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Chapter 37 by caitlynmasked caitlynmasked

How does Sadie's conversation with Marley go?

Sadie has an emotional conversation with Marley

I’ve been open and honest with Sarah about almost everything since she invited me to stay in her home and help me out financially. Of course, I knew everything that’s going on, though I’ll admit I’ve kept parts of it in the background of my own consciousness. The doctors know some, Marci knows a bit, and… and that’s about it. And since Sarah has been by my side, it means I haven’t laid out everything, from being a regular guy college student game streamer to becoming an oversexed, hypersexualized feminine college student game streamer, to anybody. And as I lay out my entire story to Marley, I hear myself saying things that sound outright scandalous.

“That’s why we hired you, to make me as feminine as possible in body and mannerisms.”

“I was overwhelmed and didn’t pay attention. It’s my fault that I’ll never have body hair again.”

“We’re thinking that the hormone dose is off, but we need a medical professional’s opinion and that’s just one doctor who isn’t available until January.”

“Well, no, we didn’t intend for me to have D cup breasts, but they’ve grown way more than we thought and with the fat grafting on top of it… well, you’ve felt them.”

“The way she laid it out was basically redirecting my sexual energies back into myself, keeping me more constantly aroused without a relief valve. It comes out as flirty femme energy on my streams. That’s why I wear the chastity devices.”

“No, they’re called devotionals, and they’re meant to keep my sexual energies directed in the feminine way. I’m supposed to be a horny flirty girl on camera and not a horny flirty guy. Yeah, I guess that’s why I got so comfortable flirting with you so quickly.”

All in all, it was a lot to say and a lot to lay out. Even as I was telling the story of ‘my’ life over the past few months, I was finding it harder and harder to believe. I’m a little surprised Marley sat through it with only the few questions he had. Where I had answers for all of his previous questions though, his last one pushed me back in my seat and made me think, even though it was just another casual question. “Okay Sadie, so when this is over and you have the money you need, you’re going to return to being… it was Nick, right?”

My thoughts raced in my head as much as my heart did in my chest. I’ve been so focused on moving forward, on getting to the next step and the next financial milestone, that I hadn’t thought about that. The answer feels like it should be obvious. Yes, I’m going to return to being Nick. I’m playing a part and that’s all this is. It feels like it should be that obvious. But retelling everything made me relive it in a way. The first time I presented myself as female. Accepting Sarah locking my genitals away from myself. Having the doctor see me as a transgender woman. Showing myself off to an audience as a girl. Flirting with a virtual audience of thousands. Flirting with Louis in person. Being kissed by a guy. Kissing a guy back. Devotional after devotional making me think of myself as a sexy girl. And even though it’s not a happy memory, it’s part of the journey… jacking Marley off and having him cum all over my lips. ‘Nick’ may have done some of that, but the ‘Nick’ I knew wouldn’t do all of it. Certainly not without a gun to his head, and while the financial reality was bad it wasn’t THAT bad.

I realize I’ve been watching my fingernails tear apart the poor sugar packet for awhile now and have left Marley’s question hanging in the air for far too long. And even though that hesitation is probably answer enough, I need to answer it TO myself. I look back up at Marley and smirk, “I don’t know Marley. When this all started, it was an easy yes. Yes, I was just playing a part to get some cash and catch back up to where I was financially. But… but now I’ve lived this. I’ve experienced things I never thought I could experience and… and I don’t hate them. I like some of them. I… I love some of them.”

I look away and take a deep breath. I knew this wouldn’t be an easy conversation, but this is way harder than I thought it would be. When I feel Marley’s hands take mine and squeeze it warmly, I don’t do anything to stop him. But when he starts to say something, I shake my head and cut him off. I don’t know if I’ll have this strength in a few minutes and it’s important to get this part out. “Marley, I know I’ve been talking non-stop for almost an hour but let me get this last piece out and then we can have a conversation and not a lecture.”

When I turn back to look at Marley, I see him lean back in his chair patiently. When I showed up here a part of me still wasn’t sure if he wanted to **** himself on me or not. Whether he enjoyed my discomfort in Vegas or not. But the more I see him allowing me the space I need, the more I believe what he’s been saying all along. That he’s sorry. That he didn’t mean it to go down like that.

“One of the big things in my mind, big lines that I’d never cross, was sex with a man. Underneath this hairless skin, behind the tits and my locked away dick, under this pink hair and all this pretty makeup, I always thought of myself as a straight regular guy. It was like a prank making guys believe I was a sexy girl. It was an act. I dreamed of having sex with Sarah, not Louis. Not you. Certainly not random guys in my audience. The exercise routines with you, especially the lessons on being more girly, were a way to make me more comfortable thinking of myself like that to my audience. Thinking of myself as a sexy girl makes it easier to play a sexy girl on TV, ya know?”

I shake my head a bit, my eyes unfocusing on the present and imagining each of these scenes as I talk about them. “But things changed. That date I told you about with Louis, he treated me like any other girl, and I didn’t think I could stop him so I was kissed. A lot. The devotionals of women with men, with big black men, all made me feel like the girl in the scene. Having you touch me all over in way more intimate ways than I expected. Flirting with you and having you reflect that back on me. Going out with Louis again. That video shoot where you touched me in more overtly sexual ways, and then watching it with you by my side as we actually made it sexier.”

