Trans Romance

Summary: Guy finds out girlfriend is trans and explores his sexuality.

Note 1: This is a short Valentine's Day 2025 Contest Story.

Note 2: Thanks to OhDave1 for editing.

Trans Romance

"Can I tell you something?" She asked, looking completely terrified. We had just returned from our Valentine's Day supper and were back at my place since my parents were gone for the weekend.

"You can tell me anything," I said, taking her hand in mine.

"This could change everything," she said looking so vulnerable.

"Nothing can change how I feel about you," I assured her, having only dated her for four months but pretty sure I was in love with her.

We met at Comic-Con.

She was dressed as Princess Peach and I was Mario.

During the Cos parade, we ended up together and well... the rest was history... serendipity.

I believe in love at first sight and although some would scoff at that notion, my parents both say they knew they would end up together the day they met... serendipity.

Anyways, besides being incredibly smart, having similar interests as me, being very pretty and sexy, always wearing nylons which was my personal fetish. Sshe was also an amazing kisser. Although, we had not yet had sex and she wouldn't let me go down or touch her below the waist (besides caressing her nylon-clad legs and feet), she loved giving me blow jobs... which, as a virgin, I sure couldn't get enough of. I mean I'm an eighteen-year-old guy in my first year of college. She usually swallowed but even let me come on her face.

I glanced down to her perfectly manicured red toenails in sexy sheer mocha-coloured hosiery which she knew was my favourite colour. My dick was hard and I tried to not adjust it in its awkward position since this had somehow shifted from romantic to serious.

"I was born a boy," she whispered, not making eye contact.

"Pardon?" I asked, not sure I had heard her correctly.

"I was born a boy," she repeated.

"Oh," I said, this not at all what I was expecting.

"I knew I was in the wrong body when I was twelve and have been taking hormone pills ever since."

After a brief pause, I began to ask, but wasn't sure how to finish the question, "So, do you have...."

"Yes, I have a penis, not a vagina," she whispered, still unable to make eye contact with me.

"Oh," I said trying to process. It wasn't that I was against the trans community, but this wasn't what I was expecting to come out of her mouth. In truth, I also had always been much more fascinated with a penis than a vagina. I mean I wasn't gay as I only found girls attractive, but there was something about a penis that turned me on. These mixed feelings had always confused me, but I had generally pushed the confusion to the back recesses of my mind.

"I understand if you want to break up with me," she said, finally looking up into my eyes with such heartbreaking vulnerability.

I didn't want to break up with her. In fact, this didn't change anything. Actually, it changed one thing... it confirmed I loved her. Somehow this moment of honesty and vulnerability confirmed it. It took me a moment to put my thoughts together before I said exactly what my heart felt, "I love you, Kara." I leaned in and kissed her. I then added as I looked into her eyes that were beginning to well up, "I love you for you."

"You do?" she asked, looking at me with a sense of disbelief.

"Yes, unconditionally," I said, as I found myself instinctively and curiously dropping to my knees before her and saying, "Let me show you."

"Drake, you don't have to," she said, as I lifted up her skirt and found a bulge in her pantyhose.

"I imagine this poor thing has been dying for some attention," I said, as I reached out and squeezed it, an odd excitement coursing through me. Suddenly, I wanted to suck her cock.

"Oh," she moaned.

I pulled her pantyhose and panties down and her cock popped out. Five inches like mine. I took it in my hand. It was so hard. While I had been fascinated by cocks and looked at many online, the idea of stroking and sucking one had only popped up in my fantasies a few times. Yet, I always thought it was gay and I wasn't gay. But now that there was one right there before me and attached to the woman I loved, I felt the urge to suck it.

I leaned forward and just did what came naturally to me... I took it in my mouth.

"Oh, Drake," she moaned.

I slowly began to bob back and forth, not really sure what I was doing, although sucking a dick wasn't overly complex. I just listened to her very genuine moans. The excitement of hearing her moan because of what I was doing gave me a major sexual adrenaline rush which pulsated right to my very hard dick.

"Drake, that feels so good."

Taking her words as encouragement, I bobbed faster, also using my tongue like she often did when she sucked me. This I found a little more challenging at first, but focused on making her happy and hearing her moan.

"That's it, Drake, suck my cock," she moaned.

Her dirty words turned me on as I kept sucking her cock trying to take more and more in which each forward bob until I was taking it all in.

"It feels so good."

I didn't know what I was doing, but I felt a surreal sense that this was a natural progression of my sexuality. She sucked my dick, I sucked hers.

It wasn't even two minutes later, that she warned, "I'm going to come."

When I warmed her, she went faster and swallowed my load, so I did the same thing. I wanted to feel her cum shoot in my mouth. I was curious what that felt like. I was curious what it would taste like.

"Get ready. Here it comes," she whimpered, a few bobs later before she came in my mouth.

I swallowed all the surprisingly warm, gooey and salty cum. Feeling her dick pulsate in my mouth made my own do the exact same thing in my pants.

I kept bobbing for a few more seconds, before she gently pushed me away, turned around and knelt on the couch and said, her pantyhose and panties still around her ankles, as she offered me her ass with lustful urgency, "Fuck me, Drake. Fuck me, right now."

I stared at her pretty ass, her dick dangling down between her legs, as I quickly got out of my clothes and moved behind her. I asked, "You sure?"

"Yes, I'm sure. Fuck me right now," she demanded. "I've wanted this since we first kissed."

So, I did, sliding my cock into her very tight, very warm ass. A very different sensation than her mouth, not better or worse, just different.

"Oh yes, now give it to me, baby," she moaned, a very different persona than I had ever seen from her.

I pumped my cock in and out of her ass... the sensation of losing my virginity in an asshole wild and yet suddenly seemed serendipitous.

Sadly, for me, the first time I fucked a woman would be a pretty quick encounter... I didn't last twenty strokes before I warned I was about to come.

"Come in my ass, baby, I need to feel you come in my ass," she moaned, beginning to bounce back to meet my forward thrusts.

"Okay," I grunted, lasting just a few more strokes before depositing my load in her ass.

"Yes," she moaned. "Fill my asshole."

"Fuck," I grunted, as I unloaded in her.

As soon as I was done, she spun around and kissed me.

"I love you, Drake," she said to me for the first time.

"I love you too."

We then kissed for a good few minutes when a thought popped into my head. I wonder what it would feel like to have her fuck me.

But that would have to wait for another time as we still had a double date at the movies with two friends.

The End