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Chapter 51
by
skedlee
What happens tonight
A perfect evening
You pace around your apartment nervously, checking and double checking to make sure that everything is in its right place for your impending encounter with Mary. Earlier, you got out and placed a bottle of red wine on the kitchen table, an 88 La Fleur that seemed to be the nicest vintage you had in stock, along with two glasses set aside and ready for use. Light jazz plays throughout the apartment and you hum along to it as you absentmindedly look into your bedroom to make sure the score of lit candles hasn't inadvertently started a fire.
You chose to dress in a form-fitting t-shirt that Carrie said, "hugs your chest and arms in all the right ways," a pair of black boxer-briefs, and a set of professional beige slacks. You weren't sure how dressed up you should get, as it wasn't like Mary and you were going out on a traditional first date that included dinner at a restaurant. You were staying in, so you had to balance dressing up to impress while maintaining a casual atmosphere, because to put it bluntly, she was coming over to your place for one reason: to have sex. Perhaps in hindsight you should have scheduled the date earlier and eaten dinner together as a prelude of sorts for the evening's festivities, but it was far too late now to change plans.
But the point was moot, you thought to yourself as you check yourself quickly in the bathroom mirror. You saw no ugly blemishes, and a quick sniff told you that you didn't smell badly. You exit your bathroom and thought about taking a swig of wine to calm your nerves when you hear a knock on door. You take a few deep breaths, and once your breathing steadies you head to the door and open it.
Mary stands at the entrance to your apartment, dressed cutely in a pair of tight jeans and a loose beige blouse that obscures all of her assets. You're glad that she's dressed similarly to you, and you're thankful that you didn't greet her at the door in nothing but your underwear and a robe, as a decadent part of you thought was a good idea a mere hour ago.
"Hey Mary," you greet casually. "Come on in." You the open the door as wide as it can go and usher her inside. As she passes you see that she's holding a medium-sized gym bag.
"Hello, John, " she returns the greeting. You close the door behind you and the second it latches closed, Mary drops her bag on the floor and brings you in a for a passionate kiss. It takes you by surprise, but it shouldn't, considering what the two of you are about to do. You bring your hands to her waist, as you're ready to get right down to business, but she pulls away, an apologetic blush on her face. "Sorry for that. But I'd be lying if I said I hadn't been constantly thinking of doing that the past few days."
"No apologies necessary for a kiss like that," you reply smoothly, as you lead Mary the short distance to the dining table. "Would you like to take a seat and have some wine?" You offer. She accepts, and you pour a half-glass of wine for each of you
You clink your glasses together and begin to sip, Mary smiling heavily as she does so, as if undecided whether to talk. You give her a quizzical look and she eventually asks, "Did you get my favorite bottle of wine on purpose? The 1988 La Fleur?"
"Well," you say slowly. "I could lie to you and say that I definitely did, but my mother always taught me to try to be honest whenever possible. The truth is that I wasn't a big drinker of wine before I met Carrie. This was the nicest red of the few bottles that she brought over. So no, I did not remember that this was your favorite bottle. I suppose that I did remember that you favor the reds," you finish with a grin. Mary chuckles in response.
As the two of you sit there, enjoying each other's presence, you mind starts to wonder, and you begin to wonder. Did Carrie give you the wine because it was Mary's favorite? She gave it to you almost a month ago; could she have foreseen this situation that you'd need it with Mary? It seemed unlikely, but you had long ago stopped doubting your girlfriend.
Seeing the quizzical look, Mary puts you out of your misery. "I mentioned off-hand to Carrie when we were in the ladies room that the 88 La Fleur was my favorite vintage and bottle. She must have remembered that conversation, and gotten you a bottle in case we ever had a double date again. What a lovely girlfriend you have on your hands. Be sure not to lose her."
"Yeah, she sure is something," you answer, but in your mind, something is not quite making sense for you. The fact that Carrie stashed a bottle of Mary's favorite wine at your apartment didn't make much sense, as if you had a double date, either the four of you would go out to a restaurant or stay in at Mary and James' house. How could Carrie have known that you'd need the bottle to impress Mary; was it possible that Carrie first began planting contingency plans for you seducing Mary that long ago? You decide not to pursue that thought any longer, as you want to focus all of your attention on your guest. "So," you begin, nodding at duffel bag on the floor. "What did you bring?"
