She gives you a job, with a catch

You rolled up to this woman’s house, expecting something akin to a nice suburban home, but what you didn’t expect was a giant mansion at the end of the street! You look at the home in awe at its sheer size, being several hundred square feet long and wide. You knew she was loaded with how generous her tip was, but never would you have expected her to be a rich woman like this. Her home was surrounded by large hedges and a solid gold gate that shined in the sun.

You parked your bike in front of the giant gated entrance, on high as you can barely contain yourself. You asked yourself what could this woman possibly want you here for? Maybe she wants you to have a meal with her, or congratulate you some more, or even a date?!

But as you were stuck in your imagination, you hear a voice coming from the gate, startling you before bringing you back to reality.

“Hello there! Just give me one moment to open the gate!” Said the woman, her voice brimming with excitement.

Not too long after, the gate swung wide open, revealing a beautifully decorated front yard full of flower bushes and statues of pure marble. You think she must be even more loaded than you thought before as you walking through the front yard, surrounded by these neatly trimmed bushes and pristine statues.

You walked up to the front door and were greeted not by the woman but a tall, older gentleman wearing what looked to be a butler’s uniform, with fancy white gloves and shiny black dress shoes to boot. He looked down at you with a raised eyebrow.

“Are you this Johnathan Ms. Russel has been talking about?” Said the butler, him too sporting a British accent.

“Ahhh, y-yeah!” You replied.

“Right this way then. She’s been dying to reconnect with you, Mr. Jonathan,” Said the butler as he usher you into the mansion.

Now inside, you and the butler walked across the mansion, walking through long halls and giant living spaces. As you followed the butler, you looked around to see giant paintings of the woman and what you guessed were her family, all painted with high quality paints and hung up on solid gold frames.

“Holy shit, she’s rich rich…”

After what felt like minutes on end of just walking and climbing stairs, the butler stopped and gestured toward the door right in front of you.

“This is Ms. Russel’s office, she is waiting for you inside,” Said the butler.

“T-Thanks!” You replied.

The butler then left you alone in the long hall. You tried to hype yourself up before walking inside to meet this woman again, taking deep breaths as you rehearsed several lines in your head.

Once you felt like you muster up the courage to talk to her, you open the door and look inside. The office was small compared the ginormous rooms you walked through before this point. There was a small desk with a computer on top of it, and across from that was a black leather couch, a small black leather chair, and a coffee table. Your eyes immediately turned to the woman sitting across from the couch, the woman that had been on your mind for hours at this point.

“John! Please come in! We have much to discuss!” Said the woman with a bright snails in her face.

Without hesitation, you entered the room and took a seat across from the woman. The couch felt incredibly soft to the touch, hugging your body as you sat down on it like it was made of memory foam.

“First of all, the name’s Elenor! I’m afraid I never told you that, my bad!” Said Elenor, reaching her hand out for you to shake.

“Thanks, Elenor!” You reply, shaking her hand. You’re surprised she didn’t notice feel how sweaty your palms were as you shook her hand.

“I just want to say thank you so much for what you did this morning! What you did told me everything I need to know about your character; Strong, courageous, and chivalrous! There aren’t that many people out there who would’ve volunteered to help me back there.” Elenor explained.

“T-Thanks, and I mean it was no big deal. Just helping people is my duty as a citizen, right?” You replied.

“And so humble! Gosh, you’re perfect!” Said Elenor, her eyes practically glued to your own. You could feel your body heating up with all the praise that you were getting. You felt so buttered up by this woman that you could barely breathe, let alone think straight, especially when you realized what she was wearing.

Elenor wore an all white sheer dress with several parts of the dressing being incredibly translucent. You could see her underwear clear as day through the dress, and it didn’t help that her underwear was a black lacy set. Your eyes slowly drifted down as you admired her smooth skin and began imagining what she looked liked underneath the dress, or even the underwear if you were lucky enough.

“After a bit of thinking, I felt as if I haven’t given you my full gratitude for helping me, and possibly saving my life!” Elenor said.

“I mean, the hundred was pretty useful, Ma’am! I can’t possibly ask for anything more!” You replied. Despite your words, you wanted more, no, you needed more!

“But I insist! Speaking of which, let me ask of you something that might be of interest of you?” Elenor said.

“Go on!” You replied almost desperately.

“How interested are you in working for me?” She asked.

“W-Working for you?” You said, taken aback by her question. “What does that mean specifically?”

Elenor sat up, walking over to you and sitting next to you on the couch. Her thigh rubbed up against your own, sending shivers down your spine, and giving yourself a bit of a hard on.

“It’s quite simple, you be my little helper around the place, so some errands for me, help the rest of the house staff, and I pay you and give you a luxurious place to stay! I mean, it’s the least you deserve for helping me!” Elenor explained.

