The Bet

Amy and I were dating for a few months. She was hispanic, 5'0" with beautiful long brown/black hair past her shoulders, cute face, with small breasts and a stocky build. Being a Latina, she was fiery in bed. She tended to be aggressive, knew what she wanted, and took it. As with all relationships we had our ups and downs. We were good at communicating and talked deeply about everything from our feelings to what was going on in our lives.

One day the topic of conversation came up about our bodies. I told her that I needed to lose weight but it would be great if she lost some weight as well. She was about 120 pounds and I was 200 lbs. We would lose about 10 percent of our weight. I would lose 20 pounds and she would lose 12. To make things interesting we made a bet. Whoever gets there last, pays for a trip to Hawai'i.

We got to the weight loss. I had done diets before and was sure that I would have no problem winning this challenge. I was thinking that in 45 days I would win the challenge. Two weeks later, Amy calls. Claiming she was the winner. I was in complete disbelief. She came over, stepped on the scale, and sure enough, she had reached her goal weight.

"It looks like I'm on the hook for Hawai'i." I said. She smiled.

Now a little background on our relationship. Amy told me early on that she was in love with me. I'm not talking about the first time someone says I love you. She told me that she was so in love with me could easily be agape love - the self-giving, self-sacrificial love that is so complete that the person surrenders themselves to the other and love them purely for who they are. When she told me that, I felt honored and privileged to hear that she felt that way.

I loved her too, but did not quite reach that level of love yet. As a result of her feeling so deeply for me she wanted me with her. When we made love she was not on birth control so I used a condom when she was in her fertile time and pulled out other times. Although Amy accepted the protection measures, she did not want to use them. I did not like condoms either and much preferred to cum inside a woman. We both had kids from former marriages. I had a son, and she had a son and daughter. I didn't think we needed to add to the count.

There was one night where I got a condom and put it on, to the objection of her pouty eyes. After working ourselves up to the mood, Amy had climbed on top of me, took me in her hand, and slid down, on top of me, entering her. We made love for a while this way. Amy reached back and with each slide started to grab the bottom of the condom and slide it up my shaft. As soon as I felt it go up a bit I lifted my legs to stop her. She wanted to take off the condom and go unprotected. I was very conflicted. In one way, I just wanted to take her unprotected and put the baby inside of her that we both, at a carnal level wanted. On the other hand, the responsibilities of a newborn rushed through my mind. It was a dangerous crossroads.

When I objected Amy quickly relented and we both had decent orgasms despite the condom. What Amy did not know is that it would not have taken much convincing to get the condom off. Had she insisted a bit more and just playfully removed the condom I would have had sex with her unprotected. Since she was on top, she could have had her way. I would have tried to pull out instinctually, but if she did not let me (and it would not have taken much convincing) I would have cum inside of her. I knew that if I came inside of her once, I would probably do it again getting into more dangerous territory each time.

Back to Hawai'i. This trip made me a bit nervous. It would be the first time we spend a complete five days together without the interruption of kids, work, and life in general. Amy had a strong sex drive and I knew that we would be having sex a lot. Using condoms every time would be a pain and I was worried that we might just skip them for the sake of convenience. This would be especially true if we had sex somewhere outside of the hotel and we forgot them. Adding to the Russian roulette, I did not know where she was in her cycle.

A bet is a bet, so off we went. We met at LAX at noon, ready for our flight together to Maui. It would be a nice five days at a resort on the beach. There was a lot to do on Maui from romantic walks on the beach, to hiking in the rain forest. There were a lot of towns and natural areas to explore.

When we landed we went straight to the hotel to check in. It was about 6 pm when we finally got to our hotel room. We were hungry from the day's travels and found a local restaurant near the hotel. We had a nice dinner and decided to walk back hand-in-hand from the restaurant along the beach. It was wonderful to feel the warm moist ocean spray hanging in the air. A fresh breeze was blowing and the ocean was crashing on the reef in the distance. The sky was tropical with some clouds hiding the stars that peeked out in between.

We went up to our hotel room and got things going between us. Amy took offer her clothes and started to nibble on my neck after I took off my shirt. I reached down and took off my pants. We kissed each other deeply and touched each other's bodies. I sucked on her breasts and worked my way down to her folds. I spread her legs and took her clit into my mouth pulling it in and out between my lips. I used my other finger to enter her between her wet folds. I slowly entered her deeply with my finger and moved the tip hitting her g-spot. I could feel Amy enjoying my touch immensely. She was getting very sensitive to my touch and quickly flipped me on my back and took my manhood into her mouth.

Amy worked me up and down getting me intensely hard. She tended to be aggressive when going down on me. As she was working on me, I reached over to the nightstand drawer where I had thoughtfully dropped in a dozen condoms. I grabbed one, opened the package and held the condom until the assault with her lips was getting me near climax.

I had to push Amy off a bit or the night would be over too soon. I reached down and rolled on the condom not wanting to, but not wanting the fruits of the an omitted condom either. I was half hoping that Amy would be aggressive with the condom idea and tell me something like - she won the bet and that includes nothing between us. I would have relented right there. Instead, Amy reluctantly agreed and climbed on top of me. We both climaxed quickly, but not as completely as we would have liked with the latex between us. We snuggled together in bed and quickly fell asleep.

The morning came of our second day and we woke up to the sun shining into our hotel room. We opened the sliding glass door and let the sounds of the waves and the warm Hawaiian air roll in. We took a warm shower together, soaping each other down and teasing each other relentlessly. We got out of the shower without having sex but both of us a bit hot and bothered from our interlude.

