Rooming with grandpa

[austin_submale]

Interesting so far...  Looking forward to seeing where it goes.

 

[labtm]

Yes definitely following this story

[Jaygusher]

Part 4

I was alone in the apartment. Grandpa left to chase a hookup so I had time to myself. I was looking forward find out what else he had to teach about gay life but at this point the timing was appropriate. His lessons, along with his brazen prankster behavior, put me at my limit for shenanigans. My penis almost went in his mouth, his penis almost went in my mouth, and he rammed his boner against my butthole right before leaving. I knew he was just joking around with me, but that last one hurt a little. I stuck a finger in my ass and massaged my hole. It was still a little sore from his tip trying to push in. I’m sure my virgin ass worked to my advantage to keep him out but what if he had managed to penetrate?

 

Holy shit! That would mean I would have almost lost my virginity to… my grandpa. That is absolutely not a story I’d want to tell any future boyfriend. Well he was with a hookup so that should calm down his pent up energy. I decided to remain naked since I was alone. Trying some of that free lifestyle he talked about. I cleaned the place up bit. I cleaned the dishes from breakfast and picked up some clothes laying about. It was the least I could do. Help with the house work as I stayed there. 

 

It was probably a half hours worth of cleaning up when I took a break. I thought about ways to occupy myself. Naturally since I stayed nude in the house, my thoughts went to my dick. I still haven’t gone off this morning so I figured I would try to blow off some steam. I went to the bedroom and laid down in bed. There was plenty more room since I was there alone. I was playing with my dick when I felt my balls touch something wet. I looked down and saw there was a white puddle on the sheets. That must have been where grandpa came earlier this morning. Oh goodness, I shouldn’t touch that. I moved up a little bit, getting my balls out of his spunk. I looked up some porn on my phone while playing with myself, stroking myself to erection. As I was scrolling through different types of websites, I saw some videos of guys using dildos. It looked pretty fun, and I had never used one before. That’s when I remembered grandpa Lewis telling me that there were drawers filled with them. The thought of using his sex toys seemed weird to me. But he wasn’t here so I figured it would be fine as long as I put it back where I found it. 

 

I went over to the dresser and pulled up in the first drawer. Oh wow! There were so many different things. There were dildos of all shapes sizes and colors. There were butt plugs and things that looked like balls on a string. And a few other toys that I couldn’t really describe very well nor could I comprehend what they were used for. I picked out a tan colored one. One that was probably about the size of my dick erect. I found a bottle of lube as well and I got back on the bed. I lubed up my dick and my ass. I played with my hole with one hand and my dick in the other. I wondered if I could get that thing to fit in me. After what felt like maybe five or 10 minutes of fingering. I grabbed the dildo and applied a generous amount of lube on it. I pointed the tip towards my ass and tried guiding it in. It required quite a bit more force than I imagined but as my hole started opening up it hurt. I took a break from it for a minute then tried it again. Then took another break. I kept going back-and-forth like that, pressing the dildo tip against my ass, trying to work it in. Periodically adding more lube to it with every other attempt. It was more difficult than I thought. I didn’t know how long I was attempting for. It felt like a long time. Eventually I managed to work the tip in. The rubber head popping in past my ring. I held it there for a minute rubbing my dick as my ass relaxed on it. I worked it slowly up inside me. After the pain and discomfort subsided. It started to feel good. So I started thrusting the dildo in and out of me. Slowly at first then I found a good rhythm. 

 

I must have fucked myself like that for a while. Stroking my dick and plunging my ass. My prostate was getting hit too and I was leaking hard. It felt amazing and I could feel myself on the brink of orgasm. I jammed the dildo in deep. It hurt a little but the pleasure outweighed the pain by a long shot. I was stroking fast and gasped. My cum shot up in the air and covered my belly, several ribbons worth. 

 

I laid there catching my breath. Dildo still firmly inside me. That’s when I heard the front door open.

 

“Kenny, I’m back.” Grandpa was home. In a panic I pulled the dildo out. It was still covered in lube and juice. I threw it in the drawer and quickly wiped myself off with a pair of grandpa’s underwear from the floor. That’s when the bedroom door opened. “There you are! What have you been up to?”

 

“Oh! Just tidying up.”

 

“I can see that. Doing laundry? Or were you having fun with my briefs?” I was still holding them.

 

“No, just laundry.” He took the underwear out of my hand and looked at it.

 

“Hm? I guess at some point I blew a load on this. I don’t remember that though. Oh well these days I forget half the places I dump my sludge.” He put it up to his face and started licking the cum off of the underwear. I thought to myself ‘No! No! Grandpa don’t! That’s you’re grandson’s cum you’re eating!’ But I kept a straight face and pretended like nothing was wrong. “Mmh that’s an unusually sweet load. My cum normally has a strong bitter savory flavor.” He finished licking the underwear in front of me then tossed it aside. “So Kenny boy. How’s about you get dressed? We’re gonna go to a gay fetish store down on Pike street. Another kinkster from my social circle works there. Sound fun?”

 

“Yeah! That sounds great.” I was excited to go to a gay shop. I’ve never been to one. And getting out of the apartment seemed like a good way to avoid any more of these close calls. I threw some clothes on. Grandpa threw on some sweatpants and a tank top and sandals. Obviously he didn’t feel like dressing up much for going out.

 

The place he wanted to take me wasn’t very far. Only a few blocks away. I took in the sights of the city while I could. Everything looked big and busy. It was a shop called Doghouse Leathers. Inside I was impressed with the vast variety of clothing and adult toys on the shelves. So many things that I didn’t know what they were used for. The guy at the counter was an older bear wearing a black leather vest with no shirt on. He looked up at us and immediately recognized grandpa Lewis.

