Learning Myself Through Jeff

Jeff continued to hold the back of my head with one hand while he pumped out the remainder of his load into my mouth with the other. When he had finished, he wiped his cock across my cheeks and chin, guiding what remained of his first load to my lips and hungry tongue.

"I'm not done with you yet, but you might want to savor this last little bit," he said. As he spoke, he reached over and opened the drawer to his nightstand and pulled out a thin leather strap that had metal snaps along one side and a steel ring through the middle.

"You ever use one of these before?" he asked. "No," I said. "Isn't that a cock ring?" I had seen them used in porn flicks and in sex toy catalogs, but had always associated them with gays or S&M freaks.

"Stand up," he said. As I did, Jeff grabbed me by my cock, which was semi-hard and dripping. "This strap goes under your balls and around your cock. Put it on tightly like this, then snap it into place. It will keep you hard and help keep you from coming too fast. I'm going to go get another drink and have a smoke. While I'm gone, I want you to go and get cleaned up -- make sure that ass of yours is squeaky clean. Then I want you to put this on and meet me back here face down and ass up in this bed. And no jerking off! Understood?"

"Ok... got it," I said. I was in full lust. Although I was scared that Jeff might tear me in half trying to get that monster dick in my ass, the bigger part of me was dying to know what it would feel like to get fucked for the first time.

It didn't take me long to get cleaned up, and, in just a few moments, I was back in Jeff's room and in position. The tightness of the ring around my cock and scrotum felt good. It also provided for good separation between my ball sack and asshole, which I figured would make it easier when the time came for my fucking.

After several more minutes, Jeff finally re-appeared. "Ah, perfect," he said. "I like that. You follow directions well. Now let's check and see how tight you got that ring."

Jeff walked around behind me. Over my shoulder I could see him bend over. Then he grabbed my throbbing cock, pulling it down and back toward my ass. The next thing I knew, Jeff began sucking my dick hard from behind. The sensation was amazing, but it didn't last long. He soon released my cock from his mouth, making a popping sound with his lips. He then went back to the nightstand and fished out two dildos -- one bigger than the other -- and a bottle of lube.

"Don't move," he said. The next thing I heard was the click of the bottle cap, followed by sensation of the top touching my ass as Jeff squeezed out a few drops onto my puckered, waiting hole. Then, with that little bit of coating in place, he pushed the entire bottle cap in past my sphincter, emptying what felt like half of the bottle of cold lube into me.

"You'll thank me later for that," he said as he removed the bottle from my butt and coated the first of the two dildos. Then, without further warning, he began working the first toy into me. Although I knew it was the smallest of the three rods that would penetrate me that night, it still felt huge. After a little more force, I was relieved when I finally felt the dildo clear my opening and glide into my rectum. Jeff fucked me with it several times before pulling it out.

"You took that one pretty well," he commented. "Let's see how you do with this one." Although the second toy was about twice the size of the first, it slid in much easier. "Now we're going to see how deep you are. Let me know if it hurts."

I could feel Jeff twisting and turning the dildo as he probed deeper and deeper. Before I knew it, I could feel the base of the silicone toy pressing tightly against my hole. "Wow," said Jeff. "I'm impressed. You now have seven inches of rubber cock up your ass. How does that feel?"

I quickly turned my head to the side and reached down between my legs to feel for myself. "Um, it feels good," I said. "Good. I want you to leave that in there for a couple of minutes. In the meantime, I need you to go to the bar and bring me my drink."

"Um, what? You mean you want me to walk out there and get your drink with this thing inside me?" I asked stupidly. "Yeah, that's exactly what I mean. And don't let it slide out either," he said.

I stood up and gingerly made my way out of the room. As I walked down the hallway, I could feel the dildo shift inside me. It was actually a pleasurable sensation. Even though it was tapered at the base, I still clenched my sphincter so as not to let it drop while I walked. I also became aware of the stream of pre-cum that had leaked out dick and was now forming sticky strings along the insides of my thighs.

When I returned, Jeff was standing in the middle of the room. He had also put on a cock ring, which made his manhood look even more pronounced. "Are you ready for the real thing?" he asked. I nodded. "Good, now I want you to come over here and suck me until I'm rock hard. But first, we need to get that plug out of your ass. Turn around and bend over."

