First Time Date with Coworker

“It is getting late,” I said with a yawn. “I should probably get going.”

“Stay a little longer,” Blair said as he glanced at the clock. “Coffee?”

“This late? I won’t be able to go to sleep.”

“Hot chocolate?”

I tapped my lip and hummed. “Alright. You convinced me.”

Blair swiftly sprung up from the couch and started to rummage in the kitchen. I sat back and let the cushions of the couch embrace me.

When Blair had asked me out at work, I hadn’t known what to make of it. He had a generally quiet personality and a soft way of speaking. We knew each other from work, but had only ever exchanged pleasantries, so it came as bit of surprise when he asked me out.

“Marshmallow?” he asked from around the corner.

“Sure!” I chirped. “Thank you for asking me to dinner.”

“I hardly call getting smoothies dinner,” Blair said.

“Oh,” I said with another yawn.

Blair was different from the guys I usually found myself pursuing or wound up getting entangled with. I had spent so much time with the aggressive, dominant guys that just wanted to get their cocks sucked—to which I eagerly participated—I had forgotten the simple pleasures of a calm evening.

“Not the traditional date, I know,” Blair continued, “or, evening hanging out, if you’re uncomfortable with date.”

“Oh no, no, sorry I didn’t mean it to come off like that,” I said sitting up. “I had a lot of fun. Really!”

Blair simply smiled, handed me a steaming mug, and sat next to me on the couch. I let the warm wisps press against my cheeks. I sipped at the hot chocolate, but it was still too hot. I set it down and tucked a leg beneath as I turned toward him.

“This is the part where you say you had fun too,” I said jokingly.

Blair blushed brightly midway through a sip of his own.

“Only kidding,” I said and rested a hand on his shoulder. Instinct or experience told me this was the part of the date where the guy did something physical; grabbed my leg or felt at my boobs or held back his shirt and unbuttoned his pants while I got on my knees.

Blair just smiled. “Can I ask you something?” he said softly.

“Yeah! What’s up?”

“You’re a—transgirl, right?”

I withdrew my hand from his shoulder. I could feel the heat in my cheeks. Why am I so embarrassed? I thought.

“Yes,” I said shyly.

“And when did you know?”

I frowned. “Honestly, I don’t know. For as long as I know I have just been—me.” I pursed my lips and fidgeted. “It is hard to explain, its like I have always seen myself differently than what others expected—like I was on the wrong side of the line, when I felt comfortable there.”

I grabbed a pillow and held it as a shield.

“I hope that question wasn’t uncomfortable,” Blair replied, “and I hope that you know it doesn’t bother me. I’ve never been on a date with a—um, I was just curious.”

“Thanks,” I whispered. “Not something a lot of people ask about.”

“No?” Blair said. “And what do they ask?”

They usually ask how big is my cock, I thought. “Nothing worth noting. To be fair, I have a bad habit when it comes to guys.”

“Oh? And how is that?”

“Forget I said that! For the first time in a long time, I am having a relaxing evening and I don’t want to ruin it.”

“Consider it forgotten,” Blair grinned. He pointed out the window of his apartment. “It isn’t a bad view of the valley at night. But I won’t keep you if you are tired.”

“I’ll stay a bit. Do you want me to get the lights?”

Blair nodded from beneath his mug.

I got up and hit the light switch, then sat back down a little closer to Blair. We talked a little more, quietly watching the sun set and the city light up around us. Blair shifted, and when I looked at him, he kissed me.

A clumsy kiss, but sincere. I kissed him back, gently running my lower lip along his. I had to fight the urge to reach for his cock, surprised to find that I could resist the temptation. Blair put his hand around the base of my neck as we kissed, tucking the hair behind my ear as it fell free.

He slipped his tongue into my mouth with a faint lick, and I did the same back. As the light faded our kissing got more passionate. Oh, I want you to fuck me, I thought. I want your cock inside of me.

I continued to fight the urge. Blair seemed content with kissing, so I didn’t push it.

“Do you—um,” Blair said pulling away, “do you want to—go to the bedroom?”

