Date Night [updated]

Chapter 1 – The Plan

You text him “It’s a date, see you at 7” into your phone it’s a date and hop into the shower. Since Covid hit it has been forever since you have been on a proper date, but half way through your shower you come to a decision, I am getting laid tonight and you start to lay out your master plan.

You turn the water off and head out to get ready, you open your closet and pull out a black cablenet knit turtleneck sweater and plaid grey pleated mini skirt, and a wide grey belt that cinches your waste. Thigh high boots, to show of your legs. Finally a size too small pair of black lace bikini briefs, stretching them over your almost overly ample ass.

You head to the bathroom and put on your makeup dark eye with red highlights, black lipstick, slight pink highlight to your cheeks covering some of your freckles. You muss your red head giving that perfectly I don’t care look. You head back out to continue getting dressed but you pause at your bedside table, pulling the discrete remote vibrator out and stick it in your panties. Your thighs holds perfectly against you already slightly throbbing clit and lips.

Next the bra that struggles to contain your huge tits, you put together the rest of the ensemble.
Skirt that barely covers ass, Check
Sweater and belt giving you a slightly bottom heavy hourglass figure, Check
Panties barely containing ass, Check
Vibrator Check

You pause and an evil grin stretches across your face, you text your date a link and a code for the vibrator without explanation.

Boots, Check

You grab your purse and make your way out to the bar down the street from your house, you are almost late.

The Date

You arrive at the bar a little after seven. As you start to scan the bar you start to feel the low vibrations on your clit 2-3 and then it stops, you see him as he lowers his phone and gives a wave. Grey henley and tan slacks some stubble from a few days of not shaving, rectangular gray plastic framed glass accentuating grey green eyes, brown hair parted to right.

He gives you a hug and motions for you to sit at the high top table. You give him a sideways look “I see you figured out what I sent you earlier.” He nods as the waitress comes over and you order drinks.
She departs and he gives you an over the glasses look, “Do you always give that out on a first date.” You watch him look you over “I like the goth look. Back to your question, I actually had Tim to program a few hotkeys.” he pressed a button on his phone.

You feel the thing beginning to pulsate high for a few seconds then low it alternates for what feels like a minute. Before going silent again leaving you wet and wanting more.
Your cheeks flushed, you take a steading breath.

“Not fair”, you say, swatting his hand, “too soon for that. I don’t even have a drink yet.” He chuckles and puts his phone down. “Alright, but I want to point out you set the tone here. You don’t want to give the milk away for free.”

You stick your tongue out at him as the waitress sets your drinks down, you reply hold on to that for later.” He gives you a puzzled look and shrugs. A holds up his drink to toast the date.

The two of you make small talk and have some apps, all the while you bide your time then about an hour later the pool table in the back opens up. You grab his hand “Come on lets play some pool.” He gives you a quizzical look but follows along. He sets the drinks down at the hightop near the pool table, he checks his phone and you start to feel a light vibration. He catches on quick, you think, good.

Time to start the show you make sure he is looking as you bend to retrieve the wrack and balls from the table making sure to wiggle your ass each time you reach for the balls. You feel the elastic in the waste of your panties snap as you reach down to get the last of balls. All that is holding your panties on now is a bit of lace.

He comes over to rack the balls as and you brush past his thigh, and grin yup he was looking. You retrieve the Cues sticks he picked, “Teach me how to break, I have never done it.” He puts his arms around you and shows you to position your hand, you wiggle your ass again, this time pressed against him you feel him already hard and twitching slightly as you press your ass against him.

As he pulls away, he gives you a look and says “You sure you want to do this.” Your response is to break and begin the game. He grins “Let’s do this”. You both know that the game of pool is a cover, every time you move to hit the ball you flash him, and he responds by varying the vibrator. And each time your panties tear a little more.

