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Older Neighbor Friend


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My mom and I lived in the house I grew up in after my parents divorced. The original thought was after I graduated high school I would go off to college, but sometimes life happens and plans get delayed or changed all together.  After high school I decided to take a year off of my education and do some local work project to build up some cash reserves.  Thinking back now, I am so glad I did. 

The summer after high school our neighbors, an elderly couple, decided to downsize and sell their home.  I recall seeing a moving truck there one day, but was too busy to see the new home owners.  A few days later I was doing some yard work outside, mind you it was summer and pretty warm, so I was already sweating and thirsty.  I didn't hear anyone approach, but soon I heard someone asking, "excuse me".  I looked up to find this very attractive man, probably late fifties, standing beside me with a cold beverage in his hand. 

"Sorry, I didn't mean to startle you.  My name is Jake, I just moved in next door and wanted to come introduce myself.  I saw you outside working hard and I thought you might need a cold drink".  Jake extended the drink out to me.

"Thank you" is all I could say as I accepted the cold cup full of iced tea. 

Jake stuck out his hand, "and you are?".

I took the cup away quickly, "sorry.  Tim, great to meet you".  I grabbed Jake's hand.

Jake held my hand a little longer than necessary and I quickly got a sense of his strength and the length of his hand. 

"Good to meet you Tim.  It seems you take great care of your yard, that is admirable", Jake said.

I chucked, "I try, but this is my mom's place and when I finally leave home for college she might have to actually hire someone to do what I do for free."

"How long until you are off to college?"  Jake asked.

"Not until next summer.  I decided to take a year off and work". 

"Smart thinking" Jake said.  "If you need some more work to do, please let me know.  I don't really have time to maintain the yard, house, and pool."

"I would love to help out, thank you for asking"  I said.

Jake said he would pay me, which I tried to talk him out of, but he wasn't having any part of it. 

"You can of course use the pool whenever you want, added perk", Jake said.

"Oh man, you have a deal then"  I handed the cup back to Jake and thanked him.

"Why don't you come over tomorrow and I can show you around.   You can swim if you want to and then maybe get started the day after?  How does that sound?"  Jake asked

"I will see you tomorrow then, and thank you again Jake, looking forward to it.  I said as we waved and Jake walked back to his house.

 

The next day, in the late morning, I strolled over to Jake's.  I decided to wear my swimsuit to let Jake know I was still interested in swimming.  Just my swimsuit and a tshirt.  I knocked and waited just a minute.  Jake answered the door, swinging it open, "Hi Tim, great to see you".

Jake was wearing a tight tank top, and very loose gym shorts.  "Please come in" he said while waving me inside.

Jake's house was very well decorated, with a lot of plants and sunshine, and very clean I noticed.  I liked that and took note to keep it that way if I was ever around by myself.

"You have a beautiful home Jake, thank you for inviting me over". I said.

"No worries, hopefully you will be here a lot more helping me out, so please get comfortable and make yourself at home.  I just finished up some work and was going to head out to check on the pool.  wanna join me?".

"that would be great".

Jake led me through the kitchen to a patio door leading out back and the pool area.  It was gorgeous, a bunch of plant life along with a nice medium sized pool.  There were lounge chairs all around, great for sunning, I was jealous.  I know how I would like to spend my days, here sunning. 

"There is another door to the patio", Jake pointed, "that leads to my bedroom", he paused for effect.  "let me show you the pool equipment and then you can swim all you want.  I am going to lay out and get some sun if you don't mind".

"no of course not, it is your pool." I laughed.  "besides a swim and sun sounds great, perfect weather". 

"The equipment is over this way." 

Around a corner, hidden behind a walled in area was the pump, filter, chemicals, and equipment.  A very easy setup and system it seemed. 

"Easy enough.  I can come by every other day, if that is ok with you".

"sure, that works great.  now for that swim.  There are towels in that cabinet there and I will be right back", Jake said and walked towards his bedroom door.

