My Best Friend Emily Ch. 06

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The three of us share tales from our sexual past.
10.7k words
4.3
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Part 6 of the 8 part series

Updated 06/07/2023
Created 10/07/2014
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Welcome to the next installment of this ongoing series. I've struggled for a bit over where to take this story next, and I think that the suggestion about flashbacks is the right way to go. As always, any similarities to anything you may have seen or heard before is a complete accident.

We ended up going out to dinner.

A few minutes after Emily's mock outburst she came back to the Jacuzzi. The three of us sat there quietly, soaking in the churning water and lost in our own thoughts.

Eventually Lisa broke the silence. "Okay, I'm really starving," Lisa said, and she rose out of the water, grabbing a nearby towel and drying herself off. Emily and I glanced at each other and followed her. We dried off and dressed and piled into my car to drive to the nearest Italian restaurant, situated in a strip mall on the main road a few blocks away. It wasn't raining anymore, but the air had the cool and humid feel that only comes after a spring storm.

All during the drive I kept glancing at Lisa, who was sitting beside me in the front seat. She was staring out the window. Our neighborhood was only partially built up, and whole blocks were either wooded areas or open fields. I could almost sense what Lisa was thinking. Was there any mud out there? Our flower bed was just a mound of topsoil. After a rain like that there must be a vast expanse of thick, cool mud in one or more of those fields. I knew that my wife was fantasizing about wallowing around in it. I thought about it too from time to time. I started to wonder if we would someday find ourselves wandering out of the privacy of our yard to indulge our muddy fantasies.

We got to the restaurant, which was really just a takeout place with some tables in the back. We plopped down at our usual table. The three of us had gone to eat there together often enough, but since we entered into our crazy threesome being together felt different. I looked at the cashier, the owner, the waitress, and the dudes flipping pizza in the air, wondering if somehow they noticed that there was anything different about us.

We ordered a couple of beers and scarfed down the bread. I got chicken parmesan, Lisa ordered a salad, and Emily ordered a pasta dish. Our food arrived quickly and we ate ravenously. When we were done we sat back in a well-fed stupor, trading knowing glances with one another.

Lisa eventually spoke. "So... what we did before..." Lisa said to Emily, choosing her words carefully as the waitress breezed by, "You've done things like that before?"

"Yeah," Emily replied, "But today was probably better than all of them put together. I don't think I've ever felt so completely fucked before." Unlike Lisa, Emily had no reservations about talking about sex at her normal speaking voice in the middle of a restaurant. I found myself glancing around nervously. Only two of the other tables were occupied, one by an older couple, and the other by a quartet of younger men and women, apparently on a double date. They were all engrossed in their own conversations and ignoring us. I looked into the front room and one of the guys behind the counter was staring in Emily's direction. I wondered how far her voice traveled.

"I was wondering about... those other experiences," Lisa said.

"Do you want to hear about them?" Emily asked.

I felt my head whip around to face Emily. She had never really told me anything about her sexual past. I was always curious about the wild sexual exploits she always hinted at but never came clean about.

"Yes, I think I would," Lisa said, "If you're willing to talk about them."

"Sure, I have nothing to be embarrassed about," Emily replied, "But we should probably pay the bill and go home first. I don't want everybody in the restaurant to get all horny."

One thing about my best friend was that she had no filter, and she enjoyed saying outrageous things to get a reaction out of strangers. Lisa blushed, and I found myself looking around the restaurant again. The older gentleman was looking right at me. I felt the blood drain from my face. He didn't look familiar, but it was a small town and he looked to be around our parents' age. There was always the possibility he knew my parents, or Emily's, or even Lisa's who lived only a few towns over. I was more worried about Lisa than anything. Her conservative Christian parents would lose their minds if they found out anything about what was really going on.

I held his gaze, not wanting to seem embarrassed or apologetic about Emily's outburst. I saw him shake his head slightly, and then he went back to his meal. I was about to snap at Emily, but luckily the waitress came by and dropped off the check. I paid it quickly, ignoring Emily's attempts to pay her share again, and we left.

"You really do have to watch what you say;" I scolded Emily on the ride home.

"Why? Who gives a fuck?" Emily said. I tried to remember how many beers she had. Two? Three? She got even less inhibited as she got drunk.

"That older guy sitting across from us heard you," I said, "What if he belongs to Lisa's parents' church? You don't know what a shit storm you could create if Lisa's parents find out."

