The Tutor

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Can you teach an old dog new tricks?
7k words
4.49
23k
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Part 1 of the 3 part series

Updated 06/10/2023
Created 03/11/2021
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"I'm going to get some homework done for Mr. Richards." said Daniel as he finished his dinner and practically ran upstairs. My wife and I exchanged quizzical expressions as our 18 year old son galloped up to his room.

Daniel took after his mother Judy, he had her dirty blond hair, green/grey eyes, full, pouting lips and slim figure, which he worked hard on to try and build muscle but with all the drinking and partying he wasn't having much success. He was 5'7" and had longish wavy hair, all of which gave the impression he could pass for a cute (borderline hot) college girl from behind.

Our eldest Michelle was 20 and away at college, after being so strict with her I went the other way with Daniel, letting him get away with murder.

Much to Michelle's resentment.

She was sharing an apartment with some friends of hers and since she was only two hours away, she still came home to visit, eat free food and get her washing done for free once every month or so.

Dan had coasted through life so far with my blessing, he was one of the most popular kids in school, never short of a date or a party to attend. The problem was that he neglected his school work to the point where he barely graduated, much to my shame.

So as his friends went off to college or left town, Daniel found himself left behind at home. This is where I belatedly stepped in with a number of house rules and demands.

Firstly that he get himself a job that would prepare him for the real world and give him some real life skills. I took him to several interviews and was pleased when he got a job as an apprentice electrician and a cook in a restaurant. These jobs would teach him both the value of hard work and give him skills that he could use for the rest of his life.

Second we would get him a tutor so he could resit his exams and "try" for college next year.

Third, when he wasn't working or studying he was under a 9pm curfew, no partying, no hanging out, no getting drunk or laid.

And finally, if he wanted something he earned it. No more handouts or freebies.

Which also meant no more gym membership.

His first week of 'real life' was a shock to his system, he was up at 6am to get to site for 7, worked a 10 hour day and came back exhausted. He couldn't go partying on the weekend because he had the evening shift in the kitchen at a local diner Friday and Saturday from 6 to 1am.

I felt that it was the right thing to do, I had failed to keep Daniel on the straight and narrow when he was at school, now I was teaching him what it took to be self sufficient.

I didn't want to admit that I had enjoyed his popularity at school, that I was living vicariously through him. My own experience at school was limited to studying, chess club and mathletics thanks to my overbearing parents. No dating, no partying, no cheerleaders or prom.

This continued through my years at college and while I graduated and landed good job straight away, I also graduated a virgin. I was naive (some might say repressed) to the point where I never watched porn or jerked off, after the kids were born I heard some nasty comments - like the only way Jenna could've got pregnant is by cheating because there was no way I was man enough to knock her up.

Dan's tutor proved a little more tricky to find as several seemed to be more interested in watching the clock rather than actually teaching.

Eventually we found Mr. Richards, he was in his late 50's a former army man, turned teacher, now semi-retired and working as a private tutor. When I first met him I was struck by his size and easy self-confidence. He projected an aura of a man who knew what he was doing and wouldn't take any shit from anyone. He was around 6', thinning crewcut, greying goatee, he could pass for a former body builder, now gone soft, especially around the middle.

He looked like a mountain of a man, with the attitude of one who is used giving orders and having them obeyed without question.

In other words, the perfect man to knock some education into my wayward 18 year old whose main goal throughout school was to drink, party and get laid as often as humanly possible.

The lessons started once a week for two hours after work and now, apparently Daniel was getting homework assignments as well. I wasn't complaning, Daniel's attitude and demeanor had improved noticably thanks to Mr. Richard's tution. He also seemed to be doing better at his jobs, he was coming home with stories of praise and achievement rather than talking shit about his bosses and customers.

Judy and I finished our meal in surprised silence, loaded the dishwasher, cleaned the table and settled down for a movie with the bottle of wine we had opened during dinner.

As usual my wife fell asleep about twenty minutes into the film I kept on watching and drinking, until I started to get pins and needles from her sleeping on my arm. I gently rolled her off me and covered her in a blanket, after more than twenty years of marriage her inability to stay awake had gone from cute, to annoying to affectionate acceptance. I knew that she would eventually wake up and come to bed.

