The first three chapters are autobiographical after that however I started to mix reality, fantasy, and just some good fiction. I thank everyone for all the wonderful comments and encouragement to come back and write some more so please enjoy the story from the start. I hope to continue this series. This was originally broken up into several shorter stories I have now put them all together for easier reading.
Love to all,
Chapter 1: Humbling Beginnings
My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbie's, the whole nine yards.
I had mostly girl cousins around me and instead of playing with my toys or my brother's toys I would always seem to choose the girl's toys. My mother has several pictures of me dressed from head to toe as a little girl. I was in pretty dresses, shoes, make-up, hats, and of course my hair all nice and curly. They thought it was cute and adorable as a small child. As I got older I quickly realized it wasn't considered cute any more and in fact there was something wrong with any boy who dressed as a little girl and boys just don't do that. These types of comments were commonplace.
A boy is expected to be a boy and girls are supposed to do girl things and that was that. Many times the comments went something like this... you don't want to do that it's a girly thing or stop that you're a boy... So needless to say my dress up days ended around the time of age 10. I only got away with it for that long by pretending I really wasn't having a good time and my cousins thinking they were getting over on me.
Little do they know how much I cherish those times in my life? My dressing and makeup parties were then resigned to raiding my mother's closets when they would be out for extended periods of time. I would sneak into her closet and raid her lipsticks and nail polishes for a brief thrill. Several times I was almost caught. It was about the age of twelve when I first realized I could go out and pass on Halloween as a girl.
I went to several parties as a girl and everyone just thought it was a blast how "cute" I was. This wonderful realization would be short lived as the hormones namely testosterone kicked my male development into high gear. I was soon developing into a man's man. This development was only on the outside. On the inside I was still a very feminine person.
The upside is I was turning into a fine looking young man the downside however is my possibility of ever truly passing was becoming evident. Genetically I was split with my parents. I got my masculine features from my father's side and my facial features however are very much my mother's. So when made up, my face was still very pretty. Genetics really suck! They can be such a cruel joke indeed on some very confused children.
Needless to say my fantasy quickly became just that, Fantasies.
Occasional make up sessions as I quickly surpassed my mother's clothing and then had none to try on any more. And as I got older I was too embarrassed to go out and purchase my own for fear of discovery. Anything Deviant from the typical hetero lifestyle was not an Acceptable behavior and serious repercussions could occur from an alternative lifestyle. Like DEATH!
For all intensive purposes my desires came to a screeching halt with the exception of constant masturbation fantasies.
My cross-dressing resurfaced believe it or not after I got married. Let's fast-forward a few years to age 21.We had a few too many beers and my wife was very horny. She pulled her cosmetics case out and brought it to the living room and told me she wanted to try something she had wanted to do for some time. I just figured she bought some new lipstick or something and paid her no mind. That's when she grabbed a hold of my face and turned it to her and told me to make my lips like I was going to kiss her. I of course put on the macho man front and told her she wasn't going to put that stuff on me. She then told me if I let her do this I would be rewarded in a big way!
So I pretended to not be excited about this opportunity. She carefully applied some lipstick and put on some eyeliner, eye shadow, and mascara. Then a little rouges and even went as far as painting my nails. I was hard as a rock!
Little did she know I was as excited as a schoolgirl with a crush. She was amazed at how pretty my face was. She told me it was a real shame that such a pretty face was on such a manly body. You see I am 6'1" and weigh about 270 lbs. Yes from an outward appearance I am all man.
That is when she glanced down at my shorts and noticed the pop tent that was now there. A very sly and devious grin came over her face. She said I see you like what I have done to you as well. How could I dent it now?
My body had betrayed me and showed the obvious excitement. She then started a barrage of questions and pressure about my fantasies. My face went scarlet red as I was thinking of my childhood and all the times I masturbated over just such thoughts. Renee is now volunteering stuff as I am simply stalling till I can come up with something other than the truth. As her enthusiasm was building and she was assuming she was right all the time I took a chance and figured I had nothing to lose.
