The Weekend Slave Ch. 03

As always, let me know what you think!

*

He had cum without permission and now she wasn't going to let him stop. It wasn't just women who could reach multiple orgasms; it was just that for men like Ryan, it was painful. Knowing that he was sensitive and that he didn't want any more stimulation, she roughly jacked him off. Ryan moaned and complained, begging her to stop. Fed up with his complaints, she withdrew the dildo from his ass and shoved it in his mouth instead. It kept him quiet while she forced his balls to give up all of their cum. When she finally finished, his dick was so sensitive that it jumped at the lightest touch. Anna left it alone for awhile and turned her attention to the boy it was attached to.

She gently fucked his mouth with the dildo for a moment, then pulled it out. Ryan coughed and spit and tried to get rid of the taste. She gave him a hard slap. "Be more respectful! I gave you a taste of your ass even as you were disobeying me by cumming!" Admittedly, she had forced him to cum with intense prostate stimulation...but that was the fun of it. Ryan whimpered and didn't apologize. "You insolent little bastard," she accused. She partially untied him and flipped him over on the bed. The puddle of cum on his stomach began to soak into the mattress instead. God, she loved seeing him so vulnerable like this. His sensitive cock ached at the sensation of being pressed into the mattress with the weight of his own body.

Tying him up on his stomach, she disappeared for a few minutes. Exhausted by tonight's activities so far, he started to doze. His eyes were closed when he heard her re-enter. Hoping she would just come lie down and fall asleep with him, Ryan was totally startled by what happened instead.

Thwack!

The paddle landed squarely on his left ass cheek, forcing his sensitive cock hard into the mattress and leaving a stinging sensation on his bottom. "Ow!" he yelped.

"I think you mean, 'Thank you Mistress'," Anna replied with a smirk as she brought the paddle down again. She loved seeing the red marks that appeared and faded. With each slap of the paddle, they faded a little less. She applied the strokes to each side of his ass. "God, I love your bubble butt," she told him. "I know someone else who will love it too." He didn't understand the comment at first, and anyway, he was too preoccupied with the paddling. Anna paddled him a couple more times before asking, "Have you been counting my spankings? I was only going to try twenty on you, since it's your first night."

Ryan groaned. "No Mistress, I didn't count."

"Well then let's start over."

And she did. At this point, the spankings came harder, but she made them unpredictably far apart or close together. Ryan shuddered and moaned softly as he felt his cock stirring beneath him. Sore and abused as it was, somehow he was still getting turned on. When they finally reached twenty strokes, she put the paddle away. She rubbed a hand over his reddened ass, loving the raw, roughened texture of his beaten skin. "Beautiful," she sighed contently. "Well my slave, it's time for bed. You have a long day ahead of you. I've got all kinds of fun planned out." She made him get down on the floor, chained one of his ankles to the bed to keep him from leaving, and then fell asleep in her bed.

*

After an uneventful breakfast (except for the fact that they were both naked), Anna disappeared into her bedroom. She didn't cuff him; he'd made it clear that he wanted to stay, even if his ass did hurt so much that he could barely sit down. He'd made a deal, he'd kind of enjoyed himself, and besides, he was a bit scared of what she would do if he left. She had that video of him, after all.

When Anna re-emerged, she was dressed casually, as if for a day of shopping. In a flowy short skirt and an off-the-shoulder top, she looked cute and casual. Her hair was pulled up in a ponytail, but as always, she wore her bright red lipstick. She was wearing stiletto heels as well. He felt his balls tingle at the memory of her heel pressing into his sack. "Are we going out?" he asked, quickly adding, "Mistress?"

Anna nodded. "Your clothing for the day is in my room. No arguments. Go put it on. I laid it out for you on the bed." Ryan curiously ventured into her room and was dismayed at what he found: a pair of hopelessly threadbare denim short shorts, a black lacy thong, and one of Anna's t-shirts, a small hot pink number that read "Fuck Me" in bejeweled black letters across the front. Ryan struggled into the clothing. The shirt barely fit over his chest: his nipples stuck out against the fabric. He had trouble with the thong; there was hardly enough fabric to tuck his cock into and he wasn't even hard. And when he finally got the shorts past his thighs and buttoned and zipped them, his cock formed an obscene bulge at the crotch. He would have said he looked flamboyantly gay, but no self-respecting gay man would have dressed in this ensemble.

