Woulda Shoulda Coulda No More Ch 01

I exhaled and sunk into the couch, my head resting against a pillow, holding my phone in front of my face. She was on the other end, looking at me, smiling, making herself comfortable, too. It was late, dark. Both of our houses were quiet and still, yet we still spoke just above a whisper. She took a long sip from her glass of white wine and then giggled.

"What?" I asked.

"I don't know," she said, looking at me through her phone. "Say something."

"That was nice."

"Always."

My heart still raced. To this day, after everything we've been through and everything we've done, I still get nervous with her. The butterflies have never gone away. "I love these nights when we're both alone," I said.

"I know. Me, too." She smiled and shyly looked away.

"I've been looking forward to this for weeks. No joke," I said. We had been talking about this Facetime session for a long time. "I wasn't sure it was actually going to happen."

"You know I've wanted it to," she said, almost defensively. "It's hard, you know? I'm so busy."

"No, no, no. I know. I know. Me, too. I'm just saying. I'm glad it happened." I smiled at her.

She smiled back. "Me, too."

I reached to pull the blanket up to cover my naked legs. I took a sip of my whiskey. It burnt as I swallowed it down, but helped slow my pounding heart. She was laying on her stomach, looking into her phone, right at me. Her hair hung over her bare shoulders, her gorgeous breasts pressed against the bed, pushed together into a deep, sexy cleavage.

"That looks nice," I said, nodding toward her chest, with a smirk.

She laughed. "You didn't get enough? You want more?"

"I always want more of you! It's never enough. You know that!" We both laughed. "So, were you wearing the shoes?"

"I told you I was!"

"Yeah, you did, but I didn't get to

see

them."

"You seemed to like what you saw!" She laughed.

"Well, obviously," I said, sheepishly. "But I'd still like to see the shoes."

She smiled, and then put down her phone, face down. My screen went black, but I could hear movement on her end. She picked up the phone and I could see her again.

She was sitting up, leaning against the back of her bed. "Ready?"

"Yes, please!"

She turned the phone around and pointed it towards her feet. There were her red shoes, my favorite ones, at the end of her smooth, bare legs. Her cute toes, painted dark red, peeked out from underneath the sexy ruffles. She moved them side to side, pivoting on the heels spiked into the bed.

"Oh my God, I love them so much! So you were wearing them the whole time?"

She turned the phone back around and looked right at me. "Yes! I told you I was!"

"That's so fucking hot. I want to do so many dirty things to them."

She just laughed.

"I mean it!"

"I know you do!" she said. "So then, when are you going to?"

My heart raced. "Three weeks," I paused, and then asked, "right?"

"You sure you want to?" she asked.

"Oh my God, yes. You just tell me when and where, and I will be there. I've been dying to see you forever."

We both sipped our drinks. After a few seconds of silence, she asked, "Why didn't we ever have sex?"

"Back in high school?"

"Yes!"

"Well," I paused. "In three weeks we won't have to ask that question ever again! Right?"

She smiled. "You're funny."

"I mean it!"

"I know! But," she paused. "Why didn't we?"

"I don't know," I shook my head and answered disbelievingly. "I wish I had a better answer. I think about it a lot."

"Me too." She sighed. "Timing, right? It was always the wrong time."

"I guess. Maybe. But we made time to do plenty of other things, didn't we?" I said.

She laughed. "Yeah, we did. I always just didn't think you wanted to."

"Wanted to what?"

"To have sex, silly!"

"Of course I did! It would've been really nice to have done it with you back then." I smiled. "You could've been my first!"

"I

should've

been your first," she said, emphatically.

"I know, I know. I don't know why, but I was always, just, so nervous."

Like I was right now.

"But why? I was nothing to be nervous about."

"Don't sell yourself short. You were fucking hot in high school."

"Stop," she said, with a laugh.

"No really! You were sexy. Something about you. You've always just, been

sexy

." I said with a raise of my eyebrows. "But...I just...I was...I dunno."

"So many missed chances." She sighed, taking a sip.

"I know! All those times in dark parking lots, on couches watching movies, in my basement," I said.

"Third floor cafeteria," she interjected, with a laugh.

"Ha! Imagine that! We could've had sex in the school cafeteria. That's hilarious!"

"Oh my God, how funny," she said, raising her wine glass to her lips.

