The Delicious Torment

by Alison Tyler

  And the next level involved Alex. Involved Alex in a brand-new role. One Friday morning, Jack took me to breakfast and described what he had in mind. He said that he felt he’d been too distracted lately with all the chaos at his job, and he wanted to spend the weekend in total relaxation. For some, this might mean a trip to Palm Springs or even a few nights at a spa.

  For Jack, this meant that he wanted to “break Alex in” to a new way of thinking.

  I had no idea what he was talking about. Jack explained in his own way. “Alex wants more. He’s been clear about that.” He stared at me for a moment, as if thinking over his past history with Alex, a history I only had the bare-bones knowledge of. “And I should have expected this type of…not rebellion, but request for extension for some time. I know you don’t have a problem bringing him into our relationship. He’s already there. Right?”

  I nodded. Yeah, Alex was there. He was there to make sure that I followed Jack’s rules. He was there to use Jack’s belt on me if he felt I was out of line. He was there, as he’d always been, a baby Dom.

  “But the thing is, Alex doesn’t really know what he wants. He switches in a way that I’ve never fully understood. I guess it’s why he’s always been so appealing to me. He likes to play with both men and women—although he does have specific types and tastes. He likes to be both a Dom and a sub. He’s malleable. But this weekend, I want to cast him in one specific role. I want this to be Alex’s time to fully experience a sub nature. And I want you to help me tame him.”

  His eyebrows went up as he looked at me, as if asking silently if I were game.

  Of course, I was game. Think of what I had before Jack. Total lack of physical and emotional input from my ex. Byron punished me by not speaking to me. By not touching me. He made me feel as if I truly were one of the least attractive creatures on the planet. I’m smart enough to know that it wasn’t true—because Byron held himself in such high esteem, why would he want to stay with a troll? But I was so beaten down by the time I left that it really took ages for me to be able to look in the mirror and not see myself through his critiques.

  Now, here was Jack, asking me to partner with him. Offering a range of yet unknown pleasures. “Yes, Jack,” I said automatically. “Whatever you want….”

  As he began to describe his plan, I felt my heart start to race. I’d read enough Victorian erotica to know where he was going when he described the outfit he wanted me to buy for Alex. And I’ll admit that this type of fetish had never been forefront in my own personal fantasies. But the idea of teasing Alex, of—as Jack had said—taming him, made my panties wet.

  Jack had a list:

  high-heeled shoes in Alex’s size

  ruffled panties

  a pretty pinafore

  a harness that would fit my slim waist.

  I had the makeup, of course, and the minor skills to use it.

  “Where’s Alex now?” I asked.

  “He’s doing errands in Malibu today,” Jack explained. “He knows to come by tonight. He doesn’t know he’ll be staying the weekend.”

  I looked back at the list, thinking of how I’d feel as I visited the different fetish stores, as I purchased the items Jack requested. Jack paid the breakfast bill and drove me back home. He had to hurry to get to work, but he hesitated a moment with the engine running. “You’re ready for this?” Jack asked, looking closely at me.

  I glanced at the list—the word harness standing out boldly to me—and looked back at Jack, responding like a soldier in his private army. “Yes, Sir.”

  “I’ll do my best to be home early. You have everything set for me.”

  “Yes, Jack,” I said, wishing there was time for him to take care of me now. Wishing he could spare the few minutes for a quick fuck that would at least buy me a little breathing room. How was I going to wait all day?

  “Good girl,” Jack said, smiling at me, clearly guessing how aroused the whole scenario was making me. “See you tonight…”

  Chapter Thirty–Two:

  Shopping Spree

  I was becoming a regular customer at several of the local sex toy stores. In fact, I’d almost lost my nervousness completely about walking down the fetish-filled aisles. (All right, I still blushed, but I could handle the situation.) This time, I was on a mission. I was actually being allowed the chance to see life from Alex’s perspective. Jack had given me a job, and there was no way I planned on failing.

