I'm an 18-year old boy, but have been dressing up as a girl since I was 16. I'm short, just over 5'1" and 130# soaking wet. When I was young, my mother, a nurse, used to let me brush her hair and help her with her makeup. It would make my father so mad, he would yell and scream saying how she would make me grow up to be a fairy. How little did he know??

One day, she was putting on this striking red lipstick and it looked so bright against her pale skin. When she had left for the day I sat down at her vanity, adjusted the mirror and lighting, and applied her makeup to myself just as she would. Her foundation was so creamy, followed by a powder foundation, a peach blush to my cheeks, mascara, and finally the lipstick itself. Even with my shorted hair I looked like a young version of my mother.

I sat there for over an hour looking at myself in her mirror. I think that was the first time in my life I thought I was beautiful. After a while I realized I couldn't just sit there, so I went back to my room to lay down. I don't know why, but I got really hard just laying there thinking about the makeup I was still wearing. One thing led to another and I started to masturbate. This wasn't new to me, but as I stroked myself I realized I hated having my pubic area covered in hair, even if it was fine.

So, I shifted from my bedroom to the bathroom and trimmed my pubic hair with my father's beard trimmer. After I was close cropped I slathered on my mother's shaving cream and working section by section removed all the hair from my shaft, testicles, and the surrounding area. I know my mother liked to covered her body with a light coat of baby powder after she shaved her legs, so I powdered myself too and it felt so wonderful.

I was still in the bathroom staring at my hairless groin when I heard my father come in from his shift job at the mill. It was them I realized I still had my mother's makeup on. I scrubbed as fast as I could with soap and water and a washcloth - the last thing I needed was for my father to find me covered in women's makeup and hairless.

The next Monday I helped my mother get ready for work, and after she left sat down and began applying the makeup to myself. I had just applied the powder and started on my mascara when she suddenly walked back into the bedroom - she had forgotten a book she was readying during lunch. She stood there for a moment staring at my reflection in the mirror, my eyes brimmed with tears and I was on the verge of crying when she stepped forward and hugged me. She dabbed at my tears with a Kleenex, took the mascara applicator from my hand and began to apply it for me.

I sat there quietly as she applied he mascara, then the blush, and finally her bright red lipstick. It felt like forever, but it was only a few minutes of her time. She even ran her brush through my hair quickly, adding some lift and life to it. Then she stepped back, smiled, and said "You look beautiful!"

The next day my father left for work at 6am and I went to my mother's room to help her with her makeup and hair as usual. This time she surprised me by saying she had called in sick to work, but wanted to spend some time helping me. She spent the next 2-hours teaching me even more about makeup and how to make the most of my high cheekbones, how to select eyeshadow (something she never wore) and even ways to accentual my lips. By the time we were done I didn't recognize myself in her mirror - I looked like I could have stepped out from the pages of Cosmo Girl or Junior Miss.

What really was the icing on the cake was when she opened her closet and took out a couple shopping bags. Apparently she had stopped at the mall on the way home and "picked up some things" for me. Before she opened the bags she looked at me and told me this had to be a secret between her and I, that I could never let my father know what we were doing because he just wouldn't understand. With that, she opened the bag and took out a set of 3 lacy panties and matching training bras from Victoria's Secret. I stripped off my shorts and t-shirt quickly, not even thinking I was now naked in front of my mother.

Stepping into the panties I was in heaven, then were high waist and silky smooth on my shaven crotch. I needed help with the bras, and after a bit of adjustment to the straps mom clasped it for me. I stood there, smiling at my reflection in her full length mirror, turning to see how the bright material molded my ass. I had no breasts, of course, but the bra still hugged my chest tightly, the material rubbing back and forth over my nipples. I don't know why it happened, I really wasn't thinking anything sexual, but I suddenly realized I was sporting a hardon in my silky panties.

Embarrassed, I tried to hide it at first, but mother pulled my hand away and smiled again. "Does this make you feel sexy??" she asked. What could I say - the truth was tenting out my new underwear, all I could do was nod. She stood there for a moment thinking and staring at me. Then she nodded. "Is this what you want?? Do you want to be a girl??" Like an idiot all I could do was nod in reply. "I'll teach you what you need to know, but you can never, ever tell anyone! Get on my bed."

