by Destiny Moon
I even surprised myself with my tone. But Simon played along, perfect prey that he was.
“I don’t think I’m good enough.” His tone was meek.
“You don’t think you are?”
“I know I’m not, ma’am. I’m not good enough for you.”
“That’s right, Tailor Boy. Now get down on your knees.”
He knelt down. Crouched on my floor, he kissed my feet. He caressed my ankles with his soft hands and I sat down on my ottoman, fully clothed in front of my naked admirer. His dedication emanated from every part of his body. I could not help but feel adored. Something told me I could get used to having Simon around.
He stroked and caressed my left foot as I brought my toe to his mouth. He engulfed it with his soft, warm tongue, which was exactly the fellatio I craved. His suction became more and more prominent as I pushed and pulled my toe in and out of his mouth. With my right foot, I stroked the ever-growing bulge between his legs, which made him moan in delight. He slid his tongue between my toes and I cradled his now throbbing hardness with my other foot until we were both in dire need of relief. I recalled the image I had of Kelly—Mistress Veronica—and let myself feel the longing I still had for her.
* * * *
Simon and I had an excellent understanding. He was happy to design and sew and cater to my needs. In return, I toyed with him every time I felt like it. It was the perfect flattering union. I couldn’t have planned it better. Simon worked busily, compiling a late summer wardrobe of light dresses and pretty blouses for me. I perused fashion magazines and picked out fabrics and shoes and accessories. His job was to say ‘yes’ to me. It wasn’t an exaggeration to say that Simon became the hobby that occupied my time in those first couple of months at Strawberry Hill.
Hal could tell how much I was enjoying the arrangement.
“That Simon, he’s quite the terrific tailor, wouldn’t you say, darling?” he asked me one night, in his study.
I loved Hal. We were so easy around each other. It was easy to love him and easy to get along with him. We liked the same lifestyle and he never saw himself as my keeper, even though he was.
“Simon is excellent,” I confirmed, lying on his beautiful cherry-wood-trimmed sofa, reading my magazines while he sat at his desk with his cup of tea and paperwork. Many evenings were spent like this. It was hard not to love his study. It was better than an office, with its brick fireplace and bear rug, its antique furniture and old style lighting.
“Simon and I are preparing a surprise for you, dear.”
“For me? Does it involve nudity and a bottle of oil?”
He chuckled quietly. Whenever we were alone together, Hal felt comfortable to voice things he would never say in public.
“No, darling, nothing so dashing. I think you’ll like it, though.”
He was so dapper, Hal. I loved to do nice things for him. This surprise—the jade dildo and my perfectly fitted harness—was my latest obsession. It might not be the kind of surprise Hal was up for, but it was the kind of thing I felt was my duty. I just couldn’t resist.
He smiled at my coyness and we went back to our silent, solitary activities. I really loved him even though we hadn’t consummated in that way…yet. I often thought about it. I wondered if he did, too. We had sort of fallen into a pattern of not fucking because that was what seemed most natural. It seemed as if we shouldn’t because his preferences lay elsewhere. But I became intent on the idea. After all, we cared about each other. It was dangerous for me to start thinking of him in that way and I knew it. Our relationship had already reached the pinnacle of intimacy because we had been sleeping in the same bed, regularly, for months.
There is something about waking up in bed together that is inherently more private than sharing bodily fluids. I let Hal see me in what I think of as the most compromising position—sleep followed by bed hair. It was one thing to show off my body and my flexibility, to leave lovers wanting more or, even in the case of Sam, to leave them confused or at least with a mental image of my physical nudity. But Hal knew what I looked like naked in the real sense of it—devoid of all airs. He knew what it felt like to hold me, to feel my arms wrapped around him at night. He knew what I sounded like when I slept, whether I snored or not. He was always such a gentleman, so I never believed him when he told me I didn’t snore, but how would I know? The only other person I could ask was Kelly and those days had been different. Hal and I, though, we had something. It was a kind of closeness, more than a platonic relationship, more than a brother-sister style relationship. We weren’t asexual. In fact, we loved telling each other about our escapades and we had been involved with the same lover, so we couldn’t have pretended not to notice each other in that way. I didn’t want to put our closeness at risk with my harness plan. I couldn’t bear the thought of Hal’s rejection. I feared it terribly, which was why it had taken me so long to get Simon to make the harness. But as our wedding night approached, I felt that there would be something satisfying about Hal and I being able to express ourselves together.
