Annabel sat on the toilet; her thighs were so damp that the toilet protector sheet stuck to the back of them, and her backside. She plucked at it, undaintily, looking behind her in the mirror in the back of the stall. Her bare legs were almost stuck together by perspiration.
She had needed a few gin and tonics to get to this point; to move somewhat gracefully on the towering stilettos she wore. Currently she rocked her heels on the shoes. When she got up, she thought she was walking straight, but she wobbled a bit. Her underarms were damp from fear — and excitement.
She was too damn hot. When she brushed her hair back, damp strands clung to her temple. Her fingers pushed them back as she walked over to the bathroom sink.
She pulled her hair back. Sometimes, if she wanted to, she could pull her hair back so that the black was more prevalent. Because her hair was damp, the burst of silver hair in the front was more evident.
Stilettos were something she did not usually buy, but the lace decor made her susceptible.
Annabel was trying a lot of things that she did not normally try, lately — this night was something that would not have been in her repertoire a few months ago.
Now she was trying so many things that she never had before, but not because she thought anything was wrong with her life. At her age, she would hope she had more success than regrets, in her life at least! She just wanted to experience things she had not experienced before.
This night was something of a personal dare to herself, to see how far she would go. The plush bed in her hotel room was very inviting, but she had not been ready to go to bed. The new beta app, that she had been exclusively invited to use, had become shinier than ever.
Based on the idea that people who went on frequent business trips might want to arrange intimate encounters, this app promised anonymity. It set people up by industry, income, sexual interests and proximity. Since Annabel was in a certain income bracket, and was kinky, she really liked the anonymity aspect. When she had downloaded the app, it had not taken her long to be presented with several options. Including one man who was staying at her hotel. Annabel had a small fear that he would be part of the conference she was attending, so when they chatted, she asked.
He was not.
Their date was set.
Letting her body cool off, Annabel looked at herself in the mirror. She looked a bit more sultry than she had for the conference, and she looked and felt better. She was ready for all the night would bring her: there was no reason to be so nervous, she convinced herself.
So that she did not think with her pussy, she looked straight into her own dark eyes and let her hand slip down her skirt. She felt to see how damp she was, and was excited because she knew that she was going to have sex. Thinking about having sex excited her, almost more than actual foreplay sometimes. Annabel bit her lower lip, as she watched herself heave with excitement. Her orgasm face escaped her, because her eyes shut tight when she made herself come.
After she had pleasured herself, and her breathing had calmed, Annabel let herself out of the bathroom. The woman that was waiting to walk in smiled at her, as she held the door for her entry. The woman was about her age, with a ring on her finger that represented sensibilities that Annabel did not share with her.
Annabel saw her reflection as she walked past the lobby desk, and into the hotel bar that had what looked like a fish tank, but with an actual mermaid in it. She loved this hotel because it was a boutique one, and quirky. It was sexy in a way she had never explored before.
Until tonight.
“Are you Miss Annabel?”
Annabel stared at the maitre’d, who was not that much older than she was, and nodded.
“Your gentleman is waiting, he told me what you would be wearing. Please, follow Stella.”
He gestured for her to follow a very attractive young woman, who smiled at her with an effortless sensuality. Stella pulled out her chair, but Annabel paused.
Her gentleman was a great deal younger than she was. She had not been expecting that, and it was hard for her to refrain from expressing her surprise. He looked at her, as she recovered and sat down in the seat Stella had pulled out for her. His eyes lingered over her body, and rested at her blouse, which was unbuttoned a little lower than she usually wore it.
“Annabel,” he said, as if he liked the vibration of her name on his lips, and looked into her eyes. Annabel smiled; she knew that look. He rested his eyes on hers, because he presumably did not want to keep staring at her body. She smiled softly: she liked that, even with their age difference, he could not keep his eyes off of her body.
“James,” she said, coolly, her composure completely reinstated.
He grinned. She could tell he liked that she mirrored him.
“So, so far, I guess this app is going to get a really good rating from me…We are very similar…”
“How can you tell, already?”
“I just can,” he said. “What can I get you to drink?”
“Gin. Neat.”
He pushed his own glass forward on the table.
“Is this OK?” he questioned. “I ordered the same. Try it.”
“I want my own.”
“I meant, taste it. This is an aged one, it was recommended when I ordered.”
“Sure, sounds good.”
“I am only having the one, for what we have on tap for tonight… I don’t want to overdo it.”
Annabel was happy that she had pleasured herself earlier. James was very sexy, and his letting her know that he was watching his alcohol intake, for what they were planning to do, let her know that he was experienced.
