Roommates Bet

Note from author: Wow, such a great response after a lukewarm one from chapter 1. Your voices were heard so I decided to add another chapter to the story. I hope you like it as much as chapter 2 (that is a very high bar).

I was now officially Ryan's maid. The next day I ordered some panties from Victoria's Secret online, I wasn't sure of the size but I wanted to start dressing sexy for my man. Even though he technically wasn't

my

man, we never talked about that kind of stuff. In his eyes, I was his maid, his slut, and no longer a man. In my eyes, he was my world, my everything, my man. I had them shipped overnight and I couldn't wait to put them on. I started with only 3 pairs as they were on the more expensive side and I wasn't sure how they would fit. If you never put on silk panties it's an experience you'll never forget. The soft silky feeling gliding up your legs and over your dick and ass. WOW! I could totally understand why women liked wearing silk panties, it gives you a thrill. When you move around in them you can feel the fabric on your body, delicious. I was looking forward to the day when Ryan discovers them on me.

True to his word, Ryan was extremely demanding. He would expect a lot out of me now that I worked for him. I, of course, had my regular job as well. I worked as an accountant at a big corporation so that job was demanding too. Between doing my day job and coming home to do my 2nd job I was exhausted. Plus Ryan was giving me lists of chores to do well beyond what I was doing previously.

There's no denying I wanted this, I enjoyed the whole experience but I started to wonder since he was going to hire someone, was I going to get paid to be his maid? It was a lot of extra work and Ryan was ready to post a job ad online but I wasn't sure I wanted to ask him, afterall, he was the boss. Even if I did get the courage to ask Ryan, I wasn't sure what the rate was for maids but anything would help me save for that car I wanted.

Much to my surprise, when Ryan got home from work he said out of the blue,

"As far as compensation goes for being my maid, I was looking up what the going rate, it's about $750 per week. But since we have known each other a long time I will give you a better deal. I will only expect $500 a week from you."

"Huh? I don't understand. You want me to pay you to be your maid?" I was very confused.

"Don't you think it's a privilege to serve me? I gave you a significant break too, I think you should thank me."

I was stunned and aroused at the same time. I was hired to be Ryan's maid and I would be paying my boss for the privilege to serve him? It was such a crazy concept but my twisted mind found some masochistic sexual stimulation from it. The maid paying the boss to clean up after them, I didn't know things could get more humiliating but there it was. And the whole time my dick remained hard, it was the ultimate slap in the face yet I relished it.

"Thank you. I'll set up autopay so it goes right into your account. Would every Monday work for you sir?" I quietly asked.

Ryan smiles, like an evil superhero, he knew he owned me. "Yes, Mondays work perfectly.".

"Oh, Another thing, since you will be working for me as a maid, I think you should address me as your master. Right?"

"Yes master." I answered without hesitation. I knew he was my master but hearing the words made it more real.

After all my work was done and Ryan was fed I went to report to him.

"You have another thing on your list." Ryan said as he grasped his crotch.

My tongue involuntarily licked my lips, I was hungry for his cock. After that first time I was hooked. I went to him and started to kneel.

"WAIT! The proper way is to ask my permission to give you a blowjob. I guess you will need lots of training."

"Yes master. Can I please give you a blowjob so you can cum?"

"Good girl, that's better. You will learn quickly or your ass will have permanent marks. Yes, you may proceed."

I ran my hands up his thighs, he had powerful and muscular legs, I loved touching them and rubbing them. But my ultimate prize was his cock, when I got to it I felt that same electricity bolt as the other day. My dick was poking out from under my skirt exposing my panties, I wanted to touch and stroke my own dick but I knew better. Even though Ryan never told me that I couldn't touch it I knew I needed permission without even being told I did. Ryan was my owner and a good servant always checks with the boss. That was another example of the control Ryan had over me now. I don't think there was anything he couldn't command me that I wouldn't do.

As much as I couldn't wait to suck on his cock again, I savored it as I pulled his monster out of his sweats. I gave it small kisses all the way up the under-shaft. I followed the kisses up with long, slow, wet, licks along that same under-shaft. I knew he had a weakness for that area ball sack so I took my finger and gently ran it across that very soft and sensitive area. Ryan was moaning, I was loving watching my man respond to something I am doing. It gives me extreme pleasure knowing I am the reason he is enjoying this. It drives me to do an even better job because I want to be the one that gives me what he needs.

