First Meeting Favourite Gay Sub

I am standing totally naked with my fully erect cock standing out straight in front of me, in my favourite dungeon. My regular sub, for over a year now, is strapped to a black leather spanking bench, kneeling with his legs forced apart. He is wearing black nylon stockings and suspenders but his very red bottom is presented naked, with six red parallel welts across it. His huge cock hanging down between his legs, fully on display, and giving me complete access. I have my favourite black leather handled rattan cane ready to continue caning his backside hard. He has goaded me into this before our meeting, by saying I have not yet found his limits, in our caning sessions to date. I have decided to give him an extreme caning today to find his limits and then fuck his arse long and hard.

THIS IS US NOW:

but this story is of how we got here and in particular, my very first meeting with the regular sub who has now become very special to me....

I am a Bisexual guy with a high sex drive, who loves bottoms and enjoys spanking them. I joined a very specialist Male to male Internet spanking site. This site has less time wasters, because all the members share the same interest. Either spanking or being spanked. Over the years I have met a few guys through the site and enjoyed spanking quite a few mens bottoms. Although, there are lots of willing bottoms, the problem for me was that I could not accommodate for spankings. Then I found a fully equipped dungeon close to me, available to hire by the hour, at a reasonable cost. Suddenly, I could accommodate and attract a lot more interest from men wanting spanking and more. Mostly though they were only one off, or just a few meets. I am very conscientious and put a lot of effort in, before and during a meet, to ensure we both have a very enjoyable time together. This extensive preparation is obviously more worth while if we go on to meet regularly. So I am always on the lookout for a sub guy for regular meets.

Then I got a message from Jon.

His profile seemed sensible, and the fairly innocent picture of his bottom in tight shorts looked interesting. Nothing like the many more explicit pictures of naked bottoms being spanked, elsewhere on the site. The message simply said "I am sub and need my bottom spanked, if  you would consider me worthy of your attention ". Again not like the normal explicit messages I get from other sub men on the site. This intrigued me and I responded,  asking if he would be willing and able to travel to the dungeon, which was at least 90 minutes from his house. Yes, was the reply.  Jon explained he was very inexperienced but needed a master to administer regular firm spankings, no sex at first.

To cut to the chase, I arranged a one hour session with him at the dungeon. He had very little experience of either spanking or sex. Only once, in his 35 years, had he had sex with a women. About 10 years earlier he had met an old man, who had spanked his bottom and little else, for about a year, before the old man sadly passed away.  No other sexual or spanking contact since then.

At this point it might be a good idea to describe the dungeon, to help you understand the flow of the story better. It has a small kitchen and as you would expect the usual toilet and shower facilities. A small dressing room caters for the ladies, crossdressers and in particular the sissies. It has a dressing table with mirrors, lots of makeup and jewellery available. Dozens of wigs in all colours and styles, hats and womens shoes, mostly with heels. Racks with a huge selection of dresses and ladies clothing of all types you might imagine. Then their is also a boudoir/bedroom which I frequently also make use of. Then the main dungeon. As you would expect, this is dark but a multi coloured versatile studio lighting system is installed, as it is regularly used for filming. It is fully equipped with all the dungeon furniture and equipment you would expect, plus a lot more you might not. Much of this, I have yet to explore and try out. Lots of fun to be had! Mostly I make use of the spanking benches, with straps for subs who enjoy being fastened down. Every type of paddle, whip, strap and cane is there, with much more, which I may use in future stories. Hopefully, you will get a better feel for the dungeon as I describe it in my stories but it has absolutely everything any Dom needs!

We met at the dungeon, where he dressed as I requested in black ff seamed nylon stockings, suspender belt and satin ladies panties. Jon presented himself in front of me in the bedroom of the dungeon. Standing very Submissive, with feet apart and his hands on his head awaiting inspection, as he had obviously been taught by his previous spanker. This is not unusual in the world of BDSM, but I had not had a sub present like this before, without first being instructed. Jon was to prove very sub indeed. A real pleasure for any Dom. I asked him to call me Sir, not Master and explained that my safe word is always RED.

