Testing the Submissive: The Story & Confessions of a Masochist


By Al Daltrey

Text copyright ©2014 Al Daltrey

All Rights Reserved

Dedicated to every dominant that learned one must never take a submissive for granted.

nd every submissive who learned that pain runs both ways.


Abigail Watson

I knew there was a part of me that was different from most, if not all, of my

every girl dreams of a beautiful wedding. We all want to fall crazy-in-love with a cool, fun, smart, sexy, successful guy. I guess I wanted that too, in a way.  But I never saw myself as a Princess.  I never wanted to be fawned upon.  There was something a little different happening in my head. 

Late at night, under the covers, in the
private darkness of my bedroom, my fingers would wander, along with my thoughts.  The storyline wasn’t rooted in romance.  Instead, I would envision myself strung up from the ceiling, hanging by my wrists, body covered in sweat, tears falling on my breasts, while some man I cherished stood behind me with a whip.

he more the guys around me in college catered to me, the less interested I became. Don’t get me wrong, I like sweet attentive men – as friends, maybe. But guys like that just don’t excite me. To find one’s way into my late night fantasies, my suitor required an entirely different style.

craved a strong unforgiving dominant that would put me in my place.


Meeting Lewis…

I guess you could say that Lewis became my pimp. Or my agent. In some ways, my owner.  Point is he arranges ‘assignments’ for me. These assignments involve whippings.  The subject being whipped, in all cases, is me.

In our discreet and underground bdsm network, I am referred to as a ‘whipping bitch.’  Clients, both inside and outside the circle, whip me for a price.  I’m paid well.  Lewis makes all the decisions, all the arrangements, and he takes his cut of the action – 30%.  For my part, I’m severely whipped on various areas of my body, or possibly
on all of it, then almost always thoroughly fucked, or used sexually in one way or another.  It’s my job, but more importantly, it’s my life.

The terms of my contract wit
h Lewis were discussed over an interview.  I say discussed and not negotiated, because I really had no say in the terms.  My input was basically a yes or no thing.  The interview ensured that Lewis had my consent.  He has never, and would never send a submissive out on an assignment, without her genuine consent.

So here I found myself: standing completely without clothing in front of a man ten years my senior. He was fully dressed of course,
and barely acknowledging my naked form.  I stood in the classic submissive pose, unbound with my wrists behind my back and my fingers intertwined.  My feet were planted about a foot and a half apart, slightly further spaced than a normal person would stand. The room wasn’t cold, but I was trembling a little, more from nervousness than the temperature.  The room itself was remarkably large. This was one of the most expensive loft suites in the city. The building itself had been around for almost a century, originally as an industrial structure. The best architects from near and far bid on the re-design with a firm from Japan ultimately winning. Each suite featured polished concrete floors, custom kitchens, exposed duct work, expansive style windows and open concept floor plans.  Indeed, this guy had money and the word was it was all self-made. Financial Services apparently. I couldn’t have been more nervous when I asked the security guard in the lobby to buzz me up.  The guy looked me over, and I couldn’t help but wonder how many other women had endured his stare.

Once inside the suite, there was very little small talk before the interview commenced in earnest. I’d been told to remove my clothing as if it was the most normal thing in the world, and away we went.

“I take it you’ve been whipped before?” Lewis asked with indifference in his voice.

“Yes,” I answered as confidently as I could.

We talked about my past.  I told him about my ex boyfriends, those early experiments in college with bondage, my first spanking, my first lesbian experience, the first time I sucked two cocks in one night.  The truth was, I was not nearly as experienced as I tried to let on.  Lewis saw through that pretty quick.  Nevertheless, he knew I had potential.  He could sense I had a high tolerance for pain, and a naïve willingness to let practically anyone do almost anything to my body.

n addition, Lewis had no hesitation talking to me like I was less than human.

So, basically you’re nothing but a dirty little tramp, aren’t you?”

“Yes, Sir.” I answered, my eyes lowered.

“A total slut, willing to be whipped like a common whore, is that what you are?”

He wanted me to spell it out. 
The humiliation of having to explain myself, reinforcing my true consent.

“Yes, Sir. I must be.
I’m sorry for what I am.  It’s true. I am a slut. And yes, I enjoy being whipped.”

“Deep down you have no idea if you have what it takes to be a true whipping-bitch, isn’t that right cunt?”

Oh fuck. How would I answer that?
  He was right.  Sure, an ex boyfriend gave my ass and thighs a taste of the cane once; and one of my girlfriends had taken a belt to my body – quite hard actually – but could I endure a real whipping?  Who knew?  All I knew was I wanted to try. I was ready to try.

“Sir, I can promise you I will do my best to endure anything done to me.”

