Roommates' Dirty Secrets... (closed for Princess)

[The_J0k3R]

Tommy

"Hey bro, is there any way at all I could crash at your place for a few days? This shitty fucking apartment I'm in has been condemned by the city and we all have to move out. I really can't afford to get a hotel and the landlord isn't returning my calls!"

It was definitely a shitty day. I had been putting up with this landlord's bullshit for months now. Leaky pipes, broken windows, busted locks, bugs... yeah the rent was cheap but this was no way to live!

"Sorry Tommy, ain't got room for you here, but let me make a phone call. I think my sister has a spare room at her place, and she could use some extra money."

That was unexpected. Brad knew about my "extra curriculars" and I was surprised he would be okay with me staying with his sister, Madison, considering the questionable legality of my side jobs.

I had had a thing for Maddie for quite a while. The girl just had these thick curves that were to die for... but we had known each other since we were kids. She was Brad's little sister, for fuck's sake! Nevermind that she was 21 and all grown up and hot as fuck. You just don't make a move on your best friend's little sister! Besides, she would never go for me. She frequently teased me for what she called a "never-ending parade" of new girlfriends, which was really only half-true.

Brad called back a little while later, while I was dropping a bunch of my stuff off at a rented storage unit. I had consolidated my stuff down to a single duffle bag, and my guitar and amplifier, for the time being. Of course, my "extra-curriculars" were stashed someplace special. Madison was cool with it, for a hundred bucks a week as long as I helped out with stuff and didn't leave messed everywhere. Deal.

Which was how I found myself knocking on her door. She had a small house near the college we both attended. She was an undergrad, and I had graduated last year. I had been unable to land a decent job, and was still basically living off what my rock n roll band could bring in on the weekends, and my little extras, of course.

"Hey," I said with a soft smile when she opened the door. "I heard you're in the market for a roommate?"

Madison

 

[princesssexci]

I couldn't believe my luck. My brothers best friend Tommy was coming to live with me. I'd recently gotten a call from him asking if Tommy could crash at my place and while I'd always had a small crush on Tommy when I was younger, I knew he was way out of my league. Besides, while I had a few side...'jobs' sometimes it was barely enough to keep me afloat and as long as Tommy helped manage my off campus apartment (because those were way more affordable then dorm rooms), it'd be cool.

And who wouldn't want an extra sexy guy living with them? A crazy person that's who! The day of his arrival I had to keep telling myself to chill. This was Tommy, I'd known him since I was five. The only difference now was that we were adults now.

About an hour and a decently cleaned apartment later there was a knock on my door. I jolted but then cleared my throat, fluffing up my hair then pulling my T shirt down, before making my way closer to the door. I mentally smacked myself. This wasn't a date, stop acting like a hoe! He's your brother's best friend I subconsciously pulled my tank top up as far as it would go.

I opened the door and smiled at his joke. "Actually, the rooms been taken, sorry." My eyes sparkled playfully at him before I opened the door fully. He was still as handsome as ever and I silently thought maybe this was a bad idea. He'd always been kind of a playboy and i wasn't sure I'd be able to handle it.

"Well let me show you around." I said pulling myself back into the real world. "This is the living room. That's the tiny ass kitchen. " I walked further into the hall where two rooms were next to one another. "That's your room, mine is the one on the left,and that's the bathroom."

 

[The_J0k3R]

The tour didn't take very long, as her place was pretty tiny. "Thank you," I said, setting my bag on the floor and placing my guitar case in the corner. I looked around. It wasn't much, but it was a lot better than where I had been living.

"I guess that's your room next to mine?" I asked, though I already knew the answer. I smirked a bit. "I hope these walls aren't too thin..." I said, giving her the same playful wink I had given her so many times before.

"So what's your boyfriend situation? Do we need to put a sock on the bedroom door if we have... company?" I asked, more out of curiosity than anything else. With a body like her's, I was sure she had plenty of suitors. Tits like those never went unnoticed. Even I had to drag my eyes away from them!

 

[princesssexci]

"Boyfriend situation? Ah, I'm single. " I said combing my fingers through my auburn hair. "My ex and I broke up like a year ago. " and I absolutely couldn't tell him about my little side jobs. He'd probably tell my brother, all hell would break lose, not to mention despite what I did on the side, I didn't want him to look down on me.

"Are you still the walking ecstasy commercial? " I teased him, even though this was sooo not a question that I needed to ask because I already knew the answer. "Do women still drop their panties at the sight of you?" Because I sure as hell want to! I silently added.

"If so, then yeah we probably should go with the sock on the door thing. I mean how awkward would that be, walking in on someone."

 

[The_J0k3R]

"Well... it's only awkward if you stand there and stare instead of joining in," I said with a conspiratorial smirk, before bending over and grabbing my duffel bag, unzipping it and dumping its contents, which consisted almost entirely of my clothes, onto the bed next to me.