An hour later you are nowhere near finishing the game, your panties having basically fallen off are stuffed in your purse, the vibrator held in place by your thighs. Every time you bend over he can see it all. You intentionally hit the 8 ball in ending the game, you straighten up and pout. Move over you pull him close and whisper in his ear “ Pay the bill and come see what you won.” You slip a napkin with your address into his pocket, grabbing his hard cock. You linger for a moment and then sache away making you sway your hips seductively on the way out. As if to have the last word the vibrator turns to fall on just as you cross the threshold.

Why Buy the Cow…

Fifteen minutes later the door opens, he finds you kneeling a few feet from the door. Gone is the skirt and the sweater and the bra. In their place a cow print sheer babydoll barely contains your gorgeous tits and a pair of crotchless panties in the same print. You beckon him toward you, he crosses to you closing the door behind him as soon as he gets near you begin to unbuckle his pants. With a fluid movement you yank his pants and boxers off. His cock springs toward you and you grab it gently squeezing the tip is already glistening. “MMM you get the cow and I get the milk”. You wrap your black painted lips around the head of his cock. Swirling your tongue around the head of his cock. Your savor the taste before plunging his cock deeper, your other hand grabbing his ass pulling him further into your mouth.

You begin to bob on his cock, then notice that your vibrator that had stopped right after you left the bar, starts up again. You look up to see his phone out , he taps a button increasing the pace. You moan around his cock as the vibrator starts a sequence of alternating speeds. You can’t concentrate, you stand up and lead him by the dick to the bed. Lean over it and exclaim “Fuck me!” as you spread your ample cheeks.

He slows the vibrator down and comes over rubbing the head of his cock against your dripping wet pussy. You moan and he thrust inside of you, grabbing on to your hips and pulling you toward plunging even deeper into your pussy. He begins with long deep thrusts pulling on your hips in rhythm. As he begins to pick up the pace he slaps your checks every few thrusts causing you to gasp, all the while the vibrator does its work against your swollen clit. You don’t last more than a minute, the vibrator and the thrusts are too much, you let out a primal scream as you cum all over his cock.

You collapse forward on the bed, you pull the lingerie off and lay back. He begins to move between your legs. You squeeze them tight feeling the vibrator press against your clit. He looks at you confused. You push your tits together suggestively and say “These need some attention too.” He climbs on top of you and sticks his slick cock between your tits, he begins to thrust as his cock appears out of your tis you open your mouth and tease his head with your tongue. He grunts and he moves his cock away, to thrust again. This game continues for a few thrusts as he moans getting closer until on his last thrust, he moves his cock into your open mouth.

He begins to thrust into your mouth, grabbing your tits roughly and slapping them as he continues, causing you to moan around his cock. You hear a sharp intake of breath and you know he is ready you swirl your tongue and flick the tip of his cock. He grunts and unloads straight into your mouth, your bob your head and he tries to pull away but you’re determined to get every last drop. You grab his ass and hold him in place as you swirl your tongue and suck the remaining cum from his cock. As you swallow you let his cock slip from your black lips with a slight pop. You release him and he collapses next to you on the bed.

You remove the vibrator from between your thighs and roll next to him, placing your head on his chest his heart still races. You gaze up at him with a devilish grin and say “That was a good start.” You Trace you finger down his chest when you hear “Why the hell is there clothing all over the place?!”

Chapter 2 – Three’s Company

You both tense and your heart races at the thought of your roommate walking into your room, in your haste you didn’t even close the door. Then a little that dirty little voice in your head, the one that started this whole plan in motion feeds you another filthy thought. How many times have you heard her scream and moan in pleasure from the guys she brings home. Your pussy throbs again at the thought of all the times you touched yourself while she was being pounded.

You feel him to move below you and try to cover himself. You push him down and whisper “wait” in his ear “this could be fun”. You see the flush of his cheeks and feel the tension in his body and you run your hand down his chest feeling his tense muscles, you see his cock twitch. You lick your lips this could be interesting.

