[MF][old/young] How I started with older men

So after I posted my first anal story (https://www.reddit.com/r/gonewildstories/comments/5iudtk/mf_that_time_an_older_man_introduced_me_to_anal/) I had a few messages asking me how I started with older men. Here’s the story.

I was 18, but only just. I was living with my mother and her long term boyfriend, as had been the case since she split with my father when I was much younger.

My father had died a few weeks earlier and I’d been packing up and cleaning out his things. His friend had offered to help, which was useful – for example, Dad had left me his Triumph motorcycle and I had no idea how to ride it. (I do now!)

So we’re moving some of my Dad’s old things into my place. At the time, and now, I lived in what we in Australia call a “granny flat” in my Mum’s backyard – basically a small cabin type of thing.

After a long day’s moving, we stopped for a break and a beer or two. That was probably a bad idea as it had been an emotional day and before long I had broken down crying. Now, I had known Dad’s friend (let’s call him Keith, as that’s his name) since I was born, so of course his instinct was to try and comfort me. He gave me a hug in his big strong arms and stroked my hair and it did help me feel better, but I couldn’t help taking in his manly scent, tinged with the sweat of a day’s work in the hot summer sun moving things for me. I didn’t want to let him go.

I still can’t explain how what happened next happened. We held on to each other for what felt like forever but was probably only a few minutes. He was still stroking my hair and I thought I noticed him taking in my scent as I was his. Out of nowhere, our eyes met and we just knew that we were going to kiss. Maybe it was the emotion, maybe it was the alcohol, the summer heat, who knows. Probably all of the above.

“Oh…Sophie, I’m sorry, I shouldn’t have done that”, he said immediately afterwards. I didn’t care. It was one of the most amazing and sensual kisses I’d had. Understand that before now, I’d had typical teenage relationships with typical teenage boys. This was an experienced man and I was a relatively innocent young girl. It was a heady combination.

“Don’t be sorry” I said, and before he could say anything, I kissed him again.

There was no stopping us now. It was hot and we weren’t wearing a whole lot to begin with, but pretty soon I was down to my underwear and about to learn my first thing about older men: they know how to work a girl’s equipment.

What do I mean? Well, my earlier boyfriend knew nothing about how the clitoris worked. He knew where it was, but he was rough with it and pushed it like a pleasure button. Keith knew that slow and steady won the race, and started rubbing me gently through my underwear.

Ohmygodohmygodohmygod before long I couldn’t stand up – so I flopped down on the lounge behind me, panting like crazy.

Keith, still standing, looked at me and said “Sophie, you have to stop me now or I might not be able to stop myself later”. It was probably a well worn line but as a teenage girl I felt like the most desirable woman on the planet at that moment and needless to say, I made no effort to stop him. I just smiled at him, in the most seductive way I knew how (which was probably not very seductive…but he didn’t appear fussy!)

Keith removed what was left of his clothes and this was my next OMG moment. This was the first real man’s cock I had seen. Such an impressive beast. Not long or thick particularly, but it seemed muscly somehow and with prominent veins and I wanted it. I knew looking at his cock that he was going to fuck me with it and I wanted that more than anything.

Gently, I took his cock into my mouth. I was no expert on this at the time and I think he made more of a show of enjoying it than my performance really warranted. But whatever, he made me feel like a sex goddess and I was so wet.

There was nothing else for it. I lay back again and put my legs up in the air (it was on a lounge, room was tight!) (Not the only thing that was tight, ha ha…). Keith didn’t need to be asked twice and positioned himself on top of me.

At that moment I had the realisation that I was about to be entered by a 50 year old man, as an 18 year old girl. Moreso, this was my Dad’s best friend who had seen me grow up. I hesitated momentarily…but it had felt right to that point and I was confident that it would continue to feel right. So I used my hand to guide him into my pussy, and then, my Dad’s best friend Keith was inside his little girl.

Well, you can probably work out what happened next. He pumped me for all he was worth, and given that we didn’t have condoms, he was honest enough to say he was about to cum and pulled out and blew on my boobs. (I discovered later that Keith very much liked cumming on my body, face, hair…it’s his thing). I didn’t have an orgasm that day – I hadn’t had one before but I did have my first one with Keith another time – but I felt satisfied, it took my mind off things, it felt right at the time.

That was the beginning of a year’s relationship that never quite turned into an actual relationship but was more than just sexual. Eventually we realised we couldn’t go on like this and I think through the grieving process Keith started to feel guilty about fucking his friend’s daughter. And, I guess, as I started to get over Dad I started to agree with him.

But that got me started on older men, and while I’ve dated some younger men since, older men are very much my thing now, and I’ve been in a relationship with a man in his sixties for a few months now (I’m 21 now).

So there you go…hope you enjoyed it, and I love your replies and questions etc so go right ahead :)

Source: reddit.com/r/gonewildstories/comments/5jjjvu/mfoldyoung_how_i_started_with_older_men