Like most people, from an early age I have been fascinated by sex and all that revolves around it.  I can pinpoint the first time I came across something overtly sexual and the feelings it elicited.  In fourth grade, I distinctly remember seeing a torn out nude centerfold on a field as I was running home from PE one day.  I was late and had to go, but I paused and stared at the brunette, voluptuous woman on the roughed up page and felt a rush of intrigue, excitement and shame.  My friends were calling me to hurry up and I knew I shouldn’t be looking, but I hovered there for 10 long seconds before sprinting like a gazelle (I was that skinny) with all my newfound energy.  

 

Little did I know, that would be the first step in a long journey of sexual curiosity.  Unfortunately for me, tangible experiences with foreplay and sex would take much longer to get started.  I went through junior high and high school as a respected nerd, if there is such a thing.  I was shy, quiet and thoughtful.  If I wasn’t studying or playing tennis, I was watching cartoons or hanging out with my parents and sister.  In 7th grade, the four biggest and most popular guys decided they would be my body guards for reasons I still don’t understand.  I remember being intentionally tripped, again in PE class, by another guy and those four jumped and beat up the culprit the most you could in a fancy Miami private school.

 

I was one big hormone during those years, but felt like I was wearing a locked chastity belt that I forged and forgot where I put the key.  I didn’t know how or when to talk to girls and therefore, most of the time was silent.  When I was bold enough to make a foray, it generally came out wrong which only discouraged future attempts.  I went on 2 dates my entire high school career, didn’t go to prom and graduated not just a virgin, but also a kissing virgin.  

 

When I got to college, the desire only intensified.  I was born in November, which makes me a Scorpio.  Depending on who you talk to, Scorpios are known for their strong passion in all walks of life.  This includes sex which gives them the notorious title of being the most sexual sign in the zodiac.  I fit this description to a ‘T’ and masturbated nearly every day.  More than that though, I wanted to learn how to be a good lover and read countless articles on the art of pleasuring a woman.  For that reason, I was more excited at the prospect of going down on a girl than I was by having sex with her.  

 

My college was in the south, filled with tons of gorgeous southern belles, most with a cute southern accent.  Thankfully, my social skills with guys had improved so that I made a core group of friends my freshman year which I kept for the remainder of my life.  They quickly learned of my predicament and made it their mission to get me laid.  They were all in the same fraternity and threw multiple parties and set me up on multiple dates to no avail.  They eventually shifted their goal to getting me to kiss a girl, but again were unsuccessful.  You might think that I was unattractive or had some physical issue, but aside from being extremely thin, I was a decent looking guy which I only came to realize much later.  I recall seeing girls smile at me in the halls and immediately checking to see if I had bed-head or had a stain on my shirt that caused it.  I was also terrible at reading body language, so at the end of dates, I generally asked my date if I could kiss her.  This sweet and thoughtful technique got me zero kisses by the time I graduated so that, again, I was a kissing virgin when they handed me my diploma.

 

Despite the constant setbacks, there was hope.  I planned on goofing around in the months after graduation and staying near the university to hang out with my friends who were doing the same that summer.  After only a couple weeks, I took a trip to New York City for the first time.   While there, I met up with a childhood friend who I had hung out with the previous New Years Eve.  Her name was Cathy, and our families were friends for as long as I can remember.  I used to sit out on a surfboard and tell Garfield jokes with her when we were in elementary on a lake my parents would take us to.   She is two years older and therefore drove me to school for a few years right as I hit puberty.  Our sisters were the same age and best friends and mine used to come back and taunt me with tales of Cathy’s toplessness while she was visiting her friend.   That drove me crazy!  On New Years, we all went out like old times, and Cathy sat on my lap in the passenger seat at the end of the night because we were a packed car.  When I later met up with her in NYC we chatted all night, ending up on the steps of a brownstone till the sun came up.  One thing she made clear was that she was hitting on me that night.  I’m glad she did, because my body language radar failed me again and therefore I made no moves.  While nothing happened that night on the steps, she said that if I came back to Miami where she was, that potentially something could happen.  Within 3 days of returning to college I was packed up and on the road back to Miami.  

 

We went out the 2nd night I returned, had a little bit to drink and predictably, at the end of the night, I asked her if I could kiss her.  She knew all about my inexperience and after asking, she turned away like all the other girls before her, so I figured I’d messed it up again.  She then quickly grabbed me and kissed me for what was probably 5 seconds, but felt like 5 minutes.  She got in her car and left and I was flying. 

 

We went out the next night, and while I could write a separate memoir on the events of that night, I will fast forward to her ending up naked on my parents’ beach.   I was so stunned that she had to call me over and we had sex on the sand.  I orgasmed 3 times (I had 21 years of build up) and we went skinny dipping after.   The next morning I went by her house to do some of the things with her I had skipped on the foreplay scale leading up to our tryst in the sand.  Unfortunately, she got a job in NYC of all places that week and left within a few days so that I was left a tad heartbroken, but finally experienced.  

