I sent her the video pt. 1
During my life, I have had the pleasure of dating both men and women. And in most cases, the "men" were mostly crossdressers or transgendered females, with one average male set into the mix. But I am getting ahead of myself here and need to back up a bit.
During the coming-of-age years, it had always dated women. And I was good at it. And good at getting them into bed. But deep in the recesses of my mind, I knew I had a lust for more. Something different, something unique, something taboo. And like most American men, I found the woman I loved, married, had children, and was working towards that suburban house, with the white picket fence and the pets. But I always knew I was different; I just never had the chance to explore it. That is until I left the "American dream" behind and tried new things. After about 8 years of marriage and some beautiful children, the wife and I didn't get along anymore. So, to stop the arguing and animosity between us, we agreed to split and start our lives over.
After the wife and I went our separate ways, I was introduced to a female whom I thought was genetically a female. But after getting to know her through ongoing conversations, I learned she was transgendered. Of course, when the chance came for us to be more than friends. I jumped at the opportunity. I dated her for almost a year. After we split, I found another transgendered woman shortly after and dated her for over a year. It was extremely enlightening and exciting to date a woman, with that something special. That something extra. A hard cock! And as much as I was loving both situations. I kept my love affairs to myself.
I kept things and these love affairs to myself for many reasons. Not too many people knew of this love(s) I had and even fewer knew of my newfound sexuality. But I have to tell you how much I enjoyed cock and giving head and even being fucked. Sadly, all of them fell short of what one may call a long-term relationship. And I surely never dated anyone long enough to consider them as my boyfriend. Coupled with the fact that my family was very religious and conservative, so to have one of their sons be "gay" or "Bi-Sexual" was unheard of and something I wasn't ready to deal with. Which isn't part of the story, just setting a bit of a background for the readers.
Long after my divorce and my second coming of "single years" I met a woman who was going through a tumultuous marriage, and was on the edge of a divorce. Seems her husband was abusive, a narcissist, and an overall possessive, judgmental, controlling ass. She married him out of pressure from her family, bought the house, popped out a few kids, and just dealt with his behaviors and attitudes because she felt there was no other way. But she was also living the lie.
When I met Amanda, she was almost 45. Her kids were almost teenagers and she had been married for about 15 years. She hated her life but would portray herself as the perfect wife, with the perfect life. But I saw right through it. She worked late every day at her job, even though she was off at 4:00 P.M. She would go out with friends as much as possible, just to get away from him and the home life she hated so much. She loved her kids and would do anything for them, but as she told me, heading home to him, was something that made her life more miserable than it already was.
As time grew on and we chatted more, she began to regale me with tales of her single years through college and the wild parties she would attend, the dating relationships she had and the fun her life used to be before she married "him". One night she slipped and mentioned having slept with a woman. Well, of course, that got my attention. Now I had threesomes before in dating relationships, as experiments, but never really found a female who was truly Bi-Sexual. So, when she let that little gem slip, I questioned her like I was investigating a homicide. Turns out as I later learned she was openly Bi-Sexual, at least to certain family members and friends. But strikingly enough, not to her husband.
Amanda told me the whole tale and I must admit it was pretty erotic hearing in full detail how she met a female and through some time, grew a lust for her, and one night when they were alone, she had sex with her. I was rather aroused and wished I had been a fly on the wall to see that. But that's not where her story ended.
According to her tales, over the course of the next few years, all while trying to avoid marrying a man her family had chosen (a religious and ethnic thing), she had the opportunity to sleep with a few other females. Seems the few experiences with the first girl had led her to want more. So, through luck (as it always seems to be) and meeting the right person, she managed to have 3 other "girlfriends" before settling down.
Amanda told me how much they meant to her and how she missed a woman's touch, eating pussy, and being in that type of situation. Apparently, Amanda felt the same as I did. She knew she was different and liked different things and managed to explore sexually as I had, but couldn't come out because of her parents and religious upbringing. She admitted several times that if it wasn't for her family and their old-world beliefs, she would have probably dated women more, and dated them more openly. In all honesty, we were the proverbial twins separated at birth, when it came to our sexual desires and experiences.
Since she was kind enough and open enough to share her experiences with me, I decided to open up about mine. Amanda was floored when I told her about my first gay experience with a transgendered girl. And she wasn't floored because she thought it was grotesque or disgusting. She was floored because she thought it was hot, sexual, and erotic and she fucking loved it. She drilled me like I had drilled her for answers. Question after question until I couldn't think anymore. When she finally asked the right question, "Did you have more than one experience?" I admitted to all I had done. And the fascination from her about my sexual experiences deepened, as it did mine about hers.
During the time of our deep and widening conversations, we developed a lust for one another and it wasn't long until the dirty erotic texts began between us. Followed by naked pictures and brief video clips of each of us masturbating and thinking about the other. And as time drew on, we started sleeping together, in the hopes that one day it could be her and I and we could lead a more open, lustful, loving, heartfelt, sexual situation. But as sad as it was, I felt until she was divorced and done with her marriage, I did not want to be the second fiddle. So, I cut that aspect of our relationship off. We agreed to stay friends and to still be in each other's lives, but just as we were before.
