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Date Night (SHG - Kenny)
🕑 Added 2023-03-15 12:35:14 +0000 UTCKenny stood outside the restaurant. He wished he hadn’t looked at the menu. This place was crazy expensive. He was thankful that Amy had sent him to a suit shop. They had measured him and the suit had already been chosen by Amy. He asked how much it would cost but was told that they were instructed not to say. He was glad of it now as he stood there feeling not as out of place as he might have.
A car pulled up and he caught sight of Amy in the back seat. She seemed to be chatting with the driver. He hurried over to open the car door for her. It seemed the appropriate gesture. “I’m sure you’ll work it out if you talk about it, Emir.” Her bright, singsong voice could be heard as the door opened. “Thanks for the ride. Hi,” she said with a beaming smile as she turned her head to him. She swung her long legs out of the car. Kenny did his best not to try and peek up her very short skirt or look down the low neckline and instead focus on her beautiful and boldly made-up face.
High strappy heels with visible painted toes set down on the pavement. She extended her hand with matching polish for Kenny to help her out. She stood up so she was face to face with him. He just stood in awe of her for a moment and she smiled back at him. She stepped out of the way and Kenny closed the door. “Was he a friend of yours?” Kenny asked.
“Amir? No, he was just my Uber driver. He was just telling me about his marital problems.” She leaned forward and kissed him on the cheek. “You look dashing in that suit. Do you recognise my dress?”
Kenny stepped back a little and looked at her more thoroughly now that he had permission. “You wore that when…”
“When I did that little strip tease for you before I was more open about getting your attention. It’s one of my favourites but it’s a little too revealing for everyday wear.”
Kenny snapped his eyes back to hers. He was at great risk of embarrassing himself with an unwanted erection. He saw a look on her face that told him she knew exactly what he was thinking. Her knowing look gave way to a smile and she snaked her hand under his elbow. “Let’s get inside and eat,” she said. “I’m famished.”
“Are you sure this is okay? It’s really expensive here,” Kenny said quietly to her.
She stopped and turned to him. She straightened his tie and tidied his jacket lapel. “I know it’s expensive but I am playing out a little fantasy here. You are my toy boy tonight and I am a wealthy older woman pampering you so please don’t worry about anything tonight. Just relax and be yourself. The pomp and ceremony of coming somewhere like this is for my benefit.”
The concierge had a moment of indecision as he took in the couple in front of him. As old-fashioned as it was, it was typical to expect the man to take the lead, especially with a woman dressed quite so provocatively. In this case, he quickly realised that the woman, who he would have put down as a young gold digger, was in fact the confident one and was older than her companion. The concierge prided himself on picking these things up quickly and he felt quite smug as it transpired that the woman was indeed the one in charge. Not unusual to see glamorous women with their young lovers but the boy in this case was no handsome charmer. If anything he was fairly unremarkable even if he did fill his suit out quite nicely. The couple would soon become quite the talking point among the staff in the kitchen as they all tried to guess their story.
Seated, wine served and food ordered, Amy caught up with Kenny asking him what he had been up to this last month. “Working, like a lot,” said Kenny, enjoying if not appreciating the expensive wine. “It was just a construction job but it was for a wealthy client who wanted it done fast. I was told that the more use I was the more I’d get paid so I tried to be as useful as I could. I went from moving things around and tidying up to cutting timber and mixing plaster. By the end, I was getting the hang of quite a few things and the pay was great.”
“How was it working with all those builders?” Amy asked. She had expected him to have a hard time fitting in.
“Yeah, it was tough at first. They made fun of me quite a lot but my dad’s friend had told me that if I can just take it and not get upset then they’ll come around, especially if I work hard. It was true even if I was upset for the first few days, I didn’t let them see it though.”
“That’s great, I’m so proud of you,” said Amy, squeezing his hand.
“I even made a friend, Jason. We got chatting when I asked him about his workout routine. The guy had great muscles. I was dying to know if he had any advice for me.”
“And did he?”
“Oh yeah. He ended up dragging me to his gym with him. Three times a week after doing physical work all day and he went hard. I thought I was going to die but I feel like I made some great progress towards my goals.” Kenny was animated and enthusiastic. Amy found it totally charming coming from the quiet and reserved Kenny.
