The Roomie

John was about to celebrate his 55th Birthday,

 He sat in his 2500 sq ft home with a casita attached and swimming pool in a luxury back yard complete with hot tub, he reflected on the last year.

His mother had passed on Christmas eve, his lone sibling refused to talk to him because he had told her the funds from their mother’s estate would be held in trust for her. John tried to explain that this was mother’s wish, but, to no avail.

He began to think about his business, and how much time it consumed, but how it afforded him the things about him and the life he led. The casita was rented to snowbirds and the occasional hook up from the web, but now at this time it was empty waiting for spring training in the Arizona desert. The depression began to return, John said to no one in his empty house. OH FUCK NO. at that very moment he decided he was done being alone, yes, the last three years making sure his mother was cared for took up almost all his free time, then his sister and her trips to jail and treatment ate up some time and provided constant worry, John realized it was done. The plan to set up his sister’s trust was formulated, the family lawyer would oversee it, he would have nothing to do with it, if she wanted no more communication that was fine, he would grant her wish.

Feeling lonely he opened his phone, scanned the cruising sites, there right in front of him, the closest in proximity was a 19-year-old 5’4” 130lb young man, his bi line read, need to find a roommate asap.

Reading down further John discovered he was into Daddies, sitting back in his antique leather and wood desk chair, he thought about it, this could be trouble. Or this could be good, a young man to have around living his life as young men do would be invigorating. He decided, he sent the message, Room for rent in Central Scottsdale, Interested? The response was immediate, yes sir when can I see it? John thought about it, he wasn’t due back to work for a few more days so he just said at your convenience my schedule is open. Once again, immediate response, what is the address sir? John forwarded it. The answer threw John for a loop. “Can be there in 10 minutes according to GPS.” John just keyed in his response, come on.

10 minutes later, a skinny good looking twink was at the door. Jim invited him in, he wasn’t sure if this kid wanted a hook up or was really looking for a room. John asked him into the living room, they sat down, “I’m John, as he stuck out a hand, “Matt Lerner, sir” John said Please call me John, “Okay John, then he stated listen, I really need a room at least for a few nights, I have plenty of money, but my roommates got arrested and I am not being let back into the apartment.  John lowered his head,” are you in legal trouble?”  Oh no Sir Matt exclaimed, when my parents kicked me out, I moved in with a fuck buddy and his girlfriend, then her parents moved in and brought drugs and well they were wanted on outstanding warrants, the four got arrested I was questioned and told I could only go back to get my clothes.

John could see the sincerity and said,” okay let me show you your two options”, he led Matt to the guest suite, it was furnished with four poster metal bed reading chair dresser and its own bathroom. Matt said, “oh what is my other option,” thinking he could not afford this, then John walked him out to the casita with its own bedroom, kitchen bath and living room. Matt just looked at him and said, “I can’t afford this. “

John said listen what can you afford? Matt explained he worked at the dollar store, and at the local assembly plant making PPE due to covid, he shrugged and said honestly if I don’t go back to school next semester, I can do 1000 a month. John just said, 600 a month for the bedroom in the house, Matt smiled and just said deal. But I would like a lease please. John liked this kid and sat in his office and downloaded a bedroom lease, the two discussed the house, John said, “listen I like to skinny dip, if that bothers you I won’t.” Matt smiled “I prefer to be naked a lot too. If that’s okay?” John smiled all good with me except when I rent the casita, he then explained how it rents to snowbirds and folks during spring training. The two agreed and the lease was almost ready. Matt got cash from his wallet for the deposit and asked how much is the rent going to be for this month? John said, “I’ll pro rate it, when would you like to move in.” Matt smiled and said, “right now please.” John laughed. Okay the two did the math together and agreed on an amount. Matt paid got a receipt and the two unloaded the clothes from Matts car, John showed him where to park. John commented,” that’s a pretty new car?” “yeah “Matt explained,” I left home with an old Mustang, but it wouldn’t pass emissions, so my grandmother agreed to cosign a loan for me. This is the cheapest new car I could find. I put 50% down and traded the Mustang, so here it is I plan on having it paid off in 18 months. John said,” great plan;” John was impressed,

Matt went to his room wondering if he would be required to sleep with the guy, he was hot for an old man.