I bit my lip. It was an obvious yes, but I was trying to fight that instinct.

“But if you’re not comfortable with it,” he continued.

“Lets do it,” I said, “show me the way.”

Blair took my hand and guided me down the hallway. I stumbled a few times, but he kept me upright. When we got into the room, I sat on the bed. I put my hands on his waist, fingers tracing the edge of his pants, but I hesitated.

He sat down next to me, and we started kissing again. Blair gently pushed me back onto the bed, kissing down my neck. I held his head closer as he kissed closer to my boobs. And then he made his move, reaching beneath my sweater to grab my bra.

I moaned faintly and he retreated.

“No, don’t stop,” I whispered, then took of my sweater.

Blair continued to kiss at my boobs, struggling to undo the strap in the back for a solid minute. I let my bra fall to the side of the bed as he started to suck at my nipple. I pulled his head in closer and moaned.

I expected that to be it. That we would keep kissing for a while, and then we would call it night. But then Blair kept kissing lower, and lower along my stomach. He started to unbutton my pants and I panted for breath.

“Wait,” I whispered as he pulled open the zipper.

“Too much?” he asked, stopping.

“No, I just—I just wanted to make sure that you’re sure about—” I said, pointing down with my chin. “I know you said you’ve never dated a transgirl, I just—”

Blair licked at my waistline then shimmied my pants off, leaving on my thong.

“Do you want me to keep your socks on?” he asked as he got my feet out of the pants legs, fingers tracing at my ankles.

“You can take them off,” I whispered. He kissed my ankle as he did, licking at my toes on one foot, and then the heel of the other. I moaned, and he kissed down my legs. He stopped briefly when he got to my thong.

He is having second thoughts, I thought. He isn’t into it, I don’t want it to be awkward, I should just say it’s getting late.

Blair pulled my thong down, and with it my tucked tranny cock. I was still a bit limp, despite being incredibly aroused.

He started by licking along my shaft, the took me into his mouth. I gasped with pleasure, my cock getting harder with every swirl of his tongue. I could feel his teeth brushing against the tip of my tranny cock. He stopped sucking with a slurp, then started to lick along my small balls.

“Flip over,” he whispered, grabbing my hips, and spinning me. “And get on your knees.”

I did as he said, flipping over and getting on all fours. He spread my cheeks with his hands, then started to eat my ass. It felt so damn good I yelped, moaning as he pushed his tongue into my asshole. I bent down, resting on my elbows.

I could feel the scruff on his face brushing against my cheeks. Then I felt a finger slide into my ass, and then two, as he fingered me.

“Don’t stop,” I said between hot breaths.

A third finger went in, and then a fourth, Blair slowly working a hand into my ass. I grabbed my cock and started to stroke it as he fingered deeper and deeper, until he was wrist deep in my ass. I had never been fisted. It was new, and exciting, and a little awkward. I glanced over my shoulder and watched as his hand slowly disappeared into me.

Blair flipped me onto my back, putting my legs around his head as he ate my ass from the front. I kept stroking my own tranny cock with one hand, grabbing the back of his head with the other.

With his tongue swirling within me, I couldn’t hold back any longer. I arched my back, my cock pulsing as I shot cum onto my own stomach. I fell back onto the bed, my ankles resting on his shoulders.

“That felt amazing,” I whimpered. I collected a bit of my cum on a finger and licked it up eagerly. “I haven’t cummed liked that in a long time.”

Blair licked up a bit of cum, then kissed me, letting it drip into my mouth.

“That was a first for me,” he said.

“Really?” I leaned forward and felt for his cock, though he stopped my hand.

“It is getting late,” he said.

I blushed brightly. “You don’t want me to—”

“Not tonight,” he said embarrassed, though I didn’t know why.

“Is something wrong?” I asked.

“No, no, it is just—I just don’t feel quite comfortable just yet.”

“Oh,” I said, reaching for my cloths and hiding my boobs.

He grabbed my hand. “But if you don’t have any plans tomorrow, do you want to grab dinner again?”

I kissed him.

“Tomorrow, then,” I said. And then I am going to fuck you like I’ve never fucked before.