Sex with an Old Man

Before I start I should give you some background on myself. I also want it to be known that this story is 100% non fiction. If you like the story, contact me via contact tab. I am a mostly straight man. I never have, and still after, the incident I am about to tell you about, am not attracted to men. I never walk past a guy on the streets and want him sexually. Sure I can acknowledge when a man is handsome but that is it. I am however into the look of a penis. What brought me onto this was watching shemale porn. It was all women but then, just a nice big cock between their legs, it turned me on. Mariana Cordoba is mostly to blame for this. She has a giant penis on her womanly frame. I love watching big dick flop around while the shemale, or even guy is being fucked. That is simply it though. I love to see big dick flop as they get fuck and my fetish goes no further. Do not worry though, this is not about me and tranny. This is about a true story of me and a man. A man that gave me one of the best orgasms of my life.

Like I said, I had a curiosity for big cock. I just could not find enough big cock bottom videos online so I one day decided to look at craigslist. I looked through a bunch of posts in my town and was amazed how many people were posting and how each person was asking for something specific. I decided to give it a try and make an ad. How could it hurt. I took a picture of my hard cock attached it to the post and wrote the following:

23 year old male here. Name is Jake. Looking for a big dick bottom. The older the better. I have never been with a guy before and would love to be shown the ropes. If you are an older bottom with an average sized cock that is okay too. Attach a picture in your response. I can not host. Hope to hear from you soon.

I made the post for older men because for some reason to be, it wasn't as weird being with a 50+ guy as it was a 20 year old. In about three hours I had about 15 replies. I will not bore you with all of them, just the one I chose. Attached was a picture of a nice probably around 7 inch cock. The man was white and had grey pubes. His response read this.

Hey, I am Tim. As you can see from the picture I am pretty well hung. I am 69 years old and married. My wife is too old and sick to do anything anymore so I am deprived. I too have never been with a man before, but the thought of a young cock like the one you have really excites me. Respond if you are interested.

I scrolled back up to his cock after reading the message and looked at it while rubbing my dick. It looked like a really nice cock, so I messaged him back. I told him how I was interested and I gave him my phone number and told him to text me. I downloaded an app that gives you a different phone number to text through that way my number had no link to this experience. He texted me and we began talking. He told me his wife was 10 years older than him, so now at 79 she is just too old and sick to do anything. He was never into guys his whole life but recently he had just been so horny he got turned onto it. I told him how I wanted to be DL and not be seen. He said he obviously wanted the same since he was married and everything.

We decided to meet the next day at the mall. He told me he would sit on the bench outside of Macy's on the second floor and have a green shirt on. I told him okay I would come up if I felt comfortable, if I wasn't there by 1:30, our meeting time was 1:00, to leave because it meant I either chickened out or didn't like what i saw. I didn't tell him what I would be wearing that way once again there was no link to me.

I got to the mall at 12:55 and scoped out the spot. At 1:05 a man in a green shirt sat down on the bench. From where I was standing all I could see was a grey haired man with male patterned baldness (only hair on the sides and back of his head). I decided to walk past him since he would have no idea. I made my way towards him trying not to make it too obvious. As I past I saw he just looked like a normal older man. Slight belly, grey scruff on his face, average height from what I could see. He didn't look gay at all which is good, I did not want that. I wanted a normal guy with a big cock I could watch bounce. With my heart beating out of my chest I circled back around and stood in front of him.

"Tim?" I said almost stuttering.

"Yes, Jake I assume?" I shook my head.

We just stood there for a couple seconds in complete silence.

"Jake I am going to be totally honest with you, I am shitting my pants right now. I am so nervous I have no idea what to do."

"I feel the same way, maybe we can go stand alone in the parking lot that way there aren't too many people around."

On our way to the lot Tim spoke, "There is nothing suspicious about this, everyone probably thinks you are my grandson."

I laughed, "Do you have any grand-kids?"

"Yes 5 of them, from age 12-26."

"Wow, so I really could be your grandson."

We got to the parking lot and we stood next to what I assumed was his car since he was leading the way and stopped next to it.

He spoke first, "So you have done nothing with a man?"

"No not a thing, and you?"

"Nope."

"Have you ever watched gay porn at all?" I asked.

"Yes I have. I don't know maybe because I am old so I just want something new, but putting something in my ass seems very arousing to me now."

