Derik's Luck 30
From TSade
[edit] Heels
Derik moaned around the ball gag shoved into his mouth and closed his eyes as his body jerked forward. He focused on the feeling of the large, smooth strap-on plunging deep into his ass and the slap of Madre’s hips against his still-smarting cheeks. Her hand cracked down and he jerked forward again, this time from the pleasure and pain mixing in the cauldron of his loins.
As she withdrew, sliding the thick hardness from his body, he smiled around his gag and opened his eyes again. His wrists, cuffed to the railing above Madre’s headboard, twisted so he could stare at his fingernails. Freshly painted, trimmed, and sparkling, they were still wet from where Madre finished painting them only a few minutes before. In the twelve days that passed, they finally healed enough to be shaped and painted. It felt like a wound had finally healed as he stared at the white crescents and deep sapphire color. He would blow on them to dry, but the gag in his mouth prevented everything but the moan escaping his throat.
Madre slammed forward and he closed his eyes, anticipating the slap against his ass. Her hand impacted against his right cheek again, redoubling the heated pain and pleasure as the thick dildo sank to the hilt inside him.
He moaned again, a long shuddering one of ecstasy, and felt his cock bobbing against her soaked blankets. She grunted and planted her hands on his hips, yanking out and driving into him as she switched to hard, powerful strokes that sent bolts of pleasure bursting inside him and his head bumping up against the headboard. He twisted his wrists to keep from marring the fresh paint on his nails.
As the thickness plunged in and out, fucking him almost as deep as the baron, he waited for the next smack against his red ass. It never came, only the rapid pumping of Madre reaching her own orgasm. He pushed back against the headboard, using his elbows, to let her plunge deeper into it, to feel the friction of his more than willing body around her strap-on. Her breath came out in grunts and he felt the first signs of orgasm, that tiny release of her magic that set the hairs on his nap on end. He closed his eyes tightly as she gave him two, then three hard pumps, then buried herself completely in him, pinning the thick pressure as she swept through her orgasm.
Pinned against the wall and a rubber cock, he marveled how good it felt. It wasn’t the baron’s, which he needed so badly he dreamed of it, but it still felt good. It felt like his place on the bed, beneath Madre’s body and impaled.
Panting, Madre plastered herself against his back, her sweaty breasts rubbing against his shoulder-blades. She gasped as she spoke curtly but with a voice filled with an afterglow of an orgasm.
“And that was two thousand swats over twelve days.”
Her hips rocked slightly and he grunted, unable to speak around the rubber ball in his mouth. Her fingers worked the strap and he gasped as she eased it out of his jaw.
“And, Dora, what did we learn?”
Derik moaned softly, pushing back on the cock.
“Spank faster?”
When she grabbed his hair and pulled back, he gasped. Her hand came down, this time flaring with magic, and he felt the sensations shoot across body, sending him over another edge of an orgasm. He groaned with pleasure, squeezing his inner muscles around her strap-on as he splattered her sheets once again with his seed.
Madre jammed it into him and rose up her hand. He could feel the magic pooling in her palm. He gasped in the feelings of helplessness and cried out.
“I don’t spank Madre!”
The second magical blow didn’t come and she released his hair. He leaned forward, feeling the strands of his hair slipping through her fingers.
“Good. Even if I do something wrong?”
Derik said nothing, thinking about the feel of his hand against her ass and also the thousands of swats he got since. His cock, despite his release just seconds before, twitched and drooled more cum into her blankets. She pulled his hair again.
“I said,” she growled, “even if I do something wrong?”
He spoke softly, half moaning as he spoke.
“I won’t do it again,” she started to release his hair, but he kept on speaking, “unless I think its important. Then, you can and will tan my ass even more.”
For a second, he thought she was going to smack him again, but she just let the hair slip from her fingers.
“Fair enough. Next time, it will be two hundred spankings for every time you do it and I won’t spread it out over a week.”
He pushed his hips and withdrew her cock, leaving him with the feeling of emptiness. He slumped to the bed, ignoring the squelch of his own cum that plastered itself to his stomach. Sated, he just smiled and looked up to his drying nails.
“Are they done?” asked Madre.
“I think so, but kind of hard to check.”
“You should know by now how long it takes.”
He thought back to the time she fucked him and nodded. She reached over to release his cuffs and he sat up, smearing his juices but still staring at his nails.
“Thank you for fixing them.”
Madre at on the edge of the bed, sweaty but smiling herself.
“It was the best I could do. They’ll grow over the next week and I’ll reshape them.”
He smiled to her.
“Thank you.”
“I guess,” she glanced away, “I should thank you also. I didn’t realize how much I was withdrawing until you came in.”
