I was nervous.
The last time I knowingly took a guy's virgin ass (though I'm sure taking a load down their throat wasn't foreign to them) was a couple of years ago with a kid that was home from his freshman year at college. It didn't go so well. I'll explain that one next time.
But this guy, I'm pretty sure is going to go differently.
He's a 50 year-old guy, for one. Married, but just recently taken the plunge and indulged in his thirst for men and cum. He's been going around the world gorging on cock, sucking down strange boys in the cities he's visits for work, but he hasn't taken the extra step to take it up the ass like he's always fantasized about. Maybe it's a cliche, but it sorta fits. He drives an expensive sports car convertible and chases guys younger than him. But he's still fit as fuck. His body drives me to shame. A smaller guy about my height, but with well defined broad chest, cut abs rippling down a naturally smooth body and clean cut face with strong masculine features. In a word, he's hot.
But I'm not nervous because he makes me feel inadequate. He's, in fact, warm and giving with affection and compliments that will ease any doubt. An eager pup excited to play. I'm nervous because of the responsibility I hold. And the fact that his kid was sleeping upstairs also kinda weighed on my mind.
I had already aborted one attempt at anal. He's already sucked me off a couple of times in the past and when he asked about anal, I let him know I was all for it. But when I got there, it was all wrong. He wasn't himself. And when I went in for the kiss, I knew why. He was drunk as fuck. Slightly slurred speech and he reeked of alcohol. I could even taste it on him. Drunk off his rocker and it was 6am in the morning. I wanted him to feel it and remember it all. Most of all, I needed to know that he wanted it and, with a clear head, beg for it. And I knew what would happen if we started.
But today, he was sober. And eager. He was waiting for me at the stoop and the long length of his driveway was making my heart pound in my ears in the anticipation with every step.
He leads me into the storage unit next to his garage. Next to a couch is a sewing machine and clear plastic boxes piled high with his wife's arts and crafts supplies, long stationed in the corner that he doesn't realize how strange it feels for a guy to walk in and attempt to fuck him in a room that's obviously his wife's retreat. But when our lips meet, he sucks at them greedily, trying to suck in my tongue and devour me. My hands fly up under his shirt as his cock starts to grow and poke out at my under his gym shorts. His soft skin and firm abs always amaze me as I trace his cut lines.
He breaks away. I look at him.
"You sure about this?" I ask.
"I think so... Yeah. I want it," he replies hesitantly. "Wait a sec."
He fumbles around and find a pack of condoms and lube. It was obviously a sec pack for his work trips. At that point, I wondered if this was really his first time.
I fumbled with my track pants to get them off and then used the lube to put a dallop on my hard, drooling meat. A big glob stayed firm from the cold air making it thick enough to hold the shape of a gum drop before I rubbed in. He was sitting on the couch, mesmerized, as I rolled on the condom and then got some more lube on my fingers. I leaned in for a kiss while I worked a generous amount of lube on his hole. At every pass of my fingers, I'd feel it twitch. Relax in slow moments before a sudden tightening. His arms showed goosebumps even though his hear was racing against my chest and his heat was strong enough to me start to sweat. Relax, tighten, relaaaax, tighten. I pushed a finger in and it was really tight. Slowly. Just a little at a time. And when my finger was fully inserted, I still felt it relax and tighten around my finger. Even in it's relaxed state, I felt the blood pulse in sphincter. A steady quick pulse like the waves of electricity across a line. And I knew, he was speaking the truth. It was definitely his first time. At this point, the making out slowed down to the point where he was just concentrating on his hole and when I pressed against the hard bulb of his prostate, he let out a yelp.
"I want you in me."
I pulled my finger out of his ass, probably a little too quickly, and placed the head of my covered cock against his hole. Even through the latex, my cock could feel his heat.
Propped his other ankle over my shoulder and then placed the head of my cock firmly against his hole. He gasped and grabbed onto my leg and started to push me back, but I kept up the pressure. Not enough to push in, but enough so I wouldn't be pushed out. My cock head was past and met a tight resistance. And that pulsing! It did wonders against my cock head. Made my cock jump and flare out over and over. It was one of those moments where I felt his hole finally relax a little and I inched in. He white knucked my thigh but I didn't let up until I was balls deep. And there I stopped. Even with it covered, I felt the strong heat of his desire. His chest was heaving as he was mumbling under his breath. I laid a hand firmly against his chest and felt his heart racing before I pulled out slowly. I wanted him to feel the entire length of his cock. I wanted it to feel like miles of man that was invading his channel. Right when I just the tip of my cock was in, I slammed it back in. On and on for awhile before I felt like he needed to feel something different, so I stayed deep in his hole and then made my cock throb to impale him with another inch. Then I gyrated in a circle to see what the next best angle should be and his quick breaths told me when I was on the right track. I fucked him mercilessly before I laid my hand on his cock. My hands weren't cold, but they felt like they were against his white hot cock.
"No, don't. You'll make me cum."
But I knew that he was already past the point of no return, just from the extra heat of my hands.
So I just grasped it firmly, letting the rhythm of my fuck be the stroke of his cock. And in seconds, he let a stream of cum fly. And another. Then two smaller spurts before he was spent. He grimaced when I pulled out.
"But you didn't cum yet."
"It's alright. That was all I needed." I got up and he did as well, albeit a bit wobbly.
"I want you to cum, though."
So I pulled off the rubber and put my arm around his shoulder and jerked it for a few seconds in a circle jerk style. He lightly rubbed my stomach and I shot a load onto the cement floor.
As I was putting my clothes on, things got a bit awkward.
"Oh yeah. It was just a bit... intense. Lots of things running through my head."
I gave him a long hug before he led me out the door. But later, he texted me begging for me to do it again.