Prom Night

This is my first original trans/cross-dressing story. I previously wrote a sequel chapter to another Literotica author's story but I'm having trouble getting it published here because the author whose work I continued hasn't published a story in over five years and hasn't responded to my requests to base a sequel story on theirs. It looks like it won't see the light of day, which is a shame as I think it's pretty good (for me).

Anyway, I hope you enjoy this story, my official first story in the trans/crossdressing space.

***

We had been friends since primary school. We went everywhere together, did everything together, and sat together in all our classes at school. We were more than friends.

We didn't have a leader but if there is a bad idea to come up with it'll be Robbie who suggests it.

This time, it wasn't so much a bad idea as just a plan that was unlikely to succeed.

The end of our final year of school was approaching and we were all still virgins. Robbie's plan was for us all to get laid on prom night.

I had no objection in theory but it just didn't seem likely. Still, what's the worst that could happen? Might as well give it a go.

Robbie had it all planned out. He was going to ask his date, Jennifer, back to his hotel room. His family was rich so he had booked a good room in the most expensive hotel in town. He was planning on the room being impressive enough to get Jen to drop her panties for him.

Robbie's plan for Mark was to take his date, Amanda, to the planetarium. It was known as a sure thing as a date destination because of the romantic sights and Robbie was hoping it would be even more certain after the Prom.

My name is Luke, although the other guys sometimes call me Lucy when they tease me for looking feminine. Robbie's plan for me was to take my date, Millie, to the lookout point, where kids with cars like to take their dates. I had the nicest car of the three of us and Robbie hoped it would be enough for Millie to open her legs for me.

I could tell Mark was as dubious as me but we both agreed as we hoped Robbie's plan would get us laid finally.

At the prom itself, everything seemed to go well. Robbie seemed to be getting on well with Jen and Mark and Amanda spent most of the time on the dancefloor together.

However, after the prom, I took Millie to the lookout point and it soon became clear I was well and truly in the friend zone. We'd been chatting well all evening and it seemed Millie looked at me like 'one of the girls' for some reason.

Disappointed, I dropped her off at her home and she kissed my cheek as she left me alone in my car.

Just then, I got a call from Robbie.

"How's it going, pal?"

"Struck out," I said in a dejected voice.

"Sorry, mate. If it makes you feel any better, so did I."

"No way! How did that happen?"

"She seemed to be into me all evening but she was a bit shocked when we got to the hotel room. It got a bit real for her and she bailed."

"Shit, sorry man."

"Yeh, no worries. How about you?"

"The usual -- mayor of the friendship zone."

"Sorry, man. Hey, why don't you come over and help me empty this minibar?"

"Sure, let's drown our sorrows."

About twenty minutes later, I was in the hotel corridor as Robbie opened his door.

"Hey pal. I called Mark but got no response. Maybe he'll be the lucky one!"

"Hope so, for him," I said as I took a seat in his suite's living room.

"Here you go," he passed me a beer.

"Cheers," I said as I opened the can and took a mouthful. "What's that?" I asked, pointing to a clothes hanger hanging on his bedroom doorhandle.

"Oh that," he said with a grin. I got the impression he was happy I noticed.

He brought the hanger over to me and I soon saw it was a barely there white baby doll negligee and a matching lacy bra and thong.

"Were these for Jennifer?"

"That was the idea," he said ruefully.

"And she ran for the hills as soon as she saw them?"

"Fraid so."

"Geez, sorry man, she would have looked amazing in these," I said, feeling the soft material.

A few beers later, I noticed Robbie looking at me and I realized I was caressing the soft material of the lingerie items again. Why was I so fixated? More surprisingly, why wasn't he taking the piss out of me for it?

"You like those," he said. It wasn't a question.

If I'd been any less tipsy, I would have tried to deny it.

"They're soft," I said, stupidly.

"I bet you'd look good wearing them," he said, but he wasn't joking or mocking, the way he normally was when he pointed out my feminine looks and build.

"Ha, yeh right!" I said, trying to brush him off, but the image blossomed in my head and felt oddly right. They would look good on me. Why shouldn't I wear them? Because I was straight, of course. But that didn't seem so important right now. I'd never thought of wearing female clothes before but it didn't seem so weird now for some reason.

"I'm serious," said Robbie, "I bet you would look great if you wore them."

