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Chapter 58
by
caitlynmasked
How does Sadie put her well practiced lesson into practice on her date?
Sadie gives her first voluntary hand job
Running in heels like these slink backs was impossible but I still tried. All that really ended up happening was me bouncing up and down as my feet minced forward in their little steps, my breasts bouncing up and down ridiculously, as I moved forward just a touch faster than a normal walk. When I get to the car I locked my knees and bend forward at my back until I can look into the low-slung sports car and smile at Louis, sure I was giving him a clear view down my halter top at my strapless bra. My quick wave, big smile and “Hiya Baby!” just made Louis cover his mouth and laugh.
Getting into Louis’ car was always an ordeal as it was the lowest of any I traveled in. The fact that I was wearing a long skirt this time didn’t help since as soon as I opened the door and stretched my leg in, the sarong skirt’s split opens up making sure I flash Louis the entire length of my leg and might have even flashed him the strap of my thong before I was able to sit down and wrap the skirt back around me. To make sure Louis doesn’t focus on the flash of flesh I immediately lean over and press our lips together in a happy kiss before settling back and asking “Ready?”
Louis went all out and actually made a mix tape for his car’s cassette player. I have no idea where he would have got a cassette, let alone something to record one. Of course, all the songs are 90s boy bands like Backstreet Boys, Nsync, 98 Degrees, and Hanson and by the time we pull up to Cool Cat Cocktails we’re both belting out “Mmmbop, ba duba dop, Ba du bop!” at the top of our lungs. When we walk in, I’m happy to feel Louis casually and confidently put his arm around my tiny waist and even brush his fingers over the skin between my halter top and skirt.
I picked this towny bar not only because of the tasty cocktails and relative privacy, but also because when Marley, Louis, Sarah and I were here all the tables had long discrete table clothes. Just perfect for keeping our waists and my hand’s activities in private view! So, when we stride in and the hostess starts walking us over to a booth I try to hide my disappointment… no table clothes are out. The tables are all nice enough that they certainly don’t need one, but of course that’s not why I wanted it.
Louis does better this time, remembering to order me a Negroni sour along with his glass of a local IPA, and we end up having a good time regardless of my plan going up in smoke. We talk for quite some time mostly about school this time. I share that my semester is done and that I’m well on my way for finishing my Bachelor of Science in Computer Science and Engineering on time. I almost **** on my drink when Louis shares that he’s working toward a Bachelor of Philosophy. I’d always just assumed he was working to be a computer engineer as well.
After we’ve had a few tasty beverages and my head is just beginning to spin a bit, we see that our show is starting soon and drive over to the local theater. I’d told Louis that I’d like to go to a movie and let him pick it, honestly hoping he’d want to see Godzilla Minus One, Aquaman and the Lost Kingdom, or even the action flick Silent Night. I giggle a bit to myself, however, when I hear him order two tickets to What Happens Later. I really don’t have anything against Meg Ryan or David Duchovny but the movie has been out for almost two months and it’s not like it even got good reviews. But then again, I’d played up girly thing about myself when we’d talked before so maybe Louis just assumed I’d like a romantic comedy.
Before getting our seats, we stop by the concessions stand and get some drinks and snacks. Louis again takes charge and orders us a popcorn to share, with extra butter of course, a gargantuan Mountain Dew for himself and a bottle of water for me. I start to correct him as I’m feeling my sweet tooth and would like to indulge in a soda myself… I could even go with a Diet Pepsi if I wanted to watch my calories… but I bite my tongue and let him have the honor of ordering for his date. I also let him carry all our drinks and snacks as we head into the theater.
It turns out seeing a two-month-old badly reviewed film has its advantages. While people were crowding in to see the new monster, superhero, and action movies, there are only three couples in this particular 150 seat theater. One couple is sitting right up front where they’ll have to gaze up at the screen. The other couple is sitting off to the right, immediately next to the wall. So, Louis and I end up at the rear of the cinema in the middle of the row.