"That," Mary answers, "is a surprise for me to wear for you, of the skimpy lingerie variety." You can't help but smile at the thought of Mary in a fancy underwear set. "I actually thought about wearing it when I arrived, underneath a trench coat of course. But I figured that you probably wouldn't want for your neighbors to think that you're cheating on Carrie."
"Unfortunately, I think most of them already know that Carrie and I are 'adventurous.' In fact, when I visited the neighbors across the hall for dinner, Victor and Chelsea, Chelsea flipped out at me, implying that our penchant for inviting other people into our bed was sinful and destined to end horribly."
"Woah."
"Neither of us really care though. Personally, I just think that she's a closed off prude, with no ounce of sexual creativity."
"That could be. Or, she might be cheating on her significant other, and is protesting a little too much."
"Huh," you answer. "I never really thought about it that way."
"Well, that's just my ladies intuition," Mary says as she drains her glass. You get up to pour her another glass but she waves you off as she picks up her bag. "Where's the bathroom?" she asks, and you stand up and point her in the right direction. As you do so, she sneaks in for another kiss, this one more tender and familiar. "Meet me in your room, while I get into something a little more comfortable and a lot more slutty, " Mary calls out as she walks away, swaying her ass like she did earlier today.
You get up and race to reseal the wine and put the glasses in the sink, and they'll be washed tomorrow when you don't have a beautiful woman waiting on you. You walk to your room, relighting one of the candles that went out while the two of you drank wine together. You try to decide whether or not you should change into something a little more comfortable yourself, and you decide to go with the silly thought you had earlier: your boxer briefs and a robe. You take off your slacks and shirt, and throw them in the laundry basket in your closet. You next put on the ankle-length grey robe that you got as a gift from your sister a couple of years ago. Taking a look at the small mirror in your room, you nod in approval at your reflection. You're rocking a very Hefner-esque vibe at the moment, which you suppose is apt because you're about to have sex with the fourth different woman in the past week.
You hear a light knock on the door and you turn around to see Mary make her entrance. Your eyes nearly drop out of your head at the vision of your gorgeous coworker in something more revealing than tight skirts and thin blouses, and while those certainly flattered her figure, they had nothing on what she was wearing at the moment. She's wearing a full set of lingerie, all in the same shade of red. Up top she's wearing a push-up bra that's working overtime to bring out the best in her medium-sized tits. Down below she has on a pair of Brazilian-cut panties, and you're dying to know how her ass looks from behind. The only other things she's wearing are a garter belt and a set of thigh-highs.
Mary walks up to you wordlessly while you're still too gobsmacked to speak. She places a hand on your chest and leans up to kiss you, which you gleefully reciprocate. While you bask in the wonderful glow that is first base, Mary undoes your robe and opens it up, revealing your bare chest. You shrug the garment off, and it falls to the floor mere minutes after you first put it on. She then guides to you to your bed, where she moves her hand to your shoulder and guides you to sit down, and you eagerly comply. Mary straddles your legs and sits down your lap, giving you a full and wonderful view of her chest. She quickly tilts your head up to resume your kiss, which momentarily ended as you sat down. As she does so, she grinds her hips onto your lap, which rapidly sends your half-chub into a full on erection that can't be contained by the slim fabric of your boxer briefs. Mary breaks off the kiss temporarily and grins at you as she feels your cock on her ass.
"Want to take this to the next level?" Mary whispers in your ear. You just nod in response, and she slides down your body to kneel in front of you, while you spread your legs to give her access to your crotch. Mary grabs the waistband of your underwear and pulls it down, and you raise your hips a couple inches to ease the process, and now, you're sitting naked on the edge of your bed while Mary looks in greedy wonder at your dick. Mary inches closer to you, so that her mouth is less than a foot away as she slowly grasps your cock. Like every woman you've been with, her fingers don't come particularly close to encircling your shaft entirely, and you smile in pleasure as Mary gives you a few experimental strokes. You groan verbally, wanting to let her know that you appreciate her delicate hands on your cock.
Not content with just giving you a handjob, Mary moves her mouth closer, close enough for you to feel her breath on your tip. She gives you a devilish grin, her green eyes gleaming in mischief as she opens her mouth and takes your penis head and an inch of your shaft and starts sucking, beginning your blowjob. You pool Mary's hair in a fist to keep it out of her face and rest your hand on her head, though you let her dictate the pace she wants to go.
