Hall Pass

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

I get a coffee from here every morning, but I don't usually stay, just pick one up on my way to and from the gym."

"Oh, so you work out. Yes, it shows ... I can see you really look after your body."

What's he blabbering on about? How does he know what my body looks like? Oh, I am wearing my best bra that lifts my somewhat mid-forties sagging breasts, and I do have a quite tight sweater over the bra. I guess I'll accept the compliment?

"Do you have a family?"

What a strange question to ask. "Err ... yes ... yes, I do. A husband and two kids but the kids are away at college now."

"No ... you don't look old enough to have grown-up kids."

What a nice thing to say, but again, I think it's a line. Is he trying to pick me up? That would be flattering but my god, at a guess I'd say he's mid-fifties. Nevertheless, he does boost my confidence. Of course, I'm back on the market, looking for a lover to fill three nights after firing Jason's cousin. However, for my revenge indiscretion, I'd prefer he be a younger man. My original target, the busy barista, is a couple of decades younger than me - and looks less and less likely by the minute, yet I draw the line at picking up an ageing charmer. My mother used to call them a Casanova.

"So, is your husband a good man? Does he look after you, treat you well? Are you a happy and contented wife?"

I am taken aback, "I don't want to be rude ... you seem like a nice gentleman but that's really none of your business."

"I'm sorry, I certainly don't wish to offend you, but I was observing you while waiting in line to order my coffee. If you'll pardon me saying, quite frankly, you look like you have the hots for the young barista here. I know that look in a woman's eyes, I've seen it often enough. In the five minutes that I was watching you, you never took your eyes off him."

Oh my god, was I that obvious? I need to deny, "That's a preposterous suggestion ... err ... if I was ... umm ... staring at him, it was more a fascination for how hard he works."

"He does, doesn't he? That's my son you're talking about."

"Oh, really! He's quite a handsome young man."

"I wish I could say he takes after his dad, but the years are taking their toll."

This man is so complimentary, having called me beautiful and suggesting I don't look old enough to have kids in college. I spot a chance to reciprocate the compliment ... "Now that you tell me he's your son, I do see a resemblance. You look good, what would you be? Fifty?"

He raises his eyebrows at my generous assessment, "I'll take that as a good guess, but in reality, I am fifty-five."

Exactly what I really thought. Still, the more I look at him, he has matured well. Very neatly dressed, well-groomed and, unlike so many men of that age, he doesn't seem to have a stomach paunch.

"So, beautiful lady, you still haven't told me how well your husband looks after you. A woman like you should always experience the best."

Again, none of his business, but this time I hesitate in telling him so. It might be too harsh. The longer we sit and talk, I find myself warming to this man. Maybe the dad is a more achievable target than the busy barista? He's making what could be an awkward approach so much easier than I could ever have contemplated with his son.

Before even thinking it through, I answer his personal questioning as if my coffee has been laced with a truth serum, "We've had a good marriage, twenty-two years of it. But these last few weeks, we've encountered a rough patch." Does that come out right and is it necessary for me to be so frank with a total stranger? As soon as the words are out, I wish I could take them back.

"Oh, honey, that's a shame. A beautiful woman like you deserves only the very best. What happened, I'll bet he's been indiscrete?"

"Why would you immediately think that? Is that usually the cause when a couple is having problems?"

"I'd say for a marriage of twenty-two years, ninety per cent of the time. Is it serious, can you work through it?"

"We are working through it." Oh, damn! Heather, just shut up, I tell myself.

"Is he over the other woman or do you think he'll keep going back for more."

"No, he tells me he's over her."

"But are you ready to forgive and forget?"

"I'm trying ... he gave me an incentive."

"Oh, really. What is that?"

Why am I being so open, revealing to a complete stranger how fractured a marriage I currently have? Is it that this man's demeanour is so warm and conciliatory? He's making it easy - too easy, I fear - for me to talk to an outsider, perhaps get a man's perspective of what I've been going through. I have this compulsion to continue now that he has drawn the subject of Jason's infidelity out of me.

