The First Time With An Old Master

This is my first writing a story, and what would be a better story than my first encounter with a dominant guy who became my master?

To tell you a bit about myself, I was always a bit Bi-curious and wrote with men in chats to exchange fantasies and experiences. During that time, I found it interesting to go to cruising areas, walk around, get the adrenalin running, and feel the nervous tingling in my body for maybe doing something in public that usually happens behind closed doors, and only with women, to this point. During that time, I got some experience with oral sex with random encounters. This was the limit to which I could push myself with men.

At some point, I became an exchange student in the US and lived with a guest family. I was still chatting with men from time to time, but the scene was a bit different and nothing interesting popped up for a while. Yet, I didn’t want to let the opportunity pass to play with my Bi side while being in an area where nobody know me – I figured this would make it easier for me to push my limits further.

At some point, I was chatting with Bob, probably Robert if I remember right. I was twenty-seven and he was eighty at that time. That was a huge age difference, but when watching porn, I also get turned on by mature men, so why shouldn’t I try this in real life and see if I like it.

We chatted about our interests and what we are into. He directly mentioned that he is dominant and likes to play the role of the master. I like the thought of being submissive and providing my body to the master such that he can play with it and get off on whatever he would like to do. I’m also strongly into anal play, the more creative and out of the ordinary, the hotter. He started joking that, if I ask for more odd and unusual things that I want him to insert into my ass, then on one sex date, he might surprise me with a landline phone.

Sure, I still grew up with these things; a sturdy base with a handle on top, the ear and mouthpiece as a big half circle, connected with the grip. Nobody used these things anymore, but given his age, he actually might. I had experience with bigger dildos but never stretched myself so far that a landline handle might fit.

We started talking about what he does with other submissive guys at his place, that he has a big shed in the garden which he uses as his sex playground, what dildos he has, and what he would like to do with me should we meet for a session. He seemed to have two favorite dildos, a rather thin double dildo, and a very thick and very long dildo – “Big Berta” as he called it. When I heard about “Big Berta” I immediately thought, please, use me, stretch my hole, do what it takes, work my hole, prepare me, and then take “Big Berta” and let this monstrous dildo vanish inside my body. I haven’t even seen a picture of this dildo yet but I knew I wanted to feel it.

Well, if I wanted to get big Berta inside me then it seemed that we needed to start talking about another interest of mine – fisting. I always wanted to feel a hand inside me, and he seemed to be a specialist. Since our interests seemed to match, I also asked him if he would like to fuck me, it would be a first for me, but unfortunately, he told me that he couldn’t get hard anymore and his dildos and other toys are the only instruments that he could work me with. So ok, time to meet, I lived with a guest family and couldn’t really prepare myself for such a date, but he said that I can prepare at his place. That’s a big step for me, from only giving the occasional random blow job to: Cleaning in his bathroom, getting dominated, providing myself for dildo play, and possibly getting fisted. Oh – and then there was the landline surprise…

We planned a few meetings which then didn’t work out because either I was too shy, wasn’t mobile that day, or I wasn’t horny. Since I’m only Bi-curious, I’m only into men from time to time, and I don’t know when I’m horny for a guy in advance.

Needless to say, he got a bit impatient with me. So, last chance, he said that we can meet early in the morning on a weekend. I never saw his face and I wanted to meet him at a diner for breakfast, eat, decide if we are still a match, and then drive to his place. This meant, I wake up early, need to be horny for a dick or at least his dildos, drive to an area where I never have been, have breakfast with Bob, and wonder what people in the diner might think about these two guys with a huge age difference and this early for breakfast. Fuck, what if I’m not horny… Alright, time to get the show started, I had early lunch and a very light dinner the day before. It actually turned me on to know that I eat little, stay a bit hungry and go to sleep, just to keep my colon empty in the morning for Bob’s pleasure.

It was time to wake up, I’m still tired, I wrote him a text message, “I’m up and I’m preparing myself,” just to assure him that the date is still on. I don’t even remember if I was horny that morning, my sleepiness might have helped to push myself for this date. I showered, cleaned my body about three times, and shaved my hole just to make sure that I’m extra clean when I meet Bob. I want to be his sexual playground and I should be a clean canvas before he starts his kinky routine. So I got nervous but still convinced myself to get to my car and drive to the diner place, “So what, worst case, its an uncomfortable breakfast.” My next text was “I’m ready and leave now, I’m there in thirty minutes.” This ride was full of excitement, adrenalin, and nervousness – Today might be the day that a man finally fucks me with his fingers and toys. Nobody knows me here, so nobody who matters can see me and judge.

