In Appreciation of Thickness

"Thanks for letting me try something I've always been curious about," I said. "Cheers."

"Hey, my pleasure - really," he replied. "So what else are you curious about?" he asked before almost entirely draining his beer. "Let me ask you something else... have you ever been fucked?"

Being more horn-charged than ever, I immediately replied, "No, but I'm open for whatever you have in mind... that is, if you're up for it?"

"Oh, I'm up for it,' Tony smiled. "I'm just not sure you will be."

I was in full-on sex mode at that point.

"Absolutely. If you can bring it, I'll try my best to take it," I said.

Tony looked at his watch for a second. "Ok, I've only got about 30 minutes, so this has to go pretty fast. You'll probably be more comfortable laying down on your side or on all fours." As he spoke, he grabbed his cock and began to stroke it. "Why don't we go into your bedroom?"

My somewhat still-hard dick began to stir again at the thought of taking on Tony's monster. I'd never had anything more that large up my ass. The thought of being able to accommodate Tony's thickness was something I'd either regret or love, but I knew it was a once-in-a-lifetime opportunity that I couldn't pass up.

"I have lube and stuff in the bedroom," I said. "I also bought some condoms, but I don't think they are going to work, so I'm not sure how you feel about that."

"I don't think we have to worry about that," he said. "It's been a really long time since I've fucked anyone other than my wife without one, but I can tell we're in virgin territory here. Unless you're not being totally honest with me, I'm ok without one."

"Ok, like I said, I've never done anything like this before. I might need a quick drink though, if you don't mind?"

"Go ahead," he said.

I quickly went to the kitchen and poured myself a shot, downed it, then drank another. By the time I got to the bedroom, Tony had lubed his cock and was arranging the pillows.

"C'mere," he said. "I want you to get up on the bed on all fours and put these pillows under you."

Already a little buzzed again and shaking in anticipation, I did as he asked.

"That's it," he said as he positioned me. He then walked up behind me and began rubbing the head of his cock along my butt crack, pausing occasionally at my hole.

"Now," he said. "Let's make sure we have plenty of lubrication. I need you to relax completely. You're going to feel quite a bit of pressure at first. If it hurts, let me know and I'll stop. I need you to take in and let out a couple of deep breaths. That'll help you relax too."

His voice was very calming, almost clinical. I could definitely tell he'd done this before.

"I want you to grab ahold of your dick," he said. "When you feel me begin to push into you, I want you to pull your dick up upward toward your stomach. That will help loosen everything up behind. Ok?"

By that point, I was aching for him to get started. "Ok," I said. "Just go slow."

"I will," he said.

I could feel the massive head of his cock pushing directly against my tight hole. Then I felt him squirt one last cold stream of lube down along my crack, drenching my hole. I could tell he was squeezing his cock with one hand as he pushed somewhat forcefully into me. Suddenly, an enormous bolt of pain shot through me from my asshole into my abdomen. I winced and lurched forward.

"Sorry, about that," he said. "Let's try something else."

The next thing I felt was Tony's finger plunging into me. He worked one, then two and ultimately three in and out, applying more lube as he went. After I was able to relax a bit, I felt him remove his fingers, only to be replaced by the head of his cock again. This time, as he pressed forward, I felt the enormous head enter me. He pushed a bit more and it almost felt like something popped inside me.

I grunted a bit, but I was no longer in pain. I felt full, but at that point, I wanted more.

"Oh yeah," I moaned. "That's it."

I could tell he was encouraged as he pressed harder, feeding another three or four inches into my now stretched hole.

"Wow, Will, you're tighter than I thought you'd be," Tony said. "You still ok?" he asked.

All I could do at that point was moan and nod.

That was when he began fucking me. He started using light, slow strokes. But as I loosened, he increased both the tempo and depth of his strokes. Within just a few seconds, I could feel his pubic hair pressing against my backside, indicating he had reached maximum penetration. I reached down between my legs passed my own balls and began caressing his, urging him deeper and deeper with every thrust.

I could only describe it as the most incredible feeling ever. At that moment, I could picture Tony's thick cock stretching every inch of my upturned ass, just like the guy I had watched in the video a couple of days earlier.

I didn't want to let go of his balls, so with my free hand, I reached down and began to stroke my own cock. I might have gotten two or three strokes off before I came in what I could only describe as the most powerful orgasm of my life. Each of Tony's subsequent thrusts from that moment on seemed to coax more and more cum from my balls.

Then, with one hard, final downward thrust, Tony shot his second load deep inside me. While I didn't feel the force of his ejaculation, I could feel a warmth spread within me. I consciously clenched my ass so as to increase the pressure and sensation of his enormous cock as he continued to empty his massive balls into my ass. At that point, I could safely say I had been fucked.

Thankfully, he didn't pull out right away. Instead, he continued to slowly fuck me until his hard-on had subsided to the point where he was no longer able to remain inside me. He allowed me to involuntarily expel him before rolling off me onto the side of the bed.

We both laid there for a few moments, completely spent.

I eventually thought to reach for a towel. Between Tony's cum and the generous amount of lube he had used, as well as my own orgasm, I was pretty much wet from my ass to my knees.

Tony laid there for a couple of minutes recovering, then he got up, wiped his crotch and began getting dressed.

"That was good," he said. "I haven't done anything like that for so long, I forgot how good it felt. Listen, I've really got to get going. Let me use your bathroom and I'll be on my way."

"Sure," I said, rolling off the bed. I could feel my legs were a little weak when I stood up. My ass also hurt a little, but the pain quickly subsided once I began to move around. The best part was that I could feel Tony's cum leaking out and running down my inner thighs.

Tony wasn't in the bathroom for long. I knew he was in a hurry to get back home, so I didn't waist much time talking. Besides, I was hoping this wouldn't be the last time he came over, even if it were just for a quickie.

For days afterward, I couldn't believe how much I had enjoyed our sex. I found myself masturbating two or three times a day to the memory of sucking his massive cock or feeling him cum inside my virgin asshole.

Unfortunately, we never hooked up again. I even worked up the nerve to call him one day, but I didn't leave a message and he never returned my call.

Amy and I resumed our relationship where we had left off, but ultimately going our separate ways. Greg also moved out and got married a few months later after he found out his girlfriend was pregnant with what turned out to be the first of their three children.

As for me, I am now twice divorced. I still enjoy the occasional mfm hook-up, but there has never been anything as remotely exciting or as satisfying as that first time with Tony.