Esme decides he's been a naughty boy

{ I know I said it takes half a day } said Esmeralda into his mind, { But there are a few things that can change that. Sometimes, the synod is very busy with other matters, so we may wind up parked outside for a while. We might be outside for a few hours, or for a whole day. There's a place for you to sleep here if need be }.
Callum looked up at her. Her elfin face, her sparkling green eyes, the wavy red hair... He had always thought that he could only love one woman at a time. And yet, Esmeralda was growing on him. He felt that he loved her too, nearly as much as he loved Phaedra, albeit in a different way. He shivered, feeling the cool air inside the caterpillar.
"Um, Esme?" he said, peering up at her with his wide blue eyes. Esmeralda looked down at him and smiled.
{ Cold again? } she asked.
"Y-yes Esme. I... Could I please have... um... Could I please have maybe a blanket or something, please?" he stammered, his voice growing quieter toward the end. It felt so wrong to ask her for anything. Did he even deserve a blanket? Maybe he should just have resolved to sit there and bear the cold, and not bother her.
{ Callum! } said Esme brightly, { Of course you can have a blanket. In fact, the Synod will probably be busy when we arrive. I think that you and I should perhaps go lie down together. Wouldn't that be nice? }
Callum's face lit up at the thought of the Alfonian's lithe, toned body pressed against him under a warm blanket. He smiled at her, putting on a brave face and trying not to shiver.
"I would like that!" he said unable to stop himself from breaking into a huge grin. In spite of himself, he shook again.
Esme looked down at him and sighed. Good grief! When would he learn to just tell her when he needed something? He was completely powerless here on Alfo Prime. There was no way for him to get anything he needed or wanted unless Phaedra or Esmeralda gave it to him. And yet, he never asked or made a request or even complained. He just sat quietly and tried not to be noticed. It was as if he assumed that he wasn't allowed to even need things. Esme was an enormous bleeding heart, and underneath the bubbly exterior was a passionate conviction that it wasn't right to treat anyone the way that humans were frequently treated on Alfo Prime. From his abusive stepmother to abusive Alfonians, Callum just couldn't seem to catch a break. The poor thing was utterly defenseless, not even able to stand up for himself against his peers, let alone powerful psychic Alfonians. Looking down at him, Esmeralda felt a mix of protective, almost maternal feelings and a strong attraction. The same impulse to protect was also an impulse to dominate, and Callum was just such a snack.

Esme placed her hand under his chin, tilting his face up to look at her, and smiled. He smiled back at her, not sure what to do with the silence but totally compliant. Coital intercourse was a special thing on Alfo Prime. Phaedra would be the first one to get Callum inside of her, although she would probably let Esme have him as well, eventually. In the meantime, there were so many ways that Callum could be enjoyed. Phaedra was so cold, so calculating... not that she didn't love those close to her deeply, but she just didn't have the kind of warmth that someone like Callum would need. Esme stopped for a moment and frowned. Was she just fabricating excuses to convince herself that Callum should be hers and not Phaedra's? Well, he was Phaedra's, for the time being anyway. And Esmeralda didn't want to compromise a deep friendship over romance. This could all be brought to a good, equitable conclusion.

She stroked his cheek, looking down at him as if he were a treasured pet. What sorts of things did he like in bed, anyway? She knew about the prostate orgasms and submissiveness, but what else? She could read his mind, of course, but really understanding another person's needs required more than just telepathy. She would have to talk to him and... touch him a bit. Esme sighed again, reproaching herself mentally. She had previously pushed him into repeated orgasms just to feed off of him, not caring about how he would prefer to have things. It was time to put some effort into getting to know him a bit better, and helping him be more comfortable in his own body. It was hard even for a telepath to know what he wanted, because even Callum didn't quite understand his own desires. It was time to fix that.

{ Come with me, sweetheart } said Esme, setting Callum gently down on the ground. She took his hand again and began to walk toward the back of the caterpillar, where the small bedroom was. He had to walk a little faster than he was accustomed to doing, to keep up with her long stride. His face came up barely to her shoulder. Esme noticed him jogging to keep up with her and slowed down so he could keep pace.