  The list was bold in my mind. Everything had to fit Alex except for the harness. That was for me. And that was the only real reason I felt insecure as I wandered through the different rows. A harness was all Jack had said. But I knew what buying one would mean. I would be wearing the thing by the end of the night, and I would be topping Alex.

  Swallow hard with me, if you want to feel that lump of fear in my throat. This was far out of my realm of fantasy. Pushing my personal boundaries to the extreme. What would it be like to fuck Alex? What would it be like to stand behind him, to grip his hips, to pull him back on—

  On what?

  Jack must have wanted me to choose a cock to go with the harness, right? He hadn’t said, and I guessed that several of our toys at home would probably work. But why not be sure?

  I picked the harness first, a sleek black leather one with silver buckles. The pierced, pink-haired woman behind the counter hurried over to my side to explain the benefits of the one I’d chosen. “It doesn’t cover your coochie,” she pointed out. “The straps go around the upper thighs, leaving your ass and your pussy exposed.”

  “Wow,” I nodded, impressed with how much information she happily offered, and thinking back to high school, when a group of my friends and I had been assigned to do an oral report on PMS for science class, and one of us had to use the words “breast tenderness.” For hours, we all stood in front of the mirror, practicing, trying to decide who could say the phrase without turning beet red. I compared that experience with this girl who had no problem at all talking to me about my coochie.

  “And you’ll want to choose one of these,” she said forcefully, leading me to the display of dildos and gesturing at the ones she liked the best for a variety of reasons. Some were stiffer. Some vibrated. One was a pure midnight blue. One was angled to reach the G-spot. (Not a bonus where fucking Alex was concerned.) I waited for her to leave so that I could make my choice alone, but she seemed glued to me. The store was empty at this early hour, so perhaps she was bored.

  Now, if I were writing a story for one of my anthologies, I would describe the sex scene the girl and I enacted in the dressing room. You can see it, can’t you? This pink-haired minx would have grabbed her favorite dildo—electric violet—explained that I really couldn’t make a confident choice without trying one out, and then led me to the dressing room on the lower floor. And depending on my mood, I would have written how I had fucked her up against the mirror until she screamed with pleasure. Or I would have described how she had undressed me piece by piece, bent me over the lilac marabou-trimmed chaise, and taken my “coochie.”

  But those are fantasy stories, and all that actually happened was that the pretty punk girl wrapped up my selections in tissue paper and handed me my silver Mylar bag and a copy of the store’s catalog. “In case you want to order anything from the privacy of your home,” she said, with a wink.

  At the next store, I bought Alex’s outfit, using my own discretion in regard to color and the amount of ruffles, keeping in mind Alex’s coloring, his build, his attitude. Trying to imagine him in the clothes. I didn’t want him to look ridiculous. I wanted him to look sexy.

  Years ago, when I was still in school, I managed a tiny clothes store in town. One of our regular customers was a transvestite who would come in dressed entirely as a man—and looking rather hunky, actually, in a Clooneyesque sort of way—and then would change into outfits in the little dressing room, adding the shoes he’d brought with him in his briefcase. It was a bit amazing that he actually fit into the clothes. Yes, he chose t
he largest sizes, but how many men can buy off the rack from a ladies’ store?

  He only occasionally made purchases. I think the thrill was more in choosing the clothes and trying them on in a public environment. For the first few times, he simply walked around the store. Then he lied and said he was looking for something for his wife. The next time, he added that she and he were about the same size, so maybe he should try on the dress to see if it would fit her. And finally, he came out of the dressing room one day wearing one of the pretty frocks, complete with nylons and high heels.

  Aside from helping buddies with their makeup before catching midnight viewings of Rocky Horror, this was about the sum of my experience in the dressing up men department. But I imagine it’s probably a bit more than most twenty-three-year-olds have.

  For Alex, I did my very best, choosing two different pairs of shoes—one stripper high, the other slightly more subdued, but still towering. Jack hadn’t said anything about a wig, but I bought one—a pink one, thinking about the pretty vixen in store number one. Sometimes being fully in disguise helps. I know that.

  Then I went home and started to prepare.