We both fell silent for a minute. I know my mind focused on those memories, still so vivid. My fingers traced the rim of my glass and I looked away from the phone. "You know what I've always thought was our best chance?"

"When?" she asked.

"When I came to visit you at college. Neither of us were dating anyone at the time. And we had your dorm room all to ourselves!"

She giggled. "I remember. I worked that out with my roommates."

"You did? Yeah, I mean, I guess I figured. God, why didn't we have sex then?"

"I don't know! Why didn't you try?" she asked.

"Well, why didn't you?"

"I didn't think you wanted to."

"I did, so bad. But, I was nervous," I said. "You did go down on me."

"I remember." She smiled, proudly.

"You were wearing red panties, I remember that. They were on one minute and then they were all of a sudden they were off. I didn't understand how. I remember asking you and you just said, 'I'm good like that.'" I laughed.

"I can't believe you remember all these details! My memory is so bad!"

"Well, I used to think about it a lot. I would think about you a lot. All throughout college. To be honest," I paused. "I've never told you this."

"Told me what?" she asked inquisitively.

"I had this picture of you, from your birthday freshman year. You had emailed it to me. You were wearing a tank top, pretty low-cut. I'd use that for, ummm, inspiration."

"Oh yeah? What kind of inspiration?" she asked cheekily.

"Oh, I think you know." We both laughed.

"Oh my God, that's so funny!"

"I'd think about the things we did. I've never really stopped thinking about it all. You've always been able to turn me on so much. Still to this day."

"There really is a connection."

"Yeah, there is." I felt it again in my stomach.

The butterflies

. "I mean, look at where we are now. It's been almost 20 years. We're still sneaking off to be together. I don't regret it for one second."

"Me neither."

Silence.

I spoke first. "Sooo."

"So yourself," she replied.

I was so nervous. "Soooo..."

"What?"

"I dunno."

"Just say something!"

I swallowed, and asked, "So, are we really going to do this?"

"Do you want to?"

"Yes," I answered, without the slightest hesitation.

She trailed off. More silence. "Are you sure?"

"Yes, one hundred percent for sure. I've wanted this for a long time," I said, unequivocally. "Do you?"

"Of course!"

"So, then if I make a reservation for that Tuesday..."

She cut me off. "Yes! I will be there!"

I smiled, took a drink, the whiskey burning my throat again. My heart raced, and I grinned from ear to ear. "Well, ok, it's settled then."

How could I think of anything else for the next three weeks?

* * *

I pulled into the parking lot and parked near the back, away from all of the other cars. I got out, grabbed my bag and headed toward the front door of the hotel. Just walking inside made my heart beat a little faster. I was nervous. Excited. Anxious. I had the familiar butterflies that she's given men since the first time we kissed in my basement in 11

th

grade. The same butterflies that I would get each time we were in the car alone heading to some abandoned parking lot.

My God, that was twenty years ago!

I smiled and laughed to myself.

This is a long time coming.

I don't remember anything about the interaction with the girl at the desk. Clearly, my mind was elsewhere. All of a sudden I had a keycard in my hand and I was standing near the elevator.

Was she really going to come? Were we going to do this?

The anticipation was driving me wild. The elevator door opened, and I stepped inside.

Down the hall and to the left, Room 414. My hand shook as I slid the keycard into the slot. Green light. I pushed open the door. As I entered the room and looked around, my excitement grew. It was perfect. I quickly imagined all the things I wanted to do with her, in all the places I wanted to do them. My mind raced. I put down my bag and fished my phone from my pocket to text her, "I'm here."

A minute passed. I stared at my phone, waiting anxiously for those three dots to pop up. My heart was pounding. Finally, she starting typing, texting back, "Be there in an hour."

I smiled and put the phone down, my hands starting to tremble with excitement. As I turned away, my phone buzzed. I turned back and picked it up. She texted a picture. I opened it as fast as I could.

She looked beautiful. Her hair was perfectly curled. Her smile beamed. Her eyes looked sexily up into the camera. Black bra straps visible on her bare shoulders, and she showed just a teasing bit of cleavage. I texted back: "OMG I love! Room 414 can't wait to see you."

I tossed my phone on the bed, stripped down to my boxers and laid out my outfit for dinner. I looked around the room, smiled to myself and turned toward the bathroom for a shower. I still couldn't believe it. She was going to be here in an hour.

