CD Rebeca Young Tranny - How I Started pt1
Young Tranny
1. How I Started part 1- Becoming a Gurlie-boy
My sex awoke slowly and over a year or so. Then, after being taken into the moment by an older man the floodgate of physical desire and sexual obsession opened full bore. As I matured I became what some people refer to as hypersexual. Nymphomania or satyriasis or whatever label you choose, my active sexual focus was extreme. I went from a somewhat willing sex "victim," to compulsive submissive plaything, then an active eager participant. Eventually I was a full wanton slut, a whimsical whore who accepted of "herself." When any regrets came and went they did so quickly and with no real impact. I found myself regretting the things I didn't do over the things I did. Then the regrets slowed and all but dropped away. Regrets were temporary and fleeting. Similar to an substance addict battling addiction, regrets were always overcome by the obsession to "be the slutty whore I always wanted to meet." I said that phrase to myself the second day I masturbated, which was also the second day I dressed up in gurlie clothes and lingerie and then acted out my imagined physical acts that whores would do. Masturbation like this quickly became an insatiable obsession. In my early adolescent years I battled my own sexual desires, straight vice bisexual, on a field of almost limitless sexual opportunity. My sex desires conflicted with societal expectations, were inverse to stereotypical male norms. My smoldering obsession quickly lept over the lines of legality and later crossed the boundaries of personal safety and common sense.
At the last days of my teen years I reached a happy middle ground with my sexuality. I embraced my deviations and differences and celebrated my liberation and pansexual freedom. I accepted how amazing it felt to embrace my carnal cravings and give my sex willingly and without limits. I was submissive, but not in the typical sense of total surrender or a person who submitted unquestioningly or needed to to submit to bondage or be pushed into sex. I was demanding but not openly dominant. I fit into no group, and I didn't mind at all. Others on the sexual societal fringes had no idea how to deal with me. I was a surprise but also a curiosity. I would play enthusiastically as a guy or as a gurl with unusual talent and zeal.
As a young guy or dressed as a gurl was different than the usual teen. I was a freak with few limits and endless desire. To gay men I was a self-degrading eager straight-looking and straight-acting bisexual boy with the eagerness and sexual skill of a down-low discreet part-time bitch-boy. I was exactly that in reality.
To straight men on a bisexual binge or opportune moment I was a disposable shameful discreet slutty secret crossdressed faggot fling. I was a secret plaything at a friend's house. A naughty anonymous bitch-boy at an adult arcade, a lipstick mouth at a glory whole, or maybe as a willing boy-toy in a department store restroom. To guys and girls, along with men and women I was a sexual treat and the answer to a deviant craving.
In my teens I had a few non-gay sex flings and a couple of long-term on-off fuck-friend relationships with girls. I also played with a few guys my own age in my teens in restrooms and even at school and on several occasions during school sporting events and once during a play. The guys my age were pretty tame compared to the men. Often the sex was even a bit lame compared to my sex-based relations with older guys. I was usually the bottom, but when I was a top, nobody my age satisfied me.
I was a teenager trying to do typical straight-teen things, but found them unsatisfying and even a bit mundane. One girl was so boring I stopped mid-fuck after she came "quietly."
As a slim and all around twink-boy in my late teens I knelt or bent over for other physically larger athletic boys. But my passion was being dressed like a gurl for them and for older men. I did fuck cute girls and even a school socialite as a race-winning male teen cross-country runner and swim team member. That girl was actually pretty fun, but she was the exception.
Under it all I knew I was just different in some ways. I was far more sexually driven. With girls I didn't really feel a compelling sexual drive like I did as a gurl. I got girls off with multiple orgasms using my firm meaty clean cut white cock, or I got them off orally, but I could take or leave pussy.
Cock was a constant craving. I would leave a girlfriend in her dad's bed still orgasmic and coated in my semen to head home fully satiated to then find myself stopping by a cruising park or an arcade to suck dick or get fucked in my ass. Everything was more satisfying when I dressed up and became Rebeca. Ultimately, at the close of my teens, I accepted that I love being Rebeca.
I accepted myself while I was cumming with a much older man. Just after my birthday taking me a teen to an adult, roughly about eight years after the first day I dressed up and came on the bathroom rug I was on my back getting fucked and about to cum. My divorced Vegas sugar-daddie's cock was punching my cum-button deep in my ass.
He knew I was going to cum too because he was making me. I moaned like a gurlie-whore and watched him fuck me missionary-whore style in the opulent hotel fuck-suite. Looking up, I watched his eyes shut in ecstasy and saw his neck craned upward to draw in deep hard breaths as he pumped himself into my wanton ass-cunt. I lay back, an expensive burnt red-orange wig splayed out around my head and neck and erotically framing my painted glistening face. Sweat dribbled down my temple while saliva and pre-cum slid down my cheek and jaw. My ass was propped up with two pillows to the best position my sex-hole, my boy-cunt, my fuck hole, for his ample more-than-seven-inch meaty cut cock to use me. My knees were directly over my face with my black stiletto pumps facing the ceiling. My hands gripped my own heels and both opened and offered my body in total surrender to his mature hips, ass, and cock. My body was supporting his weight and he was pumping into me hard enough to force the tell-tale slamming of the headboard into the wall.
I moaned as he punched my button deep in my ass-cunt and knew I was going to cum, and then...it was happening. My insides convulsed in that wonderful way, over and over and over causing my cum to drool from my stone-hard cock in a hands-free orgasm. Cum drooled down my garter belt and onto the sheets. Then I stroked myself once, twice, a third time and the second wave orgasm hit. My eyes rolled back and I breathed hard in and out as the throbs started and then shot cum in blasts. After the fourth or fifth shot I parted my eyes to see him enthralled by my show.
He grimaced at me in sexual lust and said in a guttural tone, "Fuuuuuuckkk yesssss," but then pumped really hard into me and said, "Suck me off!" His first shot in me, I rolled around as he pulled back and took him ass-to-mouth. My ass may have earned the cum, but my mouth is going to receive it. As soon as he pulled out I shifted to accept him he gave me what I was craving. My cock was still twitching from the anal-stimulated orgasm that I was swimming through as he came in my mouth. I worked him in a perfect ass-to-mouth finale.
How I started flashed through my active mind as I smoothly sucked him off. The entirety of my story caused another orgasmic tremor to strike through my body. Disjointed thoughts flashed. It was the man's fifty-third birthday. And this was his first treat of the weekend-long birthday celebration. And my ass is tight. And I'm younger than his daughter. And I'm barely a month or so away from being thirty-three years his junior. And, I absolutely relished the forbidden aspect of the age gap.
And then, mouthful of ass-to-mouth cum, I truly accepted my sex. The past eight years had been a hell of sexual journey.
The journey actually started nine blurry years before I was in that hotel with that kinky man.
One night at about 8pm I had a really bad tummy ache. I was constipated and backed up so deep that I was unable to sleep. By 10pm my mom took me to the nearby minor emergency clinic near where we lived in Irvine, California. The nice young So-Cal tanned male doctor in his 30's and his likewise So-Cal tanned buxom blonde nurse in her mid-40's kindly went to work on me with my mom in the room. I recall at one point the doctor told me, "Please remove your pants and remount the table." Then with my mom in the examination room, you know, for my safety, he explained that he was going to give me a "digital rectal" and see if anything was blocking the way. The nurse nonchalantly engaged my mom in conversation and positioned herself in such manner that my mom was facing her and not the doctor or me. She was able to see the whole thing and gave me a weird smile that I later realized was a very knowing and sly horny smile at what was about to happen to me.
I dropped her gaze and shifted in time to catch the doctor and her exchange some message with their eyes. I saw them both wink in a knowing manner that I didn't understand. The nurse shifted her posture to cause my mom to turn completely away from me and face her. As she turned the nice doctor gently pulled my legs open and parted my ass cheeks. He looked up at me and, I swear, with a weird poker-faced twinkle in his eyes he said, "Ok, this will be a bit uncomfortable."
Then he performed the medical procedure. He wiped KY gel lubricant onto my ass rim and then probed into me, gently at first, as if looking for a lost item and then less gently as if he'd found it. He had indeed found the thing he wanted. He pressed upward with a curled finger into my sex-button, my prostate gland and into the inner base of my young penis. He glanced at me to see my reaction and leered at me until I looked away and felt my eyes shut in the odd pressure.
As painful as the stretching of my hole had been, this was entirely different. It was a strange pressure that was so different I couldn't decide if it was good or bad. Well, whatever it was, it didn't hurt. Then he twisted inside me and again glanced up at me and saw my reaction as my body twitched a bit and I felt the new weird pressure. His finger came out all the way and he wiped off and then added more cool lubricant and went back into my hole. There was no pain compared to the first time. He stopped at the nut-sized gland again and, again, he peered up at me to see my reaction. I felt the pressure and looked away in an awkward mix of shame and embarrassment. Why was I embarrassed? I went through the question mentally as he then pressed further into me and something caused me to shutter and quake for a moment. Then then moment was over and he pulled back. Somehow the actual medical part of the procedure had loosened my blockage and my pain was decreased significantly.
