Emily's Choice Ch. 03

Instead she merely helped him stand and took him in her arms. He showed no reaction and allowed himself to be pulled to her though her stiff phallus prodded him, challenging. She stroked his cheeks lovingly and with a finger beneath his chin, placed a soft kiss on his closed lips. Barely speaking the words, she mouthed; "Relax, give in to me." He knew he could do nothing else.

This time he kissed her more passionately. His lust drove him and his licked her full lips, gently taking one between his and sucking it. The point of his tongue dabbed at the corners of her mouth and she allowed him to hold her chin in his palm. He was frenzied but controlled which, in his state, surprised Diana.

She allowed him his turn then guided him, sliding her lips over his to demonstrate the proper technique of how a man should kiss a woman. Her fingers caressed his cheek, which caused him to flow into her. This woman understood how a man feels and played him expertly. With only a few kisses and tender caresses he felt himself taken in her grasp.

The dildo strapped over her wide hips poked him in the scrotum, causing him to clench his jaw. He feared it but knew in the hands of a woman like Diana, it would be used with only the utmost care.

She led him to her bedroom where she positioned him by the side of her bed and, with a gentle press on his shoulder, bent him over. His weight rested on the palms of his hands and with gentle encouragement, she had him press his cheek to her fluffy bedspread. His arms reached out to either side prone on her bed.

In this position she discovered the state of his ass. It was swollen from his recent spanking, with bright red spots surrounding slight bruising. She pitied the male and knew how hard it can be for the men in this family. He had just begun his training, however, and it wasn't out of the ordinary.

She traced the outlines of his welts slowly. "You've just been spanked," she said, almost a question.

"Yes, Ms. Donnelly."

She wanted to make him feel better. "You probably deserved it, Sharon's a good woman but she can have a heavy hand when she needs to. I'd watch my tongue around her from now on if I were you, cutie."

Her hand wrapped comfortably around her shaft. She always enjoyed this side of herself; the primal urge she felt when taking a man anally, and she adored the feel of a strap on hanging almost magically below her navel.

Taking a tube of lube from her night table she squirted a generous amount into her palm. Lovingly she slathered her toy with it until its surface was coated in layer of gel. On her command he reached back and spread his asscheeks as wide as he could. Inside he was smooth and shaven, Diana noticed. Before she covered his back passage with the lube, she stroked his crack with one outstretched finger until it rested on his hole. When her hands touched his worn skin he cried out.

"Easy, boy," she cautioned.

Slowly she dripped the gel onto the softness of his bottom. Knowing too much is not enough, she spread it from the beginning of his crack to the very back of his balls. A great amount was spread along each cheek and down the sides. This was for her own pleasure, as she loved to feel the slick wetness of a boy's ass when she was inside him.

Steadying herself with one hand on the back of his neck, she directed her cock against his passage. He tensed and made a groan of discomfort.

"This is going to happen. Don't fight me or it will just be uncomfortable. Relax and give in and you will enjoy it." With a slow, practiced movement, the tip of the featureless rod penetrated him. He whined.

"I know, I know, sweetheart. I know it hurts. It's supposed to. Just let Ms. Donnelly take care of you now. I know what boys need."

He looked delicious like this. Face pressed into the mattress, one hand clenched into a fist, the other spreading himself for her, she watched his sphincter slowly dilate to allow for her member.

Grasping the meat of his buttocks in each hand, she pressed ever more slowly into him. His voice came out in a deep moan into the bedsheet. He was having difficulty but remained docile. More than likely his spanking was the reason.

She felt his ring open and her length easily slid into him. He froze from the pain and she rested to allow him time to process the feeling. Her hair rested on his bare back and she swayed it over his skin to soothe him.

Slowly he started to breathe again and Diane pulled out just as carefully. He seemed relieved by this and his entire body seemed to react. His tight anus clung to the invader as she withdrew. She reentered him and found his passage slick with moisture. It didn't hurt him as much as it did and with each successive thrust it hurt even less.

Face still pressed to the mattress he refused to admit to himself that he found it enjoyable. This was not how men were supposed to feel. A woman is made for such things. Men were the penetrators. He remembered the times he'd entered a woman's ass, feel her clench and think of how good it felt.

Diana grew more insistent as she watched the dildo slide effortlessly into his ass. With the pace she was going, she was able to free a hand to stroke her nipples as she fucked the boy. He had a beautiful ass, and watching him split and opened excited her more than she thought. Cream formed beneath the dildo harness and she wished for room to slide her finger between it to massage her sex.

His cries turned from pained whimpers to bursts of excited pleasure. To Diana it seemed he hadn't expected to enjoy it the way he did. This brought her an unexpected sense of pleasure. Not many males accept this role so soon or so easily but some take to it as if they were born for it. Emily may have found a stud with a latent bitch inside.

"That's it boy. Sit there and let yourself get fucked. Take it like a good little bitch," she taunted.

This seemed to both aggravate and excite him as he reeled up to protest only to squeal happily when her dildo brushed his g spot. Reaching under his armpits, she pulled him up so he was on his knees away from her. She whispered in his ear;

"Good boy, you know how to take it so well." Holding her hand to his back entrance to feel the slippery shaft stroke his canal she teased, "Your ass knows just how to open for me. Do you like that?"

He nodded eagerly and when she reached around to feel his cock it was throbbing and swollen. She continued pumping into him as she wrapped one arm around his chest while the other held his head and pushed his ear towards her lips. She bit his lobe, tugging it hungrily.

"Lie down. I want you on your back."

Without a show of resistance he complied. She was able to maneuver him onto his back so just the tip of her shaft remained inside his asshole. Leaving it there for a moment, she examined him.

His balls were drawn tight against his body, partly from fear and partly from a need to orgasm. His hands wanted to fist his length but remained clasped at the sheet above his head. His mouth was opened slightly, his head turned back. The expression on his face was a combination of fear, nervousness, shame and outright lust.

He was unable to understand all he felt. He knew he shouldn't give in to what he felt so easily but it was a pleasure completely foreign to him. It stung him and brought him right to the edge, holding him back from taking the plunge he knew must happen. It teased and stroked him. It felt as if someone had reached inside himself and masturbated him. It was an agonizing feeling, not being able to go any farther and, as she watched, tears started to appear in his eyes.

Her hand was on his balls now, squeezing playfully with each thrust into him. He felt like a puppet, his arms shaking on their own commands.

He reached toward her, feeling for her breasts with his eyes closed and she allowed him this pleasure. With a clumsy grasp he located one and gripped it almost tightly. This drove her to greater heights and soon she was pumping into him with a frenzy, her wide hips making loud slapping sounds in the room. He squealed with each thrust and she tugged on his balls, playfully slapping them. Tears spilled from the tightened cracks of his eyes and, before either of them were aware, he peaked.

He did not climax, at least not fully. It was more of a dull sensation turning to a pleasurable tickling before dissipating at the tip of his thickened shaft. Heavy blobs of jism shot from the head to land in patterns on his chest. Each burst was following by a high pitched wailing that lasted long after his balls had drained.

Diana held his body steady, allowing him to feel this special moment. She had not yet reached her orgasm but knew there was time for that. The lesson had just begun and there was time for her later. For now she allowed him to curl into her as she pulled her cock from his ass with a loud 'pop'.

Like a wounded animal, he breathed deeply and hid his face between her breasts. She breathed with him as she felt his tears on her dampened skin. This was a special moment in a boy's life and she was honored to share it with him.