The Diner

I couldn’t help but feel so surreal being back here, as we strolled through the doors to DiMaggios diner. Neon signs illuminated booths decorated with cream and red leather seats, like the seats from old 1950s Cadillacs, while waitresses in cute uniforms delivered milkshakes and meals to the hungry patrons.

The place was like something straight out of Grease, a romantic dream creation that banked hard on the nostalgia and aesthetics of one of America’s golden ages. I had to admit, for someone who loved places with a strong and well co-ordinated aesthetic, I really liked this place, especially as it was the kind of spot that would make you feel like the main character of your own little story eating here.

I wasn’t the only one to enjoy it either; DiMaggios was a firm student favorite, and especially an attractive date spot for couples. That was exactly why it felt so bizarre for me being back here; it had only been such a short time since I’d come here with Lisa, my own first date with my crush. As I walked behind Jimmy to one of the booths, I couldn’t help but reflect on everything that had happened.

I’d been so excited and nervous when Lisa had said “yes!” to being asked out. A girl like that, actually wanting to come with me on a date. Beautiful, smart and kind, a popular girl who truly deserved to be, someone anyone would crave being close to. My heart had definitely been racing for a good few hours after I’d asked her, so much adrenaline moving through my system, my knees weak from how much the moment had played on my heart.

It was so different from what had happened in highschool, the brutal rejection from my crush there, and the aimless, formless, grey misery that had followed until I graduated. I’d wanted college to be my fresh start, my chance to really have happiness. When Lisa had agreed to go with me on a date, and even seemed excited about it, it really felt like my dreams were going to come true.

Well… that didn’t go quite as I planned.

Our date had been wonderful really, maybe too wonderful. Perhaps I should have been more suspicious of how well it was going, at least until the twist ending when Candida revealed herself. The paralyzing fear I’d felt as she stabbed me with her spines, the sickening confusion and terror at being betrayed by “Lisa”, and the ominous weight of the words she’d spoken to me were still close in my mind, both from how recent they were, and how much they’d permanently altered my life.

But then again… in a way, wasn’t this exactly what I’d wanted?

My dreams of having a full college life, excitement and fun with new friends and rich new experiences. Romance and sex, both things on every new college student’s mind, I’d had in heavy quantities since being turned. A life full of possibilities too; well, my life had more possibilities than ever would have been possible before this.

There were other things I’d craved too, deep down…

Memories of the more secret, shameful side of me flowed up, the embarrassed clarity that would sometimes come after masturbating to some TG fantasy. Self-inserting as the girl everytime I wanted to cum, maybe imagining myself as a party slut or as a shy girl, or anything in between. The nagging, subtle fear that I should try and be normal, that this was all unhealthy. Well… those desires had been realized in a way more amazing than I’d ever thought possible.

As I smoothed out my skirt and slid in the booth, it was impossible to ignore how feminine the body I wore now was. Long, wavy blonde hair cascaded down my shoulders and back, while Ashley’s ass, though not as big as Lisa’s or especially Emmy’s, was still more plush than my real one. I was in a pink satin dress, it’s light and smooth material providing all kinds of tactile pleasure, that somehow combined the illicit, exciting thrill of crossdressing, with a powerful, girly euphoria at knowing all I needed to do was turn and see my reflection in the diner window to know every inch of my body was fully encased in a cute girl right now.

Really, I’ve been having too much fun with this…

My internal monologuing was broken by the waitress taking our orders; burgers for the both of us, with the big specialty milkshakes DiMaggio’s was famous for.

“You know, I really love this place…”

It was true for both me and Ashley. She had a keep eye for aesthetics, and while the 90s were her favorite, anything stylish and romantic with some hits of Americana appealed to her. I’d noticed since wearing her I found myself looking at people’s outfits in a different way, or even the ways signs and buildings looked. It was an appreciation she had that went a little deeper than most, and it was an unexpected pleasure of being her.

“I do too, actually.”

Jimmy smiled across at me warmly.

