The oldest guy I’ve ever been with was a friend of my dad’s. Calling him Kay. I’ve known him most of my life, but never paid him much attention. He’s 34 or 35 years older than me, been friends with my dad for decades even though they have about 15 or 16 years between them too.
When I was 18 (I’m now 24) I came to dad’s for a party (had moved out at 17, but stayed over regularly) and bored of most of the guests, I started talking to Kay. It was pretty typical, catching up on our lives; I had heard he and his long-time (male) partner split, he teased me about how I was just going to college to party. We were alone in the kitchen at some point and he put his hand on my thigh joking about all the freshmen dick I must be getting.
I looked at him, suddenly not seeing my old “Uncle Kay” but just a dude who was apparently not as gay as I expected and my next thought was, “huh, wonder what old dick is like?” (Ageist, I know, I’m sorry)
I put my hand over his, moving it farther up my thigh. I wasn’t super turned on, just curious how he’d react, so I told him, “it isn’t just freshmen dick,” letting him infer whatever he wanted. He squeezed my thigh harder and let go. I stood up and asked him if he wanted to see what my dad had done to my bedroom since I moved out. Obviously he got the hint, and followed me up the back stairs.
In my room (left unchanged, and ready for my visit) I shut the door behind us and he immediately put his hands on me, feeling me up. It was pretty thrilling to see how eager he was to touch me, and I was getting turned on. I asked him if he had experience with women, and he said it had been decades. I asked him what he missed the most, and his hands went to my waist and he said very quietly, like he was shy, “pussy.”
The details are a little blurry but the rest of this is to the best of my memory.
I did a very unsexy strip-tease while he sat quietly watching. He kept his clothes on. Then he pushed me on the bed and held my legs apart as he looked at my smooth pussy. He grunted “fuck” and started eating me out. His beard prickled my thighs, but his tongue knew what to do with my clit. I kept unintentionally kicking up the bed because the sensation was really intense, but he just gripped my thighs and pulled me back, which was kind of amazing.
I came pretty quickly, but he kept going for it. Licking my asshole to nibbling my clit. I told him to give me a minute while my legs were spasming. He took his shirt off and wiped some of my wetness off his face and beard with it. He laid next to me and his big fuzzy belly felt so nice on my over stimulated body. I wiggled around a little, feeling it brush against my smooth skin.
He put his fingers back in my pussy, thumb manipulating my clit piercing. My legs tightened around his hand. He kept tickling my tits with his beard, and I pulled him close so he would suck on them. He seemed to like my nipple piercings and his tongue felt good there too.
I asked if he was gonna fuck me, and he said he didn’t think he could look my dad in the eye if he did.
My legs fell open and released his hand which had more wetness clinging between his fingers. He licked them clean before getting up and putting his shirt back on.
I still wanted to experience his old man dick and I *very subtly* (/s) got on my hands and knees and asked if he was sure there was nothing else he wanted. That daddy would never have to know. I was probably corny as fuck. Oversexed and soaked in too much porn at that age and never knew how to be subtle about what I wanted.
But it worked.
He undid his pants and his stubby cock was dark and rigid. I remember being surprised at how much foreskin he had to hold back. He got behind me and again his hairy body tickled my skin as he thrust into me.
He fucked me slowly, still running his hands over my back, and squeezing my ass. We didn’t change positions but he sped up after while and then paused, cumming directly inside me. He didn’t pull out right away and apologized as his cum continued to hit my pussy and thighs. He seemed to have a huge load to unleash.
I said I didn’t mind, and turned around, watching him tuck his dick away and rush to the door. I think he felt guilty or embarrassed.
He said he’d see me downstairs, and I made no move to get up. As soon as he walked out, I grabbed a dildo out of my nightstand and brought myself to another orgasm. I had to clean up my sopping wet pussy and legs in my bathroom before I got dressed and went back to the party.
He avoided being alone with me the rest of the night, but kept smiling when we made eye contact. I figured we had our fun, so I didn’t want to push anything.
We never talked about or did anything together again. For a while I thought it was more fun as a one time thing. But during this quarantine I think about him sometimes and wonder if he still misses pussy.
Source: reddit.com/r/gonewildstories/comments/hu2x9c/mf_the_oldest_guy_ive_been_with
You need to tease him
Since then, have you looked to older men more?
i thought i was reading a r/gaystoriesgonewild post. “my pussy” checked out but “my clit” was the giveaway
uh, anyway hot story
It might have scared him away, the thought that your dad might come to learn of this one day. I know I’d be cursing the fuck out of myself.
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Feels like a conflicting win for him lol