I Became a Coc Sucing Fag

I became a cock sucking fag Pt 7

Jillian and I began to develop after our first night together alone, where we gave each other head. Our conversations continued getting deeper and I began seeing her when we both had the free time. As time went on, the fear of sucking dick, or being in a gay relationship (behind closed doors) subsided for me. I never mentioned her to anyone, and I never took her places I would have suspected I would run into anyone I knew. It was truly a fluent, ongoing sexual situation and I digested it very well, knowing she was - at that point - exactly what I was looking for. At least for the first few months anyway.

I was becoming more intrigued by the situation. I became even more aroused and incredibly interested in dick. I liked kissing her and feeling those fake tits, but I also really liked sliding her dick in my mouth, and by the third time we had oral sex, I did swallow her cum. As much as I was a coward by not doing it the first few times, it became customary and was something I looked forward to. I got excited when her hard dick would pop out of those panties. It absolutely amazed me to reach into her pants and feel that hard shaft. And because of my curiosity and developing interests, I was usually the first one going down and liked trying new things while sucking her dick. I like getting my hand full of lube and just jacking her off, listening to her moan and groan as I brought her to orgasm. I was becoming a cock addict and her dick was my drug of choice.

When it came to porn, I had shifted my viewing pleasure from just Shemale porn, to what some would call transvestite porn. When Jillian wasn't around, and the mood struck I was at my computer watching older videos of the true first generation of crossdressers and shemales, usually fucking or being fucked by the men they were with. All of them dressed as hot women, but having that something extra. It was riveting. I was always hard and had always put myself in the guy's shoes when watching it, so I could be the one pumping a shemales tight ass with my dick, while she was moaning and groaning. I became so enthralled by dick, that I rarely found myself seeking female connections and just really wanted Jillian's and I's relationship to continue. All I wanted was cock!

After a few months had gone by, Jillian and I had oral sex probably 7 or 8 times. And we had advanced from blowing each other, one at a time, to mutual or 69-type positions where we were both sucking each other off at the same time. There was no doubt, I was becoming cock crazy with her and I wished I could have been with her more. I learned what she liked, or didn't when it came to blow jobs. How fast, or slow, how tight I had to do it to please her more. How her hard dick felt in my mouth. Where I liked her to cum. What positions we liked best and how we both tried to make each other cum at the same time. She adjusted to my likes as well. It was incredible to have a mouthful of her hard dick, as she had a mouthful of mine. I especially liked it when she came on my face, just as I was finishing up blowing her. All the things I wanted to try; we did.

But at that point, I had never been in this type of setting before. As much as I was learning and evolving my desires, becoming more fascinated, I was also becoming more concerned about where this was going. Many of the videos I watched, strengthened my desires because I wanted to emulate the actors and be on top of my shemale seeing her dick lying there, as I watched my dick sliding in and out of her ass. Or even as exciting would have been feeling her fucking me, as my dick was hard and in my hand. It was all so exciting, but yet had not even come close to happening with Jilian. But I wanted it to happen.

One afternoon when she was by me, we were fooling around in my bedroom, and I was chest down on my bed, between her legs, with my head bobbing up and down sucking her dick. She was naked, propped up on pillows looking down watching me. I was overly aroused when I would feel her dick get hard in my mouth and she would whimper and huff as I was sucking her off.

I wanted to be penetrated and I had not asked her whether she was into that or not, but today, I wanted to feel her inside of me. After giving her head for a while, knowing she was fully erect and fully aroused, I reached over to my nightstand and pulled out a small bottle of lube and a condom. I went back to sucking her off, but just before I put her dick back in my mouth, I dribble a few drops of the lube on the tip of her dick and some on my fingers.

As I slid her dick back into my mouth, I reached behind me with my lubed-up fingers and started playing with my ass, getting myself ready for it. I was nervous, I was still unsure, but I had an overwhelming desire to feel a real dick in me, instead of my toys. When I felt I was ready, I opened the condom and slid it down Jillian's dick. I squirted some more lube on it and jacked her off, getting it all slippery wet. I started to climb up on top of her, so I could ride her. Just as I got ready to slide her into me, she started going soft. She whispered out, "It's been a long time since I fucked someone. It might not work."

