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.
She first placed her hands on each of my knees, then teasingly slid up my thighs. The material of the tight gloves skidded across my skin. She traced around my pubic area without actually touching my stiff penis. She moved down to my ass then, gripping each cheek and forcefully spreading them.
It was a very strange sensation, but not unpleasant either. After a cursory inspection, she withdrew a tube of lubricating jelly from the cabinet and liberally slathered the first two fingers of her right hand. Then using the fingers on her left hand to spread me apart again, the gloved and lubed finger-probes made straight for my back door.
I was surprised that she was going to enter me like this right away. Truthfully, I enjoyed anal stimulation. I’d just never once had anyone else touch me there. It was surprisingly good to be manipulated by her skilled hands.
She teased around the outside of my sphincter, smearing the slippery goo all around before aligning her index finger with the center of my ringed muscle. The pressure came slowly but steadily.
“Relax. It will hurt if you clench. The best thing to do, is to bear down like you are trying to expel” she instructed.
I did my best to follow her direction. She was right of course, the muscles relaxed and allowed her violation of the “Exit Only” general policy to commence in earnest.
Oh, fuck was it good too. I can’t even describe how amazing it felt to be penetrated in a sort-of gentle and erotic way. It hurt too. But I was so high on endorphins and sex hormones that I didn’t care.
Her finger pumped in and out slowly, then moved in a circular motion. Not a spinning, but rather as though her fingertip was drawing a circle. She seemed to be coaxing my sphincter to relax and open wider.
It worked. Soon she withdrew her index finger, only to return with both lubricated digits.
A few more cyclic pumps of her hand and I had a rising urge to use the toilet. I interrupted her to say as much and my naughty nurse withdrew her fingers.
“Have you ever used enemas?” she inquired. I answered honestly that I’d had a few, but it had been so long ago I hardly remembered.
“Good. I’m not going to train you with those today, but I have a bag for you to take home. In the future, anytime you have advance notice of a date with me, you are to use the bag to have a cleanse. It holds 2 quarts, and any adult should be able to take the whole bag and hold it at least ten minutes. We’ll work on increasing your volume later.”
I was speechless.
“For now, this will be enough. Have your first one tonight when you get home. I’d suggest using a mixture of 3 cups of coffee with two tablespoons of baking soda then diluted with enough water to fill the bag. Coffee is remarkably pleasant for cleansing and the baking soda will neutralize the PH of the whole batch, making it easier to hold and expel.”
She was a natural teacher and I instantly loved being her kinked student.
“The solution should be very warm to the touch, but not so hot that you can’t comfortably leave your hand submerged” she explained at length.
I wasn’t sure I would remember all of it, but I figured I could call or text for help if I got stuck.
“Also, make sure you wear stockings and a garter while having your enema tonight. A lacy top would be fine too if you have one. Lingerie should greatly enhance the experience” she suggested.
I was intrigued and amazed by this woman. Not only was she okay with my unusual sexual proclivities, she was actually encouraging them! I felt like I’d won the lottery the day she took an interest in me. I wanted this to last forever.
She returned to her dilation exercise and this time used three fingers; I was really feeling stretched open. She held that for a moment while taking out a medium-ish sized butt plug that had been covered with a condom.
She explained that since I hadn’t had an enema the condom was there to assure easy cleanup later. I was required to wear the butt plug until I could replace it with an enema nozzle when I returned home.
She grabbed the panties she’d been wearing earlier, wadded them up and shoved them into my mouth. They were saturated with her juices. I was in heaven!
She expertly wielded the condom covered butt plug. She teased me with it slowly, the hand of experience showing off its skill. Because of the size and my previous training efforts, the plug slid home relatively easily.
My new mistress wasn’t satisfied though. She drew it back out and began to slowly fuck my ass with it. She became so enthusiastic it could have been classified as rape.
Except that I had already given her carte blanche.
When the plug finally rested in my anal canal, the sensation was strange but not entirely unpleasant either. She shucked off her soiled gloves and donned a fresh pair. Then she withdrew a small fenestrated drape about 2 feet square, and slipped my male parts through the opening.
