Date: Tue, 5 Aug 2014 13:03:44 -0700 From: Victoria VanDersuk Subject: Transgender: Candy/Candy 1 Candy I was what most people called a "latchkey kid", I was pretty much on my own after school, until around 6 pm or so when Mom came home from work. Daddy was a bit later if he was in town and not on the road, and he could be gone for days. At the time he was a representative for a ladies lingerie company and was considered quite the salesman. Sometimes on the weekend he would practice his sales pitch, and since Mommy was too busy, he would role play with me, and I would play the customer. I guess I always assumed the position of a woman when we would do this and it was a lot of fun. I would watch wide eyed as he pulled samples out of his big suitcase, "honeymoon sets", corsets of all colors and fabrics, and plenty of matching bras and panties, it was all so fascinating. Sometimes we would laugh when we role played, I would make him really explain things, test his knowledge, and when he asked me for the sale I would raise objections so he could practice overcoming them. Almost from the time we started this I was fascinated with the clothes, and how much more fancy they were than the simple boys bvds I wore. "This corset is made of the finest silk and the lace has been hand sewn...I guarantee you madam this will spice up the bedroom for the lucky husbands of your customers! Now how many would you like to order for your store, and in what color? They come in purple, jade and peach...."" I laughed at Daddy's sales presentations, but I could see how much it excited him to talk about the garments and his hands would shake a bit as he handled them, so I figured all males must be the same way, kind of anxious around these things. I liked being around daddy when he was like this, he was full of excitement and energy and had a devilish twinkle in his eyes. I have to say the lingerie excited me, too. I loved to feel the material and marvel at the intricacies of the design, with lace and floral embellishments. I admit I would think about wearing them myself, what it would feel like to wear them and not in seeing a girl in them...but that's natural, right? I mean I'm just being honest. They were so sensual, and cotton garments were never part of his sales kit. Mommy told me to not get into "mischief" when I was home alone, which was never clearly defined to me. I learned I could pretty much do as I wished after school provided I covered my tracks, and like a lot of boys my age I spent a good deal of time masturbating. Oh my, I did love to jerk my little cock, even before it started to spurt. I loved the feeling of lying down on my bed naked from the waist down, humping against one of the small pillows that decorated my bed, or even against a furry stuffed animal. There was one particular pillow...it was oval shaped and pretty hard, the fabric was a tiger print, it was a velour like fabric that was very soft to the touch., Mommy had made the cover from some scraps in her sewing closet. This pillow was such an odd shape and size, I figured Mommy just never threw anything out. This pillow seemed tailor made to fit across my erection and the front of my balls, leaving the tip of my thrusting cock exposed to the air. Before I could even cum I was hooked on the incredible waves of pleasure I felt after humping the thing. I would shake and tingle and then feel very weak. When I did finally start to spurt, I was freaking out about it, but then remembered the subject of a father/son chat from year or so ago, where Daddy spoke about procreation and the magic of sperm. At the time I just squirmed and giggled. When I started squirting I was a pretty happy little guy, just full of the stuff, and the little tiger print pillow soon became crusted with the remains of my youthful orgasms. I was embarrassed for my parents to see the little pillow and tried to scrunch it down between my bed and the wall it pushed up to, but I often found the stained pillow laying at the foot of my bed along with my favorite bear after Mommy got in there to clean. You could clearly see the cum stains, but neither of my folks said a thing to me about it. The mere sight of it would being me both shame and excitement. For some reason I never thought to ejaculate into a tissue, I would just pull back my spurting cock and pump out my boyish load on the soft material, then roll off it and fall asleep. Since my Daddy worked for a lingerie company he gave my mother all the discontinued samples, many I had seen before when Daddy did his role playing with me. Some were very fancy, and Mommy usually thought they were too much for her. Daddy would give her all kinds of things, usually in front of me which added to her embarrassment, and my excitement. I