Befriending the Neighbor

Intro

This story is a work of fiction. I guess I should start with a little introduction to the situation I was in, see I was living in this apartment when I was 26 years old, I had a decent job and on the weekends I liked to relax. At the time I was single because, well, I didn't really go out much except to go to work or run errands, and frankly I didn't really meet very many women with such a mundane routine. The house next to my apartment building was home to a family of four, the Smith family. The couple that lived there, Greg and Tammy were a nice couple, closer to my mother's age, but I still got along with them, they would ask me to keep an eye on their house when they went out of town for a long weekend or vacation. Greg and Tammy have two kids, Sophia and Joe, Sophia was a senior in high school, and Joe was a sophomore, they were decent kids, but then again their parent didn't know everything that was going on, and that was fairly obvious. Sophia was the type of girl that was into sports, did good in school and strayed away from that drugs and booze. I had had a few conversations with her over the last couple years, but nothing too in depth, I knew that she liked to keep her window shades open. I'm not sure why she always did that, but if I was ever a little bored I knew that I could take a peek out my window and I might get a little show.

Chapter One

Saturday morning I woke up after having a particularly long week at work and I just wanted to relax for the day. When I came back in from smoking, I figured why not, it was a nice day out, so I decided to open up the shades and the windows. While I was sitting there, there was a knock on the door, so I got up and pulled up my pants, (alright, so I was sitting there masturbating, what of it) when I opened the door, it was Greg standing there and the first thought that crossed my mind was that Sophia had seen me doing my thing through the window, since I forgot that I had opened the shades, and that she had said something to her father.

"Hi Greg, whats going on?" I asked, hoping that he wasn't going to punch me in the face.

"Hi James, listen Tammy and I are going to visit her mom for the week, Joe is coming with us, and we were just wondering if you would want to keep an eye on the house for us again?" he asked with my relief.

"Sure, is Sophia not going with, or are you just wanting to make sure she doesn't have any parties while your gone?"

"Mostly the latter, she is staying home because of soccer practice, I guess they are starting a few weeks before school does, and she doesn't want to miss any of it and fall behind the rest of her team. I just don't want her to have a bunch of people over destroying the house. I'm not asking you to go break up anything, just if you happen to see it happening, maybe call in a noise complaint or something."

"Alright, I think I can do that. You three have a safe trip, and enjoy your visit with the mother.

"Thanks." he said with a slight tone of contempt.

So after my shower I sit back down in the living room and decide to take a little nap. When I wake up its already dark out and all I can think is shit, I just slept the day away again. When I looked out the window I happened to see into Sophia's window, and thought it best not to turn on my lights, I figured what the hell, I wouldn't mind a good show before I grab some dinner, boy was I in for a treat. Sophia had both her shades open and as always I could see right in, plus the way she had the mirrors set up in her room I knew that I wouldn't miss a thing, just then I saw her walk into her room wrapped in a towel as though she had just gotten out of the shower. Perfect, I'm going to get to see everything.

About three weeks ago, Sophia had turned 18, she broke up with her boyfriend last week because she found out he was cheating on her. Well because of this, she has been particularly honey as of late, and she likes to masturbate in her room in front of the mirror. So there she is standing in front of the mirror once again, she drops the towel and lets it fall to the floor. Sophia walks over to her dresser and grabs something out of the top drawer which I have come to know is her underwear, and she pulls on this cute little thong that comes to rest perfectly between her ass cheeks. Then standing there looking in the mirror once more, she starts to rub her tits a little, its at this point that I realize it's not just my windows that are open, hers are too, and I can hear her start to moan, while its faint, I can still hear it, and that is more than enough.

