My Best Friend Emily Ch. 04

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Our first planned night together doesn't go as planned.
11.1k words
4.66
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Part 4 of the 8 part series

Updated 06/07/2023
Created 10/07/2014
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Welcome to part four of this ongoing series. As promised, we are going to get back to the group sex motif. Any similarities to any persons, places, events, or anything you make have ever heard or imagined before is a complete accident.

*****

It was quickly becoming the slowest week of my life.

Everybody knows where I'm coming from, I'm sure. You have a full week of work or school to suffer through, knowing that you have something great planned for the weekend, and the anticipation is causing every dull moment of the week to drag. You are always looking at the clock, thinking 'is this day over yet?' Is it Friday yet? Yeah, that was my week.

It didn't help that it was a particularly crazy week. It was just after tax season and it seemed that all of my middle-aged clients wanted to go over their post-tax finances and determine whether or not they were contributing enough to their retirement accounts, etc. Usually I got a kick out of it. Maybe it was the voyeur in me. I enjoyed the glimpses into the private lives of other people that my job gave me. Sometimes we would go over expenses and uncover some interesting facts. For instance, once I was working with one couple who had spent an enormous amount of money on a trip to Europe. I pressed them about what could have possibly cost them that much. They finally relented. In Amsterdam, they said, they paid for a private sex show. It cost over two thousand dollars. It was totally worth it, the husband said with a smile. The wife blushed. In the end, I was probably more embarrassed to hear it than they were to admit to it, but I did go home and fuck Lisa silly that night. I just didn't tell her what got me so turned on.

Anyway, where was I? Tuesday? Ugh, still Tuesday? Well, one thing about that day was that I got my first taste of what all of the crazy kids out there call 'sexting.' I was working at my desk Tuesday afternoon when my trusty iPhone buzzed. I was in the middle of something so I couldn't look right away, but when I had a break I pulled my phone out of my shirt pocket and took a look. I missed a text from Emily. She probably had something to say about the ballgame that night, I thought. We always talked about the starting pitchers and matchups before games. I flipped open my messages... and was greeted by a close-up photo of a pussy. I felt my jaw go slack, and my slacks get tingly. I furtively glanced around. Nobody was around me. The pussy was shaved, so I quickly guessed that it was Emily's. It was open and inviting, the lips engorged, the slickness evident even on that small screen. Emily's text was 'thinking about you. Go Cards!' I chuckled, trying to make it look like I was just reading a funny text and not staring at my friend's vagina. But, what do I do? Do I answer her? Do I reciprocate? I was hard as a rock. I furtively glanced around. Nobody was paying any attention to me. I stood up and began to weave my way through the desks to the bathroom, trying to act nonchalant, and not draw any attention to my hard cock which was probably tenting out my suit slacks. I was relieved when I made it to the bathroom without having to make eye contact with anyone. It was your typical office men's room, with two urinals and three enclosed toilets. I peeked under the stalls. I was alone. I went into the nearest stall and shut the door. I flicked open my phone again and stared at Emily's pussy for several seconds. I took a deep breath. Was I really going to do this? I stashed the phone back into my pocket and undid my belt, unbuttoned my slacks and let them fall to the floor. I hooked my thumbs into the waistband of my boxers, and I took another deep breath. I could feel my heart pounding. I could see why people got a thrill out of this. What a rush! I pulled my boxers down and my erection popped free, all seven inches of rigid manhood. I pulled my phone out again and flipped to the camera setting. I had never taken a picture of my penis before. What were the guidelines for a good cock selfie anyway? What was the best view? I found myself experimenting with different angles. How much thought are you supposed to put into these anyway? Finally I just decided to snap a 'head-on' photo. The sound of my camera snapping the photo echoed unexpectedly loudly in the cramped stall and I jumped. Thank goodness nobody else had come into the bathroom. I looked at my handiwork. The big purple head was in the forefront, the contours of my circumcised penis clearly visible. The hole was open. From the angle you could kind of see my shaft behind it, and my hairy groin. I shrugged. I had seen lots of porn over the years, but I was 100% heterosexual and never spent any time looking at pictures of dicks, and as a result the art of taking a good dick selfie was lost on me. This would have to do, I decided. I stared at my cock for a few seconds. When it was this hard and Lisa wasn't around, usually I would just grab it and beat off, but I never jerked off at work before. No, I couldn't do it there, I finally decided, pulling up my boxers and my slacks. My erection will go away on its own, eventually. Before I left the stall I replied to Emily, texting 'thinking of you too. Go Cards!' and attaching the picture. I took one last deep breath, knowing that I was crossing yet another line, and hit send. The self-flushing toilet went off at that moment and I nearly dropped my phone, but I recovered and went to wash up like I was just doing what most people do in the bathroom.

