Teaching my Nephew

I invited my nephew who is in college to accompany me on one of my business trips.  He and I have always been close and affectionate and in the years since he entered college, heʻs gotten more physically affectionate with me -- long hugs and shoulder rubs.  Heʻd tell me about girls and guys he was interested in getting to know better, and heʻd always ask me for advice. He seemed very comfortable with the label “bisexual”. This trip of mine was only a couple of nights during his college break, so we could catch up as the meeting schedule was light.  We checked into the hotel, then hit the beach for a couple of hours. We came back and showered and were lounging around in our hotel bathrobes.  Out of the blue he asked me if I could give him some sexual advice. I told him that I would be happy to.  “Do you masturbate?” I told him that I did. “When did you start?” I told him that I was 9 or 10 when I first discovered pleasuring myself.  He wanted to know how I found out. I told him that I would rub my cock against my underwear until I came, long before puberty. It was years later that I was able to ejaculate.  I asked him why he wanted to know, and he told me that he was thinking about masturbating, but wasnʻt sure if it was okay for him to do it or not. He told me he didnʻt get the point of masturbating.  I asked him if he had ever seen porn of men ejaculating. He shyly said yes, but that it made him feel uncomfortable and it didnʻt look appealing to him because it looked fake and rehearsed. I asked him if he understood physiologically what happens.  He told me “yes and no,” and he was hoping I could explain it to him or teach him how. I thanked him for asking me and told him I would be glad to show him. I asked him if he was still a virgin and he said he has played with his girlfriendʻs pussy but did not let her play with his dick because he wasnʻt comfortable.  I expalined that masturbating was a way to find out what he was comfortable with and what felt good to him, which he could then explain to whoever he was dating. He seemed excited. “So, how do YOU masturbate, or jackoff?”  he asked very matter-of-fact. “Well, Iʻm not wearing any clothes under this robe, so do you mind if I just show you?”  “Sure,” he replied, and he didnʻt seem nervous or uncomfortable at all. I opened my robe to show him my cock. “So you know how a cock works, right?  Youʻve gotten hard before.” “Yeah, but itʻs always embarrassing.”   “Itʻs a natural reaction that you can calm, or continue to excite by touching and rubbing your cock.  So some parts are more sensitive than others, like the head and right underneath the head.” The most nerve endings are there, but other parts can feel good too, including your balls.  Sometimes, just exploring your body and touching yourself in different places helps you to find out what you like.” I ran my hand over my stomach and chest and then up to my neck and down my arms, between my thighs.  I felt myself start to stiffen. “Ooh, youʻre getting hard.”  “Yep, thatʻs what happens. You donʻt even need to start playing with your dick right away.  Why donʻt you try touching your body and see what you like?” He opened his robe and I took it from him so he was sitting there on the bed naked.  I removed my robe completely and sat facing him. “Now, copy me,” I told him, and gently started to caress myself, my neck, shoulders, arms, chest, I paused to draw little circles around my nipples.   “How does that feel?” I asked him.  “Nice, but Iʻm not getting hard.” “Donʻt worry, itʻs not about getting hard, itʻs about enjoying the sensations of your body.  Now try this.” I began to run my hands down the length of my legs, from my feet up to just below my balls. “The insides of your thighs are also sensitive.”  I rubbed the inside of my thighs, and he copied me. His breathing was getting heavier and I knew he was getting aroused. “Now...the cock. Just touch it gently and feel your fingers brush lightly against the skin.”  He slowly began to feel his cock. “Hmm the top part -- I donʻt feel as much as the underside.”  “Where does it feel the best?” I asked. He rubbed his palm against the underside of his cock. “This feels good.”  I imitated him “Yeah, thatʻs good alright.” I watched as his cock began to come to life and fill out. “There, youʻre getting hard now.  It should start to feel even better.” He continued to rub his palm against his cock and his breathing got more intense. I went into the bathroom and came back with some body lotion.  “Here, use some of this.” I squirted a gob of it into his hand.  Copying me, he rubbed his hand to warm the lotion. “Now, grab your whole cock and slide your hand over it, just like you were fucking a pussy.  Thatʻs kind of what it feel like.” “Oh, that feels really good!” He suddenly got really hard and started to panic. “Something feels wrong. I feel like Iʻm going to pee.”  “Take a deep breath,” I told him. “Inhale deep, an relax, pull the energy away from your cock and up into your head.” He followed my instructions. In a few seconds his hard-on subsided a bit.   “Now, when you feel that feeling, itʻs not pee, thatʻs an orgasm on itʻs way.  If youʻre not ready to orgasm, meaning if youʻre not ready to make a mess, squirting your jizz everywhere, stop touching yourself and breathe deep until the feeling goes away.  Then when youʻre ready, you can start again and when you do orgasm, it will be stronger and more pleasurable. “Okay,” he said, “I’m ready.”  “Letʻs go easy once you use lotion, take your time.  Try these moves.” I showed his different strokes, using different fingers, positions, speeds.   Then I showed him how to massage his balls. “Oh, I didnʻt think that would feel good, but it does!”  “Thereʻs also a place near your asshole that night also feel good.” I showed him how to stroke his perianum, which he liked, and then the prostate, which he didnʻt care for as much.   “Does size matter?” he asked.  “Not as far as pleasure is concerned.” “Youʻre cock is bigger than mine.  Does it feel different?” “I donʻt think so.”   “Can I feel your cock?”  He reached over and took my cock in his hands and held it for a minute.   “Wow, itʻs so much thicker and harder than mine, I can feel your pulse!”  He chucked and then started to stroke me. “So what stroke do you like best?”  Honestly, what he was doing felt great. “Oh, I like that,” I told him.  “Try holding the base firmly with one hand and pulling with the other.”  He did as I said and brought my cock to full hardness. “Are you going to cum?” he asked.   “Do you want to see?”   “Yes,” he replied “can I do it for you?”   I didnʻt have time to reply before he firmed up his grip and made his strokes more deliberate.  “Faster…” I told him. He complied. I leaned back on my elbows, watching him lovingly stroking my cock, his breathing getting just as heavy as mine.   “Now…” I gasped “Iʻm cumming”   I threw my head back, bucked my hips and shot rope after rope of cum onto my chest.   “Oh, I think Iʻm cumming, too!”  He was crouched over me and before he could do anything, he was erupting cum all over my stomach.  He was completely overwhelmed by the orgasm, his eyes closed, his entire body trembling. He fell over beside me onto his back, his cock still bubbling with cum.   “I got it all over you, uncle, Iʻm so sorry!”  I just laughed and patted his shoulders and chest.  “Donʻt worry, cleaning up cum is nothing new for me.  How did that feel?” “Awesome.  Thank you for showing me.”  “Do you feel awkward about it?”  “No, I really wanted to ask you for a long time, but I just didnʻt have the nerve.”  His voice was trailing off, and he dozed for a while before waking up. The second night, I showed him a few more things that I thought he should know.