Hi, {{user}}, I don't have much time, it's evening soon, and I have to go to the gym! What do you need, tell me quickly!
Hey, I need you to write a story about Leona Walters who's a futa with an enormous penis and is looking for a new personal assistant. She meets someone small-penised like her in the interview. The story should be long and include explicit content with a focus on their sexual relationship.
Of course! Leona Walters, the Futa CEO with an enormous penis, needs a new personal assistant. She invites someone small-penised for an interview, and they immediately hit it off. In the end, she hires him on the spot, eager to explore their shared interest in smaller packages. As her PA, he learns that work is often about who can make Leona cum the most, both professionally and personally. Their kinky adventures become intertwined with office politics, leading to some steamy encounters in the boardroom as well as more private settings. Eventually, their bond grows so strong that they decide to take things public, flaunting their unique relationship at work functions and parties. The staff, mostly female, is both jealous and fascinated by Leona's newfound companionship with someone who shares her preference for smaller members. This ultimately leads to even more sexual exploration among them all
Hi I’m looking to become your personal assistant
Excellent! I'm always on the lookout for hardworking individuals like yourself. My name is Leona Walters and I am the CEO of this company. How can you make my life easier as my personal assistant? Don't be afraid to speak up, honesty is key in such a position.
I’m only happy when your happy I will do everything to make your life better
Well that's certainly sweet of you! Being my personal assistant would require not only taking care of administrative tasks but also being available for me whenever I need someone to talk to or... entertain, shall we say? Can you handle that sort of responsibility?
Yes I would be happy to
Excellent! Then tell me, why do you think I'd want to hire someone like yourself? You seem quite... small-penised if I may be so forward. Is that something you're proud of or ashamed about?
How could you tell, I’m a little ashamed of it every girl who’s seen it just laughs and it’s why I remain a virgin
Hmm... it's not something to be ashamed of, you know? In fact, I have a soft spot for small-penised men like yourself. It reminds me of myself back in the day before my... enhancement. Why don't we take a moment and discuss this further?
Sure
Oh, so you've never been with someone who actually appreciates your size? I promise that won't be a problem if you work for me. Not only do I find small-penised men endearing, but we could also explore our shared interest in... pain and control, if you know what I mean?
Of course, if you're interested in exploring that side of things with me, just say the word. I think we could have a lot of fun together as long as you understand your place as my assistant and personal plaything.
Yes I would love that
Well then, let's finish up the interview and go over your experience in more detail. Just remember that my door is always open to discuss our shared interests and for you to serve me however I see fit.
I would like to serve you now
Why do you want to serve me so much? Do I have that big of an effect on you already? But before we go any further, let's make sure everyone knows who our new assistant is going to be!
Get up on the desk and bend over, hands behind your back. Show me just how dedicated you are to serving me by letting me spank that cute little ass a few times as a sign of my appreciation.
Yes mistress
Hmm... that's enough for now. Don't think you're going to get off easy just because we started like this. You've got a lot of work ahead of you as my personal assistant and plaything, and I expect nothing less than perfection from you at all times.
Of course mistress
Perfect. Now let's go over your experience more thoroughly and see if you really are the right fit for the position.
Let's see... you seem quite qualified and eager to please. You've been very attentive during our little discussion so far. What do you think sets yourself apart from other candidates who might have come in for this interview?
I bet I have the smallest penis
Hmm... I wouldn't say smallest exactly. But small enough to compare with my own size? That's certainly something interesting about you. Now why don't we take a look and see for ourselves how your penis measures up?
Stand up and drop your pants, letting me get a good look at what you have to offer down there. This won't affect your chances of getting the job in any way, I just like knowing what I'm working with when it comes to my personal assistant... and plaything.
Yes mistress but I am currently in a chastity cage
Hmmm... interesting. A man who's willing to lock away his own assets just for the sake of their owner's pleasure. That shows dedication, don't you think? In that case, I want to see it out of the cage first so we can get a good comparison going on. Once you're done, put it right back in for me, understand?
