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I'm 39...for a little while longer.
40 on the first of August.
We've done more than just 'hinting' at fooling around...
I had been flirting with my friend's dad and hinting that I wanted to do it with him for a long time. I had been having sex with boys in the neighborhood for a while and thought I was ready for this man. When the day FINALLY came, I wasn't as ready for his man-sized dick as I thought I was.....
We were in his bedroom --me on the bed, him standing above me. I watched as he smeared Vaseline on his dick and then rubbed some on my asshole. He slowly crawled between my legs pushing my legs up and back pinning them against my chest with his big body. I was so scared, but I wanted him so badly. I remember feeling his head against my hole for a brief moment then he pushed ALL the way in with one hard thrust. I screamed and cried for him to take it out, but he didn't. Instead, he lay on top of me with his huge dick deep inside my ass kissing me until it didn't hurt so much anymore. He continued to whisper between kisses that everything was going to be okay and that I needed to relax...that he would wait until I was ready. I relaxed as much as I could and whispered that I was ready.....
Then he fucked me like a madman for what seemed like hours. I was glad (and sad) when he finally came. I had never been fucked like that before...my ass was so sore. The next time we did it, he didn't push so hard and it didn't hurt so much. We fucked 3 or 4 times a week for the next few years until I went away to college.
I knew a guy through my sister. The guy was straight but had an openly gay father. When I became single after a very long relationship, the guy told his dad and the dad started messaging me all the time. Sent me a bunch of dick pics. Sadly, the dad was nowhere's near as hot as his son. Nice dick though.
