Not your average partner swap (TWAW + MysticalRose) NSFW

[ToWriteAndWander]

Sam, at 18, was playing with fire. He was on a family vacation with his parents and while that had proven to be a bit of a cock-block, he had made friends with a killer MILF. Caroline was a slim figured woman, with blonde hair and the sort of body that drove him crazy. Seeing her that first day in a bikini was not something he'd forget any time soon. She was clearly alone on her vacation, so he had approached her to make small talk - and help rub sunscreen on her back, where she couldn't reach.

There had been a bit of a connection immediately, even more so once he had gotten his hands on her. They had started talking and hanging out during the day. His parents would probably kill him if they knew he was shamelessly flirting with a woman not much younger than their own age, but they were rather preoccupied themselves. And tonight, well, to night was his best shot at getting some action if he played his cards right. His parents were going to a romantic dinner and then dancing and wouldn't get to their room until late. He had his own room, of course, next to theirs, so having anyone over was risky. But at least it gave him a window - unless he went back to her place instead.

He had found her by the pool again, socializing with other adults. He was in his bathing suit, showing his toned and muscled body off once more. He flirted with some of the girls his age, but his real desire lay with Caroline. Soon, he found himself in the large hot tub, water bubbling around them. Caroline was there, talking to other people, her back to him. Sam kept letting his back bump against hers, ass against her tight ass, all masked by the water. Letting her know he was there.

He was making small talk with the group he was with but reached his arm behind him. He slid it onto her hip, then down onto her ass, testing the waters. She didn't make a move to dissuade him so he let his hand wander lower, sliding it down even more, nestling it between her legs, starting to rub her slit through the material that covered it.

 

[MysticalRose]

Caroline had never imagined that her mini vacation away from her life would result in such a memory. After months of court to finalize her divorce, she decided to spend a little quality time with herself while her daughter enjoyed time with her best friend. The first day she spent entirely on the beach, getting in as much sun time as possible was her goal this week. After applying most of her sunscreen, she had been shocked when a younger man offered to help cover her back for her.

After spending the day talking and rather enjoying his company, she realized he was quite attractive for a younger man. Being in her late thirties, she was not bad looking for herself or so she thought at least. After parting ways around late afternoon, she found herself glancing around for him on occasion as she rejoined the others at the motel but never sought him out.

The sun had started to set once she grabbed her cocktail from the bar and slowly joined a group of people she had met earlier. Seeing Sam enter the hot tub with a few people closure to his age she gave him a small smile but returned to her conversation. Caroline could feel his backside against hers as she stood, taking it for the crowd she did not think twice about it until she felt his hand against her side. Glancing over her shoulder noticing he was deep in a conversation, she smiled as she returned to her topic she was discussing.

As she went to take a drink from her glass, his hand slid farther down and landed on it's apparent destination. Almost choking, she cleared her throat laughing about it sliding down the wrong tube. Pushing her body into his giving him the invitation to continue.The way his hands felt on her made her body crave more, wanting to feel the skin on skin contact instead of through clothing. Trying to keep her composure, she found herself sipping from glass a little more often. Letting her left hand drift under the water her fingers clutching onto the waist band on his shorts, her nails digging in slightly.

After allowing this to continue for a period of time, she had to step away from his reach before their act became noticed. Excusing herself, she left the hot tub and ventured towards the bar. Her eyes glancing over her shoulder in his direction, hoping he would follow her. Once she had his attention, she motioned towards the hotel while biting her lower lip. Taking her drink she headed for the doors, and towards the elevator.

 

[ToWriteAndWander]

Sam rubbed her slit properly through her bottoms. There was no pretending the touch was accidental now. And then he felt her own hand reaching out to touch him. He had to cover the smirk that crossed his face. He pressed his hand against her more firmly and then started to tug her covering to the side, to let his fingers touch her directly. That was when she pulled away from him. He glanced over his shoulder, thinking he had crossed the line as he felt her brush past him and make her way out of the hot tub.

The look she gave him had him scrambling after her. He quickly toweled off, excusing himself to go to the 'bathroom' and then followed her at a discreet distance. He caught up to her at the elevator, standing behind her as they waited from it to arrive. Once it did, he followed her in - waiting to make sure no one else got in and the doors had closed. Once they had, they were very much alone.

