Discovering Amber

byMs_Allison©

Author's Note: This is My amber's foray into telling her recent life story. I have decided that her reward for this is an orgasm, feel free to let Me know if she is worthy of getting one.

*

I have always enjoyed women's lingerie. From looking at catalogs to seeing girlfriends wearing it I have loved the look and feel of sexy, silky lingerie but for me it has always gone deeper. At 18 I tried on my first set of panties, oh my God that was wonderful! It was all downhill from there. Eventually I tried leg shaving and shaving my crotch but those never lasted long because I didn't want to have to explain it to anyone. I would go through binges where I wore panties and stockings under my clothes during the day out and about with friends or at work and then ran home to masturbate furiously. Then I'd go through the shame and embarrassment of having to admit that dressing like a girl turned me on so much. It got worse when I tried anal toys in my mid 20's. Wearing a butt plug was interesting at first but what really struck me was pulling it out and feeling the emptiness left behind.

Maybe I should have started this out differently "Hi my name is amber and I'm a sissy crossdresser."

So what brought me to being 26 and standing in the kitchen in black patent 5" heels, suntan stockings, a white satin with floral print corset and matching panties, blonde wig and makeup typing away on the laptop you ask? That was being discovered by my girlfriend turned Mistress. Now my penance for stretching out some of her bras and panties is documenting my story for the unseen masses to read. Oh sweet humiliation how I cherish you so!

After Allison and I moved in things were going great. She is 28 and truly stunning with long auburn hair and a short and very tight body. She always dresses nicely and has the most amazing lingerie it was only a matter of time before I had to put some of it on. It started casually enough. She works irregular hours while mine are set so it was easy because I would be home alone quite often. I still had a bag of stuff from my single days as well including some lingerie and heels as well as a 5" butt plug and stockings. That was all tucked safely in a bag in the back of the closet. At least once a week when I was home alone I would spend an hour in our room dressing and wearing heels until I couldn't stand it anymore and had to play with myself. That's how she caught me. Lets just say that more than once my performance in bed was "lackluster" because she had come home after I had spent the evening masturbating. Allison was convinced I was cheating on her. She even noticed some of her lingerie would end up in the laundry even though she hadn't worn it and blamed it on another woman.

The one thing you have to know about Allison is most people in this world play checkers, she plays that Star Trek version of chess with the different levels. She is always 5 steps ahead, always! I should have remembered this, unfortunately I wasn't that smart. Allison left for work one day calling me at my job on the way and telling me it would be a late night. I knew exactly what I would do and half way through the conversation I was too distracted with my impending masturbation session to even listen to her. Once at home I stripped and put on my girlie best. Actually Allison had this pair of jade green bikinis with a black lace overlay that I'd been dying to wear. They had a matching bra too. I put on my stockings and heels and went looking for them! When I got them on I walked in front of the mirror and turned and twirled feeling like the slutty girl I had always wanted to be. Then I just had to get my butt plug! Little did I realize that in the stereo cabinet was a small camcorder recording my every sashay and swish. That night as I slept Allison sat in the bathroom watching me masturbate in lingerie.

Most women would have been upset and accused me of being gay. No not Allison. She was the thinker and the planner so while I slept she moved the pieces around the board putting me in checkmate without my even knowing it. It was a week later before she made her move. Once again she called me saying she had closing reports and month end stuff to do so she would be extra late. Again I droned out of the conversation thinking about going home and dressing up. It was a Friday night too so I knew she would be busy at work. I couldn't wait!

I got home early and took my time getting dressed putting on black back seam stockings and black patent 5" heels with an ankle strap. Then I added a black satin and lace demi bra and filled the cups with panties. Finally I put on a pair of black satin side string bikinis with a floral detail in them and a matching garterbelt. Oh I was in heaven! Then I decided to go even further. I went to the bathroom and grabbed Allison's lipstick putting a dark red on my lips that she hardly wore. In college I had my ears pierced and with a little extra effort I got a pair of her dangly earrings in my ears. It was all almost too much and when I saw myself in the mirror I had a hard time not touching myself. Finally I had to put in my butt plug before I popped! With it in place and my panties back up my cock was rock hard. I rubbed it through my panties and began moaning.

