Ticking Off Boxes On A BDSM Checklist!

My boyfriend had been acting strange for a few days before he text me to meet him at the local shopping mall the next morning. So confident was I that I had covered my tracks, I didn't even entertain the thought he might know of my trysts with James* and Ken*. But as he strode up to me that cold, wet, dismal morning with his black, leather trench coat flapping about him in the breeze and sheets of white paper clutched in one hand, my heart was in my mouth a little. 

I greeted him casually, a quick peck on the lips, but he meant business. 

"I know about your advert," he told me, with no anger or hurt in his voice, only a questioning look in his eyes.

"What advert?" I hedged, having the nerve to look wounded. 

"Seeking a Master," he replied as I looked sheepish.

I didn't need to say a word, my guilt was written all over my face. But, to my relief, he didn't appear to know I'd had any responses to the ad, or, if he did, that I'd met with some of the respondents. Instead, as we sheltered under an awning from the driving rain, he showed me what was on the paper in his hand. It was a BDSM checklist! Rather than dumping me, he wanted to explore my BDSM fantasies with me. I should have felt like the luckiest girl in the world. Instead, I just felt awkward and uncomfortable. And more than a little ashamed. 

The relationship with Steve* came naturally to an end not long after the BDSM checklist incident. I ended things with him by, I'm ashamed to admit it now, text message. I'm sure my reasons had something to do with his wanting to explore the darker recesses of my mind. For reasons I'm not too sure of, I've always found it easier to explore the submissive side of me with strangers, or almost strangers. 

But as it turned out, that wasn't to be the last I'd see of Steve...

*names changed for privacy

Freezing My Tits Off Whilst He Snores In My Ear

After my relationship with Master James* went south, I began chatting with Ken* who, if you remember, was a father of three in his late-forties, living over a hundred miles away in Scotland. He had replied to my online advert ("Seeking Master") and we'd kept in touch even during my relationship with Master James. We were soon spending hours on Skype together, engaged in fairly innocent conversations, despite both our intentions. In retrospect, I think he was worried about coming across as predatory, given the age difference.

I had high hopes for my relationship with Ken. Because he was older, I assumed he would be more experienced. Although we'd never discussed his past experiences, his reply to my advert led me to believe he was a Dominant man. So I hoped that he could become my next Master and help me on my journey into the BDSM world. There was one big problem standing in our way; distance.

The first, and last, time I met Ken was in a hotel in my home-town. Ken made all the arrangements whilst I set up some lie for my mother as to where I was going to be Saturday night. Doubtless I told her I was spending the night with a school friend, even though I had none. My mum, though, was always so keen to believe I was making friends and having a social life that she swallowed the lie easily.

And so it was that I found myself lying on big, white hotel bed with Ken between my spread legs. He tells me he likes foreplay; he likes to pleasure a woman. Great, I think, what woman doesn't like foreplay? As the night wore on, though, I came (though not literally, sadly) to realize that Ken liked to pleasure a woman before sex because he couldn't do so during. This realization came as he huffed and rolled off me, after half an hour of rubbing and poking me with his flaccid, micro-penis.

I spent the next eight hours freezing my tits off on top of the covers, locked in his embrace as he snored contentedly in my ear. He slept soundly through the night, his attempt at sex obviously exhausting, whilst I laid awake until the sun came up.

I left as early as I could without hurting Ken's feelings. Yes, despite the awful sex I was still concerned about his feelings. And when I knew he was back in Scotland, I cut off all contact with him. I couldn't bring myself to tell him I hadn't enjoyed our night together. But I also couldn't pretend I had. So I deleted, blocked and ignored him.

And so what I'd hoped would turn into my second Master/slave relationship became the most awkward sex I've ever had; and I feel justified in saying that with more years of experience under my belt. It was also more vanilla, even, than sex with my then boyfriend who was still blissfully ignorant of my kinky explorations.

Or so I thought...

*names changed for privacy

Sitting On A Park Bench, Wearing No Knickers!

