Jackie Was Right

Story Info
Diana still has a lot to learn from former boss - FFM.
7.1k words
4.29
8.6k
16
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jackie and Diana were switching it up tonight. Usually they would have gone to their favorite bar for Friday night happy hour, but both had experienced a particularly stressful week, the kind of week that made wading through crowds of drunken college students seem intolerable. Instead, they grabbed a few bottles of wine from the store, deciding to unwind at Diana's place. They would be commandeering the living room tonight, while Diana's boyfriend, Mark, was banished to watch the rest of his game upstairs.

They were quickly finishing off their first bottle of red wine, both women were more drunk than usual, when Jackie pouted at her feet.

"I need to get these girls done for Devon soon," she said, faintly slurring.

Devon was Jackie's husband. That she would have to get a pedicure for her husband's benefit piqued Diana's interest and she asked why. Jackie plainly explained that her husband was sexually attracted to her feet.

"He is not," Diana said incredulously.

"He is!" Jackie replied, cackling with laughter, "Or, we are. He likes it and honestly, girl, so do I."

They had met five years ago when Diana started her first job out of college with Jackie's marketing group. Jackie was Diana's boss and led a network of teams that handled the bulk of the group's clients. She was a successful, capable, and confident black woman in a director's position at a major marketing firm--Diana found her utterly inspiring.

Jackie's leadership style was demanding and concise. She used few pleasantries, more willing to dish out critiques than compliments, and never sugarcoated her opinions of Diana's work. Diana worked tirelessly to contribute meaningful work to the team and gain Jackie's approval. Though rarely given, Diana coveted any praise she could get from Jackie. It eased her insecurity from Jackie's scrutiny and reinforced that she was adept at her job. Diana would come to respect Jackie's methods and was proud to have her as a mentor.

Within a year of working for the firm, Diana was promoted into another department at Jackie's recommendation, and within another year, she left the company entirely. They had remained in contact and grew even closer after she left. It started with the occasional coffee date to catch up. That naturally evolved to include regular texts and calls until they were eventually grabbing drinks together every Friday. In time, Jackie's workplace coolness melted into personable kindness, overflowing with humor and fun. She was an entirely different person outside the office and Diana loved it. They had become friends. True friends.

"Oh god," Diana continued, "so like, an actual foot fetish? What is it about feet that could possibly be sexy?"

"Everything I guess. They can be sexy. Or my feet are anyway" Jackie chuckled, "He sucks on my toes sometimes when we have sex. It tickles, but in a good way. It's more like... a mood enhancer than a pleasure spot. It gets me there."

"Well, I think they're gross," Diana said, unable to stop laughing at the thought of Devon sucking Jackie's feet.

They had never discussed sex this openly before. So far they would only allude to sex or acknowledge when they had it. This level of frankness was new territory in their friendship.

"Oh, you'd be surprised. I bet you'd change your mind if you tried it. Hell, I bet Mark likes feet too."

Diana hadn't considered this before. "Do you think?"

"I think most men do a little bit."

"Really?"

"Sure, a few of the guys I've slept with like them. It's made me feel sexy about my own. I didn't think much of them when I first started seeing Devon, but I like them now."

Jackie said this while flexing her bare foot over the coffee table. Diana had never appreciated feet before. Looking at Jackie's, she could see how they were a little attractive. Her feet were certainly cute. They were blemish free and smooth. The nails were professionally painted a vibrant pink which contrasted beautifully against her dark skin. Her toes were adorably bubbly. Diana was imagining men plucking at them like grapes from a vine when she had realized something.

"Wait," She said, her voice a mixture of laughter and curiosity, "Other guys.. You mean you've had sex with multiple men that like feet? You said you didn't appreciate your feet until Devon. So you were just putting up with a bunch of foot pervs until Devon came along?"

"Diana, you are way too curious for your own good," Jackie replied, now laughing herself and shaking her head. Then she gave a sly smile of faux-guilt, "But I didn't say I met them before Devon."

Diana stopped laughing. She was stunned by Jackie's response. Was her friend and mentor confessing to cheating on her husband? The thought of it made her stomach turn, but there was another unexpected fleeting sensation--a brief pulse in her pussy. Was that weird?

"Oh, Jackie, no," she said cautiously, "There are other guys? Does Devon know? Is this like cheating or are-"

"No, girl," Jackie smiled, "Nothing like that. Devon and I allow ourselves the freedom to... explore sex outside our relationship from time to time."