Their industry cried out for a certain degree of maturity. Always on the road, giving talks in different cities, Annabel was a much in-demand speaker and she loved it, most of the time. But sometimes she did not know what city she was in when she woke up in the morning. Often, she woke up either alone, or with a man that she would rather have woken up without. Relationships were too hard to maintain.
James nodded, as she conveyed some of her thoughts to him as they conversed.
“It is very hard to find a partner or, after I do find someone, no one wants to deal with me traveling all the time,” he agreed.
Most of the time, it was just assumed that she was not relationship material. She had had a few relationships, never married. Never wanted to. James had never married, either, and neither of them had found partners who wanted to have the kind of sex that they wanted to have.
She barely touched her gin. James studied her, she saw in her periphery, before touching her hand.
“I don’t want to rush anything, and I don’t want to presume…But whatever you want, I want,” he stated.
Annabel wanted him to touch her the way that she had touched herself. It had gotten her excited to touch herself earlier, but also calmed her, because she was not as desperate for his touch. Her sex drive was so over-the-top these days, she played with herself whenever she could. But she could not do that at the table.
Or could she? They were kinksters!
Instead, she smiled at James. He squeezed her hand, and Annabel caressed his wrist.
“I want to take off these heels, in your room or mine. And relax. I never wear heels like this! I had to have two cocktails just to calm my nerves.”
“Why did you wear them?”
I wanted,” she began, “to do things tonight I have never done before.”
“Do you want to go upstairs? My room?”
Annabel stood up; she did not need to say anything to acquiesce to what they both wanted. She was not as inhibited with him as she might have been on a typical date. They had decided that they wanted to have sex; they had decided to indulge their kink if it suited them both.
“Take your shoes off, now,” James said to her, getting up behind her.
“Right here in the restaurant?”
“Yeah, why be uncomfortable?”
“But — ”
“You want to do things you never do. Take them off…”
Without looking at him, Annabel took off her shoes. James was taller than her and, with her heels off, she was dwarfed by him. Stella and the maitre’d smiled knowingly at them as they walked out. It was that palpable, what was between them. For her, James was sexy and smart and she really wanted sex. Did his emotions mirror hers to them, as he held her hand, and took her shoes?
He wrapped his arms about her in the elevator, and she still could not look at his face. She reached up behind her to caress his stubble, and felt him smile and rub his cheek against her palm. He’d told her how lonely it could get, being on the road all of the time, and she knew that feeling well.
“I might give this app a five-star rating, as well,” she said, as he caressed his cheek against her palm.
“We are so much alike,” he reiterated.
Except for their ages, she thought to herself, but she was not going to say that to James. She had had a younger partner before, and had harped on the age thing until he told her that he was not comfortable with her being so uncomfortable with their differences.
“Don’t I make you feel good?” he had asked her, and he had, but it had been her hang up.
Tonight was about pleasure, and not feeling so lonely.
Annabel followed James. She had to admit, the plush carpet in the hall did soothe her feet. He pressed his card to the strip on his door, and the dark silhouette of the city greeted them. Her room had the same, enviable view. James walked her toward the window, until her nipples caressed the cool glass through her blouse.
“Do you like to be watched?” he asked her softly.
“Depends on what I am doing,” she answered, sticking out her tongue and almost kissing the glass.
He touched her cheek; and turned her to face him. The bright city light shone on them like a spotlight.
“You’re so beautiful…” he said, and pressed her back to the window, the coolness of the glass now on her shoulder blades as opposed to her nipples.
They kissed, and the cars on the highway raced behind her like her heart. She was surprised that she felt this emotional, kissing him. Usually she was much more blasé about her one night stands. Maybe they had connected during dinner. She did know more about him than she knew about some of the men that she had been involved with. And she certainly knew more than to get emotional about kissing. This was definitely just an itch that both of them wanted to scratch.
When she heard him unbuckle his belt, her legs quivered.
That was what she wanted, that was why she was here. He slipped his belt from his waist, and the sound was like lightning. He caressed her ass with the buckle, before he spanked her with his hand and kneaded her cheek in a caress.
“You have a gorgeous ass,” he said, letting his fingers almost stroke her labia. “Just the kind I like to play with.”
Annabel knew her ass was a crowd pleaser. Every man she was with had commented on how much they liked it.
One man had wanted to marry it.
“Let me see what you have on under that blouse and skirt, I want to see what you wear close to your skin. Slowly, strip slowly.”
Annabel reached for her breasts; she could not help but caress the divide between them. James’ eyes lingered on her fingers as she stroked the soft curves. He licked his lips, and she smiled. Slowly, very slowly, she unbuttoned her blouse. She paused for dramatic effect when she was done, before she reached behind herself. Slowly, she unsnapped the clasp at the top of her skirt, which always got stuck, so it was an extra slow unfastening.
