Unexpected Pleasures

JENNIFER TALLIN

 

I wanted to fuck Henry from the first time I saw him. I work as the curator at a local gallery, and he is an up-and-coming artist who was introduced to me by a mutual acquaintance. Sally had given me his portfolio in advance, and I was impressed. His work was rich with texture and color, and bold in subject matter. I had expected to meet a tough, testosterone-heavy artist with an attitude. Trust me when I say I have met my share over the years.

Henry was different. I knew he was hoping to get his work shown at the gallery, but as soon as I laid eyes on him, I found myself hoping for something else. I wanted to suspend him from the wall in my bedroom, hook his cuffed wrists in place, cut his clothes off his body and let him feel the wrath of my power.

Of course, I did not say any of those things to Henry. All I said, as I shook his hand, was, “Pleased to make your acquaintance.”

“The pleasure’s all mine,” he replied.

“That’s what you think,” I said under my breath.

Henry let his eyes work up and down my body. He seemed to flush when I did not release his hand right away, but I was satisfied when he did not immediately look at the floor. There was a connection between us. He felt it, too.

Our friend in common was completely oblivious. Sally blathered on about what a fine gallery I ran, how the elite players considered the art on my walls to be some of the best. She worked her way around the room, commenting on what a good fit she felt Henry’s creations were. She seemed to have no idea that Henry and I were engaged in a little game called “let’s size each other up.”

When she was finished with her tour, our friend finally shut her mouth. She looked at Henry and then looked at me. Quietly, she said, “I think I’ll let the two of you get to know each other better.”

“Good idea,” I said. Henry remained silent.

When Sally left the gallery, I turned to the young artist. “I would be happy to host your show,” I told him. “I had already decided that based on your portfolio before we even met.”

Henry started to speak, I suppose to thank me, but I stopped him.

“I wanted to get that business out of the way, because I have a few personal questions for you.” As I spoke, I locked the gallery’s door and flipped our artistic sign so that it read CLOSED on the other side. Henry’s art portfolio lay open on my desk. I wanted Henry open just like that. I looked at him. He bit his lip.

“Do you have a girlfriend?” I asked.

He shook his head.

“Boyfriend?”

“I’m not gay.”

“Then what are you?”

He drew in a breath, and I could imagine what he would look like when he came. I do not know how I knew, but I had an instant flash in my mind, Henry with his head thrown back, his eyes closed, his whole body taut. “What do you think I am?” he asked, and I will admit that I liked the spunk in him.

“I think you are a submissive,” I said. “Whether you know it or not. I think that nothing would give you greater joy than to put yourself in my hands and let me take you where you need to go.”

“Where do I need to go?”

“To my place,” I said, and he grinned shyly at me. I live only a few blocks away from the gallery. Henry and I walked there in no time, and on the way he told me that he had been single for nearly a year. He was tired of playing the dating game. His art did not support him yet, but he was not a mooch. He worked as maître d’ at one of the ritzy restaurants in town. I let him talk, learning the cadence of his speech. I am a good listener. I often pick up on things other people do not—things that are not said but implied, like the fact that Henry had never been topped before. He was used to being in control in a relationship. Why? I thought that was because he knew so deeply what he wished someone would do to him that he had no problem conjuring such scenarios for a partner.

“Have you ever delved into true BDSM before?” I asked him.

“No,” he said. “Not really. I’ve held a girl’s wrists over her head when I fucked her. Once I used a scarf as a blindfold. But nothing serious.”

When we arrived at my place, I unlocked the door, but before I let him cross the threshold, I asked, “What is your safeword?”

“I’ve never had one before.”

“Choose one now.”

He stared at me, and I knew he was trying to decide whether he would really be able to go through with this. Was he ready? I could tell from the bulge in his slacks that he was willing. He hesitated for a few seconds, and then he said, “Carnelian.” It was the name of one of his paintings.

“That’s a mouthful.”

“I don’t think I’ll have to use it.”

From the first step into my apartment, he was a work in progress. I am no artist, but I absolutely felt like a sculptor, molding something fresh from a block of clay. Henry was malleable, bending to his knees immediately when I put my hands on his shoulders and following me in a crawl when I snapped my fingers. There were so many things I wanted to do to him that my thoughts kept getting ahead of my actions. Slow down, I told myself. You need to do this right. He deserves the best you can give him.

In the bedroom, I did exactly what I had imagined at our initial meeting. Well, almost exactly. I wanted to cuff him and hang him like a piece of art on my wall. But I could not cut his clothes off. Not without him having a second set to wear. We were close enough to know we were going to fuck, but not so intimate that I felt comfortable destroying his property. So I made him strip first.