I tried several times to get her inside me, but she was more limp than hard, so it wasn't going to work. We were both nervous and scared, so instead of trying to force it, I climbed off of her and laid down next to her. We started kissing and touching, just slowing the moment down. I was jacking her off, trying to get her fully erect again, so she could slide it in me. Her hand had reached down and she was pulling on my dick as well, trying to get excited about the moment.

Jilian whispered, "Let me do it from behind, I'll probably have a better chance."

We adjusted our positions and I shifted to be on all fours, my ass in the air and her sliding in behind me, getting ready to fuck me. I could tell she was stroking herself trying to stay completely hard and after a few unsuccessful attempts, I felt her slide inside of me. It was beyond enlightening to feel her dick slide deep inside of me. There was a feeling of pressure, I'm sure from me being beyond tight. It was somewhat painful and uncomfortable, because as much I thought all the years of toys had prepared me for anal sex, the fear and apprehension of her putting her dick into me, had made me rear clamp shut. But once she was in and started slowly pumping back and forth at her pace, I felt a feeling I hadn't with any toy. And that feeling was a real dick inside me. I was excited about it.

Sadly, Jillian was only in me for about a minute and a half, until I felt that solid bone of hers, become soft and she slid out of me. I was disappointed, feeling like maybe this wasn't attractive or arousing for her. I surely hoped she hadn't cum that quickly and was already done. But just as I was turning my head back towards her, she spoke out, "I'm not good at fucking. Just being fucked."

It's okay. I replied. "I know this can be difficult." I furthered.

I spun around and lay flat on my back just underneath her as she knelt on the bed. I reached out and slid the condom off of her soft hanging dick and I slid her dick back into my mouth. Even if she couldn't fuck me, I still wanted her to know, I enjoyed her and her dick and I wanted her to cum. We adjusted accordingly and Jillian and I settled into a top/bottom 69 and were continuing to suck each other off simultaneously when she pulled my dick from her mouth and asked; "Do you want to try fucking me?"

"Yes." I groaned out, as my dick got even harder.

Jillian got up on all fours and raised her ass high in the air. It was a wild sight when I climbed in behind her and looked at her ass staring at me in the face. The same position I had seen many of the women I had fucked in the ass before. But, this time, there was a big long hanging set of balls under that hole, instead of the back side of a pussy, and it kind of threw me off.

I did my best to keep myself fully erect and slide the condom on and I did manage to slide inside of her, but fears and concerns about fucking "a guy" in the ass and HIV took over my brain function and gave me the same fading hard-on she had when entering me. I had to pull out of her and just focus on getting myself fully erect again. I took a moment to catch my breath and stroked myself a while until I was fully hard again. I got in behind her tightly, slid my dick back into her, and started pumping her ass. I watched my dick go in and out of her and for a brief moment I felt like one of those porn actors, banging his shemale girlfriend. But as my luck would have it, about 3 minutes in, I felt I was going to explode. I started moaning, I was getting close, and Jillian groaned out, "Cum in my baby. Cum in me." Which turned me on even more and sent my pumping motion faster

Seconds later as I was pumping her hard and fast, I started cumming inside of her ass and I enjoyed the feeling of releasing deep inside of her, instead of just in her mouth. It had been the first time I had cum inside someone in some time, so it was a great feeling to be in her.

When I withdrew my cock, the condom hung low with my cum all nestled at the tip and my dick was slowly getting soft as the seconds ticked by. Jillian rolled over onto her back again, her dick was flaccid and just lying across her balls. She put her knees up and spread her legs a bit and I almost felt like I had disappointed her because I had not fucked her for longer, like 10 or 15 minutes.

"I have to get you off too," I spoke out as I lowered my body back onto my chest and up towards her body.

I kissed my way up her thighs just staring at her dick, sitting, waiting for me to play with it. When I got close enough, I slid it back into my mouth. It was soft, small, and flaccid but I had so much desire to suck on her and make her happy. I continued sliding it back and forth until she became rock-hard again. I sucked her off for the better part of 5 minutes, getting her fully hard, fully aroused, and ready to cum, before she finally squirted every bit of her cum deep down my throat.

When I finished and wiped my lips clean, Jillian pulled me up to her and apologized for not being able to fuck me. I told her it was alright and I also apologized for being so quick, justifying it was my first anal with someone like her, and I was excited.

After we both realized the new boundaries of our relationship, we agreed it was best to just keep sucking each other's dicks, instead of forcing anal sex. But if or when that time arrived, we'd be open to the experience.

