Asking Matthew part 1.
I always knew I was Bi-Sexual. I got turned on by seeing naked men in pictures or videos, just as much as I did women. I just never had the chance to explore my desires. In my era, my generation, you weren't gay. You weren't Bi. It was frowned upon, looked down upon, ridiculed and chastised. So, I went along with thoughts of the era and did what I had to do to be a "regular" guy. And I didn't mind. I liked women, I loved sex with them, so it was never much of an issue. That was until my marriage failed.
I had met and befriended a Transgender girl and had several sexual experiences with her. It was enlightening to say the least. To have all the fantasies, all my intimate thoughts, all the desires finally fulfilled, was beyond my imagination. And honestly it was scary, it was odd. It was different, it was taboo. But I liked it and I wanted more. I did date other trans girls and a few crossdressers for a while after, but never had the connection I was seeking. In most of those relationship I was always the top. Giving, instead of receiving. Of course, I'd suck dick and make "her" cum, but I never had been fucked.
That was until a coworker of mine, seduced me one night and I became the bottom. The receiver. And you know what? I fucking loved it. That relationship lasted a few months and I got fucked a lot by him. He was the first man that ever penetrated me. We'd always start off orally blowing each other, but when he would get completely hard and passionate, he'd put me on my knees and ram his cock in and out of me. Usually, I would end up cumming all over the bed, or floor, as he was cumming deep inside of me. Throughout that relationship, I began to realize, I liked cock more than pussy.
I had danced around the thoughts of just dating men forever and forgoing women. But, after those experiences were over, I met girl after girl and was in what some may consider the "perfect heterosexual" relationships. So, Homosexuality or at least Bi-Sexuality never crossed my mind too often. Especially after I got married to my wife. But once that failed and I was out on my own again, those deep repressed feelings came back to life. They were even more enhanced when I began an infatuation with Matthew.
A bit of a back story.
I started playing pool on a league sponsored by a local bar. There were about 12 teams of two men / women each and we would compete weekly against the other teams in six games of 9 ball. I played on that league for years which is where I met Matthew. I knew Matthew was gay, but as I got to know him, I learned he was married to his long-term partner. I never thought much about it; or him for that matter, until I was drunk one night at a party.
The host of the league - on occasion -- would have summer BBQ's or card parties at his house and since most of the people on the league had known each other for years, we would attend the parties. One night I went to one of the BBQs to hang out and have some weekend fun. After a several drinks and a few heated games of beer pong, I was a wee bit tipsier than I should have been. I was hanging out at the improvised bar the host had set up, sitting next to Matthew. We were just shooting the breeze when he asked me why I didn't bring my girlfriend with. I explained in short detail, that we weren't doing very well and weren't probably going to make it much longer.
For some odd reason my "personal information filter" which usually works well; had been shut off by alcohol, when I slipped and said, "I should probably just start dating men again."
I think Matthew about spit out his sip of beer, pausing to stare at me. I had to follow up; and I had to explain that statement. There wasn't any way around it. So, I said, "Yes, Matthew I have dated men before."
"Really?" He asked. As if I had told him I wanted to blow him right there on the spot. He tried hounding me for more information, but I shut the conversation down by simply replying; "Yes, I have. But it was a long time ago."
The night went on and nothing happened. I eventually sobered up enough to drive home and didn't think much of it.
However, over the next two to three months there wasn't a Friday or Saturday night that I was getting a late-night text message from Matthew reading things like... "Hey, I'm almost done at the bar. Want some company?" Or, "Hey If you want, I can come by and hang out, maybe naked a little later."
I was flattered and it was nice to have a man send me messages who was clearly interested in having sex with me. And as much as I wanted a man again, I felt it was too close to home. To many people in our circle of friends who knew us intimately may think ill of the situation. Let alone, all the people on the league! Moreover, even if it was a onetime thing, or a fling, I would have had to see him weekly, even if our secret never came out, I would have been uncomfortable with it. Plus, he was married and I wasn't going to get involved with that. So, I politely told him time and time again (trying not to bust his ego) that I just wasn't interested and it was too close to our group. Furthering that I was still working on things with my girlfriend, so I wasn't going to take that chance.
I wasn't ashamed of my Bi-Sexuality, or being "out", I just didn't think he was the right fit. Knowing at the time that the GF and I weren't doing so well, I was actually hoping to meet a man or another TG, or CD to start a new relationship with. I wanted dick. I wanted to be loved in that way. I wanted to be giving head, or being fucked. I had all the toys in the world and a closet full of transgendered porn, but I just wasn't too keen on him. For whatever reason, I just wasn't.
Fast forward about 3 years.
I quit playing on the league that fall after our season ended. There were some new people that joined that I wasn't overly fond of and my partner was having scheduling issues, so it was time to move forward. I did keep in contact with some of the players on the league and time to time I would head to the bar on a Friday or Saturday to hang out with them and just shoot some pool or play darts for fun. It was always nice to see everyone and get out, but I was relieved that I didn't have the weekly pressures and commitment concerns that I once had to deal with.
By the time I started hanging back out again and going to see everyone, Matthew had separated from his long-term partner. I guess things weren't working out for them and Matthew had just gotten his own place. He told me about it in bits and pieces, but never revealed the whole story. Moreover, and thankfully, he never tried hitting on me, or tried sleeping with me. I guess he figured I had turned him down years ago, so why try now. But what he didn't realize is that I had been single for a while and I was looking for some more gay experiences and looking for dick again.
Months went by and on occasion I'd get a stray text from Matthew telling me people were heading to the bar, or to someone's house for a card game. But, in all reality Matthew kept his distance, in regards to trying to date me, or have sex. But as the time went on and the more, I was out looking for a boyfriend, or at least a Friends with Benefits, I started wanting him. But I didn't know if he wanted me anymore. Let alone (if he did) how I could get him alone away from the group. So, I concocted a plan.
Yes, as wrong as it was, I concocted a plan. I text Matthew one night and asked him for a favor. I explained in light detail that, "I was interested in a man I had met online," even though, there was no man I had met. I further explained that it had been a long time since I had been with a man and I was somewhat scared and apprehensive about having sex. More importantly how nervous I was about giving a blow job. So, I asked him for some pointers.
Matthew and I spent weeks texting back and forth and I was listening to his advice, but what I was really trying to do was to get him to "volunteer" to get sucked off, but he never got the hint. We did send naked pictures back and forth on occasion, but strikingly enough, he never asked me out or asked to come over. I jacked off to his pictures quite a few times and loved the fact that his cock, looked really similar to mine, just maybe a half inch longer. And I loved the fact that I was truly more interested in boys than I was girls. Finally, I got brazen enough to just outright ask him...
"Hey." I wrote on text. "I know it's a strange question, but do you think I could give you a blow job? And while I'm doing it, you can tell me what I'm doing right or wrong."
I followed up with; "I normally wouldn't ask anything like this. But you are the only gay guy I know. You don't have to return the favor. I just want to see what it's like to suck dick again. Would you mind? I know it's odd question ask."
"Yah." He wrote back. "I think we could do that."