Then I wondered why him venturing into my butt-hole didn't bother me. Why wasn't I upset by this? Boys, and girls for that matter, are supposed to be upset, violently upset at having their butt touched like this, and I just accepted it as a strange curiosity.
The Doctor announced that he thought he may have "fixed" me, and told me to wait a moment for him to clean up before I got up and took myself to the restroom. I was oddly relaxed and a little dizzy as I slid off the exam table. I was asked to step into the nearby patient rest room and "evacuate" myself. After a long five minutes or so I returned to the table and the good doctor announced he was going to check for any irregularities. He had me lay back on the exam table again and asked me to be to sit back and relax, we were almost done. He changed his gloves and re-lubed my hole with the cool gel lubricant and again pressed into me. This time was vastly different. With the relief I felt from finally "going" eased my entire body and I was relaxed and out of pain. Again, the doctor probed in, over, then past my prostate a couple of times. This produced the strange, "not bad," sensation. Then he exchanged looks at me and the nurse and went deeper. He went in, and I recalled paying close attention this time and noting as he twisted left and right several times, in, and slightly out several times and then finally on the way out he pressed firmly on my prostate several times. That part really caught my attention and I involuntarily rolled my eyes back into my head and closed my eyelids for a moment as something weird happened. Then I opened them to see the nurse managing to still speak to my mom and also seeing the "money-shot." I was still not sure what I was feeling, but I was embarrassed by how weird-good it felt.
I said nothing and hid my enjoyment-like fascination at the strange sensation.
Then the doctor said, "Ok, once more," and probed into me as deep as the web of his fingers would allow. He held it a moment and then went in and out several times, always rubbing upward into my prostate as he reached it. After about 15, well, certainly no more than twenty probes in and out of my hole I quaked again in an odd way. It felt strange, like an itch while pissing or a really powerful pressure releasing fart. "Weird-good, but still weird," I thought.
A moment later the doctor quietly stopped and I looked up at him as he took a tissue and wiped off my tummy. I looked over him and then at the nurse who looked warm and exhilarated as she caught me looking at her expression. She smiled and said, I bet you feel a lot better! Then she reengaged my mom in conversation.
Thankfully, my mom still looked away, not wanting to see me opened up like that.
I was truly oblivious to having been violated, but felt better in the obvious way, and strangely good in the embarrassing way.
The doctor quietly tossed the tissue and had the faintest smile as he looked at my crotch. The doctor took another tissue and wiped something from my lower tummy and hip area. Looking back I know I was milked and that the mess above the area he'd been working on was my first ejaculation. As it turned out, everyone got something from the procedure.
After the eternity of the procedure I was sent to the restroom to further relieve myself and clean up before going home and I really did feel much better. I was healed of the constipation pain, but, now I had a secret. I knew he'd liked touching me that way and the nurse had enjoyed seeing it happen. That made me weirdly excited and somewhere deep in my subconscious I really loved that he enjoyed the experience. I loved that I was part of it. I was desired and "enjoyed." But the same subconsciousness denied me the conscious realization that I'd been violated. The doctor had switched something inside me on. In a most literal sense he'd pushed my button and I wouldn't remember it for many years.
This whole experience fell into place during post-coital talk with a sex partner who asked me about my past. That partner was a ther****t with a great cock who really liked fucking my ass when I was dressed like a hot school-gurl.
A few months after after that "weird-good" clinic visit I was watching a police action movie that involved prostitutes as a part of the plot. The movie was pretty good, but the sex scenes, both the rough sex and the more tender sex, in fact the entire concept of women being paid for fucking turned me on intensely. I had my first conscious erection related to sexual desire as I watched the movie. Later in bed, I obsessed into the night and found myself touching my hard cock. I rubbed it and stretched it and even stroked it but after a while I became bored and fell to sleep.
The next day was Columbus day, a day off from school. I was old enough and trusted to not ruin the house, so I was alone at home on a day off. My dad and mom had divorced about two years before, so I was used to being on my own. I liked it. I could play with my toys as loud as I chose and could say bad words if I wanted. I re-imagined the movie scenes with perverse different endings and after a bit I felt like exploring.
I knew, in a general manner, what sex was. I'd fought many nights to not hear my mom with a guy or even my dad on an attempt to patch things up. So, I knew my mom was having sex fairly often despite barely knowing what sex was.
My mom was a nurse in training and she was fit and good looking. She was very sexually active, and, though I had no interest in my mom, I was curious about how much of a slut she might be. So, I took a break from re-playing the police-prostitute movie plot and and quietly went through her things. I skipped her nurse scrubs and went through some dresses and then some skirts, then some miniskirts that made me both cringe and turned me on.
Finally, I found her underwear and a floodgate opened. The feel of the thin silky feminine fabrics of her bras, panties, panties, and slips turned me on. I noticed my cock rise. On a whim, I stripped down and tried on a bra. Then the matching panties. Then I checked myself out in the mirror and found her stockings mixed into her pantyhose. The prostitutes in the movie had all worn stockings and...oh look, garter belts, I thought. In minutes I was at the mirror and modeling the peaches n' cream colored bra, with black lacy trim, nude stockings, a thin black garter belt, and red panties. I loved how they felt and was excited at how my own dick popped up out of the panties. But the look wasn't quite right. I went back and put on the black panties and the black bra, straining to hook it behind my back. The look was perfect and hot. I strutted and preened, my boyish, yet now oddly girlish, over-the-ear blonde-red straight hair flinging around. After a few minutes my dick leaked some clear fluid and on a whim I tasted it. In the movie one of the prostitutes had risen from off a john's cock, mouth glistening and I had figured out that she'd had the man's dick in her mouth, so, why not taste my own fluids? It tasted like thin snot. How unimpressive, I thought. Then, on instinct, I stoked myself and realized that it felt good, better, far better than it had even the night before. I stroked and stroked and preened at myself and then mouthing some of the sex-lines from the movie. I got a pillow and put it on the bathroom floor and placed my hard cock in it and pumped for all I was worth as I preened at myself in the mirror. Then I lost control of myself, or, something beyond my control happened. My insides moved and then out popped this...this...stuff! I panicked a moment as my little penis throbbed up...held, then down, then up and held...then back down. I throbbed uncontrollably for over half a minute. I saw the "stuff" all over everything and briefly considered tasting it, but did not. Instead, I had another moment of panic. I wiped up my "stuff" and sat for a moment wondering all kinds of things about what had just happened.
It had felt weird. Good even. I cleaned up the pillow again and put all the things away. It was only 10am.
By noon I'd finished my ramen noodles and lunch meat and I was bored. I knew my neighborhood friends were out of town for the long weekend so, what to do I wondered. Before long I was watching TV and saw a soap opera and one of the women was in her underwear in a robe and that was it. Filled with desire, I got up and went back to my mom's room and put the same items back on and began playing again. Then, I remembered the old "theater" trunk and went into that to find the professional-grade curly platinum blonde wig my mom had worn for Halloween last year. I put that on and went back into the bathroom and watched myself in the mirror. I was aroused before I saw myself in the mirror, but when I saw myself in the mirror that arousal actually dropped a bit. I wasn't sexy or girlish enough.
I knew what I needed. It was only about 1:30pm. I had time. I got my mom's makeup out and, using a Cosmopolitan magazine makeup guide, I put on my first makeup. Blue shadow to compliment my blue eyes, rouge, eyeliner, and lipstick. Then I looked myself over and smiled. I hot little gurl. A whore like in the movie. My cock strained and I stroked it as I watched myself. I mouthed things, awful things, things boys should never say, and I imagined that girls should say those horrible degrading things all the time. All of a sudden, with no pillow, no humping, my cock exploded again, except this felt amazing!
That day I came four times and thought I'd actually hurt myself on the last one. I cramped my crotch but after a minute the pain ended. I cleaned up and vowed to not dress up again. After all, I wasn't a faggot, I was a nice young man.
That night I stroked myself again and brought an orgasm out once more. This time, in the darkness, I licked it off my fingers and liked the fact that I was doing it, and the taste was a bit unique too. But, I held to my vow to not dress up like a girl and not be a gay boy...for at least a month.
In the meantime, the orgasms I had late at night and not dressed as a naughty girl were ok, but I craved the other part- the naughty "gurl" part.
With my mom now a fully trained nurse she began working many late and weekend shifts.
Over the weekend in early November my mom was away for work and I dressed about half the time she was gone. I played again, and again, and again. Each time I dressed up and played it ended with me vowing it was the last time.