 

“Mr. Lewis! How are you doing? And who is this pretty new thing you have with you?“ 

 

“This is my grandson Kenny. My real grandson. You remember. I mentioned him once or twice.“

 

“Oh! This is the one. Like, actual real family grandson. I guess your visit is going to be pretty tame this time. Showing him the sights?“

 

“Yes I am. Kenny boy here is gay as well and I wanted to show him his first gay store. Maybe some of the things here will catch his interest.“

 

“Aw, that is sweet of you to chaperone him around for his first time at a fetish store. I’m flattered it’s mine. Well you guys take your time and help yourselves to try out anything you like. I will be here if you need my assistance.“

 

“Will do.“ he guided me through the shop, showing me various outfits, underwear, and contraptions. He was informing me on all of their uses and the wild kinks that went along with them. There were so many things that guys were into that I didn’t even know existed. Water sports, pup play, chastity, electro shock, rim chairs, tickle brushes, floggers. I almost felt my head spin over trying to keep up with so many different things. I just let grandpa go on and on while I just smiled and nodded at everything he was telling me. It was all so much, but I was enjoying myself.

 

He asked me if I wanted to try on anything. He was looking towards the leather harnesses and gimp masks. Those were all too advanced for me. I looked at some specialty underwear that looked pretty cool. One had a zipper that started at the top of the crotch and went all the way down and up to the top of the butt. Grandpa saw me looking at that one and he grabbed it off the rack. 

 

“Here try this one on. You’d look great in it.”

 

“Are you sure? It’s not too revealing?”

 

“Of course not. It’s practically European. Come, let’s get you fitted. I want to try on some things too.” He took me to the changing rooms in the back. It was basically a corner with a curtain. He got in with me. “Okay strip.”

 

“Do you have to be in here with me? I can do it myself.”

 

“But I like helping you. Are you really going to be shy in a place like this?” He had a point. And we did spend a lot of the day nude together. His hands were already getting my clothes off. First my shirt then may pants came down. I bent over to get my shoes off when I felt something warm against my butt. 

 

“What’s that?”

 

“Just my cock, don’t worry about it. The changing room is small and you practically backed up into it. What are you trying to do? Gobble it up with your ass?”

 

“I’m just getting my clothes off.”

 

“Then do it.” He punctuated his demand by thrusting forward. His tip hit my hole. I was still lubed up and stretched from the dildo earlier so when he thrusted forward my ring opened up and hugged his tip, half of his head was poking in. But his head was much wider then the dildo so it still hurt a little.

 

“Ow, that hurts. You should take it away.” I whispered. Trying not to alert anyone to what was going on.

 

“What’s going on down there? You’re ass is very sloppy and not as tight as it was previously. I’m almost inside you. Tell me the truth young man.” He held his dick there. I was quickly working off my shoes and socks to get the rest of my pants off. 

 

“I-I played with one of your dildos, I’m sorry.”

 

“Oh is that right? Well I did say you could play with them anytime. I thought you might have had a trick of your own when I was emptying my balls. But you should have told me. Look what you did. Do you want my cock inside you?” He pressed forward more. My ass opening up more around his head.

 

“No! Please take it out!”

 

“Relax it’s not inside you. This is just a kiss. You’re still very much a virgin. What an outrageous thought, me deflowering you. He he he.” That’s when the curtain opened. The leather bear from the front register was looking at us. Me bent over and my grandfather with his dick nearly penetrating me.

 

“Anything I can help you with?” He unzipped his leather pants and pulled his cock out. It was fat and he had a biohazard tattoo right above his shaft. He was stroking it, getting it hard and he moved it closer to me.

 

“We’re fine Bruce. I was just helping Kenny try on some underwear.” Bruce wagged his dick a few times. It was erect now. He looked down at my ass and what was poking at it.

 

“I see. Let me know if I can offer anything.” He didn’t put his dick away but he backed off and closed the curtain again. I was alone with grandpa Lewis. I got all my clothes off and stood up. His dick left my ass and I grabbed the underwear to try them on. 

 

“Just a moment. Help me put on my item.” He asked.

 

“What did you get?” Grandpa held up a black butt plug. 

 

“He said we could try anything. How about you push this up in me?” 

 

“Why me?”

 

“Because you should see how it works. Plugs are a little different then dildos.” He put the plug in my hand and turned around. He spread his ass apart and revealed his hole to me. It was wet and puckering towards me. He clearly had action down there when he had his hookup. “Go on. Put it up in me.” 

 

I put a hand on his ass and aimed the plus towards his hole. I didn’t know how much pressure to apply but it went in him easily enough. As it past the widest part his hole clamped down on it with a wet quenching sound.

 

“Awww yeah. That’s it. See? Easy enough.” He stood up and faced me. I was now pulling up the underwear and straightening the waist band.

 

“Yeah it wasn’t too hard. Should we be doing this grandpa? Isn’t it kinda [banned word]?”

 

“Do you dislike spending time with me?”

 

“No not at all!”

 

“Did you dislike putting the plug up my ass?”

 

“Um, it wasn’t bad. It was okay.”

 

“Then what’s the problem? We’re just having fun. And I love teasing you.”

 

“I guess your right. I’ve been having fun too. But your teasing does get pretty extreme sometimes.”

 

“I know, that makes it more fun. Those look nice on you. Turn around let me see that bubble butt.” I spun around and showed them off. I did like the look of them. “Let’s see if the zipper works.” He reached around and undid the zipper. My dick popped out and he kept pulling it down and up the other side, revealing my ass. “Yup those work good… just a sec. Hold still.” 

 

I held still with my back towards him I heard a moist popping sound and then a forceful push against my own ass. Something went up inside me.

 

“Grandpa what is that?!” He pushed and it popped up in me.

 

“Just the butt plug. You seem to like toys in your ass and you are well lubed up so might as well.”

