Testing the Submissive: The Story & Confessions of a Masochist

by Al Daltrey

  “What did he say?”

  “He said I was lovely. He said he would give me a glowing report when he talked to you. He said Brutus enjoyed his time with me. Then he said I was totally free to go, and our session was formally over.”

  “You gathered your things and left?”

  Answering Lewis’s questions wasn’t always easy, but I really didn’t want to answer this one. I wanted to lie, but I couldn’t do that. I hesitated, trying to buy time to think. Then I asked a question of my own:

  “Sir, would you mind if, just this once, I’m permitted to avoid the question?”

  Lewis moved his chair closer to mine. He wasn’t pleased. I realized that I had made a mistake by attempting to avoid his question. After all, it was breaking our underlying agreement. I had agreed, explicitly from day one, to answer ALL of his questions with total honesty, and here I was begging off one. I fucked up. I knew it was pointless to apologize, so I sighed and waited for the punishment that was sure to come. Lewis reached under the table cloth, and started to hike up my skirt. Luckily our table was hidden from much of the commotion in the restaurant, and no one could see or notice what he was doing. My thigh was soon fully exposed, but still under the table. There were three small candles burning, each in a glass that resembled a shot glass. Lewis poured the excess wax from two of the glasses into the third, and I knew what was coming. The only question in my mind was that of ‘distance’. The difference between pouring wax from six inches above the skin, versus say, two inches – is huge. Lewis moved the glass to my thigh. Oh fuck. He rested the glass on my skin, and then tipped it over. The hot wax poured onto my inner thigh. And there was a good dollop of it! Three glasses worth. If not for being in a restaurant, I would have screamed. I bit my lip so hard I thought I tasted blood. The wax was hot as hell! It poured along my inner thigh leaving a trail of pain as it went. In fact, while I didn’t know it at the time the skin would peel in the days to come. The pain was a rude awakening as to what would happen if I dared refuse a question again. I fought back tears and whispered my apology over and over.

  I knew I was forgiven when Lewis allowed me to redeem myself.

  “Not only will you answer the question, you will do so with more detail than usual. Clearly, you’re ashamed about something, and you will spell out every detail of what it is. Take your time, and tell me exactly what happened after Grekko ended your session.”

  Just then our main courses arrived. Over dinner I told him:

  I told him about gathering my clothes and dressing myself while Grekko watched and rested from the comfort of his La-Z-Boy. During those few minutes, we made small talk. Grekko asked if I had any other plans that evening, and I told him I did not. He then made a comment that he was too tired to touch me, but if I wanted – I could stay and fuck his foot. Both his legs were extended, and inadvertently I glanced toward his foot which was resting on its heel, pointing upward. I froze. I was appalled and yet, I couldn’t deny I was still highly aroused, even after cumming all over Brutus. Grekko reiterated his offer. He reminded me that our session was officially complete, and I was under no obligation to stay. However, if I wanted to stay and fuck his foot, I could do so, as long as I cleaned it afterward with my mouth and tongue. I turned to leave and, like a zombie, I walked toward the door of his house. Reaching it, I put my hand on the handle. But I didn’t turn. I was telling myself to leave, but my body wasn’t obeying. Instead, my hands went up to my blouse and I unbuttoned it. I kept my back to Grekko until I was nude. I couldn’t look him in the eye, as I was too ashamed. Then I dropped to my knees, turned around and crawled toward the La-Z-Boy. He had slouched further down. When I reached his foot I kneeled upright and lifted one leg over, so I could squat down on it with my pussy. That’s when I thanked my host:

  “Thank you Grekko Sir, for allowing me to satisfy my slutty nature. Thanks for letting me fuck your foot. I promise when I’m done, I will clean it up before I go.”

  I continued my story, telling Lewis about lowering myself onto Grekko’s foot: I was very wet, but I had to guide his toes inside me. I maneuvered myself until his big toe grinded on my clit, and then I start to ride him. I was bouncing and rocking, literally humping his foot. I was fucking it. I was fucking Grekko’s foot. As earlier, I was cumming in minutes, soaking his toes. When my orgasm subsided I lifted myself off him, and cleaned him as promised.

