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Thoroughly Masochistic Millie

Thoroughly Masochistic Millie

The story you are about to read is true. Only the name has been changed to protect the guilty.

I’m going to do something I don’t do too often: I’m going to talk about a client. (She has given me full permission in the hopes that her story will help some young submissive not make the mistake she made so long ago.) Millie is a very special friend. The fact she is a client makes no difference really whatsoever. We became cosmically linked, so to speak, the day she first emailed me with her gut-wrenching story. And we’ve been great friends ever since. You see, that is one of the perks of doing what I do – I get to help women. And for this, they usually reciprocate with a showering of friendship. The session I’m about to mention took place late last year, before the Christmas season. I was checking my mail one December afternoon and I came across a very peculiar letter. The woman was sincere, in her mid forties and calmly talked about how her life had been ruined over the years by her father. Or, rather, by what her father didn’t do. She wanted to talk about the last spanking her father (a former Marine and strict disciplinarian) had given in which she badmouthed him, telling him he was enjoying the spankings and that he was a pervert. The father, after hearing these words from his then thirteen-year old daughter, backed down and another spanking was never administered – ever. And therein lied Millie’s problem in a nutshell.

Millie explains: “I used to dread the spankings. They were always done so ritualistically. I hated them so. He’d come in after I’d bathed and put on my nightie, with a straight-back chair in one hand and a paddle with holes in the other. He’d paddle me until I gave in – and sometimes I didn’t give in. He’d just let me up and then put me back into position again for more of the same, scissoring my tiny legs so I couldn’t move – sizzling my behind with that dreadful wooden paddle. He used to call it ‘paddling the devil out of me.’ This last time I had been playing with some boys, showing them my privates and ‘oohing’ and ‘ahhing’ over the size of their penises. This was a beating offense for sure. Their parents came over and told dad what I had done and that was when all my problems in life started.”

Millie and I communicated online with chats and on the phone for about a week as she slowly confided to me what it was that she needed. I wasn’t surprised. She wanted me to re-create that last spanking her father never gave her. She wanted to take that bath, get into her nightie and wait for an interminable amount of time on the bed contemplating her fate. She wanted no communication between us, unless it was absolutely necessary.

I came in about forty-five minutes after she’d finished her bath. I wanted her to stew a bit and think – really think – about what was about to transpire. (What we were doing was an agreed upon session consisting of “edge play,” a BDSM power-exchange in which the safe word is thrown out the window and the dominant holds all the cards as to when and where the session is to stop.) What she’d intimated to me was that since her father had backed down with that last spanking, she felt she could basically dominate men; get anything she wanted from them. This somewhat explained her five failed marriages at the age of fortyseven and numerous job changes. I was going to do everything within my power to take her back to that critical juncture where all the problems had started and re-create the pivotal scene that had dealt her such devastating results in her life. I was going to let her take her just punishment and continue on with her adolescence.

I opened the door to the bedroom. Millie was sitting with her feet crossed at the edge of the bed, very nervous, very proper. Her eyes were cast downward. I had the paddle and the straight backed chair, but she hardly noticed she was so far off into her own space – waiting for what we both knew was going to happen. What had to happen. What should have happened several decades previously.


Millie obediently stood before me, her eyes still cast downward looking at her tiny, pink toes — which were painted apple red.

“Come before Me.”

Millie complied. She even moved to my right, exactly where she knew she had to be. I instinctively grabbed her left hand and draped her gently across my lap, positioning her for punishment. I felt her body slide down to the lower edge of my right thigh, just where I wanted her; just where I could do the most damage to her near-virgin cheeks – and, after all, wasn’t that what she was asking me to do? Damage her, to undo what was omitted in that bedroom so long ago by a disciplinarian, whom, in her eyes, was now nothing more than an old man in a rest home wasting away as the years passed him by without as much as a card on his birthdays from his darling daughter. How could I fail her now? How could I even possibly think of not fulfilling her sacred fantasy? It was too important. For both us now. And you know what? I, too, was a bit nervous for this one. There was a lot riding on this paddling.

Slowly, I hiked her nightie up over her back, exposing her creamy, white buttocks. I could tell by first glance that these cheeks had not seen hand or implement of correction in an awfully long time. Her bum was completely exposed to me now. A bit moist from the bath, but nevertheless glorious in all of its suppleness. Like a bowl of Jell-O that has set perfectly – wiggling ever so slightly to the touch.

I took the paddle and placed it directly on her back. There was no mistaking it was there. It crossed her at the shoulder blades and teetered at every stroke I gave as I warmed up her bottom with my hand. (This was not a part of her punishment as a young girl, but I felt it was necessary since she hadn’t been spanked seriously in more than thirty years and, therefore, she needed a serious warm-up prior to the serious punishment she was about to undertake.)

Suddenly, the first blow landed with the paddle with the holes. Millie kicked her legs and her whole body went rigid. Then she relaxed, expecting the worst of what was yet to come. She almost wanted the paddling – begging for it.

“I want you to point your toes inward and give me your right arm,” I commanded, sternly.

I took her arm and wrapped it around her back, securing her. Her toes were pointed in a manner that she would be unable to “clench” her bottom cheeks while being punished. She remained in this position for the remainder of her punishment.

The paddle cracked twelve times across her glorious, glowing globes – six across one cheek, six across the other. This was obviously painful and she did well to take the heaviest portions of the punishment. I looked down and caught a glimpse of her beautiful, time-etched face. Those rosy-red cheeks, which matched her bottom quite nicely now, were streaming with tears; eyes slammed shut tightly. Lips pursed, come hell or high water, Millie was going to take all I could dish out on this afternoon. Of this I was sure after seeing her incredible intestinal fortitude with which she bore so bravely, so courageously.

Then I really laid it on.

I swatted her fifty times: Twenty-five on one cheek, twenty-five on the other. Hard swats. And this was the paddle with holes in it. Millie was in tears. Real tears. But still she wasn’t done.

A hundred more came. At full-force. I guess you could say, “I paddled the devil out of her.”

I left her in tears, writhing, in her nightie to collect her thoughts. She was sobbing so hard she was having a hard time catching her breath. I thought she’d cry a river and leave that robe as a Kleenex, along with all those painful memories on the floor at her feet. She cried a lot of tears that needed to be cried that day – tears that had been stuffed for many years. She left many painful memories in the bedroom as she emerged, dressed again and with a look on her face that showed a slight glimmer of hope.

Millie contacted a few weeks after her session.

“I want to thank you for giving me my life back,” she said.

She didn’t see it, but I had moist eyes that afternoon after Millie had left.

It had been emotionally gut-wrenching for me as well.

Let the healing begin.

Coming next week: Don’t miss Mark E. DeSade’s next story ‘Brandi’

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