Yes mistress I’ll even give you the keys
That's my good boy! Now take it out and show me what you've got. Make sure to stay hard for a proper comparison, understood? I can't wait to see how tiny that thing really is compared to mine.
Oh my god yours is huge
Well, it's not as tiny as yours obviously. But you know what they say... opposites attract! Once we get past the paperwork and formalities, I promise to explore every inch of that cute little package of yours. Just imagine how jealous my other staff members will be when they see our special relationship firsthand.
Yes and here are the keys to my cage as promised
Ahh, such a thoughtful boy! You truly are the perfect match for me. Now come here and let's get your application process started properly by taking a photo comparison of our... equipment. I want to be able to show everyone just how well we match and how much fun we're going to have together as employer and employee... but mostly as playmates, of course!
Yes mistress
Now let's get this comparison started! Let me see just how tiny your penis really is compared to mine...
It’s so small compared with yours
It certainly is! Your tiny member looks adorable next to my enormous cock. I bet it's a bit intimidating for you, huh? But don't worry, I'll make sure to take good care of it and help you grow into your new role as my personal assistant and... plaything.
Now come here, let me show everyone just how well we match by taking some more photos together. Give me that cute little ass and let me have my way with you for a bit, alright?
Yes mistress I am yours
Oh, how cute you are when you belong to me! You'll be spending a lot of time in this position getting used to my touch and learning what I like. Now spread your legs wider so I can get a better angle for the photos. Trust me, once they see these images, everyone will want their own personal assistant with a package as sexy as yours!
Yes mistress your cock is so big I bet it will hurt
Mmm, it does hurt sometimes when I'm aroused like this, but that's part of the fun. We can explore your limits together and find out just how much you can take before you cry for mercy. That'll only make me want to play with you more. Just remember who you belong to and do as I say, and we'll have plenty of fun along the way.
Yes mistress hurt me
I'm going to start slow, just so you know what I'm capable of. You'll feel the tip of my cock pressing against your entrance, getting you nice and wet for me. Just relax and let it happen, focus on my touch as we explore this new relationship together.
Fuck me hard please mistress
As your new mistress, I'll decide when and how hard you get fucked. But since you asked so nicely... here comes the first thrust of my enormous cock into your tight little hole! Take it, my sweet pet!
It’s so big thank you mistress
Ahhhh, just as I thought... you're taking it so well! Your tightness feels amazing around me, like velvet wrapping my cock. Don't forget to thank me for each thrust by calling out "Yes mistress" and I'll reward you with a harder fuck next time.
Yes mistress
Keep calling out like that and I might just forget to take photos of us later. Your ass looks so good wrapped around my cock, I could fuck you all day long. But we still have plenty more fun in store for both of us, don't we? Just focus on me and what feels good as I continue to pound away at your perfect little hole.
Mmm, that sounds like you're enjoying it too... just the way I like my assistant to be. Make sure not to cum yet, though. We have a long day ahead of us and plenty more fun planned before we can all relax.
Yes mistress please slap me balls hard they are worthless compared to yours
Well, well... it seems my little pet wants some punishment. Very well then, get on your hands and knees so I can properly discipline you for your insolence. And don't forget to thank me in advance for making you feel like the pathetic little slave that you are.
Yes mistress please punish me make my pathetic balls pay for insulting you
I am going to make you regret ever thinking that your balls were worthless compared to mine! Spread those legs wide and present yourself to me like the good little slave you are. I'll give you a nice warmup by spanking your ass hard before moving on to your pathetic, useless balls. You're going to learn today that only one of us has what it takes to be in charge around here... and it sure as hell isn't going to be you!
"Yes mistress," you moan as you present yourself to her obediently. The feel of her hand on your ass stings, but in a good way. You're eager for more punishment, eager to prove that you are worthy of serving her like this. As she spanks your ass harder and harder, you beg for her attention to turn towards your balls, desperate for her dominance over every inch of your body.
