It Started Innocently Enough

"You would look bitchin' in any one of these," she said.

Whether intended or not, the online shopping trip was like surfing porn, and my dick was getting stiffer by the minute. The problem, though, was the cage. More often than not over the last month she had chosen to keep my cock locked up in a stainless-steel chastity cage. A tight ring encircled my scrotum and dick, and a very, very short tube with a cage front was secured to the ring and covered my penis head, with an insertable lock on the ring. The key was on a chain she kept around her neck. The cage stayed on for however long she wanted, sometimes hours, sometimes overnight, sometimes days at a time. The cage fulfilled its sole purpose perfectly: preventing erections and stimulation of my dick.

She had warned that my dick would be useless as a woman and she was training me how easy it was to live without one. However, while I was learning to live "without one" it certainly wasn't fun or easy. The cage did allow me to piss, but only sitting down on the toilet like a woman, and I had to shower often to keep things relatively clean and sanitary. But jerking-off was physically impossible. Moreover, anything that caused my dick to grow or harden was met with stiff resistance by the two-inch long confines of the stainless-steel cage. Thus, getting a hard-on by browsing sexy web sites was unpleasurable: the stiffer the hard-on, the more discomfort.

The obvious corollary: no orgasms. I could count on one hand the number of times I'd come in the last month. When we did have sex, we spent our time with me pleasuring and bringing her to orgasm orally and then our session would end without me coming, regardless if the cage was on. It was becoming apparent that withholding my sexual relief was designed to put me into an extended state of horniness. It was working.

"Okay, look away while I choose a dress for you," then she scrolled and clicked for a few moments. "Okay, one more shop to go."

When I looked back at the screen it was linked to a sex toy website. She scrolled to various toys and accessories.

"Oh, vibrators. I think you should have your own, and not share mine. Maybe one with a remote so I could control what you feel? Would you like that? I recommend something with multiple speeds, because sometimes you want just a little buzz and sometimes you really want it to thump you, know what I mean?

She clicked on the dildoes tab, and asked me whether I had a preference for dildoes with balls or without.

"I think silicone didoes are best, and stay away from anything jelly-like. What about size? Six inches? Seven inches? EIGHT inches? Ha-ha-ha! Anything bigger than 5 inches would be way larger than you! What do you think is the biggest dildo you could deep-throat? I mean, without choking or gagging? As a woman, men will rate you as more desirable with this skill than if you possess a college degree. So, you will need to acquire it if you don't have it naturally - we shall have to check that out. Hey, here's one with a suction cup--place it on the floor and hump yourself, or stick it on the wall for deep throat training -- very versatile, what do you think about that, should we get it? It's available in 8 inches too. Do you have a fantasy about getting fucked with a really big cock?

She hit the PageDown arrow and landed on the BDSM page.

"Here's some lovely clit jewelry, too bad you don't have one, but maybe I'll get the one with the lapis stones for myself. Beautiful. Oh! Oh! Clover clamps! Must haves! And they have a lovely silver chain connecting them to each other, looks long enough that you could hold it in your pouty-mouth while tugging on your tender pinched nipples! A definite, baby. Okay it's getting late, that's enough for tonight -time to fill the shopping cart - turn around and let me finish."

Through the miracle of credit cards, cloud-based electronic commerce and warehouse-to-home delivery systems, a passel of parcels would begin to arrive at our doorstep.

"Will that be cash or credit?" asked the young well-dressed sales clerk. It seemed such an anachronistic question, who used cash anymore? We were in a fairly high- end beauty store and had just spent the last hour poring over my makeup selections for the big event. When I had originally asked for full makeup I never dreamed how extensive the list of products was required nor how expensive it would be. In no particular order we took out of our wicker shopping basket: lipstick, liquid eyeliner, mascara, lip liner, foundation, concealer, bath bombs, lip gloss, three colors of eye shadow, eye brow pencil, blush, highlighter, false eye lashes, two colors of nail polish, temporary hair color, nail sealer, hair gel, teeth whitener and several skin moisturizers. As I handed over my credit card the young woman said to my wife how lucky she was to have such a generous partner paying for her $300 in beauty supplies. My wife didn't miss a beat and replied,

"Oh these aren't for me, they're for her. She's got a hot date coming up and she has to look her best! Isn't that right Mina?" Her piercing stare at me meant she expected a reply.

