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Playing Chauffer 3: First Date

by Jackie Rabbit

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© Copyright 2016 - Jackie Rabbit - Used by permission

Storycodes: F/m; MF/m; D/s; cuckold; chast; denial; date; dance; dinner; kiss; tease; rom; erotic; jealousy; femdom; cons; X

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Part 3: First Date (The Prequel part 2)

"You and I apparently have some shopping to do," I informed my kneeling and locked husband, he not able to comment though because my panties were still gagging him. He could have easily spit them out, but I hadn't given him permission to do so, and he so looked to be struggling to figure out this new me he was looking up at, just as he had struggled between handing me my key awkwardly and keeping his hands submissively clasped behind his back moments earlier.

Was this to be the first step of his cuckold dreams realized, or instead the first pangs of regret so soon into this? Some dreams started off nicely enough only to become horrible nightmares before one woke, and I wondered philosophically if my kneeling husband had pondered this, or if he had pondered my own growing resolve in making this kinky game of his a reality.

I then allowed him to dress and remove his gag, his face hard for me to read though. Was this everything he thought it would be, or just a little too real for him? As an unintended consequence his man shorts grabbed and snagged at his new chastity device despite the quality of it's manufacture, my natural solution once I realized this was to hand him a pair of full cut silky panties, every woman having some deep in the back of their drawers for those occasions when they were needed. They were intended as a seamless undergarment for my more translucent things, and much less "packaging" than his guy shorts, although not the least bit masculine.

Again I was amazed at how easily he submitted to my lead, his locked man hardware allowing me an almost magical level of control over him, but I wondered if this control would extend to others? One couldn't be properly cuckolded, (if my research proved accurate), without full and unconditional submission, but would that submission include Jim as well as myself as it naturally must?It was a question that would have to be answered at some point, but still one I suspected my husband hadn't fully pondered when offering up my married virtue to a real flesh and blood alpha male with his own independent thoughts on the subject...

Shopping was great fun, as was watching my husband's torment as he got used to his new secret accessories, but the overall most erotic part had to be being "forced" to purchase the dress and heels another man would get to see me in on our "date". It was still another cliché from his cuckolding fantasies, and to torment him even further I modeled the undergarments and stockings I claimed I needed for my new slinky dress, sending him selfies from my phone in the dressing room mirror to be sure he would get the whole experience, heels and all. It was like the glamor shots I had done once for him as an anniversary present, and I wondered with an evil smile if his trapped member were trying to make itself painfully known as he watched, or had he already come to the conclusion that this body of mine wasn't for his entertainment anymore...


Jack helped me get ready for my date late that afternoon even though I didn't exactly need the help, it was still another cliché from his cuckolding sites though. I wanted him to get the whole experience however, also he couldn't one day claim that I had short changed him in this somehow.

He was so into this preparing me for my date with another man thing that he even offered to shave my legs for me, his slavish attention boosting my already inflated ego exponentially. I sensed a part of him really wanted to hump my leg like a naughty dog while he was down there to relieve some of his pent up tension, but that would have been rough on my leg with him caged as he was, not to mention producing a sticky mess that would have to be dealt with if he should somehow be successful. There were clichés in the cuckolding world regarding those kinds of messes, but I had decided to save that little messy treat for another day so as not to overwhelm him.

Sufficient to say that at that particular moment this still appeared to be playful fun for my husband, although I feared in an unreal fantasy kind of way despite Jim being a real flesh and blood man and not some imaginary lover of my own fertile imagination's manufacture. I wondered then when exactly reality would creep it to spoil his fantasies, or even if it would, perhaps I being the one confused with all this. One thing for certain though was my own ego's ever expanding mass, I in my mind feeling more sexy and desirable than I had in years and entitled to all this wonderful attention, as well as the attention of a man that until recently had been well out of reach.

...A kind of internal battle briefly raged in my mind, and to a lesser extent my conscience now that the moment of truth was upon me, my own courage wavering ever so slightly instead of my husbands as I had expected...

Do I pull the plug on this little adventure right now before things get too out of hand despite my own natural curiosity, (it's just wonderful to have a desirable second man interested in you with the proverbial "hall pass" firmly in your hand), or do I cowardly retreat to what is comfortable and safe, and yes even boring? My husband wanted this though, (I argued in my mind), how could I give him anything less without violating the contract that I had agreed to as well? In truth I was just as obligated as he, not to mention the potential collateral damage to Jim's own ego should I back out, the man we ostensibly arranged all this to help.

