A Special Indulgence Pt. 01

"Morning David, how's things?"

"Good thanks, you?"

"Yeah, really good, beautiful morning."

This brief exchange takes place as we approach each other across her gravel drive.

A couple of minutes earlier I'd pulled through the gates onto the enclosed drive that stretched across the front of the house, as usual she'd heard me pull in and had walked out to meet me.

Initially I'd been Debbie's twice a week handyman and gardener at her large 18th century country house, I'd done that for two years until she'd sold up and moved into this, almost as large, house a year ago. Since then I'd been her handyman as and when required. A purely work related relationship.

As we got closer I saw that, unusually for her, she wasn't in her normal attire of jeans and tee-shirt but looked very...I wanted to think business-like but that wasn't right, she looked...different. In a loose fitting gunmetal grey silk blouse, dark grey calf length leather skirt and shiny black patent leather boots, she also looked a good deal taller than her 5' 2" in trainers; I glanced down at her feet and sure enough her boots had very high stiletto heels, 4" at least, also; her lipstick was a deep red: a real departure from her usual lip balm, and her long mousy coloured hair was pulled back into a very tight ponytail. This really wasn't the Debbie that I knew.

As we met midway between my van and the house I said, "Looking good Debbie."

She smiled, "Thank you, I'm afraid I have a meeting in town this afternoon so I'm going to have to leave you to it a bit later."

"No problem, let's see what you've got for me."

I didn't realise that this could be taken a number of ways until she looked me in the eye in a rather questioning way, I didn't know what to say so just stood, after a few seconds she seemed to decide that I hadn't meant anything by it and turned towards the house.

I followed on a couple of feet behind but couldn't help but watch her bum as she walked; I'd always quite fancied her in her tight jeans and tee-shirt but those stilettos seemed to make her bum sway even more than usual and she was obviously quite comfortable walking in them, even on the gravel.

Mmmmmm, I started to imagine putting my hand on that bum.

She suddenly stopped and turned.

In that instant I realised that I had actually spoken aloud!

"Fuck!"

And I almost walked straight into her, "Shit, sorry Debbie!"

She doesn't say a word, doesn't step back, just looks straight up at me. Then, without warning, she reaches up with both hands, pulls my head down, and kisses me on the mouth. The move is a complete surprise, I'd expected a rebuke, not this. I almost pulled back but managed to withhold the automatic response.

Instead, I kiss her back, her lips are full, soft, warm and taste of lipstick.

Her lips part and her tongue slips through, probes my mouth.

Then, suddenly a shift, she pulls her mouth away, steps back. Looks at me again. Think I've made a massive error. Then her eyes clear, her frown disappears, she makes a decision. "Come on." turns and continues towards the house, I follow.

Into the kitchen. Once inside she looks pointedly at my shoes, I crouch and remove them. Without speaking she turns and walks out into the hall, stops and looks back at me, Once again I follow.

Into the hall, up the stairs and into her bedroom suite.

To find her standing in the centre of the room.

I walk up to her, stop just outside touching distance, still not sure how to proceed, she had led the way so far and I had the feeling that she was going to lead the rest.

I was right.

She stepped up to me, put her hand on my chest, slowly circled around me trailing her hand across my shoulders, over my back and around once again onto my chest. I could feel my heart rate increasing, the heat building in my groin. I had no idea where this was going but I doubted it was going to be anywhere I'd expected when I'd climbed into my van first thing that morning.

She walked away from me, stopped at the dressing table, picked up a compact and lipstick. Turned towards me, opened the compact and began to re-apply her lipstick. Considering the circumstances this simple act was incredibly erotic without being overtly sexual, I almost groaned aloud.

Her eyes flicked up to mine, she put the lipstick and compact down, again walked towards me.

Stopped an arms length away, "Take your clothes off David."

For a moment I paused; I'd known her for three years, trusted her, wherever this was going it wouldn't be bad. I took my clothes off.

I had a slight feeling of embarrassment as I straightened from taking my briefs off, the atmosphere was extremely charged and I already had a thickening cock, I really didn't know what to do with my hands: cover my cock, put them behind my back or put them on my hips? In this situation none of these options worked.

