Matt Needs a Place to Stay...

So here's my story, my names Matthew Wallace, or Matt for short, my parents never call me Matt though. I'm 18 and i have one year left to study here in Azure High before going to college, also here in Azure.

But my parents wants to move states, but i wanna stay here to finish my education, so here's my problem. They are leaving with or without me, and won't pay for me to stay here, so in short, i'm fucked, i have 2-3 days to workout a place to live, without having any money basically, i have some but not even close to what i need to rent a place here.

My mom suggested i ask all my friends if i could stay with any of them, my dad doesn't care he still wants me to come with them, and live for free as he says.

So i texted and called around to all my friends today when i woke up, didn't get to study at all, and all my friends are probably partying or getting drunk, so i probably won't get any answers for a while.

So everything in my house is being moved, i have two bags of clothes and my own stuff, ready to be lobbed into the car as my dad said for when i give up and go with them.

After dinner i texted Kyle, my best friend what i should do and if he knew any way i could stay with someone, for free.

And he said no, but that he'd ask around, ask his mom and dad and that he'd probably get back to me tomorrow, and my deadline was getting close, see my parents were gonna drive off real soon, they wanted to get out of this town and state, pressuring me to give up.

But just an hour later after i texted him, Kyle replies that he has a possible solution, his dad has a friend, basically his uncle, has a big house on the outskirts of Azure, and that he's fine with me being broke, and that he would pay for me until i get on my feet by myself.

I replied back that's awesome, and asked if i could get his number.

Kyle said he would fix it all, that we would meetup at his uncles place tomorrow, and he just needed a picture of me to send to his uncle so he knew what i looked like, i scrolled through my photos app and picked one out of me swimming and tanning a few weeks ago.

I was fit, so i wouldn't be a lazy bum and would pull my own weight around his house.

Then Kyle replied again saying that his uncle looked forward to meeting me and hoped that i would enjoy living there and that he hoped he had solved my problem.

I was so happy, and relieved, i didn't want to restart my classes & projects in another school, and this would help me get the college i want, being so close to it.

I told my parents and my mom was happy for me, my dad pretended but he was glad that i wouldn't be on the street.

I went to bed after packing my bags with the last of my stuff, ready to start my new life tomorrow, still in Azure!

Kyle picked me up in the morning, he was kinda hungover so he definitely partied last night, and i wasn't invited, but i still considered him my best friend, i've known him since kindergarten.

Then we arrive, and Kyle helps me with my bags to the door, before he leaves, shit i don't even know the guys name, i turn around but Kyle's already left, okay this could be slightly awkward.

I knocked or rang the bell aswell, and then looked around, this place was kinda huge, a big ass lawn, and the house looked very modern and expensive.

So this guy was either rich or yeah, he was definitely rich, no way he would take in a stranger.

Then the door opened as i was looking around, and i turned and saw my savior. 40 year old something guy, but oozing wealth, hard worker.

"Hey there Matthew, i'm Ryan, Kyle told me everything about you, glad i can help." He says reaching out his hand, we shake.

"Hey, i uh, don't know a lot about you uh, Kyle didn't even tell me your name." I answer awkwardly, i was way out of my usual zone with a richy rich like this man.

"No problem, we'll get to know each other. Come on in let me show you around." Ryan says grabbing one of my bags and carrying it inside, i follow.

"Wow, your house is huge..." I say marveling at the huge spacious lounge we were in, with two more floors above us, a set of stairs too.

"It is, that's why i have room for you." He says setting my bag down, walking up the stairs.

"Yeah about that... i am like basically broke, i could never repay you for letting me stay here." I say following him up.

"We'll sort that out, you know, you help out around the place, basically play housewife until you get money going." He says with a chuckle, and i guess he was right, i wasn't gonna make any money until college, so i would be living here for free for atleast a year.

Then he shows me around upstairs, and this would be where my room would be, with an adjacent bathroom, kitchen, and then he lived one floor above, the bottom floor the main floor was for a bigger kitchen, a movie theater, a living room with another TV and gaming consoles, a tennis court indoors and a jaccuzzi.

Wow, i was stunned, then we got my stuff upstairs to my room, and he cooked us dinner, and all the while we talked, getting to know each other, he also said i could bring over girls anytime, he was discreet, private, i said i appreciate that.

After dinner i helped load up the dishwasher, and Ryan came to me and said to me to shower and get a good nights sleep and be ready for school, he also gave me 500 bucks for uber or bus ride to and from school, and lunch, if i needed anything else.