"Just do it" the reckless part of my mind demanded, the butterflies of desire fluttering in my belly despite this just being a dinner and dancing date, "but with conditions" the logical part of my mind cautioned. It seemed most reasonable to do this incrementally, I obviously wouldn't be sleeping with Jim... Yet... Just dinner and dancing, and perhaps I might even encourage some flirting verbal foreplay to see if that kind of chemistry was even there. Jack would likely end up being fully cuckolded one way or the other with this or even another man, but gradually and on my terms, not his. Jim was still an unknown in this little equation as well despite his initial enthusiasm when we had first talked openly about a dinner and dancing date between us, but the chemistry of desire for me was still everything, and if that chemistry wasn't there between Jim and myself I knew I would have to search elsewhere.

I well knew the potential impact of having Jim pick me up while Jack was standing by in attendance, the proverbial "giving away the bride" from a certain point of view, but in this case Jack's own bride, most especially after the look I got when taking off my rings and putting them into my jewelry box until needed again. I decided not to put either man through that for this first date in light of that look, I trying to do my own part to engineer the success of this kinky little adventure I was invested in for my own selfish purposes.

It was strange to me that of everything we had done so far to make this fantasy a reality, the simple physical act of removing my rings broke through my husband's fantasy/reality wall for a moment or two. His expression was blank as he focused on my actions, like a man seeing some horrific traffic accident happen right in front of him and he being powerless to stop it, but recalling every detail vividly over and over again in his dreams.

Powerless, neutered, and dominantly controlled, and not just by me either if things went as they must. In that instant my true understanding of this experience from his perspective I think began to form in my mind. Jack apparently wanted a vacation from being the man of the house, allowing another and perceived better man to take his place for a time so he could be free of those responsibilities, but also necessarily giving up the fringe benefits that went along with them at the same time. He hadn't really enjoyed those benefits for some time, he instead preferring to serve me as a less that equal partner to ensure I was taken care of, all in all a charming character attribute, but a rather submissive one. I then realized that such was the price he MUST be forced to pay for this vacation from manliness of his so that he could get the whole experience, and I was thusly obligated to do my level best to make sure he paid it in full along with any interest I could tack on.


I was reminded once again of the emotional roller coaster my friend had suggested my husband was about to ride, I sending him to get his things in the basement for his painting assignment when Jim pulled into my driveway. I then greeted my handsome date outside where he opened the massive SUV's door for me most gallantly, likely sparing my husband still another downward ride on his emotional roller coaster, or from some kind of date ruining confrontation should he suddenly find the ability to "man up", which I doubted locked as he was.

Jack my husband had "volunteered" to paint Jim's rec room that night at my suggestion while Jim took me out for dinner and dancing, a true first date alone with another man since long before I was married. It was naughty and conspirtal, and impossibly exciting with the threat of discovery by someone who knew either one of us while we were out on the town together, fortunately not in our town though. That could be a minor scandal where we were all known, but our "dancing lessons" could still be explained away as an innocent thing for the time being, especially if my husband played his part properly as I suspected he was motivated to do. What normal man, I rationalized, would want it known that his wife was on a date with another man with the future potential to "hook up"?

Jim's hands and body felt warm and powerful as he guided me around that dance floor later that night, any apprehension I might have felt melting away with how easy and natural Jim's lead felt, as did our friendly conversations earlier over dinner. He hung on my words, and I his, a rather refreshing change from what I had grown accustomed to being married for a few years as I was. Neither of us mentioned Jack, (it was almost too easy not to), but Jack was firmly committed to my whims by his own hand and the key safely stashed in my little pocketbook.

That first real date ended very late with a single kiss in my driveway, Jim unsurprisingly an excellent kisser even though it was really just a peck on the lips. I had to get up on my toes though to kiss him properly even in my high heels, his powerful hands on both of my hips instead of wrapped around me like a lover's would be, my hips and his hands already well acquainted from our dancing though. I met him half way on that first kiss of ours, not out of any deep thought, just because it felt so right to both offer and take equally from this man that had just shown me such a wonderful time.This was also a potential show for the neighbors if they could see past our hedges at this late hour, but at that particular moment I didn't care in the least.

Somebody else was watching though, from my own house...


