I wasn't in the habit of answering personals ads but this one had caught my eye. Firstly, who even writes personal ads in the local newspaper anymore? These days those pages are filled with thinly veiled escort services or phone sex lines all vying for attention. Secondly, the ad stuck out, not for its boldness, but for its subdued undercurrent of impropriety. Ten low key words in 8 point Times Roman amid a sea of all-caps and exclamation points:
"resolute woman seeks cooperative man for discrete and restrained relationship."
The only nod to the modern world was the inclusion of a nondescript email address.
Every word had been carefully weighed but the message was crystal clear: here was someone looking for a bondage sub. The use of the word discrete suggested to me that she was either in a vanilla relationship or her job required her to keep her public and private lives neatly compartmentalised, perhaps a teacher or a doctor. That could also explain why she was advertising in the local paper instead of hooking up at one of the bdsm haunts in town.
I understood. At that time I was dating my long term girlfriend, a ridiculous term when you're both in your forties. Both of us were happy living apart and having our own space so marriage was never on the cards. We had a happy, affectionate relationship and the sex was still great after all the years of knowing one another. We'd fooled around a few times with tying each other up, bought a couple of blindfolds and a toy cat 'o nine tails but she was never really into it. It just wasn't her thing and I was content with that. Or so I thought.
Seeing the ad changed everything. It made me remember why I'd wanted us to try the bondage play in the first place: I loved that feeling of helplessness and loss of control when tied up and disciplined. I think that's what had turned my girlfriend off. She couldn't understand why someone would want what I was asking for and she couldn't bring herself to actually hurt me. I remembered that we'd quarrelled, made up by screwing our brains out and got on with our lives. I'd buried the feelings out of reach. Until now.
I knew I had to email this "resolute" woman straight away. I introduced myself as Tim and addressed her as Mistress making it clear that I thought I could be the right man for her needs but that I was new to the scene and basically had no idea what I was doing. She replied the next day enquiring about me and my desires. It just felt natural to open up my deepest feelings to her even though she was a complete stranger. We seemed to hit it off and spent the next few weeks exchanging more and more intimate emails.
Finally our email conversations got to the point where she extended an invite for me to visit her in person and prove that I was worthy to serve her by taking the first in a series of tests. She gave me an address and told me to expect the "scene" to start as soon as I entered the door. She asked me for a safe word so she would know when I'd truly taken all I could bear and in a slight panic at what that might really mean I randomly chose peach, having just eaten one during lunch. It seemed to amuse her since she signed off with the instruction to arrive on Friday at 9pm exactly followed by a peach and hand clap emoji.
At the time I didn't really consider that there could be an effect on my existing relationship. I didn't feel like anything had changed between us. We still met up, ate together, shared jokes, watched tv, sniffled through sad movies and fucked like we always had. We'd never declared our relationship to be exclusive but as far as I knew we had both been basically monogamous throughout our time together. On occasion one or other of us had flirted with someone else at a club or, in my girlfriend's case, had some intimate close contact dancing but usually we'd laugh about it next time we met and then make out if the story was steamy enough.
Older me, looking back now, is shaking my head at how naive I was. My only excuse is that at the time I assumed it would be a one off and I'd be done, having scratched that itch.
On the Friday I met up with some old friends from a previous job for a couple of drinks, mainly in the name of Dutch courage, but at 8:30 I left them in the bar and made my way to the address I'd been given. It turned out to be a very expensive apartment in a renovated warehouse. I pressed the entry intercom button and said clearly "it's me" into the microphone. She buzzed me in and then finally I stood at the door to the apartment, butterflies tumbling inside me in anticipation.
I'd dressed smartly but neutrally in a blue shirt, chinos and chelsea boots figuring that I'd probably be losing them within the first ten minutes anyway. I had no idea what she looked like or what she would be wearing. I took a few deep breaths and knocked on the door. I heard footsteps approach, unmistakably high heels on a wooden floor, and the door opened.
She was a few inches shorter than me, perhaps 5'10, but that was with the advantage of the 4" high heels she wore. Her legs and body were toned like a dancer's with firm, strong thighs and flat belly. Fishnets led the eye upwards to a black lace-up bodysuit made of a slick material that pressed and lifted her small boobs together. Her arms were bare apart from a tattoo of a chinese dragon that led down from one shoulder. Her left hand held a riding crop, waiting at her side.
