tagTranssexuals & CrossdressersRealistic Expectations

Realistic Expectations

byTwistedThoughts©

Authors Note: I write for entertainment and reviews help me decide what to write next. This story has consensual feminization.

I was reading the first chapter of a novel I had just bought, while drinking the house specialty coffee in the outdoor seating at a local cafe. I had developed a taste for it over the last month and enjoyed a cup every Saturday morning when I frequented a local bookstore and bought a new novel for the week.

Reading was a favorite pastime of mine, it allowed me a chance to escape into other realities beside my own boring existence. My social life was quite a dud and relationships were few and generally short lived. I have a slight frame and small build. Though not overly muscular or handsome, in the looks category, I am by no means ugly.

As I sat there reading I was approached by a beautiful woman. Her features seemed flawless and her hair was done in an exotic triple braid, one thin braid on each side of her face and a long thick braid down the back. As I looked up at her when she neared, I was nearly lost in the her gaze before she spoke.

Smiling she began, "Hi, I'm Samantha and would like to get to know you a bit. I'm pressed for time at the moment, so can't really talk now but I'm planning on having lunch here, at the cafe, around noon. If you would like to get to know me as well we could have lunch."

I was shocked, while my experience may be limited, I've never been approached like this before. After a moment I responded, "I'm Jack and a bit stunned, it's not everyday a beautiful woman approaches me so directly."

"Sometimes I'm a bit direct, is that a problem?" Samantha asked.

"No, no, not a problem. Just different."

She continued, "Like I said, I'm on a schedule. So will you be having lunch with me or not?"

As I contemplated my response, I quickly looked her over once more. Everything about her seemed perfectly in place and even her clothes seemed like they would not stray from there proper place. Her skin was smooth and healthy, her nails though not polished were perfectly cut and buffed to a shine. Her sleeveless black dress, while short, was not obscenely so and her black leather boots came up near to her knee. She was closer to perfection than I had seen in person before.

"Yes, I'll be here around noon. So we can get to know each other better." I answered, attempting to address her in a manner similar to how she had approached me.

"Good. I expect the conversation will be pleasing. I'll see you at noon then." she replied and then walked away.

As she left my eyes lingered on her perfect form and the grace of her movements. Afterward, my thoughts lingered on what it was that must have sparked her interest. Unable to come up with anything specific I had done, I decided to ask her if it turned out everything went well at lunch.

As it was a beautiful fall day, I decided to continue reading at the cafe and simply wait till noon. A couple hours flew past as I was reading and before I knew it it was noon. The sun was still shining, and with no wind, the day was starting out wonderful.

"Hello there, Jack!" Samantha said in a playfully loud voice, as she walked up from behind me.

"Whoa!" I exclaimed spilling a little coffee on the concrete beside me, because I had not noticed her approach.

I continued "You spooked me a bit, sneaking up on me like that." Looking down at the coffee which was now just food for ants. At least it hadn't landed on me.

In a stern voice Samantha said, "You're not going to just leave that there for anyone to step in are you? Clean it up!"

Without thinking I immediately reached over grabbing a few napkins and dried up the spill. "Sorry about that, I'm not usually such a klutz."

Samantha, looking me over, said "Lets hope not, I think clumsy is something that would cost to much for me to be interested in it." Continuing she asked, "So what do you do for a living and for fun?"

A bit unprepared I replied, "I have a few web-front shops online that I get commission from, so mostly I just sit back and watch money trickle in. It's not a lot, but I can live on it, though some weeks are better than others."

Samantha responded without missing a beat, "I'm basically in the hospitality industry I hold events for special interest groups and provide the service and entertainment. The rest of the time not spent planning or finding talent I spend training employees on the entertainment and protocol of the different events."

A waiter stopped by the table at her beckoning and took our order and brought drinks. She ordered for both of us. While a bit odd, especially on a first meeting, it worked out okay because she ordered me a grilled chicken salad, which I was planning to order anyway.

A bit at a loss for what to say next I just started talking, "So what was it that made you want to get to know me better? I don't think we've met before."