A few of weeks later the floodgates opened full blast. During holiday break I dressed almost daily and had three and a few times fours orgasms each day. I would also masturbate in bed late at night, but soon realized that I had the most intense orgasms when I was dressed. Over the holiday break I dressed and expanded my look into mom's shoes and dresses. I no longer preened and mouthed words, I spoke them in my best gurlie voice. I also began playing in the carpeted and far more comfortable bonus room on the side of the house. The light was good and there was a giant mirror so I could watch my own show. I found and then stole a couple of my dad's "Variations" and "Letters" magazines and read about sex as I jacked off. I would feel myself get close and then I'd hump a pillow and cum all over the pillow. The rest of the vacation from school I spent every bit of alone time either dressing and acting out or thinking about dressing and acting out as a sex object.
Next door, Mr. Carlton stood at his kitchen sink and stared down at a gentle 30 degree angle into the bonus room of the house next door as he filled a glass of water. The family next door was nice and they'd been mutually helpful with yard work and other neighborly matters. When the husband left the good looking dirty-blonde wife both he and his wife, Mrs. Carlton, had helped out. Those same nice neighbors had helped out Mrs. Carlton when she finally listened to his step daughter and step son about Mr. Carlton's "special time" with them. And then she left him, taking them with her.
Now, at his sink, during the holidays, a gift was delivered in the form of a cute little girl humping pillows in the room next door. Mr. Carlton wondered who the hell this little girl was and how had he missed her moving in. She was slender and was obviously in mom's oversized sexy things. Then the pumping changed to an orgasmic spasm. Mr Carlton's six inches of lust stiffened and he dropped his pants and stroked himself. As the girl finished Mr. Carlton was only half done. The girl stood and disappeared and after 15 minutes reappeared in a blue dress and different shoes. After a few minutes the dress came up and the girl dropped to straddle the pillow. The girl humped the pillow and then bounced up and down, then the back of the dress came all the way up and the girl sank to the floor and began a fuck-motion.
Mr. Carlton's carnal instinct knew what he was seeing, but at first didn't recognize it. Mr. Carlton rounded each stroke of his cock over his stiff cockhead as he began to piece it all together. Then, after a short few moments the figure next door arched upward in a tell-tale orgasmic thrust and then quaked and quivered for several long erotic moments. Then the body turned over, the butt sitting just to the side of the soiled bed pillow and he saw it. The girl was actually the boy next door. He recognized the face and then saw the cute little glistening cock under the garter belt, a short thirty feet away. It was all unmistakable. Mr. Carlton began to orgasm all over his sink cabinet doors. He worked himself to keep his cum flowing as the strange little girl, apparently fake, or acting out an orgasm moments before now facing him stoked herself and short her cum onto her own belly. Mr. Carlton, cock still twitching, stepped back a bit and caught his breath but still watched as the gurl or the femme-boy licked her hands and used their hand to wipe cum off her or his belly. Her's he decided. Mr. Carlton squeezed his orgasmic cock in a hard pulsing motion. Definitely a gurl, he decided. A gurl with a penis dressing up and choosing to be a sex object. What a good gurl, Mr. Carlton thought as he wiped himself off and started to harden again. He came three more times that day unable to stop peeping across the way at "her."
That night he thought, "I want her."
Five and a half months later I was about to start the first day of summer vacation. Mom was regularly leaving for work at seven and I knew her clothes and underwear very well. When I woke up I was already mentally picking though her things and imagining which whore I would be that day. I found mom's other wigs and was going with the longer of two platinum-blonde wigs, the sheer tight-topped and flowing blue dress, the black stockings and of course the matching black garter belt and the tight bra. The bra was utterly sinful and I'd noted when she wore it fer her boyfriends. It turned me on. The bra was little more than thin panties designed to cover boobs. I had my soft foam balls ready for my boobs from my secret hiding place. I knew which makeup look I was going to use and had my "Letters" page folded with some brunette porn star on it and ready as a makeup guide.
I saw mom out the door and ran back into her room as she pulled out. In thirty minutes I was dressed and on my way to the bonus room, my mom's black pumps click-clacking across the tile till I reached the bonus room's carpet. I said several well-used lines from movies of women teasing guys and then moved into my re-written and re-imagined lines for those roles. Then, as I crouched down to submit to sex and began to stroke I said the really raunchy things as I watched myself in the floor mirror and stoked my cock.
During spring break I'd dressed every day except one and had gotten much better with my makeup and my femme look. I'd developed a bit of a femme-voice and knew how to control my orgasm or "edge," before I knew it was edging. I was still having between three and four orgasms every day, but the build-up was slow and incredibly fun.
As I hit the edge of the first orgasm of the day I rolled over from the pillow and onto my back, as I'd always done. I spread my crotch wide and relaxed a full minute and slow stroked myself.
KNOCK-KNOCK-KNOCK-KNOCK-KNOCK!!! on the bonus room window shocked me and caused my heart to jump. I raced in fear to the nearby couch and hid. A familiar voice came through the window in a low, calm, almost conversational tone and volume. He was just loud enough for me to hear through the wall like you might hear a couple of people outside my mistake.
"It's ok. You are not in trouble," Mr. Carlton, the man from next door who was older than my parents said quietly through the window.
Ten minutes later he'd talked me into speaking to him through our common fence line. I went out back and there he was, almost as tall as the fence pickets and able to see me clearly through the gaps in the wood. He took his time. We had all day. After about 20 minutes he suggested I sit on the patio bench and then suggested I would be more lady-like if I crossed my legs, not laying my leg flat, but next to my lower leg like a lady. Mr. Carlton added, "Yes, gently kick the crossed leg a bit like a lady...did you know some women can orgasm doing that?"
The conversation went on for about two hours. I know this because I went in and peed and saw it was almost noon. Back outside Mr. Carlton was kind and encouraging, often saying that I was very smart and sensitive and things like "You already know this, but..." to then lead me to agree with an inappropriate statement about sex. About an hour and a half later he started leading me into how different it was to watch sex movies than look at pictures. "The sounds, the moves...oh so amazing when women cum, and guys too. You'd love it!"
Then he took the real chance. "Hey, how about you come over tomorrow and watch movies in my upstairs movie theater. I have a big TV and you won't have to worry about your mom showing up early or anything."
He'd apparently seen the five or six times my mom came home early from work. I was paranoid about that happening and he knew it. I'd nearly been caught but had recovered nicely quickly replacing her things and barely making it into the shower when she came inside each time.
He offered and I turned him down and then he started a new subject to later come back to the offer to watch porn and play in safety. Then he offered me a free set of stockings. A few minutes after that offer fell flat he offered money and even a hand-held video game. Then, thinking he'd failed, he said, "You know, I just find you fascinating. I have been watching you ever since winter break and I just want to see you up close. I don't want to touch you or hurt you. I just really find you exciting."
"No." I turned him down again.
"Ok, well, your mom may be home soon and i don't want you to get in trouble, but hey, how about, well, stand up and lick your lips for me, grab your boobs...show me your legs..."
Reluctant for a minute or so, then after him all but begging or threatening me, and then a short a private "why not?" moment, I spent the next twenty minutes posing and preening for him. I gave my first show. At first it was tame and teasing, then, emboldened by Mr. Carlton I became more risque and ultimately very sexual. Toward what was the end of the show I stroked myself for him and showed him my legs and my ass. I licked and sucked my fingers one at a time and then split them apart like they were a pussy and licked the "V".
He was stroking himself as he watched me. I couldn't see his cock, but I knew he was. After a while he directed me and I was into being directed.
"Ok, now turn around, bend over and hold yourself up on the table but pull up the dress and look at me with your sexy lips, and blow kisses...ok good, now pull the panties aside." I did and he said, "Yes, yes, yes...ok, hold it for a...haaa...uhhh minute..." Silence a moment or two then, "Yesss, good gurlll ....uhhhh ohhh!!" he moaned. He came.
Through a gap in the fence his load blasted through. I felt a rush as it happened. His load was mammoth compared to mine and it turned me on somewhere deep down. I felt so very wrong by enjoying it, but enjoyment it really was. He finished and after he invited me over one more time, I went inside and finally rubbed myself to an orgasm.
The next day he waved me over from his kitchen window. I declined, shaking my head. But, Wednesday I agreed. I went, dressed in my favorite gurlie things under my boy clothes over to Mr. Carlton's house and unknowingly began the process of being groomed. I had no idea what I had gotten myself into. He promised and delivered porn movies. He promised and delivered sexy outfits that fit me. He'd promised and delivered a safe place to play, at first.
