Warning, long story

I may have wrote about this this guy in the past, but something I read tonight reminded me how I met him. Everyone was over 18.

So many years ago, while I was still in my early days of hooking up with guys, I found that I was more adventurous after having some mixed drinks. I was recently divorced and living with my mom. I had quite a few mixed drinks one night, it was getting pretty late and I was well on my way to being drunk, but I was very horny. So I put an ad on Craigslist saying that I couldn’t travel, but we could hook up in my backyard since it was super dark and super late.

I got a few responses, but one guy stood out and he said he was interested. I told him that we would be outside and that I would meet him on the side of the house. He showed up and we moved into the shadows. I could tell that he was very nervous and he kept asking if I was sure that no one would see us. I tried to reassure him that we were good.

When we got to the spot I thought was the safest, I got down on my knees and pulled his shorts down. He was still soft so I took him into my mouth and started doing my thing. He got clubbed up, never really hard. I was stroking him with my hand and sucking his tip until he said he was ready. I pulled my shorts down, turned around and got on all fours. I felt him get behind me and start caressing my cheeks and rubbing my hole. He then pulled himself up behind me and I could feel him guiding his tip to my hole. I could tell that he was using his hand to line himself up and and any second I would feel him slide into me. He would get his tip lined up and start to push, and I could feel his tip start to push in, but when he let go and started to push, nothing. It would either slip out or I could feel his cock just kind of squish into my cheeks. He would pull back, stroke himself more and try again, but it was more of the same.

After a few minutes, he admitted that he was just too nervous about getting caught and that he just couldn’t get all the way hard. I told him it was ok and that I understood. He said maybe another time and left. Now keep in mind, even when I was sucking him, he never got all the way hard. I could tell that he was decent sized, but I never got a true representation of him. Plus, I was kind of drunk, so everything was a little fuzzy anyway. So I was disappointed that I didn’t get what I wanted that night, but I wasn’t bitter at him for it.

I can’t remember if it was the next day or a couple days later, but he did message me again. He was very apologetic and assured me this wasn’t normal for him. I told him not to worry. We chatted back and forth and he invited me over. I was still very intrigued so I agreed.

When I went over to his place (I can’t remember how much time had passed), we went to his room and we both got undressed. When I saw him naked and chubbed up, and I was sober, I was amazed at how big he was. He was a tall medium build black man, baby faced, and hung like a damn horse! He wasn’t even hard yet! I got on my knees and he stood next to front of me. I placed my hand around his cock to lift it to my mouth and give him some slow strokes and I was in awe at the weight and size of him. I started to lick his head and shaft, up one side and down the other. I opened my mouth to take him in and he was almost too big. I had to stretch my jaw open to accommodate him and ensure I didn’t accidentally scrape him with my teeth. As he hardened up in my mouth, all I could fit was his massive tip and maybe an inch or two. I do remember that he was moaning and encouraging me at the same time.

I sucked and bobbed on his large shaft as long as I could before my jaw started to ache. When I pulled off he told me to bend over the bed and so I did. He grabbed a condom and some lube and lubed me up. Once his condom was on, he once again used his hand to line his cock up with my hole. Feeling his tip pressing up against hole this time made me worry that I wasn’t going to be able to take him. I asked him to go slowly and let me adjust. He was so patient and understanding and did just that. He started to press into me and I tried to relax. I felt my other ring start to open up and stretch as his head started to press inward. When he got to my inner ring he ousted just enough to get resistance and paused, letting me adjust to him. He would rub my back and caress my cheeks as he paused. Then he started to push again and my hole would stretch open a little more before he would pause again. He wasn’t even fully in me, just the tip of his heavy large cock resting just inside my hole and I could already feel stretched and full. After some more back rubbing and time waited, he very gently pushed again and I felt the tip of him pop inside me, inside my inner ring. I remember holding the sheets on his bed and wincing as I had never been stretched like this before. He read my body language and paused again asking if I was ok. I reassured him I was and said again to go slowly. After another pause, he pushed slowly further sinking his entire length inside of me followed by another pause.

Once I was adjusted, I took the initiative and started by pulling forward as much as I could before pushing back against him letting him know I was ready. He took the cue and started pulling and pushing his large cock back and forth inside me until he had a nice rhythm going. After a few minutes he quickened his pace and I was loving the full feeling and the stretching he was giving me. I don’t know how long he was fucking me, but he warned me in our messaging that he had great stamina. Feeling his cock sliding its entire length in and out of me is a feeling I will never forget. Eventually though he said he was close. I asked him to cum on my back so he picked up his pace and started fucking me faster and harder until he pulled out of me with a distinctive pop, pulled his condom off, and then stroked himself until I felt his hot cum shoot all the way up my back almost to my neck. His next shot was mid back and he kept cumming until I had cum puddled from my ass cheeks all the way up my back. He went and got a towel and cleaned me up afterwards.

Some of you may ask how big he actually was, and to be completely honest, I don’t remember and I never officially measured him. Guessing though, I’d say he was easily 8.5 or bigger and extremely thick.