  As I bent lower, I’m not sure what smelled stronger, my juices or Grekko’s foot. I remembered he was working in the yard when I first arrived. Nevertheless I was temporarily satiated, and had a job to do. I licked every inch of that foot until it was no longer shiny with my juices, but with my saliva. I sucked on each toe and licked in between them. I lapped at the underside. I didn’t rush. Then I blew lightly to dry the area, and in my peripheral vision I saw Grekko smile. Neither of us said a word as I dressed. By the time I opened the front door to leave, I could see he had fallen asleep.

  “Your next appointment is with a couple, Trudy and Tony,” Lewis said, matter of factly.

  “Yes, Sir.” I was happy to move on to another subject, quite embarrassed about my actions on the last appointment. I glanced down toward my thigh, moving the table cloth to the side so I could see my skin. The red blotchy skin was swelling slightly. There was a clear delineation where the wax had touched.

  I couldn’t help but think I deserved the mark on my thigh.

  “It’s already confirmed. Three weeks from today. Your leg should be well healed by then. Location and payment details will follow by email.”

  I nodded my consent.

  CHAPTER 6: 5 FOR 5 FOR 5

  A month later, one week after the assignment…

  “So,” Lewis said with a smile, “what did you think about Tony and Trudy?”

  Likewise, I smiled as we chatted about the unique couple who had enjoyed my services a week earlier. My observations were confirmed by Lewis. Tony, the supposed dominant in the relationship was cleverly influenced every step of the way by Trudy, the supposed submissive. Tony was the one who had delivered every stroke. On the surface he was in charge. However, it was the mischievous nature of his girlfriend Trudy that caused me the most pain, both physical and emotional.

  They had played a game called ‘five for five for five’. Trudy’s idea of course. Five areas of my body would receive five strokes, delivered by five different instruments. My breasts saw five forceful blows from a riding crop. The back of my thighs tasted the intensity of the cane. My ass got five good ones from a wooden paddle. My nipples had their first ever introduction to the torment that a kitchen spatula can bring. And, saved for last, my pussy suffered five nasty strikes from a leather flogger.

  Lewis wanted to hear the details, and asked his usual batch of questions.

  “How were you positioned for the first one?”

  “For the breast whipping, I was made to stand with my hands on the back of my head. I was told to push my elbows outward, which thrust my breasts forward.”

  “Where was Trudy while Tony whipped you?”

  “She was sitting in a big reclining chair, naked, touching herself – watching and making comments throughout.”

  “What kind of comments?”

  “For example, after Tony’s second strike on my breasts, Trudy asked him if he remembered a bdsm video they watched where the Dom had such precise aim with the crop, he could snap it right on the very tip of the nipple.”

  “Let me guess,” Lewis said, “Tony took the bait?”

  “He did, Sir. He aimed directly for my nipple for the last three whacks.”

  “Tony was unaware of her sly manipulation, wasn’t he?”

  “Indeed. He thought she was curious about his ability to aim, but all she wanted was to cause me the maximum pain. She had a devilish grin when he hit me.”

  “Did you stay in that position when they moved from the crop to the cane, for your thighs?”

  “Not quite, Sir. I moved closer to the coffee table, and was made to bend forward, u
ntil my hands rested on it. This displayed my thighs nicely to take the cane.”

  “What kind of cane was it?”

  “From what I could tell, it was a thin wooden flexible cane, which I must say – hurt like hell.”

  “Did Trudy chirp in with any comments, this time?”

  “Not surprisingly, yes. She asked Tony if you had imposed any limits to how hard he could hit me.”

  “Ah. Very clever on her part. A timely reminder that he had no reason to hold back.”

  “Exactly, Sir. I think her ploy was lost on Tony, but it wasn’t lost on me.”

  “Did it work?”

  “Yes. It did. He swung so hard, the cane almost cracked into two.”

  “Did you cry out in pain, or were you able to suppress the screams?”

