The Awkward Girl

I put another ad on CL as soon as I got home from work tonight (technically yesterday now, Thursday).

A few spam replies in the first twenty minutes. Then two real replies with photos I wasn't attracted to. Then another spammer, and then a response from... let's call her Bailey.

Bailey is 28, and I loved her photo. Maybe there wasn't the instant holy shit I felt when I saw Seana's picture, but certainly close enough. She's a cutie. Dark brown hair. Huge brown eyes. Kind of a big goofy smile that works well for her. I sent her my pic in response, and she wrote back right away with her phone number.

I called. We talked. She sounded quite a bit more nervous than even I must have when I first talked to Seana.

Actually what she sounded was unsure. She said it was her first time. She said she was almost certain she wanted to do this.

I clarified that I probably wasn't looking for a relationship (that's going to change the instant Seana decides she's looking for one, if she's got her eyes on me at that point), and Bailey said that was fine, and that she probably wasn't either.

So, we agreed to meet up for dinner. She lives north of downtown. I took the train and met her at an Applebees.

Man, she's cute. Even cuter in person than in her picture. She has these huge glasses that are pretty far out of date, but they sort of go with her persona: adorably unsure of herself. She's probably three inches taller than me, but the way she carries herself, very awkward and halting, you think of her as smaller. She has this kind of lost kitten thing going on, and you want to give her a huge hug as soon as you see her. Which I did.

We got a booth (Bailey sat across from me, unlike Seana on Friday night) and our hostess brought us two menus and said a server would be right with us. For the moment we ignored the menus. Bailey had her hands resting on the table, and was drumming her fingertips on the surface, looking down.

"How do you feel about this?" I said.

She looked up and blushed a little. "Oh, I'm sorry. I hope I don't seem weird or--distant or anything. People think I am, but it's just shyness. I can never seem to help it."

"It's okay," I said.

"Thanks."

"So how do you feel?"

She hesitated. "I know I've always wanted this. I know I want to... be able to do it. I think I will be able to. I mean, I'm almost sure."

"But not totally sure?"

She looked down at her hands. "Not totally. I don't know." She looked back up at me, wincing a little. "I'm not trying to sound like an idiot. When I'm unsure of things, I just say everything I'm thinking. I'm sorry."

I smiled and tried to put her at ease. "Don't be sorry. We'll just take it in steps, and if there's any point when you decide you're not up for it, we'll call it a night. Even five minutes from now. Okay?"

She nodded. I could see her cheeks flushing red. I was pretty sure, at that point, that she wasn't going to go through with it. All I could think of was how grateful I was that Friday night happened the way it did.

"I guess we should figure out what we're ordering," Bailey said.

Twenty minutes later--during which we'd talked about every random thing except having sex with each other--and five minutes after the food had arrived, the moment came.

"Okay, I don't think I can do it," she said. She winced again, her eyes all apology. "I'm sorry. You came all the way up here, and I'm sure you wanted this, I'm really sorry. I just can't get there yet."

"It's fine," I said. It was fine--sort of. Obviously I was pretty disappointed. I liked her. I wanted her.

"I'm sorry," she said again. She was already getting up. Her plate still mostly full. She left a twenty on the table, gave me the apology wince again, and then she was gone. I got a decent look at her ass as she was walking away. I really shouldn't have looked--it only made me think of what it would've felt like gripped in my hands while I ate her.

Fuck.

The moment left me a little numb. When your hopes are way up, you start measuring time in smaller pieces. Like, I'd been sitting there thinking, "If she's up for it, we're probably half an hour from being at her place, maybe just starting to make out." You're on that scale, and all the sudden the thing that you were focused on is gone, and you're half an hour from... not doing a whole hell of a lot. Being on the train home.

Ah, at least I'd sort of seen it coming. It wasn't a total shock. I kept eating my mashed potatoes and roast chicken. I'd been starved before it arrived, and it was delicious. It gave me something to try to feel good about, anyway.

Ten minutes later, when I was just signing the credit card slip, my phone rang. Bailey. I answered.

"Are you still at the place?" she said.

"Yes."

"Do you still want to do this?"

"Definitely."

"I'm a block away, on my way back."

My heart was beating a little faster. This I had not seen coming. "Excellent," I said.

"Um... I'm not sure how much I want to do. Or what, exactly."

"Okay."

"Well... I sort of do know... it's just weird to say it. I don't know how you'll feel."

"I promise you, you can say exactly what it is, and if I'm not interested, I'll just say so."

"Mmmm..." She didn't sound like she believed me.

"Pretend it's a scene in a movie," I said. "And you're the director. Tell me in the most blunt terms possible... what exactly do you want to have happen, when we get back to your place?"

A heard a breath on the phone as she laughed at my phrasing.

"I don't know," she said again.

I put on my best mock-pissed voice. "Bailey, if what you're interested in is being spanked, you're already making me want to do that."

This time she laughed out loud. Nervous as hell, but still a laugh. It was the first one I'd heard from her.

"Come on, Bailey, sketch out the scene. Blunt terms. Dirty terms are even better."

