The Pizza Boy gets paid more than he expected

I sighed, sitting in my chair with my knees against my chest, twirling a stray hair, and bored out of my mind. Being a secretary for a prominent global company had its perks—unless you got stuck on the late-hour shift, waiting for the rare and foreign calls that infrequently came. I glanced around the empty office.

“Looks like it's just me, tonight,” I whispered.

From a far window I could see the sun starting to set against a backdrop of dark reds and muted yellow. The adjacent buildings shimmered, their own lights going out as people left for the night. I spun in my chair, looking out of the glass walls of my office. All the other employees had gone home hours ago.

I wiggled the mouse on my monitor so that it still thought I was active. With the company monitoring our computers, there was little I could do other than scan through documents I might need and wait.

My office, at least, was more secluded than the cubicles—even if it was just a wall of glass. I wonder what Kayla is doing right now, I thought. And Bron. It had been a month since our threesome, but it felt like it had been yesterday. My mind started to race with thoughts of his cock. How soft and warm it was in my hands. How it felt in my mouth, sliding down my throat. The way he pushed it into my ass until I could feel his balls against me.

Right then I realized I hadn’t cum since that night. Not for lack of trying, but because it was hard for me to orgasm without a dick inside of me.

A thought popped into my head. I could try to cum right now. I am alone—but, no, it is too risky. The thought of cumming at my desk started to turn me on. Despite the concern, my hands pulled at the straps of my romper. I slunk into my desk a little more, slowly pulling down the romper until it fell around my ankles.

I might get caught, I thought, pushing down my panties and untucking my limp tranny cock. I started to stroke it under my desk, my gaze constantly looking around the empty office. I pulled my knees up to rest against the desk, fingering my ass while tugging on my cock.

The thrill of potentially getting caught made me hard. I stroked faster and faster, feeling for the climax I wanted so badly. I was so close—and then I lost it, and my cock went soft. I licked up what precum clung to my fingers, then begrudgingly redressed.

For the next hour I let boredom take me, eventually ending up watching cheesy porn videos for the terrible acting and humorous sex. The one I was currently watching was of a pizza deliver boy that was offered a handjob as a tip. While mildly sexy, I found myself more hungry than horny.

“I could go for a pizza,” I whispered. I opened an app on my phone, and within minutes one was on its way.

My attention was pulled by the soft tapping of a delivery boy at the outside of the glass. I shook myself, quickly pushing out of my desk and unlocking the glass door. “Sorry—I got a little distracted.”

“I am guessing you are Steph?”

“Yup! What gave it away?”

The delivery boy smiled and looked around the empty office. “Lucky guess.” There was something about him that seemed familiar, but I couldn’t quite put a finger on it. He lifted the receipt. “It says you wanted to pay in cash?”

“Yeah, one second,” I said, rushing over to my purse. I reached into the pocket where my wallet was supposed to be, finding nothing but an empty space. “Uh oh.”

“Something wrong?” delivery boy asked.

I huffed. “I grabbed the wrong purse—I don’t have my wallet, I am sorry, this is awkward.” I blushed brightly. I looked around the room for an answer I knew I wouldn’t find.

The delivery boy scratched at an eyebrow. “Steph,” he said as if remember my name from somewhere, then snapped his fingers. “Your Kayla’s best friend!”

“Yeah—I, do we know each other?”

“No. Well sort of. You know my brother, he is dating Kayla,” he said.

“Your Bron’s younger brother?” I asked, instantly recognizing the similarity. “I thought you looked familiar.” My memory flashed with the image of Bron’s cock, and I blushed. Bron wouldn’t have told him about that though. Right?

“About your pizza though,” he continued, “if you can remember your card number—I could probably type it in?”

“I don’t remember it,” I said sheepishly. I hopelessly looked through my purse. A pack of gum, some tissues, an old condom, mascara, and lip gloss were all that I had. I tossed my purse on the desk and looked at my phone. “Unless you accept handjobs as payment, then I think I am out of luck,” I jested.

