The Delicious Torment

by Alison Tyler

  I think he would have passed out at the idea. Or maybe had a heart attack on the spot and died.

  But with Jack, all things were possible.

  Like the fact that he didn’t have to say a word to Alex, that Alex came forward, grabbed me up in his arms, whispered to me that I was so fucking sexy. “Didn’t think you could look like that,” he said, eyes roaming over my outfit. “You’re such a girly-girl usually.”

  And he was right. I am. But on this night, I was something else. How odd that I’d thought of the encounter as “Alex’s Transformation,” when it wound up being mine, as well. Jack motioned to Alex, and he nodded, grabbing my hand, pulling me back to the bedroom. Jack didn’t follow, and I realized that I was the one who was going to have to explain the next part of the scenario to Jack’s right-hand man. At least I thought I was. But as soon as Alex saw the purchases spread out on the bed, he seemed to understand.

  “You know where he sent me today?” Alex asked.

  I shook my head.

  “A salon. For a wax job.”

  I watched as Alex peeled off his clothes, revealing the smooth expanse of his broad chest. He had also very recently shaved, not relying on the early morning’s visit with the razor. I sat on the edge of the bed, surprised at how quickly, how willingly, he got naked. Had Jack prepped him? Or was Alex such an obedient assistant that he would do whatever Jack requested of him? Even when that request wasn’t verbally given?

  “What’s next?” he said, staring now at me.

  I handed over the panties, and his cheeks turned ever so slightly pink as he pulled them on. “You had to get ruffles,” he said softly.

  “They were specially requested,” I told him.

  Alex nodded, waiting for me to pass over the white pinafore, like something from Alice in Wonderland. Or something from an acid dream. A pinafore with ruffles, as well, but one in a size that would fit the well-built man standing feet from me. He pulled the dress over his head, and then gave me a mock curtsy, and I started to giggle.

  “You think I’m pretty?”

  “No. Not really.”

  He looked hurt. “Well, why the fuck not?”

  “You’re not done.” I handed him the wig, and he took it and stood in front of the dresser, adjusting the wig over his short blond hair. He was looking more like a large doll at this point than a man in girl’s clothing, or an actual girl. But I hadn’t gotten the feeling that Jack wanted Alex to look like a girl. He seemed to be making a point. Showing Alex what he could make him do. And Alex was willingly playing along. It would take far greater skill than what I possessed to make Alex look passably female.

  When he had the wig in place, I came to his side and did the makeup, going for a lighter version of Tim Curry’s look in The Rocky Horror Picture Show. No whiteface, but plenty of eye shadow, lipstick, rouge. Then I took a step back and admired the outfit.

  “Oh, wait,” I told him. “Shoes!”

  I’d gotten the two pairs, but now I realized that I’d forgotten nylons. Quickly, I rummaged around through my drawer. He’d never fit into my panty hose, but he easily slid on a pair of stockings, ones that had a self-sticking band at the top—rendering garters unnecessary. Once he’d slid the stockings over his silky smooth legs—he’d had the full wax job here, as well, I noted—I offered him the choice of heels. To my surprise, he chose the superhigh ones, and he walked gracefully in them, making me wonder if perhaps this wasn’t Alex’s first time in drag.

  “Now what?” he asked, gazing at his own reflection.

  “I guess I bring you back down the hall to Jack.”

  “He didn’t say what he was going to do?”

  I shook my head.

  “Did he dress you himself?”

  I shook my head again. “I was inspired,” I told him, “by what I’d bought for you.”

  But before we could return to Jack, the bedroom door opened and my man—our man—entered the room. He took a moment to drink in the new Alex, before sitting on the chair in the corner. He still had a whiskey glass in hand, and from the look in his eye, he seemed to be waiting for a performance to start. But Alex and I were like marionettes without their puppeteer. We had no idea what to do next.

  “You’re pretty like that,” Jack said, and I saw Alex’s cheeks turn pinker beneath the cotton-candy wash of blush I’d given them. “Very feminine. Although not quite female. A perfect partner for Sam, who has stepped into the masculine role tonight, without managing to look all the way like a boy.”

