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Chapter 55
by
caitlynmasked
How does Sadie get ready for 'her date'?
Sarah takes Sadie to the mall to prep for 'her date'
I had a feeling that I’d be overdressed when meeting Marley at the bar. Sarah went all out for my makeover and while I’d dressed sexy plenty of times in the past, this might be the first time I’d dressed up with class. Sarah’s and my first stop in the mall was the nail salon. We sat side by side while the girls gave us mani pedis. When I saw the nametag of the girl working on my nails I smiled inwardly, recognizing Song Kelly Rim’s name… she was the daughter of the owner.
Both my fingernails and toenails ended up gleaming in their pink color that matched my hair perfectly. Next up was visiting Marci for a new hairstyle. Not only did she touch up my coloring, she trimmed some of my hair off and straightened the natural curls I get. Looking in the mirror I was shocked at what a difference it made as my hair now cascaded down from my head in straight waves.
Marci wasn’t done though as she took me over to the cosmetics area and applied my makeup. I’d gotten quite good and fast with my makeup application, but I’d never put as much effort into it as March was. When she was finally done and I got a good look at myself I realized I’ve never looked this good before. Once I was done gaping at my reflection Marci put some of the cosmetics into my purse so that I could ‘touch up as needed’.
Our next stop was at the fashion store Gilded Grace Boutique. While we browsed the aisles, I couldn’t help but balking at the prices. These weren’t your normal mall knockoffs, these were real dresses and accessories by Yves Saint Laurent, Versace, and Gucci, just to mention a few. Sarah had me try on a couple dresses that looked fabulous. When I voiced my concern about the price, Sarah just smiled and told me that the more feminine I feel, the better this ‘date’ will go, and nothing brings out femininity than dressing up to the nines.
Admittedly it cost a small fortune, but the little black dress, the rose gold choker, the large hoop earrings, the shiny black peekaboo heels, and even the bangle that hangs from my bellybutton ring all came together beautifully. On our way out Sarah insisted on one last stop. Fredericks of Hollywood. I thought about mentioning that I had drawers and drawers full of lingerie, but didn’t as I knew Sarah had her mind set on this. When we walked out of Fredericks an hour later, I had an amazingly new sexy pushup bra with matching lacy strappy panties, and smooth silky pantyhose, All in pink, of course.
I was quite nervous by the time we got home, but Sarah was there to help me get ready for ‘my date’. And just as she predicted, putting on all this feminine finery really did make me feel more like a woman than I have before. My reflection in the full-length mirror didn’t just whisper cute cam girl, it screamed sexy woman.
Sarah offered to drive me to the hotel bar, but I insisted on borrowing her Mustang to drive myself.
When I finally got to the bar and didn’t see Marley, I took a seat and ordered a negroni sour. Before the drink arrived, I felt someone’s hand at the small of my back, caressing up my spine. It’s more than a little disconcerting that I recognize Marley’s intimate touch. It’s one thing to have him touch me sensually while we workout but this is different. This isn’t mimicking sensuality, it’s sensual. Turning and standing up from the bar stool I take a long look at Marley. He was wearing nice slacks, a pressed white shirt with the top few buttons undone, a pair of expensive looking shoes, and a long cashmere coat and scarf. I’ve always looked at Marley as sexy and confident, but these clothes amp that feeling up to 13.
It was just after two in the morning when I pulled into the driveway and parked Sarah’s Mustang. After pulling the parking brake, shutting the lights off, and turning the car off I sat there quietly for several moments. Even in the dimness of the driveway I could see my hands on the steering wheel, the pink nails standing out against my pale flawless skin and the leather wheel. I’ve looked at these hands for months now. They’ve been my hands long enough that trying to picture my normal blotchy, hangnail having, badly trimmed nails feels foreign. But in this moment, remembering what I’ve witnessed these hands just did… they feel like someone else’s hands. Someone sexier than me.
When I feel that I’m able to hold it together I get out of the car and stride into the house, my heels clicking confidently on the concrete. Considering our history together it really shouldn’t have been a surprise that Sarah was sitting on the couch in the living room, all the lights out, waiting for me. But there she was, waiting until I had the door locked and was starting to walk toward my room to snap the lights on and scare the living shit out of me.
“Damn it SARAH! You almost gave me a heart attack!” I find that my hand has found its way up to my throat where I can feel my heart beating as hard as I’ve ever felt it.
“Oh please. Like I was going to wait a few hours to hear about your date and lesson in the morning! Please girl!” Sarah of course seems to take no interest in nearly killing me with fright as she pats the seat cushion next to her. I can even see that she has two bottles of water and a bowl of the skinny popcorn we often share.
I close my eyes, let out a long breath, wait for my heart to regulate itself, and finally set my purse down and sit next to Sarah knowing that there’s no value in arguing. She’s not going to let up until I share. It’s not mean, it’s just her nature.
I try to get ahead of Sarah and give her the quick bullet points, hoping that they can at least hold her off until the morning where I can give her the full story. “Okay, it was… interesting. We met at the bar and shared a couple drinks. He took us up to the room and we sat on the couch where he taught me how to give a hand job through pants. I nodded along, then put what he taught into practice. Once he said I was doing it good enough we stopped, and he taught me how to transition to… um… you know… bare handed technique on the edge of the bed. I pulled him out of his pants and gave him a real hand job. He stopped me a few times to give me some pointers and we ended with him cumming.”
