Sex Mentor Teaches Me the Ropes

 I'm Adam, 23 years old, thin build, long light brown hair, with an exceptionally young looking face. I stand at 5'11", but because of my sixteen year old appearance going out to bars, casinos, and getting laid have all been a bit more difficult than I imagined.

One day while looking through a hookup app a man messaged me asking to fool around. He was a burly-looking man, my height, with short salt and pepper hair and a thick beard. I told about my virginity and asked if he'd be okay with showing me how it's done. He responded with, "Just consider me your sex mentor. As long as you want to learn, I'll teach you how two men have a good time together." My heart racing with the possibilities, I responded back, "Then consider me your student." He explained to me how to clean and prepare myself. When the day finally arrived I felt like I could be sick to my stomach with nerves, but I refused to talk myself out of it. This was happening. He messaged me his address and I started driving over, my knees shaking with excitement and anxiety. I pulled up to his house, realizing this is my last chance to back out. I steeled myself a bit, put the car in park, and walked up to his front door.

He answered the door, wearing a plain white t-shirt that adhered to his big chest and arms and a pair of athletic shorts. He smiles and asks for me to come inside.

"You nervous?" he asked me calmly. I simply nodded my head and he grins back at me. "Don't be. I'll take good care of you boy, and if you ever want me to stop, then I will...no questions asked." His answer reassured me and I worked up the courage to give him a smile back. He made me a drink to relax my nerves a bit and guided me upstairs to the loft. There's a leather futon and computer desk next to a TV mounted on the wall. Okay so how is this going to start? He moved over to the computer and after a few minutes, brought up some bareback porn on the TV. I've never even watched porn with another guy before then so my eyes kept darting between my mentor and the TV where a twink-like guy was getting plowed by a huge muscle-daddy.

"You like what you see?" he asked me, pointing to the TV. Not quite sure how to react I nodded my head again.
"Yeah, it's hot," I told him.
"Good, but you should call me sir," he replied with a gruff voice. I worried that I might have angered him.
"Yes, sir. Sorry, sir." He gave me a wide grin and I could feel his eyes feasting on me.

"Good boy. Now get out of those clothes." Before I even realized what I was doing my shirt was lying on the floor and I was slowly undoing the belt on my jeans. I approached me and rubbed his hands up from my navel to my chest, softly grunting in approval. His touch reassured me and I let my jeans slide to the ground. As soon as I did he reached a rough hand under my boxers and fondled my cock gently. With each passing moment I felt myself grow a bit more confident. I removed my boxers, leaving me stark naked. He licks his lips and points to the futon.

"Lie down on all fours. Keep your ass up high for me," he commanded.

"Yes, sir." I crawled onto the futon and arched my back so my ass was ready for him. At this point I could feel my fingers tingeling from the rush of adrenaline I was having. He moans at the sight of my hole and grabs onto both of my ass cheeks. He messages them under his coarse hands and places a soft kiss on each one. I look down and I'm surprised to see my own cock starting to drip with pre-cum. "Holy shit, this is really happening" I remember thinking to myself. He placed his tongue right above my hole then licked up and down my crack, teasing me, knowing I'd more from it. His beard scraped and tickled my freshly shaved ass, sending shivers down my spine. Then suddenly, he grabbed both of my hips, pulled my ass closer to him, pushed his tongue inside my hole.

I gasped, not having expected such a sudden change. He chuckled at my surprise and started going to town. His tongue slide in and out of my hole, shooting waves of pleasure across my entire body. So this is what it's like to get tongue-fucked. I pushed my hips back against him and I felt his tongue push deeper inside, causing me to shout out a little louder than before. He smacked one ass cheek playfully and chuckled some more.

"That's right boy, you love having that hole played with. Just look at your cock. You're leaking like a faucet." I looked down again and saw he was exactly right. My cock was getting harder and was constantly pumping out more pre-cum. I had never felt that way before and my thoughts started to lose focus. All I wanted was more of what he can teach me.

He ordered me to flip onto my back so I obeyed and laid there waiting for my next instructions. Instead he leaned down and wrapped his lips around my dripping cock. I tried stifling my surprise, but clearly it showed.
"Never been sucked before boy?" he asks while still sliding his tongue along my shaft.