"Have you ever heard of a hall pass?" Without waiting for him to answer, I go on, "My husband offered me one so I could choose a man - any man - to go do with exactly what he did with that woman. In other words, a free pass to exact revenge on him for jeopardising our marriage. For his magnanimous gesture, I might forgive him."

"So, have you exercised the hall pass yet."

"Partly!"

"How can you utilise a hall pass only partly?"

"Well, he went with this younger woman he met on a wild night out with the boys on five occasions. I insisted that I too am entitled to doing it five times with whomever I choose ... or chose."

"Oh, so you're halfway through having your revenge sex?"

"I was, only yesterday I had a falling out with the man I chose."

"So, where does that leave you?"

"Well, as you so astutely observed, I was sizing up your handsome young son as a prospect."

He breaks into a huge smile and a chuckle too. I like the warmth of his smile.

"Sorry to be the one to disappoint you, but you won't get him. He lives with a gorgeous young woman ... they are a great couple, and he is deliriously happy."

"Thank you, that will save me from heaps of embarrassment, although it does take me back to square one. It was a long shot anyway."

"You could always switch your interest to his dad ... the apple doesn't fall far from the tree when it comes to sexual prowess in this family."

"My guess is you're married; my memories of dating all those years ago were that the charming ones were always taken. I can't have a married man because I don't want to cause trouble the way that woman did in my marriage."

"Then hopefully you'll be pleasantly surprised to learn that I'm not ... not anymore. My wife passed away two years ago."

"Oh, I'm so sorry for you."

"Don't be, two years is a long time and I've learned to cope as a single man again."

"Oh, this is becoming awkward, I shouldn't have so freely unburdened my situation to you. I don't usually do this with strangers. I think it's that you have a nice way about you ... interested and inquisitive without being intrusive. I like talking to you."

"Please don't think of it as awkward. I've now known you for nearly a half-hour, so we're no longer strangers. Let me put this to you. I understand the dilemma in your marriage. I have counselled several friends - both men and women - who have gone through similar circumstances over the years. I would love to help you and even be of some service to you in whatever way I can ... be that as an advisor or a lover. I have to take a drive into the country today. I own an investment property at a small rural precinct called Parkville, not quite a two-hour drive from here."

"I know Parkville, my husband and I have stopped off there to check out the antique shops while on a country drive a couple of times."

"Good! So, you know how far it is. Well, I need to drop some stuff off in preparation for new tenants arriving at my property next week. If you don't have any serious plans for today, why don't you come with me. It will be a good chance to get to know each other better without just jumping into bed, which could, as you say, be a touch awkward. I'll pick up some food and some wine on the way and we can have a picnic on my property. You don't even have to venture inside the house, where there are beds, if you don't want to ... just to show you my intentions are quite honourable. Unless of course, you'd prefer to take it to the next level straight away ... that's your choice. We can simply get to know each other today on this journey and if it all feels good to you, then I can be your replacement revenge sex partner sometime in the next week or so."

The man makes it all sound so tempting ... and exciting. Much more feasible than my harebrained idea to try to seduce his son while he was working. We finish our coffees and he leads me out to his car parked at the kerb. I even allow him a flash of my thighs as I less than delicately slip into the passenger seat of his car while he politely holds the door open for me. Old world charm!

He starts the car and turns to me, "I don't even know your name."

I give a little giggle as I realise that I too was getting into a car for a long drive with a man whose name I don't know. "Heather ... my name is Heather."

He offers me his hand to shake, "Hello, Heather, it is so nice to meet you, I'm Robert or you can call me Bob if you like. I hope we are going to become very good friends and I will just say here and now that I am happy to be used if you decide that I will be suitable as a revenge sex partner."

"Thank you, Bob ... we'll see. While it may seem otherwise by some of the things I said, I'm in no rush to decide. Let's see how this day goes."

I settle back in the comfortable car seat and enjoy being driven, taking the chance to look at things we pass by on the familiar road out of town. I've driven this road often in the past but as a driver and one never gets to see the passing features. Robert turns out to be a great conversationalist. I can see why when he reveals that he has worked in sales for most of his working life ... salespeople usually have the gift of the gab. He tells me he is already semi-retired at 55, living off his property investments.