{ Tell me } said Esme as they walked, { I know you like to masturbate a lot. And I know that you've tried touching your prostate. Phaedra was your first kiss, and I know that too. But Callum... There's so much of sex that only comes out when you've got a good lover. There' s a lot to learn. So tell me, what do you really like? Can you help me understand? }
Callum swallowed nervously.
"I... I'll do my best, Esme. I know I'm not very good at it. But I'll try. Maybe... Um.. Maybe you could teach me? Would that be okay?" He shivered again, feeling the cold air of the hallway. Esme stopped walking, turned, and looked down at him. He sucked in a sharp breath. Was it wrong to ask her that? Esme had been so nice to him so far, so she probably wouldn't hit him or yell at him. But had he said the wrong thing? Esme was about to reassure him, but then realized that she could have a lot more fun by toying with him a little.
{ You naughty boy } she said, { You can't tell me what you like? Well, I think we need to address that... }
Callum felt his heart flutter when she said that. He was afraid, but he also felt his dick vainly attempt to stiffen against the chastity. Address it? How?
{ I think you need a little some thing to help you focus } she purred. They continued to walk until they reached the doorway at the end of the hall, which spiraled open to reveal a small circular bed. It wasn't terribly large. It was more of a resting place for times when the caterpillar could break down or needed to wait at a port. Esme led Callum into the room and the door whirred shut behind them. She sat on the bed and smiled down at him.

Callum squeaked as he felt himself plucked up off the ground. His body turned in the air so that he was face down, and he settled neatly across Esme's lap. He felt her hand take a firm grip on his hair and gently pull it back until he was facing forward. He shivered. Was she going to put her finger in his butt? He unconsciously arched his back, hoping to be milked. He yelped as he felt her hand land on his right cheek, his bottom jiggling from the spank.
"I-I'm sorry!" he cried, "What did I do?"
{ Just relax } said Esme, her voice surprisingly soothing, { Deep breaths, Callum... } The hand gripping his hair let go and moved under his chin, supporting his face. The other hand tickled the nape of his neck and teased his back, light feathery touches raising goose-flesh as her fingers made their way to his butt again. He felt her hand grope and squeeze each of his cheeks in turn, massaging and pinching the soft, naked globes. He whimpered, eyes closed and a light blush across his face. The nice, gentle massage of his ass felt so good...

Another smack, on the other cheek this time. Callum gasped, then wailed "Ow!" as he received a third spank. He was panting hard. His whole bottom felt warm, heat seeming rise to the surface.
{ That's right, you dirty boy } said Esme, { You're getting a nice, firm spanking to help you pay attention. And... } her hand came to rest on his quivering bottom, then slid down to gently cup his small, swollen balls, { If you take your spanking like a good little slut, you might just get milked... }
"I'll be a good boy," he stammered, unconsciously humping against her leg, his small rear wiggling up and down. He couldn't get any friction on his cock because of the cage but he couldn't stop helplessly grinding it into her leg anyway, whimpering and whining softly. His butt continued moving up and down, feeling her soft palm gently cupping his sac.
{ You'll be a good boy for me, you naughty little thing? I'm not sure I believe you! } said Esme with a giggle, giving him another spank. He cried out and began humping her leg even harder, making a girly "Unh!" sound as the cage slapped uselessly against her thigh. She still had one hand supporting his chin. Her thumb slipped into his mouth and he sucked it greedily. His eyes were squeezed shut and he moaned softly, sweat beading on his bottom as another slap landed. He bit her thumb lightly and a high pitched moan rose from his mouth.
"P-p-please!" he squealed, "I'll do anything!
{ Anything? } said Esme softly. Her hand rested on his twitching butt, and one finger daintily wandered over his hole. He sucked in a breath, arching his back and presenting as hard as he could. A quiet whine escaped his mouth as he continued sucking her thumb. He nodded vigorously.
"Anything!" he said, his voice sounding half-strangled. Esmeralda took her hand off his butt and began gently stroking his back again.
{ Sshh... Deep breaths, Callum... Just relax... } she said. She placed her hand on his back and felt his heart slow just a little as she lovingly rubbed the tension out of his back.
{ That's a good boy } she said approvingly. A smile crept onto his face. Was he going to finally be milked?