John stuck his head in the room and said I am making a sandwich want one.

“Oh yes please”

The two noshed on sandwiches and chips. John showed Matt the rest of the house. Gave the younger a key and a garage code. But explained the garage was for the collector cars,

Matt said that they did not really interest him, but he would respect them.

John finally said good night at 10 pm Matt returned to his room, and showered, he wondered, about the old man.

John had a hard time sleeping the kid gave him such a hard on. Oh boy.

The next morning Jim was up at 0430 he streaked his way to the kitchen and made coffee, was about to turn on the living room tv when he realized Matt was sleeping and might wake him, John took his coffee to the study that looked out on the back yard, he sat at his desk and turned on the computer and the tv he watched the news for the weather, a typical Scottsdale January. The weather was sunny and 70. He then began to write, his hobby is writing porn for a gay website, he had porn on the second screen, he did not see Matt in the kitchen, he just kept writing.

Matt woke at 5 am, he made his way to the kitchen, he saw John in the study he smiled at the reflection of the porn against the window, He poured his coffee, and thought God I want to walk in there and just blow that man. He quietly made his way back to his room and turned on the tv left the door open and masturbated on the bed hoping John would barge in.

John noticed, Matts reflection in the kitchen window, oh lord that boi was perfectly formed, such a nice tight little ass and oh lawd a perfect 7-inch cock that was still half hard from his morning hard on. John so wanted that little man but decided not to creep him out. He watched out of the study door as that tight ass made its way back to the bedroom with coffee, a minute or so later John heard the tv, he got up and decided to put on a robe, but could not resist peeking into the guest room, oh god Matt was on the bed masturbating. John grabbed his own dick and then decided that was way to creepy, he silently made his way to get a robe on.

Matt finally went and showered. He stuck his head out of the room, John must have heard him, he was wearing a bath robe. Matt went back in and put on some Hello Kitty short shorts that outlined his dick. He went to the kitchen and poured more coffee, said “Hi” as he passed the study John smiled and said, “good morning, then went back to work at the computer the porn was off.

John looked up when Matt said Hi and was absolutely tongue tied, John could only croak out” Good Morning.”

Dressed and ready for work Matt stepped into the study and said, “I’m off have a great day!” “You too “said John, dollar store huh?

” Oh yeah, till two then to the factory to make PPE till 11 then home”.

John smiled, said “I’ll leave a light on.”

3 weeks went by, Jim was up at 0430 every morning, Matt was up by 5 most mornings when he worked the dollar store. On Sunday matt was home by 3 he looked like a mess. He was putting clothes in the laundry, John stepped into the room and said, “you’re a busy man.”

Matt just nodded and said,” yeah I am going to take a nap as soon as this is done,” he was moving his head side to side to stretch his neck, Jim stepped behind him and said, put your head down, Matt obeyed John rubbed his neck till it felt loose. Matt said, “oh god thank you.” “No problem” John replied, then he continued, “Hey the hot tub is 102 degrees, and I am going to Jump in want to join?” Matt stared at him. Held his gaze for a full minute, then said uh sure,” is this okay to wear?” John smiled and said, “yes but I generally go naked.” “Ok’ Matt smiled. John retrieved a couple of beach towels from the laundry room linen closet, he grabbed his iced coffee, pointed to the fresh iced tea and said help yourself, Matt did he filled a plastic tumbler that said pool cup on it. John stripped and got in the hot tub as he sank into the bubbles Matt noticed his hard 6” cock, and how its mushroom head flared, he smiled at the thought of that in his mouth, John starred as the young man stripped and got in John offered a hand and Matt accepted.

