Roommates Bet

Note from Author:

Thanks to everyone who read and enjoyed chapter 1. If an Alpha / Beta gay story is not something that you like, move on, I won't be offended. There are literally thousands of stories on Literotica which will surely meet your needs. For the rest of you who like reading about a straight man becoming subservient to another man this should be right up your alley. Enoy.

Recap from Chapter 1:

Ryan and Don were best friends through college but their relationship dynamics started to change after a silly bet. Don finds himself slowly succumbing to Ryan's demands and finds he longs for it. Don even starts referring to his best friend as "Sir" and starts to enjoy doing even more tasks for his roommate even when it wasn't part of the original bet. Something has been unlocked deep inside his mind, a submissive side that he never knew was there, especially being subservient to another man.

The next day after work I could feel the vibe had changed, Ryan did too. It didn't take much for him to realize that I was willingly following his orders and that I enjoyed it. Roles had changed, albeit, subtly but there was a shift even though it wasn't talked about.. Without being told anything I immediately went into chore mode, first the kitchen and then I'll work on the bathroom. Ryan was on the couch playing video games and didn't even acknowledge my existence. In a twisted way it made me angry that he didn't even say hi but I knew i had work to do.

When I was finished with my chores I didn't ask for him to inspect my work, instead I started making dinner for the both of us. Logically I was telling myself that I needed to cook myself something anyway so how hard is it to double the ingredients but inside I was doing it because I wanted to. I had a desire to please this man, only a few days prior we were equals but that has changed. We both knew it but kept pretending like this was all part of the bet. When dinner was done I brought out a plate for Ryan who was watching a baseball game on the TV. He didn't say thank you and barely acknowledged me still. But I was happy to serve him his dinner and I went back to the kitchen to eat while I cleaned up the mess I made from cooking.

I noticed Ryan was done with his food so I went to grab his plate and along with mine I put them in the dishwasher. It was time to ask Ryan if he wanted to inspect my work. This was becoming the highlight of my day, I felt the stir in my loins at the mere thought of my friend assuming the role of the "boss" who would inspect my work. No question I was enjoying this man bossing me around. I felt a need for his approval and looked forward to his repercussions if I didn't do a good enough job.

"Ryan, I'm ready for my inspection now." I said

He looked up, gave me a crooked smirk and looked me up and down.

"You are? What happened to addressing me with the proper respect? Shouldn't the one in charge deserve that?" He said while staring directly in my eyes.

Instinctively my eyes glanced away, down actually as I knew he was telling me to address him with "Sir". Something that he was growing accustomed to.

"Sorry sir, yes you deserve respect." I meekly gave in.

Ryan got up to inspect my work. I followed behind like a puppy following his master. There was no doubt who was in charge now. Before Ryan said anything, I saw it, in my haste I grabbed the dirty dishes and silverware from dinner but forgot to put the silverware into the dishwasher before I ran it. That didn't go unnoticed by Ryan either.

"What is this? You do a half ass job now? This is a blatant dereliction of duties, I can't let that go without a punishment."

Fuck, I was so much in a hurry to get that feeling when I asked for him to do the inspection that I missed it. It was my fault for sure. The asking to inspect my work part of the evening I looked forward to so much, that I got careless.

"Sorry sir, I'll hand wash them since the dishwasher is already running."

Ryan finished his rounds of my work, he didn't find any other infractions which was a relief.

"Good job, other than the silverware in the sink everything else looks perfect."

I was so happy because Ryan was happy and even gave me a compliment despite my mistake. But that didn't last long as Ryan reminded me that another punishment was required.

"I'm not sure what your punishment should be but I'll let you know." He said as he returned to the couch to finish watching the game.

I think that was worse than him just giving me a punishment. Not knowing what was in store for me drove me crazy. My mind raced, what will he come up with for a punishment. Maybe he will add time to my chores, or maybe he will require me to do his laundry or even clean his room. All of those options had the opposite effect on me than a punishment should. Normally a punishment should be something you don't like so you can correct a behavior. But none of those options sounded too bad. I was enjoying doing the housework so another week would only feed my hunger to continue to serve this man.