  “A little of both, I guess. I managed not to scream out per se; but I did yelp and squirm and gasp aloud, noises like that. At least, until Trudy put a stop to that.”

  “How so?”

  “Earlier, when I was stripped of my clothing, my thong ended up on the floor, not too far from the Lay-Z-Boy where Trudy was sitting. When Tony had his back to her, she discreetly picked up my thong, and dangled it, ensuring I noticed. Then, while he was caning me, she carefully tucked it right up inside her pussy, unbeknown to her Master. She gave me an evil grin when my garment was inside her, and I half suspected where it would end up next. After one of my yelps, Trudy pulled the thong out of her snatch, and jumped out of the chair. She pretended to pick it up off of the floor as she moved toward me. With Tony’s blessing, she stuffed the pungent cloth into my mouth, supposedly to stifle my annoying outbursts. He had no idea it was still warm and slightly wet from her cunt.”

  “How did that make you feel?”

  “I was very humiliated. I felt myself blush. And yet…”

  “And yet?”

  “And yet, I did feel a tingle in my pussy. I also felt strangely proud, as if Trudy and I shared a little secret. It was weird because, shortly thereafter I shared a little secret with Tony as well.”

  “Tell me about it.”

  “After the caning, we moved on to my ass, which was beaten with a thick wooden paddle. Tony was taking good hard swings, and my butt was instantly a fiery red. By this point, the five stripes across the back of my thighs were swelling and darkening, and Trudy wanted to take few photos of my behind. She went to fetch her camera, which afforded me a moment of rest, and a moment alone with Tony.”

  “He told you he wished he could fuck you, didn’t he?”

  “Indeed, Sir. He told me that he couldn’t use me that day, or Trudy would go ballistic. I believe they had agreed in advance that there would be no sex with me.”

  “So, what did he say?”

  “He whispered something like: ’just you wait, slut, I’ll get you one day, wait until Trudy goes away to visit her Mother, I’ll fuck you yet’. Words to that effect.”

  “How did that make you feel?”

  “It made me feel cheap. Like a whore who fucks otherwise happily married men. I didn’t appreciate that Tony and Trudy are not fully honest with each other; but I know it’s not my place to judge, and I have no say in such matters. I was there to serve, and would never dream of betraying either one of them.”

  “Trudy took pics of your ass and thighs?”

  “Yes, close up pictures only to protect my anonymity. I didn’t mind.”

  “What was next in line for abuse, your nipples?”

  “Yes, but at that point they took a break to have sex. Tony had been hard for a while; he eventually removed his jeans to allow his cock room to grow. And judging from the wetness of my thong, still in my mouth I might add, Trudy appeared to be enjoying the session. They fucked right there, on the living room carpet, and it didn’t take long before they were both cumming.”

  “I’m surprised they let you watch?”

  “Actually, they didn’t Sir. They made me stand in the corner, facing it. I was instructed not to move or make a sound.”

  “You obeyed of course.”

  “I did obey. I listened of course, but didn’t dare move a muscle. That said, Trudy found a way to get me in shit regardless.”

  “How so?”

  “After they both orgasmed, they returned their attention toward me. Trudy complained that at one point, I looked over my shoulder at them. This time Tony laughed it off, as if she was kidding. I thought I was off the hook. But Trudy, as usual, was sneaky – she challenged Tony to ask me himself. So, he did. He looked at me, and asked me directly if I looked over my shoulder.”

  “How did you answer?”

  “I hesitated, looked at Trudy who was staring back at me, and then said ‘I’m sorry’”.

  “You confessed, even though you were innocent?”

  “Yes. I took the fall. I don’t think it would have caused any rift between them, but I didn’t want to go against Trudy’s accusation. I went along.”

  “Were there any repercussions to your decision?”

  “Yes. At Trudy’s suggestion, the previous five strikes – the wooden paddle to my ass – were re-applied.”

  “Did you regret being the martyr when the pain hit?”

  “I didn’t regret my decision, but it did hurt beyond words. Tony swung that paddle like a baseball bat, the force of each blow sending me forward. My ass felt like it was being destroyed.”