I got a towel, dropped it on one of the lounge chairs, and took off my shirt.  I slowly got in and did a few laps as the water was very refreshing from the warm summer day.  I didn't notice that Jake had returned, but when I looked up he was adjusting the lounger next to where I had dropped by shirt and towel.  Jake was wearing bikini swim trunks now, which didn't leave much to the imagination.  Jake finished adjusting his chair and turned to face the pool. I immediately noticed the outline of his cock, he seemed to be semi hard or very big while soft.

My eyes were stuck on the front of his shorts, and I am sure Jake noticed.  "how is the water Tim?" 

I quickly looked up at Jake, "water is great, thank you."

Jake sat down on his lounger and started to get comfortable.  "Tim, if you need anything please let me know, drinks or anything.  I am going to get close my eyes for a bit".  He started to spray on some sunscreen, "I fucking hate tan lines so try hard not to get them.  I prefer an all over tan to avoid them". 

I think I knew what Jake meant, he liked to tan completely naked.  

I got out of the pool and quickly looked around, the backyard and pool were not visible by any of the neighbors, as the walls were a little higher than normal and all of the vegetation.

"Do you ever tan naked Jake?" I asked quietly, not sure who could hear.

Jake replied, "I love laying out naked, that is what I do when alone or company that thinks the same way.  Tan lines are sexy in some situations, but not for me."

I hesitated to ask what he meant by "in some situations", but I didn't.  Instead I assured Jake that he should do whatever he normally would, about laying out naked.

"Are you sure Tim?", Jake asked.

"Sure, I don't mind at all" I replied.

Jake responded "great" and stood to slowly remove his bikini swim suit.  I did nothing but stare, how could I not?  When Jake pulled the front down over this cock, I could then see that he was definitely soft at first, because now he seemed to be growing, and growing quick. Jake's cock was beautiful; uncut, veiny, and big balls. 

Jake stood up right fully now, with his dick swinging a little.  "Thank you Tim, that feels much better."  Jake sat back down on his chair, leaned back with his eyes closed and adjusted his cock in front of me.

"Tim, if you want to lay out naked, it is alright with me", Jake said without looking at me.

I started to get out of the pool and head for my lounge chair, quickly so Jake couldn't see that I was aroused.  I quickly got my shorts off and laid on my stomach.

"I love the heat on my body", Jake said.  He looked over at me and said, "Tim you might get burnt on your ass, would you like some sunscreen?"

"Yes, thank you.  I hadn't thought about that". 

Jake sat up on his chair and took a tube of sunscreen, squirted some into the palm of his hand, then started rubbing it around my ass, from my lower back down along my inner thighs.  He seemed to pay a lot of attention to patting my ass cheeks then sliding his hand through my crack, which was now aching.

"I think I have most of it, but maybe just a little more to be sure", Jake said.

"ok" is all I could get out.

After another squirt into Jake's hand, I felt him applying the lotion again.  Now I felt both of his hands on my ass, kneeding my ass cheeks and rubbing in the lotion. I felt him use both of his hands and pull my ass apart then releasing my cheeks. 

Jake said quietly, "fucking nice.  you are definitely taken care of now".  He patted my ass and adjusted to lay back down. 

As I turned to thank Jake I could see his cock was very hard now, his foreskin pulled back tight over the head of what looked like a wet tip.

I stared at his big cock but murmured, "thank you".

"Anytime, as you noticed, I enjoyed it tremendously".  Jake said

"um, I can see that". 

Jake propped himself up on an elbow and asked, "does it bother you that I got excited?"

Finally I took my eyes off of his cock and looked at him in the face.  "Absolutely not, the opposite really".  Maybe that was too much information.

Jake just smiled at me for a while and laid back down, "good" is all he said.  He didn't soften at all, but rather seemed to get even bigger....or thicker.

After a few minutes of silence I started to settle down, I could feel my cock shrink.  Jake started chatting again, never opening his eyes, just relaxing while probing me, figuratively.

