Mistress Nurse Ch. 02: Golden Date

Getting back to work the following week, I put in 65 hours in 5 days. It was a struggle to stay focused with the promise of a lunch date. My mind kept alternating between "She's just being polite" on the one hand to playing out all of my wildest and most perverse fantasies on the other hand. The thing is, looking back now, my most perverse fantasies at the time didn't hold a CANDLE to what Oksana was about to introduce me too...

Despite the inner turmoil I knocked out a big project and I managed to find a car as well. It was delivered to my work on Friday. I looked it over and signed the paperwork. Amazing how much technology has simplified life.

I'd been so buried with things that I hadn't had a chance to "wear" anything special. So, Saturday morning I decided to add a naughty thrill to my pending lunch date. I put on a favorite thong Em had given me. I guessed she'd only worn it a few times. It was a French cut hip hugger style. It was meant to be worn high. I wore a white undershirt tucked it into my pants to cover my secret choice of nether cladding.

Oksana and I met at a cafe in the suburbs. We made small talk mostly. Just being with her was so incredible! The time passed quickly with very vanilla conversation. I was hoping to ask deep meaningful questions and have a profound connection with her. I mean, FINALLY here was my chance to have a date with a goddess that seemed to genuinely want to be with me! It was every nerd's dream. But it turned out to be nothing more than small talk (as in, with someone you don't really expect to ever see again). It was disheartening as lunch concluded and we rose to leave.

However, as we got up her purse tipped sideways and her phone dropped to the floor. She looked me squarely in the eyes, and lifted her eyebrows. The expression screamed "What the fuck? Are you seriously needing to be told to pick that up?".

She stepped sideways to give me unobstructed access. I bent over and retrieved her phone. I noticed a subtle but sly smile on her face when I handed back her phone. I walked her to her car and she simply said "follow me".

I was giddy with the prospect of spending more time with her! I felt like I could and probably would do anything she wanted. Even if no kinky fuckery took place, somehow just the thrill of her presence would be its own gift. I think most women don't understand the effect they can have on men. Maybe not the players, but the average guys can be enslaved by good chemistry. I'm sure the players have figured out that women can too. Figure out how to give a woman regular dopamine hits with witty flirting, casual touches, making out, and the sex doesn't even have to be great to keep her coming back. It's sad how easily people revert to lizard-brain mode.

We drove to an apartment complex where I followed her to her place. I was impressed with how simply but tastefully decorated it was, and especially how clean it was. Eating off the floor wouldn't be a problem with sanitizing standards like these at work.

She stepped up to me for a hug, but instead of a warm embrace, I felt her hand slide down my back, grip both my T shirt and under shirt and lift them up and away. Her other hand touched my bare back and slid down until it made contact with Lycra.

I heard a soft sound escape from her. A triumphant sound. It happened so quickly I hardly had time to understand what was going on. What I knew though was she had caught me. Being so quickly outed in the act of cross dressing (albeit in a small way) was unnerving. She knew all about my secret, but still. I was shaken. What would she think of me?

Her finger tips explored the lines of the material before stepping back. She appraised me, and again issued a directive that both highly aroused me, and caused subtle nervous tremors within me.

"Take your shirt off" was the simple command.

I hesitated momentarily--and a look of warning flashed across her face. I complied without being told again.

Standing with my shirt in hand she issued her next directive "Turn around" more softly.

I pirouetted slowly, and stopped with my back to her, unsure if "Turn Around" meant a full circle or not.

"Bend over at the waist and set those down" came her answer to my unasked question.

I did so, holding the position while I folded and stacked the linens. She stepped up behind me, her hand applying pressure to my back in a clear message to stay as I was. She moved her hands over my back, again teasing the material and sliding up beneath the waistband, pulling the strip between my legs very tight.

She gripped my waist and brought her hips up to mine, grinding into me very slightly but suggestively. I was completely at a loss. But damn it was erotic! No wonder women liked it from behind!

By this time, I was sporting a very meager but firm woody. She reached in front of me, popped the button and lowered my zipper. I stood, waiting for her next cue. She stepped back and waited.