"No,sir. It feels amazing!" I exclaimed. He slides his hands up to my chest and begins playing with my nipples. Not long after he got serious and took me all the way down to my balls. I tried to sit up from the pleasure of it, but he firmly kept a hand over my chest to keep me still. With nowhere to move I found myself bucking my hips and writhing under him as I got closer to a climax.

"I'm cumming, sir!" I shouted, but the moment I did he released his lips from my cock.
"Oh no you're not boy. Not yet. Just hold it a bit longer. We're nowhere near finished." I tried to slow my rapid breaths to calm down, but before I could, he was reaching a lubed finger into my hole. I gasped at the sudden change, but it wasn't painful or uncomfortable. He started stroking my insides with his finger, loosening my hole up. After a few moments of this his finger began to prod at my prostate and I instinctively pushed my hips against him, sliding his finger in deeper.
"Oh yeah, that's the spot. You like that boy?" he asked teasingly. I nodded again and he slipped in a second finger, adding a bit more tension. "You still okay?" he asked softly.

"Yes, sir. It feels...oh god, I don't even know what this feeling is, sir" I tried my best to explain. He merely smirked and massaged his fingers around inside me. A few more minutes and he stuck in a third and then a fourth. I had fingered myself before, but I had no way of knowing how much better it would feel to have another person massaging my prostate. Without warning he pulled his fingers out of my hole and reached into the drawer of the desk next to us. He pulled out a black dildo about 6 inches long.

"Want to take the next step?" he asked me coyly, rubbing the end of the dildo across my hole.
"Yes, sir. I'm ready." He flipped me over onto my stomach and coated the toy in lube before he began pushing at my hole. Instinctively I clenched up and he laid a hand across my back.

"Shh, it's okay boy, just relax." His words reassured me and I loosened the muscles around my hole. As I did i felt my hole stretch out wider and wider until it slid inside. At first the sensation was a bit uncomfortable, but far from painful. He slid the toy in an out just an inch or two as I got used to the size. "Take a deep breath and relax some more," he commands. I obeyed and he slid the remaining four inches inside. A large glob of pre-cum spilled onto the futon as I moaned in pleasure. I had never felt so...full before. He waited a few moments before pushing the dildo around into the recesses of my hole. I buried my face into the futon, biting down into the leather to keep from crying out. I could hear him snickering behind me, knowing I was loving every second of this. After awhile of him stretching me out, he tugged toy back out with a soft pop, and my hole twitched longingly for something else to fill it.

"Okay let's try something else now," he said gruffly. I turned around to see him pulling his shirt up over his head. He had a strong, built chest and slight beer gut. Then without skipping a beat, he dropped his shorts to the ground, revealing a monster cock. It was thick, about 8 inches long, and staring me straight in the face. "Go on boy. Show your mentor how much you want this daddy cock." He didn't have to ask me twice. I placed both my hands on his hips and brought my mouth right up to it. This close I could smell his manly musk and it felt like a drug, driving my thoughts wild. Without another thought, I wrapped my lips around the head, savoring his taste, and then slowly started working the rest into my mouth. He placed a hand on the back of my neck and started to guide me up and down his shaft. "Yeah, that's right! Swallow that cock!" I could feel him getting harder in my mouth, which only drove me more crazy for it. "Okay boy, now the whole thing," he ordered just before using both hands to pull my head down on his cock.

I felt the head push past my mouth and down my throat until my chin was touching his ball sack. I felt my gag reflex act up, but I was adamant to not let it affect me. I looked up at him to see a devilish grin spreading across his face. He clasped both sides of my head and started humping my face. Each thrust slid his cock deeper down my throat and the urge to gag grew. Not too much longer and I pushed away to get a breath of air. With a long string of saliva still connecting my lips to his cock I dove back down onto it with renewed vigor, determined to please the man who was giving me so much pleasure. It seemed to work. "Oh fuck yeah boy! Eat that daddy dick!" I continued to suck on his meat for another ten to fifteen minutes before he pulls it out.

"You wanna try the real thing now?" he asked me more gently than I would have expected.
"Yes, sir." He ordered me to get back on my hands and knees and to arch my back. He got behind me and immediately pushed his tongue back into my hole. Now that it was more stretched out it felt like he was reaching twice as deep than he did before. I couldn't hold back my moans of pleasure anymore. He pulled his tongue back out and I heard him positioning himself. Then I felt his warm cock resting across my hole as he gently slid it along my crack. I was losing my mind. Just do it already!

