Career Day, Ch. 02

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Opportunity?
2.7k words
4.73
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Part 4 of the 4 part series

Updated 06/21/2023
Created 06/05/2023
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Thank you all for the compliments. I'll try to keep it fun. This is part 2, and I'm working on 3, maybe more.

What the Hell am I doing here? I should be running out of this place as fast as I can go. I am SO not gay! But..Amber...what is she? She looks like the hottest girl I've ever seen. And, FUCK! That blowjob, my first, was so much better than anything I'd dreamed of. WHY am I here? Surely, they don't think I could look like that, DO things like that. And...WHAT would I tell my Mom? Wait, doesn't matter, I'm NOT gay...right? Shit!

All these things kept swirling in my head, until I had a raging headache. That's it, I'm leaving. Just as I stood up, though, Amber walked back in, followed by Nathan.

"Eric? You aren't leaving, are you? Don't you want answers? You already know there is nothing for you (wide gesture) out there, don't you? We (looking over her shoulder at Nathan) believe in you. You are our top pick, we can give you a life you could never imagine anywhere else." She gently pressed her hand on my chest, pushing me back into my chair. "Just give us a chance. If you don't like it, you are free to go, ok? You will only sign a contract if YOU feel comfortable, alright?" (Big smile,and she seductively licked those strawberry lips)

"I... (Dammit, she knows she has me) will... TRY it, but, I'm NOT gay, ok? I'm not sure why you'd want me."

That's when Nathan stepped closer. "Eric, does Amber look 'Gay' to you? (without waiting for an answer) of COURSE not! She is a beautiful young woman, ok, not completely, but you see what I mean, who is living a happy, successful life. We can give you that life, too." Amber is still smiling,

and nodding. "How about this; Give us ONE day, to show you how we change girls. I will personally give you $200 for the day, no questions, no strings, if you STILL think you don't fit in. We have 8 of your classmates who are giving it a shot, but YOU are the one we feel the best about. Sound good?"

Without waiting for an answer, he took my hand and shook it. "Alright, then, let's take this to our facilities!"

I still don't remember much about the hour long drive. Other than the expensive brick encased sign at the front of the drive, the building was pretty nondescript. Apparently, I was the late holdout, and my classmates were already there. After the lobby, and a few offices, there was a long hall, and smaller rooms on each side, with a larger meeting room, at the end. I was led into one of the rooms, and asked (not told, I noted) to undress and put on a hospital type gown on. A nurse came in, took my temperature, blood pressure and small sample of blood. She saw the look on my face, and said it was to match any prescriptions I may need. When I said I would only be here for a day, she smiled, replied, of course, and told me the doctor would be in an a moment.

Very soon, a middle aged man stepped in, offering to shake my hand. "Eric, isn't it? I'm Dr. Stafford, I'm just going to check you a bit. You look to be in good shape. Do you run? Exercise? I'm guessing that you'd hope to grow some mass, but it never happened. No worries, it's a bonus, here." After poking, prodding, and a few more questions, he says, "Nice to meet you, Eric, we'll see more of each other, I'm sure. That door leads to a bathroom. Please put this cream on your legs, wait 15 minutes, then shower. Oh, and shave your face, chest, underarms, and genitals, as closely as possible. There will be someone waiting for you, as soon as you finish."

Fuck! I'm shaving my cock and balls? Oh, well, it's $200, and it will grow back. The cream is to make my legs feel softer? I don't know, but can't be that bad. No one ever touched them, anyway.

The bathroom looked like something from a 5 star hotel, all marble and expensive fixtures. And the water pressure, wow! I know I was in there 30 minutes. So Relaxing. I was almost finished before I saw the fine hair on the shower floor, and saw how smooth my legs were. Crap! I won't be able to wear shorts until it grows back. Ooooh, right, they are going to 'try' and make me look like a girl. Good luck with that. I dried off and slipped the hospital gown back on, and peeked out the door, to see a woman, who looked to be early 30's, attractive, dressed in scrubs, sitting at the vanity.

"Hello, Eric. I'm Pamela, I'll be doing your makeover today. Let's get a look at you, to see how we can accentuate your features. Mmmm, Nathan did well, you're going to be so pretty. Just sit back, close your eyes, let me work my magic. You are going to want to date yourself, when I'm through."

I know I was blushing, and she worked fast, rubbing my face with something, dabbing something else, painting my eye lids, eyebrows, and then my lips. I blinked open. Wow, that feels AMAZING. Like being kissed. Never expected that.

"Ok, Eric, I don't want you looking, yet, Charlene is going to do something with your hair, or put a wig on, that's her call. You are going to love it. DON'T peek! See you soon!"