My phone buzzed again almost as soon as I sat back down at my desk (I keep it on vibrate when I'm working.) I glanced around again, trying not to look as guilty as I felt. This time Emily texted me a photo of just her mouth, wide open and shaped like an 'O' and underneath she texted 'put it right here.' A moment later she added 'btw you just made me wet :-O' I shifted uncomfortably in my chair, my erection raging and tingling anew. So much for it going away.

The day continued on pretty much like that. In between tasks Emily and I traded texts. There were no more pictures but plenty of sexual innuendo. Finally five o'clock rolled around. Unfortunately while everyone else was packing up to go home, I had another evening meeting. Worse yet, this one was a 'house call' with an elderly couple with a lot of cats and hearing aides that weren't always turned up as high as they should be. I always left there exhausted, annoyed and reeking of kitty litter. Any sexual energy I had built up during the day had drained right out of me. I staggered into the house after 8pm and ate the lukewarm fast food that Lisa had left on the kitchen table. She was already into her evening routine, preparing for the next day. There was no sexy lingerie in sight. We exchanged a little small talk and then I left her to go watch the Cards game in my recliner. I probably made it to about 9:30 before I fell asleep, waking up sometime after midnight. I turned off the TV and staggered into bed, falling back to sleep within minutes.

I was wide awake at 5am, though. Here was where I usually snuck out of bed to watch porn. Do I really need to? I thought to myself as I lay there in bed. Lisa was still sound asleep beside me, snoring softly. I thought about waking her. No, that never went well. Lisa wasn't a morning person, and morning sex wasn't her thing. I thought about Emily, the sext of her pussy in my mind's eye making me hard again. Well now I had to do... something. With a groan I rolled out of bed and shuffled into the bathroom, my erection leading the way. I turned on the shower and pulled down my boxers. I stared at my erection; letting mental flashes of the events of the last few days stoke my libido. The mud fight, the shower sex, the threesome, the food fight, the blow jobs from Emily, Lisa in that lingerie, the sexting. I took myself in my hand and started stroking, letting my mind wander from one sexual image to the next. It only took me a few minutes to bring myself to an explosive orgasm, shooting glob after glob of clear white fluid into the toilet. I groaned as I stroked myself as fast as my hand could go. I had to reach out with my free hand to steady myself on the countertop. Finally the spasms stopped, and I let go of myself, idly studying the glob of cum that dribbled onto the knuckle of my pointer finger. I took some toilet paper and cleaned off my finger, then the cum that was still dribbling off the tip of my penis. Finally, I cleaned up any cum that was stubbornly sticking to the bowl. I flushed the toilet, watching to make sure any evidence of what I did was gone. Even now, with my suddenly sexually liberated wife, I didn't need her coming into the bathroom and seeing traces of my cum in the toilet and knowing that I jerked off.

Wednesday and Thursday were almost carbon copies of Tuesday. There was a little sexting, an evening meeting with a client, a lukewarm dinner, and ending with falling asleep in front of the ballgame. Because of my ongoing sexually charged conversation with Emily, I was in a constant state of arousal. I hadn't been like that since Lisa and I first got together in the dorm over ten years ago. Back then we spent almost every free moment together, talking, kissing, cuddling, exploring each other. Lisa and I waited almost two months to have sex with each other. I know now that it was because Lisa was struggling with her sexuality, but I can't remember how I held out that long.

While I was home I saw very little of Lisa. She was hiding out in the bedrooms most of the time I was home. It wasn't unusual before, but I thought we had turned over a new leaf. I wondered what she was up to, or if we were just falling back into the same routines. I was focused on the weekend anyway. Emily and I had decided that we'd go out to dinner right after work Friday night before we came back to the house and... did whatever came naturally.

I was in my recliner Friday morning in my underwear with my bowl of Cheerios, as usual. Lisa was passing me by on her way out the door. "I'll meet you at Longhorn's after work, okay?" She said.

