Pretty... Woman

I was enjoying my vacation in New York City well enough. The city in the springtime was surprisingly pleasant. I was out on a stroll and taking in the sights when I decided to take a turn and head into Central Park for a moment, where I could just enjoy the beautiful weather and let the sun warm me up. It was a surprisingly quiet day in the city, everybody must be at work right now. I'd been staying here for two days now, taking a much needed vacation. At 28, I was surprisingly starting to feel burnt out with work. I'd been working tirelessly with little progression, and I was beginning to feel frustrated. I was fighting against stereotypes I had no control over. As a shorter guy with a slight frame, standing at 5'5" and 160lbs, I never really commanded the room and had trouble standing out amongst my more animated peers. Even if I outworked them and outperformed them where it really mattered, they always held more sway with the leadership at the top who saw themselves in this confident, outgoing young men. Who knew whatever happened to all the guys like me?

I'm wearing a light blue t-shirt, khaki shorts, and a pair of tan flip flops. I watch as people strolled by, enjoying the time alone to myself to people watch and try to forget all about work. I let out a deep sigh, leaning back deep into the park bench. I had a nice setup, the bench was a good walk away from the main path, nestled right up under some shady trees. And this was New York, who was going to come sit down right next to me? I've got this whole spot to myself.

"Excuse me, is this seat taken?" I hear a low, deep voice from over my shoulder.

"Um...." I say, looking around to try and find the source of the voice. I hadn't seen anybody approach me. I look to the left and standing there is a large man wearing a black suit. He struck an imposing figure, probably standing up to 6'5" with broad shoulders, long, thick arms, thick legs, and a slight gut protruding out between his suit coat. He sported a full head of gray hair, and a trimmed beard. "Well, I guess not..." I say, slightly moving to the side to make room for him. I didn't want to start any conflict with a random stranger in the city, so I decide to play it cool for a couple minutes before moving along with my day.

"I apologize, I must have startled you when I approached you. I didn't mean to sneak up on you, I was just coming from an odd angle when I saw you sitting here. You know, pretty people like you shouldn't be dozing off in public in the city." He says with a soft chuckle as I felt his gaze turn towards me. "I'm Alexander, Alexander Wilson. It's nice to meet you."

I laughed softly myself, as I'd never been called "pretty" before by anybody, let alone a strange man in the city. I guess this must be the quirk of traveling here. "It's nice to meet you Alexander, I'm Paul." I say, extending my hand out to shake his. I'm not sure if this is a good idea or not, but I'd rather not be rude in this scenario. He's dressed in a suit, how bad can this really go? "You're right, I need to stay alert out here."

"You're probably not from here." He says with a chuckle.

"What gave it away?"

"Well, you're in Central Park in the middle of the day. Seems like a pretty touristy thing to do to me."

"I mean... aren't you here too?"

"For sure, but I'm here looking for somebody that's not from around here."

"Oh?" I raise my eyebrows. "So you're here looking for something? And now you're sitting next to me on a bench? How can I help you Alexander?"

"Why, just you chatting with me now is helping me." He says with a soft smile. He had piercing blue eyes, they almost seemed unnaturally blue. "I'm here looking to interact with some fresh perspectives, different people unlike the ones I interact with on a day to day basis. There was something about you that called me over to you Paul. And when there's potential for something, I always take it."

Was he... flirting with me? I couldn't get a read on him at the moment. I didn't really know what to say at all. "Potential?" I say, keeping my eyebrows raised as I looked up at him. "Potential for what?" This certainly wasn't the relaxing afternoon I was expecting to have, but it was more interesting than anything I'd done so far on my trip.

"Something neither of us will forget Paul." He says as he gives me a wink.

"I'm sorry... I just have to be forward here. Are you... hitting on me?" I ask, turning my shoulders towards him. I'm taken by how much bigger he is than me, even while sitting down next to me on the bench.

He raised his eyebrows in almost amusement, laughing a little. "I guess you caught me Paul... guilty as charged!" He says, lifting his hands up into the air. "How could I not though... I mean have you seen yourself today? My goodness... you're beautiful..." he says, his voice trailing down into a low murmur as he feel his blue eyes trace me.

