Lost Bet on Vacation

This is my first submission. I welcome feedback. I hope you enjoy!

*****

I had first gotten together with Rachel 10 years ago in college. I was a Biology nerd, fit from running cross country in high school. Rachel was a sci-fi geek with a bubbly personality, but somewhat conservative in dress. Rachel revealed that she had not enjoyed the attention her 32 DD breasts brought her in high school, and so she hid her hourglass frame with loose blouses and flowing skirts.

We had been each other's firsts for everything. We had explored kissing, hand jobs and oral sex for the 5 years before having intercourse for the first time on our wedding night. I think most couples would have been frustrated at waiting for intercourse, but Rachel was very skilled with handjobs. Similarly, she found the combination of my fingers inside of her and my tongue on her clit to be electrifying. But then again, once we added intercourse, it soon became Rachel's favorite, and we quickly discovered that she was one of the rare women who could orgasm from penetration alone.

I think we would have both rate our sex life as satisfying, however I think we both noted it lacked a certain spark. Sure, we had explored with toys and ever anal sex, but both of us at our core were a bit submissive. Looking back, I think both of us really desired for the other to just take control in the bedroom and give commands. Unfortunately, neither of us had the courage to admit that this is what we craved.

Things changed dramatically for us on our 5th anniversary trip to Italy. We were there in the in the middle of April, warm enough, but before the real tourist season began. After days of hiking and site seeing, we spent the morning shopping in a quiet town. We sat down at a café ordered lunch.

While waiting, we were discussing Dr Who. Rachel commented, "I still really like the 10th doctor the most."

I countered, "Matt Smith was way better as the 11th than Michael Tennet was."

Just then a voice chimed in from behind us, "No I bet you are just like my husband and think his companion is cuter."

Rachel and I turned to see a short blond girl in her late 20's speaking to us from the next table. I started to blush, but before I could stammer a response the woman grinned and said, "Hey, I'm Alice."

"I'm Michael and this is my wife Rachel. And you are wrong, I like his mannerisms more."

We debated the finer points of who the better doctor was until another man joined us. Alice introduced him as her husband Adam. As we ate lunch, we talked more and found out that Alice and Adam were from Ohio, but they had gone to college in Minnesota near where Rachel grew up We all had a love of sci-fi shows and board games.

After paying our bills, Alice and Adam invited us to their room to play board games to get out of the sun for a while. Being tired from the hiking the previous few days we agreed. We were soon playing Settlers of Catan and having a good time.

After a few games they decided to play scrabble. As they were setting up, I said to Rachel, "Remember that time that my sophomore year roommates tried to turn scrabble into a strip game and their girlfriends walked in on them?"

Rachel giggled, "Least sexy thing they saw, 2 guys, debating the use of proper nouns in their underwear!"

Adam interjected, "I don't know, it sounds fun... It would keep people more invested."

Alice added, "I think it sounds fun... let's try it, besides we aren't just a couple of guys."

I was surprised when Rachel agreed, and so I too went along with it.

Adam asked, "So how does it work?"

I replied, "I think they played every 20 points the winner won by the other person had to take off an article of clothing."

Alice asked, "How will it work with 4 of us? Maybe the first-place winner compares their score to the 4th place person, and the 2nd place person compares to the 3rd place person. That way there will be 2 winners and 2 losers."

Everyone ended up agreeing that this seemed reasonable, and we were quickly engrossed in the game.

I ended up winning the first game with 205 points, Alice with 186 points, Rachel in a close third with 180 points, and Adam with 160 points.

Alice teased her husband, "Looks like you lost to Michael by 45 points, start stripping off 2 items!" Adam nonchalantly kicked off his sandals and then slowly unbuttoned his shirt, and then mocking a stripper, twirled it around in the air before, throwing it over Alice's head.

Alice giggled a moment, her gaze lingering on her husband's six pack, before turning to Rachel and saying, "Now it is your turn."

Rachel protested, "But I only lost to you by 6 points, that's way less than 20, so I don't think..."

Before she could finish, Adam interrupted, "Yeah, but you came in 3rd, you should at least lose 1 item, besides it's only your sandals."

Rachel looked at me, hoping I would help her out. I'll admit to being a little excited to see things progress, and just shrugged, "It does seem fair".

