My First Gay Anal

He chuckled again "That's more like it" and I was rewarded with a forth finger and an even more gentle rotation now that I was getting stretched to the point where he could penetrate me without causing much discomfort. "Now, when we do this, and you are almost ready, I'm going to squirt a bunch of lubricant into you. Ok? I have an applicator that will get it deep because I'm kinda long and I don't want too much friction as we go deep. I want this to be a good experience for you Rick. You don't mind my calling you that do you?"

Something came over me, a warm, relaxed soothing of all of my hesitations, inhibitions and most of all the religiously engrained guilt. "Charles, you can call me anything you like as long as you keep making me feel like this" I said.

His response was a gentle and loving kiss to the back of my neck and shoulders and down my spine. Sitting up he reached for whatever he was going to use and I could hear it being screwed onto the tube of KY. Without removing his fingers he pushed the tip of the plastic applicator tube passed his fingers and deep inside me. When it had gone as deep as it could I felt the cold lubricant as it exited the tube as he pulled it out. Charles used the whole tube and then reinserted the hose deep and used another tube. He then pulled his fingers from me and had me lube up his cock.

Taking the lube from him I squirted it on my hand and coated his cock with it which was met with an approving moan from Charles. "That's it, babe, lube me up so I can fuck you good" he growled. When he was satisfied with the job I'd done he spoke in a raspy, throaty voice that suggested that he was in a state of extreme arousal. "Ok, roll over" he said putting a pillow under my hips. My head started spinning with excitement and nervousness knowing that what was about to happen would never be undone. A warm hand grasped onto my left hip and cupped my cheek as he moaned out "Ohhhh Yes...This is going to feel so fucking good...for both of us" he growled. "You ready?" he asked. All I could do was nod.

In an instant I could feel him moving in between my legs and his hard cock bumping into my thigh and butt cheek. At this I moaned out in apprehension and excitement as my heart beat savagely inside my chest trying to break out. It seemed to take forever before I felt the heat of his cock touching my hole, but when it did any doubt, any reluctance vaporized with the sensation of his hot, lubed and pulsating cock touching me. Then both hands took hold of my hips and I felt a slight increase in pressure and held my breath. He must have sensed it and said with an impassioned voice "Relax, just relax and try to pushed me out.' When you do you will open up and I will slide in that much easier. I promise to go slow Ok?"

I answered with a quavering voice "Yes Charles, I trust you...please" and I opened my ass and pushed against him. He pushed forward and in a moment I felt the head of his cock slip into me. The stretching he'd done had worked. Instead of the pain I'd been expecting I felt is silky smooth, hot, lubricated cock sliding into me. I gasped in surprise. He kept still as I got used to the fact that I know had the head of his cock inside me. I felt a warm hand on the small of my back as he stroked my spine. "How do you feel?" he asked

My words were lost to me in that moment so I answered by pushing myself back onto him and he responded by pushing into me further. I let out a low, long moan as several inches of his cock disappeared into me. "Ahhhh...Charles...Yes...Charles...Fuck yes." Finally came to me as I pushed back against his intrusion.

He responded with "Fuck you are so hot...I knew you'd love getting fucked" as he pulled out one inch and went back in three. I could feel his cock throbbing inside me, his heart beat filling his cock full of blood, his body heat mixing with my body heat. Nothing could have felt more sensual. I felt the pressure of his cock inside me and the pulsing of his heart beat I could feel deep inside me. In all the times I'd used my vibrator I knew I liked it rather I loved it but it had always been cold and hard. However, what I was experiencing in that moment was so magnificently different that there was simply no comparison; though 'hard' Charles cock was also soft and alive as the blood within pulsed against my insides making me feel as though we were truly connected.

I buried my face into the pillow at my head and moaned his name "Charrrrles." This had the effect of slowing his pace of penetration so that he wouldn't hurt me. However, I was so eager that I pushed back against him and felt his cock advance into my depths several inches. At this point I honestly thought that we had at least half his cock inside me. What I would later learn was that we had only 1/3rd of his cock at that point, not quite 4 inches. Charles chose to wait a few minutes while I got used to his cock while he stroked my ass and lower back. Then I felt his hands grip my hips and his cock slip out just a little, pause and then ever so slowly advanced into me several more inches. At this point I had half of his cock buried inside me. I responded by moaning my approval.

Charles once again stopped and waited for me to get used to this latest penetration. "How do you feel?" he asked.

I responded by looking back at him and the sight of his muscular body between my legs was awesome to see, broad shoulders, flat muscular waist and abs. Though I could not see his cock I could most certainly feel it as his heat pulsed deep within me. Looking up at him I said "Excellent."

He then started to rotate his pelvis in circles so that his cock worked its way in and out just with the motion of his hips with ever third or fourth rotation driving a little deeper. Each time he did this I would moan approval and try to match his inward thrust. After a few minutes I had his rhythm down and matched his motion each time so that when he drove in I pushed back allowing his lubed snake drive into me. It was so effective that soon I felt his pelvis touching my ass cheeks. Then with a quick, firm but gentle thrust I felt the base of his pubic bone hit my ass. My response was a loud moan "Ohhhhmmmmm".