I am sitting here all dolled up and my wife is having a big old time from it. I went for broke and told her my life long desires. I told her about my childhood and the events that led to this day and the true reason for the wet stain now growing from pre-cum in my shorts.
She told me she was excited as this was going to open so many doors for us. I really wasn't sure what she was getting at but to know the woman I loved was as excited about dressing me, as I was to be dressed was more than I could ever hope for!
Little did I know my fantasy unlocked a fantasy of hers she had for a long time to dominant her man. She wanted to use me as her sex toy and totally control certain aspects in the bedroom. I would not find this out for another week. That night before the makeup came off we had some of the best sex I had ever had up to that point. I thought I was going to explode that night.
Both of our faces made up, lipsticks smearing together sliding over one another effortlessly. The slight smell of perfume that cosmetics have was utterly intoxicating as that scent filled my nasal cavity. She had never been so wet before either. She was literally dripping wet. She said it felt as though she was making love to a woman with a strap on, and she liked it!
This was the start of a very incredible journey that has lasted 16 glorious years so far. She also told me that night that she was already making plans in her head for next week.
Chapter 2: Anastasia Learns to Submit
I was getting very anxious for the next week to arrive. Thoughts were rampant through my head as to what my wife might have cooked up in her devious mind. I know she had shared at least fifty to seventy five different scenarios when trying to guess my fantasies, but nothing would prepare me for what I was about to experience. I had never been dominated before. So we were getting ready to get into uncharted territory. She would very much be in control from now on. Little did I realize just how much she would relish this dominant role?
Before this night in question would be over she would have enough evidence to destroy my life. At least put me in so much shame that I would loose my job and probably have to move to another part of the country. I got home that Friday she was not home from work yet which was unusual for her. She normally always beat me home.
I went upstairs to shower and on the bed there was a note that said, "You are my BITCH! If you don't follow these instructions to the letter a copy of last weekends little pretty up session, which was caught beautifully on tape, will be sent to your friends, family, and I am sure your work would love to see what a little sissy they have hired."
She had explicit directions for me to be hairless from head to toe minus my locks of course. I was to have my face made up on my own and my nails would be polished with at least two coats fingers and toes. I was to have all this done by 5:30. She had some errands to finish and expected me to be naked and ready for her arrival in the living room.
It was now 4:35 and without the luxury of practice I was afraid it would take me forever to do my makeup. It had been years since I had done it. I ran to the shower in a panic trying my best to be hairless. Needless to say I hacked myself quite a few times in the process. I slathered down in baby oil after the shower to try to get my skin a little smoother. I applied the nail polish as quickly as I could. You can only go so fast with polish it must dry you know between coats. So by the time I started on my makeup I had my foundation done, applied my lip liner and lipstick, I had some rouges in place, and was starting on my eyes when I heard her car come in the drive.
She bounded up the stairs and into the bathroom. I saw the look on her face and she was pissed! I smiled and tried to lighten the mood a little but to no avail.
Renee screamed, "BITCH! What did I tell you in the letter?
What did I tell you I wanted done before I got home?" I tried to stammer something out. I had never seen her so livid before. She told me if being a female is what I wanted being a female was what I would get. We weren't playing dress up she was going to indoctrinate me into the feminine world. She had too many years to make up for and I wasn't helping her by being so uncooperative. She was dead serious.
It blew my mind all this emotion. I had never seen my wife like this before. I started to speak and she slapped me across the face. It took me by total surprise. I just sat there speechless.
Renee said, "Don't just sit there slut, finish your makeup you've got a very busy night ahead of you. And we don't have a second to waste. I have not been out shopping all day to have you screw this night up. Oh yes, my little pretty speaking of screwing, prepare yourself for the screwing of a lifetime. Many women wait their entire lives to get an opportunity like you have tonight and you're getting it the first night of your womanhood. You should count yourself lucky you little bitch."