I won't go on too much further with Jillian, because I could write chapter upon chapter of our sex tales, but it doesn't get us to where I am at in life. My experiences with her were amazing, as scary as they were sometimes, it opened a lot of doors for me and gave me - what I would call - my first gay lover. She truly started my journey to being a cock sucker and gave me the opportunity, in the privacy of our accords, to suck her dick and become more accustomed to that lifestyle.

But I can say this. In the seven months that we dated, I felt at times I was dating Dr. Jekyll or Mrs. Hyde. There were moments with her that were so calm and peaceful, loving and sensual, which were incredible. But there were times when she'd disappear for days on end without calling or texting only to re-appear and scream and yell at me because of her insurmountable fears. She'd break up with me, but then come crawling back to me days later only for us to have some fantastic, dick-sucking nights with big orgasms like we never had before. It was a wild ride, no pun intended.

By the time Jillian and I quit dating, I had fucked her in the ass one other time, and I sucked her dick (maybe) 30 times in those seven months. I don't believe I ever had that "I'm in love" or hot erotic porn scene with her like I wanted. She never fucked me again and that was one of the biggest issues I had about us. As much as I would have wanted to be fucking her more frequently, she couldn't give it to me. And I wanted it. I know in some detail I make it seem like every weekend I had her dick in my mouth and that just wasn't the case. There were times I didn't see her for at least a week, sometimes two, and it drove a wedge through my internal thoughts of having a homosexual relationship, versus just dating women.

I wanted to have that "gay" relationship. I wanted to be more invested in my development. But as time went on, I could tell she was keeping me at arms distance, and with all of her fears and concerns, along with some of mine, which introduced some very angry, defensive, counterproductive debates, which just led to more time apart. The whole situation just ended up being more of a friends-with-benefits than an actual loving, dating relationship.

I liked sucking her dick and making her cum. But I also needed to know what it was like to be fucked. And I mean fucked. Hard, long, deep, and have someone cum inside of me, just as I would cum inside of them. And that wasn't going to be her.

The biggest issue for her was that she was never going to be a woman. She always felt that no matter who she dated, she was never going to be loved, admired, and accepted as if she were a real female. A real girlfriend or even daughter-in-law. And I understood that. She even asked me during one argument if I had mentioned dating her to my parents. My answer was no. She then asked me if I planned on it and I related to her that at that point I hadn't considered it yet. "You get my point," She spewed out as she grabbed her purse and left.

If she and I had been more permanent, I probably would have told everybody, including my parents. But, just as much as she felt she couldn't be a true female, which was concerning to me, I understood her. She also had to understand that this was my first gay relationship, and I was unsure how I would tell anyone I had a girlfriend who had a dick. I mean how do you breach that conversation? And somehow, looking back now, I don't know if she ever told her friends or family about me. Maybe it was a double-edged sword.

Either way, I wasn't ready to come out. I still wanted women, but I wanted someone like her as well. She was, in all reality my first step. And if we would have been so in love, that we couldn't have lived without one another, I would have taken that step. We just hadn't gotten there. I did come out years later as bisexual. But, at that moment, I wasn't ready. And she knew it. So maybe her fears were justified. If I had met her now, at this point in my life, we would have never had these issues. But back then, as much as I was enjoying being something different, trying something different, and wanting something different. I wasn't as open as I probably should have been.

Luckily for me, I learned one pointer from Jillian when it came to finding shemales on dating apps, which panned out almost immediately. I messaged and started talking to a "girl" named Geenah and I quickly realized she was a shemale too.

She was dick number two after Chuck, and she gave me more of what I needed, albeit through a pack of lies, which sent me back to women for a while, but she gave me more anal experiences and some lustful nights. For her portion of this story, I'll briefly regale you with some tales of her in the next couple of chapters.

But the heart of the matter and what turned me towards men for good was fucking my aunt. Yes, you read that right, fucking my aunt. You'll understand when you read the story, a few chapters away.

After that a brief tale of Tianna, the third shemale.

Then a gay acquaintance of mine named John who I ended up blowing frequently; and finally meeting Christian my current boyfriend.

I know I sound like a male bimbo here with a list of names, but it was a slow drawn-out process that led me to be the cock sucking fag I am today. But for now, let's talk about Geenah.