He practically screamed as she spanked him again, three firm slaps landing on his rump.
"Oh! Ohh! Nnng!" he said, humping against her leg with renewed vigor. She smiled down at him, watching his small body wracked with intense, frustrated desire. His poor little dick couldn't get hard in the cage, so all he could do was squirm in her lap and whine like a needy little whore. She slid one hand down his warm crack and fondled him through the cage. A few flecks of fluid told her that he was already dripping. His prostate was surely engorged already. But would she milk him yet?

Not yet, she decided.

Callum wailed so loud that it hurt Esme's ears a little as she dealt him another spank. One finger found his hold and just barely tickled the entrance. He moaned like a girl when she wiggled the tip of her pinky in his tight ring.
{ Oh, you poor thing } she said, her bubbly voice tinged with a hint of irony, { Do you need it, you dirty boy? I can see you dripping on my leg through that cage! What's wrong, sweetheart? Are you getting all worked up? } As she spoke, she groped his bottom, rubbing and squeezing his cheeks, stopping here and there to pinch his butt and hear him yelp. Here she would tickle his taint a bit, her fingers lightly tracing their way down the smooth, delicate, shaved skin to fondle his balls. Abruptly, she took a firm grip on his testicles, holding him stock-still.
{ My, my, Callum! They're so swollen! Are you a little turned on, sweety? }
"Yes, Esme," he moaned, his butt twitching slightly as he felt her strong grip on his sac.
{ Good boy. It must be frustrating being all locked up like that. That cage is just so mean, isn't it, Callum? }
Callum wasn't sure what she wanted to hear, so he said nothing, feeling butterflies in his stomach.
{ You know who owns your dick, Callum. Phaedra does. But right now, this little butt belongs to me. } She giggle softly, releasing her hold on his balls. She playfully flicked the tip of his penis through the cage, feeling his hips jump at the sensation. Then she slid two of her fingers into his mouth with her one hand, gently pushing them in and out and feeling him greedily suck and slurp on them. With her other hand, she gave him another firm smack, squeezing his butt tightly. He made a soft "Nnnngggg" sound, sucking her fingers deeper into his mouth. He raised his butt in the air, as if pleading for another spank, and she gave it to him. Now he began bobbing his head up and down, sucking her fingers with his spit running down her hand, and she gave him light, playful spanks in response.
{ Goodness, you slutty little thing, } she said, { You just need to get your hole filled, don't you? }
"Mmm-hmm," he said around her fingers, his little butt writhing around as she skillfully squeezed and pinched it. here and there she'd stop and rake her nails up the back of his thigh, making him squeal around his other fingers and making his little bottom jump in the air.

It went on like that for a while, until his body was covered in sweat and his whole butt was spanked pink. She took her fingers out of his mouth finally.

{ Callum } She said softly. She picked him gently up off her lap with her mind and put him down, feet-first, on the floor.
"Esme?"
{ Here, sweetheart } she said. She took a cloth from the bedside table and gently wiped the sweat and spit off of his face. She tilted his face up to look at her with one hand under his chin, then rang her fingers through his hair, smiling down at him.
{ Are you okay? } she said. He was awfully worked up, still shivering and sweating slightly. He reached up to her and she took his hand in hers, giving it a reassuring squeeze.
"I'm f-fine, Esme," he said, smiling, eyes still wide. He was blushing and his pupils were enormous, utterly transfixed by her.

{ Look under the bed. What you find there, take out and show me, okay? }
She watched him get down on all fours, his cute butt in the air as he reached under the bed. Callum, for his part, breathed heavily, wondering what he would find. Esme grinned coyly, watching him. He might just spurt through the cage when he saw what she had in store.