  Chapter Thirty–Three:

  To Be a Lover

  Home again with my purchases and my plans, I set about turning our place into the perfect party atmosphere. I’d gone beyond the list of Jack’s requirements, stopping at a stationery store to buy additional supplies. Streamers. Ribbons. I even bought silver heart-shaped balloons. We were not near Valentine’s Day, but the living room and bedroom were adorned in that spirit by the time I was done.

  When I was finished, I set out the dress, shoes, wig, and stockings I’d bought for Alex. And then I went to transform myself. I wanted to wear the harness under my clothes, and I’d known that meant that most of my formfitting jeans were out. So I’d also gone to a thrift store on Melrose and bought pants that fit over the leather harness. (Shades of working in that clothes store back in school, with me in the role of the transvestite now.) I’d bought a vintage sailor top, as well, and even though Jack had not asked me to dress up for the evening, I…well, I had plans of my own.

  With hours to play before Jack and Alex arrived, I took my time, fitting on the harness, cuffing the pants, choosing the perfect motorcycle boots. My hair was short now, and easy to slick back. I used black kohl pencil on my eyes, going for that rock-star androgynous look and succeeding to some degree. I didn’t bind my breasts, but I put on two tight-fitting sports bras for a flattening effect. When I was finished, I had to admit, I looked good. I’m too small to be any sort of threatening male presence. Too fine-boned to pass for a real man at all. But I didn’t look like me, and that was the goal.

  With a bit of Jack’s aftershave, I completed the job. And then I poured myself a glass of wine and waited. The rest was up to Jack. I didn’t know what he would have told Alex. I didn’t know how the boy was—or was not—prepared for the events of the evening. But I did know that I was growing wetter by the second.

  Jack arrived home early, took one look at me, and started to laugh.

  “Should I change?” was my instant response.

  “No, baby, you look amazing.”

  “I wasn’t sure—”

  He pulled me to standing and spun me around. He touched my heavy belt, stroked my flat chest, nodded his admiration. “It’s wonderful.” He stepped back to take in the whole effect. When he kissed me, and got a whiff of his own scent, he laughed again. Clearly delighted with my transformation.

  “That’s what happens when you date a writer,” he said as he poured himself a drink. “You give the bare outline, and a whole story emerges.”

  I sat back down on the sofa, pleased with the compliment, as we waited for our guest of honor to arrive.

  Chapter Thirty–Four:

  Like a Girl

  Did I think Jack would actually let me change his plans like that? I mean, I didn’t know what his plans actually were, but he’d given me a very specific list, and although I had bought every item he’d requested, I’d also bought several extraneous ones.

  As I sat at Jack’s side, I was aware of him staring at me. Sipping from his drink and staring. No, I’m not the first girl to try out a look like this. I’ll admit, the scene in 9½ Weeks was in my mind as I transformed myself. But was it in Jack’s?

  He looked without speaking for several moments, and then he said, “We’ve got some time.”

  “What do you mean?”

  “Alex had a few errands of his own today. He won’t be here for a bit.”

  I waited, knowing there was more to come.

  “Walk for me.”

  Without a word, I stood and crossed the room, knowing somehow what Jack wanted. To see if I had any sort of swagger. To see if I could pull off the insolence of a tough young male. Jack laughed at my stride, and I felt my face flush. But at least he found humor in my attempt at masculinity. He wasn’t visibly angry or offended.

  “Now, show me what you’ve got.”

  I hesitated this time, unsure.

  “Show me, Samantha. Drop your trousers and show me.”

  I unbuckled my belt, realizing my fingernails were still painted my favorite hue—that dark blood-red Vamp. But this was the era when boys were playing with nail polish. That didn’t matter so much. I worked the belt, pulled the buttons on my fly, and then lowered my jeans.

  The cock, which had been molded up against my flat belly, now sprang forward.

  Jack laughed harder than ever.

  I hadn’t wanted something realistic. The veiny ones with real-looking accessories had given me the creeps. This was beautiful. Midnight blue with swirls of white. Big, but not too big. I slid my hand along the shaft and Jack stopped laughing.