Lewis slapped my face, surprisingly hard. I was shocked! A slap to my ass wouldn’t have surprised me, but my face?  Yet, I had the presence of mind to regain my position.  Ever so slightly, I tilted my face toward him offering my cheek for another slap should he decide to deliver it.

“I’m sorry Sir.” 

I didn’t want to say anything in my defense.  I felt very submissive in that moment.  I wanted him to hit me again.

He did.

I think my ears were ringing from the slap.  My eyes began to water, but they weren’t emotional tears, they were simply from the impact.


He spat in my face.  I didn’t recoil.  He was testing me.  I trusted him.  If I couldn’t handle this, I could never handle a whipping at the hands of a sadistic client.  One final slap almost knocked me over.

He asked more questions, finally
saying, “I’ll send you to see a friend of mine for a test whipping, and we’ll go from there.”

I had successfully passed my first interview.


Two weeks later, one week after the test whipping…

All had gone well. Lewis’s friend Gary had given me a good report.  I endured my first real whipping like a champ.  It hurt like hell.  Even worse than I imagined it would be.  At times, I was convinced I would yell my safeword at any second, but I didn’t cave in – willing myself to hold on for just one more strike. Then one more. And one more.  I did not break.

In the end
, I sucked his friend’s cock to thank the man for his efforts.  I was a whipped whore, pleasuring the man who had just delivered a beating. The guy came in minutes, flooding my mouth, and I swallowed without hesitation.

Outside I was glad to see my car still intact. Gary’s neighborhood was pretty seedy. It made me feel even sleazier, and I wondered if that was intentional on Lewis’ part. I felt like a cheap call-girl.

Now a full week later, I stood before Lewis a second time, fully naked again, my hands in the same position.  He examined the fading marks on my body.  His friend had experimented with a variety of instruments, but most of the evidence was gone.

“Spread your legs
a little further apart.”

stood directly before me.  I did as was told. 

Can you smell something? What’s that scent?”

I blushed. This was so embarrassing.  I hoped he hadn’t noticed.  I was wet.  Displayin
g myself in front of him, in this manner was spontaneously arousing me.  In fact, my pussy had been wet the entire week following the whipping.

“Um, I…I’m sorry Sir…I think it’s me.”  What else could I say?

“Pathetic.  You should be ashamed.”

I was.  I
ashamed.  Especially when he made me spread my legs further apart, so he could run his fingers along my slit.  It was the first time Lewis touched me.  His fingers expertly avoided my clit, or I’m sure I would have cum right on the spot.  Instead, he dipped inside, feeling how wet I was – and then brought his wet fingers up to my mouth.”

“Lick your
stench from my fingers, you dirty whore.”

I did as
I was told.  My tongue extended out of my mouth, and I lapped at the wet digits presented to me.  I tasted myself. That familiar taste.  I sucked his fingers into my mouth, thoroughly cleaning any remaining trace of my essence.

“In a
little over a week I will send you to your first paid assignment.  A woman by the name of Ms. Donovan will pay $5,000 to spend 12 hours with you, during which time you will be well whipped.”

“$5,000 Sir? Wow, that’s a lot.”

“Your cut is $3,500, and you’ll earn every penny.”

So it was set.  My first paid gig
was arranged.  We agreed that after the session, in fact after every session, that I would return to see Lewis so he would examine my body to ensure none of the marks will leave a scar, as well as conduct a post-assignment interview.


Two and a half weeks later, eight days after the whipping…

Yet again I stood before Lewis answering his questions. I felt a bit like an ex-con visiting her parole officer.  These interviews were for my own good, of course, to ensure Lewis wasn’t pushing me too far, too fast.  But I couldn’t help but deem he was enjoying the process.

“How did you feel the week before the whipping?”

At first I tried to get away with giving a vague answer, but he was having none of that.  Lewis was highly intelligent, and very intuitive – and I realized in that moment that fooling him would never work.  He demanded my full and unfiltered honesty.  And he made it very clear that if I wasn’t willing to trust him, disclosing my inner-most feelings, our relationship as pimp/whore was doomed to fail.

He repeated the question: “How did you fe
el the week before the whipping?”

“I was on edge all week.  I was nervous.  At times I
was certain I’d back out.  In moments of weakness I worried I wouldn’t have the courage to go through with it.  Then, a few minutes later, I’d be wildly excited by the prospect of being whipped.”

“How did you
r pussy react, during this emotional roller coaster?”

“I was highly aroused.  My pussy was almost always wet.  I would masturbate, at the mere thought of what was going to happen, which brought some relief.  Then, five or six hours later, I was
horny again – and could barely keep my fingers away from my clit.”

“You were masturbating
at the anticipation of being whipped?”

