“That just about sums it up.” I confirmed.
“Then let me ask you another question. Did you ever have a need to go run errands or was that just an excuse to get me here alone?”
At this point, I felt the charade was more or less done. I felt I should bring the teasing to an end. It had been hours. What I was doing was delaying the inevitable. I knew this guy was into me by now, and he knew I liked getting fucked and had put the pieces together. He had deduced that I wanted him to take me inside and have his way with me.
“Well, it would seem you see right through me. I, indeed, had one errand and that was to get you alone and confirm that you are indeed gay, as I had hoped.”
“Well, I must say I am flattered.” He said ryley. “When exactly did you first think I might be gay?”
“It was your special attention to me that had me wondering, then the awkward drum on my shoulders that basically confirmed it.”
“Oh, you caught that, huh?” He laughed awkwardly.
“Yes I did. I wasn’t going to tell you to stop, so I was disappointed when you moved over to Karen, instead.”
“So now you have me alone, we’re naked, and you know I’m gay, and I now know you wanted all this to happen. What now?” He asked eagerly.
This is what we had been building up to. We knew it was going to get down to dares only eventually. I stood up and turned around facing the edge of the pool. I turned my head to look down at him.
“I dare you to get that closer inspection of my ass to determine its level of tightness.”
I climbed up the stairs and, grabbing a towel real quick, knelt on the on the towel at the edge of the pool in a doggy style position, my head resting on my forearms that were folded beneath me on the concrete. I looked back and watched him stand up and position his face right behind me. He put his hands on my ass cheeks. I was excited for him to look at my ass. I had gotten waxed the week prior. The crack, my taint and my balls were all perfectly smooth and clean. It made me feel sexy.
I felt him grab my ass cheeks and give them a gentle spread. I was laid completely bare to him. There wasn’t really anything left to see of my body, and he was very close to my goal of being inside me. It was so hot. I felt him rub my ass cheeks feeling them for firmness. In this position my ass was tight. The muscles were pulled tight… mostly.
“You have a very sexy ass, and it has been calling to me all night.” he claimed.
“Oh really?” I said with a giggle, a manly one of course.
“Oh yes,” he said. ” You’ve been wiggling this thing in front of me all night as if you want me to take advantage of you.”
“Me? Never.” I said playfully denying the accurate accusation. I then wiggled my ass a little side to side in front of his face.
“How am I gonna inspect this thing if you keep wiggling?” he said admonishing me.
After he finished admiring my hole, he shoved his face between my ass cheeks. I could feel his tongue probe my anus. He licked up and down and in a circular motion, lapping at my opening as if to gently coax it open for him and let him in. After my initial shock, I began relaxing my sphincter to let him slide his tongue or whatever else he wanted to put in me.
“Oh my gosh, Tim.” I moaned. “That feels amazing.”
“I thought you might like that.” He said with confidence.
He continued his ministrations, working at my hole to prep it for his next step. I just stayed still and let him service me. It was so naughty. I loved that this gay, chubby man was in between my cheeks, running his tongue all over my asshole. He eventually returned to probing with his tongue and I could feel him beginning to open me up. I gave a slight push of my asshole in an effort to allow him more access. I could feel him push harder and slide further in. He continued on my ass for a little while, making sure I was nice and wet.
“Now let’s see how tight you really are.”
He slid his right hand to my crack and started gently running his finger from the top of my smooth groove, down to my taint, making sure to go a little slower as he gently rubbed my ass hole. I inhaled sharply at his touch and I felt myself pucker by reflex. He did that a couple times, making me softly moan each time. After a minute spent teasing my hole, he put his finger directly on it and started moving it in circular motions. It was heaven. I love getting my hole played with. Whether it be a finger, a tongue, a cock or a dildo. It was feeling so good and I didn’t want it to stop.
I kept my eyes on him so I could see what he was doing. I liked watching him get mentally prepared to penetrate me. He put his finger in his mouth and worked up a bit of saliva all over it. I watched him pull his finger out and move it towards my eager hole. I shifted to let my legs open a little wider to allow my ass to spread wider on its own. With his left hand still placed firmly on my left cheek, he began gliding his wet finger in circular motions on my already moist asshole. He started pressing into my anus and I could feel he was having little difficulty. I relaxed further and felt him slide in about an inch. My reflexes made me clench up again instantly, restricting him from making any further entry. After a second, and pulsating my ass hole a few times, I relaxed again allowing him to go in a little further.
report “Damn, I was right. You’re fuck hole is so tight.”
He pulled his finger back out, and out of a strong urge, I moved my ass with it in a motion begging for more. He read my cue and put his finger at the entry to my hole again and paused.
“You want more?”He asked.
“Just a little more, please.” I pleaded.
Was I really pleading for him to be in me? Yes, I had been begging for this and he knew it. He pressed in again, meeting resistance, but my hole relaxed easier the second time around. His finger goes a little deeper this time and he starts working it back and forth, pushing deeper with every stroke inwards. I push back a little bit allowing him to get further in a small stroke.
“I’ve already measured how tight you are,” he said, while still working his finger inside me. “I don’t really need to keep measuring it for you.”
I could tell he was trying to be flirty and coy, but he had said it with little feeling because of his focus on his finger in my ass. He was so good at it. He was gentle with me and took the time I needed to adjust.
“Then let’s see if you can loosen it up a little for me. Maybe prepare me for something bigger?”
He gladly obliged by finally getting his entire finger inside me. I could feel it reaching the inner depths of my hole and his knuckles up against my ass. So he started fucking my ass with his finger. In and out he moved, rubbing my prostate and rotating his finger for more sensation. Inside me I could feel him pressing on the inner walls of my rectum. He started moving faster now that I had been worked open a little. I accepted it willingly. But, suddenly he stopped.
“Is that loose enough for now?”
“Yes,” I said with noticeable disappointment.
I knelt up and turned back around to find his face right in front of mine.I welcomed his invasion into my space.