  “You touch yourself like a girl.” There was both disgust and pity in his tone.

  “I am a girl.”

  “Not in that outfit. You’re trying for Sailor Joe, right? Yet you grip your joint in that wimpy manner. Oooh, look at me! I have a cock. Christ, it’s not even a cock. It’s some girly toy.” He’d nailed me. He was right. I had gone half the distance in my efforts, hadn’t been willing to go the full route.

  “Try again.” His voice was cold. The rules of the game had changed.

  I thought of what Jack looked like when he came on me, every so often, standing next to the bed, working his hand on his cock. The image made me seriously wet. When Jack gave himself pleasure, let himself go, finally reached his limits. And Jack had such serious self-control that I found that situation mesmerizing. Jack’s hand, jerking faster and faster, touching himself harder and with more power than I’d ever dare.

  With difficulty, I tried to channel that image, tried to make the vision my own. I closed my eyes and let my head go back. I stood up tall, feeling a little more powerful in my Docs than I would have barefoot, although the fact that my jeans were pooled around my ankles did limit my mobility. Concentrating, I slid my hand along the smooth plastic cock. Up and down, squeezing hard, speeding up.

  “Spit on your palm,” Jack whispered.

  I did. Or I tried. Waiting for the inevitable, “You spit like a girl” comment to come. I could have licked my palm. I could have unbuckled the toy and deep-throated it with finesse. But this was different. This was all at once a lesson—work rather than play.

  “Jesus,” Jack said, and I opened my eyes, watching as he stood up from the sofa and came to my side. He pushed me back against the wall, spit into his own palm and started to work my cock for me. And in instant, I felt as if it really were my cock. As if I were connected to this toy, or really, as if I were part of an X-rated version of The Velveteen Rabbit and the synthetic cock had somehow turned real.

  Jack’s eyes burned into mine as he stroked me, forcing the connection between the two of us. I could imagine us somewhere else. In the back room of a club, Jack manhandling me. Others watching. An audience forming because of our heat. Or out behind some bar, in the parking lot, Jack using his own spit to lube me up, knowing th
at in seconds he was going to have to stand aside, to watch me come on the dirt.

  And then another image, one that made my heart seem to still. Jack doing this. Exactly this. To Alex. And right then, as I stared at Jack, wondering if he could see the questions swirling in my eyes, the door opened and in walked Alex.

  My breath caught. Each time Jack’s hand pumped my cock, he pressed the base of the toy back against my clit. And each time I felt that connection I thought I would come. He didn’t stop. He didn’t turn or say a word. He kept going, pausing only to add a bit more spit to his palm, so that I felt he was greasing me.

  Alex froze. I’m sure some wiseass comment was on the tip of his tongue, but maybe he caught a look at Jack’s face, and that stopped him. He was able to shut the door behind him, and then he stood totally still, and I knew he was waiting for instructions.

  “You’re going to come, boy?” Jack crooned to me, but teasing somehow. Taunting me for doing this in the first place. For adding my own bits of fantasy to a script he’d fully realized already in his head.

  “Yeah, Jack.”

  “Then come.”

  My knees would have buckled if Jack hadn’t used one hand to pin my shoulder against the wall, holding me in place. The climax was almost frighteningly intense. Embarrassingly so, as I was being watched closely by the two men in my life. And then it was over, and Jack let me go, and I hiked up my jeans and sank down to the floor, letting the wall support me now.

  “You even come like a girl,” Jack said, as he poured himself a fresh drink.

  I didn’t answer that. I didn’t have anything to say.

  Chapter Thirty–Five:

  Blurring the Lines

  See? You can be dead sure that you are into one thing, focused on that concept solely, and then be demolished when something else turns you on. In all the years I dated Byron, I never thought of dressing in drag, of buying a harness, of stroking my synthetic cock in front of him. Never even remotely imagined demanding that he deep-throat my new toy, or suggesting that I get out a bottle of lube and have a serious romp between his pillowy cheeks.