My First Gay Anal Pt 2

“I have sucked your cock, swallowed your cum and taken your cum up my ass, I think a kiss is ok.” He kissed my neck and ears as he whispered.

Part 1


A Summers Schooling

After Charles had left me sprawled out on the tires in my garage I went to my bed with his hot cum still warming my insides. I had spent practically the whole day and a good portion of the evening either sucking his cock or with his cock inside me. Still I was not satisfied. It was an easy bet that had either he or I weakened and called the other first we would have been at it again. As it was I fell to sleep with his lingering warmth deep within waking in the early afternoon.

My parents phoned leaving a message saying that they were going to be back later that night and to make sure the house wasn’t on fire or destroyed. When I found out I had a full day alone I was dialing Charles when his call came through. When I answered I heard the stern voice of my former teacher on the line stating that he was dissatisfied with the lawn and that I was to come over at once to finish it. “There are several areas of the yard you missed yesterday, I don’t know where your head was but it was clearly not on mowing my lawn.’ He growled ‘I suggest you get over here right away and take care of it.”

I wasted no time getting there. On the front door was a note, “Back Patio” was all it said. Walking around to the back yard I discovered a new fence had been put up in the hours since I’d been there the previous afternoon. Opening the gate I walked through it and closed it up again. The fence was a 10′ tall and enclosed the portion of his back yard that had not been enclosed before. His neighbors were easily a half mile away in each direction which allowed him more than adequate privacy. The fence guaranteed that he had 100% privacy on his property. As he liked to lounge on his chase lounge naked while getting his cock sucked he wanted absolute privacy. Given what we’d been doing the day before, early that morning and were likely about to do again very soon, I understood the need for privacy.

“Hey there’ came his familiar voice. ‘You didn’t waste any time getting here did you?” he said.

I turned around and there he was naked on the chase lounge with an iced tea on the table. He stood up and helped me lose my clothes and had me sit on the lounge next to his. “Before we go much further I want to talk to you a little. I’m going to need you to come over twice a week for the summer to keep on top of my lawn…if only to keep up appearances. It might get suspicious if you are here to mow my lawn and it never actually gets mowed.’ He smiled at me ‘otherwise it would be so easy to just fuck the shit out of you all day. Speaking of which, how do you feel today? Sore?”

I was nowhere near sore. I had no idea what to expect after my first time. But then we had taken our time about it and he made sure that I was well stretched out and lubed before anything happened. “I feel fine. I don’t even feel sore or anything.”

Charles smiled “Good…well’ he looked out onto his lawn, smiled. ‘I hope you realized my phone call was not really about my lawn right?” A quick summer rain started that instant and drove us both inside.

“I know’ I said,’I was looking for an excuse to come over when you called me. My folks won’t be home until late tonight. So I decided I’d try to ‘finish’ the lawn today or something.’ Pausing I looked at him, ‘We could have fucked all night and I don’t think I’d have gotten enough of you” I said.

Charles paused, turned and put his hand on my shoulder. “I feel the same way. However, we needed the rest. Well, I needed the rest.” he said smiling.

Being that it was early afternoon, it was really too early for wine or beer we just decided to get on with the cleansing so that things could progress to where we both knew they would. There was no real hurry to get things going because we were at ease with each other.

Afterwards he handed me a terry cloth robe and he put one on as well and we both went to his kitchen to get coffee before heading out to the play pen couch. I noticed that it was a different configuration from the day before. It was in an L configuration with a wedge pillow on one end so that one, ‘I’, could lay back on it and hang my head down and have my throat right in line with his pelvis. However, I would not pick up on this until a short time later.

Sitting on the couch portion of the play pen we had been busy on the day before we both talked and enjoyed each other while we took this time to get to know each other a bit better, if nearly a day of fucking each other wasn’t enough.

Eventually the conversation turned to sex as we both knew it would. “”You did a great job yesterday sucking my cock. I was thinking today would be a good day to start ‘training’ you to deep throat. Had I been a bit more aggressive, which I can be in the heat of the moment, I think I could have buried my cock in your throat yesterday. As it was I didn’t want to hurt you so I kept myself contained.’ He said, ‘but it was a close, close run. So I decided that we could start today off with a slow session and work my cock a bit deeper. Who knows maybe by this afternoon I’ll be fucking your throat as well as your ass.” He smiled at me pleasantly.