So – I arrived at the parking lot. I knew what car he was driving and should be able to spot him, first, when he arrives. I wrote another text “I’m here, let me know when you are.” A moment later he responded and said that he goes in to the diner at any moment. Time to gather all my courage and get out of the car and stay close to the entrance to meet him. I stood there for a minute, still far enough from the entrance, and looked out for an eighty-year-old guy that’s about to enter the diner. And there he was – I guess – an elderly guy, walking toward me, not making eye contact and aiming for the entrance. He ignored me or at least wasn’t looking out for a young guy outside.

So, I said, “Bob?” He still barely paid attention, maybe that’s how it is in this scene, pretend to ignore it till you are at the meeting point, which was inside.

He passed by me, just a few meters, then turned around and he addressed me, “Are we here for the date?”

I said, “Yes, good morning Bob”. We shake hands…

He walked slowly and with a lot of effort. He was rather skinny and had quite some wrinkles on his face. Sure to say, I was probably mixing up the looks of a sixty-year-old man with that of an eighty-year-old. He was good-looking but not necessarily “Hot” in that sense. Yet, I was still interested, not in the “Let’s kiss all night long”, but in the “Play with my body, I want to see that you enjoy me as your toy” sense. And we discussed that I’m not into kissing anyway. Alright, let’s get back to the moment. I’m used to meeting random guys and vanishing in a small forest at a parking lot for oral sex – there seldom is any talking.

Since I already decided a second ago that I still want to go with him to his place, I said, “Do you still want to have breakfast?”

He scanned me from the bottom up and said in a bit of an inpatient and upset tone, “Are we doing this or NOT?” Probably because we had some failed dating plans in the past.

I needed to collect myself for a moment and said, “Yes…” So he told me to get to our cars and I should follow his car to his home. We started driving, still about fifteen minutes, I’m getting so nervous.

We arrived at a very calm street, with a bit of a suburban vibe, and he stopped next to his house. He got out of his car and so did I – time to enter his house. I entered his front door and we are directly in his living room. There are two opposing leather chairs, the ones you would find in a cigar bar. Very elegant. He told me to sit down to talk. Time for me to acclimate and talk to Bob about our interests.

He asked me what I’m into, what I imagine, and why I think that I want to have the session with him. We already wrote about most of it in the chat, but one thing that came up was that I like porn, and most of the time, I get horny for a cock when I see the woman giving a blow job and then getting fucked. And he said, “And you want to do the same with a man because you think you can do that too?”

I told him, “Yes, when I see a woman giving a good blow job, I also want to give a blow job and taste the dick. And when I see them having sex, then I want to feel a dick inside me too. I know that my hole can handle a lot and I think you can fuck me the same.”

Alright, the talking time was over. He said, “Ok, you said you need to clean yourself here? Let’s go to the bathroom.” I followed him. In the bathroom, he showed me the things I would need. “Here is the clister, fill it with water and squeeze it inside you. Then, use the toilet and do this until you are all clean.” He even gave me a box of vaseline in case I need it. Then he left the room. Ok, he does not take the opportunity to watch me or to clean me himself, he gave me some space.

I stood there, still fully clothed, and thought, can I do this? I want to get his toys inside me, I’m horny, but is today a good day? I walked back and forth, another adrenalin rush… ok, if I don’t do this today, I never will…. I pulled my pants down, took his clister, and inserted it in my hole. I cleaned myself a couple of times, all clear because I prepared by not eating, anyway let’s be sure for him. Every time I flushed the toilet I thought – He sits there behind the door and every time I flush, he knows that I filled myself with water and ejected it, for him. That turned me on even further.

Ok, I’m ready, I’m leaving the bathroom and let him know. We then walked to his shed, out of the house, to the garden, which was huge, and into another building. This was more a second house than a shed. When you entered, you saw a fireplace, more leather chairs, bookshelves, and a few stairs down there was a flat area with sheets.

I thought at some point he would just start touching me or grab me by the ass, but no. He actually gave me a proper tour and said, “This chair and table are for you, you can place your things here and hang your cloth before we begin.” Then down the stairs, “on this table is the double dildo, and next to it is the big Berta, I already cleaned them and put a condom on it”. Then he showed me a sealed box “I just got this from the sex store, I haven’t used it yet but its something to stimulate the prostate.” We moved to the flat area, “And here is where you gonna lay down, your butt is gonna be on the edge and I will sit on the chair before you and work with your butthole.”

He brought me back to the beginning, where he said that I can hang my cloth and said, “Ok, now you will fully undress,” he turned around and walked to his chair.

I was so nervous and horny, so I started undressing. Shirt, shoes, pants, socks, and last, my underwear. I remember very well how he gasped when I finally stood naked at this spot, looking at him when I was ready. He must have liked what he saw. He told me to come and sit at my place. I thought he would undress too, I wanted to see his dick, his body, maybe play with it – even though he could not get hard. Too bad though, in all that we did at his place, I didn’t even see Bob nacked. But that has something to it too I guess.