  “Meanwhile, you couldn’t exactly cry out, with your mouth still stuffed with the thong?”

  “No, but the tears were flowing freely at that point.”

  “What was next on the agenda, the spatula?”

  “The spatula on my nipples, which might not have been too bad, except for how tender they were from the riding crop earlier. The spatula was very much a stinging pain, and by the end my nipples looked like Rudolph’s nose. Tony allowed me to spit out the thong, which was nice.”

  “Why did he do that?”

  “My crying had caused me to sniffle, and breathing out of my nose was getting more difficult. With the thong gone, I was able to take a few deep breaths. Then Trudy said something that made me shudder.”

  “Good ole Trudy. What did she say?”

  “She casually said that since there was only one punishment left, I was going to get something to really scream about.”

  “He whipped your pussy, didn’t he?”

  “Y..yes.”

  “Where did the man whip you, slut?”

  I guess Lewis wanted to hear me say it, “The man whipped me right on my open cunt, Sir.”

  “What do you mean, your open cunt?”

  “Trudy held my pussy lips open…with her fingertips, exposing my inner folds along with my pink clit. She held me open, my legs spread very wide, while Tony flogged me with the leather flogger.”

  “Did you scream?”

  “I couldn’t help it. I tried not to, but each whack sent me into orbit. I screamed involuntarily.”

  “How long did they wait between strikes?”

  “Funnily enough, after the first strike Trudy whined about how much it hurt her hands! I almost told her to fuck-off. She was rubbing her hands, looking for sympathy, while my insides burned. She actually went to her spare closet, in another room, to fetch a pair of winter leather gloves. All to say, it was about five minutes before the second one.”

  “Ha! So, Trudy wore leather gloves to hold open your pussy lips so the flogger didn’t hurt her hands.”

  “Yup. She also slapped my face at one point with the leather gloves.”

  “Why did she slap you?”

  “My pussy was wet. Despite the abuse, I was aroused and wet. This made it difficult for her to hold open my lips, as they were slippery against the leather. In frustration, at one point she slapped my face.”

  “What did you do?”

  “I think I apologized for my slutty nature, and told her I couldn’t help it.”

  “And somehow you endured the remaining strikes.”

  “Somehow I did. Even now, the memory is
a bit blurry as it was so intense. I have a mental technique that I use, in those instances, whenever I fear I won’t have the resolve to withstand the punishment.”

  “What is the technique?”

  “Well, if I think about the fact that there are still three or four or five strikes left, I become overwhelmed. I can’t imagine how I will survive it. Instead, all I do is focus on the next one. I keep telling myself ‘one more, just one more’. I put all my mental strength into enduring one more strike. Then, after that one, I do it again. I know it sounds silly – but dealing with the strikes one at a time somehow makes it possible.”

  “Were you glad when it was over?”

  “I’m always glad when it’s over.”

  “Yet you do this by choice. I’m not forcing you to do any of this. If you’re glad when it’s over, why do it at all?”

  “As you know Sir, the entire week before I’m highly aroused. So much so, a few flicks of my clit and I’m cumming like crazy. Afterward, same thing. I can’t keep my fingers away. Even during, as much as I hate the pain, my pussy leaks like a faucet. I’m a pain whore. I hate the pain the moment it happens, but I love it every other second of the day.”

  “Did you have much time to recover before heading home?”

  “Barely Sir. They wanted to have sex again, so I got dressed as fast as possible to give them privacy. It wasn’t easy but I moved as quickly as I could.”

  “Why do you say it wasn’t easy?”

  “I was still crying. My legs were sore from being spread so wide. My pussy was still completely on fire. The slightest movement caused discomfort. When I tried to put my dress on, my ass hurt. I was still sniffling and crying, my mascara smeared a bit. My hair was disheveled from thrashing about. When I leave a Client’s house, I don’t want to raise any attention, for their benefit. I need to be fully composed. So, it was balancing act. I wanted to let them fuck each other in the heat of the moment – but I didn’t want to look like a rape victim leaving their condo. “

  “Victor was waiting for you, in the limo, out on the street?”