would watch her cringe as she held up silky corsets in pink and purple, all kinds of garter belts, brassieres and panties. Daddy told her the line he handled was an homage to Betty Page. When I asked who that was Mommy blushed and brushed me off, but when she left the room Daddy told me she was a sexy lady from the fifties who wore racy lingerie. As he told me he grabbed at the front of his pants, and I could see him absentmindedly pulling at the big bulge in his pants. The funny thing is I felt the same way, my cock would harden when I saw the sexy garments, and I just knew I would end up wearing them myself at a later time, all alone. I discovered Mommy put all the lingerie samples from him into the bottom drawer of her dresser, not mixing with her things. Mom's lingerie was nice, she typically wore full cut satin panties in pastel shades, and her bras were a bit plain. But then she was a Mom, and a member of my school's PTA, she was and is a very practical woman. On more than one occasion I overheard an argument between them. Daddy wanted her to wear the sexy things he brought home, but she refused, saying they were too fancy for her and she felt silly wearing them. The drawer filled with lacy panties, some see through or with ruffles, with matching brassieres and garter belts. The corsets I found particularly fascinating, and they were fun to play with and model for myself. Yes, I was dressing up and experimenting. All boys experiment, right? But it was the panties, those silky frilly panties that really made me little cock jump, and I came to see the items in that drawer as my own. I still remember the first pair I ever wore, I shivered as the cool lavender colored panties shimmied up my leg, the silky fabric was like electricity when it surrounded my hairless cock and smooth balls. The sheer naughtiness of it made my little cock so hard it practically hurt, and when I jerked off through the silky fabric it was the most intense orgasm of my young life. But that was a while ago, I am way past that. I discovered how intense the humping and rubbing feeling was when I did this wearing a pair of Mommy's silky underpants...pretty ones from the drawer! The feeling of the silky fabric on my little equipment was incredibly erotic to me. I felt so sexual, at the time I wasn't struggling with straight or gay or any other labels. I just loved to dress in her things, prance around and pose, and my inevitable little boners were always relieved of a never ending supply of boy cum. I tried hard, really truly I did, to not stain those garments for fear of being discovered. I didn't think my parents would understand, and I heard the chatter at schools from the other boys, talking about being queer and laughing about it, but I just couldn't help it, wearing something feminine and sexy for a few hours a day became a regular routine for me provided the coast was clear. I couldn't keep my hands off the hard little dick in my pretty panties and I did in fact end up staining some things, I tried to wash them out but I thought it best at that point to just keep the soiled panties and even the corset, hiding them in the bottom of my dresser, under the bottom drawer. Once they were stained I didn't bother to avoid spooging into them, and in fact I found I loved to fall asleep in the sticky panties. Mommy is not a large woman, and the clothes were a bit big on me, but that didn't matter. I just figured it would take me longer to grow out of them. I figured by then I would be over it and move on to something else that interested me. It started out as just something fun to do, but then I realized how much I loved that pretty lingerie! When I looked into a mirror from the neck down I looked like a girl. I was not very athletic, and the vision in the mirror made me hot, thinking I would fuck a girl who looked like that, and soon I would be off to my bed in her lingerie, thrusting my hard little pantied cock against the stained pillow. I began doing this while also wearing thigh high stay up stockings or putting on a garter belt and attaching the stockings from the drawer. And if a pair of panties had a matching bra I would wear that too, after all they were a matched set. After I came I would clean up any mess I made, and at first I would scurry into my parent's bedroom to remove the frilly garments and be composed by the time Mommy came home. She typically found me in my room, at my desk wearing a T shirt and jeans or shorts doing whatever homework I had been assigned. But after a while I was wearing them all the time, trying to be careful that evidence of a lacy waistband was hidden from view when I bent over or stretched. Once or twice My Dad asked me what kind of underwear I was wearing, saying he could see