My Downfall Is Almost Complete

My downfall is almost complete but I get ahead of myself. I had just graduated from high school and would start college in September. I worked at a summer job at a printing company. The other guys were all older, mostly late twenties and thirties. Bill took me under his wing and showed me the ropes. A few days later he invited me over to his place. We had a couple of beers each and watched a movie. He said next time bring your swim suit and we can use the pool.

I headed back the next Saturday. After changing into our suits we cooled off in the pool and then had a beer. "Nice place, Bill. How can you afford this?"

"My dad was a very smart investor. When he died five years ago I received a large inheritance. I bought this house. Nice pool isn't it? Ready for another beer?"

I figured out later that he put something in that beer. A little while and I was feeling very mellow and relaxed.

"Have you ever had a massage, John? Come on inside. Here, lay down on this bed. Oh, better take off your suit, it will get the bed wet."

I laid on my stomach. Bill straddled me and kneaded my shoulders. "How does that feel?" "Really good." "I used to be a part-time trainer for a swim team. Learned how to unwind tight muscles."

He worked his way down my body and then started massaging my legs. I was totally relaxed. He kneaded my butt. This was a new but nice feeling.

"You have a nice slim body. Tight ass. Now turn over and I'll do your front."

I lay there totally nude with my eyes closed. Bill straddled me and massaged my hairless chest and tweaked my nipples.

"Want me to massage this?" he asked as he took my limp cock into both hands. I didn't respond which he took as a yes. Why not, I was in a very mellow mood without a care in the world. Very quickly my cock started growing.

"Oh, you've got a big one! A really big one. Very nice. Do you have a girlfriend, John?"

"No, no one special," I admitted.

"Has anyone rubbed your cock like I'm doing? Do you want me to keep going?"

"No. I mean, yes, keep doing it. It feels good." Actually I had never kissed a girl, much less anything else.

Bill added some lotion and started jerking me off. My cock was big and stiff, the head became very sensitive. All of a sudden I felt a funny sensation, a good feeling, and cum shot out of my cock and landed on my chest.

"Did you like that?"

"Yes," I responded, almost as in a dream.

"How about you doing it for me?" as he pulled off his swim suit. His stiff cock popped up. It was big but not quite as big as mine. I poured some lotion on his cock and for the first time ever touched another guy. Doing what he did to me I stroked his cock. With my other hand I gently felt his balls. He coached me on what to do until he squirted all over my hand.

"Well done, John. That really felt great. Come on, let's get in the pool and cool off. We don't need suits, no one will see."

I stumbled out there with Bill helping. Wow, those beers really hit me. We played in the water and then sat by the pool drinking another beer.

"You have a great cock, John. As good as the guys in the porn videos. Let's go inside and I'll show you."

Bill started up an X rated DVD with two guys having fun together. I had seen some porn before but not gay stuff. Bill sat next to me and played with my cock as we watch the guys do 69 blowjobs.

"I would like to suck your cock, John. If I do, would you then do me?"

Before waiting for an answer he bent over and stuck the head of my cock in his mouth. This was another new experience for me. I loved it. A few minutes later I came. Bill took the first load in his mouth and the second in his hand. He then held his hand to my face.

"Here, taste your cum." I stuck out my tongue. "Very good, John. You really are a fun guy. Now come suck my cock."

It was another first for me. I copied Bill's technique and he coached me as I went along. 'Here it comes, John. Suck it all." I took all four squirts in my mouth and felt real proud of myself.

"Excellent, John. That was a terrific first time. I'm glad you swallowed."

********

Later that week Bill asked me what I had going on Saturday. I was pretty sure we would do a replay of the prior Saturday. Fine with me.

A couple of beers (and something added, I think), and I was again feeling very mellow. Bill give me another back massage. Then like before he moved downward, rubbing my legs and then up to my butt.

"Spread your legs. You have such a nice smooth ass. Like a girl's. I want to play with your anus," as he placed the tip of his finger there. I felt something cold as he slid a lotion-covered finger into my hole. "Feel that?" as he massaged my prostate with his finger. "Yeah, that's a really weird feeling." He added a second finger and teased my tight hole. It was snug and uncomfortable. "I'm going to put a butt plug in you. It won't hurt but will loosen you up some. Later I want to fuck you in the ass." He pressed the plug partway in, then back out. Back and forth until it was fully inside. "That should stay in position unless you try to push it out. Don't."