But when I looked up I realised that it didn't matter where I put them; Debbie wasn't looking at my hands, or my cock for that matter, she was still looking at my face.

"I have a little...hobby David. A hobby I'm going to introduce you to."

Her eyes hadn't moved, "Undo my blouse."

My embarrassment had gone, now I felt in a complete daze: where the fuck was this going? My erection had faded minutes before, but at those words things down there were once more on the up. With shaking fingers I worked on the top button, then the next, progressing down until the last fell open.

Turned her back to me, "Take it off."

Fingers still shaking I take hold of her collar and peel it off her shoulders and down her arms.

To find she is wearing a black leather lace-up corset!

My wildest imaginings had never stretched this far, even 5 seconds ago.

"Take my skirt off David." Her words caught me out. I was still trying to comprehend this Debbie.

I reached for her zip then realised that I was still holding her blouse, a quick glance around and I draped it over her dressing table chair. Then went back to her zip, grasped the top of the skirt and drew the zip down to a point midway between her buttocks.

Drop to my knees and, gripping the hem, wiggled it off her hips and down to her ankles, she stepped out of it.

"Don't get up."

I actually don't think I could have: I was paralysed. Paralysed with shock and lust, with fascination and awe!

She was walking away from me, which only enhanced what I was seeing. A woman wearing a figure hugging black leather corset over tiny black leather knickers, black skin-tight thigh high leather boots and, sticking out of a sleeve in the side of the right boot, what appeared to be a crop!

She stopped at the bed and rummaged in a large shoulder bag before putting it on the floor.

Then took four more paces and turned. Fucking hell!

The corset certainly was figure hugging and she filled it. The zip that ran from the middle of her ample cleavage down to in front of her knickers was straining to hold her in, but then the five straps and buckles spaced out down the length of the zip were more than adequate to finish the job. The wide shoulder straps completed the look of a leather wrapped dominant woman.

A Dom. She was a Dominatrix.

She stood there looking down at me with a very serious face, whilst slowly pulling on a pair of gloves, black leather obviously.

"I would imagine that you've guessed what my hobby is by now David?" I just about managed a nod.

A smile flickered across her face, "Not difficult I suppose. Hadn't planned this, although I will admit that I have occasionally imagined it, but events seemed to have taken over this morning."

"I want you to know that my...hobby is mine, it is about me and my desires, it's what I enjoy doing. Luckily, for me anyway, I have found that I have been able to indulge my desires, to practice my hobby if you like, on some very willing participants. Mutual gratification is a term I hear a lot."

She'd finished pulling her gloves on and was now standing with one hand on her hip and the other tapping her chin, as if she was trying to decide what to do with me.

"I suddenly find myself in a bit of a quandary, I really hadn't planned this so I need to say something, and to ask you something, before we go any further. If we continue with this we will have two very different relationships, we will have the relationship we have always had: I will be Debbie and you will be my handyman, we will not mention or even hint at this other, secret, relationship and we will only delve into this other relationship if I instigate it. We can only have this secret relationship if we have our...normal relationship, and we can now only have our normal relationship if we have this secret relationship, we can no longer have one or the other, we have already crossed the line. My question for you is, do you want to continue?"

She held up her hand to stop me from answering, "I will tell you now that I do." She dropped her hand, an invitation for me to answer.

I tried to speak but my voice only croaked, I cleared my throat, "Yes I do. I'm intrigued, I'm fascinated, turned on, definitely yes I do."

She smiled. "Good, in that case, there are some rules in this secret relationship. The first is that you never speak unless I ask you something. The second is that you do everything I tell you to do when I tell you to and the third is that you are not allowed to cum until I say you can. Nod your head if you understand David. Good. If there are any others I will tell you as we go along."

My daze had cleared long ago and the sheer eroticism of the situation was once again...reasserting itself.

"Stand up David." The situation demanded that I did as she said, this time I forced myself to keep my hands at my side.

This time her eyes looked me up and down, "I always knew that you had a good body, I used to watch you if you had your shirt off you know." Her eyes fastened on my once again iron bar of a cock; he certainly seemed to be finding the situation stimulating. "What I didn't know was that you had that."