And as she opened the door, Charlene DID enter. She was a stocky woman, mid-forties, I'd guess, with a hearty laugh. She asked if I liked girls with long, or short hair, and I told her, I just liked girls, period. She giggled at that, and decided, for today, we would go long, and pushed my hair up in a soft cap, then wiggled a brunette (my color) wig on my head. She slapped my leg and said, "All set, sweety," and popped out.

Before the door closed completely, a tall thin black man entered, with an armload of clothes, and told me he was Andre. He would hold up outfits, and asked if I like them, or not. When we agreed on one, He opened a box, and pulled out what looked like boobs. They were, silicone, with adhesive on the back, which he pressed to my chest. I have to say, I squirmed a bit. These things looked AND felt, like boobs....Or, what I imagined they would. They felt pretty real, to this virgin, anyway. Feeling the weight on these boobs, felt strange, but...somewhat erotic. I could actually imagine how girls felt, and kept looking down at them. For a guy who'd never seen REAL boobs, it was pretty exciting.

Next, he looked me in the eyes and said, "Don't freak out on me, but this next part is more personal, ok? I'm going to be tucking your balls and penis, to give you more of an appearance of being female. Right? Just trust me. Then, we'll finish getting you dressed." With that, his slender fingers slid under me, and gently pushed up on my balls. I was crimson red, but he did it so quickly, then put a strip of tape on my cock, (which had shriveled, due to my embarrassment) and taped it between my legs. The result gave my pelvis a very feminine look. He then handed me a pair of french cut panties, and slid sheer stockings up my legs. After strapping a pair of heels with ankle straps and 2 inch heels, (he smiled and said they were 'training' heels, that higher ones would come later)

Later, I thought. This is a one day thing. I just need to get through one day, collect the $200, and be on my way. ANYWAY, he had me raise my arms, and dropped a stretchy bright red dress over me, and tugged it down, until it wrapped on me like a second glove. He smiled broadly, and turned me to the mirror.

FUCK! That's me? Mousy Eric? I...I'm the woman of my dreams! Even I can't believe I'm a guy. I twist and turn, looking at my 'boobs', my waist, my hips, legs, and then back to my face. My mother wouldn't recognize me, ever. Ok, I get now, how Amber can be so hot. Damn this is fucked up, what do I do?

My question is answered, sort of, when Nathan comes in, smiling.

"So, Erica how do you like the new you? Have you EVER felt as attractive as you do now? You can see why we want you to join us, to be a part of giving people pleasure, making money at it, AND, lastly, feeling good about yourself. Now, we understand you are still...unsure...about this, so, what we are doing, tonight, is sending you and Amber, on a dinner date. You will meet a very nice gentleman, who is a special client. You will ONLY do what YOU feel comfortable, and Amber will be there to help, and, if need be, complete the task if she needs to. Does that sound fair?"

My eyes widened as I heard 'Erica', but realized that Eric would not fit, given my look. "Yes. I still don't think I can do...what you need, but I will go and see what happens. I admit, I never imagined being able to look like this, ever."

"Excellent! Let's get going, then. Amber is waiting in the lobby, and our driver will take you."

We walked down the hallway, it took the length of it to get me familiar with walking in the heels. I felt my hips swaying, and the way my ass seemed to stick out more. Yes, dammit, it felt sexy. Fuck me.

Amber stood there, smiling, watching us approach. She leaned forward, and kissed my cheek. "You look beautiful, Erica, just like I knew you would. (she looped her arm in mine) Let's go have a nice dinner, and see how the night goes!" I thought to myself, I might be in love with her, but, it occurred to me, every guy might think that of beautiful girls who give you your first blowjob.

We sat next to each other in the back seat, and the driver kept his eyes on the mirror as much as he did on the road. Amber also saw it, and teased him by cupping one of my 'boobs' and running her fingers up and down my leg. My face was beet red, but I was loving it. This girl knew exactly what to do, in every situation.

We arrived at a posh restaurant (one I couldn't imagine ever affording) and the Maitre D showed us to the table, where a tall, slender man rose from his chair, to greet us. I guessed him to be late forty-ish,

obviously well mannered, and educated. He complimented both of us, and thanked us for joining him at dinner. He ordered a bottle of wine, and we ordered our dinner. Amber and I purposely ate light. I had a feeling that a full meal might not show well in this dress. I guessed that Amber used the same idea. The dinner conversation was light. He told us what he did, places he'd been to, etc. He'd ask us about our lives, and both of us kept our answers vague. I was confident that he knew we wouldn't tell much, but was being polite. We had a second bottle of wine after dinner, and he asked if we'd care to join him in his state room. I looked at Amber nervously, and we both nodded yes. It wasn't until I stood, that I realized I was quite a bit more buzzed than I was before. I had to hold the back of my chair until I could steady myself.