“Yes.  Yes, Sir.  I would.  I would cum, just thinking that this woman I had yet to
meet would soon be whipping my body.”

smiled.  He tried to hide it.  But I noticed his eyes smiling.  He was pleased.  My answers were music to his ears.  But I also knew that, as I disclosed more about my masochistic nature, I was basically giving Lewis a green light to push my limits further.

“Tell me then, what happene
d on your date with Ms. Donovan?”

I told
Lewis about how my first few hours with the woman were not at all what I expected. She arranged to have me picked up by limousine, and we went shopping.  Shopping!  She was quite delightful, very polite and respectful toward me, and extremely generous.  She took me to the most exclusive shops in the city and we picked out a beautiful and very sexy little number.  For me, no less.  Next, we enjoyed lunch at a high-end Asian fusion restaurant downtown.   It was in the limousine on the way back to her condo that she finally started to flirt with me, and touch me.

“Why do you think she
spent a few hours with you, shopping and lunching?”

“I assume she was sizing me up, Sir?”

Lewis explained that it wasn’t so much that she was sizing me up, as she was building up anticipation. It was foreplay for her.  I blushed when Lewis informed me that Ms. Donovan had told him that she in point of fact developed a little crush on me in those few hours together, which made whipping me all the more pleasurable. 

“What happened when you got inside
her condo?”

At first, Ms. Donovan was as sweet as anything. She opened a bottle of wine, and midway through her first glass, she started to slowly remove my clothing. Once nude, she led me toward her den.  The room appeared to be a reading space, but when she removed a hanging plant, a mobile, and a few other things I realized it quickly and easily transformed into a make-shift punishment room. I was adorned with lengthy ankle and wrist cuffs that easily fastened to the strategically placed eye-hooks in the ceiling and floor.  She patiently adjusted the straps until I was pulled taunt, my arms and legs stretched wide apart.”

“Were you afraid, or excited, or how were you feeling in that moment?”

“I was uneasy. Like the calm before a storm.  I noticed it in my breathing, short shallow breaths, so I had to consciously remind myself to breathe properly. I was nervous, and yet – yes, I was aroused too.”

“Pathetic, don’t you agree?”

“Yes, Sir.” I lowered my gaze and could feel myself blush.

“What happened next?”

“She beat me. She started in on my shoulders with a rawhide knout.  The way she transitioned smoothly between a forehand and backhand swing alerted me to how skilled she was with a whip
Each strike was delivered with power and finesse. My entire upper back was in agony in no time at all.”

Did she say anything?”

right way. But a few minutes in she made comment about the ritual of athletes in every sport.  How they warm up before the game begins. Pitchers pitch. Hockey players skate around. Basketball players shoot hoops. At first I thought she was comparing herself to an athlete, but then I realized her intended point.”

“And what point was that?”

“That the rawhide knout was nothing more than a prelude. The real whipping was yet to begin. She was just warming-up, like an athlete before a game.”

Was her warning valid?”

“Oh yes.  Th
at knout laid into my shoulders without compromise, and yet the worst was yet to come, by far.  She moved through a variety of wicked instruments, and enjoyed the reaction of my skin to each one. This went on for some time. Occasionally she stopped to sip her wine, or feel my pussy.”

“When she touched you, were you wet?”

“Embarrassingly so, Sir.  Yes, I was wet. Very wet.”

“Your body was betraying you?”

“As it always does, Sir.  The pain was almost unbearable at times.  I wished for it to stop, I wished for
to stop!  I secretly hoped she would release me, so we could make love, or at least so I could pleasure her. But for the better part of two hours she simply punished my body.”

“What exactly did she use?”

“Oh, so many things. At least three different floggers, a soft deer skin one, and one which felt like fake synthetic leather. She used a bunch of belts, some thin, some wide, some heavy.  She used a wooden spatula from the kitchen on my nipples which drove me insane with agony. She used a cane on the back of my thighs, but thankfully she went easier with the cane. She used her hands at times, to spank me. She slapped my face a half-dozen or so times.  Um, oh yeah, she used a hairbrush, and a wooden paddle.”

ow did it eventually end?”

“At one point, she paused to scan my entire body with her eyes. I was
pink everywhere. Welted in many places. The skin swollen and puffy in a few tender spots. There was virtually no part of my body that was unblemished. She seemed satisfied. I was practically hanging by my wrists at that point, and she knew I was thoroughly beaten not only physically, but also emotionally.”

“Go on.”

“She put down the last instrument, and retrieved a thick rubber strap-on that was waiting nearby. She fastened it to her waist, and kept adjusting it until it was just right.”

“Ah yes, I’ve heard her tell of this strap-on, it was custom designed for her.”

“Indeed Sir. It fit her perfectly, and chiefly, there is a protrusion that faced inward, that Ms. Donovan guided into the folds of her pussy so that it massaged directly onto her clit whenever she thrust forward against any resistance.”

