Ann often felt overwhelmed in her walk-in closet. Except for the cheeky panties caressing her bum, she was surrounded by racks of clothes she didn’t particularly care for. Her indecision was compounded by the fact that she was packing for a trip and had a plane to catch in a few hours.
Typically, she would just stuff a bunch of shit into an oversized suitcase. But for lots of reasons, this trip was more complicated.
She was going to be island hopping on a small prop plane — her company’s bonus for blowing through their sales targets — and she needed to pack light. At the same time, she needed a couple cocktail dresses and heels, a bathing suit or two, and boots or running shoes, depending on how she wanted to get her exercise in the moment.
Craig nosed around her bag and noticed that she had decided on her one-piece swimsuit. The suit was sexy as hell — it went low enough that sometimes he thought her breasts might fall out if a wave hit her just right. But it wasn’t the suit he would be fantasizing about her in while she was away. “You sure you don’t want your boy-shorts bikini?” he said.
“Please don’t start with me,” she said. “It’s one of the few things I’ve packed. Besides, you really wouldn’t want me wearing that thing.”
“Oh, I don’t know,” he said. “I like it when my wife attracts attention.”
She admired his confidence but thought he was full of shit.
“Don’t you get that I’m worried?” she said.
“About what?” he asked.
“It’s going to be a crazy weekend,” she said. “Usually I’m busy on these trips and come back to my room exhausted. But this is one long party. There’s going to be so much drinking.”
“Sounds fun,” said Craig.
“I’m not joking,” she said. “What if I — I don’t know — I do something bad?”
“Or what if we’re just open about what could happen and try to prepare for it?” he said.
She had fucked around with other men before, but mostly with Craig involved — usually watching from their couch. She didn’t like feeling deceitful, so his comment was kind of a breakthrough. She still looked discomfited but she had a glint in her eye.
“How would we do that?” she asked.
“I’ll help you pack,” he said. “If something happens, you’ll be ready. If not, you can have some fun by yourself.”
She didn’t object. Craig looked less daunted in perusing her racks of clothes. “Is there anyone you want to impress?” he said.
“Maybe,” she said.
“Do you know what ‘Maybe’ wants to see you wear?” he said.
She grabbed the shortest dress she ever wore to work, a conservative blend of gray and black that nevertheless stopped short of her knees, serving as an ode to her sexy lower thighs.
“How do you know he likes it?” he asked.
She snickered but wouldn’t say. He grabbed an even shorter and more colorful dress and tossed it into her suitcase. “Anything else?” he said.
The deliberate toss was an immediate turn-on. She put her hand on Craig’s chest and started to kiss him. All she wanted to do was fuck — she could go on the trip in a comfy bathrobe for all she cared — but Craig kept her on task.
They found another dress that she thought — “Who is this guy now?” — Marc would like on her. Then Ann changed her mind about the boy-shorts bikini. Craig squeezed her ass and pressed into her, nibbling at her ear.
“If you’re going to go through with this, I need to know how this is all going to unfold so you’re packed for it,” he said.
“I don’t know,” she said. “I’ll wear one of these dresses to the cocktail party. I’ll drink enough to dance with him and then we’ll bring champagne up to my room.” Craig backed away, looking unimpressed.
“Too easy?” she said.
“Maybe,” he said. “Also, a gentleman — and I hope this guy is a gentleman — would think that he might be taking advantage of you. He’s probably got more pride than that. He probably wants to fuck you when you’re sober. You should do it in the morning. Is he a fit guy?”
Her eyes got wide and she nodded her head. “His pecs look so tight. I just want to squeeze them,” she said.
“When he’s a little tipsy you can get him to agree to go for a run in the morning. Throw on some sexy running pants and set the pace. You could find a nice ocean view for your cooldown and do some provocative stretches in front of him.”
Craig started to pull out some options for running pants and settled on a bright pair of red capris.
“I can’t wear those,” she said.
“Why not?” he said.
“Well, they’re from Victoria’s Secret, for one thing. They’re skin tight and I just don’t love the way they fit.”
“You probably haven’t found the right underwear,” he said. “There’s no reason your ass shouldn’t look amazing in these.”
He went through her intimates drawer and pulled out a cotton thong that was little more than a string in the back. She tried it on and pried the Lycra over her ass, which stretched out every single stitch of the seams to make a perfect shape. Even she was impressed looking back at her bum in the mirror.
“So what happens after our run?” she asked.
“You lie,” he said.
It wasn’t the advice she was expecting.
“Preferably a small one,” he added.
“Like what?” she said, in a skeptical tone.
“I don’t know, ‘My shower’s broken’ or ‘I have no hot water, can I use yours?’ or something,” he said. “I trust you can figure it out from there — two adults behind a closed door.”
“Except for the bathroom door,” she said, putting her hands on Craig’s beard and sucking at his lower lip.