“Huh, really? I didn’t strike this as your kind of place at all.”

He looked just a little taken a back at my comment.

“Wait, why not?”

“Well, you know… you’re always playing videogames and on discord, or partying or whatever. It just didn’t seem like your kind of place.”

“Hmm, hmm. I see. Anti-gamer discrimination. I didn’t take you for the type, Ashley.”

“No…!”

I stared laughing as he nodded sagely, infusing play-acted sadness into his mannerisms.

“… don’t act like anti-gamer discrimination is a real thing! It’s just, you know. This is kind of a jock type place.”

“Ah, I see. So, I’m officially not a jock type, not a chad. Oh, woe is me!”

His playacting reached new heights of maudlin while I laughed harder.

“Okay, okay, I was wrong! You’re a big strong chad, okay! Geez…”

“You know, I think I should commemorate this actually. So I can fit in with my new found jock status.”

“Oh yeah?”

I raised my eyebrow, quizzically.

“Yeah. I’m going to get one of the jackets.”

“Are you sure you can afford one?”

My teasing came with a deadpan seriousness that caused him to try to suppress his own laughs under his upset façade.

“You’ll see, I’ll be back in a minute.”

He stood and headed off to grab one, while I rested my head on my arm, still amused by our banter. The jackets we’d been talking about were these vintage infused varsity jackets, a collaboration between DiMaggio’s and our University. It was a surprisingly natural fit; DiMaggio’s had all the links to quality 1950s inspired local designers and apparel producers, while the College had the academic heritage and sporting tradition to inform the jacket design with a certain authenticity, even while being a 1950s throwback.

The result was a varsity jacket anyone could look good in, the school colors of red and white looking crisp and attractive, especially in the context of a classic varsity jacket. Within just a few short minutes, Jimmy returned, all smiles as he sported his brand new jacket.

I had to admit, it genuinely did look really good on him. It kinda made him look wholesome in a way, like the kind of young man a strict, conservative white dad would feel more comfortable dating his daughter. I couldn’t help but feel a perverse humor in the contrast between his currently clean and “friendly to moral society” appearance, compared to the knowledge that this was the same guy who’d just fingered me in a cinema, and the same guy I’d futanari fucked while he wore the skinsuit of a pretty young woman early today.

“Hmm, hmmm. Okay, I admit it. Now I’m officially on a date with a hunk.”

He laughed, and it was clear he was really pleased with the way the jacket looked on him.

“I’d need to be, to have landed a date with such a gorgeous girl.”

His smile was so genuine and warm as he said it, sincere feelings so obvious in his expression.

“Huh-!”

The suddenness of his attack caused my heartbeat to spike while a blush took my cheeks, a hot, girly attraction to how smooth yet real that had been bursting my heart. I opened my mouth to respond just as the food arrived, looking to the side to at least try to hide how affected I was by his words even as the waitress laid down the plates.

Woah, what the hell?? Why am I feeling so strongly at that…? Am I starting to “like” him? Or is it just all these female hormones, everything we’ve done together today, my roleplay of Ashley on a date reaching new heights…?

I tried to distract myself by taking a bite of my burger, immediately enjoying such rich flavors as it entered my mouth.

“Mhmm…!”

I couldn’t help but moan a little, causing Jimmy to laugh more.

“Hey, mphff- don’t laff-”

My words were so distorted from my mouth being full, I was barely speaking English and certainly not looking lady-like, but from the affection in the way he looked at me I could tell I was still looking cute. After I swallowed I finally got to say;

“Fine, fine, laugh it up! But you know, this burger really is that enjoyable, so the real winner in this exchange is me I’d say. Try yours actually, you’ll see.”

“Okay, okay! You don’t need to apologize for being adorable.”

“Hmpff!”

I huffed in a dramatic fashion, no doubt only furthering the adorable allegations when it was displayed on Ashley’s cute face. Jimmy’s expression soon changed to its own depiction of wonder, as my burger based claims were validated fully.

