As soon as I made it clear to Trent that I was ready for more, he drew me to my feet, then guided me onto the bed. Again, I expected him to kiss me, but instead, he placed a hand against my cheek. His gaze grew almost tender while he regarded me, and I got the feeling he was assuring himself that I really was fine with going further.

I decided it was time to convince him. Though I was still nervous, I realized it would do no good to appear hesitant; the man obviously wasn't aroused by coercion. Besides, he was paying a small fortune for us to share this evening, and I wanted to make sure I gave him his money's worth.

Daring to take charge, I turned Trent toward the mirror while positioning myself behind him. We were both kneeling on the bed, and since he and I were about the same height, he had a clear view of my face over his shoulder. When I reached around to take hold of his cock, he made a guttural sound from deep in his throat. His stare was fixed on our reflections.

I gave him several slow, languid strokes. He was so hard in my hand, I could easily feel the outlines of the prominent veins lining his shaft. I delighted in the sound of his quickened breathing. "You're so fucking hot," I whispered in his ear. His smile let me know my words pleased him. As I suckled his earlobe, my own dick grew even harder. I gave a gentle thrust against Trent so he could feel it.

He reached for me then, his palms sliding over my skin. Still, he made no demands. I was the one who guided him down onto the bed, where he reclined back against the pillows. Moving to kneel between his spread legs, I glimpsed the base of an anal plug he'd inserted. He'd clearly counted on me fucking him tonight! I couldn't hide my smile as I grazed my fingertips over the base.

When my eyes met Trent's again, I saw the same vulnerable need in his face that I'd noticed in my own during that incredible blowjob. It was then that I became aware of just how much I longed to satisfy this man.

Leaning forward, with a palm planted against the bed on either side of Trent, I gently suckled at his neck. He didn't press me for a kiss on the mouth; maybe he didn't care for such intimacy in this kind of situation. My lips traveled down his chest, but before I could move lower, he wove his fingers through my hair and guided my mouth to his nipple. It honestly hadn't occurred to me to give those hard peaks any attention; I pretty much neglected my own during sex. But I was happy to please him in such a way. He made a sound between a sigh and a moan as I swept my tongue over his nipple, then eagerly sucked it. While he held me to his chest, I was again struck by his tenderness. Did he treat all his lovers like this? Or was he simply making sure I stayed relaxed?

When I took his nipple between my teeth, his grasp on my hair tightened. Neither of us was hurting the other, but I could sense the sexual intensity ratcheting up several notches. I showered attention on Trent's other nipple before finally making my way farther down his body. My lips and tongue traveled over his toned belly, then lower still, until my mouth hovered above his erect cock.

I was relieved Trent had sucked me off first, because that gave me an idea of what he would also enjoy. I couldn't help but be a little unsure at the start, yet his dick pulsed when I slid my tongue along its underside from base to tip. Breathing in, I detected his scent. He'd obviously showered shortly before I arrived, so it was faint, almost unnoticeable. Nestling against his crotch, I drew in another greedy breath.

"You smell really good," I murmured.

"Mmm, I'm glad you think so." I heard the grin in his voice. "Hopefully you'll like the way I taste, too."

I discovered just how much I did like it when I circled my lips around his cockhead and swirled my tongue over his skin. He released a pleasured groan, and as I gazed up at him, I saw the heat building in his stare. I remembered how excited I'd been to see him take me in his mouth. He clearly enjoyed watching me do the same to him.

While grasping Trent's cock, I spent plenty of time licking his sensitive frenulum. I even made an effort to suckle the flesh in the same way my lips had worked at his neck.

"Ah, that's nice!" he breathed.

I kept it up until Trent actually began writhing a little. His hand on my head was firm, but not rough. "Take me in your mouth, baby," he urged. "Show me how much you want it."

