A Flogging Good Time

I thought it was time I wrote about the initiation of J, someone I got talking to properly online but later found out I'd met in person though my job, coincedence huh?

J is older, a widower for several years, and a man who loved his wife very much, for him she was his one and only. Lucky for them finding each other, just sad they didn't get to grow old together.

Although J knows there'll never be another love for him, that doesn't mean he's deprived himself sexually, J has several lady friends of a similar age he lunches with, and on lol. Nothing wrong with them, or him, but for J it was growing stale, he felt other urges it was getting harder to deny inside him.

We got talking in a lifestyle chat room, J very curious and wanting to explore the submissive side he suspected was inside him.

I'm the type of person most find it easy to talk to, even about their deepest darkest secrets, but because of my laid back approach to BDSM , J found it difficult to accept I was for real, not just someone who sat in a chat room bragging about things I'd done and demanding all kneel before me as a sign of respect. That's not my way at all, I don't need to be called Mistress or Ma'am or have a capital letter put on my name to tell me my status in the lifestyle, I KNOW who I am.

The look on J's face when I arrived on his doorstep with my toy bag, a mixture of fear and excitement.
Needing to put J at ease I sat on the couch and accepted his offer of coffee, chatting to him about work and family stuff while he got himself together and calmed down a little.
J has had 2 major heart operations, not a good idea to get him TOO excited, the thought of calling the emergency services and explaining how J had collapsed while naked, cuffed and bent over a dining chair being flogged and finger fucked definitely didn't appeal.

We sat at opposite ends of the couch sipping coffee and examining the contents of my toy bag, I took each item out individually explaining to J how each can be used, either for pain or pleasure.
I have to say his eyes widened at a few things, the blindfold, the butt plug and the ball gag especially, but I knew I was on a winner when I took out my leather flogger, J got an instant erection. He sat stroking the leather thongs, looking at me and practically drooling with excitement as I explained how the flogger can be used to varying degrees, to sting a little, sensitising the skin, or hard enough to cause pain and bruise.

There was a moment I thought J was going to lose his nerve, time to take control of the situation I decided, and told J to strip, it was playtime.
J asked permission to pour himself a whisky, which I gave, and I sat back watching his discomfort and smiling softly to myself. I knew now for certain J took me seriously, this was now very real for him.

Again I sensed J was playing for time, the small whisky he poured himself was taking a very long time to drink, so I reminded him why I was there, and told him to swallow the remainder down quickly
Putting the glass down on the table J looked at me and began to undo his shirt buttons, asking me if I was serious about him having to remove all his clothing. "Of course," I confirmed. "I want everything off, including your socks."

There was a horrified gasp when I said the socks had to come off, what is it about men and their socks? It's like they feel less naked with them on, well boys I have news for you, wearing socks does not prevent me seeing your cock, so get them off!

While J was busy stripping I walked through to his kitchen and picked up a dining chair, it seemed the ideal height to use as a play prop. J could bend over it, lean on the back rest or sit on it, depending on my intentions.
Once J was naked I told him to turn the chair around so he could rest his hands on the back for support and lean forward a little, with legs spread wide he now made a wonderful target for a sensitising flogging, lovely stingy lashes all over his back, bottom and between his legs so the tips of the thongs flicked against his cock and balls.

I promised J I'd be gentle with him, partly by necessity because of his medical condition, but mainly because this was purely intended as an introduction, a taster to see if he really wanted to explore this side of himself further.
After a few minutes of this J's breathing was getting heavier, I could tell by his reaction he was relaxing and enjoying the sensations, so I decided to take it up a notch.

I reached for the lubricant and put a generous amount on my fingers, then slipped the tip of the middle finger on my left hand inside his anus and resumed the light flogging.
J flinched at the intrusion and squirmed a little at the discomfort, asking me what i'd put inside him. I'm not sure he could believe that just the tip of a finger could be so invasive, he just couldn't relax enough to allow more than one finger inside him, but with patience I did manage to insert the whole finger for a little while.
At this point it was obvious J was highly excited, his whole body was trembling, and I had concerns for his well being, so as soon as he requested we take a break I stopped and helped him to sit down and catch his breath.