Tonight I put the empty wine glasses in the sink and made my way upstairs, at the top I paused, Daniel's bedroom door was open slightly and I thought I could hear voices and moaning. I cautiously tiptoed forwards and peeked through the gap in the door, Dan was in his gaming chair at his desk, headphones on, laptop open, watching a video.

So far so normal.

What wasn't normal was Dan was naked, his legs spread wide open, heels on the edge of the desk, slouched down in his chair, his ass exposed and nearly hanging off the chair. One hand between his legs, the other pawing and groping his chest.

I gasped and drew back, shocked and horrifed with embarrassment. The shock quickly wore off and was replaced by perverted curiosity, what was he watching? Why was he sitting like that?? What was he doing???

My inhibitions were lowered after the bottle of wine, so I risked another peek through the door. He was in the same position as before, he hadn't seen or heard me. I looked at the screen and saw some flat chested, college girl getting violently double teamed by two big older guys. Dan's hairless, toned legs were spread wide open like he was putting himself on display, one hand still between his legs but the movement was wrong, more of an in and out motion rather than up and down. There was also a sort of wet squishy sound and an unfamiliar sort of plasticky rattling or jangling every so often.

Mesmerised I carried on watching this curious display until Dan started panting and muttering under his breath, a few seconds more and he thrust his pelvis up, arching his back, his body tensed and he bit his fist in an effort to muffle his groan as he came. When he came down from his orgasm, he took his feet off the desk, sat up straighter, typed something on his laptop and shut it down. Then he took his phone from where it had been propped up on the desk and tapped the screen a couple of times, he rubbed his free hand over his bare torso and sucked on his fingers while looking at the screen intently. He did this three or four more times before he stood and headed towards the door.

That broke the spell, I hurried to my bedroom and shut the door as quietly as possible. I was very thankful that we had spent the extra on noise cancelling headphones as it appeared that he hadn't seen or heard me watching him watching porn. I stood with my back to the door, my heart beating a mile a minute as I heard Dan's foot steps approaching then receeding as he walked on by to the bathroom, when I heard the bathroom door shut and the lock click in place I sighed in relief.

I concentrated on my breathing until I got myself under control, it was only then I noticed my cock was hard.

The adrenaline rush faded and was replaced by a bone deep exhaustion. I was too tired and too drunk to think about what I had seen, why I had stayed to watch and my body's reaction, I just about managed to strip my clothes off and collapse into bed.

The next day I was very distracted, I was disturbed by the things I'd seen the night before and my reaction to it. I tried to rationalise it away by telling myself that I was drunk and was watching the porn, the sound effects and moaning provided by Dan were just a sound track to the action on screen.

Some part of me believed it, a smaller, darker part of me doubted it.

That night after dinner, Dan bolted for his room again claiming he had more homework to do for Mr. Richards.

Judy and I retired to the couch, with the bottle of wine and settled down for a movie.

Like clockwork, she fell asleep after half an hour and I decided to go check on Dan.

I cautiously crept up the stairs and paused at the top, sure enough Dan's door was open - a little wider this time.

He was naked again, legs spread wide, feet on the desk, giving himself as much access to his ass as possible. The fingers between his legs were moving in an unmistakeable in and out motion and were too low to be anywhere but playing with his asshole.

I watched him entranced, his face was flushed, his mouth hanging open in pleasure as he whispered something to low for me to hear over and over. His attention was no longer on the action on screen, his eyes were screwed tightly closed in concentration as he slowly worked three fingers into his hole, twisting them as he did so, elicting quiet whimpers.

My own hand made its way to my crotch and began to stroke my cock in time to Dan's slow, deliberate rhythm as he stretched his hole wide around his fingers, still twisting them in and out in a screwing motion, opening himself up, groaning as the knuckles rubbed and distended his hole, his ring now stretched tight, the skin white and oddly glistening.

Hypnotised I stroked my own cock at the same pace, now increasing as his hole got used to his fingers, soon he was ploughing those fingers in and out, his hips thrusting out to meet them, his legs tipping the desk back in an effort to get a better angle, power fucking himself so hard he was in danger of the chair toppling over backwards and taking him with it.

