Caretaker at Pup House pt 1

The day I quit my job at the Burger Train I felt pretty good, ecstatic really, I told my boss to go fuck himself and walked out with my shoulders high. Two weeks later as I sat in a gay bar with my head in my hands, fingers entangled in my mop of dirty blonde hair I was pretty miserable because I couldn't find a job. I had a few hundred dollars left in my savings account and not much in my checking but I was buying myself drinks as I tried to come up with a plan.

Piss drunk I got to my feet and drifted back to the men's room. I pushed my way inside, went to the trough and unzipped. I untucked my dick through the opening in my briefs and started to piss when l looked up to the wall and saw a unique advertisement written in black marker.

Caretaker Needed for Pups
Grown men who get together on the weekends, some weekdays, and holidays. Looking for kind handler. xxx-xxxx

I took a photo of the ad with my phone because I thought it would be a sort of laugh. I thought I'd text it to a few friends, maybe post it to social media. One of those kinky things that could only be found in a gay bar. I put my phone away, made my way out to the bar and finished my drink before I left. It was a short walk to my basement apartment in my parent's house. I crawled into my unmade bed and fell asleep.

Four hours later I woke up, drool on my pillow and I smelled like a brewery. I got to my feet, stripped off my clothes as I made my way to the toilet. I did my business then got into the shower, soaped and rinsed off, washed my hair. Every part of my lean, skinny body felt clean and I had a need so I jerked off quickly.

My legs felt squid like as I made my way back to the bed with a towel around my waist. I sat on the edge of it and started to look through my clothes when I remembered the ad on my phone. I got it out, got to the ad, read it over again. It was funny at first but I couldn't bring myself to send it. It had someone's phone number. I opened the editor, readied to wipe it out but I couldn't make the swipe. There was something about it. Someone, some people looking for someone else to play a role. I typed the number into my phone, made the call.

"Hello, this is Paul," a man said.

"Hi, my name's Brad. I uh, saw your ad on the men's room wall. Is it real?"

"Why don't we meet somewhere and talk?"

"Yeah, sounds good."

"Afterwards if you feel up to it we can go back to my house to talk."

We met at a coffee shop within walking distance from where I lived. He told me he'd be wearing a mauve polo shirt. I told him I'd be dressed in my usual white t-shirt and jeans. He greeted me with a handshake, looked me over. I kind of felt like a piece of meat but I was doing the same. He was handsome, taller than me by a few inches, well groomed. He smelled of musky cologne, the type of smell that was good to wake up to in the morning. He had an easy smile, muscled forearms. I couldn't tell his age, maybe mid-thirties, at least ten years older than my twenty.

 He made me feel at ease as he ushered me to the line where he offered to buy me a coffee. I accepted but ordered a small latte trying to remain polite. After my drink was made we walked to a table by the window where he had been sitting, there was a cup of coffee and an electronic tablet.

"I know it's a weird place to leave an ad, especially with my phone number, but my friend Matt did it. He's a bit impulsive."

"It got my attention," I said.

"Do you have any experience in this kind of thing?"

"Uh, not really, but I'm open minded, you know. I'm not judgemental."

"Are you in college?"

"Community, and I worked at a fast-food place but I quit recently."

"Really?"

"I'm looking for something better, something different."

We fell into an easy conversation after that. We talked about different things. He told me about his work as a manager at an investment fund. I told him about my film studies and my interest in the history of the studio system. I was at ease with him. I felt a connection and that he genuinely wanted to be with me so when he asked if I'd like go to his house I agreed.

"Listen, the thing is I live with a couple of people, Matt who I told you about and Adam. They're both home and eager to meet you. How would you like to meet them?"

"Yeah, sounds good," I said.

He made a quick call to let them know we'd be there soon as we walked out of the shop to his car, a red Mustang. The whole drive there I couldn't help but think of what his house would be like and the two men I'd meet. Would they greet me at the door on all fours with those pup masks on? Would they try to lick me or maybe even sniff my crotch? I was anxious about it but told myself I had to be brave enough to see it through, to have the experience.

It was a quick drive out of town on the highway, each car we passed, each light we passed meant I was getting farther away from home. He was an aggressive driver but not risky. He turned on the radio and I fell into the calm, passive state I usually achieve when someone I trust is driving. Far away from the city he pulled off the highway to a development area. We passed several newly built homes until we reached a gated community. I thought for sure we'd pass it but we didn't. He even had identification to show the guard. Just how rich is he? Just how rich are they?

He drove us through the sprawling neighborhood until we got to what felt like the last houses, the biggest houses, houses with walls and fences around them. Walls within walls, I thought as he opened the gate with a swipe of a badge. He drove up a winding path through trees and finally it was there. His house and it was larger than I could have imagined. He pulled in front, got out and started to the house but I didn't move. I was stunned and it took him coming back and opening the car door to snap me from it.

As we walked he put a comforting arm around me and asked if I was okay. I welcomed the touch and told him that I was but I was lying and I think he knew it. The front door was opened before we even got to it. In the well lit opening were two young men with their arms around each other. They looked so friendly, so eager, kind of like pups. Each of them extended a hand to me and introduced himself.

