A Weekend Escape Pt. 01: Thursday

Mark completed the booking. He knew that trying something new was probably better done in a short dose. The Thursday-Sunday trip felt perfect. Plus, with the somewhat early flight Thursday, they would be in St. Martin with plenty of time to get comfortable Thursday evening before two full days of play. Mark told Leigh to block the weekend on her calendar, and he'd taken off work as well. Flights should be a breeze, and their hotel, the Residence Adam & Eve, should be a blast. It was a smaller resort with a surprise for Leigh that Mark had intentionally left out.

While Mark's preferred fantasies included first time discoveries or finding out about pissing fetishes or simply fucking around in the woods, he knew Leigh's fantasies often included sensual or sexual behaviors with someone watching. They'd screwed around outside before, at the top of a beach house at night, on a few porches in the dark, and in a yard or two. He knew Leigh had once used a vibrator standing naked and staring out of a hotel. And they'd fucked a couple of times with hotel blinds up and lights on enough that someone walking by would be able to know what was happening. Oh. That hotel vibrator information. That reminded him.

Mark went to Amazon and looked up bullet vibrators. That wasn't it. He searched for panties vibrators. Ah yes, that's what he was looking for. Mark was going to gift Leigh a vibrator that she could wear when she was feeling daring. Leigh was usually conservative with how she dressed, shorts under dresses and as minimal of cleavage as she could manage with her DDD sized chest. Her bikinis were always securely covering, and she preferred high waisted bathing suit bottom pieces.

Leigh knew that their trip was going to be international and brief, but Mark intentionally withheld the destination from her. He wanted there to be as much surprise for her as possible. Given that it was a surprise she could reject on arrival (he knew how many alternate places to stay there were and exactly how to get to them), Mark felt quite safe in his plan.

He ordered the vibrator, it would arrive soon, with plenty of time to spare before their trip. Then, Mark remembered a second gift Leigh would love and ordered that kit as well.

A week before their trip, Mark finished wrapping both gifts he'd prepared for Leigh to have before their trip. One was to open tonight, and the other the night before they left. She was going to be home from work in the next few minutes, but he had a little bit of time to spare. When he heard the garage door opening, he logged off of his work computer and went into the living room with the gift. Leigh came in the house as the garage door was closing.

Leigh: "I'm home!"

Mark: "Good!"

Leigh: "Where are you?"

Mark: "I'm in the living room, I have a present for you. I think you're going to like it."

Leigh: "A present? I love presents!"

Leigh came into the living room and Mark handed her the gift. Leigh had been asking about this particular item before, and Mark had resisted. But he decided that this might be just the ticket to spice up their getaway weekend.

Leigh tore open the package and saw the create-your-own-dildo kit.

Leigh: "Is this to make a mold of your penis?!"

Mark: "Hell yeah, it is!"

Leigh: "Let's go do it! How does it work?"

Mark: "I think there's a few steps of prep involved, but I'm pretty sure as long as we can get me erect tonight we can get it done."

Leigh looked hungrily over at Mark, and he knew she'd help in any way she needed to. She loves getting off with her vibrators, and she also loves fucking his cock. He hoped that the mix of the two would be as fun as Leigh was dreaming it would be. Damn, she was going to want to name it though. There was no need for that.

The next few days flew by, with a couple of trials with the new toy. The mold had gone well and Leigh had gotten to approve of the new toy a couple of different times. During these sessions, Leigh had tried to pry their destination out of Mark, but he'd managed to maintain his surprise far longer than he'd expected. The night before they left, Mark decided it was time to let Leigh in on some of the plan.

Mark: "Hey babe, so I've packed the clothes that you'll need for the weekend. We're in just two carry-ons and our personal items for the flights. Also, you should know now that I plan to liberally use my normal language adjustment that I do in hotel rooms."

Leigh: "Are you planning on us having sex this weekend? Do you think I'd like you talking dirty or something?

Mark: "Multiple times, and I know you fucking like it. My bad, we're not gone yet. I have a small gift for you before we go that you can try tomorrow or not. I picked seats on the plane specifically so we could try this out."

Mark handed Leigh a small package. He watched as she unwrapped it.

Leigh: "Another vibrator? Do you think I like these or something?"

Mark could tell Leigh was intrigued and wanted to try it out.

Leigh: "Wait, you said on the plane, you want me to wear this tomorrow in the airport?"

Mark: "Well I figured you'd actually put it in your clothes after we go through security, just in case you get randomly picked to go through the full body scanner. It's supposed to be quiet enough to not be heard by other people."

Leigh: "Thank you, I'm not sure if I'll do that tomorrow, I'll let you know."

Mark had plans to attempt to help his cause. He had been stocking up on dirty stories that he thought Leigh would like, and had even downloaded a few to her phone without her knowing. While they usually had sex without aids, well aside from the vibrator assists, Mark had packed a few travel sized items to make having sex multiple times this coming weekend easier and more pleasurable. He'd even bought a few edible condoms, something they didn't really do since Leigh loved her IUD and had it nearly their entire sexual history.

