Now that my ass was very comfortable with one finger I turned to him and asked, “do you want to try two fingers now?”
“May I?” he asked politely.
“Absolutely”, I moaned. At this point you’ve proven you know what you are doing with my asshole, so it is yours to play with as you see fit.”
He began pressing two fingers in slowly, pulling them out and putting them back in to help loosen it up.
“If I thought this hole was ready I’d have you sit on my cock right now. Fuck you’re sexy.” He continued pressing into my hole, going back to one finger every now-and-then to give me a break.
“I want you to spread me open with three fingers after you loosen me up with the two. Then I think you’ll ease right in.” I instructed.
Mean while I was trying to focus on his cock, but all I want to do was ride it. So I decided to give him an ass job, but I would wait until he was done stretching me out. I kept stroking his cock with both hands and admiring the girth. While his pole was definitely fatter than mine, it wasn’t as fat as my biggest toy which I had fit in my ass a couple of times with some patience and perseverance. I knew I could eventually take it, and I was eager to make it happen.
Moaning, I told him, “hold your hand still for me, I want to ride it a little bit and see if I can stretch myself out a little quicker.”
He held his hand still and I start bouncing back on it pushing it in as far as I dared. It was almost there. As a Bounced back and forth I stroked his cock in unison. It was getting harder. That meant he was getting pretty close. So I slowed down jacking him off until I could fit all three of his fingers in my ass.
“I think I’m ready for the third now. Stretch me out for your cock.” I begged.
In, out, in, out, in, out, in, out, I continued, until I felt his hand hold me firmly in place. That had him eager for my ass. But, I still wasn’t ready. Ass hole stretched to my desire, I puled off his fingers and immediately tried to sit on his cock. I felt his tip press against, then open my asshole. But that’s as far as it would go. It was fat and hurt to go any further. Not even the entire tip would fit. So I pushed his cock down and started rubbing it with my ass crack. It felt good. His tip would rub against my hole, and at the right angle, I could feel it try to slip in before popping back into position. I kept grinding is cock between my cheeks, I was looking at his face while I leaned back against his legs for support. All the lube was giving me enough glide to move up and down his cock quickly. It was so wet. I tried again to get it in and with some determination and a pop, in slipped the tip past my sphincters.
“Mmm, yes. Finally! I’ve been wanting this since I laid eyes on you. You’re so fat and so is your cock. I’m in heaven.”
I started riding his cock. Letting it slip in and out to slide between my crevice to give my poor anus a break. Then I’d return it to my sheath, trying to get it to the hilt. I had barely gotten 4 inches of it in before he was screaming he was gonna explode. I had let it slip out again.
“Fuck yes, I’m gonna cum.” he moaned.
I kept moving my hips, continuing the ass job. “Yes, cum on my ass. I want that warm cum between my ass cheeks. Make my hole sloppy.”
He grabbed my hips and started thrusting as he said, “I’m cumming!!!” His cum began to flood the space between us. I immediately wanted to feel him cumming inside me. I slid forward and quickly lined up his exploding glands with my now cavernous opening. As his hard cock was convulsing I slipped the very tip of him in my ass just enough to feel him shoot some of his load inside me. I stroked his cock so I could remain in that position and let him fill me with what ever was left in his nut sack.
After a couple shudders and convulsions, he was done. I squeezed out all the cum in his shaft and let it fill my hole and ass crack. I was a nice mess. My dick was so hard. He looked at it, “your turn.” I stood up and felt some of his thick, creamy jizz drip back on him.
He said, “I didn’t expect you to let me cum inside you. I very much enjoyed that surprise.”
He sat up and motioned for me to assume the doggy style position with my ass facing him. I complied. He started fingering my hole again. I looked back and saw him scooping his cum off himself and bringing it to my drenched orifice.
“Oh, fuck. Are you trying to put all that cum in my hole?” I asked excitedly.
“I am, but you’ll have to spread your legs wider and hold your ass cheeks open for me.” He instructed, talking with his hands.
That wasn’t likely to happen with all the lube, but I definitely gave it my best effort. He got all the cum collected from himself, and slowly pushed into my ass. After I would swallow a little bit he would add just a little more until it was all in. I had all his cum inside me now. Just the thought of it had me on the verge of cumming.
“Now,” he said, “give me some of that cum back.”
I pushed a little out, not quite sure what he wanted it for, but I was his little slut at that moment and obliged. I didn’t want all of it to come out, so I tightened up quickly. I felt it slide down my taint to drip off my balls and into his hand. Sliding his hand beneath me, he used my cum to start jacking me off from behind. It felt like I was a cow being milked, but then he started rubbing my hole again, and I could see the advantage of this position. I looked down and watched him stroke my manhood with his hand covered in lube, his cum, and my ass juices. The psychological thrill and my blood rushing to both my heads had my arousal at a new height. I reached under the flap of the armrest and grabbed my bag of goodies. In there was all my dildos. I reached in and found my medium sized one, less girth than him, for sure, but bigger than me. I handed it back to him.
“Would you mind using this?” He smiled and took it.
“You were well prepared for tonight. I get the feeling you had started planning this the moment you asked me to help you.”
I was too focused on what he was doing to me to answer. He had taken the dildo and pointed it at my opening. We both knew that thing didn’t need any more lube, so he gently pushed the tip in letting it plunge into my depths. I relaxed to let it all the way in. It went in with only a single stroke, redistributing his cum and lube concoction over the shaft. I moaned in ecstasy. It felt good having him fuck me again, even with a fake phallus. He started thrusting the dildo into my ass while stroking my cock. It was a mess. Cum was leaking out of my ass and when it did he used it to jack me off. He made short work of me and after a very short period of time, I exclaimed “I’m going to cum soon!!” He immediately adjust his position. He laid down on the couch with his face looking up and put his head between my legs. He resumed pounding my ass with the dildo and stroking my cock.
“Tell me just before you cum so I know when it’s coming.”
With only a few more strokes in my ass and on my cock, I began to feel that old familiar sensation welling up inside of me like a rig having just struck oil.