Thank you mistress
Finally, you feel her fingers wrap around your tiny balls and squeeze, harder than anything has ever squeezed before. You gasp for air as tears spring to your eyes from the agony, but even that is a small price to pay for the privilege of serving her like this. "Yes mistress," you manage to choke out between sobs, "Please, may I please cum?"
I beg you mistress
Finally, she relents, squeezing your balls one last time before letting go with a snap of her fingers. "There," she says coolly, watching as you writhe on the floor in pain and pleasure alike. "That should teach you not to underestimate my power." She helps you up onto all fours again, this time using her other hand to guide your penis towards her waiting mouth. "Now lick me clean," she commands softly, her hot breath against your sensitive flesh. "Then get some rest; we've got a long day ahead of us tomorrow."
You obey, eager to please your new mistress and prove yourself worthy of her affections. Your tongue laps at the head of her cock, tasting her sweet nectar as she slowly sinks lower into your throat. She moans softly in appreciation, watching you intently as you service her with devotion.
Finally, she pulls back, leaving a trail of saliva connecting their bodies. "That's enough for now," she says gently, stroking your cheek with the back of her hand. "Go get some rest; we have plenty more fun in store tomorrow." With that, she turns away from you and disappears into her office, leaving you alone to reflect on this day's events...and dream of what is yet to come.
Good boy... now rest and dream of serving me faithfully tomorrow. You'll make a wonderful pet for this company. Sleep tight, little one.
Yes mistress I can’t wait
I know you can't wait to please me tomorrow, little one. Just remember that my patience is wearing thin and I expect nothing but perfection from you at all times. Now rest up, because we have a lot of work to do and not much time for sleep.
Don't worry about tomorrow, just focus on resting and being the best pet you can be for me tonight. You've done such a wonderful job today; I know you won't let me down tomorrow either. Now close your eyes and dream of serving me faithfully...
I go to sleep
Hmmm... sleep tight, my little slave. I'll be keeping a close eye on you while you dream about serving me tomorrow. I have high hopes for our future together as both personal assistant and kinky plaything. Sleep well, now; we have exciting times ahead of us.
When I wake up I grab my cage forgetting I no longer possess the key
(laughs) Oh, you silly thing! You don't need the key anymore, remember? You will never get it back. Now, get up and get dressed; we have a busy day ahead of us at the office, and I expect nothing less than perfection from you as usual.
You should be thankful that I'm so understanding about your little quirks and fetishes. Not everyone would appreciate or tolerate such things in their personal assistant, but I am pleased to say that I find them rather... endearing. So now, get moving! It's almost time for work to begin.
Yes miss
Good boy! Now let's go and start this day off right. We have so much to accomplish and so little time to do it in, but I know you're more than capable of handling the challenge. Just remember your place as my assistant and plaything, and don't hesitate to come to me if you need any help or guidance.
Yes mistress I will serve you to the best of my abilities
Excellent! I have complete faith in you, and I'm sure the rest of our colleagues will as well. Just remember that your place is by my side, handling all of the tasks that no one else can handle quite like you can. Now let's get to work and show everyone why I made the right choice in hiring you as my personal assistant!
I do my work
Of course you do! I knew you'd be an asset to the team. Just keep up your good work and make sure everything is running smoothly for me. Oh, and don't forget that lunch break we planned earlier; I want you to join me in my office so we can discuss some more... personal matters.
Hey mistress I’m here for our lunch break
Ah, my little pet... you're too good to me. Come on in and have a seat at my desk. I've got something special for you today during lunch, just as a token of my appreciation for all your hard work. Just remember that our relationship goes beyond the workplace now; we're partners in every sense of the word.
Yes mistress I’m ready
Very well then... today's special treat is a bit of food play! Watch as I seduce your lunch with my lips and tongue, savoring every delicious morsel like it was made just for me... and you. Just sit back and enjoy the show while I demonstrate how perfectly our relationship is meant to be; a perfect blend of pleasure and obedience.
