Jack pushed her into the room and unfastened the cuffs at her wrists. "Turn around and bending from the waist, pull down the thong, slowly," he ordered. Trembling, she turned and did as he asked. "Spread your legs and grab your ankles," he commanded once she was fully bent over.
She stepped out of the thong and spread her legs, wrapping her hands around her ankles. He gazed at her fully exposed pussy, the shaved lips spread wide, hiding nothing. He approached her and ran his finger through the pink folds, briefly dipping inside her, causing her to gasp at the slight penetration. He gently slapped the lips a couple of times before trailing his finger to her asshole. He pushed his finger against it, dipping just the tip in. "This is going to be so good," he murmured. "I am going to spread you so wide." Stepping back he told her to get on the bed on her hands and knees.
He pulled a few items from his bag and knelt behind her. She could feel the oil as he squirted it at the top of her ass. It slowly trickled down over her puckered hole, which he began to circle with his finger. He pushed her head down into a pillow before kneeling again between her legs. He opened a tube of lube and squeezed some onto his finger. "You ready?" he asked.
She took a deep breath and whispered, "Yes, sir."
Hesitating, he said, "Steffie, you don't have to do this if you really don't want to. Just say so and we'll stop."
She thought for a moment and replied, "No, it's OK. Ever since you first mentioned it, I've been thinking about it and I do want to try it. As you can probably tell, it's getting me very excited."
Or course, he had noticed how wet she was. Her pink lips were glistening wet and some was even running down her thigh. "OK then, here we go," he said as he pushed his lubed finger at her tight hole. He had to push hard but it entered her and he slid it in to the first knuckle.
She gasped and cried out. She was surprised that something as small as his finger would hurt. He pushed in further until his whole finger was inside her. Twisting, he pulled out and then pressed back in.
He pulled out and lubed up two fingers and then pushed them inside. She bit her lip trying not to cry out. He slid them in and out of her and the pain began to fade into pleasure as he finger fucked her ass. She groaned her pleasure but it was soon replaced by another gasp of pain as three fingers worked their way inside her and began to pump in and out.
He pulled them out and she felt lube again being applied to her hole. She could hear him squeezing more out of the bottle and soon something was pressing at her ass. "A little toy for you," Jack explained, a smile in his voice. "A slim dildo." He pushed the phallus hard and it slid into her, spreading her hole.
Steffie pressed her face into the pillow and screamed as it stretched her. Oh how it hurts, she thought. How was she going to be able to take his cock if she couldn't take this thing?
Jack pumped the dildo in and out of her ass, trying to get her used to it. The pain she was feeling again faded into pleasure and she moaned. "Does that feel good?" he asked her.
"Yes, sir," she murmured.
"Good, you're ready for the next step," he replied. "The butt plug."
"A butt plug?" she asked as she felt the dildo removed and something bigger pushing into her. This one was really spreading her. She could feel that it was getting wider the deeper it went. Suddenly it became smaller and was fully inside her. She lifted her head from the pillow she had been screaming into. "Is it in?" she asked, her voice shaking.
"Yup, it's in," Jack confirmed, staring at the base of the toy. Grabbing her leash, he tugged on it, "C'mon, let's go show Cal."
She winced as she stood, the plug pushing in deeper. They descended the stairs and she was blushing as Jack told her to turn around and bend over.
"Hey, right on!" Cal exclaimed, seeing the base snugged up between her ass cheeks.
A sudden thought struck Jack and a wicked gleam appeared in his eye. Grabbing the leash again, he pulled her from the room. "C'mon!" he ordered, hurrying up the stairs. He stopped in his room and quickly grabbed the vinyl thong and then proceeded to Steffie's room.
"Put these back on," he said, tossing them to her. "Put on that really short, tight mini skirt you have and one of your thin short tank tops. No bra," he ordered.
She dressed as he ordered and he stared at her. Lifting her top, he removed the nipple clamps that she had forgotten all about. The pain in her ass far outweighed the feelings those little clips produced. He lowered her top back down but left it slightly bunched, revealing more stomach. He also bunched up her skirt a bit so that it didn't quite cover her ass. The very bottom curve was visible when she walked.
He walked her back downstairs and showed her to Cal. "What do you think? Does she look like a bitchslut?"
"Hell yeah," Cal replied, leering at her nipples that were hard and straining at the thin cloth of her top.
As he unclipped her leash, he said to Cal conversationally, "You know what Cal? We seem to be completely out of fresh porno mags. I think bitchslut and I should take a stroll to the smut shop on the corner and buy some."
"That sounds like a great idea!" Cal enthused.
Steffie went pale. He couldn't be serious! The store on the corner was much like any other corner store except they also sold the most obscene magazines and the young men behind the counter always leered at her whenever she went in. She couldn't possibly go in dressed as she was, with a plug up her ass!
Jack saw her mortification and confirmed her fears. "Oh yes, we're going." He saw she was resisting and held up the leash. "Now don't make me use this," he threatened cheerfully.
On trembling legs she headed for the door. Best to just get it over with. As soon as they stepped onto the street, people stared at her, men with lust in their eyes, women with disgust. She could feel the plug pushing in her ass with each step she took. They reached the store and she hesitated before going in. He gave her a shove in the small of her back and she stumbled in. The two young men behind the counter looked up and couldn't help but smile wolfishly at her. "Smile and wink at the nice young men," Jack whispered in her ear.
Obeying she turned and smiled saucily at them, giving them a wink. Jack slid his hand down to her ass, squeezing her cheeks as they turned and walked to the magazine rack. Sure enough, the usual assortment of dirty titles were on display. Jack picked up a copy of Anal Invaders and began to flip through it. He handed it to her, saying, "I think we should get this one. And this one too." He grabbed a copy of Butt-fucked Beauties. He handed her every magazine they sold on anal sex and a couple on bondage and proceeded to the counter.
The guys behind the counter blatantly stared at her breasts, the hardened nipples plainly showing through the thin fabric of her top. Jack saw the direction of their gaze and squeezing one of her breasts, he asked, "They're nice, aren't they?" Much to her horror, he lifted her top and fully revealed them. He pinched the hardened nipples before lowering it again.
Tearing his eyes away from her tits, one of the guys began to key the magazines into the cash register. After a few he mentioned, "You guys like the butt action, don't you?"
"Oh yeah," Jack replied. "My bitch here has a plug up her ass right now!"
Steffie was so stunned that she couldn't even think to react when Jack turned her and lifted her skirt, pulling her thong aside so the guys could see the plug in her ass.
"Very nice," they commented. "Hey, is her pussy shaved?" one of them asked.