I wasn't sure where this was going, so I sat down while mother went to her dresser. She can back with a blue jelly vibrator. I'd seen this before when I'd gone through my parent's dresser drawers, about 7" long and just thin enough I could wrap my hand around it and my fingers would touch. She came and sat down beside me; "this is a vibrator, it's shaped like a man's penis but is soft." turning the base it began to hum, "and it vibrates, which can help a woman - or a man - reach orgasm."

I sat there, staring at the blue vibrating cock and didn't know what to do. Mom just sat there, looking at me while it vibrated in her hand. Suddenly, she reached over and took my hand, placing it on the shaft of the vibrator. As she held my hand there she began to move it up and down, in much the same way as I jerked off. Of course, this blue cock was much longer and bigger around than my real cock. We sat there like this for a couple minutes, side by side, the two of us jacking off this imaginary blue cock before she stood up.

All right, I think it's time, get on your hands and knees. I don't know why, maybe it was the authority in her voice or the fact I trusted her, but I rolled over and scooted up onto the bed further. Meanwhile, she went to the side table and took out a tube of KY Jelly lubricant. There I was, in full makeup and lingerie on my hands and knees with my ass high in the air and my mother standing behind me with a big blue vibrator and I wasn't worried or scared in the least. I loved my mother, and I knew she loved me.

She ran the buzzing vibrator up and down the crack of my ass over my new panties. I could feel the vibrations deep inside my ass, as well as over my balls on each down stroke. I thought my cock was hard before, but it pressed and throbbed in time with the vibrator and my heart beat. My breath came in quick, shallow breaths and I gasped as she tugged my panties to the side. I felt her finger rub around as sphincter, circle it then begin to push it. But, we were both dry and I heard the top of the KY pop open and suddenly everything was cool back there. Then her finger circled again and pushed in, invading inside my ass where nothing had ever gone in before, just out.

She pushed her finger in until I could feel her hand against my ass, then it slipped out in one smooth motion. After that, the vibrator began circling around. I could feel her breath on my hip, she was panting as much as I was. "When you take a man in your boy pussy, especially for the first time, it might hurt some. You just need to relax, use plenty of lube, and take it as slow as he will let you." I could feel the pointed tip of the vibrator at my opening, hard, insistent, pushing.

Suddenly, my anal ring relaxed and the head of the blue dong down through the molded head popped inside me. With the head inside me the vibrations shook my entire ass. I could feel them from my balls right up through my stomach and it FELT WONDERFUL. Mother began twisting the vibrator, turning it one way, then the other, slow pushing and pulling. Another cold dollup of KY and another half inch went inside me. "When a man takes you like this, from behind, he's going to grab your hips and fuck you deep and hard." she said, pushing the vibrator in a little further. "You should use your hands to push back against him, fucking him right back." I began to rock back and forth, helping her fuck my ass with the blue jelly vibrator.

My climax took us both by surprise, my cock just suddenly started squirting shot after shot into my new panties. As it did I pushed back hard, burying the entire 7" length deep into my ass. As the last short left me I collapsed on the bad panting, gasping for breath. I had just been made-up and dressed-up like a girl and then fucked by a well hung man and I loved it. Mom pulled the vibrator from my ass and took it to her bathroom. I could hear the water running, but I really couldn't move. I was exhausted, physically and mentally.

When she came back she helped me remove my cum filled panties and bra, then she used a wet washcloth to clean the sticky mess off my groin. We spent the rest of the day going over tips on makeup removal, as well as how to hand wash my new lingerie (and how to get cum stains out from them).

The next day I helped her get ready for work again, but before she left she watched me put my makeup on as well. I also put on a pair of my new panties and training bra underneath my regular summer shorts and t-shirt. Before she left mom gave me her blue vibrator and the little bottle of lube and said - "You need to practice each day, learn to relax and take as much of you can. One day, you'll meet the right man, and it will be important for you to know how to handle him well. You should also practice sucking on it, but with the motor off. Don't want to chip any teeth, dear."

I practiced like my mother suggested every day. We would help each other with our makeup, them I would spend the day reading all of mother's magazines about how to be a woman. How to walk, hold my head, conduct a conversation, how to sit in various types of skirts. I practiced talking in a light falsetto voice (not difficult since my voice was always pitched very high), mother even bought be a set of heels to practice walking in. I didn't leave that rubber cock alone either, every day I lubed it up and worked it around my ass, pushing, feeding my need until I could get the entire length inside me. Some days I would lick and suck on it, working my mouth over it and swallowing. I found blowjob tips on Google and practiced on bananas until I could finally work my throat open and take the entire length that way as well.