After a minute, Mary pulls off, slobber around her mouth as she does so. She pauses a moment before going back down, so, the concerned gentleman that you are, you ask her, "Are you okay?"
"Oh yeah," Mary replies immediately to assuage your concerns. "Just...how do I say this in a way that won't inflate your ego to an unbearably high level...Your cock is a little harder to deal with than I'm used to."
"Because it's bigger?" you say, the smile on your face unmistakably smug at the moment.
Mary rolls her eyes before responding, "Yes, you are both longer and thicker than I've ever had. Unfortunately for you, I can only stroke one thing at a time, your dick or your ego. Which would you prefer?"
"My dick," you mumble, properly chastised for your gloating. "Don't worry, though. As frustrating it is to suck my dick with my mouth, it pays off ten-fold when you take my dick at the other end." You pause then clarify, "Your pussy, not your ass. Anal is great and all, but it takes a certain level of preparation that I'm too impatient for tonight."
Mary gives you a muffled hum in agreement and continues her blow job, and you lean back and bask in ecstasy under the direction of her expert tongue. This continues for a couple minutes before her fellatio proficiency starts to bring you to the precipice of ejaculating, so you gently pull her off you. The look of disappointment in her eyes is almost enough for you let go of her so she can get back to pleasuring on your cock.
But tonight is about getting Mary addicted to you, sexually at least. And since you don't have Carrie, the world's best wingwoman, you have to be laser-focused on your performance tonight. And, at least in your experience, the best way to impress a woman sexually was to ensure that she came before you did.
Which meant that the oral pleasure you received needed to become mutual.
"Up on the bed," you order, coming out with a bit more steel than you had initially intended. Mary raises at eyebrow at your tone, but before you can say anything she bolts onto the bed, and you get the impression that she's definitely willing to play along with just about anything you want to do tonight.
Once Mary is on the bed lying on her back, you go immediately for her panties and she takes off her bra as she does so, leaving her clad only in the garter belt and thigh-highs, which you are fine with staying on at the moment, as they accentuate her nudity. You slide up the bed so that your face is next to Mary's and resume your kissing from earlier. As you do so, you slip a hand down to her nether regions, where you carefully insert a finger into her cunt, and it slides in easily. Pleased that Mary is so aroused, you add another finger and saw them in and out, while stimulating her clit with your thumb for added pleasure. Mary moans into your mouth, and reciprocates by taking your cock into her hands, stroking up and down in rhythm of the light music that still plays throughout your apartment.
Once you're sure that Mary is properly wet for you, you disengage from the kiss, intent on moving down to perform cunninglingus. Mary, however, stops you with a hand to your chest, and decides to straddle your face, lowering her pussy to your mouth where you can eat her out, while she lays down on your body, and thankfully she can reach your cock with her mouth.
The two of you sixty-nine for several minutes, and you've been grabbing onto the firm globes of Mary's ass for the vast majority of the time. She, in turn, was massaging your balls with one of her hands, trying to coax the cum out of you. For the past minute you've been on the edge of cumming, and you're holding back with all you've got, because you sense that Mary herself is very close as well.
Eventually, Mary can't help but succumb to your ministrations and as you feel her shudder in the pleasure of her first orgasm of the night. The pure act of getting Mary off, combined with her expert cock-sucking skills herself, cause you to unload yourself, and Mary swallows down your load, milking you through your orgasm..
Mary rolls off you and lies down on her back next to you with her head still near your crotch. You life your upper body up off the mattress and smile slightly as your gaze roams over Mary's mostly nude body. You cup a hand on the inside of Mary's thigh, tracing the edge of her thigh-highs and decide that you like it, and note to yourself to mention it to Carrie, because you know that she'll wear them more often if you mention it.
You snake your hand up to Mary's pussy to continue stimulating her, but she slaps away your hand. Your hand retreats at the rejection and you settle on caressing her calf.
"Not quite yet," she says in a breathless voice. "I get super sensitive immediately after cumming." She turns to look towards you, but your erect cock is at the forefront of her vision, having not softened it the slightest since your recent orgasm. She gulps at the sight, and takes her left hand and begins stroking you, a casual pace that would never make you cum but excels superbly at keeping you hard and raring to go.
