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"I think it's time to lose your jacket," he finally said, pulling up her dress until it just barely covered her boobs. "Get your carry-on on out of the overhead, put your jacket in it, and while you're at it, get your nipple clamps from your bag."
"Oh my fucking God, Sir. We're gonna get busted for sure," Heather was close to panicking from the risk.
Her legs were wobbly as she stood and stepped over him in the aisle. It took all of her willpower to not pull her skirt down, but she knew her rule and left the dress just as he had adjusted it. The fabric was a bit clingy, so the skirt did not drop very much, even when she wiggled her hips a bit. Brad held out his hand, suggesting that he hold her jacket while she got down her carry-on. Standing in the aisle in just the tube dress felt very exposed, she could feel all the eyeballs on her. As she reached up to open the overhead, she realized her next problem. She would need to stretch and stand on her tiptoes to reach the bag, and either her skirt would ride up to expose her pussy, or maybe her boobs would pop out. Or maybe both would happen, since she had no control over what her dress did. She reached up with her left hand, since that was towards the front of the plane, and no one was there to see that side, but in the end she needed both arms to pull the suitcase. She could feel the hem of the skirt lifting, but all she could do is stand close to Brand and hope that if she flashed her pussy that it would only be to him. She struggled to get the suitcase out, and when she arched to her right while lifting the bag out she felt her left nipple pop above the dress. She basically just dropped the bag and leaned over him, cowering in the hope that no one else could see her exposed breast. She looked at him, silently pleading with him to cover her up. He smiled, reached up to grab the top of her dress, but pinched her nipple instead. He pulled and twisted it painfully for several seconds before covering her back up.
"Careful there, you kind of fell out," he said loud enough for others to hear, as if she weren't embarrassed enough.
She managed to put the jacket away, toss the chain with the nipple clamps onto her seat, and get the bag back into the overhead without any more mishaps. As soon as she was in her seat, he kissed her passionately, making her want to melt into his arms. They broke it off when the flight attendant came around to collect their glasses, but Brad's hand stayed on her upper thigh, earning them a slightly disapproving look.
Once the coast was clear, Brad got up and got a blanket out of the overhead, handing it to Heather. He suggested she bundle up for a nap, although she wasn't really thinking he'd let her sleep. She spread out the blanket, and tucked it around herself, feeling better covered than she had all day. But it was not to last. He leaned over and whispered that she needed to hand him the dress before putting on the nipple clamps. Heather stared at him in disbelief, and waited for him to smile, laugh, or just say that he was kidding, but he stared at her stone-faced.
"We're going to get arrested for sure," she hissed.
"You worry too much. Now hurry up before I spank you."
As unobtrusively as possible, Heather worked the dress down, tucking her feet under the blanket so it would hide her dress coming off. She handed him the dress, and she was stuck completely naked under the blanket. This was fucking crazy, she was completely fucking naked on an airplane. She could feel herself starting to hyperventilate, this was just so crazy. She tried to settle down a bit, trying not to think about how easy it would be for the flight attendant to catch them. Once her heartbeat slowed a little bit she went to work putting the clamps on her nipples. This was a little easier, since she turned a bit to face the window and no one could see her under the blanket. Once done, he made her let him have a peek, and he gave a couple firm tugs on the chain. She could tell she was going to have sore nipples pretty constantly while she was with Brad.
"Okay slut," he whispered in her ear. "I'm going to relax and read a bit. You should edge for the next 10 minutes, I'm kind of looking forward to seeing you do that in person. Be careful though, you wouldn't want to attract too much attention."
Heather rolled her eyes at the last comment, but she knew he was serious enough. She laid back in her seat, snuck her hand to her crotch, and slowly diddled herself under the blanket. It didn't take very long before her body was tensing up, her hips arching off her seat. She closed her eyes, and hoped that no one noticed her behavior, or the outline of the clamps showing through the blanket. The ten minutes seemed to last forever, but finally the timer on her phone buzzed, and she reluctantly moved her hand away from her clit. She pouted at him, hoping that he would take mercy on her and let her cum before too long. Like as soon as they got to the hotel.
