Let’s just get this out of the way, I have an obsession with foreskin. Beautiful, uncut dicks, hiding in their cute little turtle necks, all cozy…until you make them angry. You wouldn’t like them when they’re angry. Except, I do.

Unfortunately, I have a circumcised penis, so my two options for appreciating a beautiful intact penis is to either watch porn or go try to find someone in the real world that will let me play with theirs.

Having spent so many hours fascinated by uncut cocks online, I decided to go on a little real world treasure hunt of my own. Searching for my ‘white whale,’ as it were. A smooth, uncut dick, the bigger the better, well-moisturized and smelling of heaven. 

I wasn’t quite sure where to begin my hunt, as I don’t get out that much, but I knew there was a fun gay bar in the area where I might meet some cute trans girls, and if I was charming enough, they might let me snuggle and smooch them, and possibly ogle their cute cocks at some point.

Before heading out, I checked my fit: a smart buttoned up shirt, tight jeans, and some nice leather boots. I thought I looked good, and smelled good too. My dating experiences with people other than cis females was fairly limited up to this point, as I had only recently started exploring my attraction to other gender identities. I was already a little awkward as a human, and I felt more awkward in those new spaces I was exploring, like I didn’t quite belong or was intruding in some way. Hopefully, my awkwardness would be endearing to someone, and they’d just think of me as a cute dork. 

Oh, well. I was gonna be brave.

Making it successfully to the bar, I headed inside and ordered a beer. It would give me something to nervously sip on while I (hopefully) was successful in advertising that I was single and ready to mingle. 100% prime dork meat, come and get it! 

Looking out into the crowd, I was surprised by a tap from behind on my shoulder. “Oh, hey James!” my friend that had secretly snuck up on me. 

“What’s up? Whatcha’ doing here? Out for some fun?” he inquired.

“Yeah, something like that. Just seeing if there are any cuties who would like some dorky company for the night.”

“Gotcha. I should introduce you to my friend, Jane. She’s cute. A real sweetie. Just FYI, she is trans. I’m not really sure what your dating goals are. I never really see you with anyone,” he said with a slight laugh.

He was right. It wasn’t often my friends saw the people I dated. It was few and far between, and brief. 

“Yeah, I’d love to meet her,” I replied, anxious to start talking to someone. That was the whole point of coming out tonight, to try and meet someone, possibly more.

We moseyed on over to where his friend was and he introduced me. “Jane, this is my friend Luke. Luke, Jane.” 

I waved awkwardly, with a nervous smile, which she reciprocated. 

“Hi.” 

“Jane is a painter. She’s really good. You should see some of them. Watercolors,” James offered, jumpstarting the conversation.

“That’s cool. I have no artistic ability whatsoever,” I offered with a nervous laugh. 

“That’s okay. I’ve been doing it for a few years. I was pretty bad when I started,” she replied.

From there, the conversation mostly started flowing, with a few hiccups here and there before a new topic for discussion was brought up. James could tell we were hitting it off, and eventually excused himself to disappear into the night.

I was feeling far less nervous at this point. I think Jane had a lot to do with that. She was sweet, and kind, and seemed to appreciate my awkwardness, my lacking any fake veneer that some people put on. We had a few more drinks, well I had one, because I’m a lightweight, but the rest of the night went by quickly. Eventually, it reached that decision point of going our separate ways, or going somewhere else together.

We decided to leave together.

We wandered around on sidewalks, continuing our conversation, and laughing quite a bit. I’m sure my slight inebriation helped with that, making me less of an uptight square.

Standing at a stop sign, waiting to cross, Jane turned to me and asked, “Hey, um, you seem really nice. And I was wondering if you’d like to come back to my place for a bit?”

Even though things had been going well, I did not expect to find someone as cool as her tonight, and be invited to her place. But yes, of course I wanted to.

“Yeah,” I said, trying to play it cool, but secretly beginning to sweat through my shirt. 