"Find out? From what?" Emily asked. "Me talking about sex in a restaurant? They're going to deduce we're all fucking each other?"

"You met them a couple of times," Lisa said, "At our barbecues. You didn't notice how uptight they are?"

"I may have said hello and goodbye to them," Emily said, "I didn't hang out with them. Are they really that bad?"

"They would go crazy enough just hearing second or third hand that Lisa was talking about sex in a restaurant," I said.

"Wow, you poor repressed thing," Emily said, "No wonder you're all fucked up."

"I'm not all fucked up," Lisa huffed.

"It's okay," Emily said, "We'll take good care of you. Let doctor Emily fix you," she added, and burst into giggles.

I rolled my eyes. Drunk Emily could be a handful. I pulled into our driveway and we went inside. We settled in the living room and I put the Cards game on, but only as background noise.

"So..." Lisa said to Emily, "This wasn't your first threesome?"

"Nope," Emily said, and she giggled again.

"Would you... would you tell us about it?" Lisa asked.

"Sure," Emily said. "Let's see... the first one... I'll tell you about..." Emily was pausing for shock value, watching Lisa's face as she revealed that she had more than one threesome in her past. Lisa's eyes grew wide and Emily grinned at her. "Was when I was at NYU. I went to a bar one Saturday night. I was well, horny, and I went there looking for a hook-up. I saw this guy sitting there at the bar. He was soooo hot... tall... muscular... well-dressed. I got wet just looking at him," Emily giggled.

"The only problem was, well, he looked like he was in the process of picking up a girl already. And what a hottie she was... long blonde hair, perfect makeup, tits out to here," Emily stuck her hands out as far away from her as she could reach. I'm sure she was exaggerating. "I thought to myself, whatever's going on here, I want to be a part of it. So I sat down next to the guy and I said hey handsome. Well he whirls around to face me and he just smiles. Behind him I could see the girl checking me out. Like, who is this pushy bitch? I was in my little black dress with four inch heels and I hadn't cut my hair yet, so it was down to here," Emily said, gesturing halfway down her back.

"I bought him a drink, and we just sat there, barely saying a word to each other. Then the guy says wanna get out of here? And the girl says which one of us? So I said I think he means both of us. Well I figure the girl was either going to kill me or storm off, but she gave the guy a look and she just kind of shrugged and hopped off the barstool."

"Didn't they cover this on Big Bang Theory a couple of seasons ago?" I interjected. "Penny goes, if I pick up a guy at a bar, and he picks up a girl, does that mean I picked up the girl?"

Emily laughed, "Yeah, something like that," she said. "So we walk out of the bar, and he hails a taxi, and the three of us pile in, the guy in the middle, and he gives the cabbie an address uptown. Before the cab was even moving the two of them were making out. I just watched them for a while, but finally I was just like hey, what about me? So he turns and kisses me, and it was like, wow. I could smell his cologne and her perfume, and I could taste her lip gloss on him, so I broke the kiss with him and I said I want some of that lip gloss, so I reached across him and grabbed for the girl. And she just rolls..." Emily tries to clumsily reenact it, "so that she's straddling the guy in the taxi," and from there she kisses me, and well, it wasn't the first time I'd kissed a girl, but it was the first time I'd kissed like a random hookup like that. She was amazing. The softest lips..." Emily paused and smiled.

"So we're making out, she's grinding against the guy, and I'm grabbing one of her boobs. At one point I felt the cab swerve wildly. I think the cabbie was trying to watch us and the road. We're lucky we made it there in one piece. Finally we get where we're going, and I see the guy slip the cabbie a fifty and we all pile out. We're at this posh apartment building with a doorman and all that shit. I follow them in and he goes into the elevator and pushes the button for the penthouse, and I'm thinking who is this guy? Obviously he's loaded. The two of them are making out in the elevator. They're already starting to undress. He's trying to get her dress off and she's undoing his belt, and I was just standing there watching them. I don't think I've ever been that horny."

"The elevator door opens and we walk right into this huge loft suite, and it's like a fucking movie, like who the fuck can afford all this stuff? I mean, he had a giant HDTV on the wall, and this was 10 years ago, who had that then? Half the space was windows looking out on the city; the other half was covered in expensive artwork. Leather sofas, granite countertops, this place had it all. I don't know how long I stood there by the elevator with my mouth hanging open. The guy fucking claps his hands, like he has a fucking clapper, and everything comes to life. The stereo starts playing smooth jazz, the fireplace starts roaring, the lights come on low."