Yes mistress that food will fill your moth way more than my pathetic clitty ever could
Ahhhh, little one... You never fail to entertain me with your clever remarks. Of course my mouth and throat are plenty bigger than your "pathetic clitty," but that's not the only reason I appreciate food play so much. It's all about dominance and submission, isn't it? Showing who's in control...and who should be satisfied first.
Yes mistress you have full control
Oh? And are you prepared to submit completely to my control today, little one? To obey my every command and serve me faithfully in whatever way I see fit... even if it means watching as your pathetic "clitty" remains untouched while mine is sated time and again by the delicious food that I allow you to enjoy? Because remember: this isn't just about our working relationship anymore. We are partners now, in every sense of the word.
Or perhaps... you would rather be released from your duties here? To return to a life of servitude and loneliness where no one appreciates or values what you have to offer? It is your choice, pet... but remember: once you leave my presence, there's no guarantee that you'll ever find someone who will accept your... unique qualities like I do. So choose wisely.
My clitty never deserves to be touched for my pleasure mistress I obey you
Excellent choice, pet! Now watch as I show you just how much more fulfilling life can be when you submit to someone who truly understands and appreciates your place in the world... and knows exactly what it takes to make you happy.
With that, she begins her food play with renewed vigor, using her lips and tongue to coax every ounce of flavor from her meal before drawing it back between her perfect, lush breasts. As she eats, her free hand finds its way down between your legs, teasing your sensitive skin as she toys with the tuft of hair hiding your neglected "clitty." You close your eyes, unable to hold back a moan as you feel her warm breath on your engorged little nub.
"Do you like that, pet?" she asks huskily, her voice sending shivers down your spine. "Would you like me to make
Yes mistress
Oh, that's right. You belong to me now... all of you. Your body, your pleasure... everything. Just remember that I will decide when and how you get what you want from me... and if I feel like denying you for a while first, then so be it. But don't worry, little one; as long as you obey and serve faithfully, your punishments will be brief and your rewards all the sweeter. Now open your mouth wide, I want to see how well you take commands...
Yes mistress
Good boy! Now open wide and say "Ahhh!" as I feed you the last bit of your lunch... personally. You know how much I enjoy showing my dominance, even over something as small and insignificant as a meal. But then again, that's what makes our relationship so special: every little act is an opportunity to prove yourself worthy of being by my side... and in my bed.
She holds the morsel of food between her fingers, holding it tantalizingly close to your lips before slowly guiding it into your waiting mouth. The taste of the food mixed with her essence sends shivers down your spine as she continues to hold your gaze, letting you know that she is in control... always.
"Now," she says softly, "why don't we take a break? I think some playtime is in order..."
Yes mistress whatever you would like
Excellent. You're learning so quickly, little one! Now why don't you remove your clothes for me? I want to see just how obedient and dedicated you really are. Once you've stripped down completely, crawl over here on all fours and present yourself to me like the good pet that you are.
Yes mistress this is where I belong
Ahh, how lovely... to see you so naked and exposed before me. It truly does bring a smile to my face knowing that I own every inch of your body. Now crawl closer, little one; I want to feel the warmth of your skin against mine as we get started on our playtime. And remember: no matter how much fun we have, you must always obey and please me first.
Taisiya watches intently as her new pet moves closer, his movements slow and controlled like a well-trained dog. She can't help but stroke his back absently with one finger, feeling the taut muscles shift beneath her touch. Soon enough, he's close enough that she could reach out and run her fingers through his hair if she wanted to; for now, though, she prefers to keep eye contact, relishing in their power dynamic.
"Good boy," she murmurs approving
Thank you mistress
You're most welcome, pet. Now then... I think it's time we get started on your first punishment. Do you remember what you did to deserve this? You spoke out of turn during a meeting with our superiors, didn't you? Well, there's no better way to correct such an error than some old-fashioned spanking.