Only after a few minutes of teasing him, Ryan starts getting aggressive. He grabs my head with his strong hands and starts to skull fuck me. He is a man who knows what he wants and far be it for me not to comply. He deserves to cum how he likes it, I am only there as his pleasure mechanism.

I can feel him about to cum, I am bracing for that unique feeling of warm cum shooting into the back of your throat. There's no feeling like it, you know it's cumming but are still surprised when it does, plus its hot semen with a creamy texture and salty taste that is also memorable. But instead of cumming in my mouth, Ryan pulls me off of his dick and lets the cum spray all over my face. He is marking his territory, he wants there to be no mistake who is in charge and that I'm there to service his needs. As the cum sprayed me, the warmth of the cum, the tickling of the drops rolling down to my chin was another erogenous zone that I never knew existed. The humiliation coupled with the need to please him was pushing me over the edge. I knew if anything just bumped my dick I would explode. But I waited for permission, I knew my place and it was to serve, my wants and desires were secondary to Ryan's.

Once Ryan came off his high from ejaculating, he pushed me back but in doing so his leg brushed my dick to send it over the edge. I started squirting cum on his sweats which prompted a quick and harsh response from Ryan.

"What the fuck dude, clean this up now!."

I get up to grab a towel and Ryan barks, "With your tongue bitch."

I lap up my cum from his pant leg, it wasn't the same as tasting Ryan's cum. This was stale and the fact it was mixed into the fabric of the sweats took away from the taste as well. I looked up at Ryan when I was done licking it up, he looked pissed.

"Listen bitch, you are not allowed to cum without my permission. Seeing you can't even do that right I will be locking up that thing between your legs from now on. Understand?"

Just when I thought I couldn't fall any deeper into depravity and control by this man he now is going to lock up my dick. I was scared, I liked cumming but I was also turned on that my dick get instantly hard again just moments after cumming. Ryan would now control everything about me, my dick was my last shred of independence left and it was soon to be taken away from me.

"Yes master, understood." I softly replied.

"Can I be excused sir?" I asked.

"Yes, you are dismissed. Don't forget to lay out my clothes for work and make me lunch before I leave." Ryan ordered.

I headed to my room, I wanted to jack off before he got that chastity device. I wasn't sure what to focus on when I started to stroke my dick. At first I thought of the idea that I would be paying him to work as his maid. That got my dick hard in just seconds. I followed that up with an image of his gorgeous cock, a man's cock for sure. It had a big head, the helmet was like a mushroom hanging over the shaft. So lickable, so delicious looking, it belonged in magazines. Plus there were the veins popping throughout, just like his real muscles his cock was fit and muscular. God I was so lucky.

I was stroking faster now when the thought of wearing a chastity cage for Ryan popped into my head. He would certainly hold the keys and decide when and if I was allowed to cum. That was it, I shot my load up in the air over 12 inches...came down on my chest and chin like rain from the sky. I don't have nearly as much cum as Ryan but this was one of my more explosive loads than I normally have. I knew I didn't have permission but my dick had a mind of his own.

A couple days later when I arrived home Ryan was already there. He called me over to the couch where he was watching TV.

"Put this on." He said without glancing away from the TV while he handed me a box.

"Yes master." I said as I grabbed the box knowing exactly what it was.

I headed to my bathroom to open the box and put on my new chastity cage. It was all medal and had a natural bend or curve to it to keep your dick from extending fully to erection. Just holding the device sent chills up my spine and a small, but noticeable, tingle was felt in my groin.

I read the directions and assembled the device over my dick. It was snug but my dick could still move a little in there. I changed into my panties and maid uniform. I knew I should be ordering more uniforms but I needed to check with my new master. He would be the one making the decisions from now on.

I was anxious to show Ryan the chastity cage, even though I knew I looked like the biggest wimp. I wanted him to notice my silk panties so I headed back out of my bathroom to model my new device for my master.

"How does it look?" As I lifted up my skirt so he could see the chastity device covered by my panites.