I decided her actions could only mean one thing. Without a word, I slowly lowered my pants to my ankles. When she didn't say anything else, I kicked out of my shoes and again bent over folding my jeans neatly on top of them. She admired the view throughout.

"Come sit down" she said while pointing to the couch adjacent to where she sat down.

"Now then, I see that you enjoy wearing women's panties. Your sisters at least. And that's fine. However, I want to understand your entire sexual history, everything you've ever done, ever fantasized about, from the very earliest you can recall."

Her tone was like that of a standardized test examiner, explaining the parameters of an oral essay whose outcome would determine the quality and intensity of my education from that day forth. And really, that's exactly what it was.

I explained the vanilla parts, about rubbing out orgasms while reading erotica, and cross dressing which she already knew. She was pleased that interest extended beyond simply wearing panties but also included lingerie; something I knew my sister would out me for sooner or later.

With her propensity to barge in on me without warning she had more than once caught me fully outfitted. The last time this happened I'd tried to cover up, but she yanked back the robe to study my choice of attire. Em smiled a bit, actually complimenting me on my scrawny feminine build, then walked out. Whatever issue bringing her into my room in the first place, apparently discarded.

She asked about Emily and her friends. I explained about our dynamic and that it had kind of always been that way and even how when we were younger, we used to play with her barbie dolls together. She even insisted on dressing me up in her clothes as a pretend girlfriend.

"Makes sense--that's how your interest in cross dressing started."

I hadn't really considered it before--but yes, that was certainly the genesis of my interest in women's underwear and cross dressing. It didn't seem strange at all to play dress up as a kid. It wasn't erotic or anything. Just kids being kids. A fundamental curiosity about the differences in the sexes and what life must be like as a different gender.

I thought about it for a bit longer then described a couple of other memories from early childhood. Innocuous times when either Emily or my best friend and I would put on our sisters' dresses. Again, though there wasn't anything sexual about it. Just a simple curiosity. Bear in mind, this was way before terms like "Gender Fluid" were coined.

I explained about later-on, being a horny teenager and being girl crazy--but hopelessly shy--and how I'd eventually read a lot of stories and had especially enjoyed the sissy boy stories.

I'd first taken a pair of Emily's panties while in high school, and that was a whole new level of exciting. Finally, as I graduated from college and found my current place, we moved in together. She expected me to do her laundry--so with the easy availability of her underthings it just sort of took off from there. It was easier to find a local mall store or even online seller of lingerie, so my underwear drawer had grown dramatically since the move.

I opened up about how deeply ashamed I felt though. It was so painful that, while I loved doing it, I really only occasionally wore frilly panties because it just felt to weird otherwise. I only wore lingerie at home while getting myself off. If I'd had a Mistress to do it for, then who knows what my cross dressing would look like. I didn't think I wanted to transition or even go out in public in a wig and makeup. But I LOVED how it looked and felt. I did wonder if my fascination was simply the displacement of my desire for a healthy connection with a woman, and this seemed like the closest I could ever get?

I hadn't really put two and two together before this moment. But there was something about sharing my story out loud that made some pieces fall into place. Innocent childhood games and not-so innocent adult fantasy had definitely paved the way for my journey.

And just like that. Bingo.

Apparently, Oksana was 'almost certain' that a sissy-in-training like me would be exactly the boy-toy she was looking for. The fact that I had a panty fetish, not just a panty sniffer but a panty wearer; the fact that I willingly went along with a sister who dressed me in her clothes AND underwear meant I was docile and had a low threshold of resistance to doing unconventional or kinky things.

And that was perfect for her fucked up purposes!

"Tell me more about your fantasies now Jake. What do you crave, but are too ashamed to ask for? Don't worry about how it sounds. I won't judge you. Just be honest and see what comes of it" she probed.

I reluctantly recounted the story of the pool house. She smiled and seemed very entertained or pleased, or both. But she didn't offer any feedback. Simply asking "what else?"

