enough that I can slide him back into his pants.

With that done I smile back up to Louis but have to pause and giggle quietly. He’s laid back in his chair, eyes closed, with the biggest smile on his face. He’s almost a caricature of satisfaction. Turning back to my water I finally bring it up to my mouth to wash this formidable and seemingly everlasting flavor out of my mouth, only to find out that I have barely a splash left. It’s not even enough to fully wet my mouth down, let alone help me clean out the remainder of Louis’ cum and taste.

Setting my empty bottle into the cup holder I glance longingly across Louis at his humongous plastic cup of Mountain Dew. A quick look shows me that he’s still grinning like an idiot with his eyes closed so I gently lift up and start reaching across his relaxed body for the sticky citrusy sweet soda that will help me overpower the sticky musky sweet cum. Just as I lift the cup out of the cupholder, however, I hear Louis’ voice in my ear whisper lustily “C’mere babe”

One of Louis’ hands reaches around my body, letting him cup my hanging breast and pull me to his chest, while his other hand cups my cheek and turns my face toward his. Before I can even ’eep’ in surprise I find Louis’ lips pressed to mine. The surprise of the kiss mixed with the awkwardness of this position makes me reach around Louis’ neck with one arm for support and grab at the seat with my other hand to avoid falling down. As I melt into Louis’ kiss, I simultaneously curse myself as I hear his Mountain Dew tumble to the ground and spill.

To Louis’ credit, he doesn’t seem to mind kissing me even though he has to taste his own cum. Lord knows I continue to taste it as we make out for the rest of the movie. I’m sure Louis must think I’m in heaven myself as I can’t stop squirming in his grasp. Unfortunately, I just don’t have the heart to stop our make out session to tell him that the arm rest is digging uncomfortably into my side. About twenty minutes into our kissing session Louis lifts me up just enough to raise the arm rest out of the way before spinning me onto my back and resting me back onto his lap. I get a brief moment to feel his hardon press into my back and marvel at how quickly he’s recovered before he lifts me up and resumes making out, one hand holding me up by my shoulders and neck, the other spending time roaming between my breasts, tickling around my belly button ring, and cupping my ass.

Louis’ ability to kiss me without minding his own flavor seems to have cursed me. It was nearly midnight when the movie let out. Or rather it was nearly midnight when the staff interrupted us as the credits had finished rolling, the lights were on, and the theater was entirely cleaned except for our row. With both of us blushing, Louis led me out to lobby where I disappointedly found the concession stand closed. He then drove us over to the nearby college bar. We never got out of the car though, and instead just made out there for nearly an hour and a half. By the time even Louis admitted he was thirsty, the bar was closing, and we weren’t allowed in. Sheepishly Louis said we’d better call it a night and drove me home.

After a final kiss, I made my way inside. Sarah thankfully waited until I was in with the door locked behind me and Louis had driven out of the driveway before turning on the light and excitedly patting the couch cushion next to her. Using my thumb to point at the kitchen I tried to say that I just needed to get something to drink, but before I could do more than say “Sarah I just need to…” Sarah had stood up, grabbed my wrist, and pulled me down to sit next to her.

For the next hour I had to completely relive the night, including the hand job and licking my hands clean, in great detail. Only when Sarah was satisfied was I able to get into the bathroom and brush my teeth for ten minutes or so. When I was finally changed into my nighty and laying down into bed I counted backwards and realized I had Louis’ cum coating my mouth for a good four hours. Long enough that even the extended brushing didn’t seem to get rid of that phantom flavor.

I’m not sure if my subconscious was working with me or against me, but my dream was almost a completely realistic replay of the night’s events. The bar, the theater, the long wait, the buildup, the hand job, the licking, the making out, the drive to the bar, the making out, the drive home, and talking to Sarah. By the time I woke up, I swear all I could taste was Louis. Louis’ cum.

I didn’t let that get me down though as I quickly showered and got dressed. I made a quick breakfast for Sarah, and I then shooed her to get ready before she drove me over to the dealership where we were able to pick up my car. I think it’s a combination of me becoming more comfortable being Sadie, being surrounded by a girly girl vibe almost all of the day and of course going out with Louis and Marley recently that let me just girl out for the whole experience. I let myself get giddy and actually jumped up and down in my loose skirt when they drove my car out for us to see. I believe the technical term for the sound I made as I sat behind the wheel and revved the engine of my pink and purple convertible is ‘Squeeing’. I Squeed.

Driving home was a blast. Sarah’s car was fine and as the only car that I’ve driven all semester, the only benchmark I could really compare against. Her car had plenty of oomph, but it was old and heavy and comparatively lumbering. My car… and I absolutely loved thinking that… MY CAR!... on the other hand is light and spry and quick. No one was going to mistake this car for something truly fast like Marley’s Mercedes or even Louis’ Corvette, neither were as light and nimble as my little racer. Unfortunately, late December may be the worst time to pick up a convertible Miata as I was able to put the top down while driving home but unable to get it back up until I had the car parked. At which time I was practically frozen myself.

But it didn’t matter as there wasn’t much on this white earth that could tamp down my raised spirits. In fact, waiting for us in the mail, was only something that rose my spirits higher. The Osaka Dragoon Con packet. I’d of course received all the information earlier in the year, but this was the actual airline tickets, the hotel reservations, the lanyards to get access to the backstage areas, and of course the entrance tickets to the event every day.

