Window Watching

Story by HarryHobo on SoFurry

, , , , , , , , , , , , , , , , , , ,

After catching sight of his busty mature neighbor undressing, a young collie boy becomes obsessed with her.


His name was Jamie. He was a fourteen year old smooth collie boy who had too much free time on his hands ever since school had its summer break. He was leaving middle school and heading into the high school once. He was slowly becoming a man and with that, his body was going through changes. He began getting funny feelings about girls. Finding himself staring at them and realizing just how cute they are to him. His school had him and a bunch of other boys watch a video about their changing bodies which only made him feel more nervous about the erections he sometimes gets at the worst possible times. A changing body sucks. Puberty is just the worst when you are young and you don't know how to control your primal urges.

Luckily, Jamie found a way to handle these urges. First came the internet. Sites dedicated to porn taught him about how to masturbate at the computer. He first masturbated with his clothes on and came in his underwear. Sadly, this left some major evidence that his parents took notice of much to his embarrassment. His father told him to use tissues instead with his pants down so that he can just throw out the mess. And for a good while, it worked out for Jamie. But sadly, his computer was hit by several viruses thanks to the kid's lack of proper spyware protection, leaving him without a computer for a little while before his dad can get it fixed. It was during this time that the most amazing thing had happened.

He was at his chair next to the window. Bored out of his mind. Jamie was glancing out his window when he spotted something unexpected. His window was facing towards the house next door, and in the window across from his was the bedroom of his next door neighbor. She was an older woman who lived on her own. Jamie remembers hearing that she was a widow with two sons who are living on their own. Jamie never really bothered knowing much about her beforehand. Never finding any interest in her until just now. For within the view of her window, she was getting undressed.

Jamie nearly fell over in his chair when he saw the woman in her bra. His eyes shot down towards her large breasts. The young pup only just now noticing how large chested this lady was. She usually wore such plain and old lady clothes. Never catching anybody's eyes with how unfantastic her style was. She wasn't exactly young looking either. She had wrinkles under her eyes and her golden collie fur had started to turn grey with age. Her sight was ebbing away so she is forced to wear thick glasses all the time. Which is probably why she hasn't spotted him staring at her as she was starting to remove her bra.

Her glasses were off. And surprisingly, she had a very beautiful face if a bit aged. But still good enough to be on the cover of a very adult magazine. Or porno site. Something a teenager has much easier access to in the privacy of their bedroom. And speaking of teenage boys...

Jamie's legs grew shaky as he watched. His young boy parts tingling with excitement as an erection grew from his pants. When those fluffy white tits came out of her bra, he had lost all control. He ran into the bathroom and rubbed himself out a new one. A new pornographic image of his next door neighbor taking up his mind's eye. It was from that day forward that the youth took up a new hobby. Spying on his large breasted milfy neighbor.

He kept it covert. He always had the blinds down so on the off chance she might see him spying on her, he can quickly shut the blinds. He has a box of tissues nearby so that he can have quick access to it whenever she starts undressing. The young teen takes note of when she was up and about. Checking the times and discovering the patterns. Once he got it down pat, he was finding a regular time to spot her undress. Jamie looks forward to these peepshows every day. Finding any excuse to go up to his room, take off his pants, and fap away to the sight of the mature collie getting out of her clothes. It was the best thing in the world for him.

Jamie can't get enough of seeing those huge tits of her's. Sure, they were a little saggy but that is what makes them so much better than the boobs on the internet. This was real. These breasts were the real deal and all natural. She was perfect. Even right down to the pudge of her stomach to the thickness of her ass. Jamie masturbated to every part of her. Once his computer was fully functional again, he began taking pictures and uploading them onto his PC. Using those pictures instead of the websites to fulfill his sexual desires. But simply looking at photos wasn't enough. He wanted more.

Learning his neighbor's pattern, he figures out that she always left the house for work every morning at 10 AM and returns every 3 PM. Jamie also knows for a fact that she never locks the back door to her house since she figures nobody will go over the fence. Ofcoarse, she never expected that a horny teenage will do just that. Every day, at around 11 AM, Jamie hops the fence and carefully moves around the house. Always taking his shoes off before entering inside so not to leave tracks of mud anywhere. He searches the house for her bedroom and looks through her laundry basket. There he will find his prize. A used bra that she had worn the other day.