I sat on the edge of the bed as he undressed. His body was lean and hard, and he had unexpected tattoos hidden under his longsleeved T-shirt. He did not comment on the fact that I was watching him disrobe, but I could see that he was nervous—and aroused. His erect cock was long and thick, and seeing how turned on he was turned me on, too.

“You like the thought of me punishing you, don’t you?” I asked. My voice was casual. I might as well have been inquiring whether he would like a glass of water.

“Yes,” he said softly, as I cuffed his wrists.

“You felt the heat between us from the moment you walked into the studio, didn’t you?” As I asked the question, I turned him to face the wall and attached his cuffed wrists to one of the formidable hooks I had installed just for this purpose. He looked beautiful like that. His back was muscular, and his ass was tight and firm. I could not help but reach down and cup both cheeks in my hands. I squeezed firmly, and he sighed.

“Even before,” he said, surprising me. I was reaching for a flogger as he said, “I’ve been to shows at your gallery before. I’ve watched the way you interact with men.”

“Interact,” I repeated, menacingly. I gripped his cock as I spoke and pressed my lips close to his ear. “What do you mean by that?”

“You’re like a tiger,” he whispered. “You look as if you could devour a man.”

“Don’t you wish,” I sneered, stepping back and snapping the flogger against his ass. He jumped, but did not make a noise. I struck again, the many tails of suede caressing his skin. I know precisely what this implement feels like. I would never use a tool on a lover without experiencing the sensation myself. The flogger delivers a sting right from the start, all those tiny tails hitting the skin at once. But with steady application, that sting transforms into a long, slow burn.

I peeked at his cock, which had been hard before, and saw it was now so erect I could have hung the rope handle of the flogger on it. His face was a mask of concentration. He was processing the experience. I stepped back and struck again, several times in a row. He did not moan or shift his stance. I was proud of him. Before I brought out the next of my tools, I decided to give him a reward. I grabbed a bottle of lube from my nightstand and slickened up my right hand. With finesse, I gripped his hard-on and started to jerk him off. As I pumped him, I used the palm of my left hand to spank his cheeks—hard.

Henry did not know what to do. He arched his body forward to fuck my greasy fist, and he flinched at the fresh spark of pain I was inflicting on his flesh. I knew he liked the warring sensations, because his cock leaked precome and he started to moan. I slid my hand between his thighs to stroke his balls. He whimpered as I used the tips of my nails ever so softly on this most tender skin. The whole time, I continued to work his cock like a pro.

“You are going to come,” I told him. “You are going to cream all over my wall, you bad boy. You will have to take your next round of punishment looking at the dirty mess you made.”

His body stiffened. I sensed he was getting close. To his obvious dismay, I let go of his erection and went to my closet of toys. I gripped a paddle in my lube-free hand and returned to his side. “Each blow of the paddle gets you one stroke of my hand on your cock,” I told him. “I will deliver both in sets of five.” He understood. His eyes were wet with longing. I landed a stinging blow with the black side of the paddle and then another and another until I had hit five. Then I resumed the hand job, jerking his rod quickly five times. He lunged forward, trying to force me to continue, but the chain attached to the cuffs did not have the slack he required to pull it off. I spanked him five more times, even harder, and he stifled a moan by biting his lip. Now, I gave him those five palm strokes he had earned in slow motion, my firm fist truly trying to drain the seed from his body.

I was proud when he stood straight and tall, preparing to take the next set of blows. “How many more do you think you will need,” I asked him, “before you make that lustful image on my wall?”

He looked at me. He was clearly trying to do the math through a haze of bliss.

“Five?” I asked. “Ten?”

“Ten,” he said.

“If you are wrong,” I told him, “I will have to find a different way to punish you. I might put on my favorite strap-on and ream that tight little asshole of yours.” I looked at his face again. His mouth was open. He looked as if he did not know what to do or say. He wanted to tell me he would like that, but he could not make the words come out.

“But maybe that wouldn’t be punishment. Maybe you would like that too much.”

“Yes,” he groaned. “Yes, I’d like that.”

“So we will call that your reward,” I told him, giving him something to think about. I stood back, and then I gave him ten of the most blistering spanks I could deliver. When I was done, his ass looked as red as the flipside of the paddle.

He might have been able to come from the spanking alone. In fact, in the future I hoped to train him to do just that. But right now I would give him what I had promised: ten beautiful strokes with the palm of my hand. Of course, I had not promised that was all I would do. While he watched, I lubed my fingers and palm. I wondered if he could guess what I planned to do next. Both of my hands were glistening, and I gripped his cock in my right hand as I slid a finger from my left between his muscular cheeks and started to tickle his anus.

“Oh fuck,” he groaned.

“That is not my name,” I corrected him. I stroked his cock again, long and sweet and firmly. As I did, I started to press my pointer into his back door.

