One New Year's, I was walking home from a party about 1:30AM. I was coming up on one of the bar/restaurants that I frequent in the neighborhood and one of the bartenders I knew was outside taking a breather. Tall, blond, goodlooking, sweetheart kinda guy whom I rather fancied, but never made any moves because he was dating one of the waitresses and presumably straight. I stopped to wish him a HNY and he surprised me by giving me a big hug and kiss on the cheek. We chatted for a couple of minutes, and he tried to get me to come in and hang out some, but I was pretty tired and had to get up again in the morning to make brunch for a bunch of people. I said goodbye and continued on home.
About 3:15, the phone woke me up. I thought it probably was one of my relatives or friends on the west coast, but when I looked at the caller ID, it said it was the front door of my building. Great. Drunks ringing the wrong apartment. I answered and it was the bartender. Whuh? I was hoping he and his GF weren't stopping by to party some more. I said I had been sleeping and wasn't up for partying with the gang tonight. He apologized for waking me and told me it was just him, and asked if he could just come up to see me for a little while. Now I was curious about why he would come over alone to see me in the middle of the night. I buzzed him in, put on a robe, opened the door and waited for him to come up.
A couple of minutes later, he arrived, holding a bottle of Dom Perignon. He seemed nervous, which was very unlike him, and I sensed it had nothing to do with being a bit tipsy from celebrating with his customers earlier.
Once inside, he apologized again for waking me up but he needed to see me real bad about something. I grabbed some champagne flutes while he was hastily opening the bottle and asked him what was going on.
He poured the bubbly, passed me a glass, then raised his. "My number one resolution is to stop lying to myself and the world and admit that I'm gay." He clinked my glass and took a sip, then continued. "And my second resolution is for you to be the first man I actually have sex with, if you're cool with that." He downed his champagne and started pouring more. I was just plain in shock.
I sat us down in the living room to make an attempt at having some kind of a dialogue about his revelation, but it was apparent he really wasn't in the right frame of mind for that just then. I could tell this was something he had been building himself up to for some time and not just some drunken whim. On the other hand, he certainly must have had enough booze to muster the nerve to come over and drop this bombshell.
We drank in silence for a few minutes before I asked him "what about your girlfriend? Have you told her yet?"
"No, no one else but you. I know you've helped other guys with coming out and I really need your help building the confidence to face everyone else. But what I really want more than anything right now is to be with you and let things go where ever they go."
I told him I wasn't sure it was a good idea to just jump into having sex before he thought things through some more, but he cut me off. "Man, you don't get it. I've been wanting this for I don't know how long. I don't know why, but from the first time I saw you at the bar a couple of years ago, I've had this craving to get with you. You don't know how many times I was thankful that I was behind the bar and wearing an apron that you couldn't see I had a raging hardon in my pants. Many times when I was making out with my girlfriend, I kept wishing it were with you. I feel so comfortable around you, and you're such a cool guy. You're real, you're not into the DC games, and I know I can trust you to not fuck my feelings over."
With that, he came over and sat next to me on the sofa. He clasped my hands and looked in my eyes. I was very uncomfortable, but I knew that if I sent him away, it would be a devastating rejection for him. I thought about the emotional hell I lived in for years when I was coming to terms with my own sexuality and just couldn't turn my back on him.
I put my arms around him and let him rest his head on my shoulder. After sitting like that for a while, he let out a sigh that sounded like nothing less than the entire weight of the world had been lifted from him, and he seemed to be dozing off. I looked at the clock and saw it was almost 4AM and realized I needed to get some more sleep, too. Not wanting to disturb him, I just leaned back a bit, closed my eyes, and drifted off as well.
I half-woke up to find my robe had been pulled open and that all so wonderful sensation of a warm mouth surrounding my cock. I remembered where I was and who was there and I almost was startled, but his somewhat clumsy but sincere effort of sucking me was simply too delightful to interrupt. I ran my fingers gently through his hair while his tongue explored my shaft and foreskin, and he became increasingly adept at getting more of my dick down his throat each time he tried swallowing me before he started gagging.
I realized he was still fully clothed and told him to stop for a minute and lose the clothes. He shed them in a heartbeat and I was rewarded with a view of his beefy, somewhat hairy body that I had only been able to guess about until then. He was also sporting a nice, thick six incher. I pulled his dick to my mouth and swallowed him whole. Apparently, no one had ever done that to him before and he nearly lost his balance from the rush. He started moaning and whimpering, and his cock was throbbing like he was about to blast his load in my mouth right then.