Sarah and I sat down and started to plan the trip out. We’d be flying out on January 3rd with the Con starting on the 5th. There wasn’t really any question of Sarah accompanying me, as she’s more than earned it. We decided to pack mostly normal streaming clothes but also a few more con like outfits, including twin Japanese schoolgirl uniforms that should drive our audiences wild. We’d also be including almost an entire vlogging setup with a laptop each so that we could stream from anywhere.

When I see Marley again for our exercise routine we don’t get much beyond the stretching as I tell him about my date with Louis. I can see the mixed emotions in his eyes as he’s both proud of me and a little jealous of Louis. To his credit, however, Marley is both supportive and a good friend. We set up another ‘date’ that night so that we can train further. It’s not until he’s walking out and says over his shoulder “Don’t forget to bring extra lipstick” that I realize he probably thinks I’m ready to move past the hand job. Which I am not!

Sarah doesn’t take me shopping this time but does lend me one of her fancier dresses that I wear to the same hotel bar where Marley picks me up. After a couple drinks, and a similar pleasant reaction from the assorted customers, Marley pays our tab, takes my hand, and guides me up to the room. I’m more calm this time, more confident, but I still feel butterflies in my stomach as the door closes behind us and Marley pulls me into a kiss.

When Marley breaks the kiss, I take the initiative and let him know in the quickest way I can come up with that I don’t want to work on orally pleasing Louis. Although on reflection, I probably could have been a little less crude. “Marley, I’m not sucking you off tonight.”

Marley completely breaking up into laughter seems to let me off the hook and I eventually join him in amusement at my declaration. When Marley’s laughter starts diminishing, he cups my cheek and rubs his thumb over my lips. He’s gentle enough that none of my bright glossy pink lipstick is transferred to his thumb, yet the sensation still sends thrills down my spine. “Sadie, that’s not a problem at all. We’ll only go there when you’re ready and we don’t ever have to go there if you aren’t ever ready. Did you want to work on a different form of pleasure for your date then? A breast job? Or more advanced techniques for hand jobs?”

Once I indicated that I wanted to stay on hand jobs, Marley laid out the positions that he thought added an extra thrill to the man. Me kneeling in front of him while he stands, me kneeling in front of him while he’s seated, and reaching over his shoulders while he’s seated. They each had advantages that made sense to me. If I were to kneel in front of him while he was standing, it would invoke a large power imbalance. Kneeling alone brought me to a servile position, but if he’s also standing, he’s looking down at me, making me seem even smaller. Weaker. By comparison it makes him feel bigger. Stronger. If we do the same with him sitting, it’s still a power imbalance, but it keeps us closer. I can be between his legs, giving us more points of contact and it’s much easier for us to maintain eye contact. And finally, if I lean over his shoulder and reach down his body, it can easily put our faces together where we can kiss and make out.

Each position, however, had its disadvantages. With the man standing, he was likely to be off balance when he orgasmed, probably falling back into a seated position or worse, trying to lean on me for support. If he’s seated, there’s the problem of where he cums as it’s likely to get on whatever he’s sitting on, and probably his pants and underpants unless he’s nude from the waist down. And with me behind him, I have very little control in preventing a mess at all.

For the next two hours, I get to experience variations on all three of these positions while Marley also gives me guidance on the actual hand job technique. From the method and pace of stroking, to changing it up with rubbing, caressing, and playing with his balls. Using my palms, fingers, thumbs, and fingernails. And while none of these positions lend Marley a position to physically please me, besides when I’m behind him and he can kiss me endlessly, I still feel a pleasure welling up from within. I can see that I’m making Marley feel good. Not just making him proud with my ability, though there is that too, but his sexual attraction to me is being fed and he’s sexually pleased.

We work on the positions in various states of dress. With him fully dressed and slipped out of his zipper, with his pants undone and just down to his thighs, and finally with his pants completely off. I can immediately see the benefit of no pants as I can add so many more touches to his legs and even reaching around to play with his ass while he’s standing. All three positions are great, but even though I only get to be kissed when I’m behind him, I find that I like kneeling in front of him. When we’re back in the standing position, Marley says there’s one more thing I can do to add extra spice to this act. A thing that men will go mad over. I can either apply my lips to his cockhead just before he cums, directing it all into my mouth with very little contact between my mouth and the cock, or I can simply direct the orgasm to cum on my face.

Marley evidently could sense my hesitation as my hands were slowing down on his cock, but his voice never grew frustrated or even tense, though I could feel he was close right then and there. “Look Sadie, I know you’ve masturbated to porn. Before your transition, you were picturing being the man. Which did you find more erotic, a woman jacking a guy off and directing him to cum onto the floor? Into her hand? Into her mouth? Or onto her face?”

I have to swallow hard as Marley puts it simply and plainly. He could probably have talked until he was blue in the face and not changed my mind, but as I imagined back into what felt like another lifetime, remembered pulling up Pornyhub and watching the money shot, I realized he’s right. I’m sure it would be different if a woman were actually kneeling in front of me and jacking me off, but it was far FAR less erotic when she directed it to the floor or her hand.

I could only nod and agree with Marley. So once again the night ended in a way that I hadn’t expected.

How does Sadie use her lesson with Louis?

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