Jon is a tall, good looking guy, with a very fit toned muscular body (from regular gym exercise) and a very fit spankable bottom too. I enjoy nicely rounded bottoms, not too slim and Jon's was indeed a very nice bubble butt. He allowed me to inspect his body with no objection. I took advantage, feeling his muscular chest, then I felt his legs through the  nylons and then his very attractive bottom though his panties.  He continued to stand in his Submissive pose whilst I felt his cock through the ladies knickers. I was surprised to find how huge it was and it grew as I touched it. I took advantage of Jon's submissiveness and enjoyed feeling his bottom and cock for quite a while. He was obviously enjoying this attention but remained in his submissive position throughout. My cock was already beginning to harden. I was looking forward to this session now.  Taking my time, feeling under no pressure to perform and also feeling very comfortable with Jon. I was fully in control and able to proceed at my own pace. Jon was obviously enjoying giving his body for my enjoyment. Already I could see that Jon would make a very compatable partner for me. We had discussed the session a little beforehand and I had fully planned out what I wanted to do and from our discussion I knew this was also what Jon  was looking for. Jon's main stipulation was no sex at our first meet. This disappointed me, but left the opportunity open for sex at future meets.

I had positioned a chair ready and sat down and instructed Jon down across my lap. I was naked and could feel his cock touching mine through his panties. I lifted Jon's silky top to expose his bottom and continued to feel his delicious arse through the silky knickers.  It was a very fine arse indeed, perfect for spanking. I felt his legs encased in nylons running my hand along the seams all the way to the top. Very sexy. I was enjoying this but must now get on with the spanking. Starting over the panties, quite gently, as this was our first meeting. Getting a feel for Jon's levels and preferences.  I always take time to try to understand my sub and his needs. Sessions are more fun for both, if you are giving your sub what he needs and enjoys too. Jon's experience to date was over the knee spanking, so I knew he would really love this.  Spanking and feeling his bottom through his panties.  Then my hand wondered down his stockinged legs and back up between his legs. Feeling that enormous cock trying to break out of the panties. Wow! It was getting even bigger. Felt so good. It was so much larger than my own penis. A good indication of how much he was enjoying this. Spanking over panties, then my favourite bit. Gently pulling the knickers down, but that big cock at the front was preventing them coming down. Stand up! Knickers down! Oh! my first view of that huge cock naked. I was certainly not disappointed.  It was long and thick! I rubbed it a little and it continued to grow even more. I did not think it was possible to get any bigger but it just continued to as I rubbed it! Back over my lap, you naughty boy.  I resumed spanking this now bare pink bottom. I could now feel his enormous cock rubbing against my legs and against my cock too.

Building up the intensity of spanking to make his bottom red. He reacted well. Obviously, still no where near his limit yet. Seems like this guy would take it quite hard. I would be surprised at just how hard in later sessions, but for now I was just enjoying working out his limits. Always so exciting with any new sub. The anticipation of whats to come and just how far things will go and how the new sub will perform. Its all part of the enjoyment.

I instructed Jon to stand up. His huge cock standing out in front of him. What a sight.  This guy was a real find. I took his cock in my hand rubbing and squeezing and feeling it growing in my hand. It felt so good, my cock was hard now too. We had not discussed this but I forced him down to his knees with his face in front of my cock. I knew he had not sucked cock before but he seemed willing to try. His inexperience showed but he tried very hard to please me. i am not a great lover of oral but i always enjoy being sucked to get me hard before sex. My cock grew and became hard we hadagree no sex this time unfortunately.