Each day the rest of the week I watched porn movies and jacked off watching them and myself in the array of mirrors he'd placed around his dimly-lit upstairs playroom. The room was a converted loft with a working restroom and a small bedroom of to each side of the top of the stairs and on the back edge of a large rectangular open space with a love seat. The floors were hardwood then the loveseat, then the thick padded rug, then the TV stand. To the left of the TV was a red vinyl bench-bed and a double-curtained window. The TV on the stand was pretty big and had two DVD players hooked up and mirrored set of doors in front of the DVD storage shelves. On each side of the TV were tall floor lamps with dim red bulbs that created a very sexual feel to the room. There was a single strip of regular dim white lights overhead that were positioned between the TV and the love seat. The effect was to light the padded rug area and the love seat while keeping the rest of the play space dark. It worked well. There were ten or twelve mirrors of various larger sizes placed all around the room so that anyone, like me for instance, in the center of the room on or near or love seat was viewable from the stairs or the small bedroom or the bathroom or, well practically anywhere.
Mr. Carlton usually stayed back in the dark area of the bedroom doorway, discreet, but visible if I really strained.
At first, my days were fairly similar. I found myself using the bathroom to do my makeup and came out to find porn playing on the TV and then did a short turn-and-pose routine before he urged me to enjoy myself while he went downstairs "to take care of something."
Each day I usually came twice before noon and then once or twice more after lunch. Each day I came over and he played porn videos for me while in turn he watched me enjoy myself on the well-lit loveseat facing the TV and all the mirrors. He was out of sight and in the darkness. So, I gave him a show while ignoring him, and that suited me just fine.
About the third time over, the following Monday I think, I had lunch and put on a gift he left for me in the back bedroom. Then I watched another movie or maybe two, and came once or even twice more in my own black baby doll set with garters and stockings that were brand new. He even bought me shoes! I came watching myself hump pillows, preen, and make lewd gestures at myself. I watched myself almost as much as the movies. The movies changed and became more and more racy too- straight, straight groups, gang bangs, interracial, interracial gangbangs, then lesbian and bisexual girl-man-man, then transsexual movies, and finally some really nasty home made movies of gurls like me. Those movies took me up to the following Monday.
Throughout the initial grooming process I caught a few glimpses of Mr. Carlton and I knew he was watching me, but I focused on the movies and watching myself as I came. We each got what we wanted. I wanted porn, and he wanted to watch me playing with myself. He provided me with more and more cheap slutty sexy lingerie and a sexy schoolgirl Halloween costume and all the KY jelly I could ever need.
The next week started with several home-made movies of CDs and transsexuals. I came five times that Monday, the first day and left with a deep sexual cramp in my body. The second day, likewise and he noticed I liked a redhead gurl. The third day there was a red wig in the upstairs bathroom I used as a changing room and he had four movies with redhead trannies in them. Thursday he played the first movie and half and hour into it I realized he was in the room behind me and off to one side, just barely in the shadows. I looked over at him in the mirrors. He was nude except for some black cowboy boots.
Then, stroking his cock in time with me he crossed directly in front of my view of the TV screen, hard glistening daddy-cock in hand, and sat on the other side of the love seat. He slow-stroked a minute and when I did nothing like get up and run away scared, he stopped, turned to me, then back at the porn movie and released his cock. Then another minute passed with me also stopped in my stroking. The two of us watched the movie in silence. Then he moved. His arm came up and he crossed it over me as his large hand curled around my neck. As he did the red head tranny porn queen was on her knees sucking a cock, twisting her head and doing it with gusto.
Mr. Carlton said "Let's see if you've learned anything."
I knew what was about to happen like it had already occurred. I knew he was going to make me suck his cock. I knew it and my heart pumped hard and fast in anticipation of very wrong erotic action.
Over and over my mind raced through protest after protest. Each weak protest of why I shouldn't just do it was answered by "No one will will know." My crotch throbbed and my stomach turned in protest then settled, overcome by my hyper-sexual brain. I was overwhelmed in the moment and Mr. Carlton saw it. He'd known it would be like this for me and took it slow enough to not frighten me, but continued forward firmly enough to make me either let it happen or commit on my own. Just as I was about to commit to becoming a cocksucker, even if it was only once, I told myself, he took me.
I had wanted it deep down and parted my lips to sink down on him, but he was just ahead of me. Later he told me he thought I was about to back off and shy away, so he reached over to make it happen. Mr. Carlton, fit guy in his forties, tall, with about six and a half firm inches of meaty clean-cut cock pulled me over and pushed my face into his big daddy cock, smearing my lipstick over his wet cockhead.
The first time you do anything, good or bad, it is a new experience and whether or not you are any good at it may, or may not, be important to the experience. But, how much you like it is. Hitting a baseball, making a basketball shot, shooting a gun, even fighting the first time all leave an indelible impact on you. I liked sucking cock from the moment he made me.
The lust of the moment and the wanton desire combined with the twisted aspects of it being lees-than consensual sodomy all were a powerful aphrodisiac. I liked it the first time it went in, but, still wedded to societal pressures, I was embarassed and hated how much I liked it. But I did it.
His cock went in as I was pushed downward. He reached the back of my throat and he said, "That's a good gurl, now close your lips and suck on the upward stroke." Then he firmly and almost gently guided me up, then down, up, then down...nice and smooth...calm, collected.
From the very first push of my face down onto his cock he coached me. I moaned involuntarily and possibly in protest at first and then I realized how hard I was, I'd forgotten to let go of my own cock, and I stoked.
At first my senses rushed to feel every little nasty sensation and movement. His skin over my lips, his little hairs against my nose, the dank sweaty smell of his crotch, the smooth saliva and pre-emmission from his shaft, the hardness, the way the head plugged my throat and halted my breathing. All of it. Then I realized something. I hated that I loved it so much. My identity was altered by his cock and my own willingness to not just submit, but to willingly accept him in me. As I was going up and down on him, so I told myself "I like it...but so what." With each head bob I leaped through entire debates in my mind. Self recrimination led to personal name calling then the cock would hit my throat and I'd reset to "Mmmmm that feels amazing..." Then I mentally went through the same faggot or straight boy debate. "What are you doing? You are ruining yourself? You are degrading yourself!! You are a good young man, a good boy!...Oh wait, cock! Absolute lust and raw sex...hard cock choking me a little...Amazing! MMMMM!!! I kind of a whore! I am kinda a slut!! Hottttt!!!" Over and over the same debate took place in split seconds as I sucked him off, then at some point it all dropped away and I just stayed in the moment. I liked being a whore, or probably more accurately, I like playing like I was a whore, just like I had done since the very first orgasm. Now it was real.
As all that flashed through my little cocksucking head Mr. Carlton noticed I was physically situated poorly. I was sitting on my right ass cheek and leaning to my side, sucking him off sideways. He felt my teeth sc**** him and pulled me up to the top of his cock.
He said firmly, "No fucking teeth! Now slide off the couch and get between my legs like a good gurl. Be the gurls in the movies, and suck my cock!"
I complied and slid into place and worshiped his daddy-cock. Enthusiasm was high, but my skills were poor. I went down and up and followed his directions. Then after probably ten minutes and at the end of the sex scene in the tranny movie he pulled himself free and stoked himself to completion. He held my lips at the top of his cock and stoked, his fist bumping my lips each time and actually giving me a fat lip later. Just before he came he breathed in and out rapidly and moaned a bit. It excited me beyond imagination. I knew he was going to cum. It made me even hotter.
Between hard deep breaths Mr. Carlton said, "Fuck yes you are so fucking hot, I am gonna make you perfect...stroke yourself and open your mouth little whore!"
I stroked myself and opened as he pushed to my lips and shot his semen into my tight small mouth. As his orgasm shot and then so did mine. I felt and tasted him and loved it.
In a minute we were done and I was in a mild shock, silent and orgasmic, but also in a post physical violation shock. Later, when I confessed all this to a different psychoanalyst - who was balls-deep fucking me from behind at the moment I described my fist blow job to him, this exact story - he said, "Yeah, sure, that was probably mild shock. You were overwhelmed and violated."
With Mr. Carlton's semen coating my mouth, afraid to swallow, 'cause, well you know, I wasn't a faggot, I went from kneeling on the carpet to slumping onto the padded rug, kicking my high-heels forward and looking like a little girl not sure what to do next. Legs outstretched in a wide "V" and breathing hard myself, and of course still coated in my own cum and some lube. I looked at the Mr. Carlton's cock and leaned back and away a little, arms propping me up and legs extended even wider. I let myself smile, closed mouth, cum still in my cocksucking mouth.
I looked down and saw my cock was still hard and slimy. His was too. He smiled at me kindly. He searched my expression to determine if he had a problem now or the most wonderful thing in the world.
I knew what he'd done. How he'd manipulated the whole process. I went through the same toxic debate in my little overworked mind and set it aside and consciously decided to accept and enjoy the moment. I made my first life decision and smiled up at him.