"Impressive, though," Mary says out of nowhere after a couple of minutes of silence. "Staying hard immediately after cumming. Not all guys can do that. Carrie's a lucky gal."
"Hmm," you ponder, thoughtfully. "I've always had a bit of a high libido, so I've definitely done it before. Though recently, it feels like it's been happening a lot more often." you say with a shrug.
"It could be a situation where you're benefiting from the Coolidge effect," Mary suggests.
"Like the president? What's that?" you ask.
"It's a biological phenomenom, where if a male gets a new female partner, their sexual interest is raised and they can continue sexual intercourse even if they were tired out before."
"That could be possible," you said slowly. Was this something that Carrie knew about? You'd have to ask her when you next talked to her.
"All right, I'm ready for you again. Let's fuck," Mary says without preamble, as she releases your cock and shifts into a sitting position.
"Any requests?" you ask, a smile on your face. Mary looks like she's about to speak, and even opens her mouth, but she closes it and shakes her head.
"Nah. Give me the vintage John Doe experience."
You stay silent a place a hand on Mary's cheek. "Are you sure. You don't have to hide anything from me, at least sexually."
Mary's gaze lowers as she's unable to meet your eyes. You remain insistent, not backing off. A gut feeling's telling you that this is of utmost importance.
"Maybe," Mary says quietly, so quietly that you can barely hear her over the soft music playing in your apartment. "If you don't mind, would you be...a little rough with me?"
"Rough with you? How so?" you ask, wanting to make sure you knew exactly what she wanted.
"You know..." Mary pauses, the blush on her face now unmistakable. "Like spanking me. Hard. Hard enough that tomorrow at work I'm wincing every time I sit down. Or **** me, causing a bruise that lasts for several days, and I'm reminded of our night together whenever I see myself in a mirror. Things like that."
"Sounds hot," you state, making sure that Mary doesn't get the impression that you're kinkshaming her. You try to think back of your previous experience with rougher sex. It happened with Carrie, of course, and you certainly liked it, though to be honest, you liked every manner of sexual encounter with Carrie. So you did have a little bit experience with this particular fetish. "We should probably have a safe word, just in case. Got any ideas?"
"Pancakes," Mary says quickly. She realizes that she said it a little too quickly, so you take a moment to tease her, just a little bit.
"Thought about this before, have you?" The blush suffuses her cheeks fully, matching the little bit of crimson lingerie that she still has on.
"I've always wanted to try it before," Mary speaks contemplatively. "And I figured that if I'm having sex for one time with my handsome coworker and close friend, then this is my one opportunity to do it.
You definitely hope that this encounter won't be your only one with Mary, which means that you're going have to be rough with your friend, not that you mind in the slightest.
"Wait," you say, realizing something. "If you wanted me to be rough, does that mean that you didn't really want me to stop stimulating you after you came, even though you were sensitive?" Mary shakes her head demurely, and you let your anger flare up and demonstrate it to your partner. You grab Mary and flip her over on her stomach, getting off your bed and positioning yourself beside it so that you're right behind Mary. Mary gasps at the sudden surge of action from you, but you're not done. You grab her covered legs and pull her off the bed so that her pelvis is at the edge of your bed and her feet can rest on the ground.
"You know what that means? It means you wasted five minutes of our time, when I could have been fucking you immediately, rather than waiting for you to cool down. And that misstep, my dear Mary, deserves a consequence." Mary nods meekly at your hard words, and you put your left knee up on the bed and place your left hand on the small of her back, pinning her down and preventing her from escaping if she wanted to. You wind your free hand back and slam it down on her unprotected lightly tanned ass.
*SMACK*
Mary makes a sound that's half a gasp and half of a moan, and pause for a moment as you stretch your hand, as the impact caused you to wince for a moment, and you're glad that Mary can't see your discomfort.
*SMACK*
You bring your hand down again, this time on the other cheek, to balance out of the pain that Mary feels. Plus, it would look weird if only one half of her bottom was tinted red. This time you don't wait long before subsequent hits, as you trust that if Mary needs to use her safe word, she will.
*SMACK*
*SMACK*
*SMACK*
Three spankings in straight succession results in a series of longing moans from Mary, and requires you to take a break, for your hands sake. You slide your hand between her legs to check her pussy, and it is absolutely sodden, even more than it was earlier.
