Sexy Competition for Married Couple

She quietly said that I was probably right, even though I knew every guy would be checking her out even more than usual. I felt a little guilty and even offered to withdraw the challenge because I really did not want her feeling uncomfortable on our favorite date night of the year. Linda said that it was a challenge and she was going to accept it, but asked that I at least get her a drink as soon as we arrive so she would feel a little less self-conscious.

We kissed and headed down to the party. As they usually did, they had a check-in table that was followed by a photographer. Linda really did look amazing in that dress especially in her perky state. We walked in and as promised went straight to the bar to get a couple of drinks. As I expected, guys were definitely checking her out a bit more than normal when it was not obvious to their wives. It seemed that we were being asked to be in a few more small-group selfies with other couples than in previous years as well. I was on cloud nine as I danced with the sexiest woman at the party knowing that every guy at that party wanted to be me and would probably be thinking about my sexy wife when they were fucking their wives after the party had ended. We had a great time at the party and as it counted down to the new year we had a passionate kiss to bring in the new year. As was the norm, a few of the guys would take advantage of the situation and would go around to some of the best-looking women and give them a New Year's kiss. Linda was usually tracked down by about a half-dozen guys and this year was no exception. I watched as the normal set of very intoxicated guys came to Linda and brought in the new year with a kiss on her luscious lips. The kisses were always quick, but I did notice that one of our friends appeared to give a quick grope of her breast as he moved in for his kiss. It was so quick and she did not react, so I figured it was not a big deal. Needless to say, when we got up to our room we had a lengthy love making session as we role played what could have happened if she had accepted a dance from another guy and it went too far.

So, those were some of the more memorable challenges that we had given to each other during the first 6+ months of our competition and it led to me being in the lead 16 to 11, only 7 points away from winning. After the new year, time flew by quickly and neither of us had issued any new challenges for the first few months of the year. We were anxiously awaiting our getaway to Punta Cana in March and I'm sure each of us were thinking about the types of challenges we could do there and what challenges we might be faced with as well. When the time finally arrived, we flew to Punta Cana on a Tuesday and were taken to our all-inclusive resort. It was a beautiful resort with a gorgeous beach, 4 swimming pools and several restaurants to choose from. One of the other highlights was that they had R-rated evening entertainment and pool games, which happened to take place by their Party Pool which also allowed topless sunbathing.

The check-in was fast and they walked us to our bungalow. It was on the second floor with a balcony that had a beautiful ocean view. We quickly unpacked, put our swimsuits and cover-ups on, packed a beach bag and headed to one of the restaurants for lunch. After lunch, Linda wanted to go to the beach. I was hoping to go to the Party Pool for games and topless watching, but agreed relaxing on the beach would be nice. We found a couple of chairs, applied some sunscreen and started to relax.

Just as I was about to fall asleep, Linda said that she had a double challenge for me. She smiled as she handed me a speedo swimsuit from her beach bag and informed me that the first part of the challenge was that I needed to wear that for the next few hours while we were laying out in the sun. I've never worn a speedo in public before, but figured no big deal and went to the nearest bathroom to change in it. While I was changing, I was thinking of how I would fuck Linda later that night, which was giving me a nice bulge for the front of the banana hammock as I like to call speedos. I returned to our chairs and Linda had me turn around and then applied some sunscreen to my newly exposed upper thighs. My bulge was getting harder and it was becoming even more noticeable.

At that point, she said that for my second challenge that I needed to go offer and be allowed to apply sunscreen to a woman lying about 15 feet from us, who was probably 60 years old and at least 300 pounds. Not wanting to just give Linda two points, I grabbed a bottle of sunscreen and walked over to her. I politely told her that it looked as if she was getting a bit red in a few areas and offered to apply sunscreen so she would not get burned. She looked at my face and then at my speedo covered hard-on before calling me a pervert and asking me to leave her alone. Totally embarrassed and knowing that multiple couples saw what happened, I meagerly walked back to my chair.