The longer I am in the car with him, the more I think of having him sexually. I steal glances across at him, studying his face, imagining how those lips will feel on mine and on my nipples. I really do get myself quite excited and I'm guessing I could even be wet already down in my hidden pussy. I even look at his lap, expecting - actually hoping - that I might see a tenting in his trousers, and I can gauge what size his dick may be. I doubt though that I will find another of the proportions of Michael.

By the time we pass the sign indicating we are entering Parkville, I am convinced that Robert will replace Michael for the remaining three dates of my hall pass from Jason. I look across at him and wonder how he will be in bed. How will his sexual technique differ from Jason and Michael? Is every man different? Having to even ask myself that question makes me realise what a sheltered sexual life I've led.

Robert stops the car in the township, outside a group of shops and rushes off into a delicatessen and a liquor store. Looks like he is really serious about us having a picnic together on his property. He is back within five minutes, and we drive on out of the other side of town. He shortly turns the car in at a farm gate and we travel down a long gravel driveway to a farmhouse in the distance.

He gets out of the car and opens the back door to retrieve a box from the back seat. "Heather, you're more than welcome to come in and look around if you wish, it's up to you, or you may prefer to stay here, and I'll drive us down by the river that runs through the back of the property. I'm only going to be a minute here."

I am tempted to go inside. After all, there will be beds in there and by now, I see this man as my new hall pass partner. How easy it has been to find him after wrestling with names of guys Jason and I know. I choose not to go inside, instead liking the idea of having a picnic down by the river with this man.

As good as his word, Robert is back in no time. We drive on toward the back of the large property where rolling hills lead down to a river. What a wonderfully secluded spot and what a great setting for us to consummate our new sexual arrangement. Nobody is likely to see or hear us here.

Robert rushes around to open the car door for me again and I reward his courteous manner by getting out really slowly, deliberately parting my legs, planting the lead foot on the ground while still having my trailing foot linger for a moment in the car and my skirt riding up high on my thighs.

I look up at Bob's face as I rise up out of his car. He smiles warmly and all he says is "Nice! Thank you!" obviously appreciating my overtly sexual gesture. I wonder how much thigh he saw ... my skirt did ride up a long way, did he spot my panties?

He retrieves a rug from the car, spreading it on the grass above the riverbank. What a beautiful spot this is. There are enough trees to afford us some cover from the harsh midday sunlight. He has placed the blanket where I can choose to sit either in direct sunlight or in shade from the large overhanging tree. I select the shade, kick my heels off and drop down onto my knees, hoisting my skirt up to mid-thigh level.

Bob brings his purchases from the car, starting with the bottle of wine. He must have grabbed two wine glasses from the house, quickly filling them, offering one to me. I enjoy wine and he has chosen well ... I like the taste. Then he proceeds to lay out a salad and some cut sandwiches.

The impromptu lunch he has organised is wonderful. The wine, the sandwiches, the salad ... it all makes for a lovely relaxing occasion. Who knew when I got up this morning that I would so easily find a replacement for Michael and that I would be eating lunch two hours drive from home, almost without a care in the world? With this charming older man who has offered to help me utilise the remaining days of my hall pass. I feel in an almost euphoric state. Life is good and the longer I remain in Robert's company, the more I want him.

I can't help but feel that I am in a romantic scenario. This man seems to be seducing me with his charm, his wit, his persuasive patter, and with the support of a nice wine. My hunger appeased, I lay down on my left side on the rug, stretching my legs out, not bothering to push the hem of my skirt back down, leaving it at mid-thigh, which I would think affords Bob a generous display of my legs that are fortunately cellulite-free in spite of my age.

I close my eyes, Robert takes this opportunity to shuffle his body closer to mine. I feel his fingers gently caress my inner thighs above the knees. I am happy to have him making such a move. Not wanting to seem too obvious - yet it probably comes across as such - I let my upper leg bend at the knee to give Bob more inner thigh to work with.

Those gentle fingers softly caressing my inner thighs are captivating, stroking from above my knees up under my loose skirt nearly to the crotch of my panties, each time stopping maddeningly close to rubbing my pussy through the thin material. I keep my eyes closed, implying my complete relaxation, hoping he will go further.

