Me From the Past

My name is Ashton Geert. I've been spending my days as an average 25-year-old man with a decent job. Most of my family and friends think that I'm gay. You don't have to come out to you mother if you don't date a single woman in your entire adult life.

I do have this funny aunt that thinks I'm a stud that just keeps it casual with countless women. Our conversations can take weird turns at family gatherings. She'll ask me how many hearts I've broken recently; meaning how many girls I've fucked recently.

I'll say something along the line of "You know how it is!" Everyone around us would keep quiet, not wanting a homophobic rant out of the otherwise nice older lady.

This woman thinks I'm a breaker of hearts because of how I look and how I maintain my physique. I work out constantly just to keep myself out of the heavy depths of depression. I am a six feet tall muscle machine that didn't want to look like this in the first place.

--

I have always felt like there was something wrong with me. I was attracted to girls, but I didn't want to have sex with them. I figured out I was not straight when I saw how my straight friends acted like around women.

I was not even that attracted to guys. Sure I could picture myself with some of the guys from college. But there was some form of fear in the back of my mind whenever I pictured being intimate with a guy. Men are a little more intense when it comes to sex. Then I realized that I was not gay either.

I was able to discover myself properly once I was could afford a place of my own. It didn't take me too long to figure out that I liked feminine clothing. I had trouble figuring out exactly what I liked about dressing up as a woman.

But by that time, I was already pretty successful as a man, getting an above average income working at a big company. I was being all man out in work, and dressing up as a delicate little flower in private.

That discovery came at a price though. The price was intense self-loathing. There was a period of months where I felt like I have failed as a man and I will not be worth anything.

--

That's when I started hitting the gym. I thought that stronger and bigger muscles would make me feel manlier.

News flash: It did not!

Now I was a muscular man that still liked dressing up as a woman. Only this time, I looked bizarre in the skimpy dresses and underwear.

But let me tell you something else. Women have a wide variety of clothing to choose from. And not all of them are that bad. There are really nice dresses that can suit a six feet tall muscular man. And let me tell you, when I'm wearing a proper and elegant dress, of course I bought those too, I want to bend myself over from time to time. But those dresses are expensive. So I just take pictures before getting naked and jacking off.

I thought about quitting the gym once I came to terms with who I really was. But I quickly figured out that I got addicted to it. I used to laugh at people when they said that gym is their therapy. But quitting the gym for a while made me realize that there were some nasty thoughts that can lurk around your head. The voices that tell you that you've wasted your life and you will never be happy with someone. You know you're only 25 and your life is not over. But when that voice tells you, you're much more inclined to believe it.

So I kept going to the gym five days a week, keeping my body ripped and mind somewhat calm.

By that point, I knew that I was attracted to beautiful people, no matter what they had in their pants. But I didn't know exactly what I wanted until I met that one person.

--

I saw Kyle in the gym as I was waiting to buy some workout supplements. He was there in front of me.

There was something about the way he carried himself. It seemed like I was looking at a different version of me. The way he was standing, the way he was speaking, all of the mannerisms were eerily familiar to me.

He was friendly with me from the beginning. I learned that he's a 22-year-old fresh college graduate that joined the gym recently. He was in line to buy his pre-workout supplements. He talked about lifting some heavy ass weights. I told him that I would be more than happy to help him out.

I felt like I was looking at me from four years ago, denying who he really was and pumping irons. He had a recent buzz-cut hair. He was probably growing out his hair before deciding to 'be a man.' He was wearing loose clothing, but I could notice his puffy nipples, most likely the result of being overstimulated. And not to mentioned how thick his thighs seemed compared to the upper body.

The most telling part was not his body, but his attitude. He tried to appear tough at every second, even standing in the line. He glanced around nervously for a moment before squinting his eyes to show a false sense of bravado.

He was all smiles and sunshine when I started chatting him up. I don't think I need to tell you that he has a beautiful smile.

He's slightly shorter than me; with dark hair and green eyes.