"Wow," you taunt, as you continue to slide your fingers in and out of her pussy. "You weren't kidding. You love this." You pause to wait for a response, but when one doesn't come you remove your hand, and that causes to Mary to reply instantly.
"Yes, I love it," Mary admits as she buries her face into the mattress.
"Thank you for admitting that," you state as you reposition yourself behind the beautiful brunette. "And going by soaked you were, it's long past time to fuck you." You move Mary's legs further apart and hold your cock and slowly rub your cockhead up and down her lips, teasing the entrance to her pussy. Seeing no reason to deny either of you pleasure any longer, you slowly sink in, entering your once platonic friend.
An inadvertent groan escapes your lips as you plunge into Mary's depths. She's wet enough that you encounter no resistance in bottoming out, even though her pussy grips your cock in an extremely delightful manner. You're certainly glad that you blew a load into Mary's mouth earlier, otherwise, you might cum too quickly. Now, though, you're ready to fuck her for a long time.
Mary utters a moan as you entered her, punctuated by a yelp when you give her a light smack on her ass.
*SMACK*
"Now, let's get this swinging session really started," you inform your coworker, as you grab a fistful of her hair with your right hand and pull towards you, arching Mary's back and lifting her upper body off the bed. Feeling no need to deny yourself, you palm one of Mary's tits in your free hand, groping her hard. Mary gives off a gasp, tinged with delight and you know that you've struck gold.
You begin to pump in and out of Mary, slowly ramping up in pace. Before you hit maximum speed, however, Mary interrupts you.
"Oh FUCK yes!" Mary screams out loudly, as her twitching pussy informs you of the telltale sign of an orgasm. You're a bit shocked, as it took a less than a minute for Mary to cum, and even Carrie took longer to orgasm than that, and your girlfriend was always turned on when you had sex. And you didn't even stimulate her clit in the process, it was just pure fucking. You don't slow down, but neither do you increase your pace as you were originally going to do, fucking Mary with deep, long strokes.
"Wow," you say, making conversation with your sexual partner. "You were really on a hair trigger. How much did you need that orgasm?" you ask. When Mary doesn't respond, you give her a quick swat on the ass, which compels her to answer you.
"More than you know," Mary panted out. Since Mary had just orgasmed recently, you decide to switch positions, withdrawing your cock from her pussy. Mary mewls at the sudden loss of your dick, but she stops when you flip her over and go in for a long, adoring kiss. Eventually, you can't help but miss her pussy, so you end the kiss to focus on fucking Mary again. Before you fully pull back, you feel a wave of possessiveness, and you want to mark Mary. You lean down to her neck and bite, sucking a little bit and applying enough pressure that you know will leave a hickey on her neck, for all the world to see. You know that people will assume that her husband James gave it to her, but you'd know the truth. James would know the truth. And most importantly, Mary would know the truth. For the next week, every time she looked into a mirror and caught glimpse of the slight bruise, or whenever she was talking to somebody and their eyes would flicker down to her neck, she'd know who gave it to her, and be reminded of the time that she got fucked better than she ever had before. Even if she covered up and wore a turtleneck exclusively until the hickey faded away, someone would surely notice her atypical choice of attire with the spring weather only growing warmer.
You withdraw your face from Mary's upper body and move yourself into a modified missionary position, with Mary showing off her flexibility with her left leg all the way up on your right shoulder. Her other leg curls around you, hugging you from the back. You position your cock on top of her mons, and the two of you look at how your dick looks menacing and stands out on the lower part of her torso.
"Please, John. Fuck me more," Mary pleads with you, and as you fix your eyes on her you see that hers are hooded with lust. Never one to purposely disappoint a beautiful woman, you shift back so that you can insert your cock once more in Mary's taut pussy. You slide in forcefully, and Mary's drenched cunt easily accommodates your entrance, and you sigh in contentment at being back in Mary.
"Did you like marking me, John?" Mary asks once you bottom out inside her. Apparently, you were not nearly as subtle as you thought when you gave her the hickey.
"Yes," you croak.
"I liked it too," she confesses through several moans, and you're fairly certain that your current position stimulates her g-spot nicely.
"Good," you state confidently, fucking Mary harder and harder, and rattling your bed frame, causing it to bang up against the wall loudly. Thankfully, the wall your bed leans up against is an exterior wall. Otherwise, the complaints about the noises that you and Carrie made would be threefold, and you might have been evicted by now. "The mark will serve as a reminder for you as well. Once it fades, it means that it's been at least a week since you've been fucked properly, and high time for you to come visit me again. Will you do that?"
