Timmy's Adventures in Dog Sitting: The Affair

Timmy exited the school bus with a sense of relief he had not expected. The knowledge that this was the last time he’d ever have to do it felt like a literal weight was being taken off of his shoulders. Timmy was probably even more excited to never have to ride the bus again than he was about never having to go back to school.
Although Timmy had been Eighteen for almost nine months and got his driver’s license over two years ago, he still didn’t have a car of his own and his Mother worked most days so her vehicle wasn’t an option. He wanted a car of his own more than anything but money was tight and with college approaching it just wasn’t an expense that they just couldn’t afford.
What made it all the more frustrating was that Timmy could afford it. He had been filming and posting videos of himself in women’s clothing doing all sorts of sexual acts since a week after his eighteenth birthday. He charged anywhere from two to five dollars a video and business had been very good the last six months. This wasn’t a conversation Timmy was looking to have with his mother, though so he opted to just keep riding the bus.
As he was just about home Timmy heard the distinct sound of heavy breathing approaching behind him and turned to see a midsized dog trailing about ten feet back. The dog almost looked like a small German Shepard but with short, mostly dark grey fur apart from a few black patches here and there. Timmy had been doing a lot of canine research lately and was willing to bet this was an Australian Cattle Dog.
Timmy looked around in an attempt to spot an owner but there was nobody else in sight. There was a collar and a tag around the dog’s neck so Timmy assumed it wasn’t a stray. Plus, he was pretty sure he had seen it around the neighborhood a time or two.
That was before Timmy had discovered his newfound doggy desire though. The lust and craving of puppy love had come from Chester, a half mastiff-half boxer mix that belonged to his mother’s fiancé, Mark. Timmy had been left in charge of the dog while Mark was out of town and after an unexpected blow job from Chester, Timmy’s life had changed forever.
It had been almost a full week since Timmy’s wildly amazing sexual adventure with Chester and all he could think about since then was doing it again. If he couldn’t have Chester back then maybe this dog could make for a solid replacement. Even if only a temporary one.
He bent down to check the dog’s tag and concluded it was the one he was thinking of. Or at least it lived on the same street as the one he was thinking of. Timmy had occasionally seen him while on his afternoon runs but hadn’t really thought anything of it. There had even been a couple of occasions when the dog had escaped the confines of its backyard and briefly followed Timmy. Usually for no more than half a block though.
Timmy flipped over the tag on the collar to learn that the dog answered to Milo and without warning the animal began to sniff at Timmy’s crotch, even giving a couple of swift licks to his jeans. Timmy quickly stood up and looked around to see if anyone was watching, relieved to discover that the street was still completely empty.
Though the lick was brief and through layers of clothing it had been enough to get Timmy’s mind racing. He hadn’t even really been serious in thinking about this dog in a sexual manner but now all he wanted to do was find a way to get Milo home and see if he was down to fuck a time or two. He knew the dog was at least curious and that made Timmy excited.
He figured his best bet was to just continue home and hope the dog kept following. And follow he did. Before Timmy knew it he was making his way into his backyard with Milo at his heels. They entered through the sliding glass door into the kitchen where Timmy filled a bowl full of water and set it on the floor. Milo went straight for the bowl without hesitation. Timmy still wasn’t sure that this was going to go as planned but he figured this might be the only chance he ever got with Milo and that he should make the most of it. He decided that while the dog was preoccupied he would go get changed and maybe set up a few cameras.
*
Timmy was back within a few minutes, now wearing nothing but a lacy and very revealing pink thong. While trying to pick an outfit it had occurred to him that he’d never shot a video in the kitchen, not even a solo one, and since Milo was already there anyway he figured now was as good a time as any.
After tying an apron around his waist, Timmy turned on both of the cameras he had setup and checked them to make sure the entire floor of the kitchen was visible. Once satisfied he put on a black baseball cap and dark sunglasses in hopes of hiding his identity. He was pretty sure he’d never share his doggie videos with anybody but it didn’t hurt to keep them anonymous all the same.
Timmy got down on his knees near Milo before lowering himself to all fours so that the two were face to face. He played with Milo for a bit, rubbing behind his ears and telling him what a good boy he was before softly planting a gentle kiss on the dog’s mouth. Milo didn’t respond as Timmy had hoped so he tried again but this time holding the kiss until Milo darted his tongue out. Timmy opened up just wide enough to let the dog in and for a few brief moments the two were making out.
Timmy closed his lips around the dog’s tongue and sucked it in before twirling it around a bit in his mouth. Just as Timmy was really starting to get into it though Milo pulled out and began sniffing at Timmy’s crotch again. Getting back up onto his knees, Timmy lifted the apron to give the dog better access and Milo instantly began licking at the panties, eager to get at what was behind them.