I return to the present as I come to that one most singular changing moment. The moment that I’m still processing weeks after it happened. Looking into Marley’s eyes I say, “And then there was Las Vegas. I know I looked like a sexy woman. I pushed that to its limit to help you. I acted like it to help you. And while I know I can’t drink like I used to, I did that too. I can’t say with any certainty if I knew it when we walked into my room after yours was flooded, but I knew that we shouldn’t be close to each other like that in private. Even if I knew what that tattoo meant to you, even if I wasn’t three sheets to the wind, I was playing a sexy woman who has been flirting heavily with you for weeks and you were on top of the world after losing your long-term girlfriend with a girl you admitted you were attracted to.”

I feel my chest growing tight as the images flash before my eyes. I don’t take my eyes away from Marley but seeing him sitting respectfully back from me while holding my hand is broken up with images of him in the hotel room. Looking down at his cock. Feeling it against my lips. Hearing his smooth bass voice tell me he was feeling good and that I was making him feel that way. Feeling his huge maleness in my hands and feeling it throb and shake like a firehose. But I still push on. “Look, I never imagined myself as a girl, but step by step it just became easier and easier to present that way until I can’t present as a man now if I wanted to. Being with a man is like that. I never imagined being with a man, but step by step it just became easier and easier. But there’s no sneaking up and suddenly being okay with handling a man’s… a peni… a dic… with handling your cock.”

My view of Marley starts to blur as I know I’m starting to tear up. When I feel his hands squeeze mine again, I know he’s about to talk and I push through it and make myself get to the end of what I wanted, needed, to say. “Look, I never in a million years would have wanted to do that. But now that it’s done, I can say that it… I liked parts of it. I liked how it made me feel. How you made me feel. I don’t think I’m… I… I don’t know how to even quantify what this means or how I feel. I’m a guy who is more girl than guy. I’m attracted to women, so does that make me a lesbian? But I can’t lie and say I’m not getting sexual pleasure from men. Even from what we did together.”

I suddenly pull my hand from Marley’s and pick up my phone. After turning the recording off I set the phone down with more **** than I intended and look back up to Marley. “Look, we don’t… I don’t need that anymore. I can see that I can trust you. But I hope you can see how confusing this is for me. To get to the end of what I wanted to say, what I wanted to tell you, is that as long as I’m going to still be Sadie for several weeks, several weeks at least, I’d be doing a disservice to myself if I didn’t explore both sides of this. I’m going to explore the more emotional sides with Louis as that feels more natural and I have a stronger barrier to keep up with him. But, if you’re interested, and willing to help me through what I’m obviously struggling to get through… I’d like to explore physical sex with you.”

I wipe away the few tears that escaped my eyes with the palm of my hands. After taking a look around, imagining a horrified barista standing behind me, and seeing that the coast is clear, I turn back to Marley and **** a half real, half fake, smile onto my face. “So… does that sound crazy?”

Marley breaks down and laughs, which completely feels like it resets our conversation. It takes all the suspense and tenseness off my shoulders, and I join him in laughing. When he can stop laughing Marley gathers up both of my hands and kisses them. “Sadie, I’d love to help you explore your sexuality. And to be honest, I kind of thought that’s what you wanted to talk about and was afraid that you were going to be more emotionally attached to me. I say afraid because I don’t want to have a romantic relationship right now. I don’t think I’d be a good boyfriend right now, but I still find you sexy as all get out. And now knowing this side of you, hearing how you persevered and pushed through something so amazing… well I think that’s the strongest thing I’ve ever heard someone do.”

With that dam finally broke, Marley and I chat for another couple hours. I hear about our relationship, from working out to flirting to feminizing exercises to the video and video editing to finally the time in Vegas, from his perspective and realize just how mean it all was. By not telling him that I had no interest in physically being with a man, I was leading him on. He’d been attracted to me at the onset and that attraction only grew more intense as our routines grew more hands on. It culminated when he broke up with his girlfriend and had me help him with the Vegas presentation. He honestly was looking at me as a ‘rebound girl’.

If I’d had just told him from the get-go that I wasn’t interested in being with a man, he would have never gone that far. And now, because of my error in judgement, he feels awful about what happened. I can certainly appreciate his feelings even as I tell him that he’s not to blame. Lord knows that in these modern times, I’ve worried about going too far with a girl on less than ideal or clear consent. I’ve worried about the times that in the heat of the moment I may have come on too strong and crossed into that sexual harassment, sexual ****, and maybe even **** area. And now I’ve put Marley into that very same scenario.

We both overtly apologize several times. Me for not being open with him, him for taking my silence as consent. In the end, Marley agrees to help me. We start by first agreeing to picking up the exercise and feminizing lessons. I really do need the workouts as I feel I’ve lost some flexibility without the constant pushing that only Marley can provide. We also lay out a basic rule, that no sexual act will occur without spoken and direct consent. If I can’t provide that consent, whether it’s an emotional or mental or physical block, Marley will stop, and we’ll talk about it. No more assumptions, no matter how interested I appear to him.

We also agree that while neither of us are looking for an emotional, romantic, relationship, we have to be open to one happening. We’re starting with me exploring that side of myself with another man and with Marley already being attracted to me. We agree that if either of us start feeling that way, that we’ll open up and share it with the other person to prevent any more hurt feelings.

And finally, while there’s nothing being done at the moment, I agree to help Marley out with his gym. He’s already signed paperwork with Mr. Bellamy and they’re targeting soft opening a gym by early spring.

Getting through that emotional wall feels like I’ve just physically had to bore my way through a wall and I’m exhausted. Marley offers to drive me home, but I politely decline saying I need to get myself in the right mindset first and a bus ride will give me some alone time to process this since I’ll have to get online and be ‘Princess BabyDoll’ as soon as I get home. Thankfully Marley accepts my reason, and we part ways with a kiss that fits firmly between chaste and passionate.

How does Sadie's day with Louis go?

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