“Oh, Jennifer,” he moaned.

“Ms. Jennifer,” I snapped, and he repeated my name again, his voice hoarse. I tightened my grip on his unit and continued to probe his asshole. He seemed completely demolished by the way I was touching him. If he had not been held upright by the cuffs, I could imagine him falling to his knees in supplication. That would have robbed me of my current pleasure, though. I did not even count anymore. I pulled his cock and finger-fucked his tight hole, and soon he was coming hard, just as I had promised him, splattering my wall.

As soon as he had shot his load, I lifted the handcuff chain from the hook, but I did not uncuff him. I brought him to the bed and spread him out on his stomach with his head toward the wall he had disgraced with his come. “Now it’s my turn,” I told him.

He turned his head and looked at me, his eyes filled with desire.

I added more lube to my hand and spread his cheeks wide apart. I lubed him up until the valley between his cheeks was glistening wet. Then I retreated to the bathroom, washed my hands and got my favorite harness and cock out of the bottom drawer. I stripped and prepared myself. There is nothing sweeter to me than taking a man’s back door, especially an unexpected sub like Henry.

When I returned to my bedroom, I found him exactly as I had left him: on his stomach in the center of the mattress with his head turned toward me. Good boy, I thought. He might have moved to a sitting position, his back against the headboard. He might have gotten up and started pacing. I was pleased, but I did not praise him. I wanted him to worry a little bit about what was going to happen next.

He did not say a word as I climbed onto the mattress, but I saw that the muscles in his back had tightened. He was breathing in short and slow, as if trying to calm himself. I reached under his body and got my hand on his dick once more. It was still hard. I smiled to myself.

“Henry,” I said, “have you ever been good and properly fucked before?”

He hesitated at my question. I think he was probably trying to figure out the correct answer. Sure, he had been part of relationships in the past where the fucking might have been lovely. But this was different—and we both knew it.

“I mean,” I continued slowly, and now I started to work the head of my cock in between his cheeks, “have you ever had your asshole stretched around a nice, hard cock?”

He answered that question right away. “No,” he said, then seemed to remember his place and added, “Ms. Jennifer.”

“Are you ready?” It was almost too late for me to ask this question, because I knew he could feel the head of my synthetic cock opening his hole.

“Ready,” he murmured.

“You remember your safeword?” I asked kindly.

“I won’t need it,” he assured me.

I slid in a little more. Henry groaned and bucked his hips. Ah, the boy liked it. I had thought he would, but the way he moved let me know I was right. I pulled back and reached for the bottle of lube. This time, rather than simply slicking up the toy and his hole, I poured a river of the clear liquid between his asscheeks. The cold temperature made him suck in his breath. The feel of the cock against his asshole made him exhale in a rush. I liked that I was controlling him down to the very core of his existence.

“Lift up,” I told him, and instantly he went up on his elbows, his ass higher in the air. I gripped his hips and began to push inside him. I knew that at some point, I would be banging him hard. But right now, I wanted him to grow accustomed to the sensation and to fall in love with the way it felt to be reamed.

I worked as slow as I could until I felt Henry push back. That was the signal to let me know he loved every inch. Now I could really be me. I began to fuck him faster, but keeping a steady rhythm to my thrusts. Every so often, I would reach around and tug on his stiff cock. He kept his ass lifted up for me, and he moaned when I penetrated him to the deepest point. If I’d had a real dick, he would have felt my balls slapping against him. As it was, I simply ground my hips hard and then pulled back once more.

Someday, I would fuck him like this with his hands free. Then he could reach underneath and jerk himself off while I pegged him. This time, I continued to give him the occasional stroke, until I sensed that both of us were nearing our peaks. As I worked him to the finale, I held on to his cock and did not let go. I stroked my hand on his rod in time with the way my cock thrust into his ass. The whole experience became too much for me, which is odd. Usually, I can keep myself in check. But this time, the feel of his cock in my hand, and the moans he was making, took me over the edge. I let my clit press against the base of the dildo as I came, bucking against Henry. He shot his wad against my sheets seconds later, and then sighed and shuddered against the mattress.

Gingerly, I pulled out of his asshole and unbuckled the harness. I discarded the toy and pulled the boy into my arms. He lay against me, breathing sweetly as I reached for the handcuff key.

“You are released,” I told him. “I am setting you free.”

He surprised me by reaching for the cuffs and setting them back in place on his wrists once more.

“I don’t want freedom,” he said, looking at me with those darkbrown eyes. “I only want you.”

I kissed him and sighed, pleased that I had found a new artist for the gallery and a new lover on the same day. Meeting my unexpected sub had given me an abundance of unexpected pleasure.