the outlines but I just told him they were my boy's briefs and he would smile. I was a good boy, other than sneaking around in lingerie and masturbating. Oh, and the whole sticking things up my butt thing...but I will talk about that later. Mother kept threatening to throw out the entire drawer of lingerie whenever my father hassled her about wearing something sexy for him, and I hoped that day would never happen. One day I was playing in the lingerie drawer, and I found a cylindrical white object under the corsets at the bottom of the drawer. I took it out and looked at it, it had ridges on the bottom of it and the length was about 12 inches. There was a little dial on the bottom and when I turned it on it vibrated in my hand. I laughed and put it back under the pile of clothes. The older boys on the school bus were talking about sex, about fucking and putting their cocks into a girl's pussy, and I listened but didn't say anything. When I imagined some of those buys doing that it made me feel kind of funny, nervous I guess. I was really horny when I got off the bus and got back to my house. I immediately ran to my room, stripped down and went into my parent's bedroom to play. I pulled out this purple and black corset. It didn't have any straps. I slipped into it and pulled on the long laces on the back of it to tighten it up. I felt it get snug and I tied it off, making a bow of the strings in front of my waist. I added some black stockings with elastic tops that were in the drawer, also a pair of black satin panties with three rows of black ruffles across the back. I felt really sexy, and went into the bathroom to see how I looked. Amazing. I turned around and viewed myself from all angles and they all looked hot. My cock was really hard and sticking the front of my panties out. My panties...I had grown to think of anything in that drawer being mine. I put my hands on my ass, and played a bit, pulling down the ruffled panties to expose my crack. My bottom was really round, and it was exciting to see my bare bottom while in the pretty outfit. I wet my finger and pushed it inside me, it felt good. I did it again, this time with two fingers, and decided I liked the way that felt. I began to relive the conversation those nasty boys on the bus had, and wondered what it must feel like for a girl to be fucked. I don't know what came over me, but I went to the drawer and pulled out that vibrating thing that looked like a big dick, and I watched my face as I poked it at my hole. My cock was really hard, and I figured if I put some hand soap on it might feel better. I removed the panties so I could have access to both my little cock and balls, and my eager bottom. It did feel better and I jumped after I pushed two or three inches of it inside me. I remembered the dial on the bottom and turned it. I swear I squealed as it started to hum and vibrate and my eyes nearly bugged out of my head. My cock jerked up and down and started to leak clear juice a little. I had to hump the pillow, and squirt my juice, so I went into my bedroom and positioned myself, the little pillow against the underside of my dick, and I laid down and started to hump. I kept the phony dick inside me, I found it really excited me to have it in me, but my ass kept wanting to push it out, so I reached back with my right hand and held it in there, and moved it in and out a little as I humped. My head was down against my blue chenille bedspread, and I felt so good, so excited! I was tingling both in my ass and also my little prick, and I felt something I hadn't expected. A firmer, bigger hand pushed mine away from the phony dick, and when I realized it I jerked and tried to spin around. When I did my Dad used his other hand to hold me down. He had a wicked smile on his face and I felt SO embarrassed. "Daddy I can explain!" "No explanation necessary! Don't stop son, you're doing great. You just keep doing what you're doing and I will make sure your pussy feels really good." "Daddy, I'm sorry about getting into Mommy's things...I know it's wrong." "Nonsense Andy, you look absolutely adorable! That is last year's edition of the corset from the Purple Passion line, a very sexy choice, and a well made garment to boot. And I like the way your ass is gobbling up that vibrator! Damn son, you've got six inches up in you!" "Dad, I should stop." "Absolutely not, sport! It's only natural for you to experiment and I don't want to hold you back! You know you look damn sexy in that corset and stockings, Daddy will help fuck your boy pussy with Mommy's vibrator. Now you just go ahead and shoot your cum on that little pillow, like you always do. Say, you really like that vibrator in your pussy, don't you?" "You know about the pillow, Dad?" "You