The Neighbour

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Jon's neighbour catches his eye after gettting caught.
4.6k words
4.48
115.6k
51

Part 1 of the 5 part series

Updated 10/23/2022
Created 10/28/2010
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I made my way up the driveway, after having a few with the guys to end off the week. I was in no hurry to get home because I knew there wasn't anything going on tonight. The wife was out of town for the weekend and the other guys had stuff of their own going on. So I made my way up the rest of the driveway in this hard hitting thunderstorm. As I was almost to to the house my eye caught a light on in the neighbours daughters room. Maybe it was the few drinks or what but I was bold enough to just stand there in the rain looking to the window. As she entered the room, she's only had a towel around her and another in her hair. Within seconds she peels off the towel and is walking around the room completely naked. My interest holds me there as she goes to a dresser and pulls out some sexy bra and panty set before holding them up for her own approval. She first starts by sliding the thong up her legs and adjusting it. She then wraps the bra around her and fastens it at the back. Walking over to her closet she must have realized the curtain was still open. As she reached to close it I tried my best to get into the door of the my own house. As all this happened a huge flash of lightening and a crack of thunder rolled.

I got into the house with my heart just beating from the sight I had just seen and the fact she might have caught me. Not really feeling the urge to go to bed I turned on the TV and searched through some channels. I made my way to the porn and got looking around in there. I read some info on the movies before deciding on one. I turned to one that had talked about lingerie and that was enough, I read no more of it and just clicked on order. When the picture appeared it was just starting. Some hot blond was walking into this office with a very sexy outfit on, only to be met by another woman with the same style clothes on. After some cheesy porn pick up lines they began to kiss and caress each other. Within no time they were both down to some sexy lingerie and feeling each other up.

What happened next surprised the shit out of me, as the one girl grabbed a hold the other's panties and pulled them down, a large healthy looking dick fell out. Then I realized this porn was about trannies and crossdressers. But with the order already made on the TV I thought I'd make the best of it. My cock got hard while I continued to watch as the two went at it. I was then startled as there was a knock at the door. Without even thinking of what was on TV I got up and went to the door only to find Sara, the daughter from next door standing there. I opened the door and she stepped right in out of the rain. She was dressed to kill in a very tight tube skirt that showed just enough leg at the bottom and just enough cleavage at the top.

"Thank god your here. I hate being home alone when it's like this. And even worse our power just went out so that was it I seen a light on still over here so I came right over. I hope that's alright?"

"Yah sure no problem," I said.

"Some friends and I were supposed to go out tonight but pretty much all of them bailed with this weather," Sara said, "I hope I didn't bother you."

"No, no I was just watching some TV," I said without even thinking about what was on.

"Ohh mind if watch with you for a bit until the power comes back on," Sara asked as she headed for the living room.

My heart sank as there was no way I could stop her before she got to the TV. As I followed her into the living room she just stopped and paused looking at the screen. As the two chesty women were both rubbing their cocks furiously as they rode up and down on a double ender. Sara didn't say to much just sat down on the couch still in shock I think. Not really knowing what to say or do I too just sat down on the couch and watched the movie. After about half and hour and a couple more sex scenes, Sara finally spoke.

"Those look just like mine," she said as the woman on the screen was dressed in much the same bra and panties I had seen Sara in earlier. "Don't you think?" Sara questioned, "you know the ones you seen me in before." I agreed as my face must have lit up. "Yah I saw you at the door there. I was just getting ready to go to the club." With marbles still in my mouth I didn't know what to say. But before I could even get a word out Sara stood up.

"I'll be right back," she said as she made her way back out the door. I just stayed sitting there in shock and fear. Not knowing what was going to happen or what I should do or say. Within about ten minutes I heard the door open and close again and in she came with two big bags in her hands. She dumped the one on the table in front of me. The clothes and lingerie in front of me had me a bit puzzled.

"Get up and take off your clothes," Sara said. With little hesitation I did as I was told and began to strip down. With some embarrassment and hesitation I slid my boxers down and stood in front of her completely naked.