I jumped. I never told Lisa our plans! How did she know? "Oh my God, did I forget to tell you?" I said.

"It's okay, Emily texted me," Lisa said, and she smiled at me enigmatically. That was odd. What was she hiding? She turned and walked out the door, leaving me to wonder.

Friday was blissfully quiet compared to the rest of the week. I just had to catch up on all of the paperwork that had piled up, especially after meeting with all of those clients and changing their investment strategies. I even found time to make a few calls to other clients, you know, to try to drum up more business. A salesman's work is never done.

Around lunchtime my phone buzzed. It was a text from Emily. She texted me 'so excited about tonight' and attached a close-up of one of her nipples, hard and puckered. I laughed, but how do I respond? Another dick selfie seemed redundant. I surreptitiously snapped a picture of my tongue sticking out and texted it to her without comment. Emily's response was 'I have plans for that.' I glanced at the clock again. 5pm couldn't come fast enough.

The end of the day finally arrived and for once I was out the door with the rest of the office. I made it to Longhorn's in record time and found Lisa waiting for me, dressed in the same white blouse and long skirt she was wearing that morning. Emily arrived a few minutes later, dressed in a tight white blouse and gray slacks.

At dinner I was struck by the change in attitude between Lisa and Emily. Since Emily was my best friend we had all gone out to dinner together many, many times before. For the most part those social outings were dominated by me and Emily, and Lisa sort of kept to herself, shut out of our conversations about sports, or our reminiscences about our teenaged experiences. Tonight, however, Lisa was very involved in the conversation with Emily. I wondered yet again what had happened between the two of them that past Sunday when I was gone.

There was something of a 'foreplay' feel to dinner. We all knew that Emily was coming back to our house afterwards for a night of wild sex. Emily and I kept trading knowing glances and winks. At one point during the meal I felt Emily's leg brush up against mine from where she was sitting across the table. Lisa was sitting next to me, and at another point I felt her place a hand on my thigh. I reciprocated, sliding my hand along Lisa's thigh, and brushing my leg against Emily's under the table.

We were held up several minutes because the server disappeared before we could ask for the check. Exasperated, we discussed everything from trying to track him down in the restaurant to just dashing out the door. Finally he breezed by and dropped the check on the table. "Whoa, buddy!" I shouted before he had a change to rush off again. I slapped down a credit card and asked him to come back quickly because we were in a hurry. He paused, looking from my beautiful wife to my gorgeous best friend, and then back to me. His face suddenly broke into a huge smile. "Sure thing, boss," he said, and disappeared.

Emily was trying to slip me money for her meal. I refused. "Are you kidding?" I said to Emily, pushing the money back to her. "Do you know how much money I made this week?"

"It wasn't from selling dirty pictures, was it?" Emily asked without missing a beat.

I froze. I didn't tell Lisa about our sexting adventures. I glanced at her. She was looking at me curiously. Luckily the waiter came back with the receipt, giving me a way out of that awkward moment.

We all were in separate cars, so we drove in a sort of convoy home. Three cars at once was more traffic then my otherwise empty street had ever seen. We pulled into the driveway one by one and then crowded into the house. We kicked off our shoes and I put my work bag down in its usual spot on the ledge by the front door. Emily brought in a stuffed overnight bag. This time she was completely prepared for spending the weekend with us. I went into the bedroom to quickly change out of my suit, putting on a t-shirt and jeans. I plopped down in my usual spot in the recliner. Lisa sat on one end of the sofa. Emily sat on the other end of the sofa. I looked at Lisa. Lisa looked at me. I looked at Emily. Emily grinned at me. Lisa and Emily were looking at each other. The wild sex was going to start any moment now...

Nothing was happening. We all seemed to know what we wanted, but nobody seemed to know how to go about making it happen. Last weekend's sexual adventures were a result of years of pent up sexual tension, anger and jealousy and passion. We had worked through all of those issues, it seemed. We all wanted to have sex again, but we needed a catalyst...

"Did Lisa tell you that we'd been texting?" Emily suddenly asked me.

I glanced at Lisa. She met my eye almost defiantly. "No," I said.

