The direction this night would take all started long ago. We had been out at a local bar and I had mentioned how hot I find you and how lucky I was to have you as my wife. I told you how I wouldn’t mind seeing you let loose a bit, just to see what happens. You have a great body and definitely know how to drive a guy crazy on the dance floor. You’ve always been a good dancer and while I’ve had the close up view I decided I wouldn’t mind sitting back and watching you work your sexy ass up against a stranger or two.
To start off we decided that we would go to a bar and get a little tipsy. After a drink or two I would stay situated and enjoy a few more drinks while you went off, danced and slutted it up (just a bit) with a few guys while I watched from across the way. Just how easy you would pick up these guys was no surprise. What did surprise me however, was just hot I found it to watch you out there. Seeing you dance like you were a single, college girl again was quite the turn on for me. But again, this part of the story is just to setup the next, so I’ll get right to the point.
While you won’t admit it, I know and I think you do as well, that you can throw out a flirtatious wink or sexy look and pretty much hook any man you want. And that’s exactly what you did. A cute guy caught your eye from across the bar. You exchanged looks and soon enough you were working your way through crowd, letting your ass brush up against a few pleasantly surprised strangers along the way. Within seconds he was smiling and buying you a drink. You exchanged the typical pleasantries and soon you had him by the hand leading him towards the dance floor. The music quickly had you in the dancing mood and soon your hands were up over head as you hips worked in circles up against him. You were both enjoying yourselves (as was I from my vantage) With each passing minute he would get braver with his hands. They would repeatedly find their way up the sides of your ribs, each time inching closer to your breasts. Soon they found their way along the under side of your beasts, lifting them slightly as they slid past before heading back down towards your hips and ass. Each time his hands searched your body your back would arch and your ass would press further into him.
By now you could feel his hard cock through your thin skirt. His hands now began to slide to the inside of your thighs and would soon find themselves working ever higher. Soon you could feel his fingers brush up against your clit. His hands continued to explore your body and the next time his hands traveled up your sides they didn’t stop below the breasts. He took a handful and you let out a slight moan as your back again arched and your ass pressed deeper into him.
You can feel he is rock hard now. You spin around and Straddle his legs. This time it is your hands that find their way to his waist and you let them linger. They are soon tracing the outline of his cock through his pants. He bites your neck as you let your hands explore a bit as your body continues to mesh into his.
You can see I am enjoying the show from across the room. I let out a smile as I point to my watch and give you a wave. You can imagine how hard I am right now and why I am eager to get you home (that is if we can make it all the way home before tearing into one another).
Knowing your time is up, you let his hands once again find your pussy and circle your clit before whispering to him
“I have to go. My husband is waiting and wanting to fuck me.”
A surprised and disappointed look comes across his face but is soon replaced by a laugh and a smile. You kiss him and grab his cock once more before turning towards me. He slaps your ass and you turn, give him a wink and blow him a kiss. He watches as you return to me, straddle my leg and kiss me.
“Get me out of here and fuck me or I’m going to let this guy do it” smiling I reply “you’re the boss” and we exit the bar.
That night had turned out better than expected, now I wanted to up the ante.
This idea started with with a typically dirty thought that slipped into my always horny head. It was a challenge I wanted to pose to you. What exactly is this fantasy you may be wondering?
First things first, we get dressed up and have a few drinks. You wear something sexy, something that will quickly get you noticed. Of course I can’t resist and begin removing your clothes faster than you can put them on. You know there is only one way to get me focused, so after a little quickie, you finally have a chance to “fully” dress with minimal interruption.
