Painful Pleasures and Unlikely Redemption: A Forbidden Encounter

Chapter Five: Pain For Pleasure

The man reached up and brushed a few strands of hair from Angel's face. He put a finger under her chin and tilted her head up to look at him. She kept her eyes low, much to his disappointment. He leaned down, gently placing a kiss to her lips, ever so softly.

She timidly pulled away from him, but he pulled her back to kiss her again, running the back of his hand across her cheek and down her neck. He pulled himself closer to her, kissing her a bit more passionately.

He ran his hands down her shivering body. Her lip trembled as he did so. She was not sure why she seemed so afraid. She had done this numerous times, but this time it seemed different. He was much more gentle than other clients. He was soft, almost caring. And he didn't rush things. He didn't just strip her naked and shove himself between her thighs and up into her. He was slow, letting his hands explore her so softly that it caused goose bumps to appear across her flesh.

He let his hand wander under her sheer pink and black laced nightie, and his fingers carressed her stomach. She watched his hand, her own were resting above her head, her body laid submissively under his touch. He glanced up at her, making sure she was still ok with his wandering hands.

She bit her lip timily as he lifted her nightie up and over her head, exposing her torso. Her body shook a bit, but he gently kisses her lips to reassure her. He continued to kiss her as he moved himself in between her thighs. She tensed, gasping softly when she felt her inner thighs against his body. She looked down, noticing his pants were still on and up, although they were unbuttoned and unzipped, which she had done earlier.

He put a finger under her chin and lifted her head, but she continued to keep her eyes low.

"It's ok" he reassured.

She tried to relax, but she was still nervous and tense. She couldn't wrap her head around the idea that she was so frightened of this man.

"We don't have to do this" he whispered to her, assuring her that he would not be upset of she called it quits right then and there.

She glanced to the door. Could she really run the risk of not having sex with this man after he already paid, and risked getting caught by Frank if he chose to check up on them again? She knew if Frank found out she wasn't doing her job, her already bruised ass would be even more bruised, and her body would scream in pain.

She wrapped her legs around him, urging him to continue. Not fucking him was a risk she was not willing to take. He watched her, almost studied her. He knew she did not want what she was urging him to do. But he also knew that she didn't have a choice. Her entire life depended on the business she delivered and the money she made.

He gently pulled her sheer pink thong down her legs, freeing first her right leg, then her left. He glanced up to see her bite her lip nervously. He rubbed her thighs before leaning down to kiss her. "Relax" he whispered to her "I'm not going to hurt you."

She turned her head, refusing to look at him. Her eyes closed. She knew what was going to happen next and she urged herself not to fight and to just let him do as he pleased. She felt his hand between her legs and she jumped, startled a bit. Ever so softly, he began to rub her. She was dry, and he refused to do anything until that changed. He licked his fingertips and continued rubbing, moistening her with his saliva.

She whimpered, squirming slightly and wishing he would just get on with it and be done.

"Shh, I said I wasn't goint to hurt you, and I'm not. Trust me, this will help."

She stilled. He rubbed a bit more before inserting a finger. She gasped and squirmed again. He hushed her, assuring her that it was ok. He slowly moved his finger inside her, a bit deeper before pulling it out and inserting two. She whined, her body still tense, but she didn't move or fight.

He continued to gently push his fingers into her, slowly and softly. She whined still. Glancing at him, she noticed his brow furrowed. She cowered a bit.

"Shh" he said softly, pressing the palm of his freehand on her pants line "it's ok sweetie." He continued gently moving his fingers inside her. He could feel rough and bulging scar tissue inside of her, and from more than just a ripped hymen.

He leaned down to spit gently on her vagina, letting his saliva moisten her even more. He massaged his saliva into her before pulling his fingers free from her. He leaned over her and gave her a kiss on her cheek. "Are you sure?"

She nodded, wanting him to continue.

He let out a soft sigh as he freed himself from his pants.

She turned and watched him lick the tip of his thumb and slide it over the tip of his member before gently rubbing his length against her, getting himself wet.

He aligned himself with her opening and slowly pushed his way inside. Her body tensed at his intrusion, and he paused to make sure she was still ok with his actions.

She kept her head turned away from him. He gently turned her to look at him. He pushed a bit further into her, clearly seeing her wince. He stopped. "What's wrong? Does it hurt?"

She swallowed hard, clearly uneasy with the amount of concern he was showing. "Pulling" she whispered.

He looked down, moving his hand from her face, gently rubbing her pussy around his member, adjusting her around him so he didn't pull or pinch her.

She glanced up at him, catching his eyes as he focused back on her facial expression.

"Would you like to stop?"

She shook her head. She knew what the punishment would be if he didn't finish.

He pushed into her again, seeing her wince. His concern raised, but he soon began to realize that some of her pain he would not be able to ease. She had been hurt so much in the past that pain was inevitable for her, and that was clear as he could feel the long scars inside her as she tightened around him. It was sad, and he was not sure he would be able to finish. How could any of her client, feeling what he could feel? But he had to remind himself that working girls such as Angel rarely, if ever, got a client that actually cared about what they were feeling.

She felt him slow to a stop. Glancing at him again, she saw his brow furror from his own thoughts. She tried to sum up some explination for his behavior. She could not explain his kindness, nor his concern, but his sudden lack of stimulation down under... She couldn't lose him as a client. Oh, the trouble she'd be in.

