My name is Bryan, and I'm a middle school guy taking sex ed. I was really interested at first, until I realized that they didn't cover anything useful – just a lot of biology stuff. What I really wanted to learn about was how to do it!

Tom is my older brother. He is in his second year of Junior College and lives at home. I went to him for help, saying, “Sex Ed at school is really lame – can you teach me about sex?”

“Hmm,” Tom replied, “I suppose I can – let's start with you getting accustomed to my cock in your mouth.”

“No thanks!” I shot back, “I'm no faggot!”

“That's not the point,” Tom said, “It's simply part of a well-rounded education – and its entirely between us.”

“Maybe later,” I replied, hoping for a better deal later.

For the next couple days, I couldn't help thinking about sucking Tom's cock. I'd never been interested in that, but he really got me wondering. I knew that some guys really loved sucking cock – what did they ever get out of it?

I went back to Tom and said, “Okay, I'll suck your cock, but want your promise that you'll teach me about fucking.”

“Oh, you'll learn all about fucking,” Tom assured me, “Shall we get started?”

I nodded and Tom unzipped, taking out a cock much bigger than mine. He told me to undress, which I did after he insisted that it was part of the education. Tom seemed to know exactly what he was doing, so I went along with it.

Tom told me to get on my knees and open my mouth. I did so and soon Tom's big cock filled my mouth. It didn't all fit in, but it felt strangely good. It was almost like cocks and mouths belonged together – maybe they do.

Tom told me to explore the contours of his cock with my tongue, and I found myself starting to like it.

“Now stroke yourself to erection,” Tom directed, and I began to stroke. Soon I was hard and getting very aroused. By now I was really starting to like Tom's cock.

I stroked faster and felt my climax approaching. “Don't cum on the carpet,” Tom said, “Shoot into your hand.”

After another minute I shot my load into my hand, with an unusually strong climax. “Now lick it up,” directed Tom, but I hesitated, not wanting to go that far.

“Do it – do it now!” Tom insisted, and I reluctantly complied. “I want you to get used to the taste,” said Tom. From now on every time you cum I want you to lick it up.”

I never thought sex was going to be like this, but at least I got to cum. That sure never happened at school!

I wondered why Tom wanted me to get used to swallowing cum, but I did as he told me and after a few times I found myself liking the taste and looking forward to it. It was then that I realized that the next time Tom would probably have me suck him off.

On my next lesson that's exactly what happened. Tom told me to keep myself hard while I sucked him and to hold his load in my mouth after he came. Aroused as I was I eagerly sucked him and welcomed his hot load. It tasted a little different than mine but had the same strong taste.

With Tom's load and spent cock in my mouth I stroked myself to completion, swallowing his load as I came. After catching my breath, I licked up my cum.

I didn't know why, but for some reason sucking Tom off was a real turn-on for me. I sure would never learn this in Sex Ed!

“Next time we'll try something new,” said Tom. I thanked him for teaching me.

I told Tom I was really looking forward to the next lesson but hoped that I could continue to suck him. Tom assured me we could start out each lesson that way.

For the next lesson I undressed and got to my knees to suck Tom. He told me to stoke just enough to stay hard as I sucked, but not to cum. That was the difficult part, but I struggled not to cum. Tom rewarded my efforts with his hot load, which I held in my mouth, enjoying the manly taste, and then swallowed.

Tom told me to get onto his bed and to kneel in jack-off position. As I stroked Tom put lube on his fingers and reached between my legs and touched my asshole. Nobody had ever done that before, but it felt kind of nice. Tom moved his finger around, which added to my arousal.

“Now this will be new to you but you're gonna like this – just relax and enjoy.”

Tom pressed on my hole and a finger slipped in. It was a strange feeling, but I liked it. He worked his finger in and out as I got more and more turned on. Then he pulled out and slipped two fingers in, spreading them apart, opening me up further. Then he started wiggling his fingers inside me and that sent me over the edge – once again cumming in my hand.

“That was great!” I said. This was getting better and better!