One morning, as the sun shone through the white curtains, I felt his morning erection against me. I didn’t do anything about it, though part of me wanted so badly to slip underneath the covers and to take him in my mouth. I couldn’t do that kind of thing with him. He wouldn’t like it. In fact, I was quite sure he would have to be extremely turned on if he was ever going to let me use the jade dildo on him. I might even have to plan it in conjunction with a visit from Timothy or one of the new boys of which Hal was so fond. But that idea saddened me. I wanted it to be between the two of us. I wanted to be able to seduce him myself. It was the ultimate challenge.
Maybe what he needed, or what I needed, was more masculine signifiers, I thought as he put his still sleeping head on my chest. I lay there propped up on his pillows with my arms folded behind my back, and he nuzzled into me. Conventionally, our postures were the reversal of what our genders dictated, which only led me to further think about the possibility. Maybe I should take Simon shopping. Maybe I needed cologne. Maybe I would look great in tweed pants and a white collared shirt and a tie. Maybe I should learn to smoke a pipe. I smiled at the idea. It was no longer about Hal. I should feel as comfortable to do that as anything. Why not?
I’d been laying there in my private thoughts, looking out of the window, when Hal woke up. He looked at me.
“I can’t wait to be your wife,” I said. “Let’s do it soon.”
“If it were up to me, I’d bring the minister out today. We could do it right here, right now.”
“Minister? Like from a church?”
“Is there any other kind?”
“I hope so. Hal, I’m hardly a believer.”
“Oh,” he said. “Well, what would you like?”
“How about a pagan ritual?”
“Your absolute disregard for tradition is very charming.”
“What’s not traditional about paganism?” I asked sarcastically. “After all, it’s been around a lot longer.”
“I prefer a minister, dear,” Hal said. “For the sake of the guest of honour.”
“Who?”
“My benefactor. The reason for the wedding, the owner of Strawberry Hill and all of its surrounding acres.”
“Why have you never mentioned this before?”
“In good time, Julie. We’re still just getting to know each other.”
“Oh.”
There was an awkward silence and I realised that Hal was not going to offer any more information on the matter. I asked, “This arrangement isn’t just about us, is it?”
“No, it’s a little more complicated, I’m afraid. Let’s just say you’re the missing piece of the puzzle.”
“I am?” I was still confused.
“So I insist on a real minister. I hope you can find it in your heart to cooperate with that plan.” Hal looked at me over his reading glasses.
I settled into the calm awareness that what we were engaged in was unfathomable by the
church. For that reason, there was no need to feel hypocritical. We were free spirits who were marrying for the sake of the state. If Hal felt it best that the church be involved, then who was I to interject? I wasn’t here to make a religious statement. I wasn’t even here to enter the sanctimonious union of marriage in its ideal form. I was here because I loved Hal, I was ready to commit to him and I didn’t need God’s approval for that.
“Let’s have one of those lovely fall weddings,” I urged.
“It might seem too soon, too contrived,” Hal argued.
“I thought sooner would be better than later… For you, I mean.”
“It is, but I’ve managed to buy myself some more time. It looks suspicious when a man of my age, and in my situation…”
“Hal, you’re second guessing yourself. There’s nothing to be secretive about. People fall in love all the time. It’s quick. It’s passionate. It’s perfectly normal,” I assured him.
“You don’t know my benefactor. Why not let yourself behave like a proper kept woman and let me be in charge, dear?”
I looked at him, baffled. Had I not been behaving like a kept woman? I was unnerved by his secrecy but he was right. It’d be best to let him worry about it.
