disillusioned by any and all kinds of relationships with my contemporaries, the summer I graduated college (at 21) I fully indulged in my attraction to older men. up until then, I had only been with generational peers but sex with them started to feel too superficial and almost competitive at times. I felt self conscious. my foray into a wider range of partners, older men in particular, taught me so much about myself and what sex could be.
I've actually written about some of these hookups maybe I'll blog them but I just generally loved the way older guys were more communicative, sensual and slower, more indulgent. I was also was able to share my own inexperience ( I had only been sexually active for like 3 years at that point) with them without being judged and several guys took time to teach me stuff, which was hot tbh.
the oldest person I've hooked up with was in his 60s and I was 21 at the time. I was extremely horny and deliberate in my quest for someone older lol. this person happened to be available and we had an afternoon tryst I often think about still. He was an older white gentleman with gray hair (all over) which I found to be so sexy. He was clean and natural. He was soft spoken and easy going. He let me really take the lead that day and that made for an extremely sexy dynamic considering I was the novice.
an expectation of mine for hooking up that day, was to finally bottom. because of the couple of hookups with older dudes that took place before this one, I realized how much more at ease I was with a mature partner. I had always heard that you gotta relax when bottoming so, I figured what better partner than one that I am at EASE with. I never accomplished my goal of stuffing my hole that day. but ultimately I didn't care because we had so much otherwise. In fact he wasn't hard for a lot our time together and i didn't mind. I still thought him extremely sexy, giving and open. I actually find flaccid cock hot too. I remember his fluffy white pubes being a big turn on for me. I found myself burying my face in his pubes and pits a lot.
He looked older with clothes on if that makes sense. probably because his style really dated him. I remember thinking his body looked younger than his face which is sooo something a 21 year old would think smh. he had an average build with a slight belly that i adored. he was bald except for the temples and had a little bit of stubble which I loved. he was an amazing kisser. And because I hosted in my empty house and had the whole day to myself, I spent most of the time naked while he would dress himself whenever we weren't in the bedroom (he took smoke breaks). the whole clothed vs nude thing turned me on a lot.
My biggest takeaway from meeting him the one and only time was seeing how liberating sex can be when the goal is pleasure and not strictly escapism or dominance or whatever else I had known it to be up until then. He let me be myself and that was so hot. especially bc I was having body image issues at the time (and i was such a snack smh) and he was so obsessed with mine for whatever reason and I thought his totally sexy without any stigma about it regarding age or whatever. He never came and neither did I. I had just been dripping LOTS precum throughout, which he couldnt get enough of, constantly cleaning it up with his mouth. And I remember learning then that sex didn't always have to end with orgasm. Wish we got to do one more time before I left town, but it's ok.
in terms of "fucking" tho.... one of my "daddy" hookups made me top him and that was my first time topping. it wouldve been hot except for the fact that he had snuck me into his marital home and I found myself fucking him in a room full of family portraits. he was an Indian cab driver and didn't talk much. Even so, he was commanding and it felt very intense and a little rushed and obviously risky (it was an AM hookup in the middle of the work week). because of that, topping him felt like a lot pressure. So yes, I was hot and hard and sticking my dick in someone for the first time was AMAZING but his silence and my brandnewness made me feel like I had to perform in a certain way.
pretty much I got in my head. I tried communicating to him that I wasn't going to cum like this, thinking maybe it was the doggystyle we were doing but idk what he understood because next thing I know, he turns around, yanks the condom off, lays on his back, flips he legs up and drills my dick back in him. Writing it down, I realize how problematic it was. And I for sure knew I didn't want to be fucking raw but I had admit it felt so much hotter. Even with the changes I knew I wasn't cumming anytime soon and by that point I had broken into a sweat. I guess the pressure was on for him too, bc he sort of sits up a bit still me still inside, rubs my sweaty belly and chest and kind of pulls away. letting me know it's ok to stop. He then takes my throbbing dick and sucks me off.
he was amazing at oral but didn't really allow me to do it on him. in fact this guy never got hard either, which again is fine but he was definitely strictly a giver and made no space for me to please. except for my rock hard virgin dick that at the time could become erect at the gust of mild breeze, so it wasn't that surprising that I could fuck and still not get off... He was nice enough. He finally let me kiss him as we showered together. That was probably also where my lil shower fetish manifested, as I found it extremely sexy to be washed/bathed my another.
Anyway. this was fun to reminisce about. I haven't had sex in a while and I myself am a bit older now. Idk how the whole older younger thing would play out these days. I dont have a type and I'm not opposed to going younger I just never have. I hope the dads and grandads would still have me and didn't just hookup with me at a time when I was just barely grown haha. only time will tell