"Now aren't you a sight?" A voice came from the bedroom door.

Those words ended my secret life and my world as I knew it. I was busted. Really what could I say? "Oh sorry honey I don't know how I ended up in all this stuff!" or "Oh I mistakenly put this on I thought it was mine!" No that wasn't going to work. I looked over to see Allison leaning against the door frame with her arms folded under her breasts. I wanted to run but where the hell was I going like this!?!

"Oh don't move sweetie," Allison said walking towards me, "I want a better look at you."

Allison slowly walked around me occasionally adjusting a strap or tugging on my lingerie.

"So what comes next?" Allison asked while unbuttoning her blouse.

"What do you meant?" I asked sheepishly knowing she could easily see my raging hard on.

"Come on now sweetie," she said removing her blouse exposing a hot pink satin corset I had never seen before, "I know what comes next but I want you to tell me."

I couldn't even speak as I watched her undo her skirt to show white lace top stockings and a small hot pink thong. She looked amazing with her hair pulled back and her strapless corset pushing her breasts out. Allison walked slowly over to the bed and sat on the edge crossing her legs slowly. I felt my resistance crumbling.

"I'll tell you what," She started, "why don't you change my shoes for me while you try to compose your thoughts." I looked at her quizzically until she continued. "These heels are for work I have a pair much better suited over by the stereo cabinet. Go get them." Walking to the cabinet I saw the shoe box on the floor next to it and went to pick it up. "Oh no sweetie," Allison's words stopped me in my tracks, "keep your legs straight and bend down to get it from your hips." I steadied myself on my heels and did the best I could to pick up the box as she ordered. "Look to your left inside the cabinet," Allison said with an authority in her voice I had never heard before, "see that in there?"

At first I didn't see it but then it stuck out like a mushroom cloud. I felt my ass clench around the butt plug as I saw the camcorder with a small piece of tape over the red light.

"It was there last week too when I worked late," Allison called out from across the room, "and I saw everything." She let the last word sink in a bit before she continued. "Even you putting that cute plug up your ass." My heart sunk and ass puckered as I realized all she had seen. "Now get my heels bitch!" Allison demanded.

I picked up the shoe box and walked uneasily back to her. My head was spinning and my mind was racing and I really thought I would pass out. This was the moment where I realized just how trapped I really was.

"Kneel down before you fall down sweetie." Allison said in a softer voice.

I knelt in front of her while she described how she had felt seeing me in the video and even cried as she watched it wondering what she would do. She had thought of moving out and leaving me but she loved me. The next day she had off work so she went online and researched. It was now clear to me that Allison was playing Star Trek chess and I was actually playing tic-tac-toe with crayons. As she told me more her stocking clad foot found my still rock hard cock inside my panties and began to rub it. The feeling was amazing, I had never felt anything like it before and I didn't want it to stop. That's when she hit me with the rest of it.

"I can't have you stretching out my panties anymore," She said teasing my cock with her foot, "or wearing my stockings so we will have to get you your own." I could only nod yes. "You will listen to me and do everything I say for you to do tonight or else this little dream of yours is over and I'll move out tomorrow." She continued. "The word no has now been removed from your vocabulary. You will listen and you will do what you are told and that is all there is to it, do you understand?" She asked pressing her foot painfully against my swollen balls. I nodded and winced. "Oh no muffin," Allison said moving her foot a little crushing my testicles in the panties, "I need to hear it."

"Yes," I gasped, "yes I'll do it all."

"Yes what?" She asked relieving the pressure a bit.

"Yes ..." I stammered knowing these words would seal my fate, "Yes Mistress."

"Mmmmmm good girl!" She said triumphantly. "But for now let's go with Ms. Allison."

"Yes Ms. Allison." I replied glad that her foot was now stroking my cock again and not crushing my swollen balls.

"Now put the shoes on my feet." She ordered.