“Now, that’s the spirit,” he said.
She thought the plan might actually work and was starting to pity his confidence.
“Are you done yet, because I really want to fuck you?” she said.
“We haven’t even gotten to the toys,” he said. “I assume he’s going to need a little help if you’re going to have a really strong orgasm, right?” Craig had a hopeful look for the answer to be yes, which she thought was adorable.
“Probably,” she said.
“What do you think you’ll need?” he said.
“I don’t know,” she said.
“Well, how do you think you’ll come?” he said.
“It’s funny you say that,” she said. “I’ve had these very specific fantasies about him. I’m laying back with my legs spread in the air and he’s over me but not right on top me, so I can still get a good look at him. He has this long dick so he’s leaving me plenty of room to massage my clit with a vibrator and he’s still going in me pretty deep.”
“How do you know he has a long dick?” said Craig.
“Well, when I wear that dress I showed you, he gets a little chubby,” she said. She put her hands on Craig’s crotch and started to feel down him, a couple inches past his dick. “He goes right about here,” she said.
Craig rummaged around their sex cabinet until he found the longest dildo they owned. He paired it with a travel wand that made the most of two AA batteries. “Show me,” he said.
She pulled her pants and thong off and the dildo popped right inside her. She turned on the vibrator. It took a few strokes to get the jerking in sync with the vibrator, but once she had them in rhythm it seemed like she was already on her trip.
Craig continued to pack. “Do you need a mattress pad?” he asked.
“That would make me look like an old lady,” she said.
“Aren’t you going to come?” he said.
“Yeah, but probably all over him,” she said. “Don’t worry, I’m sure it’s a room with a double so it’s ok if things get a little messy.”
“How is he going to come?” he said.
“At that point, any way he wants,” said Ann.
“Anywhere?” he said.
“Maybe,” she said. “After our run, I’m guessing he’ll want to stick it where the sun don’t shine.”
“You’ll let him?” he asked.
“If he’ll fit,” she said.
Craig grabbed a couple bottles of lube and sealed them in a ziplock bag.
“Do you want any lingerie?” he said.
He had too much nervous excitement to notice that Ann was starting to breathe heavy and was losing a little patience for the exercise.
“For what?” she said.
“I don’t know, later that night,” he said.
Getting no response, he stuffed a full-body fishnet with a thong, some crotchless panties, and a few boy-short options into her bag.
“Which Outlander are you on?” he asked.
“An Echo in the Bone,” she said without any sense of irony.
He grabbed it from her nightstand and slid it into her suitcase with a half a dozen condoms concealed underneath.
Ann had the dildo by the balls and was fucking herself pretty hard as the vibrator was dialed up to full speed. “Oh my God,” she said. “Stop packing. Fucking touch me.”
He came up from behind her and pushed his crotch into her cheeks — his dick was leaking through his jeans — and squeezed her breasts until her nipples were pinched between his fingers. It was all she needed to put her over the edge. The dildo dropped with a thud and bounced off the floor a few times. Ann started to scream. He felt a wet warmth seeping into his pants and there were two or three successive splashes onto the floor as she continued her joyful wailing.
She collapsed in his arms and he held her up, knowing he couldn’t let her go and never wanting to. After a few moments, she glanced at a clock.
“I need to leave in five minutes,” she said. “And you still need to make your mark.”
She led him into the bedroom. He fucked her from behind and exploded, leaving his stain inside her. It was a little fuzzy after that. They collapsed on the bed and he remembered her waking him up, giving him a quick kiss and rolling her suitcase out the door.
He rolled around in bed reliving that moment. How long had she been gone? Only two days? It felt like two weeks.
When he had gone to bed last night, he’d seen that her company had posted some photos on Facebook. She was in a group photo with Marc, looking happy. He got a quick goodnight from her by text with nothing resembling an update, and he went to bed sad and horny.
She was four or five hours ahead so he wasn’t surprised by the buzz of his phone in the early light. He opened it up to a picture of her with her back end towards a mirror in those red running pants. She was a little sweaty and her free hand was wrapped around her breasts. The shower curtain in front of her was open and letting out steam.
“You’re a fucking good planner,” she said.
He found the whole setup confusing until he noticed the bathroom counter. He didn’t see any of the typical bathroom gear — a brush, face wash, eyeliner — at her fingertips. Instead, there was an orange and blue razor with too many blades to count, shaving cream, aftershave, and hand lotion.
“Marc’s room,” he thought.
Craig grabbed his dick, which already had the hardness of morning. He let his mind run wild with images of what might happen next. He didn’t bother to get up for a stack of tissues. He was content to make a mess. He wouldn’t have to worry about being interrupted by the kids. It would play through his head quickly. It would only be a minute or two.
Looking for more of Ann’s hotwife adventures? Try out “The Networked Wife” below on MyErotica.com.
