A Freshman's Summer Class Ch. 06

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The freshman goes deeper into the rabbit hole.
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Part 6 of the 9 part series

Updated 06/10/2023
Created 04/24/2020
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**All characters are of legal age for adult content.**

Trying to get these out faster, and writing more, but sometimes life just doesn't play along. Please enjoy, will probably wrap up around Chapter 9 before our hero heads back to school with all that new training!

Chapter 6

The next few weeks went by pretty quickly. Nothing much changing in my life further, thank goodness. I needed a break mentally. The chastity cage stayed on for 2 weeks straight, and it was extremely hard for me to deal with all the sexual encounters between Ms. Kelly and Mark.

They must have sensed that I needed a break, as we did not hang out after work much over those few weeks. I thought maybe they were unhappy with me, but I knew better. I was doing everything they asked of me, and giving such pleasure to both of them.

On the few nights we did meet up at Ms. Kelly's, it was more of the same training for me. I would go down on Ms. Kelly and lick her to completion. She would direct me and tell me what to do. She incorporated her asshole into my oral attention lessons more and more. I was fine with this, as Ms. Kelly had a beautiful pussy and asshole, and I was in love when I was between her thighs.

She made Mark watch most nights, without touching himself. She would have me look over at him in his lingerie, at Marcie, and Marcie's throbbing cock bouncing around as his body thrusted at the air. Ms. Kelly would tell me how I was doing that do him. I was turning him on so much, and the anticipation of the pleasure I would grant him had him bulging for release.

I would look over at that lovely cock of my best friend, then dive back in for more of Ms. Kelly's sweetness. I was drunk on sex, lost to thoughts of release and my own explosion of pleasure and cum.

There was no release for me though, my cock staid caged up. I would get hard less and less though, my penis knowing that the cage only brought restriction and pain, so it was learning to stay soft while caged. I didn't have much time to think about it more than that, as there was a woman, a real goddess, for me to please right in front of me.

It was after those 2 weeks or so ended that things started changing again. Ms. Kelly had told me to tell my parents I would be gone for the weekend with Mark again...just like most weekends. Obviously she had some plans for this weekend, as she demanded it, not a request.

So Friday after work we headed over to Ms. Kelly's. She was warm and inviting when we arrived, and she gave us both a shot of whiskey and a beer chaser. She started early, as I could smell the alcohol on her breath. God, what a woman!

We caught up and laughed for a bit before Ms. Kelly got down to business, so to speak. She said, "My good gurls, this weekend is going to be very busy...but fun. I promise! Tonight we are just us, but tomorrow afternoon I have a few friends coming over, so I want you both to dress up and serve my guests and me all evening. Can you do that for me? For your Mistress?"

We both nodded quickly, excited to make her happy, to please her. Having more women around to please was also a very attractive proposition. I found myself drooling slightly at the thought of eating more pussy. Ms. Kelly certainly noticed, and smiled at me while running her hand along the side of my face.

"Ok ladies, go get cleaned up and dressed, so we can get to work tonight," She instructed. "Wait, hold on Marcie. Here's Allie's key, go ahead and release her so you can get all cleaned up. No funny business though, I mean it!" she emphasized that last line with an all business stare.

Mark and I both went to what was now called 'my room' upstairs. We quickly undressed and threw our work clothes and dirty panties and bras in the hamper. Mark unlocked my chastity cage and released my pee pee. Oddly enough, after over two weeks in chastity, I did not get hard.

Entering the bathroom together, we helped each other prepare our boi pussies by doing our routine enemas with each other. Over the last two weeks, Mark had worked with me on doing these things together to save time and make it easier. This was nothing new to me at this point.

We cleaned up that mess while getting the tub started with hot water. As the tub filled, we applied hair removal cream to each others bodies. We both spent too much time on the genitals, but it felt stupendous to be rubbed there without the cage on. I got hard momentarily from his handling, but the smell of the hair removal cream made any sexual excitement leave quickly.

After the directed amount of time, and good amount of burning feeling on our skin, we got into the tub together and washed one another down. Using the only soaps and body washes available, we smelled wonderfully fruity at the end. We both looked completely hairless and smooth, just like we know our Mistress wanted us. My excitement level started rising quickly thinking about getting back in to my lingerie set.

Marcie told me to just put on my panties and some knee high socks. We would be wearing silk nightgowns, he called them. So he passed me the pink chemise - naturally it was pink - and I slipped it over my head and shoulders. It was as light as air, slipping down my body smoothly and effortlessly.