"No sense living out of a bag," I said. I looked up at her again, letting my eyes drag over her thick curves. She had grown into a downright delicious-looking young woman.

"So, I want to thank you, again, for letting me stay here. I promise, I'll be finding my own place as soon as possible... but... uh, here," I said, pulling out a wad of cash, three hundred dollars. "First month's rent? And you're gonna let me take you out to dinner tonight. Deal?"

 

[princesssexci]

I rolled my eyes at Tommys comment despite the fact that my body tingled at the thought of joining in anything sexually with him. "Well I'll let you get unpacked..." I started before he stopped me and handed me three hundred.

His invite for dinner despite being an invite didn't even sound like it was a question. Thank god I hadn't booked any appointments tonight. "Um, sure. Deal." I said with a smile trying to remain as cool and calm as possible."okay I'm going to let you get settled in."

As I moved out of his now room, I smiled to myself and headed into my own room trying to find the perfect outfit. I probably should've asked him where we were going but then decided maybe going with sexy casual would be okay. That way if this was just Tommy being nice, my outfit wouldn't scream that I thought this was a date.

 

[The_J0k3R]

"Great," I said. I couldn't take my eyes off her voluptuous curves as she walked out of my room, especially her thick butt. I think I even licked my lips, subconsciously of course.

I turned on some music on my iphone and set about unpacking my clothes. I opened the closet and found some wire hangers, and there were just enough for my shirts and pants. I stuffed my tee-shirts, underwear, and socks in the old wooden dresser.

My cell phone buzzed a couple times while I was unpacking. I checked my messages once I was done, and sure enough, I had some work to do. It would definitely be better if Madison didn't know about my side-job just yet. I would tell her in due time, of course.

"Hey, Maddie, I've gotta run out for a bit, I'll be back in a couple hours," I called out as I left my room, not sure where she had wandered off to at the moment.

 

[princesssexci]

After pulling out my clothes for later this evening, I heard Tommy call out that he had some things to take care of. I peaked my head out of my bedroom just as he was heading out the door and smiled. "Okay, I'll see you later then."

Once he left, I'd received a text from one of my customers. Usually they came here but with Tommy living here, I wondered if that'd be a good idea.

Since Tommy said he'd be gone for a few hours, I was considering it but since I didn't know when he'd come back...despite what he said earlier, it probably wouldn't make the best impression to see what I did.

I grabbed a pen and a pink sticky note and wrote,

'had to meet with a classmate for a study group, totally forgot. Will be back soon.

Maddie'

Then stuck it on his door before heading out.

 

[The_J0k3R]

I got in my car and headed down the street. One of the calls was for a sophomore who still lived on campus in the dorms; I'd be meeting him on the Quad. The other was for a grad student who stayed a few blocks away from my new place with Maddie. I'd stop in there on my way back from the University.

I got to campus and found a spot in one of the parking garages. I had enrolled in a single class this semester, just so I could keep coming around campus as a legitimate student. I parked the car and grabbed a bookbag, peering around first. Satisfied, I opened the bag and checked my stash: several eighth-ounce bags of high grade, American-grown medical marijuana, each of them sealed in airtight plastic. It was still illegal here, even though so many other states had legalized the drug. I also had a number of small baggies with a variety of other items, but I knew this guy only wanted his usual bag of pot.

I took out one of the bags and slid it into a pocket of a different backpack, the one that actually had books and pens and my tablet it in. I stuffed my stash-bag down back underneath my carseat. I knew I needed a better system but this would have to do for now.

I headed to the Quad and met up with Mark. We did a walk-about, bullshitting along the way. We had done this plenty of times before, and within a few minutes we had casually made the exchange of money for drugs without anyone seeing anything, and I was headed back to my car.

 

[princesssexci]

"God, I thought you'd never get here." Jeremy said as I stepped into the cheap motel room. I flashed him a quick smile. "Why couldn't we meet at our usual spot?"

Jeremy had become one of my more needier customers. Before Tommy had moved in, I'd been having serious trouble with earning enough money for school. One of my girlfriends, Paisley, had jokingly suggested or at least, I assumed she'd been joking, that I suck cock for money.

Crazy, right?!

It didn't help that she was like super model gorgeous and I was just me, so yeah, of course I thought she was joking. She wasn't. She'd even had me sit in a few times with her to show me how easy it was.

6 months later, I had my own clientele. No one knew except Paisley. Sometimes, depending on the customers kinks we did it together, but charged extra so she'd get her cut. It's surprising how many guys out there were attracted to the more curvy type of woman. "So did I come here to talk or..." my voice trailed off as I started unbuckling his jeans.

 

[The_J0k3R]

I headed back towards Maddie's place, stopping in at Steve's on the way. Steve had actually been my roommate, sophomore year, and we still got along really well, so it was hard to say no when he wanted to hit the bong as soon as I gave him his bag.