The young lab would bring the bra up to his nose and take in a huge whiff. Sighing out loud as he absorbs in the smell that the older woman carried. He licks the inside of the cups as he tastes where her juicy milfy tits have been. Jamie ravages that bra with his mouth. Makes out with it. And eventually zips down his shorts and starts masturbating with it. Each cup on either side of his young dick as he imagines himself having sex with the dog woman's large breasts. Jamie does this every single day. He sneaks in, goes through her laundry, faps with her bra, cums in her king-sized cups, puts it back in the basket, and leaves so to repeat the cycle the next day.

The young teen has been spending more than half of his summer vacation repeating this routine. Every morning he watches the old collie wake up from bed and get dressed. He waits for her to leave the house so that he can sneak in and masturbate all over her dirty clothes. He then leaves the house and does other, far normal, summertime activities. Once he gets back home, he checks to see if she came home yet. He goes to his bedroom to edit pictures he had taken of her so that it looks like she is giving a blowjob or tittyfuck to a selfie picture of his erect penis. Once that time arrives where she goes to sleep, he watches her undress and goes to bed. Rinse and repeat for every day during his summer vacation.

Things were pretty routine until one day he found that the back door to the woman's house was locked. Jamie thought this was a little strange. She never did this before. The young pup left a bit disappointed as he had to skip one part of his usual routine. Things only got stranger for him when he found that she had pulled down her blinds when he tried viewing his nightly peepshows through his blinds. Jamie felt a bit uneasy.

The next few days were the same. That young black and white furred pup knew something was up. She was blocking his access to her! No more peeping. No more fapping. No more of pictures to add to his porn folder dedicated to her. Jamie was at a loss. This lack of new boobage is causing him to be incredibly pent up. He needed to see that next door lady's boobs again desperately. But he isn't sure how.

One day, while he was going by the mail box, that neighbor woman was also heading up to her own box. Jamie nearly choked on his saliva as he looked at her. She was wrapped up in a sort of bathrobe that most adults he seen wear in the mornings. Her body was pretty well concealed, but Jamie took notice of the chest bulge that she had produced while wrapped up. The young lad stuck around the mailbox awkwardly as he pretends to be grabbing his mail. He took several glances at his crush as her grabs the mail and pulls it out. Flipping through the letters and pretending to be looking through them.

The neighbor woman was standing next to Jamie now. This was the closest he had ever been to the older woman before. Her blonde fur was long and rough. Common for collies like her. Some of that fluffy fur poking out from the top of her robes. Where her giant boobs were at. Jamie felt a bit nervous as he stood next to her. Her wide birthing hips inches away from him. A boner starting to develop as he found himself losing control of his thoughts...

"Excuse me." A motherly voice interrupted his train of thought. Jamie jumped as he turns his head to the collie next to him. She was facing him directly. As in, she was looking straight at him. Making eye contact for the very first time. "Oh dear! I didn't mean to frighten you."

"Oh!" Jamie stutters as he tries to recover his senses but ends up dropping some of family's mail, "I wasn't frighten! I was... oops! Um... Just very focused on this mail. That I'm picking up..." The poor boy was dying. As he bends down to pick up the fallen mail, he was silently glad that he did. Using this as an opportunity to hide his growing erection so that the woman doesn't see it.

"I see..." The old collie says as she looks down at the boy, "You must really be interested in that mail. You've been going through the same envelopes about twenty times just now."

Jamie hisses to himself as he thinks up of an excuse. "Well... yeah! You know... gotta keep an eye out for forgeries!" "Forgeries?" The collie asks in bewilderment. "Y-yeah! Yeah! There are people out there that try to get your money... by pretending to be the government and... they will take the money you are using to pay your bills!"

