Be Careful What You Hope For

Bob slowly regained his faculties while I finished my drink. I asked if I could get him a towel or something to that effect, not knowing what he had planned for us.

"Sure. You can grab a clean dishcloth from the kitchen while you're getting us some refills.", Bob said jokingly trying to imply some dominance.

"Well... yes, Masta!" I played along.

He smacked me on the ass while I got up and headed away from him toward the kitchen. If I wasn't wearing shorts, it probably would have stung pretty good. Up until that point, I had never really thought highly of pain involved with sex. I was quietly hoping that Bob wasn't "into" that. While I totally trusted that Bob would never cause real harm to me, I really hoped that his deeper interest sexually wouldn't clash with mine. While we had already had a great time together before, it was all pretty vanilla sex. Other than being man on man sex, there wasn't a lot of kink about it.

I got our drinks and a towel and headed back into the room we were in to find him no longer there. A door was flung open to the outside and I headed in that direction. Bob was laying buck naked on an outdoor lounger. His cock glistening in the moon light caught my eye immediately. I still was amazed that he carried that thing with him all the time. It really was magnificently huge. I handed him his drink and sat down next to him.

"So, what do you have planned for us this weekend?" I asked.

"Well....I was hoping to pick up where we left off last time." Bob replied.

"Well, of course. Obviously, I want that too." I said while I could still taste his cum in my mouth.

Bob continued, "I was hoping to show you one my toys."

"What kind of toy?" I asked expecting some type of dildo or plug or something.

"Well, it's kind of a harness...something to keep you from getting away." he said with a grin.

"Umm.. I've never really been into the whole domination/pain thing. I'm not going anywhere so you don't have to keep me captive." I explained.

"I don't want you to misread what I'm telling you. It's really just a way to allow you to totally let go. It's nothing crazy, I promise. But we'll get to that later. Why don't you get more comfortable?" suggesting that I join him in the nude.

I stood up and slowly undressed. While I wasn't playing into the whole strip tease thing, he was certainly enjoying the show. I could tell he loved my younger body. I made sure to turn around and bend over real good to show my ass as I was pulling down my shorts. My semi hard cock sprang forth and bounced as I stood back up and turned around. He motioned for me to come over to him and I obliged.

I straddled the lounger that he was lying on and presented him with my cock at about his face level. My cock paled in comparison to his but he didn't seem to mind it at all. The breeze off the ocean was just perfect. The temperature was perfect. The time was perfect.

"This is going to be a great weekend!" Bob said.

And without saying another word, Bob opened his mouth and took my cock in down to the hilt. It totally caught me off guard. He just jumped right on it. He applied a gentle but constant sucking on my cock as my cock head bumped the back of his throat. He slowly backed off of it resting his head on the lounger. He reached behind me grabbing my ass and pulled me toward him I grabbed hold of the top of his chair and he started to lick my balls. He washed me thoroughly.

"I want you to fuck my face." he demanded.

As I held the chair, I moved my cock to his lips. I started to push through as he closed his eyes. He created this amazing hole in his face with his mouth for me to fuck. I worked into it slowly, totally savoring the moment. As I reached the end and started to withdraw my penis, he stuck his tongue out to caress my balls. That drove me absolutely wild. I picked up my pace and started to drive in and out... in and out. He manipulated his sucking around my thrusts. He started guiding my rhythm with his groping hands on my ass, pulling me back in as my cock head had just exited his lips. I grabbed his hands and held them back above his head against the chair. This way, I was in control of the rhythm. He seemed to love that I recognized this and just gave in to my thrusts. I started fucking his face harder and harder. I had just about reached the point of exploding when I had an idea. I knew he would be responsive.

I slowly withdrew my cock from his mouth and turned my body around, straddling Bob in the lounger with my ass in his face. I presented him with my pucker as I bent down and took his revitalized cock into my mouth. He knew what I wanted and was eager to please. He dove right in like he was ass starved, lapping away at my ass, darting his tongue in and out. Somehow he knew that I wanted to ride his cock. He wanted me to ride his cock. He got my asshole ready. I was just toying with his cock, enjoying his tongue and fingers in my ass. Finally, I felt ready.

I turned back around and straddled him again facing him. He was prepared in the fact that the little table next to the loungers had some supplies in the drawer. He pulled out a bottle of lube and a condom.

"Bob?" I asked.

"Yes?" he answered.

"Are you totally free of std's?" I inquired.

"Clean as a whistle. But I'm fine with playing safe." he answered.

"I'm clean too. I really want to feel your bare cock in my ass but I'm scared of getting something."

"I totally understand. I'm clean. I believe that you are too. And I respect whatever decision you make."

I grabbed the bottle of lube from him and squirted some into my hand. I rubbed it up and down his long, thick cock. I then put some on my asshole. I grabbed his cock and slowly lowered my self onto him, his cock head resting on my loosened pucker. I pressed down a bit and knew right away that this would be a strain. I was afraid of the initial pain. I gently rocked up and down using his cock to loosen me, to relax me. He took my hard cock in his hand and massaged me while I worked my way onto his tool. I kept working down a little bit further. It seemed to take forever but I knew that if I rushed it, that it could possibly ruin the experience. Eventually, I felt confident in my readiness. I pushed down further and his cock head slipped into my ass. Wow! It popped right in beyond my sphincter. It hurt a little but I knew I was in good shape. I slowly started to work my way up and down his cock taking more and more in as we went. He continued to play with my cock which help with the little bit of pain. I worked up and down and next thing I knew, I was flush with his hips and his balls were touching my ass cheeks. His whole monstrous cock was inside me. It felt so wonderful. I just rested there for a moment, feeling his member stretch me to comfort.

"God, this is good." I said.

"It really doesn't get any better." Bob agreed.

And with that, I started to ride his cock, up an down. It felt so good. I started to squeeze his cock with each thrust. He began pushing upward to meet my downward stride. Now that we were in full swing, I could initiate my idea. We got into a rhythm where I'd ride his cock for a minute or so and then I'd stand up and fuck his mouth. It was amazing to ride such a magnificent cock and then shove my cock into his mouth and fuck his face. Just as I'd get close to exploding, I'd pull out and pounce on his cock again and just as he was getting close to creaming my hole, I'd pull off and be ready to fuck his mouth some more. This went on for quite a while under the island moon. We were lost in the moment and really couldn't have cared if we had an audience of a thousand people. We were just loving being with each other again.

"Please finish me" he begged.

I accepted the challenge. I got down on that cock. I started to ride that thing so hard, squeezing him for all I was worth. I leaned back some to get an angle on my prostate. He loved that I was loving his cock. I felt so full... so fulfilled.

"I'm gonna cum!" said Bob.

I rode him steadfastly, his cock swelling in my ass. I could feel him throbbing and then it happened. He flooded my ass with his seed. It was so warm. It was heavenly. He held me on his cock.... totally impaled on his pulsing cock. This feeling pushed me over the edge and I stood up and slammed my cock in Bob's mouth. Only a couple of thrusts later I was experiencing one of the best orgasms I'd ever felt, shooting my cum down his throat. His tongue massaging my shaft the whole time.

After my orgasm subsided, I collapsed on the lounger next to Bob's. I could still feel his warm cum deep in my ass. My cock was tingling with satisfaction. I was truly in paradise!