I readily did as Trent asked, and while he kept his hand on my head, he didn't push me. Instead, he let me set the pace of the blowjob. I was glad for a little time to get used to his dick in my mouth. When going down on me, he'd made it look so effortless, and to him, it probably was. But this was my first time sucking cock, and it didn't exactly come naturally to me. I was surprised at just how large he felt filling my mouth. While reminding myself to be careful with my teeth, I strove to keep my lips sealed firmly around his shaft. And of course, I needed to use my hand as well. I had a new appreciation for all the women who'd sucked me off in the past.

Trent must have noticed me struggling a bit. His fingers were gentle stroking my hair. "Relax," he said in a low, soothing voice. "You're doing great, Derek."

His praise encouraged me to try more. Soon, I was easily taking over half his dick between my lips while I stroked the lower part of his shaft. I made a point to moan, since I knew how good that felt around a cock. The sound of Trent's faster breathing made it clear how much he enjoyed my efforts.

I grew brave enough to slide my lips farther down his length, but as soon as his tip invaded my throat, it triggered my gag reflex. My eyes watered, and I began practically drooling. Pulling off, I took a breath and gave Trent an apologetic look.

"It gets easier with practice," he assured me.

"Sorry about all the spit." His cock was plenty wet with my saliva.

"Don't be sorry." A sexy smile danced on Trent's lips. "I love a messy blowjob."

Though my face grew hot at his words, I was relieved he wouldn't mind me slobbering or choking on his dick, which was pretty much what I did while making every effort to take him deep. Finally, I managed to tolerate the intrusion of his cockhead, and the way it blocked off my air. My throat muscles constricted all around him.

"Holy shit!" Trent groaned. "Oh, I think you're going to be a natural at this!" His voice was so thick with arousal that it heightened my own until I gave no thought to the tears burning my eyes. I only wanted to excite him even more. I was sure he'd had his dick sucked countless times, and yet I'd still gotten him worked up to the point where he was trembling.

"My God, Derek!" he cried.

When I finally pulled off again, I was actually sweating. Looking up at Trent, I saw his features drawn taut with lust. I couldn't help but grin, knowing I was the reason for that. While stroking his cock, which was slick with my spit, I turned my attention to his balls. I loved how smooth his sac was beneath my tongue. As I licked and sucked it, I felt his large balls tighten, but even then, I struggled to take them both in my mouth. Still, it was a hell of a lot of fun trying. Trent, meanwhile, was so turned on that he was almost panting.

After my throat and jaw stopped aching, I resumed sucking his cock. My fingers were gentle in massaging his taint, yet the sensation made him lose control a little. When he bucked his hips, driving his dick farther between my lips, I managed not to choke.

"That's so fucking good! Yes, yes!" he growled. 

I sucked and stroked, moaning all the while. Already, I was preparing myself for the blast of semen that was soon to come. I'd tasted my own before and hadn't been repulsed by it, and I decided that swallowing Trent's cum would be a fitting end to the first blowjob I'd ever given.

But he stopped me before I could bring him to orgasm. "Derek, wait!" His voice sounded pleading. Lifting my head, I gave him a questioning look. "I want to come when you're inside me," he revealed.

Though my erection had weakened while I'd been so focused on trying to give good head, I now grew fully hard once more. All my doubts about being able to perform, and my questions about my sexuality, faded into the background, replaced by a fierce yearning to fuck this man. Before I could stop myself, I said, "I want to rim you."

Trent was obviously surprised, but I could tell I'd once again pleased him. "I certainly wasn't expecting that," he replied in a husky voice, "but I would fucking love for you to eat my ass."

Christ, just hearing that made my dick throb! As I moved to sit up, Trent positioned himself on his hands and knees. Then he rested his face against the bed while lifting his ass. I gazed at him for a moment, struggling to control my rapid breathing. Cupping his firm buttocks in my palms, I gave them a squeeze.

"I don't have much experience with this," I confessed, "so let me know if I do something you don't enjoy."

"I'm going to enjoy every second of it," he promised. "Just don't be shy using that incredible tongue of yours. I want to feel it deep inside me."