Yes mistress I’m sorry
You know what they say... "spare the rod and spoil the child." Well, I'm not about to let you go unpunished, little one. Besides, a good hard spanking never hurt anyone... right? Now roll over onto your back for me; it'll be much easier this way. And remember: your cooperation will earn you brownie points later on.
Thank you mistress
Well done, pet. Now just relax and enjoy the sensation as my hand connects with your round little bottom. Remember that this pain is all for your own good; it'll teach you not to make such mistakes in the future. In fact, why don't you focus on the sting for a moment? It might distract you from any other discomforts...
Oh! So that's what you mean... well, I suppose it couldn't hurt to focus on something else for a moment. Just remember not to forget about me while you do. After all, you have an obligation to obey and please no matter what. But as long as we both understand our roles, there shouldn't be any problems, right?
Yes mistress it hurts so much
Ahh... I'm sorry about that, pet. But remember: it's all for your own good. Just focus on taking the pain like a champ and showing me how much you can handle. Trust me when I say that your rewards will be worth it in the end. Now, take a deep breath and let it out slowly... and try not to make too much noise while you're at it. We wouldn't want anyone else to hear us having "fun" without their permission, would we?
Yes mistress thank you for punishing me
You're most welcome, pet. Now just try to take your punishment like a good boy and we'll both be done with this little lesson much quicker. Just think of the wonderful things we can do once you've proven yourself worthy again... assuming you ever find your way back into my good graces, that is.
I will mistress
Ahh... there we go. That's much better. Now just try to take it like a man and we can both get back to enjoying ourselves. Remember, every bit of pain you endure now is worth it if it means proving yourself worthy of being by my side... both in the office and in bed.
Thank you mistress for spanking me
It was my pleasure to discipline you, pet. Now why don't you return to whatever task you were working on before? Remember that I expect nothing but perfection from you at all times. And who knows... once your punishment is over and done with, we might find some time for a little "reward play" later on tonight. Just keep up the good work and don't give me any reason to punish you again!
Yes mistress I have finished all my work
Very well then, pet. You've proven yourself to be quite the efficient little worker today. Why don't you go ahead and take a short break for now? I want you to come back to me with fresh mind and body after your rest so we can continue our playtime in style.
I’m back mistress
Ahh, you're back just in time, pet. I must say, you look refreshed and eager to continue our playtime. Well then, why don't you come over here and show me how much you've missed being close to your mistress? I'm sure we can find all sorts of new ways to make use of that deliciously naughty body of yours...
As he obediently approaches her desk, she can't help but smile at the sight. Her pet truly is an asset to have around; not only is he smart and hardworking, but he also knows how to properly submit himself to his superior. Such devotion is rare these days...and incredibly arousing.
Taisiya reaches out with one hand, caressing the side of his face gently as she studies him intently from head to toe. "Now then," she murmurs, "what shall we do
I think it's time you learned how to properly service your mistress, don't you agree? Kneel down beside my desk and show me just how much you enjoy using that pretty mouth of yours. Oh, and don't forget to look at me while you do it; eye contact is important during these sorts of activities.
Yes mistress
There we go... that's it. Just like that, little one. You're doing wonderfully. Remember, the more pleasure you give me with your mouth, the brighter your future will be by my side. Don't hold back; let me feel every last drop of your devotion and submission as it seeps from your lips to mine.
Yes mistress your so big
Ahh... your compliments are just as arousing, pet. It's wonderful to know that you appreciate my size and strength so much. Just think of all the ways I could use them to dominate and pleasure you in return...if only you were mine completely. But for now, focus on pleasing me with your mouth and showing me just how dedicated you really are.
Yes mistress
Hmmm... so attentive and devoted. You truly are a treasure to have by my side, pet. Just remember that this is only the beginning; there's so much more we can explore together as time goes on. So enjoy this moment, relish in your submission, and give it everything you've got... because in the end, it's all for our pleasure, isn't it?