Fun On The High Seas

I had been dating Stacy for about five months before I decided at the last minute to join a bunch of buddies on a week long Caribbean cruise. Although I had grown fond of Stacy and would almost even say that I loved her, sex with her at times was in a word a struggle. I by no means consider myself to be an expert but have had enough sex to know what is good and what is bad and this was bad. If it wasn't bad enough Stacy was not someone that would stay wet enough for easy penetration but she also was not one to give blow-jobs and as a result when would feel guilty if I tried to go down on her, which would leave sex to seem more like a chore on the honey-do list than an enjoyable activity.

As I am getting ready to leave for my cruise Stacy tells me that if I want to find someone that will blow me on the cruise that is okay with her as long as I don't have sex with her. With this new found freedom I began to anticipate a good trip. Although past vacations didn't result in much sexual contact I was tackling this trip with an agenda and was going to pursue any possible lead. I started out the first night by approaching Wendy in the disco. Wendy was a slightly attractive girl and seemed to show some interest and I felt things were looking up until she left me high and dry on the dance floor. Unfortunately the rest of the night did not go much better.

Not to be deterred the next day while hanging out with my group of friends we joined up with a group of girls from the Chicago are. The two groups seemed to hit it off right away and my focus went to Diane, a very attractive girl with long blonde hair, soulful brown eyes and a set of tits that were doing the best to break out of her bikini top. I wasn't able to get a good read on Diane's interest but kept trying to make my move. At the same time it had been quite obvious that Jenny was the wild one in the group. Jenny wasn't a model but there was something about her that caught my eye. She was a about 5' 4" and a bit of chubby girl with mid-length hair and ample breast. She had a slight Queen Latifa look to her. As the afternoon progressed I found myself looking at Jenny more and more often.

As the afternoon ended and the two groups separated we said our good-byes and headed back to our cabins to get ready for dinner. Having had more than a couple of drinks that afternoon the thought of Jenny had left my mind but the plan to get laid was still in the forefront of my mind. After dinner and more drinking at the piano bar we found ourselves at the disco where shortly after Jenny and her entourage arrived. Sensing an opportunity I approached Jenny and started to chat her up and was a little wounded when she started to question me about my friend Jason who although an ass never seemed to have trouble ending up with the girls.

As I was starting to stew over yet another failure Jenny came back to me with a big smile on her face. When I asked her what was up she tells me how boring Jason was and in her next breath asked me if I wanted to get out of there. With my rapidly inflating ego I agreed but she said that before we could leave I would have to kiss her. I was thinking this was just going to be a quick church-tongue type of kiss but was surprised when it turned into a deep knee-buckling type of kiss.

We had decided that we would head to one of the outside bars because it would give us a quieter atmosphere so we could talk and get to know one another. Little did I realize that our walk would require us to make several stops for quick make-out sessions and I sure that our kiss exchange in the glass elevator put on quite the display. We eventually found the bar and like giddy school kids continued to steal kisses every couple of minutes. Our talk consisted of the particulars of if either was dating anyone, married, where we were from, what we did for work.

Sitting even closer now, to make kissing easier, I kept one hand caressing Jenny's thigh, and as I landed for another kiss she looks me deep in the eye and says "just so you know I am not going to fuck you"

Realizing our kissing was becoming more and more passionate I suggested we head back to my cabin. Jenny's first concern was my cabin-mate but when I assured her that I had room to myself we were settling up the tab and making our way back to my cabin. After entering the cabin it didn't take long for us be sprawled out on the bed arms caressing each others body while our tongues seemed to be as one. The more aroused I became the more my hands started to roam and one had found its way under dress and was heading up her leg in a gentle motion. Just as I was about to reach my target I was informed that she wasn't wearing any panties and with that nugget of information I nearly exploded. She informed me that she only told me so I wouldn't be surprised but to this day I think I would have preferred the element of surprise.

Once my hand reached her honey pot I couldn't believe how wet she already was and with deep moans I heard with my finger fucking I felt her previous comment about sex might change. With our clothing getting in the way our clothes quickly became a tangled mess of laundry on the floor. With already knowing how wet she was I needed to find out if she tasted as good as she felt. Being no stranger to going down a woman I loved the fact that Jenny helped me along by moving my hands to where she wanted to enhance her pleasure. Keeping my face and tongue buried I was becoming hypnotized by her sounds and movements.

Needing a breath of air I came back up and started to kiss Jenny some more to her get a hint of how good she tasted and as this is happening Jenny proclaims "I love the way you cock feels against my clit!!" With that being said she was on top of me and I was deep inside her enjoying every thrust. The rolling seas and swaying boat added to our own motions. It was site to behold, her facing contorting with the enjoyment and her tits bouncing in time with our movements. We both exploded in what seemed like and endless orgasm. Jenny collapsed on top of me gave me kiss and said how glad she was that it was only the beginning of the cruise. I smiled, agreed and began to envision what other fun lied ahead.