I have this friend who seemed to despise me from the start and since he was pretty intimidating, it took us many years before we actually talked, had a conversation. It turned out we actually have a lot in common: Warhammer 40k, interest in 20th century wars and tanks (well, I’m more just interested and he’s more knowledgeable, so I get to listen to him), RPGs, whiskeys, mechas, etc. So we actually had a lot to talk about when I got him to talk to me. It took me an entire day of effort to get him to actually open up (and a lot of whiskey, as we had a tasting at a mutual friend’s house), but it was worth it, because he’s a nice guy with a great, if dark, sense of humour, even if he is a bit awkward.
There is also a generational gap between us, as he’s in his early 50s and I’m in my late 20s, and it shows, but I find it funny more than anything. One major difference is taste in sex. I enjoy it rough and kinky, he can’t stand the idea of exerting control over someone. I have experience, he has been married to one woman, his only partner, and it wasn’t good in any way. Still, they had children, the oldest one is as old as I am. It took him some time to get used to me being close, to be able to just touch someone again, but in the end he was happy to kiss me, hug me, and spend time together. We’ve had dates, mostly going together to eat and browse used book stores, but we also had a Friday night date where we went to eat at a fancy place and then had cocktails in a nice bar, just because he had never really done that, and we spent the night in a hotel together, just talking and making out, nothing serious.
This week we had another date planned, where we would go see theatre and then I would spend the night at his place. It was such a fun day, even if I was nervous, worrying about being awkward myself or just not finding anything to talk about. We got to spend some time walking around the city in a snowstorm while watching the Christmas lights and holding hands. When we made it to his place, went to the sauna, had a weird conversation like always, and cooled ourselves on the sofa.
After the sauna, we had a little heart to heart, where we talked more seriously about life and our pasts. It turned to a lot of touching, holding hands, blushing, and then kissing. We had done this before, kissing and cuddling, but he pulled me to his lap so we could kiss better. I could also feel how hard he was and we ended up grinding to each other, and it felt so good. I was wet, so I ended up dripping and spreading my wetness on his pants because I had no panties under my nightgown, but he really didn’t mind.
When we made it to the bedroom, I did not know how far I should go, or what he actually wanted. So it was just a lot of touching and kissing for the most part, but he really wanted to finger me too, so I let him. He needed some guidance, as he was very cautious and I needed him to put some pressure on my clit. I guided his hand, showing him where it felt best, and his fingers slipped to touch my vaginal opening too, which felt nice, and my moaning as well as all the small sounds I made from the touch made him excited. He said after that seeing and feeling someone so wet just for him made him happy and even more aroused, and quite flattered.
I wanted to pay back the pleasure, and it took a few moments for me to actually get the words out to ask him if I could take his cock in my mouth, which he gladly agreed to. It was fun and I did my best to pleasure him. While he might not like exerting control over others, the fact he kept his hand in my hair, the other hand on my shoulder, and applied some pressure, was arousing, and while it might have been unconscious or for him to control himself, it also satisfied my kinky heart a bit.
When I say he was hard, I mean it, as it surprised me when I kissed the tip and wrapped my lips around him, licking it all over to feel it. He was nicely sized and the fact he was so hard made it easy for me to just go up and down, tongue stroking the underside and at times just licking it from every side, then going back to sucking it and pleasuring him with my mouth and lips. When my hair didn’t fall in front of my face, I loved to watch his face, utterly in pleasure and trying his best not to come right away, as I learned after. He had to stop me after a bit, as he had to ask me to stop because he was about to cum, but I said just cum in my mouth, it’s okay. I was so pleased with myself when I took him as deep as I could, deepthroating him, and finally got him to cum down my throat and a bit on my tongue.
He was over the moon after that, and I found out only after that that he had never had anyone give him head, not even kiss his cock. He had also joked about being so old he might not even get it up or if he came, it might as well be dust, but clearly there was no problems with his dick <3 Just a bit of closeness and gentle touches from a young lady did the trick. While I won’t make it a habit to just give men around me what they haven’t tried before, I will continue being friends with the man and try to make him understand he is still lovable and attractive. Not just because I’m into older men, but because he is who he is, someone fun, reliable, truthful and trustworthy man who’s more than a bit nerdy and geeky and actually really interesting and smart.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/1006059/fm_deepthroating_my_51m_friend_for_the_first_time/
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