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Chad had just graduated from my high school when I saw him at one of the local gay bars. We both were shocked not expecting to meet there. He stammered "Teach, I didn't know." I put a hand on his shoulder saying "No more teach, call me Jeff now. After All we're equals in here." I motioned for the bartender to bring us 2 beers. We moved to a side table where we could talk. I knew the boy had questions. I was willing to be his teacher one more time. He had what seemed like a million stupid questions. I knew immediately that this was his first gay bar. He finally got around to questions about sex. Did it hurt? How do you know if the guy is the one? What happens after the deed is done? I asked him bluntly if he'd ever fooled around with his buddies. He had not gone beyond jerking off with them. So I asked him what he wanted to do the most. He was very honest telling me that he wanted to feel a cock in his ass. I explained that the size of the cock could affect his enjoyment. He sheepishly looked down at the table asking "How big are you?" I was stunned never having thought of sex with a student. I told him that I was average, about a bit over 6 inches, maybe 7 when erect. He reached across the table to grab my hand. Then he whispered "Do you think that size will hurt me?"
I stood grabbing his hand and showing him my erection in my jeans. I drove to my place telling him that no one must ever know about this. Once inside I poured myself a stiff drink for liquid courage. Meanwhile he slowly undressed in front of me. I don't know what I expected. But I was pleasantly surprised to see his toned, tanned body with a 5 inch hard cock. He was basically hairless except fot some around his cock. He moved to sit on my lap asking me "Does this seem Ok to you?" He leaned in to kiss my lips softly. He reached down to unzip my pants, freeing my hard cock. I moaned then said "You know the first time will hurt. Are you ready to endure the pain? I promise to be gentle." He nodded and sank to his knees to lick my now dripping cock. I raised him up and moved him to my bed. I pulled out some lube and poppers telling him that these would ease any pain.