I might have observed a little too much of Kyle as he looked down my crotch once. We did not speak that day after buying our supplements.

He soon became a regular at the gym. He was not able to join me on the exercises I was usually doing for the first month. We greeted each other almost every; and more than a few stolen glances were shared between us every day.

My suspicions were mostly confirmed with the way he would look at me, and a few other gym members. It was his second month in the gym, when he started lifting heavier weights, I offered to spot for him. Kyle was glad with my help.

We started talking pretty regularly after that point. He would often ask for my help from then on, and I was glad to provide. I came to know that he started a job as a junior executive at an ad agency.

After seeing what he was going through, and what road waited for him in the future, I decided to chat with him about his sexuality. But I had to take it slow. It started with me touching him and complimenting on his improved form in the exercises. I would always tell him that he had a nice body, mostly while I was holding his hips.

The way he looked at me when I asked him if he had a partner or not told me much more than I needed to know. I knew what I had to do. It was not going to be easy.

Kyle has to know that working out like a maniac is not going to change who he is as a person.

--

I started flirting without any subtlety as he said he was single. I would touch him everywhere other than his crotch, as we became workout partners.

It was when he was comfortable with touching my pecs after bench presses, I decided to make my move. I asked him out for coffee on an afternoon. I was about to take the biggest leap of faith of my life with him. It would be my first proper date after graduating college.

--

I was slightly nervous when I wore panties before going out on my date. Of course I was wearing tight fitting formal shirts and pants that accentuated most of the prominent muscle groups of my body.

But I was determined that I was going to come clean and just tell him that I knew about his sexuality. I wanted him to know that bigger muscles are not going to make him feel like more of a man. The only way to make him understand was to show him that I felt the same way. I had to tell him that I painted myself into a corner after so many years.

What I did not plan on was that Kyle was planning on coming out to me at the same time.

I was absolutely floored when I saw him approaching me as her. She was wearing a red dress that went down to her knees. I did not recognise her until she was standing right next to me.

That was mostly because of the gorgeous shoulder length wig she was wearing.

"Ashton!" She called me out.

"Kyle?" I said, bewildered by the stunning person standing right in front of me.

"You should probably call me Kylie when I'm dressed like this." Her voice was a little higher than before.

"I... I had no idea." I was flabbergasted and did not know how to respond.

Despite knowing that Kyle most likely wanted to be Kylie beforehand, seeing her in front of me completely fried my brain at the moment.

"You're not turned off by women I hope." The poor girl was having trouble looking me in the eyes.

"You look beautiful." I said as I grabbed her chin to make her look into my eyes. "Let's go inside!"

Both of us were dressed too nicely for just a coffee date. But we did not care about what others thought about us. Not when we're together.

Kylie let me know that she felt safe enough around me to come out in public dressed as a woman.

"Is this the first time for you," I asked. "To get out of the house in feminine attire?"

"Yes!"

"You're so fucking brave." I commented.

"What do you mean?" She tried brushing the complement off. "Lots of people do it."

"There are more people hiding their true selves than you'd ever know." I let it out.

"Huh!"

"There are people who keep their true feelings bottled up deep inside them." I started speaking. "People filled with self-hatred, trying to be a man at any cost. Going to the gym all the time, thinking that muscles are what men are made out of. Once they get completely ripped, they realized how nothing changed for them. Then they start to hate themselves even more."

Kylie had her mouth open when I finished talking. She was smart enough to figure out who I was talking about.

"I hope you're not turned off by me." I added.

"You..." She paused for a long time. "Do you... have you experimented with women's clothing before?"

"I'm wearing women's underwear right now."

"Can I," Kylie had her eyes closed. "Can we go to your place right now?"

"I..."

We paid the bills and hurried back to my place.

When we were alone in the elevator, I gave her a glimpse of my panties. Kylie let me grab her soft and bouncy ass in return. We started kissing like long time lovers as soon as I got inside my apartment. Kylie told me that she really wanted to see me wearing a dress.

She mentioned being really attracted to me, and wanted to see how I would look like wearing dresses.

