One fun vacation (Part 1)

[funtimes444]

I've read a bunch of posts on the board and they've been amazing and fun to read. So much so, that I'm now ready to come out of my shell to tell my story, which happened about six years ago. It's kind of long, so I'll ask you to bear with me -- it'll be worth it as in the end you'll see how mind blowing it is.

Before I begin, I guess I'll give you all some background. I'm currently a white make in my 30's. I was born and raised in an affluent suburb or Philadelphia. I had a fairly "normal" childhood in that both my parents were professionals who had a pretty mundane marriage but stayed together. My younger sister and I were "normal," suburban kids who had nice friends, received good grades, participated and excelled in sports (field hockey for her and soccer and tennis for me) and ultimately went off to prestigious colleges and embarked on successful careers.

But that's where the normalcy ended for me. Though post-puberty I was a good looking kid who was always in shape (a hair over 5-10 and about 170 pounds) and never had trouble getting girls, I was mostly bored out of my mind with most of the chicks I met. This didn't change when I moved to Manhattan out of undergrad to take an investment banking job. These were the "loosey-goosey" days on Wall Street when the money was flowing and guys like me ran around The City like they owned it.

For more than the first half decade I was in Manhattan nothing really changed. During the week, I worked hard at the bank, and during the weekend, I worked hard at the bars picking up girls who bored me to death.
Then I met Jessica and everything changed.

I first saw her at my neighborhood supermarket then at the gym, where the place was chock full of young, pretty girls -- all in amazing shape -- who were living off their parents as they tried to complete their Mrs degree by landing a wealthy banker, lawyer, or ad exec. Despite the dozens of hot chicks on the treadmills, stair masters, and ellipticals, there was something about her that really caught my eye.

Maybe it was the tight shiny spandex that accentuated her amazingly taut 5-04, 115ish pound body, or maybe it was her dark curly hair (at a time when every chick in Manhattan was trying to straighten her locks) and piercing brown eyes, or perhaps it was her sensual walk, the way she shook her ass just a little as she moved around the cardio room. At any rate, just looking at her made my blood boil like no girl before her.

We finally met one day as we exited the gym at the same time. She actually spoke to me first my saying, "You don't miss a day, do you?" That was my in. Within two minutes I had her laughing and within five I had her phone number.

The first several dates were a lot of fun. Each time we went for dinner and each time the conversation was free-flowing. Surprisingly, unlike a lot of hot girls in Manhattan with wealthy parents, she was down-to-earth and easy to talk to. We also shared a lot in common like favorite food, movies, etc. But there was something else, this sexual tension that we had, even though in the beginning we didn't do more than kiss good night.

I should have known something was up when at the start of the second date, she looked at my pink Hugo Boss dress shirt, ran her hand gently down my chest and said sweetly, yet seductively, "Love the shirt." She then delivered a five minute monologue on how too many guys in New York were "boarish," had no sense of style, and had to get in touch with their feminine side. Again, I felt the blood boiling.

I guess I'll stop here for a second. I think a big reason why I had been so bored with women up until that point was that I was never attracted to girls who liked boarish men. I mean, I played sports my entire life, but they were soccer and tennis, not football. And speaking of football, I wasn't the type of guy who would spend his Sundays wearing the jersey of his favorite team while stuffing his face with wings, chips, and Michelob. Oh, and while we're at it I liked to read (things other than the sports pages), didn't mind shopping and "metrosexual" wasn't a four-letter word.

Getting back to the story (and don't worry, it will get REALLY hot REALLY soon), as Jessica and I continued to spend more time together we realized we shared even more in common. And when we finally slept together -- around our tenth date -- it was great. While we didn't do anything remotely kinky, it was by far the best sexual experience I'd ever had. Her body was as good as advertised, she was well groomed, and she had this unbelievable intensity about her, especially when going down on me. And, I'll say she felt the same about me.

Things progressed nicely and within a few months it was winter, and we planned a great get-away vacation to a five-star resort in St. Martin. And about two weeks before we left, things started to get exciting.

We were out for dinner one night and were taking about some of Jessica's gay friends (and she had many of them) when she confided that she had "a thing" for gay guys and found "hot" ones "sexy." She also mentioned that she enjoyed watching gay porn. None of this really scared me and before I knew it the main course came and we devoured our meals.

Later that night, however, as we were hooking up and she was massaging my balls, she suddenly went "south" to a region she had never been to before (at that point in my life only one girl had ever gone there before, and like most guys, I quickly moved her hand away). But this was a different time and a different kind of girl, and before I knew it, I was experiencing pure, unadulterated ecstasy as Jessica's finger, aided by the Vaseline she kept on her night table, probed my butthole. She didn't say anything -- she obviously enjoyed hearing me get completely turned on and, to be honest, she was quite turned on by this herself. I came without even having sex, and, once I ejaculated, there was no mention of what had just happened.

The next two nights were carbon copies of the night described above. We'd hook up, I'd eat her out till she came than she would finger fuck me. I LOVED it. In fact, I would fantasize at work, on the subway, and at the gym about it. But it went unmentioned between us.

On the fourth night a strange thing happened. Instead of putting her finger in my ass, Jessica teased me by massing my balls then gently caressing the area underneath them, but when it came time to insert her finger between my cheeks, she never did. She could so tell how badly I wanted it and actually gave this sinister, shit-eating grin when she saw how much she was tormenting me, but that was it. I had to "settle" for plain, vanilla sex.

The same thing happened the next several nights, and Jessica obviously loved tormenting me. She'd blow me for a little while, lick my balls, and even lick right underneath my balls, but when it came time for either her finger or tongue to touch my asshole she'd fold up shop and start kissing me. Man, I wanted her to play with my ass so bad, but was just too afraid to say anything.

Several night before we were due to leave, we had a little fashion show in her apartment. Jessica, who worked as a PR Agent in the fashion industry, decided she was going to go shopping for me and "dress me" on this trip. I've told you already that I'm fashion forward, and since I liked the way Jessica dressed herself (super sexy, yet classy), I didn't have a problem with this. The result was plenty of linen pants and shirts, designer sandals and loafers, and even a man purse. None of this really phased me.

Later, we had just gotten into bed and were lightly kissing and caressing each other when she asked, "So did you like what I bought you?" to which I responded that I did. Then suddenly she added, "Listen, there's something else I bought you and I don't know how you'll feel about it, but I'd really like if you wore it." I was totally confused by this point and responded with a "Try me." She took the slightest of deep breaths and said, "I bought you some bikinis that I'd like you to wear."

At first I thought she meant women's swimwear, which, despite my open-mindedness would have been odd. Then I realized she meant what was known to most of us as "Speedos."

"Oh, so you bought me some Speedos?" I asked. To which she responded, "Speedos are what 16-year-olds wear for swim team. Bikinis are what hot guys wear on foreign beaches."

I guess I seemed hesitant because just at that moment her finger magically appeared super close to my butthole and she whispered sensually in my ear, "Baby, if you wear a bikini for me I will give you an amazing rim job." I was sold.

Before we knew it, we were taking off from LaGuardia Airport in 34 degree blustery weather only to land mere hours later in an 87 degree tropical paradise. Within minutes, we picked up our luggage, cleared customs, and caught a cab to the beachfront luxury hotel.

It was around 3PM and we were both in a rush to go outside and grab a couple hours of Caribbean sunshine before it got dark. I stripped out of my winter clothing and was about to put on my board shorts when Jessica said, "No fucking way...you promised" as she handed me what almost looked like a girl's panties.....

Stay tuned for more