Despite the fact you again have me wanting to remove your freshly donned clothes, we manage to make it out the door, and head off towards the bar. We are definitely going to need a few drinks to accompany the evening activities. Arriving at the bar, with a kiss and a slap of your ass, I grab a table and send you off for a few drinks. You’re suspicious that I have some secretive plan for the night, but you can’t seem to put your finger on it. Regardless, you’re excited for this rare night out. It’s not often you get the chance to dress up and feel sexy. You are, I might add, looking quite sexy. As you walk off I realize you must have pre-gamed little harder than I realized. You flash me a peek or two as you make you way across the room
We finish our first couple drinks as I lay out my idea for the night. As you know, I think there is nothing sexier than a wife who lets lets loose and explores her sluttier side from time to time. I get off from watching you and I’ve expressed my interest in seeing you pleased in some “unconventional” ways. Well tonight, if all goes well, will definitely fall in the unconventional column. Ideally tonight is all about me watching you explore your sexual confidence. Call it a flashback to your slightly younger (and admittedly sluttier) days when you let loose, with little, if any reservation. After some thought and a little convincing you start to scout the bar for potential “targets”. You know you have limited time and can’t be too picky, you have to be decisive. What exactly are you looking for you might be asking? Well the challenge is…
Could you, my sexy MILF of a wife, pick up a compete stranger and have him agree to film you giving him a blow job to completion for my viewing pleasure.
I have no doubt this would be of very little difficulty for you if it wasn’t for the fact you only get 30 minutes for this little challenge. Also, there was the tiny detail of finding a spot in/or around the bar to where you could blow a guy and get away with it. But of course, you love a good dick and couldn’t wait to taste some new cock, you were up for the task.
As your eyes scan the room you notice a few possible candidates. There are plenty of cute guys, but you wish you could see them naked. Who wants to waste their “hall pass” on an average or below average cock. You’re feeling horny and are craving a dick your lips can barely contain. You’re eyes finally settle on a cute grad-student type. You catch my eye from across the bar and cutely bite your lip in excitement as a huge smile fills your face.
You approach him as he trying to order a drink from the bar. He isn’t having much luck getting the bartenders attention. You ask him what he’s drinking and he says “Rum and coke.” Grabbing the $10 from his hand you tell him “leave it to me.” You lean into the bar, purposefully letting you ass bump up against his thigh. At first he thinks this is honest, incidental contact, but soon realizes you have deeper intentions. He soon notices you aren’t wearing any panties. His hand brushes against your short skirt and nervously finds its way to your bare ass. Wiggling from side to side you let him know you welcome his advances.
You easily get the attention of the bartender (obviously I mean look at you…) and order a rum and coke for your new friend, and of course a Long Island to top off your own supply of “liquid courage.”
Collecting the drinks, you turn around and again our eyes meet from across the room. You shoot me a quick glance and a smile as you turn to sit next to the good looking stranger. As you flirt with him he seems excited you’ve taken a liking to him (little does he know your intentions). You feel out of practice as if you have no idea how to flirt with guys anymore.
He says he had been waiting to meet up with his friends, but much prefers your company. Hearing this you now feel as though after all these years you’ve still got it.
As you are talking you see your already limited time is quickly slipping away. You also happen to notice your pussy is already drenched. Flirting with this stranger and thinking about what’s coming has you more worked up than you realized. You can’t hardly wait to be on your knees, pulling his (hopefully) nice, thick cock from his pants. Trying to think of a way to bring up the subject you decide the best strategy is to just come out and say it. You lean over and whisper in his ear.
“My husband is across the bar and has made me a bet.”
To which he replies: “wait, you’re married?, what bet?”
You tell him: “He bet me I wouldn’t be able to pick up a guy and suck his cock within 30 minutes of meeting”
“What?” He said slightly confused
“Let me put it this way…I want to suck your cock and taste your cum. Think you’d like that?”
He looks shocked and isn’t sure if he believes you. He looks around, trying to see which one of his friends is laughing in the corner, thinking they must have put you up to this. Instead he sees me on the other side of the bar and I give the two of you a wave. You don’t have time to waste and you decide there is one way to let him know you are serious. You lean towards him and grab his arm. Pulling him closer you whisper “I’m not fucking around, I want your cock.” You pull his hand up your dress, pressing it against your wet pussy.