Matt was a bit of a punk with a mohawk, piercings, and tattoos, a band around his forearm made me think he might be into fisting. He wore a sleeveless, muscle shirt that looked as if he'd made it himself. I could see his bare sides, his muscle and hints of more tattoos. It gave me a chubby.

Adam was more of a choir boy, a mop of blonde hair and he was dressed in a button down white shirt and slacks. He looked to be my age. And there was something mischievous in his eyes.

Wanderlust- Christmas Vacation

My first few weeks at college were a blur of ceaseless activities, everyone wanted to get to know everyone else, if only to know who to avoid in the future. There were many late nights, studying at odd hours like four in the morning just before the test, and talking to friends about the meaning of life, homesickness, and careers. But nothing classified you more than the frat experience. Some pledged to fraternities out of their league, while others like myself reluctantly joined a house only after my roommate, Michael, bothered me about it. We didn't pledge the same frat. He was more enthusiastic about the prospect than I was because he was a legacy at an elite frat. I joined a bunch of fellow hay seeds.

There was very little homosexual and homoerotic activity where I pledged. There was a paddle involved and a lot of us just being in our underwear, but it felt so casual, guys walked around in less in the dorm bathrooms. I didn't ask my roommate but I heard rumors about what he had to endure. I assumed there was a lot more paddling and humiliation to it. One person told me he spied on them once, saw all the pledges in cloth diapers. Another person told me they sodomized each other. Possibly the most accurate was a pledge having to lie naked in a coffin with his fraternity brothers around while he confessed everything he had ever done wrong so they'd know his secrets. My first thought was blackmail but the person I was talking to said it was for protection. I dreamed of being a fly on the wall when my roommate was doing it.

At over six foot tall he was a head taller than me and I had seen him naked around the room, in the bathroom. He was broad shouldered, muscular, and well hung. It was difficult imagining someone paddling him but not impossible because he had this kindness to him, a sense of humor. I knew he came from money but he never lorded it over anyone. He was actually generous with his time and his money. That's how I ended up going to his family's home for Thanksgiving and Christmas.

We'd been talking about our home lives one night when I mentioned I'd be staying on campus. He told me the school mostly closed but there was a traditional meal for students, faculty, and administrators who had nowhere to go. I made a sarcastic remark about a tin of beans and some canned ham which he laughed at a little but then he invited me to go to his family's home. I declined at first because I didn't want to impose but he told me to think about it. When I finally accepted he got a little excited about it, started naming things we'd do, things I'd get to see.

Thanksgiving was just a two day thing. We traveled up the day before, slept in his old room, me on the floor and him in bed, got up the next morning with everyone else. His father was a strict, intimidating man who had to win a handshake. His mother was a polite woman who I seemed to think of herself as being better than most people though she'd never say it. He had two brothers and a sister. One brother was older, the other was three years younger and his sister was the youngest, barely a teenager. They were polite to me but reserved. I kind of felt like I was getting the cold shoulder and about to think the whole thing was a disaster but Michael wouldn't let me get negative.

He took me around his hometown a little, showed me where he went to school and we got candy from a little store on Main Street but mostly it felt like we were killing time. That night everyone ate too much at dinner, we smoked and drank with the men in his father's study then went to bed. The next morning we left and traveled back to campus. We said it was to study, which we did a little but mostly it was to be on our own without people looking over our shoulders. His mother sent along supplies that lasted us a day and a half, after that we made trips into town to eat at one of the diners.

Christmas was different because for starters it wasn't at his father's home, instead it was at the family home, an old estate out in the rural, farmlands. But it wasn't a farm exactly, though they had horses and other farm animals, it was a mansion. The extended family was there so again we had to share a room but there were more servants, people who took care of things.

For once the holidays were about playing and fun, not full of chores and responsibilities. We did the things we were supposed to do, church and family time, but we also had a sense of personal time that we could do whatever we wanted. For Michael that usually meant hiking in the snow. The only good part of that is when we'd get back to the house, back to our rooms, and strip down for bed. Our room had its own fireplace but Michael wouldn't let me sleep on the floor as it was so cold outside. He insisted that we bundle together.

Everything was fairly ordinary. His parents did have an extra stocking by the chimney for me and it did have a few presents, though less than others. I had only thought to get him a gift, a pen and pencil writing set. He got me an engraved, metal bookmark. Really the gifts weren't the important parts though. The important part was not being alone, that and drinking with the other men after supper. Most of it was uneventful except the last night there.

The last night there we strolled back to the room arms around each other, drunk on brandy. We fell onto the bed together, a fire having already been made for us the room wasn't very cold. Side by side we chatted a little about things until we fell asleep. An hour later I woke up to the sound of him sleeping and an erection strained against the inside of my jeans. I barely gave it a thought, at least there was no worry, as I began to rub my dick as I stared at him. I worked myself until all I wanted was to have an orgasm and that's when he woke up, looked to me and smiled. At first I thought it was just the liquor and I half expected, wanted, him to turn over but he didn't. He sat up a little on his elbows, looked to me.

"Having fun?"