Ryan blushingly returned to Anna's side in the living room. She looked him over, smirked, and then led the way outside. He felt like he was going to pop out of the shorts with every step. He kept looking down to make sure his cock was still restrained. She instructed him to drive and they got in her car. He wasn't sure where they were going, but the whole way there, she rubbed his cock through the shorts. From an obscene bulge, it was now a lewd, vivid impression of his cock, pressed to the fabric of the thong and shorts, nearly ready to pop out the leg of the shorts. When they finally arrived and he looked around, he realized that they were at the mall a few miles away from the college. It wasn't the closest one; most college students went to one nearer the college. But there was still a slight chance of meeting someone they knew. He was terrified.

Anna got out of the car and indicated for him to follow. He stayed close, trying to hide his erection by walking close behind her. His ass was nearly hanging out of the shorts. As they began to stroll through the mall (and Anna kept a leisurely pace), people stared and murmured. Mothers drew their children quickly away, older observers expressed disgust at 'young people today.' Finally, Anna stepped inside a small store. Belatedly, Ryan realized it was a popular local lingerie store. Anna clearly knew the clerks there from the way they greeted her. "This is my latest boy, Ryan," she told them, pulling him forward. Just then, a young man entered from the back room. He was a rugged kind of handsome, all strong jaw and stubble.

"He's our latest boy," a salesgirl whispered to Anna. With a smirk, Anna pushed Ryan to a waiting salesgirl. "Take him to fitting room 3 to try on some panties of his own. Make sure no one else is back there."

The salesgirl liked Ryan instantly. He was cute and obedient...She slipped her hand to his crotch in the dressing room. "Let me help you out of those pants," she said with a smile. He didn't protest, unsure what Mistress Anna wanted. The salesgirl stripped off his shorts and smiled interestedly at his cock in the black thong. Pre-cum made a wet spot against the fabric and he blushed. "Here, try these on. Anna likes to see her boys in these," the girl said. But as soon as he'd removed Anna's lacy thong, the salesgirl was twisting her hand up and down his cock.

By the time Anna ventured back to the dressing rooms, leading the new male clerk by his tie, the salesgirl had given Ryan a handjob leading to an erection of massive proportions. "Oops." she giggled, and slipped out as Anna and the new boy came in. "I told you he'd need a punishment," Anna reminded the new clerk. Paul, as was his name, smiled at her. "You were right, dear." Ryan noticed that he didn't have to call her Mistress.

"Ryan, bend over. Facing away from us. Yes, let Paul see your pretty ass." Ryan obediently turned and bent over, his legs apart. He blushed as Paul slid a hand over his reddened ass cheeks. "Nice job," the man complimented. Ryan heard a zipper but didn't dare look up. Paul's hand remained on his ass. As slurping sounds began, Mistress evidently giving the lucky man a blowjob, Paul directed some of his fingers into Ryan's asshole. Finally, Mistress stood up and Paul asked, "Ryan, what does your shirt say?"

"Fuck me?"

"Sure." And with that, Paul rammed his cock into Ryan's ass. He wasn't as long as Ryan, but he was thicker and it hurt. Ryan moaned but Mistress told him to shush. She sat down on the bench in the dressing room and spread her legs in front of Ryan's face. She wasn't wearing panties. Ryan, torn between enjoying the sensations and resisting, buried his face in Mistress Anna's pussy. She held his head to her cunt and dug her fingers into his hair. Paul's hips were thrusting Ryan's body back and forth, in and out of Anna's crotch. Reaching underneath, Paul rubbed Ryan's cock. "Don't you dare cum, slave," Anna panted and Ryan tried to resist. He humped Paul's hand until Paul finally let go, instead grabbing Ryan's hips and pulling him back onto Paul's cock as Paul started to cum.

Ryan collapsed on the floor when Anna let go of him, satisfied. Cum leaked out of his ass. "Put your clothes back on," she instructed him and waved to Paul as he left the cubicle. But even with the thong and shorts on, cum leaked down Ryan's thighs. His cock bulged rudely and precum dripped from it, creating a large wet spot on his shorts.

It was just like this that Mistress Anna made him walk through the mall at her leisurely pace, all the way out to the car.

To be continued...