Of course I took a few hits, and had a couple beers. The bong always did it's job well, delivering massive hits that never failed to get me good and lit. We wound up hanging out for about an hour, just rambling on about random shit. I asked him if he was still seeing Kaitlyn, and he shook his head.

"No man, I ain't got time for that anyways. Gotta focus on school. Gotta graduate. But I'll tell you what, I think I found the best possible situation."

"What's that, Steve?" I asked, watching the ceiling fan twirl idly, lighting up a cigarette.

"I found this girl, she'll come by once a week and suck me off for a hundred bucks. I don't have to take her out, I don't have to text her all the time, she doesn't want to talk about her feelings, none of the bullshit. It's the best thing ever."

"That's ridiculous," I said, but then again, I never had a problem finding a booty call when I wanted one. Steve, on the other hand, didn't exactly have girls falling over themselves trying to get in his pants. So maybe it did make sense...

I headed on back to Maddie's place and went inside, finding the note she had left on my door. I shrugged and took it down, tossed it on the desk and cleaned myself up a bit in anticipation of taking her out for dinner.

 

[princesssexci]

Wiping his cum off my lips, I stood up and held my hand out as Jeremy readjusted himself, buckled his pants up and pulled his wallet out, handing me the 100 dollars.

"Thanks babe. I'll text when I need more help."

Rolling my eyes, I grabbed the money and walked out of the room. Heading to my car, I groaned and laid my head on the seat. Hopefully, this wasn't something I'd have to do for long.

About 15 minutes later, I pulled up and headed back to the apartment. It was time to forget about all my dirty deeds and smiled to myself. I couldn't believe he was taking me out to dinner. Not that it was a date or anything.

He hadn't said it was a date so maybe I was getting a little too over excited. As I made my way into the apartment, I heard the shower going indicating Tommy was home.

Since I desperately needed a shower, I walked into my bedroom and patiently waited for the bathroom to be available pulling my clothes off the hanger and debating if my outfit looked too desperate or not.

https://s-media-cache-ak0.pinimg.com/564x/a8/0d/e7/a80de7193185fc4146cc216eab534508.jpg

 

[The_J0k3R]

Taking a shower all good and stoned had always been one of my favorite things. I had picked up some beer on the way home, and was enjoying one of those as well while I scrubbed myself clean. I had the music going on my phone, loud enough to hear over the sound of the water.

After a thorough cleansing, and still feeling a nice weed buzz going on, I got out of the shower, drying off a bit, and I wrapped my towel around my waist before stepping out into the hallway.

I immediately noticed Maddie's open door, and realized she had returned from her study group. "Hey Maddie!" I called out as I headed for my room, next to hers.

 

[princesssexci]

"Hey Maddie!"

I turned hearing his voice as he passed my room only briefly catching him in nothing but a towel. My eyes rolled in the back of my head as I held back a moan.

This was definitely a good idea. "Hi!" I called out as I grabbed my clothes and headed into the bathroom. I spotted the beer sitting on the soap dispenser then rolled my eyes.

I thought about taking it to him but then shook my head. He'd just have to wait for it since he couldn't remember to grab it. Closing the door behind me, I started discarding my clothes and then stepped into the shower to scrub the filth of desperate horny male off my body.

 

[The_J0k3R]

I closed my door behind me and tossed the towel aside, and was just pulling my boxers on when I realized I had left my beer in the bathroom.

"Dammit," I muttered. I didn't want to leave it there, as it would probably be warm by the time she got done in the shower, and warm beer is just nasty. But it was probably infringing on personal roommate space to knock and want to come in and get the beer. I heard the shower turn on.

Then again, I had known Maddie for years and years. Since we were kids! Surely there was an exemption in there somewhere...

Maybe... I was hoping to catch a glimpse of her sexy, thick body...

I pulled on a pair of jeans and went out into the hallway. I knocked on the bathroom door.

"Hey, Maddie! I left my beer in there! Can I grab it?" I called out through the door.

 

[princesssexci]

Hearing the knock and the request. I bit my lip. Honesty, one would think that if I sold oral sex it'd be easy to just let him come in and grab his beer. Not at all true. I pursed my lips because at the moment I had nothing to really cover myself with. It also didn't help that I was in the middle of washing my hair.

"Can it wait? I'm in the middle of washing my hair." I called out.

I began scrubbing the soap and then started on rinsing it out, "What?" Water was in my ears so I couldn't make out what he was saying so just yelled sure as soap got in my eye. "Fuck!" I whimpered.

 

[The_J0k3R]

She asked if it could wait, and I replied: "okay!" And then said, "just let me know when I can come in!"