I didn't say anything. I just kept stroking the soft material.

"You could take it in the bathroom and see what you look like," said Robbie after a while. "You don't have to show me."

"But if I do come out and show you, you'll laugh at me for a week and mock me about it for the rest of our lives!"

"Dude, look at me, I'm serious. I will never mock you for it if you do wear them... I would just like to see what you look like."

I looked at him for a long time, trying to work out if he was serious or if he was setting me up.

Eventually, without saying anything, I got up, taking the lingerie with me into the bathroom.

Robbie smiled as he saw me go but I didn't see any sign of victory in his expression, like he'd set me up.

In the bathroom, I found a brand new collection of makeup and a pair of white high heels. I'd never tried using makeup before but I knew the basics from seeing the girls touching theirs up in class.

I had a go at a subtle makeup job with a bit of shadow to accentuate the feminine features of my face. I examined it in the mirror and was pleased with my work. I may be biased but I couldn't tell it was a first timer's job.

Happy with the makeup job, I removed my clothes and put on the thong. I loved the feel of the cool, soft material against my skin. The snug fit across the top of my ass cheeks and the way it hugged my little cock against my abdomen gave me a feeling of security and comfort.

I checked myself in the mirror and was surprised by how sexy I looked.

Next was the bra. There wasn't much to fit in it but it helped the look. Finally, the baby doll negligee and the white three inch heels.

I pulled my long blond hair out of its usual ponytail and it naturally fell around my shoulders.

I looked at myself in the mirror and was shocked with what I saw. Looking back at me was a sexy blonde in gorgeous lingerie.

Not even a five o'clock shadow or hair to take care of on my arms or legs -- I could never grow much hair. I only needed to shave my face once a week and I never had more than very fine, very pale hairs on my arms and legs, which never showed up. I didn't even have much pubic hair. Just a little tuft above my little cock, which I felt expanding slowly against my abdomen.

Could I do this? I knew Robbie was expecting me to come out and show him but what if he just laughed at me?

Then I thought of all the effort he'd gone to. To get in Jennifer's panties. But then I realised, Jen was at least a D cup and the lingerie he'd bought was an A cup. And the heels were in my size, not Jen's, too.

Had he ever expected Jen to come back to the hotel with him?

Had he really done all this for me?

If so, because he actually thought I would look good or as the ultimate prank?

My heart felt like it would beat through my chest as I considered my options.

I couldn't do it. Could I? He seemed genuine. But then he had seemed genuine when he made Jeremy think he was on national radio and got him to say a bunch of funny things before he realized it was a prank.

But would he be that cruel to me? We had been friends forever.

Before I could decide what to do, my hand turned the door handle and opened the door to the bedroom.

With a deep breath, I walked through.

"Whoa," said Robbie in a low voice.

I had been expecting his phone camera flash to go off and then laughter but he was just sitting meekly on the edge of the bed, his jaw hanging open and his eyes wide.

I slunk my way into the room in my best girl's walk, swinging my hips slightly, showing more confidence than I was feeling.

"You like?" I asked uncertainly. My voice automatically sounded softer and more feminine than normal.

"Wow, is that you?"

I just nodded.

"Give me a twirl?"

I moved into the middle of the room, directly in front of my friend, and slowly turned on the spot.

As I moved, I didn't move my eyes from his face, watching his expression for a hint of a smile of amusement but none came. His eyes were stuck to my body, especially my rounded ass partly framed by the lacy thong material.

He seemed to genuinely like what he saw. Could it be he really wasn't pranking me?

"I wasn't sure you'd actually do it."

"Nor was I," I said, still using the softer, feminine voice I'd used since I put on these clothes.

"I'm really pleased you did."

I shyly played with my hair. I'd never used that gesture before in my life, it was so girly, but it felt natural now.

"You look really pretty," said Robbie, carrying on.

The thought occurred to me, he'd successfully got me into these panties, was he now trying to get me out of them?

I realised I was swaying my hips side to side to imaginary music.

"Would you like to dance?" he asked me.

I curled my hair around my finger again, "okay," I said shyly.

Robbie suddenly seemed reluctant. I was starting to get cold feet about all this but then he finally stood up and I saw why he had been reluctant -- he had an impressive bulge in his trousers.

"Oh, my!" I said and averted my eyes demurely.