My cock was as hard as a rock! I just could not believe this behavior was getting me so excited. I could not believe my little Renee was as passionate in dominating her man as she was. She had always been so demure. She told me to hurry up and finish up then take my ass into the bedroom. I was stunned at her presence.
I was just staring at her when she slapped me again. The stinging brought me out of my trance and I figured if I didn't want her beating the shit out of me I better get finished up here. I did a real quick job on my eyes and I knew my makeup was not good. I rushed into the bedroom and she quickly confirmed this notion.
She told me my face was totally unacceptable and that I would need practice. I would practice everyday if necessary. But before the next session my face would look tremendously better or there would be hell to pay. She had a bunch of bags on the bed and I was getting very nervous. Every bag was from a different boutique or ladies apparel store. She informed me that tonight I would be putting on our very own fashion show for her and her girlfriends.
Fear passed over me as those last words rolled off her tongue. Friends... no one ever said others would be included. That's when I heard the giggling. Her two best friends were standing in the hall the entire time. Melissa and Audrey came into sight. I was totally humiliated. Bare naked with my face all painted up not to mention my pretty nails. I tried to cover my nakedness but that just caused them to bust out laughing.
"Look at the little sissy Melissa. What a little pansy she is."
Then Melissa chimed in, "I never knew you were such a little bitch. Oh Audrey we are going to have a great time with this prissy little bitch."
Renee wouldn't be left out. "We are going to have a great time girls. ALL of us girls, isn't that right dear?"
She told me from here on out my name would be Anastasia or Anna for short. When the girls got together from now on they would no longer recognize my male persona in fact as far as they were concerned my male persona was dead to them. I would be required from here on out to be a female in their presence and a female in every way. All my mannerisms from now on where to be as feminine as possible everything from looks, walk, dress, expressions, gestures, to the point that I was no longer allowed to pee standing up. I would now squat to pee as all ladies do. I would no longer refer to my cock as so, now it is a clitty.
With that said she dumped most of the bags contents on the bed. My eyes were treated to a vast array of colors, textures, and styles of every kind of garment imaginable. She did some serious shopping. It was obvious she was serious. There was an entire wardrobe from head to toe. She then went to the closet and pulled out some more bags. The contents of these were cosmetics that she told me I would be getting VERY acquainted with. The other bags she pulled out were for later she said. The contents would be getting use on the girls sleep over. My first all girls sleep over!
What am I saying? I was excited about this idea! I was really happy about this forced feminization. What was wrong with me? I should be in full protest of this by now and I am just going along with this as if I was already one of the girls. My clitty is throbbing at full mast so I guess my answer is simple. Yes I am enjoying this totally. As I was pondering these questions my world came back to focus when I felt extreme biting pain. The girls are putting on these nipple clamps that feel like it is ripping my nipples off.
I yell out in pain and am rewarded with a slap in the face. "Stop being such a little pussy. Your clitty is throbbing you obviously are enjoying this. Not to mention women have endured great pain over the years. It is time you start getting your share of the pain. Anna gets dressed now. It is not very lady like to be exposing your clitty in company. I mean I know it's just us girls, but you need to learn manners and a proper lady isn't naked in front of others. That is considered a tease and you aren't going to be a tease. You will be a real woman and satisfy others."
Melissa tells Renee she wants to see me in the white silk lingerie as it is only fitting for a virgin to be in white the day she gets her cherry popped!
"You heard the woman Anna pick up the white set and get dressed if you need any help we will be more than willing to show you this one time. You will need to learn quickly as you have a lifetime to catch up on."
I start to ease the panties up my freshly shaven legs and the feeling is so erotic my clit is just bobbing with every heartbeat.
Audrey busts out laughing. "Look at this little sissy Bitch. She is all fired up about a pair of panties!"
Renee bellowed. "Oh this just won't do. You will never appear ladylike with that huge clit showing through those panties of yours. You are going to need to learn to hide that thing away."