There was another long pause. Maybe five seconds. I could hear her footsteps on the sidewalk, and the grumble of traffic.

Then she exhaled deeply, took another breath and said, "I want you to get naked, sit on my couch, and let me kneel in front of you and eat your pussy. And then I'll probably want you to leave. Is that okay?"

I laughed. "It's a hell of a lot more okay than what I was looking forward to sixty seconds ago."

She breathed another laugh. "I'm almost there now."

"I'll meet you at the door."

Six minutes later we were shutting her entry door behind us and kicking off our shoes. Everything was still awkward as hell, though we'd talked a lot more openly on the walk from the restaurant. I'd told her about Friday night. She'd asked me a lot of detailed questions, and looked a little unnerved by the answers.

Now, inside her place, we just stood there inside her door for a second. I was pretty sure she didn't want me to kiss her.

"So..." I said. "Do we just... get right into it?"

She made a face a kid might have made standing on the high-dive board in front of a hundred people. Then she said, "Yeah. Definitely."

She nodded for me to follow her into the living room. Her place was very neat. Very normal. A little sparse.

"I can turn away while you're... undressing," she said.

I laughed. "Are you planning to have your eyes closed when the tip of your tongue is in my vagina?"

"Jesus," she said, and went quite a few shades redder than she had at any time in the restaurant.

"You can undress me yourself, if you'd like," I said.

She bit her lip. "You're sure?"

"I'm pretty much certain."

She took a nervous breath. "Okay."

She stepped closer. Tapped her teeth together a few times. Then she undid my shirt buttons carefully, and when they were all undone, she slipped it off my shoulders and set it on the couch. She reached behind me for my bra clasp. The move put her face close to mine. I saw her eyes in better detail than before. Such a beautiful girl. I wondered if she was this anxious around men. I doubted it. She finished with the bra and set it on my shirt.

She hesitated before reaching for the button of my jeans. Now or never, she seemed to be thinking.

Then she knelt in front of me, unbuttoned and unzipped them, and slid them down with my underwear. Just like that, her face was five inches away from my pussy.

She stared. Caught her breath. When she started breathing again, it was at an accelerated pace.

"Want me to sit down?" I said softly.

She nodded, just noticeably.

I was already standing in front of the couch. I eased down onto it, with my ass much further out at the edge than I'd have normally sat. Then I parted my legs and leaned way back into the couch. The lean served to tilt my pussy upward for her.

I was wet already. I think her tension translated into some fairly serious arousal on my part. I loved being the focus of feelings this intense.

She rested her hands on my thighs. Sank into a lower kneel. Leaned forward until her mouth was almost touching my cleft.

She closed her eyes for a second and inhaled. And smiled deeply. I knew the feeling--I'd done the same thing with Seana.

And then she stepped off the high-dive. She sank her mouth into my pussy. I felt her tongue slip deep between my inner lips. Felt myself getting wetter by the second, in response.

I watched her expression as she ate me. Sometimes her eyes were open, staring at the traces of stubble on my mound, but most of the time she just had her eyes closed... with a look of absolute relaxation on her face. Finally.

She looked like she loved it. She did it like she loved it, too. It felt amazing. After a few minutes she turned her attention mostly to my clit. I felt my orgasm on its way.

I wasn't sure what amount of contact she wanted from me. I took the chance and let my hands rest on top of hers, where she was gently holding my thighs apart. She responded, interlacing her fingers with mine. It turned me on a little more... and that was about all I needed, at that point.

I whispered her name, and then I sucked in a deep breath and came almost as hard as I had for Seana the first time. Hips bucking involuntarily on the couch. Bailey trying to hold on. I kept crying out and telling her not to stop--right up to the moment when the sensation got painful against my clit, and I laughed and reached down and softly pushed her away.

"Sorry," she said.

I managed a tired laugh. "Do not apologize..."

She carefully planted a kiss on my folds, below my clit, and I felt her tongue go in for a taste of my juices. Not sure if she sopped much of them up or decided to swallow; I was pretty much out of it for the next minute, eyes closed, upper body sunk into the couch.

When I recovered enough to open my eyes, she was still kneeling there between my legs, looking very satisfied with herself.

"How'd you like it?" I said.

She sighed. "Even more than I hoped I would."

"You're still sure you don't want me to return the favor?"

She made a trace of the wince from the restaurant. "I don't think I'm ready for that yet. I know it's weird. I'm just not. Sorry..."

I laughed a little. "It's okay. Really. Nothing to explain."

She just shrugged, like she wished she could, anyway.

And that was that. I got dressed, and a few minutes later I was on the train heading back. I called Seana (we've talked on the phone a few times this week) and gave her the fun details. She got a kick out of it. Said she'd had the same thing happen to her a couple times.

She talked to me for the whole train ride. A really nice conversation. I wanted very badly to ask if I could come to her place, or if she could come to mine, but I didn't want to push it. I don't want to be clingy. I'll let her set the pace with us, assuming--hoping like crazy--there's going to be one.

I said goodbye to her as I left the platform and headed alone for my building, and after we ended the call I kissed my phone and put it away.