Diana was floored. This was further stunning information and it fascinated her. Her and Mark had previously broached this subject themselves. They had discussed having a threesome somewhere down the line. It was a relationship bucket list, though Caitlin was unsure if they would ever be able to follow through with it. She was worried she'd be painfully jealous if she had to watch Mark have sex with someone else. On the other hand, she was titillated with the prospect of finally having sex with a woman. Diana had always considered herself a little bi, but so far her bisexuality was limited to porn, drunkenly kissing girls, and her wildest fantasies.

Despite her reluctance, Diana wasn't a prude. Once, she had jerked off Mark in the back of a cab until he came in his pants. Sometimes when they went out, she would make out with a woman at the bar while Mark watched, then they'd talk about it at home while they fucked. She even had sex in the same bed as a girl friend after a night of partying in college. It was her friend's idea. They had remained with their respective partners and the two girls kissed while their boyfriends fucked them in the missionary position. The boys did their best to sync up, and both climaxed at the same time, firing their loads over the girls' bodies. It was the wildest thing she had ever done. She loved this last story in particular and would casually bring it up with trusted company to revel in their surprise.

People often assumed Diana was a normal innocent girl, sweet and a little shy, incapable of anything lascivious. Her appearance added to this perception. She dressed modestly, always opting for outfits that, more often than not, concealed her petite figure, even outside of work. Her breasts and ass were small and perky, cute, but she was far from being a voluptuous sex goddess. Altogether, she was beautiful, with pale skin, freckles, and a comely smile.

"How do you not get jealous?" She asked. "I mean I've had group sex next to another couple, but never with another person. I'm worried I'd get too jealous."

She wondered if this sounded stupid to Jackie, like the petty fears of a teenager. Jackie was in her mid-30's, roughly ten years older than Diana. This age difference always made Diana self-conscious of her lack of life experience. She tried not to remind Jackie of it whenever possible.

"Wow, Diana, you are bad! I never would have guessed!" Jackie said, giggling as she gently touched Diana's shoulder and took another sip of wine. "Well, jealousy is sort of the fun part. Really, sometimes it does make you jealous. Other times it's just hot and jealousy doesn't even cross your mind. It's freeing to experience someone wanting your partner and knowing someone else wants you. That you can want a man and take him, and well... it's not just men either."

"Stop. You're kidding."

"Hey, I've been known to dabble in the kitty from time to time, okay."

They both laughed. Diana almost couldn't believe it. Her friend and former boss was a sex freak. Her and her husband would fuck other people together, and not just that, she was apparently bi too. It was a lot to take in so suddenly.

The more Diana considered it though, the more it made sense. Jackie was fierce, charismatic, and had an amazing body. She wasn't thin like Diana, in fact, she was a little on the chubby side. The weight suited her. She had the figure of a woman who both exercised and embraced the pleasures of food and drink. She was buxom, with large breasts and an ass one could only get from good genetics and consistent gym time. It must have been hard to confine a woman like that into one sexual relationship.

It was amazing how a little information had drastically changed Diana's perception of her friend. Being bi-curious, she had developed a girl-crush on Jackie when she had first started at the firm, but her crush was innocent, stemming solely from an appreciation of her beauty and an admiration of her work ethic. Something about tonight was different though. This sexual insight into Jackie's life had inflamed a dormant fancy of Diane's. The innocent girl-crush had become sincere; now she was feeling shy around Jackie, aroused by her, maybe even desirous of her.

Diana suddenly noticed how low Jackie's top was compared to what she wore around the office. How much it accentuated her expansive cleavage protruding from her top. Her breasts were usually suppressed with office appropriate layers. Now they were free from the blazer and bouncing as she was doubled over with laughter. Diana had a sudden longing to see those breasts.

Jackie leaned her face closer to Diana's. "Diana," she said playfully, "are you staring at my tits?"

Diana froze in embarrassment and shifted her gaze to Jackie's eyes. She was surprised to see they had a new gleam in them. Her demeanor was also different, somehow heavier than usual. There was a stillness in the room now. A latent energy surged between them waiting to explode. They shattered the moment simultaneously as they both burst into laughter and sank to the floor.