Linda thought it was hilarious as she informed me that she had just gotten two points. She then admitted that she had talked to the woman while I was changing into my speedo and told her what to say. Her initial intent was to have me do all kinds of poses in the speedo while she took pictures on the crowded beach, but then saw the woman and this idea popped into her head. I told her that I thought that was cheating, even though I knew that I would probably have refused to do the posing on the beach as I was sure she would have made that even more embarrassing. She said there was no rule about setting something up, but that since she was getting a little jealous of the ladies checking out the bulge in my speedo, she would allow me to change back into my regular swim trunks. So, the score was now 17-13 since I received one point for putting on the speedo and she received 2 points for me failing in my attempt to apply tanning lotion. My mind was racing with how I could challenge her.

While at dinner, we reviewed the entertainment and activities for the evening. One of the items that caught our eyes was a couple's game called 'The Not So Newlywed Game' and it said that there would be prizes awarded. It sounded like fun, so we decided to go to it. The game took place in a ballroom that had a stage in front. The host of the show was the head of the entertainment team and was named Enrico. Linda looked stunning in a short dress that showed off her amazing cleavage and perfect figure. When Enrico asked for volunteers, Linda's and several other guests hands shot up. He walked slowly around the front of the room and picked four couples, one of them being us. We were asked to go to a table and provide our information while Enrico highlighted the other entertainment going on this evening and some of the activities for the following day. While we were waiting for the show to start, Linda said she had a challenge for me and by the look on her face, I knew it would not be good. She told me that if one of the questions was how long is my cock, I had to answer that it is almost an inch when soft, but a full 2 inches when fully erect. Just for the record, it's actually about 6 inches when hard.

Enrico then introduced each of the couples and said that as a thank you, each couple would be receiving a voucher for $25 off at their gift shop and that the winning couple would also get a free couple's massage. My hope was that they would not ask the cock size question as I looked across the audience of probably 50 couples that we'd be spending the next week or so here at the resort together. Enrico had picked a diverse group of couples from an age and race perspective, but there was one common element. Each of the women were very attractive. During the introductions, he seemed particularly fond of Linda as he put his arm around her while introducing us as the last couple and then keeping it there while he explained the rules of the game. The first round of questions was pretty tame as he asked each of the husbands three questions, with the most risqué being the name of the guy that broke her virginity, which was of course me with Linda. After round one, we were tied with another couple for the lead having gotten each of the three answers correctly.

When they escorted us husbands to a small room to begin round 2, each of us got to know each other a bit. The husband from the couple that was in the lead with us was named Steve and he and his wife had seen my failed attempt to put sunscreen on the women at the beach. When I started explaining my side of the story, he said that he and his wife Sara had also witnessed Linda setting it up with the lady, so they just had a great laugh at my expense.

After about 25 minutes, they called us back into the room to join the wives. Enrico explained that this round was going to consist of 2 questions valued at 10 points and then the bonus question worth 25 points. He came to me with the first question of the second round and asked if Linda agreed to let me have a free pass to do anything I wanted with one celebrity who would it be. I thought a few seconds before saying that I would not want the free pass, but if I had to provide a name that I figured Linda would say Jennifer Aniston. Enrico congratulated me on the correct answer and then asked Linda to stand. He then commented to the audience that Jennifer Aniston is not near as hot as Linda is. She blushed a bit and sat down. The other three husbands each answered the same question with 2 of the 3, including Steve, getting it correct, but Enrico did not ask any of their wives to stand to pay them a similar compliment.

Enrico went to husband #1 to ask him the second question of this round. It was if any of the audience members wanted to see their wife's boobs on this trip, how likely was it going to happen. The possible answers were; they have already been on display at the Party Pool, they have not yet been on display at the Party Pool but will, or she is planning to keep her puppies covered. Since Linda has frequently gone topless when allowed, even if I had to beg sometimes, I knew she would answer that they had not yet been on display but will. After I answered that and Enrico confirmed it was correct, he commented that people better plan to get to the Party Pool early the next few days to get a chair, as he suspects it will be quite crowded waiting for the unveiling of Sara and Linda, who had each answered the question the same way. It at least seemed somewhat more comfortable since he did not single Linda out again.

