Siena Ch. 02: What If

A couple days passed before I had a chance to check in with Siena. It's funny how life gets in the way of connecting with people.

"Sup?" I texted to her, eloquently.

It wasn't until later in the day she responded. I concluded that she was working. It was always so difficult to follow her crazy schedule - I had stopped trying long ago. She was never that far away from her phone unless she was at work.

"Work, kid, puzzle, work..." she replied.

"Exciting." I texted.

"#totes. What's up with you?"

"Wife, work, kids, sleep, repeat." I sighed as I texted this. Life in a pandemic had become just a bit too predictable. Still, I was working and my family was healthy, so it was hard to complain.

"Hey," I typed, "you and Richard ok with everything that went down?"

She took a bit to reply. I was just about to put down my phone and do something else, when I read: "overall, it went better than we even planned. You did a great job! I cannot thank you enough. But, I had to talk to Richard a bit after, he got so quiet."

I smiled at her gratitude. It was sweet, especially since she knew from the decoration I left on her chest how much I enjoyed it.

"Did you get to the bottom of it?" My mind suddenly flashed to Richard pulling Siena to him, her pushing back in doggy style. He certainly got to the bottom of it. The memory made me chub up just a little.

"Ya," she wrote, "we talked. He wasn't too happy that you kissed me or came on my tits..."

"Oh!" I replied. Again, the image of her fingers between her legs, turning to offer up her chest for me flashed through my mind. And how I squirted all over her tits. The chub was officially semi-hard.

I started to text out an apology. I kept writing and erasing it until her next text interrupted me.

"But I told him how it wasn't a big deal. You and I are friends and it was fun. That was it. And I said, 'I didn't suck his dick or anything, he just jizzed on me'."

I could totally hear her voice saying that and I laughed out loud. "LOL!"

"Then he asked me if I wanted to and I told him I was tempted. Anyway, I came clean on most of it, how I was going to break up with him, how you offered to help, and either he was ok with it or he wasn't. It took a bit, but I think he's fine. He might be the jealous type, ugh 🙄"

There was a lot to parse through in that sentence. "I don't know if I would have told of him about our plan, but I admire you for being honest with him."

"Ya, fuck being fake. If he doesn't like it, there are ten more behind him."

Again, I laughed. She was too funny, blunt to a fault.

I shook my head and reread her long response. "Wait, you were tempted?"

A couple minutes passed while she replied. I shook the phone, "type faster, woman!" My cock was officially erect. All the memories flashed through my mind. I rubbed it a bit as it was demanding attention.

"Umm, ya, duh. When you were on the bed and he was eating me... omg... I so needed to suck dick."

I stared down at that. "Huh. I KNEW you needed something. I asked you." Stroking it just a little, I remembered just how much I wanted to.

Siena's reply arrived in seconds, "ya, well, 🐔"

"Haha, you are the bravest person I know. I was severely tempted to just do it," I replied honestly.

"We are friends, Derek. I wouldn't do anything to mess that up." she wrote, and seconds later, "you were?"

"Ya, totally. But, Richard and..." I shook my head.

"and..." she prodded.

"And I didn't want anything to change in our friendship. I know we promised nothing would, but that was a line I wasn't crossing. If I hadn't set my line before, I definitely would have." And my turgid cock agreed, nodding up and down.

"Oh," she replied.

"Is that ok?" I asked.

"totally. It's why I chickened out. But, seeing you stroking yourself so close... ugh, I did want it." My in real life touching definitely was getting a bit more... serious.

"What do you think would have happened to us?" I asked.

She said, "I think we would have been fine. Sex is just sex." That is the Siena I know.

"Indeed," I replied. I was working up towards a point where I knew I would have to cum when I heard the kids and wife downstairs. The window had passed and my day had to get started. I gave a silent apology to ol' one eyed Willie.

"Hey listen, I gotta jet," I texted her. "Continue this discussion tonight. I want to hear your thoughts about what if"

"What if?" she asked.

"Ya. What if I had pushed myself towards you and did what we both wanted in that moment. Don't say now, let's leave it for tonight."

"Ok, it's a date. Later loser"

"See ya, dog face" my cock giving one last twitch at "date" as I got myself dressed.

================

That night, it took forever to get kids settled and wait for the wife to sleep. I shot a text over to Siena.

"Ok, you avail?"