"Please, sir. Put it in," I pleaded with him. He started grinding my crack with a bit more intensity.
"Beg for it boy. Tell me how much you want this cock inside you." I felt like I could pass out from the surrealism of it all. I never imagined myself to be capable of dirty talk, but this man knew exactly how to work me up.
"Please, sir, I'm begging you! Stick your cock inside me. Give it to me please, I can't take it anymore!" I was rubbing my ass along his cock while I was panting like a bitch in heat. He chuckled again.

"Good boy, I'll give you exactly what you want!" he muttered before sliding his thick pole inside. He was definitely bigger than anything else I've had up my ass so far, but once again it wasn't painful. In fact, despite how much of a tight fit it was, I could feel my ass swallowing him up inch after inch until he was balls deep. To feel a hot, throbbing cock pulsing inside of me, was both the strangest and most amazing feeling of my life.

He started thrusting slowly, letting me adjust to his girth. I expected him to be the one to want to switch tempo first, but after only a minute of him being inside me I was begging him to fuck me harder. He didn't hesitate once I asked him and started to drill my hole. Feeling his hard body slapping against mine while his tool stretched and filled me up was pure ecstasy. My eyes rolled to the back of my head and my moans of pleasure, became more shouts than anything else.

Without saying a word he flipped me onto my back with his dick still inside me. He raised my legs up over his shoulders and started pounding my hole with even more vigor. I stared up into his eyes as they devoured me. In his eyes I could see what he was thinking. "This boy is mine. Mine to tease, mine to play with, mine to fuck to my heart's desire". And he was absolutely right.

"Stand up boy." I obeyed him and he commanded that place my hands on the futon with my ass in the air. I did as he told and without warning he drove all 8 inches of his thick man meat into my hole. I nearly came right then and there, but managed to hold it as he started to pound me harder than ever before. He slid his hands up my stomach to my chest where he started to pinch my nipples again. I arched back into him, letting my hole swallow the entirety of his massive cock. How could I have waited this long? Why was I so afraid of this?
He placed his hands on my hips and fucked me ravenously. Each thrust sent a new wave of electricity through my body. His pace quickened and he started to grunt and growl like a wild animal.

"You want this load boy?" I shouted and begged for him to give it to me and he buried his dick as deep as it would go. He gripped my sides tightly and bit down into shoulder as his cock pulsed rapidly. He growled deeply while his load continued to pour inside me and soon it felt like I was going to burst. When he finally finished my mentor pulled his cock out slowly and started laughing to himself.
"Look at that cum just oozing out of that hole. You want to see your used hole boy?" he asked, still panting from his orgasm.

"Yes, sir." I surprised myself once again with how much I wanted to see. The thought turned me on so much I got rock hard. I heard the click of a camera and he shows me his phone. I gasped slightly at just how much cum was flowing from my hole down to my ball sac. He started nibbling my ear as I stare in disbelief. I reach back and slide two fingers into my hole and I'm instantly greeted by the feeling of thick, warm semen. I spread my hole open and looked beneath me to see thick trails of cum pouring out of me. How much did he pump inside me exactly?

Without speaking he laid me flat on the futon and stuck his dick into my mouth before I could even try to complain. With one hand he held my head in place as he fucked my throat and with the other he jerked me off. The taste of his semen on his cock made me want him even more so I feverishly sucked my mentor harder. I could feel myself about to climax. A few moments later I finally came, but it was the best climax of my life.

"I'm gonna cum again boy!" he barely managed to say before my mouth and throat were flooded with his thick warm cream. I swallowed as much as I could, but it was simply too much. I pulled my head away and it drained from my mouth as he continued to shoot his cum all over my face. He sighed happily and rolled onto his side next to me.

"That was really good boy. You sure that's your first time?" he asked sarcastically.
"Yes, sir. I hope I did alright."

"More than alright boy. How about I hit you up next week? We can do this again, or maybe I could invite a friend or two over. You like the idea of a group of daddies using you boy?" His offer turned me on so much I got another erection. He laughs softly and grips my cock firmly. "I'll take that as a yes boy."