"Tim, I am guessing you know I am gay"

I laid my head down, so it faced him.  I couldn't seem to stop staring at his cock.  "Yes, I kind of figured".

Jake continued, "By your reaction to my...situation and the way you reacted to me applying lotion to your ass, I am thinking you might also enjoy those same things.  Am I right?   Have you experienced things with men?"

I had been staring at Jake's cock so had noticed he had turned his head toward me after he asked that question.  As I processed my answer I glanced up and noticed him staring at me.

"Jake, I don't know how much I should share, but you are somewhat close to right.  I have only sucked someone before, but fantasized a LOT".  I was rock hard again answering that, thinking back to all of my fantasies that involved me being fucked.

"Do you mind if I ask what your favorite fantasy is?"  Jake asked.

I thought for a moment and decided to turn over, at this point I didn't care if Jake knew I was aroused.  As I settled in on my back I started to relive my fantasy.  "It isn't anything super sexy or special really, but since I knew I wanted to be with a man I have wanted a man to be inside of me, deep.  I have had a toy in me and masturbated often like that, but never gotten to enjoy that for real".  I realized I was breathing hard. I wanted so bad to wrap my hand around my cock and masturbate furiously.

I kept my eyes closed and asked, "I hope I am not sharing too much". 

I heard Jake move on his chair next to me so I looked over at him.  He was now on his side, cock straining, "absolutely not!  I am very intrigued and interested in what you think about and fantasize about."

I looked at Jake and asked, "can I ask you some questions about what you like?"

"oh yes, please do" Jake answered.

Thinking about the pictures and online porn I have seen I asked, "do you like to fuck or be fucked?"

Jake didn't hesitate at all, "I like to be the one fucking for sure".

I quickly asked, "why?".

Jake took off his glasses and started to look past me, as though he was flashing through memories.  As he started to answer I saw his hand slide down and hold his big balls in his hand.  "For me Tim, I guess is the feeling of a man's ass on my cock, there is nothing like it.  I love the slow penetration, watching him enjoy my cock as I slide into him slowly.  I enjoy that naked contact of skin on skin, my cock all the way in him, and his pleasure finally taking over him.  Simply amazing".

Jake was slowly sliding his foreskin over the tip of his cock, back and forth, long slow strokes.  His cock was just so nice, big and meaty. 

"Jake, do all men enjoy you that way?  You seem to be pretty big".

Jake let go of his gorgeous cock and laughed.  "I think there is a compliment in there somewhere, but yes, they all do.  It is the way that I fuck I guess.  I don't believe in pushing in hard or forcing my dick into someone, no I would rather go in slowly and let him get used to me.  Does that make sense Tim?".

"Yes it does Jake, very much".  I closed my eyes again and muttered, "just as I imagine it".

"whew", Jake let out.  "I have to go cool off, if you know what I mean and not just because of the heat". 

I opened my eyes to see Jake stand between our chairs.  that big cock just bounced in mid air.   Now that his cock was closer, it was truly amazing. Thick, long, and now I could see leaking wet.

Jake turned to pick up a towel and bet over in front of me, his balls were huge and low, which I find very sexy.   He turned back to me and said, "I hope to continue our conversation in a minute, just need to cool off".  While he said cool off, he grabbed his cock again, right in front of me.

He turned and I watched him head for the pool.   He dropped his towel near the side and jumped in.  I laid my head back down and tried to calm down as well.

I laid there thinking about Jake's cock and really how his hands felt massaging my ass cheeks, it felt so good and wanted more.  No way I could tell him that, of course, way too forward for me, but I could certainly think it.

"uh um", Jake cleared his throat.  I hadn't heard him get out of the pool, but he was standing next to me, already dried off.  "I see you didn't cool off much in that time", he said as he saw I was still very hard from the thoughts and our conversation.

I looked up at him, he was now only semi hard, but still...a thing of beauty.