For good order’s sake, we had to make a big event of our big event. We invited all of Hal’s associates. We hired photographers and caterers, planners and extra servers. Simon took a week away from Strawberry Hill to personally pick up and escort my wedding dress back home. He had to go all the way to New York City, to one of the world’s finest bridal boutiques to pick up my custom gown. Or so he said, but I’d never heard of a successful American company that did not use the postal service or a courier.
I did my part and focused on making Simon very busy. He had to tailor a new tuxedo for Hal, and we both browsed catalogues and magazines for cuff links befitting the situation. No expense was spared.
Chapter Twelve
Throughout the planning, the most important accessory I could think of was my cock. I wanted what Sam had had. But I wanted the best that money could buy. Simon had listened to all my fantasies. The best part about him was that he listened not just as a tailor, but as a lover. I’d started to visit his studio. I called on him to give me one last fitting of the leather harness. It felt so good around my hips. The top of the leather came down in a heart shape in between my ass cheeks, and it stayed snug against my skin even with the beautiful jade cock at the front. He had hand-stitched the piece together. He had ordered the custom cock straight from a jade dealer in Beijing. It really was the finest package money could buy.
“What do you think?” I asked Simon as I emerged, naked, from behind his lacquered room divider. I was naked with my giant erection. His eyes almost came right out of his head.
“You look amazing,” he whispered, then gulped. I had managed to make him uncomfortable yet again. Simon was so darling and shy. I almost couldn’t help myself but go to extra trouble to make him nervous. I flipped my long hair out over my shoulders and licked my lips. He stood facing me, awkward, not knowing whether to avert his eyes or to ogle me.
“Come here, my boy.”
He walked over to me.
“Kneel down, sweetheart.” I said. He stood stiff, as though he hadn’t heard what I’d said. Then, like clockwork, he fell to his knees.
“I know you want to,” I said, combing my fingers through his hair. “You think I can’t tell, but I can. It’s too obvious. I know you want to suck my cock.”
He nodded in silent appreciation of my bountiful endowment. I really did have the most perfect and massive cock I had ever seen. I stood in front of him, stroking myself. It felt so good to move my palm up and down my shaft. I felt large and powerful and so completely free to express myself. Whether consciously or not, I had wanted to feel this way for as long as I could remember. I thought back to the first time I’d taken Tommy’s cock in my mouth, back on my parents’ farm, in the orchard. I had been so hidden away. Tommy had been so timid. It was as though he’d been ashamed of enjoying his cock.
Not like me. I was proud. I held my head high as I stroked myself and felt myself getting stiffer. It was in my head, I guessed, but my palm really did register a stiffer cock as I touched myself. My clit sprang to attention in a way that had not happened before. The sensation was just different. I wanted to take my time. I wanted my first blow job. I wanted to fill Simon’s mouth with my abundance even if it gagged him and I was quite sure, with my deep-rooted need, that I would gag him.
I pulled his mouth to my cock. He kissed the tip of it and opened his lips. Suddenly I felt contained, totally surrounded by the soft flesh of his mouth. I still had his hair between my fingers and stood standing in front of him as he thrust himself onto me. I guided him with my firm grip. He choked.
“I can’t… I can’t,” he muttered through his gurgling noises.
“You will, Simon,” I heard myself say. This experience had brought out something new and refined in me. I loved the way I felt. I grabbed his cowering head and shoved it onto my cock, as though Simon was a catalyst for my pleasure and container of what was to come. Tears started to form in his eyes, as if he were drowning in the sensation of being forced to take the entirety of my cock.
“You want this. I can tell. You need my cock,” I told him firmly as he sucked and sucked. Even hearing the words come out of my mouth made my clit harder than it had ever felt. I wanted to fuck him. It was a strange feeling, like being removed from myself and being with myself. I thought of how men had looked at me. That feeling they’d seemed to emit, especially when they’d grabbed me and held me tight and thrust my pelvis up and down on top of theirs or when, in the missionary position, they’d penetrated me, then thrust rhythmically in and out. I had that feeling. Like I wanted to prise Simon apart and get inside him and push myself deeper and deeper into him. I was surprised that one little alteration—a harness and a cock—could make me feel this way. The long-dormant feelings were finally able to come out with this chemical reactor, this most perfect prop.
