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  • — When I Was a Kid —
    Bi-Sexual Male / 44

    When I turned 12 years old I got three profound birthday gifts.

    The first was my grandfather's gold pocket watch. He took it to France with him during WWI. The second was my late father's very large stash of porn filling six trunks. Mom saved it for me as Dad had said he wanted me to have it and she felt I was old enough. Most was the more common stuff like my Dad's playboy collection going back to the first issue and a lot of Penthouse, Club, Hustler etc. Then about a quarter of the magazines were hardcore porn showing full insertion and some was gay porn which surprised and intrigued me. There were also about fifty VHS cassette tapes of some pretty intense but standard porn. Some were fetish stuff but most was fairly vanilla. The third profound birthday gift was a video camera, tripod and lighting.

    That was thirty two years ago and five years ago Mom died.

    But I'm getting ahead of myself. At twelve I had long blond hair and was kind of slender and short for my age. I was what Mom called effeminate. She got my both of my ears pierced when few boys had either pierced. I was soft and soft spoken. I had the smallest dick of any boy in my middle school gym class and that included 5th through 8th grade. I was in 7th. I also had a very humiliating pair of ridiculously huge boy boobs. When we played flag football, which seemed nearly every day, I was ALWAYS on the skins team which made it worse. It wasn't a coincidence. The gym teacher preferred to arrange teams by alphabetical order than have two team captains pick the boys for the team. So what that meant was instead of randomly being on the skins team fifty percent of the time I was on it 100% of the time based on the gym teacher deciding at the beginning of the year that boys whose last name begin with the letter "G" are on the skin's team. Despite being slender I had C-cup tits. I know, Mom measured me for a bra at the beginning of the year but I successfully talked her out of making me wear one. The only thing more humiliating for a 12 year old boy in the locker room than having C-cup boy tits bouncing around is taking off a c-cup lace bra to show them off in that gym class.

    Other than the daily humiliation of gym class, school went fairly OK considering I was the permanent butt of all jokes, especially emasculating jokes.

    So my birthday was a welcome distraction. I was permitted to invite girls over for my party for the first time but since most of the girls liked to ridicule my lack of masculinity I declined, except for Jenny. She was really nice to me. While she frequently pointed out my feminine side as she called it and of course my lack of masculinity, she did it in an extremely affectionate and gentle way. Jenny would whisper in my ear and told me I was very pretty that day and she liked the way my hair was styled. It was always in a pony tail but she would gently describe how cute and pretty I would be if I let her put it in pigtails. On one occasion I let her talk me into letting her make-up my face. Mom thought I was pretty and begged me to leave it on for the rest of the day. Since Jenny said she would make out with me if I did I agreed. I think my dick burst into flames the instant I first tasted Jenny's tongue. Now Jenny could have talked me into strutting into the boy's locker room wearing nothing but a pink laced bra, garter belt, fishnets and pink patent leather pumps with make-up on and hair in pigtails announcing free blow jobs as long as I got to make-out with her. She was the prettiest girl I'd ever seen. And trust me I did NOT like that kind of humiliation, she knew it and would never have asked but she sure did tell me how pretty I would look if I did this or that. So she arrived early the morning of my birthday not so much to be the first at the party but to help me get ready. She was as it happened, my best friend or I should say pretty much my only friend.

    She very badly wanted to do me up like a girl but I was having none of that. I'd do it for her alone or maybe her and mom but NOT in front of my grandparents, little sister Hannah and big sister Rose, my aunts, uncles, cousins, neighbors and the two boys in school who didn't call me faggot 100 times a day, Bill and Jim.

    We compromised. I let her put my hair up in a single French braid and tie off the end with a black silk ribbon Mom gave her to use. I wore jet studs Mom loaned me as they seemed a bit more masculine than my giant cubic zirconia studs. They looked like two glass paper weights trying desperately to be diamonds. I liked them at first but I felt more and more girly when I wore them and the only other ones I had were to rings that look like pirate earrings and I usually only wore one at a time alternating ears. She insisted upon giving me a manicure but at least she only used clear polish. Then she wanted to touch up my face a little. She used tiny dabs of concealer to cover a handful of blackheads that just wouldn't washout. She blended a couple of lip glosses to apply to my lips which I only agreed to if they were very near to my natural shade. As it happened the result was only a slightly brighter version of my natural lip color. Then she applied a light brown mascara to my blond eye lashes which kept them natural looking but made my eyes pop slightly. She wanted me ready for the red carpet and I think my mom would have agreed but I wanted none at all so we compromised on subtle. Anyone who didn't know me might not have noticed I was wearing make-up but people who knew me might. My two blind buddies didn't notice but then they didn't notice Jenny was female either. Mom noticed and exclaimed I was going to be "The pretties girl at your party, er I mean the cutest boy!" You can't unring a bell. The bell had rung loudly and any concern Jenny had about my pigment being slightly too pale evaporated in an instant.

