Asking Matthew

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."

We went back and forth that night and following nights trying to figure out a date and time, finally setting a night aside that worked for both of us. Later evening Thursday night he came over after work and dinner. I was so nervous when I saw his car pull up in front of the house. Heightened even more as I watched him walk up my walkway to the front door. I thought to myself, I'm really doing this!

Here's a guy that years ago would have fucked me right at the party we were at. Hit on me for weeks trying to get me alone, who I turned down. And now that I want dick so bad, that I could taste it; that I invited him over for a blow job and he's come over.

Matthew entered my house and we sat on my couch for a while just catching up. The conversation was good and flowing, but I knew we were both nervous, knowing why we were here. Finally, I got up and excused myself heading to my room, grabbing a bottle of lube from my drawer. I wasn't expecting anal sex or anything, but figured I may need it incase I had to stroke him off during it.

As I retuned to the front room, I spoke, "Alrighty Matthew, I guess I should honor my word and do as I promised."

He had that Deer in the headlights look on his face as he adjusted his body slightly to sit more upright on the cushion. I moved my coffee table out of the way and got down onto my knees right in front of him. The lube bottle in my hand.

"I am a bit nervous about this Matthew, just so you know." I spoke.

"I am too." He replied.

I leaned in and unbuckled his belt. He shifted his hips a bit more as I unbuttoned and unzipped his pants. I grabbed his pants at the sides, by the waistline and slid them down and off. He looked ghostly white and almost panicked as if this was his first gay experience.

"You alright with this is asked?" As he sat in his purple boxers.

"Yah, so far." He replied.

I ran my hands up and down his legs and upper thighs, just trying to alleviate some of his nervousness, as well as mine. My hand lightly glided further and further up, until I was rubbing over his cock and balls with the palm of my hand. I could feel his bulge, but he wasn't hard yet. I had a bit of a "tingle" going on in my pants, but I was so nervous, that I wasn't fully hard either.

When it was time, I slid Matthew's underwear off. His legs opened back up revealing his cock hanging down over his balls. He was partially hard, but like me, was probably too nervous to get fully erect. He had shaved his balls and trimmed the top, but still had a patch of hair over the base. It looked so erotic and sexy to be looking down a man's legs again, seeing a dick. My mouth watered and my heart raced.

I popped open the lube bottle and poured a bit out onto my palm. I reached in and grabbed his shaft and started slowly stroking it. I was looking up at him, as he sat there with this panicked glazed look on his face, as his cock slid through my hand. I didn't want to kiss him, or have some heated make-out session. I just wanted to suck his cock and make him cum.

As he got harder and harder, I focused my attention on my hand sliding up and down his cock. How erotic it felt having it in my hand as I slowly stroked him, getting him more and more turned on. Seeing his cock sliding up and down inside my hand, the tip poking out, his balls hanging below, made me hornier than I had been in a long time. I could hear faint little whimpers and even now and then, he'd mumble; "Yah, just like that."

I was getting harder, but still wasn't fully erect or fully turned on. This was my first cock in over a decade, so I was just focused in on playing with him and touching him. When I knew the time was right, I edged myself in further. I leaned down and placed his cock into my mouth. It slid all the way in without resistance. The lube, coupled with my saliva, made it slide in easily.

I was so excited to have a hard dick in my mouth again. I felt Matthew's hand come down and rest on the top of my head, as he edged his ass cheeks down the couch a bit further. "Oh yah, just like that." He moaned out as I slowly started bobbing up ad down.

I wanted to make this last a long, long time. I wanted to make this the best blowjob he ever had. I picked up my pace a bit and started thrusting my head up and down faster and faster, as he breathing and moans increased.

I was so proud of myself. Even though I wasn't all that interested in him, in the sense of being a boyfriend; I was sucking cock and I was going to make him cum. I was starting to let the fear and anxiousness release as I bobbed up and down. I stopped at points when his cock was deep in my throat and just held it there for a few seconds, feeling my mouth encompassing every inch of him. Then I would slowly pull my head back upwards, letting his while shaft slide out. Then ramming it in and out of my throat as hard as I could.