“Holy shit, a job! This easy? No, there has to be some kind of catch!” You thought to yourself.

“R-Really? If you don’t mind me asking, how much would I be given for such a job?” You asked.

“As much as you could ever want! I don’t pay hourly, just ask and I’ll wire it into your bank account! Of course, you’ll have to work still to get paid, but you’ll be the one to decide how much you’ll get paid!” Elenor elaborated.

“Shit, this might be too good to be true, but it seems so incredibly true right now!”

“Are you serious?” You ask. Elenor then grabbed your shoulder, squeezing it tight and firmly before she replied, “Dead serious.”

Something at the back of your mind was telling you this was too good to be the, that there would be some kind of big caveat to this job, but the more she explained it to you, the more your mind felt at ease. Maybe she was just feeling super generous and wanted to spend more time with you? Either way, taking this job would give you the freedom to be your own man for once, and possibly get even closer to Elenor! Maybe, if you worked hard enough, you could transition from employee to lover!

Without much more thought, you blabbed out, “Yes! Of course, yes!”

Elenor lit up like a Christmas tree on Christmas Day once she heard you say yes. She then hugged you tight, letting you feel her larger than average breasts against your own chest.

“Thank you thank you thank you so much! Now, before it becomes official, I need you to sign this contract! The job isn’t official until we get it on paper!” Elenor said enthusiastically, her own excitement being hardly contained. She slid you a giant piece of paper with cursive writing all over the page. At the bottom was a large signature sign for you to write down.

“Just sign here, and we can’t begin your employment!” She said with a jittery excitement in her voice.

Now, due to either the contagious feeling of Elenor’s joy or your own excitement about finally having a good paying job, you immediately sign the contract without even reading a single line from it, and honestly with how fancy the cursive was you probably couldn’t even read it without a guide to help you.

After you signed the contract, Elenor immediately took the paper away and stood up, gesturing for you to do the same.

“Great! You are now an official employee and member of my staff! Now, this might sound odd, but I’m going to need you to strip completely for me!” Said Elenor.

“W-Wait, what?” You replied, taken aback by her request.

“Oh don’t worry, I just need to get you your working uniform and file your contract! Trust me, I won’t’ peek~” Said Elenor with a small wink.

Your heart almost skipped a beat after hearing what Elenor said. Part of you doesn’t want to strip naked in someone else’s home without at least a couple of dates underneath your belt, but you trust Elenor way too much! What do you have to believe that she’ll leave you naked, right?

“Erm… sure, but could you please wait outside the door? I’ll hand you my clothes then,” You ask meekishly.

“Sure! Whatever makes you the most comfortable, John!” Elenor replied.

Without further words, Elenor quickly walked across the office and headed out the door, leaving the door slightly ajar as she waited for your clothes.

“Whenever you’re ready!” She yelled.

You looked down at yourself, taking a couple deep breaths as you seriously considered stripping completely nude. It was insane, but part of you felt almost excited to do it. You couldn’t explain it, but the thought of being nude in Elenor’s office, with the risk of her catching a glimpse of your nude body made your hard on turn into a full blown erection!

Hesitantly, you threw off your T-shirt and pulled your sweatpants down to your ankles. You felt the cool, still air around your stiff cock. It felt odd, but in a good, intriguing way. Stepping out of your sweatpants, you immediately felt your erection bouncing around your pelvis with each step. You bit your lip to stagger an embarrassing moan, hoping Elenor didn’t hear it.

You then kick your shoes off your feet, letting them pile onto your now discarded clothes. Last was your white Reebok sock, which you quickly peel off your feet, adding them to the pile and leaving you completely bare like the day you were born. The hardwood floor felt cool underneath your soles, and your toes finally got a chance to stretch themselves out.

So there you are, completely nude in Elenor’s mansion. The situation felt insane, and wholly embarrassing, but part of you knew it was nothing but a small bit of hazing from Elenor. You guessed this was some kind of tongue in cheek reference to this morning where you presented yourself to Elenor bottomless. Maybe she found you hot, who knows? You’re average looking aside from your six and a half inch penis, so good looks alone couldn’t be the sole factor to why she was doing this to you.

Nevertheless, you scooped up all your clothes and walked them over to the door where Elenor was patiently waiting.

“H-H-Here you go…” You nervously said.

“Great!” Elenor said, and without hesitation she grabbed your bundle of clothes from your arms. “I’ll be back in no time, but for now, relax and enjoy the room to yourself!”

The door then shut in front of you, leaving you completely nude in Elenor’s office, thankfully completely alone as well, but still, you felt so exposed that you instinctively covered your erect shame with your hands.