Friday Night

I'm not convinced that I knew with any certainty why I chose this night to work up the courage to walk into what was known to be a gay bar in a neighborhood not far from where I lived. All outward appearances would mark me as straight, but I had a secret desire to be with men for many years. I sometimes dated women, and there was the occasional time when I would hook up with a guy, but that was an infrequent occurrence. Lately I had begun to feel restless, unhappy with where my life was now and I wanted to follow my instincts rather than my logic. I decided to let my guard down and see what would develop if I openly sought the company of gay men and that decision ultimately brought me to today.

Every journey starts with the first step and the first step of my journey began tonight. I sat in my car for a few minutes before finally deciding to get out and enter the bar. Not knowing what to expect was the worst feeling and once inside I immediately felt better. I was greeted by a friendly bartender and no one seemed to take much notice as I walked in and took a seat at the bar. I looked around and was glad to see some men like me and I wondered if this was the first time for any of them.

I chatted with the bartender on occasion, but he was kept busy by the customers and couldn't spare too much time to talk to any one person. A few other guys took seats next to me when it started getting a bit crowded, but those conversations were just pleasant pastimes and no real connections were made. Perhaps I was too optimistic in believing that one foray into the gay bar scene would produce the results I was hoping for, but I was realistic enough to understand that it takes time to meet people, specifically the right people.

Around midnight the place started to empty out and I was preparing to head home myself, a little disappointed but at least I could say that I went into unfamiliar waters and had some fun in the process. As I started picking up my money from the bar a nice fellow took the seat next to me. I looked at him and smiled. He smiled back and asked, "You're not leaving already, are you? The night is just getting interesting."

"Well, you might just be right. Perhaps I should reconsider, what do you think?" I responded.

"Definitely you should," he said.

I put my money back on the bar and called the bartender over. "Let me have another Jack on the rocks and what can he get for you?"

"I'd like a Grey Goose on the rocks with a twist. Thank you and my name is Cory by the way," he said.

"I'm John but most people call me Jack," I replied.

Just like that, when I was getting ready to leave, Fate intervened. Cory and I had a nice conversation and a few laughs. He told me that he was new in town and came here hoping to meet some people that he could connect with occasionally. I told him how this was my first time in this particular place and how fortunate it was that I didn't leave five minutes earlier. Clearly, Fate was at work.

After about half an hour and our one drink together, I said that I should be heading home since I had an appointment in the morning. Cory understood and said that he probably should leave as well. I paid the bill, took my change and Cory and I left the bar together. Outside, in the parking lot, Cory said that it was too bad that we had such a short time together and wished that we could extend the evening. I agreed and with that Cory said that his hotel was not too far away and while their bar was probably closed, he had a great mini bar in his room if I was interested in a nightcap. I had just enough alcohol in my system to make a quick decision on this invitation and I agreed to follow him to his hotel in my car.

Parking our cars next to each other in the lot, we walked into the lobby and took the elevator to his suite on the executive floor. His rooms were nice, a living/dining area and a separate bedroom with an en suite bathroom. Very nice accommodations.

Once we got inside, Cory told me to make myself comfortable and he would get a couple of drinks. I looked out of the window at the skyline and after placing the drinks on the coffee table in front of the sofa, Cory shut off the lights saying, "It's a much better view at night with the lights off, don't you agree?"

"Yes, it's great," I replied and walked back to the sofa, taking a seat next to Cory.

After we took a sip of our drinks, Cory said, "You're a nice-looking man and I hope that you don't mind me saying so."

"I'm flattered actually, and I appreciate the compliment," I responded. "Your quite attractive yourself and I'm glad that we met tonight."

Cory leaned over and kissed me on the cheek and then turned my head so that he could kiss me on the lips. I kissed him back and felt his tongue probe my mouth. He moved lower and kissed my neck, eliciting a low moan on my part. His kisses stayed on my neck for a few minutes and then he went back to my lips.

I was breathing heavily now and Cory clearly liked my reaction to his kisses. He stopped kissing me long enough to ask if I wouldn't be more comfortable in the bedroom so that we could get out of our clothes and stretch out on the bed. I said, "You may take me for a slut, but yes, I would."

Cory laughed and said, "I do."

We went into the bedroom and once there I stripped off my clothes very quickly. Cory watched me and then said, "Undress me."

I looked at him as his words and demeanor seemed different. He stood in the bedroom and had watched me take off my clothes without moving and then simply said "undress me." He seemed very attentive to me when we first got to his room but now his attention appeared more focused on himself. Nevertheless, it had been really nice so far so I went along with his request and removed his shirt and pants and then his tee shirt and boxers. He sat on the bed and raised one foot then the other so that I could remove his socks. Once he was naked he moved to the center and then up so that he could rest his head on the pillow. "Come suck my dick," he said.