"Here put these on first," Sara said as she handed me a white frilly garter belt and white stockings with frills at the top of them too. With having not much of a choice I began to put them on. Once they were on she handed me a pair of white frilly panties, and those to I slid on. Next came the bra, again I put it on and waited for my next instruction. Sara came over to me and pulled open the loose bra.

"Here's something to help fill it out a bit," Sara said as she filled the bra with some silicone breastforms.

"We got all this last year for Halloween, that's why it's to fit you not me," Sara continued. "And let me tell you it has made a world of difference with me since then." I didn't really say a thing, not really understanding what she exactly meant. Next she gave me a plaid skirt, and like half a white dress shirt. I just took them and continued to put it all on. While I was doing this she was starting to straighten and tidy up a blond wig. When I finished she reached to my head and put the wig on with some pins of some sort to hold it there.

"Now let's do a little touch with some make up," Sara said as she reached and began to apply some bright red lipstick and some other stuff to my eyes.

"You look just like Matt did," Sara sort of snickered. Matt being her boyfriend. "Like I said before after him wearing this it made a huge difference between the two of us. Now how about you check out your new look," Sara guided me to the mirror in the end of the hall. As I stood in disbelief I looked back at myself. I looked like a porn star dressed as a slutty school girl.

"What do you think?" questioned Sara.

"I look like a real....a real.....woman," I said.

"I could tell that this was the perfect thing to do after seeing that movie before and how hard you were when you answered the door," Sara said with a smile. "Now there's some more things that Matt and I did that night that you may want to try out?"

"What's that?" I asked not figuring it could be much worse than me dressed as a slutty school girl with my neighbours daughter giving the orders.

"Well," Sara started walking over to me and seating me down on the couch. "You can start by taking care of this for me," Sara said as she pulled her skirt up just enough for a long rubber cock to fall out of the bottom. Without a word she moved it to my mouth and I began to slid it inside. I began sucking on the cock, and Sara began to thrust back and forth sliding the cock further in each time. I could see my own lipstick marks on the cock as she pumped it into my mouth. She too was liking the feeling because I could hear her panting and moaning.

"Once I started using these toys I couldn't get enough of them," Sara said as she reached over emptying the second bag onto the table while still keeping the cock jammed in my mouth. From the corner of my eye I could see quiet an extensive collection of sex toys.

"Let's try something else that will help me keep rhythm a little better," Sara smiled as she grabbed another dildo with harness and fastened it to my chin. She then guided me back in the chair and began to straddle my face. Once she was above my face she reached down and guided the rubber cock on my chin into the hole in her harness and into her wet waiting hole. She then continued reaching down and guided the rubber cock on her harness into my mouth.

Again I carried on sucking on the cock and she thrusted up and down on the cock now in her. This went on for quiet some time, sometimes the pace would be soo fast I could hardly keep up to her and others were slow and sensual. As she must have tired of this position she led me to lay on the floor and carried on with much the same, straddling my face, she carried on pounding my mouth. Through Sara's moans I heard the door to the house open and close. As fear raced through me Sara just kept on pumping my mouth full of cock as so I could not say a word.

"Holy shit, looks like the fun has already started," said the voice that entered the room.

"Sorry dear I couldn't help myself," Sara responded, "but no worries you can join right in." As I could barely see through Sara's thighs that were confining my head, I did manage to see Sara's boyfriend Matt standing there. Within seconds I could feel him crouch down over top of us and began to make his way up my body to Sara. They both reach down and begin to readjust. As the rubber cock from my chin is taken out of Sara it was then replaced with Matt's own cock. The rubber cock that was in my mouth now just bobbles back and forth up and down my face. And to my surprise the rubber dong that was sticking from my chin was then guided into Matt's waiting asshole. Within seconds they continued on pumping each other right above me, and with the rubber dong in Matt's behind I was forced to stay right there for the show.