Enrico went through the scores, with Steve and Sara, and Linda and I tied for the lead with 35 points, but reminded everyone that the final question worth 25 points could change it all. That's when the worst thing that could happen did. Enrico said the final question that he asked the ladies was how long is their husband's erect cock and that their answer must be within one inch of our answer. I sat there with a blank stare on my face as he asked the first two guys the question. One of them successfully answered moving them temporarily into first place with 40 points. When Enrico asked Steve, he said he was 10 inches but Sara had said 7 inches, so it was down to me. If I matched Linda's answer we would win the couple's massage. The question was what was Linda's answer. When Enrico came to me for my answer, there was no way I was going to give them the 2-inch answer Linda challenged me with, especially when all of the answers before me were at least 5 inches. So, I looked at Enrico and answered six inches, which resulted in Linda giving me a big hug and kiss as Enrico announced that we were the winners. She also whispered in my ear that the score was now 17-15 since she got those 2 points. After the game show ended Enrico gave us our $25 off certificate for the gift shop and the free Couples Massage voucher. Linda asked what other activities were going on and he suggested we go to one of the lounges that has a piano player and they do music trivia. That sounded the most relaxing of the options he mentioned, so we decided to do that. To our surprise, Enrico said he was done for the evening and asked if he could join us for one drink. We said sure and made our way to the lounge.

Enrico was very friendly answering questions that we had about the activities that would be occurring at the resort as well as excursions that we might want to consider. After his drink, he commented to us that he hoped to see us at the Party Pool the next day as there were a lot of fun games scheduled. We were both tired so we decided to head back to the room shortly after he had left. On the way to our bungalow we passed the gift shop and decided to see what we could use our $25 on. Linda had a craving for some chocolate, as I did as well, but I saw a thong swimsuit bottom that I figured would work perfectly in a challenge. So, I had the clerk ring it up while Linda was not looking and had her charge it to the room.

We slept in a bit on Wednesday as we planned to stay at the resort all day. When I was reading the scheduled activities to Linda to decide where she wanted to lay out, she told me it was my choice since she picked the beach the previous day. I told her I thought we should check out the Party Pool since it had several activities scheduled for the day. She laughed and said that she guesses that meant it did not matter which bikini top she put on since it would probably be coming off anyway.

After we had a late breakfast, we stopped at the spa on the way to the Party Pool and booked our couples massage for later in the week. We found a few chairs and got ourselves set up for the day at the Party Pool. As soon as Linda settled into her chair, she made the day for me and every other guy there by taking off her top. After we applied sunscreen and worked on a crossword puzzle together, we decided to cool off in the pool. I grabbed a foam float and let Linda lay on it while I held the raft by her head. The view I had looking down her body was incredible. Her perfect breasts, down her tight abs to her long sexy legs was giving me a hard-on as I slowly pushed the raft around. Linda closed her eyes, so I made sure to push the raft as close as possible to guys checking her out from the pool-side as well as in the water. While doing so I noticed Enrico had arrived and gave me a thumbs-up as he stared down at my sexy wife. When Linda was ready to return to the chairs, I had to adjust my shorts as my cock was rock hard. Over the next few hours we participated in a few of the question & answer type games that you had to write your answers on a sheet of paper and turn them in to the Entertainment Staff for scoring. Overall, the games were pretty tame, which was probably a good thing so Linda would not be hesitant to return to the Party Pool later in the week when I heard things were a bit wilder. We listened to the music, relaxed and just enjoyed the sun.

Whether Linda was laying on her back or front, she was definitely getting a lot of looks. Several guys seemed to be taking the long way to the bar and restrooms just to be able to walk past our chairs. For much of the time I put a ball cap on and sunglasses and pretended to be napping so I could watch the guys checking out my sexy wife as she was usually either sleeping or reading her book. During one of the breaks from the activities, Enrico walked over to our chairs while Linda had gone to the restroom. He commented how beautiful she was and that many of the other guests seemed to be enjoying her being topless. He also joked that he would be glad apply sunscreen to her if I needed any assistance.

