Jason Ashley Valentine (Trap Content)

The epiphany came to me in the same exact moment as I began unleashing a torrent of spunk into Ashley’s mouth.

The familiar face, the computer science degree, the flat chest, Ashley was Jason’s middle name. I just nutted into my best friend’s mouth. Ashley wasn’t a girl at all, or maybe they were transgender, I had no idea. It was never the case while I had known them, but I hadn’t spoken to Jason in half a decade, things may have changed. I then realized that Lindsey had never been specific about Ashley’s gender, neither of them had even used any pronouns, and I hadn’t either so they couldn’t correct me.

“Gulp, hulp, mmmn gulp!” my friend was swallowing my sperm as eagerly as Makenzie had done, and looked just as blissful, if not more so. This was so strange, we had only ever just been friends, and I never even knew Jason was into guys. Besides that, I understood perfectly well why I hadn’t recognized them sooner, but did they not recognize me? Surely, I didn’t look much different from when I was in middle school. If this was Jason, why didn’t they say anything? Also was it bad that I was thinking of them as Jason? Was I deadnaming my friend in my own head?

“Jason?” I asked, once my lengthy ejaculation had ended.

Their eyes shot up to mine and widened slightly. They pulled away from my rod, slurping loudly as they did. When at last the tip popped out, a string of cum still connected my tip to their dark red lips, and their mouth was full of the remnants of my seed.

“Gulp… gulp… fuck,” they gasped, “uh, hi Jack.”

“Is it really you?”

They blushed and poked their index fingers together bashfully, “um, yeah, but I go by Ashley now.”

So, I had been deadnaming them, my bad, “Wow,” I laughed, “I had no idea it was you! I can’t believe we’re going to the same college. I missed you!”

Ashley blinked, seemingly a bit surprised at my reaction, “You’re uh, not mad at me?”

“Mad?” I asked.

“Well, I-I recognized you from the very beginning and I didn’t say anything… I also didn’t tell you that I was… you know… a guy before I sucked you off.”

I scratched the back of my head, “Oh, yeah I guess you didn’t. How come?”

Ashley blushed furiously, “Well, I was afraid you wouldn’t… you know… let me if you knew who I was. Look, I know it wasn’t fair and I shouldn’t have tricked you, I’m sorry. I was just so nervous because I didn’t know how you felt about guys, you only ever seemed to be into girls back then.”

That made two of us, frankly, I had no inkling Ashley had ever been attracted to guys either. Also, I was pretty surprised at how well I was handling this, perhaps I hadn’t been as straight as I thought I was either, “Well, I’m not sure how it would have made me feel back then. But you’ll be happy to know I’m much more comfortable about my sexuality now. Honestly, I’m really not too bothered by it, and this is the first time I’ve ever gotten a blowjob from…” I paused, realizing I might have been about to make a big misstep, “sorry if this sounds rude to ask, but are you transgender?”

They actually smiled at this question, it seemed I made the right move at least as far as Ashley was concerned, “Honestly, no, I’m just a crossdresser. But I don’t want people to walk on eggshells when it comes to my pronouns. I’m not picky about them, refer to me however is most comfortable to you.”

Okay so I hadn’t been making a horrible mistake this whole time, “Okay that’s good. This stuff is still kinda new to me, so I never know how to deal with it.”

“I’m kinda unique in this way, but I like when people use female pronouns cuz it feels kinda like a compliment, you know? I try damn hard to make myself look like a girl so it’s nice to get involuntary recognition. When I get called male pronouns its also pretty hot because I’m being correctly identified in spite of this getup. But anyway, you’re really okay with the fact that I just sucked you off and drank a lot of your sperm, knowing that I used to be your best guy friend?”

“Well first of all, yes, I’m okay with it. Honestly more okay with it than I thought I might be, but here we are, all the better for it. Second of all, you still are my best guy friend. No past tense about it. I’m happier than I’ve been in a long time, honestly. I’m so glad I will actually know someone up here.”

This seemed to strike a deep chord in him, he was slack-jawed for a moment and then he smiled wide with flushed cheeks and I saw tears start to form, “You have no idea how happy I am to hear that.”

“By the way, you do a great job. I legitimately had no idea you were a guy. It took remembering that Ashley was your middle name for me to finally realize it.”