I sat his glass down, bent over and placed my hands on the edge of the bed. After Jeff had removed the toy, I turned around and sat down where I was presented with Jeff's cock. As I began sucking and stroking his cock, I noticed that my stomach felt empty -- almost as if I'd just had a huge bowel movement.

After a few minutes of sucking his cock and licking his balls, Jeff tapped me on the shoulder and motioned for me to get up on the bed. I immediately resumed my doggy position and waited as he applied more lube to me, as well as a generous amount to his own cock.

This was it, I thought, as I felt him run the head of his dick along my crack. With his cock in hand, Jeff positioned the tip at my opening. He entered me in one quick motion, which caused me to grown and lurch forward a bit. "Wow, that hurt," I blurted.

I quickly reached back to in an effort to get him to pull out, but he brushed my hand aside and pressed on. My ass felt like it was on fire. Next, I felt a 'pop,' followed by the sensation of feeling extremely 'full.' With my ass still burning, I suddenly became very aware of my breathing, which was rapid and shallow. I was also moaning audibly.

Sensing my obvious distress, Jeff paused. "Do you want me to stop? Just so you know, you've got the hard part behind you already. I've got the head all of the way in," he said.

I remember thinking to myself, "What the fuck? That was just the head?" It felt like I'd been rammed by a telephone pole.

"Gimme a second," I said through my groans and pants. "I think I'll be alright. Just give me second."

Jeff kneeled there patiently as I raised up and grabbed my drink from the nightstand. After gulping it down, I took a deep breath and motioned for Jeff to keep going. It's amazing how much courage a little taste of alcohol will give you.

Jeff then began to fuck me using short, gentle strokes. Slowly, I began to feel the pain and discomfort give way to that full, more pleasurable feeling I had gotten earlier while walking with the dildo in my ass. With the pain giving way to pleasure, I was now determined to stay along for the entire ride. "That's better. It feels good. It doesn't hurt anymore," I said motioning for him to continue.

"Deeper? You want more?" he asked. "Yes," I said. "Fuck me all the way. I want you to fuck me hard! I want to feel you cum inside me!"

His strokes became longer and deeper. I knew I wouldn't be satisfied until I had taken every inch. I began to push back hard, impaling myself deeper and deeper with each stroke.

Then, just as I was sure he was ready to climax, he stopped.

"Turn over," he said. "And hand me a couple of pillows."

He pulled his cock out just long enough allow me to turn, then he grabbed my legs and raised my lower body off of the bed. He placed the pillows under my low back. With my feet and calves now dangling over his shoulders, he plunged his cock back into me, picking up the pace where he had left off. I'd never even considered two guys could fuck in missionary position, but it felt amazing.

He was sweating and breathing heavily. I could tell he was getting closer. As he fucked me, I stared at my cinched cock and balls, which were angled directly at my face.

Suddenly, he pushed into me hard. I could feel his body spasm as he began releasing his second load of the evening -- only this one was going straight up my ass. He continued to fuck me using hard strokes at first, then he tapered off as his orgasm subsided. With his still hard cock inside me, he grabbed my dick and began jacking me. Within a matter of seconds, he had me coming in large spurts. The first shot hit me across the mouth and some went up my nose. The rest soaked my neck, chest and stomach.

When I finally came to my senses, Jeff had pulled out and was sitting beside me on the bed. As I sat up, I tasted the splash of my own cum that had run down into my mouth and along my chin. I could also feel Jeff's cum oozing from my well-worked asshole.

"That was fucking incredible," I said. "Wow!"

"You're welcome," he said laughing.

Epilogue

Jeff and I only had sex a few times again after that night -- each time was as satisfying as the first. Not surprisingly, I did end up getting his firm's account -- which eventually led to a promotion and ultimately me starting my own shop. Jeff was among my first investors -- and -- my biggest!

We remained good friends until his untimely death from a car accident. We even went on a double-date once with two ladies that worked at his firm -- one of which I ended up marrying (and subsequently divorcing) several years later.

It's not every day that special people like Jeff come into our lives. If nothing else, he taught me the importance of putting one's fears and preconceived ideas aside, and the pleasures and rewards that can come from it.