Simon beckoned for more. Kneeling in front of me, he gave me the most intense pleasure by virtue of his position. He was so lovely. His blond hair and sculpted body made him a most perfect candidate for this household. I didn’t know if Hal took advantage of his presence as heartily, but I hoped he did. I could only imagine what their union would look like. Probably a lot like my own.
I pushed Simon onto the floor and placed a cushion under his head. I could no longer deal with the anxiety and excitement of what was happening. I crawled on top of him and placed myself carefully, cock in hand, over his mouth. I stroked my cock while his tongue found my pussy. I felt the need to come on him like I’d never experienced the feeling before. In my mind, I could see a whole army of cocks spewing forth their cum, and I was the sergeant major. I was the one with the most bountiful prize.
I made circles on Simon’s mouth as he grasped at my hips. I may have come close to suffocating him a bit—at least, his urgent moans suggested that—and I didn’t care much. If it was that dire, he’d struggle harder, I reckoned. I didn’t have time for distractions. My cock felt so good in my hand. I felt large and stiff and ready to explode on Simon’s face and all I could think of was a fabulous stream of my juices running over him. It was splendid, this kind of urgency, this kind of need. It was so different than coming with something inside me. Internal orgasms felt like pulling in. Whenever I came with a cock inside me, I was convinced that my tightening muscles were pulling on my companion’s shaft, bringing him deeper. This was an entirely different sensation.
I was rocking back and forth on Simon’s mouth, his nose up against my clit, his stifled moans against my pussy, my hands still grabbing at his hair when I felt the building climax of the greatest feeling ever. He stiffened his tongue just slightly and I pushed one final time against him, then let out a massive, satisfying moan. I knew part of it was my imagination, but it was like coming straight through my cock, covering him with my semen.
He was drenched. I pulled away feeling as if I were a sexist pig and he was my little tart. I even smiled at the idea.
I’d never wondered what it was like to be a man before. And just because I’d donned a cock didn’t mean I was any closer to understanding. But I did think of myself a little differently. Even the way I looked at Simon was different from how I would ordinarily look—I imagined—after an orgasm. And he just seemed stunned. Minutes went by before we exchanged any words at all. I bent down and he held me to his chest. It was oddly comforting to be held after sex—another thing that made me feel different. I felt like I could doze off into the most perfect sleep with him stroking my hair as he was.
“Oh, Julie, that was amazing,” he said.
I smiled. I was a stud. I had never questioned what kind of a man I would be if I were a man and now, without exaggeration, I had waltzed right into being a stud. Oh, most guys would be so jealous. Imagine working your whole life to attain this kind of sensation. Imagine having to get over all those male insecurities, and here I was with my giant cock and what was more impressive was that I knew how to use it. I just knew, instinctively. It made me want to fuck absolutely everyone. I went over a list in my mind of various charming girls and boys. I thought of Kelly first. I thought of Hal. Oh, it was delightful.
“I feel so close to you right now, Julie,” Simon whispered. “No woman has ever made me feel like you do before.”
“Uh…” I didn’t know how to respond. I was too tired and too spent to be mean to him about this. It was inappropriate. What did he mean? I vaguely paid attention. “Thanks, Simon.” It seemed the only worthy comment.
“You’re always saying not to be afraid, so I won’t be afraid. There’s something I have to tell you. I think I love you.”
Whoa, whoa, whoa. Now this was something I absolutely was not ready for. It was a buzz killer. Here I’d thought we were having the most perfect time and he’d had to go and ruin it by talking about feelings. Feelings didn’t enter into this, didn’t he know that? Had he lost his mind? He was a good fuck. He had a gorgeous mouth. But love? I was confronted with the ultimate liability. I was too good a guy for my own good. I was too talented with my cock. That was what this was about.