"Of course John! If you want it, I'll give it to you."
"It's not about what I want," you reply. "It's about what you need."
"Yes, you're right," Mary cries out. "I need it."
"Though to be perfectly honest, for a slut like you that needs to be fucked roughly, once a week isn't nearly enough. You need to be fucked well every day, or at the very least, every other day. Would you like that?"
"Fuck yes!" Mary screams out.
"After all," you continue. "If we want to keep your nice, lightly tanned cheeks their current, beautiful pinkish hue, then regular, daily, spankings will definitely be necessary."
"Yes! I need to be spanked." You didn't think that Mary actually wanted that, as the lack of comfort from having her ass hit daily to the point of being reddened combined with the fact that her job included sitting down for large portions of the day, but that wasn't the point. The point was, Mary was so turned on at the moment that she would find just about anything you said to be immensely arousing. Knowing this piece of information, you try to push the envelope a little bit.
"Fortunately for you, I'll be around to take care of all this for you. Especially since your husband can't do this for you."
"What? No," Mary denies, but her words sound hollow when they're interspersed with pleasurable moans.
"I'm sorry, Mary. But it's true. There's a reason why you never told him that you wanted to be handled roughly in bed. Because, in your heart of hearts, you knew that he would disappoint you with his lackluster sexual proficiency and ruin your fantasies before they had a chance to come true." You feel a little bad for saying these things about James, who unlike Chet and Ted, was a stand-up guy. You do take solace in the fact that he won't find out about these things you're saying about him, and it'll be a secret between you and Mary.
"But.." Mary says futilely.
"But you won't have to live with being denied anymore, dear Mary," you interject with a vow. "You will have the best of both worlds now. A romantic, white picket fence love with your husband. And with a quick text, you can contact me and have all the filthy and depraved sex you desire."
"All I desire?" Mary says slowly, tempted by your proposition.
"Certainly. Anything you want. Even things that you haven't admitted to yourself. We'll begin a sexual odyssey together, " you enthuse, "like the one that Carrie and I embarked on with each other. And trust me, I can't wait for Carrie to get into bed with us."
Mary begins to ramp up her moans and you smile the fact that Mary is certainly aroused by the idea of Carrie sharing a bed with you. You can't wait for your traditional threesome with Mary and Carrie, as your previous two threesomes were exquisite experiences.
The downside of this dirty talk with Mary was that it aroused you too, and you felt the beginnings of an orgasm approach you. Being a huge fan of simultaneous orgasms, you decide to go into overdrive to stimulate Mary to get her biggest cum of the night.
You release your hand from holding onto Mary's stocking-clad leg and move it to her breast, while your other hand goes to her pussy to attack her clit. The new burst of stimulation shocks her, and soon Mary is like you, on the precipice of exploding.
"Cum with me Mary," you order, looking to Mary's eyes. She meets yours and a few seconds later you explode inside her, and that triggers her as well. She clenches around your dick, milking all of your semen inside her. Your orgasm is so powerful that you almost collapse on top of your cubicle mate, but you use your last bit of strength to pull out and lie face down next to her. You do have the foresight to turn your face towards her so you can look upon her beauty.
"That... was honestly incredible. Better than I could have ever imagined," Mary gushes, and you give her a smile while you study her beauty. Right now, post orgasm, a faint sheen of sweat covers her body, making her look like a sex goddess. Or rather, more than she usually does.
"You're welcome," you reply, before giving Mary a wry smile to let her know that you're joking. Mary still gives you a mock pout while she slowly repositions herself in a normal sleeping position, with her head on your pillows. You drag yourself up next to her to share her company for just a little bit longer, because you assume that fairly soon she's going to take a shower and return home to her husband.
Over the next few minutes, the two of you enjoy the silence together. Eventually, Mary breaks it by saying, "As an aside, the reason I didn't tell James about my rough kink was I genuinely though he'd think less of me because of it, not that he couldn't do it properly."
"Yeah, I figure," you reply. A part of you doubts Mary, but that might just be Carrie' influence on you. Ever since she told you that the idea of keeping sexual secrets from your partner to be inane, you've felt that doing so was a red flag. Or at the very least, a yellow flag. "Anyways, I didn't mean to be so rude about your husband, and I'm sure he satisfies you adequately." You see Mary nod along to you absentmindedly. "Because I like James," you continue, "Especially compared to the husbands of Carrie and my previous two threesome partners, who I don't like at all."
