Frustrated

I posted an ad to get laid with big ass women or bbw, and this married guy answered me by asking if I would be interested in fuck his big ass. At first I thought he probably had answered to the wrong ad, but he said no, he saw the pictures of my cock and he loved how perfect look with a big shinning mushroom head and that this would be his first time. He sent me pictures of him spreading his ass, and it seemed a really tight hole.

I agreed in doing it, as long he made me a blowjob and let me cum on his mouth. This guy never have done nothing like this and he was uncertain about the blowjob, but 100% in getting my cock deep in the ass.

After some more messages, he finally decided in blowing me but I wouldn't cum on his mouth.

We met after two days on a cheap hotel room and he was really nervous about it.

I assured him that I wouldn't push my cock down the throat and cum inside.

He seated on the couch with the eyes closed and waiting to feel my cock in his lips. I started by using my big mushroom head as a lipstick and told him to start to kiss it and slowly start sucking it like a ice cream and let it go inside until he couldn't more. He clearly had no experience and asked me to basically do everything. I could feel my cock head beating in the back of his head but just ask him to suck my mushroom until I cum right on his face. Something that he wasn't expecting but didn't seem to care.

After washing the face he took a good look at my cock and started having doubts that he could handle everything deep inside the ass.

I grabbed my lube bottle and put that big ass in position to be penetrated. That butthole was indeed super tight and I knew that this is going to take time to get the hole relaxed and with enough lube to make sure my big mushroom head would go inside automatically. I explained that he needed to relax and let my fingers start to open the door. The moment he felt his hole getting stretched by my cock going inside he started panican and wanted to stop. I told him to hold on my cock inside him. I tried going full on, but he couldn't stand the pain. He rapidly got dressed and until run out the door. It was a frustrating moment... I barely got 10 cm inside and the blue pill was kicking in.

He never replied to my messages since then.

Comments

Anonymous

by Anonymous on Mar 26, 2025 at 8:33 AM

Only time I did anal was with a roommate in college, we had been exchanging blow jobs for about three months and both left for holiday break. When we returned I was not even in the room five minutes and he wanted to suck on me, I am standing there ejaculating in his mouth and when I finish he looks up at me and asks if I will do anal with him, he wants to feel what it is like with a real cock. When I said sure, why not but told him I did not want the experience done to me he was fine with it, stood up saying he was already cleaned out hoping I would say yes. He grabbed this tube of lube from a drawer, knelt down and sucked me until I was hard again then spread lube all over it. He got up on his bed on his knees with his ass up and I slowly worked it in there listening to him moaning the whole time, strange feeling compared to a pussy, just like fucking a tight ring really with not pressure on the head once in there. I started just pushing like an inch past my head then pulled back out for another nice tight plunge into him. I had to admit it was feeling really good for sure.

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