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The Chance of a Lifetime

Category: Gay Male
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If you told me a couple of years ago that I’d one day be having sex with a man, I would have laughed in your face. I’m straight. I’ve always been straight. I was married for eight years and have always loved dating women. I love women, the way they look, the way they smell and the way that they feel. I love to eat pussy and always will.

Lately, I’ve been fantasizing about being with a man. Not dating one per se but experimenting with one. The need to suck another man’s cock has pretty much consumed my thoughts for weeks. I finally decided to do something about it.

I had been using a dating site to find women and one day instead of man seeking woman I clicked on man seeking man. I don’t find men all that attractive so I really had no idea who I was looking for. Most of them were older or too gay looking so I just browsed around for a while, got bored and shut off my computer. A little later that day I got an email from the dating site saying that I had a personal message from someone. I logged on and saw that a guy had responded to my personal ad. His name was Jeff, he was a little older than me and attractive, I guess. I sent him a message back saying that I wasn’t really sure I wanted to hang out with a dude and that I was sorry for misrepresenting myself. He replied and said no problem, if I change my mind to drop him a line.

A couple of days went by and I couldn’t stop thinking about it. When I got home from work I sent Jeff a message that I’d like to meet for coffee. He agreed and we made plans to meet the next day. The entire day I had butterflies in my stomach. I really wasn’t sure if I could go through with it but then I decided it was just coffee and that I wasn’t obligated to do anything else.

We met at a chill little coffee shop in a pretty hip part of town. He looked just like his picture, dark hair, blue eyes, a little taller than me and in great shape. We ordered our coffee and sat down. I was so nervous I spilled my coffee three times. Jeff laughed and totally put me at ease.

“Have you ever been with a guy before?” Jeff asked

“I haven’t and I’ll be honest with you I’m not totally sure that I want to be.”

“Why did you want to meet me for coffee?”

“I’m just confused I guess. I’ve always been a ladies man but lately I can’t stop thinking about…” I blushed and looked away.

“Thinking about what?” Jeff asked.

“About… giving a blowjob.” My dick was starting to throb in my jeans just saying it for the first time.

“I totally understand. I’ve only been with two guys before myself. I like the ladies just as much.”


“What do you mean?” he sounded offended.

“No it’s not that. I mean you don’t look gay or anything. I just thought you were more experienced than me.”

“Listen, this is no place to be having this kind of conversation. Why don’t we go back to my place, I live right around the corner.”

“Wow,” I said, “That’s usually the line I use when I’m trying to get into a girl’s pants.”

“We don’t have to do anything you don’t want to do. I promise.”

I thought about it for a second and said, “What the hell. Let’s go.”

We left the coffee shop and walked to his apartment building.

His apartment was amazing. The living room was huge with a beautiful sofa and a view of the whole city. He walked into the gourmet kitchen and opened the refrigerator.

“Make yourself comfortable. Do you want a beer or some wine?” he asked.

“Have anything stronger?” I asked as I sat on the sofa.

“Like what?”


Jeff returned with a bottle of tequila and two glasses. He sat down next to me, poured tequila in the glasses and handed me one. I drank it down in one gulp. It burned like hell going down but had an almost immediate effect. I leaned back and relaxed into the soft cushions of the sofa. Jeff put his hand on my thigh.

“I guess you really needed that.”

I looked at his hand on my thigh. “Yeah. I’ve been a nervous wreck all day.”

“Are you still nervous?” his hand started to caress my thigh.

“A little.”

He took his hand away from my leg and poured some more tequila. It went down much easier this time and I sighed after drinking it down. I was feeling a little lightheaded and becoming less inhibited, so I put my hand on Jeff’s thigh. He moved a little closer to me and leaned back into the sofa putting his hand back on my leg. He moved his hand up and down my leg and was coming very close to touching my rock hard dick. His hand finally found my cock and he started to rub it through my jeans sending electric shocks through my body. I started moving my hand up and down his thigh finally seeking out his erect cock. I rubbed his dick just like he was rubbing mine. Jeff leaned in to kiss me.

“Woah.” I said “What are you doing?”

“I was going to kiss you.”

“I don’t know man.” I said.

“Just try it.” He leaned in again and this time I didn’t stop him. His stubble scratched my face a little as his lips touched mine. He gently eased his tongue into my mouth and soon we were making out each of us rubbing the other’s cock through our pants. Jeff moved his hands from my lap and started to undo his pants never breaking our kiss. I opened my eyes and looked down as he pulled his beautiful cock from his pants. It was about seven inches long and very thick. Big veins bulged from its sides and the head was purple and angry. He leaned in to kiss me again and put my hand on his cock. It leapt at my touch and seemed to grow harder and bigger in my hand. I stroked it gently, feeling its warmth. Jeff moved his hands to my lap again. He rubbed my cock through my jeans and then started to open my zipper. Suddenly, I realized what I was doing. I was kissing another man and stroking his cock. I stopped, my head swimming.

“Wait a minute. This is all happening very fast. I’m sorry but I can’t…”

“What’s the problem?” Jeff asked. “Aren’t you enjoying it?”

“I am enjoying it. A little too much I think. I just think we should slow things down a bit.”

Jeff sighed heavily.

“I’m sorry. Really. I think I should leave.” I said.

“Hey. You don’t have to leave. It’s okay. We’ll go slow.”

“Are you sure? You’re not upset are you?” I asked.

“No, not at all. It’s just that…”


“Well look at my cock. You’re so hot and got me so worked up, I’m dying to get off. Could you at least give me a handjob?”

His dick was huge and throbbing. I couldn’t help myself and reached out and grabbed it. I started to slowly stroke it again as Jeff leaned back and sighed.

