This is equally on the topic of “FIRST TIME STORIES” or “TRANSSEXUAL” and is an updated version of the story I sent less than 24 hours ago ***

My Life As A Sissy

From the earliest awakening of my sexuality I felt a strong desire to be girly. I was the smallest boy in my grade at school and my slender body was milky white and nearly hairless. I felt that my penis was unusually small as well, and I didn’t have any pubic hair until at least a year later than the other boys. My first reaction was to shave it off, which I did on summer vacations so it wouldn’t be noticed in the shower at gym. I was back to being deliciously smooth, and by now I was starting to get erections and masturbate, though I hadn’t had an orgasm yet. My favorite way to arouse myself was to tuck my penis between my legs and squeeze my thighs together – and when I was shaved I looked a lot like a young girl. Soon I experienced my nipples, they made me feel a fantastic pleasure that I wanted to never stop, I couldn’t think about anything else when I was in nipple pleasure land. My precious pink tender nipples, I can’t imagine sex without them! One night when I had my wee little dick tucked between my legs and was fondling my nipples into ecstasy it happened, my body had a fiery explosion and there was all this white fluid that gushed out of me – I didn’t know if this was normal or if was dying! But you bet the next night I tried it again and I knew this was my fantastic secret passion, something I would look forward to every night in bed. My orgasms came from deep in my body and radiated all through me – different from the normal stroking technique I soon learned, though I wasn’t so interested in being ‘manly’ or rough in the way of ‘normal’ boys. I came to think of this as my natural way of having orgasm, and it made me feel like a girl… so delicious.

A few years later I started having sexual relationships with girls and women – actually it never occurred to me to be attracted to men, I certainly wasn’t gay. A man with body hair and man smell could never turn me on. I experimented with anal sex by myself, kind of exciting sometimes, but not that pleasurable for me. It wasn’t until many years later that I started to discover where my deepest desires could find expression.

Ladyboy Paula was taller than me, especially on her heels, and hot looking with her long black hair and makeup. I had thought about having sex with a transsexual and sucking my first cock for years till I finally came across her ad and showed up at her place, ready to take the plunge. We stood facing each other, looking each other up and down then she drew me close and put her arms around me and whispered, “Yes baby, relax now, this is what you want baby”…. she took my hand and pulled it down where I could feel that she had a good sized cock in her silk panties, then she started removing my clothes and had me lay down on the bed. I was stripped, laid out nude, and with my slender hairless body and pale skin I felt very girly-submissive. She looked down on me and starting caressing and pinching my nipples, smiling as she saw me react like any girl, my body twitching, hearing me whimpering in pleasure. When someone touches my nipples I get so aroused I can’t stop, I’ll do anything. She bent down and her long lovely hair brushed over my face as we started kissing on the mouth, working tongues into lips, damn sure I was totally hot now! Then she pulled off her panties and I got a look at her (his) cock for the first time, hanging halfway hard. I let out a sigh, it was substantially larger than mine, I stared in awe. Paula slid onto the bed and straddled me, thighs across my chest, and stripped down to just a bra, revealing a chest that was quite flat. Her large cock was poking my chin, staring me in the face, daringly close to my mouth ….. and she gently ordered me “open, open baby”, and for the first time I took the tip of a penis in my mouth, running my tongue over the tender pink skin, exploring the fold underneath and the opening at the end and I was lost up in sucking the shaft as it swelled to full length and stiffness … my god I’m really doing this! Paula started fucking my mouth in slow small thrusts, and soon the most wonderful thing happened…. I tasted my first *oh-my-god-sweet* drop of pre-cum and I knew that all of this came naturally for me, that I would always crave this sex honey, that I was hot as hell for a full mouthful of it! She was breathing harder now and grasped my head with one hand, pulling me to just the angle for her ultimate pleasure… then, close to orgasm, whispered “lick my balls baby!”. OMG I was licking and kissing her balls, the ultimate act of willing submission and emasculation. I thought, no real man does this, only a queer one … and I was so frickin’ excited about finally acting out my craving for queerness and having a hard dick! Paula was moaning and stroking faster and she let out a gasp as streams of hot sperm squirted across my face landing in one eye, in my hair, running down my cheek, and inserted the penis-head into my mouth for one final spurt…… the cum was thick and warm and the taste was indescribable, sweet and salty and viscous……. it might take a little getting used to…. and before I could think about it I had swallowed my first creamy load. That was the first day of my life as a cock loving sissy faggot *

Every day I think about taking a cock in my mouth, making it cum, tasting the creamy love, and of course I swallow after savoring. Each time I let myself go more completely, and I began to accept that I was not just curious and bisexual. I didn’t think about dating women, I was having more fulfillment being sissy gay.