* * *

She threw her head back as she laughed, her beautiful smile beaming, her radiant skin glowing in the soft candle light. I tipped the wine bottle upside down and into my glass, making sure to finish every last drop.

The waiter graciously picked up the check with a nod and headed back towards the kitchen. I scanned the restaurant; seeing only a few tables left finishing up, I figured it was time for us to head upstairs. As if I needed another reason to get her alone.

"Ready?" I asked.

"Yeah," she answered, brushing her hair from across her eye. I wondered if her heart was racing as quickly as mine. So excited, but so nervous. I couldn't believe we were actually doing this. 4am had happened so fast, there wasn't time to even think. But this was different; we had talked about it for years. And now it was happening.

As she stood, I couldn't help but take another long look at her. She wore exactly what she promised -- a simple black dress, tightly hugging her curves, low neckline showing off her luscious cleavage, black stockings, and of course, my favorite red heels. Like a cherry on top of my own private dessert. I walked around the table to her side.

"Good thing we don't have to go far, huh?" she said.

I put my arm around her, hand on her waist. "Yeah, I think we can make it four floors."

"Good call on picking a hotel with a good restaurant."

"Oh, I know what I'm doing," I joked, flattening my tie.

"Oh yeah?" she said with a flirty smile.

"Full confidence."

"We'll see about that," she said, her eyes flirting with mine. "Confidence goes a long way."

"Indeed it does." I grinned.

We walked into the elevator, and before the door even closed, she turned to me, thrust her chest into mine and pushed me against the back wall. She whispered into my ear, "Are you ready to finally fuck me?"

The doors closed with a quiet thud. Leaning back against the mirrored wall, I reached around her body with both hands and grabbed the bottom of her ass. Squeezing, I felt no panties. Immediately, I felt a surge run straight to the tip of my cock. I placed a heavy kiss on her lips, parting her mouth and seeking her tongue with my own. "I'm ready to do a lot of things to you."

"Mmmm, yes," she giggled and smiled as we kissed. The bell rang and the doors opened. I reached down to rearrange things in my pants. She noticed, then looked up into my eyes and grinned. She stepped out and turned towards room 414. I followed her down the hall.

By the time I shut the door behind me and took off my shoes, she was already sitting on the bed.

"No, no. Not yet," I said as I loosened my tie and started to unbutton my shirt. "Come here first." I motioned toward the bathroom with my head.

"But wait," she said, stopping me in my tracks. I turned back to her. She lifted her legs, curled them to her side, the red shoes still on. She looked down at her feet and then back up at me. "What about these?"

My shirt unbuttoned, I smiled and undid my belt, giving some temporary relief to the bulge that was growing inside my pants. My eyes glued to her sexy heels, I took a few steps towards her and asked, "Can I?"

"Of course. You know I'm wearing them for you." She sat up and placed her feet on the ground. I approached her. "But first, let me help you with this," she said, unbuttoning and then unzipping my pants. I shivered as she grabbed the elastic of my black boxer briefs and pulled them down over my cock, already achingly hard from our short elevator ride. Once freed, it sprang to full attention just inches from her face. My balls were freshly shaven, and hair trimmed tight, maximizing my sensitivity. As she pushed my pants down my thighs she smiled and looked up at me. "You can't expect me

not

to do something with this first. I've been thinking about it all night," she said. She took me into her hand.

I gasped, shivering at her touch, her hand freezing against my hot, throbbing shaft. "Cold?" she asked, almost apologetically.

"Maybe a little, but..."

Before I could get another word out, she pushed the tip of my dick back, tilted her head and leaned forward to take my balls into her heavenly, warm mouth. Burning pleasure flooded my body as she gently sucked me in, her expert tongue rolling my balls around inside of her mouth. She lapped at the underside of my balls, coating me with a thick layer of her hot saliva. Then, she looked up at me, locking her beautiful brown eyes on mine and slowly—

so slowly—

drew her tongue up the full length of my shaft. My upper body tensed and my knees got weak as she pressed her warm tongue against the back of my engorged cockhead; I could have exploded right there.

I grabbed the back of her head, her thick curls between my fingers. All I could manage to say was, "Whoa."

She took her mouth off of my steely cock, now moist with her spit and glistening in the dim light. She giggled. "That better?"