Feet touched under the water, John did not move Matt rubbed them with his John played footsy back, Matt moved closer to his older friend, John smiled and said, “listen, I am way older than you. Are you going to be okay where this is going, we still have to be roommates.” Matt just smiled and said, “I’m good with it” John wasted no time, Matt submitted to the older man John started at the youngers feet then worked his way up legs an paid special attention to that firm tight ass John lifted his boi and sat him on the edge of the Hot tub, John took the whole of Matts nice sized cock int his throat, Matt exploded instantly John swallowed, turned the boi over and began to dine on fresh hot flesh tonging that pink rosy hole till Matt was moaning,

John picked the boi up, wrapped Matt’s legs around his waist, and carried him to the master bedroom. He laid the boi down and reached for lube he lubed his dick and began to rub it on the rosy hole. He rubbed Matt with more lube and inserted his finger. It was tight. But Matt had his eyes closed and seemed to be enjoying the finger fuck. Matt began to masturbate. John put his swollen mushroom head at the bois opening and pressed. His head slammed through the tightness so fast John froze. Matt was wide eyed. John just held the bois legs to his chest after a minute Matt nodded yes, John had to pull out twice to lube up but 10 minutes later Matt had cum 2 more times and John’s seed was traveling around inside Matt.

Matt curled up to his Daddie, John held him till he fell asleep John then covered him in sheets and blankets.

John crawled into bed at 10 that night, Matt slept the afternoon away, he woke when John came to bed. But just snuggled up to Daddie and fell asleep again. At 4:30 john woke to Matt holding his hard cock and drooling on his hairy chest.  John woke him. And said,” Hi.” Matt woke slowly. Then realized he was holding John’s dick. He stared to remove his hand but thought better and began to stroke it. John relaxed back into the pillow and enjoyed. Matt then reached over and grabbed the lube. And began to ride his Daddie. John took the bois cock to hand and made him cum as the boy used his oh so tight ass to pleasure the older cock. John obliged and filled his boi up again, the two then went into the master shower and soaped each other up and enjoyed each other’s bodies. John opened the bed room closet, Matt walked in and said,” Shit what I could do with this!” smiling John replied, “You like clothes, “Yes that is what I want to do, have something to do in the fashion industry, that’s what I want to go to school for. John wrapped a super soft robe around his little man, it fresh from the towel warmer, Matt loved the way the soft warm cotton felt against his skin. The two got coffee and began to get ready for work.

The next weekend Matt had worked himself sick, John had noticed how thin Matt seemed to be.

John knocked on the bedroom door. Matt was in the bathroom puking; John just walked in and held the boi’s long hair from getting in the toilet. Without a word Matt let John shower him and put him to bed.

John was at the desk in the study, he was going over the latest proposal to buy his business. Matt came in wearing Hello Kitty shorts, John was naked.

“How are you feeling,” Matt just burst into tears, John scooped him up and held as the tears fell,

“what’s wrong? “

“It’s so fucking hard, I am working my ass off and I can’t get anywhere. I am so afraid I will lose my savings.”

  Matt went on. John just held him and listened, When matt finished, he grabbed John’s dick, John stopped him, “Hey you don’t HAVE to sleep with me. “

Matt gave him a confused look.

“Oh I love fucking with you, You are hot, but don’t feel like you have to.”

Matt shook his head, Why don’t you take a day or so and figure out what you want,

Oh, I am so screwed I’m never going to get ahead.

John raised his voice, “Bull shit.”

Matt started to cry again.

John smiled, you need to take a day or so, meet with your friends, enjoy the hot tub, do whatever. But not work, John grabbed the boi’s side, “And Eat!”

Matt agreed to take his vacation from the dollars store and use his 3 PTO days from the factory.

The following week

John had accepted the buy out of his company, He sighed as he pulled into his drive, Matts car was there.