"I... well..." I say, flustered at the forward nature of this man. "I mean... Alexander... I'm not gay!" I say, quite surprised I'm even encountering this at all. I've never had to turn down a man before, or even turn somebody down at all for that matter. "I'm very flattered, but I just don't go that way."

"Really?" He says, a look of surprise breaking across his face. "Well, this is a surprise to me for sure."

"Do I seem gay to you Alexander?" I ask, feeling a bit flustered.

"Hmmm... I just think you shouldn't speak so definitively about what you are, you know?" He says, stroking his beard as he looks down at me. "I mean... you're still so young!"

"I'm 28, I'm old enough to know I'm not gay."

"And I'm 55. I'm still learning new things about myself every day. It's what's made me so successful in business. Confidence and competence are great, but self knowledge is the ultimate answer to making it in this world." He says.

"I'm sorry Alexander, I'm seriously flattered but I think I'll have to pass." I say.

He softly touches my forearm. "That's a shame, I had quite the evening planned out for us."

"You had a plan already?" I say, raising my eyebrows. I'm not sure who this man is, if he's even a successful business man. Maybe he's just a crazy guy with a suit?

"Oh absolutely"

"And what, Alexander, did you have planned?"

"Well, I was going to give you a new experience. Something to shape your self-knowledge, and allow me to indulge in one of my favorite experiences, opening that knowledge."

"You're saying you know something about me that I don't? I'm sorry, but this all just seems too crazy." I say, putting my hands down on the bench to get up.

He reaches his hand out and touches mine. "Paul, please don't go without giving me a chance." His hand is huge, and completely engulfs mine as he keeps his on top. He looks into my eyes, he's asking with his words but he's telling me with his eyes.

"Umm... okay... you can tell me the plan. But I'm not going through with it, no matter what." I say, leaning back on the seat, feeling his hand leave mine.

"Well, Paul. I think you're beautiful. But I have an idea of how you could be more beautiful...Now, stay with me here. That outfit is nice, but I think you could look a lot better if you... changed up your wardrobe."

"To wear a suit like you?" I ask, my skepticism growing.

"No Paul, I want to dress you up in something a bit more... refined and elegant."

"Elegant? What do you mean by that?"

"Paul, I think you would look mesmerizing in women's clothes."

I laugh, bending over as I sofly tap his thigh with my hand. "Oh gosh, Alexander, you are seriously messing with me. I was beginning to think you were being serious about something."

"Oh no, Paul. No no no. I am being very serious right now." He says, his voice remaining calm and controlled. "It's normal to hear that for the first time and react this way. Society tells you there's only one way for you to be. So you don't question it and live that way."

"Alright Morpheus, when do I take the red pill?" I say, laughing as I begin to stand up again.

And again, he takes my hand, this time clasping down on it. "Paul, please. Are you sure? I know I have my selfish reasons for this, but I see you and I can see you need to take this journey with me."

My eyes look down at those large hands again. Goodness, he's a lot bigger than I am. I let out a sigh. "If I'm getting this straight, you want to put me in women's clothes and then eventually... hook up with me?"

"I think that's a bit more of an over-simplified explanation of what would happen between us Paul. I can't deny it, I'm very attracted to you Paul. And I can tell you really need to have this, maybe more than I do. Can I not convince you?"

"I am seriously flattered... and maybe even a bit curious what exactly you're thinking... but no, I really can't be convinced."

"Here, I'll make you a deal Paul." He says, reaching into his suit jacket and pulling out an envelope. "There's always a middle ground. No haggling, this is a take it or leave it offer. But here in this envelope I have $50,000 in cash. Since money is involved, we're going to do things my way. For this whole envelope, you will go back to your hotel room and shave your entire body. Just leave your pretty head of hair alone, and get rid of everything else. Then, you will meet me at Thompson and Richards Department Store. It's a boutique department store where we will go shopping together. I'll buy you clothes, not counting against your cash reward, and then you will come back to my penthouse and we will share some wine. When the bottle is finished, you'll get the envelope. I have no expectations of you doing anything with me you're not comfortable with in the bedroom. Do we have a deal?"

"Ummm.... Wow..... uhhhh...." I say, stunned at the sudden offer sitting in front of me. He is holding a fat white envelope, appearing to be stuffed with something. "Is there actually money in there?"