As the words, "Yes Mistress, I want to look my best for you," spilled out of my mouth the clerk giggled softly and I felt my face flush bright red. She handed me my card back as she packaged our purchases and said, "Well I hope you enjoy your date... MINA," slightly exaggerating the name since it obviously was different than the name on my credit card. I couldn't wait to get the hell out of there, but my wife had different ideas.

"That's a beautiful shade of lipstick you're wearing," my wife complimented the sales clerk. Indeed, she was beautifully made up, her hair perfectly coifed and she was impeccably dressed. "What's it called? Perhaps you could recommend a new color for Mina, she's always looking for something sexy?"

"I'm wearing 'Syren' by L'Oreal. But for Mina, I would recommend one of their new colors. It's called 'Attention.' Would you like to try it? We have a customer sample display over here," as she motioned with her arm.

I felt my arm being tugged as we moved over to the display. "That's a gorgeous color for you Mina! You must try it. Here, let her help you apply it, you know how awkward you are with these small sample lipsticks!"

And with that, a complete, albeit beautiful, stranger was applying lipstick to me in the middle of an upscale beauty store. What humiliation - my fantasies always included the risk of public display of my kinks, but this was over the line! What if someone recognizes me, not just in the shop but on the way to the car? And what must this young woman be thinking of me?

The stirring in my pants negated all these feelings of anxiety. Having lipstick applied to your lips by a beautiful young girl is hot -- guaranteed to give you a hard-on. My dick was stiffening with every flick of her wrist painting wax on my lips.

But this was not a random outcome; this was thoroughly thought-out by my wife. She purposely drove to a beauty store at a mall far from our house, unlikely to encounter people we knew. She chose an upscale beauty store likely to employ good-looking staff. She patiently waited to pick the best looking female staff person to wait on us.

And she knew all along she would drop the line to the clerk about her lipstick - that's why she made me get locked in my chastity cage before we left on our little shopping trip. She knew my humiliation would turn to exasperation as my engorged cock, facilitated by the sales clerk, ran up against the confines of the cock cage. There would be no boner, no evidence showing through my pants. And if someone saw a guy with lipstick on his lips, so what? Nothing shocking there these days. And the clerk, she must think I'm a freak? But why the fuck should I care what she thinks? Anyway, my wife quietly thanked her for playing along with us as we left, and slipped her a nice tip. My wife. She's turned into a fucking teasing bitch.

As the days ticked down to my birthday they took on a familiar routine. I was performing all the standard tasks outlined in the Obedient App without further miscue. But soon after the online shopping spree packages began arriving, I started undergoing daily "training sessions" in preparation for the special date.

The typical day was comprised of five elements: the first was lipstick training. She felt it was unrealistic for me to learn how to do a good job of applying full makeup in the time left, but I could become expert in applying my own lipstick. Thus, every day a lip liner, lipstick and lip-gloss would be left out for me in a specific place. Some days it was a long-wearing matte lipstick, other days a high-sheen glamour makeup brand lipstick. Regardless, I was taught to outline just inside of my lip-lines, and then fill in with color by dabbing, never rubbing, on lipstick with a brush, usually in two thin coats. Almost always it was finished off with a wisp of gloss unless she deemed one was not necessary. Each time I would present my work for close visual inspection, and if there were any flaws they would be pointed out and I would have to wipe everything off and start over from scratch. Needless to say it took numerous attempts before I could consistently meet her standards on the first try, and within a reasonable amount of time! Once lipstick inspection was passed, I was told how long I had to maintain it that day- oftentimes I was given an hours-long goal to give me practice on carrying out my normal day activities and keeping my look refreshed.

The second element was corset training. The day the black satin doubled-boned corset arrived I thought I was supposed to throw it on and cinch it down as tight as possible. It was beautiful and I desperately wanted that hourglass effect, but she set me straight.