She explained that while this wouldn’t be a sterile field fit for surgery, it would make what she was about to undertake much safer. That pronouncement made me worry. Then again, I’d read a lot of medical fetish erotica so I had a pretty good idea what sorts of procedures were on the menu.
She used Betadyne sterilizing wipes to clean all the exposed skin. The moist antiseptic towelette was cold in the open air and didn’t help my manhood any. When she was satisfied that everything was clean, she took out a set of long and highly polished stainless-steel rods.
“These are called ‘Sounds’ because I will use them to sound your depth. This is a Rosebud type because of the bulbous tip”
My beautiful tormenter-to-be made a puddle of sterile lubricant on the drape, and dipped the tip of the metal rod into the lube. With her left hand, she firmly gripped my cock. With thumb and forefinger, she pried the head apart, opening up the slit.
She made eye contact with me to make sure I was still OK, then aligned the rod with my opening. She twirled the sound and spread the lubricant around. And just like that, it was plunging into me.
I cannot really describe the sensation. The first sound she used was relatively small so there wasn’t a painful stretching sensation. I expected that it would be incredibly painful but it actually wasn’t. When I went pee later, yes, THAT hurt like hell. But the act of being sounded was actually, almost pleasant. Like jerking off from the inside. She kept twirling the rod in slight circles, and allowing its own weight to drill it deeper into me.
When several inches had disappeared, she angled the sound down, away from my torso, so instead of pointing straight up, it was pointed more to my knees. It suddenly went in easily several more inches before encountering resistance. It seemed that was as far as it could go without risking injury because she held it there while removing the panties from my mouth and then asked me about the experience.
“I’m really enjoying this actually, Miss. Thank you for teaching me to be a good patient for you. Anything you want, I’ll do” I offered, wanting to reassure her that even if I seemed apprehensive, that I wasn’t going to screw up a good thing. Not this time around.
“Excellent. Well, Sounds are measured in an archaic scale referred to as ‘French’. The sound I am currently testing you with is a 16 French. It is smaller than a number 2 pencil. The good news is, I have lots more, going all the way up to 44 French. Those are almost as large around as my thumb!” she seemed gleeful at this pronouncement.
I had no doubt that I couldn’t possibly accommodate a sound the diameter of her thumb. Not even the size of her pinky! She withdrew the first sound and set it aside; next producing an 18 Fr sound.
She repeated the procedure, first pointing straight up, then as it probed deeper and encountered resistance with the natural contour of my urinary tract, she followed the angle. I could tell this one was larger, but not unpleasantly so.
It wasn’t until she started with the 22 Fr sound that I started to feel painfully stretched. She pressed against the underside of my cock, pushing against the sound. She followed it down, pressing against my perineum, all the way until she came to the butt plug. Apparently, the sound was nearly to my prostate.
When it came out, she explained “I’m going to use size 24 next. It will hurt, but you shouldn’t bleed. The goal is to determine what your present size is, and then set up a stretching routine. It will take time but eventually you’ll be large enough to accommodate my fingers.”
I was skeptical, but hey who was I to question her?
“Unfortunately, the male urethra is banded by tissue that isn’t especially stretchy. The female urethra doesn’t have that problem. It’s possible for a woman to stretch hers so much that she can take a penis inside. It’s quite impressive from an anatomical perspective, although why any woman would ever want a penis in ANY part of her body is a mystery to me” she explained.
I hadn’t really caught what she’d said. I was still playing over what she’d said at first ‘you shouldn’t bleed??’ You mean, bleed out of my dick hole??? That didn’t sound good at all! She could see the concern on my face and sought to allay my fears.
“The level of pressure and pain you would experience leading up to stretching to the point of tearing would be highly unpleasant. The real risk comes with the use of topical lidocaine. By numbing the pain receptors it’s quite easy to push through. We won’t do that. For now. Perhaps later, if you find you are unable to continue increasing your size this way…” she trailed off.