A few minutes later she wrote, "yep. Was in the shower, squeeky clean."

"Pics or it didn't happen" It was nearly a reflex response.

"You wish."

"I do"

And the ritual was complete.

That out of the way, I deliberately set the phone down and waited. Impatiently, I may add.

Ding! Grinning, I picked up the phone. "So, what if?" I had her. Curiosity killed the cat, or at least got the pussy wet. Something like that.

"Let me set the scene for you," I began.

"You were... Actually... do you mind if I call? Texting this will take forever."

"Ya, five minutes. Let me switch to the bed."

Five long minutes later, I gave her a ring. She picked up the phone.

I started talking immediately, she didn't even get out a hello. "So, you were laying there, legs hanging off the end of the bed, his face between your legs. I was beside you on the bed, close enough I could reach out and touch you. And I was tempted. In fact, later I couldn't resist tweaking your tit."

"Mmm hmm," I heard her breath into the phone, "I remember"

I could imagine her laying back, eyes closed, listening to me talk.

"Richard had teased you, at my direction, and then he had trapped your clit between his lips and was tugging on it gently. Your chest was heaving and I was slowly stroking myself, enjoying the show."

"Ya..." the reply was dragged out and I could tell she was remembering.

I pulled down my shorts and my rock hard cock waved briefly before I grasped it.

"I asked you what you wanted. I could see you thrashing, nearly overloaded with pleasure, with no hope of going over the edge. You told me you needed to get fucked. What if you told me the truth. Put yourself there again and tell me." I kept my voice low.

I heard rustling on the other end and Siena's response. "Mmm, I, uh"

Her shortness of breath was hot as hell to hear. She did not answer and the moment dragged on just a tad.

"Siena, what do you need?" I asked again.

She whined at the other end. I swore I heard a short clipped moan and then a brief period of silence. Whispering, almost inaudible, I heard, "I need to suck a dick."

"What's that? Couldn't hear you?" I asked, a grin on my face

"I needed a DICK in my MOUTH," she said, loud enough for me to temporarily move the phone away from my ear.

I laughed good naturedly.

"Jerk," she stated, and I knew she didn't mean it.

"In that moment, stroking my cock like I am now," I paused and I could hear her notice. "I would have pushed up in the bed and thrust myself towards your mouth. It was already open, it would have been so easy."

"Mmm, hmm" was all she said.

I took a chance. "You are touching yourself right now, aren't you?"

"Yessss" she hissed. "Don't stop."

I thought I was hard before. Now, it was almost painful. That didn't stop me from gripping it and giving a few long strokes. "My cock would have pressed to your lips and I would have slowly eased my way in."

"Oh... mmm," she panted. "Are you touching it, right now too?"

"I have been stroking for like ten minutes now," I replied. "Tell me what you would have done. Imagine the what if and describe what's in your head."

Heavy panting over the line. I knew her fingers were buried inside her and she knew my cock was in hand. How was it that she could get me into these supremely hot situations?

"I, uh," she stammered, clearly struggling with her words. "I would have sucked your dick."

Laughing, I pressed her, "No, slow it down. Describe what you think would happen. Paint a picture with your words" I waited while she put together her thoughts. I think she temporarily ceased manipulating herself to do so.

"Sigh," she sighed, "fine!" She drummed her fingers on the phone and said, "My mouth would have opened just the littlest bit and I would have made you push between my pursed lips."

I reached over on my nightstand and squeezed a bit of lube onto the tip of my dick. Grabbing it firmly, I forced the head reluctantly through my fist. "Yes, I can imagine that," I said. "I am pushing myself through my hand right now."

"Oooo." she said, resuming, "My hands needed something to do, so I would have reached between your legs and fondled your balls. I would have grabbed your whole package and pulled you deep in, using my tongue on your shaft." I stroked longer now, closing my eyes to imagine how that would feel.

I said, "I would put my fingers through your hair and apply a little force on the back of your head. You are in control, but I would press the matter."

Siena's panting got a bit more pronounced, "Would you fuck my face? Force your dick in and out of my mouth?" she moaned/asked.

"Once you did not pull away, I would indeed thrust in and out. Your hair would be in my fist and I would take more and more control. Just like I am forcing my cock through my fist now."

"Egad, that's hot," she said. "I would twist my hand on your shaft and touch my nose to the bottom."

I was stunned. "You can do that?" I asked.