"I can't take this Ryan, i mean-" I start protesting but he didn't want to hear it.

"Nonono, you live here know, under my roof." He says sternly, and leaves, okay he was really hospitable and nice, and rich as fuck.

I shower upstairs and it's just divine, the water has to be different, god this is amazing.

Standing in the mirror, looking at myself, my new life, my new home, this was going to be great.

My new bed was so comfy, i slept like a baby, and by the time i woke up Ryan had already left for work.

And school was tedious as always but i got a lot of stuff done, i came back to my new home before Ryan was back, so i decided to do my duty as housewife, cleaning whatever in the kitchen, vacuuming the whole house, except for his room, i'm not gonna infringe on his privacy.

*A week passes*

I've lived here a week now and my god is Ryan a hard worker, no wonder he's rich, i've started making food or dinner for us almost every day now, he likes it, and after dinner i'm gonna take my clothes out of the dryer, i washed all of my stuff, so they were fresh for use.

But something went wrong, and they were all discolored and had a weird smell to them, i asked Ryan if he could help me or if i could use his clothes, and he told me he would buy me new ones, and loaned me a shirt for tomorrow.

Then on friday he came home, and bought us pizza for dinner, we ate together in the living room watching TV, he asked me if i were gonna party this weekend, i said maybe, didn't wanna reveal that i was a total nerd yet.

We stayed watching TV til midnight, when we both said goodnight, he went to his floor and i to mine, but oh right i'm out of underwear, well clean underwear, i'm gonna ask him now instead of in the morning, he might not be here when i wake up even.

I go upstairs to his room and go inside, but he's not in his bedroom, the lights from the bathroom are on though, he's probably showering, or taking a shit, i better look before i shout or ask him.

I tip toe quietly by the door and look inside, and oh! He's not showering, or on the toilet, he's jerking off, he told me he doesn't have a wife or girlfriend cus of how much he works and that he's stressed alot.

So he was releasing stress right now, god he's really beating his dick, he's kinda big from where i was standing, Why was i biting my lip.

And why wasn't i just leaving, why am i looking at his cock, he lets out a groan and i instantly turn and leave.

I'm all flustered when i get back to my room, i didn't even get a pair of underwear, i just stood there watching him jerk off, his dick was really big though, oh god stop Matt, just go to bed.

I slept weird, i was rock hard, and i jerked off two times, cumming in my own hand, wiping up whatever dribble on the sheets, i can't stop thinking of his dick, it was fucking huge, compared to mine, and i always thought i had an okay size, shake yourself out of it Matt.

And to make it even more awkward for me, Ryan was awake and home when i got up, he made me breakfast and said he would buy me new clothes today, i was thankful and he told me to just relax today and swim in the pool and work on my tan if i wasn't gonna go party.

I said yeah, that sounds nice, i can go party next week.

But then i remembered, my swimming trunks were ruined, i had none, he laughed and told me to go naked, there's no one around. And that there's towels in my bathroom, okay that sounds good.

So he left to buy me clothes, and i got naked upstairs in my bathroom, god i looked good, my butt has gotten bigger but, no one ever sees it, and i like to keep my hair down there trimmed, all the hair, like baby smooth, makes my dick look bigger, but now after last night, it doesn't look that big.

Why am i looking at myself naked, i wrap the towel around me and head downstairs, and outside to the pool area.

This was luxurious, and i put my towel down and went for a swim, this was life, i'm gonna enjoy living here, even if it's just until i get a job, well then i have to find a new place but you know.

I took a few laps before getting up, laying down on one of the sun beds, and let the sun paint me, everywhere, still naked, i was almost asleep when i heard Ryan.

"How was the pool?" He shouts, and i stand up in a rush, oh shit i'm naked, i put my towel back around, phew, i don't think he saw me.

"Amazing." I answer and he comes over, wearing a pair of swim trunks, he jumps in, and swims a few laps way faster than me.

"That is good, i put your new clothes up on your bed, lets go take a look." Ryan says as he climbs up, the water running down his body, god damn he was fit, and his muscles, made me look like a wimp.

"Uh yeah, yeah." I say stuttering looking at him. We walk up to my room.

And the stuff on my bed is all uh, from uh womens and girls stores, victorias secret etc, he was joking with me right, obviously.

"Here, try this on." He hands me a small bag, and i pull out a pair of laced panties.