Alice encouraged her, "Come on... it's only your sandals. They aren't even covering much of anything."

I saw Rachel hesitate a moment longer before acquiescing and kicking her sandals off under the table.

The second game was more technical with 2 and 3 letter words played strategically. You could see Rachel fiercely looking to score every point possible. I loved when she got competitive at home. Adam and Alice continued having a good time, joking throughout the game at bad hands.

The second game ended with Rachel winning with 190 points, Adam coming in second with 184 points, me with 143 points and Alice with only 122 points. I was surprised to see such a wide grin on Rachel's face as she turned to stare at Alice, "Well, do you want me to do the math for you?"

Alice blushed some, and I saw Adam wink at her. She hesitated a moment longer, then stood up.

"Stop smiling so much honey, nothing you haven't seen before once or twice." Alice kicked her shoes off, and then swaying her hips, slowly untied the knot holding her dress up. Alice made seductive looks at Adam, and even once winked at Rachel, then let her dress fall to the floor around her ankles. She gracefully stepped out it, and over to Adam.

Alice turned her back to Adam, while facing Rachel and me and said, "A little help please dear."

Adam obliged and unhooked her bra clasp. She allowed the bra to slip off of her arms and the cups fell away from her breasts. I gasped a little seeing her pointed firm nipples poking out, before trying to look up at her face pretending to be as gentlemanly as possible.

I was a little worried about how Rachel would respond to my looking at Alice's perky breasts, when Adam broke the tension by pointing out it was my turn. Alice sat down as I took off my shoes and slipped my shirt over my head, a little embarrassed to be sitting around the table without my shirt, but still more clothed than going to the beach.

Alice, sitting in only her blue silk panties and not wanting to be the only one near naked, suggested we play one last game. I agreed it was getting late but could manage one more (okay let's face it, I just wanted to spend more time staring at her breasts, and my wife might not notice so much if she was thinking about her next turn). Rachel agreed, seeming confident by still having most of her clothes.

Adam however pointed out, "Alice, you only have your underwear what if you lose by more than 40 points again?"

She bantered back, "I think you should be more worried that I'll kick your butt by way more."

Adam seemed to sense an opportunity for fun and replied, "How about if you lose, and you don't have the clothes to pay you have to do a dare for every 20 points you lose."

I felt a bit jealous, watching their obvious foreplay and I saw Rachel blush a little. Alice taunted him, "Fine, I would love a long massage tonight after I win."

We all agreed to keep playing. Rachel even seemed a bit giddy as well and I was hoping that this might serve as a bit of foreplay for us too. It seemed like her nipples were poking out from beneath her bra and shirt. It was a lopsided game, and while I did poorly, Rachel had a hand full of vowels and then eventually turned it over into a hand full of consonants. Meanwhile Adam taunted Alice playing words like vagina and turning (a horrible move on my part of) "gas" into "orgasm" to score a double word score as well. Alice finished the game playing "fluster" getting a triple word score and a bonus of 50 points for using all of her tiles.

Alice gloated with her clearly winning score of 274. Adam came in second with 192, I had 129, and Rachel had 110. At first Alice gloated, giggling, but as the math was quickly done in our heads, Alice's giggles turned into a devilish grin. Alice straightened her back, as she looked at my bare chest and down to pants. She shared her grin with Adam and they both looked at Rachel, who blushed and began to stammer as they undressed her with their eyes. The winning couple shared another meaningful look.

Alice asked Adam in a tone that was more of statement than a question, "Should we make them get undressed first and then figure out their dares?"

I was a bit stunned, realizing that I was going to have to get naked in front of another couple.

Rachel reluctantly stammered, "Hey, this was fun, but maybe we could just go to bed?" Then trying to distract them added, "You two can spend some time together then."

Alice replied, "Maybe later, but first I want to see you strip down. I won fair and square and besides I'm just in my underwear."

I glanced over at Alice, her nipples seemed to be getting harder. Adam tried to diffuse the situation a little by suggesting that Alice go easy on the dares. She agreed that if Rachel and I danced while stripping each other it could count as a dare for both of us.