Then all of a sudden he stopped.

With visible effort he pulled his sticky fingers out of his wet hole, strands of juice connecting them, he sat up straighter and looked at his phone, licking his fingers clean as he did so.

I beat a hasty retreat to my bedroom, as quickly and as quietly as possible.

Once there I stripped naked and lay on the bed, my cock standing 5" proud and erect. I wasted little time working it up and down frantically, I had never played with myself before but watching Dan's display had flicked a switch and I wanted to cum.

I was desperate to cum.

As I stroked myself hard and fast, I rubbed my full, hairy balls with my other hand, moaning as quietly as I could. My fingers let go of my balls and moved lower, tentatively exploring my ass crack. I jumped when my fingers found my hole, it was so sensitive it felt like an electric shock!

The pleasure was so intense it was painful!

I withdrew my fingers, coated them in some of my precum and returned to explore my hole. I was stroking myself slower now, the frantic urge to cum faded as I focused on this new discovery, I stroked my cock slowly, deliberately keeping myself aroused and on the brink of orgasm. This only heightened the sensations of my lubed fingers exploring my hole. I rubbed my fingertips around my hole, gently tapping the centre, then returning to circling, alternating the pressure from feather-like tickles to hard, firm presses.

Sometimes adding another finger or even two as I continued to experiment, to discover what felt good and what felt better.

I was moaning louder now, lost in the pleasure of playing with my ass, I was barely touching my cock now and it was still hard and oozing precum, which I used to continually lube my fingers and keep my hole nice and slippery.

I slipped a finger inside my hole to the first knuckle and slowly moved it in and out, teasing myself, driving myself crazy, the feeling of having something inside me was setting off a fireworks display of pleasure, I lightly teased the sensitive head of my cock as I fucked myself, once, twice and came hard on the third stroke as I pushed my finger in to the second knuckle.

I think I might've passed out from the intensity of the orgasm.

When I came to, my belly was covered in cum. I hurried to the ensuite and wet a towel to clean myself off and went to bed.

I slept like a baby, the after glow of my orgasm left my body warm and tingling all over.

Happily the next day was Friday and at work everyone was so focused on the weekend that no one was very productive and no one noticed how distracted I was.

Or that I had trouble sitting still.

Friday night was also when Dan worked in the kitchen at the local diner, so I didn't have to worry about catching him avidly finger fucking his ass.

Or my reaction to it.

The night passed uneventfully, we ordered thai food and made cocktails of lychee juice, malibu and lime.

That night I had a strange dream, it started with me going upstairs to check on Dan. He was naked in his chair, legs spread wide, fingering himself as he had been the last two nights. In the dream, he turns and sees me. He pulls his fingers out of his sloppy, wet ass and beckoned me forward with them, suddenly I was on my knees between his legs, face to face with his juicy, volumptuous ass hole. It looked like the most kissable thing in the world, Dan ran his sticky fingers through my hair and pulled me forwards, I leaned in and kissed his warm, wet hole.

I woke up with copious cum stains on my boxer shorts.

Saturday morning and the wife had gone shopping when I got a call from Mr. Richards. He said that he was pleased with the progress that Dan had made in just two months and that he would like to offer him the use of his personal gym on Sundays, if that was okay with me.

He would throw in some additional tuition whilst Dan was there at no extra charge, that was music to my ears! More tuition for free and Dan got to go to a gym again as reward for his dedication and hard work. It was perfect and allowed me to tell him that this was because of the effort he had put into his studies.

Dan was delighted when I told him. He spend a good amount of time getting his bag packed and ready for Mr. Richard's gym session tomorrow.

We had pizza together that night before Dan left for his job and Judy and I settled down for a Netflix binge.

After the unsettling dream last night, I made sure I drank more than normal so I would sleep better.

On Sunday, I decided that I would give Dan a lift to Mr. Richards so he wouldn't have to catch a cab or walk back post workout.

We arrived five minutes early, Dan hurried to the door and knocked. A few seconds later Mr. Richards opened the door, he was as handsome, tall and imposing as I remember.