A smile comes across his face and you can see he is excited. You turn towards him and slide his leg between yours. Your hand runs up and down his leg as his cock grows. His fingers circle your clit as you slide your hand down his pants and slowly stroke his rock hard cock.
He fumbles through his words: “uh, yeah I think I’m down for this” You look at the clock and realize you have 10 minutes to make him cum. You tell him to hurry and both get up looking for an empty corner or table, somewhere, anywhere with some privacy. You decide it is best to exit the bar and utilize the alley. Not the most classy, but probably the most private (plus you know I love alleys, so you’ll score major bonus points :-). Having not had time to fully explain the situation to your new friend he is confused when you hand him your phone. You tell him he has to be quick and also needs to video it for you.
He definitely thinks you are a bit crazy, but thinks to himself who really cares he’s about to get a blowjob! You find the most secluded spot by some shipping containers and hit your knees. You realize if someone walks by they will have little trouble figuring out what’s going on, but no time for caution, you don’t have much time. He presses record on the phone as you take off his belt and bring down his zipper. His pants hit the ground and your pussy is now dripping. Seeing the “enormous” task laid before you, you realize you must have a 6th sense when you chose this guy. He smiles as he sees the shock and excitement on your face. No time to stare and admire, only 5 more minutes…
You waste no time and take him into your mouth. Quickly you feel as though you can’t take him any deeper, and realize you’re only mid-shaft.
Never being one to shy away from a task, you push through, your lips stretch as you take him further into your mouth. He bottoms out deep in your throat and let’s out a moan as you slide your lips up and down his massive, thick, cock. You want nothing more than to pull back in admiration as it wags in front of you for a few more seconds. You’re dying to take your time and enjoy the feeling of his cock sliding back and forth across your lips. He’s rock hard and you can feel his cock pulse with every stroke. Your pussy is throbbing and you start to rub your clit, waiting for him to fill your mouth. You can’t help but laugh from the joy of knowing your husband is never going to let you forget the fact “he told you so” and you are in fact “quite the MILF.”
3 minutes…and you know he’s close. His legs are weak and he’s starting to wobble. He tries his best to contain his moans as he fights the urge to cum. It’s a losing battle and you both know it. 2 minutes to go…Just as you as starting to think you’re going to have to stand up and walk away, leaving him on the edge of orgasm, you feel his knees buckle. You know you’ve won. You feel the warmth rush into your mouth as it fills with cum.
You smile as his cock slips from your mouth. He falls back against the wall. Your pussy is throbbing and completely soaked. You definitely want to sit on his fat cock. You’ve tasted him, he’s stretched your lips, your pussy is dying for the same treatment. But that will have to wait for another night. You are ready to head home, suck familiar cock and get properly fucked. You grab your phone, stand up and give your new friend a quick kiss on the lips. You pull your dress back down across you ass and walk back inside to meet me. You’re all smiles as you make your way back to me. You tell me to hurry up and finish my drink. Eagerly, you tell me how you want to show me the video, but most of all ride my cock, finishing what you started with stranger from the bar.
Back at the hotel you stroke my cock as we watch the video. You look so hot, seeing you suck his enormous cock with ease, I cum quickly. We grab the “big” dildo, sticking it to the headboard. You take me into your mouth again as you back up and your pussy slides down over it.
You are so wet you nearly cum as it stretches and fills you to the max. You slam up against the head board over and over as you ride the dildo and take me into your mouth. By now we both wish we had invited the guy from the bar home and checked another item from the bucket list. Oh well there is always another bar, another night, and another cock…
Source: reddit.com/r/eroticliterature/comments/c5lnn3/30_minute_bar_challenge_fantasy_story_i_wrote_for
Great story. Been sharing my wife for years and have got to play this one out more than a few times. Amazing when she comes back with a story to tell. As a good shared wife she would purposely leave some of the other mans cum on display . Always hot !!