Mikes First Transgendered Pt. 13
Nis 22, 2023 // By:analsex // No Comment
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Please read 1 — 12 before going reading this one.
After Cheryl and I parted ways, I changed jobs and started working for another Big Box Store. That’s when I met Katie. Katie was 5 years younger than I was. She had long blonde hair, big brown eyes, 44 D breasts, hips to match and wanted me like no other woman had. We spent weeks flirting, courting and talking about everything under the sun until I finally asked her out. Katie agreed and we went on our first date. Katie and I started a relationship and dated for just under 3 years until we finally parted ways. I ended the relationship, because of Katie’s lack of sexual experience(s), more like desire to try new things and just an overall sense of disappointment in where things were and where they were going. I never did tell Katie about my situation with Sara, Enna or Cheryl or my desire(s) for men. There were points throughout our relationship that I was infatuated with her, enjoyed making love to her and having pussy again. But somewhere in the deep recesses of my mind there was always the thoughts and longing for dick. I thought about asking her if she wanted two men at once, hoping we’d land a Bi-Guy and just taking advantage of the situation, pretending it was my first time, or something I wanted to try, seeing if it would lead to more. But I knew that wouldn’t be her cup of tea, so I kept it all to myself.
Since we worked together, through our years dating, I decided I did not want to be around Katie after we split up, so I changed jobs and started working for one of those Big Coffee Houses a short time later. I was there about a year, single, just living my life, hanging with friends and enjoying my time when things changed for me again. Almost every Sunday afternoon a usual customer would come in and order his drink, chat it up with my co-workers and I, get his drink and leave. I never really thought about it much until one day he asked me my name?
“I am Mike,” I told him.
He said, “HI, I am David.”
David was about my height 5’10, styled light brown hair, medium build, with brown eyes. He dressed business casual and was always friendly and a good tipper. I learned through conversations with him that David was in his mid-40’s and managed several businesses in the area. Over the next few weeks, we started talking more, but nothing that made me think of dating him. Besides most of my “gay sexual experiences” were with transgender women and an older softer / loving dominatrix, so I never saw myself with an average man. Until that one Sunday anyway.
As usual late Sunday morning David arrived for his coffee. He was wearing a cologne I had never smelled before and the scent was intoxicating. It caught my attention the minute he stepped up to the counter. I asked him. “What cologne are you wearing?”
He smiled and replied, “I don’t remember the name of it, it was a present from my old boyfriend.”
For some odd reason the term, “My old boyfriend” absolutely caught my attention, plus that cologne sent my brain and hormones into overload, so on his coffee cup I wrote, “Have a great day David, I’d love to chat more. Call me” And wrote my phone number down.
Later that night I got a text from David. He wrote; Mike, it’s David from the coffee house. I was surprised you wrote your number down, but happy you did. I’d love to chat more too. This is my number.
Over the next few weeks, we chatted back and forth pretty regularly via text. Of course, I’d see him when he came to pick up his coffee and we’d make small talk, but have great, deeper conversations via text. One day, David asked me if I wanted to meet for dinner one evening when I was off. Of course, (nervously) I agreed and looked forward to seeing him outside of work. I met David for our first dinner at a restaurant downtown. We had a nice quiet pasta dinner and spent some time chatting and getting to know each other better. He revealed to me that he was married right out of high school and had one little girl who was now 15. David told me, he knew about 7 years into his marriage that he was gay, finally told his wife and filed for divorce. David related right after his divorce he found a guy and dated him for a length of time, Pendik Escort but unfortunately “he was not the one.” David furthered by telling me he had dated a few men over the years, but still hadn’t found the connection he wanted. Throughout or messaging and getting to know one another David asked me about my sexuality. I admitted I was bi-sexual, or at least had experienced gay activities with a couple transgendered women, but usually ended back up with genetic girls afterwards. I didn’t want to reveal too much, because if we didn’t click, I didn’t want him hounding me for sex or blasting my personal information to my co-workers. But deep inside I was already developing an interest in him and was hoping things would develop.
After our “dinner date” David and I continued conversing through text and on occasion we would meet for drinks, play pool or shoot darts at a local bar. After a few weeks of spending more time with him, I found myself becoming extremely attracted to him. I started thinking about him more sexually than I had before and wondered if he felt the same about me. One night as we were leaving the bar, I gave him a hug and planted a kiss on his cheek. I think he was surprised but excited I had done that. I decided it was time to make my move. I wanted dick again and I was having those feelings of desiring homosexual sex and being in a homosexual relationship and hoped maybe he would be my next Boyfriend. I was concerned though, considering I have never dated an “average man”, but men who were more like women. But I decided I was going to take a shot and see what happens. I asked him out to dinner for the next Saturday night and booked us in to the finest steak house our town had to offer. The place is small and quaint, very poorly lit, very expensive, but I figured it was going to be the most “romantic spot” I could find.
