Dolores Park after Dark

When we were walking through Pride earlier, he mentioned that he thought the men in utility kilts were hot and, more significantly, that he thought I would look hot in a utili-kilt. The he, in this case, was Carter, the hot guy I hoped would eventually become my boyfriend. And this outing to Pride was our fourth date. At first I scoffed at the idea of wearing any kind of skirt, even a kilt marketed to gay men: I was forced to wear more than enough skirts when I was a girl... and I always felt awful in them.

As the day wore on, I kept thinking about the look on Carter's face when he said that he wanted to see me in one of those kilts. It wasn't the look of a gay man thinking about a girl, it was the look of a gay man thinking of a sexy man that he wants to fuck. I mean, it made sense... despite the fact that I was assigned female at birth and still have my factory-direct pussy, no one has looked at me and thought "girl" in over a decade now and that's how I like it. It does, however, make sex and dating a little ummm... complicated.

Carter's jaw dropped when, on our second date, I told him that I'm trans. Living in San Francisco, he knew transmen, but all of the one that he knew were originally from the lesbian community and still had some of that aesthetic... and I didn't look like them at all. I look like a pretty normal gay dude and that seemed to throw him off. I was kind of surprised when he said he didn't care and wanted to keep seeing me. Though we definitely had chemistry, I thought the pussy thing might be a big turn off for him... he had never had any interest in women and, if we got that far, mine would be the first he'd ever seen.

But back to our fourth date: After thinking about it for hours, my curiosity got the better of me and I decided that I wanted to see what I would look like (and how I would feel) in one of the kilts. I saw an opportunity when Carter ran into a group of friends who were visiting from out of town and wanted to get drinks. I told Carter to go hang out with his friends and that I would text him later to get together again. He followed his friends toward the bars and I rushed back to try to find the utili-kilt booth before they packed everything up for the day.

It seemed like I got there just in time. The salesman, a hot bearish guy with a rugby build, was just starting to put the display kilts away when I rushed up. After a little flirting with the salesman, I went into their makeshift fitting room and tried on a bunch of different kilts. It was only when I took my shorts off that I remembered I had only worn my jockstrap, which left my butt and pussy exposed, underneath them. I eventually found a kilt that I liked. I also found that I looked pretty hot in it...and that I didn't look—or feel—like a girl at all. I paid for the kilt and decided to wear it for the evening. I got a bag for the shorts that I had been wearing and texted Carter to tell him I was headed his way. On my walk back toward the Mission, I noticed that I could feel the breeze hitting my bare butt under my kilt and, as I thought about Carter and what I hoped would happen later that evening, my increasingly wet pussy. I thought about finding a bathroom to go into to rub one out, but I knew that finding an available bathroom in this neighborhood during Pride weekend was a long shot.

By the time I reached the bar where Carter and his friends were drinking, it was getting dark and all of us were ready for some food. A couple hours later—the lines were long because of Pride—we were finishing up our meal at Taqueria Cancun. Carter, who finished his food quickly, was sitting next to me with his hand on my thigh, up under my kilt. As his friends chatted with us, he kept moving his hand higher and higher up my thigh, until his pinky was only an inch or so away from my packer and, underneath it, my hard, throbbing, 2" clit. My pussy was so wet by this point that I was worried my lube was dripping everywhere—I knew the insides of my thighs were covered. When Carter slid his hand a little toward the inside of my thigh, I knew he hit my slickness. I looked at his face and watched as he registered what had happened... how fucking turned on I was and how much my pussy was leaking for him. He removed his hand from under my kilt and, as if he had realized that he had some food on his hand, brought his fingertips, wet with my cum, to his mouth and subtly licked them. I looked down at his lap and saw his cock, clearly hard, making a huge tent in his jeans. Luckily, his friends, who had each had several drinks by this point, hadn't noticed that anything was going on. I decided that I was ready to go, so I went to the bathroom to try to dry my pussy off a little and to give my hard clit a few jerks... and to text Carter.

"Wanna ditch your friends and go make out in the park?" I texted.

"Fuck yeah," he quickly replied.

Though I realized it was a futile effort, I made one final attempt to dry my dripping cunt and then went back to rejoin our table. We quickly said goodbye to Carter's friends and made our way towards Dolores Park. When we hit a light, Carter pushed me up against a wall at the corner and pushed his tongue into my mouth. As we made out, he put one of his legs in between mine and pushed his thigh up into the juncture between my legs, directly against my packer and my needy clit, and ground into my hardness.

We finally made our way to the park. Because it was well after dark by this point, there were only a few lights illuminating the park and most of the folks who use the park by day for drinking and sunbathing had left. We took over one of the few benches and resumed our making out, first sitting side-by-side. When that got too uncomfortable, Carter straddled the bench and I sat on his lap facing him, spreading my thighs to straddle his, with my kilt completely covering both of our laps. As we continued to make out, I reached down and pinched his nipples through his shirt. He moaned in response and I could feel his steel-hard cock throb underneath me as I rubbed my packer-covered clit up against it. The feeling was amazing and I was now very glad that I had decided to wear the kilt. As I continued to play with his nipples he pulled away from our kissing and groaned into my ear "God, I want to fuck you."

