Losing My Virginity

I moved to Orlando after graduating high school. I was a shy 19 year old and was a virgin. Never had sex with anyone ever. I didn’t even masturbate often and I had never seen porn

I moved to attend a school. I had my own apartment so I quickly learned I had so much privacy to do as I pleased. One evening I looked up and watched porn. I started with straight porn but I had been so curious about guys for so many years that I typed gay porn in google.

There I sat in a shirt and tighty whities with my dick about ready to rip out of my tighty whities. Seeing a guy get fucked made me cum as soon as I touched my dick.

Then I discovered Craigslist casual encounters. I was so nervous that I was jittery. But I saw a guys ad saying he was looking for first time guys. So I messaged him. He was in his late 50s. I was very attracted to older guys. Something about letting an older guy take my virginity really turned me on

A few days later I’m at him house stripping to my underwear. He saw me in my tighty whities and said I definitely can tell your a virgin.

He had me on his bed in doggy position. My ass was lubed and he was stroking his dick with lube as he had a finger in my butthole. He told me this is gonna hurt at first so just breathe.

As he worked his dick in me I could feel my butthole stretch wide open. It hurt but it oddly felt good. Once his head popped in he held still saying I’m in then slowly went in balls deep

It was just a few minutes before he started saying your butt is so tight. He began to moan and said I’m gonna cum. He unloaded in my butt. As he pumped his load into my rectum I was stroking my dick and I came all over his bed. Thankfully he put a towel down

As he slowly pulled out he spread my cheeks to have a look at my leaking hole and said you’re officially not a virgin anymore.

As I got dressed my butt was sore. I left not knowing that I’d have cum leaking into my tighty whities. It was messy but a reminder that I had lost my virginity