Not even contemplating the consequences, I roll over onto my back, adopting the most vulnerable position for a woman. His fingers are unrelenting. At last, I feel them touch the crotch-piece of my panties, seemingly fiddling there. What is he doing? I feel human skin touch my pussy lips ... he must be pulling the pantie crotch to one side because now I feel those fingertips rolling up and down along the crease of my labia. A finger touches my clit and my hips hump upward. For the first time, I can feel how wet I have become, simply from the anticipation all through lunch.

I peep through lidded eyes to see that Robert is sitting alongside my right hip. He has rolled my skirt up so that it lies around my hips; he must be able to see my exposed pussy, the lips of which his fingers are exploring. Shamelessly, my body begins moving with his touching, my pussy chasing his fingers if it feels like they are moving away. They've gone, where have they gone? But almost immediately, before I might protest the loss of his sweet fingering, I feel a large blunt force at my very wet pleasure passage entrance.

My god, that has to be his dick, of course, and very erect. I never felt him move his body over me, but his legs are suddenly between mine. He has executed that move so smoothly. I open my eyes, the glare of the sunlight momentarily blinding me. By the time my eyes adjust, I can feel his erection - hard, very hard - at my vaginal entrance. He earlier assured me that today was simply a getting-to-know each other day. Yet now I feel the head of his dick is inside me. I am not unhappy with that outcome ... just surprised.

"NO!" Even as I loudly utter a negative word, I know in myself that I don't mean it.

"What do you mean no?"

I see his smiling face hovering only inches above mine, feel his still fully-clothed body resting on top of my almost fully-clothed body, feel the head of his dick lodged inside me. What now? I do want him, I just didn't expect this so soon, "No, I'm sorry, Bob ... I don't mean no ... really, I don't. You just took me by surprise ... I mean, I didn't even see you take your dick out of your pants. It was just suddenly there and inside me. You told me nothing was going to happen today, we were just going to get to know each other."

"That is true ... was true. But then you lay down on the rug. You looked so relaxed and comfortable ... sexy and inviting and I touched you with my fingers and you look like you were enjoying that. I was in a quandary ... fingers or cock! I needed to make a quick decision ... I chose cock over fingers. I figured we'd both like the feel of that much more than just my slim fingers."

I look up at him, his face is so close. I see his huge look of anticipation there ... he's waiting for my approval, even with his dick partially inside me. Of course, I want him inside me ... I have since we started the journey down here to this lovely village, and his remote property. While I don't want romance; I only want sex to pay back Jason, I can't help but feel wrapped up in the romance of this situation. A handsome older man is about to fuck me - illicitly. We are outdoors, in sunshine and some shade ... I've never made love outdoors in my whole life. The sounds of water ... the river that runs by us not more than twenty feet away.

It all combines for me to tell Robert, "Yes, of course, Bob, much better than fingers. Please ... please do it. I want you now."

Without even a moment more hesitation, I feel his erection push quite strongly up inside me until it bottoms out in there. I bring two arms up impulsively to wrap around his back. Oh my god, his dick feels wonderful inside me ... solid and thick. It's a shame that I never got to see it before he buried it up inside my vagina. He fills my passage, but not overly so as Michael did. No extraordinary length here, but he must be thicker than my Jason because I do feel extremely filled. He's tight inside me ... but not uncomfortably so.

I settle back onto the rug beneath me and feel Bob withdrawing his erection until only the head clings to me. Then, a strong forceful plunge back up inside me until our pelvic bones crush together again. A fuck is under way on the riverbank.

He develops a rhythm, and it feels really nice ... a gentle pulsing begins deep inside my lower body. That's good, everything is working nicely. But I am alarmed when I very soon hear Robert's breathing becoming loud. No, no, not yet, I silently say to myself, wondering if I have the right to say something aloud at this point ... to ask him to not cum too soon. I've never had a problem with Jason ... he always waits for me to cum, and with Michael ... well, he was quite extraordinary; I enjoyed multiple orgasms with him.

1...89101112...14