Once again my heart was in my throat, only this time there was no fear or apprehension. It was all passion at this point. There was nothing I wanted more than to have his cock in my throat.

I smiled and sipped my coffee then said “Charles, I will do what you instruct so long as you promise to fill me with your cum over and over again.”

Charles just sat there staring at me. He said nothing for a long time, he didn’t have to his robe had fallen open and his cock was at attention twitching and clearly ready for whatever happened next.

However there was something else in his eye so that when he put his coffee cup down he grabbed mine and put it next to his. He then pulled me to him and kissed me. His lips touched mine his tongue parted my lips and I responded in kind. There was something going on that had not happened the day before, more than simple lust.

Breaking it off he whispered. “I’m sorry, I, I haven’t kissed anyone since Jacob left’ he paused, ‘hell, I haven’t been with anyone since he left. I, I hope you don’t mind” he asked.

My response was to kiss him like he had just done me. After which I broke off and said “Charles, I have sucked your cock, swallowed your cum and taken your cum up my ass, I think a kiss is ok.””

He then turned me so my back was to his front and we sat on the couch with his arms around me and we had our coffee in silence listening to the rain and a new wave of thunder claps which were moving ever closer, in a way mimicking the growing storm that was approaching inside his living room.

I could sense his passion and drive increase as he wrapped his arms around me and kissed my neck and ears as he whispered “I wanted to see if we could work on your deep-throat first. Then, if you are up for it I can fuck you again and again…and again. Hell,’ he paused to kiss my neck ‘I’ll fuck you until I’m too tired to fuck anymore.”

Outside a thunder clap shook the foundations of the house which happened to coincide with my hand reaching for his cock and grasping it firmly. I closed my eyes remembering the day before and what lay in store for us that day. My hand stroked his cock as I remembered the feeling of his warmth as recently as that very morning in my garage.

Turning my head so I could face him and said, “After I master taking your cock all the way. I want to see your face as you fuck me and fill me with your second load and third and however many as you can muster.” I stroked his cock with the open palm of my hand as I contemplated sucking him off.

He laughed softly as he rocked his pelvis to increase his cock’s motion in my hand “When do you want to start?” he asked.

I moved to the wedge on the edge of the couch hanging my head over the edge testing it to see if it would be comfortable, it was. Lifting my head up again I looked at him smiling and said “Now”.

Charles smiled and moved to the edge of the couch immediately. My head hung down and was perfectly supported by the pillow as well as perfectly aligned with his cock. Then Charles explained without my having to ask. “Jacob was an upholsterer in a custom car shop before we met. He made that pillow custom for us to use when he wanted to suck my cock for a long time. He enjoyed deep throat as much as he enjoyed getting fucked but hanging his head off the bed hurt his neck, so he made this to make it more comfortable. I hope you find it helpful.”

Settling in I found my spot, took his hands and placed them on my cheeks and opened my mouth.

That was his cue and he stepped up so that the head of his cock was inside my open mouth. My hands reached up and grasped his wrists and I squeezed his wrists twice to indicate he should start going in. My squeezing his wrist twice was the signal to ‘go in’ once was ‘slow down’ and three was ‘stop’. We had already, the previous day while watching the storm blowing outside, discussed the signals we would use when doing this. So it was already a known language to make it both comfortable and safe for both of us.

I was already used to his size so he slid his cock into my mouth slowly, but then suddenly he pulled out and ran to get something. “Nearly forgot the lube. I bought it this morning from the adult book store. It’s flavored and has a pain relieving agent in the gel to ease the discomfort of deep-throat. It was made for the porn industry to assist in training new talent so they could get to work quickly and not waste time working up to the ‘money’ scenes.” He said as he lubed himself.

I looked at him and smiled. He smiled back, shrugged “I wanted to make this as easy as possible for you’ he paused, ‘I don’t want to hurt you.”