I went to bed that night still unsure of my punishment. As I laid there I thought of how quickly I was becoming used to this new role. I was also enjoying the role more than I could admit to Ryan, even though I was certain he had picked up on the fact that I was willing to do whatever he said. I was also taking on additional responsibilities like cooking even though that had not been part of the bet. I reached down to feel my dick hard, I slowly started to stroke it thinking about all those crazy thoughts going through my head.

I was so tired that I didn't even finish jacking off, but instead fell asleep and dreamed.

In my dream I was interrupted by Ryan as I was masturbating.

"Did I give you permission to masturbate?" Ryan asked in a loud voice.

"No sir, I didn't know I needed permission." My response was as I still slowly stroked my dick.

"Take your hand off of that dick, I say when and where you can cum."

Which I immediately did as directed. Ryan came to the side of the bed, his dick now hanging out of his shorts.

"You want something to stroke, here you go sweety.

I reached up to grab ahold of his cock, it was big and powerful. Unlike my dick, this was a real cock attached to a real man. I felt privileged to even be able to hold it but I slowly ran my hand up and down his shaft. The strength, girth, and power of his cock was evident, I found myself in awe of it. I even licked my lips as I couldn't take my eyes off of it.

"That's a good girl, stroke daddy's cock." Ryan said in a husky voice.

I took my other hand and started stroking my dick at the same time. I was ready to explode when I felt my hand get slapped away from my dick.

"What did I tell you, you need permission to touch your dick. I think I will lock that dick up from now on since you have no self discipline." Ryan admonished me.

"Please sir, I need to cum so bad."

"No, you need to make sure the man is taken care of first."

I whimpered at the thought that I wasn't allowed to touch my dick but that only made me more aroused. And the thought of locking up my dick was putting me over the edge.

Without even touching my dick I felt an involuntary muscle jerk from my balls as I came all over myself just as I woke up from the dream.

I never had a wet dream before but that clearly qualified. I wasn't sure if I came from just the dream of if I was actually stroking it in my sleep but there was no question that I had cum over me.

The next morning I felt refreshed, so I quickly made breakfast and lunch for the both of us. I stopped questioning why I was doing it, instead I was just doing it. There was definitely a part of me that just assumed it was now part of my duties. When Ryan ate all his breakfast and grabbed his lunch while heading out the door he thanked me. Once again, that feeling inside me of pleasure knowing I did something good for him was like a drug. I needed it, more of it and all the time.

When I got home from work Ryan wasn't there yet. I quickly went back into cleaning mode without any thought. I was only about 20 minutes into my daily chores when Ryan walked in.

"I've figured out your punishment." He said as he walked into the apartment.

Shit, I forgot I had a punishment coming. What could it be, I wondered. I was fidgeting waiting to hear from Ryan what he came up with.

"Donny..." He never called me that, it was one more indication that he was viewing me as his subordinate and not his equal.

"I bought you something." as he handed me the bag he had when he came home.

I opened the bag, it was from a halloween store, I pulled out a sexy french maid outfit that you would see some of the college girls wear at Halloween parties. I looked up at him with a quizzical look on my face.

"I think it's appropriate for the maid to dress like a maid, don't you?"

"You want me to wear this?"

"Yes, as your punishment for the duration of the week you must dress like a maid."

"Ryan, I can't do that. I'm not gay." Even though the night before I had a very gay sexual dream about Ryan.

"This isn't a choice, apparently giving you extra chores doesn't seem to be working."

"But...this is really gay. Isn't there another punishment you can give me?" I pleaded.

"NO! I decide and this is YOUR punishment! And if you don't go put that on right now I will have to take you over my knee to remind you of your place." Ryan yelled.

OMG, my dick stiffened immediately at the thought of being laid over Ryan's knee to be given a spanking like a child. It was sick to think about, 2 best friends yet one was giving the other a spanking for not following his orders. But it was probably the most erotic thing imaginable at that moment. I could see in his eyes he was serious, and I can feel in my dick that I was getting aroused. I couldn't let him spank me with a hard on, that would be more humiliating than wearing a maid's uniform.