But it was her face that made me catch my breath. She was naturally very pretty, wearing the bare minimum of makeup to accentuate her eyes and cheeks. She had a round face peppered with freckles and an enchanting smile. Short jet black hair cut into a bob framed her features perfectly. She could easily have passed for thirty even though I knew she was closer to fifty.
I barely had time to register this before she ordered me inside.
"Stand there," she said, indicating with the riding crop. "Feet apart and hands behind your back. Don't look at me unless I give you permission."
I complied, feeling nervously excited. She closed the door and I heard her turn the lock, sealing us in.
"Do you remember your safeword?"
"Yes Mistress, it's peach."
"Yes, peach, so apt," she said with amusement in her voice. "When will you use your safeword?"
"When I can't bear it any more." I replied.
She swung the crop and it stung me on the side of the face and I cried out without thinking. It was only later, when I understood how practiced she was with the crop, that I knew she'd controlled the position and force to perfection.
"You will always address me as Mistress."
"Yes Mistress, I won't forget in future."
"When will you use your safeword?"
"When I can't bear it any more Mistress," I repeated correctly.
"When you can't bear what?"
"The pain Mistress."
"Yes," she replied. "Use your safeword when the pain is unbearable or if you find the situation too intense. I will stop and give you time to recover yourself or bring it to a close. Don't be afraid to use it."
"Thank you Mistress."
"Do you know why you are here?"
"To prove myself worthy of serving you Mistress"
"And if you fail to prove yourself worthy?"
"I will cease all contact and will never see you again Mistress." We had discussed this by email in the run up to tonight.
"Correct. Now strip and place your clothing by the front door. You won't need it until you leave."
I kicked off my shoes and socks, removed my shirt and trousers leaving my boxer briefs on for the moment. I folded everything and placed them on the floor beside the door. Steeling myself I removed my briefs and stood back in place with my hands behind my back, naked in front of a woman other than my girlfriend for the first time in many years.
I felt her critical gaze on me even though I could only see her feet. Self consciously I held my stomach in. I wasn't fat but my body lacked definition and in comparison to her glowing toned skin I felt pasty and flabby.
The tip of the riding crop touched my arm and then tapped firmly against my chest.
"When was the last time you exercised?" she asked
"I haven't exercised for a while, Mistress," I said, "I used to do some weights but I got out of the habit."
"If you pass tonight's test then I shall expect you to exercise properly. Your body will belong to me and you will not disrespect my property by treating it like this."
"Yes Mistress."
The crop moved around my body touching and patting various parts until she tapped it on my penis which twitched in response. She lifted it up on the riding crop, moving it this way and that to check it over. I felt my face redden.
"Uncut... interesting," she said
She flicked her wrist again and whacked my penis twice with the tip of the crop. I gasped at the sudden pain.
"On your knees now," she snapped. "Face against my shoe."
I folded up onto my knees, grateful for the protection it offered my penis although acutely aware that my rear end and balls were now exposed. I pressed my nose and lips against the leather toe of her shoe. The crop tapped its way across my body, a little dance down my back and along my side sending shivers down my spine. She pulled her foot away and I heard her walk behind me followed by the feel of the crop against my buttocks. It tapped rhythmically and then slid down to rest against my hanging balls. I tensed myself, prepared for an explosion of pain. I felt a bead of sweat drip down my forehead and along my nose.
"I could have you crying for mercy in thirty seconds," she said flatly. "Your whole body is shaking. Are you sure you're strong enough to serve me?"
"I am Mistress, I want it more than anything."
I felt the crop leave my balls and I braced as best I could. I heard it swish through the air and I heard myself cry out. There was no pain. She brought the crop to rest against my scrotum again.
"I haven't even started yet and look at you whimpering on the floor. I don't think you're cut out for this at all. You should get your clothes and leave."
I felt her step away but I didn't dare lift my head to see where she was. I processed what I'd heard. She hadn't ordered me to leave. She was testing me, giving me one last chance to step back to my vanilla life. Red pill or blue pill.
"Please give me a chance to show you that I can do this Mistress. I've wanted it my whole life and I don't want to throw away this one opportunity I have to be my true self. I'm scared, yes, but it's because I'm on the brink of a chasm and I don't know how deep it goes. Mistress, please guide me and I will forever be devoted to you."
She made no sound. I knelt there in the unbearable silence.
"Please... Mistress" I murmured.