I'm Brent, and my older sister, Sandra taught me some amazing things about sex when I was thirteen. She was a couple of years older and must have been very active sexually because she knew a lot about what feels good to guys. As a gymnast, she was amazingly agile, and encouraged me to do stretching and bending exercises to increase my flexibility.

At first I could see no point to it, and then she told me that most boys would suck themselves off if they could, but most just cannot. I didn't believe her until she showed me some internet pictures of guys actually doing it. They had much bigger cocks than I did, but Sandra assured me that my cock would grow, partly from changes during puberty, and partly from pulling it when I jacked off.

She told me that with practice I could suck myself off too. I told her I wasn't so sure and she said she would help me if I liked. When I asked her how she would help she just said, "Tomorrow after school I'll show you."

Our parents both worked and didn't get home until more than two hours after we got home from school. The next day I hurried home, anxious for what she had in mind for me. She told me to get undressed and lay on my bed. I stripped down and got onto my bed as she walked into my room. It felt a little odd being completely naked in front of my sister, but when she touched my leg, I knew I liked it.

I was semi-hard and she said, "That's a start – we'll have to work on that."

She told my to lift my legs as high in the air as I could. I did but failed to see the point of it. Then she grabbed my ankles and pulled my feet over my head. She kept on pulling until my cock was about six inches from my mouth, and I said, "That's as far as I can go!"

She stopped and said, "I want you to do this kind of stretch every night before you go to sleep. In time you will be able to bend further, and as your cock grows, soon I'll be watching you suck yourself off!"

She told me to hold onto my legs so I stayed in that position, while she reached to my cock and began to stroke me. I quickly got hard and Sandra said, "I'll stroke you to climax, and when feel you are getting close, just open your mouth and I'll squirt you into it."

I had no idea what cum tasted like, but I trusted her, so I went along with it. Sandra massaged my balls as well, adding to the excitement, and then ran her fingers along my ass crack and stopped at my hole. She gently rubbed it while asking, "Like that?" to which I quickly agreed.

"Most guys do," she said, "But they rarely admit it. Being honest about what feels good is really important!"

She let go of my cock and told me to continue stroking – she would be back soon. I stroked my cock with one hand while trying to keep my legs in place with the other. Sandra returned with a bottle of lube. She put some on my hole and it felt cold, but when she touched me there again it felt great!

She moved the tip of her finger across my hole and gently pressed on it, while continuing to stroke me with the other hand. "I'm getting close," I said.

"Open your mouth as wide as you can," she said, and I did, not sure this would work.

Soon I was cumming and Sandra's aim was good – most of my load when right into my mouth, with a little bit splashing on my face. I wondered how many times she had done this before.

As I came, she pushed her finger into my hole, which felt wonderful!

Sandra put my legs down and I rested. She left to wash her hands and when she came back she said, "See, no mess – just a little on your cheek."

I wiped the cum from my cheek with a finger, licking it clean. "All gone," I said. Cum had a funny taste – unlike anything I had ever tried. It was strong tasting, but I kind of liked it, and swallowed.

We both laughed, and Sandra asked if I liked what she did with her finger. I told her I loved it and wanted her to teach me as much as she could and that I would always be cooperative.

She told me that my homework was to stretch like I just did every bedtime, and to practice jacking-off into my mouth. That was a homework assignment I didn't intend to miss!

That night I worked on stretching as Sandra had instructed. I found that if I lifted my legs up over me and was able to put my bare feet on the headboard, I could "walk" them down farther, giving me a little more stretch. I pulled on my cock, wishing Sandra was there to assist, but just thinking about it was arousing enough, and soon I came. I missed my mouth, but shot my load all over my face, but it was good. I put my legs down and rested a bit, intending to get up and wash my face, but I drifted off to sleep before I could.

I woke of the next morning with my dried cum on my face. As I rushed off to the bathroom before my mother saw me, Sandra was coming out and greeted me. She looked right at me and pulled me into the bathroom. "Let me take a closer look," she said, pulling me next to the light.

"I see you missed your target," she said, "But that's alright – you'll get better with practice." She left me to get cleaned up. I was surprised that she recognized dried cum on my face but realized that she had a lot of experience. I was glad Mom didn't see me like this.

