First Time Man Fuck

My First Time (and second) Getting Fucked. In my previous writing I talked about my first time fucking a guy and how awesome it was. The guy was enjoying getting fucked so much I just had to know now what it was like taking cock and how it felt. I live in a small town, I was not out so it's not so easy to hook up with someone I felt safe enough with to try. After many long weeks I finally met a guy online, back in the good ol Craigslist days when post was really open and full of nude pics. He was in my same town and just a few years younger.

We decided to meet in a parking lot with a discreet and dark back area. He was a good-looking country boy and we seemed to hit off well. After some talk about what we were interested in and some now hard cocks, we unzipped and pulled out our hard cocks. His was about 7" with a big mushroom head...really big...lol. I'm about 6" but was hard as a rock. We enjoyed fondling and some quick sucking and decided to go to his house nearby.

After getting naked and watching some hot porn we enjoyed some 69 sucking and he wanted to top me. Well now was my chance but that big head had me worried. He said don't worry I will go easy, and you will love it. I had to see and even with lots of lube I was tight, and he said just relax and I will just thrust it in, that's the best way to get used to it. Well, he thrust in hard and fast and ...it wasn't good...lol. Hurt like hell and I made him pull out... I now know that was totally the wrong way for first time. We jacked off and called it a night.

A couple months later a bit older guy I met at the gym invited me over to his place to hang out with beers. He was a really nice guy and we enjoyed hanging out. He said let's sit out back nude and get some sun. He had a nice body and nice medium cock too. One thing led to another, and we ended up in the bedroom. I told him about my first time and he said, no that guy was wrong, you need someone to ease in especially the first time.

He lubed up his cock and first just rubbed around on my eager hole, then slid just the head in and out a few times which made me relax and crave more. Then he went in and out just an inch or so going a bit deeper each time, slowly working his hard cock into my eager ass. It was so much better and I relaxed and started to really enjoy it. Our bodies skin to skin, face to face his cock filling every bit of my hole. He then said for me to squeeze my ass muscles as he pulled his cock out, then relax as he thrusts in. Fuck that felt so good to my prostate and the intense pleasure I'm sure was all over my face as I moaned with pleasure.

He pulled out to get some more lube and I wanted that cock back in me as soon as possible. Damn getting fucked by someone who knows what they are doing is so fucking good. After a few minutes I told him I was about to cum and he sped up fucking and I could see by his face he was about to also. I couldn't hold back any longer and shot a load of cum all over my chest and stomach as he shot his load deep in my ass. After he pulled out, I could feel the warm cum running out of my ass and down my legs. Man I had cum in me and all over me. It was awesome.

Now, I have an occasional bud that stops by sometimes to get naked, watch porn and jack off. He is partnered and didn't want to do more wanting to be loyal to his bud, even though he says the sex is no longer there. He is a good looking guy with dark hair, hairy chest and a big 8 1/2" thick cock. Man I kept thinking I'd like to see if I could take that monster.

He kept talking about some guys couldn't take it but he knows how to ease it in so the bottom can enjoy it. I kept trying to get him to try and he was really wanting to but afraid to in his situation. I said just rub the head on my ass hole while I jack off and it will make me cum buckets I know. He agreed to and put some lube on the head, got in position and started just pushing the head in and out a bit.....well I was moaning with the excitement and of course he started going in a little deeper.

Fuck he did know how to work that big cock in and wasn't long until he was half way in and I was in heaven, loving every inch of it. I was jacking my hard cock as he started fucking me just half way in until we both shot our loads. I loved it and he enjoyed it totally too but after he was so scared. I assured him I was safe and negative, no worries but he said we can't do this again. Famous last words...ha-ha.

I later started on PrEP and we soon were fucking bare back and he was thrusting that big cock all the way in. If he goes hard and fast the full length is a bit uncomfortable but slower and an inch less and it's pure pleasure. We even fucked once while another guy watched and jacked...that was hot. We are still buds and occasionally hang out but not so much now so it's on to more adventures.

Next up...group fun.