 

Things moved pretty quickly for me after that.  Within a couple months, I got my first girlfriend, a tall blond athlete at the University of Miami.  A few months after that, I met a gorgeous model at a party on South Beach.  We were so struck by each other, we only talked to one another from the moment we met till the end of the party 5 hours later.  One of the things she told me is that I could model like her if I wanted.  As stated earlier, my self-image was fairly low so I thought she was pulling my leg when she said that.   To prove it, she said she’d bring another model to photograph me on the beach the next day.   I didn’t believe them, but I went anyway the following day and they were there with 3 disposable cameras.  We took a variety of pictures and they helped me choose the 5 best.   Armed with those, I went to open calls for a few of the major modeling agencies on South beach and the 2nd one I went to offered me an exclusive contract to sign with them.  I was obviously shocked that all this was happening, but I just kept rolling with it. The next year and a half was filled with part time jobs, modeling gigs and decadent South Beach parties the likes of which I could never have imagined during my shy high school days.  As silly as it sounds, one of my goals in returning to Miami at the end of college was to work on my social skills which I considered a glaring weakness in my life.  After a few months of modeling I turned that weakness into a strength, and every day gained more and more confidence.  

 

Over that time, I found some sense of a sexual identity.  I was finally able to put all the sexual knowledge I had acquired during my virgin years to good use.   I eventually started dating the model I met at the party and, given that she was 7 years older than me (which was a big deal at the time), she taught me a lot which I couldn’t get enough of!  One of the highlights of our time together was a boating trip we made with friends out to a sandbar near Miami.  We were 7 girls and 4 guys and after drinking and daring all day, eventually the girls’ tops came off.   Two of the girls (neither my girlfriend), then pounced on me and took off my suit.  After that we were all naked in the water to the amazement of other boats.  I’ll never forget that gaping mouths of the onlookers while they slowly drifted by.  We chicken fought with the girls which was a lot of fun before a storm chased us back to shore.  

 

My dad eventually told me I had to shape up and do something with my brain, so I applied to graduate schools.  I was accepted into a Financial Mathematics program in California so away I went.  The stark difference between cavorting every night in South beach and being back in a classroom surrounded by some of the brightest and most ambitious mathematical minds in the world was nearly too much for me.  I came very close to quitting my first quarter there, but stuck it out and graduated a year and a half later.  That resulted in me taking a job in NYC which was the beginning of the next phase of my sexual exploration.   

 

When I arrived to NYC in 2001 I had just endured a painful breakup with my model girlfriend and for the first time was, single, sexually experienced and not living at home.  In addition, the internet was slowly becoming a legitimate platform to meet other people on for all sorts of activities.  Despite all of my exploits and experience, I still found it awkward and forced to pick up girls at bars.  A few years after my move to NYC, that is where the first dating websites filled a perfect niche to meet girls who were themselves looking for something to do in the big bad city.  

 

I never to this day signed up on what I consider legitimate dating websites, Match.com or Eharmony.com.  I really just wanted to meet girls to have sex with and if I came across a special one that was relationship worthy then that would be icing on the cake.   There were multiple websites even at that time that fit that description like Nerve, Plentyoffish and the “Intimate Encounters” section on Lavalife.  The other benefit of using the internet, was that it was easy, efficient and inexpensive to find girls you’d have a potential match with vs. the alternative of going out to bars or clubs.  Despite being in my mid 20s, after working stressful 10 hour days in finance, I didn’t always have the energy to drink at a bar.   Again, the internet came to the rescue, helping me set up dates with girls that intrigued me.   Over time, I perfected my first and second date repertoire and became quite experienced in the art of seduction.  

 

After a while, I yearned for something more.   I never took drugs, was a social drinker and never really had any vices.  I decided that sex was the one area of my life where I wanted to explore and take more risks.   A former coworker had moved to Argentina where I visited him after a year there.   He told me about some secret parties that occurred in hidden locales in Manhattan that I might be interested in.   They were swingers parties from his description, although I came to realize over time, that most of them hate the connotations that go along with that name.  He gave me the contact info of a friend who put them on and I visited her website.  Apparently, she had been throwing them for years and, to join, I had to write 4 essays related to sex in addition to sending pictures and adhering to the strict code of conduct.   As stated above, I was committed to learning more so I did everything she asked and they accepted me as a member.  It still took me a year to work up the courage to attend my first event.  

 

It was at those parties, that I expanded my sexual horizons to places they had never been before.  I learned about the different levels of participation: from voyeurs to exhibitionists to those that play and interact with the other guests.  It spun my head in all sorts of directions, but I loved it.  The sex was fun, but more than that, I enjoyed being around open minded, sexually adventurous people that were similar to me.  It didn’t hurt that the majority of them were attractive which isn’t always the case at those types of parties, I came to learn.  Physical attraction is vital in those situations so even though I wanted to be high minded, chemistry is not something you can nor should fake.  

 

I became friends with the organizer of the parties and she invited me to write about them in exchange for free admission.   I loved learning about the people who attended.  Some were new couples, going for the first time.  Others were married couples with kids who flew to NYC for the weekend to escape their parenting lives for a couple nights a year.   There were also single women (single men are not allowed at those particular parties) who were bi-sexual or bi-curious and had the courage to explore on their own.  All of the events were themed which created a fun, erotic atmosphere to find mischief and debauchery if one so chose.  The best events were held in summer on a sailboat around Manhattan at night.  Whether you participated in the naughtiness or not, the sight of the Statue of Liberty on the water by the moon is breathtaking.  Doubly so if someone(s) happen(s) to be pleasuring you at the same time.

 

I have many wild tales to divulge at another date, but hopefully you enjoyed the story of my sexual evolution.  Many hugs, kisses and spankings to you all.