Her head snapped back to stare at him, “But! That doesn’t mean you have permission to lay your hand on my ass again.”
He giggled, then froze at the sound of it. Madre smirked and held out her hand.
“Come, you need to get cleaned up, we are doing something different today.”
“Is that why I’m up at seven in the morning?”
“Yes.”
She drew him into the bath and he was relived to find out his nails were dry as they washed each other. Later, sitting at her desk, he leaned forward as she brushed out his hair.
“What made you come in here? It seems rather bold for you.”
Derik sighed and closed his eyes.
“I... I had a lot of reasons, I guess.”
“Such as?”
“My mother and Nightingale.”
She froze in mid-stroke.
“Nightingale?”
“I-I never realized you loved her that much.”
Madre sighed and continued brushing his hair.
“It’s hard being Madre. I can’t have favorites otherwise the girls complain. But, when I was just Rachel,” she sniffed, “I was so much in love with Gale. Neither of us dated or went out because we had each other and the baron. I didn’t need anything else. If I knew what would change when I became Madre, I may have never done it.”
He felt the brush in his hair and just leaned into it, feeling the strokes of the bristles and the soft breath of her skin. A tear formed in his eyes at the thought of Madre’s loss, trying to understand how much that could have hurt.
“Why did you?”
“Become Madre?”
“Yes.”
“The baron asked me to. I was the first to really understood what he was doing to the girls. I could help that first time after they ride his shaft. That ‘life-sucking cock’ as you put it.”
“What is it?”
She hesitated, but finished her brushing before answering Derik.
“It isn’t my story, Dora, and I don’t exactly know. But, I trust you to never tell anyone about it. He isn’t a danger to anyone as long as we are here, but it is his secret. If it gets out, more than you’ll just be hurt.”
“But, it hurt me already.”
“Yes, it always does the first time.”
“Not for you.”
“No, even for me. I just hid it better than others. And I had my Nightingale. But now, you are now his woman. Next time,” she paused as she set down the brush and picked up the long blue cord he used for braiding, “next time, it will feel like he’s fucking your body and your mind. Its an orgasm that you will probably never forget.”
He shifted at the thought, his body still craving that hardness inside him. His manhood rose at the memory and she chuckled.
“I can feel you thinking about him, that speeding of your heart and the heat coming off your body.”
He sighed himself, rapping his head on the desk.
“Why do I want him so badly?”
“Because you belong here and to him, body and mind.”
As she braided his hair in his now favorite style: a complicated five strand that integrated the cord as the sixth and always made him feel like it was part of some magical spell. He smiled and remained still, listening to the palace and her body.
“Why your mother?”
He jumped as she asked her hesitant question. He closed his eyes as a dagger seemed to spear his heart.
“She drank herself into Oblivion.”
“I’m sorry. How old were you?”
The memories were still painful, but he managed to speak about them.
“I last saw her when I was five, just over twenty years ago, and a few months before she was killed.”
Madre’s hands faltered, “I thought she drank herself to death.”
New tears ran down his cheeks.
“No, I said to Oblivion not to death. S-She was killed by a guard.”
“I don’t understand.”
“She was a whore on the south side of the town. Drank away the money her pimp let her keep. I had to steal to find enough food to eat. But, she drank too much one day and passed out at the Buggered Unicorn. She woke up long enough to make a deal with a mage, a Dimensional-something, when he decided to pay for one more use of her body. She never came back.”
Madre’s hands fell away as Derik spoke in a monotone. He heard her gasp and speak through her hand.
“Seven Gods!”
“He used her to open the rift to Oblivion. Twenty years ago, when the demon invasion came pouring into the city. I didn’t find out until I was ten, when I met the captain of the guards who finally killed her and sealed the gate.”
He sniffed, remembering the pain of that second memory, of a black-haired thief sitting in cuffs on the edge of a chair and listening to the captain tearfully apologizing.
“Oh, Derik!”
Her arms wrapped around him tightly, holding him as she pressed her head against him. He pushed back the memory of it, only letting a few tears roll down his cheeks as Madre held him. He cracked and let out a sob, fighting it every way, but soon he could let the memory fade again.
Sniffing, he wiped the tears from his face.
“After that, I became a th-”
He started to correct himself but Madre interrupted him.
“A thief?”
Derik froze, his heart pounding. He tried to think of a thousand things to say, but he just nodded.
“Yes.”
Madre leaned back, turning his head to face her.
“Did you steal anything here?”
“I haven’t taken anything from the palace.”
It was truth but not the full truth. He thought about the burning sapphire orb above the main room, then pushed his thoughts away from that also.
Madre’s lips tightened and he cringed, waiting for her to call the guards.
“Were you going to?”
He sighed, turning away from her as shame burned on his cheeks. He spoke before he could think about it.