Sara then reached down and helped me to lift my head a bit. Knowing what she wanted I began to lick. My tongue found it's way to her clit and I began to lick. But within just seconds she reached back down again and pushed the top of my head, forcing me to aim lower. With my tongue still out, I then felt Matt's shaft, as it was sliding in and out of her. With not much of a choice I continued on licking the cock that was right above me. The moans that were coming from Matt told me he liked it. As I licked away at the shaft, Matt's balls would sometimes run over my face. Without another thought I then moved to licking and sucking to them. This really drove Matt crazy because his moans became even louder.

We continued on like this for only a short time before the two of them where screaming in climax. Sara started as Matt continued to thrust into her. Next was Matt, but as he began to moan with the orgasm starting Sara reached down and pulled his cock from her hole and turned it down right into my mouth. I got a quick taste of Sara's juices before the salty goo from Matt shot to the back of my throat. With my mouth full of Matt's cock and my chin cock locking me in place there, there was nothing I could do but just keep on doing what I was. I kept on sucking on Matt's cock swallowing his goo as he pumped in and out of my mouth When they had both finished they climbed off of me and allowed me to sit up. As I did, I finally seen Matt standing there in front of me dressed in much the same outfit as Sara.

"So I take it you got the note I left on the door?," Sara asked.

"I sure did and when it said to put on the outfit on the bed I knew it was going to be a good time," Matt answered.

"Yah, I had someone checking me out tonight through my window. And when our friends called to cancel I thought that I would take advantage of the situation, and there no sense having a good night go to spoils. But to my surprise when I got over here it looked like he was going to start without me. The dirty little slut was watching some tranny porn, so I knew he was in for the same thing I was thinking and in no time at all here he was laying here sucking my big dick."

With nothing really to say and no real way to defend myself I just gave a half smile and began to lift myself up off the floor. Matt and Sara did the same. We all began to straighten our clothes and as I looked over to Matt he to had even the same panty set on as Sara. He just looked back to me with a smile as he tucked his cock back into his panties.

"That's a real nice outfit our little slut has on," Matt said.

"Yah you remember the fun we had with it hunh?," Sara replied.

"How could I forget it's been one of the best things to ever happen to me," Mat continued. "Those are even the huge silicone tits we got too hunh?" Matt reached over to give them a squeeze, and a playful hit as they just jiggle back and forth on my chest.

"The glue on them should be dry by now too," Sara said.

"What! what glue?" I exclaimed in fear.

"The glue I put on the backs of them, they give you a much better feel if they're actually glued right on," Sara explained.

"Yah she's right," Matt agreed, "it makes a huge difference, take it from me."

"Don't worry I have the solvent that will take them off when we're done," Sara said as she too walked over and gave them a playful hit and watched them wobble on my chest.

"Well I'm going to go get changed into something else," Matt said, "and I'll be right back."

Not really sure why he'd be going to get a something different on, I just looked to Sara.

"Trust me you'll like it. You've already shown me that you would."

Sara walked over to me and began to rub her hands all over my body. She would squeeze my ass and tits and rub her hands down to my crotch. I followed her actions and began to do the same to her. We quickly got faster feeling and groping each other. I reached down and began to stroke the end of the ruber cock peeking out the bottom of her skirt. Sara smiled as I did. Without another thought I began to lower on to my knees infront of her and take the cock into my mouth. As I slid her skirt up a little higher to give me full access I could smell her musty excitement. I began bobbing on the cock taking a little more in each time. Sara just looked down to me with a huge smile on her face knowing that I was having as much fun as she was. But before we got too carried away with ourselves Matt came back into the room.

"What do you think?" he asked.

"That's fuckin hot," Sara replied. "And we all know she'll like it," she continued with a giggle.

As I slid the cock from my mouth and turned to see Matt, he was standing in the doorway with pretty much the same outfit as the tranny's in the movie had on earlier.

"Sara thought you might like this outfit," Matt said, as I just looked over his entire body. He was fully dressed. With some high 'fuck me' heels and sexy sheer stockings going up his legs, with just a little of the stocking tops showing beneath the bottom of his skirt. And the full skirt blouse and jacket that made him the secretary from the movie. He too had two giant silicone tits under his outfit, as he walked over to us they swayed side to side.