I stared at him, momentarily trying to gauge if he was serious or simply trying to be funny. "What did you say?" I remarked.

Cory looked at me sternly and said, "I said, come suck my dick. Don't make me repeat myself, Jack."

Since this is what I secretly hoped for tonight, I slowly inched my way onto the bed and then brought my head up to his abdomen. I looked into his eyes and then, dropping my gaze, wrapped my lips around his stiff cock. Cory moaned as his cock slipped deep into my mouth and I began to move my head up and down. "That's a good cocksucker," Cory said.

I was startled by his words since I had never been called a cocksucker before even though that is what I was doing. There was also something else about the tone; his voice was hard and the word cutting. "Suck that dick and take it deeper. I want to feel it in your throat," he commanded.

I took it as far as I could while still being able to breathe but he was not pleased. Cory grabbed the back of my head with both hands and forced my head down onto his cock cutting off my air. I held my breathe until I couldn't hold it any longer and then pulled back. Cory laughed and after a few seconds grabbed my head again and forced his cock down my throat. Again I lasted about fifteen seconds before pulling away gasping. Cory relented and only pushed my head down far enough to hold his dick in my mouth while allowing me to breathe as well. He then moved my head up and down, fucking my face.

As much as I was startled by what was happening I also found it exciting. I had gotten an erection and my dick needed some attention. My erection did not escape Cory's gaze so in the next minute I was told to move up higher on the bed and to place my face between the pillows. I did as I was told and then heard the night table open and I felt Cory's fingers, covered in lube, push their way into my anus. I grimaced and grabbed the sheets, burying my face into the pillows so as not to cry out. Clearly, Cory liked my reaction and said, "Oh, you're a good little cunt. A nice tight pussy just aching for a stiff cock to take care of that hardon of yours. Nothing like a good ass pounding to relieve an erection. How does that sound, cunt?"

I could not say anything. It was not supposed to be like this according to my imaginings. Cory asked again, "I said, how does that sound?"

I heard myself say, "Wonderful."

Cory leaned close to my ear and whispered, "Wonderful, sir."

"Wonderful, sir," I replied.

"That's better. You'll soon learn your place, you little cunt."

Cory climbed on top of me and pushed his stiff cock into my ass, balls deep. I cried out, "Oh, God, that hurts! Please go easy."

Cory pumped even harder and responded, "God won't help you now, little cunt. This is what you're made for and this is what you're going to get."

I grit my teeth and clenched the sheets while Cory proceeded to fuck me, jamming his dick into my ass as hard as he could. At one point he reached one hand up to my throat and started choking me but only enough to make it difficult to breathe not impossible.

After a few minutes I felt his body stiffen and he pushed into me as far as he could, shooting his load of hot semen deep into my bowels. He groaned and pushed, emptying every last drop of cum from his balls before rolling off and lying next to me.

I rolled over and stared at my deflated cock. Cory was right, a good ass pounding does relieve an erection. Cory looked down at my dick as well and said, "I'll bet that you would like to cum too, right? Well, go ahead, stroke it."

Not knowing exactly what to do I reached down and gently touched my dick. "That's a good cunt," said Cory, "stroke it harder. I want to see you cum."

Suddenly my cock woke up and before long I had a beautiful hardon. I stroked it as instructed and Cory got some lube for me to make it more pleasurable. My groin started to tingle so I knew that I was close to an orgasm but I held it back as long as I could. As I started to moan and my stomach muscles started to tense, Cory leaned his head down and wrapped his lips around the head of my dick just as my semen exploded into his mouth. He held my cock in his mouth, letting all of my cum accumulate until I was drained, and then leaned up and spit it all into my mouth, saying, "Swallow it cunt." I did as I was told.

After we cleaned up, Cory got another drink for us while I dressed. I wasn't sure what to say so I said nothing. Cory broke the silence, "You were very good tonight, Jack. Most guys, those that don't lean towards being submissive, wouldn't do what you did without taking offence. You may not have liked all of it, but you did as you were told. That's a good thing. We will see more of each other and it will become easier for you each time, as long as you listen and follow instructions."

"I think that I understand," I replied.

"Good," said Cory. "You will come here Sunday evening at 9:00pm and we will continue your training. Do you understand?"

"Yes," I responded.

"Yes, who?" Cory shot back.

"Yes, sir." I replied, "Sorry, sir, it won't happen again."

"You're a sweet cunt, Jack," said Cory.

"Thank you, sir," I replied and walked to the door.

Cory stopped me and kissed me on the lips saying, "See you Sunday, Jack. Don't be late."

"Yes, sir," I said and walked out.

I was sore and drained with a load of my own semen in my stomach, certainly not what I expected when I went out tonight. It was enlightening and, as I walked to my car, I felt myself looking forward to Sunday.