“Very nice,” James said, undoing his tie. “Take off just the blouse and skirt.”
She did not rush, but she was ready for another orgasm. The effects of the one she had given herself in the bathroom had worn off a long time ago. She let her blouse float off her arms, and pulled her skirt down over her hips.
“Stop. This is nice.” He kneaded her ass again, and she moaned. “We haven’t even started yet, do you want to moan?”
Annabel did not say anything.
“Turn around,” he said, and she did. James unhooked her bra, the two hooks that kept her large breasts in place. Loose, they bobbed heavily against her ribcage. “Put your hands on the window, don’t move them unless I tell you to.”
The glass was cool underneath her palms, even as delicate as her touch was on it. He slapped her backside with his hand, and then rubbed the buckle over the small of her back.
“Spread your legs,” he groaned.
When she did, he clutched the crotch of her thong and pulled it down from between her thighs. The window mostly overlooked the highway, so only people in their cars could see her with her breasts flopping and her bare thighs.
“Are you going to spank me?” she asked softly.
Emotionally, she felt much like her body did: exposed and unsure.
“Beg me to, beg me to beat your ass.”
“Please,” she pushed her hands against the window harder. “Please.”
“Please, what? Ask me for what you want, so I can give it to you.”
“Beat my ass please, please?”
“You’re such a sweet girl,” he said, playfully smacking her ass. “You are a good girl, you don’t deserve a beating.”
“Hurt me,” she croaked. “Hurt me.”
The first slap of the belt was on a soft part of her ass that made her clit trill. If her legs had been together, she knew she would be completely damp and sticky there.
“More?” he asked, as he caressed her lower back with his belt.
“Yes, harder.”
The streetlight blurred before her. She never moved her body as he spanked her, but her eyes overflowed with tears. She did not make a sound, either, nothing that would indicate to him that she had reached her limit.
She felt James rub her backside, before he kissed the nape of her neck.
“You’re beautiful,” he said. “And such a good girl. you did not even flinch. I was afraid I was not smacking you hard enough!”
“Fuck me.”
“You are topping from the bottom!” he laughed. “But I do want to fuck you.”
Licking her lips, Annabel spread her legs more. Her sense of hearing was keen, since she could not see him, but heard his rapid movement. She heard him open a condom package.
He caressed her backside, before he felt between her legs. She knew she was wet; he had gotten her so excited, more so with each stroke of his belt. He was wet when he pushed into her. The lube had surprised her, but she liked it. It was not hard for her to get wet, but she liked a little extra wetness. Menopause had heightened her libido, and she was having sex more often than she had in her younger days.
She needed sex more than she had before.
Her eyes glazed over again, and the highway became a blur, as he moved inside her. He felt so good inside her; all the moaning she had resisted while he spanked her rolled over now. Pleasure and pain escaped her mouth in even measure, as they moved against each other. James mimicked her sounds of pain, and she wondered if he had demons to expel, as well. They gave and surrendered so much as they coupled, Annabel was afraid her hands were going to go through the glass when she pounded it under the sensation of her orgasm.
James kissed her hands after he came, and took one to lead her to the bathroom. The bathroom was redolent with the scent of roses; James kissed her as she stood in front of the mirror. She did not want to look at their reflection, to see what they looked like, because it was a mirage.
His arm still around her waist, he turned on the warm water. She loved that they had fucked with him still wearing his clothes, but now he slowly took them off. Equally slowly, she pulled off her bra and thong. The suds of the bubble bath were overflowing, and she wondered how he had gotten so much of the luxurious, rose-infused bath gel from housekeeping. Lying with her head on his chest in the tub, she did not care. The warm water felt soothing, as he held her close to him and she curled her body against his. After the bath, she bent over on his command so that he could put lotion on her ass.
“You never flinched…” he said again, incredulously, kissing her bottom.
Annabel was drowsy after the bath and his attention to her bottom, and fell asleep easily beside him. When she woke up, she was still clinging to him, and he to her. She could not get out of his embrace, which both panicked and soothed her.
She had no choice, just as when he spanked her and had told her to strip. He had orchestrated everything, right down to her now being trapped in his embrace. She fell asleep again, and woke up when he moved, significantly, beside her. It was Saturday, and she did not have any commitments until the evening. Even then, it was just cocktails to end the week of work.
“Can I see you tonight?”
“I have a thing,” Annabel answered, savoring the feeling of his arm pressing her breasts in an embrace.