"Have another beer. Then we'll go get something to eat." "With this thing in me?" "Yeah, get dressed. No one will know it's there." I was in a mellow fog and didn't object. We went to a local restaurant. Sitting in the booth I couldn't help but squirm around. "Try not to do that, John. People will notice." The plug was massaging my prostate and making me horny.

Finally we headed back to Bill's place. I went to the bathroom and pulled out the plug. "Get on the bed, butt in the air." He pushed against my anus but his cock head only went in halfway. Back out, then pushed again. After about six pushes the head slid in as I adjusted to its size. A few more strokes and his cock was in most of the way. I gasped as his cock passed through into my rectum. I felt the tightness around his cock and an unfamiliar fullness. Then he started stroking in and out, finally fully sinking up to his balls in my tight ass. I moaned in sync with his thrusting.

"Terrific. I didn't know if you could take it all. Your ass is so tight. You doing ok?"

"Yeah, it's really a good feeling. But it hurts some. Don't move until I get used to it."

Bill fucked me for at least ten minutes before pounding hard. I felt warmth as he held my ass and pumped spurt after spurt deep into my rectum. I was sorry when he pulled out.

********

Two days later I was back in his bed.

"I really like how your cock feels in my ass. Just keep fucking me, nice and slow." I relaxed my body and concentrated on the fabulous sensations. So nice. Each stroke created a tingle as his cock head rubbed my prostate. I had a mellow, glowing feeling as his cock slipped in and out of my slippery channel. All too soon he slammed into me and ejaculated. I again felt a sense of loss as he pulled out. I wanted more.

"Nice. Very nice. I'd let you fuck me but your cock is just too big. You would tear me up. But how about instead I give you a blowjob?"

"That was really good," I thanked Bill afterwards.

"I have some friends who would probably like to fuck you," Bill suggested. "Interested? I could set up something."

********

"John, I'm having a party Saturday afternoon. A few people over to watch the baseball game. Come if you can. We'll have fun afterwards."

A couple of guys from work came plus other people I had not met. We drank, swam, made small talk. Played pool. Ate some good BBQ. By early evening most guests had departed, leaving me and Bill and three guys I didn't know. We sat around on the pool deck. I figured the fun was about to begin and I was ready.

"John, take your clothes off. Show my friends your cock. Rub it and get it hard."

I had always been proud of my big cock. Growing up I knew it was much bigger than average. So I enjoyed showing it off to Bill's friends. It was hard as a rock.

"Nice cock, huh guys? OK, bend over the table and show us your ass. Spread your cheeks and show my friends where I put my cock last Saturday. You want it in your ass again? I told my friends what we did. Guys, you should have seen us in the restaurant. John squirming with the butt plug massaging his prostate. I'm surprised he didn't cum in his pants!" he laughed.

"Here's your butt plug. Show us how it fits. Yeah, push it in and out. Get your ass stretched and ready for us. Keep it in and walk around."

My cock jutted out in front. I was getting horny with the butt plug and started playing with my cock.

"Bend over. Show us the plug. Good. Now pull it out and use this dildo. Here's some lube."

Bill handed me a large dildo. I spread lube on it and positioned the tip at my anus and pushed until it was fully in my ass. It felt almost as good as his cock. Without prompting I pushed it in and out. Bill told me to jerk off while I fucked my ass with the dildo. I stood in front of the guys and performed. I stroked my cock in tempo with the dildo. A few minutes later I shot cum several feet onto the pool deck. The guys congratulated me on a great performance.

"Now it's our turn. You won't need that dildo anymore."

I don't remember the names of the guys. One after another they stuck their big cocks in me. I humped back, trying to get each one in as deep as possible. My rectum was super lubricated with all their cum. After the last one came someone took pictures of my stretched hole with cum streaming out. Bill was the last to fuck me. His cock slipped in easily.

In the morning I awoke with a very sore ass.