"Very good. I'm going to use the restroom, and then probably take a nap for a bit. We have a busy night planned. Don't go anywhere now," he added with a chuckle.
Heather didn't think she could get any more nervous, but when Brad left her alone, taking her dress with her, she could feel a herd of butterflies in her stomach. What if he didn't give her the dress back? Would he leave her here naked, waiting to be discovered? Even if he did give it back, what if he waited too long and everyone was up and moving before she could get it back on? What if the flight attendant asked for the blanket back? She closed her eyes, and tried as hard as she could to not think about all the bad things that could happen.
*
Brad had a raging boner when he got in the restroom, but there was no way he was going to masturbate when he had this little hottie he could play with for the next couple days. He seriously considered if it were possible to fuck her here on the plane, but it was just too risky. He was already taking some serious chances, but he knew he had to take advantage of the situation. That said, he pretty much had not stopped being terrified since he had met Heather at the airport. His fear that she would have him arrested and carted off for extortion had been replaced by one or both of them being arrested for public indecency. He had worked very hard to keep up a cool exterior, like this was no big deal, but he had come close several times to chickening out and just telling her to get dressed before something bad happened. When her nipple popped out while she was getting her bag had been the most terrifying. He was pretty sure the people behind them saw, and all they would have to do is complain for all of his plans to be ruined. Things seemed a little less risky now, at least if you didn't count that Heather was alone at her seat, completely naked under the airline blanket. At least since everyone had seen her before in the strapless dress, it wouldn't be that strange that they couldn't see it while she had the blanket over her.
He had wanted to wait here a while, to make her suffer a bit longer, but he was too nervous to stay long. He rearranged his hard-on so it wouldn't be too obvious and returned to his seat. He gave Heather another kiss, which went on for quite a while allowing him to pull her nipple chain some and finger her pussy a bit more. She was a really good kisser, so as nervous as he was, she made it a lot of fun. He settled in to rest for a while, telling her that she'd get her dress back before landing. He actually gave it to her when there was still over a half hour to go, he didn't want to cut it too close. He enjoyed watching her shimmy under the blanket to get the dress back on, and he enjoyed watching her stow the blanket in the overhead even more.
The benefit of having her with the dress was that he was able to stroke her thigh again as the plane descended, brushing his fingers along her pussy lips, even dipping them in now and again. He finally had to stop as the plane landed, mostly so his erection would subside enough for him to walk off the plane. He draped his arm around her shoulder as they walked through the airport, brushing his fingers against the tip of her breast. He got a few disapproving looks, but that was probably as much about being a fifty year old guy with a girl in her mid-twenties as it was about touching her tit. He also took several opportunities to grope her dress covered ass, while pushing her skirt up as an added benefit. She was clearly struggling not to adjust her dress, but he was impressed with her resolve as she never actually tried to fix it.
They got their luggage, and he used the app on his phone to get a limo. Once Heather settled in behind the driver of the black sedan he reached over and pulled her hem up. He had to nudge her to lift her ass a bit so he could get the skirt above her hips. She looked at him with a horrified expression, but she kept her thighs spread with her cunt in plain sight. As long as the driver kept his eyes on the road he shouldn't be able to see the state of Heather's dress. To up the ante a bit, he gave her nipples some very firm pinches, moving her dress down as he did it, so that her areolae were just barely covered. He placed his hand on her crotch and spent the rest of the ride fingering her sopping wet pussy, spreading her juices around her thighs. If the driver heard the squishy noises or had any idea what they were doing, he gave no indication.
He whispered in her ear that she could pull her skirt down a little bit when they got to the hotel, but that she needed to exit the limo with her legs spread wide, and that she'd better do a good job flashing her pussy as she climbed out. She looked scared, but she nodded.
It was a hot and humid summer day, and Brad enjoyed the view of scantily clad women walking or jogging along Central Park. He'd always enjoyed the "scenery" that came with warm days in Manhattan, but he'd never seriously thought that he'd have the chance to bring a woman here who would participate in the exhibition. The driver pulled into their parkside hotel, and Brad jumped out the passenger side to hold the door for Heather. She slid across the seat, and spread her legs wide as she put her feet out, giving him a perfect view of her wet and swollen pussy. He was pretty sure the bellhop got a view too, but it was over too quick to get anyone to react.