“Cool,” she said, before grabbing my hand and leading me in the right direction. I was slightly behind her, admiring the way she looked in her dress. A very cute, slightly floral dress that bounced around her legs as she walked. I couldn’t help wondering what she looked like without it. 

We got to her place, a small apartment on the second floor that wasn’t that far of a walk from where we had been. Her decor was very cozy. Houseplants dotted the apartment, a cozy woven rug beneath a clean coffee table with a candle on it. A slight glow coming from string lights that were on. Much nicer than my place. If you saw my place, you might swear that some kind of transient serial killer lived there. It’s not quite that bad, but compared to her place, bad.

She played the good host, asking if I wanted anything to drink. I was already kind of at my limit, or at least wanted to try and be clear headed for the rest of the night, so I declined, but asked for a water. All this talking was making me dry. 

We sat on the couch toward each other, her with one leg crossed over the top of the other, dangling playfully and very close to my leg. We were mostly just talking about dumb nonsense at this point. Making stupid jokes, making each other laugh, you know, stupid shit. Like when you know you’re both into each other, and maybe just a little tipsy, and you just want to make the other person like you more. Your body language giving off subtle hints to them, ones that you may not even be aware of. 

She had just finished making some dumb joke about “Being transgengar.” She was into pokemon, and herself trans, and there’s a pokemon named Gengar. I think that was the extent of the joke. She really got me with that one, but I recovered from my laughing as I felt her dangling foot start rubbing my leg. I stared at her, and she at me, us both knowing what we wanted and what we needed. 

I leaned in to kiss her. 

It was very nice.

My head was swimming a bit. The alcohol had probably mostly worn off for me at this point. I think the kiss and my arousal were responsible for the intoxication I felt.

“Do you wanna…” she suggestively asked, without fully finishing. I nodded slightly, my face feeling flush. 

She stood up first, taking my hand and leading me to her bedroom. 

If the rest of her apartment was well-decorated, then her bedroom seemed like heaven to me. I admit, part of that may have been my horniness talking, but I could fully see myself spending hours in this bedroom with this woman. Together in bed, not necessarily having sex, but just being there with her, close to her, running my fingers over her body.

I looked around for a moment taking it in, before she regained my attention by pulling me down to sit next to her. I scooched a little closer, my hand on her back, and leaned in for another kiss. This kiss was deeper than the last, as she laid back, and I partially on top of her. We began to make out, our hands exploring our still clothed bodies..

I wanted my clothes off. 

I stood up, unbuttoning my shirt in front of her as she stared at me, still laying down. Then I  unbuckled my pants, unzipped them, and pulled them off. All while staring at her, lying there, wordless. Both of us drunk on the moment.

As I stood in my underwear, she crawled up onto her knees, facing away from me. She worked her hands under her dress and began to wiggle, then getting down on all fours, to coax her underwear the rest of the way and past her feet. 

She turned to look at me and did her best to throw them playfully at me, catching me in the chest with them. I felt like a half-naked bridesmaid catching the bouquet, right before getting to have sex with the bride. She then slowly lifted the hem of her skirt, revealing her shaking little butt and the other part of her. Between her legs hung a beautiful cock, on this beautiful woman, who for some reason brought me back to her apartment. 

Well this was just going swimmingly.

So, I’ve never had anal sex. I’m assuming it’s similar to regular sex, just different place, but I didn’t know what the hell I was doing. I moved up behind her, too high on the moment to be that nervous. My cock so far was doing its part, standing at attention for this beautiful woman, still wiggling slightly. I did know enough to know I probably shouldn’t go in without some lubrication, so, seeing none nearby I spit down onto my hand, rubbing my cock first, then again lubricating her asshole as best I could.

Thank god I started drinking that water when I got here. Never know when you’re gonna need to spit on that thang.

I tentatively poked her asshole with my cock, not sure how hard I should be pushing. I could hear her breathing heavier as we moved closer to our goal. Being persistent, I was able to push inside of her, the warmth hugging my cock. Now I was feeling very high.