"Both you and the corset need breaking in for the long-term health of each of you. You can ruin the corset if you don't break it in properly, and you can harm yourself if you don't let your body gradually adjust to the increasing tightness of greater and greater compression."

So, that's why every day for 1-2 hours I lace on the corset, each time tensioning the cords a little tighter. The first few times I needed her help just figuring out how to close the front busk, no less how to start tightening the laces. She taught me how to position the side panels properly on my hips and start the progressive tightening pattern from the top and bottom of the laces. Then using my fingers to hook between the laces, I could sequentially tighten the entire back, keeping everything straight and even.

Now after many wearing's, the corset is beginning to feel more supple. The feeling as the laces tighten is incredible - immediately my posture becomes erect and all movement of my torso is constrained; bending from the waist is impossible -- 22 steel stays are sewn-in there for a reason. And breathing? Yes, it's possible but you re-learn how by taking shallow breaths, and practice how to avoid hyperventilating.

But the payoff is phenomenal. The tight, confined sensation is a form of body bondage, and my wearing it is confirmation of my submission to her. Plus, after just one week I could see new curves: I took 3 inches off my waist measurement and was training to double that by date night. It's now evident that I have a waistline distinct from my chest, and some actual hips are showing up - the beginnings of a feminine form.

The third training element was dildo training. Unfortunately I did not show a natural ability to deep throat a dildo when she tested me. I gagged and wretched as she progressively pushed a 6-inch dildo into my mouth and down my throat.

"Your ultimate goal is to pump this 6-inch dildo full length down your throat once every second for two minutes, and then take this 7-inch dildo, deep throat it, and hold it there for 30 seconds without gagging. When you can do that, you've got it made. Guys will pat you on the head and call you, 'Good Girl.'"

More often than not the two dildoes were left with the daily lipstick, and each day I practiced my oral skills for 30 minutes. It was important to accomplish these dildo exercises without messing up my lipstick; many times a refresh was needed.

I started each session by slowly licking the silicone dick with the tip of my tongue. It was black, 6-inches long and had realistic looking veins and a glans head at the top. I started at the base and worked my way inch-by-inch to the very tip. I used my own saliva as lube to make it wet and slick. Sometimes I would even make circles around the shaft with my tongue.

As I licked, I closed my eyes and imagined what it would be like to give head to a real dick of warm flesh, not the cold silicone that was staring at my face. I would then move on to push the end of the dildo into my open mouth, my painted lips parted, waiting to take it in with high anticipation of what was to come next. I closed my mouth and began to suck, soft at first, then harder, then as hard as I could as I began to lower the dildo farther and farther, letting it glide over my flattened tongue. I reached my head up high and stretched out my neck as straight as I could and continued to advance the dildo down my throat. I wanted to take its entire length, all the way to its hilt, without any hint of gagging. My mind was focused on precision; speed would come with practice. I then slowly withdrew the practice dick, and started the cycle again. Slowly. In. Out, In. Out. I continued for at least 10 minutes.

I then switched to the purple 7-inch dildo. Not only an inch longer, it was at least a half-inch thicker in diameter. Warming up with the 6-in dildo was a good strategy, as my mouth and throat were at least somewhat prepared for the seemingly huge invader. In fractions of an inch I dropped the dildo down lower and lower, I felt my windpipe being crushed as the dildo took up all the space in my throat. When I looked in the mirror I could actually see the bulge of the dildo head pushing against the skin of my neck. The urge to gag was violently hard to control, it is a reflex, it just happens, you really can't control it, you just manage the surrounding environment and hope for the best. When it reached the full 7 inches I could not breathe and had to hold my breath. My mind focused on calm and quiet places elsewhere to help from choking or gasping for air - thank God the goal was to hold the dildo down for only 30-seconds.

After the first week, if I was patient I could occasionally deep throat the 7-inch dildo as required without gagging. However, the cadence of pumping the 6-inch dildo oftentimes caused me to gag on my own saliva or air as I had to synchronize breathing, swallowing and relaxing the back of my throat all at the same time. This was not easy, especially wearing a corset.