Not a moment later she appears in the door holding your lingerie and his jeans. “What the … “ the sentence days in her throat as she takes in the scene. Her face making almost perfect :-O face. You look at her and she is wearing dark blue scrubs that hide most of her shapely form. T
he V-neck can’t completely hide the cleavage; her large DD tits that look even larger on her small frame, even though her ass is comparatively small, looks amazing in the cut she chose.
You smirk at her as you feel her eyes linger on your luscious ass and tits, as she meets your gaze subtly nod and shift your gaze to his cock and you know without looking she is doing the same. You look back at her face flush with embarrassment but the look in her green eyes is one of lust. You shift and say “well don’t just stand there either get out or” you straddle his face rubbing your dripping wet pussy over his nose and mouth. “Join us!”

She gives you a look and drops the clothing she is holding, and you see her walk off. You sigh but that is short lived as his tongue flicking your clit and your sigh turns to a moan of pleasure. You look down to see his cock stiffening and grab the base and begin to flick your tongue on the head of his cock. His tongue continues to dance across your clit and suddenly he sucks in your lips into his mouth and your moan taking his cock fully into his mouth, you close your eyes reveling in the pleasure. You bob your head on his cock a few times when you feel a soft pair hands around your head the fingers intertwining into your hair.

You open your eyes and you see your roommates face inches from yours, a lust filled look in her eyes. She pushes your head down onto his long thick cock pushing it deeper into your throat. “I want to see you choke on that cock you little slut.” You moan around his cock as he picks up his pace, flicking your clit with his tongue as you start to build to orgasm, she moves your head setting a steady slow pace, as you moan around his cock. Right as he is about to send you over the edge you feel his tongue leave your clit and feel him turn his head and he bites into the tend flesh of your thigh, sending you right over the edge. As you moan and begin to twitch, and she pulls your mouth off his cock with a pop. She kisses you, probing your mouth with her tongue, she breaks the kiss,. “Mmm, you’re a little slut you already took a load in your mouth. Did you swallow it?” Breathlessly you stammer “yes’ as you continue to twitch, his tongue moving in and out of your pussy. “Good” she smirks “Now turn around I want to see that fat ass bounce on that cock.

You look at her beautiful face, her gorgeous tits bouncing as she begins to take his cock into her mouth. You wonder when you lost control of this situation. You feel him moan into your pussy, as she sucks his, she looks up and pulls off his cock, slapping you tit she says “now slut!” and you realize it was the moment your eyes. You dutifully do as she says and turn around he kisses you. You moan as you taste yourself on his lips and face, as she easily slides his cock into your pussy. You feel her fingers sliding against your pussy and dancing across your asshole your ass twitches in anticipation but her fingers withdraw and you hear a slight squirting noise.

You move with his cock hardly able to focus on that as you wonder what she has in store for you. You don’t have to wait very long as you begin to feel a cool wetness at your opening. She pushes you forward your tits pressing against his chest as he thrusts into you. She pulls your head back by your hair. “ I have wanted to fuck you for a long time.” She pulls your hair as you feel what you think is a dildo into your tight ass. It is too much and you cum almost instantly as she pulls your hair back and he grabs your tits forcefully to steady you. There is no movement for a moment, they is a moment where you just feel full, as they begin to work out the rhythm and the begin to fuck you together, you realize as her hips meet yours that it’s not just a dildo but a strap on.

The rhythm picks up as they begin to work together. You watch him as he handles your tits, flicking his thumbs over your nipples as thrusts into the strap-on guiding his cock right to that sweet spot . You feel her fingers intertwined into her as she begins to thrust harder. She pulls you head back, his hand moves to your throat what was probably meant to be a steading action turns darker as she commands “That’s right choke the little whore.” You look into his eyes, and realize he is waiting for you to make sure you are ok “you let an O god yes as hits your g-spot again” and he increases the pressure.

