Two Days a Month Pays Rent

Down on her luck college girl takes matters into her own hands and leverages the one currency she has to achieve her goals.

June was easy, but July was handcuff month and definitely not so easy. I spent nearly 48 hours with my hands cuffed behind me. I had to eat that way, pee that way and of course get fucked that way. Face fucking takes on a whole new meaning when your hands are tied. July was definitely one of the harder rent payments of the year.

Maybe we should start at the beginning. You see, I'm 21, a curvy 5' 3" redhead with big curly hair and a drive to succeed. I'm also an accounting major at a prestigious NW college. My family was not able to help me and by my Junior year, I was living out of my minivan trying to make ends meet, while also working two part time jobs and a full class load.

That all changed one drizzly Saturday afternoon. I had finally saved up enough for first and last on an apartment and was scouring ads on marketplace. I was using the local coffee shops WiFi and getting very frustrated not being able to find anything in my meager price range. The gentleman sitting next to me at the bar was equally lost in his phone, but politely (and probably mistakenly) asked how my day was.

I let loose, barely able to contain my tears as he sat back and listened to my tale of woe. It probably didn't help that I was wearing a rain-dampened cotton top and an inappropriately short skirt (it was laundry day). He was easily in his early forties and sported salt and pepper hair, a confident smile and not a ring in sight.

"I have an idea that you may or may not like..." and he wrote an address on my napkin. "Swing by later today, I have a pool house that might just work for you." Explained Mr Confidence. I wasn't sure whether to be delighted or scared.

I looked at the napkin and immediately recognized the street, it was lined with mansions set back off the road and smelled of old money. I smiled a meek smile and thanked him as he got up and walked away.

Three failed apartment viewings later I was parked at the ominous gate to Mr Confident's compound. Fuck, what was I getting myself into?

The box crackled "Drive through and park on your right" as the gates swung open. I did as instructed and pulled up in front of a cute little house surrounded by lush gardens with a substantial mansion in the background. As I got out, fighting my tiny skirt and hoping my nipples weren't poking through my shirt, he popped out of the front door with a welcoming smile.

"Glad you made it, I haven't been in here in months, so I was walking through the place making sure it is presentable, I think you'll like it. Quiet, not far from school and already furnished."

That did sound dreamy, but my tight budget had pushed me away from a handful of places that weren't a fraction of the beauty of this one and I was dreading asking him how much it would cost.

He waved me in and we did a quick tour. It was easily the nicest home I'd ever been in and had views that made me want to live there for the rest of my life.

"I'm Randy, I work in tech and live in the main house. Let's see, utilities would be included, there is a small car in the garage and my butler will stock your fridge if you are comfortable with that."

I nearly fainted, and barely worked up the confidence to ask the cost, almost dreading the answer as I scanned the tasteful furnishings and the glorious views.

"I have not had anyone live here in years, so let's say $2000 per month with a matching security deposit."

I nearly cried. I was sketchy handling $500 per month and was feeling very foolish that I was even here.

"Oh my, I'm a struggling college student and paying my own way, I'm very sorry I bothered you..." And with that I pivoted and headed to the door, no longer able to hold back my tears and secretly realizing I may have to live in my car for the winter.

"No worries Christy, if you change your mind, here's my number." Shared Randy as he handed me his card.

I looked back at the gorgeous home, the park-like setting and then to my crappy van and in a moment of pure desperation, said "Can I pay you in some other way?"

Randy raised an eyebrow and gave me a once over with what I suspect was with a completely different perspective. He asked very carefully "What did you have in mind Christy?"

"I'm not sure, I can clean for you or maybe help prepare food, anything you want, I'll do it, I love this place." I explained with an undeserved level of confidence. I really had no clue, but honestly, I would have dropped to my knees and sucked him off if he'd asked, just to live here for the winter.

"Those duties are already fulfilled here, but I appreciate your 'let's make this work' attitude." Stated Randy with a wry smile on his face.

At this point I had nothing to lose and decided to lay it all out. "I've lived in my car for the last two months, I can't keep that up, particularly through winter and will do anything you asked of me to pay my rent, if you want to fuck me, I'll do it. Use my body for a weekend every month, how does that sound? I'll do it, bring you coffee in the nude? I'm on it, this is really the only currency I have left at this point."