"I'm not good at makeup at all." I mentioned. "It's just dresses for me."

"Don't worry about it." She reassured me. "I don't think I'll be disappointed."

I looked down to see the bulge in her crotch area. I nervously walked up to my own room. I was glad that I had shaved my legs before going out.

Not wanting to keep Kylie waiting in an aroused state, I quickly got dressed in a floral sundress over the panties I was already wearing. The panties did not match the dress, but I did not care.

"This is just one of the dresses I own." I said as I walked out of my room. "I never go out wearing these though."

I was way too self-conscious about my muscles and how it might make me look like a freak. But not to Kylie. Her immediate reaction after seeing me was to run up to me and give me a tight hug.

"I knew I felt like this about you for a reason." She said. "What should I call you?"

"Ash I a pretty non-binary name I guess." I mentioned.

"Okay Ash," She said straight up. "I don't know how you feel, but I would like to see if we have something."

She was proposing a steady relationship, while holding me in a tight hug. My dick was already hard in my panties when I started getting dressed up. After her confession, I started leaking precum.

"I don't know if I'm ready to go out into the world as a woman." I confessed. "After all this time, I don't know if I'll ever be ready."

"You don't have to do that." She broke the hug. "I just want to know if you'll have me as your girlfriend."

I gave her a kiss before saying, "You are so fucking pretty; anyone would be lucky to have a girl like you by their side."

"Then I don't care if you're a man or a woman; I just want you by my side."

I was trying to be emotionally strong at the moment. But her sweet talks were not helping me.

We started kissing, while rubbing our crotch together. We made out until the front side of our dresses were completely ruined. We discovered each other, both physically and emotionally, that night.

Kylie laid on her back as I went down on her for the first time. She came in my mouth before I started rimming her.

A few minutes later, she just asked me if I was clean or not. I knew what she wanted. So I just said yes and brought out a tube of lube. Our first time was missionary as we kept kissing each other until I finished deep inside her. By the time I came inside her, Kylie was hard once again.

Both of us were laying on our back, completely naked.

"I think I want to keep my penis." Kylie said out of nowhere.

"Huh?" I was confused.

"I don't want to remove..."

"You don't have to do anything you don't want to." I told her. "You know... you can fuck me with your penis... if you want to."

"Really?" She said with a lot of enthusiasm.

"Of course." I reassured her by saying that I am not a virgin.

She got on top of me at lightning speed and we started making out once again. Only this time, our naked penises were rubbing against each other.

Both of us were hard and leaking precum by the time Kylie asked me if I was sure about it. I told her to start fucking me quickly before I start having second thoughts.

Kylie had a sly smile before penetrating me. It felt so fucking good knowing that the person on top of me might just be the one for me. She kept playing with my dick while working her dick in and out of my ass. Both of us came at the same time nearly five minutes later.

Kylie went down on me and started cleaning my cock straight away. After she was done, I told her that she could take her wig off. Once again we were laying side by side, with our legs hanging from the bed.

I was enjoying the silence when I turned around to see that Kylie was crying.

"What?" I was shocked. "Did I do something wrong? You can put the wig on if you want to."

"That's not it." Kylie said in between sobs. "It's just... you don't think I'm a freak?"

"You're the prettiest woman I have ever seen." I mentioned. "Absolutely nobody is going to see you as a freak."

"It's just..." Kylie explained. "All my life... I thought there was something wrong with me for feeling the way I did. I thought I was abnormal in some way."

"First of all," I stopped her. "You're my girlfriend now. Nobody is going to dare call you a freak. I'll make sure of it. You know what," I stood up as I said. "You're going to move in with me. You'll get rid of all of your man clothes. If your work does not allow you to continue like that, just quit. I make enough for the two of us."

Kylie's face went a little red as I was talking about being the man in her life.

"But what about you?" She asked me.

"What about me?"

"You said you felt the same way." She mentioned. "Aren't you going to?"

She was sitting down now as I straddled her much softer thighs before speaking.

