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She lay with him, thinking about what was happening in her life, and how it indicated that she was a bit fucked up that she was enjoying it, until he stirred and said they should probably get ready for their night out. He at least seemed a bit more chipper after a little nap. He got a dress out of his suitcase and handed it to Heather. It was a pleated chiffon skirt with a halter top that tied behind her neck. The halter top was completely backless, and it plunged between her breasts all the way to the beltline of her skirt, right at her navel. Basically it was two wide bands of fabric, about an inch apart, coming up from the beltline and tying behind her neck. At least it adequately covered her boobs, and although the fabric was thin, it wasn't sheer. Her nipples would show a tiny bit, but compared to some things she had worn for Brad, it was almost prudish. He also gave her a pair of black thigh-high stockings. She didn't even bother to ask if she got any underwear.
Brad dressed in a cobalt blue dress shirt, tie, and navy blue suit. She smiled at the thought that he looked pretty good for a guy his age. They'd probably still get a lot of stares tonight because of their age difference, but at this point Heather didn't give a fuck. She was his little slut, and she didn't care what people thought. She finished her makeup in the nude, put everything back on, and was ready to go. As the elevator doors closed, Brad let her know she wasn't quite completely dressed.
"I have a little something more for you," he said as he pulled a stainless steel, jewel ended butt plug out of his jacket pocket. "Hold this in your mouth to lube it a bit."
He put the plug up to her mouth, and she took it in obediently. He lifted the back of her skirt, pulled out the small tube of lubricant and quickly lubed her asshole. This would make quite a sight if the elevator doors opened now, a jeweled butt plug in her mouth and his finger up her ass. He took the plug back, and eased it into her ass. It was good that her ass was well prepared, it didn't take too long to get it in. He finished just before they reached the ground floor, and she sighed in relief when he lowered the back of her skirt.
The ride to the restaurant was relatively uneventful, with him just stroking her upper thigh as they chatted. She began to find out a bit more about him, what he did for work, even a tiny bit about his previous marriage, although that seemed a sensitive topic. The restaurant was one that she had heard of, run by a celebrity chef; it was clear he was working hard to impress her. They sat in a booth, with him moving to sit next to her. She figured that allowed him more access to play with her, as well as block the view of most of the restaurant. Right after they sat down he whispered in her ear that for the rest of the night he wanted her to sit with her bare ass on the seat. It scared her a bit to be so public like that, but she shifted in her seat and got her skirt out from under her. It was difficult, because lots of people were sneaking looks at her. Wearing a dress like this without even a wrap was definitely getting attention, and she could tell lots of guys were checking her out.
They sipped some champagne, and continued to chat as Brad took more and more liberties with her body. He caressed her upper thighs, finding the bare skin above her stockings, stroked her arms, brushing his fingers along her breasts, rubbed her bare back. Heather was getting more aroused by the moment, and she started to worry that she was going to leave a wet spot on the bench. Once the menus arrived, Brad reached in his pocket and handed her something.
"Just because I'm so nice," he murmured in her ear, "I'm going to let you go to the women's room to insert this. But I will check on it's placement once you're back."
Heather looked to see the horseshoe shaped vibrator. She looked around, rested her hands in her lap, and casually snuck the vibrator under the skirt.
"That's okay Sir," she batted her eyes at him a bit. "I think I can do it right here."
Heather felt so dirty and wanton, lining one side of the horseshoe up with her opening, and sliding it into her sex as people watched her. Well, only Brad was really watching, but if someone else walked up to the table they would see everything. Her pussy was so wet that it slipped right in, and she shivered at the sensations.
Brad had an amused look on his face as he pulled his phone out of his jacket. He made a few quick taps, and she felt the vibrator buzz to life. It seemed to be set to be more active on the internal side, stimulating her g-spot more than her clit. She knew this setting was going to drive her crazy with need before too long, and she snuggled against him while her thighs bounced open and closed. He casually stroked her bicep and read the menu, brushing his fingertips against her breast. She couldn't stifle a small moan when he pinched her nipple through her halter top.