“Are you okay with this?” he asked. I nodded my head and stroked his cock a little faster. A drop of precum appeared at the tip. I licked my lips and saw that Jeff was watching me.

“Go ahead.” He said. “You can lick it.”

I was mesmerized. Before I knew what I was doing I leaned over and licked the drop of precum from his dick. Jeff moaned softly.

“That’s so hot.” He said.

I continued to slowly lick the head of his cock, savoring its softness compared to the hard shaft. I put the head in my mouth and sucked it softly. Jeff leaned his head back and moaned again. I took his cock out of my mouth and jerked it slowly.

“Yeah, just like that. You’re gonna make me come.”

It was like I’d been waiting to hear those words all my life. I slid off the couch and kneeled in front of him. I stared at his cock, worshipping it. I licked the underside and took the head into my mouth again. I slowly started to move my head up and down the length of his cock, sucking him. His breathing became more rapid and I felt his balls tighten. I bobbed up and down his cock faster. Jeff put his hands behind my head and guided me.

“Oh shit. I’m gonna come. You better stop.”

I moved faster, making my mouth as wet as possible. The first gush of sperm hit the back of my throat.

“Oh fuck. Fuck.” Jeff yelled.

I slowed down a little and jerked his cock, letting his sperm fill my mouth. It was salty but not unpleasant at all. I continued to slowly suck him as I swallowed his load. I licked the last drops of cum from his dick and sat back on the couch.

“Whew. So much for taking it slow.” Jeff said.

I laughed. I realized that my own cock could cut diamonds at this point and shifted uncomfortably. Jeff saw me and immediately went to my lap and undid my jeans springing my aching cock free. He leaned forward and engulfed my cock like a starving man. He sucked me like an expert and it wasn’t long before I was shooting my load down his throat. Jeff sucked it down with abandon. We got cleaned up, exchanged phone numbers and I left. I was dizzy as I walked home. What had I just done? I told myself that I wouldn’t see Jeff ever again.

Over the next couple of months Jeff called several times. I never returned his calls and eventually he gave up. I went out with as many women as possible. I was a madman for pussy. I fucked all of them and ate their pussies for hours on end trying to convince myself that I wasn’t gay but I couldn’t get Jeff’s cock out of my head. I broke down and called him. Understandably, he was a little pissed at me. I told him that I was just confused about what had happened and that I needed the time to get my head on straight. I asked him if I could come over and he said yes.

I arrived at Jeff’s and rang the doorbell. He answered the door wearing nothing but a bathrobe.

“I was just about to get in the shower.” He said.

I closed the door behind me as I entered. I got down on my knees in front of Jeff opened his robe and put his cock in my mouth. I slowly sucked him and felt him grow hard in my mouth. He ran his hands through my hair and moaned softly. I started to suck him faster trying to milk the cum from his balls. I held his heavy balls in my hands and massaged them as I bobbed up and down on his gorgeous cock. I felt his balls tighten and knew he was close to coming. I looked up at him and saw that he was watching me with lust filled eyes. His grip on my head tightened as he unloaded into my mouth. I jerked all of his cum into my mouth and swallowed it all, loving it.

“Wow. Nice to see you too.” He said.

I stood and kissed him passionately.

“I’m gonna get in the shower.” Jeff said.

“Can I join you?”

“Yeah, absolutely.”

He walked me to the bathroom. The shower was big enough to fit ten people. Jeff turned on the water and adjusted the temperature as he dropped his robe and entered. I quickly disrobed myself and got in with him. The water was warm and felt really good as we stood under it. I took the soap and started to wash Jeff’s body. I soaped up his chest and back and massaged his ass as our cocks were pressed together. Jeff reached down and started to stroke my hard cock as he eased his tongue into my mouth. I slid my hand down and felt that his cock was starting to get hard again. We stood there making out and stroking each other’s cocks. Jeff moved his hand behind me and started to massage my ass. He slid a soapy hand down my crack and gently massaged my asshole. I’d never had anyone touch me there before and the feeling was indescribable. His cock was rock hard again as I jerked it up and down.

I turned around and let Jeff slide his cock into the crack of my ass. He kissed my neck and continued to stroke my dick. I held onto his cock and moved it to my puckered asshole.

“Do you want me to fuck you?” he whispered into my ear.

“Yes.” Barely getting the words out of my mouth. “Fuck my ass.”

Jeff soaped up his cock and slid the bar of soap up and down my ass. He aimed his cock at my asshole and slowly pushed. I put my leg up and leaned forward a little to make it easier for him. The head of his cock was making its way into my ass. He pushed a little harder and that’s when the pain hit me. I winced and cried out.

“Are you okay?” he asked.

“Yeah, just go slow. Let me get used to it.”

He pulled his cock out and slowly put it back in. The pain was going away and was being replaced with the most extreme pleasure I had ever felt. Jeff worked his big cock back into my ass. He started to fuck my ass slowly at first and then picked up the pace.

“Oh yeah. Fuck my ass.” I said. It was like I couldn’t help myself. I wanted this man to fuck my ass forever. I wanted to make him come any way I could. In my mouth, in my ass, it didn’t matter. My cock was so hard as I stroked it in time with his fucking.

Jeff started to really fuck my ass now.

“God you’re so tight.”

“I want you to come in my ass.” I said.

He grabbed my hips and pounded my virgin asshole, grunting and sweating behind me. I jerked my cock and came hard, my sperm splashing of the tile floor of the shower. My asshole clenched and this sent Jeff over the edge. He pushed his cock all the way into me and came really hard. I felt his warm sticky sperm splash the inside of my ass. He slowly eased his softening dick out of me. I turned around and hugged him.

“Thank you.” I said. “That was the most wonderful experience I’ve ever had.”

“Hopefully it won’t be the last.”

“It definitely won’t.”

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