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Chapter 40 by caitlynmasked caitlynmasked

What's next for Sadie?

Things calm down for Sadie

I spend most of Sunday talking with Sarah. I go into far more descriptive detail about Saturday including my feelings as I made out repeatedly with Louis. I share my concerns about him finding my secret and my concerns about how physical he’d want us to become if we start dating. I can tell that Sarah has stronger opinions, but like a psych major she turns the thinking back on me. She blows past being nervous about how physical we’d be and moves right to how physical we WILL be.

I’m a little blown away as she lays out options like she’s setting up a sex menu for me and Louis. Per Sarah, Louis getting more physical can include him disrobing my top and playing more aggressively with my breasts. That would include his hands, his mouth, and even his cock. And yes, she forbid me calling his cock a penis. She said if I trusted him, he could also go into my panties, but only from the rear. With my clip on he could then finger my ass like Marley did in Las Vegas.

Then there’s the physical options I can do. There’s kissing and playing with his nipples, but Sarah says that most guys want to move past that fairly quickly and move on to something more overt. There’s basically one part of him that I get to touch and or use. His cock. I can give him a hand job, with or without his pants or underwear on. I can give him a tit job. I can give him a blow job.

Before I can consider if I’d even want to do any of these things with Louis, Sarah drops the next bomb to my psyche by saying that I should probably practice all of these acts with Marley before trying them on Louis.

In the meantime, I agree with Sarah that I need to talk to Louis about it. The story we both think will work is to say that I’m a virgin and was brought up conservative enough to want to remain so for as long as possible. Not only will that vibe with my early nervousness on camera and awkward dating, it will help me when we proceed to more intimate forms of affection.

After having dinner and setting up more social media posts for tomorrow, I get surprised by a call from Louis. I remember trying to stay strictly to the three day rule. Don’t call the girl until three days after a date. But Louis’ manliness doesn’t seem to be diminished whatsoever by his breaking that rule and calling me earlier. We chat happily for an hour or so and then continue via face time for another couple hours.

When we finally part ways I clean up and get ready for bed. Just as I lay down and pull the covers up I feel my watch buzz on my wrist. A devotional. It takes me a moment to set the scene up as the devotional directs, but soon enough I find myself kneeling next to the bed with the phone mounted on my night stand looking at me from the side. Resting on the comforter is the ‘Louis’ dildo, wetted and lubricated by my own spit.

I let out a low groan when the directions appear on the screen. I consider briefly backing out as I doubt Sarah would be upset enough to call the whole thing off for this, but eventually I relent and start.

First thing I have to do is spit between my own breasts then rub that around. Frankly it feels disgusting, but I know it’s only going to feel worse from here. Next, I arch my back which I admit presents my breasts beautifully, and then lean forward trapping the dildo between them.

Evidently the phone needs to be at my side to see if I’m actually putting the dildo between my breasts and posing as the devotional directs. As I’m to keep my eyes either on the ‘cock between your tits’ or ‘up toward your lover’ I have no video to watch while I perform my tit job. I’m not sure if not having a video is a good thing or not. Having videos to watch help me imagine being in the moment they portray. But not having it doesn’t give me an imagined moment to live in. Instead, I’m left to my own devices. And any thought I had that Sarah wasn’t targeting this devotional went out the window when I heard Louis’ voice start coming from the speaker. Hearing him tell me how good I’m making him feel, how beautiful I am, how sexy I look ‘down there’, just makes my imagined moment become more real. I’m not in some AI generated world, instead I’m being directed to imagine I’m giving this tit job to Louis.

The five devotionals vary my techniques which mainly means how I use my mouth as my hands remain pressing my breasts around the dildo. Sometimes I’m kissing the cock on each pass, sometimes I’m taking time to suckle on the head, and sometimes I’m licking and kissing and ending with the suckle as ‘Louis’ screams out and ‘cums’ in my mouth.