On my next lesson Tom showed me a small zucchini about eight inches long and a little over an inch thick. “You liked anal last time, so I thought we'd take it to the next level – now get ready.”

I quicky stripped down and began to stroke while sucking Tom. He cautioned me to not cum, so I just kept myself hard while sucking him to completion.

Tom praised my sucking and then told me to get up on the bed on my hands and knees, feet hanging over the bed. Tom lubed his fingers and pressed two fingers into me and spread them. Next he slipped in three fingers and spread me open further.

He pulled out and said, “Now just relax and enjoy this.” Tom pressed the lubed zucchini to my hole it slowly entered. He stopped to let me adjust to it, and the pressed it in until bottoming out.

It was different from his fingers but felt great just the same.

“Now tighten your ass muscles around it as hard as you can while I count to five, then release.”

I did so, and then repeated five times. “These are Kegel Exercises, which strengthens your ass muscles. I want you to practice this once or twice a day until you can do twenty of them.”

He had me get on my knees in jack-off position, holding the zucchini in my ass while I jacked-off.

I came a larger than usual volume with my ass filled, and once again thanked Tom for the lesson.

For the rest of the week I practiced the Kegels every day with the zucchini in my ass. After my exercises I jacked off and then clean up the zucchini for the next time. By Friday I was up to 20 Kegels and it was time to throw the zucchini out. I wondered what Tom had planned next.

On Saturday morning I was taking a shower when Tom entered naked. He took the soap from me and soaped up his hand, then slipped a few soapy fingers in me, spreading as he had done earlier. As he worked his fingers in and out, he asked, “Ready to learn about fucking?”

I nodded and Tom slipped his soapy cock between my cheeks and against my hole. By now I welcomed any entry and instinctively pressed against his cock. The slippery soap was a great lube and soon he was inside me. It felt better than the zucchini!

Tom put his hands on my hips and pumped in and out of me. “Now do your Kegels,” Tom said.

“I love your ass!” Tom said as he fucked me faster and harder. In a few minutes he thrust deep as he came.

“I'll stay in while you jack-off,” Tom said. I stroked myself off, shooting my cum on the shower floor.

Tom pulled out and washed off his cock, and then left the shower. My ass tingled from the soap, but I managed to finish my shower and dry off.

On my next lesson I found Tom laying naked on his bed. He told me to suck him to erection, but not to climax. When he was hard, he told me to lube him up and sit on his cock.

I knelt over him and slowly lowered onto him, thoroughly enjoying the entry. He told me to “ride” his cock and see if I could make him cum. As I rode him I did my Kegels, which is what I think they are for. It seemed to take a long time, but Tom came in my ass once again.

Tom said I had done well, and to jack off as I sat there. It didn't take long for me to cum. As usual I caught my cum in my hand and licked it up.

I got off Tom and we both went into the bathroom to clean up.

At bedtime Tom stopped by my bed and I sucked him off. I really enjoyed everything Tom had taught me, but I think sucking him is the best!

When I first asked Tom to reach me about sex I had sex with girls in mind, but what I've learned is SO MUCH better! I don't think I'm gay, since I'm not at all attracted to guys – just their cocks.

Is there such a thing as a straight cocksucker? If so, that's me. Then there is the part about getting fucked – I love that too. I guess that's pretty gay too.

Well, no matter – I still have to keep it secret. As much as I enjoyed Tom, I really wanted to blow other guys as well but had no idea how to safely find them. I suppose I would have to be content with Tom for now.

I sucked Tom nearly every day and twice a week practiced my Kegels on his cock. He bought me a dildo to do my Kegels other times, so I worked up to doing fifty reps. That allowed be to squeeze Tom's cock hard on every stroke. I mentally counted as I rode him, and he nearly always came between forty and fifty strokes. One time I got to seventy strokes and he still hadn't cum, so I got off and wiped his cock clean, then sucked him off.

One day Tom gave me some bad news. He had applied to several four-year universities and been accepted in two. He had not yet decided, but when he graduated from junior college he would be going to school out of state. That was a good deal for him, but it left me without his cock.