Charles then stopped moving and stroked the small of my back with a loving caress as I got used to his cock as it pulsed inside me. It felt magnificent and the fact that it felt alive and warm only added to the pleasure I was feeling at that moment. In that moment I knew I'd do this again with him as often as I could. Had I bothered to pay attention to the time I would have noticed that in taking his time with me it had taken us nearly a half an hour to get to this point.

I would have changed a thing as he had done such a masterful job that at no time did I feel anything close to discomfort much less anything like pain. Considering the size of his cock I would have expected some discomfort at the very least. As it was I had his entire length buried to the hilt so that I could feel his pulse and body heat mixing with my own. Not only this, but I began to notice a sort of tingling that gave me pleasure beyond what I was already experiencing.

When we had waited a bit he lay on my back and pulled the pillow out from under me and we lay flat on the cushions. This caused him to move out ever so slightly but the motion was divine and I felt the 'tingle' hit me as my cock slipped in between the cushions. As we settled in he whispered in my ear "I want you to get used to our connection before we fuck. I'm afraid that it could hurt you if you aren't ready" he then kissed my neck and pressed his pelvis hard against me forcing his cock just that much deeper.

I could do nothing but moan my approval. It was better than I had imagined having a hard, hot cock buried inside my ass. His whole length was there and I felt it all. "Charles' I sighed 'This feels so good."

He hugged me close and drove his cock into me deeper still and whispered "I'm glad. Your first time should always be gentle. I'm glad I was your first." We lay silent for a while as he kissed my neck and rotated his hips in circles to get me used to his cock. To be honest I thought I was going to cum from just his motion and I said so. "That is a good sign that you will enjoy a good fuck."

I responded back with "Well, then lets fuck" and we did. He pulled me up off the cushions so that I was on my knees and he behind me. He paused and then pulled out slowly and inch or two and shoved himself in again. My voice release a groan of approval and he pulled out further and shoved back in to which I responded with an even deeper groan which was followed with his pulling out the whole way leaving the head just inside and then with one long, slow motion buried his entire length back into me.

I gasped in what he took to be pain and he responded with "Sorry, didn't mean to hurt you"

My response was "You didn't...You didn't hurt me at all. Do that again please...again" and he did. "Yes" I cried "Yes" as his hips came against me. Pretty soon we had a nice piston action going that was perfect for the two of us filling the living room with the sounds of our skin coming together and my calling his name "Charles, yes...oh Charles...yes...more" I moaned.

After a while he said "I'm getting close. Are you sure you want me to cum inside you?"

I lowered my head and said "Yes...please...please..."

With that he quickened his pace and soon the room filled with puk, puk, puk...sounds and my moans and whispers of "Yes,,yes...yes.." Until he pounded me with three massive, hard, full strokes before he slammed his entire length into me and cried out "AAAAAUUUUUGGGGHHHH!! As I felt his cock swell...and then release hot jets of his semen into me. That was enough for me because my own orgasm had come upon me quite by surprise and suddenly and as his cum shot into me my brain exploded with a white hot flash of light as my insides exploded and shot my cum all over the place. To my astonishment I felt Charles still pumping his balls into me he was twitching...and exploding in what had to be a multiple orgasm. Then there was his last explosion...where he moaned into my ear "G-g-g-g-gaaaawd" his cock twitched and released one last load.

He pulled me close to him and said "Don't move...please...I haven't cum like that...ever. I thought my cock would explode" he said with a laugh.

Thunder clapped outside and we covered up with a blanket and listened to the rain come down as we remained coupled at the hip. An hour later we got up, took a shower and headed back to the hot tub which had reset and was once again warm enough to enjoy. I left his place about 4 in the afternoon and walked into my empty house. I missed him. So I called him.

"Charles...you busy tonight?"

I could sense he was smiling on the other end "No, actually I'm not" he said.

"Good..because I'm all alone in this big house...and my pants just fell off. Would you mind helping me?" I said.

He was at my back door, having parked his car in the lot behind my house. I greeted him at the door naked with a glass of wine for him. As he sipped his wine we moved to the living room and I pulled the curtains..turned off the lights...dropped to my knees and I sucked his cock. However I couldn't get him to cum because it had been so soon after. So we cleansed my hole again to ensure that we could have a good time, cleanly and pleasantly.

This time I leaned over the couch in the living room and with the lights off Charles entered me again, slowly...and completely. We fucked the night away until close to midnight when he decided that he had to leave.

When he got home he called me and we talked till dawn. At which point Charles came back again and fucked me in the garage filling me with his cum again before leaving again.

That summer was the beginning of a whole new life for me. I finally learned to deep throat him but that is for another time.

Continued...