My First Time

My who life I had always been curious about being with a guy. But I had always been afraid to take the plunge.

I’ve been married since I was 25. My wife and I are still happily married but after 3 kids the sex life definitely faded a tad. All of our kids are grown up now so being empty nesters it’s giving me the opportunity to watch porn when my wife is at work.

Three years ago I watched gay porn for the filter time. Seeing a guys dick slide into another guys butthole got my dick really hard and excited. Sitting there on the couch in just my briefs and a shirt I pulled my hard dick out the fly of my briefs. I watched as the guy took dick and it only took me a minute of jerking myself till I was cumming all over myself. Something about that kind of sex really turned me on

So I did some research and stumbled upon a few gay hook up apps. I signed up for one. I used a picture of me hard in my white briefs as my profile picture. My heart was racing as I set up my profile. Didn’t take long before I had messages from a few guys. Told them I just wanted to start with getting a bj and go from there

A few days later after work I met with another married guy in a parking lot. He got in my truck and I opened my pants. He held my briefs under my balls as he sucked my dick. What an amazing bj. I kinda worried at first that I was too hairy for a bj but that didn’t seem to matter. He sucked good. Licked my shaft and really sucked my big head. I came in his mouth.

Laying in bed that night I couldn’t help but wonder how it would feel to get my butt penetrated. My dick rock hard in my briefs thinking about it. My wife felt my hard on in my underwear then asked if I needed help with it. So I fucked her that night. But I couldn’t get the thought of getting fucked out of my head

A few days later while I was at Walgreens picking up my prescription I decided to buy some condoms. There was a guy who was wanting to fuck me and both being married we both agreed on protected sex. Buying condoms was still awkward at that age. As I’m buying them I had to think the last time I bought any.

It probably had been a good 30 years since I bought rubbers. My wife and I stopped using them after we got married. But there I was buying a box of Trojans. The pharmacist said nothing.

A few days later I was at the guys house. It worked out perfect that both our wifes were nurses who worked the night shift. And he was an empty nester too.

There on his bed he popped my cherry. It was definitely everything I was expecting. It hurt at first but felt great once he was in me and actually fucking me. He finished in the rubber.

As he put his boxers back on I took a minute to let my hole relax. It was definitely stretched wide open and a bit funny feeling. As I got up to put my briefs on he said how about we do this more to get you used to taking dick.

So once a week I was getting fucked by him. I was only buying 3 packs of condoms because I had to keep them hidden. But one night after we had been having sex for 3 months I told him I needed to stop at a store on the way over to get some rubbers. He messaged back saying how about I just creampie that hole

So I let him. That feeling really turned me on and it obviously turned him on too.

As I’m putting my briefs back on I could feel cum leak out of my butt. He said it’s a good thing you wear briefs and not boxers. He asked if my wife wife would find out and I told him nope I typically do the laundry and she’s not examining my underwear for cum since she knows I cum on them when I masturbate

But the drive home I was leaking cum. That guy has big loads