“What are your goals then?” she asked.
Kenny shrugged. “Just to not be such a string bean any more. I would love a body like Jason's but I don’t have his build. I guess I just want to get stronger and not be the stooped, nervous guy I was. You helped a lot with that, you know.”
“I did?”
“Come on, you know you did,” said Kenny with a smile.
Amy gave him a bright smile, her teeth shining white under her dark lipstick. “I hoped that I had. I can’t take responsibility for all of it though. You took what I started and ran with it.”
“Well, I’m grateful,” he told her, the sincerity of the moment making him shy.
Conversation flowed freely over the extremely fancy dinner until the last course. Amy pulled out her phone and said “I’ll book an Uber. Do you want to go anywhere else or should we go back to the hotel?” Those words were laden with meaning, evident in her sultry gaze.
“I’d like to go back to the hotel. Looking at you all night in that dress has got me keen to find a bed.”
Amy looked at Kenny with her mouth open in a look of shock and glee. “Kenny, I’m impressed.”
“Really, because I wasn’t sure about it when I said it.”
Amy burst into laughter. “So close. Just lose the self-doubt and we’ll make a lothario out of you yet.” She leaned over to him, her dress revealing a generous amount of chest. “I liked what you said and I was thinking the same thing.”
Everything was pleasant and civilised all the way back to the hotel. It didn’t escalate further than holding hands in the back of the ride. They walked arm in arm into the foyer of the hotel. Amy had already checked in and she led him to the elevator. As the door closed she turned to him and reclined against the wall. Kenny approached without being invited. The small show of confidence impressed her as he put his hands on her waist, the thin fabric only enhancing the feeling of her skin. He leaned in and kissed her. Their mouths opened and their tongues entwined. His hand slid down her body and pulled her thigh up. She hooked her foot around the back of his leg. His hands felt rougher than they had before on her thigh but she didn’t mind it, in fact, she liked it.
The elevator pinged and they separated. She gazed at him and used her thumb to clean some of her lipstick off him. They only just caught the door before it closed again. She pulled him by the hand to their room. As the door closed she already had her lips locked to his. Now, in the privacy of the room, Kenny was more assertive. He was soon pulling her skirt up over her head. Her breasts caught on the fabric so she helped him free herself from it and then delighted in the feeling of it running over her arms as he lifted it over her head and her skin reacted to being exposed to the air.
She was now naked apart from her heels and Kenny was still in his suit. She loved the feeling of being naked with a clothed man. There was something in the imbalance of it that excited her. Her nudity made her feel slightly vulnerable and it turned her on. They kissed like this for a moment. Kenny’s hand took the opportunity to cup her large, soft breast in his hand. They were familiar enough with each other now that there was no hesitation in him. He knew that his touch would be welcome and it was.
Amy tried to pull him down onto the bed but he resisted, clearly having other plans. She liked that he knew what he wanted and she allowed her hands to be gently pulled from his neck and he lowered her to the bed finally letting her drop the last little bit. She giggled as she dropped and her breasts bounced invitingly. Kenny was more interested in her toned legs as he lifted them up. He caressed her calves and feet before putting them down and pulling her knees apart. Amy could feel the cool air on her wet slit as Kenny exposed her. It quickly became apparent what he wanted as he kissed down her thigh before pulling her close to the edge of the bed. She realised that he had become stronger and she let herself enjoy being moved around with such little effort.
Kenny tenderly kissed her smooth pussy lips. He took his time. He had been thinking about this pussy since he had gone away and he wanted to welcome it back. He slowly ran his tongue over her slit, each lap working from base to tip and working a little deeper each time until he needed to use his fingers to part the lips to get access a little deeper and to wrap his lips around her clit. He made sure to remember the lessons she had taught him in the past and he judged by her soft moans and the way her body moved that he was getting it right.
Amy had assumed that she would get fucked. A needy young man like Kenny would surely want to fuck as soon as possible and yet here he was, head between her legs and doing a great job. She had been so turned on by their little adventure. Every look, approving or disapproving she got only fuelled her lust. Nobody in that restaurant had worn something as revealing as her dress and she knew that many of the patrons were judging her. It made it all the sweeter. That long-term tension was nay being stroked further by Kenny’s tongue and her orgasm was already close.