Actually, I was certain I hadn't seen her before. I could not have forgotten someone who looked so perfect, though I was probably forgettable at least by my definition.

Samantha, without batting an eye, said, "Would you believe a fortune-telling mystic? If not, I have nothing." she finished with a smile.

After that my wit came to play and I just had to ask another question. "So why does a fortune-teller point you at me? Am I your one true love or maybe a knight in shining armor to rescue you from something?" I asked grinning.

Coyly she responded, "Well, if I told you what for, it might invalidate the prophesy. You know how fickle the future can be. One minute your drinking coffee and the next a hot woman walks up and starts to talk to you. Wouldn't want to break up the mojo would you?"

"Of course not! Let's keep the the future going the way it is. It looks very good from here." I said, praying that it was taken as a complement, not an insult.

Mischievously, she responded, "Well I was only hoping for you to be 'the one' I was sent for, and I think perhaps you are. Would you like to make a little side money, perhaps have some fun doing it?"

Curiously, I asked, "Well that depends on what that involves."

Hesitantly she said, "It's not exactly easy to describe, perhaps you would be willing to try it out for a day, and then decide?"

I felt like I was getting the run around and said "I'm not sure; everything here seems just a bit off, like you're not telling me something."

With a sigh, Samantha explained, "Well, I intend to start a new service teaching, but I will need someone to practice with, as well as someone to serve as a model for what people should expect to take away from it. The training will be a lengthy process to complete, so I thought perhaps a student who was paid would be the best option for research and honing of skills."

Reluctantly I replied, "I guess I could give it a day, and see where it goes from there. How well does it pay?"

Samantha responded, "Actually, I had planned on paying with room and board at my house and a generous weekly stipend, but since you already have constant income perhaps we can work something else out."

Encouraged by this possible extended interaction, I enthusiastically responded, "I think your original offer might be nice. Right now I have a roommate who is absolutely atrocious. I spend half my time at home cleaning up messes that he made."

Hopeful, she said, "Really? You think that would be sufficient? I think it is the only way to reach perfection in training. It would be superb if you accepted my offer, but we'll really have to see how well you actually take to the training. It does require a certain amount of special motivation."

As nonchalantly as I could, I added, "Sure, I was already looking for a possible alternative place to live so this would be a good stepping stone, and extra money never hurts either."

Excitedly, Samantha reached into her purse and pulled out a business card. "Great! Here's a card with my address on it. Be here at 9 o'clock tomorrow morning and we can get started. On second thought, here's another it's for a spa downtown, go here at 2pm today and tell them Samantha sent you. I'll call ahead they'll take care of everything. They do great work and I'm sure they'll take care of you."

This was a bit quick, but it included the potential to get more interesting since it had an added benefit of living in the same house. But the spay part through me off and I replied, "Cool. But a spa, why would I need that?"

She explained, "You'll be the initial student and demonstration of what the training will provide, I need you to look your best. If you are the one the fortune-teller sent me to I don't think it should be much of a problem for you though."

That seemed reasonable. "Okay, Well I'll stop by the spa then I guess. I didn't have any real plans for today anyway."

The food arrived then and as we ate we continued making small talk find out each other's interests and hobbies. When the waiter came with the bill she snatched it up and paid without even giving me the chance to pay for my own food. After which she promptly left for another appointment.

As lunch ended, I thought about what this could mean. An invitation to live with a beautiful woman doesn't just happen everyday. What kind of training does a person offer that includes room and board as incentives? Maybe I should have insisted on some more specifics; too late now I suppose.

When I arrived at the spa I had the distinct impression that very few men ever had appointments there. The entire interior was done in shades of pink and purple with potted flowers all around. There was a very bubbly receptionist who took my name and reference and then bounced up and veritably ran to the back to get someone.

I had barely had time to take a seat before someone came out looking for me.The lady was stunning with wavy dark hair in a ponytail, stunning dark eyes and a tanned complexion. Her name tag read 'Susan - Owner' and her clothing was fashionable accentuating all the right areas.