I met David at his apartment complex and he drove to the restaurant. I dressed up more than usual for our date and cautiously flirted with him all night. Afterwards, we spent time in the restaurant bar, just having a few drinks talking more. I couldn’t believe I was out on a second date with a man I was interested in. I didn’t have to put too much effort into Sara, because she had asked me for sex and now, I was trying to maneuver through the red tape of “dating interest” to see if we had a spark between us. As the night progressed, I felt comfortable with him. I felt like there was an attraction and felt that maybe this was going to be my new man. I had fantasized about him and really started to feel the old feelings of wanting a “man” in my life. I was yearning for the taste of cum in my mouth, yearning for a hard cock in my ass and wanting to be in a similar situation that I was with Sara or Enna where I was cock crazy for someone.
As the night drew to a close, David said, “Common, I’ll drive you back to your car.”
I didn’t know what that meant? Was he disappointed in our night, or did he want to leave to head back to his place? Either way, we started making our way home. I wasn’t sure what to do when we got there. Should I try to kiss him goodnight? Will he try to kiss me? Should I just leave? What if he asks me in for a nightcap?
We pulled in the parking lot just as it was starting to rain, the only spot left in the complex parking lot was way in the far back corner, under an old broken street light. It was dark and quiet and I could feel the sexual tension and anxiety between us. I was turned on, nervous, anxious and very horny, but still wasn’t sure where this was going. David and I sat in the car for a bit, not wanting to run through the rain. We talked more and had a few cigarettes before beginning to make our dash onwards. Just as we were about to make our way out into the shitty weather. David stopped me and said, “Mike I’d like to talk to you about something before you go.”
“Sure, what’s up David.” I replied.
David said, “Over the past few weeks I have enjoyed having you in my life and I have become interested in you as more than a friend.”
I smiled at David and said, “I have to David, I have truly enjoyed our time together.”
I leaned onto my left hip to Kurtköy Escort face him more and placed my hand on top of his hand and looked into his eyes. I could tell he was scared and nervous, so I said to David, “Come here.”
I leaned towards him as he started leaning towards me and I kissed his lips. It was a closed lip kiss, but one that send excitement running through my bones. I felt giddy and the butterflies in my stomach began dancing. I had been missing dick in my life and now I am kissing a man I am interested in.
I pulled away from David to see him smile. I placed my right hand along the left side of his face and leaned in again. This time our lips parted and our tongues touched for the first time. I was so excited I nearly leapt out of my seat and onto his lap. I leaned further in towards him as our tongues swirled around each other’s mouth. I felt him place his hands on my arm as we continued engaged in this hot sexy romantic kiss. I felt my dick starting to get hard and all the passions and desires of homosexual sex came flooding back. I started think to myself, I wonder what his dick looks like? Is he getting hard too? Is he shaved? Does he cum fast?
David and I continued kissing for the better part of 10 minutes. The car was still running, the wipers swooshed every now and then as the rain danced on the roof. We’d break from our kiss occasionally to shift into better positions, but go right back to kissing. We started rubbing and touching each other’s bodies, but neither of us — probably out of fear — reached for the others dick. Finally, after rubbing up and down his chest, his stomach and his legs I decided it was time to make my move. I slid my hand up his inner thigh and reached his crotch. I felt the bulge in his pants. David’s excitement increased as he drew in a deep breath. I rubbed my hand around his cock over his pants, just feeling the outline of his cock. I felt David’s hand finally reach in-between my legs cupping my hard cock and balls over my dress slacks. We both lunged forward towards each other more as our passions increased. We sat kissing for a few minutes, just rubbing each other’s crotches until I wanted more.
I lifted my hand away and upwards and started to unbuckle his belt. I struggled with it at first, but finally got it apart. I wanted his cock and I wanted it now. I unbuttoned and unzipped his pants and reached my and down into his pats, but over his boxer shorts finally getting a good feel of his hard dick. His dick felt long and thin with a bigger head. I rubbed up and down on it as I felt David undoing my button and zipper. I felt his hand slide deep into my underwear finding my hard cock. He grabbed my shaft with his hand pulling it upwards to let it stand erect. He stroked my cock softly and gently as I moaned in pleasure. I pulled my hand from the top of his underwear and slid it deep into his boxers. His cock was long and thin and did have a big head on top. It felt as long, if not longer, than Sara’s 7 inches. But the way I looked at it, the longer the better!