I opened the box and saw the heels she had picked out. They were hot pink and white with a 1" platform and towering heels that had to be 6". They looked so hot I couldn't wait to put them on her. Her foot slid into the first easily. The stocking matched the heel perfectly as did her corset. It was almost too much and I could feel the precum leaking out of my cock like a river. When I put on the other she had me hold her hand as she stood. Ms. Allison towered over me and standing directly in front of me I could smell the musk of her pussy, it was intoxicating.

"Stand up." She ordered. "Now walk over to the mirror." I did as she said without question or reservation. "Look at yourself muffin," She instructed, "what do you see?"

"I see a guy in lingerie." I replied sheepishly.

"Now what do you see when you look at me?" She asked.

"I see a gorgeous woman in lingerie Ms. Allison." I replied drinking in her reflection.

"We will fix that soon enough you realize don't you muffin?" She smirked.

"Yes Ms. Allison." I replied wondering exactly what that meant.

"Now I asked you earlier what comes next in your little cross dressing night of fun," she started, "now answer my question and tell me what comes next."

This wasn't a question it was a demand and I knew if I did not answer that she would move out in the morning. Allison is a wonderfully loving and amazing woman with a stubborn streak true of her Irish heritage, if she left she'd leave for good.

"Ummmm ..." I stammered trying to find my words, "usually I ummm ... jerk off."

"Jerk off?" Allison taunted. "No muffin, real guys jerk off. They take out their big manly cocks and stroke them they don't dress up like slutty women and shove a cock in their ass before they do it." I went to protest but Allison saw it coming. "Are you going to try to tell me that's not a cock in your ass?" She asked taunting me more and walking towards me. "Tell me then what do you call something that's long and hard and put into a willing orifice like that?" As she asked Allison pushed on the base of the plug and wiggled it making it dance in my ass, the feeling was so intoxicating I couldn't answer. "That's right it's a phallus and something that trains your ass for what is to come." Her hand never left the plug as she spoke. "Now pull that dripping shaft of yours out of your panties and stroke it for me." I complied quickly and began to stroke furiously while Allison played with the plug base.

My mind was in overdrive and I didn't know what would happen next but what I really needed was to cum. I had never masturbated in front of anyone before so this was all so new but so incredible as well. I would pop in no time, then Allison turned up the heat and I was done for.

"That's right slut," She hissed, "show me how you play with that clit of yours! Show me how you orgasm like a good little slut! Fuck that clitty! Fuck it like the slut you are!"

I had never heard her talk like this and that was all it took. My body tensed so much I could feel my heels lift off the ground then Allison pushed the plug in as deep as she could. She put her hand in front of my cock and caught the explosion that shot out of it. My knees buckled and I almost fell but her hand in my ass held me up. I came buckets filling the palm of her hand with my hot seed. She ordered me to milk my cock's contents until it was soft which I did willingly.

"Now what do you normally do after you cum?" Allison asked.

"I just get undressed and put my stuff away." I replied completely exhausted.

"Well that's not going to happen," Allison informed me. "Now the question is what to do with this mess you've made in my hand?" I looked at the contents of her hand amazed at how much I had cum. "Have you ever tasted yourself before?" She asked with a gleam in her eye. I answered that I hadn't then watched as she stuck a finger into the pool of cum and rubbed it around coating the entire first knuckle of her index finger. "No time like the present right?" She asked lifting her cum covered finger to my mouth. "From what I understand little sluts love the taste of cum!"

The look in her eyes told me I wasn't going to get away with saying no to her or keeping my mouth shut. I reluctantly opened my mouth like a child being fed his vegetables and wrapped my lips around her finger sucking it softly. It was warm, salty and thick like clam chowder.

"That's my good girl," She said triumphantly pulling her finger from my mouth, "just one more to prove to me you really like it."

This time she scooped a bit dollop of it onto her finger easily giving me twice as much as the first time. The look in her eye was electric and I could tell she was thriving on the power she had over me. I sucked her finger dry and as she pulled it out she took her cum soaked hand and smeared its contents on my belly rubbing it into my hair and flesh. It dried slowly tightening on my skin.

"Now why is it that you see a guy in lingerie when you look at yourself?" She asked staring at me in the mirror. "What is the difference between you and I when you look at our reflections?"