He kept the vibrator running while the waitress took their order, making Heather's voice quiver while she spoke. She could feel the woman stare at her flushed cheeks, the side of her boob, and the bare skin of her thighs above her stockings; Heather felt more humiliated and more turned on than ever. Once the waitress was gone, she kissed Brad passionately, probing his mouth desperately with her tongue, pulling his hand to her needy crotch.
"Slow down there slut," he laughed as he pulled away from her, "you're going to cum too soon if you keep that up."
"Too soon?" Heather asked as he tapped his phone and she felt the vibrator diminish to a very soft flicker on her clit and her g-spot. "Does that mean you ARE going to let me cum?"
"We'll see," he pinched her nipple again,"it depends on how good your are."
Heather's mind was in a fog through the rest of dinner. She did notice that the dinner was extremely good, the fish was probably the best she had ever had. Under normal circumstances that would have made this a fantastic date, but since she was sitting in a barely there dress, with a plug in her ass, and a vibrator in her pussy, the food kind of faded into the background. All through the meal he did his best to keep her on edge, stroking her bare flesh, tweaking her nipples, varying the settings on the vibrator, to the point she felt like she was going crazy. By the time they finished dessert and left for the theater Heather actually had to use her napkin to wipe her crotch and upper thighs. She was totally humiliated by the wet spot she had left on her seat, but there was nothing to do about that now.
Thankfully he turned the vibrator completely off for the short walk to the theater, letting her recover slightly. He had chosen to take her to "Avenue Q," probably based on a chat they had had way back before all of this had started. He had made some reference to it, and so he knew she hadn't seen it. She was looking forward to something light and funny, to offset the nervousness she felt not knowing what he would do to her. As they sat down he whispered a reminder that she shouldn't sit on her dress. The guy sitting next to her on her right looked to be in his seventies, so she just hoped that the old guy couldn't see that well. She flipped her skirt up in back a little just as she sat, and she felt like she had managed to do it without mooning the entire audience. The guy on her right started chatting with them, and Brad was clearly enjoying her discomfort at having to talk to this old man as he leered at her barely covered body.
Just as the lights were going down, he tapped his phone a few times, and she felt the vibrator coming on strongly, both inside and out. Probably not strong enough to make her cum, but since she was already turned on, in public, and with a plug up her ass, she wasn't sure that she could hold back. Once the theater was fully dark, she felt him reach across her, pull her halter top to expose her right breast, and grip the nipple tightly. She wanted to protest that the guy next to her would see, but before she could do anything she felt a strong clamp attach to her right nipple. She had to bite down to stop from gasping, but at least he covered her nipple before the stage lit up and her neighbor might see her. She still had a chain coming out of her dress and across her chest, which he seemed to enjoy tugging as she squirmed in her seat from the vibrator. He didn't even wait for the lights to go down to attach the other clamp to her left nipple, but at least he was able to cover her tit with his hand while he did it, and everyone in the audience was looking up at the stage anyways. He attached this clamp so the chain came out by her bicep, letting him pull both her nipples to the left with one tug on the chain.
It was a surreal experience. The show was outrageous, inappropriate, and just about the funniest thing she had ever seen. Unfortunately, she was so distracted it was difficult for her to really appreciate it. She couldn't stop rocking in her seat, letting him tug on the chain and her nipple clamps, trying to get any extra stimulation that might let her get closer to orgasm. She still wasn't close, but she hoped it would keep building on her.
Suddenly he pulled out his phone, and she felt the vibrator surge to life, and Heather literally jerked in her seat from the intense stimulation to her clit and G-spot. He tugged on her nipple chain, and leaned close to her ear.
"If you can do it before this song ends," he whispered, "you may cum, slut."
Heather's mind spun as she tried to understand what he was saying. Cum, right here? There was no way she could do that and keep quiet enough to not be noticed. All of a sudden, she realized the song was called "You Can Be as Loud as the Hell You Want When You're Makin' Love," which wasn't exactly what she was doing, but close enough for her to be allowed to make some noise. The thought made her giggle, and she wondered how long Brad had planned this. She did her best to relax into the sensations.