She went into the other room and returned with a lock box in hand. She placed it in my field of view and opened it. She withdrew something and held it out for inspection while explaining “Now then, I’m going to fit you with a special custom-made device.
It is a stainless-steel penis plug and cock cage, with a threaded opening at the tip of the penis. Into that opening I will install a hollow silicone tube. It’s like a sound, in that it will stretch you but being hollow will allow fluid to pass in or out as I desire. You’ll also notice a tag that dangles from the lowest point. It is an engraved dog tag.”
She held it closer and I was able to read the machine etched lettering “Mistress Nurse’s Pet”
My heart fluttered excitedly. She was collaring me as her pet! She brought it closer to my face.
“Kiss your collar, slave”.
I leaned slightly and kissed the cold metal. She didn’t immediately draw back so I tentatively licked it as well.
“Now then my pet, you belong to me. You are my property. My plaything. My entertainment. I’ll do with you, and TO you, exactly what pleases me. Do you understand?”
“Yes, Mistress Nurse. Thank you!”
“Do you wish to serve me? Will you obey completely and without question?”
I responded affirmatively on both counts.
“I expect you to keep this on as long as possible. You will wear it every day. You are to text me EVERY time you put it on in the morning, and obtain my permission every time you wish to remove it, so that I have an exact record of your training efforts.”
She emphasized this multiple times. It struck me that she seemed curious to know how long I could wear it–probably as a test of obedience, or to learn my pain threshold?
Or both. She knew from previous experience that it is hardly noticeable for an hour or so, but after that it grows increasingly painful, exponentially, until it’s all the wearer can think about.
She held up the translucent tube with a threaded metal fitting at one end, and also the cock cage. She then dismantled the cage and installed the base ring around my cock and balls. The cock cage portion locked onto the base ring.
It was like a metal half globe, with a large hole at the tip. When it was fitted up, I noticed how tight and confining it was. It wouldn’t be pleasant to wear for extended periods.
“I’ll also have you train with this. In the case of urethral dilation, it is important to withdraw the silicon sound each hour. The soft material shouldn’t chafe or cause bleeding the way the metal probes can, but because of the stretching, blood flow will be affected. It will be necessary to withdraw for a few minutes each hour to ensure there are no complications”.
She explained all of this rather off handedly, but I was really nervous. Excited, but with an undeniable undercurrent of fear.
She aligned the silicone tube, and fed it into me. Sure enough, it was every bit as invasive as the metal sound. Thankfully there was no real pain to it (yet), no more than a little distracting.
“What are you?”
“I am your slave Mistress Nurse”
“Mine exclusively and without reservation?”
I knew I had no reservations. I wanted this. I wanted her. I wanted to be everything to her. I was sure I would never meet anyone who so completely embodied my ideal physical and sexual type.
“I’m completely yours Mistress. Mind and Body. To use and abuse in any way that will bring you pleasure.”
“That’s quite an offer. You might not enjoy being on the receiving end of some of the menagerie of kinks I will indulge with you.”
That one gave me momentary pause. I knew in the world of fetish sex, that it was easy to cross lines and destroy scenes. Even entire relationships. But I was also willing to serve her in the ways that pleased her because I knew she would also serve me in the ways that I craved most I needed to be submissive to a woman every bit as much as she needed to dominate a male.
It would be a mutual exchange. It might not be exactly as I would always choose, but I was certain that the balance would land heavily on the side of mutual satisfaction.
“Yes Mistress. You can do anything you wish with me, so long as there aren’t permanent adverse affects. I exist to serve you. To please you. I may not understand all the ways that I may be allowed to please you in the future, but I am fully committed to doing so.”
“Marvelous. Such a good patient! A good slave, really.”
She removed her gloves and cleaned up. Then, she made of show of pressing her fingers against her pussy, forcing the thin fabric into her folds; then bending over and reaching beneath her skirt to pull down her skimpy thong. It slid over the garter straps and stockings and down to her ankles. She stepped out of it, and picked it up.