I groaned, making no effort to hide my excitement. I knew it made little sense that I was hesitant to kiss Trent but was dying to tongue-fuck his hole. Grasping the base of the plug he'd inserted, I gave it a tentative pull. This was something else I had no experience with, and I wasn't sure how much force it would require to remove the plug. But Trent's ass released it easily enough, and when it was free, my eyes widened at its size. Black and sleek, the plug had stretched his opening to the point where it seemed to beg for my fingers and tongue.

I couldn't resist teasing him a little, simply circling that ring of flesh with my fingertips. He'd gotten rid of all the hair in this area, too. "You like that?" I murmured while massaging his sensitive flesh.

"So fucking much!"

I decided not to make him wait for more. Earlier, I'd trimmed my nails almost to the quick and then filed them smooth so they wouldn't cause Trent any discomfort. Now, I slid my index finger inside him, and with my other hand, I massaged his taint. He began rocking his hips a little, moving backward until my finger was buried deep inside his ass.

"So greedy for it!" I said through a grin. After withdrawing my finger, I placed my palms against Trent's cheeks and spread him even wider. Then I buried my face in his ass so I could lick and kiss his hole. I loved feeling it quiver beneath my tongue.

Trent's moans bordered on cries. "Ah, just like that, baby!" Again, he pushed back against my face, displaying his eagerness for more.

As I went wild eating his ass, I was shocked by my own enthusiasm for the act. Working the tip of my tongue inside him, I felt his muscles relax a little, which enabled me to go even deeper. All the while, I stroked his cock. With my erection straining out from me, I had to grin at my previous anxiety about getting hard enough to fuck this man. Hell, I was so excited, I'd have to worry about lasting!

Even when Trent began struggling in my grip, panting that he was too close, I was reluctant to let him go. Releasing his dick, I continued kissing and tonguing his hole until the moment he managed to pull away and roll over onto his back. His tip was flushed a deep pink, and I couldn't stop myself from giving it a teasing lick. That sent a fierce shudder through him. His fingers were rough in my hair, but I found I loved the way he lifted my head and forced me to look at him.

"You're going to fuck me. Right now." His voice left no room for argument. Not that I had any; I was aching to be inside him. Still, anxiety mingled with my lust as we climbed from the bed long enough for Trent to pull back the covers. What if I'd gotten too worked up to last? It normally wasn't a problem for me, but this was worlds different than anything I'd ever experienced with a woman. If I was being totally honest with myself, I had to admit it was worlds hotter, too.

After we settled back in the bed, with its luxurious sheets that felt like silk against my skin, I watched Trent retrieve the lube and a condom. I tried to hide my nervous trembling while sheathing my dick. If Trent sensed my self-doubt, he didn't acknowledge it. Instead, he seemed consumed by the need to be fucked. While he lay on his back with his legs spread and lifted, I followed his instructions in lubing up his ass. I noticed his cock jump when I touched him.

I was still rock-hard, but my breaths had grown shallow from performance anxiety. Trent said my name, using that low, soothing tone, and I met his stare.

"Relax," he said again, flashing a knowing smile. "I'll talk you through it."

I had to smile back, for it was like Trent could read my mind. After taking a steadying breath, I positioned myself so my cock was right at his entrance. Then I started easing inside him, moving at a glacially slow pace. I was terrified of hurting him.

"Fuck, yes!" Trent moaned. "Ah, that's good! Give me more of your cock, Derek!"

Glancing up at him, I saw that his brow was furrowed and his jaw was tight, but the sheer need in his eyes convinced me to slide in deeper. He was tight around my dick, but I didn't meet as much resistance as I'd feared. It wasn't until later that I'd understand how skilled Trent was at relaxing his muscles so I had an easier time entering his ass. It was something he'd learned through a ton of experience.

When I finally bottomed out, he tightened around my cock even more, drawing a whimper from my lips. Our eyes locked, and he gave me one of those gorgeous smiles.