    Mom likes to throw theme parties so she decided to do a 70's party. I didn't care about theme. She'd dug out her old white polyester bell bottoms and a polyester satin pink paisley blouse for me to wear and a pink patent leather belt that was about two inches wide. Mom said they were all unisex and that both boys and girls wore them. I hoped nobody would notice the buttons and fly were on the wrong side. Everyone noticed. Grandpa, my uncles and my two guy friends asked why I was wearing girl's clothes. Can't unring a bell. There was no point changing out. I wasn't just a faggot I was a sissy faggot. But Jenny's kiss full on the mouth in front of Grandpa and the other guys cleared up my sexual orientation for them, or at least my little erection did. It was tiny but in polyester everything is visible.

    So other than the initial humiliations everything actually went pretty well. Nobody said anything further about my girly appearance except my grandmother pointed out my French braid was coming undone and she and Jenny re did it for me secretly switching my black ribbon for a pink one. I hadn't noticed until I reached around to scratch an itch hours later to discover it felt different and then held it out front and wondered how it turned pink. Nobody'd said a word.

    We had dinner, happy birthday was sung and gifts were given. I loved all three gifts mom gave me, the clothes my grandparents and aunts gave me and I usually don't like getting gifts of clothing but this time I did. Jenny saved her gift for last. My best buds gave me yet more Legos which I had not quite outgrown.

    Jenny gave me her gift when everyone was gone. She and I went up to my bedroom where she turned around and locked the door. She had gotten an idea when she saw my video camera. She made me promise to not show it to anyone and I promised. Then she told me that she would let me make a video of her stripping naked and playing with herself so I could watch it and jerk off to it when I was alone. Those words alone nearly made me cum in my pants. We'd only ever kissed before. But then she made me promise to let her do anything she wanted to me and I had to accept any other gift she wanted to give me and let her use it on me or she wouldn't do it. I'd have agreed to let her cut off one of my balls and thought it a trivial price just to see Jenny naked for the first time ever.

    I put the camera on the tripod and set up the lights and made the video as Jenny did a slow sensuous sexy as hell strip tease. Then, naked she laid down on the bed and spread her legs and went on about how pretty I was and how much she liked seeing me as the girl she knew I truly was and so on and what sexual things she planned to do to my tiny dick and little balls and big sissy tits and on and on as she frigged her self like crazy. Finally she came which almost caused me to cum just from watching.

    I was going to watch that video every night forever. It inspired thousands of cum loads over the next few years.

    After that Jenny told me her price was I had to let her do a real make-over on me and let her make me as girly as she wanted. Small insignificant price to pay for what I had just witnessed. Also she kept reaching down giving my clit size dick a little squeeze. I couldn't say no. An hour later my hair was in pigtails, my face fully made-up, big dangling earrings hanging from my ears, blood red lipstick, darker more defining eye make-up. She opened the door and called to my mom that I was ready. I had sat their shirtless. Mom walked in with more gifts. She had me open them and among the gifts were pink lace bra, panties, garter belt, garters, fishnets, pink patent pumps, a frilly pink satin party dress with puffy sleeves and a big pink petticoat which held the dress out like a big bell. I was spritzed with perfume, handed a pink patent leather purse with $200 in it. Mom then finished off the look with a set of white faux pearls and a rose gold ring with a pink tourmaline heart. Then Jenny ran downstairs and grabbed a suitcase. While Mom and I watched, Jenny stripped naked, remarking it was OK since we were all girls, and I got to see her bare pussy again only this time mom was watching me seeing her bare pussy and said nothing. When Jenny was all dressed again she had a similar pink satin and lace party dress. If you recall, the 1980's were the time of big hair and big flashy clothes. By this time it was nearly midnight and mom announced she had another surprise. We were, that is to say, Jenny and I were going to a midnight show of the Rocky Horror Picture show which I hadn't even heard of but she was an expert on. Jenny knew about it but I was clueless. I was petrified of the idea of anyone seeing me in drag let alone such frilly pink drag. I had nothing to fear. Not only was I not the only dude in drag but I bumped into two of my classmates who insisted I was way prettier than either of them and these were two of the many boys who had on many occasions ridiculed my lace of masculinity in gym class. One of the boys even said he wished he had real boobs like mine so his dress would look fuller. Mom jokingly offered him a couple of socks to stuff his bra with. As I watched the movie I realized that while Jenny had attempted to make me look realistically like a young teenage girl she had opted to make herself deliberately look like a not so subtle drag queen.

    one advantage of wearing a big dress in a darkened movie theater is that nobody notices a hand slide up under your dress. Mom noticed but didn't say anything until she had to wash my cum stain out of the petticoat. And even then she merely mentioned that she was going to give me a box of condoms to jerk off into so I wouldn't make a mess. Mom had never even brought masturbation up as a topic of conversation before and now she was talking about my sexual habits as casually as though she was talking about my favorite foods and which ones she made that I enjoyed the most.