She walked right up to me, "Hello, Honey, I want you to know were here for anything you need. Your scheduled to get the complete treatment so it'll take about 3 hours. Samantha always schedules her time here in our private area so you'll have the added luxury of picking music from our selection and a choice of aromatherapy while your here."

As I followed Susan to the back, she showed me my option on a pamphlet and I picked some meditation music and a jasmine scent. I was then waxed, massaged, my eyebrows were plucked just enough to soften them, a manicure, and a pedicure finished the trip.

I felt a little strange as I left the spa, but it was nice to be able to relax for a while. The whole ordeal left me feeling a bit out of place and a bit feminine, but they said it was what Samantha had asked for. Actually, I kinda liked it, and I think I actually looked really good except for the light pink polished nails, and I felt fantastic.

Going home I found that I was so relaxed through the evening that I had no problems going to sleep and I had odd dreams of floating on clouds and being rocking on a hammock in a warm summer breeze. I woke up feeling warm and comfortable looking forward to whatever the day may hold in store. I was especially anxious to get to see Samantha again and find out what exactly it was she had in mind for me.

As I pulled up to the house I was immediately impressed by the estate. Samantha lived in a beautiful mansion of a home surrounded by several rolling acres of meadow. As I pulled up the winding driveway to the house I noticed a detached garage and what appeared to be a small building sitting alone in the middle of a garden a little way from the house.

Samantha met me outside as I parked and went to the door. She had her hair up and was wearing a bright sundress. Her smooth fair skin contrasted against her glistening a bright shade of red lips.

"It's beautiful isn't it? I love the gardens at this time of year. So how open minded are you?" she said.

"Well I like to think I'm open minded nothing really bothers me that much, and I don't have a problem enjoying myself when something new comes along that entices me." I answered, wondering where this line of thought was going.

Giving me an assessing look she continued, "Okay. So are you willing to give this one day your all? This is an all or nothing situation so if you decide it's too much you say so, though I hope you just say yes."

"So what is it exactly that you are planning that you need me to be a student for?" I asked, wondering what a woman like this could possibly want from me.

"Well, I think that if I explain it you may find out your not as open minded as you think you are. So I plan to try to introduce you to it a bit at a time then you can have a little time to decide if this is okay for you." Grinning Samantha added, "I've think a quick tour of the house is in order. Most the staff is off today so I'll show you around."

As we went from room to room I noticed a distinct themes throughout of the different areas of the house. Some tropical rooms, some warm and cozy, others were fairly utilitarian, there was a lot of openness and Samantha confirmed that the different areas were designed to host different events.

We had an uneventful lunch and there was small talk the whole time. As we finished up I was taken aback as Samantha changed topics abruptly.

"Your nails are beautiful Jack. Would you keep them painted if I asked?"

"The world can be different Jack. You could be different and if it is something you can do, then maybe you can have me. I had intended on working up to this but I'm not one to be subtle when I don't have to. "

She moved alongside me looking directly into my eyes she placed one hand around my waist and the other she began gently stroking the crotch of my pants. "You're pretty Jack. After the spa you're looking absolutely lovely. I want you Jack, but I come with a few strings. "

Beginning to walk around me, running her fingers in delightful patterns across my body she began her monologue. Her eyes entranced me as she began to speak, they were lined in darkness highlighting the natural color and pulling my gaze to beautiful eyes.

"As you may have guessed from your visit to the spa I have certain, tastes. I have things I hate like plain clothes and body hair. I have things I love like smooth skin and manicured nails. I love pretty hair and pretty features. As it turns out I'm also interested in you."

She continued, "There is something that makes you special, as not many people are, but I have realistic expectations nothing changes overnight. You can change the surface in a moment, changing the whole of a person takes time. So here I offer something unique do you want to try?"

Thinking it over I thought I could see where this was going she wanted a girlfriend, though I wasn't quite sure where I fit in the picture. I had always wanted a woman to submit to someone who could twist me and my mind to her whims and maybe even my pleasures.