Before we could speak, Adam got out his phone and started playing some music. Alice smirked encouraging us to stand up and start dancing. I awkwardly got up, offering a hand to Rachel, who had placed her arm over her chest even though she still had her dress and bra on. I wrapped my arms around her waist, and she draped her arms over my shoulders. She buried her face into my neck, trying to hide as we began to sway to the slow music.

After about 30 seconds of trying to get comfortable, Alice quipped, "Keep going."

I whispered to Rachel, "do you want to go first or me?" She looked nervously at me, pleading with her eyes to be allowed to keep her clothes on for a little longer. I placed a hand over hers and moved is to unbutton my shorts. Her fingers slowly pulled the zipper down inadvertently teasing my cock. My shorts fell to my feet and I kicked them aside, pressing myself up close to Rachel, hiding the obvious erection straining against my boxer-briefs.

"You turn next," I whispered to her as I reached one hand to gently tug at the zipper on the back of her dress. Despite my best attempt to be gentle and pull slowly, I swear a zipper has never sounded so loud before. I looked at her flushed face and kissed her to keep her mind off her embarrassment in being stripped in front of 2 new acquaintances. As our tongues entwined, I slipped the dress off of her arms allowing it to fall from her body. I heard Adam whistle as her purple bra and panties were revealed. I briefly opened my eyes to see Alice broadly grinning as she surveyed my wife's ass.

Rachel tried to hide herself, without anything to hide behind, and so pushed herself against me tighter, rubbing my cock against her panty clad pussy. I moaned softly into her mouth as my fingers worked to unhook her bra. I felt her nervously bite her lip, as she slipped it off as well.

We continued kissing, my hand reassuringly petting Rachel's back. When the next song came on, Alice prompted, "And now the rest of your clothes, unless you think you need our help?"

Rachel's hands seemed frozen around my neck, and so I moved my fingers top pull on the elastic of my boxers, allowing them to slide down to the floor. My erection sprang forward hitting Rachel's thigh. I looked to see Alice's reaction and she motioned to continue.

I kissed Rachel one more time and whispered, "I love you." Then I knelt down in front of her.

Rachel kept her eyes closed. I was shocked to see the large wet spot on her panties and her aroma seemed unusually strong to me as I hooked my fingers around the elastic of her panties and pulled them down. Her labia were glistening from her wetness. Adam clapped as her panties hit the floor and Alice snickered, "Her panties say that she's pretty excited, despite all the blushing." I saw Rachel bite her lip at Alice's comment.

I was unsure what to do next and then Adam chimed in, "Keep dancing." So I got up again, and wrapped my hands around my naked wife, and started to sway. She buried her face in my neck, trying to hide her embarrassment. My cock throbbed against her pussy, and I could feel her firm nipples against my chest. As we danced, my cock slowly slid against my wife. We started to kiss again and my hands began to wander over Rachel's back.

Just as we began to build a rhythm, Alice announced, "I think it's time for your next dare."

We broke apart, both blushing furiously, as we came back to the reality that we were being watched. We turned toward the other couple, awkwardly trying to cover ourselves with our hands. I eventually gave up and Rachel, kept an arm over her breasts.

"Please be nice," Rachel muttered, looking at the ground.

Alice grinned devilishly, "Let's go to the bedroom. I want Rachel to be on all fours and then I'll tell Michael how he can touch you." We headed to the bedroom, and Rachel obediently got into position in the middle of the bed. Alice and Adam settled on the bed off to one side, while I continued to stand there. Rachel closed her eyes as the couple slowly looked her over.

Adam pointed, "Look at how her breasts hang under her."

Alice added, "And her nipples look so big. Michael why don't you pull down on her nipples."

I reached under my wife and pinched each nipple between 2 fingers pulling down gently.

Alice giggled, "How does that feel?"

Rachel could only let out a moan.

Alice asked, "Do you want him to do it harder?" Now normally Rachel doesn't like that much nipple play, so I was surprised when she nodded. Alice cued me to continue, as I pulled down and pinched her nipples. Occasional gasps escaped my wife's lips.

Adam observed, "I can't believe her nipples are getting even larger." I have to admit, while it was a bit embarrassing to be taking instructions from someone else on pleasuring my wife, I was enjoying the opportunity to have some prolonged nipple play.

After a few more minutes, Rachel's moans began to increase and she began to add, "Please... more."