I let his cock slowly slip from my mouth and began sucking his balls while gently playing with his nipples. He was breathing heavily and quivering and shuddering like it was the first time he'd ever had sex at all.
He was laying back on the sofa now and just instinctively began raising his legs as my saliva was running down his asscrack. I used my goatee to tease him under his balls and between the cheeks. All he could do was mutter nonsense and moan. I pulled his cock back toward me and started sucking it some more, slobbering gobs of spit out that I was swiping and fingering his ass with. The combination of his dick in my mouth and a finger working its way into his tight ass had him muttering praises to Him On High and saying over and over that "I'm yours! I'm ALL yours! Anything you want, man, I'll do it for you!"
I brought him to the edge at least 3 or 4 times in rapid succession and decided that he was ready to go all the way. I pushed his legs wider and began teasing his wet hole with the head of my cock. He began pressing against me, trying to snag the head so it would go in. He finally succeeded, and I began slowly pushing into him as he pushed back toward me. He was way fucking tight. I knew from the way his ass was throbbing, the tentative rigidness of it trying to crush my cock if it couldn't push it back out, that this was definitely the first time anything had ever gone up his hole. I asked if he was OK or if he wanted me to stop. "NO FUCKING WAY, MAN! I NEED YOU INSIDE ME! I NEED YOU INSIDE ME!"
He finally started to relax enough that I could gently slide back and forth a few inches. I realized his eyes were fixed on me, that he was creating a mental recording of how he finally became a man. He seemed to become hypnotized watching my pulling away and pushing back into his ass, and his ass finally accepted what was happening to it enough that I could get in all the way.
That did it. Three strokes at most against his prostate and his cum erupted like a milkshake out of an uncovered blender on high. And it wasn't stopping. After the initial blasts, cum just kept gushing, then oozing out of his cock. I was getting really close and he knew it. "Oh man, don't even think of pulling out! I gotta have your cum inside me. I gotta have what I've been dreaming of forever!"
His ass clamped on my cock again, and he reached down and gently squeezed my nuts. That was it! I filled his ass with one huge load that was already starting to ooze back out and I was still shooting! I collapsed on him and we just lay there, still panting, unable to move. I finally slid out of his ass, pulled him up and into my arms, and we dozed off again.
I woke about 8:30, and tried to extricate myself so he wouldn't wake up. I covered him with my robe and went to make coffee. I came back, lit a cigarette, and just watched him sleeping. He looked so angelic, so totally at peace -- a complete 180 from how nervous he was just a few hours earlier. I didn't want to wake him, but couldn't avoid it since I had to get brunch started. I waved a cup of steaming coffee near his nose for about a minute and it finally got him to open his eyes. He sat up, took the coffee, lit a cigarette for himself and stared at me with a kind of dazed, puppy dog expression.
"How are you feeling, bucko?" I asked?
He looked at the empty champagne bottle on the coffee table then back at me. "This is the most incredible thing. I should have the hangover from hell after all I drank last night, but I feel like I'm ready to run a marathon. That was the most incredible sex I've ever had. No woman has ever made me cum like that, even if I didn't jerk off for a week before. And, oh my God, I have never felt anything like I did when you shot your load inside me. I thought I was going to cum again just from you cumming!"
"And now you know why they say only another man knows how to really make a guy cum."
"No fucking shit, man! I can't believe I've been running from this! Man, what the fuck was I thinking?"
I gave him a Cheshire cat grin. "Welcome to the club, bucko."
I offered him a shower and invited him to stay for brunch, but he begged off, saying he had to get home to do the obligatory New Year's Day calls with the family. He looked in a mirror as he was dressing, and commented that he definitely had the proverbial "fresh-fucked look." I asked if he was sure he wanted to head home looking like that. "Hell yeah! It's a new year and I'm a new man and I want the world to know it." We hugged, kissed, and he left.
We've been good buddies ever since, regular "fuck buddies" but never went the route of becoming romantically involved. It would have been too much, too soon for him back then, and would have made it very difficult for me to also be a mentor at the same time. He moved out of the area a few years ago and I only get to see him once or twice a year when he comes to visit, but when we get together, it's like that first time we fucked. He officially ditched the girlfriend a week after we got together. She went double-atomic when she found out many months later that I was the man who "turned" him. Needless to say, I avoid eating at restaurants where she works.
Happy New Year, y'all.
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