"Okay good, so you don't want to fuck me back right, because I don't want that."

"No, I will let the young guy have his fun."

"Where do we go for this?"

"I was thinking a hotel, we go home get a little overnight bag so it doesn't look odd to anymore at the hotel and we check in, you pretending to be my grandson."

"That is actually a really good idea."

"I would pay of course. I was thinking we would meet at the Hilton around in one hour?"

"That works for me."

We said our goodbyes and I went home to pack a bag. I just throw 3 things in it to look like something was in there and headed over to the Hilton. I met Tim in parking lot.

"Now, don't get nervous Jake, no one knows anything remember that."

We went up to the counter and Tim spoke. "Hi I have a room booked for my grandson and I for tonight." He gave the woman his information and she handed him a key. We took the elevator up to the 4th floor and went into out room. It was a normal hotel room. 2 beds, nothing fancy.

"Now Tim, I do not want to kiss, or anything like that."

"That is fine Jake." I looked at him. He definitely looked his age. Wrinkles were on his face and neck. I could not believe what I was about to do. "Would you like me to get nude first Jake?" I shook my head. "First there is something I have to tell you. That picture I sent is from about 5 years ago. I did not want you to back out so I did not say anything, but I can no longer get hard."

"Do you have Viagra?"

"No I actually don't. Do you still want me to get naked?"

"We are here already, so I guess so." When he finally took his underwear off he revealed a 3 inch soft cock with grey pubic hair. It had a big blue vein down the center. I was still aroused by seeing it. I took off my clothes and popped out my semi hard cock.

Tim walked over to me and grabbed my cock. He moved his hand back and forth until I was rock hard which was no time at all. "I miss the feel of a hard cock, although mine was never this thick. I looked down, my cock was 6 inches long and very thick. I saw his soft cock resting on his balls. "Want to put this inside me?"

"Yes." He walked over to his bag and got some lube out and threw me a condom. I put the condom on as Tim lubed his asshole. "Okay I want you on top of me so I can get a good view of your cock."

"There is no way that fat cock is getting in my ass like that. Nothing has ever been in there. We need to start doggy so you can get some force." Tim got on the floor and raised his old saggy wrinkled ass into the air. I got behind him. This was not much of a turn on for me since I was just looking at an old flat ass. I pushed my cock into the opening of his ass. I instantly knew it was not going to me easy getting in.

I worked my cock into his ass. It took about 5 minutes and plenty of more lube before I was totally in. "How does that feel?" I asked him.

"Actually pretty good." With that I started to fuck him. I looked around the room because I did not want to look at his old ass anymore. I quickened my pace and he began to grunt as I shoved my cock in him faster. After doing that for a while I asked if he could get on top now.

I laid down on the bed and waited for him to get on. He turned around and I looked at his cock. It had grown. It did not get hard, it just grew. It was now this 5 inch soft floppy cock between his legs. He looked down. "Wow, I have not seen my cock this big in about 5 years." He squatted over me and guided my dick into his ass. Once he was all the way down on it his cock was resting on my stomach.

He started to bounce up and down on it. His cock was going everywhere. It would go up hit his stomach, then come back down and hit mine. It was the hottest thing I had ever seen. The entire time I was just starring at his big soft cock bounce around. It looked so big as it moved around. I reached across my body and grabbed onto his dick.

I am not going to make stuff up in this story for erotic pleasure. I am telling it as it actually happened. Once I grabbed his dick I felt like I was going to cum. There was not turning back, and I filled my condom with cum.

"Did you just cum?"

"Yeah, sorry. It was just really hot."

"No need to be sorry, I am a man not a woman I know how it feels when you just can not hold on any longer." He took my cock out of his ass. I took my condom off and put it back into the wrapper I did not want to leave it behind as evidence. Tim was now just standing up with his big soft cock between his legs.

"So you liked getting fucked in the ass?"

"Yeah it was a good experience, I mean I did not even know my cock could get this long so it must have really turned me on." There was an awkward silence after that and I started getting dressed, so did Tim. When we were both dressed we left the room and went into the parking lot.

"We will be in touch?" Tim said, and he got in his car and drove away.

Tim and I were never in touch after that day. I do not know why, we just never contacted each other again. Since then I have always been looking for an older guy to be with once again.