The collie crosses her arms as she listens to the boy. "Is that right?" "Um... yes? I... I don't know really. Just something I heard from somewhere." Jamie stumbles with his words as he got up. Using the letters in his hands to covertly cover his crotch as a bulge was poking out from it. The teenager wishing this wasn't happening to him at such a terrible time. Jamie begins moving back to his house awkwardly as he tries to escape from the horribly awkward conversation he was having.

"Well! It was nice talking to you! Bye!" Jamie lies as he heads for the door. "Wait! You have-" His neighbor shouted after him but he already was closing the door after himself before she could finish.

Jamie goes into the kitchen and drops the mail on the table. His lungs burning in pain as his heart raced at the speed of a hare. Jamie spent the next couple minutes recovering from his encounter with the milf next door. It was the worst experience he had in his whole life. He never thought he could embarrass himself like he did until just a few minutes ago. Jamie wishes that he could just go back in time and stop himself from ever talking to her. He made himself look like a complete fool to the woman he had been masturbating to almost the entire summer.

The young dog sighs as he checks through the mail for real. Separating the letters addressed to his mother and father. But while he did that, he found envelopes addressed to somebody named Dorothy McCain Anderson. Jamie looked at those set of letters as he found that he has no idea who that is. He figured that he would have to ask his mom later but he heard a knock on the door. It took him till the third round of knocking before he finally answered the door. As he opened the door, he asks, "Who is...."

He became slack jawed as he saw before him the image of his large curvy neighbor. She stood at the door with her hand clutched to the front of her robes. They seem to be slipping off of her for some reason. Jamie was staring up and down her body. Idolizing it. Up until she finally spoke. "My mail?"

"Ex-excuse me..." Jamie shakes his head to clear it then asks, "What was that?" "My mail. You had it in your hands while we were at our boxes earlier. The mail man might have put in your box by mistake. I tried to tell you but you ran off before I got the chance. And I am not exactly the best runner to give chase." "Oh jeez! I'm sorry..." Jamie felt extremely embarrassed for his actions, "I didn't mean to... I'll get them right now!"

Jamie scrambled towards the kitchen. Leaving the busty mature at his door to wait. His elbows banging against the doorway into the kitchen. The boy clumsily grabbed the stack of mail and brought it back to the woman. He was nearly out of breath as he handed the letters to her. "Here you go!" Jamie exclaims nervously.

"Wow... Thanks." The older woman said as she grabs the mail and sorts through it. She hands Jamie back the envelopes that bare his parents' name. "I don't think I'll be needing these. Thank you anyway. Tell your mom hi for me!" the old collie woman waved as she turns and walks away. Jamie didn't say a thing as he stares at the woman's flicking tail and rear. Continued to watch her walk up the drive and back into her house. Not stepping on the wet grass between their homes because she wasn't wearing any foot coverings. The young boy closed the door and walked into the kitchen as if he was a zombie. He tossed the letters onto the table and sat down. His poor heart finally went out and he fell flat down onto the table.

His morning was unexpectedly exhausting.


A couple days had passed. Jamie did his normal routine. He spied on the woman whose name he finally learned. Her window had decided to stay open in the most recent days. He even took some new photos that he photoshopped together with pictures of himself so that it looks like she is having sex with him. He masturbated regularly to the images of the older woman in those pictures. Absorbing in the pleasure his climaxes gave him. Things were finally getting back to normal after that little dry spell.

But there was still one thing he wanted to do. Something he missed so much. He would check regularly. Once Mrs. Anderson left her house, he would sneak over to her backdoor. He would jiggle the handle and see if it was unlocked. Sadly, she still kept it locked so he couldn't sneak inside. Jamie didn't give up though. He was determined to get inside. He wanted desperately to find those robes that Mrs. Anderson wore that morning they first spoke. He wanted to take in that morning fresh smell the collie has. He wanted to rub that scent all over his cock until he cums. He fantasizes himself spraying his seed all over the inside of her robes. So that she can wrap that sweet body of her's in his spunky musk.