It took only a few minutes to check in, and they headed to their suite, leaving their luggage to follow. Heather got a lot of stares in her strapless dress pulled down to expose most of her breasts and hiked up to show off her thighs. Her nipples, pussy, and ass were covered, but it was still much more sexy than folks were used to seeing mid-afternoon. She actually seemed oblivious to that, totally absorbed by the hotel and it's amenities. It was a very upscale place, and she seemed pretty happy to be staying here. Not that he imagined that it made up for the fact that he had blackmailed her to get her here, but he did want her to enjoy as much of this as she could. He shook his head at how fucked up this was, but none of that stopped him from groping her ass in the elevator.
As soon as they entered the suite he pinned her against the wall, kissed and groped her for a few seconds, then peeled her dress over her head. He guided her past the living room, into the separate bedroom, and then out onto the terrace. He'd never stayed here before, but he'd been pretty sure that the terraces would be reasonably private, and no one would be able to see them. That wasn't 100% true, someone with a good pair of binoculars from a taller building a block or more away might be able to see them, but at least no one else at the hotel would be spying on them. Of course Heather didn't know that, and she stopped with a small shriek when she realized he wanted her to go outside completely naked except for her high heels. He was persistent, pulling her arm firmly to get her onto the terrace. He guided her over to the railing so they could look out at Central Park.
"Nice view, eh?" He moved in behind her, reaching around to grope her breasts while he nuzzled her neck.
"Holy fuck Sir," she panted. "This is un-fucking-believable, but I'm really scared being out her naked."
"Oh you're going to be naked here a lot, so I'd just get used to it." he pulled her to grind her bare ass against his crotch. "The bellhop will be here in a second, but I want you to stay right where you are, just enjoying the view."
Brad moved one of her hands down to her pussy, and guided her finger to rub her clit. They looked out at the city while she masturbated as he pinched and pulled her nipples. It was so hot that it took all his will not to just pull down his pants and fuck her on the spot. The sound of the doorbell broke up their little dance, but he reminded her to stay right there and keep doing what she was doing. He went to the door and let the bellhop in. The young man followed Brad back to the bedroom, carrying the suitcases. Brad smiled as he saw Heather, clearly visible in profile through the sliding glass door, stark naked as she looked out at the park. He couldn't really see what her hand was doing from this side, but it was definitely in her crotch, and it was definitely moving. Brad saw her glance in a couple times, but she surprisingly didn't panic or cover up, she just kept following her instructions. The bellhop set down their bags, and was starting to explain the thermostat when he looked over Brad's shoulder and obviously saw Heather. He stopped talking, and his jaw dropped open. It was almost like a cartoon, and Brad couldn't stop from chuckling.
"I think we can manage all that," he said slipping the younger man a tip. "As you can see, I got something to take care of. Thanks so much for bringing the bags."
The bellhop managed to close his mouth and and nodded. Brad walked him to the door, and then made sure it was locked behind him. He was pretty sure the guy wouldn't cause any trouble. After all he'd just gotten a free peek at a naked woman, not really anything to complain about. Brad stopped at his suitcase, grabbed some supplies, and rejoined Heather outdoors. He stood behind her again, grinding into her naked ass. He slapped it a couple times too, enjoying the view of it rippling, and the faint handprint coming into view. He couldn't believe that he was really getting to act out these fantasies.
"I think it's time to see how your training on your other holes has gone," he unzipped his fly as he spoke.
He bent her over the railing and glided his hard cock back and forth along her slit. She was wet and wide open so it only took a couple thrusts to find her entrance and slide in. He took about two half strokes to spread her lube a little, and the thrust all the way home. Her pussy was a delight, warm and tight, and as he pumped Heather squealed, a noise he wasn't sure was in ecstasy or discomfort. In some ways, that turned him on even more, that he didn't really have to care. He was doing this for his own pleasure and that was all. He had developed the habit of always being a sensitive, gentle lover, not letting out his inner beast, the secret pervert inside, but here he could really cut loose. He used his left hand to grab Heather's hair, and his right to reach around her and grab her nipple. He used those two hand grips to fuck her furiously.