1. How I Started part 1- Becoming a Gurlie-boy
My sex awoke slowly and over a year or so. Then, after being taken into the moment by an older man the floodgate of physical desire and sexual obsession opened full bore. As I matured I became what some people refer to as hypersexual. Nymphomania or satyriasis or whatever label you choose, my active sexual focus was extreme. I went from a somewhat willing sex "victim," to compulsive submissive plaything, then an active eager participant. Eventually I was a full wanton slut, a whimsical whore who accepted of "herself." When any regrets came and went they did so quickly and with no real impact. I found myself regretting the things I didn't do over the things I did. Then the regrets slowed and all but dropped away. Regrets were temporary and fleeting. Similar to an substance addict battling addiction, regrets were always overcome by the obsession to "be the slutty whore I always wanted to meet." I said that phrase to myself the second day I masturbated, which was also the second day I dressed up in gurlie clothes and lingerie and then acted out my imagined physical acts that whores would do. Masturbation like this quickly became an insatiable obsession. In my early adolescent years I battled my own sexual desires, straight vice bisexual, on a field of almost limitless sexual opportunity. My sex desires conflicted with societal expectations, were inverse to stereotypical male norms. My smoldering obsession quickly lept over the lines of legality and later crossed the boundaries of personal safety and common sense.
At the last days of my teen years I reached a happy middle ground with my sexuality. I embraced my deviations and differences and celebrated my liberation and pansexual freedom. I accepted how amazing it felt to embrace my carnal cravings and give my sex willingly and without limits. I was submissive, but not in the typical sense of total surrender or a person who submitted unquestioningly or needed to to submit to bondage or be pushed into sex. I was demanding but not openly dominant. I fit into no group, and I didn't mind at all. Others on the sexual societal fringes had no idea how to deal with me. I was a surprise but also a curiosity. I would play enthusiastically as a guy or as a gurl with unusual talent and zeal.
As a young guy or dressed as a gurl was different than the usual teen. I was a freak with few limits and endless desire. To gay men I was a self-degrading eager straight-looking and straight-acting bisexual boy with the eagerness and sexual skill of a down-low discreet part-time bitch-boy. I was exactly that in reality.
To straight men on a bisexual binge or opportune moment I was a disposable shameful discreet slutty secret crossdressed faggot fling. I was a secret plaything at a friend's house. A naughty anonymous bitch-boy at an adult arcade, a lipstick mouth at a glory whole, or maybe as a willing boy-toy in a department store restroom. To guys and girls, along with men and women I was a sexual treat and the answer to a deviant craving.
In my teens I had a few non-gay sex flings and a couple of long-term on-off fuck-friend relationships with girls. I also played with a few guys my own age in my teens in restrooms and even at school and on several occasions during school sporting events and once during a play. The guys my age were pretty tame compared to the men. Often the sex was even a bit lame compared to my sex-based relations with older guys. I was usually the bottom, but when I was a top, nobody my age satisfied me.
I was a teenager trying to do typical straight-teen things, but found them unsatisfying and even a bit mundane. One girl was so boring I stopped mid-fuck after she came "quietly."
As a slim and all around twink-boy in my late teens I knelt or bent over for other physically larger athletic boys. But my passion was being dressed like a gurl for them and for older men. I did fuck cute girls and even a school socialite as a race-winning male teen cross-country runner and swim team member. That girl was actually pretty fun, but she was the exception.
Under it all I knew I was just different in some ways. I was far more sexually driven. With girls I didn't really feel a compelling sexual drive like I did as a gurl. I got girls off with multiple orgasms using my firm meaty clean cut white cock, or I got them off orally, but I could take or leave pussy.
Cock was a constant craving. I would leave a girlfriend in her dad's bed still orgasmic and coated in my semen to head home fully satiated to then find myself stopping by a cruising park or an arcade to suck dick or get fucked in my ass. Everything was more satisfying when I dressed up and became Rebeca. Ultimately, at the close of my teens, I accepted that I love being Rebeca.
I accepted myself while I was cumming with a much older man. Just after my birthday taking me a teen to an adult, roughly about eight years after the first day I dressed up and came on the bathroom rug I was on my back getting fucked and about to cum. My divorced Vegas sugar-daddie's cock was punching my cum-button deep in my ass.
He knew I was going to cum too because he was making me. I moaned like a gurlie-whore and watched him fuck me missionary-whore style in the opulent hotel fuck-suite. Looking up, I watched his eyes shut in ecstasy and saw his neck craned upward to draw in deep hard breaths as he pumped himself into my wanton ass-cunt. I lay back, an expensive burnt red-orange wig splayed out around my head and neck and erotically framing my painted glistening face. Sweat dribbled down my temple while saliva and pre-cum slid down my cheek and jaw. My ass was propped up with two pillows to the best position my sex-hole, my boy-cunt, my fuck hole, for his ample more-than-seven-inch meaty cut cock to use me. My knees were directly over my face with my black stiletto pumps facing the ceiling. My hands gripped my own heels and both opened and offered my body in total surrender to his mature hips, ass, and cock. My body was supporting his weight and he was pumping into me hard enough to force the tell-tale slamming of the headboard into the wall.
I moaned as he punched my button deep in my ass-cunt and knew I was going to cum, and then...it was happening. My insides convulsed in that wonderful way, over and over and over causing my cum to drool from my stone-hard cock in a hands-free orgasm. Cum drooled down my garter belt and onto the sheets. Then I stroked myself once, twice, a third time and the second wave orgasm hit. My eyes rolled back and I breathed hard in and out as the throbs started and then shot cum in blasts. After the fourth or fifth shot I parted my eyes to see him enthralled by my show.
He grimaced at me in sexual lust and said in a guttural tone, "Fuuuuuuckkk yesssss," but then pumped really hard into me and said, "Suck me off!" His first shot in me, I rolled around as he pulled back and took him ass-to-mouth. My ass may have earned the cum, but my mouth is going to receive it. As soon as he pulled out I shifted to accept him he gave me what I was craving. My cock was still twitching from the anal-stimulated orgasm that I was swimming through as he came in my mouth. I worked him in a perfect ass-to-mouth finale.
How I started flashed through my active mind as I smoothly sucked him off. The entirety of my story caused another orgasmic tremor to strike through my body. Disjointed thoughts flashed. It was the man's fifty-third birthday. And this was his first treat of the weekend-long birthday celebration. And my ass is tight. And I'm younger than his daughter. And I'm barely a month or so away from being thirty-three years his junior. And, I absolutely relished the forbidden aspect of the age gap.
And then, mouthful of ass-to-mouth cum, I truly accepted my sex. The past eight years had been a hell of sexual journey.
The journey actually started nine blurry years before I was in that hotel with that kinky man.
One night at about 8pm I had a really bad tummy ache. I was constipated and backed up so deep that I was unable to sleep. By 10pm my mom took me to the nearby minor emergency clinic near where we lived in Irvine, California. The nice young So-Cal tanned male doctor in his 30's and his likewise So-Cal tanned buxom blonde nurse in her mid-40's kindly went to work on me with my mom in the room. I recall at one point the doctor told me, "Please remove your pants and remount the table." Then with my mom in the examination room, you know, for my safety, he explained that he was going to give me a "digital rectal" and see if anything was blocking the way. The nurse nonchalantly engaged my mom in conversation and positioned herself in such manner that my mom was facing her and not the doctor or me. She was able to see the whole thing and gave me a weird smile that I later realized was a very knowing and sly horny smile at what was about to happen to me.
I dropped her gaze and shifted in time to catch the doctor and her exchange some message with their eyes. I saw them both wink in a knowing manner that I didn't understand. The nurse shifted her posture to cause my mom to turn completely away from me and face her. As she turned the nice doctor gently pulled my legs open and parted my ass cheeks. He looked up at me and, I swear, with a weird poker-faced twinkle in his eyes he said, "Ok, this will be a bit uncomfortable."
Then he performed the medical procedure. He wiped KY gel lubricant onto my ass rim and then probed into me, gently at first, as if looking for a lost item and then less gently as if he'd found it. He had indeed found the thing he wanted. He pressed upward with a curled finger into my sex-button, my prostate gland and into the inner base of my young penis. He glanced at me to see my reaction and leered at me until I looked away and felt my eyes shut in the odd pressure.
As painful as the stretching of my hole had been, this was entirely different. It was a strange pressure that was so different I couldn't decide if it was good or bad. Well, whatever it was, it didn't hurt. Then he twisted inside me and again glanced up at me and saw my reaction as my body twitched a bit and I felt the new weird pressure. His finger came out all the way and he wiped off and then added more cool lubricant and went back into my hole. There was no pain compared to the first time. He stopped at the nut-sized gland again and, again, he peered up at me to see my reaction. I felt the pressure and looked away in an awkward mix of shame and embarrassment. Why was I embarrassed? I went through the question mentally as he then pressed further into me and something caused me to shutter and quake for a moment. Then then moment was over and he pulled back. Somehow the actual medical part of the procedure had loosened my blockage and my pain was decreased significantly.