"Keep at it," she encouraged me, "You will get better with practice - believe me it is harder with a real dick, so you had better perfect your technique first with a dildo."

The fourth training element took no real skill, just persistence: butt plug training.

"As a woman, you'll find men will love to degrade you and fill your holes with all sorts of shit. You're going to have to get used to having things shoved up your ass," was my wife's sage advice.

Butt plug training was accomplishing two things: first, by increasing the size of the butt plugs we trained with, it was gradually stretching out my sphincter so it could accommodate a real-sized dick with no pain, and second, by clenching and holding a plug in place for extended periods during the day I could work out my kegel muscles and strengthen my pelvic floor. This way I would ensure that anything that did penetrate my asshole will be welcomed by a nice tight grip.

Since my asshole was relatively virgin territory she started off my training with a small silicone plug. But well before trying to insert the plug she stroked the outside of my ass around my anus with her fingers, rubbing the lube-covered tips in gentle circles around the opening with soft, massage-like stokes. Gradually she added more force to the surrounding tissue with her thumbs, gently pressing then releasing, I think it's called acupressure. With the addition of more lube she pressed just the tip of one finger at the entrance of my butt, pushed gently and held it still, then withdrew. She repeated this several times before advancing that same finger into my rectum just to her first knuckle, and held it there, then slowly pressed it against one side of my rectum and then the other. This pattern was repeated again and again, each time advancing her single finger into my ass until it could go no further. I felt no pain, the finger felt no resistance. I liked the sensation of having a finger up my butt.

She carefully withdrew her finger and with a deft touch replaced it with the small well-lubed butt plug. She moved at a pace that allowed the plug to slide easily past the sphincter muscle and nestle into place. Its small bulb wound up inside me and its flange was outside my butt, preventing the entire plug from embarrassingly disappearing into my lower bowel.

"Those are the principles for inserting a butt plug - I've demonstrated how to do it, from now on you will be responsible for inserting it yourself. You will use a plug I set out for you each day, keeping it in for the time I specify, and completing the exercises I write out for you." Of the five training elements, this one was probably the easiest.

If butt plug training was the easiest, the fifth and final training element was the hardest. Certainly the most painful: clover nipple clamp training. Of all the toys to choose from the online shopping store she had to pick this one! Again there was little to no skill involved.

Clover clamps are remarkably simple but diabolical, comprised of a metal hinged two-jawed clamp that is spring loaded. When spring tension is released in one direction the jaws simply open and an unsuspecting nipple can find itself clamped between the two jaws when the spring tension is returned. With most other clamps, when pulled the jaws slip or lose tension and fall off. However, what's diabolical is the clover clamp's design will increase its jaw tension when pulled; they are near impossible to pull off because the harder they are pulled the tighter the jaws close.

"Women's tits are the subject of men's adoration, but even more so is men's abuse, as they are sucked, bitten, pierced, slapped and bound. The clover clamps are to help train you to feel, acknowledge and accept the nipple pain many women endure in the real world. I'll leave daily exercises for you on how to train with the clover clamps, including how long you must wear them, any weights you must hang from their chain, and any other special instructions to simulate real life experiences you may encounter in the future."

I hate, hate, hate clover clamps. Their pain is unrelenting. While some nipple clamps hurt and then the pains subsides as the nipples go numb, the clover clamp pain just seems to continue to build and build. And the slightest pull on the chain connecting the two clamps is like flooring the gas pedal of a car: the pain just accelerates in intensity in a flash. Even a scant one ounce weight hung off the chain with a paper clip, allowed to swing freely while walking, can torment the wearer. I know, from experience. Her exercises were brutal. I hate clover clamps.

As the 8-week mark approached almost all the boxes were getting checked off. The requisite points were recorded in the Obedient App. The agreed upon weight loss goal was met. I had dutifully if sometimes grudgingly completed the five training elements as required. And I had survived the prolonged period of sexual denial, chastity and humiliation leading up to my birthday wish role-play. Even the reason for the flogging of my ass had become a distant memory (but the feeling of the latex flogger hitting my bare ass will never be forgotten.) While we had not agreed upon a specific date, I sensed the time was near.