"Wait," Mary says, whipping her head over to you. "Your previous threesomes were with married women?" You swear to yourself; you completely forgot that you hadn't revealed many details about your threesomes to your coworker because you didn't want her to know you were targeting married women.
"Yep," you confirm, slightly fearful for Mary's reaction.
"Anyone I know?"
"Uhh," you say, pausing for a moment. That wasn't what you expected her to say, but you decide to answer her honestly. "It was Carrie's best friend, Natalie. And the other one was Helen."
"Wait, Helen? Like, Ted's Helen?"
"Ted's Helen," you validate.
"How'd you manage to pull that off?" Mary asks in wonder. Again, not the reaction you were expecting, but you remember that Mary once referred to Helen as a 'stuck-up trophy bitch who deserved Ted.'
"I told him I'd tank his performance bonus if he didn't send Helen over to sleep with Carrie and me," you recall, smiling as you do so.
"Damn," Mary muses, mostly to herself. "That's fucking hot."
"Yes it was," you say. The talk of your previous conquests, and more specifically, the memories of those sexual encounters, arouses you. Lying on your stomach with a burgeoning erection feels uncomfortable, so you flip over on your back, with your hard cock, bobbing in the air.
"Are you kidding me?" Mary exclaims when she sees your dick. "You're still hard. I haven't managed to drain you yet?"
"What? You were the one to cause this. Making me talk about my past conquests like that. That would drive any man into a lustful state."
"Uh huh. Let me guess, for your next threesome, you going to brag out me in the same way to get up for round three."
"Well, hopefully my next threesome with Carrie will be with you," you say with a wink. Mary responds by rolling her eyes, but she does blush as well. "After that? Probably. You certainly seemed impressed," you add on, which earns you a second eye roll.
Mary scoots towards you and takes your erection into her closest hand, her right, and begins to pump you up and down, guaranteeing that you won't go soft anytime soon. "Just for the record, I'm doing this because I pity poor Carrie. To have to deal with your stupidly high libido all the time while getting fucked to multiple orgasms every night? I pity her pussy."
"Suuuuure you do," you say sarcastically.
"I'm serious," She claims, but the incorrigible smile on her face denies said claim. "My pussy is worn out from just one of your orgasms. All you're getting the rest of the night is a handjob, maybe a blowjob if I'm feeling generous."
"Really?" you ask as you reposition your left arm, curling it around her body and grasping her neck in your left hand. Mary gasps as you do so, but she doesn't pull back or try to escape your grasp in the slightest. "And what if I decide to just...take you. As I want to. I haven't heard our safe word yet."
"Correct, you haven't." You can't see Mary's expression from your current angle, but you know that she's glad you caught on.
"Ride me this time. I can't be expected to be on top all of the time. You need to earn your keep," you order as your release her neck. Mary scrambles up on top of you, straddling the upper portion of your thighs, as she continues to slowly tease your cock. You give Mary a wry grin, though in this temporary downtime, you can't help but think about your darling girlfriend, who is occupying James at this very moment. To be honest, the moment you saw Mary, you totally forgot about the plan to shut off her phone to prevent it from receiving phone calls. Mary's phone hadn't gone off during the sexual session to your knowledge, though to be honest, the two of you wouldn't be able to hear it anyway, with Mary's bag and purse in the main part of your apartment. You wonder just how Carrie managed to pull it off. You're sure that it will be an interesting story. Her stories always are.
A/N: Sorry for the delay with this chapter, I wanted it out by Christmas but it kept getting longer and longer, ending up as my longest chapter at well over 6,000 words. Hopefully you find it a nice gift to start your new year. As I've mentioned in a comment previously, the next chapter, the 50th, will be a Carrie POV, most likely in 3rd Person, though I haven't fully decided on the POV. As always, thank you all for the likes, comments, follows, bookmarks, and views. I greatly appreciate each and every one of them.
Meanwhile, across town
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The “Anything” Promise
The girlfriend who’ll do ANYTHING
Your new girlfriend says she’ll do “anything” and she means it
Updated on Jun 12, 2026
by Harst
Created on Oct 7, 2018
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