"Sorry, carried away in my thoughts", I said.

Jake sat down again, facing me.  "Continuing our conversation, what were those thoughts you just had, if you are ok to share?".

I wasn't quite sure how to share those thoughts, because it is like a rabbit hole to me, but I shared this.  "When you were putting lotion on my butt, the way your hands moved, where you touched me at, I loved that and was replaying it in my mind, over and over".

"Tim, you have a great ass, I hope you didn't mind me exploring a little". 

I could see Jake's cock twitch when he said that.  "No, I actually loved it".  I was now breathing hard.

"Well, in that case, I would love to apply more lotion or even better, give you a nice rub down.  If you want".  Jake said

I really didn't know how to response, all I could come up with was "yes please".

Jake said, "great!" and stood up.  Now I could tell his cock was getting harder.  Jake held out his hand for me to help me up.  I took his hand and got up from the chair.  Jake then turned and led me towards the patio door entry to his bedroom.

When I walked through the door the bedroom was dark and it took me a few seconds for my eyes to adjust.  Jake's bedroom seems normal enough, not sure if I was expecting some gay dungeon, but it was just a normal room.  A big bed, night stands, dressers, TV, etc.  Jake turned to me, getting closer until I felt the wet tip of his big cock brush against my thigh. 

"Let me get a towel for you and then you can lay on the bed".  He said.

Jake turned, leaving a small wet spot on me where his dick touched me, to get a towel from the bathroom.  Jake returned with a towel and what seemed like a larger bottle of oil or lotion, I couldn't tell.  He laid the towel out and asked me to please lay down on my stomach. 

I crawled onto the big bed and laid down as instructed.  I then felt Jake get on the bed behind me.  I felt him move up so he was straddling my lower legs.  I felt some oil being dripped onto my lower back, down over my ass cheeks, and on my upper legs.

"Let me know if anything is uncomfortable for you Tim", Jake said softly.  I just moaned.

Jake's hands started on my lower back, above my butt.  He was soft at first, while moving his hands down over my butt cheeks to my upper thighs, using as much of the oil as possible.  It felt great and I told him so, "that feels very nice".

Soon Jake's hand were at my lower back again but this time applying more pressure and slowly moving them down ass, kneading my ass cheeks with the oil.  I was lost in pleasure when Jake softly said, "you have such a beautiful ass Tim". 

"thank you" is all I could get out.

Jake's fingers continued to caress my ass and then lingering in between them, over my ass hole, rubbing the outside of my hole and then moving on again, either to my lower back or down over my balls.  I had never experienced that, but it felt so damn good!!!  Jake did this a couple more times and then I felt him get up a little and lean in toward my ear.  As he did this his hands were on either side of me, I noticed because at the same time I felt something else, hot and hard, laying on my ass crack.  'HIS big cock'. 

"It seems as though you really enjoyed that last bit Tim.  I hope you it all.  I am going to work your upper back a little now".

I just moaned softly. 

Jake leaned back but his big cock staying in my ass crack.  I felt some oil being poured on my shoulders, and ten some drops dripping on my ass crack, must be falling on his big dick too.  As Jack started in on my shoulders his cock slid up and down my crack, his thickness spreading my cheeks apart.  I started to feel things I had never felt before and only wanted more.  I am was not sure why, but I started pushing back slightly on his cock, not really sure if he was noticing. 

When I was sure he didn't notice me push back on his cock, one hand left my shoulders and held my ass cheek, pulled it apart to let his cock head actually touch my hole.  electricity surged through me.  Then I felt a small pat on my ass and his hand returned to my shoulder.

"I like that boy.  It seems like your ass is aching". 

"mmmmmmmm.  yes sir, it is aching".  I managed to get out. 