To which she shortly replied with a "sure!" And I wasn't totally sure just what that meant, but I sure hoped it meant I could grab my beer, because I was already opening the door to slide in real quick.

I wasn't sure what I was hoping for; the shower curtain would block my view of anything at all, unless she opened it on purpose and flashed me! I grabbed the beer off the counter. "Thanks Maddie!" I said quickly. I stopped at the door.

"Got any requests for dinner?" I asked, smirking a bit to myself.

 

[princesssexci]

My eyes were burning. This was just what I needed before a date, red eyes. I'd probably look like a drug addict or something.

"Tommy, can you grab me a wash cloth, I got soap in my eye" I said directly after he asked about restaurant preferences, peeking my head out from behind the curtain slightly. It wasn't enough to give him a full of view of the goods but enough to hug my curves.

"And foodwise, I don't know. I'm usually good with burgers and fries."

 

[The_J0k3R]

I looked around the bathroom, still not sure just where she kept all the different toiletries and accessories. I started opening drawers in a cabinet searching for washclothes.

"Uh, how about pizza? Chicago-style deep dish? There's this little hole-in-the-wall down on 9th Street, and that stuff is just the best..."

I kept searching, trying not to look over at her and see just how well that curtain clung to her curves, but then I finally found them and turned and I couldn't help it but my eyes definitely lingered on some exposed side-boob.

"Here ya go," I said, taking a step towards her and holding out the washcloth for her. I stifled a chuckle at the sight of her with soap running down her face.

 

[princesssexci]

This was not how I'd planned my evening, scrubbing soap out of my eyes,"It's not funny!" I huffed hearing him chuckle. My stomach was starting to grumble with hunger. "I could've gone blind and I'd have to use you as a walking stick for all eternity." I said stifling a giggle as I finished getting the soap out.

"Umm, pizza sounds really good right now." I smiled as his gaze wandered and stayed glued to my breasts,"but I have to get dressed. I'm pretty sure it's illegal to go to pizza places naked, hole in the wall or not."

Then I immediately started blushing when I realized I was flirting with him!

 

[The_J0k3R]

"Probably," I replied with a smirk, turning and stepping towards the door. "But if you didn't want to put clothes on, we could always get something delivered..."

Did those words really fall out of my mouth? Her flirtation had brought it out in me naturally. It was kind of a good idea though...

"I'm sure the delivery guy would love a tip like that!" I said, laughing, not leaving quite yet.

 

[princesssexci]

I bit my lip sorely tempted to take him up on that offer and then shook my head. "Nope. Sorry buddy. Your specific words to me were 'You're letting me take you out to dinner, deal?' " I smiled then added,"Technically you're not taking me out if we order in."

"Besides, I don't let a guy order takeout while I'm naked that easily." Oh my god, was I seriously--did I seriously just say that out loud? I bit my lip and laughed nervously, "Now shoo, so I can get dressed."

 

[The_J0k3R]

"Alright, alright," I said, chuckling a bit as I walked out the door and shut it behind me, shaking my head a bit to myself. Damn, she had a stunning body. Those curves were just to die for!

I took a drink of my beer as I walked back into my new room, and pondered which of my half-dozen shirts to wear out with her tonight. I opted for one of the nicer-looking ones, a white button-up.

My mind swirled a bit, still pleasantly buzzed off the weed. I wondered if she thought this was a "date." I wondered if it actually was a date. I couldn't remember the last time I had actually gone out on a date. My "dating" life generally consisted of bar or party hook-ups, and the occasional Netflix-and-screw.

I waited til I heard the bathroom door open and shut, and then called out to her. "Hey, you want a beer before we go out?"

 

[princesssexci]

After a few more minutes of scrubbing, I got out of the shower and then dried myself off, wrapping my towel around my curvy body I brushed my teeth and headed to my bedroom.

"You want a beer before we go?" Tommy called out.

"Sure!" I called out as I started putting my clothes on. I decided on a white tank top with blue skirt and a red pair of laced panties. Since my tank was actually a spaghetti strap, it would've been tacky to wear a bra with straps so I opted for a white laced strapless bra. Once I was dressed, I headed to the living room taking my beer from Tommy, he'd already opened it for me.

I took a sip then decided to ask what had been on my mind all day,"So, is this a date?"

 

[The_J0k3R]

I just barely caught a glimpse of Maddie in just her towel traipsing across the hallway, and then she was gone into her room. That sight alone was just enough to inspire a bit of a rush to my loins.

I headed to the kitchen and grabbed a couple beers, and then sat down in the living room to wait for her. My mouth about dropped when I saw her walk in, wearing that white tank top and short skirt, her curves perfectly displayed.

She sat down and took a drink and then asked if this was a date.

She was so blunt and forward about it, I very nearly spit out my beer! I gulped it down though, and chuckled. I gave her a conspiratorial look.

"Think your brother would be okay with that?"