After the trailers play and the last lights dim, the movie starts, and I snuggle up close to Louis. He makes sure his huge soda glass isn’t in my way and puts the popcorn right where we can both get to it. I can only barely follow the movie… they’re right, it’s not all that good… as I keep waiting for Louis to make his move. I know he’s too much of a gentleman to start something as overt as I have in mind, but we’ve gone out enough times and made out enough times that I expect my hand to be held, to feel his thumb rub over the back of my hand, to feel his breath on my neck, for him to brush my one ponytail out of the way before finally turning me to face him and pulling me into a kiss.
But that doesn’t happen.
After twenty minutes or so, I start dropping little hints where I can. I ‘miss’ the popcorn at one point and end up grabbing Louis’ hand. Instead of letting it go, I mimic his own motions of rubbing my thumb over the back of his hand. I try to subtly blow on Louis’ ear to get him to at least look my way, but he only brushes his hair over his ear. I bump his knee with mine and keep it pressed there but after thirty seconds of that Louis ‘politely’ moves his leg out of the way, giving me more space.
After the movie is about half done, it finally occurs to me that Louis is probably playing the gentleman role to its ****. I’d told him I was nervous about going into a theater before without going into the exact why, so maybe he’s just respecting my boundaries? Or at least what he thinks my boundaries are?
While I really don’t want to steal Louis’ romantic thunder, I don’t want to waste this perfect opportunity or the amount of pure will I’ve built up to try this. While it’s easy to think of pleasing ‘my boyfriend’ in the abstract, it’s difficult when I imagine my hand actually rubbing over Louis’ pants and feeling his cock respond to my touch. If I build myself up like I have tonight and don’t end up doing it, I’m afraid I might not actually be able to build myself up again. And even if I do, will I get another opportunity of sitting in a dark theater, dozens of yards away from the nearest people, all of whom are also taking advantage of this privacy and making out?
Like every cheesy teen romantic movie I’ve ever watched I take the opportunity to yawn and stretch my arms out. Instead of replacing my hands into my lap though, I let my arm snake over Louis’ shoulders where my hand can reach up and run through his hair. And just as though the fates were setting me up, when a particularly romantic part of the movie comes up I tug just a bit on Louis’ hair and pull him into a kiss.
Thankfully Louis isn’t fully dense and he responds, letting us truly start to make out. He still seems slow to act so a few minutes of kissing later, I direct his hand up to my breast and moan into his mouth as he takes the hint and starts cupping and rubbing me. And finally, it’s Louis’ turn to moan into my mouth when I take the plunge and shakily move my hand in between his legs.
I probably shouldn’t have been surprised that when my hand lands on Louis’ jeans I find him already fully hard. I don’t know if it’s his normal position, fate, or just dumb luck but he’s grown down his left pant leg making it perfect for my right hand to grip and start rubbing him up and down. I’d felt Louis hard in his pants before, both as I sat on his lap and with casual touches but I’d never really gauged his size other than knowing he was much larger than me. But after my practice with Marley and the practice with the Louis dildo, I realize Sarah and I may have misestimated Louis’ size. As my hand slowly rubs up and down his full length, I mentally compare and see that Louis is only an inch or so shorter than Marley. And if possible… thicker.
From the way Louis is grinding up against my hand, holding my head to his, and kissing me so passionately and aggressively, I can tell that he’s really into this and probably won’t last too long. That makes it even more surprising when I feel his hand grip my wrist and forcefully pull me away from his pants. I pull away from his kiss with a questioning look as I can clearly see the passion in his eyes, even in the dark theater, but his answer throws me for a loop. “This isn’t right Sadie.”
Before I can say that I want to do this he instead pulls me in to continue kissing me, to continue playing with my nipples and making me wiggle and moan even more. My mind races for a bit until I realize what he means. While I think it would be hot to have a woman, especially a woman as sexy as I am now, rub me off through my pants in a theater, Louis has been with a lot of girls. He probably expects more and is telling me it isn’t right to tease him. That he doesn’t want to cum in his pants and doesn’t want the blue balls from me rubbing on him and NOT cumming in his pants.
Gathering up my previous resolve and digging deep for all that I have, I pull away from the kiss. Both of us are still breathing hard and it makes my words come out sounding breathy and, to be honest, quite sexy. “Baby, let me take care of you.”