Alice beamed upon hearing these remarks and instructed me to pull down a bit harder. As I did she asked Rachel, "What more do you want?"

Rachel managed to pant, "Inside me, please. I NEED it!"

Alice responded, "Well maybe Michael can just touch on the outside for now. I'm enjoying your squirming." She laughed, adding, "Don't get to close to her clit, she looks like she might explode before too long."

Following her instructions, I moved to behind my wife, and reached out to touch her dripping pussy lips.

Adam added, "Just use one finger on the outside for now." I traced my finger down her labia, several times. Hearing her begin to pant again, I began also slightly parting her lips with my finger. She began to start to thrust her hips back, trying to get my finger in deeper. Alice quickly noticed and firmly instructed Rachel to stop moving. Rachel gave a disappointed whine but followed the command.

After several more minutes of teasing, I noticed Adam was now naked and slowly jerking his cock while watching. Alice, still wearing just her panties was slowly grinding her pussy against a pillow. Rachel's body was flushed and sweaty at this point.

Desperate to help my wife who needed relief, I begged, "Please, let me at least put a finger in side of her." Alice nodded in agreement. Rachel let out a deep moan as I slipped a finger inside of her. I slowly started to thrust in and out, amazed at her wetness which quickly started coating my finger and dripping onto my hand.

Her hips again started to push back into my hand, trying to get the finger deeper and maybe get friction on her clit so she could cum. Seeing this Adam, lightly grabbed her hair, making her look him in the eye, and then said, "Remember what we said about the hips!" Rachel again gave a disappointed whine but followed the instructions. He let go of her hair and continued to slowly jerk his cock while not even 2 feet from her face.

"Good," Adam continued, "Now Michael is going to slowly thrust into you 50 more times, and then I think you will have earned getting more inside of you." I did as I was told, slowly counting out loud, as Rachel's panting continued. Sometimes Alice and Adam made me stop or repeat strokes if they deemed them to be too fast, all the while teasing me about how desperate we both were for me to finally stick my cock into Rachel's pussy.

Rachel was reduced to begging, "Please... Please... Please," over and over again during the last 10 strokes. As we reached 50, I was excited to finally give her the relief that she was desperately craving. Having been corrected over a dozen times for fingering her too fast, I knew better than to just start fucking her.

I optimistically asked Alice and Adam, "Please may I put my cock in her?"

"You may," Alice replied, "But you can only bury yourself deep in her, no thrusting without permission." I quickly positioned myself behind Rachel and slid my hard cock into her pussy.

"Oh FUCK," Rachel moaned. I knew that tone well, she was about 5 thrusts away from orgasm. I held still hoping good behavior would be rewarded for both of us.

Alice grinned at Rachel, "How bad do you want it?"

Rachel could only pant in reply, words eluding her at the moment.

Alice continued, "You can thrust one more time, Michael."

I quickly withdrew almost completely, trying to make each millimeter of cock count, and thrust as deeply as I could back into her. As I stopped, I felt her pussy contract involuntarily around my cock. Rachel continued panting. I had never seen her so turned on and desperate to cum before. I was shocked to find that her excitement and just 2 thrusts had gotten me close to cumming. As I felt my balls start to tighten I took several deep breaths trying to maintain control.

Alice chided Rachel, "You didn't answer me yet. How badly do you want it?"

Rachel begged between panting, "Please, Alice, I need it so bad."

I saw Alice exchange a knowing look with Adam before she replied, "'Then why don't you give Adam's cock some attention. When he cums, you can too."

Rachel turned back to look at me, shocked, but with a pleading look in her eye. I couldn't leave her so desperate and I was feeling my own developing need to cum soon as well. I nodded to her. She turned back to find Adam's cock right in front of her face. She quickly enveloped her lips around it, starting with a shallow bobbing motion that became longer and longer.

I heard Adam groan a bit and I became optimistic that he was getting close. I think Rachel did too as she became more aggressive in sucking. I felt hips start to thrust back against me, creating a bit of friction, that I knew would be enough for is both to get off with in just a few more seconds. Adam noticed her hips however and quickly pulled her hair to get her to stop moving. I heard her let out a desperate moan as she did. Adam pulled her head up and looked her in the eyes.

"You can't move your hips." Adam chided, pulling on her nipples for emphasis.