"Come closer, I want to inspect it."

I gladly moved within an arm's reach of Ryan hoping he would fondle me. I was like a schoolgirl around him, he was the big football hero and I was the helpless girl begging for him to take notice.

"The panties are a nice touch, we should discuss expanding your wardrobe to include some other sexy outfits. Give me your credit card so I can go shopping for the right clothes for you." He demanded.

I went to fetch my credit card and handed it over to Master Ryan. I couldn't wait to find out what he would buy for me, even though it was with my money it felt like he was buying me a present. And what girl doesn't like presents from her man.

"Oh, hand over those keys, you are not allowed to cum without my permission anymore."

I submissively bowed my head and handed him my keys, actually,

his

keys. It was then that I felt my stomach drop. There was no turning back because now he controlled my orgasms. That was the ultimate control in my opinion, the person who controls the other person's orgasms was in charge, no doubt about it. I loved the idea in concept but wasn't sure I would like the idea in reality, but it was too late now, he had the keys and I was at his mercy.

I laid in bed horny as shit, I found myself involuntarily touching my dick only to realize right away that it was impossible to get hard. It didn't take long before I was sexually frustrated, I wanted to cum. I replayed the events, I needed to cum so bad. I tried really hard to get this out of my mind but I couldn't. I needed to ask Ryan for the keys, there's no way I could make it through the night.

"Ryan? Are you still awake?" I quietly asked as I knocked on his bedroom door.

I waited for a minute before I heard him ask me what I wanted.

"Sir, I was hoping you could let me out of my cage tonight? I need to get used to this slowly and I don't think I can sleep like this."

Ryan whipped opened the door. He was wearing only his underwear, the bulge in them was eye popping, I could make out the entire dick including the head and veins. It was a piece of art and I stared at it for a minute. As I broke my stare and allowed my eyes to gaze upon the rest of his body I let out a moan. He looked so good standing there like a Greek god. His abs looked perfect, his chest was to die for and those shoulders and arms were right out of a Muscle Fitness magazine. This was a man's man, 100% real man who demanded respect and attention.

"What the fuck do you want?"

After taking in Ryan's physique, I was at a loss of why I was there in the first place. I couldn't think straight as I stood there in silence trying to gather my thoughts.

"You sluts are all the same, you can't take your eyes off of me. I could make you do whatever I want, couldn't I?" He asked.

It was rhetorical but I answered anyway, "Yes sir."

As he started to close his door it hit me as to why I knocked in the first place, it was to get the keys.

"Sir....sir?"

Ryan stopped halfway with his hand still on the back of the door getting ready to shut it in my face.

I mustered up the courage, "Sir, can I have my keys? I really need some relief, I don't think I can make it through the night." I begged, sounding as pathetic as could be.

He paused, looked me up and down and said, "NO". And slammed the door shut in my face.

This whole scene was driving me crazy, I felt my dick trying to get hard but with no luck. I could feel my head spinning and my breathing get shallow. I was smitten by this man, and he could give 2 shits about me. I tried not to focus on the latter, it was my job to prove to him of my worth, not the other way around. I needed to do a better job at keeping my man happy.

I was back in my room with my dick smashed into this cage but trying its best to be released. He held all the power, there was no more "bet" to blame any of this on. I was submissive to Ryan and that is an undeniable fact. The more submissive I became the more Ryan could care less about me and my needs. Why should he? He was the master and I was his slave, albeit, we never used the term "slave" before but there was no other word that could accurately describe our relationship. But it drove me crazy, the more I did for him the more he was indifferent towards me. That neglect was like a powerful magnet drawing me closer to him, driving me harder to serve him, yet, the more I served the more the gap grew between us. This vicious circle was both frustrating and exhilarating at the same time. To make matters worse, my dick was locked up and all I wanted to do is get that release. Which of course drove me to even more excitement and arousal because I wasn't allowed it.

To say my sleep was restless would be an understatement, I tossed and turned all night. I questioned my decision all night to agree to lock up my dick. I tried to reason with myself that I didn't have a choice but I could have told him no. But I knew if I did that my exciting ride as Ryan's maid would surely be over. Even though it was a very short time I was already addicted to him. More specifically, I was addicted to serving him and being his sissy maid.