He opens the envelope and shows me a very fat stack of dollar bills sitting in there. "I was holding onto this for a deal I was supposed to make today, but I feel this is more pressing for me."

"And I don't have to do anything other than shave my body, shop, and drink a bottle of wine with you... for $50,000?"

"That's correct Paul." He says as he tucked the envelope away in his suit jacket. "You don't even have to make up your mind now. If you want to join me, I'll meet you at the department store at 4:00, that should give you plenty of time to make a decision and then make the necessary preparations." He says, as he stood up himself and looked down at me. "It was nice meeting you Paul, I sincerely hope this is not goodbye." He walked back towards the sidewalk as he stopped and turned around. "By the way, I'll be referring to you as Paula at the department store. It just helps really build things for me." He says with a wink, walking off along the sidewalk and back towards the busy city.

I sat on the bench for a few minutes. $50,000??? I wouldn't have said this but I mean I'd probably suck a dick for that much money. But to get it without having to do anything like that, I mean I couldn't really pass that up, could I? I shrugged my shoulders and got up, looking for the closest pharmacy to find some disposable razors and extra shaving cream.

I got back to my hotel room, and quickly began to shave my body. I started with my legs, that made the most sense. I them moved up and shaved my chest, my armpits, arms, and then my stomach. I was fortunate to not have any hair on my back, so I was able to skip what was probably the most challenging part. Then I conducted some classic manscaping, and then attempted to tackle my ass. I managed to get everything off, and observed myself in the mirror. I felt almost... more nude than normal. LIke things were on display that I'd never shown off before. I twirled around in front of the mirror to see everything. Admittedly, I didn't mind the look of myself shaven. I was never overly hairy anyway, and in some ways I think it always made me feel less than, like I wasn't as much a man because I didn't look like one.

I took a deep breath, and checked my phone to see that I had 30 minutes left to get to the department store. I looked up the store, and fortunately it was only a 5 minute walk. How strangely convenient.... I got my things ready, got dressed, and made it out the door with enough time to show up a few minutes early. As I entered the front door, Alex approached me from behind a rack of shirts.

"Paula, I am so glad you came... And you're early! I hope you're as excited as I am."

It was weird to be called Paula, but I wasn't as upset about it as I thought I would be. Maybe the $50,000 helped me feel a bit more amenable to the arrangement. "Hey Alexander, let's get this started then." I say with a polite smile.

The department store was relatively empty. "I made a call, they're closing the women's department on the 2nd floor early for me."

"Really? What is it you... do exactly?" I ask, having stopped to wonder what kind of man I was about to pay me cash. How did he have so much in paper money?

"Let's just say I find things that people need that are hard to find. Just like you, I help them make dreams reality." He says, leading me up the escalator as a group of upset women went down, voicing displeasure at the store closing early. "I helped the owner with a particularly complicated problem, so he helps me out with favors when needed." We step off the escalator and the entire store is empty, just a couple clerks working at the registers. "They won't bother us Paula, not until I have to pay of course." He says with a wink. "So, Paula, what are you thinking first?"

"This uh.... Really isn't my area of expertise Alexander. I think maybe you should lead the way on this one." I say, a bit overwhelmed by the selection. I knew very little about women's clothing, and I certainly didn't know what to wear or what size I was.

"Oh, if you insist... I'm very happy to take the lead." He says while smiling at me. He begins by walking around the floor, pointing out colors he liked, materials he favored, and styles that he felt were classic and timeless. He asks me about my life, what I did for work, and listens to my frustrations about my professional experience.

"I'm sorry you aren't noticed for your contributions Paula, I happen to think you're incredibly bright with a good head on your shoulders. You'll get noticed soon, I have no doubt." He says with a smile.

"Thank you Alexander" I say, smiling back up at him. The compliments were certainly a nice change of pace from my usual lack of any acknowledgement. "You're very kind."

"Well I'm just being honest Paula. You're quite beautiful. I'm a bit shocked you aren't the belle of the ball at the office."

"Maybe I should have you as my boss." I joke as we stop by the streetwear section.

"I would like that very much... I think having me over you would be very beneficial..." He says as he stands in front of me, looming over me. He's truly got an entire foot on me, and I'm almost straining to see his blue eyes.