 

“Grandpa that was in your ass!”

 

“Now it’s in yours. It’s basically the same as sharing a Coke. Leave it in.” He zipped me back up. The plug firmly planted in me. His ass juices were probably mixing in with mine. “Come on, get dressed. It’s time to head out.” 

 

This was crazy. I had something that was inside him, up inside me. We both got dressed and wandered toward the register. As I walked the plug felt weird. Almost like it was going to fall out. But it’s shape wouldn’t allow that. We got to the register and the leather bear still had his dick out.

 

“Just the underwear?” He asked.

 

“And a butt plug.” 

 

“Okay come around the counter, I’ll need to scan it.” I walked around to where he was. He bent me over the counter and pulled my pants down looking for the tag. “Ah, it’s on the inside.” He reached for the zipper and unzipped it all the way to the back. “Here we go. I’ll need to type it in. Nice ass.” He put a hand on my back and leaned over me, his cock pointed at my ass. He started typing something in the register.

 

“No funny business now Bruce.” Grandpa seemed a little apprehensive.

 

“Just gonna put these numbers in” Bruce swung his hips back and slammed forward. I slammed into the counter. “What? Oh! Theres the plug. Cheeky bastard.” The plug obviously stopped his dick from penetrating me. I guess now it didn’t seem so bad.

 

“Just ring is up you horny fucker. I knew you’d try that. Kenny boy here is a virgin and I don’t plan on throwing him to the sharks yet.” Bruce took the price gun and scanned the bar code on the base of the plug poking out my ass. Grandpa payed for the two items and I zipped myself up. 

 

We walked around down town for a while. He showed me cruising spots and places to eat. All the while I was walking around with a plug up inside me. We spent quite some time in town until it got late. Before heading home grandpa had one last place to show me. We were on Summit Avenue and saw a discrete building.

 

“This is Steamworks Kenny. It’s a gay bathhouse where men come to hook up with each other. It may be a little advanced for you for now but I will take you here when you’re ready.”

 

“Really? I had no idea a place like this existed.” 

 

“It’s not meant to be heavily advertised. A lot of the men here like discretion.” I looked at the building for a while. Then grandpa took me by the hand and we walked back home in the dark.

 

When we got back grandpa immediately threw off his clothes and let it all hang out again. he loved being naked. He took me by the hand and brought me to the bedroom where he proceeded to take my clothes off as well.

 

“Today was fun grandpa. Thanks for taking me out.“ 

 

“It was my pleasure Kenny boy. Get on the bed for me, I want to inspect that plug up inside you.” I now had all my clothes off. Even the new underwear were thrown aside. I got on the bed and lay down I was rubbing the plug inside me wondering if I should take it out yet.

 

“It’s been in there for quite a while grandpa.“ He got on the bed with me and grabbed my legs and put them over his shoulders, his hips almost met with my ass. “This is a very awkward position grandpa.” 

 

“I can better inspect you this way.“ He grabbed the plug and started thrusting it in an out of me. It was causing my dick to get hard.

 

“Maybe you shouldn’t do that.“

 

“Yeah you’re right, you don’t need this anymore.” Grandpa pulled the plug out of my ass and started sucking on it. “Mmm, sweet.”

 

“Isn’t that dirty?“

 

“Nope, you’re clean inside. This is just your sweet love juices. Well yours and some of mine.” His dick was resting on my butt hole. I could feel it getting hard.

 

“Grandpa I think you should move your dick.” Grandpa put the plug down and wrapped his hands around my thighs. He moved his hips forward, his cock head pressing up against my ass. My hole easily opening up and wrapping around his tip.

 

“Whatever you say Kenny boy.“

 

“No! That’s gonna go in!” Grandpa pulled his dick away and let go of my legs.

 

“How was I supposed to know that? You should be more specific.“ I sat up.

 

“You like to push your jokes far. But we can’t actually do that. That would be… incest. Wouldn’t it?”

 

“Hey, a hole is a hole. If it feels good, you should just let it happen.“

 

“But, you have…”

 

“AIDS, I know. But that doesn’t change how good my cock would feel in your virgin ass.“ I was starting to feel uncomfortable. I couldn’t tell if he was being serious or not. I sat there in silence looking away, sensing my discomfort he change the subject. “Since you know I like to hook up, and I’ve shown you some of the ropes around here. I think tomorrow I’m going to have one of my tricks come over. He and I are going to play around here. You don’t have to stay and watch, but it would be a great lesson for you. A visceral demonstration on how to properly fuck, and some more kink demonstrations too.”

 

“Oh, uh, I guess that would be interesting to see.” Could I really watch my grandfather fuck somebody? Wouldn’t that be as awkward and uncomfortable as walking in on your parents having sex? But grandpa Lewis wasn’t a parent. He was technically my grandparent, but he’s so carefree and sex positive. My thoughts went back-and-forth on it being weird and it being an interesting learning experience. Mostly leaning towards the learning experience.

 

“Well it’s getting late. Time for bed I say.” It was late and I was pretty tired from the day. I looked around to find some pajamas to wear. But grandpa stopped me. “No need for those, we can sleep in the nude. We walk around the house naked. We can sleep naked as well.“

 

I guess that was true. I was a little concerned about his dick rubbing up against my bare ass in the middle of the night. But if it got too frisky, I could always just move to the couch.

 

“Yeah, alright.” We got ready for bed and got under the covers. Grandpa was sitting up looking at our position, contemplating.

 

“Okay last night was a little cramped so let’s try something different. How about you lay down on the bed and I’ll just rest on top of you.”

 

“Wouldn’t that be kinda smothering?”