I headed into my bedroom to change. The costume had a frilly skirt, lacy apron, fishnet stockings and even came with a wig. I struggled to put it on but managed to somehow make it fit. Immediately I could feel my dick stiffen like I was meant to be in this ridiculous outfit. Then I heard Ryan shout out,

"What's taking so long? Do I need to come in there to give you another punishment for keeping me waiting?" Ryan said with a chuckle at the end.

Just hearing those words got my dick to stir again and I hurried back into the living space where Ryan was sitting. I felt embarrassed but Ryan got up to check me out. I was nervous for some reason that he wouldn't like it.

"Not bad, maybe get some heels and makeup you would actually pass as a girl." Ryan said with a laugh.

"Fuck you dude, this is embarrassing enough." I snapped back in a rare instance of defiance.

Ryan seem to let it slide and in an act of what I can only describe as kindness he said,

"Okay, I'll tell you what, if you at least try it one day I'll knock off a day to your punishment. Plus you won't have to worry about getting your own clothes dirty from all the cleaning." Ryan added as if that would be a reason for me to do it.

But one less day of chores didn't sound so bad, especially since I had already got added a day for my first punishment. I thought, who cares, no one will see me and I'll get a day knocked off then why not.

"Okay, but no one can know about this."

"Sure no problem buddy. Now I think someone has some chores to finish, let's go." Ryan ordered.

I guess it couldn't do any harm to try it while cleaning so that's what I did. I began cleaning like I had been doing all week but this time it was wearing a maid's outfit.

After a while I didn't even notice it...in fact, it made bending down a lot easier because my legs were not restricted by pants. I quickly finished my chores and reported to Ryan as it was now a habit to ask if he wanted to inspect my work.

"How did it feel? Being dressed like a maid doing girls' work" Ryan asked with that smirk on his face.

"Honestly, I didn't mind it but you said only for 1 day so tomorrow is it, right?"

"Yep, absolutely, but let me do a quick inspection to make sure you aren't starting to slack off again. Otherwise another punishment would be in order." Ryan said as he got up.

I followed behind him, Kitchen was spotless and Ryan acknowledged that I had done a great job. I blushed from the compliment and thanked him. It felt good to do a good job for him so I was excited for him to see his bathroom.

"What's this? I see toilet paper on the floor behind the toilet?"

"What? Really? I thought I got everything. I'm sorry, let me get that picked up." As I hurried to bend down to grab the toilet paper.

As I was getting back up Ryan closed the distance between us and was now right behind me. I felt his bulging muscles pressed up against my back, he leaned in to whisper in my ear.

"Do you know what this means?" He whispered.

I knew...he was going to punish me and I had no excuse. "Yes sir, I need to be punished" I meekly said.

Then he pushed me down over the sink, swiftly pulled up my skirt, pulled down my underwear and started spanking me. OMG, it hurt like hell, the stinging was sharp and the slaps were loud. It echoed in the bathroom like a concert hall, I was afraid our neighbors could hear.

"You brought this all on yourself, didn't you?" Ryan yelled into my ear.

"Yes, I'm sorry, I'll do better next time." I cried.

"You think I'm joking with you? When I tell you to clean my bathroom you don't seem to take your job seriously. Is that it? I don't deserve a clean bathroom? Is that what you are trying to tell me?

"No sir, you deserve it to be spotless. I will try harder next time I promise."

"Damn right you will, and I expect you to wear this uniform the rest of the week. Do I make myself clear?"

"Yes, I will wear it and do a better job cleaning, I promise, Please stop!"

Ryan did stop spanking me, my ass was on fire but there was something else on fire, my dick, it was rock hard. I was getting sexually aroused from being spanked by Ryan. Ryan spun me around to look at me in my eyes. He couldn't help but notice my dick poking out from underneath my skirt, my underwear still around my ankles. He looked me in the eyes but I darted my own eyes towards the floor in a very submissive manner. Then he grabs my chin with his strong hands, raising my head back up forcing me to look into his eyes. He had this magnetic stare that I knew I couldn't look away from. I was under his control and I would do whatever he wanted me to at that moment.

"Looks like that may have not been so much of a punishment after all. Someone liked it," as his eyes glanced down to my still hard dick.