He flushed and his eyes went wide.

“Sorry, bad joke!” I said quickly. “There was this video—I mean I was reminded of something—that was poor taste, sorry.”

“You’ve been around Kayla too long,” he joked back. He looked around briefly, then spoke softer. “I, um,” he whispered, “I would—accept a handjob.”

I laughed and waved a hand, thinking he was joking. “Seriously?” I asked coyly.

“If you’re serious,” he said nervously and grinned.

I bit my lip as I thought, considering it. I could probably call Kayla and get her to cover for the pizza, then pay her back later. I looked at Bron’s younger brother, and curiosity got the better of me.

“Alright,” I whispered. “But only because I am starving. And on one condition. You have to promise not to tell Bron. Or Kayla. It has to stay between us.”

“I promise,” he agreed, setting down the pizza box on my desk. He shifted awkwardly, uncertain what to do. “Should I—um—sit down? Stand?”

“Have you ever—had a handjob before?” I asked.

“Sort of.”

“Sort of?”

“On the outside of my pants once,” he said with a shrug.

“Wait. So this is going to be your—first handjob?”

He nodded wordlessly, trying to casually cover a growing bulge in his jeans.

I could feel my cheeks red from the blush. “Here,” I said, pulling his arm. “Sit in my chair.”

He sat down, looking from side to side. I kicked off my shoes and knelt down, pushing open his knees and gently tracing my hand up his thigh. “Don’t worry, I will do most of the work,” I said. The tips of my fingers pressed against his cock. “All you have to do is relax and let me know if you see anyone coming.” I gripped half of his cock. “And wiggle the mouse on my computer every so often, if you don’t mind.”

I reached up and slowly unfastened his belt, intentionally exaggerating the moments while I undid the button first and then the zipper. I reached inside his boxers. He has a nice cock, I thought. I pulled the pants at the hips, dragging them and his boxers down to his knees.

His cock bounced out of his pants. He nervously covered himself and laughed. I grabbed his hands and pushed them to the side. “Relax,” I whispered, grabbing his cock with on hand, the other on his thigh. He wasn’t as thick as Bron, but just as long, and with a slight curve. “If you want me to stop—”

“No,” he replied instantly. “I—am just nervous.”

“Would it help if I talked?” I asked, running my fingers up and down his shaft. I grabbed his cock with both hands, holding the tip close enough to my mouth so that he could feel the heat of my whispers. “Do you like it when I stroke the tip like this?”

I put the tip of his cock in my palms, stroking and twisting in a way that focused only on the tip. He moaned ever so gently. “Yes,” he whispered. I kept doing it, cradling his balls with my other hand. A dribble of precum dripped onto my hand.

“And what about when I do this?” I spread the precum along his shaft, slowly stroking from tip to base.

He moaned again. I noticed when he relaxed his legs, sitting back into my chair. I held his cock close, looking up at him, holding the tip against my bottom lip. I let a little bit of spit spill over my lips and onto his cock.

It was slicker now with my spit, and I was able to move my hands up and down his shaft rapidly. I tried to figure out what he liked based on his moans. When I grabbed his balls. When I gripped him with both hands. When I focused on just the tip.

He closed his eyes. I know that look, I thought. “Are you going to cum?”

I kept stroking as he moaned, waiting for him to cum. But he didn’t. “Are you—holding back?” I asked.

“A little—” he confessed.

“Why?”

“It feels good.”

I giggled and kept stroking. “It would feel better if you cum,” I whispered. “I want to feel it, warm and gooey, dripping over my fingers.” He moaned and I felt the faintest pulse in his cock.

I have him close. Just a little more. I wonder if he can hold back if I do this—

I held his cock against my bottom lip again, looking up at him. When he looked at me, I parted my lips and took him in my mouth. It was just the tip at first, keeping my eyes locked on his as I swirled my tongue, tasting his precum.