He pressed up against her from behind, hands exploring over her exposed skin as he pressed his groin to her ass. He kissed her shoulder tentatively. "Couldn't take it anymore?" He whispers into her ear, boldly letting his hands slide up to grope her perk breasts through her bikini top.

 

[MysticalRose]

Letting her hands grip onto the wall before her, his hands exploring her body. Caroling gasped feeling his groin pressing into her ass as he added pressure. A small moan escaping as his lips played across her shoulder, goose bumps appearing over her soft skin as his warm breath spoke into her ear.

"I would rather not keep my pleasure quiet." She replied, her back arching into his chest as his hands could be felt traveling upwards. The way her breasts fit into his hands perfectly made her body tremble. "Besides, this way I can do this." She remarked as her left hand left the wall and snaked between their bodies, grasping onto his manhood that was already standing at attention. Slowly grasping it through his swim trunks, her thumb rubbing across the tip of it.

"Pleasure is a two way street. I don't get unless I give." She whispered, hearing the elevator ding and quickly stepping away from him. Making her way into the hall and into the door to her room. Holding it long enough for him to step through before turning and backing into the room.

"Now where were we?"

 

[ToWriteAndWander]

He liked a bold girl. A bold woman was even better, so blatantly grabbing his cock in his shorts as he felt her up. "I like the way you think." He murmurs, stepping away from her as the elevator dinged. Luckily, no one was on the other side and he quickly followed her down the hallway to her room.

She held the door open for him so he stepped inside, already moving towards her before it had fully closed. He could only imagine what anyone would think, seeing the older woman and the teen boy coming together as they were.

"Somewhere along here..." He murmurs, pressing her back against the wall - chest to chest, his hands back on her breasts as he leaned in to kiss her on the lips. His sizeable erection poked into her stomach and his hands squeezed her breasts even harder than before.

He nipped her lips with his a few times before pressing his tongue into her mouth. He had never hooked up with an older woman before but she was something else. She had the sort of body girls his had, but was more mature and sure of herself than any of them.

 

[MysticalRose]

Caroline gasped as he pressed her against the wall, his words made he bite her lower lip. "This feels about right." She replied to his comment as his hands found their spot on her chest. Resting her arms, crossed over her head she moaned as he nipped her lips.

Without hesitation she allowed his tongue to enter her mouth, hers playing car and mouse with his. Arching her hips, she moved against the erection that was pushing against her naval. Letting her hand fall, her fingers raked through his hair pulling just enough to break the kiss. "Why not put that tongue of yours to good use." She remarked before nipping his lower lip.

For a boy quite younger than she, her body reacted to his every touch. Caroline was craving more by each second that passed. If this would only be for the night, she would take it and run with it. Knowing that once she returned home she could never really speak of this. Dragging one of her feet up, flat against the wall giving her self a better feel of his erection against her. She arched her hips farther into his as her knee rested against his hip. "Finish what you started." She whispered against his lips as her took over the kiss, slightly more aggressively that his.

 

[ToWriteAndWander]

Sam slid his hands down to her firm, perk ass, groping and squeezing it as she lifted a leg. He wrapped an arm around her waist and lifted - sliding his other hand down her leg to lift it up around his waist. He mashed his lips against hers once more, slow walking towards the bed while he carried her, showing off his strength. It helped she was a petite woman.

He climbed up onto her bed with his knees then gently laid her down - pressing his body on top of hers. He ground his erection directly against her pussy for a few moments then slid downwards. He trailed his kisses over her collarbone and pushed her bikini top upwards, exposing her perk breasts. He gorged on them, kissing and sucking her breasts, lashing his tongue over her nipples, sucking on those hardened little nubs. Then he continued.

He kissed his way down her flat, firm stomach until he was between her legs. He undid the straps of her bottoms and tugged them out of the way, exposing her completely. His eager mouth found its way to her beaver, kissing her nether lips. He moaned against her, tongue lashing up and down along her slit before he slid a finger into her tight opening.