You’re not sure how long this goes on but at some point in goes his cock hitting against your cervix, then the dildo slides into your his cock down into your g-spot, his fingers tightening around your throat, her had pulling your head back by your hair. Your pussy convulses squeezing his cock you, feel yourself push him out with a rush of pleasure you black out.

You come to you are not sure how long later but you feel the dildo retreat and you roll off him out of breath. You see him breathing a little hard, looking at you, your roommate is kneeling on the edge of the bed, her gorgeous tits slightly flush, the strap-on protruding from her thighs, only about an inch wide, but at least 9 in length. Holly fuck you think that was in my ass. You look at the two of them with stupid grins on their faces and ask “what?” she points down to between them, “you made a bit of a mess” They both laugh. You look down to see a puddle. “You squirted sweetie.” She says “you rest a little, but in the meantime I am going to steal him for a minute.” She steps off the bed and bends over to remove the strap-on. You see a green shamrock, nestled between her shapely cheeks. You look at your date as he looks at you. You both look back at her. She has a shit eating grin on her face, “your timing here could not have been better, I had that in most of my shift. Now bring that cock over here.” She bends over and puts her hands on your legs. “ no rush sweetie but when you are ready bring that pussy over here.”

Chapter 3 – Fantasy Fulfilled

As you recover, you watch as your date lines himself up behind your roommate. You have heard your roommate and imagined what it would look like. Your imagination pales in comparison with the reality. You watch as her body begins to move the way her tits sway and ripple as he begins as he sets a pace. She begins to moan and yell as he picks up the pace, everything you had heard from afar she is load when she is having sex and you love it. Your hand reaches out and intertwines into her curly blond hair. You pull her head up so her brown eyes meet yours. “Rachel you have no idea how long I have listened while your dates have fucked you and how much I wanted to watch you.”

She looks at you a coy smile on her face and laughs, He slows down slightly confused “Don’t stop sweetie, it is just funny Kat and I have been roommates for almost two years and we missed out because we have been to stupid to realize that this… was something we both wanted.” Her begin to tighten on your legs and you scoot forward pulling her beautiful face between your thighs.

He picks up his pace again as she begins to lick your clit, her face being pushed in with each thrust of his cock. She moans directly into your pussy causing you to vibrate her pleasure transforms to yours. Your free hand finds your nipple and begins to tweak and roll it between your fingers. Your hand grips her hair as the two of you begin to moan as almost in unison. It does not take long for the two of you to orgasm together. She collapses into you, as you release your grip on her hair and cum all over her beautiful face. He stands slightly bewildered still stroking his cock.

Rachel looks up at you and you and says “He is your date I think it is only fair to let you finish him. Now let me watch that gorgeous ass as he fucks you.” You switch places and get on your knees in front of him. He slips his cock into you and you nearly lose it right there from how sensitive you have become. She puts her hands on your ass cheeks to steady you. She begins to slowly massage your ass cheeks, cupping and kneading them as he continues to thrust into you. As he picks up the pace so does she, begin to slap your ass every time pulls back, he trusts in deeply now till his hips hit yours, his balls slapping against your clit with each thrust in.

After only a minute it is two much and begin to spasm in orgasm, your ass still in the air. You feel her pull him towards you placing his cock between your ass cheeks, after only a few pumps he explodes all over your ass. You feel her tongue on and fingers clean off the mess. You turn over collapsing back. Her face moves in her lips meeting yours she kisses giving you the combined test of you and him on her lips.

She breaks the kiss and nestles onto your breast, you feel her squirm a bit as she removes the plug from her ass. Your date comes up and kisses your forehead before snuggling into your other gorgeous breast. You feel Rachel snuggle in more “Mmm comfy. By the way I am Rachel.” She gives a slight wave and a bit of a giggle. “Mike.” he responds with a nod and a grin. You place your arms around them both and you all snuggle in for the night. As you begin to drift you feel her look up at you, you open your eyes and meet hers. “Seriously though you better make sure this isn’t the last time we do this.” Your grin is enough for her and she snuggles back in.