 

“Hey now. I’m no fat. Well I have a bit of a belly here but I’m fairly light for my size. Just get into position. This will save space.” I laid down as instructed. I wasn’t too sure how this was going to work. Grandpa crawled on top of me, and laid down. His head rested on my back. I felt his cock rest between my cheeks. He wasn’t very heavy but it was still a weird position. 

 

“Are you comfy like that?” I asked.

 

“Oh yes Kenny. You’re very warm. And your bubble butt is very cushy.” We got comfy and tried going to sleep. Grandpa managed to fall asleep faster then me. I heard him snore quite a bit. The weight of him laying down on my felt like it wouldn’t allow me to fall asleep but I tried. 

 

I eventually started nodding off. Waking up here and there in the first part of the night. I couldn’t help but think of his dick between my cheeks. But I managed to fall asleep. 

 

In the middle of the night I woke up to something poking me. Grandpa was snoring still and he had another hard on. It felt uncomfortable so I tried to wiggle around a bit. It wasn’t working well since both our bodies were pressed against each other. The only thing I could reach was my ass. His dick was so hard it hurt as it jabbed my butt cheek. I may have been slender but my ass was pretty round so there was a lot for his dick to poke against. 

 

I thought about my options and the only thing I could come up with was grabbing my ass and spreading it. I did and grandpa’s dick stopped poking my cheek and slipped down to poke at my hole. It wasn’t ideal but my cheek didn’t hurt anymore. I allowed myself to fall back asleep like that.

 

My dreams were nondescript. I couldn’t make heads or tales of anything. But through out my dreams I had a strange feeling on my ass. The feeling grew more intense as I dreamt away. Then the feeling went painful. That’s when I woke up. It was still night but my ass was hurting. Grandpa was still on top of me snoring away. But it felt like his dick slipped its head into me. I could feel my hole stretched open and it hurt. I may have had practice with his dildo earlier but there’s no way I was ready for some thing of his size. Now that I think of it, it was probably a bad idea to practice stretching my hole with that dildo earlier in the day, and more so not good to have had a plug in me the latter half of the day. Otherwise his dick might not have gotten inside of me so easily. I was still. I didn’t know how to correct the situation. I didn’t want to wake him to find his dick inside me. That would have been too embarrassing. The longer I laid still the more his dick slowly sank in. Eventually it stopped sinking. It felt like half its length was in me. 

 

‘Oh god, hes inside me! Am I losing my virginity like this? No, this doesn’t count. He’s not awake and he’s not actually fucking me. This is just an accidental slip. What do I do? This is bad.’ No matter what, I couldn’t think of anything for my predicament. The only thing that could possibly work is if I just went back to sleep and if he woke up first in the morning he’d realize he slipped in and pull out on his own. Hopefully he’d avoid mentioning it to me. I closed my eyes and focused on sleep. It was hard. And not just dick in my ass hard. But I managed. My ass relaxed and grew accustomed to the fleshy intruder and I fell asleep again. 

 

My consciousness faded in and out. That in-between state of sleeping and waking was over me as I was trying to stay asleep. I dreamt that I was having a hard time keeping my balance. I felt like my hips were being rocked back and forth. A weird pressure sensation in my ass as my hips moved back and forth. When I partially awoke, the bed was shaking up and down a little and my body shaking with it. The source of the movement felt like it was centralized around my butt. I was too drowsy to recognize what was going on, and I drifted back off to sleep.

 

It was early in the morning by the time I woke up. My my eyes slowly opened up, looking around the room. To my dismay grandpa was still asleep on top of me. He was still snoring and I felt drool coming out of his mouth and running down my shoulder. But more importantly, his dick was still inside of me. It was hard to believe that it stayed like that inside of me all night. It had to have gotten soft at some point. It must’ve been morning wood? I kept still, pretending to be asleep, waiting for grandpa to wake up and pull out of me. Periodically his dick would twitch inside, keeping me very aware if it’s presence in me. 

 

Grandpa wasn’t waking up yet so I tried wiggling my ass, hoping it would gently shake him awake. His snoring stopped and he started moving around. I went back to pretending to be asleep. He propped his hands on the bed and stretched, arching his back and driving his hips down as he yawned. The stretch caused his hips to drive his cock deep down in my ass. Almost full length sinking in. I merely gasped. I tried my best not to respond to it. It felt so intense having the thing go so deep in me. 

 

“Oh, what’s this?” He whispered to himself looking down at where his tool was located. He patted my shoulder gently to see if I was awake. I maintained the act. I wanted him to pull out so he could act like everything was normal in the morning. But he didn’t pull out yet. Instead he started gently moving his hips up and down. What?! Why’s he doing that?! His movement was subtle but consistent. 

 

There’s no way he’s actually fucking me. He wouldn’t. This has to be his attempt at gently wiggle his cock out of me without waking me. I was sure that was the case, so I laid there letting grandpa do his thing. The sensation of his cock wiggling around inside me was stimulating my prostate. I didn’t want it to feel good but my body betrayed me. It felt good wither I wanted it or not. 

 

I thought to myself ‘sorry for sorta enjoying it grandpa’ it seems like he was having a hard time pulling out so I slowly tried spreading my legs a little without him noticing. Giving him easier access to maneuver. I wanted him to succeed in his efforts. I thought ‘That’s right grandpa. Keep doing what you’re doing. I’ll try to make it as easy as possible for you to accomplish what it is you were trying to do.’

 

His breathing started to get a little labored. I guess attempting to wiggle out of me was physically demanding for him. Especially with all of his attempts to do it as gently as possible without ‘disturbing’ me. Then his hips started raising up. His cock was exiting my ass. ‘Great, just a little bit more.’ He stopped with the head of his cock still inside me. Then he grabbed his shaft and started stroking it fast. I thought ‘that’s a weird way to pull it out’ he kept stroking for a while and his body started trembling. I heard him whisper very quietly “yeah that’s a big AIDS cock in there. Gonna shoot it. Gonna shoot my AIDS load….” What? Did I hear that right? His words were barely audible. His cock was repeatedly twitching and I felt his head expanding in me. No way. He wouldn’t be trying to ejaculate. That’s really dangerous!