A year later I met Jennifer at Obsession Bar and went with her several times. It got so I looked forward to being with her like nothing else, my appetite for her and her package was truly obsessive. Jennifer was a long legged beautiful Thai T-girl, her sex tool was big in every way, and so I developed my preference for long tall T-girls. I loved feeling overpowered like a girl, looking up her impressive cock and into her eyes, having her insist that I suck it, and she encouraged me to relax and enjoy my feelings of femininity….and when she bucked and gushed in my mouth and her hot cream streamed on my tongue I thought, I don’t want this to ever end, I want to spend the rest of my life with her cock and her cum in my mouth!

Our penises together were a sight… mine looked like a half size version of hers, and more pink and feminine. When soft the hood shrivels down it becomes tiny. Jennifer said that I wasn’t at all manly, that what I had down there wasn’t a dick but a ‘clip.’ She slowly sensually masturbated my clip with thumb and forefinger as she looked intently into my eyes. God, I could almost cum just by looking at her long bare legs around me! The excited sounds I made were high pitched for a guy, she seemed surprised and smiled amusedly. She pinched my nipples with her other hand and soon I was twisting helplessly and sounding just like a girl in orgasm, making a gooey mess in Jessica’s hand, oh sweet release, I feel like a girl when I cum, it’s the real me, it’s the me I love being.

Sayuri is a Japanese post-op transsexual nurse that I fantasize about often. I imagine she knows the depths of my sexuality. She is obviously comfortable with her full transition to female, and as I indulge myself more and more in my relations with ladymen I think of how exciting it would be if I made the final step myself. I would love Sayuri to be the doctor who emasculates me and forms the new pussy between my legs.

Her words to me ***************

Bobbi… I want you to consider having sexual reassignment surgery – removal of your undersized penis and testicles and surgically reforming your sex to become female. You know that your baby-like weeny is only good for giving a woman’s vagina a bit of a tickle, nothing like the penetration she craves from a man. Bobbi I know you dream about having a pussy down there, an itchy pussy slit between your smooth shaved legs! We could perform your castration today, starting by getting you nude and strapping you to the operating table with your legs spread wide open, on display; my pretty nurse assistants will anaesthetize and shave you baby-smooth down there, giggling as they play around with your useless limp pinky. Maybe they’ll fondle and suck your nipples and listen to you whimpering like a young girl. Without your balls your penis will be just a soft, hanging appendage, no shaft, just shriveled skin over a penis head the size of a pink jellybean. You can get used to living this way for a while, we’ll dress you in silk panties so you can experience your emasculation, aware that girls are thinking about little Bobbi, stripped of his manhood.

Then you’ll be ready for your penectomy – becoming dick-less. Feminized guys like you find this so deliciously exciting, being separated from your male part, impotent as far as exciting females; a man without a penis is hardly a man any more! The moment the scalpel passes through the base of your little organ you fathom the irreversible separation as your tiny member falls into the nurse’s hand with a quick spurt of blood; you gasp as you realize it’s final, and it passes from eye to eye as all the girls present in the room see the shock on your face. “His manhood is gone…”

You may as well get used to wearing a skirt now Bobbi, we know you’re already into stockings, high heels and lipstick, you even paint your toenails fuck-me red and shave your legs, you little sissy faggot. Now that you’ve been snipped, you’re almost one of the girls! Vaginoplasty is the final step; you’ll have a pair of hungry pussy lips around your tight slit… we make a precious pink clitoris out of what was once your dick. You’re gonna love to play with it all day……

Time to begin your hormone breast enhancement, you’ve always wanted to have soft round titties with perky female nipples, then it will be obvious to everyone that you’ve become a gurl. All that sperm you’ve been swallowing has already started to affect your hormone activity, hasn’t it? So that more and more it’s the sight of a cock that makes you hot, not pussy anymore. I want to see your nipples all erect and pink, standing out against your powder soft white skin, your nipples turn you on, little bitch! Oh Bobbi, the sensation of having your tits fondled and your nipples sucked is pure ecstasy, making you lay back in total submission; you’ll eagerly open your legs for the hand reaching into your panties, sliding a finger over your wet clitoris, working into your tight cunt… then with your pretty legs and ankles pointed at the ceiling, you feel your tender cuntlips taking the man-sausage inside you, quivering at the entrance, ohh the sweet penetration!

I hear you whimpering and moaning, you’re intoxicated by the thought of all this! I know what makes you pant and squirt in your panties……. you’re a dickless sissy gurl, Bobbi!