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Chapter 9
by caitlynmasked
What do Sarah and Sadie talk about?
Sarah explains her past and how it affects Sadie's future.
When we got back to Sarah’s place… to home… Sarah walked in at her normal confident pace while I had to take my small unconfident steps. As soon as I closed the door Sarah called out from the kitchen “Leave the shoes on. You’ll need practice in raised heels. Those are the most comfortable shoes you’ll have for it.”
That didn’t exactly bode well as my feet were already aching from being arched and feeling like I was walking on my toes all day. Regardless, I followed her advice and met her at the kitchen table.
When I sat down, I didn’t even have the opportunity to open my mouth, let alone ask a question. Instead, Sarah put her hand up to hold me and started “Look, this isn’t going to be easy for me to say, so let me tell my story without interruption. Just so I can get it out. Then I’ll let you ask any question you like. Okay?”
Okay being a rhetorical question, Sarah began her tale. “When I grew up, I was confused. My parents were traditionalists. They didn’t want to teach me about anything. I mean I never even got ‘the talk’ from either of them, let alone subjects like homosexuality, trans-genderism, or other more fetish like things. When dad left, just as I was entering high school, mom became distant. I was losing myself online and just starting to play games and have people watch me, so you can imagine I found out what I was curious about on the internet.”
I notice she isn’t even making eye contact with me. It’s like she’s lost in her own memories. “I’d noticed I wasn’t interested in men, in boys, so I just thought I was a lesbian. I tried being with a couple girls, but it didn’t feel right.” Imagining Sarah being with another girl made me shift in my seat, my penis starting to grow hard. “It’s when I noticed that all my close friends were boys that it started to click. I didn’t like big burly guys. The football players, basketball players, the weightlifters and the gym rats…. None of them appealed to me. But a cute guy with effeminate features… a boy that looked androgynous at best and sometimes even downright girly? OH wow, that got my motor running!”
“Grahm was my first. He’d come over to study and we’d watch anime together. When we played games, I was always the hulking beast and he was always the healer. The most fun games were when he’d have to play a girl to my guy character. Anyway, when I asked if I could put some lipstick on him, he just agreed. I didn’t stop at the lipstick though and I didn’t ask him if I could go further. Once his lips were cute and kissable, I added a few brushes of blush and some eye shadow.”
Sarah looks up at me for just a second, takes sharp breath in, then looks away and continues. “He didn’t look sexy or anything, but he looked more, I don’t know, more right. We made out for a bit, but we both decided to not pursue anything more. It turns out Grahm was gay and we stayed friends. I even set him up with his boyfriend. Last I knew, they were planning their marriage.”
Sarah gestures around, evidently indicating college life in general. “Here, it was different but kind of the same. In high school all the guys were trying to be those buff manly men. Here, a lot of the guys already accepted that they wouldn’t be that. A lot were experimenting more than I had. I had three boyfriends that let me play with them, each going further. Paxton let me really practice my makeup on him. He dropped out soon thereafter and is now a professional drag queen. We met up a few weeks back and he thanked me for turning him on to that path. He admits though, that he’s found himself to be asexual. He’s not interested in sex with anybody, just living his life as ‘normal’ and going up on stage in all it’s glory as often as he can. Angelo and I went much further. He was my first truly girly boy. I not only played with his makeup, I got him some clothes. He wouldn’t do much to change his body, but he’d wear whatever I wanted and let me make him over each night we made out. I lost my virginity to him… or rather I gave it to him since I had him tied up and was riding him to my own beat. He loved it. I think eventually we’d have made a great couple, but his grades were bad, and college was never going to work out for him. He ended up moving back home and I haven’t heard from him since.”
She looks up at me and takes a moment, biting her lower lip in a way that tells me everything I needed to know. Going through these memories turned her on. It took a lot of effort on my part to not mimic her action as my lip for some reason just felt like it needed to be nibbled on. “And finally, there was Andy. Andy added something to my repetiteur and opened up a whole new side of me. You see, until I met Andy, I just thought I was into effeminate men. But he showed me all kinds of stuff online about submission. Mistresses, and dominatrixes. I learned about safe words and chastity and…” I see Sarah actually squirm “… just all kinds of things. We made a deal. I’d be his mistress. He’d be my girly boy. I learned later that he was kind of topping from the bottom, giving me hints on what he wanted me to **** him to do, but the feminization of him… that was all me.”
Playing with her fingernails, Sarah sat quietly for a long time. I almost asked a question several times, but decided to let her continue when she was ready. She’d already said so much that explained a lot and yet opened so many more questions. Eventually she just picked right up where she left off. “I was still learning my way about being a domme. At times, I was mean just to see how far I could push him. He had a safe word, but while he didn’t use it, he was still being pushed further than he wanted. He was the first one I took to Marci. He hadn’t wanted anybody to know about his femme side, but I’d told Marci. And she did her magic, just like she did for you. I then took him to my stylist, who you’ll be seeing tomorrow. She gave him a mani, a pedi, and made up his face better than I could. I had her use this long lasting makeup so that it would stay on for days. I took the choice from Andy as this was mid-term week. He had to go to class with his new hair and his face made up.”
I see a tear go down Sarah’s cheek. I get up to offer her some comfort, even though it sounds like she did some awful things and deserves to feel bad. She stopped me with another hand up ‘hold’ gesture and went on, without any effort to wipe the tears away. “He was made fun of incessantly. I mean, everybody knew it was him. His reputation around campus was ruined. All because I wanted to have some fun and it turned me on to femme him up. He never did use his safe word. But the next week, all of his stuff was moved out of his room… your room now… and he was just gone. I haven’t heard from him and have no idea how he ended up.”