I started pushing in and out, as she began helping me with her body. For being my first time, it felt pretty good. And it sounded like she was enjoying herself. This continued for a few moments, me withdrawing once to generously re-lubricate with spit before continuing to fuck her. Her moaning grew louder, her breathing quicker. 

But…it never quite progressed past that point. Both of us seemed to be having trouble reaching orgasm, even with our continued rutting. We both sensed this, and I pulled out, my cock starting to shrink slightly. I sat down on the bed, and she joined beside me, still sweet and rubbing my chest.

“Can I use your bathroom quick?” I asked.

“Yeah, it’s right down the hall,” she replied. I gave her a quick kiss that threatened to go longer before I pulled away. Finding the bathroom, I turned on the hot water, soaped my hands and washed them and my cock awkwardly. I dried off with some toilet paper, checked myself in the mirror and headed back.

Jane was laying on her side on the bed, rubbing a hand over the comforter. “Hey,” she said, turning her attention to me. 

“Hey,” I offered back, going to lay next to her. “Sorry about that, it was just hard for me to cum. That was my first time, uh, with anal.”

“It’s okay,” she said, putting a hand on my chest. “You were great,” which reinflated my ego somewhat.

“Could we try something else? I’ve also never given a blowjob before.”

She smiled, stroking the back of my head, “Yeah, we can do that,” she cooed at me. She scooted cutely over to the edge of her bed, as I stood up and walked in front of her. She teased her skirt up her legs slowly, making me wait, and I got on my knees. 

As I was on my knees, and saw what was in front of me, I realized my prayers had been answered.

Dangling there between her legs, was a gorgeous, uncut cock, larger than mine. I placed my hands on it, before remembering some lubrication and brought one hand back to spit on.

She interjected, “Let me help you with that,” and spit into her hand as well, before greasing her ladyboner up and down before me, seeming to take extra pleasure in seeing me, on my knees, watching her stroke her beautiful cock. It had to be obvious how much I wanted it, and she seemed to be relishing it. “There, that’s better.”

I placed my hands back onto her now well lubricated dick, moving my hands up and down her shaft, much like I would with my own cock. She was laid back propped up on her elbows, and I could see her hips moving as I stroked her.

I loved watching the way her foreskin glided up and down her cock, partially covering the head of her penis before retracting. I couldn’t wait any longer to get a taste of her, as it appeared she was now leaking a small amount of precum.

Her cock entered my mouth, the first time any cock had been in my mouth. Inexperienced as I may have been, I suppose instinct took over, having watched so many videos of blowjobs being given by pornstars over the years. 

I swirled my tongue around the tip, as I knew that would be sensitive. At least, mine was sensitive there, and why would her uncut cock be different. One of my hands stroked her shaft, and the other moved to her stomach, to feel her moving and perhaps be another way for me to stimulate her.

This went on for a few minutes (I honestly lost track of time). Her breathing getting heavier, me recognizing the signs that we were getting her close. Her thrusting slightly in my mouth, me accepting her thrusts, grateful I was finally able to pleasure this woman.

When she came in my mouth, it was still a surprise to me. I tried not to cough, and only gave a snort, but my mouth now had a warm meal in it that I didn’t know what to do with. I continued to pleasure the head of her cock, my lips closed more tightly around it, as I didn’t want to spill. Just the thought of her cum swirling in my mouth as I continued to pleasure her makes me hard to this day.

She sighed heavily and fell back onto the bed, her sex now spent. I sat there on my knees for a moment, mouth full of her cum, deciding what to do, before just swallowing it.

Down the hatch.

It wasn’t the best thing ever, but I had just had one of the best nights I’d ever had, and I was impatient to get up on that bed and go snuggle with an angel.

I crawled up beside her, as she lay there slightly blissed out. Her hand reaching out to my face and brushing my cheek, “That was so good. That was your first time?” she asked, slightly out of breath still. “I don’t believe you,” she laughed. 

I laughed too. Then I kissed her, my mouth still slightly tasting of her cum. We made out a while longer, before settling in beside each other in her bed. Snuggling to sleep. 

This was heaven.

And that’s the story of dick and Jane.