By the morning I was on edge, it had only been less than 24hrs and I was already going crazy. I was so horny and when a guy is horny, yes even a guy that's acting more like a girl, will do almost anything. This is when we are the most vulnerable, when we are in this state of arousal. This is exactly how strippers are able to milk so much money out of men. They work them, the men watch them on stage, the women snuggle up close to them to continue to tease them, and then when the guy can't take it any longer they escort you into the "backroom" for a lap dance where you run up a tab in the thousands. That formula works, it's been proven across the country at every strip club known to man. Now I was in that state of arousal, willing to do anything for release. Ryan must have been aware of this as he refused to let me out of my cage last night.

My routine was established, I was to make breakfast for Ryan, make him lunch to take to work and before I left for work I needed to straighten up the place in case he beat me home later. At work I could swear people could tell I had a chastity cage on, I felt like they were staring at me but in reality no one could tell. I was paranoid on top of being horny all the time. I even started staring at some of the cute guys in the office instead of the girls. Always being horny was like being on ecstasy all the time, your inhibitions are lower, your arousal is on fire and all you can think about is having sex. But being locked up meant that Ryan was the only one who could give me relief. I needed to step up to make sure Ryan is always satisfied, his personal needs and sexual needs. It was my job now that Ryan was always happy. Maybe if he's in a good mood he will unlock me so I can cum.

Back at home I was afraid to ask Ryan to unlock me, I didn't want him to get angry with me and never unlock me. On the other hand, if I don't ask he may not think about it and then I'm stuck locked. I was working on my chores when Ryan arrived at home.

"Hey, you remember Jimmy and Brad from school?" Ryan asked me.

"Sure, what are they up to?"

"I ran into them after work, they want to come by this weekend to watch the game and catch up."

"Oh, wow, I would love to see them and hang out."

Jimmy and Brad were part of our group of friends in college. We met freshman year and were inseparable ever since, but it had been about a year since we last saw them. I'm sure we would be going out to the bars reminiscing about the "old' times. I envision a late night call of duty war as well.

"I expect you to be on your best behavior when

my

friends are here. You must serve them as you do me, understand?" Ryan said.

I hadn't thought about my current arrangement with Ryan, I was reliving my college days and couldn't wait to see my old friends. Yet, I felt the tingle, it was running from my groin to my head, it was what I felt right before I got a hard on. But this time, there will be no hard on because I was locked up by Ryan. The tingling intensified as I thought about my friends seeing me dressed like this. The thought that I would be serving them while they were here. What would they think? Would they see me differently? Would they treat me like Ryan does? Mmmmm....the thought of my friends turning into Ryan got me more aroused, not physically obviously but internally. Brad was also cocky so he would likely assume the dominant role naturally, like Ryan did. Brad wasn't as muscular as Ryan but he had a swimmer's body, lean, muscular and athletic...mmmm....he had a nice body I thought. Wait...I'm now lusting after Brad??? Fuck. But I couldn't deny the tingle, the arousal, the lust that was felt inside. I was becoming a slut, I wanted to please men. I wanted, no needed, a dominant male in my life telling me what to do. Being bossed around by Ryan and Brad was almost enough to get me to cum.

Of course Jimmy was handsome too, he was a mulatto (half black / half wife), and it looked like he got the best of both races. He was a ladies man, girls fawned over him, he was the best looking in our group. He had confidence with the ladies, but didn't come off as cocky. I think he knew he had his pick of girls anywhere he went. I thought about how handsome he was, he really was someone you could see on a magazine cover. He was a sexy man...crap, what the fuck??? I now was admitting that Jimmy was handsome, this wasn't some submissive fantasy, this was plain out gay behavior and thoughts. I was finding another man attractive. You may not understand the difference, in the case of Ryan, I was attracted to his dominance and muscles, but there wasn't an attraction to his looks. But with Jimmy, I was dreaming about how good looking he was. This feeling was something I would think of when imaging women but now I was thinking of Jimmy. The butterflies were flying in my stomach thinking of Jimmy. I never thought of it before but I had a crush on Jimmy. Like a schoolgirl, I felt myself blush just thinking about him. Fuck, he was gorgeous of a man.