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Fun on the High Seas

By: SexySoxFan



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. 

Fun on the High Seas Ch. 02



Before I realized it the two of us had drifted off to sleep. A short time later I awoke to natures call. Returning to bed and wanting nothing more than to snuggle up next to Jenny I was saddened to find that Jenny had repositioned herself in the middle of the bed without room for me to use on either side. I tried to give her gentle shake but she was dead to the world. Since I had a spare bed in my cabin I decided to stretch out and from angle it gave me a wonderful view of both her ass and vagina. With lustful thoughts running through I was sound a sleep in no time. At some point Jenny must have woke up and disappointed that I was no longer beside her because I was woken the sound of a slamming door.

The next day when I finally woke up I was decided to catch some rays by doing some sun worshiping on the top deck. In my groggy state I realized that I was staring straight at Jenny and her friends. At first they seemed to be staring me down. Not wanting any hard feeling I made my way over and started to smooth the waters.

"Hey J- what's going on?"

All I got was a simple and curt response of "Nothing!"

"Are you mad at me for some reason?" I shot back.

"You can grasp the obvious pretty quickly, can't you?" she said coldly.

Sitting down beside her I smugly said "You know if anything I should be upset at you for hogging the bed and not letting me in."

With a glazed look she questioned "what are you talking about?"

"That's right!" I said. "I get up to go to the bathroom and when I come back you are smack in the middle of the bed and wouldn't wake up no matter what I tried"

Looking some what embarrassed she leaned in gave me a small peck on the cheek and apologized. A little more at ease I positioned myself behind her in the chaise lounger. Jenny must have liked this because she leaned back and grabbed my arms and wrapped them around her. The midday sun was becoming a little more intense and Jenny decided that we should take advantage of the ships Fun Day at Sea. With no arguments coming from me, we stopped at the bar on the way by and grabbed a bucket of beer and headed off to my cabin.

Wanting to waste no time Jenny had already started to take off her bathing suit while still in the hallway waiting to get into my cabin. By the time we crossed the threshold she was already in the buff and working on my clothes. Pulling my bathing suit down my already erect penis sprung to attention. This must have caught Jenny's eyes because she dropped to her knees and started to give my shaft a wonderful tongue bath. While thoroughly enjoying the blow-job at hand I needed to get involved in the action. Stopping her in mid suck I expressed my desire that we both share in the oral delight.

Pushing me down on the bed Jenny straddled my face and lowered her inviting love pot onto my waiting mouth. As Jenny returned to sucking my cock she soon started grinding my face in the same rhythm. With her expertise she had me ready to explode and just before I lost my load I was stunned when Jenny quickly stuck a finger in my ass. In addition to starting me it set off a chain reaction of my orgasm followed quickly by one for Jenny.

As luck would have it a rain storm started to pass over so we figured there was no sense in leaving the room. Calling up room service we ordered some drinks and snacks and stretched out on the bed knowing that if we started anything it would soon be interrupted by room service. Luckily it didn't take too long for the food and drinks to arrive and locking the door behind them we were good to go. Placing the food and bucket of beer next the bed we assumed our positions on the bed. Reaching in the bucket Jenny took out an ice cube and started to rub it around her nipples and those puppies looked like they could poke and eye out they were so erect.

With a little tongue play I was soon fully erect and Jenny took the opportunity to climb aboard and start riding me like there was no tomorrow. Bucking back and forth she had me on the edge of orgasm when in one quick motion she pulled up and I could hear the suction as my throbbing cock exited her wet vagina. Sliding down Jenny placed my cock in her cleavage. The fact that I was still wet from her love hole there was plenty of lubricant as she started to give me an incredible tit fuck. Sensing I was about to explode Jenny let go of her tits and my wad of cum rocketed towards her face. The second blast barely made it to her chin and the after shocks splashed down of her heaving chest.

With four more days left on the cruise I could only image what kind of fun we could find.