I explained about how I'd read stories on just about every topic. I was completely heterosexual, had no desire to be cuckholded, but I enjoyed lesbian and group sex stories. I'd read a lot of very sensual vanilla stories. Classical romance themes...

Seeing an impatient on her face, I took a leap. "I've also read a lot of incest stories. But no, I've never fooled around with my sister".

She must have wanted to hit this topic because she relaxed and gently asked "Would you want to?"

"I don't know... The fantasy excites me sometimes. So maybe; but I know actually acting on fantasy is a very mixed bag" I offered.

She hummed and hawed to herself, then asked again what else. I explained that I'd also enjoyed stories of forced feminization, sexual servitude, diaper lovers, light BDSM, and power exchange, even medical role-play. She seemed very pleased that my list of interests was so comprehensive.

"Do you have any experience with any of those?" she queried.

"Uhhhhhhh, not... really" I answered tentatively.

Wanting to understand more she asked "Do you want to try any those things, or are they just nice stories to read while you touch yourself?"

Sitting before her naked like this, it was difficult not to cover myself in shame. I probably should have been erect with arousal, but I wasn't. Feeling exposed on several levels, I folded my hands in my lap. I was partially covering myself without actually adopting the cliché pose of cupped hands over male parts. I looked at the floor, feeling sheepish and expressed that yes, I had a strong desire to explore the things I'd read about and stated that I was willing to try basically anything within those arenas, assuming she wanted to do any of those things with me...

"Let me ask you this; would you rather fuck a pussy or eat a pussy?"

For me, there was no question whatsoever. "Of course I would rather eat a pussy." I LOVED the smell and taste of pussy. I dreamed of being smothered in pussy sauce. Getting my own 'boy pussy' reamed while another femme used my face as a seat--so hot!

Clearly pleased, her demeanor changed. She must have made a decision.

"You need to understand a few things. First, we will not be 'dating' in any conventional sense of the word. We are not in a relationship" she paused, watching my expression.

"We will spend time together--on my terms, but I'll always drive and you'll always ride bitch" she said matter of fact-ly.

Turning and walking around a little bit she continued to explain things. I was surprised by it all, but I wasn't about to challenge her either.

"Before you get your hopes up too high, know that our arrangement has an expiration date. I don't know what that date is, but we will continue for as long as you meet my needs and wants", she said this quietly, almost pensively. She paused thinking for a bit, then continued.

"I saw from your blood work and medical history that you don't have any communicable social illnesses. We wouldn't be here if you had any, by the way. I'm fastidious about my health which you'll soon learn for yourself. As a nurse, good hygiene and sterile technique were constantly emphasized in school and now at work too. A simple staph infection could kill someone with a compromised immune system" she paused to communicate the seriousness of this proclamation.

"This means that for the duration of our arrangement you will be mine exclusively. If for some reason you wish to terminate our agreement, you may do so at any time. But once you exercise that option, you will never have the option of going back. All contact will be terminated. Permanently."

Her tone made it clear there was no negotiating any of this. I tried to take it all in as best I could.

"If you don't agree to that, there's the door. Also, if you every try to assert yourself with me, you will severely regret it. I know ways of hurting you that you cannot even imagine. Ways even the most intense masochists would not enjoy. Don't try me" Her tone was stern and unforgiving. I was at a loss.

And more than a little turned on!

"Secondly, I don't want to know ALL about you, or your past. I don't want to get to know you on every level, do you understand? If it isn't part of your sexual history or an answer to a direct question, keep it to yourself. In order for you to keep my interest--in order for this to work, you are an obedient plaything to me, and nothing more. You will be my very obedient and willing experimental subject. You'll have to sign a notarized contract to that effect. Do you understand?"

At this point in her explanation, I was both puzzled and thrilled. Did this mean we would engage in sexual activities? The mere prospect of pleasing this woman tied my insides in highly pleasant knots!

Without much thought, I readily agreed, flattered to have any chance at intimate physical contact with such a gorgeous statuesque woman.

"First things first. Here's the contract. Read it. If you agree, we'll have it signed before a Notary. While you are doing that, I'll take a few minutes to prepare some additional wardrobe for you. Oh, and also--I'm not a charity. Do you have two or three hundred dollars on hand?" she asked directly.