“Mhpfff… Yeah… Oh My God. You were right, this is fantastic.”

“Hmm, hmm. Yeah. That’s what I thought.”

My smile was smug as I idly ate one of the fries, seeing Jimmy enjoy his own meal being almost as good as enjoying my own. It wasn’t long before we’d scoffed the whole lot, a comfortable fullness suffusing us as we basked in the aftermath of such delicious flavors.

“Aaaand, here’s your milkshake too!”

A cheerful waitress slid a large strawberry milkshake with lots of whipped cream on top and two straws between us, before skipping off to see other customers. I peered at it in curiosity, interested to try it mainly as Ashley’s memories told me it was her favorite flavor.

“Strawberry, huh?”

“Well, you know it is your favorite.”

Jimmy had a smile as affectionate as it was a little embarrassed, remembering the small details in a passing conversation he’d had with Ashley at a party at my house a few days ago. It was cute he remembered… and also a trip for me that I did; seeing my own apartment through Ashley’s eyes, in her memories, while my own memories confirmed I’d been there in Lisa’s skin at the same time.

“How cute you remembered.”

I teased, leaning forward and drinking from the straw closest to me as I pushed a stray lock of blonde hair behind my ear.

“Mhmmm…”

I couldn’t resist moaning a little as the taste danced on my tongue, the sweet pop of flavor being like energy and happiness rolled into one. Ashley’s sense of taste absolutely didn’t disappoint…

Jimmy joined me, his face close to mine as he drank too, a light blush coloring his cheeks as he heard my moan.

The two of us, drinking from the same milkshake in this diner… this is such a classic couple image.

A thrill tingled around my heart thinking about it, the strange but wonderful pleasure of being a part of something like this and knowing I was the girl making me feel really, really good. Before I knew it, we’d finished our milkshake, and were leaving the diner. I’d offered to pay, but Jimmy had insisted he get the bill.

That dummy…

I could tell Ashley really appreciated it, and I enjoyed stealing her positive feeling of gratitude as I wore her personality, but still…

Trying to act the gentleman, when I know he’s really just as broke as me.

The campus was beautiful, even in the evening when so few people were about. A lot of old, traditional buildings added a romantic flair to the grounds, with the modern buildings splashed in emphasizing the University's dedication to making its place in the future as much as honoring its position in the past. Walking back to Ashley’s apartment, I couldn’t help but reflect on the date we’d just had.

“I’ve had a really lovely time tonight Jimmy… I think I’m seeing a side of you I never did before.”

He gulped a little at that, but his slight nerves just added some adorableness to proceedings. I smiled at him, enjoying the mood, and the feeling of being Ashley in this moment, before my thoughts were broken by the falling temperature.

“I guess it’s really cooled off, huh?”

I remarked, noticing the red and orange tones beginning to creep into the leaves of the trees we were walking past, as the cool breeze chilled me just a bit. As much as I’d loved wearing this satin dress, it was so light with so much bare skin; it really wasn’t keeping any heat on my body at all.

Just as I thought that, I felt something warm come around my shoulders, comfort seeming to envelope me all at once.

“Huh…?”

Jimmy was smiling as he lay his jacket on me, the new varsity jacket warming my body, and especially my heart.

“Jimmy…”

“Hey, don’t worry about it. I’m always going to be your knight in shining armor.”

A pessimist might have disliked such a sincere and cheesy line, but I didn’t, and wearing Ashley’s personality, I could tell she loved it. For a girl like her, a secret romantic who’d been let down before, these were always the kind of moments she’d craved. My heart melted as I pulled the fabric closer around me, as it felt like a hug.

I was so lost in the moment that I didn’t even realize I’d made it back to Ashley’s apartment, standing on the steps to her building. Jimmy stood behind me, his nerves beginning to dissipate fully now, all the enjoyment he’d felt over the date and getting the opportunity to be the gentleman feeling way too good for him.

As I turned to him, I only had one question;