I took a bite of popcorn followed by a long swig of water, feeling my mouth going dry as I tried to push through the memory of tonight. Before Sarah could take advantage, I pushed forward. “Afterward he gave me some more pointers and we made out some more. Before he got too hard, we parted ways, and I drove home. Easy Peasy. Now if you don’t mind, I’m tired and want to…”
It was worth trying to get out of giving Sarah every single detail even if I knew it had a small percentage chance of working. Sarah let me know that it wouldn’t be enough by interrupting me before I could say that I wanted to go to bed. “Whoa whoa whoa, there’s no way you’re getting out of this with just that!”
At that point Sarah gripped my chin and turned me to face her. Sarah’s entire demeanor helped calm me down. This wasn’t some serious interrogation that was meant to embarrass me. This was a friend honestly being curious. With her head tilted to the side, her eyebrows raised almost all the way to her hair line, and her eyes wide she looked like an anime character making me relax and giggle.
“Okay okay. What do you want to know?” I asked while taking another swig of water and moving the popcorn bowl between us on the couch.
Sarah curled her legs under herself, grabbed a pillow to clutch, smiled broadly, and said excitedly “Start with the date part. How did he look? What did you have to drink? What did you talk about? Did other people notice you two? Was the bartender cute? What was he wearing?”
I giggled again, relaxing further with Sarah’s genuine interest. “Okay, fine. Yes, the bartender was cute. His name was Brad, and he was really talented. I just had time to order my Negroni before Marley got there. He was… well, he dressed up real nice. Better than he did in Vegas. He even had this new cologne on that, I mean, wow, it smelled REALLY nice. And you know Marley, he could see that I was nervous and just made everything seem normal. The way he talked, the way he ordered drinks, the way he chatted with Brad, the way he drank, the way he gave me room to talk, it all served to make it feel just… normal. We were two people out having fun. A couple out on the town. I saw that other people noticed us, but not in a bad way. They weren’t like ‘Look at those people, they shouldn’t be here!’ or something like that. The look I saw in their eyes was more like ‘Aw, look at the cute couple up at the bar!’.”
“We might have been there for about thirty minutes or so. I had two Negronis and Marley had three beers. I was going to order another, but Marley said we should slow down and keep **** from being a factor. That was honestly the first time since he got there that I remembered what we were doing. That we were there for a lesson on sex and not just there to have a date. He was that good at relaxing me. Anyway, we finished up, Marley paid the tab with a hefty tip, and we went up to the room. I was kind of surprised as I figured Marley would get just a normal room. You know, a bed, a bathroom, a TV, and that’s about it. But he splurged for a full suite. We had a living room, a little desk and dining area, a bathroom with a jacuzzi, and a complete separate bedroom.”
At this point I was lost in memory. I could see that Sarah was just as drawn in, but the vision of Marley walking me in the room and putting the ‘do not disturb’ hanger on the door was more vivid to me at that moment than Sarah munching on popcorn right in front of me was. “I figured we’d just jump right in either side by side on the couch or on the edge of the bed, but Marley sat us down in the living room. He sat me in the chair while he sat away from me on the couch. Like, he was making sure to give me the space I didn’t even know I needed. He went over what we were going to do, reminding me that at any point I could pause what we were doing or even stop what we were doing for the night. That this was entirely for my benefit and not his enjoyment. He… he really calmed me down when I didn’t even know I was getting tense again. Once he knew I was on board, he then laid out his plan. We’d start in the living room area, and I’d get used to playing with him through his pants. We wouldn’t… you know… finish as he really didn’t want to mess up his pants and he didn’t want to have to start over from the beginning if and when we were ready to… you know… move on to the bare hands.”
I pause and let the grin play out over my lips, remembering how Marley not only let me lead us, he made me take charge. Sure, he was talking and teaching me and letting me know what to do and what he was feeling and what would be good and what would be bad, but instead of telling me to sit next to him he asked if I’d like to start. Instead of putting my hand on his pants, on his crotch, he said he was ready for me and made no move to touch or **** me. He was beyond gentlemanly. He gave me no reason to fear him whatsoever. It was almost the exact opposite feeling I had when in Vegas when I felt completely out of control.
“Look, maybe someday I’ll give you all the step-by-step gory details, but for now suffice it to say that he let me be comfortable with touching him through his pants. With feeling him get hard and respond to my touch. He reminded me that any man getting that attention was going to want to respond, either with trying to move forward faster by unzipping himself or at least by starting to make out. He even coached me on how to control a guy without being a bitch about it. It.. it really made me feel strong. Feel in control. And I knew he wasn’t acting, that doing what I was doing, rubbing him through his pants, tickling and gripping his girth and length, made him feel good. And yeah, I controlled how fast and how forward we went. Sure, he or any man that I’d be doing that to could push and try to **** me to do more, but I could also simply stop and get up and move away. Marley even emphasized that at one point when I was really into it, reminding me that it would never be okay for a man to try and push me further or faster than I wanted to go and that if they were insistent that getting up and leaving was perfectly fine.” I let my voice dip down in a bad imitation of Marley’s deep bass, “A guy that doesn’t understand that is an asshole and doesn't deserve this type of attention from an angel like you.”
I’d thought I was going to that hotel room to learn how to give a hand job. To learn how to give pleasure to a man with my hand. Instead, I left learning how to be a strong woman. How to please a man, but not let a man **** me into more than I wanted to give. And that’s not something I thought I’d have to be taught in a million years.
I only realized I’d stopped talking when I felt Sarah lean over and wrap her arms around me. Her hug is the exact encouragement I needed. There was no joking or chiding or trying to make me blush. No teasing or provoking. Just a good friend letting me know through physical contact that she supports me. And as much as I loved Marley for the gentle way he taught me tonight, taught me to be strong and independent and sexy and me, I think I loved Sarah just as much for being a friend and letting me know that I was strong and independent and sexy and me.
How much detail does Sadie give about the rest of her lesson?
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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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