Allison was maybe an inch or two shorter than me as we stood but the differences were quite evident. Despite my just having cum the bulge still showed in my panties and while my body was slight, I'm only 5'8 and slim, my chest and leg hair certainly set us apart as did her long hair and delicious B cup breasts. I told her the differences that I saw and she just nodded and smiled.

"Stay right there." Allison said walking towards our bathroom.

Just before entering it she looked over her should at me to see me staring at her bare ass. She looked simply devastating in that corset and stockings and I'm pretty sure she knew it. I thought nothing of hearing the bath running but eventually she returned and without a word took me by the hand leading me to the bathroom. There I saw that she had lit candles and filled the tub, I could smell the scent of the bath salts already, she loved the smell of lavender.

"First things first," Allison said putting her hands on my hips from behind me and walking me to the vanity, "lean forward like before." I leaned forward at my hips feeling my butt jut out toward her. "Good girl." She teased as she pulled down my panties exposing my ass. "Now just relax."

Allison grasped the base of the butt plug twisting it in her hand a little. She slowly worked it around pulling it out a bit and letting it slide back in or letting it go and having it pop back in on its own. She teased me about my ass not wanting to let it go as I felt myself getting erect again. Finally she pulled it out completely dropping it in the sink in front of me.

"Clean your toys first." She ordered.

I washed the butt plug with the antibacterial soap and hot water before setting it aside. This was now the longest I had spent in heels and my feet began to ache. Then Allison brought me towards the tub and undressed me slowly from top to bottom leaving the heels for last.

"There we go," she said with a smile, "now careful when you step into the tub."

"You're not joining me?" I asked as I stepped in the hot water.

"No muffin this is all for you." She smiled.

I lowered myself into the steaming bathwater and tried to relax. Allison soaked a small towel and folded it putting it over my eyes while getting me up to my neck in the water. The smell of lavender permeated my nose. It was impossible to feel masculine at this moment particularly with the hot water tingling my asshole. I'm not sure how long she left me there but I was so totally relaxed by the time she came back I didn't really want to get out. Thankfully that wasn't what she had in mind right away.

Allison had me sit up and began to wash my hair. I could smell the shampoo was hers, it smelled like roses. My hair is pretty short but she conditioned it as well. She drained some water out of the tub and then had me stand. The bathroom was warm but still my skin chilled a bit. Allison began to smear warm shaving cream over my chest before handing me a razor. She walked me through shaving my chest and used the handheld showerhead to rinse me off. Soon my chest was smooth as a baby's bottom. I was ready to get out when she started to rub the shaving cream over my crotch. Allison had me change the razor blade and shave my crotch leaving a thin strip of hair directly above my cock which Allison kept referring to as my clit. She walked me through shaving my legs as well and finally my arm pits. Before I stepped out of the tub my body from the neck down was devoid of hair save for the small strip at my crotch.

"There you are nice and smooth," Allison said helping me out of the tub, "now to keep you from getting razor burn."

Allison handed me a bottle of scented lotion and helped me rub it all over my shaved body. It smelled of cotton candy. I was now completely smooth and awash in a cornucopia of female scents.

"Now lets get you back into some lingerie and see what you think about yourself." Allison said with a big smile.

I recognized the bag on the counter as being from Victoria's Secret. I couldn't believe whatever was in the bag was going to be for me! Allison pulled out a peach thong and handed it to me. She didn't have to tell me I stepped into it and pulled it up. The feeling of the satin against my shaved skin was so much different and I loved it! My cock instantly grew hard. Allison then handed me a camisole that matched the thong perfectly, it had delicate spaghetti straps and a lace inlay where my breasts would be. I looked in the mirror and smiled a bit, then Allison stuffed the cups of the built in bra with panties giving me the shape of breasts which made me smile much more. I couldn't believe how it all felt against my skin and my cock was aching for attention.

"Now have a seat." She instructed.

I was an obedient puppy in her hands and sat on the small padded stool she used when she did her hair or makeup. It felt odd to have the plush material touching my bare ass but then again everything felt odd tonight.

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byMs_Allison© 28 comments/ 188070 views/ 61 favorites

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