Jamie kept at it until one day, on a Saturday, the back door finally opens. Mrs. Anderson had left around the usual time and Jamie went down to check the door. He had expected it to not open so often that he was surprised when it did happen. In his excitement, he forgone taking off his shoes and went upstairs into her bedroom. Inside, he went over to the master bathroom's door and found the robe hanging there. Excited, Jamie presses his face into the hung cloth and takes in a big whiff.

He felt so light-headed from the scent that was there. It was the strongest smell he ever found coming off her clothes. It was fresher and cleaner. He can even tell what kind of shampoo she was using. It was a tropical scent. It was... pomegranate? No. Rainforest. Maybe even ocean breeze. It doesn't matter which kind. Just the thought of her pouring that gooey stream all over her large wet mounds was giving Jamie the hardest stiffy he ever had.

He has no choice. He needs to masturbate all over it. Jamie went over to the laundry basket to dig out a bra and a pair of panties. Sniffing each one to see which had the best smell. When he gotten his favorite combo, he went over to bathroom door and pulls down the robe. He pulls off his shorts and underwear and then wraps the panties around his hard on. He then wraps the bra cups around the underwear covered cock. He spreads the robes onto the floor and lays on top of it. With one hand on his underwear covered wang, he starts throttling it while he rubs his face all over those robes. Sniffing and licking the cloth.

Jamie was in heaven. Titty scented heaven. The boy was going crazy with the older woman's bathrobes. He imagines Mrs. Anderson wearing them like she did that fateful morning. Wiggling those big juicy titties in his face and begging him to fuck them with his dick. Jamie then imagines himself doing just that. He rubs himself harder as his imagination had him fucking the older collie's breasts with vigor. They bounced up and down his cock as her screams of pleasure echoed through his mind. They probably felt amazing to fuck. Like two pillows squished together around his dick. Which Jamie only did once as an experiment before realizing too late that he'll have to sleep on them later.

Jamie takes a bunch of bathrobe into his mouth. His fantasies causes his jerking to become more and more frantic. He saw himself fucking the older woman he always daydreams about. Her tits banging against his face as she cries out to him. Calling his name and begging for him do her faster. Harder. He was drawing close to the edge. He needed to cum and cum hard. He quickly stops his pumping and took off the bra and panties from his cock. He tosses them aside so that he can aim for the inside of the robes. The parts that will be wrapping those big titties of her's.

He wanted her. Jamie wanted her titties to be covered in his boyish scent. To have those plump jugs pressed against the cum soaked cloth every single morning of every single day. She won't know it but it will turn Jamie on so hard whenever he will see her in those robes. Knowing that he had indirectly jizzed all over his favorite pair of tatas. And if the future will allow it, he plans to paint a fresh coating of his sperm as often as he can. Even if it was a school day. Even if it was snowing. Raining. Or the end of the world. He will find a way to stick his dick between her bra and cum all over her clothes.

The boy hisses as orgasm struck. His burning cock spewing out the white colored fluids from his tip and all over those robes. Jamie groans loudly as he came. Pausing briefly so that he can redirect his dick to another part of the robes so he can finish unloading upon them. It didn't take him long to sigh in relief. His dirty deed finally done.

"So my little intruder has finally been caught red handed." The voice of an older woman rang into Jamie's ear. The boy's heart stopped. Fear clutched into his chest and tightens its grip. The boy turns his head to the doorway and found that busty old collie woman standing there with her hands on her hips. Her face was stoic. He cannot tell if her expression was reading as mad, angry, upset, or utterly disgusted. His hands were trembling. His whole body was trembling! Here he was. Kneeling on his neighbor's robes after cumming onto them. Her bra and panties not too far away.

There was no out of it. No escape. The truth was clear as day. Jamie knew... that he was going to be in so much trouble.

"Oh god..." Jamie whimpers. His body felt so weak until realization of what he did had sent him into a mad fever. "Oh god! I'm so sorry! Oh god oh god... I didn't mean to... I... I... Oh my god! Please... PLEASE! Don't tell my parents! Shit... worse. Don't call the cops! I won't do it again! Honest!" Jamie quickly picks up the bra and panties so he could stuff them back in the laundry basket. Doing the same with the very messy bathrobes. Tears welled up in his eyes and were pouring down his face. The dog boy knew that his days were numbered. He was going to be arrested and thrown in jail for sure.