"I look at the girl and she's taking off her dress. She just shrugs and it falls off her shoulders, like she was keeping it on her with will power. She's wearing stockings and garters and this black lace bra and panty set, her tits were huge, and the heels, she looked like a fucking porn star. Maybe she was. She takes the guy by the hand and they go over to the leather sofa. She starts undoing his pants, and I'm still standing there. So I think, what the hell, and I took off my dress. I wasn't wearing a bra, just a pink lace thong underneath. My nipples were hard as rocks rubbing up against the dress! The girl pulled down the guy's pants and sits him down on the sofa, and his back is to me, so I start walking around so I can see."

Emily paused at that point, looking across the sofa at Lisa and me. "How do you like it so far?" She asked.

"Good story," I said.

"Yes, go on," Lisa said.

"Okay," Emily said, "Where was I... oh... so I get around the sofa, and the girl is pulling the guy's cock out, and it's huge, I mean..." Emily starts doing hand gestures, trying to demonstrate the size, "Don't get me wrong Joe, you have an amazing cock, but this thing was porn star caliber, and I'm thinking again that I walked into some kind of fucking porno shoot, and now I'm watching this girl suck on this foot long cock. And she's a pro at it. I hadn't given many blow jobs at the time, and the ones that I did give I didn't have the time to do right because we were always in some kind of hurry, or the guys blew their load in 15 seconds," Emily giggled, "But she knew what she was doing. I learned a lot about what I now know about blow jobs that night. Anyhow by now my clit is throbbing so I slid a hand inside my thong and started touching myself."

Emily paused again, looking back and forth between Lisa and me. "Is this doing anything for you?" She asked.

"Yes," I said. I was hard as a rock. I shifted in my recliner.

Lisa was staring at Emily. She nodded her head.

"Okay, good," Emily said, "So she's sucking on that cock and I'm getting off watching them. After a few minutes I make eye contact with the guy and he just sticks out a finger and crooks it like this," she pauses to make the gesture, "Like come here, so I come closer, and the girl stops her blow job to look at me, and she takes him in her hand and points his cock at me as if to say, okay, it's your turn. So I get on my knees and take the cock from her. And it's even bigger up close! I could hardly get my hand around it. I put it in my mouth and I start sucking on it. I couldn't get much of it in my mouth, and the girl starts giving me pointers, like how to open my mouth and get my teeth out of the way, and how to relax my throat so I could take more of him without gagging, really teaching me how to give a good blow job."

"We were passing him back and forth, and the guy was just standing there. Every once in a while he would just grunt. I remember thinking any other guy would've cum by now, two hot chicks sucking on his cock. Eventually the girl says 'you massage his balls like this' and she shows me, and while I'm doing that she deep throats him, and I mean she swallows the whole fucking thing, and he just loses it. Ooh, ahh, oh baby, he starts moaning, and starts fucking her face. He must have shot a huge load because it was dribbling down her lips."

"When he's done she kisses me, and we start swapping his cum back and forth. It must have gone on for a few minutes. Eventually the guy puts a hand on my shoulder, and I look up, and he's holding two glasses of wine, one for each of us to wash out our mouths. So we all sit down on the couch and we're drinking the wine, and the guy says 'why don't you two get better acquainted while I recover?' So I look over at the girl and she smiles at me, and she stands up and takes my hand, and leads me over to the fireplace."

"There's this big white shag rug in front of the fireplace. She stops to take off her heels so I do too and I realize we're the same height in our bare feet. She grabs me and kisses me and I reach behind her to undo her bra, and I pull it off and her tits are huge! Did I say that already? I knew they were fake from when I felt her up before but they were perfect, E cups, maybe bigger, with these big pale nipples. I tell her I want to suck on them and she goes over and lies down on the rug, and I kneel down beside her and start playing with them with my hands and kissing them."

