Alan and Me

After our amazing first encounter, ending with Alan and Jake double-teaming me and filling my mouth and ass with their cum, I talked to Alan on the phone late into the wee hours of the morning. I was no longer a virgin with men and he was ready to talk to me and sort out any confusion I might have. It had all been so intense, I needed to "debrief" with someone. Alan wasn't just fantastic in bed, with beautiful, big cock and hot body. He was smart and understanding, too. The perfect mature guy for a first time exploring my man-on-man fantasies.

We agreed to meet at his place the next day for "Round Two," as we called it.

"I'm bringing over a porn that I watched a million times years ago," I told him. "Do you have a working VCR?"

He told me that, even after all these years, he had the out-of-date technology we needed.

I arrived at his home that evening. The place was extremely clean and smelled nice. Maybe he had been burning incense or something. He gave me a quick tour and showed me the bedroom where we were destined to spend a lot of time together, and the shower we'd end up sharing when it was time to wash off and hold each other and kiss.

"Here's the tape," I said. We were in his living room where he had a nice big couch and a flat-screen TV. I stripped down to my underwear, a pair of tight black briefs that made my cock look huge. He was wearing a short robe and silk boxers. He pressed PLAY and snuggled up closely to me, shoulder to shoulder. He was wearing colonge I couldn't identify but it smelled intoxicating. He was seducing me all over again.

"This video has a scene that fueled my fantasies for years," I told him.

"Yeah? Is this a straight video?"

"It is," I said. "I was watching only straight stuff back then. It stars this famous pornstar named Tom B. He's in hundreds of straight pornos, with too many different women to count. He just keeps coming up, over and over, in every porn video. Anyone who watched videos in the 80s and 90s has seen his big dick in action."

The scene began onscreen and there he was, Tom B, naked by a pool on a sunny day. He was with two women, a chubby one with big jugs, and a slender one. Both had natural tits and the slender one had one of the hottest asses I had ever seen.

The chubby one was on her back next to the pool and Tom B was sitting on her face. She was gripping his asscheeks and eating him out, her legs spread wide. The other woman was on all fours in front of him, devouring his dick. He was in heaven with these two women working him over with their mouths.

Then it started to rain.

"Rain?" he said. "It doesn't rain in California." The scene immediately cut to the three of them in a bedroom. Tom B was plowing the slender woman's pussy, mounted missionary-style. The other woman was behind him, sliding two fingers into his asshole. She stopped to lean in and eat his ass, then went back to fingering him. His ass was so perfect. Completely clean and hairless. His big balls were tight as he continued hammering away at that pussy.

Then he pulled out and, with a sweet whispering groan, unloaded his cum all over the bed. The two women cooed with satisfaction, watching him make a puddle on the sheet. He was slick with sweat and glassy-eyed, holding his sticky cock in his fist.

"That's it," I said to Alan. "Now I've watched this a million and one times. I'll never forget it."

Alan held me close to him. He kissed my cheek.

"I've never seen that guy before," he said. "Somehow, I missed him in all my years of watching porn."

"He's just in straight stuff," I said.

"You got obsessed with him, huh?"

"Yeah, I did. For a while I was sick of seeing him again and again, but after this video, I developed a huge crush on the guy."

"I thought you were into middle-aged men like me," he said.

"That came a little bit later. My fantasies with men started with Tom B. I had never seen anyone get rimmed and I desperately wanted to give it a try. That monster dick is pretty nice, too. That was in my dreams."

"Was there a porn with older men that got you hard?" Alan asked.

"Yeah, there was. I found a European porn that was dubbed into English. It wasn't that good, but it had a scene that made me rock hard, like this one."

"Tell me about it," he said. I pulled my underwear off and he grasped my stiff penis. He knew what I needed. "Keep talking."

"The star is a woman who looks like she's maybe in her mid-twenties. She's blonde with really nice, natural tits. Nice curves, too. In the narration, she says her mother died so now it was just her and her father. Then you see her father, who is a mature man who is a little dumpy and not very sexy at all. He's drunk and stumbling home. In the evening, she lays in her bed naked and positions the blankets so her tits and her shaved pussy are visible.

