My Shy (but Hung!) Grandaddy

After my first few experiences with David (see my other stories), I wanted to sample a bit of variety. I was regularly cruising online and chatted to a few guys but was quickly finding out that older guys who are versatile was a big turn off for me. I realised I was looking for selfish tops. Men who wanted to be sucked and who wanted to fuck. They wanted to cum and that's all they were interested in.

On a website that specialised in connecting young guys with silver daddies, I got chatting to a man called Harold. Harold was 86 and at first just wanted to chat. He lived in a town about 45 minutes away from me and was a widower. He told me over the course of a few weeks of conversations that he had always known he was attracted to males but because it was so unacceptable when he was young he had never acted on it and then had got married and put it to the back of his mind. It was only since he had become a widower that he felt he should finally live out his fantasy while he still had time. He said he was still in working order where it mattered and masturbated regularly.

Importantly, we established that Harold was a total top. I sent him some pictures of myself and he liked what he saw, and he sent me a face picture showing an elderly, but still handsome man. Obviously slim, with a strong jaw and thinning hair. His profile said he was 6 foot 2", which I liked (and I can't say I hadn't noticed he stated his cock size as large!). But he said he was nervous of meeting as he hadn't done it before and he didn't want me to be disappointed by his age and the fact that he wasn't as mobile as he used to be. I reassured him by saying that I was pretty new to meeting up with men as well so I would still be nervous too, but that I was happy to do most of the work and let him sit back and enjoy the experience. I also told him we could just talk or sit and watch some TV for a while if that made him more comfortable. Eventually he agreed to meet and we set a date and time for the next weekend.

I arrived feeling just as nervous as I had on my first meeting with David, but much more sure of what I wanted to happen. He invited me in nervously and we sat on the sofa exchanging pleasantries. He said he wasn't sure how to act and admitted to feeling anxious about the situation. I said we could just watch some TV to relax and he could let me know if he wanted to try anything. He said ok and we turned our attention to whatever rubbish was on TV.

After about half an hour of hoping that Harold would make a move and initiate some activity I thought that maybe he had changed his mind so I asked him whether he wanted me to leave. He said that that he definitely didn't and that he just didn't know how to begin. I said if he was happy to let me, I could take the lead while he watched TV. He nodded.

I reached out and placed my hand on his thigh. His body tensed up, but he didn't say anything, so I carried on. I moved slowly up his thigh to where I could see the outline of his cock resting against the inside of his leg. He subtly spread his legs ever so slightly to give me better access. As I slipped my hand over it, I could feel through his linen trousers that he was still soft, but that he was big. I gripped it and gave it a stroke through his trousers, but I knew I'd have to get it out to get him hard.

I undid his flies and reached in past his boxers and grabbed his thick soft cock. I freed it from his trousers and noticed that he was circumcised it had a nice round shiny red head at the end of his thick, soft shaft. He breathed heavily as I started stroking it gently. I could feel from how much it was stretching when stroking it soft that it had the potential to get big.

As much as I was enjoying playing with the big soft cock, I sensed that it was going to take something more to get it hard. I climbed down on the floor in front of him and got on my knees facing him. I undid his belt and trouser button and tugged at the sides, letting him know I wanted them off. He raised his hip up and let me slide them down, along with his y-fronts, over his legs. I pulled his knees apart so I could shuffle in between them. I lifted up his soft cock and gave it a big lick all the way from the bottom of his droopy balls to the tip. He moaned and I felt his dick twitch in my hand. His balls were big and hairy and hung low, so I lifted them up and sucked on one at a time. I could taste a little perspiration, a nice hint of saltiness, and I put each testicle fully in my mouth and sucked as I rolled my tongue around it.

When his balls were nice and wet, and he still wasn't hard, I licked my way up to the tip of his cock and then put his head in my mouth and rolled my tongue around it. He sighed heavily and I felt it twitch again. I moved further down taking more and more into my mouth until it was all inside and I was able to lick his balls at the base of his cock. I moved up and down sucking and rolling my tongue around as I did to try to get him hard. After a while he started to grow a bit, which gave him considerable length but was still only semi-hard at best.