When I’m told that my nightly devotionals are complete and bid to sleep well, I put the dildo away and go into the bathroom to clean up. While there’s only a bit of spittle on my breasts to wash off, I still spend a lot of time cleaning my face again. The devotionals are just too realistic, and I feel like Louis has cum on my face or between my breasts many times tonight. I even brush my teeth again to remove the imagined cum taste away.

The next morning I don’t have time to catch Sarah before I’m getting ready for Marley’s and my first real workout session in weeks. Marley thankfully thinks of everything and knows I might be nervous after what happened in Vegas and our discussion at the coffee shop. He assures me that workout sessions are to be spent on working out. Yes, they’ll continue to be sensual, but they will not cross into sexual activities. Only when I say that I’m ready to move on to that step will he set up a time and place where we can work on it.

Feeling relieved, I dive into the workout. As I expected, I get much more out of the stretches and exercises with Marley there to push me both physically and mentally. Feeling his hands or other body parts on me is initially off putting, but I quickly grow re-accustomed to it and by the end am back to enjoying it and becoming aroused by it.

For a while, my days become good and I almost consider them routine. I stream. I chat with Louis and start planning our next date. I chat with Sarah. I stream. I work out with Marley. I have affirmational devotionals, sexy devotionals, and sex with Sarah. The sex with Sarah comes in two flavors and I start thinking of them as ‘my’ sex and ‘her’ sex. My sex involves her taking me anally from behind, filling the room with every sensation she can to make me feel like Louis is there making love to me. Her sex involves her riding my face and teasing at my cage. The only frustrating thing is that once Sarah realizes I can orgasm from ‘my’ sex, she varies her routine to prevent that final culmination. We still have sex for hours, but she’ll slow her pace as she feels me getting close and sometimes overtly stop. Only once did I manage to have an orgasm and she pulled out completely as I started, leaving me to dry hump the bed as I dribbled out cum from my caged penis.

Everything seems to culminate the week of Thanksgiving. I finally get up the nerve that Sunday afternoon to call and talk with Dad and Dallas. I’m on the brink of having a nervous breakdown, fearing that they’re going to grill me on why I haven’t called and talked before. But all my nerves are for naught as they simply accept that I’ve been busy and are just happy to talk with me. They both say they appreciate the texts and emails that I send. They’re a little disappointed that I’m ‘feeling sick’ and can’t come home for Thanksgiving but say they understand and wish me a good time here.

I’d suspected Sarah has been tapping my phone for all messaging and voice calls but it’s confirmed when she comes in as soon as I hang up and just gives me a hug. After she holds me for a long, wonderful time she kisses my cheek and says that I won’t need a devotional that night.

Monday morning after working out with Marley I finally tell him that Louis and I are having our second date on the day after Thanksgiving, and I’d like to work on ‘sexual activities’ with him before that. We talk a bit about what Sarah said about the options and Marley suggests we work on hand jobs. “That will show him that you’re interested in his pleasure which is normally the female mindset. It’s a real aphrodisiac to men.”

We set up a time on Wednesday night and I even put out social media posts letting my fans know I won’t be streaming then. Marley suggests we use a hotel room for what he calls our ‘workshop’ as it won’t be familiar to me but won’t feel like I’m in his domain either.

My streams continue to go fine and my audience numbers continue to climb, especially when I peppered in some of the self-bondage. It was a little too on the nose when I bound my legs and arms to the chair for Tuesday’s night Obey/Command Me! date night stream. I didn’t even know this was a possible scenario but in the game my demon roomies tie me to a computer chair and take terms forcing my avatar to give them blow jobs. When I see what’s starting to happen I barely have time to stretch and get to the keyboard to put the content filter up, blurring the sexy bits and letting my audience instead focus on me.

My audience, being the group of naughty boys that they are, were sure to capture the video of me lunging forward in my chair. With my mouth open in surprise. They cropped it well and looped it so that they could upload it as a animated gif looking like I was giving head while tied up in a chair just like my avatar had done in the game. They loved it, I was embarrassed as all hell, and I earned a shit ton of money.