"Ya, I am pretty sure I could get you all in. You are not as long as some of the others I have blown, and I could probably even lick your balls with your cock in my mouth."

"Wow," I said. "Impressive." On each downstroke now, I used my index finger covered with lube to fondle my sac, imagining it was her tongue. I thought to myself that I was going to cum from this eventually, and was excited by the prospect.

"And when having your pussy was too much and Richard started fucking you, what then?" I asked, going faster with my hand.

"Um... uhh..." she said.

"Siena, grab one of your toys and use it as a memory aid." I waited as she put down the phone and heard a drawer open and close. When she came back on the line, I said, "And take off all your clothes, I want you to be naked."

She laughed. "I have been naked almost the entire time," she said.

I remembered how I heard rustling in the start of the call and should have known. I shook my head and slipped off my shorts completely, joining her in being naked. My heart was thudding.

"Ease your toy up and down your slit, just like Richard did to you," I commanded. It was just like the directing I did with them, except this time it was Siena following.

"I'm doing it. Mmmm, that feels wonderful. But, I need it inside of me," she said.

"I know. I know. What are you doing to me in our what if?" I ask.

"I am doing my level best to give you the best blow job of your life. My hand is squeezing your balls, sliding my middle finger towards your bum and pressing in. My mouth is bobbing up and down and I am basically jerking you off on the upstroke."

I saw it as if it was happening. And my hand did it's best to simulate it. I had to get more lube and apply it on.

"Holy, man. I missed that? What the fuck was I thinking?" I asked. Hearing her panting getting more urgent on the other end was doing things to me. My balls felt that familiar tingling. I slowed down just a bit so that I didn't shoot off too early, it was not time for me cum yet.

"Ease your stand-in dick into your dripping pussy. Start fucking yourself for reals."

Nothing but heavy panting on the other side. Just hearing it made me want to drive over and launch myself at her.

"Is that you inside you, yet?" I asked coyly.

"Uh uh, mmhmm, ya."

I had a flashback to a couple nights ago. The picture in my mind was Richard's cock disappearing in her pussy. Her bare sex revealed it all. Her clit stood out straight, begging for attention.

"While you are sucking me off and he's fucking you..." I trailed off.

"Mmm. What? Tell me," she gasped.

"I would scoot over enough to touch that clit that is staring me in the face. My fingers would feel directly how soaked you really were, having a guy pound you on both ends at the same time. I would smack the top of your pussy with my hand."

I heard a distinct clapping sound over the phone and realised Siena was mimicking my words. Her fingers were now on her little clitty, probably rubbing it like mad.

"You dirty girl," I said, not even realising it was out loud.

"Oh, I am. Use me like a slut," she said to my distinct surprise.

"Keep smacking that thing. Do you remember what happened next?" I asked.

A couple smacks over the phone and she groaned, "he fucked me doggie style," she accurately recounted.

"Do that now. Get on your hands and knees."

Her phone went down and all I heard was rustling noises. It seemed to take a bit longer than I expected.

"I'm ready," she said, with a sexy little moan.

"Why did it take so long, Siena?" I heard breathing and moans and an echo and realized I was on speaker phone. "You naughty girl, what are you doing?"

"Ugh, tell me I'm a slut again. Tell me, tell me.." more sexy utterances.

"My dirty little slut, let me fuck your mouth while Richard takes you from behind. Only dirty girls do two guys at once."

"Oh... My... Gawd," she cried and I heard her cum. I nearly lost it right there, but my curiosity stopped me.

I repeated my question. "What are doing, dirty girl," I asked.

"I don't want to say," she whined, still breathing heavy.

"Come on, tell me," I coaxed.

"I'm... mmm... I'm fucking my wall," she said.

I was confused. "Say what?"

More throaty moans, some wet slapping sounds. "I own a big dildo that sticks to the wall. I put it up. And then backed my fat ass onto it. I'm fucking my wall."

I was blown away. I remembered vividly the noise of flesh smacking together when her and Richard were doggie style. One last squirt of lube, and I picked up the pace of my stroking.

"Only a dirty slut fucks her wall," I heard her hiss in response.

"I'm a dirty girl," she moaned.

"Maybe you wanted me to pull myself out of your mouth and spank your ass with my cock as Richard pounded you."