Her eyes came back up to mine, "But that's for later. You're not my usual...type David, in more ways than one. And we've become friends over the last three years, so this will be different for me. Unfortunately, as I said, I have a...meeting to go to, so I can't stay too long; still, I can start your education."

"Lie face down over the end of the bed. A little higher. Good. Don't move."

I can hear the faint creak of the leather as she moves, sense her standing behind me.

Feel her touch my bum, stroke it with her gloved hand, the leather almost soothing. For a moment, and then, smack! A sharp stinging pain on my right buttock makes me jump and yelp: as much in shock as pain, but immediately her hand was stroking, soothing me again.

Her hand slips into the crack of my arse, fingertips pause at my anus, brush up and down across the puckered hole; I'd done this a hundred times to women but never had it done to me, I was surprised at how much I enjoyed the sensation: her touch was light, delicate. Unconsciously I squirmed against her fingers.

Instantly, her fingers froze, still touching, not moving, "Don't move David, not unless I tell you to." Her voice commanding, severe.

Her fingers begin again, brushing up and down. And by not being able to move the sensations seem to be amplified. I felt a tingling that travelled all the way up my bowel then spread between my arse and my balls. If she kept this up I was going make an awful mess on her bed, instructions or not!

I do the only thing I can, or at least the only thing I want to do, I focus on not cumming, probably focus on not cumming as much as I've ever focused on not cumming in my life! I thought of just about everything I could think of except Debbie standing behind me dressed completely in leather, stroking my arse with her fingertips. And it works, or at least it works for as long as I need it to; although I can't vouch for how much longer it would have worked if she hadn't stopped when she did.

But, thankfully, stop she did.

"I could see that that was a bit of a struggle David. But you did still move I'm afraid."

Smack! That's as big a shock as the first time she'd slapped me, or is this a spanking? Smack! She hit me again. And again. Alternate cheeks each time, and it stung. Hadn't been smacked since school back in the dark ages, but old Mrs Lees certainly hadn't had the same effect on me that Debbie was having. And why the fuck was I thinking about Mrs Lees? That really was weird.

Then she stopped, Debbie that is. She stopped spanking me, I'd settled on spanking, far more erotic than smacking. She stroked my bum, again going from cheek to cheek, "My, they are nice and red David, I do like a man's bum, probably as much as you like a woman's bum. I'm going to show you two of my most favourite things now. Don't move David."

And her hand stopped stroking me, went away. Left my hot stinging arse. I so wanted it to come back, to start stroking me again, even to spank me again, just wanted the hand back.

But it didn't come back, at least not in the way I'd wanted it to, although pretty soon I realised that this was just as good.

I could hear her, hear the leather creaking, hear her breathing, hear her doing something, but I didn't want to look, I was beginning to enjoy doing what I was told, enjoying not knowing what was coming.

And then it was back, just the one hand, fingertips stroking across my buttocks, from one to the other but slowly getting closer and closer to my arse until she was doing it again: fingertips flickering across that sensitive ring of nerve endings; god that felt good.

Then a very different sensation: cold, wet, on the tip of a finger, a gloveless finger: I can feel the sharp edges of her nail right in the centre of my anus. I analyse the sensation, doesn't take much, I know what's coming. The fingertip traces a circle, then carefully pushes against me; I try not to tense against it, pushed back instead, testing myself.

"Mmmmmm, bad man."

She continues to press into me, feel her enter, the sharpness of her nail, then her slim finger probing through my sphincter, then beyond, felt as though it had entered a cavity, her fist pushed up against my bum, her finger in as far as it will go.

Which isn't far to be honest: she is only 5' 2" after all, at least that's what she is without those stilettos, and her hands matched her stature. But even so, the finger squeezing passed my sphincter felt inordinately large, and my bum wanted to squeeze it back out again.

It was an urge I resisted, it wasn't painful; having a finger up my bum. In fact, knowing it was Debbie's finger made it extremely erotic, especially the version of Debbie I had standing behind me right now.