They were lying side by side on the carpet together. Jackie reached out and held Diana's hand. Diana's heart started to beat faster and she felt dizzy. She didn't know if this was from her drunkenness or arousal. She realized she was the wettest she had been in a long time.

Unable to stop thinking about it, realizing this might be her only chance, Diana broached the subject again.

"You know what, I would consider doing that. Sleeping with other people. We want to have a threesome eventually, I'm just so shy. I don't think I could initiate something like that. I'm not like you."

"Shit, what do you mean, not like me?" Jackie cackled, "I do what I want. You could too. You seem interested. Just do it."

"No, shut up. I just mean you're so confident and cool and decisive about all this stuff. I've been with Mark for years, and we've talked about it. It just doesn't ever go anywhere. I think it makes us both nervous, so we just play with it as fantasy."

"Girl, you just gotta do it. Like leaping into the deep end. We started with a dating app. It was easy. Now we have couples we meet up with once in a while, or sometimes we'll hook up with people separately when we're traveling for work. There's even parties. Those get fucking wild."

"That's insane," Diana said, "See, I'd never have the courage to meet up with a total stranger for sex. I couldn't do it. I'd have to know them first."

Diana rolled on her side and tucked her head into Jackie's shoulder. She nuzzled her neck playfully as she smelled her hair. It smelled wonderful. They had never been this close before. Diana's pussy was lightly throbbing just thinking about it. The erotic implication was overwhelming. She could feel it and was almost positive Jackie could too.

She continued, "I wish there was a way Mark and I could do it safely. I feel so timid and stupid sometimes. I'm usually the submissive one during sex. I love when someone else is taking control. I don't know how I'm supposed to be sexy with strangers and I suck at being forward. The idea of going at it with such confidence.. it's intimidating. I wish someone was able to, I don't know, instruct me, or... mentor me somehow..." she broke off.

Diana was already staring at Jackie as she turned her head to look at her.

Jackie refused to play aloof.

"Diana, I think I would be too much for you. I don't think you'd want me testing your jealousy."

"Maybe, but I don't think so. I feel comfortable with you right now and this feels right. I understand though with Devon not being here--"

"Devon doesn't need to be here. I told you we play apart sometimes. You don't understand. Sexually, with women, I can be... a lot. Similar to how I am at work. Direct. Meaningful. I like to be in charge."

"That's perfect. Really, I think that would be perfect. I know you and how you can be. I handled it everyday for a year, I can do it again. I've never been with a woman before or had a full on orgy. I think I need someone to guide me so I don't feel like an idiot."

Diana was already feeling like an idiot. She asked herself why she was doing this. This felt so out of character for her. Why did she want it so badly?

"You should know, I can actually be worse than how I am at work. I can get a little.. mean," Jackie said seriously.

"That's okay," Diana said. She had a rough idea what Jackie was alluding to and it excited her. She now yearned for that assertive feminine energy.

She leaned her face toward Jackie's, eyes fixed on her full dark lips. Jackie reached over and held Diana's chin with her well-manicured hand, "Fuck it," she said with the trace of a smile, "Why not," and she kissed Diana deeply.

"Oh fuck," Diana panted, as Jackie brought herself on top of Diana's body, straddling her as they kissed. Jackie held her by her wrists as she darted her tongue into Diana's mouth, enveloping Diana's tongue with her own. Diana tried to fight Jackie's hold, eager to explore her body with her hands, but Jackie was too strong.

She had resigned herself to Jackie's lead when Jackie broke off the kiss. "Isn't this supposed to be a threesome?" She asked. "Go grab Mark."

Jackie's tone had shifted as she suggested it might. The build up was sensual and inviting. Now her direction to grab Mark had sounded similar to an order she would make at work.

"Okay," Diana said resignedly, regretful the kiss had ended so abruptly when she was so horny.

She returned a few moments later with a bewildered looking Mark in tow. He had been briefed on this outrageous development. He was shocked to say the least, but he didn't complain, and he was all for it.

"Why wouldn't he be?" Diana thought, "he was just told he's going to have a threesome."

They found Jackie sitting gracefully on the couch. Her white blouse was now unbuttoned, revealing her heavy breasts that bulged from the cups of her bra.

"Hi Mark," she said with a wave.

"Hi Jackie," Mark replied sheepishly, "Are we.. is this for real? Like, is this really happening?"

"Oh, it's really happening," Jackie said, the seduction back in her voice, "Our Diana insisted on it and I'm happy to oblige if you're okay with it too."