He realized he wouldn't last too much longer, in spite of cumming earlier in the day. He needed to make his move now. He pulled the tube of lubricant from his pocket, pushed her down firmly against the railing, and squirted a large gob of lube down the crack of her ass. He worked one finger, then two into her ass, reaching around with his other hand and pinching her clit to make sure she stayed on edge. She moaned and grunted as she thrust her ass back onto his probing fingers.
Once she was well lubed, he put a copious amount on his penis, and lined it up to her rectum. Again, he started slow, only putting about a quarter of his cock in her and rocking back and forth to make sure the lube was spread. He snaked his right hand over her shoulder, grabbing her right tit and pulling it up harshly as he thrust hard all the way into her ass. They both let out grunts as his cock slid in balls deep. He reached around to cup her cunt in his hand, sliding a finger into her slit. He pistoned in and out of her ass, fingerfucking her and banging his palm into her clit. He had to let go of her tit, and he moved her hand down so she would finger herself. He pushed her head down so her tits were pressed against the railing, and then grabbed her hair for leverage as he fucked her. He used his free hand to spank her ass several times as he pounded in and out of her ass. He was so turned on that all he could think about was using her, and cumming in her ass. It didn't take very long at all for him to go over the top, and he thrust himself deep inside her as the orgasm overtook him. He must have spasmed and pumped jism into her for over thirty seconds, and his legs began to tremble. Finally he plopped out of her ass and collapsed onto a patio chair.
"Oh my fucking God Sir," Heather panted as she kept rubbing her pussy. "Holy fuck..."
Brad saw the the trickle of cum leaking from Heather's red rectum, and a wave of remorse overtook him. How could have he done this to her? He was ashamed of how his lust had overcome him, but he didn't know what to do.
"Go jump in the shower and clean yourself up," he said wearily. "I'll be along in a second."
She looked at him with a blank expression, and went back inside. He waited a few minutes, trying to collect his thoughts. He knew how fucked up this was. He was finally getting what he had always fantasized about, and now he was succumbing to guilt rather than revelling in it. He knew this arrangement with Heather wouldn't last forever, so he reminded himself to buck up and enjoy this for all it was worth. Years from now he wouldn't want to think that he wimped out and turned soft, missing his chance to live out his fantasies.
He joined Heather in the shower, and instructed her to clean him off, first with soap and water, and then her mouth. But his heart wasn't really in it, and he only got semi-hard. He decided to tell her they should rest before their big night out. He made like he was tired from the trip and the fucking, and as soon as she dried him off he climbed in bed. She nestled in next to him as he closed his eyes. He didn't think he would sleep, he had too much on his mind, but that only lasted a few minutes. Before he knew it, he drifted off.
*
Heather stroked Brad's chest hairs, and watched him sleep. Part of her was seriously pissed at him. How could he fuck her like that, get her so close to cumming, and then just leave her hanging and unsatisfied? She idly rubbed her pussy, wanting to cum, but knowing that he wanted her to wait. Her asshole was buzzing, and her boobs were sore, but she was hornier than ever. The way he had taken her, just used her, the whole experience had been so hot. She had been terrified when he'd lifted her skirt and fingered her for the limo ride, almost as much as she had been while naked on the plane. And then letting the bellboy watch her while she masturbated had been so difficult, but so erotic too! She felt like every nerve ending was tingling from all the stimulation.
And then the way he had taken her. Like he was some beast possessed, taking her to serve only his need. It had been so raw, so animal, she had never been fucked like that. A real solid fucking, no pretense at being love making. It had been... wonderful. Not that she would want all sex to be like that, but she knew herself well enough to know she would frequently crave just being bent over and have her brains fucked out. But once he had cum, he seemed to have changed. She had really thought that he was going to let her cum, but he had been so quiet then. Had she done something to displease him?
