Meeting Jeff Pt. 1
For as long as I can remember I have always wanted a boyfriend. I wanted that "something" different. That taboo, that lust for someone who like me, had the same equipment I had and knew how to use it. But like most men at that age when my curiosity peeked, you weren't gay or bi, you dated women. I met and fell in love with a woman. We married and had kids and were living the American dream. A few years later the honeymoon phase was over and troubles started. No doubt I (we) got married too young and as most who do, the marriage fell apart.
I wasn't saddened that my marriage ended because, in all reality, the amount of arguing, fighting, and resentment was not doing either of us any good. And to be honest, the opportunity to date again, and find better was more inviting than staying with a woman I wasn't in love with anymore. But I wanted something different. Those feelings from years ago had not changed. I wanted intrigue. I wanted suspense. I wanted dirty. I wanted off limits. I wanted to feel different. I wanted to love different. And to be loved differently. Simply stated, I wanted cock. I wanted to know what it felt like to suck dick. To be fucked. To be in love or at least lust with a man. To wake up next to him. To be his.
During those following single years outside of loosely dating women, I met, befriended, and dated a shemale. And after that ended, I found another and dated her. For almost two years of my life, I was in gay relationships. I was learning new ways to love. And to be in love. I was learning how to suck dick. How to fuck and be fucked with someone who had a dick just like me. Now I kept these relationships secret from my family, friends, kids, etc. Several factors unrelated to this tale kept it that way. But I must tell you, as weird and wild as it was at first. I fucking loved it. I still loved and admired women, but I knew I also had a lust for men.
As the years progressed, I met and fell in love with a woman named Amanda. Through it all, fate, destiny, ties, and complicated issues kept us from being together. And when a life-changing job opportunity arose for me in another state, I jumped at the chance. (See the; I sent her the video series, regarding Amanda). As hard as it was to leave friends, family, and my grown children behind, it was time for a change and a time to live life the way I felt it needed to be.
As soon as I got to Florida, the change started. I felt liberated. I felt excited, I felt born again. See I was away from family, my ex-wife, a host of overseeing eyes, and a cast of people in my life who would have never understood my lust and desire for dick. I was going to change my life and live how I wanted to live. I was going to find a man, a transgendered female, or a passable crossdresser. Someone with a good hard dick and someone I could lust for. Build a relationship with. And have the same passion and desire for her as I did in every other relationship, with a host of new freedoms I never had before. The change and determination to find someone with the same part was coupled with the fact that I had just lost - whom I believe was - the love of my life, at least spirit-wise, so it was time for me to live the way I wanted to live. And by God, I was going to do it.
I signed up for every gay and bisexual dating site I could find. I was leaning more toward the transgender or crossdressing individuals, but I would take anyone whom I got along with, who was normal and decent. I checked them often and was trying hard to meet someone new and exciting. Some time into it, I received a message from a man named Jeff. Jeff was the only man that approached me with dignity and respect and seemed like a normal person. Jeff was two years older than I was.
Jeff was an attractive man. He had light brown hair, short and parted to the side. He was just about my size, a bit chunky around the midsection, but surely not overweight, or looking like he was 7 months pregnant. In conversations with him, I learned he was a business account and worked the basic Monday through Friday 9 to 5. He was a few years of out a divorce from his husband and was looking to find someone new, just as I was.
We chatted a lot and eventually got the opportunity to meet for dinner. Even though he was a friendly, nice, and a handsome man I was still really hoping to find a transgender female, but at that point, that didn't seem to be happening. As time went on and my conversations with Jeff grew more frequent and more in-depth, I started to feel an attraction for him.
Our second date was a little more relaxed since we had gotten that first one out of the way. We went out to eat again and after we just sat outside the restaurant talking for a while. I could see he was interested in me and as much as he was growing on me, I was still a bit leery. Only because he was a regular guy. Not someone that looked or even dressed as a female, like I had known before. Oddly enough, even though I was still having reservations about being with him, I was finding myself more and more intrigued by him and liked the slower pace this was developing at.
A lot of late-night thoughts and fantasies started running through my head. I wondered what he kissed like. What he looked like naked. How big his dick was. Did he shave down there? I started to feel those tingly little feelings in the pit of my stomach thinking about him and where this could lead. It didn't take long after our third date to have all my questions answered. And to start the life I was looking for.
We went to dinner and afterward, Jeff asked me if I would like to go see a live band, he followed at a larger outdoor bar and grill. I was up for the adventure and thought it might be more fun than just sitting around chatting. We ended up driving for a bit eventually pulling into the far back parking lot. Inside the bar, there was a four-piece band playing covers from the '70s and '80s. An era of music I am all too familiar with. Jeff and I sat way in the back and had a few drinks, enjoying the beautiful fall evening, and listening to the music. At one point during the evening, after it turned dark, Jeff reached over and placed his hand on top of mine. I looked down, almost in disbelief that he was doing it, but also very excited he had shown some affection to me.
I wasn't worried about anyone seeing us holding hands or being affectionate, I was just happy his interest in me was growing, as my interest in him was developing. Throughout the remainder of the night, Jeff and I sat hand in hand. Or arm in arm. We leaned in closer to each other and were having to talk in each other's ears because the music was loud. But it was nice to be there with him, becoming closer to him and having that romantic warm touching that lovers do.
As the night drew to a close, Jeff still had to drive me back to the restaurant where my car was at. As we got into his car and drove away, I leaned into him up against his shoulder. His right arm was interlocked with my left arm and we were hand in hand. And I was - without a doubt - becoming excited. Even though this wasn't whom I had envisioned my newfound homosexuality was going to be with. I was happy he had spent the time and energy pursuing me.
I was hoping that at minimum tonight we were going to have that first kiss. I wanted to see what it felt like to kiss the average man. I was actually ready to try. To have that moment of lust and desire and move to that first true display of affection. And in some way hoping my wants would soon become fulfilled.
As we arrived in the big strip mall lot where my car was Jeff parked in the outlying middle part of the lot with the back of his car facing traffic, which was hidden by bushes. The lot was still fairly full and busy, but he found a nice little area, where no one was near us. He leaned into me just after he turned the car off and placed a long slow closed-lip kiss on my lips. It was rather unexpected in the aspect that he "went for it", but this was what I was hoping for, so I was glad he did.
As he pulled away, we sat quietly and just looked into the eyes of each other. His handsome face, his light skin, his perfect nose just starring back at me. And that's when I realized, I was more than just casually interested in him. I was interested in him. I wanted this and I wanted him. I moved my head forward, closing my eyes as I approached, and placed my lips on his. When our mouths parted, his tongue softly and gently touched mine and the passion began. His kiss was soft but meaningful. Manly if you will. Strong but not overbearing.
His breath quickened, as did mine, as we dove deeper into the moment by coming even closer to one another. I had been longing for this for a long time in my life Albeit in my head it would have been with someone more feminine or at least who looked and dressed feminine, but at this moment, I was overcome with happiness and desire.
Our kiss continued for minutes on end. No words were spoken, and no breaks were taken. The more we delved deeper into one another the more turned on I got. I was overstimulated and so aroused that all of the memories of "male" counterparts I had before all came rushing back. The feeling of being alive and overly excited. The finding of a hard dick between her legs. The leaning down, or getting on my knees to suck her dick. The feeling of that hard cock sliding in and out of my mouth. The feeling of her mouth wrapped around mine and both of us (on occasion anyway) penetrating each other deep and hard doubled my desire.
