This is a story about a guy slowly becoming a servant to his crush, her friends, and boyfriend. Hope you enjoy!
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How the hell did I get myself in this position? It started with an innocent crush on a girl, back when I still had self respect. Now I was serving her and all of her friends. I was completely naked except for a small pink chastity cage that prevented me from getting erections. I finished pouring the wine and placed the glasses on the tray and lifted them up. I took a deep breath and looked down at my naked body. This was what I signed up for, to be a servant to Cassandra and her friends. It all started with a small favor.
I stepped through the kitchen door…
I started working at this prestigious steak house where a bunch of other twenty somethings also worked. We all earned more money than we should have and everyone else was so young and hungry they’d blow it all on partying. Parties that I never got any invites to.
Cassandra was my trainer. She was gorgeous. Wasian with luscious black hair, pert breasts that filled out her uniform and a toned butt that I stared at as she gave me the tour.
“This is the dish tray. When it's full we push it to the other side. Could you lift that please?”
“Of course.” I passed the dish tray to the dishwashers. Cassandra squeezed my bicep and said, “Strong boy!”
I laughed too hard. That was all it took. I was smitten with Cassandra from then on. After that, every time I had a shift with her I made sure I was helping her with her load of the work. The compliments flowed for a while but eventually she started to expect it of me. How could she not? I always assured her I was happy to do it.
At one point, the manager asked her to wipe the bread plates. She looked at me and with the sweetest smile said, “Get started on the dishes, please. I have to use the ladies room.”
It wasn’t an ask. It was a gentle command. That was maybe the first time I started to feel like I was under her spell. I jumped at the chance to make her happy and just said, “Yeah, no problem.”
She thanked me and left for about twenty minutes. I finally finished the dishes and went to go look for her. I couldn’t find her in the whole kitchen and saw that a different person was leaving the single bathroom. I finally went outside where people took their smoke break and saw her making out with another server named Leo. He had his hand on her plump ass and his tongue down her throat. I stood there for a while waiting for them to notice me. When they made out for far too long, I quickly cleared my throat. Cassandra finally turned around.
“Dishes done?”
I nodded my head. She turned to Leo and told him that fun was over and she had to get back to work. Leo said he was off anyway. He spanked her as she walked away. I followed behind her as she went and told the manager the dishes were done. He inspected them and told her that was the best job she’d done yet. “We aim to please!” She said. I kept waiting for her to say that I did all the work, but she never did. She also didn’t technically lie either. SHe just said the dishes were done but didn’t claim she did them. I guess I couldn’t be too mad at her. Besides, it got me some brownie points with her.
She turned to me and waited for me to say something. She was probably wondering why I didn’t speak up for myself. Or why I wasn't yelling at her for taking credit. Then after a moment of waiting she finally said, “You really like to be helpful, huh?”
“Uh,” I said, “Yes! I love it, Cassandra! Thank you for the opportunity to help!”
Then I walked away. I thanked her. For doing the task she was assigned and letting her take credit for it. I felt like such an idiot. I thought I had made myself look like a pathetic loser, but later that night as I walked to my car, I saw Cassandra arguing on the phone, presumably with Leo.
“You’re not. You’re already drunk?! You were supposed to pick me up, asshole!”
She yelled at him as I looked at her from my car. I waved at her goodbye. She then said on the phone, “Wait, nevermind. I think I have a solution.”
Cassandra then called out to me! “Hey! Arthur! Can I talk to you for a second?”
“Hey, Cassandra!” I said, “Wh-what’s up?”
“Ugh, my jerk of a boyfriend got drunk and he was supposed to pick me up. Is there any chance you can give me a ride?”
“Sure, Cassandra! Anything to be helpful!”
“Thank you so much! You’re the best. Way better than my stinkin’ boyfriend.” Then Cassandra reached out and hugged me. I smelled her floral perfume and felt her breasts touch my chest. I hugged her back and she pulled away, “Which one’s your car?”
I drove as she gave directions. When I pulled into the right neighborhood, she pointed and said, “it’s that one with the lights on.”:
It was a very quiet neighborhood outside of what looked to be a very busy house. I drove up to it and club music was blasting from it. There looked to be several cars parked outside as well as people I knew from work going inside.
“Uhm, this is your house?” I asked.
“No, silly!” She said, “It’s Morgan’s house. She’s throwing a party and Leo is already there. Isn’t he the worst?” I pulled up next to it. She gave me a smile. Was she about to invite me in? Was this my opportunity to get into a party thrown by the cool kids?
“Thank you soooo much,” Cassandra said as she gave me a hug and opened the car door, “You don’t have to worry about picking me up. I’ll just drive Leo’ car back home, or crash on Morgan’s couch. You’re the best! See you at work!”
Then closed the door and walked into the party, leaving me behind without so much as an invite.
The next morning everyone was talking about the amazing party they all went to. I mostly kept to myself, trying not to show how hurt I was. Cassandra walked in looking hagard. She had an iced coffee in one hand and sunglasses in the other. Morgan, the one who threw the party, pointed at her and said, “Biiiitch! How the hell are you showing your face after last night?”
“Ugh, girl, I don’t know. I’m not sure how I’m still alive.”
I was between both of them as they talked. I figured this was my in so I chuckled and said, “What happened last night?” Morgan glanced between me and Cassandra and said, “She got so drunk she took-”
Cassandra made an ‘x’ with her arms and just said, “Stop! Ugh, Stop! Artie’s a good boy. He doesn’t need to know what a naughty girl I was last night. You have too much respect for me, right?” Morgan giggled and waited for me to respond. Cassandra and Morgan were both staring at me. My mouth watered at Morgan finishing her sentence. Did she take her boobs out? Did she get naked and everyone saw but me? Cassandra was this sweet little angel but I desperately wanted to know what she was like when she cut loose.
“I mean…” I started. I looked at her pouty face as she stared at me expectantly.
“Wow,” Cassandra said, “I guess I could tell you. I just thought you cared about me beyond looks.”
“I-I do!” I said, “I promise I don’t want to hear about what happened last night.”
Morgan let out a giggle and Cassandra reached out and patted my cheek, “Good boy.”
I blushed and squeezed my legs together. Her touch was causing me a warmth in my groin and I looked down.
Morgan said, “My tables just got sat. Remember what we talked about, girly!”
“Oh right!” Cassandra said, then looking at me, “I brought you up yesterday.”
I blushed even richer red, “You-you what?”
“Yeah! Some of the girls wanted to get together and thought that a little dinner party just the girls would be so fun. Doesn’t that sound great?”
“Y-yeah! That sounds amazing!” I said. Was she really about to invite me to a dinner party? With just the girls? I’ll be honest, I didn't do well in a direct competition with other men so this might be my most ideal environment.
“Great!” Cassandra said bubbly, “because we thought it’d be sooo cool if we hired a little server that day, and since you love to help, I suggested you! Isn’t that so fun?”
My face dropped. I felt a pang of humiliation. I was being invited to the party, just not as a guest. As a servant. I shuffled my feet but I was unable to meet Cassandra’s intense gaze. Then out of my mouth came the words that changed everything:
“Sure. I’d love to.”
To Be Continued…
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