And so my first experience of kink was sitting on a park bench, wearing a mini-skirt with no panties on underneath, in the freezing cold night, whilst James* (a man I'd just met) slid his hand up underneath my mini-skirt and I began to shiver; partly from arousal, mostly from cold!

The relationship with James did not last long, a matter of weeks in fact. Because of school-work, my 'vanilla' relationship and his full-time job it was difficult to find the time to meet. Adding both of our living situations into the mix, me with parents and him with flat-mates, it was amazing we ever managed to do anything but chat over a pint! But we did; more commando trips to pubs, with James choosing my outfit for the night, a few more public play sessions, but always in the dark; a few years later found me 'upgrading' to shagging in a bush with my long-term boyfriend in broad daylight, whilst dog-walkers walked by! And, of course, my relationship with James was my first time, but definitely not the last, with an older man (albeit not as 'older' as some would turn out to be!)

As it turned out, the death knell for our relationship was my, somewhat unhealthy, obsession with vampires. The "Twilight" series had not long come out and I had become convinced, or convinced myself at least, that I was a vampire. I believed myself to be a more modern vampire, similar to the Cullens ("Twilight"), but one that definitely didn't glitter! And so, feeling I could trust my new Master, my new mentor, I confided in him, over drinks at the local, that I believed I was a vampire. I'm not sure what I hoped for out of this reveal; I think I just wanted to make it 'real.' But, naturally, he was incredulous and, when I insisted, became angry. Eventually he stormed off, with the parting line; "If you wanted to end things, Daphne*, you didn't have to make up some bullshit about being a vampire!" 

And so began, and ended, my first Dom/sub relationship. And, shortly after, began a new one...

*names have been changed for privacy.

Losing My Virginity On His Parent's Sofa!

I lost my virginity at sixteen, in a somewhat uncomfortable position on the sofa in my boyfriend's parent's front room. This was after we had, unsuccessfully, tried the kitchen counter and the kitchen floor (too high and too cold, respectively.) In retrospect, I'm sure my boyfriend, Steve*, had probably been watching porn, which is where this idea of sex on the kitchen counter came from, at least, and, when that failed, he moved onto other possible surfaces.

Like many, I'm sure, my first time was unremarkable; awkward and over far too quickly. From then on, sex with Steve was quick and frequently interrupted by his overbearing mother barging in on us without knocking.This led to me wearing skirts and dresses for 'easy access' and to save me some face! It certainly was not an adventurous sex life, unless you count the sofa shagging as adventurous, but sex was a novelty for us both and, so, exciting enough. Or so I thought.

At the time I was seeing Steve I was reading a lot of fanfiction online and, somewhat unsurprisingly, I came across some of the erotic kind and a world I hadn't known existed: a fetish world. Soon I was reading erotic fiction nearly every day and engaging in ever kinkier fantasies, which I would frequently get myself off to. But instead of talking to my boyfriend, and perhaps exploring the fantasies with him, I posted an advert online - "Seeking Master."

Knowing what I know now, nearly ten years on from my silly, sixteen year old self, I realize how stupid and naive I was. Both in thinking that sites like Gumtree were a safe place to find a sexual partner and in thinking the first guy who told me what to do was a Master. I was a school girl with no knowledge of the real world or of the BDSM world I wanted to inhabit. But, of course, I was flooded with emails (being young and reasonably attractive was as much of a rarity on these kind of sites then as it is today) and I began to talk with two males who professed to be interested in becoming my Master.

One of these men was Ken*, significantly older, married with children, and living over one hundred miles away in Scotland.

The other, James*, was local, older than me but not much, and quite good-looking! And so, after a few emails back and forth, I found myself meeting him for a drink in a local pub where he whispered in my ear over a Malibu and Coke; "go to the bathroom and remove your knickers."

It was as I was stuffing my sexiest knickers into my clutch bag and tottering back out to the table, in my ridiculously high heels, to James that I realized I had become a part of the world I'd only fantasized about till now. I'd taken my first tentative steps into the BDSM world, and I knew then that there would be more...

*names have been changed for privacy