"She acts like she's asleep when he father stumbles into the dark room in his sleep gown. He sees her on the bed and gets naked. He has a belly and doesn't look like much, but his penis is long and thick and curved. It looks really good. He leers at his naked daughter, climbs into bed with her, and pulls the blankets off. Then he pushes her knees up to her shoulders and slides into her pussy. One smooth thrust, all the way in. He's over her, fucking and looking at her face, when she pretends to wake up and they lock eyes. He keeps fucking her. She moans how bad she wants his cock buried in her cunt.

"She says, 'Fuck me every night, father.' He mumbles something and keeps going while she grabs his shoulders and starts bucking. Then he pulls out and paints her face with cum. Her mouth is wide open."

"Holy shit," said Alan. "That's pretty hot."

"The rest of the video is her fucking every horny guy in the village, which was mostly played for laughs. Every guy says something like, 'I heard about you. You're the village slut whose been screwing her father.' Her attitude is "Whatever. Just fuck me.'

"I watched the whole video a bunch of times, but it was the scene with her father that stuck with me. I started to get attracted to that older guy. He wasn't really my type, but something about him getting naked and fucking her made me really, really horny."

"I guess I don't really look like him," said Alan. He slid his boxers off. "I mean, I don't have a belly."

"You're a thousand times hotter than he was. I guess it was something about his age."

"That's your incest fantasy," Alan said. "Father and daughter fucking. That's taboo."

"Yeah. That was a huge turn on for me. I wasn't comfortable admitting that to myself at first. But eventually I gave in and stopped feeling bad having those fantasies."

"But you never wanted your dad to fuck you?"

"No. Never. He was gross and he was a real asshole. Nothing about him entered my mind when I was jacking off. I think it's the idea that I'm young, ready to dive into gay sex and mature guys know what I want. That's a huge turn on."

"That's where I come in," he said and laughed. "You and I had this passion right from the first moment because I can fulfill your fantasies."

"You haven't fulfilled all of them yet, daddy," I said. "You've fucked my mouth really good and you drove me crazy eating my ass, but we have a lot more to explore."

We kissed deeply. I reached out and started stroking his penis. On the TV, a hung guy was fucking a slutty woman in a parked van. That didn't hold my attention. Alan's dick was what I wanted then. And his ass.

He broke off the kiss for a moment.

"I'm so happy we met," he said. "Jake knew exactly what he was doing when he introduced us."

"Should we invite Jake over?" I asked. "Another three-way?"

"No," Alan said. "Tonight it's just you and me. I don't want anyone else right now. We're going to concentrate on each other, two men exploring our fantasies."

That was music to my ears. I was falling for this guy. We had just met, but between the sex and the late-night conversations, I was 100% hooked.

I stood up and let him take a good look at my body. I had spent years getting into shape, with a flat stomach and a muscular chest. I loved making him horny. I slowly got on my knees and took his beautiful dick into my mouth. He held my head and thrust his cock deeper. I loved every stroke, even when he made me gag because it was so big and he forced it too deep into my inexperienced mouth. I knew I'd get better at giving head, but at the time I was so new to it all.

I continued deepthroating that throbbing middle aged cock and then I knew I had to have his ass. My fantasies about anal sex were so intense. I couldn't hold back any longer, not with Alan right there giving me everything I craved. I got my hands under the backs of his knees and pushed up. He scooted on the couch and I had his asshole directly in front of my face.

Of course, he had cleaned up before I arrived. I knew he would. I shoved my face between his cheeks and started rimming him. He said my name over and over while I ate his hot ass, unable to stop for a second and come up for air. I reached down with one hand to stroke my rock-hard penis and continued eating him out. He laid back for me and let me do everything I wanted. We savored it together.

Then he gently pushed me away. He leaned over and got a bottle of lube from the little lamp table next to the couch. I grabbed it and smiled up at him. No words needed. He spread wide, legs pulled back, and I squeezed a load of lube all over his asshole. I accidentally squeezed out too much.

"Oops!" I said. "Sorry, daddy. I made a mess."

"That's okay," said. "Rub that fat cockhead on my hole, okay?"

I positioned my cock against his slick asshole, gripping my shaft.

"Now," he said.

I pushed in. I tried to go slow but I lost all control. I slid all the way inside him and groaned. It wasn't like pussy. His ass was clenched on every inch of my shaft, so fucking tight. It felt better than any pussy I was going to find. He held my shoulders and moaned while I pumped in and out. He bit his lip and I started slamming in harder.

"Love this, daddy," I moaned. "Need you so bad."