I tried to push it between my legs but it would not go so hard.
"Bitch I said tuck it now!"
She reached over and smacked my clit right on the top of it. I thought I was going to pass out. It had the desired effect as it went soft immediately. Audrey was there on my right.
"Don't cry sissy. A woman needs to learn to be strong and accept pain if it is eventually going to get pleasure in return."
I tucked my clit between my pussy crack. I was no longer allowed to refer to it as my ass. It was now my pussy. So I smoothed my panties and went on with the dressing. The bra came next but it was hard for me to snap the hooks. The girls showed me to attach it in the front and spin it in to place. The stockings were next. They were so sexy. The girls stopped me first and told me to put my garter belt on next so I had something to fasten my hose with.
My clit had snapped out again and Renee told me we were going to have to find a better solution to hide that clit. Renee showed me how to roll the stockings and slid them up my legs. As I did this electricity shot through my body. It was such an awesome feeling.
Next up was the ultimate topper, shoes! I was overjoyed. I had never had heels on before and I was about to step into them. They had about a three-inch heel on them.
"You will start at this height, and work your way to five or six inch heels."
I took my first step and about broke my neck! I never realized just how difficult it was too walk in these things. The girls were rolling on the floor with laughter. I was probably turning fifteen shades of red. Renee quickly grabbed my arm to steady me and told me girls need to learn to walk gracefully and practice will be necessary for me so I would not brake an ankle. She showed me the proper way to walk and it took quite a little coaching and much ribbing from the other girls before I could walk right. The girls were getting very excited as I started to learn a little more of the feminine ways.
"I believe she is ready to take the next step into womanhood, what do you think ladies?"
Renee looked to the other girls for an answer and Melissa said," I thought you would never ask. I am so horny my panties are soaked and I am ready to get to hard core fucking in."
Audrey wasn't to be left out. "This bitch is ready for her cherry to be bust wide open I can see that."
I was now terrified as I wasn't sure what was going to happen next, but given the turn of events I was shuddering thinking of what was probably getting ready to happen.
Chapter 3: Anastasia's Cherry Gets Popped
I didn't have to wait long to find out what was going on in the minds of these devious women. I was pushed to the bed face down and Audrey grabbed my left hand as Melissa grabbed my right. Wrist restraints were quickly put on my wrists and I found out I was in no position to go anywhere. My wrists were strapped one to the footboard and one to the headboard.
Renee told me," Get on your knees Bitch!" I was struggling with the restraints and the awkward position I was in. SMACK! I felt a very sharp pain on my ass. SMACK, SMACK, SMACK. "Bitch I said kneel and that is what I mean." I scurried as fast as I could to a semi-kneeling position. I had pillows being stuffed under my stomach.
Audrey came behind me and harshly pulled my panties down nearly ripping them from my body. "This won't due Renee this bitch is going to have to take these panties all the way off. I want her pussy wide open when I bust that thing." Renee quickly pulled my legs down and yanked the panties off. "Now back to your position bitch. I want to see that ripe pussy that I'm going to bust open."
I really started to get scared because I wasn't sure just what was going to bust my pussy open. I thought all the Ladies were looking at my ass when I discovered Audrey and Melissa were really elsewhere and were now standing in front of me with these huge strap-on dildos. Melissa's was long and fat and looked very real with veins and flesh colored. Audrey had an even bigger cock that was real looking only hers was black.
Renee said, "I'll be back in a few minutes, while you ladies start getting this slut ready for her breaking in. Melissa told me, "open wide bitch you are going to want this cock nice and slick before it goes into your pussy. So I suggest you do some serious cock sucking to get my cock ready for your pussy." Audrey on the other hand got behind me and started putting some lubricant of some kind on my pussy. "My big black cock is going to look great sliding in and out of this pretty white pussy. I think I better get you nice and loosened up because you're going to need to open this pussy up to take my sweet cock." Audrey laughed as she said this.