"I'm sorry. I ... couldn't help it," Robbie seemed unusually vulnerable.

"It's okay," I said, approaching him, "it's a compliment really," I put my arms round him and started moving to an imaginary beat.

Robbie joined me in slow dancing, pressing his hard cock into my stomach. Even with the heels on, I was still inches shorter than him.

"This is nice," I said, my head resting on Robbie's shoulder. "thank you for buying these clothes for me."

He looked at me briefly.

"The bra and shoes are in my size, not Jen's," I said, explaining.

"Oh right," he said as we returned to our slow dance positions. "Mark and I have thought for a long time that you would look great as a girl."

"Apparently, you were right."

"More right than I could have ever dreamed! But we also thought that you sometimes acted ... girlishly too, like maybe you would feel comfortable as a girl as well as looking good as one."

"How did you tell that?"

"Lots of little things. Nothing to really point to but just an overall vibe over the years. We tried telling you but we were dumb about it and made it more of a running joke. If I'd known the direct approach would work, I would have tried this years ago."

I let that sink in. Apparently, my friends knew me better than I knew myself.

"How did you know I would strike out with Millie?"

"You always strike out with girls. I think they sense the same thing Mark and I do in you -- that's you're one of the girls, not a guy trying to get into her knickers."

That did make sense. Every time I've tried dating a girl, I've always been put squarely in the friend zone right from the start.

"Well, thank you. Tonight has been revelatory to me."

"Any time."

I could feel his breath on my neck as we danced slowly around his hotel bedroom.

I don't know if it was the alcohol I'd had earlier, the romantic embrace we were sharing, or the confidence I seemed to get from being shown something fundamental about myself I'd never known before, but something made me move my hand from around Robbie's neck, moving down over his strong pecks, over his washboard abs, down to his straining hard cock. I realized now, I'd always had a bit of a fascination in cocks but I never let myself act on it or think about it consciously.

"Oh God," Robbie moaned as I rubbed his cock through his trousers and boxers.

"Wow, I never knew you were so big," I whispered in his ear.

"You never checked me out in the changing room?"

"I always avert my eyes and get through the changing rooms as quickly as possible."

"Well you can check it out now if you like."

"I do like," I whispered as I continued stroking his hard member.

"You ... wanna see it?"

I looked into his eyes and smiled. He'd read my mind.

I moved back to give him room. He unzipped his trousers and pulled them down with his boxers, his hard cock springing up to point straight at my face.

"Wow," I half moaned at its sight.

I slowly lowered myself to my knees in front of him, the compulsion to inspect his impressive cock too much to resist.

It was long and thick, giving off an aura of power, a sheen of precum reflecting the lights in the ceiling as it twitched with his pulse.

I stroked my finger over his spongey cock head, in awe of his size and power.

Without thinking about it, I felt myself leaning forward and kissed his cock head.

I looked up at him and he smiled down at me.

I licked my lips and had my first taste of precum. It was a little salty but not unpleasant.

Robbie placed his hand on the back of my head and gently urged me closer to him, his cock aimed at my mouth.

I found myself opening my lips and taking his spongey cock head into my mouth, savoring the feeling and taste of his manhood, my tongue swirling around his tip, making him shudder.

"Oh my God," he said, closing his eyes in ecstasy as I started to suck on his cock head.

He added a little more pressure to the back of my head, urging me to take more of his impressive member into my mouth.

I started bobbing my head on his cock, my cheeks hollowed out as I sucked on him and I looked up into his eyes, which were full of urgency and desire.

Being in a position to give or withhold so much pleasure gave me a feeling of power Like I'd never felt before.

"You're so good at this," he groaned and I started to speed up my head bobbing and tongue swirling.

"Ooooh, fuck," he moaned and his breath became shallow and urgent and I knew he was close.

"Yes, that's it, yes," he took a more solid grip on my head, "take my cum!"

With his grip so hard on my head, I couldn't pull away if I'd wanted to. I had no choice but to take his cum in my mouth.

It was so much more than I expected. Compared to my usual teaspoonful of cum, his climax was more like a hose as it blasted into my mouth.

I had no choice but to swallow as fast as I could, gulping quickly to keep up with the constant flow, and I still choked on it a bit.

When the flow finally ended, Robbie released his grip on my head and sat back down on the bed, spent.

"Don't swallow that last bit," he said urgently.

