MEETING MISTRESS GERTRUDE

The Beginning

We were sitting in Martin’s basement. In a room he called his ‘Games Room’. This is where we played cards or pool every few weeks. A few years ago, before Martin got married, we used to go out a lot more, but now, with the rest of the guys getting married and settled, well, our get togethers have also become ‘settled and tame’. Today, Martin, Richard, John and I were playing a game of pool that was getting very slow and boring…very quickly! I looked at my friends and once again noticed how our interests and our lifestyles had diverged in these last couple of years.

All us guys met in our early twenties when we started working for one of the investment firms in the city. Back then, we used to go out every weekend and get up to all sorts stuff. These days, my friends were becoming domesticated and boring. I was the only one still wild among them, I wasn’t married nor did I have a serious girlfriend. Life is too short to get tied down like that and I had no trouble finding a gorgeous babe for some fun times (or sometimes more than one, but that is another story!). All of the other guys have become seriously tied down and because of all that we were now in the basement instead of upstairs because Lana (Martin’s wife) didn’t like us upstairs.

"Your turn Tony" I heard Rick say, so I got up and hit one ball in the pocket and then the another, the second missing the hole.

"Did John tell you about that new blonde who started downstairs?" I asked them. "I’m gonna get her to suck me off by the end of the month" I added. They looked up at me and John smiled.

"Yeah, she’s hot, I wouldn’t mind fucking her too," John was getting very enthusiastic, and I just couldn’t help myself.

"Yeah, I bet your girlie would think it would be hot too... maybe you should have a threesome!" I laughed, as I thought of the shit John would be in if his girlfriend, Sally, found out he was even thinking of fucking someone else. That shut him up! So I continued.

"I should get her to bring a friend when she’s sucking me off. I wouldn’t mind two of them having a go!" All of them were looking enviously at me. I was the only one who ever had a threesome among us, the only one who tried anything different. I bet none of them even got a blow job from their chicks, they all looked too uptight to me. I was getting so bored here!

"Hey, one of Lana’s friend was telling her about this guy she knows who went to visit a dominatrix or something and apparently got his ass whipped raw! Ever tried anything like that Tony, you wild boy!?" I could hear the sarcasm in John’s voice.

"No, but I went to some BDSM Club with this chick and she volunteered to go up on a stage and had this gimp looking guy in a mask drip wax over her bare tits. She was a good fuck too, maybe I still got her number", I said, trying to change the subject. But John was persistent, he was trying to ridicule me in front of the others.

"Maybe you should go to a dominatrix Tony, it would do you good if some hardcore woman taught you a lesson. But you couldn’t handle that. I bet you would never do it", John continued. Then the others joined him, mocking me and saying that the only women I ever went out with were ones I could control. That I’ve never been out with a ‘strong’ woman and that I couldn’t handle it if I did.

"OK" I said. "Get me the number, I’ll prove it to you. I’ll go to some dominatrix and we’ll see who will whip whose ass!" I was sick of their bullshit little games. Maybe going to some dungeon would be pretty interesting. One more experience for me, right?

One week later I had a phone number of some chick called Gertrude. I called up her number and after I was sure the person on the other end was Gertrude I began to joke around.

"Hey Gerty, is it you I call if I want my ass spanked?"

"You must have the wrong number", a woman’s cool voice said. I must have hurt her feelings or something so I toned down my kidding. I did bet the guys that I could get photos of my adventure, so there was a lot to lose. "OK, OK, look I got your number off someone who said that you’re the best dominatrix to call when you need a BDSM experience…Hey! I can pay you good money", I said as I tried to rectify the situation.

"Go to a BDSM club, I don’t deal with novices", she asserted.

"I’m no novice, well I am, but I really want you to do it! Look sorry, could you do it please? I really want to be your slave!" I nearly laughed out loud when I said that, what a cool line to a dominatrix. There was a silence on the other end of the line, I thought she was about to put the phone down when she sternly replied.

"You know, I will do you after all, I haven’t had a nice cheeky ‘boy slave’ like you for a while. But because it is your first time you will have to go through an initiation ceremony. That takes two days. You will get picked up in the morning and come back on the evening of the second day. You will need to sign release forms stating that you agree to anything we decide to do to you…so that you don’t sue us if you get a bruise on your ass. And let your loved ones know you will be gone for the two days and the night so they don’t start searching for you. Think you’re still up to it?" she almost sounded cheery.

"Yeah, of course. When can we do it?", I said and then made sure that it was possible for her to take photos so I would have ‘a little momento’. So it was settled! In two weeks time I would be getting my ass spanked by a dominatrix, or maybe I would spank her!

Two weeks later, I was waiting at the train station for a woman who would be wearing black and was going to get me to sign the release forms. An hour later another woman was to approach me and take me to the dungeon. I was holding a bunch of red roses with three blue balloons. This was how they were to recognise me. At the agreed time, this stunning redhead wearing black leather pants and a tight leather vest underneath her coat walked up to me and handed me a few forms which I quickly signed.

"Hey maybe we should get together sometime?", I tried my luck, I could just see her ass spread as I was fucking her from behind. She didn’t even look up at me.

"You will end up doing whatever Mistress Gertrude lets you" she replied as she walked off. Oh well, you win some you lose some, I thought, as I watched her sexy ass disappear into the crowd. I went into a cafe to get something to eat and drink as I waited the hour until my dominatrix showed up.

After the hour, I moved back to my position, I was beginning to feel stupid with the three balloons and a bunch of flowers. "Tony?" I heard someone ask. I turned around behind me was an amazing looking blonde also wearing black leather.

"Gertrude?" I asked, this was going to be fun!

"No, I’m Mel" she giggled. "I am going to take you to Mistress Gertrude and I may assist her with your initiation. You’ve never been in a dungeon have you? You’re in for a surprise!" she giggled somewhat menacingly.

"You can initiate me anytime." I murmured to her as we caught the train. After a few stations we got out and walked out onto some seedy street which we turned down God knows how many streets and alleys. Finally, we arrived at a non-descript door which Mel opened with her keys. We walked inside. It looked like some kind of a store room, with boxes, brooms, mops and broken furniture everywhere. Mel led me through a couple of extra rooms and corridors until she opened another set of doors which led to a dark foreboding basement. We walked downstairs to a small looking room which had several more doors leading god knows where. There was a couch in a corner, a couple of pretty funky armchairs and a mini bar.

"Let me fix us a drink while we wait for Mistress Gertrude." Mel said, as she opened a bottle of vodka. "Straight?" she asked as she handed me the half filled glass.

"To your initiation!" she said as she downed her own drink and so did I, the strong vodka burning my throat. She then sat there without speaking, I was beginning to feel a little anxious but the vodka hit my system I began to relax a little. After a few more quiet moments, Mel suddenly got up and swore.

"Shit, I nearly forgot!" she took something that looked like a studded dog collar out of her pocket and put it on her neck.

"Is that a dog collar?", I wanted to ask. But only when I couldn’t, did I realise that my relaxed state had turned into a numbness, a numbness which led me into a blackness that had begun to envelop me.