 

At this point, pretending to be asleep wasn’t an option anymore. My only other choice was to fake waking up and get him to pull out. He kept stroking his cock with the head lodged in me as I thought to myself. ‘What would I say? Wouldn’t it be fairly awkward afterwards? Aren’t I technically no longer a virgin anymore? I need to do it now, wake up and ask him to get off…‘ But my thoughts were interrupted as grandpa started to softly grunt…

 

[negchaserlooking]

Hot - now Grandpa - did you or didn't you?

[Jaygusher]

36 minutes ago, negchaserlooking said:

Hot - now Grandpa - did you or didn't you?

There’s the million dollar question 

[Mvillebottom]

Damn  jaygusher  I absolutely love this and your other stories.  Can't wait to read more

[drew4fun]

I'm really enjoying this writing buddy, thanks Jaygusher!

[labtm]

Got me boned here at work. Thank you I am a big fan. 

[cumhole1919]

This reminds me of when I was negative and thought I was playing safe.  Back then if a man I was blowing pulled me up and turned me around to fuck me bareback, I wouldn't object, because I wasn't in control of the situation.  I surrendered all responsibility to him once he let me suck his cock.  I assumed no one would fuck me bareback unless they knew they were negative.  Naive, huh?  Now I know that many men would assume that I was poz because I let them fuck me without a condom.  I probably took a number of poz loads back then before I finally converted.    If a man like Mr. Lewis was doing this to me (yes, please) I would have left it up to him.  If I knew he was poz, I probably would have assumed he'd pull out before he came in my ass.  I wasn't chasing, but I wasn't running away from it, either.

You're a great writer, and remembering those days has given me a big boner.

[Jaygusher]

Part 5

 

Grandpa was inside me. Stroking his shaft and getting dangerously close to orgasm. I heard him starting the quietly grunt and that’s when I had to fake waking up.

 

“Oh fuck here it comes…Yes…oof. Oooh! Yeaaaaaaaaah! Ahhhhhhhh….”

 

“Grandpa? What’s going on?” I asked with a groggy tone. He stopped all his movement and placed his hands back on the bed.

 

“Good morning Kenny! Looks like I accidentally slipped a little bit inside you durning the night.” He acted like someone who wasn’t about to cum. Was he really working to orgasm previously or was he actually working his way out?

 

“Oh no! That’s not good. You should take it out.” 

 

“Are you sure? Does it hurt?” Grandpa let his body lay back down on me. His cock sinking in, still hard as rock.

 

“Ah! Uh no but it’s dangerous.” He wiggled his hips a little.

 

“You’re perfectly okay, I want you to feel it in you a bit. How is your first cock? Never mind it being mine. I want to know how you like it. How do you like it knowing your virginity is gone?” I didn’t know what to say. It felt good. I love cock but I can’t let him stay in me.

 

“It’s, uh, it’s fine. It feels good”

 

“And you feel amazing Kenny. My snake found a good home.” Grandpa gave a few thrusts in me then pulled out with a wet popping sound. I finally had it out. It was in me for so long I was wondering if my ass would ever recover. We both slowly got up. My body was stiff and my ass was sore. I liked having a cock inside me but my first one being grandpas was not what I had in mind. My first time was incest. I felt so embarrassed.

 

“Grandpa, would it be okay if you don’t tell my dad about this?”

 

“Absolutely! This will be our little secret. No one will know what goes on in here.” That made me feel a little better. We got up and his cock was still hard. It was shiny from my ass juices. He was playing with it. “I said today I’d invite someone over. I think ill go get him now. I’m really horny and need to blow desperately. I can show a few fun things that way.” 

 

“Okay.” Grandpa headed for the door in the nude. 

 

“Stay naked for me Kenny. My hookup will love to see that beautiful body of yours too.” He left me alone again. I was surprised that he left naked. Would someone see him? I stood around the living room. Playing with my ass. My fingers could easily go in. Not surprising since it had a huge cock in it all night. I thought back to what grandpa was saying while he was stroking his cock inside me. It sounded something like he was going to shoot something. He said it very quietly so I couldn’t really say for certain what it was. After a few minutes grandpa Lewis returned with a friend. It was the older big guy from the first day I got here. “This is my friend George. He’s graciously agreed to let me demonstrate on him for you.” George walked up to me. He looked at me like some predator. He was tall and fat. Balled and tan, like one of those older men at the beach that like to darken in the sun. 

 

“…Hi there.” I greeted meekly. George started stripping and grandpa helped him. They were headed to the bedroom and grandpa had me fallow. George got on the bed and got in a doggy style position. His ass was huge, and his hole was like a juicy round doughnut. Grandpa wasted no time slamming his dick in there.

 

“Look here Kenny. This is how you properly fuck a man.” His hips were violently plowing away. George was grunting in the pillow. It was definitely a shocking sight, seeing two older men fuck in front of me. “Get closer Kenny. Watch my cock slide in and out of him.” I stood beside the bed and watched the to go out it. Grandpa‘s hard veiny cock was working its magic, and the big juicy asshole was eagerly excepting the tool as if this was not the first time it had. “Get your face between my legs Kenny, I want you to watch my ass hole and balls twitch as I unload in him.“ I moved around to look at grandpa‘s ass. It was shaking back-and-forth and I didn’t want to make contact with it. Grandpa reached behind and grabbed me by the head and pulled me towards him. My forehead slapped up against his ass and my face went into his large sagging balls. I was getting slapped by so many parts of him at once. My face was getting wet from his sweat and musk.

