I wasn’t entirely sure where to start my search since I don’t get out much, but I remembered a fun gay bar nearby where I might meet some cute trans girls. If I played my cards right, maybe they’d let me cuddle, steal a kiss, and, if I was lucky, admire their cute cocks.
Before heading out, I took a moment to check my outfit: a crisp button-up shirt, tight jeans, and some sleek leather boots. I felt like I looked good—and smelled good, too. My dating experience with people outside of CIS women was still pretty new, as I’d only recently started exploring my attraction to other gender identities. I was already a bit awkward as it was, and stepping into new spaces felt even more uncomfortable, like I didn’t quite belong or was intruding in some way. But I hoped my awkwardness would come off as endearing, and that someone might see me as a cute dork.
Anyway, I was gonna be brave.
When I finally made it to the bar, I stepped inside and grabbed a beer. It gave me something to sip on while I tried to signal to the world that I was single and ready to mingle. Prime dork material, right here. Come and get it!
As I scanned the crowd, I was caught off guard by a tap on my shoulder. “Oh, hey, John!” My friend had sneakily crept up behind me.
“What’s up? Out for some fun?” he asked.
“Yeah, something like that. Just seeing if there are any cuties who want some dorky company tonight.”
“Gotcha. I should introduce you to my friend, Jenny. She’s cute. A total sweetheart. Oh, and just so you know, she’s trans. Not sure what your dating goals are, but I never really see you with anyone,” he added with a laugh.
He wasn’t wrong. My love life was pretty nonexistent, and when it did exist, it was brief and under the radar.
“Yeah, I’d love to meet her,” I said, eager to start talking to someone. That was the whole point of coming out tonight, after all.
We wandered over to where Jenny was, and John made the introduction. “Jenny, this is my friend Jim. Jim, meet Jenny.”
I gave an awkward wave and a nervous smile, which she returned with one of her own.
“Hey.”
“Jenny’s a painter,” John said, kicking off the conversation. “She’s really good. You should check out some of her stuff—mostly watercolors.”
“That’s cool,” I said with a nervous laugh. “I have zero artistic ability, though.”
“That’s okay,” she replied. “I’ve been painting for years. I was terrible when I first started.”
And just like that, the conversation started flowing, a few stumbles here and there, but nothing major. John could tell we were hitting it off, so he quietly excused himself and disappeared into the crowd.
I was feeling a lot less nervous now. Jenny had a way of making me feel at ease, and her kindness made me feel like my awkwardness wasn’t something to hide. She seemed to appreciate that I wasn’t trying to be anything I wasn’t. We had a few more drinks, well, I had one, because I’m a lightweight, but the night sped by. Eventually, the moment came: do we go our separate ways, or do we take this somewhere else together?
We decided to leave together.
We strolled along the sidewalks, continuing our conversation and laughing more than I expected. I’m pretty sure the drinks helped loosen me up, making me less of a stiff, uptight guy.
As we waited at a stop sign, Jenny turned to me and said, “Hey, um, you seem really nice, and I was wondering… would you want to come back to my place for a bit?”
I hadn’t really expected to meet someone as cool as her tonight, let alone get invited back to her place. But, of course, I was all in.
“Yeah,” I said, trying to keep my cool, but internally, I was starting to sweat through my shirt.
“Cool,” she replied, before reaching out to grab my hand and guiding me down the street. I found myself trailing behind her, admiring how she looked in her cute, floral dress, the way it bounced around her legs as she walked. And I couldn’t help but wonder what she looked like without it.
We made our way to her place, a cozy little apartment on the second floor, just a short walk from where we’d been. Her space felt warm and inviting, houseplants scattered around, a soft woven rug under a clean coffee table with a lit candle on top. String lights cast a gentle glow, making the whole place feel snug and lived-in. It was way nicer than my place. If you saw my apartment, you’d probably think a transient serial killer lived there. Okay, maybe not that bad, but compared to hers, it felt like a disaster.
She played the perfect host, asking if I wanted a drink. I was already kind of at my limit, or at least I wanted to stay somewhat clear-headed for the rest of the night, so I turned her down, but asked for some water. All the talking was making my mouth dry.
We sat on the couch facing each other. She had one leg crossed over the other, her foot playfully dangling just inches from mine. Our conversation had turned into a string of silly jokes and dumb banter, the kind that flows when you’re both into each other, a little tipsy, and just trying to make the other person laugh. You know the vibe, those subtle body language cues that you might not even notice, but they’re saying everything.
Trying to reduce the tension, she had just made a couple of ridiculous jokes, but it caught me off guard, and I laughed harder than I should’ve. As I finally caught my breath, I felt her foot gently rubbing against my leg. I glanced up at her, and we just locked eyes, both of us knowing exactly what we wanted.
Without thinking, I leaned in and kissed her.
It was really, really nice.
My head was spinning a little. The alcohol had mostly worn off by this point, but the kiss and the heat building between us were still making me feel pleasantly off-balance.
“Do you wanna…” she said suggestively, trailing off without finishing the sentence. I nodded slightly, my face flushing.
She stood up first, taking my hand and guiding me toward her bedroom.
If the rest of her apartment had been cozy and well-decorated, her bedroom felt like a small slice of heaven. Maybe it was just the moment, or maybe it was my desire talking, but I could see myself spending hours in that room with her. Not necessarily doing anything specific, just lying together in bed, close, my fingers tracing the curves of her body. It felt like the kind of place where you could just be, without the need for anything more.