"Well I guess I better get changed too then," Sara said as she walked over and out the doorway Matt had just returned from.

As I turn my head back to face Matt, he already had the front of his skirt pulled up and his semi hard cock looked back face to face with me. With his feet in the heels and his legs wrapped in the sexy stockings being held up by a sexy garter belt I could now see, I knew exactly what to do. He smiled down to me as I opened my mouth and took it in. I slowly began to lick the tip of my first real cock. With all the cock sucking I had just done in the last hour with Sara it was no time at all before I was right to the base of his cock. I slid my mouth up and down his shaft as he gave some small moans in approval. As I did before without even thinking I raised my hand and began to play with his balls as well.

I could hear Sara walking back into the room and letting a small gasp as she entered. I could imagine her thrill seeing me as a school girl on my knees, with her boyfriend as a sexy secretary, with his cock buried completely in my face and me fondling his balls. I stopped and turned to Sara as she was standing there rubbing some lube on to her big black strap on. She had changed into a leather type outfit that almost looked like a mans suit with tie. And in her one hand the black rubber strap on that glistened with lube in the light, and in the other a long blue double ended dildo.

"Well I guess the student was being punished by the teacher or working on some extra credit," Sara joked. "So I take it I must be the stern principal then?"

Sara walked over to us and locked into a long kiss with Matt above me. With nothing really to do, I went back to what I had been doing most the night and took Matt's cock back into my mouth. When they're kiss broke above me they just stood for a moment and watched as I worked away at Matt's cock. Sara then made her way behind me and began to squeeze and caress my ass. She then lifted my skirt and began to work to pull my frilly panties down just enough to get to what she wanted. I didn't lose any rhythm I just kept on doing what I was. Sara then reached to the pile of toys on the table and rummaged through them. Within seconds I could feel a cold hard object at my anus. With the toy all lubed up she slowly began to work it inside of me. I groaned and part pain, part discomfort and part pleasure. Once the toy had made it's way inside she slowly started working it back and forth.

"A real slutty schoolgirl takes two at once," Sara said as she quickened the pace and turned on the vibrator.

This only lasting a little while before my muscles had relaxed and she removed the vibrator and began to work on inserting the strap on. With more pain, more discomfort and definitely more pleasure, she slowly fed the whole rubber cock into my anus. Once she had it buried right to the hilt she just stopped and paused for a second. Then slowly began to thrust in and out of me.

"She's so tight you'd almost think it was her first time," Sara said with sarcasm.

"I don't know but it looks hot from up here," Matt replied.

They both continued on fucking my holes. Matt's moaning was getting louder and closer, so I knew he wasn't going to hold out much longer. I sped up on sucking and cupping his balls. Sara must have sensed this too and kept up with the rhythm and began pumping my ass even faster. Matt's balls began to lift and I knew what was coming. His first shot had so much force it went straight to the back of my throat and forced me to swallow. Next couple came and began to fill my mouth with his salty load. I swallowed again trying to keep up with him. As I did he slowed the pace and shot the last couple shots and I swallowed them down too.

Matt walks away from the front of me and I collapse onto the couch infront of me. Sara still behind me slows down with the cock and gently pulls it from my behind. The two of them began into the kissing again while I just lay there trying to catch a breath. They fondle each other's tits and ass. They make out like this for some time, Sara often reaching down trying to bring some life back into Matt's cock. As her efforts begin to pay off I turn to see them dropping to they're knees behind me. As Matt comes the closest to me and Sara behind him, they both reach below them. Matt helps to guide Sara's strap on into his own arse. With a little work I could hear it slide inside. Once this was all done behind me Matt then turned his attention to me. He guided his now hard cock to my hole. He pressed the tip against my hole with steady pressure. It slowly opened and he pushed inside. All of us connected together like train cars slowly began to sway.

"Your right, she is tight," teased Matt.

"I knew you'd like it," Sara replied with a giggle.

They continued on rocking back and forth. They'd pick up speed and then slow down, then pick up again and slow down again. This carried on for only a little while.

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