They woke up the next morning and made it through security without issue, finding their gate easily with plenty of time to sit and people watch in the airport. Mark leaned in close to whisper to Leigh.

Mark: "Your new toy is in your backpack, I made sure it was easy for you to get to if you want to try it."

Leigh: "I don't think I'm in the mood for that, it's too early."

Mark: "Well if you want to get more in the mood, go find a note in your phone titled 'exhilarating stories', I know, very subtle and clever of me. There's also a couple of items in your downloads.

Leigh: "You're really want me horny for this trip don't you?"

Mark: "I think you'll have an excellent time, and pardon me for finding my wife hot and wanting her to experience physical pleasure both due to me and due to my efforts."

Leigh rolled her eyes. But Mark saw her open the file and click on one of the links. He knew she'd stop reading if he looked over her shoulder so he started playing a game on his phone to pass the time. A few minutes later, Leigh went to the bathroom and took her bag with her. A snapchat notification popped up on Mark's phone from her.

Leigh: [picture of the little vibrator]: I'm putting it in place and coming back out to sit. DO NOT TURN IT ON. I want to see if I can be comfortable at all sitting with it in.

Mark decided that didn't need a response, and soon saw Leigh walking back over to him, her face clearly, to him at least, evaluating whether the vibrator was going to cause her any discomfort. Again, Mark decided it was best to act disinterested or Leigh would give up on the experiment.

Leigh spoke after a few minutes: "It's not that uncomfortable, I'll let you know if there's a need for it."

Mark acknowledged this assent, but decided against joking about controlling it even without direct approval. Mark continued playing games and Leigh went back to her phone until they went to board. The first flight was less than an hour to a layover, Mark kept an eye on Leigh to see if she shifted uncomfortably at all. Leigh looked plenty comfortable, she'd laid her head on Mark since airplane mode had been engaged. She usually slept on flights, even trying on an up and down.

As they got off the plane, Mark decided it was time to let Leigh in on some of the plan.

Mark: "We have a little over an hour for our layover, we need to find the next flight to St. Martin."

Leigh: "St. Martin, have we been there before? Sounds fun. And sunny. And beachy."

Mark: "First time for me at least. So probably for both of us. It should be sunny, and beachy."

Mark was considering when to tell Leigh about the resort they were staying at, and was wondering more if she would use her new toy in her underwear when he realized that one may lead to the other.

Mark: "I downloaded some of the hotel info into a note on your phone. Look for one titled 'Water bottles'. [Leigh looked skeptical at him] What? I didn't think you'd open a note with that name. Am I that bad at being sneaky?"

Mark knew the words "clothing optional" "on all beaches going topless is optional" and "enjoy naturism" were in the description. This was really a moment of truth to see how Leigh would react to the potential for a fantasy becoming a reality.

Leigh: "Are we really staying at this place?"

Leigh squirmed a little in her chair and kept reading, Mark estimated she just got to the all beaches are topless part.

Mark: "Yeah, three nights. Surprise! Are you... feeling... positively... about this?"

Leigh looked a little bit wide-eyed into Mark's eyes, and pulled up the vibrator's app. She made a show to him about turning it on, and he saw in her eyes the moment that her pussy started being massaged.

Leigh: "You're going to join me in my choices, this weekend, right?"

Mark: "That's my plan. I brought a new bathing suit for me for the beach in case you wanted to participate and wanted me to be closer to your level of undress."

Leigh giggled and quietly asked: "Did you get yourself a speedo?"

Mark: "Yes, this place is very European and also I thought you might enjoy me wearing it. I know I'm usually a grower not a shower but hopefully I'll at least have somewhat of an obvious bulge while wearing it.

Leigh's hand squeezed Mark pretty tightly, alarming Mark but when he looked over at her, he realized it was because of the vibrator in her clothes.

Leigh: "If we had a blanket right now, I'd make this flight go even better for you."

Mark: "Trying to join the mile high club? I'm probably in."

Leigh: "Oh my God this thing feels good."

Mark: "Feel free to fuck yourself silly with that. Don't forget to read everything about where we're going though. I've got a list of possible activities lined up as a schedule. Also, I've not only packed every toy we have, but also added in some lubricant and edible condoms and shit like that in case we want to aid in our fun times."

Leigh: "How many times are you thinking we'll have fun this weekend?"

Mark: "I was aiming to be prepared. But hopefully a couple of times per day."

Their conversation was off and on for the remainder of the short flight. Their flight arrived in the early afternoon, which Mark felt was an ideal time to be able to arrive, check in, get the lay of the resort, get dinner, and then rest before the next day. He'd arranged for a taxi at the airport, and the trip across the island was scenic and calm. They arrived just after four in the afternoon to their resort.

As they checked in, the host, clothed, informed them that the entire resort was clothing-optional. Mark had communicated some with the host ahead of time, and had accepted suggestions for their trip but had decided against setting anything up because he wasn't sure how excited Leigh was going to be. Now, Mark was certain they'd spend plenty of time at their getaway and not just out and about escaping the nudity by going to the island.