    That night Mom invited Jenny to spend the night and in my room no less, something she'd never done before and despite my feminine guise I was felling very grown up and very very naughty. On prior sleep overs the activities were confined to the living room where Jenny would sleep while I went up to bed in my own room. This time for the first time Mom suggested Jenny sleep in my bed with me "after all that's what two girlfriends do on a sleepover." If I'd known that letting them dress me up in drag would get me in bed with Jenny I'd have done it a long time ago.

    As soon as Mom left the room and locked the door behind her, Jenny insisted I get out the camera again. This time it was my turn to do a strip tease for her. So I did mimicking what she had down as well as I could. I even frigged my little clit size dick instead of jerking it off as I usually did. She joined in a few minutes in and I shot my load just as Genny started grunting out "I want to lick your pussy Missy, the name she had dubbed me when I was fully dressed earlier. Then she got a towel and wiped me off and we took off our dresses and petticoats and kept on the lingerie and cuddled up. I fell asleep with her hand on my "pussy" another on my tit and her tongue in my mouth.

    Mom was a pack rat. I finished growing up with Jenny as my best friend and girl friend. By our senior year things got far more liberal. Jenny insisted I go to school in drag at least once a week. Gym class had evolved from taunts and ridiculed to having seven fellow members of the weekly Rocky Horror Picture Show Drag Review in my gym class and I was regularly voted most feminine queen of the review. Jenny had confessed to me that she was a secret "half Lesbo" as she put it which I think was her self deprecating way of saying she was bi but wanted to only date a guy that looked like a girl. Even by my senior year I hadn't grown much. I was five two and 90lbs and I'd swear half that was in my natural double DD monster boy titties. I stopped worrying about people staring at my cleavage. Periodically guys would ask me for make-up advice which compared to middle school was surreal and at first somewhat awkward but at least the ridicule had by then almost completely stopped except I found I kind of missed it a little. I used to get secret boners when a pretty girl called me a sissy faggot and told me my tits were bigger than her grandmothers and she'd her from her best friend's brother who was in my gym class that I had a clit instead of a dick. She wanted to see it. I thought she was just teasing but she really wanted to see it.

    I graduated and Jenny and I went to the same community college together. I got a general education diploma but took classes that prepared me for a BFA at the state college though I never went. Jenny became an LPN after two and a half years of nursing school.

    Jenny and I moved in together the middle of our first year at the community college. I went to class full on drag every day now but my style had toned down a bit. I still wore pink but a little bit less flamboyant and by this time my hair was down to my knees and I always kept it in a French braid. We didn't have any classes together so we only saw each other in passing throughout each day.

    So all this leads up to five years ago when my Mom passed away. I went to her place to clean out the house and prepare it for sale. I went to my old room and found she kept everything I'd thought she had thrown away including that first dress and petticoat. I found that first vhs tape and looked around and was grateful to find she also kept my first VCR. I looked through the tapes and found that one where I did the strip tease in front of Jenny at 12. I popped it in the VCR and fast forwarded the tape until I got to my strip tease. I had since developed an interest in little boys though hadn't done anything about it. I was curious what a 12 year old sissy in drag would look like jerking off in front of "her" lesbian girlfriend. Today my cock is only a half inch longer than it was that day and that brings it to just under 3 inches. My tits are now EE cup and bounce around in the most delightfully painful way that reminds me of what a sissy faggot I truly am. I watched myself do the strip tease. I was throbbing hard in an instant. Two minutes later I spontaneously ejaculated without even touching myself as I watched a gorgeous little sissy fagot in full make-up and drag and pretty long blond hair jerk off to the instructions of the preteen girl giving her instructions on how and all I could think about was how much I wanted to kidnap and r*pe the living shit out of that gorgeous little preteen faggot. At that moment, for the first time in my life, I really wanted to fuck myself, badly. I am so glad Jenny made that and all the hundreds of other videos of me jerking off, me fucking Jenny me eating her out, me eating her ass, her pissing down my throat, her tying me up and whipping me with the flogger Mom gave her as a birthday gift, her teaching me how to give sister's boyfriend a blow job and on and on. Every day I frig my little "pussy" with Jenny while we watch old home made k********n together and talk about how badly I want to do really bad things to that little sissy faggot on the TV.

    #44403 — Comments (2) — May 8, 2019 at 8:19 AM — That's Juicy! (4) Remove This.
  • 1
    So what was the third significant thing you got for your birthday?
    11 days ago
  • 2
    i would very much like to see the tapes of you and jenny
    5 days ago




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