"Yes." I replied smiling, "I think I would like to try"

As a smile crossed her face she said, "Follow me, let's see how fast we can change the surface."

I followed her into a guestroom which was setup with a vanity, full length mirror and an attached bathroom. There was a vase with fresh cut flowers on the vanity scenting the room with a light rose scent.

Samantha began as she went to the closet, "I've read some about this and so much seems to be about the clothes. Let's test that theory shall we? The walk-in closet has two sides, ultra-feminine and chic. Why don't you take a look and see what you'll be wearing for the first week."

Taken a bit due to the directness, I asked "Can I take a minute? I need to think for a second this all a bit quick."

"Fair enough, I'll wait." She said, sitting on the edge of the bed and crossing her smooth enticing legs. "Do you mind if I talk while your thinking, maybe help you get some perspective?"

"Sure, go ahead"

"I've got enough, but I've got issues I need things, without them I'm a bit empty, but what I'm looking for doesn't come in normal packages. I think that perhaps you can become what I'm looking for and ordinary or plain is nowhere close to what I need. I'm talking about love, sex and partnership what is it that you need?"

"I've never found what I'm looking for. Truth be known, I'm not sure what it is I need , but you intrigue me and I think as unconventional as this is maybe this is what I'm looking for. So call me odd but this feels right."

"So what do you want to pick?" she said a bit of intrigue in her expression.

"Do you prefer to laugh or relax?" I asked.

A sparkle in her eyes, "I prefer to laugh, why do you ask?"

"Let's go with ultra-feminine then. From what I saw in that closet that side will inspire nothing but mirth."

Giggling she said, "Okay we'll do that then, I'll send someone in to help with makeup though, let's shoot for pretty not clownish."

"So this will be your room, I'll give you some time to settle in and change, everything you'll need is in here. I'd recommend you shave before your makeup is done, five o'clock shadow doesn't really go with foundation very well."

"Dinner will begin at six. I'll see you then if not before, take you time." Then she walked out with a noticeable sway in her hips and she looked back to see me watching her just as she rounded into the hallway.

So I set about cleaning myself up taking a shower and shaving, I picked an outfit from the closet and dresser and got dressed. At about that time a lady came in without so much as a knock.

She began, "Hello, darling. I love the outfit. I'm Cara, Samantha asked me to come up and help with your makeup tonight. Pay close attention because you'll be needing to do this yourself soon enough"

Cara sat me down at the vanity and proceeded to go to work, explaining what everything was and how to apply it and how you could do things different to achieve different effects. I think it took an hour just to put on the makeup with her explaining everything to me.

By the time Cara finished and left there was only half an hour before dinner. I took the time to pick out a matching pair of shoes and try to learn how to walk in them. Aside from a few pairs of fluffy slippers there

As I entered the dinning room a bit nervously, as soon as Samantha saw me her eyes brightened. Her assessing eyes taken my new look in for the first time.

I was wearing a very short light pink ruffled dress. it had very short lace sleeves which puffy, several layers of ruffles with black lace trim, pink lace armbands pink satin panties with black lace trim, sheer black thigh-high stockings, and black two-inch strappy heels. Samantha was wearing a simple yet lovely little black dress.

Clapping her hands together, Samantha exclaimed, "How lovely. Can you curtsy?"

I tried to curtsy and almost fell over. Samantha laughed a little and said, "Well it appears the surface has changed but that doesn't change the inside does it. I have realistic expectations it'll take time to get you into the role." Stirring her drink with her straw she continued, "So how does it feel?"

"I kinda like it, it feels nice against my skin. The clothing rubs against me in interesting new ways. Although I must admit I feel a bit silly, embarrassed and vulnerable with so few clothes. and them being so feminine."

A few second later my wit came to me, "So how do I look? Does this make my butt look big?" I said as I turned and leaned forward, sticking my butt at her, causing the dress to ride up revealing my pink lace panties.

Laughing she responded, "Oh dear, my girl. I think you may have accidentally became a slut. Be careful, I might like that. As a matter of fact," she walked in close and began to rub my ass through the satin."I think I just decided I do."

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