"What happens between us behind closed doors," I said. "Is our business. But I'll still be the man out in public. But I don't want you to limit yourself like I did."

"You know," She said. "It's not too late for you."

"I know it's not." I replied. "But if you are there by my side; I can endure absolutely anything."

We made out once again for fifteen minutes before getting up for dinner.

I cleaned the dishes when Kylie crawled between my legs and started blowing me. After putting the dishes away, I bent her over the kitchen counter and fucked her.

We took a long shower after that and thoroughly explored each other's body over the next hour.

We were completely naked, facing each other, talking about the future in my bedroom. I told Kylie to let her hair grow a bit. She agreed and said I should also grow my hair. I told her that I'll think about it.

Kylie positioned herself a little higher for me to penetrate her easily. Now we were hugging each other, with Kylie's back against the wall. I slowly worked my dick in and out of her ass.

Both of us lasted for much longer this time, and I was also able to take it slow. I was still hugging her really tightly when I discharged my semen deep inside her. Once again, we were laying down side by side, reeling in our afterglows.

Now it was my turn to get emotional.

I don't know why, but I started feeling like there was a well formed deep inside me that was about to overflow. Tears slowly started streaming down my face. It felt like I was not in control of my emotions as I started weeping.

"What happened babe?" Kylie asked me. "Why are you crying?"

"It's nothing babe." I reassured her. "It's just... I was feeling really good, and..." I could not explain it to her the reason behind my tears.

"It's okay," She kissed me before saying. "You should not keep your emotions all bottled up. You can tell me how you feel."

This was still the first night of us being together. But for some odd reason, I felt like she was the missing part of me, and I was complete.

Maybe that's why the excess tears started coming out of me. There was no space for tears inside me anymore. We were still facing each other in bed when Kylie kissed me on the forehead.

"I don't care how you look on the outside." She said to me. "But you better not try to be a 'man' with me. From now on, you tell me exactly how you feel, okay?"

"Okay Kylie." I said as she started wiping the tears away from my eyes.

Which in turn produced a lot more tears. For the next fifteen minutes, Kylie kept kissing different parts of my face while wiping away my tears.

My life had a new meaning after that night. I am a completely different person who has something to look forward to. Every single time I see her smile, I feel like all of the shit I went through to get to her was worth it.

I was happy to be able to provide for her. She quit her job a few months after moving in with me. And, with my encouragement, she started hormone replacement therapy.

--

I was still not ready to take her home for the next family gathering. I was nervous before leaving her alone to go to our family home. She knew how I felt about it, and kissed me gently before leaving.

I already told my mom I was seeing someone. She didn't ask a lot of questions about my partner. She's one of those moms who are happy as long as you can feed yourself properly.

One of my older cousins announced that she was pregnant with her second child. Everybody was happy for the couple.

And of course, aunt Helen was still as nosy as ever. I still don't know why she's obsessed with me fucking countless women. Her own son came out when he was 19 and she disowned him. Maybe she saw me as a son that's having sex with women all the time.

"How's my stud of a nephew doing?" Helen said as she approached me in the backyard. "How many hearts did you break this year?"

"You know how it is." I gave my usual response before switching it up a little. "But it's getting scary with the amount of women I'm doing all the time."

"What do you mean?" She was confused.

"What if one of them get pregnant?" I explained. "I don't want a baby out of nowhere!"

"There are precautions," She started speaking.

I decided to say whatever came to my mind. She's the one that got overtly familiar in the first place.

"You know precautions are no good once you get going." I said as I noticed her slightly uncomfortable face. "So I started almost exclusively going for the back door lately."

"What?" She exclaimed and one of my cousins stifled her laughter.

"But the problem is," I continued. "Most women don't like it up there."

From the look on her eyes, I could tell that she was trying to figure out if I was coming out as bi to her at the moment.

"So I'm thinking about settling down with someone who likes it in the butt." I said. "I don't have to keep looking for someone all the time. And if she's the right one, maybe kids can come into the picture later in line."