  He took a sip of his liquor and continued to stare for a moment before saying, “It’s been a brutal few weeks for me, and I was looking for something different tonight. Something unusual. I don’t know exactly how this idea came to mind. Maybe I took one too many drives past the windows of that sex store on Santa Monica Boulevard. Or maybe I’ve always wondered what Samantha would look like in the driver’s seat.” He was thinking aloud. That’s how it seemed to me, and Alex and I remained silent, both his audience and his tiny cast.

  “Kiss her, Sam,” he said, and I realized he wanted me to kiss Alex, and that Alex was—for the moment—“her.” I did so automatically, stepping forward, cradling Alex’s face in my hands, kissing his mouth. Not able to think of him as a woman, but easily able to be turned on by the gloss of his lipstick smearing onto my own mouth.

  “No, not like that,” Jack sighed. “Kiss her like you like to be kissed. Kiss her the way I kiss you.”

  My mind whirled, but I thought I understood. I gripped the back of Alex’s neck, taking charge, pulling him toward me, and I kissed him forcefully, the one in power, the one making the rules. I bit his bottom lip when we parted, and felt Alex shudder slightly at that tiny insignificant spark of pain. He towered over me in his shoes—towered even in bare feet—but still, I was the one in charge.

  “Better,” Jack said. “Much better.”

  And then we were waiting again, standing there in front of him, two actors before the director, or two naughty juveniles before the headmaster, waiting for the next command—the next direction—the next…

  “Spread her out on the bed. Make her feel wanted.”

  Crazy stuff, this. But, of course, I didn’t argue. Instead, I led Alex to the bed and he willingly lay down on his back, looking up at me. I saw trust in his eyes and that made me feel scared. He had faith in me. Faith I didn’t have in myself. But when I continued to meet his gaze, I felt a bit of power transfer from Alex to myself, and I knew what to do next. If I were Jack, I’d be binding this pretty doll’s wrists over her head. And so I did, without a command from my man, without a word of instruction, taking Alex’s wrists and cuffing them easily, then looping the chain over the hook above our bed. Jack chuckled at this little bit of improvisation, and I could tell he approved.

  I could tell Alex approved as well, because his pinafore had become a pup tent—reminding me of men I’d massaged in the past, of all the tents I’d had to avoid during my several years as a legitimate masseuse. But this was different. The tented pinafore turned me on instantly, gave me more confidence than I’d had all evening. I almost felt my own cock twitch in response. At least, it did so in my imagination.

  With Alex captured so, I waited for Jack’s next word, but when I looked at him, he simply nodded. So I understood that he liked the direction I was taking. I was on my own now—for the moment—I had to be creative. And I had to be in charge.

  But what did that mean exactly? I thought for a moment, considered what I most wanted to do. My eyes returned to the pup-tented pinafore, and I knew. I climbed on the bed between Alex’s legs and lifted the dress. Alex’s eyes were on me. Focused. I easily slid his panties down his thighs, pulling them all the way off, even over the skyscraper heels, and then I crawled back to my spot, regarding Alex’s massive hard-on for only a second before dipping my head down to taste…

  Chapter Thirty–Six:

  Maybe Just Once

  Alex groaned darkly as my mouth welcomed his cock. He arched his hips
and pulled on the chains that bound his wrists, tugged with a vibrant intensity even though I knew he didn’t want to get away. I licked around the tip of his cock then bobbed my head, taking more of him inside my mouth with each passing second.

  Yes, I was turned on by the whole scenario, but mostly because of Jack watching. The fact that Alex was dressed as a doll didn’t make me wet. It was being in charge, feeling the harness and silicone toy still in place under my jeans, and knowing precisely what I was going to be doing with them before the night was over.

  Jack sipped his drink. I could feel him watching me. I could feel his eyes wandering over my body, taking in every motion. I performed for him, licking Alex, working to make his whole cock disappear down my throat. I was lost in this world, shimmying my hips, tossing my hair out of my face, until Jack’s hand was on the back of my neck, gripping me like a cat grabs her kittens. Momentarily stunned, my body tensed, and I had to work to meet Jack’s eyes.

