In the Summer of 2001, there was no Craigslist nor were there apps you could download on your phone to help scratch that proverbial itch, just chat rooms where you hoped to find someone close by for no-strings attached sex. For me, it was Yahoo chat.
I was a 21 year old college student who had just broken up with his girlfriend and extremely bi-curious. I had, for several months, gone into straight chat rooms and pretended to be a woman. I had jerked off hundreds of times to the thought of taking a hard cock in my mouth and sucking it until it rewarded me with a load of cum. I pretended to be a woman and allowed hundreds of men to jerk off imagining me on all fours while they drove their hard, pulsating cocks deep into the pussy I didn't have. Looking back, this was all in preparation for when I finally went into a gay chat room.
At 5'10 & 140 pounds, with smooth abs and a bubble butt, I epitomized the term "twink" and I used it to my advantage. In gay chat rooms, I was immediately drawn to older, professional men and they thankfully were drawn to me. One in particular, from the very beginning caught my attention, and made me seriously question my attraction to women. His name was Edward, lived 45 minutes from my parents and was willing to meet me on my terms. He had been divorced for several years, had two teenage children, and owned his own business. We chatted for several weeks, before I finally felt comfortable giving him my phone number and when I did, we talked for hours on the phone that evening.
After several more weeks of chatting on the phone, I finally had built up the courage to blurt out "so when are you going to ask me out for a drink?" After a long awkward pause he said "just a drink, you don't want dinner or a few drinks?" We both laughed and agreed to that upcoming Friday.
Friday arrived and I couldn't wait to finally meet him. In our phone conversations he admitted to me that he liked young men with smooth bodies, so after getting home from work, I took extra care in shaving my body. I especially made sure that my ass and balls were completely smooth.
I walked into the bar we agreed to meet at, my heart was racing and for a split second I began to second my decision to meet him, but the minute I saw him sitting at the bar I immediately felt at ease. He turned around, smiled, greeted me with a hug, and whispered "you're way better looking in person." He placed a hand on my lower back and guided me to the bar, where the minute we sat down his hand went immediately to my leg, and my cock immediately began to swell. I looked in his eyes, smiled bashfully, and apologized "for running a few minutes late, took a little longer than I expected to get ready."
After a couple rounds of drink, we ordered dinner, and then began telling our life stories. Within less than hour, I knew more about him than any girl I had ever dated and I had opened up to him like I had never done before. When Edward asked for the check, I couldn't possibly even have imagined what lay in store for the rest of evening and night.
As we got up to leave, Edward looked over at me and asked if I was interested in going to his apartment and without hesitation I responded "I would love to." He lived a short distance from the bar and as we stood in the elevator he finally reached over to hold my hand. I turned to look at him, smiled, then moved closer to him. By this point, I was extremely turned on and wanted him to know it. Without hesitation, I leaned in closed and gently kissed his lips.
Once in his apartment, I was shocked by the amazing view and made my way to the balcony. As I stood admiring the view, I felt him wrap his arms around me and kiss me softly on the neck. Letting out a soft moan, I turned around and placed my arms around his neck, looking deep into his eyes I whispered "you definitely know how to make a boy feel good." He smiled, kissed my lips and said "baby, you have no idea how good I'm about to make you feel." With that our lips locked in the most passionate kiss I had ever experienced. I had fully succumbed to his charm and wanted to please him in every way.
In the midst of our kissing, we both began undressing the other, my hands unbuttoning his pants while he removed my shirt and vice versa. Within second we were both totally nude and caressing each others body. Having never been with a man, I slowly slid my hands up his chest and down his back, pinching his nipples gently. I caressed his muscular ass and pulled him close to me, our hardened cocks now fighting for real estate. The feeling of his cock against mine was surreal. It wasn't until I finally came back to my senses that I realized what it was that I pulled back from him far enough to slide my hand between us and wrap my hand around it.
Looking into his eyes, I pulled myself up on to my tiptoes, and kissed him romantically while I stroked his cock. He pulled away from my kiss, looked me up and down, then said "you sure you're up for this?" I did not hesitate when I said "yes".
Taking my hand, he led me to his bedroom and disappeared into the bathroom, where he began to run bath water. Reappearing several minutes later he again took me by the hand and led me into the bathroom where a whirlpool bath awaited the two of us. He asked me to climb in and then returned to the bedroom. He came a minute later and joined me.