"I want you to fuck me," I moaned back in response.

I took a look around and realized that it was dark enough and the park was empty enough that we could probably get away with it. I reached down under my kilt and found the straining zipper to Carter's jeans. I worked to unzip his jeans and began to wrestle his stiff cock out of his underwear and through his fly. Carter drew in his breath sharply when he felt my hand against his bare cock.

"I'm so close" he nearly whispered, clearly trying not to cum already.

I kissed him again while I gently rubbed my thumb over his cockhead, spreading the copious precum leaking out of his slit, and then I stroked his cock slowly a few times, moving his foreskin up and down over his head. I was too horny to wait much longer. I pulled my jockstrap up a little so my packer rested a little higher and my big clit was exposed beneath the jock. I made sure his foreskin was pulled back and began to rub his exposed cockhead up against my clit in classic swordfighting motion. He drew in his breath sharply again.

"Fuck, that's hot," he said. "Is that your...?"

"My clit or cock... I don't care what you call it." I responded, way too horny to do Trans-101 at this moment.

"It's so hard," he replied. And I kissed him again before he could say anything else.

After a minute or so of that, I couldn't wait anymore and decided that it was time to get things moving. I began to stroke his cockhead up against my dripping hole, mixing his precum and my lube together over both of us. I then tilted my hips down and allowed his cock to barely penetrate my hole, not even his whole head was inside me. I leaned toward him and pressed my lips up to his ear.

"You already felt how hard I am for you. Do you want to know what it feels like to have your cock inside me? How hot and tight and wet I am for you?"

He groaned in response, clearly turned on beyond words.

Still gripping his cock, I shifted my weight and pressed my pussy down, taking his entire length inside of me. His cock filled me up so completely.

"Oh my god," he gasped, "my cock is inside of you, inside your pussy..."

"How does it feel?" I asked, moving my hips back and forth, feeling his cockhead knocking into my cervix and imagining his precum dripping out of his slit deep inside of me, mixing with my lube and prepping me to receive his load of swimmers, his DNA.

"I love how your head is hitting my cervix and your balls are slapping against my ass." As I said this, I reached behind me and fondled his huge balls, appreciating their heft and thinking about how much semen they held. When I felt them tighten in my hand, I realized how close to cumming he was, and decided to try to keep him from cumming for another few minutes, to prolong this fuck.

I sat down fully in his lap so that he was completely inside me and I moved the hand that I had been using to fondle his balls up to my clit. I began to jerk my clit and, still not moving my hips at all, stimulated his cock by squeezing my pussy tightly around him and then loosening up. I felt his cock throb inside me in response, but this seemed to give him opportunity to get himself back under control again.

"I can't believe we're doing it raw," he said, "it's been so long since I've been inside someone skin-on-skin."

"I know," I moaned in agreement, "but I really need to feel you shoot your load inside me. It's been so long and my pussy is so hungry for it. I want your sperm swimming up inside me, I want you to breed my cunt," I said breathlessly.

"Oh god... I wanna breed your cunt. I'm gonna shoot you so full of my seed," he moaned loudly as I felt his head expand deep inside me and his balls pull up right against my ass and throb. And then I felt warmth and a pulsation deep inside my sheath as his throbbing member released the contents of his nuts as deep inside me as he could. Based on the number of throbs I felt from his cock, he must have shot close to a dozen streams of semen into my hole.

The feeling of him cumming inside me set my orgasm into motion, so I started thrusting my hips back and forth and I reached down to continue jerking my clit, wanting to cum around his cock before he got soft. As I was about to cum, I saw a flashlight beam pointed our way and quickly approaching. I stopped moving my hips and stopped jerking my clit just in time as the police officer came into view.

"Fellas, as you might have noticed on the signs, this park is closed after dark. I know it's Pride weekend, but you gotta find some other place to hang out." As the officer talked to us, Carter flexed his still hard cock inside of me and, at the very same time, I felt some of his cum starting to drip out of my hole. It was pretty hot that the officer had no idea we were still joined, Carter's penis still plugging my cum-filled vagina and his sperm searching for my womb, as the cop talked to us. It made sense though, it wouldn't really have been possible for two cismen to fuck in this position, and the cop had no idea that the organ Carter was buried in even existed.

"Thanks for letting us know, Officer. We'll get going in just a minute," Carter replied earnestly.

That was apparently enough assurance for the cop, who told us to have a good night and began walking toward one of the areas where a few folks were, based on the smell drifting our way, smoking weed.

"That was close," I said, as Carter helped lift me off of his lap. My pussy made a liquid noise as his hard cock popped out of it and I could feel his semen already running out of my hole and down my inner thighs. It took Carter a moment to stuff his still-hard cock back into his jeans and boxer-briefs. He then grabbed me by the shoulders, looked me straight in the eyes, and said, "That was amazing. We will definitely be doing that again very soon...I still can't believe how great that felt."

I grabbed his hand and squeezed it as we began the long walk to Carter's apartment. To be continued... (the night isn't over yet!)