She turned it inside out, and brought the very wet crotch panel to my nose. Shit, but she had an amazing scent. I took several deep breaths, closing my eyes and delighting in the naughtiness of sniffing her freshly discarded panties.
She left them sitting on my face, and I tried to stick my tongue out and sample her flavor, but just then she tightened the chest strap and waist strap, and slipped out of her shoes. She walked away for a couple of minutes. When she returned, she pulled the underwear off my face. I got a good look at her, and saw that she had put on an unusual type of harness.
There were multiple leather straps. One that went around her waist like a belt. It was studded with subdued chrome points. There were two straps that came down in front, forming a small V just above her slit. The V then split out with two straps that went down the inside of each thigh. They connected, just below her tailbone, to a small metal ring, which connected to the waist belt with a single strap.
Finally, there were two more straps from the sides of her hips that went straight down and attached to the two straps that cradled her ass crack. There were a few other straps as well, but the overall effect was that when this harness was fully secured, it spread her incredibly firm orbs of flesh apart in a highly provocative way. I could easily see her winking brown eye.
She climbed up onto the table, straddling my waist. If it hadn’t been for the highly confining and stretching cock cage, I surely would have been hard enough to pound nails through a 2×4. She lowered herself against my stomach. Then she gyrated her hips over my body, pressing her hot dripping flesh against my stomach.
I sucked in my breath to give her better contact. She moaned with approval. It was so fucking erotic, to be her personal sex toy!
She shimmied up my body, so her delectable naked pie was mere inches from my chin. She instructed me to study it carefully. She took the opportunity to educate me, explaining how she liked to be touched, licked, and kissed.
I was so glad to see that she was completely shaved. Full Brazilian laser hair removal sessions every two months kept her smooth as a baby’s ass all the way from navel to tailbone. My mouth was watering. She was expert at teasing, getting closer only to draw back.
She moved to get up and I was afraid that was the end of it. but she actually turned around, this time her stunningly beautiful ass was almost sandwiching my chin. I drew in deep breaths, noting the mixture of her natural scent mixing with a mild perfume.
I rocked my head, trying to make contact, hoping to give her pleasure. She cocked her head and looked back at me, smiling devilishly. I was dumbfounded by the beauty and perfection of her feminine flower. The delicate outer folds gently parting, and glistening with a suggestion of lubrication.
And then it happened. My un-enumerated fantasy of so long, came true. She scooted back, and lowered herself onto my face.
Her puckered ass hole was directly over my mouth. I’d never actually rimmed anyone before but I’d read about it and fantasized about it so many times that I immediately took to it.
My tongue darted out, teasing circles. She rolled her hips a little too, only to pull back, looking over her shoulder, down at my face.
“What do you want my pet?” she asked coyly.
“Please Miss, let me eat out your incredible ass. Please let me be your oral slave, pleasing you anytime you wish, any way you wish!”
That was clearly the right answer. A wide smile broke across her face and she lowered herself back down. I again teased circles around her back door. Large circles at first, but growing tighter, until the tip of my tongue was gently swirling around the crinkled entrance.
“Yes, Lick me. Lick my anus. Put your tongue inside my ass hole” she ordered.
I rolled my tongue into a stiff little tube, and pressed into her. I pumped it in and out a few times, going deeper each time. There wasn’t a strong taste or smell thankfully and my confidence and enjoyment grew.
I pressed into her as deeply as I could go. She rolled her hips and I could tell she was rubbing herself. “Yes, my slave, tongue fuck me in my bottom. Use your tongue like a tiny cock and fuck me.”
I was thrusting back and forth and twisting and twirling my tongue inside her. I wasn’t used to this level of oral motion and my mouth and tongue were rapidly moving from tired to burning with the effort.
Finally, I had to just hold my tongue and head still and let her ride me. I willed myself to lengthen my little tongue-cock as much as possible, penetrating the murky depths of her ass. Her muscles alternately clenched and relaxed, accommodating my meager length.