I looked in the mirror at my reflection and was impressed by my sexiness. I looked just like a young lady with my long hair now going slightly past my shoulders. "Marcie, you think maybe you can help with my hair tonight?" I asked my best friend.

He smiled and nodded, taking my hand and sitting me down at the makeup desk. Grabbing a brush he smoothed out my wild tangles and set a baseline for my hair when left alone. From there he took some scissors and made a few minor cuts to add some layering affect. I don't know where he learned this, but it worked. He pulled a few strand bundles back from my temples and bobby clipped them discretely to my head. I couldn't believe how cute I looked!

Marcie said then, "We have to do our makeup tomorrow, we will look so cute together. We will drive those guests crazy, I promise, Alli!"

Who was I to argue, after what Marcie was able to do with just 5 minutes, scissors, and 2 bobby pins?

Downstairs we went then, and Ms. Kelly's eyes exploded with lust when she saw us...when she saw me with my girly hair. Her smile went ear to ear, and her eyes looked extremely hungry. The huntress was back, and I was just a little gazelle under her gaze. Gosh this woman had such an affect on me...

She squealed then at us, "O.M.G. you look so cute, my gurls! Alli, I love your hair, its so pretty and easy looking. Well done!" Clearly Ms. Kelly was drinking a bit more while us gurls were upstairs getting ready.

I explained to her that it was Marcie's doing that made my hair look so good. She said something about making sure I thank her properly later, accentuated with a wink.

We got fresh drinks and made our way to the living room to talk and drink, drink some more, talk some more. After about an hour of giggles and light touches to thighs, we were all feeling it then, and ready to move this to the bedroom.

As we made our way upstairs, I finally remembered that Marcie didn't put my chastity cage back on. I don't know how I hadn't noticed until now? I hadn't gotten hard at all during the last few hours, something had to be up with me. Must be the alcohol.

Ms. Kelly embraced us both, making out with one of us, then the other, then pushing our faces together so we could make out too. She smiled and leered at us while our tongues explored one another mouths. Mark was pushing me down to the bed then, laying on top of me as I willingly submitted to his physical directions. Our mouths only leaving one another momentarily.

Ms. Kelly began to disrobe herself, sitting down at the edge of the bed next to us. Her hands immediately started playing with her breasts and vagina. She absolutely got off on watching too gurly bois making out with one another. I could then feel my dick harden, finally, and push against Marcie's. Our shafts rubbing against one another with our panty fabric between them.

"Now, now, Alli, you know you're not allowed to get release like that here! You're pee pee needs to go back in its cage it would seem. Marcie, be a good gurl and go get Ms. Kelly an ice pack out of the freezer," she instructed then.

With my panty buddy gone, Ms. Kelly then told me what was next, "We are going to use a different cage for this weekend my dear. I can't have you getting hard tomorrow and shooting your cum cums off prematurely when you just see a vagina!" Her giggles and laughter really brought me to heel. The humiliation trickled in with how aroused I was, was truly breaking down my mental barriers. This woman had complete control of me, and I was ok with that more and more with every session.

When Marcie got back then with the ice pack, he was instructed to place it on my pee pee. To shrink it back down for my new cage. Ms. Kelly produced a smaller metal cage this time, and I was gripped with a little fear.

Ms. Kelly noticed my fear then, and started to describe the device to me. She said, "This one is metal this time, sweetie, so I'm sure it looks scarier. I'm sorry for that, but don't you worry your pretty little head, be a good boi for me, and everything will be alright." She switched back to calling me a boi, but she said it in that way that always made me more docile, more agreeable.

I simply nodded my head to her. She continued, "Look, this one even has what's called a urethral sound! Its exciting, right?"

Not exactly confident that this was an exciting prospect, as it was clearly a small tube that was going to be inserted into my pee pee, I just stared blankly.

With the cold pack having done its job, and the added bonus of my fear making my erection all but disappear, Ms. Kelly moved over to me then and started installing my new cage. This device was certainly different than the last, it was all one piece, with a swivel for the shaft portion that allowed it to move out of the way as Ms. Kelly slipped my balls, one at a time, through the device ring.

She grabbed the lube then and started applying it to the catheter portion of the cage. I was worried at this point, as I had no idea what to expect. She soothingly stroked my hair and head, telling me how it was all for the best, and it would be alright. She had Marcie distract me some with his cock, as she then started pushing the tube into my pee slit, swiveling the cage down over my shaft at the same time.