I sat down, and he put a latex glove on and proudly showed me his oil “Gun Oil” if I remember right. He said that we will start with the fist training, starting with one finger, then two, and so on. He wanted me to get into a doggy position for this, but I preferred missionary because I wanted to see him when he plays with my hole. This seemed unusual to him and he was afraid that I can’t hold my legs up to long, but I was sure I can make it work or switch positions later. I lay back spread my legs and let Bob do what he wanted to do.


He started oiling his pointer finger, the oil dripped all over it and then he moved toward my little hole. And a second later, I felt his touch – he didn’t enter me though, he spend enough time to oil my hole, the area around it, massaging it into every winkle on the outside. I was less nervous but full of anticipation. I was slightly distracted by the time he took to apply the oil that I almost missed the moment. And there it was, after all the circling around my hole, massaging the area, the one moment when there was just a bit more pressure on his finger when he slid from the bottom of my hole to the top. There he was sliding – just a bit – inside me.

The first finger of a stranger inside my hole. But after spending this much time on my outside, he almost didn’t spend any time to push it in all the way. So, his finger is all inside me, then he slowed down again and dripped more oil on me and took his time to oil my inside too. He moved his finger in and out, and I remember, he leaned in with a bit of weight when he was pretty much all the way in already. Then he started turning his single finger, round and round, in and out, applying more oil every time. It was fun, but I thought, “Come on I need more than this, deeper or wider, anything, please.” Well how foolish I was, I will think back to this moment later and wish it remained that easy… But I didn’t meet Bob for something easy, did I?

What I didn’t know, Bob treated every additional finger exactly the same. He started with one, it didn’t matter if I was already wide enough for two fingers or even the dildo. No, I got one finger, and only after his routine, I got the next one. So it went, I got the second one, fun but not a big challenge.

When I’m alone, from time to time I get a cucumber and push it all the way inside me – just as a reference – but Bob knew that too. Yet I’m more trained for depth than width.

After his routine on finger two, I got finger three. Uhh…, there we gained some traction! Especially when he twisted the three all aligned and leaned in with a bit of weight when he was fully inside. Then he hit me at some spot where I got the odd feeling that I might squirt some of the cleaning water at him. That’s when I asked him for a quick break to let this feeling settle.

Back and ready, I thought ok: three fingers in, I’m all horny and excited so I asked him if we can use the double dildo now. But no, Bob wasn’t done fingering me, we continued with three, then with four – there was the challenge. A little bit of stretching pain, and now my hole needed to show what it can do in these morning hours. But I kept quiet, Bob can already feel that it gets tight in there, the only thing I could do was relax, and help a bit by grabbing my butt cheeks and spreading them.

I thought, “Get your fingers in there Bob, play with me, I want your hand, stretch my fucking young hole as you please, I’m here to please you!” Bob spent some time, working my hole with four fingers, and every angle that might get a bit tight was stretched thoroughly, just with a little body weight of him leaning in – ahhh, of course, I’m gasping every time it becomes difficult or he hits the right spot. Since a lot of time went into the four-finger procedure, I started looking at his pants, it was very loose, so nothing to see, and he said he could not get hard, but a dick does not need to be hard to get sucked.

Should I touch him? will he see that I’m looking at it? But no, I was busy spreading and holding my legs and he was too focused on stretching me out. But at some point, he started to use his other hand and played with my dick. Just a little bit. No squeezing, no ball torture – oh, I wish he would have grabbed my balls hard. But I got the torture a different way, no reason for complaining.

Bob decided that we stay at four fingers for this session. He pulled his finger out and stood up to get the double dildo for the next act. I had a similar double dildo and knew that I can fit that thing completely inside me – but let Bob find out by himself. Time for some fun in the deep. So he oiled the dildo, told me to lay back, and imagine that I get fucked by “someone.” He aimed the tip of the dildo at my hole which was standing wide open, had lube in every little winkle, and was hungry for more objects.

Needless to say, Bob didn’t need to push much to get the tip of the dildo inside me. At least as far as he already was with his fingers. And then he fucked me with only the tip, probably three inches, I knew that more was to come so this time I enjoyed the easy part for the moment. I leaned back, closed my eyes, and let Bob fuck me with his dildo. His view must have been amazing. Drawing the lips of my hole to the inside when he pushed the dildo inside me, and watching how my hole is grabbing the dildo and gaping when he pulled it outwards.

Everything is nice, creamy, and oily. Let it only be three inches but he fucked me hard with that tip. Up to the point when I wanted more.

So I asked him to push it deeper. To this point, he didn’t pass the internal sphincter nor passed through the first turn, that’s probably six inches in. So I begged him for it. I love when the dildo pushes against the turn and slides far into my colon. So he was about to do it, it was amazing, completely different as if I do it myself, and passing this control on to Bob was “hot.” He pushed it carefully inside me to the point where the first turn is and the resistance got higher and it requires more force to push beyond this point. He played with that spot, he drew back the dildo and hit against the spot without wanting to pass it.