I grabbed his hard cock pulling it upwards slowly stroking him. I could feel a patch of hair at the top of his shaft, but the rest felt shaved. We both sat there arms crossed over each other’s, stroking each other off as we kissed deeply. I opened David’s pants as far as I could and pulled down the front of his boxers, letting his cock out of his pants. I stoked him harder and longer because now I had better access. I broke from our kiss and kissed my way down his chest across his shirt. I got onto my knees on his passenger seat, leaned over his center column and just licked the big mushroom head tip of his cock. David sat back in enjoyment, surprised I was going to blow him right there in the parking lot. I was amazed at how sexy his cock looked. It was a bit thinner than Sara’s, but just as long with a bigger head. It was sexy and erotic, hard as a rock and awaiting my wet mouth. I kissed the tip and swirled my tongue around the tip of him teasing him for a few seconds. I took his long thin cock deep into my mouth getting my first taste of him. I bobbed up and down on his shaft just working it with my lips and Kartal Escort tongue. I took his cock all the way down feeling it hot the back of my throat, followed by me slowly withdrawing it back up to the tip. “Umm” I moaned out as I slid it all the way back in again. I was so excited so turned on and so amazed at my lust for cock.
In my head I was thinking, I AM SUCKING DICK AGAIN and I FUCKING LOVE IT! I was so horny, so hard and so ready to suck David to orgasm. I bobbed up and down on his cock making sure I pleasured him every way I could. His cock was soaking wet with my saliva as hot sexy slurping sucking sounds emanated in the car. My ass was tingling and wanting to be fucked. David was moaning, “Mike, OMG, I am so fucking hard right now.”
I was sucking David off and now knew — without a doubt — that I loved cock more than I loved pussy. I was finally free from my thoughts, my worries and my concerns of my sexuality. As I bobbed up and down his shaft I was thinking, I love cock, I love sucking cock, I love swallowing cum, I love being fucked in the ass. I want cock. Period!
I continued sucking David’s’ dick for about 10 minutes until he finally came in my mouth. I swallowed every bit of that hot sticky load own my throat. I couldn’t get enough. I wiped my mouth clean of Cum and saliva and sat back down into my seat. David was sitting there with sweat glistening on his brow, as I was sweating from sucking him off. After he caught his breath and started to put his package away, he looked at me and said, “That was the best blow job I ever had! Where did you learn to do that?”
I smiled and said, “Practicing on Sara!”
David leaned over onto his side, reached over and pulled my shirt out of my pants. He kissed me deeply as his hand started exploring my dick and balls. He was turning me on and was surely going to retune the favor of a blow job, but had to get me hard again. We whispered romantic sexual things to each other and within a few seconds I was rock hard with his hand wrapped around my shaft. David pulled my pants down a bit further and he leaned over his center column and he placed my throbbing cock into his mouth. The feeling was incredible. I was getting a blow job from a man I was attracted to and it felt so good. David slurped up and down my shaft making me hotter and harder than I was before. He sucked my dick with passion and vigor trying to bring me to orgasm quickly. It didn’t take long until I was moaning out, “David I’m going to cum!”
David picked up his pace and with the assistance of his hand brought me to orgasm. I exploded in his mouth releasing every drop of my cum deep in his throat. My legs were shaking and I was finally getting off after being alone and sexless for a long time.
David pulled his mouth from my cock and he leaned back in his seat, wiped the sweat from his brow and took a long deep breath, as I sat there with my pants partially down with my hard dick dripping out the last bit of cum.
We sat there like that for about 25 minutes before we both started getting dressed. We had a few more smokes and talked ore about “us” as the night progressed.
David told me, “Before this goes further relationship wise, I want you to know, I don’t mind giving head, but when it comes to penetration, I am a top only.”
I said, “No problem, I like being the bottom anyway.”
And I did. There was no doubt with him or any other “average man” I would date, I would be the bottom. I was really interested in being the girl of the relationship more permanently and just pleasing my man anyway I could. There was no doubt from word one with Sara that I was going to be fucked by her cock. Same with Enna. Then years later fucked without incident by a strap on dildo from Cheryl. I knew in my heart where my place was. And to be honest I wanted it. I wanted cock, I wanted to be fucked, I wanted to suck dick and I wanted to be the more feminine role in a relationship. Period. So, fuck me all you want David, I am here to be your little girl.
David and I parted ways that evening relieved we had both finally shown the interest in each other and had taken out first steps into a new relationship.
As I drove home, I was more excited than I had been in a long time, regarding relationships anyway.
I kept chuckling to myself as I repeated over and over in my head as I drove home, “Mike likes Dick, Mike likes Dick.”
Looks like it’s a good start for David and I.
To be continued…
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