Testing the Submissive: The Story & Confessions of a Masochist Page 2

  “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? Tell 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 my 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 moment.”

  “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?”

  Again, I hesitated, “yes…yes it is.”

  “Will you masturbate when you get home, after our interview?”

  “I’m sure I will. Knowing me, I’ll likely start in the cab ride home, rubbing myself through my jeans, as long as I can do so discreetly, without the driver noticing.”

  “You are nothing but a fucking whore.”

  “I know, Sir. I’m certain that I am. I’m sorry for being what I am.”

  “No need to apologize for being what you are, you’re the one who’s going to suffer for it. I’ve arranged your next appointment, unless of course you no longer wish to continue with our arrangement?”

  “I’m ready for my next appointment, Sir. Ready and willing.”

  “Good. You will visit a man by the name of Grekko. He will introduce you to his thick rubber strap. He can only afford $1,500 so your portion will be $1,050. Not as lucrative as the previous one, but it will be just as painful, if not more.”

  “I understand, Sir. I’ll be prepared.”

  “Then it’s set. I will email you the details once finalized, but it will be in about a week at his farmhouse. I will give him six hours with you.”

  CHAPTER 4: A DREAM

  Three days later, in the midst of a dream…

  Lewis appeared to me in a dream. He was as handsome in my reverie as he was in reality. With his rugged good looks, not the pretty-boy looks of a Brad Pitt or a Bradley Cooper; but more like Russell Crowe. He was a good four or five inches taller than me, so I’d say just over 6 feet. He kept his hair short. In fact, his thick dark hair was near perfect, just falling over his forehead with a slight wave to it. Lewis had a definite charisma, or presence, or gravitas – whatever you want to call it. Point is, when he spoke everyone within earshot wanted to hear his every word.

  In the dream we were in some kind of log cabin up in the mountains. I was lying on a bed, and he was approaching me, with a pair of handcuffs.

  “There’s a bad storm coming…” he said.

  I didn’t say a word, but put my wrists together so that he might cuff them.

  “No,” he continued, instead taking my left wrist and cuffing it to the one bed post. He took my right wrist and did the same thing to the other bed post.

  I was about to say, “Will you whip me?” but before I could do so, we could both hear the sound of a freight train approaching. The most powerful wind I’d ever seen began to envelop the room. As is surreal in dreams, everything inside the cabin started swirling and flying around. I could see through the windows that the same thing was happening outside. Trees and objects, massive rocks, including all sorts of debris were flying around. Then it dawned on
me what was happening.

  “Tornado!” I said. “Shouldn’t you release me?” Fastened as I was to the strong bedposts there was no way for me to seek shelter.

  Just then, the entire roof of the cabin lifted off and flew away into the vortex of the tornado. All of the furniture and objects around us were also sucked up into the void. The tornado was directly above us, but everything seemed to be happening in slow motion.

  “The cuffs!” I pleaded again to Lewis, as if to say ‘release me’. But he lay over me to protect me from whatever debris was still flying around. He took hold of the same bedposts with his strong hands.

  I awakened to a feeling of peace and unequivocal trust of the man who had taken command of me.

  CHAPTER 5: THE STRAP HAS A NAME

  Sixteen days later, six days after the strapping…

  This time Lewis decided to conduct my interview in a restaurant, over dinner, which surprised me. I was both pleased and disappointed at the same time. Pleased that we’d be having dinner together, out in public; yet disappointed that I wouldn’t be naked before him. That said, the venue was secondary. I found myself excited to be in his presence again. Excited both emotionally and sexually.

  “How have you been?” Lewis started with a benign question.

  “Pretty good Sir, considering I can finally sit on a chair again.” Lewis laughed at my joke, understanding exactly what I intended. He knew that Grekko concentrated on my ass.

  “I assume there is still evidence of bruising?”

  “Very much so, but it’s healing well. I’m sure I’ll be completely clear within a week.”

  “When you go about your day, how does it feel knowing there are marks under your clothes?”

  “I love it, Sir. I know that sounds strange, but I enjoy knowing the marks are there.”

  “How so?”

  “If I’m out in public, or even hanging with friends, I love the feeling that I’m carrying a kinky secret. The marks represent that secret. No one has a clue that under my jeans my ass is purple and blue. It’s fun!”

  Just then our waitress arrived, and Lewis and I both ordered drinks. He ordered a red wine, and I ordered white. Once our server was out of earshot, the conversation continued.

  “So, when you arrived at Grekko’s farmhouse, were you surprised by his appearance?”

  “Yes. He was working on some landscaping when the limo pulled up into his long driveway. At first, I thought he was the groundskeeper or something, but then when he paid the limo driver, my heart sank, and I realized this would be the man using me.”

  “How did he appear?”

  “He was disheveled, unshaven, and somewhat sweaty; his clothes confirmed he was working outside all day.”

  “How did that make you feel?”

  “It was a strange feeling. On the one hand, I was somewhat repulsed by the idea of this man touching me. Yet, a part of me wanted to serve him for that very reason.”

  “Why so?”

  “To prove to you, Sir – that I’m yours to share with anyone you desire, that I have no say in who uses me, or how. Whether a man or woman is attractive or not has no bearing on the fact that they can whip me, use me, fuck me or whatever. It reconfirmed my position as an unequivocal whipping-bitch.”

  “What happened from there?”

  “Grekko and I made our way inside the home, and in no time I was up in his bedroom, on the second floor. He undressed me like a child opening up a Christmas present. Then he said something which at first confused me.”

  “Let me guess, he mentioned Brutus?”

  “Yup. Exactly. He said he wanted to introduce me to Brutus, so I thought he had invited a friend to join us. Momentarily I was concerned, as I know you would have told me in advance if others were to be involved.”

