Day 9: Of course!

A few hundred paces from their agreed meeting spot, Lucas waited. He wanted to keep Eldrin off-balance, to deepen his dependence on him, and so he was intentionally late. He knew it was manipulative, but he relished the uncertain expression the inexperienced Elf got whenever he was... encouraged to do something outside of his zone of comfort.

For all his intent, though, his own eagerness at their next session together put him into motion less than a quarter of a bell after they were supposed to meet.

Eldrin's head shot up as soon as he entered the alley, anxiety fading into tremendous relief. He made his way over, almost breaking into a run.

Lucas almost didn't recognize him. He was wearing a new dress. It was deep red and form-fitting, a little shorter than the blue one he wore before, but not immodest. His feet were clad in brown sandals with a small heel--if Lucas' eyes didn't deceive him--that clacked against the stones as he approached. The biggest shock was his face, though: he had highlighted his cheekbones and eyes, making himself look every bit like a girl on a night out. As he got closer, Lucas could tell this was the first time he'd applied make-up, but the Elf looked so elated he decided not to say a word.

Eldrin halted right in front of him and nervously smoothed his dress. He was crimson-cheeked and out of breath, more out of excitement than from the brief exertion.

Lucas made a show of looking him up and down.

"D-do you like it?" Eldrin asked in a tiny voice, peeking up at Lucas through his eyelashes. "You don't have to lie. I know it's not very good. I've only had one day of practice and..."

"Hush," Lucas said, raising his hand. "I like it a lot. You look even sexier than the last time I saw you."

Eldrin looked astounded. "Sexy? R-really?"

Lucas grinned. "Definitely."

The Elf rushed the remaining distance between them and wrapped his arms around Lucas, burying his face in the man's chest. Lucas was a little surprised by the sudden contact, but gently placed his hands on Eldrin's back all the same. He resisted the urge to slide them down further. There'd be time for that later.

When they broke their embrace, Eldrin looked up at Lucas questioningly, eyes shining with anticipation. "Where are we going today?"

"Eager, are you?" We're going to have a couple of drinks, but I have a surprise for you first. Bend over for me."

"B-bend over?" Eldrin asked, the fragile confidence draining from his expression. "I don't... I don't understand."

"Do you trust me?" Lucas asked, putting as much warmth in his voice as he could.

"I-I..." He gulped, then nodded. "Yes."

Lucas just stared at him, patiently, saying nothing more.

The Elf was a picture of nervousness, fiddling with this dress, refusing to make eye contact. Finally he came to a decision, took a deep breath, and leaned against the stone wall, looking over his shoulder at Lucas. "L-like this?"

Lucas moved to stand next to him. He placed one hand on his left shoulder, feeling the shudder that drew through his body.

"Shhh," he whispered. "You'll like this, little Elf, I promise."

Feeling some of the tension leave Eldrin's body, he placed the other hand low on his back.

Lucas noticed Eldrin was still practically upright, so he pushed firmly on his shoulder. Eldrin made a soft noise that was almost a squeak, but resisted only a little, slowly bending at the hip until his upper body was almost horizontal, his ass pushed out enticingly.

"Perfect," Lucas said.

He let his right hand drift down the Elf's body until it cupped Eldrin's ass through the thin fabric of his dress.

"Ahnnn," Eldrin whimpered, another shudder drawing through his body. Lucas grinned, suspecting this one wasn't borne of fear, nor of embarrassment.

He held it there for a while, enjoying the Elf's warmth, then continued his journey down Eldrin's leg. When he arrived at the hem of the dress, he took hold of it, then pulled it up and over Eldrin's ass in one smooth motion, exposing his panty-covered backside to the cooling evening air.

Feeling the fabric slide off him, Eldrin's body jerked upwards, but Lucas' grip kept him from moving more than an inch or so. He remained there, bent over, waiting, breathing shallow.

"I see you decided on panties tonight?" Lucas teased. "Those will have to come down, at least for now."

"A-all right."

Eldrin then surprised him by reaching back and pulling them down over his ass himself, then placing his hands back on the wall. Pleased to see the Elf so acquiescent, Lucas placed his hand back on his now bare ass, enjoying the warm smoothness of the skin against his palm. He squeezed gently, just to get a good feel.

"Your ass is perfect," Lucas said. "Firm and round and soft."

"Th-thank you." Eldrin whispered.

Lucas felt his eyes drawn to the narrow valley between the two cheeks. He let a finger drift downwards and inwards. He heard a sharp intake of breath from the Elf besides him, then he forged onwards until his finger brushed lightly against his asshole.

"Ah!" Eldrin moaned, tensing the tight star involuntarily.

Lucas let his finger rest against the sphincter, rubbing in small circles around the outer rim, taking care not to push in. He could feel it clenching and unclenching in rapid succession.

"Nnnn...!" Eldrin mewled. "That's... That's... Mmmm..."

"See?" Lucas laughed. "I knew you'd like this. Do you want more?"

"Nnn... I don't know."

Lucas put a tiny bit of pressure on the tight ring, causing Eldrin's moans to deepen.

"I think you do know. Tell me what you want." Lucas commanded, applying a tiny bit more pressure.

"I-I want more." Eldrin admitted. "Put it inside... Please..."

Lucas smiled to himself. He knew curiosity--or lust--would win out. He quickly spat on the opening for lubrication, then began putting pressure on it. The first knuckle of his finger penetrated rather easily, but then the involuntary muscles clamped down on it, trapping it in place. Eldrin's breathing quickened, and his knees seemed to weaken beneath him.

Lucas didn't thrust in or out; he simply left his finger there, waiting until the involuntary muscles relaxed.

"D-don't..." Eldrin whined. "S-stop..."

Choosing to believe those words came together, Lucas continued pushing pushed his finger past the tight sphincter. Eldrin was tight, unsurprisingly, almost painfully so, but the spit helped his finger slide in past the second knuckle, an then right up to the third.

"Ahh, ahh, ahhh!"

Eldrin gasped in discomfort, but otherwise did not interfere as the older man invaded his hole.

Once his finger was fully inside, Lucas began slowly thrusting in and out. The pain in Eldrin's voice was obvious as his sphincter stretched to fit the shape of Lucas fingers, but there was a clear pleasure in it as well.

Lucas put his lips near Eldrin's ears. "Are you enjoying this, little Elf? Having your tight little ass fucked by my finger?"

"Ughh!" Eldrin cried. "Oh, oh, oh! Yesss, it feels... It feels good."

"Are you ready for your surprise now?"