Jake's hands started moving down my body again, over my back muscles to right above my ass cheeks.  I could feel his cock between my cheeks, still hard and I was still pushing back on him slightly and I knew he was enjoying that.  Soon Jake's hands were kneading each of my cheeks, his thumb would move under his big cock and brush my hole, first one once in a while then with every passing of his hand.  Before long his thumb would get stuck on my ass hole, each time it would get stuck it would poke in a little or pull my hole open.  I was feeling very very exposed to him and I really enjoyed it.

"Fuck Tim, your ass looks so good and is so eager for something in it.  Damn you really have me going."  Jake said..panting hard.  "Tim, I do have to apologize, I have made a bit of a mess....this whole time I have been leaking precum all over your ass."

Jake reached over and took my hand, guiding it behind me to feel his precum all over my ass and crack.  I was amazing I hadn't felt all of it already.  I was very wet back there.  He then guided my hand to his swollen, and very wet, cock.

"ummmm...I told you, I am  leaking like crazy."  Jake said.  "That's it, hold my big cock in your hand, milk some more out of me". 

I was definitely milking Jake's big cock.  I had never felt one that big and only fantasized about it to this extreme.  I wanted something inside of me, needed something inside of me, needed Jake's cock inside of me, BAD!

I held Jake's cock in my hand and turned to ask him 'the' question.  "Jake, will you fuck me?".

Jake leaned down close to my face and said, "yes Tim, I would love to".  Jake then kissed me fully, his tongue in my mouth, not sure I would have liked that, but I found it so sexy and sensual.  I wanted more.

Jake raised up and I started to spread my ass cheeks for him, but instead of his big cock, I felt his thumb slowly enter me.  "Tim, I think I should fuck you with you on your back to start with."  I looked at him with a puzzled look, I didn't understand.  Jake continued, "Since it is your first time, and my cock is a little big, I can take my time and see the reaction on your face and now how fast to go.  Plus the angle of my cock entering you will be easier this way.  I know you want a cock in you from behind, and trust me I want to fuck you from behind, but let's start with this position."

I felt Jake pull his thumb out of my ass, I felt so empty and wanting more.  "Turn over Tim", Jake said while helping me turn over so I was on my back. Jake's fingers went right back to my ass, playing with me and then stroking his amazingly hard cock that was bouncing right in front of me.

"Tim, I am going to lube you up to help me sliding into you".  Jake grabbed a bottle of lube from nightstand drawer.  I felt him drizzle some on my hole and then watched him lube up that big cock.  It was so impressive to see.  My own cock was twitching just watching him.

Jake then took my legs and put them over his shoulders.  while holding his cock with one hand, Jake asked, "are you ready Tim?".  I nodded my reply, it was all I could do. 

Jake rubbed his wet cock head around my hole.   "Tim, I want in your ass so fucking back, I am leaking everywhere.  I hope that is ok".

"Yes Jake, I love that feeling".

"Tim, I want in you so bad, but I also need you to know something".

"ok"

"Tim I am hiv positive.  Do you know what that means?", Jake asked. 

I felt the pressure of his cock at my ass now, slightly pushing.  "Yes", I said letting the conversation drop.

"Tim, I am on medication, and truly  undetectable, but I wanted you to know before I push into you.  I have been leaking in your hole for a few minutes now, but at this point it is your decision.".   Jake stopped pushing.  He looked into my eyes and I knew I wanted him in me so fucking bad.

"Jake, please fuck me". 

Jake smiled and started to push in again. "Tim, you should push out a little, like you are taking a shit, but don't push that  hard.  It will help you accepting my cock.".

I started pushing out a little, and at the same time Jake started pushing in.  I felt a lot of resistance by my ass, not wanting that big thing in me, but our will power overwhelmed us both.  In an instant it was like a 'pop' and I felt his cock head expand my ass open wider than I had ever felt before.  It was painful, but at the same I just wanted more!

Jake paused, "thank you baby, fuck that feels so good.  I am going to start pushing some more".

Now Jake had his hands on my hips and alternated looking into my eyes and looking down to see his cock disappear.  "Good boy Tim, you have taken half of my cock already.  here comes the rest".