My tongue was long enough to penetrate her outer and inner sphincters when I really pushed hard. It was indescribably erotic to be so deeply inside her bowels. With her own efforts at clitoral stimulation, it didn’t take long for her to climax.
As the building intensity peaked, she gave a loud groan. Her little crisis was powerful and captivating. I was floored by the intensity of her pleasure, and in awe that I’d helped her to feel so good.
She held her position for a bit, but my tongue and mouth were getting very sore so I just held still. She turned to look at me, scooted down a bit, then brought her dripping fingers to my mouth. I cleaned each of them meticulously, as though the precious drops of her cum was the only liquid I’d have to drink that day. It turned out–it wouldn’t be.
She turned back around and knelt, her engorged pussy directly over my mouth and nose.
“I have another desperate need. Will you serve me in this also?” she quietly asked.
“Will you be good, and drink everything I give you? If we are going to continue our arrangement beyond tonight, we are going to cover the whole gamut. At different times, I’ll pee for you. I’ll pee on you too, on your cock and balls, on your chest and face. You’ll also take my golden fluid in your mouth. You will drink my nectar straight from the sacred fountain head. Do you agree?”
I had never participated in any sort of watersports either. I had read all about it and knew there were men who liked to drink pee. I’d even seen it in pornos. But since I had never been peed on before, this was well above my level of experience.
If I’m going to be honest, the truth is that in calm moments, the idea was somewhat repellent. But, when fully aroused and fully switched over to sexual-submissive mode, it seemed like a mystical alignment of the stars was taking place to manifest one of my kinkiest fantasies.
A thought jumped through my mind rapidly that even though the idea of pee play was rather erotic I knew that reality was often very different from fantasy.
But again, bikini girl walking out of the pool room while saying “too bad” flashed through my mind. I wasn’t going to blow this now. I responded with as much enthusiasm as I could muster “Yes Miss, please let me drink your nectar. Every last drop.”
She smiled broadly and used her hands to spread herself apart in front. Aided by the harness straps. I could see the very prominent urethral meatus within; like a closed eye. She took a long moment to relax. I inspected every nook, every crevice. It was absolutely beautiful. Her muscles rippled slightly, and then the eye opened. Tears flowed in drops–at first a trickle. I extended my tongue to collect the drops of rain from a salty and bitter storm cloud.
She lifted herself slightly, and tensed her abdominal muscles. The dribble rapidly gained gusto becoming a gush of golden liquid. Her movement caused her stream to migrate from my tongue, up to my lip before settling squarely into my mouth. Her hot flow splashed around inside my mouth. It was bitter. But she must have been in the habit of drinking a lot of water each day because it wasn’t overpowering either. I was able to swallow with my mouth open so she didn’t have to stop.
After the slight movement of my head and neck that signified several swallows, she clenched tightly and pinched off the stream to allow me to finish swallowing and catch my breath. Then she grabbed my hair and pulled my head up off the table to engage with her pussy. I opened as wide as I could and tried to draw her labial folds into my mouth. The flow resumed.
This phase in flow was accompanied by a subtle but noticeable sound. A soft sort of grunt that signified her intense pleasure that I had actually swallowed. I hadn’t choked or spit, or tried to turn my head away. Looking at her face I saw that she was flush with excitement and that she was profoundly pleased that I had done this for her.
The taste was different than I expected. Salty to be sure, but milder. There was a subtle bitter after taste that came on after a few seconds. But even that wasn’t really “bad”. It was just different.
“There’s more my pet, much more of that. I hope you are very thirsty indeed” she admonished.
Her perfectly muscled abdomen flexed and relaxed. Once again, the flood resumed. I had a hard time keeping up now because she didn’t entirely stop. It was tricky to swallow time and again with my mouth open, while breathing between swallowing, but I had practiced the technique drinking from water jugs held above my head when there weren’t any cups available.
By the time her flow tapered off, I was feeling bloated, water logged. It was an amazing feeling though. Shit. I couldn’t believe how hot it was. In the moment I felt a transcendent peace wash over me, a sense that I’d connected with a purpose I’d never known I had, but which had always been there. Just waiting for someone like Oksana to unlock it.