Then I wondered why him venturing into my butt-hole didn't bother me. Why wasn't I upset by this? Boys, and girls for that matter, are supposed to be upset, violently upset at having their butt touched like this, and I just accepted it as a strange curiosity.
The Doctor announced that he thought he may have "fixed" me, and told me to wait a moment for him to clean up before I got up and took myself to the restroom. I was oddly relaxed and a little dizzy as I slid off the exam table. I was asked to step into the nearby patient rest room and "evacuate" myself. After a long five minutes or so I returned to the table and the good doctor announced he was going to check for any irregularities. He had me lay back on the exam table again and asked me to be to sit back and relax, we were almost done. He changed his gloves and re-lubed my hole with the cool gel lubricant and again pressed into me. This time was vastly different. With the relief I felt from finally "going" eased my entire body and I was relaxed and out of pain. Again, the doctor probed in, over, then past my prostate a couple of times. This produced the strange, "not bad," sensation. Then he exchanged looks at me and the nurse and went deeper. He went in, and I recalled paying close attention this time and noting as he twisted left and right several times, in, and slightly out several times and then finally on the way out he pressed firmly on my prostate several times. That part really caught my attention and I involuntarily rolled my eyes back into my head and closed my eyelids for a moment as something weird happened. Then I opened them to see the nurse managing to still speak to my mom and also seeing the "money-shot." I was still not sure what I was feeling, but I was embarrassed by how weird-good it felt.
I said nothing and hid my enjoyment-like fascination at the strange sensation.
Then the doctor said, "Ok, once more," and probed into me as deep as the web of his fingers would allow. He held it a moment and then went in and out several times, always rubbing upward into my prostate as he reached it. After about 15, well, certainly no more than twenty probes in and out of my hole I quaked again in an odd way. It felt strange, like an itch while pissing or a really powerful pressure releasing fart. "Weird-good, but still weird," I thought.
A moment later the doctor quietly stopped and I looked up at him as he took a tissue and wiped off my tummy. I looked over him and then at the nurse who looked warm and exhilarated as she caught me looking at her expression. She smiled and said, I bet you feel a lot better! Then she reengaged my mom in conversation.
Thankfully, my mom still looked away, not wanting to see me opened up like that.
I was truly oblivious to having been violated, but felt better in the obvious way, and strangely good in the embarrassing way.
The doctor quietly tossed the tissue and had the faintest smile as he looked at my crotch. The doctor took another tissue and wiped something from my lower tummy and hip area. Looking back I know I was milked and that the mess above the area he'd been working on was my first ejaculation. As it turned out, everyone got something from the procedure.
After the eternity of the procedure I was sent to the restroom to further relieve myself and clean up before going home and I really did feel much better. I was healed of the constipation pain, but, now I had a secret. I knew he'd liked touching me that way and the nurse had enjoyed seeing it happen. That made me weirdly excited and somewhere deep in my subconscious I really loved that he enjoyed the experience. I loved that I was part of it. I was desired and "enjoyed." But the same subconsciousness denied me the conscious realization that I'd been violated. The doctor had switched something inside me on. In a most literal sense he'd pushed my button and I wouldn't remember it for many years.
This whole experience fell into place during post-coital talk with a sex partner who asked me about my past. That partner was a ther****t with a great cock who really liked fucking my ass when I was dressed like a hot school-gurl.
A few months after after that "weird-good" clinic visit I was watching a police action movie that involved prostitutes as a part of the plot. The movie was pretty good, but the sex scenes, both the rough sex and the more tender sex, in fact the entire concept of women being paid for fucking turned me on intensely. I had my first conscious erection related to sexual desire as I watched the movie. Later in bed, I obsessed into the night and found myself touching my hard cock. I rubbed it and stretched it and even stroked it but after a while I became bored and fell to sleep.
The next day was Columbus day, a day off from school. I was old enough and trusted to not ruin the house, so I was alone at home on a day off. My dad and mom had divorced about two years before, so I was used to being on my own. I liked it. I could play with my toys as loud as I chose and could say bad words if I wanted. I re-imagined the movie scenes with perverse different endings and after a bit I felt like exploring.
I knew, in a general manner, what sex was. I'd fought many nights to not hear my mom with a guy or even my dad on an attempt to patch things up. So, I knew my mom was having sex fairly often despite barely knowing what sex was.
My mom was a nurse in training and she was fit and good looking. She was very sexually active, and, though I had no interest in my mom, I was curious about how much of a slut she might be. So, I took a break from re-playing the police-prostitute movie plot and and quietly went through her things. I skipped her nurse scrubs and went through some dresses and then some skirts, then some miniskirts that made me both cringe and turned me on.
Finally, I found her underwear and a floodgate opened. The feel of the thin silky feminine fabrics of her bras, panties, panties, and slips turned me on. I noticed my cock rise. On a whim, I stripped down and tried on a bra. Then the matching panties. Then I checked myself out in the mirror and found her stockings mixed into her pantyhose. The prostitutes in the movie had all worn stockings and...oh look, garter belts, I thought. In minutes I was at the mirror and modeling the peaches n' cream colored bra, with black lacy trim, nude stockings, a thin black garter belt, and red panties. I loved how they felt and was excited at how my own dick popped up out of the panties. But the look wasn't quite right. I went back and put on the black panties and the black bra, straining to hook it behind my back. The look was perfect and hot. I strutted and preened, my boyish, yet now oddly girlish, over-the-ear blonde-red straight hair flinging around. After a few minutes my dick leaked some clear fluid and on a whim I tasted it. In the movie one of the prostitutes had risen from off a john's cock, mouth glistening and I had figured out that she'd had the man's dick in her mouth, so, why not taste my own fluids? It tasted like thin snot. How unimpressive, I thought. Then, on instinct, I stoked myself and realized that it felt good, better, far better than it had even the night before. I stroked and stroked and preened at myself and then mouthing some of the sex-lines from the movie. I got a pillow and put it on the bathroom floor and placed my hard cock in it and pumped for all I was worth as I preened at myself in the mirror. Then I lost control of myself, or, something beyond my control happened. My insides moved and then out popped this...this...stuff! I panicked a moment as my little penis throbbed up...held, then down, then up and held...then back down. I throbbed uncontrollably for over half a minute. I saw the "stuff" all over everything and briefly considered tasting it, but did not. Instead, I had another moment of panic. I wiped up my "stuff" and sat for a moment wondering all kinds of things about what had just happened.
It had felt weird. Good even. I cleaned up the pillow again and put all the things away. It was only 10am.
By noon I'd finished my ramen noodles and lunch meat and I was bored. I knew my neighborhood friends were out of town for the long weekend so, what to do I wondered. Before long I was watching TV and saw a soap opera and one of the women was in her underwear in a robe and that was it. Filled with desire, I got up and went back to my mom's room and put the same items back on and began playing again. Then, I remembered the old "theater" trunk and went into that to find the professional-grade curly platinum blonde wig my mom had worn for Halloween last year. I put that on and went back into the bathroom and watched myself in the mirror. I was aroused before I saw myself in the mirror, but when I saw myself in the mirror that arousal actually dropped a bit. I wasn't sexy or girlish enough.
I knew what I needed. It was only about 1:30pm. I had time. I got my mom's makeup out and, using a Cosmopolitan magazine makeup guide, I put on my first makeup. Blue shadow to compliment my blue eyes, rouge, eyeliner, and lipstick. Then I looked myself over and smiled. I hot little gurl. A whore like in the movie. My cock strained and I stroked it as I watched myself. I mouthed things, awful things, things boys should never say, and I imagined that girls should say those horrible degrading things all the time. All of a sudden, with no pillow, no humping, my cock exploded again, except this felt amazing!
That day I came four times and thought I'd actually hurt myself on the last one. I cramped my crotch but after a minute the pain ended. I cleaned up and vowed to not dress up again. After all, I wasn't a faggot, I was a nice young man.
That night I stroked myself again and brought an orgasm out once more. This time, in the darkness, I licked it off my fingers and liked the fact that I was doing it, and the taste was a bit unique too. But, I held to my vow to not dress up like a girl and not be a gay boy...for at least a month.
In the meantime, the orgasms I had late at night and not dressed as a naughty girl were ok, but I craved the other part- the naughty "gurl" part.
With my mom now a fully trained nurse she began working many late and weekend shifts.
Over the weekend in early November my mom was away for work and I dressed about half the time she was gone. I played again, and again, and again. Each time I dressed up and played it ended with me vowing it was the last time.