Life changed for me just a few months later when I had the chance to move for work, taking on a promotion in another state. My kids were old enough to be on their own and I wanted to break free from the stagnant little piece of the world I called home. I took the job and moved to start all over. But that's when doors opened for me, I hadn't been able to have back home.
Amanda and I spent one last night together before I left. It was a night of passion, sexuality, and fun as we just ravaged each other before she left to go home. She was crying as she sat in her car, probably believing this was going to be the last time we'd ever see each other. I was saddened too, but I couldn't wait anymore. I had a life-changing opportunity before me, and as much as I was going to miss my sons, who were on the cusp of starting their adult lives; and with their blessings, I left.
See back home with family, friends, and children nearby, I was never able to date whom I wanted - man wise - or have them be a more intricate part of my life. I had always wanted a boyfriend. I had always wanted to be in that gay relationship, even if it was just for a few months. I wanted it and I could never have it. I could have sex, but never the commitment. I never had the overnights. The going places together, being out in public as a happy loving couple. But now here in my new home, thousands of miles away from the ever-prying eyes. I could. And I did.
As soon as I got to Florida, I felt free. I was away from my family, and their outdated ideals. My ex-wife and other things which were holding me back. And I was going to change my life to be what I had always wanted it to be. And since I felt that I had lost the love of my life, my focus was to find that boyfriend and be sucking dick in a full-time gay relationship.
I put myself on every gay and bisexual dating site I could find. I searched profile after profile of men, crossdressers, and transgendered women seeking that new perfect partner. It wasn't long until I received a message from a man named Jeff. Jeff was the only one that approached me with dignity and respect and seemed like a normal person. Jeff was a business account for a firm just outside of Miami. He reminded me of myself. He was in his mid-fifties. A bit overweight. Short brown hair, had to dress business casual for work and in his case, had been divorced from his husband for about 2 years.
We chatted a lot on the dating site, eventually switching over to text messages before we finally met. And even though I could admit he was an attractive man. I was still hoping for a transgendered woman "with that special part" which I have had before. But I figured as nice as he was and as flowing as our conversations were, he might be a good fit.
Jeff and I went on several dates before we had that first kiss. But when it happened, his kiss was deep and loving and through his kiss, I felt his interest and passion for me. Our first heated make-out session was after an outdoor local band concert, where a few too many fruity cocktails led to a long and intense goodnight kissing session ending up with me blowing him in his car. And him returning the favor. It was so hot and erotic sucking cock again and - in all reality - I was falling for him. Moreover, it was the first form of sex I had since being in Florida, so it was great to be with someone again.
Over the next few months, Jeff and I saw each other regularly and even though I had always been the "man" of my gay dating situations. This time, he was the man and I was the girl. And I liked it. I liked spending the night at his place, or him by mine. I liked giving him blow jobs and I liked when he climbed on top of me and fucked me missionary-style until he came in my ass. I was still hiding him from most of the world, especially when family or friends came to visit. Jeff would give me the space and time I needed to visit, without throwing a fit to be introduced to them. He understood their positions and let me have the privacy I needed. He knew all too well what it was like to come out at his pace and his time with his family and friends.
But Amanda knew it almost instantly. I told her all about him from the word go. Even though I was gone from St. Louis where she lived, she and I still talked regularly. Seemed not even 1000-plus miles could keep us away from each other. I know she was heartbroken, but she was honestly intrigued to know more about him. She wanted to see pictures of him, learn what he did, and how our relationship was developing. She was very happy for me that I was living the life I had wanted to lead for a while. Maybe in some aspects, she was living the life she wanted to lead through me.
One night when we were talking dirty about the sex, I was having with Jeff she wrote, "I wish I was a fly on the wall to see you sucking his cock." And even though I chuckled at those words, they gave me an idea.
I was over at Jeff's a few nights later. We were just sitting on the couch relaxing when I remembered Amanda's text message. I wondered if he'd let me film it on my phone, while I was sucking his cock. I didn't want to come right out and ask. But I wanted to film it and send it to her. I got really turned on thinking about it and wanted to make it happen. I started slowly and seductively hitting on Jeff. I wanted to play this right.
I slid off of the couch and onto my knees in front of Jeff and was slowly rubbing up and down his legs over his dress pants. I was overly horny and very turned on thinking about giving him head and filming it. I unbuckled his belt tossing the leather to the sides. I reached in further and unbuttoned his pants and unzipped the zipper. His smile was wide and glowing because he knew I was going to suck his dick.
Jeff lifted his hips slightly and I pulled his pants down off of his body. I started rubbing my hands up and down his bare legs, getting closer and closer to his cock. His cute little brown boxers holding the dick I wanted more than anything.
"What brought this on?" He asked.
"I want to please you," I replied. "After your long day of work. Plus, I want your cock." I replied more trying to play this off as I just was horny.
"Can I ask you something, sweetie?" I mumbled to him.
"Sure, what's up?" He asked.
