I'm 29, and prematurely shamed by divorce. Following a great four years at Brown University, I hurried to marry the first love of my life. My wife, Alexandra, was great, truly. But somehow we both knew that it wasn't for keeps, so to speak. And so, at the ripe age of 28, we parted ways. There are two things I will always remember about her: the way she flipped her medium length chestnut hair behind her with confidence, and the way she used to ride me. I had never had any inkling that I could be gay until after our divorce. I had never had a problem performing sexually, and I was hot for women. The vagina was my temple, and I worshipped in it as often as possible. In college, before meeting Alexandra, I had sex with somewhere around 10 women. I guess I was a bit of a man-whore, but who cares. I had always taken peeks at men, and envied the better bodies and penises of men, but I had never thought that my quick glances were unusual. I assumed that every man was curious of other men, and so I was normal.
After my divorce with Alexandra, I began to see why I was different. After an eventful 8-year marriage, my sex life came to a halt. We had been having sex regularly for that length of time, and there I was, left with my fist and a tube of lube. I moved to New York City after the divorce, taking a new job with a prestigious law firm. I was young, hardworking, and I had prospect for the future. At the same time however, I was lonely. I sort of sunk into a lull in life for a while, about half a year, where I worked, slept, ate, and jerked off. I would sit in my tiny Manhattan apartment, watch porno tapes, surf the net, chat, and masturbate. It was almost like I was a teenager again, but I had nothing better to do. One day, I had gone to the gym and worked out. Normally, I never bothered to shower or anything at the gym, with my apartment only a few blocks away. That day, however, I felt like relaxing in the Jacuzzi at the gym, and so I found myself showering afterwards. I looked around me and all I saw were muscular, toned men with good-sized dicks and fantastic bodies. It was then that my curiosity was struck. On my way home, I somehow struck the nerve to buy a Playgirl magazine, and I went right home to examine it. I looked over the pages of men, with their smooth shaved bodies and rigid, hard dicks. The veins were pulsing on their 10-inch cocks, and I realized that the cock is what I had craved all along. I slipped off my clothes, and I sat on my couch in a pair of black bikini Calvin Klein underwear, and as I looked at the pictures, my cock began to swell. It was pushed up the side of my underwear, and was pushing to be exposed. Eventually, after staring down each page of the magazine, I grabbed a tube of lube from by my bed, and I squeezed a glob onto my hand. I slowly began to rub the lube onto the head of my cock, slowly working down the shaft.
I consider myself an attractive man. I am six foot three, with a fairly toned body. I have dark jet-black hair, and greenish gray eyes. I have small tufts of hair on my chest, expanding from one nipple to the other, and lightly attaching to my belly button and trail to my pubic hair. I have an ample bush, but it does nothing to hide my cock. Flaccid, it's only a few inches, but erect it stretches at least 7 and half inches.
Anyway, I was about to tell you about jerking off the first time as a gay man. I started to slowly fist my cock, twisting my fist around, giving attention to both the head and the bottom of the shaft. In my mind I saw the pictures of the men from the magazine, and I wanted their cocks. I wanted to feel their velvety skin in my mouth, swallow their cum. I had never craved anything in such a way before, and I knew that I had to get some. I remember jerking to an incredible orgasm, shooting cum right onto my face; it dripped down my chin. I had never before tasted my own cum, but that day, I stuck my tongue out and licked the cum around my lips. Though I thought the taste strange, I didn't mind it in the least. As a formerly straight man, I had no idea how to just start being gay. I wasn't really sure that I was gay, but I did know that I was sexually frustrated, and I craved a man.
This entire realization of my homosexual fantasies came about in late June, and I was about to take a vacation to Barbados in the Caribbean, in an attempt to move on from Alexandra. I had no idea that I would move on in the direction I did, however. I packed my bags, including my large tube of lube, with the expectation of hotel porno and a few uneventful jerk sessions. I did however, have the best sex of my life.
When I arrived in Barbados, I took a taxi to my hotel. It was a resort, all inclusive, write on the beach. It had two private beaches that were excluded from any of the strips. My room was on the third floor of a thatched building, with palm trees around it. I had a balcony that looked over the pool and the beachfront, the beautiful crystal clear water of the Caribbean. When I arrived, I noticed that most of the guests were European, sporting skimpy Speedos or trunks. Me, the common American, with a large bathing suit, craved the attention of something a little more risky. I had always had the fantasy of wearing a Speedo, and so I indulged at the hotel gift shop. I bought the only one they had in my size, a blue thin Speedo with a drawstring. Though slightly hairy on my upper legs, I decided to venture out into the resort sporting my new bathing suit. I blended in with the crowd, or at least I thought I did. I layed on the beach for the first day without incident, sipping margaritas and minding my own business. I read a few good books, and enjoyed the tranquil sound of the waves hitting the beach.