The summer went on like this for several more weeks, until one day my father came home early. He works first shift at the mill, normally 7am-3pm 6-days a week. Today the mill shut down his section for annual maintenance and sent everyone home with a full shift pay. Dad stopped at Jack's bar as usual and tossed back a couple drinks before walked in the back door. There I was kneeling in the middle of the living room floor, naked except for my training bra, lowering myself onto my mother's buzzing vibrator. My laptop was open on the coffee table in front of me, my favorite shemale porn playing - a well built bald man was fucking a very passable shemale in the ass.

Between the humming of the vibrator and the porn audio I never heard him walk in. I was bouncing up and down no the vibrator when I saw him out of the corner of my eye. He was just standing there, his pants open and his thick cock grasped tightly in his calloused hand. I tried to get up, but he grasped my hair and pulled my mouth into his groin. There was the scent of the paper mill around his clothes, but also a thick, heady musky smell to his cock. The head was thick and bulbous, much larger than the blue vibrator, which was still shoved deep in my ass. Suddenly, the head was at my mouth and he was pushing it past my lips, insisting on entry.

I tried to resist, but he's a large and powerful man and my mouth was suddenly open and his shaft was pushing into my throat before I knew it. Once into my mouth he grabbed my head with both hands and began fucking my mouth. Long, hard strokes, each one pushing until his balls were on my chin and my nose buried in his thick public hair. In and out the large shaft went, bringing copious amounts of spit up with it. I tried to push him back, or to keep him from thrusting it all the way in, but I couldn't stop him. This went on for some time before he pulled his cock out, and dragging me by my hair threw me over the arm of thee sofa.

I felt the vibrator yanked form my ass and heard it drop on the floor. One large hand grabbed my hip hard, almost vice like, while the other positioned his cock at my ass. Like my mouth there was no foreplay, no preparation, no words of love and adoration. He pushed forward until his hips met my ass cheeks and I thought I was being split wide open. His cock mas much longer and thicker than the vibrator, harder and less yielding too. As both hands squeezed and pulled my hips he began and steady, hard fucking. Each thrust bringing his cock right back to my anal opening, then pushing forward until his hips hit mine. Hard, steady, pounding. I loved it. My cock was rock hard, aching to be touched. I tried to reach down underneath me, but his weight kept me pressed to the couch arm.

This went on for a couple minutes before he stiffened and pulsed. I could feel his cock throb with each blast, each shot of his cum shooting into by ass, my boy pussy. As his cock softened he pulled out and walked off to his room to shower and change. I lay there for a few minutes, his cum leaking from my ass, as I stroked my cock at last reliving the entire ordeal. I know it was wrong, but I can't say I didn't like it, in my own way. It only took me a couple minutes but I quickly filled my hand with my own cum.

In the hall bathroom I washed off the makeup and took a shower. When I came out my dad was gone, but that night I could hear my parents arguing. The next morning mother helped me with my makeup again, but this time she put on a bit more blush and eyeshadow than normal, and rather than her bright red lipstick she used a dark purple I'd never seen her wear. As she gathered her things for work she turned to me and I realized she had tears in her eyes. "Your father is staying home from work today. Remember everything I taught you, especially about relaxing and using plenty of lube."

That was 2-years ago. When I went back to school the next year I wore makeup and dressed as a girl. My parents told the school administrators I was self identifying as a girl, and even went so far as to have my name legally changed to a girl's. I was told to simply tell everyone my new name, that I was a cousin come to live in town. That the boy had gone off to a special school. I'm not sure how well it worked, but few questioned me.

I had several boyfriends those last 2-years of school. I looked at acted more feminine than most girls at school and could suck cock better than any of them. It was intimidatingly easy how well I could make a man mine. A little flirting, a hand job in the back of a car, a suggestion or two on what I needed him to do. I told all of my "boyfriends" I was saving myself for marriage, but I was willing to suck them off - even let them fuck my mouth. But nothing below the waist.

This fall I'm heading off to college and am registered there as a girl. I don't even own any boy's clothing anymore. I'll miss my parents, after all my mother made me into the girl I wanted to be, and my father made me into the woman I am. I still let him fuck me once in a while, sometimes my mother even watches while she uses that blue jelly vibrator on her own ass.