“This way, when she fucked you, she was able to grind out an orgasm herself.”

“Which she did. After the whipping she released my ankles, and then my wrists. I all but collapsed to the floor.  She took me from behind, doggie style. She slid the strap-on deep into me, and started to fuck me hard, pulling on my hair for leverage.”

“Did it take her long to cum?”

“Not at all. Her strap-on worked like a charm. Every time she plunged into me, I could hear her moan, and I knew the special part of the dildo was serving its purpose, stimulating her clit.”

“What about you?”

I paused. But I knew the truth must be told, “I came too, Sir.”

“Filthy fucking cunt.”

“I’m sorry, Sir. Although I assure you, Ms. Donovan didn’t mind. Not at all. In fact, I genuinely believe she was quite pleased that my orgasm hit on the heels of hers. We just about came at the same time.”

“What makes you think she was pleased?”

“She taunted me about it, but in a good way. She called me her little fuck-toy, and boasted that since I seemed to be enjoying myself so much, she’d beat me even more the next time.”

“Was that her only orgasm?”

“No, Sir. She had two more.”

“The same way?”

“No. The other two did not involve the strap-on, which she removed right after fucking me. She made me lay on my back, on the floor, and she spun around, literally sitting on my face, facing my body.  Her shins pinned my shoulders down, and she started to grind her very-wet pussy all over my mouth.  In no time at all, she began to spasm and then orgasm.”

“Then what?”

“She caught her breath by resting a while.”

“You rested as well?”

“I did, although I can’t say it was easy to catch my breath”, I jokingly remarked, “my mouth was still completely covered by her wet pussy, and I didn’t want to make any audible gasps, in order to not disturb the Mistress. Best I could, I took my breaths quietly, through my nose, whenever it wasn’t fully buried between the cheeks of her ass.”

“How did you feel in that moment?”

“I felt an inner peace, Sir. My body was still stinging from the whipping, yet I felt content that I was able to bring sexual pleasure to Ms. Donovan.  I was happy simply that she seemed happy.”

“That type of sentiment is indicative of a true submissive.”

“I realize that Sir, and I agree.  In that very moment I remember feeling proud. I didn’t dare speak, but if I had I would have told her she could beat me, hurt me, use me, anything – I didn’t care, I just wanted to be at her disposal. “

“Did she say anything during her respite?”

“She mumbled a bit,
‘sooo good’
, she softly whispered as if speaking to herself, and ‘
lovely just lovely’
, things like that. I smiled right into her pussy lips.”

“You said she had three orgasms, how did the third occur?”

“After the second one she led me by hand to the couch, where we cuddled under a big comforter, and with the TV on in the background, we kissed and made small talk. She fell asleep with both her arms and a leg wrapped around me. I was careful not to stir, and an hour later she awakened. She pushed my shoulders lower, and I understood her command.”

“How long did it take the marks to fade from your body?”

“There are still a few remnants remaining, but 90% of the marks are gone. What little is left is barely visible.”

“Did you have sex with anyone during the past week?”

“No, of course not, Sir.  My intention is to abstain from sex, other than in the appointments arranged by you.”

“Did you masturbate?”

I hesitated, slightly embarrassed by the question, “Yes Sir, I must admit, I masturbated quite often.”

“How often?  T
ell me.”

“At least two or three times per day, I think I came five times on one particular day.”

“Did you use a vibrator, or some sort of toy, or your fingers?”

“Most often m
y fingers, Sir.”

“What were you thinking about while your fingers were busy?”

“I would close my eyes and remember various moments of my time with Ms. Donovan, replaying them in my mind over and over.”

Give me an example of one such

“At one point Ms. Donavan was using a long riding crop on my shoulders. One lash wasn’t delivered properly
, and the end of the whip curled underneath my armpit, with the very tip cutting into the underside of my right breast.”

“You enjoyed the pain?”

“Not when it happened! I hated it. It was beyond my pain threshold. I glanced down fearful that she had actually broken the skin, that’s how bad it hurt.”

“If you didn’t enjoy it, why masturbate to it?”

“That’s just it, Sir. I can’t explain it. When it happened the pain was not pleasurable. But when I remember it, when I think about it now – God, it’s so hot. Anytime I envision her whip striking my body, I feel a tingle in my pussy, and I want to touch myself.”

“Give me another example.”

“When she sat on my face, after her second orgasm, the recollection of her soaking wet cunt mashed all over my mouth and lips. At one point, she reached down and started to pull and twist my nipples tormenting me further.”

“You enjoy that memory.”

“I love it, Sir. My cheeks were slimy with her juices, and I can still remember her musky smell. Plus, I find it hot that she was simply sitting there, casually oblivious to my discomfort.”

“Is it arousing you now,
telling me all of this?”

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