I was loving this attention but wanted to move things on into the dungeon for the next stage. He pulled his panties up and followed me through. I think he was surprised and overwhelmed by the dungeon but before he could take everything in, I began to fasten him to my favourite spanking bench. I had put the straps in place earlier and had the hand and leg cuffs ready. Then I placed a strap over Jon's back so that he was firmly secured to the bench. Bottom up, legs apart giving me access to all areas. I had chosen two paddles, a riding crop and a cane from the dozens available around the walls of the dungeon. Not sure what he can take, but I think the cane may be pushing his limit this early in our relationship. However it's my intention to try to establish his limits and then extend them each time we meet. Commencing with a few hand spanks over his panties,  feeling his bottom,  rubbing my fingers down his crack and pausing at his hole then continuing down to his balls and cock through his panties.  His cock still hard and huge. Then rubbing the paddle over his arse and down his stockinged legs. Slowly bringing it back up between his legs and gently rubing his cock and balls. then back over his nylon clad bottom again, preparing him for whats to come. Then paddling his pink arse, gradually increasing the intensity until I begin to get some reactions. This is reaching the right level for now. Just a few more and then change to the other paddle, which I know gives a harder impact. Gauging the level, I'm enjoying this and decide I need to see Jon's bare bottom again, so the bit I always enjoy again, pulling his knickers down to see his now red butt. What a view, bubble butt, with cock and balls hanging between his legs. I am enjoying this so much and decide I need my cock sucked again. Moving to the head of the spanking bench I offer up my cock and Jon stretches his mouth across to service me. More training needed but very enjoyable and I can still reach his bottom with the paddle to encourage him.

Before I get too worked up, I return and use the black leather riding crop on his bottom.  i love the smell of leather and the feeling of the leather handle in my hand. So tactile. I always delight in giving the long strokes necessary with the crop (or the cane). The secret with the crop is to let the leather tail do the work. The impact is in a small area only, which it is very effective. Jon took the riding crop well. It's sharp impact in a tight spot can often be too much for some subs. Jon was already proving to be an excellent sub for me.

His cock and balls are on view for me and I cannot resist feeling his warm soft balls. Rubbing between his bottom and his balls and then taking his massive cock in my hand. As I rub it up and down it grows and becomes harder. I cannot find the words to describe it adequately. Enormous, giant and massive. It's long but also has a huge girth in my hands. Such a pleasure to have it in my hands. It is easily the largest cock I have ever seen in the "flesh". I feel so lucky to be playing with it. A little pre cum, but my sub knows he must not cum without permission. I am not ready to let him cum. I must find out if he can take the cane. The cane I have chosen has a comfortable leather bound handle and is nice and whippy. I swing it through the air teasing Jon with the sound as it swishes through the air. OK. Cannot wait any longer. How hard dare I hit his bottom with this first stroke? He has taken everything so well until now but I don't want to go too far, too quickly. So decide on a medium hard stroke to begin with. I always like to leave the hardest stoke for the last one in each sequence of six. Can Jon take six? The first stroke shocks him a little but he quickly recovers. One thank you sir he says. Good - I will continue at a similar level for the first three. Then I feel his warm bottom which now has three red parallel welts. Well done. Three more now; increasing in intensity. Expecting to get more reaction now. Yes, he know his caning is getting harder, I can hear it in his reaction and counting which is coming with some delay after each stroke now. Four thank you sir.... five thank you sir.... then the final hardest stroke a delay then six thank you sir. For a first meeting, with an inexperienced sub, I cannot believe how well he is taking his punishment. Shall I leave it there? We agreed no sex but I think I deserve to cum and I think Jon deserves to cum too. So I rub my hard cock up and down his bottom. Simulating anal sex without penetrating. I am so ready to cum! Wish I could get my cock Inside his bottom - but I did promise. Maybe next time! For now I must be satisfied to cum on his bottom. I explode, squirting cum up his back. Then I take his massive cock in my hand and wank him until he erupts. Squirting a huge volume of cum over the bench and floor. I think he is very satisfied for a first meet.

We do go on to meet very regularly for the next year and more; so look out for more stories outlining Jon's development as my regular sub. We have both experienced so much pleasure together as Jon's submissiveness and experience have grown over the last year.