Every time he pushed against this spot, I felt this Kinky pain, it’s pain but it’s very arousing, I love to play with it myself, and going past the point where you are stretched enough inside is insanely rewarding. Bob knew to play with this pain and he did, he observed me and felt the resistance – he knew exactly where he was with the tip of the dildo inside me. He played a bit back and forth a few inches before this spot and – again – pushed the dildo rather rapidly right to the spot, but not past. My pre cum was dripping like crazy. This guy was teasing my intestine – “Oh yes please!!” And then “He” wanted more.

He moved to the spot and stayed there for a second… and then? Fuck – Bob leaned in with his body weight and strongly pushed the dildo into the turn and into my deeper colon. He made it past the turn, there was no back-and-forth motion, no jiggling, no mercy! An all-or-nothing forward push deeper inside me. It was an amazing sensation. The dildo still stood out about half of its length. Room for more, but Bob started fucking me to the newly reached depth for a while, pulling it out, pushing it back in. “Yes, play with me as you please.”

I asked him to push it further, and he did it, fucking me deeper and deeper and he started to hit the upper turn. Still, two inches missing for a complete insertion. I told him to push it all the way inside me. I want this dildo inside and my hard fucked hole to close behind the handle. But Bob was holding back, he was afraid that we won’t get it out, not sure if some of his subs had this problem, but I assured him that I can push it out. So he made me prove it, he pushed it in almost all the way, I pushed it back out, and now we are good to go.

So he pushed it all the way inside and used his finger to push it even further to get past my hole. My hole closed behind it and the dildo vanished. He hasn’t seen this before and loved it. I wish he would have made me sit up, pull out his dick and suck him for a round while his dildo stayed inside me. He made me push it out, my hole opened, he grabbed it and he continued fucking me with the full length of this fucking double dildo, all the way to the upper corner of my colon. He hit this corner again and again while fucking me with that double-dildo – I should feel a bit sore in that spot the next day, but the sensation at the moment was worth it.

We have been doing this for a while now, a couple of hours, but we still had energy. One of the benefits of doing it early in the day I guess. Bob said that it would be unrealistic to use “Big Berta” on me in this session. It had the circumference of more than a hand, and I only made it to four fingers plus some depth training. But he asked if I want to try his newly acquired prostate plastic toy. “Of course, I like to be your test object, and I’m not sure if my prostate was ever stimulated directly.” He went to get the toy and we figured that it was time to change me to doggy for this part. This toy was not too long, had a thicker ball on the top, and was heavily bent to hit the spot. I presumed the doggy position right before bobs face, I pushed my back through as the woman do it in porn, and I spread my legs in the kneeling position.

My hole was in the right position and I served it to Bob for his pleasure. With all the stretching and fucking for hours, my hole stood open just by itself, especially in this butt-up doggy position. And it seemed to be enough motivation for Bob to take his beloved “Gun Oil,” hold it above my hole, and let it drip on my hole, where it flows right inside me without any assistance. I actually felt this colder liquid, making its way inside me where it spread. It was his favorite lube, what can I say, if he wants to fill me up with it then so be it. Let it flow. I had this oil everywhere, inside me, on my dick, all over my cheeks, just everywhere.

Then he started to use the prostate stimulator on me. This thing did slide in right away, with no resistance, no objection. But Bob operated it very strongly, first he fucked me hard with it, just in and out. Then he started to aim the tip in various directions inside me, pushing hard against my inner walls. He also massaged my dick while he was having his way with me. After a while, my hole was thoroughly fucked by Bob’s toy and he started to find the spot after wildly swirling it around inside me, I asked him if I am allowed to jerk myself and cum. He allowed it and placed a piece of paper where I can cum.

He was still pushing this toy hard inside me and pushing against my prostate so it didn’t take long until I came hard. Not those smaller loads that come when you watch porn. This was a huge load, I don’t even know if I ever ejaculated this much. I came, and Bob continued with the toy for a bit longer just to finish me off to the very end and let me cum body jerking continue while I was coming and after. Then he stopped and told me to stay right there. He got a wet washcloth and started cleaning my but and my dick very thoroughly. Just like you would treat a toy, the toy that I wanted to be to him, use it, and when you are done clean it well and stow it back in its place.

Now I could stand up, he let me wash my hands, I dressed, and got all my things. Then he gave me a brief hug and we went to his main house from which we said goodbye and I then went to my car. The goodbye was very quick. So now I was driving home, still feeling where Bob fucked me with his dildo and my hole which was anything else but tight. Unfortunately, we didn’t get his hand inside me, “Big Berta” remained cold during this session and the landline phone surprise didn’t happen – this time – Doing these things takes training and time. I may write part two of my encounters with Bob, I hope you enjoyed the beginning.