"Are we going to have any more problems? Or do I need to go get my fraternity paddle and really give you discipline?" Ryan continued.

"No sir." I said as tears were rolling down my cheeks.

"Good, now get out of my sight."

I went to my room, my dick rock hard and still wearing the maid uniform. I locked my door, I laid down and started stroking. I knew exactly why I was so horny, I liked being submissive. I liked the humiliation, being subservient to an Alpha male, the spanking and of course being dressed in a maid's uniform. All of this was too much for me to handle, my mind (and dick) were on overload. It only took a minute to explode all over myself.

I knew why but didn't know much else. I never felt submissive before, I never was attracted to Ryan, I was never interested in men. But in my messed up mind, I wasn't a man being submissive to Ryan, I was a girl being submissive to him. Girl submitting to a man isn't gay, it was natural, just like what I witnessed with Ryan's dad and mom. I was assuming the role of the woman even though I never had any gay or feminine tendencies. Everyone saw me as a good looking, athletic male. But here I was, dressed in a maid's uniform only a couple minutes after being spanked by my roommate covered in my own cum from the most intense orgasm I've ever had.

The next morning I got out of bed, headed into the kitchen to make some breakfast and make my lunch, not realizing I was still in my maid's uniform from last night. It was out of character but Ryan was actually awake that early and came into the kitchen to eat his breakfast.

"Damn girl, you love that uniform that much that you even put it on this morning just for me?" Ryan joked.

"No, no, no, it was just that I fell asleep in this and haven't jumped in the shower yet." I tried to explain not even realizing I was still wearing my uniform.

"Well remember, I'll need to do an uniform inspection before you start your chores and I better not see those wrinkles from you wearing this to bed."

Inspection? I should have been offended but instead I was excited. I could feel my dick start to stiffen and knew I would have to iron this before tonight's inspection. I then turned my attention back to Ryan asking him if he wanted to make him eggs for breakfast falling deeper into the role of a housewife instead of a roommate.

Once breakfast was over and I made his lunch I hurried to jump in the shower to get ready for work. I was running behind and didn't want to be late for work. By the time I got out of the shower and was heading out the door I saw a note from Ryan.

"6pm sharp you should be in your uniform and ready for me to inspect your uniform. Then you can start preparing my dinner. -Ryan"

I read it twice, it made me feel good. I stuffed the note in my pocket and hustled off to work. All day I would randomly reread his note and each time I could feel the butterflies in my stomach. Did I have a crush on Ryan? I mean, he is a good looking guy with an amazing body, what girl wouldn't have a crush on him? Then it hits me immediately, but I'm not a girl and I'm not gay. Why am I thinking of him that way? Why do I want to please him so badly? Everything felt turned upside down but at the same time it felt right, like it was my calling.

I missed my bus so by the time I got home it was already late, around 5:45 pm. I knew I had to get ready for my inspection so I raced into my room, plugged in the iron and got undressed as quickly as I could. While the iron was heating I put on my fishnet stockings and wig. I even grabbed some colored lip balm that I picked up on my lunch break. I quickly ironed my uniform to take out the wrinkles and put it on. One last look before I head to the kitchen, my lips really were noticeable in this shade of pink. Just as I made it to the kitchen the door opened and it was Ryan.

I stood at attention as Ryan got up to inspect me. He walked around me checking me out.

"Not bad, did you put on lipstick?" Ryan asked.

I was embarrassed and immediately denied it.

"Here, put these on too." As he handed me a bag.

I peeked inside and saw they were high heels, very sexy high heels. Probably 5" with an ankle strap and closed toe. They were very shiny, like patent leather as I pulled them out to admire them.

"I figured since you are now my maid you should dress the part. Don't you agree?" He asked.

"Yes sir." I said with a smile.

"What do you say to your boss when he buys you a gift?"

"Thank you sir. It was very kind of you." I said without hesitation.

"Good girl. From now on I expect you to wear that every day when you are cleaning and waiting on me. Now get going on your chores and don't let me down or you will regret it." He said in a very commanding tone.

"Yes sir" I said as I hurried into the kitchen to clean and prepare dinner.