I continued fucking his sweet, tight ass. Every thrust made me crazier. I loved being inside him, watching his big dick throb while he took every inch I could give him. I was getting close to cumming, but I held back. I pulled out for a moment to catch my breath.

"No, no," Alan said. "Keep going."

I shoved my dick back inside and we both groaned. I was feeling years of fantasy come true and it was better than I had imagined. I pounded while he whimpered, holding me. He started sweating and I felt myself getting closer to unloading. I was going to ask where he wanted my cum, but I no longer cared what he wanted. I felt like I was in control of him and we were both getting off on it. I had never felt a lover submit to me like that.

I pulled out, stood up, and started stroking an inch from his face. He opened his mouth wide and I yelled while I shot thick ropes of semen on his tongue and into the back of his mouth. It kept coming, making me lightheaded as I had the most powerful orgasm of my life.

Finally, the cum stopped and I stood there in front of him, gasping and sweating. I moaned his name, leaned in, and we kissed. We shared my load on our tongues. It tasted so good. I licked his chin and smiled. He was panting, gasping for breath. I sat next to him and lightly traced my fingertips over his cockhead while we pressed up against each other, two men enjoying the afterglow.

"You're such a good fuck," Alan said. "I want to do more to please you. Want to see me jack off?"

"Fuck yes," I said. "Put on a show for me."

He laid back on the couch while I got on my knees on the carpet. With both of us naked and sweaty, he spread his legs and slid his fist up and down his cock.

"You're the perfect size," I said.

He stroked harder and grinned.

"This cock has been in so many mouths and so many asses," he said. He leaned back and closed his eyes, stroking at a nice even pace. I had trouble resisting pushing his hand off and sucking him. My mouth watered while this sexy guy drifted into ecstasy.

"Let me have that cock every day, okay Alan?"

"Yeah, baby. We've got something now, you and me. We're not going to take a break from this any time soon."

"How many young virgins like me have you broken in?"

"Oh god," he said. "At least six, maybe seven or more. The older I get, the more sweet horny, pent-up gay studs like you I come across. I've learned all about you hot young guys and I know what you need."

My dick was still stiff. Watching him was magnetic. My head swirled with visions of the future, where Alan and I make love every day. I had taken a deep dive into man-on-man sex and it was overwhelming me.

"Was I too rough with your ass, daddy?" I asked.

He moaned a little, eyes still closed.

"Yeah, you were a little rough," he said. "But you're going to gain control over time, with practice."

"We're going to practice a lot," I said. "And you're going to watch me fuck other men. That's okay, right?

"Oh, son. You know we're not exclusive. That's part of your old sex life, back when you were getting laid with women. Guys like you and me don't get upset when our lovers suck and fuck other guys. It makes me happy knowing what's coming up for you, all the men you're going to please."

"Maybe you can share me with some other guys. Do you know local middle aged men who you want to share me with? I want you there when I'm tasting new cocks and feeling what it's like to get fucked by multiple men."

"Guys like that who I know... not a lot of them are local. There's Jake, of course. Maybe one or two other dudes like me and Jake. But the really hot men I know who are my age are out of state."

He paused.

"I'm gonna come for you," he said.

"Do it," I said. "I love watching you jack off."

"I'm going to take you to Florida to meet my friend, Billy," he said.

"Oh god."

His penis erupted with a fountain of cum. Pumping out in thick spurts. His body shook. I reached out and pinched one of his nipples, hard. He said my name over and over, whispering it and cumming.

Finally, the thick semen stopped and he laid there on the couch quietly. He was breathing with his mouth open, totally spent. I stood up and picked him up off the couch. I cradled him in my strong arms, walking slowly to the bathroom. I carried him into the shower stall and stood him up, turning on the hot water from the showerhead. We spent half an hour in the hot spray, kissing deeply and touching each other everywhere. I snuck my cockhead into his asshole for a moment, teasing him like I was going to take his ass a second time that afternoon. But I knew it was time to pause our lovemaking.

We turned off the water, got out, and dried each other off. It was a repeat from the day before. When that happened, I had my first three-way, with Jake fucking my ass while Alan pounded my mouth. Now it was just the two of us and I wanted to treat him tenderly.

We went into the bedroom and got under the covers. I kissed his mouth and we held each other, slowly drifting off to sleep. We both knew a lot more was coming in our relationship.