"Uhm, Ryan these are panties, for girls uhm..." I say, stuttering, holding the surprisingly soft womens underwear in my hand.

"I know but, i'd bet they feel good and would look good on you." He says, siting down on my bed.

"Yeah but, i'm a guy, like i get that this is a joke, okay it's kinda funny." I say and laugh, putting them back in the tiny bag and look through a few other ones, but they are all filled with womens underwear, panties & bras, yoga pants, skimpy tops, skirts. This is one elaborate prank.

"It's not a joke dude, you live here for free. The least you can do is dress for the part." Ryan says, stone cold serious, okay, was he not joking?

"So it's not a joke and you uh, want me to wear, womens clothes?" I ask, as i keep looking around.

"Around the house yes, only panties when you got out and to school, you know." Ryan then explains, shit, he's fully serious, i pull up another pair of sexy little panties and look at them.

"Try them on, not infront of me obviously, just see how it feels and if you can't do it then..." Ryan says, shrugging his shoulders, and i look at him.

"Then you can't live here, i have to kick you out, it's one of the things you can atleast do for me." He follows up and stands up, and walks to the door.

"I bought you mens clothes too but, show me your serious about living here, or you can get out." He says closing the door.

Leaving me with a choice, i mean he was totally fair, i lived here for free in a luxurious expensive big ass house, and he even gave me money for rides to school and whatever else, i bought starbucks today i mean.

And god i'm actually considering this, i mean i can't tell my parents or Kyle that i crashed out of here just cus, you know i can't tell them the exact reason, and they're not gonna help me.

God i think i have to do this, if it's just some kink or is he just pulling a prank, but he seemed really serious, fuck it i'm gonna put them on, he won't tell anyone he's very private about his house.

I go in my bathroom and slide them on, god damn this is smooth, and feels really good, hugging my skin, and they make my ass look even bigger, and my dick even smaller, i grab a shirt from one of the other boxes that looks nice, don't care if it's a girls shirt, and i swallow hard and confidently by the door, anyhow this goes, i'm either calling his bluff or he's actually serious and i get to keep living here for free, and it's just wearing panties i mean, or around the house more girly, and then when i leave, only panties, i think that's fine, no one's gonna know.

I walk out of my room and over to the couch on my floor where Ryan's sitting, i clear my throat again walk up to him, swaying my hips, presenting myself to the older man, my baby smooth shaved legs, with a hint of tan already.

The black panties hugging my skin so tight, his eyes were fixed on me, now i've read all about mating rituals and Alphas and betas and girls, and Ryan was definitely an Alpha, successful rich, stressed, and he took me in, and he's clearly seen me as weaker, as a beta.

No girls no partying, and he probably saw my little dick by the pool, and he was testing me now, and i was walking right into his trap, because i needed to live here.

The clothes was his way of testing me.

I present myself infront of him, he stands up, towering.

He was much bigger than me, the Alpha male looked over me with a smile on his face, he liked that i had done what he asked.

"Looks good, what did i tell you." He says, as he takes a step around me, looking me over, oh shit he's gonna see my butt, and it looked great in the mirror. Another sign pointing me in the direction of a beta.

"Haha yeah, it looks alright, feels good too..." I say with a nervous chuckle, as he takes a lap around me, satisfied, happy that i want to keep living here, doing this one thing he wants.

"Now you remember our deal, i gotta go get dinner in town for a meeting, your other clothes are downstairs, get everything into your closet." He says, before he leaves.

I swallow hard again, and then as he's gone i race back to my room, and pull my new sexy panties to the side, and my dick springs free, god it kept it down so good, i had a boner the whole time, while Ryan inspected me.

I jerked off and then spent the next hour sorting all my new clothes, even the girl clothe into my closet, and it was bigger than i had ever had, i had no male underwear, Ryan made sure i couldn't cheat, so after finalizing my new wardrobe, i tried on some bras, and they were surprisingly nice and actually made my boobs look great, and the yoga pants, god holy shit, i would probably wear them all day everywhere if they weren't so feminine, they were so awesome.

So i kept the panties and yoga pants on, and the same shirt, making dinner for myself, and then eating it in my room, watching TV.

I had to make sure to always be wearing panties, and girly clothes around the house, or i would be out on the street with no place to live and no way to find one.

Ryan came home later that night and said goodnight, and went straight to bed, i was in the kitchen making smoothies for tomorrow.

So i went to bed aswell, i thought about looking into his room, but it was too risky, i have to lay low, he's seen me for the weaker beta that i was....