A few of weeks later the floodgates opened full blast. During holiday break I dressed almost daily and had three and a few times fours orgasms each day. I would also masturbate in bed late at night, but soon realized that I had the most intense orgasms when I was dressed. Over the holiday break I dressed and expanded my look into mom's shoes and dresses. I no longer preened and mouthed words, I spoke them in my best gurlie voice. I also began playing in the carpeted and far more comfortable bonus room on the side of the house. The light was good and there was a giant mirror so I could watch my own show. I found and then stole a couple of my dad's "Variations" and "Letters" magazines and read about sex as I jacked off. I would feel myself get close and then I'd hump a pillow and cum all over the pillow. The rest of the vacation from school I spent every bit of alone time either dressing and acting out or thinking about dressing and acting out as a sex object.
Next door, Mr. Carlton stood at his kitchen sink and stared down at a gentle 30 degree angle into the bonus room of the house next door as he filled a glass of water. The family next door was nice and they'd been mutually helpful with yard work and other neighborly matters. When the husband left the good looking dirty-blonde wife both he and his wife, Mrs. Carlton, had helped out. Those same nice neighbors had helped out Mrs. Carlton when she finally listened to his step daughter and step son about Mr. Carlton's "special time" with them. And then she left him, taking them with her.
Now, at his sink, during the holidays, a gift was delivered in the form of a cute little girl humping pillows in the room next door. Mr. Carlton wondered who the hell this little girl was and how had he missed her moving in. She was slender and was obviously in mom's oversized sexy things. Then the pumping changed to an orgasmic spasm. Mr Carlton's six inches of lust stiffened and he dropped his pants and stroked himself. As the girl finished Mr. Carlton was only half done. The girl stood and disappeared and after 15 minutes reappeared in a blue dress and different shoes. After a few minutes the dress came up and the girl dropped to straddle the pillow. The girl humped the pillow and then bounced up and down, then the back of the dress came all the way up and the girl sank to the floor and began a fuck-motion.
Mr. Carlton's carnal instinct knew what he was seeing, but at first didn't recognize it. Mr. Carlton rounded each stroke of his cock over his stiff cockhead as he began to piece it all together. Then, after a short few moments the figure next door arched upward in a tell-tale orgasmic thrust and then quaked and quivered for several long erotic moments. Then the body turned over, the butt sitting just to the side of the soiled bed pillow and he saw it. The girl was actually the boy next door. He recognized the face and then saw the cute little glistening cock under the garter belt, a short thirty feet away. It was all unmistakable. Mr. Carlton began to orgasm all over his sink cabinet doors. He worked himself to keep his cum flowing as the strange little girl, apparently fake, or acting out an orgasm moments before now facing him stoked herself and short her cum onto her own belly. Mr. Carlton, cock still twitching, stepped back a bit and caught his breath but still watched as the gurl or the femme-boy licked her hands and used their hand to wipe cum off her or his belly. Her's he decided. Mr. Carlton squeezed his orgasmic cock in a hard pulsing motion. Definitely a gurl, he decided. A gurl with a penis dressing up and choosing to be a sex object. What a good gurl, Mr. Carlton thought as he wiped himself off and started to harden again. He came three more times that day unable to stop peeping across the way at "her."
That night he thought, "I want her."
Five and a half months later I was about to start the first day of summer vacation. Mom was regularly leaving for work at seven and I knew her clothes and underwear very well. When I woke up I was already mentally picking though her things and imagining which whore I would be that day. I found mom's other wigs and was going with the longer of two platinum-blonde wigs, the sheer tight-topped and flowing blue dress, the black stockings and of course the matching black garter belt and the tight bra. The bra was utterly sinful and I'd noted when she wore it fer her boyfriends. It turned me on. The bra was little more than thin panties designed to cover boobs. I had my soft foam balls ready for my boobs from my secret hiding place. I knew which makeup look I was going to use and had my "Letters" page folded with some brunette porn star on it and ready as a makeup guide.
I saw mom out the door and ran back into her room as she pulled out. In thirty minutes I was dressed and on my way to the bonus room, my mom's black pumps click-clacking across the tile till I reached the bonus room's carpet. I said several well-used lines from movies of women teasing guys and then moved into my re-written and re-imagined lines for those roles. Then, as I crouched down to submit to sex and began to stroke I said the really raunchy things as I watched myself in the floor mirror and stoked my cock.
During spring break I'd dressed every day except one and had gotten much better with my makeup and my femme look. I'd developed a bit of a femme-voice and knew how to control my orgasm or "edge," before I knew it was edging. I was still having between three and four orgasms every day, but the build-up was slow and incredibly fun.
As I hit the edge of the first orgasm of the day I rolled over from the pillow and onto my back, as I'd always done. I spread my crotch wide and relaxed a full minute and slow stroked myself.
KNOCK-KNOCK-KNOCK-KNOCK-KNOCK!!! on the bonus room window shocked me and caused my heart to jump. I raced in fear to the nearby couch and hid. A familiar voice came through the window in a low, calm, almost conversational tone and volume. He was just loud enough for me to hear through the wall like you might hear a couple of people outside my mistake.
"It's ok. You are not in trouble," Mr. Carlton, the man from next door who was older than my parents said quietly through the window.
Ten minutes later he'd talked me into speaking to him through our common fence line. I went out back and there he was, almost as tall as the fence pickets and able to see me clearly through the gaps in the wood. He took his time. We had all day. After about 20 minutes he suggested I sit on the patio bench and then suggested I would be more lady-like if I crossed my legs, not laying my leg flat, but next to my lower leg like a lady. Mr. Carlton added, "Yes, gently kick the crossed leg a bit like a lady...did you know some women can orgasm doing that?"
The conversation went on for about two hours. I know this because I went in and peed and saw it was almost noon. Back outside Mr. Carlton was kind and encouraging, often saying that I was very smart and sensitive and things like "You already know this, but..." to then lead me to agree with an inappropriate statement about sex. About an hour and a half later he started leading me into how different it was to watch sex movies than look at pictures. "The sounds, the moves...oh so amazing when women cum, and guys too. You'd love it!"
Then he took the real chance. "Hey, how about you come over tomorrow and watch movies in my upstairs movie theater. I have a big TV and you won't have to worry about your mom showing up early or anything."
He'd apparently seen the five or six times my mom came home early from work. I was paranoid about that happening and he knew it. I'd nearly been caught but had recovered nicely quickly replacing her things and barely making it into the shower when she came inside each time.
He offered and I turned him down and then he started a new subject to later come back to the offer to watch porn and play in safety. Then he offered me a free set of stockings. A few minutes after that offer fell flat he offered money and even a hand-held video game. Then, thinking he'd failed, he said, "You know, I just find you fascinating. I have been watching you ever since winter break and I just want to see you up close. I don't want to touch you or hurt you. I just really find you exciting."
"No." I turned him down again.
"Ok, well, your mom may be home soon and i don't want you to get in trouble, but hey, how about, well, stand up and lick your lips for me, grab your boobs...show me your legs..."
Reluctant for a minute or so, then after him all but begging or threatening me, and then a short a private "why not?" moment, I spent the next twenty minutes posing and preening for him. I gave my first show. At first it was tame and teasing, then, emboldened by Mr. Carlton I became more risque and ultimately very sexual. Toward what was the end of the show I stroked myself for him and showed him my legs and my ass. I licked and sucked my fingers one at a time and then split them apart like they were a pussy and licked the "V".
He was stroking himself as he watched me. I couldn't see his cock, but I knew he was. After a while he directed me and I was into being directed.
"Ok, now turn around, bend over and hold yourself up on the table but pull up the dress and look at me with your sexy lips, and blow kisses...ok good, now pull the panties aside." I did and he said, "Yes, yes, yes...ok, hold it for a...haaa...uhhh minute..." Silence a moment or two then, "Yesss, good gurlll ....uhhhh ohhh!!" he moaned. He came.
Through a gap in the fence his load blasted through. I felt a rush as it happened. His load was mammoth compared to mine and it turned me on somewhere deep down. I felt so very wrong by enjoying it, but enjoyment it really was. He finished and after he invited me over one more time, I went inside and finally rubbed myself to an orgasm.
The next day he waved me over from his kitchen window. I declined, shaking my head. But, Wednesday I agreed. I went, dressed in my favorite gurlie things under my boy clothes over to Mr. Carlton's house and unknowingly began the process of being groomed. I had no idea what I had gotten myself into. He promised and delivered porn movies. He promised and delivered sexy outfits that fit me. He'd promised and delivered a safe place to play, at first.