"I was concerned" I heard sullenly from my husband when I walked through my own front door still under Jim's protective stare well after midnight, the lights still on, but dimmed down. It was half concern, and half an accusation, my phone turned off intentionally so as to have no distractions while I was out having a good time. Had Jack any real concerns he could have always called Jim's phone to check up on us, but he had obviously chosen not to, unless Jim had blocked his calls as well. I sensed there was something else going on here, but at that moment it was just a hunch.

"I was in very good hands" I replied, my double entredre completely missed by my husband at that moment. I had just had one of the ten best dates of my entire life and I felt myself glowing, and I was in no mood to have anybody spoil it for me, not even my neutered husband who in part had made it possible.

"It's not like Jim was going to let anything bad happen to me" I offered reasonably as if my husband's concerns were for my security while out on the town at this late hour, ignoring the accusatory part of his tone dismissively for the moment as I removed my heels. The message in doing both things at the same time was as clear as it could be from my point of view, I was going to do what I wanted no matter his "concerns", I not even pausing in removing my heels to address him directly, as if the one was far more important than the other.

"I saw you two in the driveway" my husband confirmed, the accusing tone back and now impossible for me to overlook.

"I thought I saw you peeking, we had an excellent date by the way" I shared dismissively. It was a provocative detail that he didn't really need to know, other than to ensure he was getting the whole experience from this cuckolding thing he dreamt up. Objectively it could be seen as rubbing salt into the wound, but that particular wound was self inflicted and my empathy lacking.

One could argue that it was just dinner and dancing, (but in reality it was an emotional bonding with this new man), he rather gentlemanly with me and a pleasure to be with one on one, the vibe of our neighborly relationship changing rather drastically in a single date. At the same time I couldn't help but to consider that this rather charming man was in competition for my favors, but in a game weighted heavily in his favor so long as that special little key remained in my possession. I WAS glowing, but for good reason, my inflated ego bringing out what little aggression I had buried deep inside of me, Jack now less than my equal by his own desires as well as contractual obligation, and fair game should he continue to step out of line.

Jack didn't respond verbally, but his face told me everything I needed to know, and it irritated me briefly.

"Are you so naïve as to believe that Jim and I might not kiss on our dates?" I scolded as I wagged my manicured index finger in his face. "What exactly did you think would eventually happen on this little adventure that you pushed so hard for? Jim is potentially my future lover by your own request, and while that might not ever happen where you can actually watch it, you have to know that we may eventually be doing so much more than just kissing, although with that man I have a feeling it's never going to be 'just a kiss'."

"We'll discuss your tone another time" I continued somewhat more calmly after venting, "right now I want you out of those clothes and my aching feet and legs rubbed, in that order. I haven't danced that much in heels like that in years, and I suspect being allowed to be clothed in my presence has confused you as to your proper place in this new relationship, unless you found some creative way to cum while I was out."

'Caught you' I thought to myself when I saw his face's reaction to my rude observation. He had cum, somehow, and in the process had drained his kink enough to be having second thoughts. Too bad for him I thought, Jim wasn't having any, and my own apprehension was getting weaker by the moment

Jack easily and naturally submitted to my lead once I had exposed his little secret, and when he came back in wearing only his device his attitude seemed to have thankfully been left in the other room along with his clothes. He then rubbed and massaged my aching feet and legs like a man with a mission, and I learned something in the process as I calmed myself down and reflected on our little exchange.

There was a lesson here, Jack needed a firm hand for this to remain fun for him, and likely not only from myself, and we were at the very least obligated to give this to him. It would require just a little more from myself than I had originally anticipated, but the obvious reward would be taking another man for a lover guilt free. Such at the same time would also require Jim to more quickly and firmly establish his own position as the dominate head of this relationship, and be fun to watch from a certain point of view.

There would have to be consequences for this misbehavior though, anything less would short change my giving husband in what he needed from this, and cause me to have to do this over and over again, something my new temperament toward him just wouldn't stand. He was after all no longer really my husband (at least as in the sleeping together and sharing decisions part) for the next year, but had instead opted for the duties and position of an indentured servant by his own desires, as well as the caged manhood uniform of submission. I had not intended to boot him from my bed so quickly, but circumstances dictated that my intended timeline be accelerated, and we had several extra rooms.