Then she walks over to her bed to grab something else and walks right back over to the mirror, where she plops herself down in front of it on the floor where she had dropped her towel. I watch as she takes this brand new dildo out and starts sucking on it until she seems satisfied that its wet enough. She pulls of the thong that she had just put on, then she takes a little bottle of lube and starts massaging some into her already wet, recently shaved pussy. I'm sitting there on the living room floor daring not to make a sound for fear of her hearing me, and she takes this dildo and slowly starts rubbing it on her pussy lips, taking her time and making all sorts of noise in the process. After a couple minutes, she slides this pink 7 inch dildo into her tight little pussy, getting it all the way in she shifts her body so that she can prop herself up on it, resting the dildo on the towel covered floor. Slowly she starts moving herself up and down taking it into herself and enjoying every thrust as she goes deeper and deeper. The moans start to come louder and louder. At this point my dick is rock hard, and in my hand as I'm slowly starting to pull on it, still hoping not to make a sound. I look back over and watch her start to move quicker, her head rolls back again and at this point each thrust is punctuated with a "Yes, oh god." As I'm watching she cums, very loudly, and she collapses, falling back, and laying there on her back for a couple minutes, dildo still resting in her pussy and one hand on her tit. I can see that she's trying to catch her breath, and while she clearly enjoyed herself, she just looks like she's not quite done yet.

After a couple minutes of waiting, I watch as she reaches down and grabs the dildo from her pussy, she brings it up to her mouth and and starts to lick it like a lolly pop. "Alright, it's now or never, I'm going to do this, I just have to do it." I hear her say to herself curiously. The next thing I know I watch as she reaches over and grabs something a little smaller that was just out of sight. With her sitting there, she takes the bottle of lube and starts to put some on the tip of this little butt plug. While this thing is not quite the size of the dildo that she just got done using, I can clearly see that it is bigger than she is ready for. I watch as she gets onto her hands and knees. She reaches back with the hand that she had just used to lube up the plug and starts to rub some onto and into her tight little ass hole. I can see her wince as she pushes her finger inside of herself. At first it doesn't seem like it wants to go in, but then all of a sudden she lets out a little squeal as the tip of her finger slides in, with that she stops for a moment and just holds it there. Then she starts pushing again, ever so gently, she start pushing her middle finger into her ass, and then slowly starts working it in and out. After about a minute of this, she pulls her finger out completely and takes a rest.

"What am I waiting for, I just need to get it in. I can do this." she coaxes herself. She grabs a hold of the lubed up butt plug and reaches back once more, as she lines up the tip of the plug with her ass hole, she takes a deep breath and slowly lets it out as she starts pushing the plug into her ass. After only a few seconds she stops pushing, and lets back on the pressure, then she starts pushing again. After doing this about six times, she finally manages to get the butt plug into her ass all the way. As she takes her hand away, and it stays put, she lets herself just rest there for a moment.

"Alright, it's in, now what the fuck am I supposed to do." I can see that she has an intrigued look on her face. Slowly she starts to shift her body so that she's laying on her back again, then she reaches down and starts to rub her pussy again. The next thing I know she grabs the dildo off the floor and starts pushing it back into her pussy again. Again she cums, hard, moaning the whole time, and crying out with each thrust of the dildo. After she came, and lay there for a few minutes, she manages to get herself up to take the plug out of her ass. She then grabs both the butt plug and the dildo and exits her room I assume to go clean them and herself. I decide that this is the best time to get myself up, close my shades and turn on the lights. After that show, I was thoroughly worked up and decided that it was time for another shower so that I could finish myself off. This was the first time that I saw Sophia with the butt plug in her ass, but little did I know that it wouldn't be the last.

Chapter Two

The next day was Sunday and I knew that I had a bunch of stuff to do, since I had slept most of the day away yesterday. So after I got myself dressed and looking like a normal member of society, I took the laundry down to get that going. I only lived about a block away from the laundry mat, so I just walked down there. On my way home I happened to pass by the neighbors house and saw Sophia sitting out on the front steps on the phone. As I passed I waved and try to make myself look as normal as possible, not like I had just watched her fuck herself in the ass the night before. Suddenly she got up and put her phone away as she walked towards me.

"Hi James, how are you doing today." she asks as I pause, thinking oh god, she knows.

"I'm doing alright, what's going on with you?" I ask, silently praying that she didn't see me the night before.

"Alright I guess. Hey, could I ask you a huge favor?"