As soon as he said it, I knew what my next challenge was going to be. I told him to stay fairly close because I may take him up on that offer. He had a surprised look on his face and said if I was serious he would be over at the bar for a bit. When Linda returned, she played right into my plan by asking me if she was getting red at all. I looked her over and said no but that she should still put some more sunscreen on. As she was grabbing the lotion from the beach bag I informed her that I was challenging her to let someone of my choosing apply the sunscreen to her entire body. As she sat silently for a moment I reminded her that I was currently leading by a point, so if she refuses, I will be up by 3 points, but that if she accepts and completes the challenge we would be tied.

You could tell she was a bit upset when she said fine let's do it. I told her to lay on her stomach while I go find a volunteer.

When I walked up to Enrico and handed him the sunscreen bottle, he had a big smile on his face as we walked toward the chair. The smile got even bigger when I told him that she would need to apply it to her back and front. When we got to the chair he said hello, which surprised her but I sensed that she was happy that it was one of the staff instead of another guest. Enrico squirted some lotion into his hand and I watched as he started spreading the lotion gently on her back. After he had a thin layer covering her back, he begun to rub it in more deeply. He started on her shoulders before rubbing the lotion into her arms and back commenting how smooth her skin was. Once her back was completed Enrico poured more lotion into his hand and moved down to her legs. Again, he gently spread the lotion across the backs of each of her legs. He then started with her right foot and slowly worked his way up to just below her bikini bottom being sure to rub every square inch of her exposed skin. Linda had spread her legs a bit allowing him to rub the lotion into her inner thigh as well. He repeated the process on her left leg and I could tell that her breathing was getting heavier. If I had really thought this through, I would have tried to get her to wear the thong bikini bottom, but even with her scrunched high cut bottom, my cock was rock hard watching him expertly apply lotion to my wife's gorgeous body.

As he finished her left leg, he calmly informed her that he was ready to do the front side. Linda slowly rolled over and again spread her legs slightly. He poured the lotion into his hand and spread it lightly across the fronts of her legs. Enrico again started with her right foot and slowly moved up her leg rubbing the lotion deeply into her skin. He repeated the process for left leg. Enrico moved so he was directly over Linda's stomach. Just as he was about to pour lotion into his hand to work on her belly and amazing breasts, Linda shook her head and said that she would do the rest herself and thanked him for his assistance. Enrico commented that it was his pleasure, winked at me and left to join the other Entertainment Staff members in the game that was about to begin.

Once he had left, Linda looked at me and said that we need to go back to the room now. I was shocked at her comment and quickly put our belongings into the beach bag. Linda did not bother putting her bikini top back on, instead just draping a towel over her shoulders and covering her breasts. She was practically speed walking back to our room as I had trouble keeping my flip flops on trying to keep up with her. As soon as we got in the room, she closed the door and gave me a very passionate kiss. When she broke off the kiss, she looked at me and said that she needed to be fucked right now and wanted me to pretend I was Enrico and finish applying the lotion. I went from being aroused watching Enrico rub in the lotion, to being worried by her abrupt end to the lotion applying and the need to leave immediately, to now feeling like my cock was going to explode.

Linda laid on the bed as if she was laying on the beach chair by the pool and closed her eyes. I grabbed a bottle of body lotion from our bathroom and poured it into my hand and lightly covered her stomach. I proceeded to work the lotion in as Enrico had done while I watched her breasts heave in and out with every breath she took. After completing her stomach, I poured the lotion needed to rub in to her amazing breasts. Instead of applying a light coat, I slowly pushed my hands up between her breasts before moving them apart and across each of her breasts gently rubbing her nipples. Linda moaned loudly as I continued to massage her breasts paying particular attention to her very sensitive nipples. After a few more minutes of me working on her breasts, she said Enrico I need you to fuck me now. She got up from the bed, went over to the balcony, opened the door and then moved to the railing on the balcony while spreading her legs.