"Yeah," Mark said with a grin, "Yeah I'm completely okay with this."

"Good," Jackie said, returning the smile as she removed her blouse, "Let's get right to it then. Why don't you come here and unbutton your pants, Mark. Diana, kneel here next to me."

Her direction to Mark was lustful and sweet, while her direction to Diana, like before, was sterner. Diana had noticed, and it made her shrink slightly. It also heightened her arousal. "So" she thought, "she really is the same micromanaging bitch in bed as she is at work."

Diana walked to the couch to sit but Jackie stopped her.

"Not on the couch," she said, "I told you to kneel."

Diana, again caught off guard, obeyed, and knelt on the floor next to her while Mark approached with his belt unlatched and pants unbuttoned.

"Perfect," Jackie said, "Now let's see your boyfriend's cock. Take it out, Diana."

Diana laughed airily, "Well," she said to Mark, trying to cut some of the tension, "I guess we're really doing this, babe."

"Diana," Jackie interjected, "Moving forward, I don't think you need to speak unnecessarily. Let's save comments for when you're being addressed directly."

It was like Diana was an entry level employee all over again and Jackie was rebuking her for speaking out of turn in a meeting. Diana knew she should be embarrassed but a shiver of pleasure ran down her spine, tingling her pussy. She nodded and removed Mark's member from his pants.

"Ooo," Jackie said, her eyes staring fixedly on Mark's throbbing cock as Diana slowly stroked the length of his shaft. "Now that's a cock. Mark, I had no idea you had such a big dick. It's marvelous, honey. Diana, suck his dick."

Without hesitation Diana immediately swallowed Mark's cock. Jackie began holding the back of Diana's hair, forcing her to take Mark in deeper than she ordinarily would. Eager to please, excited to show Jackie how well she gave head, Diana took him down until she gagged. Mark groaned in pleasure.

Diana was overjoyed. This was exactly what she wanted. Someone to guide her through this process and dispel all the awkwardness she imagined came with a threesome. She always worked best with Jackie giving her direction and this didn't seem to be any different.

Diana continued to suck off Mark while Jackie reached around her, unbuttoning her blouse. She removed it entirely then unclasped her bra. She groped Diana's bare breasts from behind, her fingers running tenderly over the exposed nipples, hardening them.

"They're cute, but they're a little small," Jackie said appraisingly, as if she were reviewing one of Diana's work projects. The slight was erotic fuel for Diana. She moaned with Mark's cock deep in her throat.

"The funny thing about Diana, Mark," she continued, "is she works best with constructive criticism and clear direction, and today we're gonna utilize that for our own pleasure." She pinched Diana's nipples until she winced. Again, Diana's pussy throbbed.

"Excellent job, Di. You seem excited. I like that. And what about you, Mark, are you excited? You should be, because you, sir, have a decision to make... Who do you want to fuck first?"

"I mean, I'm okay either way," Mark said with a nervous laugh, "What does Diana want?"

Jackie answered before Diana could respond. "Diana wants to have fun," she said, "Isn't that right, Diana?"

There was too much stimuli for Diana to properly assess how she was feeling. It was true, she was aroused, but her first threesome wasn't happening as she thought it would. While exhilarating, Jackie's officiating had started to make her feel disconnected from Mark. It was as if the moment was truly for her and Jackie, and Mark was just there, an extension and tool of Jackie's power. Diana was flustered, conflicted, and incredibly turned on. Not knowing exactly how to answer, how to articulate these overwhelming feelings, thoughts, and sensations, Diana quietly nodded her head in affirmation.

"Good," Jackie said, "Okay then, Mark. We'll figure out the pecking order as we play. In the meantime," she brought Diana's face back to Mark's cock. "Suck him," she ordered, and Diana did.

She had only been blowing Mark for a few minutes when it finally happened. Jackie reached over and wrapped her hand around Mark's shaft, stroking it tenderly while Diana sucked the tip. She kissed Diana along the neck and cheek, then without warning, she pulled Mark's cock from Diana's mouth, smiled at her, and put it into her own. Diana knew that Jackie would inevitably have to touch Mark, it was a threesome after all. She just thought there would be something more to signify when that would happen, some semblance of ceremony for the changing of the guard--but there was none. Her friend had taken her man's cock from her mouth and put it in her own without permission or a second thought.