Randy stared at me processing my words. I'm pretty sure his original plan to help a cute college girl did not include sex, but here we are.

"Ok Christy, I can see we may have differing narratives on paying rent, but I do really like your willingness to do whatever it takes to achieve your goals. Let's go up to the main house, grab a coffee, with our clothes on and you can walk me through your situation and maybe even your long term plans."

It still felt very businessy, considering I had offered him my body in trade for rent, but I had little to lose at this point and my instincts were telling me Randy was not the type to keep college girls chained up in his mansion.

We ended up having a very frank and somewhat explicit talk that lasted well into the night. He was very single, a chronic workaholic and did not date much. He also traveled a lot and liked the idea of someone living in the property while he was gone. The coffee had moved onto wine and he had Chinese delivered. I was dead honest and explained I thought he was attractive and I shared my propensity towards mildly kinky sex, he did the same and we seemed to have more common ground than either of us had anticipated.

"Ok, so I like your weekend a month plan, how's this, Friday night to Sunday afternoon, once a month pays your rent. You show up wearing what I ask, do as I ask, this only involves us and then we go back to our business when we are done. I'd also like to take you with me once a year on a week-long trip to Europe or Asia and you would serve me during that period as well." Stated Randy as if negotiating the purchase of a property.

I liked his simple plan and I'm sure the wine was helping me deny the fact that I was trading my body for rent. "Ok, but I want the car and the butler service as well." I stated in a firm tone.

Randy raised his eyebrow again. Almost amused that I had come back at him with specific demands." How do I even know you're good at this?" He asked as if daring me.

I pulled my top off and said "Tell you what, I'll show you right now, but it means I sleep in the little house tonight." And with that I dropped to my knees and unzipped his pants. Before Randy could even respond I was balls deep on his cock and his words were little more than appreciative moans.

"We'll call this an equivalent to checking credit, so I'm more than happy to show you I'm worthy of your trust."

I breathed before dropping back on his cock. In spite of a very hard dick bumping the back of my throat, I felt empowered to have taken the proverbial bull by the horns and used the tools I had to make things happen.

Randy moaned for the next ten minutes while I delivered a porn quality sloppy blowjob, only stopping to rub my tits up his wet shaft and ask if he thought he'd be able to handle 48 hours of this.

His moaning increased and I could feel a firm hand in my hair. I knew he was close and was more than a little proud of my work. He bellowed and held my face on his cock as he shot down my throat. I swallowed it all, making exaggerated gulping sounds so he knew what I was doing before slowly pulling off and just licking the tip.

"My god, that was spectacular, I have not cum that hard in forever, I would say your credit check came back with a high rating." Shared Randy between heavy breaths.

I moved back to the couch, but left my shirt off and went back to sipping my wine.

"Do we have an agreement Mr. Smith?" I asked, looking him dead in the eye and licking my lips.

"We certainly do Ms. Chisholm, we certainly do. You are welcome to move in tonight and I will expect you back at the house this Friday to pay your first month's rent in full." Stated Randy in a commanding tone.

I was almost giddy, but tried to maintain my composure. "Yes sir, we have an agreement." I stated, reaching over to shake his hand realizing my tits were still hanging out.

I grabbed my shirt and strutted, still topless towards the door and my new home. Not having much stuff, it only took me a few hours to get moved in. I also checked out the "little car" Randy had mentioned and found it to be a brand new Miata. I knew it might be wrong, but I got a little wet.

The next morning I was doing an online class and admiring the view when there was a knock on the door. My heart fluttered and I made myself ready to explain why we had to wait until Friday.

To my surprise, a well dressed older gentleman holding a box of groceries was standing in the entryway looking back at my van. Before I could ask, he pushed past me and headed to the kitchen while explaining his role and intent.

"I'm Charles and Mr Smith explained you are our new tenant, I took the liberty of picking up the basics to get you started and have attached the info for our grocery app as well as all my contact info. Please do not not hesitate to reach out if you need anything. It's lovely to have a fresh face on this stodgy property." Explained Charles with a comforting smile before heading back to the door.