"I think you're still hitting on me..." I say, my voice wavering as I feel some resistance begin to wane. There's no harm in him hitting on me, right? It's all in the name of that pay day. "Is this the... streetwear section?" I say, gesturing to the racks of clothes as I try and break away from our pause.

"Why yes it is. I think it would be good for you to have some clothes to wear on our walk back to my place." He says, walking through the racks and checking the folded clothes table. "Hmm... I was thinking something like this" he says, lifting up a pair of black yoga pants. He reaches across the table and finds a white sleeveless crop top. "What do you think Paula?"

"Wait... I've got to wear these... out in public??" I say, my shock showing through.

"Why of course, we have to get you back to my place for the wine somehow. I'm two buildings over, it's not far at all." He says, gesturing his hand back down at the table.

For $50,000, why not. "It's on this block?" I ask, making sure I understand the stipulations.

"Yes Paula, practically next door." He says with a soft smile. "Now, how about you try this outfit on for me? We'll see how you like it."

I slowly take the outfit and head to a dressing room, I look back as he's taking a seat on a chair facing the dressing room hallway. "I'll be right here." He says, smiling as he waves me goodbye. I find the first dressing room and slip in. I slowly slip off my blue tshirt and khaki shorts, noticing my boxers. These probably won't fit well with the yoga pants, will they? I stand there for a moment, naked before I hear a knock on the door.

"Hello?" I call out.

"Hey beautiful, it's me" Alexander calls from the other side of the door. "I think we forgot to get you something. Can I show you?"

"Umm, sure" I say, opening the door slightly and poking my head out. I see Alexander there, holding a pair of pink lace panties. "Ohh.. my gosh you're right! I was wearing boxers, so this works much better." I say.

"You're not going to be needed those old clothes anymore today.... Wow... you've already stripped down. You must be excited." He says, seeing a slight bit of my exposed shoulder through the crack in the door.

"Oh hush, I'm just trying to do this the right way." I say as I begin to close the door.

"The only right way to do this is to be yourself Paula." He says as I close the door. "I'm very excited to see you."

Just be myself? It didn't feel like that was a likely outcome. I raised my eyebrows as I held the panties in my hands. Oh well, you don't make a cake without breaking a few eggs. I slip them up my legs, the soft material gliding up my thighs and then settling in snugly around my waist, the thing running up my ass cheeks as my cock is somewhat held in check. I wasn't very big, maybe 5.5" on a good day, but these panties were so tiny it almost looked like I was going to burst through it. I looked at myself in the mirror. It felt... not as foreign as I'd anticipated. I didn't know how else to explain it. They fit me surprisingly well. I had a pretty round ass from years of playing sports, and my cheeks almost hid the thong entirely. For some odd reason, I jiggled my ass a little in the mirror. I didn't know what came over me, it just felt more appropriate in the panties. I grabbed the yoga pants and slowly pulled them up my legs. They hugged my skin tightly, gripping at every inch and leaving nothing of my legs to the imagination. I turned around again, noticing how much my ass poked out with the skin tight leggings on. Not bad, I think to myself before I grab the crop top and slip it on. It leaves a good bit of my stomach exposed, and the tank top allows my smooth arms to be shown off freely. I slip back into the flip flops and make my way out of the door, taking a deep breath before opening it.

I walk out the hallway and over to Alexander. "Paula.... Wow.... thank goodness I'm sitting down. You've knocked me off my feet." He says, looking up at my as I see him lick his lips.

I smile, strangely appreciating the kind words. It feels... good to be doted on. It feels... nice to be appreciated. "Thank you Alexander. All thanks to your vision." I say with a smile.

"Are they comfortable?" He asks, "Do you like them?"

"You know... more comfortable than I thought. I could probably shop in these, walk down a street." I say.

"Good." He says as he stands up. "Because I want to check out that ass while we shop..... Goddamn...." he says, peering his head around. Instinctively, I turn slightly to give him a better look. "Mmmmmmm..." I hear him groan. It's strange, I've never had somebody be interested in my ass before. And here was this stranger... this man... almost lusting after it. I'd never experienced this before.

"Do you.... Do you like it?" I ask sheepishly.