"See? It's all there! I didn't steal anything! Oh god where are my pants?!" Jamie screams as he groped around the floor. "Jamie." Mrs. Anderson says to him in a stern tone. "In a minute! I'm leaving! Don't call anybody!" "Jamie..." Mrs. Anderson repeats herself a bit more softly. "I'm not a criminal! I'm too young to go to jail!" "For the love of god boy! Unless you stop that blubbering, I'll send you there myself!"

Mrs. Anderson was running low on patience as the poor teenage mutt became hysterical right before her eyes. He went on rambling as tries to get back into his shorts. Putting them down the wrong hole and taking even longer to leave. At the rate he was going, the poor boy was going to jump out of the window in a desperate attempt to escape from the situation. The old collie needed to calm the lad before he hurts himself. She tried talking to him but he is too panicked to listen. She even tried shaking and yelling at him to shut up but that didn't do much but made him louder. Mrs. Anderson had only one other option she had yet to try.

Jamie quickly finds himself get muffled. His crying and whimpering was muted as he found himself getting pressed into two soft pillows. His heart began to beat slowly as he finally calms down. He gives a sigh and snuggles into whatever his face was in. He heard a woman's sigh and his brain started working again. He lifts himself up and stared down at the greatest sight of his young life. His neighbor's bust.

He didn't get the chance to notice at first what she was wearing due to being sent into a panic, but on closer inspection he found that she was wearing her sweater vest with the plaid patterns. It is very ugly and tacky, but she made it look good with the size her chest. He also believes he might have saw that she was wearing a long skirt but he wasn't completely sure. Her chest seems to be the only thing getting his attention. It is the thing that was making him stand up in attention too.

"I see that you finally calmed down." Mrs. Anderson says to Jamie. "Ahuh..." The boy barely replies as he is hypnotized by her ginormous bust. "I thought you were gonna leap out of my window at any second." "Yeah..." "Eyes up here champ." "Wha..? Oh! Sorry!"

Jamie glances back up into Mrs. Anderson's face. Her expression was a bit easier to read now. It was full of concern in a motherly way. The kind of face that can make a boy feel guilty. It is also the kind of face where you know that you are about to get a big lecture from. Jamie's ears folded back as he silently waited for her to speak. When nothing was said, he broke the silence.

"Um... Am I... in trouble?" Jamie pathetically asks. "To a certain degree, yes. But as far as police are concern, I don't think I need to call them this time. Despite the number of laws you've clearly been breaking." Mrs. Anderson spoke clearly as she sets Jamie onto her bed. She sat right next to him. "For the past few weeks, I've been noticing a few strange things. Whenever I do my laundry, my clothes smell funkier than usual. And I've been seeing these blotches of yellow stains on my whites."

Jamie's face is burning from embarrassment. This was becoming dad and the underwear talk all over again. He tries to speak up, but his throat felt like it was shut tight. Guilt squeezing its hand around his neck with a powerful grip. Mrs. Anderson continues as she saw that the boy won't be making any arguments. "But the one thing that REALLY got me paranoid was that whenever I am getting undressed, it always felt like I was being watched. That feeling was getting worse and worse by the passing day. First it was the bedroom. In my shower. Anywhere inside my house. Even when I'm not at home! Honestly... I was getting really scared. I had to lock all my doors and windows, and shut every blind because I wasn't sure who would be watching."

Hearing all this broke the poor lad's heart. He never meant to make his neighbor so uncomfortable like this. He now understood why she shut herself out for that long time. Jamie finally realizes just how horribly selfish he was being this whole time. Just how bad his actions really were. A couple tears drip down his face as the older woman went on.

"I honestly thought that I might have been going insane. Maybe that I was just imagining it all. Have my mind stuck in the sewers when it came to those stains. I could have just been really sweaty. But then... I met you and it all clicked." Jamie perks his head up for this. "The way you acted and the way you constantly kept staring at me, it all made sense. And for first time in weeks, I felt relieved. All this time, I thought that I was being preyed upon by some dangerous sexual predator. Instead it turned out to be just a horny teenager."