Emily paused to shift in her seat, crossing her legs. "So I'm sucking on her tits, and I feel her hand slide down to my crotch, and she starts fingering me over my thong, so I slide my hand down into her black lace panties, and I feel she's completely shaved. It's the first time I'd seen that too," Emily said with a wink. "So we do that for a while, and we both start moaning and gasping. Eventually the girl moans 'take this off' meaning my thong, so I stop what I'm doing and pull my thong off, and she pulls her panties off, and she grabs me and pulls me down to the rug beside her, and she leans over and starts sucking my tits."

"I'm so turned on by now, everything is tingling, and I'm moaning, and I don't want to touch myself because I'll cum right there. She kisses her way down my body until she reaches my pussy, and she gives my clit one lick, just one long lick, and I cum. I'm screaming and thrashing on the rug, and she just looks at me and smiles, and swings her one leg over me and now we're in a sixty-nine."

Emily paused again, and I glanced at Lisa. She was fidgeting, like she didn't know what to do with her hands. "Let me guess," I cut in, "Your first lesbian sixty-nine?"

"Actually, no," Emily said, "Not really. My first one was... well... I can't tell you when or with whom because I was sworn to secrecy." Emily grinned at me, and I was left wondering who she had a lesbian experience with. "So anyway, we're sixty-nining, and I've got this pussy in my face, and I'm trying to make her cum. I'm licking her clit and fingering her pussy, and she mumbles 'stick a finger in my ass' so I slide a finger on my other hand in up to the knuckle. She starts moaning and shaking, and she lets out this squeal and cums, and I was thinking yeah, I just made this world class hottie cum. She recovers and attacks my pussy again, and I'm still working hers."

"All of a sudden there's the shadow over me. I'd completely forgotten the guy was there. He's standing over us, and he's fully hard again. He gets down on his knees over me and grabs the girl's hips, and I just get out of the way and he plunges that cock right into her pussy. Now I'm basically lying underneath them while he takes her doggie-style. The girl is still playing with my pussy while he fucks her and I'm still playing with her clit. He's only getting maybe nine inches into her and she's grunting with every thrust, like ugh, ugh, ugh. After a couple of minutes he pulls it out of her and points it at my mouth, and I take my cue and start sucking on it the best I can."

"After a few seconds he takes it and puts it back into her, and well, they just go at it. I mean, fifteen minutes, half an hour, I completely lost track of time. He's pounding into her, and every few minutes she cums, and I start to wonder how either of them have the stamina for this. I mean, I was just lying under them and the girl was playing with me the whole time, and I had maybe two orgasms, and after a while I felt like I could just go to sleep! Finally the guy starts grunting and he pulls out of her and starts jerking off all over her back and ass."

Emily pauses to demonstrate, grabbing an imaginary cock and jerking it and grunting and laughing. "So the guy gets up and walks away, and the girl pulls herself up and off of me, and leaves me lying there. After a minute I get up and the girl had cleaned up and is getting dressed, and the guy's getting dressed, and I'm thinking wait, we're done? I didn't want to say anything and sound naïve so I put my thong back on and walk over to where my dress was and put it back on. The girl comes over and gives me a kiss and says 'thank you.' And I was just speechless. Then the guy comes over and hands me a $100 bill and says 'this is to make sure you get home safe.' And I'm just like whoa, just like that? And I don't even get a chance to try out that cock? And the guy, he just looks me up and down, and says, 'honey, you've gotta start small. This thing would break you in two.'"

"And I'm about to protest, but he takes me by the shoulder and walks me to the elevator, and that was it. I got a cab home with plenty left over, but I felt cheap, and cheated. I could've handled that cock, you know. I kept going back to that same bar for weeks after looking for them but I never saw them again. I never saw another cock that big again," Emily said. She had a faraway look in her eye, like to this day she still wondered what it would've been like. "It took me a while to realize that they were a couple, and that they went out together to find people like me to bring home with them. Anyway, that was the best threesome I ever had... before us," she added. "Did you like the story?"

"Yes," I said. I looked over at Lisa. She was still just staring at Emily. "I can't believe you would do something like that," she finally said, "Just go off with two complete strangers like that. Anything could've happened."

"Well, when you're 19, you really don't think about things like that," Emily said. "I always used to think that when I was older, like 30," she added with a giggle, "I'll have all these great experiences to reminisce about, you know, when I'm too old to do anything. I know I put myself in some dangerous situations, and believe me, that wasn't even the worst by a long shot, but I got through it okay." Emily took a deep breath, looking from me to Lisa and back to me. "Okay, so who's next?" She asked. "Joe?"