“Yes.”
Inside, he screamed out at rage, at himself for speaking and for everything that led up to that moment. He found new tears, but it was that hand on his chin that forced him to look back at Madre. He stared into her brown eyes and saw tears shimmering in them.
“Why didn’t you?”
It was a low, almost whispered question. He struggled with his answer, opening his mouth then closing it. He tried to look away again, but Madre held his chin in place, her eyes boring into his very soul.
“I-I,” he swallowed hard, “I’m happy here. Happier than I ever been. I-I,” the tears were burning down his cheek, “I want to stay.”
Madre’s eyes flickered as she focused on him. He sniffed, waiting for the guards or for him to attack him.
“What?”
“Huh?”
“What were you going to steal?”
Panic rose up inside him and he clamped his mouth shut. Madre, listening to his heart as she always did, sighed.
“Don’t keep this a secret, Dora. Just let it out.”
He came within half a heartbeat of confessing. Then, he flung himself away, ripping his chin from her fingers.
“I-I don’t want to go.”
His chest hurt from the tightness that squeezed him. Hot tears splashed down on the desk as he trembled. Madre said nothing then she hugged him again sightly.
“Someday, Dora. Just tell me before its too late.”
“I-I’m sorry.”
“I know, but thank you for being this honest.”
He was in shock that she didn’t call the guards. After a tight hug, she returned to his hair, braiding it in silence. He remained still, fighting with a storm of emotions and memories that her questions brought up to the top. It hurt to think about his mother, but those memories had faded over the years and were worn smooth with time. Instead, he just thought about the Eye of Hamel and berated himself for not just telling Madre. He even opened his mouth once to tell her, then closed it out of cowardice.
Working himself into a deep funk, he jumped when Madre finished and set a box on the desk in front of him. It was wrapped in brown paper and had his name neatly written on the top.
“What is this?”
Madre chuckled and sat on the edge of the desk.
“Many people call it a present.”
He looked up, stunned.
“What for?”
“Many things, I guess: becoming the baron’s woman, pulling me from my sorrow, being honest with me. Turning everyone on?”
“Oh,” as he spoke, he felt his blush rising again in his cheeks. Madre chuckled and stroked her fingers along them.
“You blush so pretty. Now open your present.”
Still shocked, he reached over and delicately opened the package, careful of his nails. The paper tore loudly as he pulled it off. The box was inlaid with gold trim and made of polished wood. Gasping, he ran his fingers over the smooth surface.
“It’s beautiful.”
She smiled and gestured.
“Open it.”
Fingers trembling, he worked the latch and opened it up to find a pair of sapphire shoes inside. Gasping, he stared at them nestled into the black velvet. They had short heels, maybe three or four centimeters, but the tiny row of sapphires that ran along the edge to the narrow tip stole his breath away.
He sobbed with surprise, delight, and confusion. Madre chuckled and reached out, taking one out and holding it with her fingers.
“I’ve never given a girl her first pair of shoes, but after seeing you move, I think these would be perfect for you.”
“I... I... I don’t know what to say.”
She answered by setting another box down in front of him. He gaped at her until she gestured for him to open it. This one was also stored in polished wood, but with a different color and symbol on the seal. Shaking, he worked the latch and pushed it open.
It took him a moment to realize he was looking at a dress of the purest dark blue he had ever seen. It was shimmering and soft on his fingers, as sensual as his silk underwear. Tears ran down his cheeks as he stroked against it.
“I can’t.”
“Funny, I don’t recall asking you.”
He just stared up at her, tears on his cheeks. Madre slid off the edge of the desk and stood up. Pulling him to his feet, she smiled.
“Come on, we need to teach you how to walk like a woman before we go shopping.”
“S-Shopping?”
Madre grinned, “Yes, I need new boots and you need to get out.”
He stammered as she pulled him into the center of the room. Then, she helped him slip on his first pair of heels and stand up. It was intense, a feeling of standing higher, but also his feet perfectly fitting into the silken sheath of the shoes. He shivered at the sensations and at the feeling of the backs of his legs tightening. His calves felt like springs as he balanced on them, using his acrobatic training to find his center despite the change in posture.
Firmly, Madre walked him through crossing the room, guiding and holding him until he could balance. It only took two tries before he could move without help. Then, she worked on the sway of his hips and the bob of his movements. Wearing nothing but the shoes, his manhood stood up straight and drooled precum with every step.
Soon, Madre gave her approval.
“You are very aware of your body, Dora. I didn’t think you’d pick it up so fast.”
He circled the room, feeling very sexy as he grew comfortable with moving. In many ways, it wasn’t that different from the stilts he used for a while as a clown.