After we had a heart-felt discussion, Tom agreed to find me guys, and said he would get on it right away.

Two days later he introduced me to Ben, another junior college student. He was also graduating but was staying in town and going to work. I gladly stripped down for Ben and blew him. He really loved my work, and I have Tom to thank for teaching me to be such a good cocksucker.

Ben had his own apartment, so I ended up going to his place and blowing him several times a week. Tom also found two other guys to blow, Dan and Chris. Between them I gave blowjobs nearly every day.

While I was swallowing cum regularly, I wanted someone who would fuck me when Tom left. Once again Tom came through for me.

He found a guy nearby who was listed in the sex offender registry. Tom met with him and found that he liked to fuck boys but hadn't had any boy ass since his release from jail and didn't want to be busted again. This was perfect for me since I knew he would keep my secret.

Tom bought me a larger dildo so I could get ready for an adult cock and told me how to be discrete in visiting Mr. Lindford, the sex offender.

I was to go to the local shopping mall and meet him in the east side men's room at 5pm. I was to go to the end stall and tap on the door two times, then three. It all sounded like spy movie stuff, but I was eager for it.

On the day of the meeting I went to the mall men's room and knocked on the stall door as directed. I heard the door unlatch and he whispered, “get in here”.

I entered the stall and he stood up, telling me to sit down. I did and soon his huge cock was inches from my face. I took him in my mouth and did my very best for him. Soon he rewarded my efforts with an appropriately huge load, which I swallowed gratefully.

Afterward he handed me a paper with his address and instructions on getting there. I left, looking forward to visiting him.

I looked forward to my visit with Mr. Linford and practiced daily with the large dildo. It was quite a stretch to get in at first but each time was easier. I practiced my Kegals, rewarding myself by jacking-off when I got to fifty.

I thought about Mr. Lindford's big cock, which was very impressive to suck, but would be even more impressive in my ass. It was thicker than my large dildo, so I knew that even when I could take it easily that his cock would stretch me more!

On the night of my meeting with Mr. Lindford I loosened up with the dildo and did my Kegals, but didn't jack-off. When I removed the dildo I put extra lube in my ass, then left to meet him.

Because he was on the Sex Offenders list he wasn't supposed to be anywhere near kids, so I had to be sneaky about this. He told me to cut through the subdivision behind his house and come through the back yard and lightly tap on the back door at exactly 7pm.

I did as directed and he opened the door and motioned me in. “Did anyone see you?” he asked.

“No,” I replied.

“Good,” he replied, “You must never be seen here.”

He told me to undress and soon I stood before him, naked and erect.

“Have ever had a cock this big up your ass?” he asked.

“No, but I'm looking forward to it,” I replied.

He took me into a bedroom and had me get on the bed on my hands and knees, my ass pointing toward him.

He put lube on his fingers and started by slipping three fingers in me and spreading me wide until I cried out. I tried not to but couldn't help it.

Undeterred, he slipped in four fingers, and it felt like he was going to force his fist into me, but he stopped short of that.

He removed his fingers and the inserted something hard. I thought it was a dildo at first – much bigger than mine. He pushed firmly but gave me time to adjust.

“You're doing fine, just relax and you'll be taking it all in,” he assured me.

Finally, the widest part was in, and the rest slid in easily. He pushed it in until he bottomed out, with a bit if it still out of my ass.

“That's good for now,” he said, “We'll go for depth later – for now just hold it in.”

He had me get off the bed and kneel before him, with a hand holding the big object in place while I sucked him to erection.

The first time I sucked him it was dark in the stall, but here in full light I could see how enormous his cock really was!

When he was fully erect it really stretched my mouth open. He pulled out and said, “Are you ready for this?”

“I think so,” I said, “I know I want it!”

“Clear your ass for me,” he ordered, and I pushed the object out.

I was surprised to find that I had a full-sized cucumber up my ass! He ordered me back onto the bed and put more lube in my ass. He pressed his cock into me. I still had to stretch, and soon he filled me up. I had never had so much in my ass and I hoped I could handle it.