I burst out laughing when J thanked me and said he'd just rest a few minutes before getting dressed, he thought his experience was over, he thought wrong. A session is not ended until I say it is, and in this instance I was not stopping until J had an orgasm. If this was to be his only foray into the chocolate side of life I wanted to make sure it was memorable.

Off came the 4 inch heels I was wearing, and out came the fur lined, leather, buckle up wrist cuffs I own. J was instructed to present his wrists and after each was fitted his arms were put behind his back and the D rings on the cuffs fastened together using the clip on bar.
Next on went the blindfold, J eagerly accepted it. I asked him to confirm he wished to continue, J assured me he did, so picking up my Japanese Clover nipple clamps I allowed the chain to jingle a little, a warning to J of what to expect next.

Putting the nipple clamps on I have to say i was quite sadistic, I pulled each nipple out firmly and just quickly fitted the clamps, not giving J time to slowly ajust to the intensity of their grip. If you've never tried clover clamps I can highly recommend them, especially those with a chain joining them. Gives a very intense sensation when you tug on it.

J let out a low moan, his head moving slowly from side to side. I tugged the chain hard, and I could resist whispering in his ear, "So do you still think I'm all talk hmmm? I'm not, am I J?"
His urgent "No" was all I needed to tug the chain again, and this time ask him to thank me for the pleasure I was providing.
That "Thank you Mistress", has to be one of the most satisfying I've received thus far.
J was instructed to sit with his legs wide open, exposing his cock and balls to my ministrations. With every flick of the flogger J's cock grew harder and harder, standing up so straight it was like a flag pole, delicious.

My second favourite toy after my flogger is the Warternburg wheel, something so simple, yet extremely effective in sensation play. I instructed J to hold the flogger handle in his mouth, effectively acting as a gag, but with a much faster safety release.

Very slowly I rolled the wheel across J's clamped nipples, down his stomach, then relocated to the base of his penis. Rolling it up the shaft of J's cock I could gauge from his reaction it was causing him a pleasure/pain sensation, one that is often very finely balanced. By the time the wheel reached the head of his cock J was oozing pre-cum freely, his excitement impossible for him to disguise.

There soon came a point where J could no longer hold the flogger in his mouth, so feeling generous I removed it and informed J that as he'd been such a good boy I was going to allow him to cum. I released his hands and instructed him to stroke his cock, then with the occassional tug on the nipple clamp chain I rolled the wheel across the head of J's cock, lingering over the eye each time I crossed.

By now J was so turned on he was stroking his cock faster and faster, desperate to cum, which he already knew he was not to do without begging for my permission.
To my surprise J now began begging for a cock to suck, something we'd discussed several times, and J had said he'd never do. Well, well, what a turn up for the books, J is more submissive than he realised, and also very eager to please me.

When I knew J was at bursting point I gave him permission to cum, pulled hard on the nipple clamps and waited for his cum to spurt.
A huge jet of creamy cum shot out of his cock, something else I knew J had never done was taste himself, which I'd assured him was something he would do with me. J was just as certain he would not.
Imagine his surprise when scooping up some of the hot spunk I pushed my fingers into his gaping mouth, making sure to spread it around inside. As his spasms slowed J began to react to tasting his own cum, pushing saliva out with his tongue to try and get rid of the taste. I just grinned from ear to ear and waited for J to come slowly down to earth, it took a while, but he eventually calmed down, his comment of "Well that was different", had me in gales of laughter, such an understatement for his obvious display of ectasy.

J has been asking me constantly for a second session, so I think even after J has had time to reflect he's eager for more, in every way, even begging me to take another man with me so he can suck a cock for my pleasure.




"The most powerful sexual organ in the body is our brain, open your mind and allow your fantasies free reign, mutual pleasure between consenting adults is a wonderful thing."
DanesWood