Wednesday morning came and I guess I shouldn’t have worried about being nervous with Marley as he admitted he was nervous too. He reiterated both before and after our workout that I would be in complete control and that this wasn’t a situation where no meant yes. No would always mean no and stop would always mean stop. Seeing as he was making so much effort to keep me comfortable, I took the opportunity to move up to my tip toes and give him a kiss on the cheek, thanking him. We both broke up in laughter when I told him “Now get out of here. I’ll get my hands on you later tonight!”

After cleaning up, making some social media posts, and having a quick vlogging stream about my hair style, I get ready for lab. I’d love to skip today and avoid Todd all together, but the lab was promised to be quick and just a practical quiz. Do the work, turn it in, and leave. I had studied the material and had a good plan on what I’d do so hopefully I’d get out before the majority of the other students, not letting Todd keep me late again. After last week with his discovery of my breasts and me not returning as he ordered, I have no desire to see what he wants to do.

As much as I want to avoid Todd, I decide to hope for the best and prepare for the worst. I pick out clothes specifically that will give Todd access to my breasts without having to remove my top. A tight tank that he’ll be able to pull down instead of up and an athletic bra that will be easily removed. While the temporary tattoo is faded and close to gone, it’s still visible and would surely just upset him all over. I consider wearing my clip instead of my cage so that he won’t see my bulge under my panties should he go exploring further, but I realize I’d prefer him to see me as male down there. In no way do I want him to try and ‘explore’ with me as a female under my skirt.

The bus ride to campus is quick and I file into the lab with everybody else. Todd seems busy and rushes through our quiz. Unfortunately, the practical he lays out isn’t the one I prepared for and I have to pull out my book to remind myself how to do it. When I figure out what I need to do I get the equipment and materials I need and get to work. All the while I see students working faster and even finishing up and leaving. I fail the experiment a couple times and have to repeat until I can get the correct result.

When I see that I’ll be one of the last students to leave I pull out my phone and text Sarah, asking her for a ride home. The bus won’t be here for another hour and that might give Todd enough time to come find me even if I get out early. I sigh in relief when Sarah quickly replies and says she’ll be here to get me in a few minutes. She even says she’ll wait for me right outside the chem building.

When it’s down to me and three other students I notice Todd eyeing me more and more and know he’s trying to make sure I stay late with him again. He even goes over and starts helping the other students so that they get out before me. When I get the correct result, I rush through cleaning up and closing out my station. Todd directly glares at me as I drop off my paper on his desk, but he can’t say anything as there are still two other students present. Instead of telling me to stay he puts up another roadblock by locking the doors. If I want to leave the normal way, I’ll have to have him open the door.

With a wink and a flick of my hair I wave at Todd and head to the storeroom we used the other week, remembering there was a secondary exit there. I don’t hear Todd get angry or anything but as I’m skipping down the stairs toward the exit my phone buzzes and I see a text from Todd. “Get Back Here NOW!”

A part of me says that I should stay. Todd has the power here. But I’ve been pushed and pushed and pushed and just need to get out and not experience this for a week. I still have all of December to get used by this lech, but I need this week off.

When I get outside, I look around for Sarah’s anime printed pink Mustang that stands out like a sore thumb in the crowd of Hondas, Toyotas, and Kias that most other students drive. When I don’t see it in the pickup area I slow down and start looking through the parking lot. As it’s near the end of the day for classes the parking lot isn’t exactly full and I’m able to discern that she isn’t here. Pulling my phone out again I see that she texted me at the same time that Todd did. “Sry, stuck in a stream. Can you take the bus?”

I start to type out a reply, letting her know how important it is to get me when I feel the hand on my shoulder and hear Todd’s tense voice behind me. “There you are!”

What does Todd do with Sadie this time?

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