"Turn up the inside bit as high as it can go, and the one on my clit to medium," she whispered in his ear. "Please, Sir."
By this point she was so on edge, that even with everyone around her she probably wouldn't have been able to stop from cumming even if she wanted to. She grabbed his hand, clenching it and pushing it away from her so the chain would pull on her nipples even harder. Her legs were trembling and jerking as she got very close, and her head rolled back and forth.
All at once she went over the edge. Her body spasmed uncontrollably, and she knew that anyone around her would know what was going on. But she was too far gone to care. The intensity was beyond anything she could have dreamed of, orgasming with all these people around. She held on to his arm for dear life and let the sensations wash over her. Her ears were ringing, and she felt almost like she was receding out of her body. She thought she might be moaning or maybe even yelling, but honestly she couldn't trust her senses. The whole world faded away from her as she came over and over.
*
Brad tried to remain calm as he worried whether they would get kicked out of the show. He had thought the idea of having her cum during that particular song would be funny, and he had been proud of how clever it was. Now we was more than a bit nervous by all the dirty looks we has getting from audience members around them. Heather had made more noise than he'd expected, especially the small screech that came out when she pushed his hand away hard and the clamps had ripped off of both her nipples. That had to have hurt like a bitch, but it only seemed to make Heather's orgasm go on even longer. People shifted in their seats and looked that them a bit, but thankfully no one said anything or got out of their seat to get an usher, so they were probably safe for a bit. Heather just leaned against him and held his arm tightly, her face buried against his shoulder. He wasn't sure if she was even conscious, but he decided no matter what they had better get out of there before there was any real trouble.
As soon as the lights came up he could see for sure how many dirty looks they were getting. He guided a somewhat dazed and unsteady Heather to the aisle, and then as quickly as they could out the front door. She had a sheepish smile on her face once they were outside, and didn't seem too upset that they hadn't stayed. It was only a little over a mile walk back to the hotel, and even though Heather had heels on she thought it would be better to walk and help clear her head. She just asked not to go too quickly.
He put his arm around her and she leaned into him as they walked. She slowly became more alert as they walked, and she began telling him about how intense the experience was from her perspective. It seemed like she didn't remember a lot of what had happened during the show, but she was clear that the orgasm had rocked her world.
As they walked, he slid his hand down her bare back, then down onto the short scrap of skirt covering her butt. He was enjoying the firm feeling of her ass cheeks through the thin material when to his surprise she grabbed his hand and guided down below her hemline and back up on to her her bare buttocks.
"Please play with my ass, Sir," she said while keeping her eyes downcast. "I'm not scared anymore."
Brad ran his fingers up and down the crack of her ass, pinching and pulling the smooth flesh, giving the butt plug a firm tug. He stopped and pulled her in for a kiss. As their tongues intertwined he tried to work up his courage. On one hand he felt like he shouldn't push his luck any further, but on the other hand he wasn't sure he'd ever get another chance like this. He kept kissing her and used both hands to lift up her skirt in back and tuck it into her waistband. This fully exposed the lower half of her ass to anyone passing by. He grabbed her butt cheeks hard, totally exposing the jewelled head of the plug. He grabbed the plug, and pulled it slowly but firmly until it popped out of her asshole, making her grunt softly. He pushed it back in, popped it out again, fucking her ass with it while they kissed. Finally he left it in and broke off the kiss.
"Let's keep the excitement level up," he grinned at her. "Let's walk with you just like this."
"Of course, Sir. Yes, Sir." came her obedient reply
Brad wasn't entirely sure what was up with her more compliant attitude, but he figured that he should take as much advantage as he could. He kept his hand wandering over her ass and guided her to keep walking down the street. He thought he might have heard a shout from a block or two back, but no one was near them, so he wasn't too worried. After about a block and a half he stopped and pulled her in for another kiss. This time he paid more attention to her breasts, groping them and pinching the nipples. She jumped a bit when he pinched, confirming they were very tender after having ripped off the nipple clamps, but she just moaned into his mouth and didn't do anything to stop him as he continued to abuse her tits.