bet. You've got the damn thing permanently stained, and it reeks of your boy juice. It's OK, all boys masturbate, though your methods are a bit...unusual. Now get humping, son...before your Mother gets home from work." I continued to thrust my little cock against the cum stained pillow. "Daddy, why are you calling my ass a pussy? I'm a boy!" "Well I call any hole that gobbles up cock a pussy, Son!. Do you know how girly your body looks in that outfit, Andy? I can see why you wear this stuff, it really suits you. You have the cutest round butt honey. Go ahead and hump and I'll keep the vibrator in your boy pussy for you. You know you can always count on me, baby. Let Daddy help." I focused on fucking, and rubbed harder against the pillow. It was feeling so good, Daddy was gently moving the vibrator in and out of me, slowly and sensually, trying to time his thrusting with my back and forth rubbing. As I humped and he seemed to know how to do it really, really well! I found myself trying to flex my little hole to accommodate more of the white plastic cylinder. I'm going to cum, Daddy...I'm going to cum!" As my body froze and began to shake Daddy pushed a few more inches of the vibrator into me and held it there. I screamed and pumped and pumped, soaking the pillow, and I went limp. Daddy slowly removed the vibrator from my ass, and he patted me on the ass cheek. "That was great honey, very sensual. You took almost all of the cock...er, I mean vibrator. Now let's see how much of a mess you've made." I rolled off the pillow and held it up, it was covered with lots of my sticky hot cum, more than I think I ever made. "Oh heavens! Now be a good girl and lick it off the pillow, baby. Go on, clean up your mess." "But Daddy, isn't it queer to eat cum?" "Not at all! Go ahead now quickly before you get discovered by Mommy!" I had sniffed my cum before, and even tasted it on my tongue once or twice, it wasn't that bad. Daddy smiled and nodded as I started to lick the globs of goo on my little pillow. I could see he had a big boner watching me. "That's a good girl...you should never waste a cum load honey, not even your own. There, you almost have it all, you're a good little cum eater aren't you? Don't miss any, it's full of vitamins! Now hurry, get it all, and then get out of those clothes and get to work on your homework." Dad tousled my red hair and left my room before I could ask him why he was calling me a girl, I figured it was just more role playing. I stashed everything away and when I left my room I could see the door was closed to my parent's bedroom. I crept over and listened and swear I heard a smacking sound, and Dad moaning. Gosh, Dad like to jerk off too. I listened a minute and then sneaked off to the family room to start on my math assignment. That evening was pretty normal. Mommy came home and made dinner, and Daddy would wink at me when she wasn't looking, we shared a secret. When I excused myself for bed and went to my room, Daddy followed me and went to his supply case and put something behind his back. Mother was down in the family room. "Daddy what are you hiding?" With a big smile he showed me the prettiest little jade green nightie! It was very slinky, and had matching lace above the breast line and a small rose in the middle. "Here, honey. Try sleeping in this, I think you will enjoy it. Just be sure to hide it under your mattress in the morning and don't let your mother see it. I'm sure a horny little thing like you will need to rub one out later, just pick up the hem of the nightie and pull it above your titties before you squirt." As I listened to Daddy and held the silky nightie in my fingertips I felt my little cock stiffening in the scratchy bvds. I couldn't wait to feel that silky nightie against my body. "You know Candy, I''m really glad to have someone in the house who understands my business and appreciates my merchandise! Now let's keep this secret between you and me, OK honey? " I laughed. "Daddy, you called me a girl's name...Candy! That's funny!" "Well I can't call you by a boy's name when you're wearing these frilly girls clothes, can I?" "Umm, I guess not." "Besides, you're such a sweetie, you always have been. Now go brush your teeth and then come back to your room and put on your nightie. No panties, honey...you will enjoy the lovely nylon tricot of this garment. Feel free to rub up against it all you like, I'm sure you will enjoy the luxurious fabric, most women do." Daddy leaned down and gave me a kiss on the forehead. I held the pretty nightie in my hand and couldn't wait to try it on! I looked up at his handsome frame, all sturdy and muscular. My eyes trailed across his crotch and I saw his hard cock pushing against his khaki pants. "Goodnight, Princess."