 

“Grandpa that’s too close-“ as I opened my mouth to speak his balls swung back and entered my mouth. I could taste them. They were moist and salty. I spit them out and kept my mouth shut, grandpa‘s hand firmly holding my head in place.

 

“Sorry George I can’t make it last as long as I usually do. My balls got primed up quite a bit earlier so I’m going to shoot it now. Oh fuck! Oooof! Oooooh!” As grandpa reached orgasm his ass cheeks clenched my forehead. I watched his balls raise and lower as they pumped load after load of cum into George. After he deposited his load, the three of us stood there for a brief moment, grandpa catching his breath, George enjoying his back door breakfast, and me taking in the sight of it all.

 

I pulled my face out and sat up. Grandpa pulled out of George and a glob of cum poured out of him. Grandpa was spreading his cheeks so I could get a better look at his hole.

 

“Now Kenny my boy. I’m going to teach you about rimming. Look at all George’s cum shoot here. Doesn’t it look delicious?“ He was presenting it to me like it was some sort of meal.

 

“Yeah, make the boy eat out of my ass.“ George mumbled through the pillow.

 

“That’s for him to decide old boy. So how about it Kenny, want to dive in and get your tongue up in there?”

 

“No! That’s a bit too much. Besides it’s covered in your cum. Aren’t you positive? Shouldn’t you have worn a condom?“ Grandpa chuckled, George scoffed at the idea.

 

“I already told you, I never use those things. George doesn’t care what he gets. He just loves cum, but if you’re not going to lick up that savory protein then I will. Watch closely.” Grandpa put his face between George’s ass and started licking the cum that was seeping out. He dug his tongue up in there and kissed his ring. I knew about rimming but obviously this was the first time seeing it in action. I guess as long as the hole was clean it seemed pretty hot in theory. I would like to try it sometime, but I’m not sure if I wanted to try it with George. 

 

The rim job continued for a few minutes, grandpa sucking away down on that ass like a ravenous animal. George was moaning, I watched his toes curl with each probing. George had big feet, bigger than grandpa‘s. He looked like he was really enjoying the service. Grandpa finished up and got out from the cavernous hole.

 

“Hey Mr. Lewis. How about some coffee? Why don’t you put on a pot?” George asked.

 

“Yeah all right. I could go for a cup myself. You two behave yourselves.” Grandpa got up and left the bedroom, closing the door behind him. 

 

I was now alone with George. The first time I was alone with a naked man other than grandpa. I got up off the bed and I was heading towards the door to go help grandpa with the coffee, but then I felt hands on my shoulders and a belly pressed up against my back. George wasn’t letting me leave.

 

“Not so fast boy. Let me play with your ass.” George roughly rammed two fingers up inside me, it made me gasp little. “Damn I thought a virgin boy would be tight. You let your grandpa fuck you?” His finger assault on me continued, I was too scared to say anything. “Get on the bed and stick your ass up for me. I haven’t gotten off yet, and I need to shoot my rancid cum in some thing.”

 

I tried to protest but George guided me back to the bed. He pushed me down onto it with my ass up in the air. He grabbed my hips and propped me up and spread my cheeks apart.

 

“Sir please, we shouldn’t.“ George was now slapping my ass hole with his cock. His belly resting on my ass, his other hand pushing down on my back. 

 

“Don’t worry slut, I’ll make this quick. But you’re definitely going to hate what my balls are carrying. If Mr. Lewis has been fucking you then it doesn’t really matter.” 

 

”Sir no!-“ George slammed forward and I felt the entirety of his cock go up inside me. My ass had some recovery from the morning so it was a little bit of a shock when he slammed in balls deep. He wasted no time picking up a fast fucking pace. 

 

“Oh fuck yeah. Virgin boy my ass. But fuck it still feels good.“ His movements kept my face buried in the pillow. Plow after plow I felt George assault my ass with his cock. I was scared, but I had to admit it did actually feel really good. I never thought I would be fucked like this by an older fat guy, but here I was. There was nothing I could do but let George drill into me. He held onto me tight, his fat belly weighing down on me.

 

“Oh fuck boy. Here it comes. Gonna shoot my dirty load up inside you.” Oh shit he was going to cum? What did he mean by dirty load? All I could do was lay there. I was paralyzed.

 

“Hey George, do you want cream and sugar- oh! What’s all this now?” Grandpa came back and saw George mercilessly fucking me.

 

“Just a moment. Gunna empty my balls.”

 

“George old boy. I didn’t give you permission to fuck him. How about you stop this silliness?”

 

“But fuck! It’s right there! This boys ass is gunna drink my diseased cum! Oh fuck! Oh fuck!”

 

Grandpa looked at me, rubbing me face.

 

“Are you okay with George here blowing inside you? Let me know now.” I looked at grandpa and mustered out a few words.

 

“Get him out please.” Grandpa reached for George’s cock as he started cum

 

“Aaaah! FUCK! There it is!” George slammed forward. Grandpa was gripping at the base of his cock and trying to pull out.

 

“Come on you old creep. Let’s get this out.“

 

“Aaah! Yes! Fuck!” Grandpa managed to pull out George’s cock. It popped out and his cum ribbons blasted my ass and back. He aimed my ass towards him to inspect it.

 

“Not good. Looks like there’s a little bit in there. OK Kenny, looks like you’re going to get another lesson in rimming. I’m gonna lay down and you sit on my face. Focus on pushing, I’m going to suck all that dirty cum out of you.”

 

Oh my God! There was cum inside me? George managed to shoot some in there? Grandpa laid down on the bed and I immediately position myself over him. This was something I wasn’t ready for, but if it was going to help then I was eager to try it. I sat down on him and grandpa started sucking on my ass hole. His tongue digging inside licking up however much cum was inside. Besides the fear of what George did, grandpa‘s tongue action actually felt incredible. Having a tongue swirl around inside you was so much different than a dildo or a cock. I was trembling, I felt like my body was melting on him.