We went downstairs and had a nice buffet breakfast by the pool. Beautiful waterfalls around us with fresh fruit and all the food you could want. We discussed what we wanted to do together for the day and decided to go snorkeling. Amy had never been because she did not know how to swim. I told her that we would use a life jacket and go see the underwater world that awaited us.

We left the hotel and went to rent snorkel gear. We both got situated with fins, mask, snorkel, and an inflatable dive jacket. We took the rental car and drove up the coast for a while to a little snorkel spot that I have gone to before. We parked the car and walked down a small narrow path through a beautiful Hawaiian forest and came to a large bay.

The coast was rocky which worked well to put on our fins with getting sand in them. I geared Amy up.

"Remember to breathe calmly thorough the snorkel. It will feel a bit weird at first. Dip your head in the water and just let it float. Your ears will be under the water." I said. I had her breathe through the snorkel before we got in. I inflated her life jacket, put on my gear, took her hand and we slid to a lower rock.

"Just slide in on your stomach. Use your hands to walk across the sand and rocks until you are in deeper water. Then just use your fins." I told her.

Amy was looking a bit hesitant as she started to work her way into the water. I climbed in a bit ahead of her so she would know where to go. I stopped Amy in the shallow water and had her breathe for a minute or two in a place she could easily sit up if she had to. Amy got used to it quickly and was ready to head off.

I took Amy's hand and we started to swim. I showed her how she just needed her legs and to let her arms float next to her. We went out a ways and saw beautiful schools of yellow fish, an eel, and larger mutli-colored coral eating fish that we could hear crunching away at the coral around them.

Amy was quickly getting her diving legs and getting used to her surroundings. I let go of her hand and dove 10 feet below her, swimming between the coral with my spear trailing just behind me. She watched me as I dove and swam around the bottom of the sea coming up to greet her often. I started to tease her a bit swiping my hand gently on her leg, pinching her butt, stroking across her breasts every so often when I came up from a dive.

After an hour Amy was getting a bit chilled so we headed back to the rocky beach. The sun was getting higher in the sky and we quickly got warm after drying ourselves off and taking off our gear. We found a little quite area under the trees to spread out our towels and sit for a while.

"That was absolutely amazing." Amy said as we sat together overlooking the bay. Amy reached over and started to kiss me deeply. I returned her kiss and held her in my right arm. I put my left arm on her naked stomach between the two parts of the new bikini she was sporting after losing so much weight.

Amy did the same with her hand. As we kissed I was getting harder. She could feel me getting worked up. She started to stroke my manhood outside of my pants. I reached up and felt her breasts on the outside of her bikini. Amy untied the string to my bathing shorts and reached her hand inside, gently stroking me. I grabbed the string on her back and gave it a quick tug with my right hand. The bikini top sagged and I scooped up her breast with my left hand, slowly circling her nipple.

Amy broke our kiss, pulled down my shorts a bit and started to go down on me. She stroked up and down knowing exactly how I liked it. I reached my hands around to the sides of her bikini bottoms and pulled the strings. Her bottom fell open between her legs. I reached behind her and stroked my middle finger between her folds. The outside a bit sticky from the dried seawater, but as I reached deeper between, I felt the silky wetness of her hunger.

I gently pushed Ana onto her back removing her bikini top over her head as she did. Ana was lying naked before me with eagerness in her eyes. I dropped my shorts and slipped them off past my feet. Spreading her legs I gently licked in between her folds tasting the salt from the ocean and her sweet sent combined. I stuck my tongue inside of her as she moved her hips a bit from my pleasureful intrusion. I felt her get wetter and knew she was ready for me to enter her.

As I was moving up to her I knew that we did not have condoms and that this was her fertile time. I gently slid inside of her and worked my way deep to her cervix. It felt so good making love to her without anything in between us. We made slow, passionate love for some time just enjoying the rhythm of the movement between us.

I could feel myself getting close. Amy felt me getting harder inside of her. She knew I was ready to let go. Feeling so good, but so conflicted. A beautiful place to have a beautiful ending to our love making by cumming inside of her. Knowing she was unprotected I wanted to pull out. I started to back out. Amy wrapped her legs around me. I felt so enveloped. I knew what she wanted and part of me deep down wanted it as well. Without much other thought I came hard inside of Amy. She felt me cum and had a huge orgasm as my sperm coated her insides.

We both took a few minutes to recover. It was done. I had finally cum inside of her. Amy smiled and looked up at me with that agape love in her eyes. She had finally felt what it was like to consummate our relationship with beautiful surroundings to add to the moment.

"Thank you." Amy said. "I will never forget this moment."

I smiled at her and hugged her. "It was an amazing moment together." I said.

We spent the rest of the day exploring the island. We drove around the North end and watched the large waves crashing on the cliffs with water blowing through the blow holes. We stopped at little villages and bought local crafts. At 6 pm we reached the hotel again after a blissful day together.

Once we got into the hotel room we showered and went to dinner. This time we ate at a restaurant right next to the ocean. We shared a Margherita and ate a wonderful seafood pasta together. After dinner we walked along the beach, hand-in-hand like we did the night before only this time it felt different. We had a deeper connection now that we made love in such a meaningful way and spent the day touring together.

We made our way up to the hotel room. Amy immediately jumped on top of me. She started playfully kissing me. She took off her clothes and then worked on taking mine off giving me kisses up and down my body along the way. She took my manhood in her mouth and worked her usual magic. She then climbed on top of me excitedly and slide me inside of her. I thought about the condoms in the nightstand drawer next to me but thought, what is done is done. We won't be needing those for the rest of this trip.