"Well, you can ask, but I was just about to run some errands, what's up?"

"I was just going to ask if you could run me over to the mall, when mom and dad left they accidentally took the keys for both cars with them and forgot to leave me with a way to get anywhere. They said that I should ask you if you weren't busy. I can get a ride home, but my friends are already there and they don't want to come all the way over here to pick me up, just so they have to bring me home again in an hour. Please."

"I guess I can do that, it's on my way to the grocery store anyway. Does this mean that your going to need a ride to soccer practice all week?"

"Thank you so much, I owe you big time, I promise I'll pay you back somehow, and no, one of my team mates said that she would swing by and pick me up and drop me off from practice, no worries. Were you planning on leaving right away or did you need some time to get ready."

With this question I pause for a moment and I have to stop myself from saying anything inappropriate. I look at her and her tight little outfit. "No, I'm ready to go now, I just have to run up and get my keys quick, I'll be right back if you would like to wait for me by my car."

After I take her over to the mall, I head over to the grocery store to get what I need and head home after I pick up the laundry. When I get into the house I unload the groceries and put things away, sit down in the living room and watch television. After a couple hours I finally decide that I should probably turn on the lights, plus it time for a smoke again, after I come back in, I happen to see that the neighbors lights are on, quickly I go over and turn the television off, so as to not give away that I'm here. My shades were closed this time so I don't have to be as careful, but I do have to move them slightly so that I can get an unobstructed view. Perfect, both shades are wide open again, this time, it's not just Sophia in her room, but she has a friend with her. Slowly and gently I slide my window up a little so that sound can get in. Of course, with a friend over, the likelihood of me seeing anything at this time is slim to none, but that doesn't mean that I'm not going to wait patiently. As I'm watching, I hear Sophia telling her friend about the butt plug and the night before.

"Wait, which one did you use, the small one or the big one?" Her friend asked.

"This one, and it was great, it took a little effort to get it in, but once it was in, it was fantastic. I have never cum that hard in my life."

"Jeez, that's bigger than the ones that we bought, did you even try the other one first or did you just go straight for the big one?"

"Well, I started with my finger, cause I knew that I could get that in, then I figured fuck it, go big or go home." she responded with a little smile on her face.

"You are home, and didn't it hurt. It took some real effort for me to get the small one in that we bought together. And I've kind of been regretting it all day."

"How much lube did you use? I used a fair amount and it wasn't too bad, that's why I picked up the bigger bottle today, I want to do it more often but that little bottle just isn't going to be enough."

"Well I used some, but I didn't want to use too much because I knew that I was going to be going out with it in all day and I didn't want to feel like it was sliding out the whole time."

"Wait, it's in right now? Let me see." she said with some excitement in her voice.

I was just barely able to see Sophia grab her friend by the hips and pull her skirt up so that she could look upon her friends gorgeous thong clad ass. From my distance I couldn't see the butt plug, but the ass on that girl was almost as nice as Sophia's. I watched as Sophia grabbed her friends thong and simply pull it to the side, revealing the glint of something metallic in the light.

"Wow Jenna, so how long have you had yours in, or did you put in just before you left home?" Sophia asked Jenna with some curiosity in her voice.

"Well, I put it in about an hour before I left home, so that I could make sure that it was going to be comfortable enough, it did take me a little effort to find the right underwear so that it wouldn't push it further in, but these seem to be working perfect. So when did you play with that one?" Jenna asked trying to get Sophia to let go of her ass.

"Um, well, last night was the first time with anything but my finder in there, but this morning after I was done in the shower I decided to try and go all day with the smaller one in." she says as she turns slightly to stick her ass out. Sophia was wearing a pair of very tight leggings, of which I couldn't see anything because of the distance, but I could tell that her ass was quite impressive.

"HOLY SHIT." Jenna pauses, "Why didn't I notice earlier, wait didn't your neighbor give you a ride to the mall? Jesus, Sophia, what if he had seen something, those pants don't leave much to the imagination, I can see every line of your thong as it is, but now that I actually look at it, I can even see the outline of the plug a little."