  “You suck cock like a girl, too,” he said, an echo of our conversation out in the living room. Yet however cold his tone was, I realized he was right. I might be wearing the strap-on dick. I might be dressed—to the best of my abilities—like a boy toy, like one of those hunky men for hire out on the strip. But I was a girl. Heart and soul of a girl. Hungry mouth of a girl. Jack had my body in his strong grip, and I felt as if I wouldn’t be able to breathe again until he gave permission.

  “You’re trying to turn me on,” Jack said. “You think you’re starring in some porno film, with all your hair flicking and your overacting.”

  He’d nailed me, yet I didn’t know what he wanted, didn’t know why he was chastising me.

  “Like this,” he said, shocking me with the rough way he pushed me aside, so that I fell back on the mattress, tripped by Alex’s thigh, coming to rest on the far side of the bed. Jack gripped on to Alex’s shaft, his fist firm, and he jerked the boy’s cock, using my own spit as lube. Alex looked as if he were going to pass out. The mix of his current pleasure and the fear of impending pain were both vying for first place in his eyes.

  Jack worked Alex with finesse. Fast and furiously, his fist pumping on Alex’s cock, his face, when I dared to look up at it, intent, as if he were on a mission. There was a dangerous look in his eyes that made me quiver. I knew right then what was going to happen next. What this whole night was ultimately about. Somehow, I understood, and I felt as if the world had stopped.

  No, that’s not right. I felt as if my world had shattered.

  But Jack managed to surprise me once more. As if he were playing his own cock, as if he were the one being jerked off, Jack seemed to nail Alex’s limits to perfection. Right before the boy came, Jack glared over at me.

  “Get back here.”

  I scrambled into position.

  “Use your mouth.”

  I did my best. I opened my lips and sucked Alex again, this time trying to imagine I really was a boy. That Alex was my partner. That I knew all there was to know about cocks and how they worked. I sucked him harder than I had before, and Alex groaned and raised his hips, and as I felt the first shock wave of his orgasm rush through him, Jack pulled me back once more, so that Alex wet my cheeks, the edge of his pinafore, and the bed.

  I wiped my face on the back of my hand and sat back on my Docs, feeling stunned. Feeling as if a movie I’d gone to see had changed midway from a comedy to a drama. Jack didn’t pause for a second. He used a sheet to wipe off Alex, tossing the rumpled cotton onto the floor as he walked to the cupboard where he kept his favorite toys. I stood and moved over to the wall by the door. My heart started to race as I wondered who would be on the receiving end of Jack’s wrath—wondering where his current mood had come from. He’d been easygoing out in the living room. And now, now he was a towering, frightening Dom. Alex seemed not to have sensed the change in the atmosphere, momentarily whipped by the pleasure of his climax.

  Jack searched through his range of toys until he found a paddle, and I watched him grip the handle and return to the bed. I pressed back against the wall as Jack unhooked the handcuff chain, but left the cuffs in place.

  “Ass in the air, now, you know the drill,” was all Jack had to say. Clearly, Alex did, rolling over on the mattress and getting onto his hands and knees. He was still in those stockings and shoes, that white dress, but now he looked like a doll after the dance, rumpled and ruined. Jack flipped the hem of the dress, revealing Alex’s muscular haunches, and then he motioned to me.

  I’d been watching, heart pounding, and now I was being called into duty.

  “How would you spank him?” Jack asked, handing over the paddle.

  I looked at Jack, looked down at Alex, and gripped the paddle. This shouldn’t be difficult, right? I’d been on the other end often enough. I hesitated another moment before letting the paddle connect soundly with Alex’s ass, and then again, on the other cheek, spanking steadily, firmly, until Jack stopped me. He didn’t have to say the words—you hit like a girl—but I could hear them in my head. I thought he would demonstrate proper paddling methods, but he surprised me.

  “That’s not how you’d do it, kid. I know you. You’re trying to please me.”

  I looked at him curiously, not understanding the comment. Of course I was trying to please him. Pleasing Jack was my mission. Pleasing Jack was all I understood. And now he was changing the game, changing the rules.

  “How would you spank him? If you had the freedom to punish him any way you wanted. How would you do it?”