It didn't occur to me to disobey him. I stayed kneeling on the deep pile carpeted hotel room floor, the last drops of my friend's cum in my mouth.

The taste was more intense than the precum had been but still not unpleasant.

When he'd recovered enough, Robbie reached for his phone and sat up on the edge of the bed.

"Open wide and stick your tongue out," he said, aiming his phone at me.

I did as he said and he snapped my picture and sent it to someone.

I hoped he wasn't sending the photo to the whole school.

"Okay, you can swallow now."

Again, I did as he said.

A moment later, he answered a call on speaker.

"Hey Mark."

"Wow, that picture is amazing!"

"I know right, the plan worked better than we dreamed!"

"I can't believe you got her to go so far!"

"Me too. She only took a little nudge in the end. You coming over to say hello?"

"I'm on my way now."

"Great, see you in a minute."

Robbie hung up. I still hadn't moved from where he'd put me.

He smiled at me.

"You can get up if you like. Maybe sit down on the bed?"

I stood up and sat next to him on the bed.

"You talked about me like I was a girl," I said timidly.

"Don't you think you look like a girl, Lucy?" he asked.

I looked at the mirror on the bathroom door and a hot blonde girl with cum on her chin looked back at me.

Absentmindedly, I wiped the drop of cum from my chin and licked it from my finger.

"You planned all this with Mark?"

"This was always the plan. To make you see what we've seen for years. It just worked better than we ever imagined."

"Thank you," I said, simply.

"After that blowjob, I should be thanking you!"

I giggled a little. I had really enjoyed giving him pleasure.

"I always thought you were just kidding with me."

"We thought you knew and were just in denial. We were telling you we were cool with you as a girl, in the only way we knew how."

"Well I'm glad you thought of a new way. It was eye-opening."

Just then, there was a knock at the door and Robbie let Mark in.

"Hey man, well done!"

They shook hands and made their way to the bedroom, Mark seeing the new me in person for the first time.

"Whoa, you look even better in person," he said.

"Thanks," I said demurely in my new feminine voice, moving my hair over my ear shyly.

"And I saw you gave Robbie some attention in that photo."

"It just happened organically," I said, a little evasively.

Mark came close to me and caressed my face softly.

"I'm so glad you see now what we have for so long."

"Me too," I smiled.

Mark leaned in and kissed me.

I looked to Robbie. He smiled so I returned the kiss.

Before long, Mark had his hard, throbbing cock out and I was once more on the floor giving my friend oral sex.

Mark wasn't quite as big as Robbie but he was much bigger than me. Longer and thicker.

I worshipped at his cock as I had earlier worshipped Robbie's.

As I did my work, Robbie pulled at my hips, repositioning me with my legs straight and bent at the hips, my mouth never leaving the cock I'd been given to please.

I felt Robbie push my feet farther apart, then he moved the narrow thong to one side and I felt something cold at wet at the entrance to my butt.

I carried on licking and sucking at Mark's straining cock as Robbie prepared me for the next step. It didn't occur to me to object.

Robbie started slowly easing a finger into my butt, rotating it to spread the lube around.

I relaxed my muscles as much as I could to help my friend take my anal virginity.

Robbie added a second finger and continued stretching me as I continued bobbing my head and sucking Mark's sloppy cock.

When Robbie got his third finger inside me up to the knuckle, he said 'that's my girl,' and playfully slapped my ass with a little laugh.

I concentrated harder on relaxing my muscles as I felt him lining up his hard cock with my ass.

"Are you ready for this Lucy?"

"Mmhmm," I mumbled and nodded my head without missing a beat on pleasuring Mark's cock.

"She's a real giver," said Mark with a bit of a laugh.

"She sure is," said Robbie as he thrust into me.

Now I was fully a girl. I had a large, throbbing cock inside me, taking pleasure from my boy pussy.

"Mmmm, yes," I moaned into Mark's cock.

Seeing Robbie take my ass sent Mark over the edge and I was once more drinking my friend's hot slimy cum.

I guzzled and swallowed until the flow finally ended. I licked the last of the cum from his softening cock and swallowed it with a moan of delight.

Robbie pulled back and thrust in again and again.

I pushed back in time with him.

"Oh yeh, take it," I moaned in my new, soft voice. "Fill me up, give it to me, use me!"