"Would you like some help moving this vehicle into one of the garages?" He asked with a tone that I suspect was more about removing an eyesore than protecting my van.

"I will leave a door open in the rear garage and an opener on the bench in case you need to retrieve it later." Stated Charles before closing the door behind him.

I stared at the box of groceries with a bit of disbelief. Was this even real? What was real was the class that I was now missing and needed to return to. A few hours later, I finished cleaning out my van and had parked it in a row of garages fifty yards or so behind my new home. It was now sitting next to a dusty Ferrari and a McClaren that could not have even been street legal. I laughed a little and walked back to the little house. I guess I am a Miata girl now.

Walking up to the front door I noticed a box, maybe Charles forgot something? I grabbed it and went in, pondering what I could make for dinner out of the basics he had left me.

Later in the evening I grabbed the box, sat down at my small dining room table and opened it up. It was immediately obvious this was not from Charles. The butt plug, lube and pair of handcuffs made that more than obvious. It was topped with an elegantly written note stating this was the beginning of Friday's outfit and he looked forward to my August rent payment. I was wet again.

I got through several more days of school and even tested out the Miata, grabbing lunch on Friday. It felt really good to drive a convertible and kinda even made my nipples hard to feel the wind. Maybe I'm just a horny bitch, hard to say.

After taking the scenic route and touring local backroads, I returned to the house around 4:00 only to be greeted by another box on my porch. It was a lot heavier than the last and I was a little giddy pouring the contents on the table. An elegantly boned basque was followed by strappy heels, stockings, a tiny g-string, an ominous leather collar and a small bottle of perfume. My eyes grew wide.

The note slid out last and read "After shaving yourself smooth, put on everything in the first box and then the contents of this box. Wear nothing else and come to the back door at 6:00 pm."

I did remember seeing a back door by the garages, but that was a good hundred feet away and exposed me to, well, I guess just trees as the property was absolutely hidden from the road and neighbors. I got even more tingly before heading to the shower.

I had not shaved my pussy in quite some time, this was luxury homelessness did not afford and thanks to Charles I was stocked up to pamper myself in the bathroom. Within the hour I was perfectly smooth and more than a little wet. I padded into the bedroom and stared at the jeweled metal butt plug. Was I really supposed to put something in my own butt? Although I had never had a cock up there, I did have a previous boyfriend that would snake a finger in when he ate me out. I didn't really mind it, but we had broken up before he had the opportunity to put anything else in my ass.

Well, here goes, I rubbed lube into my hole and then a bunch onto the metal plug and pressed it home. A few deep breaths to relax and it popped in with little pain. I felt full and more than a little dirty.

Next up was nails and makeup and then the lingerie. The stocking and panties felt luxurious on my smooth skin and the collar very naughty as I locked the keyless padlock and spun it around to the back. I was greeted with rhinestones spelling out FUCK ME on the front. I stared at my reflection for a few minutes and then got back to drying and brushing out my red curls. What had I got myself into and how did he know my sizes?

The basque was more of a boob shelf and made very little effort to cover my nipples and the heels were devilishly sexy and I think made my legs and butt look pretty good. I continued to stare at myself in the mirror marveling at was probably the first time in years I felt genuinely sexy until my alarm rang, signaling it was time to walk to the main house.

I opened the front door and took a deep breath. I'd never done anything public before and was terrified and turned on at the same time. Luckily the night was warm and the sensation of heels and a butt plug distracted me from pondering the possibility of any potential public humiliation. By the time I made it to the main house, I had regained my long lost ability to walk in heels and was genuinely enjoying the sensation of something in my ass.

Before I could knock, Randy opened the door, dressed in khakis and a loose shirt he asked "Are you here to pay the rent Ms Chisholm?"

I replied, "Yes I am sir, and I do hope you find my payment satisfactory." As I pushed my boobs up and licked my bright red lips.

Randy guided me into a room I had not seen before, it was softly lit with jazz playing in the background. Pretty sure I had seen this In a movie and also sure my makeup would not survive the night.