"Oh yes, I love it," she clearly was building towards another orgasm. I felt this was going to be her big one, and vowed to time mine with hers.

"While I was behind you, I would push my finger into your anus, see how you react."

"You wouldn't," she said between loud fleshy thumps. I imagined her riding her wall toy hard, her cheeks giggling as she slammed against it.

"You know I would," I countered.

"Yes, put it inside there. I want it" she said.

"You little whore. You like that, don't you? You're fingering your own ass right now in real life, you filthy girl."

It was more of a statement then a question and I heard her moan a yes, her breathing getting ragged. It was time to step up my pace on my end. My fist was tugging up and down, my grip firm.

"Maybe you wanted me to join Richard. Have him lie down under him, you pushing down. And then have me enter your ass," I said.

"Umm, ugh, no, you wouldn't, you wouldn't dare," she said.

"Maybe you are right, but you pictured it, you fantasized about it. As I finger your ass, you might even crave it." I was getting there and I let my breathing blow out so that she knew.

"We're almost there, Siena," I heard her "uh huh"

"One more thing..." I let it hang in the air a bit and listened to the wet obscene sounds coming from the other end.

"Name it," she cried, "but hurry, I'm so so close."

"I want you to accept my video call right now and push the phone directly underneath you, looking up. I want you to show me how you are being a little harlot. Show me!"

I quickly hung up and pulled up a video chat app, opening a connection to her. We had used this one before to chat, so I knew she could do it. It rang and rang until it timed out.

"Come on, Siena, pick up," I said out loud, and tried again.

This time, she answered. I was already looking directly up between her legs. She must have set it up so that it would already be in position. As I watched, I saw her wall mounted toy disappear inside of her and reappear a moment later. I could see her pink wetness. It was an amazing view.

"That's it, Siena. I'm watching you fuck the wall. I can see your shaved pussy from here. I notice you probing your backdoor. You are so slutty!"

"Slap that pussy for me," I could see and hear her do it.

"Mmm, such a naughty thing. Richard is fucking your pussy and I am poking your ass. You love it, don't you?"

"I do, I do! Make me your whore. Use me." I could hear the desperation in her voice. How close she was...

She grunted. "Tell...me...what you...are...doing," I could just barely see up to her chest and realized she couldn't really see me.

"I'm stroking for all I am worth. My cock is so hard right now. I could cum at any time, but I'm waiting for you..."

Siena picked up her pace, "I am almost there..."

I felt myself on the brink, "I'm about to squirt, hon. I'm going to cover your gorgeous ass in my jizz as I finger your ass. Or maybe you want it inside your ass, my cum gushing into your tight asshole, you dirty..."

All of a sudden, Siena started jerking her body, pushing it tight against the wall and arching her back. Loud moans filled the air. She came spectacularly. I felt like clapping, it was a stunning performance.

I wasn't too far behind.

"I'm cumming," I announced, and watched as she reached between her legs to pull the phone towards her. Understanding what she wanted, I aimed the phone so that she could watch me shoot my load all over my belly and chest. I don't know if I had every cum as much as right then. I was absolutely covered.

I collapsed back and I could hear a distinct "shoop" as Siena dismounted her wall dildo. I gazed down at myself and laughed.

"I probably should have brought a towel with me," I said.

She giggled and pointed the camera to her soaked thighs and nearby hand towel. "Rookie mistake," she said, smiling.

"My Lord, my heart is beating like a mile a minute" I said.

"Me too!"

"Thank you," she said, and I shook my head.

"Oh no, thank you! That was incredible," I replied.

"Are you bummed that didn't happen for real," Siena asked.

"I would be lying if I said I didn't regret it at all. But, no, not really. You're too good a friend to mess stuff up. It was perfect. And so was this."

"Good. My thoughts exactly. I regret it not being real a little too, but this was wonderful."

I stretched and yawned. "It's so late, my gosh. I should sleep."

"Typical," she said with a huge grin, "cum and roll over to sleep."

"You know it. Except this time I need a frickin shower. Maybe two." I winked at her and showed her how covered I was.

She licked her lips suggestively. "Mmm, nice."

"Nothing has changed," I said.

"Nothing's changed," she confirmed.

"Good night, Siena, thanks for the what if."

"Totally welcome. Night," and she closed the connection.

I wistfully slipped into slumber wondering what was next in store with Siena. Only time would tell. But, I suspect it would be fun as hell.