With the help of the lube, it went in relatively quickly. There was pain, certainly. It was sharp and quick, making me jump a bit. But they were both holding me down so I just stirred around on the bed as Ms. Kelly locked my pee pee away in its new prison. I looked down at myself when she moved away, and could only see a small metal nub sticking out above my balls, with the flesh of my pee pee head pushing through the metal bars of the device. It had an integral locking cylinder, so it was all very compact.

I would have started panicking then, but Ms. Kelly was quick to direct me to roll over on to my stomach, and get on all fours. I complied as usual at this point, making sure my Mistress was happy with me. She stroked my back down to my plugged anus a few times, making me feel very girly. To my surprise, she then gently removed my butt plug.

"Its time for this toy to get changed out too, my dear. This is far to small for you after wearing it for so long now! Let's get you upgraded, yes?" she inquired.

I didn't answer, as it wasn't my choice. My Mistress owned my body and could do as she saw fit.

Producing the lube bottle one more time, and now a larger butt plug with a big pink jewel at the hilt, she glided it into place with little trouble or resistance from me. I was so used to having something up there at this point, I'm pretty sure my boi pussy didn't close anymore.

"Good gurl, you look so cute and beautiful all locked up! I absolutely love this new you tonight. Now let's get to thanking Marcie for making your hair so pretty, yes?" Ms. Kelly stated.

After shaking our heads in the affirmative, I was instructed to lay back down on my back, and Marcie was to sit on my chest, facing me, and lay back on top of me. It was a weird position to be in, for sure. Right beneath my chin was Marcie's pretty boi pussy and above it her balls then cock.

The pressure and weight of Marcie making me grind a little against her, reminding me of both my new penis infiltrator tube, and the larger plug in my boi pussy. I was a bit conflicted with the pain, but the pleasure was also there, certainly. And being this close to my best friends smooth cock had me drooling again.

Ms. Kelly then began to stroke Marcie's cock, just with her thumb and pointer finger. I was instructed to start orally pleasing to thank Marcie for helping look pretty and cute. So my tongue found its way to the smooth ball sack in front of my face. I loved the smell of my best friend, and due to our recent shower, it was enhanced with girly soaps and perfume.

Marcie started grinding toward my face after a few minutes, so her balls would slip up to my nose, and my mouth would get pushed between her ass cheeks. Ms. Kelly tapped my head and told me to keep licking, no one told me to stop. I should be thanking Marcie, remember?

So with an eyeful of ballsack, and a mouth full of ass, my tongue then got to tasting and exploring Marcie's boi pussy. The flavor was familiar, as it was not my first time performing a rim job. Sure, it had always been Ms. Kelly's beautiful pucker, but Marcie was pretty too, and smooth, and cute, and clean. It was a momentary pause, if that, while I considered my actions. Truly imperceptible, as I was quick to accept my role in this perverse dance of ours.

I must have been doing a splendid job, as Marcie started bucking, and Ms. Kelly quickly pushed his cock down and toward my face. Marcie slid down my body from the force of Ms. Kelly's hands, and her cock went right into my waiting mouth as it exploded with a torrent of creamy white goodness into my awaiting maw. The normal three squirts of cum hit my tongue and I immediately swallowed the bounty. A surprise fourth and then fifth weaker squirts also went off then, to my great joy.

I savored the extra cream given to me by my best friend and rolled it around on my tongue. Ms. Kelly was kissing me deeply before I knew it, stealing as much of the cum as she could. Immediately, she moved to Marcie's mouth and spit as much into her as possible.

Ms. Kelly was ravenous then, as she manhandled Marcie off of me, and in a flash was straddling my face. She was completely drenched from our debase acts, and I knew what she wanted. I spent the next fifteen minutes or so cleaning her up and pleasuring her orally as best as I could. She had a body shuttering orgasm and fell off my face then.

I was contempt with pleasing my two partners, it felt so good that I completely forgot about the larger plug stretching my ass and the tiny cage constricting my pee pee.

We all fell asleep together then, one big happy mess of bodies, arms, and legs. Content with our actions, with our pleasure.

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3 Comments
liz33ndliz33ndover 3 years ago

what a erotic chapter, thanks and keep giving us more, we (I) crave more of this transformation.

AnonymousAnonymousover 3 years ago
very hot

I so want to be alli

AnonymousAnonymousalmost 4 years ago
Pick me

Omg this story is so hot I wet my sissy panties , Lacie 😘

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