And then I took him deeper in my mouth. Slowly working up and down. Pushing his cock past my tongue and down my throat. I gagged, pulling off with a gasp and his cock slick from my throat. I licked along his shaft, blowing him harder and harder.

But still he didn’t cum. I kept sucking for what felt like fifteen minutes. After deepthroating him again, I stopped for air. “Are you still holding back?” I said between breaths.

“It feels really good,” he replied.

“Was I at least close to making you cum?”

“A lot of times.”

“Alright,” I said, reaching for my purse. “Lets see if you can hold back this time.” I grabbed the old condom, tore open the package, and slid it over his cock.

“What are you doing?” he asked as I stood. I pushed at the shoulder straps of my romper, letting it fall to the ground.

“Stand up,” I whispered. Then I turned around and dropped my panties to the floor, leaning over my desk with my ass toward him. I reached behind as he stood, grabbing his cock, and leading it to my asshole.

“I’ve—never been with a transgirl,” he said.

“Well, there are really only two things you need to know about transgirls,” I said as I pushed his cock into my tight asshole. I moaned. “They have tight assholes, and know how to please a cock.”

I was glad when he pushed in slowly. It was so tight, but felt so good to feel him inside of me. He grabbed my hips, spreading my ass cheeks and watching as his cock disappeared in my ass. I guided him with my hand, pushing and pulling as he thrust.

My tranny cock started to get hard against my desk as he pounded me from behind. I gripped the edge of the desk, pressing against each thrust as he fucked my asshole. My limp cock quivered, then pulsed as he made me cum. I moaned so loud I was afraid someone from another office might hear us. I felt my stomach slick with my own cum as he thrust faster, and faster.

And then he slowed, pushing his cock deep inside of me. And then I felt it.

There it is, I thought blissfully, savoring every pulse from his cock. I could feel his cum, a lot of cum, warm in my ass. I opened my eyes. Wait.

As he pulled his cock out with a thwap, I felt a bit of cum dripping along my thigh. I looked down at the condom, broken and scrunched against the base of his cock. He stumbled backwards into the chair, breathing heavily, and looking from my ass to the broken condom.

“I—I didn’t mean to break it—sorry,” he said.

“It was mostly just to lube my asshole anyways,” I said. I pushed his legs wider, spreading my ass over his cock. I felt the warmth dripping out of my gaping hole and onto his cock. I watched him with a grin as he watched the cum spill out.

I’ve never had so much cum in my asshole before. I turned, then got on my knees again. I let the cum drip into my mouth from his cock, sucking up the rest, and letting him watch as I swirled it around with my tongue. I sucked what was left out of his cock, giving him one last glance before I swallowed the load.

He sighed happily. “Wow—I, don’t know what to say.”

“Did you enjoy it?” I asked, sliding into my panties, and pulling up the romper.

“You have no idea,” he said, standing and zipping up his pants.

“That makes me happy,” I said. My stomach growled, unsatisfied with just the cum. I opened the pizza box and got a slice.

“You—um,” he said, pointing to the corner of my mouth, “you have a little—something.”

I brushed my cheek where a bit of cum still clung. “Thanks,” I said, then took a bite of the slice. Pizza had never tasted so good.

“I am so late now for work,” he said.

“Sorry about that. Next time I won’t forget my wallet.”

He made himself presentable, turning to leave but stopping at the door. “Do you mind if I get your number?” he asked sheepishly.

He fucks me so hard I am left gaping and dripping with cum—and still is nervous to ask for my number? “You’re cute,” I said, “and yes.” I wrote down my number on a piece of paper, tore it off, and handed it to him. “Not exactly what I would have expected for a first date. But fun!”

He smiled, awkwardly kissed my cheek, then scurried out of the office.

I sat in my chair, cringing against the pain of my stretched asshole. It felt good. I leaned back with complete satisfaction. I could still taste his cum in my mouth, and my lips were still sticky. I looked at the cum stain on my desk and sighed. Totally worth the mess.