“Fuck that was amazing. You really are a kinky ass-licking bastard” she moaned.
Pleased with myself, I smiled. She lowered herself back down onto me. I forced my tongue up inside, teasing the opening of her pee hole. I wished I could force the tip up inside of her vagina a bit but the angle was wrong. She soon rolled her hips forward a bit more.
I got the message, and went to work on her clit. Soon she was thrashing and grunting. The orgasm that overtook her was incredible. She even squirted. The taste was quite different. If anything, I liked it even more. Fuck, Oksana was a squirty girl too! Could this get any better?
The taste lingered in my mouth as she climbed off and loosened my restraints. I was directed to get up get dressed. She gave me clear instructions about wearing the butt plug until I could have an enema, and penis plug until bed time, if I could manage it that long.
She also told me I was to wear both devices each day. I could remove it for up to one hour if I was sore, but then it had to go back on. I was to text her immediately if there was a problem. Otherwise she expected complete adherence to her training program because she had big plans.
I dressed and hobbled down the stairs to my car. It was difficult to sit down because of the pressure being applied to the plug. I drove home in mild discomfort, shock, and riding a post-coital high.
Even though I hadn’t actually climaxed, it had been the most intense and fulfilling sexual experience of my life. And it was only just the beginning, if I played my cards right!
I couldn’t wait to see what she had in store for our next special date! It became clear over time that when it came to orgasms, what Oksana liked most and wanted from me (well, demanded actually) was lots and lots of oral sex. She wanted it in every position imaginable and some that I could never have imagined. Think “Kama Sutra Guide for the Gifted” and you’ll have an inkling of the stuff she came up with.
Thankfully I have no problem giving her oral for long periods of time. It’s been good to strengthen my facial muscles because I’m definitely increasing my endurance with practice. I’ve come to really enjoy worshiping and servicing her delectable little anal rosebud. I love watching it move and flex as she relaxes, tenses, or bears down.
The discovery that I could learn to love servicing a bottom as much as a pussy was a powerful one. I get a tremendous erotic flush from putting my face squarely on target between her flawless nether cheeks.
I came to learn that Oksana was enthusiastic for every type and variant of anal play. She more often preferred to administer to me. But there were occasions where I was invited to return the favor. I never did “top” her. I did exactly and only what she authorized me to do.
It was still intensely pleasurable for me to violate her in such a perverse manner. She actually loved to receive enemas as much as I came to love them. And that was astonishing to me because I’d never once had someone respond positively to the invitation to share enemas in all my online and in-person dating.
If you had asked me before I’d met Oksana, I would have said it sounded like a hot fantasy, but I’m not sure I would have actually done it for the simple reason of hygiene and sanitation. But actually, trying it was so far beyond anything I imagined. I was hooked. It helped that she was fastidious about her presentation. I never once had a complaint about conditions as she lowered herself onto my face.
My Cumming on an infrequent schedule relative to hers was an understood part of the deal. I knew that once I got off, I suffered from the condition that the majority of my male counterparts do. I have a desire to Cum and Go. Go to sleep, Go home, Go wherever mentally. I just lose all interest after climaxing.
But as long as I haven’t cum yet, I’m fully invested in the experience. So, I didn’t have any hard feelings when she forced me to hold off. Even when she put me in chastity to have assurance that I only came with her permission, so as to be maximally ready to serve my Golden Goddess Nurse.
Truthfully it was a good deal for me. When she did allow me to cum in her presence, she almost always did it herself with her hands or a vibrator.
It always felt great. Best of all, the medical role-play experience we’d had in her bedroom was just a vague foreshadowing, for what happened next!
*********************************************
Thanks for reading, positive/constructive comments are always welcome. I’m not great at dialog so I’m desperate for editing help! Hopefully I’ll get Pt 3 loaded soon. If there is demand for the illustrated version of the story, I’ll work on that too.