"It's been an... interesting conversation," Emily said. She was pulling her phone out of her slacks, and I felt a little rush of anxiety. She probably still had that picture I sent her of my cock on there. What if Lisa saw it? "Come see," Emily said, patting the spot beside her on the sofa. I warily stood up and moved beside her. Emily held up her phone so that I could see her conversation. I didn't have to look too hard to see there were photos attached. Dirty photos. Breasts and vaginas. The name at the top said 'Lisa.'

"You guys have been sexting each other?" I asked incredulously. I was starting to focus on individual things in front of me. I saw Emily's shaved pussy. In fact, she sent Lisa the exact same photo she had sent me on Tuesday. I had looked at it enough times to recognize it anywhere. I saw a picture of Lisa wearing the lingerie she had worn for me on Monday, a full mirror selfie. Then I saw a different pussy. With its hairy brown bush I knew it belonged to Lisa. I turned to Lisa, shocked. She stared back at me, smiling enigmatically. "You've been doing this behind my back?" I blurted out.

"Big deal," Lisa said, "You've been doing it too." I turned back to Emily. She had scrolled the phone and now there was a picture of a cock there. My cock. It was still her conversation with Lisa.

"You sent that picture to Lisa?" I almost shouted. Emily shrugged. I turned to Lisa again.

"You never send me pictures of your penis," Lisa pouted. It barely registered with me that she wasn't angry. She was mocking me.

I was so disoriented at that point I didn't know what to say. "But..." I started to say, and then thought better of what I was going to say. "You..." I started to say... "A week ago... you would've been angry... I don't understand!"

"It's okay Joe," Emily was saying beside me.

"Maybe it's not okay, okay?" I was still shouting. "All these years Lisa was this... this... demure little housewife... and then you come along and suddenly it's... threesomes... and lesbians... and sexting... I don't understand!"

"But it's what you wanted, isn't it?" It was Lisa talking.

"Yeah... but... you were never like this for me! Why during all these years didn't you ever want to try new things with me? I was so frustrated, and you didn't care! And now... and now... you'll do just about anything... and I'm just supposed to say lucky me and go with it... but you know... maybe I should stop and ask why... why now?" I looked at Lisa, and then I looked at Emily. Neither of them answered me. "Fuck this," I shouted, and then I stormed out of the living room and into the master bedroom, slamming the door behind me.

I stood in the bedroom, breathing heavily. I felt so angry at Lisa. Why did she resist my efforts all these years? She was a lesbian, I was sure of it. She was just going through the motions of her marriage with me. She was using me to get to Emily just as much as Emily was using Lisa to get to me. What would they call me, a cuckold? Yeah, that's what I was, a cuckold. We had a sham marriage and all this time Lisa had been waiting for her chance to bring a woman into bed with us. She was so clever; she made it seem like an accident. Like she didn't really want it, and she had to be talked into it, coerced.

A few minutes passed with me stewing in the bedroom, and then there was a knock on the door. "Joe?" It was Lisa.

"What do you want?" I snapped.

"Joe, come outside and let's talk about it," Lisa said.

"I don't want to!" I shouted, and I sounded like a brat, even to myself.

I heard the door handle jiggle, and then the door opened. I didn't lock it behind me. Emily entered, alone, although before she closed the door behind her I could see Lisa standing a few paces behind her in the hallway.

"Dude," Emily said.

"Dude," I mumbled.

"What's eating you?" Emily asked.

"I don't know," I mumbled, "It's just... you... and her... I mean... where was this woman all along? Why couldn't she have been like this all along?"

"Okay," Emily said, "Think about this. Would you have married Lisa if you knew she had a lesbian past?"

"Yeah!" I said. "I think so... if she had told me about it from the beginning and I knew that she was committed to me."

"Do you think that Lisa's cheating on you now?" Emily asked.

"No!" I said. I looked at Emily. "How can you call this cheating? We're all sleeping with each other."

"But you weren't expecting Lisa to want to do this," Emily said, and she paused. "Do you remember when we watched Wild Things?" She eventually asked.

"Yeah..." I said slowly. There was a threesome in that movie. Denise Richards. Neve Campbell. And... the guy.

"I remember you said that if you ever found yourself in a threesome you'd consider yourself the luckiest guy in the world," Emily said.

"Yeah," I said again, remembering my 18 year old self that watched that movie with Emily on her living room couch, trying to hide his erection from her. He wouldn't be questioning anything that resulted in him having sex with Emily, or Lisa for that matter, but especially not both of them together. "So..." I started to say.