That afternoon I rushed home again, eager to see my sister. I stripped down and lay on my bed, stroking myself to erection.

"I see that you are filled with anticipation," she said as she walked in, "Now see if you can get into position on your own."

I brought my feet up over my head and "walked" down the headboard, which impressed Sandra. She told me that I'd earned something special, and squirted lube on my hole. She told me to stroke myself while she assisted and with one hand she massaged my balls and with the other she put one, then two fingers into my hole. She pushed in all the way and then began to wiggle them. I barely got my mouth open before I began to cum – Sandra really knew what she was doing!

This time most of my load got into my mouth, with just a splash on my chin. I went to wipe it with my finger but Sandra stopped me. "From now on," she said, "Any cum on your face has to dry there."

"But Mom could see," I protested.

"Don't worry, little brother," she said, "I won't let you get in trouble – you can wash it off before she gets home. I like to see dried cum on your face."

"Why?" I asked.

"I think it's sexy," she said.

"It turns you on?" I asked, and she nodded.

"How does a girl jack-off?" I asked. Sandra explained that she just fingered her clitty. I asked her to show me and she invited me to her bedroom. Still naked, I sat on the edge of the bed while Sandra lay on the bed with her legs spread. She slipped a couple of fingers inside her and got them wet, then began to rub herself with her wet fingers.

Soon she was moaning loudly and her back arched for a bit, and then she went back to rubbing herself. She began to moan again and then stopped. "Did you cum?" I asked and she nodded.

"Twice!" she said, smiling. I was learning that a great many things were different for girls.

I continued to practice my stretching every night and Sandra assisted me after school each day. After a while she stopped fingering me and used dildos and vibrators on me, which was an entirely new feeling that made me cum even more!

On my birthday she gave me a special present. I opened the package and it said, "Vibrating, expandable butt plug."

Sandra explained that when she wasn't there to assist that I should lube it up and insert it. Then I could pump it up by squeezing the attached bulb, and then turn on the vibrator, adjust it to the speed I liked.

I looked forward to trying it tonight, but for now I wanted Sandra's assistance.

A lot of my friends didn't get along with their sisters, but Sandra and I were as close as any could be.

By the time I was fifteen my cock had grown and I could get the head in my mouth. I was anxious to show Sandra and she assisted by inserting her largest vibrating dildo into me. My mouth around my cock head felt wonderful – so much better than stroking. Sandra worked the dildo in and out of me and soon I came into my mouth.

It felt better than anything before, and I thanked Sandra for all she had done for me.

Now that I could suck myself off I did it as often as I could. I liked the feeling, but I also liked swallowing my cum. It knew it was very taboo, and that made it all the more desirable to me. I wondered what it would be like to suck someone else. That was especially taboo, and maybe that's why it interested me. Of course, it could be risky. Sucking myself was completely safe – nobody else knew except for Sandra, and she wasn't talking. Then it hit me – maybe she could find someone for me to suck who would be safe.

She was surprised when I asked her, responding, "I suppose you've just developed a taste for cum, and want some more."

"Maybe that's it," I agreed, "But really want to try it on someone else, but I don't want them to know it's me."

"That could be complicated," Sandra said, "But I have an idea. Mike, my boyfriend has been begging me for a blowjob."

"And you wouldn't do it?" I asked.

"You like it, not me," she said. I let it drop at that.

"In order for Mike to not know it's you, he can't see you," she said.

"How about if you have him over and I wear a ski mask when I suck him?" I said.

"It can't be here, or he'll figure it out. The ski mask is a good idea though, but let's do it at his place," she suggested.

"Works for me," I said, "Just tell me when."

Two days later I arrived at Mike's after school, as Sandra had arranged. She said she would have him aroused and ready for me. I texted her to let her know I was there, and she said she would come to the door. She opened it and let me in.

"I'll take you to the bedroom where you can suck Mike off," she said, "But first put on your ski mask."

"Shit!" I said, "I forgot it."

"Got an idea," said Sandra, "I'll blindfold Mike and you can do him that way. Come stand outside the bedroom door until I call you but stay out of sight."