When she looks up at me I can see an intensity in her gaze that I hadn’t seen before. “Look Sadie, I didn’t go into this thinking that you’d inspire these feelings in me. I honestly just wanted to help you out. Yes, streaming as a girl gets you a LOT more money and it was honestly the only way, you’d develop an audience fast enough to make a financial difference. At least that’s my opinion. But I told myself that I wouldn’t ‘Andy’ you. I’d keep that side of me at arms length. But God Sadie….” I couldn’t help that she was using my new femme name which must be fanning its own flames within her “…this is like the dream come true that I never knew. I guess technically you could break our deal and run. It’s not like I could come after you for financial recuperation… but you KNOW that I can teach you how to earn that money and without me you’d be stuck. You’d either drop out and ruin your future or ask for money and ruin your dad and brother’s future. Either way, doing what I say is your best way forward.”
Sarah swallows hard, still squirming in her seat “So you HAVE to do what I say. It lets me be a domme without having to worry about if you want to be submissive to me or not. And of course…” she gestures at me “…I’m actually REQUIRED by our deal to feminize you. And in the very direction my fantasy goes. Not just turning you into a girl, but into a girly girl. That’s why I kissed you. It’s my fantasy side coming out into our professional side. And I honestly don’t know if I’ll be able to keep those separate.”
She finally lets out a breath like she’d been holding it in that entire time while spreading her hands apart, giving me permission to talk.
It takes me awhile to gather my thoughts. She’s laid a lot out and it’s a lot to process. My dad had always said I was a pragmatist, and that side of me finally wins out. I let out a breath of my own and say “Look, that’s a lot to take in. I imagine it’s going to matter more later and it might… well, no, it probably will bother me more, later. But for now, I don’t see that anything has changed. You’re right, I’m stuck. After the fire, I was adrift in the ocean about to drown, and you were an amazing life preserver that I found. Now that I find I’m tied to the life preserver and that it’s changing me in ways I honestly didn’t want… well, it’s still a life preserver. You’re still saving me. I can’t promise that I won’t end up like Andy and running away, but… that’s not how I was raised. Honestly Sarah, I’ve been attracted to you since I saw your first steam. When I met you in person, when you sat down next to me, my heart went wild. So, hearing that this might become more… I don’t know the word… intimate? Yeah, hearing that this might become more intimate is enticing. Sure, I didn’t imagine being your girly boy, but that kiss was amazing and the thought that I had pink hair, was wearing panties and a bra, and had lips bigger than yours didn’t even enter my head.”
I bring my hands up to gesture at myself “I guess if this is what you like and it’s what I need, then this might work out for both of us.”
Sarah’s smile was infectious. When she stood up, walked around the table, took my hand in hers, and had me stand I honestly had no idea what she intended. But maybe this was just a taste of what our new ‘intimate’ relationship would be. Instead of kissing or hugging or walking me to a private area, she instead sat down. Then, with a grin she directed me to straddle her lap. As my stocking slid along her velvety skirt I felt a shiver go up my spine. It only intensified when she ran her hands up to cup my panty covered rear with one hand. The other hand slowly made its way up my back, played at the back of my neck for a bit, before going higher and gripped both of my ponytails into her hand. Using that as a handle, she brought me down to her lips where she kissed me.
We weren’t kissing as a couple. WE weren’t making out. Every action, every motion of hers, made it clear that she was kissing me. She put me where she wanted and I was her toy to be used. Just when I was growing accustomed to her tongue sliding into my mouth and mauling my own tongue, she withdrew and tilted my head back so that she could start kissing and sucking on my neck. I let out a moan as I remembered being in the same position as Sarah. Having a girl at a party straddle my lap while I sat on some couch. One of my hands cupped and gripped her ass while the other tilted her head back so I could kiss at her throat. And just like it drover her mad, it was driving me mad.
But where my time with the girl at that party led us to a private bedroom and us making love, Sarah did one of her amazing gear changes and pulled us apart. With little effort she got me to get off of her and she stood up next to me. “Good. You’re my girl now. I think you’ll have fun, but that’s not the point and I won’t pretend that it is. Your safe word is Oklahoma. This isn’t a normal domme sub relationship, so I’m not making any commitment to stopping if you say it, but if we’re out in public and you don’t feel right in letting me know you disagree with something, Oklahoma is your way to tell me. As for now, go to your room and think about what’s coming. We still need to finish making you beautiful, teaching you how to maintain your beauty, setting up a schedule for you, and then getting you prepped for your big debut.”
Sarah’s grin is half sexy and half intimidating this time. “Sunday night everybody gets to meet my Princess BabyDoll. And I’m betting she’s going to be sexier than even you can imagine right now!”
When she turned and started heading back to her bedroom Sarah was walking in a provocative manner that I hadn’t seen her use before. Her hips were moving back and forth enough to send her skirt bouncing. She was obviously trying to send mixed signals though when she looked over her shoulder and said in a sing-song voice “Oh, and no cumming for you. Not without my permission. So, no jacking off. I’d better not find sticky or crusty panties on you!”
I’m sure she knew how difficult that would be as my hardon was pushing my skirt up. I’m fairly sure most of my blood was down there as I’d never felt this hard before in my life.
Can Sadie abstain for the night?
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Git Gud
Nick's an up and coming game streamer meets one of his idols
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- sissy, chastity, crossdress, feminzation, crossdressing
Updated on Jul 20, 2024
by caitlynmasked
Created on Nov 13, 2023
by caitlynmasked
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