Her hips began to work, looking for firmer stimulation and Kenny must have remembered her former instruction as he took her nonverbal prompt and ran with it, clamping his mouth onto her clit and firmly working his tongue on it. As the pleasure intensified, she reached out and grabbed his head as her orgasm hit. She let go and fell back on the bed while Kenny ran his hand over her body. “Oh my god, that was so quick,” she said, laughing. She groaned and writhed a little. “That was so good. You remembered just what I like.”
“I’ve always been a quick learner,” he joked.
Amy shifted her position and jumped up onto her knees. She brought herself level with his face and kissed him, the taste of her own juices still on his lips. She began unfastening his trousers and said, “Do you want me to suck the first one out of you so you will last?”
“I think that would be good. You look so beautiful tonight, I don’t think I will last long.”
She smiled at his compliment and kissed him again as her hands pulled his cock out. Still kissing him she began to stroke it, the hot head brushing against the soft skin of her torso. She lowered herself down and took a moment to admire the large tool, watching it move as her hand worked up and down its length. She didn’t pause for long before she opened her mouth and put him inside. She was getting used to the extra effort she had to put into opening her jaw to fit him inside. She doubted she would ever be able to deepthroat him as she had with some of her smaller lovers in the past but at least she could control her gag reflex enough to not get overwhelmed by his size. She hummed softly as she moved her mouth around the increasingly familiar cock.
Kenny let out a groan of pleasure and satisfaction. Fatigue had kept him from jacking off as much and he was feeling seriously backed up. The sight and sensation of Amy sucking his cock was manna from heaven. She looked up at him and he made eye contact with her. A little part of his old self wanted to look away out of shyness but he made himself hold her gaze and he felt a strong connection with her as she luxuriously sucked his cock and looked so happy to be doing so. It was her eyes that turned him on the most at this moment. It was difficult for him to hold her gaze but that made it all the more rewarding. Of course, in that intimate situation he didn’t last long. He filled her mouth with ropes of cum and he enjoyed the slight look of surprise on her face and she began swallowing. He was not concerned about his quick orgasm. They had both expected it and he felt comfortable enough with her now that he did not fear her judging him for it.
Amy sat up, scooping a little escaped cum from the side of her mouth and licking it off her finger. “That was the biggest load yet,” she said with a grin. “Do me a favour and pass me a bottle of water from the fridge. He did as she asked and she swished the water around her mouth before swallowing. “I didn’t think you’d be into kissing me after that big load,” she said, draping her arms on his shoulders. “Unless you are into that in which case I’ll remember for the future.”
“No, I appreciate the consideration. Not into that so much.” He leaned forward and kissed her. Her lips were cold from the chilled water but quickly warmed up again against his.
Amy began steadily unfastening buttons until she could peel his shirt off him. Her dainty hands explored his shoulders and upper arms. He was a slightly built guy but he had definitely bulked up since she had last seen him. She liked to think that she wasn’t so shallow as to be seduced by a man's muscles but she took a guilty pleasure in feeling the hard bulges of muscle under his skin. She pulled back from him and said, “Take the rest off and join me on the bed.”
She moved to lay comfortably on the bed and put one arm over her head. She was posing for him and it made her feel very sexy as he admired her while removing his trousers. She could see his large cock had not gone down and a tingle of anticipation ran through her, not only for the feeling of being filled with it but also the anticipation of having no restraint on how long they could go. Her heart rate picked up at the idea and she wet her lips with her tongue.
Kenny climbed onto the bed. As he moved to join her he took the opportunity to run his hand over her from her feet and up her long legs. He slid his hand over her hip and the dip of her narrow waist. He slid it over the silken softness of her breast, over the bump of her stiff nipple and over her chest and onto her neck. She turned her head to meet his hand as it moved onto her face before taking it in hers and moving it to her lips to kiss it.
“You are in a romantic mood tonight,” she said, smiling at him, holding his hand on her cheek.
“It feels like you are really mine tonight,” he told her.