We smiled and waved at each other as I drove off.

Two hours later I returned to pick Dan up, I had arrived 10 minutes early as Mr. Richards was the sort of man that believed that early was on time and on time was late.

I walked up the driveway, noting the well kept lawn and knocked on the door. A minute or so later Mr. Richards answered, he was sweating lightly and wearing a football jersey over lycra shorts and flip flops.

He welcomed me inside, complimenting me on my punctuality. I noticed the row of shoes at the front door and so paused and took my shoes off.

When in Rome.

I followed Mr. Richards barefoot into a well appointed kitchen, all minimalistic clean, white surfaces and tasteful lighting.

I felt like a child trailing their parent, this was a man with a magnetic force of personality, who had lived a life full of experiences, had risked his life on the field of battle and then chose to serve his country by teaching the younger generations.

I was an office drone, with a sarcastic sense of humour, wife, mortgage and two kids. I got married at 24, had the kids and then settled into the surburb life.

"Smoothie?" he offered in his sonorous voice.

"Yes please" I answered, still in awe of this commanding, ruggedly handsome, older man.

He poured me a thick, creamy coloured drink, I sniffed cautiously, it smelt blandly sweet. I took an experimental sip, it was rich and creamy, tangy and sweet, warm with subtle spices, with a slightly bitter aftertaste.

"It's very good" I said, taking a bigger sip.

"Post workout recovery shake" he explained, "my own secret recipe, helps eliminate fatigue and stimulates growth and repair."

I kept drinking while he was talking, there was something addictive in that almost familiar taste, like having a word on the tip of your tongue but able to think of it.

"Danni was just finishing in the sauna, he should be here soon" Mr. Richard's said.

He nodded at my empty glass "Would you like another?"

"Yes please"

He grinned and poured me another glass full, which I drank thirstily.

"Mmmmmm!" that is good!" I exclaimed.

"Let me show you around the place, while we're waiting."

I nodded.

Mr. Richards gave me a brief tour of his house, we started in the kitchen and walked through his open plan dining room to the lounge as he pointed out various paintings or souvenirs he acquired during his travels and tours of duty.

He opened his office door briefly, explaning that he did some amateur video production as a way to keep himself busy, earn some money and help out local struggling artists.

We went upstairs and he showed me around four large bedrooms all complete with ensuite. I assumed one of the rooms must've been his but I couldn't tell as all the rooms appeared to be the same, white walls, with one being fully mirrored, large bed with expensive looking bed linen and old fashioned cast iron bed frame and head/foot board.

Oddly, all four rooms had cameras on a tripod set up in one corner, covering the bed, entrance and mirrored wall.

He led the way back downstairs, I watched his ass and thighs under his shorts. I admired his broad back, big shoulders and arms thick with muscle.

He showed me his gym, which was full of the usual machines and a good free weights area with a separate area for stretches. Lots of mirrors so you could check on your posture and form. Some dance/trance/house music pulsed through the speakers, a subliminal hypnotic beat, some repetitive chorus droning in the background.

Just off from the gym area was a smallish room that had a hard wooden floor and several leather benches or boards of varying heights and angles. What looked like leather straps of differing shapes, lengths and thicknesses neatly lined one wall. Two walls were covered in mirrors and the door to the shower and toilet had been removed. There were three cameras mounted on tripods in the corners of the room. In the centre of the room hung what looked to be a sort of sling, could've been two or three judging by the number of ropes and chains suspended from the ceiling. The same pulsing hypnotic beat continued endlessly in the background.

"This is my pilates/yoga/physiotherapy room" he explained with a hint of amusement in his voice. As I walked around exploring, I went to the wall of leather straps, running my hand along them, cooing softly at the cool smoothness (there's just something about black leather), noting the different textures, one or two almost looked like whips or cords. "The cameras allow me to record the sessions so I can review the strength and conditioning of the muscle group that is being targetted."

Mr. Richards gave me a minute to take it all in, there were some weights displayed on a small table, but they looked too small for a workout. On another there were also some stainless steel bars and bracelets, the biggest of the bracelets looked to be about the size of a handcuff, the smallest was barely an inch wide, I had no idea what they could be used for.

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