"John, you hoped you liked last night. You were great. My buddies loved fucking your tight ass."

"I had a great time - four cocks in me! I'm glad you invited your friends, I really like the feel of cocks inside me. But they stretched my ass. It still hurts."

"It will go back to normal. You just need to be fucked more. You have a cute face and a nice slender body. Not to mention a great ass. Plenty of guys would like to stick their dicks in you. I intend to let them fuck you - if they have money."

"What do you mean? You're going to whore me out?"

"You bet. You'll make some money. Besides, we got good pictures of you being fucked and your ass leaking cum. If you don't cooperate those photos will be all over Facebook. I don't think you want that."

The next weekend Bill took me to a local bar and grill. I was very uptight. Bill suggested I drink some of his drug so I wouldn't be so nervous. There were several guys waiting for me in the back room. I sucked some cock. Some pictures were taken. I stripped and laid on the carpet, ass in the air. One after another I was fucked. I was relaxed and zoned out and let it happen. My ass was sore but not as much as before. Afterwards Bill gave me $600, my share.

That became the routine for the next several months. I was making over $2000 per month. After that party with Bill's friends I figured it didn't make any difference. I sucked cock and took cocks up my ass. I preferred ass fucking. My mouth would start to ache after a couple of blowjobs. I experienced cocks of all sizes. Some small, most medium. A few like Bill's but none as big as mine. I was addicted to cock and looked forward to each time.

Bill said next weekend a black guy with a huge cock would be there. Many women wouldn't let him fuck them and none in their ass. Bill said he would charge him $500 to try me. I had sucked and fucked some fairly big cocks by that time so figured what the hell.

Hell it was. The plan was to let others fuck me first and get my ass opened up. Then with some extra lube I should be ok. That was before I saw Jamal's cock. I fondled it with both hands and estimated it was twelve inches long. And an amazing 2 ½ inches in diameter. The biggest I ever had was less than two inches and that almost split me open. I tried to suck it and could get only the head and a couple of inches of shaft in my mouth.

Bill squirted some stuff into my ass. He said it would numb it up. Then he added a huge amount of lubricant. I emptied the rest of the tube directly on this guy's cockhead. I knelt on the floor with my ass up. Jamal pressed the head to my hole and pushed. Nothing happened. He pushed harder and I could feel my anus open up slightly. I pushed back like I was taking a crap to relax my anus muscles. After almost a minute the head finally popped in. It hurt like hell in spite of the numbing stuff.

Over the next several minutes my ass was progressively split more and more open until about eight or nine inches was inside. Then he started fucking me with each stroke going in deeper. My insides were hurting as his cock went past my rectum and into my colon. I felt stabbing pain with each stroke. I struggled to get him out of me but he held tight to my ass.

"God damn, this motherfucker took it all. Somebody take some pictures." About this time I fainted. It didn't matter. Jamal continued fucking me until he filled me with a ton of cum. Pictures were taken of my gaping asshole with cum and blood seeping out.

Bill took me back to his place and had me soak in his tub for a long time. Then he steered me to a bed. I was exhausted and instantly fell asleep. In the morning I could barely get up to take a piss. My stomach hurt. My ass hurt. There was blood on the bed sheets.

"Bend over, John. Let me see your ass," Bill said. "Damn, guy, your asshole is still gaping open. I thought it would have closed by now."

I took a shower and felt back there with my fingers. I could easily put three fingers in my ass. It hurt to sit so I laid back down on the bed. I awoke several hours later feeling somewhat better.

Bill looked at my asshole. It had mostly closed. "I think you'll be ok, just give it some time. I had no idea his cock was that big. But it was too late to back out. I'm going to give you all of his $500."

I wasn't fucked by Bill or anyone for the next two weeks so my ass would heal up. When we did try it Bill said my ass was much looser than it had been. It had not fully returned to normal.

"That will be a problem, John. Most guys that would fuck you are my size or smaller. You are definitely stretched. I don't know if you will ever again be tight enough. But maybe guys with bigger cocks might be interested. Guys like that black guy."

"You can't be serious. That guy probably ruined my ass and you want me to take on more like him?"