I asked Harold if he minded if I got undressed. He shook his head. I stripped down in front of him until I was totally naked. I turned around and showed him my bum, as he had said that he liked my bum on my online profile. I asked if he liked the real thing. He nodded. I reached down and grabbed his hands, and holding onto them while I turned away from him I placed them firmly on my ass cheeks, inviting him to play. At first he just held them still, unsure of what to do next. But eventually I felt him squeeze both hands and start to move them around. He stroked my ass from the bottom to the top and back down again a few times. I pushed my bum out towards him, encouraging him to spread my cheeks and expose my hole. He stroked closer and closer to my hole but repeatedly stopped just short of it. Eventually impatience got the better of me and reached back to take his fingers and place them on my boi pussy.

He took the instruction well, and rotated his finger around my hole, gently caressing it. I bent forward a little, giving him more access, and dropping a hint of what I wanted next. I felt his finger settle on the hole and then he pushed forward. I moaned as his finger slipped easily in. And although he hadn't used any lube, David's large cock had made it comfortable for fingers to enter without assistance. He slowly finger fucked me and I enjoyed the feeling, as well as knowing now that he was enjoying himself.

This was confirmed when I bent further forward and looked back through my legs to see Harold's cock standing firmly to attention. And. It. Was. Big! Probably over 9 inches long, perfectly straight, and pretty thick too. He was stroking it with his spare hand while he fingered me.

I wanted it now. So I stepped forward away from his hand returned to my knees to worship it. I put his bulging head back into my mouth and felt it swell as he tensed and tasted pre-cum immediately. I sucked as deep as I could, but it wasn't that far now that he was at full length. I licked him up and down from balls to tip a few times for good measure and then reached down to my trousers that were beneath my knees to pull out the lube from the pocket.

I squeezed some onto the tip of his now rock-hard cock and stroked it all the way down, and then I stood up and put some onto my hand, which I rubbed around and into my ass hole. I told him we didn't have to do this if he wasn't sure. He said he was sure while stroking his big cock.

I turned away and backed into where he sat on the sofa. His legs were spread wide and mine went inside them. I put my hands on his thighs and lowered my down until I felt his cock touch my bum. I reached around and moved it into position against my hole. I was desperate to feel him inside my, so I didn't waste any time. I pushed down against it, and felt the head slip inside. I kept pushing, feeling that slightly painful stretch that I'd grown to love. Harold grunted and placed a hand on my shoulder and started pushing down. He was obviously enjoying himself. I didn't resist and pushed downwards, feel more and more full as his length went inside. It was only when it got to the last inch or so that it felt really painful. But I persevered and sat all the way down on him.

When I was at the bottom, it felt like I could feel him in my chest. I savoured the feeling for a second before starting to slide back up. This got another grunt out of him. I went back up almost to the tip and then sat back down, quicker this time. I slid back up slowly again, and sat back down quicker again, and then again and again and again. I was loosening up for him nicely and started to really work hard and faster shortening the range of movement to make sure he didn't blow his load too quick.

After a few minutes my legs were aching from maintaining a standing squat position. So I lifted myself off his hard length and enjoyed the gaping sensation as I turned around and climbed on to the sofa, placing my feet either side of his hips and lowering myself down towards his cock. I braced myself for his entry and relaxed my hole to let it slide in smoothly. I sat all the way down, and it was only at the bottom I realised that this position would allow him to go even deeper inside and I felt the stretching pain again as my ass adjusted to the final centimeters.

I rode him again, and he helped me by grabbing my ass cheeks to lift me up and down. Before too long he began to breath more heavily, and I told him to tell me when he was going to cum as I wanted it in my mouth. Either it was a total coincidence, or me telling him that I wanted to eat his cum aroused him to the point of explosion, because he pretty much immediately shouted "now!"

I quickly slid off his big cock and jumped down to the floor in front of him. But I wasn't quite quick enough, because just as I grabbed his massive hard cock and was moving my face in to put it in my mouth, he grunted loud and squirted once across my face and hair. I managed to get my mouth over it for the second, third and fourth squirts, which were lovely and warm and went straight down my throat. I stroked hard and sucked to get the remaining cum to seep out and into my mouth.

I carried on sucking until he went soft in my mouth, and then asked if I could use his bathroom to clean the cum out of my hair. When I came out of the bathroom Harold was dressed. He watched me get dressed and I told him I needed to get going. He thanked me for coming. I gave him an awkward kiss on the cheek and he let me out. We continued to chat online, but unfortunately didn't meet up again.