"I know you like Chinese, so I have a light dinner before we get to our financial transaction." Explained Randy with a wink. We both knelt at a large coffee table and sampled a half dozen bowls of my favorites, chopsticks and all. God this felt sexy. I washed it down with a few glasses of wine before noticing he was staring at me.

"You know you're absolutely gorgeous, right?"

I blushed a little and responded "Do you say that to all your tenants that pay their rent with their asses?" He smiled.

"Speaking of asses, how is yours?"

"It feels naughty and full," I shared as I stood up and pivoted around, pulling my cheeks apart to show him the plug. "I've had fingers in there before, but I think I kinda like this, too." The wine had clearly diluted any inhibitions I may have previously had.

"You're certainly going to get more than fingers in your ass tonight" breathed Randy as he stood and threaded his fingers in my hair, pulling me in for a hard kiss

His other hand wandered around my body, kneading my ass, pulling on my nipples and brushing against my clit eliciting a moan out of me with each move.

"Get on your knees and show me how you plan to pay your rent Christy."

I'm not normally one to take orders, but my knees buckled and I was dropping his pants before I could even think. His cock was rock hard and swung out with a vengeance. I must have looked like such a slut, but it just didn't matter anymore. I was totally into this role and kinda liked it.

He stepped out of his clothes and it was the first time I realized how in-shape he was. A hand in my hair soon reduced my view to his angry cock and I went to work paying my rent.

He seemed to be enjoying my efforts and I'll be honest I was kind of liking the feeling of his hand threaded through my thick mane. He used that grip as a handle and gently guided me back to my feet, twirling me around and pushing me over the coffee table. I could feel him move behind me and play with the plug before guiding his dick into my soaked pussy. I was almost embarrassed how wet I was, but he seemed to be enjoying it and had dropped into a steady fucking that was pushing me towards an early orgasm.

I had not cum at a man's hands in easily a year and even then I had to help. This time I was as much a wet, warm hole as I was a sexual partner and I was ok with that. His fucking increased and with each down thrust his body pushed the plug into my asshole. The sensation was out of this world and It didn't take long before I was enveloped in a full body orgasm that had me screaming and flailing my hair across the coffee table. Fuck, I'm not sure where that came from, but I hope it happens again.

"Good little tenant, did you know your pussy tightens up when you cum? It's very hot, think you can cum again before I do?" Asked Randy as he pounded into me.

"Fuck me, just keep fucking me, I'll do whatever you want aghhhhhh fuck" and I came again triggering Randy to slam into me one last time and holding my hips he let loose in my twitching pussy. I laid on the table, feeling his cum run down my thigh and desperately trying to catch my breath as he pulled away.

The next sensation was a soft towel cleaning me up and a gentle kiss right above the gleaming plug. I sighed and hoped we were not done for the night.

"Come over here and clean up the mess you made tenant" demanded Randy, looking down at his still semi hard cock. I crawled over and licked my juices off him with loud slurps as I felt his hard on returning.

"That's very hot, now sit up and then lay back on the floor" instructed Randy

I pulled away, and then laid back onto the soft carpet. Knees now bent and pussy and ass exposed to his gaze, I luxuriated in the combined sensation of lingerie and expensive rugs before feeling hands on my inner thighs and a tongue on my hungry clit.

He pressed on the plug as he sucked on me and I was cumming almost immediately. Hips now arched off the floor and moaning like a whore, I came twice before he let suction off my hard bud. Fuck, he was good.

"Roll over Christy, show me the plug."

I moaned and did as I was told. The carpet rubbing my sensitive nipples as I pushed my ass up in the air, feeling Randy push my legs apart and place himself between them. Face down and ass up, this had to be the sluttiest moment of my life and I was loving it.

The plug eased out of my ass and I moaned loudly at the sensation, increasing in volume as his hard cock replaced it. Slow and steady, he pushed himself into my virgin ass while

I moaned and begged him to fuck me. It took a while, but my clit was brought back to full attention by the grazing of massive balls. Oh, that was pretty good. I was so lubed and prepared, there was hardly any pain and now I just felt fucked and the ball/clit contact transformed it into that pre orgasm tingle I knew so well. Could I actually cum from having my ass fucked? I now hoped so.