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.