My legs wobbled, I could barely keep my balance. "Um, yes. Very much." I stepped out of my pants and pushed my socks off. I reached down to guide her feet back up onto the bed and then ran my hands up and down her calves. She leaned back on her elbows, and shuffled towards the edge of the bed, bending her knees upwards, her heels spiked into the bed. Her skirt fell back to reveal the lacy tops of her thigh high stockings—

my favorite

.

"So, are you excited to see the shoes?" she asked, turning her feet to the side.

"Oh my God, of course."

"Well, what are you going to do?"

A second of uncertainty came over me. "I just—I guess, I don't really know what to do. You know?"

"What do you mean? You talk to me all the time about it."

"Yeah, yeah, I know," I said, nervous for the first time all night. "But, you know, I...um...I never thought I'd actually be able to

do

anything with them, you know, while you are wearing them."

"Here. I have an idea. Take your shirt off," she said, coolly. I obliged, wriggling out of the sleeves of my dress shirt, letting it fall to the floor, then pulled my undershirt over my head. I stood in front of her. Naked. But completely comfortable. It felt so natural to be with her this way. She motioned me to her with one finger. "Come closer."

I stepped toward her. She lifted her feet off the bed and gently pressed the platforms of her heels to my stomach. I looked down to watch as she gently nestled her the stiletto spikes into the tight tuft of hair above my cock. "Go ahead. Touch them," she ordered.

Topped with their bows—to me her heels were like lingerie on her feet. Her cute toes peeked out, dark red toenails showing through her stockings. My hands glided up and down her calf and onto the arches of her feet. I caressed them, gently running my hands over every subtly sensual nuance of her shoes and feet. It felt incredible to my touch. I drew one of her feet to my face, and kissed the arch, opening my lips slightly to take it into my mouth. The satiny ruffles felt amazing on my lips and cheeks and even the tip of my tongue.

My heart was racing. "My God, I never knew I'd like this so much," I said, looking down at my stiff cock, stronger and harder than ever. "I mean, I've made myself cum looking at your shoe pics so many times. But I really, really had no idea what this would actually be like."

She smiled and answered, "I love that they can do that to you. It's so sexy."

I rested her heel on my shoulder. She inched her other foot down near the base of my cock, I gasped as I felt the soft ruffle brush against my sensitive balls. "Oh fuck, that feels good."

Smiling, she moved her foot down a little further and rubbed the bow underneath. "Oh God, yes, right there. Don't stop," I sighed breathily, turned my head and pressed her foot against my lips and mouth.

"Touch yourself."

"Oh my God, really?" I asked excitedly.

"Show me what my shoes do to you."

I grabbed my cock with my free hand, and tightened my grip around her toes with the other. I started to slowly pump myself—my balls skimming lightly against the ruffles, tickling my most sensitive area with every stroke. It was pure ecstasy.

I looked down at her. Her mouth open in a blissful half-smile, clearly enjoying the sight of me pleasuring myself. I brought her foot down away from my face and guided it right next to my dick. I cupped the heel to hold it in place, my fingers wrapped around the spike. My cock softly rubbed against her shoes with every stroke. My mouth fell agape as I stared at her shoe in my hand and watched her massage the other underneath my balls. I threw my head back and let out a long groan, squeezing myself as I paused at the bottom of my stroke. A clear drop of pre-cum dripped down the head of my engorged dick.

I let go of myself and took her other foot into my hand. "Do you know what I really want to do?" I asked blushingly.

"Mmm, yes, I think so," she answered, smiling back at me.

She always knows.

"You can do whatever you want to do to me."

I didn't hesitate. I gently set her feet on either side of my cock, stiletto spikes underneath my balls, the platforms resting right above the base of my dick. My heart was pounding. My cock stood tall in between her sexy shoes, her toes peeking through, so cute and so sexy at the same time. As a drop of my pre-cum rolled down my cockhead, I imagined cumming on her toes...

Her feet and heels were now exactly where I wanted them, my thumbs resting across her toes, the satiny ruffles under my fingers, my pinkies resting on the arches of her stockinged feet. I slipped my cock down between her insoles and pressed the shoes lightly against myself. And then...I started to fuck them. Hips thrusting gently, sliding my cock back and forth between the soft insoles of her shoes. My God, it felt incredible. And the sight of my cock thrusting between her feet and shoes was so fucking erotic; I'd been fantasizing about doing this for years. I moaned and sighed with intense pleasure.

"Do you like fucking my shoes?" she asked, looking up at me.

"Oh my God, so much," I said, staring back at her, not breaking my stride.