As I move back into our kissing, I move my hand back into Louis’ lap. But this time instead of targeting his cock, I move to his belt. It takes Louis a moment to catch on to what I’m doing and by the time I have his belt undone and am pulling down his zipper he tries to go for my wrist again. This time I don’t let his gentlemanly politeness get in the way. I can be just as accommodating as his previous girlfriends and am going to do this!
After actively slapping his hand away, I work my hand into Louis’ pants, being sure not to scrape my nails across his sensitive skin. Just like with Marley I’m doubly occupied as I continue to make out with Louis while I carefully snake him out of his boxers and jeans. I’m grateful that Marley emphasized working on this part as it isn’t as straightforward as I thought it would be. Because of the practice though, I’m able to get him out of his pants without any scrape or pain. Following the combined lessons from Marley and my devotionals I break away from our kissing but keep my eyes on Louis’ as I bring my hand up and start licking at it. I make sure to make the appropriate appreciative moans until my hand is slick and I reach back down to wrap my fingers around him.
Louis’ eyes are almost popping out of their sockets and I wonder if he thought I hadn’t ever done this before. I mean, technically I hadn’t, but I’d never tried to push a narrative that I was virginal either. I could only hope that I was doing it right and comparing well to his other girls. I was so into my own internal comparison and reviewing of my lessons that it only struck me as I started slowly stroking him up and down that I’d passed the part that I thought would be difficult. Licking my hand after handling his cock. In retrospect there wasn’t much flavor to it. Maybe a slightly muskier flavor than that of my own skin but that also may just be my mind seeking that out.
At this point I don’t dare look down at my hand and instead do as both Marley and my devotionals taught me. I continue making out with Louis. As expected, Louis’ excitement is translated into his own actions. His kissing is more passionate and his playing with my breasts is more fervent, much to my delight. I’m also thankful that he’s remaining the gentleman and not attempting more than I’m offering. Louis is making no move to encourage me to change this hand job to a blow job, nor is he moving his hand to my skirt.
Louis continues to kiss me and make out with me more and more heatedly until I feel his impressively thick member start to twitch and throb in my seemingly tiny hand. At the same time, he starts groaning in a frighteningly similar way to Sarah’s virtual Louis in the devotional. Just as his hips jerk upward, I’m pulled out of my comparison and realize this isn’t practice. It’s really happening. My other hand barely makes it down to Louis’ cock in time to catch his shots of hot sticky cum.
Our faces remain close together as Louis’ whole-body jerks in orgasm, coating the palm of my hand over and over with his seed. Between catching Marley’s cum and all the devotional orgasms I’d caught I’m actually left without surprise and instead can enjoy watching the **** pleasure play out over Louis’ face. Even after his body stops jerking, his cock continues to leak out cum, spreading it over my still gripping hand. Finally, when he seems finished, he relaxes back into the seat and smiles at me.
I feel a swell of pride. I knew if I could get past my own nervousness, that if I could do this, I’d enjoy making Louis feel this pleasure. But this pleasure is ten times better than what I’d imagined.
Just as the devotionals taught, I bring my hand up to my mouth, flatten my tongue, and take a big lick. As my tongue starts licking Louis’ freshly deposited cum from my hand, my eyes catch the pile of napkins on his lap and I suddenly remember that this isn’t the sweet donut cream… I’m actually licking real cum from my fingers. Louis’ real cum.
What's next for Sadie and Louis dating?
Gamer Gurl: Part II
Get Gudder
Now that Nick has transformed himself into Sadie, the female streamer that goes online by Princess BabyDoll, he needs to start earning money. He needs to pay back Sarah for everything, as well as earn money for next semester. In the meantime, Louis, a fellow streamer, continues to befriend Sadie and Marley continues to work out with her and help her be as feminine as she can be. Sarah has let Sadie chart her own course, but she's still making sure Sadie's mind is as feminine as her body is physically.
Updated on Jul 30, 2025
by caitlynmasked
Created on Jul 20, 2024
by caitlynmasked
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