Kneeling down he kissed me then stood up and resumed his previous position. I took hold of his wrists, opened my mouth and squeezed twice. The taste of cherry met my tongue as wells as a very, very slick sensation quickly followed by a tingling warm sensation that didn’t numb my senses but did make opening my throat a bit easier because the resistance was significantly reduced by both the lubricant and the pain killer mixed. Slowly he fed his length into me following my instructions via hand signals.

Closing my eyes I concentrated on his cock sliding into my mouth. As he approached the limit of my depth I squeezed his wrist once to slow him down. He did but he kept coming. When he had reached the limit I squeezed his wrist three times and he stopped holding his position.

It was here that I opened my hands and started stroking his arms tenderly as I readied myself for the next push. Almost instinctively Charles pulled out an inch or so. When I squeezed his wrists he slowly fed his cock to me in one slow, constant motion and I felt it pass my former limit with surprising ease meeting another limit where I nearly gagged. Squeezing his wrist once, he slowed and then stopped without my having to do anything and we waited.

He pulled back out just a little and I relished the feeling of his warm cock sliding out. I squeezed twice and he pushed back in as I stuck my tongue out and felt it slide over the top of his cock I was so surprised by the ease he was sliding in that I forgot to slow him down and he broke past a barrier I’d never breached before but the lube kept it from being excessively painful. I’m sure the pain killer was also a factor.

I began to recognize a sort of warming, numbing sensation as we progressed. That was the deepest anyone had gone down my throat so far and I was thrilled and nervous at the same time.

Charles looked down at me smiling and said “You’ve so got this, you so have this, just a few times more and you’ll have my entire length swallowed.” He beamed at me like he was proud of my accomplishment.

My heart was beating in excitement at taking his cock so deep. I squeezed his wrist again once and he slowly pulled out a few inches, paused, then slowly went back in. I felt his lubed cock slide over my tongue and into my throat with just a hint of a gag reflex presenting, then with a quick twitch of his pelvis I felt his cock head slip even deeper, deeper and deeper still until I felt the skin of his pubic bone hit my lips.

My eyes had been closed up to that point and opened the moment I realized that I had his entire length in my throat. He looked down at me with genuine affection and stroked my face “You have all of me. I’m going to move out slowly and let you take a breath and move back in slowly, Ok?”

I answered by squeezing his wrists. Now that I had taken his cock deep I wanted to keep him there to let my esophagus stretch but I also had to breathe so he pulled out slowly.

When I was able to get a breath in I grabbed his thighs and pulled him back deep loving the feeling of his long cock sliding into my throat. When did this I heard him gasp in pleasure and unconsciously rock his pelvis so that his cock went in a fraction deeper.

The third time his cock entered my throat I felt his balls hit my face. Their velvety surface felt warm and I reached over my head and stroked and caressed them and gave them a gentle squeeze.

Charles moaned out a soft “Ohhh yes, stroke them babe, just like that” he moaned. I pressed them to my eyes and took in the sensation as I realized that soon their contents would be shooting down my throat…but not too soon…not yet.

My gag reflex had diminished to the point that it hardly surfaced by the fifth plunge. By the sixths excursion down my throat Charles could feel the difference as he had pulled out his entire length and in one slow, steady movement drove his cock deep until his balls hit my face again making a dull ‘slapping’ sound that turned me on.

This was made clear to Charles when I grabbed his ass cheeks and pulled him even deeper in my lust to feel his cock in my throat. Unconsciously I grasped his wrists and tried to signal him to fuck my throat, to abuse me.

Somehow he understood my want but made the choice to not abuse me. “No…I’ll cum…I’ll fuck your throat…but you aren’t ready for my savagery…not yet.” He did however pick up the pace and begin a regular thrust motion into my throat.

It was probably the best he didn’t because the numbing gel on his cock had the effect of delaying his orgasm. It was meant to do just that both numb the recipient’s throat and to diminish the sensation of the cock so that they could film an extended scene sequence.

Anyway…I was enjoying my first real deep throat session with Charles. It had only been a day since he’d introduced me to how wonderful full penetrative gay sex could be. I wasn’t even sore and we had pretty much fucked the whole day and I was even now with his cock in my throat wishing for another cock in my ass. I was becoming a cock whore, more accurately I was becoming Charles cock whore.

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