And then it started to move: she pulled it nearly all the way out, then pushed it all the way back in, I could feel the shape of it as it rubbed against my sphincter, had a mental picture as it pushed through, the nail then each knuckle, then in reverse. Then the finger started to rotate, then curl; each movement a variation on the last. My mind jumped to the memory of the times when I had had my finger in a woman's bum and how that had felt to me, and now I was on the receiving end, and how different that felt.

Then it changed, the finger had paused. I felt a second finger probing; slightly thicker, that mental image showed me a middle finger alongside an index finger. And, even though those fingers were each very slim, the two together became a very different dimension.

That pushed up against that tight muscular ring, pushed and released, pushed and released; she didn't force it, knowing full well that eventually she would get her way; each time she eased a little further into my body. And each time I relaxed that little bit more as the stretching pain backed off until I felt her fingers pass the last resistance and once again her fist pressed against my bum.

She didn't wait, she immediately started fucking my arse with her fingers, that thrusting, twisting, curling fucking that totally filled me. A fucking that built on the pleasure I had felt before, that once again sent ripples radiating out into my groin, that quickly replaced any initial pain and very quickly reignited my flagging erection.

And just when things were beginning to approach boiling point it all changed again.

Her fingers disappeared, and left, what felt like, a yawning chasm of an arse. But were immediately replaced by something that wasn't Debbie, at least not in terms of flesh. It was still Debbie but not in a way I'd truthfully expected, but then up until an hour or so previously I hadn't expected anything. But this, this was something very different.

And I knew immediately what it was, what was pressing up against my already shrinking hole, trying to force its way in.

I tensed.

It was harder and smoother than her fingers, actually felt a bit like a cock but, unless I was 100% wrong about Debbie, it wasn't that. It also felt inanimate, no feeling of...life. Those couple of seconds of surprise and thought quickly accepted the situation: if this was the second of her favourite things, who'd have guessed. And I'd actually enjoyed her fingers up my arse, so I suppose that this was the next step, and I've always said I'll try anything.

So I relaxed, I consciously relaxed my arse: gave into Debbie's pressure. And felt my arse begin to spread. But this was much bigger than her fingers, at least that's how it felt, and despite the copious amounts of cold gel I could feel spreading across my bum it felt huge.

But now I wanted it in me. I wanted to experience more of Debbie's favourite things, so I pushed back, pushed back against her and, despite the eyes screwed shut, fist and jaw clenching pain, the thick hard intruder slowly sank into me. The head of this thing spread my sphincter until, with one last eye watering effort, it plopped into my rectum.

I released my long held breath.

"Mmmmmm, well done David, I won't punish you for moving this time but just remember what I said."

And with that she pushed it further into me. Which was when the realisation hit me that she was gripping my hips, she was fucking me! Which meant that she was wearing a strapon! Now that was seriously erotic. She was fucking me doggy style. One of her most favourite things was fucking men!

And that is what she did. She fucked me. There was no finesse to her fucking, her pleasure was coming from her feelings of dominance over me: she had me before her on my hands and knees with her 'cock' up my arse and she was fucking me as hard as she could.

She pulled me back onto each thrust, my sphincter once again spread to accept the intrusion and, as the underside of her strapon rubbed across my prostate, the feelings of pleasure once again replaced all those of discomfort and pain.

She had built herself into a rhythm and each time she ploughed into me the straps and buckles smacked up against my arse. And each time her cock slid across my prostate those tingling feelings yet again radiated out until once again I knew the brink wouldn't be too far away.

And then she gasped, "Don't you dare cum David. Don't you dare!"

And even in my state I could tell from her voice that she was about to cum herself: so it wasn't just about dominance, She actually got a physical pleasure out of this, maybe I didn't have to hold on for too long, if I could j...

That was as far as I got, "Aaaaaargh!" It was Debbie, gasping on the end of her cock, she'd given me no warning, I hadn't sensed her being near, she'd already been on the brink when she told me not to cum.

Now I could feel her, shaking and panting behind me, cock buried to its hilt, hands in death grips on my hips. Then she dropped across my back, leather, buckles and straps digging into my flesh, sweat dripping onto the side of my face. "Mmmmmm, that was...mmmmmm."