My Second Date with Blair Didn't Go as Expected

I checked my makeup for the third time in the mirror as I pulled up to Blair’s apartment. “Why are you so nervous?” I asked the reflection. “Just a second date.”

A part of me knew it was more than just a second date. I hadn’t spent two hours doing my hair and makeup for just a second date. I adjusted the shoulder strap of the romper beneath my cardigan. A bright pink string peeked at the corner from the lingerie I wore beneath.

It was what I thought was my sexiest wear. A pink lace pushup bra and tight thong, thigh high black stockings that connected to a garter around my waist, and a butt plug to keep my ass ready. I grabbed lip gloss from my purse and plumped my lips.

“Just a second date,” I said again, though this time even less confident.

The night before with Blair had been incredible. And while it had ended with me naked and satisfied, I had hardly touched Blair. Not that I hadn’t offered or attempted. There seemed to be some hesitation he wasn’t expressing that left me with conflicting thoughts.

He said he never had been with a transgirl, I thought, what if he didn’t enjoy it? What if he doesn’t find me attractive, or doesn’t want the intimacy to go both ways?

I shook the thoughts away. No, he asked for a second date, that meant something. And I wanted to show him that I could pleasure him just as much as he pleasured me. I thought about the way he had taken off my cloths and kissed down my body; how he fisted my tight ass, and how hard I had cummed.

Blair lived on the top floor of a large apartment complex. I had gotten there a little earlier than expected, finding myself anxious as I got into the elevator. When the doors opened on the top floor, I could hear voices echoing down the hallway. It was Blair’s voice—and some other girls.

I froze in the hallway.

Who is he talking with? I panicked. Does he have a girlfriend? Did he have a date before we were going on ours? Why did I have to come up early? I tried to relax. So what if he has a girlfriend. We have been on one date, that doesn’t make us exclusive.

I noticed I was biting my lip.

You’re being silly, Steph, I reassured myself. Why am I acting this way anyways? I’ve hooked up with married guys before, now all the sudden I am—jealous?

There was another giggle from down the hall. And then, was that a kiss I heard? Then the door shut, and I heard the shuffle of feet coming toward me. I pretended like I had just got out of the elevator as I passed the girl in question. She was cute.

I waited for her to be on the elevator before I knocked on his door.

“Oh hey,” Blair said opening the door. His shirt was unbuttoned, like he was still getting dressed. “You’re early. Come in!”

I could smell the faintest hint of perfume as I entered the room, and the couch cushions were scrunched to one side. I blushed. What am I, a fucking detective? Get yourself together, Steph! I smiled at Blair. Damnit, I think I really like you.

“Its nice to see you, again. I am excited about tonight,” I said.

“Me too,” Blair said, “I think you will really like this restaurant.”

Not exactly what I meant, I thought, consciously feeling the butt plug currently in my ass.

“After, we could go to the movies if you wanted?” Blair asked.

“You didn’t want to come back here?” I asked almost too eagerly.

Blair hesitated a breath. “We can definitely do that, if that what you would like.”

I pushed him against the fridge and kissed him. I ran my tongue along his, finishing with a nibble to his lower lip.

“That was unexpected,” he said, “and—welcomed, of course.”

“You know, sometimes I don’t know if I can read you,” I said. He glanced at where my cardigan and fell over my shoulder, exposing the edge of my frilly bra.

“Thank you?” he replied. “Hungry?”

“Ravenous,” I said.

Dinner had been nice. We ate, and talked, and for a time I completely forgot about all my worries and concerns; all the questions of his hesitant intimacy, and the mysterious girl that had been at his apartment earlier.

On the car ride back, I decided to make my move.

“So,” I said, placing a hand on his knee when he parked, “any ideas on what movie you’d like to watch when we get to your place?” I let my fingers fall to his inner thigh. I reached for the zipper on his pants.

“I haven’t thought about it,” he said, grabbing my hand from getting anywhere. “It is getting a bit late.”

“Oh,” I said, pulling my hand away, “I don’t want to impose. I guess.” I slouched against the window, defeated.

“We can always watch part of it now, and the other another day,” he suggested.

I perked up. I really don’t understand what is going on in his head. Could it be that he just wants to hangout?

I got an idea as we started up the elevator and my heart started to pick up its pace.

“Do you mind if I use your bathroom?” I asked as he opened the apartment door.

“Not at all,” he said, pointing down the hallway.

When Blair turned out of sight, I crept into his bedroom instead. I threw off my cardigan then slipped out of the jumper. I laid down on the bed, my stockinged legs crossed in the air, resting on my arms. “Blair,” I called.

Blair coughed as he opened the door. “Woah!” he said. “Wow—you look—are you wearing lingerie?”

I spun off the bed and met him at the door. He grabbed my hips as we kissed, tracing a hand to rest along my boob. As he pulled me in closer, I pulled at the button on his pants.

“Wait,” he said, pushing away slightly.

“If you don’t want me to go down on you, Blair, you can just say so.”

“It’s not—it isn’t that,” he said.