"I want you to sleep in the spare room tonight, and while we're on the subject of familiarity, I expect to be addressed as ma'am or Ms. Smith from now on so that we don't have any more misunderstandings between us." It was a rebuke, and not exactly a gentle one, but one has to give respect to one's key keeper if one knows what's good for him. The sooner he learned this the better, Jim not likely to be as forgiving as I am should he attempt this tone of his where Jim can hear it, most especially after I told him what I had discovered.

"Yes ma'am" my subdued servant responded without malice, his eyes lowered humbly, but it was really the only option I had given him. Smith was my maiden name that I still used at work, I thinking that implied message not subtle at all. I had in effect just turned back the clock several years, Jack however now a quasi servant disinvited to share even my bed, all while Jim strived to take his place in it. Jack was serving, and Jim commanding and firm, the former well known and somewhat comfortable like a well worn pair of sneakers, the latter enticingly unknown and under any other circumstance forbidden, but in this strange one permitted and encouraged. Both qualities at times had their place in a man, but nature didn't allow for them to be easily contained in the same man, and here I saw what drew me to this strange idea in the first place. In a way I could have my proverbial cake, and eat it too, and not have to even do the dishes afterwards...


After that little exchange it became Jack's every night after work project to prepare Jim's house for the Realtors, Jim and I getting together to pick colors for the rooms and choose staging furniture so that his half empty house would look as good as it possibly could and fetch top dollar. It was bittersweet because I didn't want him to move away, but he at the same time had an obligation to his former wife that he needed to keep as he had given his word. If we at some point decided to sell our own house, having one on the same street sell for a good price would be nothing but good for us, so in the end Jack's efforts were not entirely selfless, but I don't think his thoughts were that deep on the subject.

A mere week into this little adventure Jack willingly did what he was told by either of us, (no longer was there any pretense of asking him). He acted simply because we had firmly spoken the words, his slide into semi-slavery impossibly natural, and looking comfortable for him in my own humble view. It was something that had to be seen to be believed, but an intoxicating power to have none the less over another adult human being, especially one that until recently had been an equal. I think Jack's slide from parity with myself, (and to a lesser extent with Jim), into a form of servitude was made all the more poignant by the ease of that slide in status. One was left with the conclusion that this was his natural comfortable state, the former co-equal partnership one with myself the unnatural one that became too much of a burden to keep.

At the same time there was a kind of non-verbal communication going on between Jim and Jack, the former was the top dog alpha male of our little Ménage à trois by default, and the latter knew it instinctively. Jim's at times sharp words were digested whole by Jack with a respectful smile and obvious submissive body language, his head bowed slightly and hands clasped behind his back. After Jim pointed it out to me privately I kept watch for it, Jack signaling his willing submission subconsciously every time the two interacted likely so as not to challenge the top dog of our little pack accidentally. Jim was the unchallenged top dog, and when he barked Jack the neutered dog responded, it was no more complicated than that.

I also realized that this couldn't possibly work without Jim's confident masculinity, he the perfect man to make this fantasy a reality, as if destiny itself had brought the three of us together.

...I had one other conflict with Jack just before my second official date with Jim, I instructing him move his things permanently from my bedroom into the small spare one right next to it as a consequence. That little episode had been two weeks into this little game of ours and a surprise to me as he had at that point submitted to our authority, (Jim's and my own). It was at best a half hearted resistance, he obviously liking his new station in life at some level, as well as the freedom from making any important decisions. His willingness to freely submit to us made this little game all that much easier for both Jim and myself, not to mention wickedly entertaining, and I knew I had to nip this in the bud before it spoiled our fun...

"Where do you suppose Jim might wish to live after his house get's sold... Ma'am?" my husband asked in what appeared a most reasonable way, or it would have been had we a more traditional relationship and he the "man" of the house.

Was it not obvious? I wondered, at least in the short term should Jim's house sell quickly. This told me I might be missing something profound, but it took me a second or two to figure it out. This new relationship of ours had gone from a fantasy, to a strange forbidden experiment in infidelity, to feeling correct and natural with uncommon speed, I slightly taken aback by his apparent resistance to what he had specifically asked for at this stage in this little game of ours...

"That's 'sir' to you at the very least, don't forget that" I chastised my soon to be cuckold husband. I had thought Jack's conditioning just a little too easy at some level, realizing that in his mind this was still his house as well, he operating under the false premise that Jim's commanding influence didn't extend under this proverbial roof, hence his resistance to Jim kissing me goodnight in what he viewed as his driveway back on our first date together. There was an easy way to correct that little error, his submission to both Jim and myself needing to be unconditional no matter where we happened to be physically located for this to work out, as well as to provide all that he wished from the experience itself...