"Just think about it. If your ass is already permanently stretched it won't matter. You should be able to take big cocks without a problem or further stretching. Why not give it a try?"

Bill put out the word that his guy, me, liked big cocks. The bigger the better. Several guys expressed interest. Although I hated to admit it bigger cocks now fit fine. The biggest I previously had was seven inches, about what Bill had. Several guys now had eight inches or a bit more. They easily slid into my ass. Two guys said they had ten inches. We talked about it and I decided to give it a try. Both guys were a bit snug but able to bottom out in me. They loved my ass. Their cocks were big but didn't hurt like Jamal's.

"John, I got a call from Jamal. You know, the black guy with the twelve-inch cock. He wants to fuck you again. What do you think?"

I didn't want to be stretched more but he had already been there once. And part of me saw it as a challenge. I agreed. His black cock was as big as I remembered it. Maybe bigger. He taunted me, saying he was going to make me his bitch now that I was properly broken in. I played along.

Bill lubed me up. Jamal pressed his cock head at my anus. It still took more than a minute of slow pushing just to get the head in. It hurt but not too bad. The rest of his cock slid in much easier than that first time.

'Damn guy, I guess last time I really did a number on your asshole. Your ass now fits my cock like a glove."

He fucked me hard for at least ten minutes. I pushed back on each stroke. All twelve inches were inside, reaching deep within my bowels. I challenged him to fuck me harder. He did. Each thrust caused momentary pain deep inside me but I loved it. I felt his warm sperm fill me up. He pulled out leaving my ass gaping open, his cum running down my ass. Jamal said he was going to put out the word to some of his hung brothers and I should get my ass ready.

During the next three months I fucked a dozen guys all with cocks like Jamal. Bill gave them a discount. One night four guys had me, most more than once. I liked these huge cocks. One guy, showing off, forced his hand into my ass, fisting me. That hurt like hell and I tried to fight him off. He laughed as he forced my sphincter wide open. Twisting and pushing, he first worked four fingers in me. Then his hand up to the knuckle. Worming his way in he stretched my ass to the limit. I groaned with pain as his entire hand penetrated. My ass was throbbing but somehow I liked it. I felt his hand flex and massage my prostate. I came with a shudder. My ass gaped obscenely after he pulled out. The next guy complained I was too loose for his cock. My ass leaked for hours afterwards.

Bill took me back to his place and fucked me. I tried to tighten up my hole but he said I was much too loose. He said we should hold off a while on the really big cocks. Bill invited his three friends over the next week. They all fucked me. I could barely feel their cocks in my ass. Bill suggested I take on two cocks at once. I squatted over one of the guys and dropped down on his cock. Bill moved behind me and pushed his cock in next to his friend's cock. It actually felt good and they both came.

Bill said he didn't think he could get me much work anymore. Not many guys have really big cocks and would pay to fuck me. My ass was much too loose for average cocks. I had outgrown my market except for Jamal and his friends.

I now had no income. Jamal said he would pimp me out to his brothers. He takes me to parties. I'm the white boy fuck toy. Most times I'm used by five or six guys, usually more than once. The guys he invites all have really big cocks and keep me loose. Even a day later my ass leaks in my underwear.

Jamal set me up to do a porn video to make more money. I sucked three big black cocks and took them in my ass. After I was full of cum one guy fisted me. It went in much easier than the first time and he kept pushing until half his forearm was embedded in me. Something hurt inside but I wanted him to continue. Jamal said I looked great with this guy's black hand and arm in my white ass. He paid me $400 for the video shoot.

I performed in lots more. Young white boy with tight ass takes on huge black cocks. After they finished fucking I would be fisted. I actually took one guy's arm up to his elbow. Jamal said that was the most amazing thing he had ever seen. He started inviting guys to watch, charging them ten bucks each. He wants me to take two cocks at once. Next time. My videos are very popular.

I still see Bill and his friends from time to time. They don't fuck me since I'm so loose but I'm good at sucking cock. I'm obsessed with huge cocks and fisting. I wonder how deep an arm can go. When I'm not being fucked I watch my porn videos. I enjoy being a star. I know what I'm doing has totally wrecked my ass. But I can't help myself.