We walked to the elevator, with him in the middle, with arms around each of us. Understandably, Amber handled her wine better, and was a bit flirtatious with him, bumping hips playfully. She wrapped her arm around his back, gently squeezing my arm, and giving me a wink. Being buzzed may have been a good thing, as I was nervous enough already. He dropped his arms from us long enough to pull his key card free and swipe it. We stepped in and my jaw dropped. I'd never seen any place as beautiful. He led us to a grand couch, where he directed, again, one on each side of him as we sat.

Amber took the initiative, and planted a kiss on his lips. Then, leaned further, to kiss me! They both smiled, and he stunned me by kissing me. I know my eyes and mouth went wide. Hell, I'd barely ever been kissed by a girl, much less a man. Amber stroked my face as he kissed me, and she kissed his cheeks, then mine. It may have been the wine, Amber, or just the weirdness, but I kissed back. I closed my eyes and pretended I was Amber, kissing this attractive man. In all this crazy petting, I did not notice that Amber had unzipped his pants, and pulled his cock free. I heard him moan in my mouth, but it didn't connect, until I felt Amber pull my hand onto his smooth throbbing cock. Oh Fuck, what now?

She kept her hand on mine, gently sliding it up and down. He pulled away from the kissed, leaned his head back, eyes closed.

Amber guided her eyes down to his cock,obviously wanting me to follow. She leaned down, licked the head of it, then, eyes on mine, waited for me to. The look on her face, as her tongue danced on his cock reminded me of what she did to me. I shrugged my shoulders and leaned closer. She kissed me and pushed my lips on him. "I knew you could do it, Baby. I'm so proud of you," she whispered. I felt his cock jerk as it filled my mouth. My face crimson red, my eyes locked on hers as she licked on his balls and the base of his cock, kissing me every time our lips were close. Who WOULDN'T do ANYTHING for her?

This time, I felt HIS hand on my head, pushing me on him. He was moaning faster, and Amber was smiling bigger. "Get ready, baby, he's ready." By the time I figured out what she meant, I felt and tasted his blast of thick cum. It filled my mouth, went in my throat, and in my nose. I was desperately trying not to choke, swallowing and swallowing. She pulled my face to hers hard, and locked lips, forcing her tongue in my mouth. She was fucking my mouth with her tongue, while mining for his cum. She leaned down, cleaned his cock clean, then stood, pulling me up, too.

"We need to freshen up, if it's ok, " she cooed, and he just nodded. She pulled me into the massive bathroom, kissed me again, then pulled makeup out of her purse. "God, Erica, that was SO hot! I knew you could do it!" she was wiggling as she touched up my makeup, then hers, stopping only to hug me several times.

I didn't know what to think. I really DID do something I couldn't have ever done before. I SUCKED a guy! The craziest part it, I didn't feel gay. I FELT like a girl, making a guy feel good. Damn, I GET IT!

We went back out, he said we had worn him out, that maybe we would do more, 'next time'. He handed each of us a hundred dollar bill, and wished us a good night. Amber tiptoed up to kiss his cheek, and I followed. Seemed only right. I wrapped that bill tightly in my hand as we rode the elevator down.

Amber turned to me and said,"Ok, Erica, we have 2 choices. We can call for our ride or, (she waved toward the bar) we can have some more fun. There are ALWAYS lonely men, mostly married, desperate for a good time. My mouth dropped open, but I did stop to think. She leaned closer and said, "either way? I'm fucking your brains out tonight."

God, that smile.....

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AnonymousAnonymous11 months ago

Oh, he's definitely gay! It took nothing for him to accept another guy sucking his cock and even less for him to do another guy. This could have been good, the coercion and technique to force him into the mindset of a women. Instead, because he's a virgin, he magically goes gay his first night out and he's hooked.

AnonymousAnonymous11 months ago

Sorry, A straight guy wouldn't do any of that. Maybe get dressed up for the $200, but not spend his night with another guy and certainly not suck a dick. Interesting premise that got out of hand. Too unbelievable, even for fantasyland.

EricaDoesNowEricaDoesNow11 months agoAuthor

Here is a recap: Below average guy with no real prospects. Desperate to find a job/career.

EricaDoesNowEricaDoesNow11 months agoAuthor

Hahaha. Sorry I disappointed. But, that IS why everyone can submit stories the way THEY like them to go.

AnonymousAnonymous11 months ago

The first part was good, this one not so much. Instead of being very suspicious about their motives, he dives right in. Doing things like a physical and blood draws are not things to allow when not employed and they kept acting like he was already in. Most in that circumstance would have been much more adversarial and observing without participating. Disappointed. Most of these stories are like this, the author lays out a good concept, then has the MC magically fall into everything presented.

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