Taking the rest of Jake's big cock was more of the stretching and dull pain that there at been, but I could tell the pleasure was also increasing.  I looked down at Jake's waist, which was so sexy but it is now I noticed my cock was only semi hard, but oozing a continual stream of precum.  I had never done that before!  I knew right then I needed more, much more!

Finally Jake's hips were touching the back of my legs.  "There baby boy, I am all the way in you, fuck it feels good".  Jake said.

Jake took one leg in each hand and started to slowly slide in and out of my ass.  Jake's face and an intense look of passion and lust.

"Your ass is so tight Tim, you are milking my cock"  Jake said while watching his cock slide in and out of me!

Jake pulled his cock all the way out of me and I was left open and panting, wanting more.  I felt so empty!  Immediately he pushed all the way in me, up to his balls.

I moaned out loud...no it was more of a very loud whimper.

"yes baby, take my big cock", Jake said.  "You love it don't you boy?"

I moaned a loud, "YES"!  I was in pure ecstasy .  I had never felt anything like it, the true fucking of a true man.   My eyes rolled back into my head

I felt so full with Jake in me, full of that massive cock.  I looked at Jake again, his eyes were open and staring at me as he slid in and out.  Jake pushed all the way in me and bent down between my legs so his face was just above mine.  He then kissed me deeply and I returned his intensity and wrapped my legs around his back.

Jake broke the kiss and looked me in the eyes, "baby, I need to cum so bad.  I will tell you and then pull out and shoot my cum on your stomach and cock". He paused, looking at me.

It look me few seconds to think, and I asked him, "is that the best way for you to cum Jake?"

"No boy, I would love to fuck you fast and deep and then cum deep in you, but only if you wanted that too." Jake said.

Again, I paused and thought, then looked into Jake's eyes, "I want you to cum in me sir, please". 

Still looking into my eyes,Jake began to smile and I almost thought I felt his cock swell a little more.

"That makes me so happy Tim, good boy."

Jake rose to kneel again between my legs, taking each leg in a hand.    His look was of pure desire now, and that turned me on even more.  Jake removed his hand from one leg and wrapped it around my hard cock.  "That's it boy, we are going to cum together".  He started picked up the pace of his cock sliding in and out of me.  Each thrust back in me I felt his cock head touch an area I didn't know existed and heard the slapping sounds from his waist hitting my ass.

"fuck yes boy.  you want my cum, don't you?".  Jack said while breathing hard.

"yes daddy, please! I want you to cum in me".   The pressure of Jake's big cock sliding in and out of me, hitting every pleasure spot, and his hand on my hard cock was all I could take.  "Jake I am cumming, I am cumming"  and shot my load all over his hand as he jerked my cock up and down.

"fuck Tim, I am cumming, take my load boy".  Jake pushed in deep and I felt his cock grow and then felt the pressure of a stream of liquid in that deep place in my tummy.  Jake was shooting his hot cum into me...four...five...I felt the streams in me.  Jake was cumming so much.

Jake stayed buried in me....hand still on my cock.  I noticed Jake was shaking a little as every drop of man cum left his body.  Slowly, he stopped shaking and then his eyes opened and a big smile crossed his face.

"oh fuck Tim, I am still dripping in you!  That was so fucking hot.  Your ass feels so good on my cock.  Did you enjoy it too baby?"  Jake asked

I smiled wider than I had in a long time.  "yes daddy, it was better than anything I could imagine".  

Jake slowly pulled his softening cock from in me and collapsed on top of me, head on my shoulder.  He was breathing harder than me and I just wrapped my arms around him. 

I whispered to him, "I would love that again sometime".

Jake raised his head from my shoulder and looked at me.  "Tim, anytime you want me inside of you please let me know.  I loved fucking you.  Honestly Tim, I want to breed you so much".

I closed my eyes and smiled, and then I felt his cum load making its way through my insides.  I smiled even wider.

 

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