I did have the money though, I always carried a few hundred in cash. But I felt a little uneasy. I didn't want to hand over a wad of cash only to be a sucker and never see her again. I also suddenly worried that perhaps she was a professional dominatrix or that she was trying to set me up as a pay pig, which I absolutely was not.

She saw the look of concern on my face and added "The money is so I can buy some things for you. Either things we'll use together or things you'll wear. None of the money is for me. If you wish to buy me gifts which are cogent to our arrangement, that is fine. I'll leave that to your discretion. But I'm not asking for you to pay me in any way for our time together."

Her explanation calmed my anxiety about money becoming a factor. So, I decided to roll with it and withdrew three Bens.

Handing her the bills she smiled and said "Excellent. Now then. You've read a lot of stories, but what kind of practical experience do you have pleasuring a woman? I don't mean with your penis either. You won't need it here."

"Uh, I've given oral a couple of times. I don't have a lot of experience but I absolutely love doing it. It makes me feel good to know I can give a lot of pleasure to a woman. And since getting her off is more important to me than getting off myself, I think I'm an enthusiastic under-study" I explained.

This was actually a lie. The only "Oral" I'd given was to used panties. But I didn't want her to change her mind, and I knew I would be very enthusiastic about it.

"That's very good. I can teach you the techniques. A strong desire on your part is all I need for now. A man more intent on giving, than getting is the best kind-- not hung up on getting his own rocks off but focused on MY pleasure first and foremost. Yes, that will do nicely for my purposes."

She arose from the couch and gestured for me to take her hand. I was nervous being naked before her, and tried to cover myself. She chided me for my shame, and insisted that I could never cover myself. I dropped my hand to my side and let myself be led into her bedroom.

Apart from a large king-sized bed, I noticed the massage table. There were some triangular bolsters on the floor beneath it which she arranged on the table as a makeshift backrest. There was also a cabinet tucked neatly beneath the table, with drawers that pulled out from the end.

The big shock was the modification to accommodate knee crutch stirrups. She secured those in place, then pointed to the table. I understood her meaning. I turned around and sat on the edge of the table, between the stirrups. I scooted back and laid down, then hoisted each leg into the stirrups.

She was pleased with my ready compliance and said as much while she stepped up and secured my legs in place with extra wide Velcro restraints. I hadn't noticed it before but there were torso, wrist, thigh, calf, and waist straps. Once fully trussed up, I could hardly move.

She went to the large walk-in closet, turned on the light and pulled the door closed behind herself. I wondered what she was doing. The few sounds I heard gave nothing away. I couldn't turn my head fully, but enough to see the door with peripheral vision.

When the door opened, I almost gasped! She stepped out wearing the classic naughty nurse outfit. High heels, white thigh highs, a micro mini skirt that nicely showed off the tops of the stockings and garters, a very tight button down top, opened to below the line of a white lace bra, and a little while nurses cap.

My cock instantly stood at attention. She showed herself off to me, pleased with my admiration of her transformation from RN to Exotic Naughty Nurse. She then withdrew from the closet a wheeled stainless-steel instrument cart with a draped tray on top. I had no idea what was coming, but I was both nervous and excited.

She strutted sexily towards me, arranging the cart conveniently at the foot of the table. Then she walked directly away from me, bending down at the waist next to her bed to retrieve a wheeled examination stool. She pulled it out from its nook, and gave me a stunning view up her very short dress.

I could make out a white thong along with the garters. It was my absolute favorite outfit, and here this stunning woman was modeling it for me in the most provocative ways. It was a fantasy come true. While I didn't know what the future held, this moment was perfection. And totally worth whatever else may be.

She positioned the stool at the foot of the table, between my spread legs and took a seat. Pulling open a cabinet drawer beneath me, withdrawing a pair of long-sleeved examination gloves, her face covered with a plain white surgical mask--I could see that she was smiling at me beneath it, seemingly pleased by my physical response to this situation.