About half way through I pulled his dick out of my mouth, looked up at him and asked, "How am I doing?"

"It's perfect." He replied.

I dipped my head back down, hoping to be down there sucking his cock for another 10 to 15 minutes more. I wasn't done! I have been wanting this for so long. Dreaming about this moment, where I was down on my knees giving head again. It was so erotic, so taboo and such a turn on knowing it was my mouth, my lips and my tongue wrapped around his cock. I wasn't ready for him to finish. But I wanted to suck him dry. I wanted to suck him until his skin was raw. I wanted to be rock hard in my pants, getting more and more excited, while I was awaiting his cum! I was being the blow job bitch! And the more I was sucking his cock, the more I wanted cock permanently!

"Oh yah!" He moaned out. "Just like that."

"Aggghhh, you're gonna make me cum." He whispered deeply.

I could feel my cock getting hard in my pants and I wanted him to tell me to bend over and ram his cock inside me. I wanted his cum down my throat; or all over my face. I wanted it all! Oh, my fucking God I wanted this!

"Yah suck it... fucking suck it." He moaned out. As my head kept bobbing up and down on his hard cock.

"I'm gonna cum. I'm gonna cum," he started stuttering out, as I continued slobbering up and down on his cock.

Before he could get the next words out, I felt the ooze of his cum hitting my tongue and cheeks. I was so surprised he came so fast, but yet excited that he was cumming in my mouth. I swallowed the first big blasts down, as I kept sliding my mouth up and down his cock, tasting the last bits he was shooting out.

"Fuck!" He moaned out. As he kept dripping his salty, warm sticky load into my mouth.

I was fully erect by this time and just being on my knees sucking dick for the 3 minutes or so that I was blowing him, coupled with feeling him shooting his load down my throat, brought back all the times of my previous experiences. I wanted a cock in my ass so bad! I needed him to be behind me ramming me as I shoot my load all over the bed. I wanted him sucking me off. But he had just cum and I knew he wasn't going to be able to fuck me.

I slowly and deeply slid up and down on his cock getting every last drop, until I knew he had finished. I pulled his cock from my mouth as I looked up at him. I licked my lips and swallowed down the last drops.

"How was it?" I asked.

"It was fucking great!" He replied. "Best blow job, I've had in a long time. You're amazing at it."

"Thanks." I replied.

I knelt there starring at his cock, still fully erect, still glistening with my saliva, the lube and remnants of his cum. I wanted to just keep going. Keep playing with it, keep sucking it, getting my fill of it and keep making him shoot load after load. But I knew (as all men do), that it would be a while until he was ready to go again.

"Whew!" He choked out, as he laid his head back onto the cushion, catching his breath.

"Wow!" he said. "That was wild."

I knelt down in front of him for a while longer, just watching his cock turn flaccid and seeing liquid pooling at the base.

"Let me get you something to clean up with." I spoke, as I got up from my knees.

I went to the linen closet and grabbed a small hand towel returning to him.

Matthew wiped himself clean and handed me the towel back.

I sat down on the couch next to him, almost proud and gloating that I had just sucked his dick and made him cum pretty fast.

"So, How'd I do?" I asked.

"I wouldn't change a thing." He replied. "You surely know how to give head." He furthered.

Matthew and I sat talking a bit more. He literally didn't put his underwear or his pants back on until just before he left. It was rather erotic sitting on my couch, starting at his half naked body (bottom down), as we talked more.

After he left, I straightened up and went to bed. I did stroke myself off that night thinking about his cock. How it felt in my hand. How it felt in my mouth and how I could still taste him cum dancing around my mouth. I wanted more. I wanted to call him and tell him to come back and fuck me, but it wasn't the right time. I got off pretty quickly thinking of him and I swallowed down my own cum that night.

I fell asleep naked fairly quickly after masturbating, with cock on my mind. I had wanted it for so long, it was a relief to finally get some. But now I wanted more. No, I needed more and I had to have more experiences. And I needed a boyfriend!

Thankfully Matthew was happy to help.

I'll tell you all about our second night in the next chapter.