Hello, I'm going to tell a story that started after I turned 18 and has continued and is still continuing at this point. This will probably be long, so sorry if it's too long to read.

This all started shortly after I turned 18. I was quite shy still, probably the result of growing up in a sexually repressive household. I had fooled around and even had sex a few times with people from school but I was shy and just couldn't get out of my head enough to really enjoy it. I decided I should do something to try to get more out of my sex life. I was nervous to get sex toys in case they were discovered (I was still in high school and living at home at this point) as my mother is notorious for snooping. I decided what would be best would be to find a partner who doesn't know any of the same people as me so I wouldn't be nervous about anything getting back to anyone or being the subject of gossip.

I ended up looking on a website that does buying and selling of items as well as having a fairly anonymous personals section. I decided posting would be too risky with many people messaging me, so I looked through the postings that were up. As I scrolled I saw a posting that appeared to have been up for a while and hadn't gotten much traction (at least from my not great internet detective skills). I won't give the exact details of the ad but it boiled down to M late 50s divorced looking for similar age F. I hadn't thought about someone that much older. I didn't know anyone in that age range as it is sort of between my parents and grandparents generations. I sent a message saying I was outside of his age range and we messaged back and forth a couple times and agreed to meet up at a coffee shop on the outskirts of town to talk. I pretended I was going to my best friends house after school and let her know where I would actually be (we have covered for each other many times before).

I was so nervous I drove around the block twice before pulling in to a parking spot, once there I carefully sat in my car and looked around carefully, making sure noone I knew was anywhere around. Upon being satisfied I went into the coffee shop. It was fairly empty and we had shared enough information to recognize each other. He was already there so I bought an iced coffee and we sat at an out of the way table. We chatted and got to know each other. He has 3 kids that are early to mid 30s. He and his wife were in a dead marriage and separated then divorced after the kids went away to college. I shared some details about my life as well. We then discussed what I wanted and I told him I wanted commitment free, discreet, judgement free experimentation. He seemed incredulous that I wanted this with him but was very eager to accept. We decided to meet back at his place to discuss further. I had him show me his ID and sent his full name and address to my friend and told him I was doing this. I told him to buy some condoms on the way home just in case and I would meet him there.

I'll give a description of us both (at the time) here.

Me: 18 yo, 5'7" about 140 lbs, DD boobs, big ass, blonde hair that goes almost far enough to cover my nipples, generally considered hot by guys my age.

Him: 58 yo, 5'10" maybe about 200 lbs, kind of a dad bod, grey, short hair, looks fairly good for his age but overall average looking. I would later find out he has a 5.5" ish circumcised penis.

It turned out he lives in the outskirts of town with a good size driveway, hedges and a double garage. This worked well for my nerves about getting caught as I circled the block and let him get home before me, then was able to pull right into the garage to hide my car. Going into the house I could see it was very nice and well maintained. Once inside, we sat in the living room and got down to discussing this. He told me he had had a vasectomy and had not been very sexually active since his divorce. This was good as I was not on birth control at the time. I told him I thought we should both get STI tested but if he showed me proof of the vasectomy and being clean I wanted to try raw. He was very eager to follow my demands and said he would get the best test he could ASAP.

At this point we were both feeling a little horny and he asked if we could have sex today. I told him we could touch each other and have protected sex. He came over and told me to stand so he could remove my clothes, I obliged and I was being slowly stripped while his hands ran over me everywhere, my hips, back, ass and tits. It felt soooo good. He finally pulled my panties down, rubbing his finger on my clit, then sliding it into me. I was so wet at this point. I pulled off his shirt and then took off his pants and boxers, giving light strokes to him as I went. He moaned a little which was hot. He wasted no time in putting on the condom and then sat down on the couch while I got on top of him. I didn't really know what I was doing and was still a little shy. So suggested we change positions after a few minutes. I bent over the couch and he entered me from behind. It felt good but he finished before I could have an orgasm. I still viewed this as a win as I felt we had gotten past the awkwardness.

This is where I will leave the story for now. There is lots more that happened and new stuff may even happen, so I will add more parts when I have time to write them. I will just add a few disclaimers here:

I don't wish to share any photos of myself for my own privacy. Nor will I include any identifying details like locations, tattoos or piercings we may or may not have.

I'm sure your penis is very impressive, but I don't need to see it, nor am I interested in giving my location or getting together with you.

If anyone wants to call my stories fake they can, I'm not interested in arguing or proving it. I'm trying to get better at writing in general. I also feel like maybe my story and the feelings associated will help someone, somewhere, sometime and that makes me feel good.