John smiled knowing he was not alone.

The music was flowing from Matts room, laughter coming from the room was welcome,

John went to his room and showered the day off and dressed in casual shorts car show t-shir and bare feet,

He made his way to the laughter; he stuck his head in and said, “Hi.” Matt turned down the music, “Hey there, this is my high school buddy, Rachael, John smiled and said nice to meet you. He then exited and went to his garage to spend some time with his car.

A couple hours later Matt came out, “Is that okay I had her over?

John looked confused, then said, “well hell yeah! Listen John said as he sat down ,

“I want for you, to have the best life. The best career of your choosing, the best of friends, and to be surrounded by the things that make you happy.”

Matt laughed, “I wish I knew how to do that. “

I can help, but it takes hard work,

Matt said, “I don’t even know what I want.

John smiled; “you shouldn’t know yet.”

John spent a lot of time explaining his life and business and how he got there.

Matts mind started to create a life,

Another month goes by.

John came home from 2 weeks at his beach house in Mexico, the house was clean but there was a clear sign of a party. John deposited his bag in his room, put on his customary shorts and car show T-shirt.

He looked out at the pool Matt was there with another young man.

Matt noticed and looked like he was caught red handed. John came out and said,” hi boys. “

Matt introduced Jimmy, John said please to meet you.

“Hey matt we are having folks in the casita next weekend,”

Matt relaxed and said,” ok no nude sunbathing after next week”. John smiled and said, “yeah but just for a few days.”

Jimmy Piped up, You nude sunbathe,

Matt seemed to not know what to say. John chimed in. “hell yes we do.”

John said, “I am going to unpack you two have fun.

John snuck a peak outside and both boys were bare ass up taking in the sun and holding hands.

“Hey Daddie” Matt began as he entered the master bedroom. John smiled and said, “hi sexy boi.”

“Are you mad at me for having Jimmy over?

“oh, hell no, remember what I told you I want for you, the best life?”

Yes, sir I do.

“Well, that means the best of relationships too.”

“Oh, “

“Are you in a monogamous relationship with Jimmy?”

“oh fuck no” he is hot but, he doesn’t have a clue, still lives at home. He works at the dollar store with me.

John looked concerned, “Is he a minor?”

“Oh no he is 19” “he says his parents gave him a year off to decide what to do, If he doesn’t have a plan for college by the fall he has to go in the army or navy.

John laughed. “Ok that’s sounds interesting. “

Matt crawled into Johns reading chair with him.

Matt kissed his Daddie. “I missed you.”

“I missed you too.”

The couple enjoyed each other’s body. John made Matt cum 3 times with his hand before he filled his boy with seed.

John had just pulled out. when Matt said, “I want to fuck you.”

Oh yes please.

Matt pulled John up on his knees and buried his tongue in John ass.

John got lost in the warmth of tongue probing him.

Then the full ness of a hard cock entering his ass. The length was perfect, Matts head was just tickling the spot at the top, in no time John was having his first annal orgasm in years. Then he felt Matt fill him with warm creamy seed. Matt continued to piston in him. The cum had him so lubed. That the orgasm continued, John thought he was going to pass out when Matt unloaded again. John felt the boy go limp and slide from his creamy tunnel. John gasped for breath, “where did that come from?”

“I tried to fuck jimmy because he wanted it, but he was so tight when I got in, he could not relax, but oh man did that warmth feel good, and your ass is so nice and hot I came twice!”

“Wow’ was all John could say. Matt cuddled to him all night. John was standing naked in the kitchen the next morning When matt came out. He cuddled up to his Daddie as they were standing in the kitchen, and said I have a plan for work and school, want to see?

John said, “sure” the two sat at the kitchen table with coffee, and John listened to a well thought out and researched plan for one job and college.

John just said. “Wow that is an excellent plan, I think you should go for it. Matt smiled; “can I stay here?”

“Of course, you can.”