I glanced around for a moment, taking in the room, before she pulled me back to her, guiding me to sit beside her. I inched closer, my hand resting on her back, and leaned in for another kiss. This one was deeper, more intense, as she reclined, and I leaned over her, partly lying on top. We started kissing more urgently, our hands roaming over each other’s still-clothed bodies.
I needed to get my clothes off.
I stood up, unbuttoning my shirt slowly as she watched me, her eyes fixed on me while she stayed stretched out on the bed. I then unbuckled my pants, unzipped them and pulled them completely off. I stood there in nothing but my underwear. I kept my eyes on her as she lay there, silent, both of us lost in the moment, caught up in the unspoken tension.
She knelt up, turning her back to me. With her hands under her dress, she started to wiggle, then dropped to all fours, coaxing her underwear down and past her feet.
She turned to look at me, tossing them playfully in my direction and catching me right in the chest. I felt like a half-naked bridesmaid trying to catch the bouquet. She then lifted the hem of her skirt. Slowly revealing her now shaking tiny butt. But I was more focused on what hung between her legs: a beautiful cock.
Well, this was going perfectly.
I didn’t know what I was doing. I had never had anal sex before. I moved in behind her, too caught up in the moment to feel nervous. My cock, however, was playing the part, standing at full attention for this gorgeous woman.
I didn’t see any lubricant around. Using a little of my spit, I began to poke her asshole with my dick. I could hear her breath quicken as we got closer to what we both wanted. Driven by the moment, I kept pressing forward, eventually closing the distance between us, the warmth of her insides now hugging my cock. Now, I was on top of the world.
I began to move in and out, and she met me with each shift of her body. For my first time, it felt better than I expected, and from the sounds she was making, it seemed like she was enjoying it too. As it continued, her moans grew louder, her breaths quicker. But things were not progressing past that point. We were having problems reaching our climax. We both sensed this. I then pulled out my dick and sat on the bed. She settled beside me, still gentle, her hand softly rubbing my chest.
“Can I use your bathroom real quick?” I asked.
“Yeah, it’s just down the hall,” she replied. I leaned in to give her a quick kiss that almost turned into something longer, but I pulled away just in time.
I found the bathroom, turned on the hot water, and awkwardly soaped up my hands and cock, rinsing them off. I dried my hands with some toilet paper, gave myself a quick glance in the mirror, then headed back.
Jenny was lying on her side, absently rubbing the comforter. “Hey,” she said, turning her gaze toward me.
“Hey,” I replied, moving to lie down beside her. “I am sorry about that. It was hard for me to cum. It was also my first time with anything anal.”
“It’s okay,” she said, resting a hand on my chest. “You were great,” she added, and it definitely gave my ego a nice boost.
“Hey, uh, could we try something else? I have never given anyone a blowjob before.”
She smiled, gently stroking the back of my head. “Yeah, we can do that,” she murmured softly. She scooted playfully to the edge of the bed as I stood up and stepped in front of her. Lifting her skirt up slowly, she made me wait, and I sank to my knees. As I knelt there and took in what was before me, I realized my prayers had been answered.
Hanging between her legs was a gorgeous cock, larger than mine. I gently placed my hands on it and remembering how there was no lubricant, I brought one hand back to spit on it.
She interrupted, “Let me help with that,” and spit into her hand. She then proceeded to rub it all over her throbbing hard dick. Up and down. It was obvious at that point that she took extra pleasure in seeing me on my knees, watching her stroke that beautiful cock of hers. It has to be obvious. “There, that’s much better.”
Placing my hands back onto her dick, I started to move my hands up and down the shaft. It was not different from how I work my own cock. She leaned back, propping herself on her elbows. I watched as her hips moved with every stroke.
It appeared that she was now leaking a small amount of precum. I couldn’t hold back any longer; I needed to taste it her. I then dove in, her cock entering my mouth. This was the first time that any cock had been in my mouth. Inexperienced, I relied on my instincts. My tongue swirled around the tip. And while one of my hands continued to stroke her shaft, the other moved to her stomach. I needed to feel her movement.
This went on for a few minutes, honestly, I lost track of time. Her breathing grew heavier, and I could tell by the signs that we were getting close. I could feel her slightly thrusting into my mouth. I accepted those thrusts, grateful of being able to pleasure this woman.
Then it came! Or I should say, she came…into my mouth. It caught me by surprise. I tried to hold back a cough, but ended up just letting out a small snort. My mouth was full, and I wasn’t sure what to do with the warmth I now had. But I continued to pleasure the head of her cock, lips tightly closed, being careful not to spill. The idea of her cum swirling in my mouth continues to drive me crazy, to this day.
She let out a heavy sigh and collapsed back onto the bed, her sex now spent. I stayed on my knees for a moment, just taking it all in, mouth full of her cum. Down it goes. I swallowed that delicious payload.
I’d just experienced one of the best nights of my life, and I couldn’t wait to get up on that bed and curl up with an angel.
I crawled up beside her, watching as she lay there, a little blissed out. She reached up to brush my cheek with her hand. “That was amazing… was that your first time?” she asked, still catching her breath. “I don’t believe you,” she laughed softly.
I laughed too, then kissed her, my mouth still faintly tasting of her cum. We kissed for a little while longer before settling beside each other in her bed, snuggling close as we drifted off to sleep.