"I'm... sorry..." Jamie finally said as he sat there. The older woman grins and pats her hand onto his shoulder. "Yeah, I figured you would be. You don't look like the raping type anyway." Jamie flinched from that word. It didn't make what he did any less wrong. Mrs. Anderson lifts up the boy's snout by his chin then began wiping his tears away with her hand. She wore a smile as she did this for him. "I wasn't a hundred percent sure if it was you though. So I decided to set up this little trap. I opened the blinds to my window so I can catch your attention. Then I had the idea to unlock that back door you've been using. I would leave my house and take a short drive around the block. I would then come in and see if you caught my bait. Ofcoarse, I didn't expect this to work on the first try."

The smooth coat lad blushes hard. He cursed himself for being such a gullible and stupid stooge. He felt so stupid in front of the mature collie he had been crushing on for so long. But there was something that bugged him about all this. "Are... Are you going to tell my parents?" "...I don't think so." Mrs. Anderson says in a blank tone. "I considered it, but I don't think they would like to hear about how perverted their little angel really is. And by the looks of things, you are really sorry. So I think that I'll just let you off with a warning." "Oh... Thank you." "No problem."

Afterwards, Jamie went home. He gathered his clothes, said his farewells, and went back to his house. He went straight into his room and lies down in his bed. Thinking. Thinking back to everything. His neighbor. Her body. The weeks of masturbation. Everything. It was all maddening. It all came in too fast and he was just too young to see where it was all heading. Is this what it was like to be an adult? That was the question Jamie thought to himself. He never felt more exhausted in his life. All the adrenaline in his brain drained out of him as he settles back down into reality.

Jamie is not sure what to make of all of this. Were him and Mrs. Anderson really on good terms? Will they be awkward with each other from now on? Is she going to be keeping her bedroom window shut and covered? Is this the end of his peep shows? Jamie grimaces. Does he even deserve to look at her body after this? Was his longing and lust for her breasts really worth it if it had turned him into some kind of psycho creep?

The boy gives a heavy sigh as he sat up in his bed. He glances over to his computer. Remembering all of the pictures inside. He forces himself off of the bed and turns on the power. He then went into his folders and looks through them all. Over a hundred different pictures were there. Plenty of them with either his dick or himself edited in. One by one, he deleted nearly half of them. A lot of repeats of similar looking positions she had done. Those of poor quality were removed as well. None of the pics with him in it survived. Only a good handle of Mrs. Anderson stayed intact.

He was tempted to delete those too. It was easy enough with the others. But... Her body. Her form. It was all too beautiful. It'll be a waste not to atleast keep these pictures. Besides, he purged more than enough gross pictures today. He can atleast keep some for whenever he is in need of a good wank. He moved his mouse over to the garbage bin and right clicks. Hovering the cursor over the permanent delete option. He clicks.

Jamie sighs as a weight has been lifted off his chest. He lies back in his seat and looks up at the ceiling. Once his guilt had been lifted, he could think back to that wonderful moment when Mrs. Anderson held him into her bosom. Not only did he finally get to feel her breasts for the first time, but he had his face in them! They were so soft yet firm. It was actually better than he could imagine. These thoughts quickly cast a spell on his loins and a tent was formed in his pants. Jamie sits back up and looks ahead at those nude photos of an undressing mature babe.

He hard. He was horny. Might as well let off some steam.

Pants down and hand thrashing up and down his dick, Jamie sits back as he watches a slideshow of erotic images of his busty neighbor. Meanwhile, behind closed blinds, a collie woman was spying on a boy through his open, uncovered window. She wore nothing but the clothes that same boy masturbated on. His scent still so fresh. Her left hand fingers kept the section of window blinds spread open to peep through. The fingers one her right hand were stuffed into the front of her panties. Occupied with another task. The woman watches as the boy jumps his cock so openly. Beads of semen already spilling out. His tongue lapping at the air as he panted. She drools at the thought of where that tongue of his can go!