“I am leaving in the morning…”
“I don’t know what time the thing is going to be over…”
“Stay a while, then?”
Annabel did not answer, she just acted with him. She stayed longer, and they did not talk about leaving, or anything else. Getting up to go to the bathroom, Annabel saw her body in the mirror. The hotel room was filled with mirrors, and she could see every angle of herself, including the bruises on her ass. With her ass turned to the mirror, she turned just her neck. James had not done a lot of damage to her, but there was some bruising, and she was proud of it. Later tonight, she would sit among her colleagues during cocktails and remember he had done that to her.
When she came back out, James was on his phone. She was not sure what to say, so she just sat down on the bed beside him. She saw the word beta, out of the corner of her eye, and realized that he was using the app.
“I gave you five stars,” he turned the phone to her. “and I saved you. So, if we are ever in the same place again…It will let me know.”
“Do you want me to save you?” she asked.
“I am beyond saving…” he grinned.
Cocktails that night were as uneventful as she had expected they would be. She drank gin and tonics like she had not done the night before, because she kind of wanted to be somewhere else. If alcohol would take her there, whatever. She opened up the app on her phone, when she was alone for a period of time. She saw that James was no longer lit up as being near her. People that were matches for her were illuminated like stars on her grid. When he left to go to the airport, she had not wanted to be there so she had said that something came up. It would have been too much for her to be sentimental about their encounter. But now, seeing he was not lit up, she found that she was, a little.
Other men were lit up, for their proximity, but not as much for their compatibility to her. Unlike people who were really compatible to her, who lit up like stars, these men looked like distant lights that blinked intermittently on her phone.
The next morning, she saw James lit up, even though he was not close to her. She had discovered that she could make only people with all her criteria light up, and not see the others’ dimmer signals.
For months, she only ever saw James.
And he was never close to her.
Then, one day, he was. Her finger froze when she saw him. She did not want to be the first one to message. They were in the same hotel again, several cities away from the one where they met. But she did not message him. Deep inside, even though they had had a good time when they were together, Annabel realized it was only sex, and she was older than him.
He did not message her, and her secret feelings came more into focus.
After a grueling day at the conference, she practically dragged herself through the lobby. That was when she saw him.
James was sitting in an armchair, with a neat gin, or so she assumed, and he stood up when he saw her.
“Hi,” she said, as she walked, inevitably, toward him.
“You did not message me…” he started.
“You did not message me…”
“I saved you, I showed you…”
Annabel looked at him, bleary-eyed. James caressed her cheek.
“You look tired.” He pulled her hand, so that she would sit down beside him. “Take off your shoes.”
“I am not wearing heels today.’
“Take off your shoes.”
She took off her shoes. James picked up her feet, one by one, and rubbed them. She let her toes touch the buckle of his belt with each foot as he massaged them.
“What do you want?” he whispered.
Barefoot, she slipped her legs over his and looked into his eyes. Her fingers caressed his belt buckle as her toes had. He put his hand over hers, and they played with his belt buckle as if to open and close it.
Lying in her hotel room, this time, beside him, she reached for her phone. He held her loosely about the waist, and she noticed a notification from the app.
James is very close by. Message him?
Annabel smiled; she had more than messaged him. He had called her a very good girl, as she stayed perfectly still while he administered her spanking. Only her breasts moved, her eyes, and the wetness between her legs, with each lick of the belt.
Her ass ached, beautifully, when she put the phone down and rolled onto her back. James covered her.
This time, she left first. He wanted her to let him take her to the airport, but she did not want it to be sentimental. She wanted a clean break because she did not know if, or when, she would see him again.
They had both talked about how hard it was for them to have a relationship, when they first met. She was not even sure she wanted that, that she wanted anything more than what they had, when they had it. Even though she was pleased when he told her he had not been waiting for her accidentally in the lobby, that he wondered if maybe she had deleted the app, or not saved him, and he had wanted to catch her. She was glad he had sought her out, but now she wanted him to go, without any fuss.
He left her room, grudgingly.
Annabel got dressed, and packed. Her ass looked shapely in the skirt she wore, but no one knew the extra cosmetic aspects of it that lay underneath. She walked, and on each cheek lingered the sensation of what he had done to her.
She thought of him when she was on the plane, briefly, and every time she looked at the app. He seemed to be her only star, except for stars that were further away from him. She would continue to see him in every city, and sometimes she only wanted to see him in her city. Especially during a long conference, when she was lonely, when her skin was lonely.
The app had helped her find James, but no one else.
It was still in beta, and maybe the next upgrade would expand her horizons.
Bring her more luminaries.