Each day the rest of the week I watched porn movies and jacked off watching them and myself in the array of mirrors he'd placed around his dimly-lit upstairs playroom. The room was a converted loft with a working restroom and a small bedroom of to each side of the top of the stairs and on the back edge of a large rectangular open space with a love seat. The floors were hardwood then the loveseat, then the thick padded rug, then the TV stand. To the left of the TV was a red vinyl bench-bed and a double-curtained window. The TV on the stand was pretty big and had two DVD players hooked up and mirrored set of doors in front of the DVD storage shelves. On each side of the TV were tall floor lamps with dim red bulbs that created a very sexual feel to the room. There was a single strip of regular dim white lights overhead that were positioned between the TV and the love seat. The effect was to light the padded rug area and the love seat while keeping the rest of the play space dark. It worked well. There were ten or twelve mirrors of various larger sizes placed all around the room so that anyone, like me for instance, in the center of the room on or near or love seat was viewable from the stairs or the small bedroom or the bathroom or, well practically anywhere.
Mr. Carlton usually stayed back in the dark area of the bedroom doorway, discreet, but visible if I really strained.
At first, my days were fairly similar. I found myself using the bathroom to do my makeup and came out to find porn playing on the TV and then did a short turn-and-pose routine before he urged me to enjoy myself while he went downstairs "to take care of something."
Each day I usually came twice before noon and then once or twice more after lunch. Each day I came over and he played porn videos for me while in turn he watched me enjoy myself on the well-lit loveseat facing the TV and all the mirrors. He was out of sight and in the darkness. So, I gave him a show while ignoring him, and that suited me just fine.
About the third time over, the following Monday I think, I had lunch and put on a gift he left for me in the back bedroom. Then I watched another movie or maybe two, and came once or even twice more in my own black baby doll set with garters and stockings that were brand new. He even bought me shoes! I came watching myself hump pillows, preen, and make lewd gestures at myself. I watched myself almost as much as the movies. The movies changed and became more and more racy too- straight, straight groups, gang bangs, interracial, interracial gangbangs, then lesbian and bisexual girl-man-man, then transsexual movies, and finally some really nasty home made movies of gurls like me. Those movies took me up to the following Monday.
Throughout the initial grooming process I caught a few glimpses of Mr. Carlton and I knew he was watching me, but I focused on the movies and watching myself as I came. We each got what we wanted. I wanted porn, and he wanted to watch me playing with myself. He provided me with more and more cheap slutty sexy lingerie and a sexy schoolgirl Halloween costume and all the KY jelly I could ever need.
The next week started with several home-made movies of CDs and transsexuals. I came five times that Monday, the first day and left with a deep sexual cramp in my body. The second day, likewise and he noticed I liked a redhead gurl. The third day there was a red wig in the upstairs bathroom I used as a changing room and he had four movies with redhead trannies in them. Thursday he played the first movie and half and hour into it I realized he was in the room behind me and off to one side, just barely in the shadows. I looked over at him in the mirrors. He was nude except for some black cowboy boots.
Then, stroking his cock in time with me he crossed directly in front of my view of the TV screen, hard glistening daddy-cock in hand, and sat on the other side of the love seat. He slow-stroked a minute and when I did nothing like get up and run away scared, he stopped, turned to me, then back at the porn movie and released his cock. Then another minute passed with me also stopped in my stroking. The two of us watched the movie in silence. Then he moved. His arm came up and he crossed it over me as his large hand curled around my neck. As he did the red head tranny porn queen was on her knees sucking a cock, twisting her head and doing it with gusto.
Mr. Carlton said "Let's see if you've learned anything."
I knew what was about to happen like it had already occurred. I knew he was going to make me suck his cock. I knew it and my heart pumped hard and fast in anticipation of very wrong erotic action.
Over and over my mind raced through protest after protest. Each weak protest of why I shouldn't just do it was answered by "No one will will know." My crotch throbbed and my stomach turned in protest then settled, overcome by my hyper-sexual brain. I was overwhelmed in the moment and Mr. Carlton saw it. He'd known it would be like this for me and took it slow enough to not frighten me, but continued forward firmly enough to make me either let it happen or commit on my own. Just as I was about to commit to becoming a cocksucker, even if it was only once, I told myself, he took me.
I had wanted it deep down and parted my lips to sink down on him, but he was just ahead of me. Later he told me he thought I was about to back off and shy away, so he reached over to make it happen. Mr. Carlton, fit guy in his forties, tall, with about six and a half firm inches of meaty clean-cut cock pulled me over and pushed my face into his big daddy cock, smearing my lipstick over his wet cockhead.
The first time you do anything, good or bad, it is a new experience and whether or not you are any good at it may, or may not, be important to the experience. But, how much you like it is. Hitting a baseball, making a basketball shot, shooting a gun, even fighting the first time all leave an indelible impact on you. I liked sucking cock from the moment he made me.
The lust of the moment and the wanton desire combined with the twisted aspects of it being lees-than consensual sodomy all were a powerful aphrodisiac. I liked it the first time it went in, but, still wedded to societal pressures, I was embarassed and hated how much I liked it. But I did it.
His cock went in as I was pushed downward. He reached the back of my throat and he said, "That's a good gurl, now close your lips and suck on the upward stroke." Then he firmly and almost gently guided me up, then down, up, then down...nice and smooth...calm, collected.
From the very first push of my face down onto his cock he coached me. I moaned involuntarily and possibly in protest at first and then I realized how hard I was, I'd forgotten to let go of my own cock, and I stoked.
At first my senses rushed to feel every little nasty sensation and movement. His skin over my lips, his little hairs against my nose, the dank sweaty smell of his crotch, the smooth saliva and pre-emmission from his shaft, the hardness, the way the head plugged my throat and halted my breathing. All of it. Then I realized something. I hated that I loved it so much. My identity was altered by his cock and my own willingness to not just submit, but to willingly accept him in me. As I was going up and down on him, so I told myself "I like it...but so what." With each head bob I leaped through entire debates in my mind. Self recrimination led to personal name calling then the cock would hit my throat and I'd reset to "Mmmmm that feels amazing..." Then I mentally went through the same faggot or straight boy debate. "What are you doing? You are ruining yourself? You are degrading yourself!! You are a good young man, a good boy!...Oh wait, cock! Absolute lust and raw sex...hard cock choking me a little...Amazing! MMMMM!!! I kind of a whore! I am kinda a slut!! Hottttt!!!" Over and over the same debate took place in split seconds as I sucked him off, then at some point it all dropped away and I just stayed in the moment. I liked being a whore, or probably more accurately, I like playing like I was a whore, just like I had done since the very first orgasm. Now it was real.
As all that flashed through my little cocksucking head Mr. Carlton noticed I was physically situated poorly. I was sitting on my right ass cheek and leaning to my side, sucking him off sideways. He felt my teeth sc**** him and pulled me up to the top of his cock.
He said firmly, "No fucking teeth! Now slide off the couch and get between my legs like a good gurl. Be the gurls in the movies, and suck my cock!"
I complied and slid into place and worshiped his daddy-cock. Enthusiasm was high, but my skills were poor. I went down and up and followed his directions. Then after probably ten minutes and at the end of the sex scene in the tranny movie he pulled himself free and stoked himself to completion. He held my lips at the top of his cock and stoked, his fist bumping my lips each time and actually giving me a fat lip later. Just before he came he breathed in and out rapidly and moaned a bit. It excited me beyond imagination. I knew he was going to cum. It made me even hotter.
Between hard deep breaths Mr. Carlton said, "Fuck yes you are so fucking hot, I am gonna make you perfect...stroke yourself and open your mouth little whore!"
I stroked myself and opened as he pushed to my lips and shot his semen into my tight small mouth. As his orgasm shot and then so did mine. I felt and tasted him and loved it.
In a minute we were done and I was in a mild shock, silent and orgasmic, but also in a post physical violation shock. Later, when I confessed all this to a different psychoanalyst - who was balls-deep fucking me from behind at the moment I described my fist blow job to him, this exact story - he said, "Yeah, sure, that was probably mild shock. You were overwhelmed and violated."
With Mr. Carlton's semen coating my mouth, afraid to swallow, 'cause, well you know, I wasn't a faggot, I went from kneeling on the carpet to slumping onto the padded rug, kicking my high-heels forward and looking like a little girl not sure what to do next. Legs outstretched in a wide "V" and breathing hard myself, and of course still coated in my own cum and some lube. I looked at the Mr. Carlton's cock and leaned back and away a little, arms propping me up and legs extended even wider. I let myself smile, closed mouth, cum still in my cocksucking mouth.
I looked down and saw my cock was still hard and slimy. His was too. He smiled at me kindly. He searched my expression to determine if he had a problem now or the most wonderful thing in the world.
I knew what he'd done. How he'd manipulated the whole process. I went through the same toxic debate in my little overworked mind and set it aside and consciously decided to accept and enjoy the moment. I made my first life decision and smiled up at him.
2 years ago