“I get it if you think the other girl could please you better,” I said, not really thinking about it.

“Other girl?” Blair said.

“The one that was here earlier.”

Blair laughed and pulled a family photo from a nearby wall. “You mean this girl? That is my sister.”

I blushed uncontrollably. There I was, standing in my lingerie, embarrassed. “I—I can’t express how awkward I feel right now,” I whispered.

“Don’t! Honestly. Wait, were you—jealous? You thought I was with someone else before our date?”

“I didn’t know. And yes, a little jealous. Its just that, well I think I really like you,” I said. “And you were so sweet to see my needs were met yesterday, and now I want to do that for you.”

“Steph, I like you too,” Blair began

“But?” I asked.

“But I—it is embarrassing. And I am self-conscious about it.”

“More embarrassing than standing in your lingerie while accusing the guy you like of hooking up with his sister?” I asked.

He forced a smile. “I just don’t want to disappoint you.”

“What do you mean? I orgasmed so hard yesterday, believe me there was nothing disappointing about that!”

“I—okay, I’ll just say it—I don’t have the biggest cock,” Blair whispered.

“What?” I asked.

“I just—wanted to make sure that I could pleasure you without it, you know, in case I couldn’t.”

“You're joking,” I said.

He looked down.

“Blair!” I said. “Listen to me. One, you did pleasure me. I seem to remember you sucking my half limp transcock—and I loved it. Second, and honestly, I don’t care how big or small your cock is, really.”

I kissed his cheek. “I know this isn’t the sexiest way to ask, but can I give you a blowjob?”

Blair laughed.

“Seriously! I have been thinking about it all day.”

“I am so nervous,” he whispered.

“How about this. I won’t break eye contact with you at all while I do it. Just me looking at you.”

“Are you—sure?”

I nodded and slid to my knees. He shifted uncomfortably at first, unsure what to do with his hands.

“Relax,” I whispered, running my fingers along his waistband. I spread my knees so that my ass was sticking out just a little. I unclasped the button and slowly pulled down the zipper.

I kept my eyes locked on his as I slid his pants down to his ankles. I felt at his boxers with a hand. I could feel the edge of his cock. I let the boxers drop, catching a glimpse of his cock in the periphery of my vision.

I grabbed him blind, my one hand able to encase his entire cock. I stroked him slowly, feeling every bit of his shaft. He bit his lip as he watched me, our eyes still locked. I stuck out my tongue and guided the tip to my lips, feeling ever ridge with the edge of my tongue.

And then I took him in my mouth, pushing until I got my lips to the stomach, and I could feel his balls against my chin. The tip just barely reached the back of my throat. I slid my lips along his shaft, back and forth, still looking at him.

I stopped sucking and started to stroke him with one hand. “Can I tell you something?”

“Yeah?”

“I love your cock,” I said. “Seriously. It’s perfect.”

“Really?” he asked.

“Really. Come here,” I said, guiding him to the bed. “Lay down.”

Blair stretched back onto the bed, hiding his cock with his hand. I crawled between his legs, letting him look at my feet and ass. I looked at his cock for the first time. Soft shaft, nice ridges, it really was perfect.

“Do you like this?” I asked, licking his sack. I held his shaft back and lifted a ball into my mouth.

Blair groaned with what I took as a yes.

“What about this?” I licked along his shaft slowly, like it was a lollipop, working my way to the top. I could taste the precum in my mouth.

I grabbed his hand and put it on the back of my head. “I’ll let you choose how fast I go,” I whispered, then started sucking him slowly. My lips slid up and down along his shaft. I felt his fist tighten around my head and he pushed me back and forth.

It got faster and faster, spittle dripping over his cock as I sucked. He grabbed my head with both hands, thrusting gently at first and then harder. I cradled his balls, squeezing, and then shoving them in my mouth when I reached the bottom of his shaft.

I held his cock and balls in my mouth, Blair pushing my head down onto his cock forcefully. When I pulled back, I gasped for air.

“Don’t stop,” he said.

Unable to catch my breath fully I kept sucking, struggling to breath. But I didn’t care. I was giving Blair a blowjob, that was all that mattered to me. I moaned, slurping the spit from his cock. Then he let go of my head and braced against the bed.

The first pulse from a cock cumming was always the best. His dick throbbed against my tongue, cum shooting into every corner of my mouth. I kept my lips locked, holding every drop. Then I locked eyes with him.

I opened my mouth to let him see the cum. I could hardly keep it all in my mouth.

“Don’t swallow just yet,” he panted. “Can you play with it?”

I opened wide, pulling at the cum with my fingers and letting the long strands fall back into my mouth. I swirled my tongue, then gargled until I felt bubbles collecting at the back of my throat. Then I licked the last bead of cum from his cock and swallowed.

“Steph, that felt amazing,” Blair said.

I continued to hold his small but perfect cock. “Oh, I am not done with your cock just yet,” I whispered, taking him in my mouth again. “I am going to blow you until you don’t have any cum left to give me.”

Blair reached down and squeezed my boobs as I gave him another blowjob. And the night is only getting started.