She gently slid her fingers down his chest, her hips slowly gyrating against him. He looked at her, confusion on his face, but she continued, pressing her body to his. If needed help to keep it going, then she was going to have to help.

He slowly pressed all the way into her, her body tensed as she let out a soft, pained gasp. He paused and she relaxed, knowing she had to keep up the "I-love-what-you're-doing" act. Slowly he pumped in and out of her, letting her squirm a bit to adgust as he did. She leaned up and burried her face into his next and let out a bit of a faked moan.

But he caught her in it. "You don't have to lie and pretend to like this." He began to slow again.

"No, no" she began to panic.

"Shh" he hushed, trying to calm her and gently kissed her lips. He stared deep into her eyes "I know you are afraid."

Indeed, her eyes did show her fear, and she was practially shaking with it.

"It's ok. You are in control of this. If you want to stop, just say so."

She swallowed hard.

He kissed her again. He needed her to know that he was not like the others she had been with.

She tried to relax. It was comforting to know that he was willing to stop at any time, but she didn't fully trust that he would.

"I want you to get pleasure from this."

She cowered back a bit. Since she was first sexually active at age seven, she had been taught to never enjoy it. She had never had an orgasm, never came, in fact, she had never even come close to climax. It was pretty easy for her, since the pain was always there. She was taught that girls...whores...do not get to be pleased. They are only for pleasing.

The man sat up, looking down at her frail body. "Sweetie, have you ever been pleased?"

She stayed cowered down beneith him.

"I want you to feel pleasure. I want you to enjoy this." He was genuine. He truly wanted to help the girl.

She wasn't sure if she believed him.

"Let's see if we can reduce some discomfort" he whispered softly to her. He rubbed his hand against her cheek gently. "Does that sound ok?"

She nodded, still pretty uncomfortable.

"Ok" he sighs, gently lifting her left leg. He bent her leg at the knee, gently holding it up to his side as he put her right foot on the bed, bending that knee as well. "This angle should help a bit, ok sweetie?"

She nodded again and he slowly pressed into her. He was right, it did relieve some of the pain. Granted, there was still pain, but it wasn't as bad. She relaxed a bit more.

"That's it, good girl."

Her eyes fluttered a bit as he continued to slowly pump in and out. Ever so slowly he picked up speed. She shivered, her back begining to arch. She whimpered, afraid of him, afraid of herself.

"Shh" he kissed her again "just relax."

She timidly ran her hands down his chest, still hoping he would finish quickly.

He took her hands in his, holding them gently, fingers intwined with her's.

She let out a quick and sudden yelp, making him stop just as quickly.

"What? What?"

She pressed her body against him, trying to roll onto her right side. She broke his grip on her hands to press hard on her left him.

Seeing the discomfort sourcing from her him, he held her left leg close, pressing over her hand on her hip, realizing her hip was cramping. Quickly, the pain dissolved and she relaxed once more.

He continued his slow pumping, kissing her again and again. Her hands were on his chest again. She noticed his toned body for the first time, feeling him tense and almost shake. He was close.

"Come" she whispered, wanting him to finish.

"Come with me" his body was starting to get clammy as he held back.

She bit her lip, whimpering softly. She needed to please him to get him to finish, but she was uncomfortable with the demand. "I...I don't..." she stammered before cutting off.

"What? What is it baby?"

"I...I don't know how."

He slowed, looking at her with a puzzled look.

"I don't know how" she repeated. "I...I've never..."

"You've never had an orgasm" he finished for her, sighing. "It's ok" he assured "I'll teach you."

He shifted a bit and continued thrusting into her. She gasped loudly. Her body tensed and started to shaked. He was pressing against her g-spot, but she had no clue what he was doing. He continued as she arched her back and pressed to him. She let out soft, muffled moans and whimpers as she burried her face into his chest as he leaned down to hold her.

"Feel that?" he asked, recieving no response. "Hold onto that feeling. Hold it. Hold it baby" he encouraged.

She tensed, unsure of what he meant, but trying desperately to please him until he finished.

"Good girl" he moaned, almost growling in pleasure. His moans increased, becoming even more throaty and growling.

She whimpered, unsure of what to do.

"Baby, come with me" he almost begged.

"How?" she whimpered.

He moaned, forgetting that she was new to such pleasures. "Push. Push on me. Push like you are trying to push me out."

She gritted her teeth as she bared down, moisture spilling freely from her. He moaned, his thrusting increasing in speed. "Good girl" he praised, tensing and growling again as he came with her. Liquid continued to pour from her. She whimpered and squirmed, concerned about what was happening. "Shh, it's ok, you're a good girl. Relax."

She tried to relax again, the liquid slowing to a stop.

"Good girl, you came" he panted on top of her.

She shivered, whimpering softly. She was light headed, but she felt relaxed, almost exhausted, but uneasily calm. The sudden thought that she was in trouble begain to invade her mind. The thought that she may have actually enjoyed the experience was suddenly frightening and almost toxic to her relaxed body. He must have sensed her fears, because he hushed her and ensured her that she was not in trouble.

He pushed himself off the bed and walked to the bathroom, his pants hanging on his hips. He returned with a towel and gently patted her groin dry. The front of his pants, wet from her ejaculation, were then patted dry as well. He helped her roll onto her side. "Get some rest, sweetie" he soothed, gently rubbing her back.

"Sir?"

"Hmm?"

She was quiet for a moment before whispering "thank you Sir."

He smiled, almost chuckling as he rubbed her back "call me Dante." But he heard her faint snoring. She was already asleep.