I followed her down the hall and stood just outside the bedroom door as Sandra blindfolded Mike and gave his cock a few more strokes. Sandra called me in, and I climbed up on the bed where Mike was laying. I took his cock into my mouth and it felt wonderful. It was nothing like sucking myself – it was the actual sensation of the cock in my mouth that felt good – it seemed completely natural – like cocks and mouths were supposed to be together.

When I sucked myself I usually had just the head in my mouth, but now I could put most of Mike's cock into my mouth. It felt strange and wonderful as I felt him touch the back of my mouth, causing me to gag. Normally that would have been unpleasant, but this actually was nice, and as I sucked I found myself pressing my nose to his body, forcing his cock in all the way. All the time Sandra was kissing him, so he knew it wasn't her that was sucking him – just some mystery sucker. I liked being that mystery sucker and hoped I could do more of this.

All this was a wonderful adventure for me – an adventure that was cut short when Mike came. I'm not complaining – I really wanted to taste his cum, but I hoped it would take longer. I held him in my mouth while he finished pumping. Before pulling off Mike I looked up and was horrified to see that he'd taken off the blindfold and could clearly see me! I felt like my life would be ruined!

Mike smiled and said, "Thank you Brent, and thank you Sandra for bringing you brother over to suck me – I hope you'll be back."

I could think of nothing to say, so I just backed off and left. When I finally got outside I realized that I still had a mouthful of Mike's cum, and swallowed. As I traveled back home, I realized that I didn't mind so much that Mike saw me – in fact that was kind of hot – if only he can be trusted to keep my secret. I wanted to suck him more.

When Sandra got home, she came to see me, and said, "I swore Mike to secrecy and told him if he ever told anyone we were through."

I thanked Sandra – she was a wonderful sister. "I really liked sucking Mike," I said, "You suppose I could do it again?"

"Mike asked about that too," Sandra answered, "I told him I'd try to talk you into it, so don't seem too anxious – he'll appreciate it more if you make him wait." She obviously knew how to keep a boy under control.

I sucked Mike the next week, and once the following week. Then Sandra told me that she was going to start her period and didn't want Mike getting interested in other girls, and asked, "Would you suck him as often as he wants it?"

"Sure, but shouldn't I make him wait for it?" I asked.

"Normally yes, but not in this case," Sandra explained, "I want you to keep his desire level low so he doesn't look around for other girls." Sandra was a clever girl – guys often complained how their girlfriends nearly ignored them when they had their period – Sandra was giving Mike an alternative way to quench his desire. I agreed and she gave Mike my cell number so he could text me for service.

For the next week I sucked Mike every day after school, and Mike asked if I would suck him other times as well.

"What about Sandra?" I asked, "Shouldn't you be with her?"

"I will be, but need more," Mike replied, "But let's just keep this between us."

I understood because I usually sucked myself off twice a day, so I was sure that Mike needed more than Sandra would give him.

I continued to secretly suck Mike a few times a week without Sandra knowing. I asked her to tell me when she was starting her period, so I could take care of Mike, pretending that I'd been looking forward to it for weeks.

This was a really nice arrangement, but one day Mike and Sandra broke up, and I thought I'd be cut off from Mike's cock. A few days later he texted me, "Would you still suck me even though I'm not with your sister any more?"

I agreed and stopped by his house after school but didn't tell Sandra about it. Soon she had a new boyfriend, Ted, and forgot all about Mike. In a few weeks she asked me if I'd be interested in sucking him, and I quickly agreed. This time there was no need for secrecy, so she just had Ted come to our house and got him aroused before calling me in to suck him. Sandra had her blouse open and bra pulled away from her breasts. Ted played with her tits while I sucked him and I was glad to receive his load.

Sandra told Ted that we could do this from time to time, but especially during her period, when I would do him in private.

Now, five years later Sandra has had a few more boyfriends, and I continue to suck them all, though she doesn't know it. I still suck myself off and am forever grateful to Sandra for teaching me so much about sex and giving me an ever-increasing stream of cocks to suck.

Everyone should have the kind of sex education I had!

Special thanks to my online friend Danny Ross, for inspiring this story

  To be continued . . .

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