After handing them their key, the host personally walked them towards their room. It took only a few steps before they spotted their first fellow guest walking around bare. Mark glanced over at Leigh and she seemed pointedly not looking at the man's cock and balls. He was partially shaven, allowing Leigh a thorough opportunity to fail to be surreptitious in her evaluation of his physique. Mark thought she'd rate him slightly above average, although the man was currently pale, he was also glistening - seemingly ready for full body tanning - and Mark suspected his shininess might boost his points for Leigh's rating. He simply smiled and gave a small wave at them and their host as the moved towards their room. The host opened the door and as he did, another guest walked out of the next door room. This time it was Mark's turn to try to be subtle as he looked this new guest up and down, her breasts bare and body also oiled for tanning, Mark suspected that maybe she and the first man they saw were together. Mark looked over at Leigh, who seemed split on seeing this other woman boldly walking around naked and checking on how much Mark was noticing. Mark decided one more glance the new woman's way as she walked towards the pool area was safe, and decided quickly that he wanted to see Leigh's ass walking around like that lady's.

Leigh: "Were you checking out that woman?"

Mark: "I'm pretty sure we both were, and both of them we've seen. Not every day that we see other people glistening and they're just walking around with their fuckin' cock and tits out and shit."

Leigh laughed a little: "yeah, that's true. Want to walk around the rest of the resort?"

Mark: "Yeah! Are you happy with this surprise?"

Leigh moved in towards Mark, and kissed him on the lips. She looked in his eyes intently.

Leigh: "Yes. And seeing the other guests made me even happier with it."

Leigh kissed him again, this time tugging a little at his pants. Mark was not sure whether this was just to get him properly dressed for the resort or if she had more physical pleasure in mind. She pushed his shorts down and felt one hand on his dick.

Leigh: "Is this for my kiss, or for who we just saw?"

Mark: "Babe my cock is all for you, any time you want to fucking have it."

Leigh: "Well that will have to be later because I have to pee and I do actually want to go tour."

Mark: "How are you going to be dressed? Personally I vote for either nude or at least topless."

Leigh: "You packed for me, what are my options?"

Mark: "I over-packed for you. You've got a couple dresses and sleeveless shirts and skirt combinations."

Leigh: "Pass me a skirt while I pee."

A few minutes later, Mark was very unconfidently nude but ready to walk around the resort and Leigh looked a little nervous as she wore just a skirt.

Mark: "I think you look really damn hot. I'd have to consider asking about swinging if I were another guy around the resort."

Mark was just trying to reduce tension, and he was pretty sure that's how Leigh took it as well. She finally nodded towards the door and they went out into the evening.

Across the next few hours, they learned that the naked bodies they'd taken turns appreciating earlier belonged to Harry and Sarah, who were on holiday from England and on their fourth trip to this resort. They seemed a little older than Mark and Leigh, but close enough in age that conversation was easy. Harry and Sarah were helpful, introducing them to an older Italian couple that the four of them couldn't communicate easily with. Their host called them Tony and Sofia. The two other couples staying hadn't yet arrived, per their host, so for conversation Harry and Sarah were their primary companions. Mark managed to arrange some dinner to be brought to them (and clothed himself before retrieving it), and they enjoyed their dinner poolside. Mark noticed that Leigh's attention to her leg position reduced across the evening, and so he managed to catch a couple glances of hair covering her pussy. Harry and Kara went back to their room right after the sun disappeared, still jet lagged (although Mark suspected that was at least partially fictitious based on some not subtle looks they had exchanged). Around 9, they agreed to go to their room and get ready for bed.

Mark: "So we can obviously hang out here tomorrow in whatever lack of clothes we want. There's also a few beaches in the area, at least one is fully clothing optional and some or most are topless. It's a European style island."

Leigh: "That sounds fun, I think though if I'm going to be topless you should have to join me in the adventure, so let's go to the nude beach."

Mark: "You just want to see my cock being out in public don't you?"

Leigh: "I mean, I'm not going to be mad about it, that's for sure."

Mark: "Well we have to come back here if it decides to perk up and that gets your pussy hot and bothered. No beach fucking allowed. I'm not about to get arrested out of country."

Leigh: "Because you get arrested at home all the time?"

They got ready for bed, Leigh changing into a chemise but still foregoing underwear to keep with the weekend theme. Mark decided that this was going extremely well as a surprise. Both of them were pretty tired from the early morning, travel, Leigh's plane orgasm, and high emotional intensity of being nearly or completely naked around bare strangers for the first time. Mark spooned Leigh as they got in bed, naked body sculpting around her's covered in her soft chemise.

Mark: "I love you, I'm so happy that you like this surprise."

Leigh: "I love you too, thank you for putting all of this together."

Mark: "One minor question though that I knew was an issue before we came here."

Leigh: "Which is?"

Mark: "What all do we tell our families about the trip?"