Losing My Virginity To An Older Man

I was a senior in high school and I had just turned 18 two weeks before I found out about Craigslist casual encounters. I’d surf that at night to look at and masturbated to all the pictures of guys dicks on there.

But one in particular I kept going back too. His post said he was 58. His dick looked to be anywhere from 6 to 7 inches and it had a natural bush which I thought was hot. I was extremely nervous as I messaged him.

He emailed back. I told him I had just turned 18 and was a virgin. We met in the Walmart parking lot a few days later around 5 pm. It was after he got off work. He told me to come by his house tomorrow after school and he’d be there and we could see what happens

I showered in the locker room after school then headed to his place.

We got to it right away. I was sucking his dick within minutes of being there and I was so hard in my pants while sucking him. He has me strip naked as he watch. As I’m pulling off my underwear he says shaved too I see that’s sexy. Yes all my pubes were shaved off it was the popular thing to do for guys my age.

As soon as I was naked he took me to the bedroom and said get on the bed in doggy position. He got behind me after getting lube out of his bathroom and he said I want to pop your cherry

When his head first popped in it hurt. I pulled off real quick but he said it’s gonna hurt at first. So I got back in front of his dick and he penetrated me. Slowly he went balls deep. I could feel his pubes against my butt.

He had ahold of my hips saying I forgot how tight 18 year old pussies are. My hole was definitely stretched wide open. It hurt but also felt great. He was slowly picking up the pace and my dick was leaking precum like crazy.

As he’s dirty talking saying he’s gonna breed me. Fill me with his cum my dick can’t take it much more and I start to jerk it. I cummed on his bed. Shot a big load on his sheet. As I cummed and moaned my dick clamped down on his dick

He shot his load in me moaning too. I’m finished cumming and he’s still cumming saying you clamped down so hard that it milked me real good.

He slowly pulled out and looked at my hole as he spread my cheeks. He said that is a great hole

After getting cleaned up I’m standing in my tighty whities and he told me cum can leak out so be prepared for that. I watched as he put his tighty whities on and then his jeans.

As we are talking he says I can come back any time if I want to have sex again. Said he would like to continue to break my hole in

So I took him up on that offer. We had sex for 5 months. Many times a week.

I reconnected with that guy last week. He’s now 70 and still loves to fuck. We had sex last week and he says my hole is still as good as he remembers it and he’s glad he got to take my virginity.