They continued walking, only this time her boobs were exposed as well as her ass. He kept pulling the plug to just come out of her asshole and push it back in as they walked. Every once in a while he'd look down to watch the sway of her exposed nipples. It was really all he could do to not just strip her and fuck her right there, but the risks they were taking were already more than was really smart. He could feel how shaky she was, but he wasn't sure if it was a leftover from cumming in the theater, or from walking half naked across Manhattan.
When they were a block from the hotel he stopped to kiss her some more, and then he rearranged her clothing to be just slightly more discreet. He didn't put his hand under her skirt while they walked through the lobby, but he did grope her a few times. As soon as they were off the elevator on their floor, he pushed her against wall and began kissing her forcefully. He put her arms up over her head and used his left hand to pin her hands together against the wall. He used his other hand to lift her dress up entirely, stripping her completely nude. She gasped and kept looking up and down the hall nervously, but she didn't protest, and kept kissing him.
Brad grabbed a secure hold of her left nipple and used it to pull her down the hallway. She whimpered for a moment, but followed without trying to cover her naked body or to protect her sore nipple. He found himself more and more impressed with her resolve. She seemed more determined than ever to see this through.
He made her stand naked with her hands on top of her head while he unlocked the door, just to accentuate her embarrassment. Once in the suite, he pinned her to the wall and they kissed passionately. He groped her relentlessly, and she massaged his rigid cock through his trousers.
"I've been really naughty," she panted when they broke of their kiss for a second "I think I deserve to be spanked."
Brad thought about this for a second, and pondered where this was going. He knew he couldn't let her get too far ahead of him. He needed to regain some control. He slapped her ass hard.
"Don't fucking tell me what to do," he smirked.
He used her tit again to pull her over to the sofa, and bend her over its armrest.
"Don't hold back, Sir," Heather whispered, her voice trembling slightly. "Use me. Use me any way you want."
Brad hardly knew what to say. This was surpassing all expectations. The only thing that made sense was that she had decided that submitting more completely was going to get all of this over sooner. He smiled, thinking how it was going to backfire on her. There was nothing she could do that was going to make him relent. He rubbed his hand across her butt cheeks for a few seconds, lifted his hand, and spanked her with a loud whack. He fingered her wet slit and played wiht the plug in her ass for a bit before spanking her again. He kept it up, alternating between fingering her and reddening her ass. He was enjoying the way she was moaning and wiggling, and the way her ass was getting red. But he didn't want to bruise her, and as much as he wanted to continue, he figured he should move on.
He spun her off the sofa, scooped her up, carried her to the bedroom, and tossed her on the bed. He dropped his trousers and underwear. He pulled her back up, grabbing her hair.
"Suck it," he commanded.
She took him into her mouth, working his hard prick enthusiastically. She licked it all up and down, tickled the underside of the shaft, and then took him deeper. He kept his hand in her hair, but as long as she was so into it, he opted to let her move freely. She had other ideas though, pulling away for a second.
"Fuck my face again Sir," she looked him in the eye. "Please."
He figured that wasn't something he could argue with, so he twisted her hair tighter in his fingers, pulling her head onto his cock. Heather grunted softly as he slid to the back of her mouth. He backed off slightly, not wanting to hurt her, but she reached up to grab his ass cheeks and pulled herself closer to his hips. It took her a couple tries, but she managed to get his cock all the way into its base again. Her lips were pressed against his hips, her nose buried firmly in his pubic hair. She bounced her head just slightly, somehow getting him even deeper down her throat. She even managed to stick out her tongue a bit, just touching his balls. He didn't think his cock had ever been harder. He began rocking his hips and moving her head, pistoning his dick in her throat. He'd pull out long enough for her to catch a breath or two, and then went right back to fucking her throat. The feeling was unbelievable, it made his head swim. He knew if he didn't stop soon, he was going to cum before he'd finished his plans.