I was stunned by his question for a moment before I could think of just how ashamed I should have been. I had taken our intimacy, our friendship, for granted. This was it, it's over, I thought. But he just smiled at me, then he did something I didn't expect, he reached for my dick. He had hold of it for a moment until I pulled away, pushed myself to the edge of the bed, dizziness stopped me from moving away more and getting up.

"I won't tell anyone," he said. "It's normal."

My face flushed, my fingers tightened on the denim, and I could smell the fire burning a few feet away from us. I felt the bed shift as he got to his knees behind me and moved to my back, cautiously, gently, he wrapped his arms around me. I feared for a moment that he'd attack me though he had never been violent with me before but still I felt it. Instead he pulled me into his embrace, put his head on my shoulder. Our cheeks touched. It felt electric. His fingers moved up my shirt, his hands were so certain as he unbuttoned my shirt, pulled it from my body. Next was my undershirt before he pulled me backwards, lay me at his side as he moved his body partially over mine. He unfastened my belt, my jeans and pulled them down where he hesitated for a moment with my shoes.

Once they were off my whole body relaxed despite him pulling off my jeans and socks next. He ran his fingers up my legs through my thin growth of hair until he reached my white briefs, my aching dick. He slipped a few fingers under the band at my thigh, tickled the fleshy head until he peeled back my foreskin. I gulped for breath and spit as he traced it with one finger. I reached for him with my nearest hand. I was barely able to touch him back when he ran his finger up to my bellybutton. He lay his palm on my tummy as he moved to kiss me. Our burning lips touched, there was a flick of tongue and then he pulled away.

"You can't tell anyone," he said.

"I promise."

"Good because I want this to be special."

He kissed me again as he pushed his hand back down to my underwear, put his fingers inside to my slippery cock. I rolled towards him a little, finally got a hold of him with my far hand, felt his hip, his belt and tucked in shirt. He was still completely clothed and I was almost naked, definitely the most vulnerable, so I pulled at his shirt until it came loose, unfastened his belt and slacks. I grabbed hold of his dick as it poked out of the fly of his boxers. We worked each other like that for a while as we continued to kiss. Finally I pulled away from him.

"I want you to fuck me," I said.

His head fell, his face half buried in my shoulder.

"I've never done much more than this. I've sucked a little, usually the other guy does the same. I've never, you know, done it."

I squeezed his dick until he looked me in the eye.

"I'll show you how," I said.

"Really?"

"Yeah, but we should get under the sheets. It's cold."

He pulled away from me so I got to my feet as he did the same. I pulled back the covers, then watched as he stripped down completely, his dick stuck out from him and bounced as he got back into bed. I pulled off my underwear, got back in on my knees, straddled him as I pulled the blankets up over my back. I squashed his dick and mine between us as I kissed him some more, played with his nipples until they were hard points and he began to fidget at my touch.

Satisfied that I had worked him into a passionate desire, that I had his consent, I kissed my way from his neck down to his dick. In the darkness under the sheets I licked and kissed it, nibbled and spit until it felt slippery, then I spit into my own hand and rubbed it on my asshole until I thought we were both prepared. I moved back up him, over his dick then back onto it. Slowly I worked it inside of myself with the help of some more spit until I settled to the base, my balls touched his pubic hair for a moment before they retracted as I played with my own dick. I worked myself slowly as I was conscious of the way it made my asshole contract. I felt him there. He was inside of me but I was the one who really had him. He was subject to my desire, my will.

I rose up and sunk back down slowly, listened to the way he breathed. I grabbed at his chest, twisted his nipples some more until he moaned. He grabbed at my hips but I pushed his hands away. I wanted him, his need, to be under my control. I lowered my head for a kiss and he tried to raise his head up to meet mine but I dove in shorter to his chest, his neck. I sucked at his flesh and gave him my fingers, stuck them in his mouth. His lips were like smoldering coals that came to life with my touch. His tongue, his spit, my fingers went to the back of his throat, back and forth, in and out as I continued to ride him.

Sweat ran from my shoulders, pooled at the small of my back. He groaned and grunted to my manipulation. I bucked a few times, then slowed, a few more times as I reached back and took hold of his balls. I pulled them a little, tickled them. He tried to take hold of me again but I pushed his hands away. I slid off of him, scooted up over his arms, pinned him to the bed, stuck my dick to his lips. He sucked at it eagerly so I pushed inside until he gagged, then I pulled out to let him catch his breath. I took hold of the back of his head and told him to lick my balls which he did without complaint.

I toyed with my dick as he licked me down there, sometimes his tongue went a little deeper but not by much. He kept at until I knew I was close to a climax. I moved back down, took hold of his dick and worked it back inside of me. It didn't take much more to send me over the edge. My ejaculate shot up to the headboard, into his hair, onto his face. That was when my body gripped him the tightest and he also ejaculated inside of me. We moaned in pleasure and pain, then fell silent. I pushed myself from him, fell beside him, put my head in the crook of his arm, let one arm settle over his chest.

We smelled of sweat, but I didn't want to move as my senses came back to me, not until we had cooled off and then it was only to pull the blankets and sheets up over top of us.