She found herself swept into his mood. “I am,” she replied and pulled him to her. “Take me, Kenny.” Kenny moved between her legs, positioned his cock and pushed forward. He felt her body tense as he entered her, a look of bliss on her face. “God, Kenny, yes. I needed this,” she told him as he fully entered her. Her hand reached up to grip the back of his head, her eyes, locking to his again. He had a serious and earnest expression. It made her feel like she was important to him. Her lips parted and she gave little noises of encouragement as she urged him to start moving.
Kenny began to move his hips. There was no rush and Amy could feel every centimetre of him sliding in and out. She fancied she could feel every bump and vein as he filled her so completely. Their eyes stayed locked, their faces close together as he penetrated her. “You can go faster if you want, I’m okay,” she said, wondering if he was perhaps being cautious.
Kenny shook his head. “I want to keep doing it like this if that’s okay?” he said.
“Uh-huh, it’s good. It’s really good.” She felt happier now she knew that he was setting the pace he wanted rather than worrying. It was intense. Not just from the point of view of the sensation but also the connection between them. She couldn’t remember the last time she’d had slow sex. While it lacked the strength of stimulation, the closeness and eroticism of it was more than compensating. “Your cock feels incredible,” she told him.
“God, you’re beautiful,” he said with genuine disbelief on his face. “Thank you for everything you’ve done for me.”
“You make it sound like this is the last time we will be together.”
“I hope not. In fact…” he trailed off looking a little shy.
“Go on,” she urged.
“I wanted to ask you if we could do it more often,” he confessed.
She was relieved it was something so simple. Since he had gone away, she had been thinking much the same thing. She was getting tired of considering Peter’s feelings when he clearly wanted her to be doing things behind his back. She had been holding back to not get carried away but she was fed up with being reserved. That was what this trip away was about. She had wanted to indulge in Kenny’s cock. In some ways, it felt like her first true act of infidelity. With Kenny at home, she could be sure that Peter was assuming they were up to something and vicariously giving his consent. This time she had lied and he had no reason to think that she would be here like this.
She thought that she should feel guilty but she didn’t. In fact, she was enjoying it more because of that. She realised that it made her a bad person but she never truly claimed to be a good one. She still loved Peter but he wanted this part of her to shine and this part of her had a weaker moral compass than the good wife she had been pretending to be. She was a slut. She always had been. Her life with Peter filled a need in her for comfort and stability but the side of her who pressured her best friend into bed just for fun regardless of the impact it had on her, the side that got drunk and took home two guys at once, the side that wanted Kenny and Beth and who knows who else, that was a part of her too. Maybe she would have lived a happy life suppressing it out of love for Peter but he had opened this door for her and she was no longer tentative about stepping through it. “I think that’s a great idea,” she told him and she could see how happy that made him and feel it in the way he pressed into her.
He continued his steady pace. It was achingly intimate as she pulled him close to cling onto him as she let the pleasure run through her. She could feel his breath on her neck as she slid her hands over his increasingly toned back and he in turn gripped her thigh. She lifted her legs up and wrapped them around him possessively. She was getting close to orgasm and could feel that Kenny was too. Even at this second orgasm, he hadn’t been going long but his large cock was making her cum quickly too. She pressed her body up against his and he gripped her flesh tightly as willed himself not to cum.
Whether it was his orgasm that made her cum or hers that finally pushed him over the edge was impossible to tell. They came together. Kenny lifted up his head and kissed her deeply. They both panted as he held his head against hers. She stroked his head, her orgasm making her feel emotional and affectionate. “That was so good,” she told him, softly kissing him again.
“Yeah, thanks for letting me go slow.”
She shook her head. “I didn’t expect it but I liked it a lot.”
“Can we really do it more often?”
She grinned at his childish disbelief. “Of course. How often do you want to do it?”
“Every day?” he suggested.
Her eyes went wide but she smiled at his words. “Every day, huh? That might not be doable for sex but I can probably make you cum most days if that will do.”
“Really? That would be amazing. I was half joking. Well, not joking as much as being over-optimistic. Thank you.”
Amy laughed. “You don’t need to thank me. I want to do that for you. At least as much as I can.” Kenny had an unusual look on his face. “What is it?” she asked him.
“I was wondering if we could keep going. I’m still hard and finding out we will do it more has got me worked up again.”
“Baby, you can fuck me for as long as you want tonight.”
Kenny grinned at her and she pulled him into a quick makeout before they started again.