"Its fine, I picked this combo for a reason. Between the thong and the pants, that thing is not going anywhere, and to be honest, after my fun last night, this one went in pretty easy this morning. It has been in all day so far, and I'm not going to lie, I am super horny. I think the next thing I'm going to try is that dildo. That way I can get my self really going and I want to try and cum without touching my pussy once. You think it can be done?"

"It can be done, but it's going to take some real effort." Jenna responds quickly. "I think that's something that you have to work yourself up to, but hey, if you want to, we have that other thing that we bought today, did you want to try that out, while we both have the plugs in, or did you want to take them out."

Sophia didn't say a thing, or if she did it was inaudible, all she did was leaned in and started kissing Jenna, full on the mouth, with tongue. As they were making out, they started to move over to the couch that was in the room, this put them even more centrally located within view of me. Sophia started to take off Jenna's shirt revealing her bare C cup tits. They were bigger than Sophia's but neither girl had a bad rack. I had to stop to think if I should be watching this, I knew that Sophia was 18, but was her friend, wait, you have to be 18 to buy sex toys. Jenna had to be 18. I started praying as I went back to watching them. At this point Jenna reached over and started to pull off Sophia's shirt. While the larger breasted Jenna wasn't wearing a bra, Sophia was, but then again, I think she was trying to make her B cup tits look closer to a C. Either way, Sophia's bra was off quicker than I could think about it, followed by Jenna's skirt.

I didn't even know that Sophia was bi, or that she had thought about having sex with a girl, I knew that she had had sex with her ex boyfriend on multiple occasions, but never anything weird. Right now, with Sophia still in her tight leggings, she pushed Jenna onto the couch and got her face right into her friends crotch. She very carefully pulled Jenna's thong off completely and started to lick her pussy. With one of her hands she started to play with the butt plug a little by lightly pushing on it. Jenna looked like she was in heaven, and slowly Sophia pulled out the plug and set it onto the floor, with Jenna's permission, she grabbed the large plug and started putting some lube onto it. Taking things very slow, with more lube, she started to push a finger into Jenna's ass, while licking her clit and causing her to moan loud enough for me to hear. Soon a second finger was introduced and after a minute, both fingers were removed, leaving her ass slightly open. Sophia then takes the larger butt plug that she had used on herself the night before, and starts to slide it into Jenna's ass. Jenna starts moaning even louder, telling Sophia to go slow.

After a minute of slowly pushing and trying, she manages to get this larger plug into Jenna's ass hole, with Jenna panting and holding her ass cheeks. "Oh, My, God, I have never felt so full in my life. I can't believe that you managed to get that thing in me."

Sophia pulls her mouth away from Jenna's pussy and licks her lips, "Now, we're going to give that new toy of ours a test drive. I hope your ready, this is new to me and I'm not sure how this is going to work." Jenna starts to rub her pussy, while Sophia gets up and goes over to the black bag sitting on the floor that I hadn't even noticed. Slowly she pulls out a package with what looks like another 7 inch dildo. She opens the package and this is when I notice that it's a strap on dildo. Holy shit. I was not expecting this. Taking a look at it Sophia ponders for a moment. She slowly takes off her pants while Jenna just lays there patiently waiting, rubbing her own clit, and moaning. With her pants now off she leaves her cute little thong on, and pulls the strap on on over it. After taking a moment to tighten the straps around her waist, she makes sure that it's sitting properly between her legs. Slowly Sophia saunters over to the front of the couch where Jenna can see her standing there with the fake dick hanging between her legs. With some lube on her hand she starts pulling on the dildo as if it were the real thing, she positions herself in just the right place so that she can get the dildo into Jenna's pussy, slowly pushing all 7 inches into her friend. With a kiss, Sophia starts fucking her being gentle but deliberate, taking her time but making it count. In and out the dildo goes, with an increasing rate of speed, like a piston warming up on a cold night, with each thrust of the fake dick, Jenna lets out a moan even bordering on a squeal from time to time.