After a few seconds of this, Milo seemed to get a bit frustrated and so Timmy finally pulled the panties aside and allowed his dick to float free. The dog was after it in a heartbeat, focusing mostly on the head with short, excited licks. Timmy was just starting to get hard when suddenly it seemed as if Milo had lost interest again. He began sniffing around Timmy’s thighs before making his way around to the back where he gave the anus a brief lick and then started working his way down.
Milo was licking Timmy’s bare feet now when the young man decided he’d go back down to all fours and pull the panties aside in the back, giving Milo plenty of access. This was seemingly all the motivation the dog needed. He quickly began licking up and down Timmy’s ass crack before focusing on the anus in full. Timmy reached back and spread his right cheek open and now Milo was darting his tongue in and out of it in quick but deep little bursts.
Timmy began to moan as he rocked back and forth with the rhythm of Chester’s tongue. He had forgot how good this felt. But, yet again, before he could really get into, Milo had lost interest and moved on. Before Timmy could even turn around to see what the dog was doing he had pounced on him. Milo grabbed Timmy firm around the waist with his paws and began humping furiously.
The dog was just hitting air though until Timmy spread his legs apart, lowering Milo’s target. Two more thrusts and Milo hopped back down and started licking again. Timmy knew it was only a matter of time before the dog tried again and so he lowered himself just a bit more, making sure he was ready for it.
Milo indeed tried again and this time he hit his mark on the first thrust, jamming his dick into Timmy who was more than a little surprised by the punch this relatively small dog had. It wasn’t just the size of the cock but the speed and quickness that Milo was slamming it in that caught Timmy off guard. It was a hard, rough fucking and Timmy was loving every second of it.
Timmy could feel Milo’s dick growing inside of him and pre cum was begining to dribble from the tip of his own shaft as he felt the knot begin to swell. He didn’t even need to reach down and stroke himself, the aggressive ass fucking he was receiving had done all the work for him and now Timmy was exploding with pleasure as he shot load after load onto the kitchen’s linoleum tile.
Milo gave one last final thrust, even harder than the rest before suddenly turning around on Timmy and unloading his own torrent of semen deep into the young man’s ass. Again, though, Milo seemed to have lost interest and tried walking away, still fully knotted up. Timmy winced at the sudden pain and instinctively backed himself up a few steps before grabbing a hold of one of Milo’s legs.
“Stay,” was all Timmy had to say and the dog did as he was told.
Timmy relaxed and went back to enjoying the feeling of Milo’s pulsing cock unloading a river of jizz into his ass. As he opened his eyes between moans, Timmy noticed that he had backed himself up enough that his face was directly above the rather large puddle of his own semen. With very little hesitation he began hungrily licking it up off the floor.
He licked and slurped for a good thirty seconds, making sure he got every drop of his jizz, even the bits that had seeped between the tiles. By the time he was satisfied he had gotten all that there was to get he could already feel Milo’s knot beginning to shrink.
The dog began walking forward again and this time the pain was much less, almost pleasant as Milo’s knot slid out with relative ease. The dog turned back around and, much like Chester had always done, Milo began licking up the semen as it flowed out of Timmy’s ass. Unlike Chester though, Milo seemed to be really into it.
He licked Timmy clean until the jizz had stopped flowing and when that was over he didn’t just wander off to do his own thing. Milo made his way forward so that his ass was directly next to Timmy’s face. Timmy took the hint and grabbed Milo’s still hard and dripping cock, pulling it back between the dog’s legs and immediately began sucking on it.
It was just small dribbles of cum now but Timmy found he could work a little more out of it if he stroked the shaft while he sucked. He loved the taste of it too. Maybe not as much as his own, he certainly wouldn’t lick it up off the kitchen floor just to get a taste but straight from the source was pretty damn good.
Eventually, Milo got bored of this too and made his way towards the still open sliding glass door that led to the backyard. Timmy was glad now that he had made sure to shut the gate outside. He still had hours before his mom returned from work and he planned on making the most of his time.
As great as Milo had been, and even though Timmy fully intended to take his dick as many times as he could in what time there was, he couldn’t help but feel guilty. As if he were cheating on Chester, a dog he wasn’t even certain he would ever see again, let alone have sex with again.
No, Timmy needed to move on and accept the new gift that had literally wandered into his life. The only thing to do now was to figure out a way to make this happen on a more regular basis.
Thank you for reading, I hope you enjoyed it. Stay tuned as Timmy fully embarks on the life of a fulltime Dog Sitter. New clients means new dogs and new dogs means there are some wild new experiences in store of Timmy.

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