Ashley wiped away the tears and sniffed before responding, “It helps that I’ve always been kinda scrawny and androgynous. That way when I started taking hormones it worked absolute wonders,” as he explained this, he was bashfully twisting his finger in a lock of his hair.

“Oh, hi Ashley,” It was only in that moment that I realized there was no longer the sound of running water. Makenzie was standing in the doorway with a mess of wet hair and a towel haphazardly wrapped around her torso. I was happy to see that even without her umbral makeup she was pretty cute.

My friend turned to look at her, “Oh hey! Nice to see you again!”

Makenzie smiled slightly and made her way over to the dresser, retrieving a pair of black panties and slipping them on under her towel, “Yeah, same.”

“Did you have a fun vacation?” Ashley asked.

“Ugh, no,” she said, removing the towel, unleashing her massive breasts. My gaze shifted downward, and I was amused to see Ashley do the same, “I stayed at Nick’s place and he was so fucking boring. Thank god I met Jack on the bus, and he ordered me to break it off with him. Nick was kinda clingy.”

“I mean, I can’t blame the guy. Have you seen your rack? I’d be clinging on for dear life too.”

I had to laugh at this, not necessarily because it was funny, though it was definitely silly, but because I had almost exactly the same thought when Makenzie had first told me about her ex’s clinginess.

“You,” Makenzie shot a finger at Ashley before pulling a black t-shirt with a purple broken heart on it from out of her dresser and then donning it, “turned down that opportunity. I don’t wanna hear it from you.” her tone was teasing, not really serious.

I blinked. It almost sounded like Ashley had turned down a relationship from Makenzie. I might ask about that later. In response to this accusation, Ashley just laughed a bit awkwardly and then glanced at me before returning to the busty goth.

After donning the shirt, that wasn’t quite revealing enough for my fancy, Makenzie went to her phone on her desk and looked at it, “Shit. Hey, sir, I know I said I’d show you around, but a couple of my friends want to hang out. Mind if I bail on you?”

Before I could even answer, Ashley chimed in, “I don’t mind giving him the tour. It will be good to catch up.”

Makenzie threw up an eyebrow, “You two know each other?”

“As it happens, we do,” I said, “Jas— I mean, Ashley is a childhood friend. He moved away back when we were in middle school, though.”

“Oh, well that’s cool. Glad you guys found each other again.”

“It’s a hell of a coincidence,” I smiled, and was glad to see Ashley smiling too. Then I turned once again to Makenzie to address her top, “Hey, before you go out, would you mind taking a pair of scissors to that top of yours to turn it into a crop-top?”

“Will do,” Makenzie nodded then started to make her way to the bathroom, “I’ll see you later.” She then disappeared into the bathroom, presumably to do her makeup.

“Let’s go! I can’t wait to show you all the best spots to hang,” Ashley said, excitedly, getting up, grabbing my arm, and yanking me toward the door. I barely had enough time to zip up my pants and get rebuckled before I was out the door completely. I had left my new notebook on the desk, forgotten in the excitement of having my friend back.

Ashley’s tour of the campus was trimmed down and very bare bones, except when he was showing me a place he particularly enjoyed. Still, I got the basic gist of all the facilities I would need. He explained which road I would need to take in order to go down into the town that sat adjacent to the campus, Autumn Ridge, and explained that a bus ran directly between the university and the town’s bus station. This made it pretty convenient to get to anywhere else in the city if needed.

He admitted that while he would love to be the one to show me around town, he had a friend who would be a much better option, as she was a local and actually had a car to do it with.

Otherwise, the trip around campus was a good excuse to catch up with my best friend, to find out what he had been up to in the six years since we had seen each other last. A lot had happened in such a short time to Ashley. He became friends with Lindsey after I had moved away from our hometown at her new school and mentioning this made me realize I’d seen her before as well though we never really knew each other while we were kids. The two of them became fast friends, and Ashley admits that Lindsey was the reason he had become kind of a slut. But she had also taught him to be more comfortable with his true self and what he wanted. She was the one who encouraged him to start crossdressing, and even helped getting their peers to accept it and start calling him Ashley, for the most part.