  I was quiet for several seconds, and then I said to Alex, “Stand up.” He moved immediately. “Bend over the bed.” He obeyed as if Jack were making the requests. I lifted Alex’s dress, and the movement of doing so, the drag of the fabric on his freshly shaved skin, made my pussy clench.

  And I got it.

  The delight in standing there, in watching Alex bend over for me, in seeing him do what I said. In watching him wait for the first blow to land. And I understood Jack’s taunts—you come like a girl, hit like a girl, lick like a girl. He was trying to raise the power up inside of me. He was pushing me, verbally punching me, trying to get me to break out of my submissive shell, if only for a moment. If only for a night.

  Never stay still. Never become stagnant.

  I hefted the paddle once more, and as I did, I realized I wasn’t doing this to prove something to Jack. I was doing it to prove something to myself. Which is what Jack wanted all along.

  Chapter Thirty–Seven:

  Free

  Honestly, I didn’t know why Alex was on the receiving end of this evening of punishment. I didn’t know why Jack had decided to dress him in ruffles or have me do his makeup. And here’s the truth: I didn’t care.

  I was aware only of the way the occasion made me feel. The heft of the paddle in my hand, the power behind each blow I delivered. I wasn’t Dom enough to whisper any threatening words to the handsome man bent over in front of me. Even though I knew the words that would have made me the wettest had I been the one in Alex’s supplicant position. Instead, I focused on the blows, striking evenly, admiring the instant rosy flush to Alex’s pale skin. He had—I will say—a perfect ass. I’m not even into rear ends—why would I be, as a die-hard sub? But Alex was a fine male figure, the ideal type for an artist’s model. A Michelangelo sculpture come to life.

  And now, I was in charge of him. At least I was for the moment, slapping the paddle against his tender skin until I could feel the heat of the action in my own muscles.

  Alex didn’t cry. I wasn’t able to inflict that sort of pain, and I’d already seen him take far worse at the club under Jack’s sturdy care. He didn’t beg, didn’t even look at me. Stoically, he took what I had to give. Almost as if he truly were a model, as if Jack were using him as a training model for me. But what would that mean?

  I couldn’t think about meanings now. I could only think about action.

  Finally, Jack took the paddle from my hand and pushed me aside. I resumed my spot at the wall,
watching as Jack undid the handcuffs and tossed them aside, then lifted Alex to standing position, removed that silly dress from him, pulled off the wig. Now, we saw Alex in the remnants of his finery—the smeared makeup, the hose and heels. He was fully hard again. My spanking had created that one response, at least. Jack could have led him around by his cock if he’d wanted. Instead, Jack said, “How do you feel?”

  Alex took his time answering, completely at ease standing nearly naked in front of Jack. It was clear he didn’t know what Jack wanted him to say. He weighed his words carefully, eyes focused on his boss, before trying out the word, “Fine.” Simple. But would it pass?

  Jack shook his head. “How do you feel about submitting to her?”

  Alex wouldn’t look at me. He continued to meet Jack’s gaze steadily, but I saw his shoulders sag slightly. “I didn’t submit to her.” He seemed confused that Jack would ask this.

  Jack gripped his chin in one strong hand, holding him tight. “What do you mean?”

  “I submitted to you.”

  Jack smiled. His easy smile. His natural smile. It was as if Alex had won the million-dollar prize. “Good answer.” It was, quite obviously, what he wanted Alex to feel. To think. It didn’t matter who wielded the belt or the paddle. Didn’t matter as long as the initial instruction had come from Jack.

  And there I was, leaning against the wall, proud of myself for already having mastered this lesson. I’d been living with Alex as Jack’s right-hand man for months now. I knew all about punishment by a second party. But there was more to Jack’s night of instructions. Of course there was. Jack wouldn’t be satisfied with something so simple as a post–blow job spanking. As putting Alex in his place. As showing him that there were other facets to being “more involved,” as Alex had stated he wanted to be.

  “Get dressed,” he told Alex. “In your own clothes.”

  Alex kicked off the heels immediately and pulled off the hose. Then he stood unconsciously, so beautifully naked, and dressed once more. He looked different now. Even in his slightly rumpled preppy gear. With the makeup still on, he had that rock star edge, and I found him actually sexy—something I hadn’t really considered before. Up until now, he had simply been an extension of Jack.