It all depends on how you look at it. I have technically been kinky my entire life; I just never really shared it or expressed it with anyone until a couple years ago. If you count the years from when I first realised I was kinky, it was probably around my 12th kinkiversary last summer. If you count from the time I realised my interest in spanking and bondage was something sexual, it would be somewhere around my 6th kinkiversary. If you count the years from when I first made an online profile on alt.com, it would have been my 2nd kinkiversary last September. What I am referring to in this entry is my first time out playing with someone. And even that one takes some explaining.
Before attempting to meet anyone in person, I had played a bit online. I had met a lovely man from Australia, named Kurt. Kurt was my first peak into the world of domination and submission. We played online, using a web cam and instant messenger…until his wife found out. I had asked him earlier if he was attached to someone, and if that someone minded. He said that he was married, but that his wife would not mind. When she found out about our play, she got very upset, telling me that she did not wish this to continue and that she is not comfortable with it. I understood completely, and told Kurt that we could not play. He contacted me a few times, secretly, but I told him that I would not talk with him any more, and furthermore that I did not appreciate his dishonesty from the beginning. From this, I learned that if a person is married or attached, I should talk tot he other party directly, instead of just taking someone’s word.
I met a man named Hans on alt.com, and started chatting immediately. We talked online at first and then on the phone. He walked me through how to fuck my ass with a dildo – and it felt great. I almost came from it. I had finally gotten up the courage to meet him. The plan was to meet him at a hotel room. Stupid. The night before I was supposed to meet him, I had the strongest gut feeling to call him and cancel. Something just did not feel right. Following my instincts, I called him and told him that I was sorry, and that I was not ready to meet up with him.
What happened next almost broke me. He told me that I would never be ready, that i was too immature to ever be ready, and that I was stupid for listening to my gut. He said a bunch of other things, but thankfully, I have pushed them out of my mind. What I took from this experience is that I should always go with what my gut says, and that I should always meet someone in person, and have coffee with them before playing.
Looking back, my first time playing should not really count. It was…rather boring and uneventful, to say the least. I had been chatting with Dieter for about six months on alt.com, before deciding that it was time to meet for coffee. I hopped on a bus and went to my favourite coffee shop – Second Cup. While waiting in line for coffee, someone tapped me on the shoulder and said hello. I jumped a little, nervously ordered my coffee and waited for his order to be made before stumbling to a table and sitting down. My coffee was a prop. I did not drink it; not one sip of it. It was merely there for me to stare at and fiddle with. We chatted – well, he chatted – I just concentrated on breathing, and then decided to head over to a hotel, where he had booked a room. The play was light and less than what I had expected and wanted, and the chemistry was not right. He drove me home a couple hours later and I went in, processing what had just happened. I remember distinctly feeling numb, as though I had just had an out of body experience.
The next month, I ventured a little further outside of my comfort zone. I had been talking to Erwin for a little over a month and we had set picked out a day for me to come over and play. This meeting was different. For one thing, I was going to him, he was not coming to me. I pretty much set myself up for murder. I took a subway further down the Bloor line than I had ever been. I spent all of twenty minutes chatting with him, I got into his car – into a car with a “stranger” - and I had not left a note on my desk, informing my parents of where they could find my body if I did not come home.
Things were different this time. I had made it a point to get there half an hour early so that I would have some time to breath and drink my coffee. I also brought some philosophy homework along, so that my mind would be distracted by something. I knew it was Erwin the minute he had walked through the door. Scruffy hair, black glasses and a hoodie similar to one I would wear; exactly as I had pictured him. He sat down in front of me and eased my nerves a bit, talking lightly about life and kink. Soon after, we decided to leave and head back to his place.
It is a lovely little place just off the boardwalk downtown. The apartment was nice and fit his personality. There, I met his girlfriend at the time, Brigitte. She was quiet at first and stayed in a different room at first as we played. Erwin had tied me, bent over a spanking bench and was teasing me with a flogger. He then gave me a light swat, and then a harder one, and then an even harder one. He also taught me how to count the swats, and informed me that I would get hit if I did not call him “sir.” He then pushed a butt plug into my ass and continued to spank me.
After more spanking with different implements, Erwin tied me up with my breasts exposed. He put nipple clamps on me and stuck the chain into my mouth, telling me not to drop the chain. He then put my legs up and spread, on to a spreader bar that was hanging from his ceiling. He then fingered me…hard. Until this time, Brigitte had been in the other room, studying for school. It was not until I had started making noise that she came in and watched us play. He later removed the clamps and replaced them with chopsticks held together with rubber bands. He brought out a flogger and started flogging my breasts. I flinched a little before each lash, anticipating the sting. After he had decided that my breasts had had enough, he used the flogger to flick the chopsticks off my nipples.
Leaving me tied in that position, he called for Brigitte to come. He ordered her to take her pants off and bent her over me. She was bent right over my face, as he fucked her…hard. It was such a beautiful sight, much better than any porn I had seen. When he was done, he untied me, but told me that he wasn’t finished. He reddened my ass a little more, and with Brigitte holding me down, he scribbled something down in permanent marker. A souvenir for me to take home.
Before he drove me home, there was still one more thing he wanted to do with me. He wanted me to put my mouth onto his cock. It was a big step for me, because I had never done it before. Furthermore, the idea grossed me out, mainly because piss and cum come out of a person’s cock, and I had (and still have) a fear of bodily fluids. He let me experiment and explore with his cock, using my hand to jerk it a little, running my fingers up and sown the shaft, playing with the sensitive tip. I stalled as much as I could before putting my mouth onto it, but enough was enough. I had until the count of three before he threatened to tie me down and stick his cock into my mouth. I closed my eyes and slowly sucked on the tip. I let his cock go a little further into my mouth, and then pulled away. I did this another thirteen times before Erwin was satisfied with me.
We then cleaned up and he drove me home. I consider that night to be my first play session. It was like nothing I had ever experienced before, and I wanted more. Unfortunately, life got in the way, and I never played with Erwin again. For what it’s worth though, I am still thankful that I had the experience. It was the first little push I got into the kinky world.
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- 1st Kinkiversary! Almost…Maybe. Part I
- 1st Kinkiversary! Almost…Maybe. Part II