  “Personally, I think its goofy how he refers to Brutus as a person, but I guess that’s part of the eroticism for Grekko; and a good submissive should happily accept the whims of her dominants.”

  “Very true Sir, and instinctively I did that very thing – I think I said ‘it is my pleasure and honor to meet you Brutus’ when he showed me the strap.”

  “What did it look like?”

  “It’s a very thick, heavy rubber strap, moderately flexible, with a custom made handle. When Grekko held it before me, I peppered Brutus with soft kisses, as a sign of respect.”

  “Were you worried?”

  “VERY worried. I was not looking forward to the agony that Brutus was about to bring me.”

  “And your pussy?”

  “As usual Sir, as much as I was worried, fearful, apprehensive….my pussy did have that familiar and predictable tingle. I didn’t want to be there, and yet – my desire couldn’t be ignored.”

  During our conversation Lewis and I scanned the menu, ordered appetizers, and were into our second drink. I found myself increasingly attracted to Lewis. I enjoyed answering his questions. In fact, I practically hung off his every word.

  “Where and how did Grekko deliver the discipline?”

  “He made me kneel over storage chest at the foot of his bed. I wasn’t tethered, but told to remain still. Brutus came down hard and heavy across the back of my thighs. The sting was worse than I imagined, and I was also surprised by the weight of the strap. It was like a heavy blow to my body. The pain was fierce. I wasn’t sure if I’d be able to endure a beating like that.”

  “But you did, of course.”

  “I did, Sir. One strike at a time, I endured it. He continued on the back of my thighs for at least a dozen more, before moving upward toward my ass.”

  “Then?”

  “For forty-five minutes, about once per minute – Brutus came crashing down on my ass, with great force. My butt was on fire. I was crying. I was trembling. I did my best to stay cool. Occasionally Grekko would bring Brutus up to my face, so I could plant a kiss or two on the strap.”

  “Was there much conversation?”

  “Grekko barely spoke. But there was a permanent smile on his face. He seemed content; at times he would rub his callused hand over my ass, perhaps to soothe me, perhaps to gauge the warmth of my skin, I’m not sure. Instinctively, I spoke to Brutus during one of our kissing moments, and Grekko’s cock, which was already hard, seemed to get even harder. I took that as a cue to speak to Brutus more often during the beating, and Grekko appeared to revel in it.”

  “What sorts of things did you say to Brutus?”

  “I would kiss Brutus, and lay the side of my cheek against the rubber, then say ‘thank you Brutus, thank you for teaching my ass a lesson’ or ‘sorry Brutus, sorry for trembling so much, when you’re ready please hit me again’. Finally, Grekko laid the strap to rest on his dresser, and I knew the beating was over.”

  “Did Grekko fuck you at that point?”

  “He wanted a blowjob. He made me kneel before him, which wasn’t easy with my ass on fire. I was instructed to keep my wrists behind my back, and use only my mouth. In less than a minute, my mouth was flooded with his cum. I swallowed as I sucked and did not remove my mouth from his cock until several minutes after he released.”

  “Was there relief for you?”

  “There was. Grekko motioned for me to stand. He picked up Brutus again, but somehow I knew he wasn’t going to hit me with it. He tapped my inner thighs, and I spread my legs. He turned the strap on its side, and with the very edge of the rubber he began to slide it along the length of my slit. In no time Brutus was wet and slick with my juices, which allowed the instrument to slide easily along my cleft, pressing against my clit in long smooth strokes. In as little time as it took Grekko to cum, so did I. I gyrated against Brutus, cumming as the strap worked its magic on my needy cunt.”

  “I imagine you were required to thank the strap for this additional indulgence?”

  “I thanked Brutus by kissing and licking every inch of that strap, until any evidence of my essence was unquestionably gone. Grekko patiently watched me the entire time, still standing right in front of me.
Eventually, he took Brutus away, and swept me into his arms – kissing me himself.”

  “Interesting. Grekko kissed you? And how did that feel?”

  “Again, respectfully Sir, he isn’t exactly the most attractive man. His breath was stale, his stubble irritated my skin. His hands were roaming all over my back and ass, which was still stinging. And he kissed me very passionately for quite a while, so it was full-on high school necking, if you will.

  “Did you return his kiss, or were you holding back?”

  “I returned it, for sure. My duty and willingness as a submissive far outweighed any hesitancy because either; I barely knew the man, or because of his appearance. I kissed him with as much passion as he kissed me. When his tongue explored the inside of my mouth, then I explored the inside of his with my tongue. I held him tight. I softly moaned. I ran my fingers through his hair. In one instance, I almost giggled, but other than that, I was one hundred percent into the kiss.”

  “What caused the giggle?”

  “Grekko has a big-gut, as you know. So much so, I practically had to suck in my stomach to make room for his beer belly, and that caused my breasts to rest on the top of it. I imagined we looked like Ying and Yang from the side, which almost made me smile into the kiss. However, at the same time, both his hands wandered down and he grabbed my ass, sinking his fingers into my flesh. Still being tender and raw from Brutus’ work, the pain snapped me out of any notion of giggling.”

  “You waited for Grekko to break the kiss?”

  “It happened very naturally. His cock was returning to form. While we kissed, he guided my hand toward it, and I started to jerk him off while we stood. We did that a while. Soon he was rock hard again. I thought he might want to fuck me, but when he pressed down on my shoulder, I knew he wanted another blowjob. I slowly kissed my way lower until he was once again fucking my mouth.”

  “If memory serves correct Grekko is a two-orgasm Client, which means he was spent after this one.”

  “Yes, he sure was. I was barely able to finish swallowing when he sat heavily in a nearby La-Z-Boy with a peaceful look of contentment on his face. He was sweet when he expressed his satisfaction verbally.”