 

George was standing on the bed looking down on me. He was clearly enjoying the sight of me getting eaten out. He turned around and spread his big ass, puckering his hole towards me. I couldn’t move because I needed grandpa to do what he needed to do with my ass. George moved closer and his ass pressed against my face. His hole kissed my lips. He grabbed my head and held me in place. I had no choice but to rim him. I stuck my tongue out and tasted his ass. It taste like spit and cum. It wasn’t as bad as I thought. He was flexing his hole open on my mouth and I felt him push. There was still some cum in there. He was feeding me grandpas cum! It was bitter and strong flavored. I swallowed it and kept rimming him while grandpa was below rimming me.

 

It must have been quite the sight. I was the middle piece of a human centipede. Ass to mouth with two older men. But I actually was enjoying myself. I felt like I was getting over some of my hang ups about playing with grandpa, but just a little. I knew what I was doing was wrong. What if dad saw me? I can’t imagine how he’d react. Being gay would be enough of a shock for him.

 

The double rimming went in for a while. The big bears ass plopped in my face and grandpa eating me out. At some point we broke it off. Grandpa wiggling out from under me and me pushing off George. 

 

“I think you’re all good to go Kenny boy. George here can be quite the greedy bastard when he wants to be.”

 

“The boy has a nice ass. I couldn’t help it.” 

 

Grandpa ushered George to the door. He got dressed and began to leave. Grandpa was done with him and wanted quality time with me. I felt safer with just the two of us anyway.

 

“How about you send the boy to my place some time? I could really have some fun with him.” George asked.

 

“Maybe, but he’s still knew to all this. I wanna make sure he’s properly trained before anything extreme.” Grandpa shut the door and we were alone together. “How’s about some breakfast?”

 

We cooked breakfast together in the nude of course. A can is spam and eggs. It would be good to get a real breakfast in so I could get the taste of George and grandpa’s cum out of my mouth. We ate and watched the news in silence for a bit. Then he asked the question I suspected he would eventually

 

“So Kenny boy. You’re no longer a virgin. How does it feel?“ I knew that was going to come up sooner or later. I wasn’t completely ready to answer. Having a dick in me felt good but it was his so I was conflicted. 

 

“Isn’t it bad that I lost my virginity to a family member?” 

 

“Don’t forget George. The fat old bastard just had to sample ya.” That’s right! I was fucked by two guys. George even came a little inside me which grandpa sucked out.

 

“He was kinda scary. He shouldn’t have tried cuming in me.”

 

“I don’t see any problem. You loved it didn’t you?”

 

“Well, yes but…”

 

“But nothing. You loved it, that’s all you need to focus on. If you ever want me to fuck your brains out my cock is available anytime.” He stroked his cock getting it semi hard again.

 

“But, the risk of getting anything from it…”

 

“I can pull out of you want. I’m a master at controlling my orgasms.”

 

“I guess so. But still we shouldn’t.” I wasn’t entirely convinced. Could I really ask grandpa to fuck me? Sure I had his cock in me all night but that was an accident. And the fact that he had AIDS added an ominous shadow to his proposition. 

 

“Besides, you seem to be eager to try it. Hell, you sucked my cock in you durning the night. Shame on you for taking advantage of your dear old papi. He he he.”

 

“That was an accident! It slipped in by mistake.” 

 

“If you say so. We’ll see if it ‘accidentally’ slips in again tonight.” 

 

“Perhaps I should sleep on the couch?”

 

“No, I forbid it. You sleep in my bed with me. I want to make sure you’re warm and taken care of. Besides, your ass is a very welcome heat pad for me.” 

 

“…okay, if you say so.”

 

“Good. Now then. What would you like to do today?” Grandpa laid back on the couch putting his feet up on my lap. He was stroking his now hard again cock in front of me. How was he still horny?

 

“Didn’t you just get off?”

 

“I’m never satisfied. It only takes a few minutes for me to be ready to go for another round. See these large balls of mine? They refill fast and always demand for release.” His orbs were impressive. But we had done so much I want sure what else there was to do.

 

“Um… do you have any recommendations?”

 

“Hmmm. I have plenty. But I doubt you’d be interested…”

 

“Maybe…”

 

“Well okay. Rub me feet. We’ll see if you get into foot play kink.”

 

“Your feet?!” I looked at his feet sitting on my lap. They had a little bit of dirt on them.

 

“Yeah I love having me feet played with, especially by young boys who are hungry to lick the sweat and grime from between my toes. Go on, rub them for me.”

 

“I don’t know…”

 

“I can have you go over to George’s place. He’d love to have you worship his feet. Of course I’d send you alone and who knows what else he’d have you do.”

 

“No I’ll play with these!” I grabbed his feet and started rubbing them, even though they stank and were a little dirty they were soft and cushy. He kept playing with his dick while he watched me. 

 

“Yeah that feels good. How do you like them?”

 

“They’re nice. Soft” 

 

“Getting you turned on?“

 

“Not really. It’s just a massage after all.”

 

“Then try licking them. I’ve been told they taste great.” I looked at them for a while. I’ve tasted ass this morning, but these?

 

“I don’t know.” He then raised a foot up to my face. Pressing his toes up to my mouth. 

 

“You’ve done worse. Come on, suck your grandpas toes.” He was rubbing them around and I reluctantly opened up and and licked them. They didn’t taste as bad as I thought they would. But it did feel degrading. “Yeah, that’s it. That’s a good boy.” He kept stroking as I licked his feet. He rubbed them on my face. Loving it. It was a little humiliating but it wasn’t bad, it was kinda nice. 