He began to stroke in and out. I felt completely stretched, but still tried to tighten around him. He filled me so much that it felt like there was no room for him to move, but he stroked as I tightened as much as I could, often bottoming out, which was a little uncomfortable. Finally he grabbed my hips and made a final thrust as he shot his seed into me!

“You got a nice ass!” he said, “I'm gonna be fuckin’ you a lot!”

He pulled out and said, “Your ass is really gaping now,” and he slipped the cucumber back into me, which slid in without any resistance.

He told me to wait there, which I did. He returned and took a couple of pictures of my fiiled ass, then he put a couple of long strips of duct tape across my cheeks to hold the cucumber in.

“I want you to leave that in for at least half an hour,” he said, “Now get dressed and don't let anyone see you leave.”

The cucumber was held firmly in place by the duct tape but stuck out of my ass a little because I couldn't take it all in. I couldn't sit down with it in me, so I just walked around for a while. I wondered what Mr. Lindford meant by “we'll go for depth later” – was he going to train me to take it all the way in? It did seem like it would be great to be able to fuck without bottoming out, but I didn't know how that would happen.

As I walked around the cucumber constantly reminded me of its presence. Even though I loved anal it was becoming uncomfortable.

Finally I slipped between some bushes for cover and dropped my pants. I removed the duct tape and let the cucumber slip out and onto the ground. I went home and put some soothing aloe lotion on my well-used ass.

My ass was really sore the next day, but only hurt a little for the next two days. By that time the fucking was a fond memory, and I was looking forward to the next time.

I didn't use a dildo until after my ass was recovered, and even then, it didn't feel as good. I decided that getting my ass stretched that much was no fun at all, resolved not to go back to Mr. Lindford. I didn't resume my Kegels with a dildo for three weeks, and once again could enjoy anal. During that time, I continued to blow my regulars, but invited them to fuck me in the near future. Two of them agreed, and I hope that I can satisfy my anal desires with them.

One day I got a call from Tom, who invited me to come stay with him at his school for a weekend. There was a party in which I could be the "designated cocksucker" and blow any of the guys who wanted it. He asked if I would be interested and I jumped at the opportunity.

Tom convinced my parents that he was showing me the university so I would get better grades and qualify at a good college. Before the big weekend he drove home and picked me up right after school. I sucked Tom’s cock most of the way back to the university, sucking him gently so he didn’t cum while driving. Tom pulled off at a rest stop just before we arrived and I finished him off.

He drove to his fraternity house where he introduced me. He took me to his room and showed me where I would be sleeping. Two of his fraternity brothers came in and asked I would blow them. I looked to Tom and he nodded for me to go ahead. I dropped to my knees and eagerly blew them both. They really loved my work and I was grateful for Tom teaching me so well.

Throughout the evening seven more guys stopped by for blowjobs and I loved swallowing so much cum! The next morning Tom took me into the group shower and fucked me with five other guys watching. Once he came, the others took their turn and I really loved it. It had been several months since Mr. Lindford had stretched me out so badly – I finally had recovered to the point I could enjoy a good fucking once again. Tom promised he would have more guys to fuck me tomorrow morning.
By evening Tom got me ready for my role as “designated cocksucker”. He set me up in a small bedroom with a pillow to kneel on, since I’d be on my knees for most of the night. I sucked off twenty-seven guys that night, and had to stop because I just couldn’t swallow any more cum.
The next morning Tom got me up and told that guys were waiting form me in the shower. I jumped out of bed and rushed into the crowded shower, filled with hard-cocked guys. Tom got to go first, and soon he was deep inside me. It only took a few minutes for him to cum. From nearly an hour I had dozens of cocks up my ass – one after the other shooting their loads into me. Tom stayed with me the entire time. When the last guys finished I got to my knees and held Tom’s cock in my mouth as I jacked off.

After showering I got dressed and after breakfast Tom drove me home. I owe him so much for teaching me what I really needed to know about sex, and opening up so many opportunities for me!

  To be continued . . .

Feel free to contact me with your comments or requests.
    –Bill Beaumonte (oral_guy_2000@yahoo.com)