“I owe Lindsey a lot, she’s been a really good friend. When I told her I was gonna go to college up here she dropped everything and came with me without a moment’s hesitation.”

“That’s great. Seems I owe her a lot too,” I said.

Ashley looked at me, eyebrow raised.

“Well, she not only kept my best friend company, she helped you find yourself. That’s a pretty big deal.”

Ashley blushed and smiled, “Dude, quit being so awesome.” He then gave me a playful shove, “I get why you’re our messiah now.”

I smiled and rolled with the compliment. I wasn’t exactly sure how I should feel about that title yet. I certainly didn’t feel like I earned it. Then again, do messiahs generally earn their title? I wasn’t sure.

“So where are we headed next?” I asked, to change the subject.

“Well we’re just about done, I gotta show you the Victoria building, it’s one of the student common areas, and it’s my favorite. You’ll see why when we get there.”

I nodded as we made our way. All the walking today was starting to make my feet sore, but I tried not to think about it. I was having fun, so thankfully the pain was easy to ignore. We were slowly approaching the building when I heard someone calling out to us.

“Excuse me!” It was a woman’s voice, low and delicate. When I turned to look, I immediately blinked in disbelief. It was as though I had just been approached by a pair of time travelers from bygone eras.

It was a man and a woman, the former of whom looked exactly like what I might have imagined if someone told me to think of a vampire. He had slicked back black hair and a pair of deep red eyes that must have been the result of colored contact lenses. He was sharply dressed in an outfit that looked like it was straight from the 1920s, complete with a deep black slacks, a vest, and a vivid red button-up shirt beneath. No tie, and the first few buttons were stylishly undone. He was tall, kinda lanky, and honestly didn’t look all that fun to be around.

If the man looked out of place in terms of time period, the woman looked ancient by comparison. Her outfit appeared to be from a macabre Victorian-era funeral, specifically from the casket. She was wearing a jet-black corset dress with frilled lining that looked fairly stylish albeit out of place in the middle of a college campus during the summer. Luckily the climate tended toward colder temperatures in this part of the country. A great deal of cleavage was on display, and this woman had an ample amount to show. Not quite as much as Makenzie or Lindsey, but still quite a bit. She was otherwise quite light-skinned, with pale blonde hair that was nearly white done up in a fashionable bun, and a dazzling pair of green eyes which were surrounded by the traditional gothic makeup.

“I’m sorry to bother you but—” the woman began, “oh my, it really is you. The real Jack Lantern, standing in front of me.”

“Uh, hi,” I replied awkwardly.

“This is fortuitous indeed,” the man added in a tone that I already hated for all its snobby and slight nasally qualities, “though I expected the chosen one to be a little more… sharply dressed. It is an honor nonetheless.” He then bowed. Not only did this guy look out of place, he acted like it too.

“I am surprised as well, I at least expected him to be in gothic garb,” the woman said.

“Sorry, there wasn’t much in the way of gothic stuff where I came from, and I never had enough money to delve too deeply into it.”

The two shared a look, but the woman replied, “I had never considered the idea that our own messiah would have financial troubles. What a world we live in when one of the most important religious figures of our time can be in such dire straits.”

“I suppose that does explain it,” the man nodded, rubbing his chin thoughtfully, “ah, but where are our manners. I am Sebastian, and this is my girlfriend, Elizabeth.”

“My friends call me Eliza,” she said, smiling warmly at me, “but you may call me whatever you please.”

I had to admit, I already wasn’t much of a fan of these two. They both seemed pompous and spoiled, and their archaic manner of speaking was driving me nuts. The guy, Sebastian, was especially rude and seemed like kind of a dick. The sort of guy who wouldn’t have even given me the time of day if I wasn’t literally his faith’s most important person. He reminded me of those people in my high school who used to pass roleplaying notebooks between each other, and who took it way too seriously. I felt like the only reason this guy was anything other than a shut-in was that he actually had a pretty hot girlfriend.

Speaking of the girlfriend, Elizabeth was stunning. She had a similar taking-roleplaying-way-too-seriously vibe, but unlike Sebastian she seemed a lot less rude and uptight. One of those people that was full of themselves but still managed to be a nice person in spite of that. And any drawbacks her personality might have had, her sex appeal made up for in spades.