 

I could feel my own dick getting hard. Not necessarily because of the feet but the intimacy of what we were doing. I started stroking mine as well. 

 

“I can see you’re enjoying yourself. Good. Keep playing with yourself, I want you nice and horny.” 

 

I licked up and down his feet. If he was enjoying it then I was glad to be of service. I was rock hard and stroking. Grandpa and I were now jacking off together. I continued the service for a while, but after a few moments grandpa took his feet away.

 

“Get on the floor Kenny. On your hands and knees. I want to step on your face.”

 

“You won’t do it hard will you?“

 

“Of course not. I just want you to experience what it’s like to have a man dominate you with his feet.”

 

I got on the floor and got into position like he asked. Grandpa stood over my head, his huge cock and balls swinging above me like a pendulum. He brought a foot up and put it on the back of my head, pressing me down to the floor gently. My head turned to the side and he ran his toes down the side of my cheek. I had to admit, this was quite the humiliating task I had before me. Would other guys want to do this sort of thing? If I ever got a boyfriend would he want to do this? I guess if I really liked the guy I would be willing to accommodate it. Grandpa‘s feet are fairly soft, so it actually feels quite nice.

 

Grandpa went behind me and placed a foot on my ass. He was rubbing my cheeks and then brought his big toe close to my hole.

 

“What are you doing?“ He was circling it around, then began to press in a little.

 

“It’s all a part of the foot play my dear boy. You should know what it’s like to have a man toe fuck your ass.“ He pressed his toe all the way inside me and started thrusting his foot in and out. This was by far the strangest thing he has done, but at least it wasn’t his cock. Grandpa kept toe fucking me for a while. I was stroking my own cock while he was doing it. It was actually quite enjoyable. I could feel myself getting close.

 

“Grandpa I think I’m going to cum.“ His foot work inside me continued.

 

”Yeah that’s it my boy. Cum for grandpa. Cum because you love my feet.”

 

“Yes grandpa, your feet are going to make me cum.” Grandpa then took his toe out of me and got on his knees. His cock was resting on my crack.

 

“I want to see it better. I want to see you blow your load on the floor then lick it up.“

 

I was actually missing his foot action. I wanted something in my ass to help me get off. I was aware that his rockhard boner was right there on top of my ass, but I didn’t have the heart to ask him to put it in. That would’ve invited way too much danger. I tried stroking the best I could while grandpa was rubbing his hands on my ass cheeks and back. I couldn’t help it, I needed him to stick his toe back inside me. I wanted to feel him foot fuck me. As embarrassing as it was I tried asking.

 

“Grandpa put it back in please I’m so close.“

 

“Do you want me to stick it in? Are you sure?“

 

“Yes grandpa please I need it.“ I felt him reposition and plop something warm against my hole. He pushed forward and a hot boulbous thing popped in past my ring. “Fuck yeah grandpa that feels good. I’m gonna cum.”

 

“Damn I could cum as well Kenny.”

 

His toe felt so good in my ass that I didn’t care if he shot his cum on me. I was about to blow and it was only fair to let him blow too.

 

“Yeah shoot it grandpa, go for it. I’m going to!“

 

“Fuck you’re asking me to cum? You don’t have to tell me twice.“

 

I started to orgasm, I let out a pretty loud grunt and started blasting my cum all over the floor.

 

“Aaaah! Fuck! Yeah!” I’m pretty sure I made quite the mess on the rug. I had a feeling that grandpa wouldn’t mind an extra stain. I was expecting a shower of jizz raining down on me but then I felt his toe sink deep into my ass, very deep, wait that’s not his toe. “Grandpa what is that?“

 

The question was rhetorical, I knew exactly what it was. Grandpa stuck his cock balls deep inside of me. I then realized that it was his cock the entire time. He was fucking me fast. The assault on my ass was insane.

 

“That’s going to be my cum shooting in you soon Kenny boy. Just like you asked for. Such a good boy. I’m going to make sure to blow deep in you.” He was drilling away inside me, he was breathing hard and I felt his balls slap against mine.

 

“No grandpa! Not inside me! Please pull it out!“

 

“Really? You just said to shoot it in you?!”

 

“I thought you had your tone inside me grandpa. Please don’t cum in my ass.“

 

“Fuck! Fine! Turn over! You’re going to drink it!” He pulls out of me with a pop. I got on my back and sat up. My ass sitting in my own cum puddle. Grandpa brought his dick right up to my mouth and before I could have time to say anything he slammed it down my throat. I was almost gagging on it. He put his hands on my head and started violently fucking my mouth. It was big and I thought I was going to suffocate.

 

“Fuck! Here it is! Drink it pig boy! Drink all my poz cum!” The huge head of his cock was lodged down my esophagus as I felt him throb and twitch in my mouth. His cum blasted out and I reflexively swallowed every drop. His cum was hot and bitter. He held his cock in my mouth for a while as he sighed in relief. He looked down on me caressing my face.

 

“You were such a bad boy Kenny. Giving me your ass then taking it away again. I hope you make it up to me. From now on I want you to suck me off whenever I ask you to. Yes?“ With his dick in my mouth I gave a nod “Good. Start with sucking my cock now. I want you to work another load out of it.“

[plymsleazebear]

Fucking hot, it won't be long before Kenny is embracing his inner pig.  Hope Frank gets to help train him on piss, & will Tommy help convert Kenny?.  Are their any vacant apartments there?  Sounds like the ideal place to move into!

[Mvillebottom]

Another sizzling hot chapter!!   You have an amazing knack for writing stories that make me extremely horny 😈🥵   Thank you!!  Can’t wait to read more of your writing 🤤

[Petereater]

Fucking NASTY!.. loving it ☣️

[gamerslut]

Awesome story so far!

Can’t wait to learn what happens to Kenny ☢️

[sdcigarpig]

So far a very hot story