“I got this idea when I saw you bouncing off the ceiling. I knew this one battle mage, the class victor actually, who fought in heels and you moved like her. That was the nastiest fight I ever had; bitch took me out with a powered jump and a flaming fist to the head. Shift your weight a bit more, there, that’s good. And, damn, Hime did a great job with you. With a dress and you tucked back, I bet no one could tell you were anything other than a woman.”
He blushed hotly as he came to a stop. His legs trembled only slightly but he could feel his juices dribbling down the side of shaft and his thighs. Madre caught sight of them and sighed playfully.
“You get wetter than any girl I know though.”
“Sorry.”
“Don’t be. Now, get out of the heels, time to get you into your dress.”
His dress. It sent a tiny thrill through his loins as he slipped out of the shoes, almost sad to part with them. When Madre pulled out more clothes, the passing faded as he stared at a new pair of underwear, a black thong that looked very snug. It wasn’t until she pulled out the corset that he realized he had a desperate ache in his balls.
Madre chuckled.
“Go on, masturbate, but clean up with a rag, we don’t have time for me to fuck you again if you try to lick it up.”
He did so, a quick and hard orgasm against her sheets before he returned. Madre helped him slip on the thong, tucking back his cock and balls into place and settling the fabric over his hips. It felt delightfully exposed while still holding him firmly. The line of fabric up his ass sent a tiny shiver up his spine as she circled him.
“I hate that priestess some days. Well I don’t, but I do, you know what I mean. Bitch did everything right and I have no doubt I’m not going to hear the end of it.”
“Is she coming back, Madre?”
Madre nodded.
“Yes, she cashed in her favor yesterday. The baron agreed to replace Forbis with her and to maintain the marks on his harem. Including yours.”
“Just for me?”
Chuckling, Madre patted him before wrapping the corset around his chest and underneath his breaths.
“Not entirely you. The baron pays good money for caring for his harem and her church needs the money.”
“Oh.”
She gave his ass a playful spank, sending another bolt of pleasure coursing through his system as her palm connected to the red cheek. He moaned but she snatched her hand away.
“Better not turn you on anymore, I’d have to call in Teri and Sherrel to drain you and they aren’t ready to see you yet.”
The corset was tight, with its many straps, but it held his chest in and made it a bit uncomfortable to breath. However, when he looked in the mirror at his breasts cupped in the corset, he was stunned at his appeared.
“I-I’m beautiful?”
“You will be,” came the cheerful reply.
Finishing up the lacing, Madre helped him slip the dress over his head, snuggling into place. It clung to his body, hugging his hips and reaching down to his mid-shin. Two slits ran up both sides, stopping only inches from the curve of his waist. Underneath, black satin trimmed the edge so he could see tantalizing glimpses of his thigh as he turned around. His corset, with the same satin trim, peeked out of the front of the dress, giving him a deep cleavage and breasts that ached to be touched. The sleeves were short, but also trimmed in the same black. His waist looked tiny in the mirror, but he was stunned at his own appearance.
Madre stepped back and nodded again in approval.
“Hold on.”
Opening her door, she called to Teri. A few seconds later, Teri ran to the door, then stopped just inside it, her mouth opening in surprise.
“Holy fucking gods!”
“Teri!”
Gulping, Teri stared at Derik and he blushed even hotter at the sight of her lustful gaze. Turning around slowly, he looked at her through lidded eyes, holding his hands against the fabric that still sent tiny shivers through his body.
Neither said anything for a long time before Madre cleared her throat. Teri jumped and looked sheepish.
“Sorry, Madre.”
“You are better at makeup-”
Derik let out a soft whimper.
“-and would you please put some on Dora? We are going out.”
Teri, still surprised, came up to Dora and sat her down in front of the mirror. As soon as Madre began to dress herself, she leaned forward and whispered in Derik’s ear.
“I want to fuck you so hard right now.”
Her hand slid into the slit of the dress, stroking a finger along the thong and sending a hungry moan to erupt from Derik’s lips.
Across the room, Madre snapped out.
“Teri! No molesting her. Just do her makeup.”
Snatching her hand from Derik’s wet crotch, she giggled and pulled out a dazzling array of makeup. Derik lost himself in her commands as she applies eye color and lipstick, mascara and even blush. It felt strange, being dolled up, but his head swam with the image of the woman looking back at him in the mirror.
Finally, he was ready. Standing in his heels and looking every inch a woman, he couldn’t tear his eyes away from the mirror. Teri leaned against the bed, one hand pressed against her pussy as she watched. Madre smiled warmly and took Derik’s arm, peeling him away from the mirror.
“Come on, I need new boots.”
She was also beautiful, but Derik kept trying to look at himself in the mirror as she pulled him out of her room.