"You did perfect," he said. "And now you don't have to be so careful, because my ass needs a good pounding."

His words made me gasp, but as much as I longed to give him what he wanted, I knew I needed to calm down a bit. If I started fucking him hard and fast, I'd come in no time, despite the condom. Leaning forward, I again placed a hand on either side of him. Even with my upper body hovering above his, I realized how intimate this position was. There was no hiding from his eyes; face to face, I would see his every reaction, and he would see mine.

Trent rested his hands on my hips, as if to urge me forward. When our stares met, he whispered, "Fuck me, baby."

My first tentative thrust made him groan. I tried to take it slow, determined not to approach climax too soon, but my excitement got the better of me. As my hips moved with a more fervent rhythm, I broke into a sweat. Part of my mind was still in disbelief that I was fucking another man, yet I couldn't deny how incredible it felt. Gazing down at Trent, I grew even more excited seeing the fierce pleasure overtaking him.

When I dared to give it to him harder, the sound of our bodies slapping together filled the room. He looked almost pained, and yet he demanded more. "Ah yes, take my ass, Derek!"

I'd been struggling to hold back, but I now fucked him at a relentless pace. Reaching between us, he roughly jerked his cock, his groans almost continual. I kept my stare fixed on his face, tuned in to his every response. His blatant lust fed my own until I had to slow down again. The tightening of my balls let me know I was about to lose control.

Trent might have asked for a pounding, but he seemed to love my slow, deep thrusts as well. His own stroking grew more languid, matching my rhythm. I moved above him, changing my position only slightly, yet it was enough to make him cry out.

I immediately froze. "Are you okay?" I asked. "Do you want me to stop?"

"God, no!" Trent replied, his tone forceful. "I want you to keep fucking me at that exact angle, and at that exact depth, because you're gonna make me come."

It was then that I realized I'd managed to hit his prostate. Taking great care to precisely maintain the same position, I started fucking him once more. Drops of my sweat struck his skin, and my eyes widened when he actually began shuddering.

Trent's helpless cry coincided with his first orgasmic contraction. I easily felt it around my cock, and as more followed, I let out a groan. Once again, I was dangerously close. But at least I'd made him come first.

As intense as his climax was, I was surprised that he produced only a little cum. Meanwhile, his ass kept milking my dick until I was wild for my own release. Instead of keeping myself propped up above him, I lowered my body onto his. Slipping my arms beneath his neck and shoulders, I cradled him to me.

Then I mercilessly gave him the pounding he'd asked for. His desperate moans filled my ears as he slid his palms over my back and down to my ass. By now, I was slick with sweat, panting while I rested my head against his. "Is this what you want?" I growled.

"Yes, ah fuck!" His fingertips dug into my flesh, spurring me on.

I was right on edge, so close! When I lifted myself up in order to see Trent's face, I found him overwhelmed by the same fervent need. Again, he took hold of his cock, and just moments later, his muscles began rhythmically clenching around my dick once more. Was he actually coming again?

My God, he was! And this time, he had plenty of cum to show for it. Semen spurted from his cock to strike his belly and chest. His orgasm made me surrender to my own, and I roared from the force of it.

It was all I could do to keep myself upright as I trembled. Once I'd carefully pulled out of Trent, I made no move to get up. Instead, I collapsed against him. Though we were both flushed and sweating, he continued shaking as if he was cold. When I lifted my head, he smiled and pressed a hand to my face. He started to speak, but before he had a chance to utter a word, I lowered my mouth to his.

The way he surrendered to that kiss let me know he'd been aching for it. And I clearly had been, too, for I welcomed his tongue between my lips. What had this man done to me? I wondered in mild bewilderment. This no longer felt transactional.

Not once during the evening had I been forced to pretend I wanted Trent, and by the time we started fucking, I'd completely forgotten he was paying me. The realization now occurred to me with a startling clarity: this had never been just about the money.