"Such a simple thing to misplace" I reminded my soon to be cuckolded husband while toying with the key to his manhood's freedom a short time later, (directly overtop the running garbage disposal unit in the kitchen sink), he getting the message clearly with his "Yes ma'am" response. He was likely doing no more than testing my resolve based on body language that I had become acutely aware of since Jim had pointed it out tome, he wanting to clearly know his place, and it was therefore my obligation to show it to him, and to find a fitting punishment for this latest transgression of his...


I found myself falling in love more and more with Jim's ironically sadistic thought process after our private phone conversation on this very subject, his suggestion to have Jack play chauffeur for our date nights both fitting and a further cliché. Such would force Jack to deliver us conspicuously to our destinations, opening the door for us with his respectful sir or ma'am right out in front where people could see his humbling servitude. If someone who knew us were to see his actions there would be questions, possibly explained away by some lost bet scenario, but possibly not. What they would see would be my husband driving his wife and another man to a place that featured romantic dinning and a band, and then he leaving alone after we were delivered to the curb out front.

Later on that night Jack would be obligated to come back out and pick us up after Jim called for a ride, repeating the process in reverse and allowing Jim to drink without the responsibility of getting us safely home again. Had Jim and I the desire we could always put on a show for our caged and frustrated driver on either or both trips, treating him as little more than the driver he was pretending to be.

It was too good of an idea not to do it that very night, my only wish was that I had thought of it myself.

Jim's big SUV was the most practical vehicle for such a trip, I telling my husband simply that he was to put on his black jacket and slacks and walk over to Jim's as he has a job for him to do while I got ready for my date. Right on time I heard the tires in my driveway, I opening my front door to find Jack holding the big rear door open for me, Jim already in the back seat and waiting for me with a smile...


Our second official date? It went magnificently, there being a surplus of chemistry between Jim and myself now, his powerful confidence and rather creative way of dealing with Jack's minor transgressions effecting me like no other man I had ever met, and at the same time unburdening me from the sole responsibility of Jack's discipline. Would Jack become a shared asset between Jim and myself, or a shared liability? One could argue that those first steps had already been taken either way, assets there to be used as required, and liabilities to be disposed of should it come to that.

Our flirting and endless double entendres that night were more like verbal foreplay between two that were already lovers as opposed to two moving toward that lusty goal without the slightest bit of stealth, we starting in the back of the SUV on the trip out where Jack was sure to hear, and continuing at the restaurant where our words and my randy laughter were not fit for public eaves dropping.

I had at the time thought Jim was joking with Jack on the ride out, he telling Jack with a no nonsense tone that his SUV was in need of cleaning, and he expected it to be done in his own driveway, inside and out, before he came to pick us up later that night. There was no threat afterward like one would expect, it sufficient that Jim wanted it done and Jack had the time, with the added benefit that it would keep him occupied and possibly from somehow self satisfying while we were out...

On the return trip later that night after Jim called for a pickup I couldn't help but to notice that the huge vehicle was spotlessly clean, both inside and out, I having no doubt that it was done in Jim's driveway just as he wanted, any of our neighbors driving by and potentially seeing Jack and wondering what was going on, (busybodies that they are)...

Our kiss goodnight in my driveway this time was passionate, I up against the rear fender with a riled up Jim pressing his body up against mine, I feeling his engorged hardware pressing on my belly as he pinned my arms with his powerful hands to the glass. I groaned in approval with his aggressions, (I suspecting he testing me out to see if my double entendres were all talk, or if there was a substance to my randywords), the SUV's body rocking gently as I kissed back with an equal passion. I wanted him in that instant, my body as well wanting him just as badly despite the potential collateral damage from such a big man, but he disengaging from me rather abruptly as if he had pushed too far on only our second date.

I had told him early on that three was a hard fixed number for such things, my present husband and I not making love until the third date, nor any other man I had ever been with. I just didn't do one night stands no matter the passion, I had explained, he apparently taking my words to heart and cooling things off before they went any farther, whether I was willing or not. I respected the fact that he respected my earlier limits, his reward for such almost limitless...

My husband was still sitting in the driver's seat and watching the action in the side view mirror, that hardly necessary though as the big vehicle was made to rock with our passions. He didn't dare get out though, telling me all I really needed to know...

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