CD Rebeca Young Tranny pt3 Gurlie Growth Pains
Young Tranny
3. How I Started part 3- Gurlie Growth Pains
Seconds after my first fuck Mr. Carlton released my hips and pulled out of my asshole. As he did his cock drew out some of his cum. It slid off his shaft and onto my upper inner thigh and onto the floor. I learned to call this wonderful feeling a cream pie. I could see all of this well in one of the mirrors that was angled upward and gave a full view of his mature cock and my smaller cock and balls. My cock was still dripping. His cum flowed slick and clear down both of my upper thighs and then down to the tops of my stockings where it disappeared into the sheer and shiny fabric.
Mr. Carlton, now backed up and away from me, said nothing at first. He was still orgasmic and stroked himself a bit and then, after looking me over and searching into my eyes for a hint of my state of being, he stepped back and fell onto the love seat with a thin satisfied smile.
I was stunned and probably in shock. I focused and stood as strong as I could, backing away from the short bench a little. I willed myself to not show myself to be a weakling. He seemed to be satisfied by his conquest of me and I resolved to not give him any more satisfaction.
Looking back, I am convinced he was definitely satisfied on some level with his conquest, but he was more likely basking in his favorite post-coital glow - after a tight young virgin gurlie-boi ass.
I turned toward him, expressionless and quiet, feeling humiliated in my gurl's clothes and awkward in my high heels. A drip of sweat trickled down my temple. I looked down and saw my shiny wet cock, still somewhat hard and waving right and left. I caught my breath and waited for him to say something. I was a surrendered person. I was taken...powerless and submissive. A flash of self-recrimination shot through me- "Stupid! What did you expect?!!"
Instead, stood there, a freshly fucked gurlie-boi, and put it aside. I calmly stood awaiting instructions like beaten prisoner.
Mr. Carlton, an older fit man whom I'd know pretty much my entire life as my nice next door neighbor was now also the man who'd just patiently made me his sex toy. He smiled at me more fully and gently said, "Take some time." Then he paused and with his brow furled in a a thoughtful manner he added in an equally thoughtful tone, "This is a big step for you."
He looked away then then back at me considering me a moment and then continued, his tone changed and more commanding and firm. "But, you need to know, you can't leave. I have the doors locked and your clothes are downstairs and locked away. A lot has just happened to you, so we will take it slow now. You take some time in the bathroom and compose yourself. Don't say anything right now. In fact, don't say anything, nothing at all. Not for a while. Not till I tell you its ok. Don't say anything you haven't thought through about five of six times. Nobody knows what just happened and if you think about it you know parts of you really, really liked it. Be honest with yourself, but do not react yet, at least not by saying anything."
He paused again and smiled, and now in a lighter almost playful tone he went on saying, "Just...embrace your feelings and...and, ahhhh, enjoy the moment. Everything is ok. I think that you will know you liked it in a few minutes..."
He closed his eyes and relaxed, ending the moment and silently sending me on my way with the wave of a hand. Then he added, firmly again, "And fix your makeup young lady."
Still stunned, I paused and then a moment later, when it was clear I was at least temporarily dismissed. I stepped away from the bench in my high heels and slowly made my way toward the small bathroom at the top of the stairs. I noticed like never before how the five inch high-heels perked my ass upward by design. I strutted away, despite not being in a perky or strutting mood.
I stepped into to the full bathroom and peered across to the dresser in "my bedroom" and saw that the bottom drawer was in fact open and empty. He'd taken my clothes. Even if I wanted, I wasn't going to escape easily. Skipping a typical look at myself in the mirror I reached out and shut the door, not slamming it in a melancholy manner that matched my defeated attitude. I stepped to the toilet, my heels click-clacking on the floor and sat on the throne and answered a compelling need to go to the toilet.
I sat and did my business on the toilet, but at first nothing came out. Then I relaxed and a wet fart and a liquid blast shot into the bowl. I took a minute or two for more to happen and then I realized that I didn't really need to go, I just had a weird feeling reminiscent of needing to use the toilet, but it was very different. Like an ache, but also like relief, but at the same time, and yet also like a void that needed filling.
I looked at my cock, saw it was half-hard and touched the head. I was still horny, well my cock was. It wanted to cum. Well sort of. I took my hand away and noted how slick and wet it was. I had cum...and I wanted it again. I'd seen a lot of cum flow from me as he fucked me, but my cock was still horny. Then, my mind emerged beyond the melancholy haze of my post-sex shock. I realized that my mind was also horny. Very horny. The haze lifted nearly completely and I composed myself on the toilet and realized I was done and stood. Now, well composed and sexually excited again, I was surprisingly comfortable in my high heels. I considered briefly how I was far too comfortable in these naughty pumps. Then out of curiosity I looked into the bowl and saw that my fart had only popped free Mr. Calrton's cum load. It was a pale pinkish color that looked like someone who had blown their nose after it was long healed. The cum was not "bloody" it was just pink and thick. My mind delved into a weird detached curiosity instead of revulsion and a my inner voice said, "Huh, that's not too bad at all."
That revelation provoked me to take a personal inventory. Was I hurt on the inside in a very real way? No, I was not. As part of that check I clenched my asshole and felt a dull ache and...something else. An answering and unexpected orgasmic throb passed through me, so I was definitely not on the hurt list. But something was off...or maybe...different. Yes, that was different. Not off, strange and unfamiliar, different; a better or more accurate status. Instead of hurt, I was embarrassed and also excited me in a very wrong way and in a far more different and intense manner than ever before.
Continuing my personal check for damage, I squatted half way down and reached under my cock and balls and stuck a finger up my still-open asshole and found that I had little puckered ass-lips. I later learned to call this ass-cunt-like condition "gaped." I found that I was sensitive, but again, I was not in pain and not really bleeding. There was a huge amount of cum inside me. Perhaps only half had flopped out of me into the toilet. Far more of his semen covered my small fingers. Over and over I searched for damage and found none. I eased my fingers in and out, shallow at first and then deeper, never finding any real blood or pain. This eased my anxiety, but only a bit. I thought that I should hurt, even now, my fingers probing me felt good. I should be grossed out, but I wasn't. When I stood, I looked again and saw the large cum load in the toilet bowl, as if it had been shot there, but it had cum out of me when I farted. A part of me felt an odd accomplishment.
Then another part of me masquerading as "normal and sane" stepped in to halt my fleeting comfort with my new reality as a fucked gurlie-boi. The "normal" part told me I shouldn't feel what happened was an accomplishment, or pleasure...or fucking alright in any way! "What's wrong with you? You're not supposed to like that! You were violated! What the fuck is wrong with you?"
Self recrimination flowed over me and I looked myself in the eyes and felt only a small tinge of mild embarrassment when I should have felt extremely degraded and embarrassed. I didn't feel that way, not really. It wasn't bad or good. I wasn't gay-faggy-boy or straight. The sex was was physical and mental...and emotional. It was stunning and shameful, delicious and awful. Wait, no, was it awful?
As the recriminations flowed I looked at myself in the mirror out of habit and it fell away. I was the same sexy gurl Mr. Carlton had seen also. Red hair, black teddy, stockings, too much makeup, messed up mascara. I smiled a little, my first since he'd done what he'd done to me.
Then, the very last of the self recrimination flowed away and I felt a little proud. I felt I'd earned a moment of satisfaction.
Then, out of habit and completely in line with the grooming process, I did what I was used to at the mirror. Just like the four or five times I did every day I played there, I looked myself over in detail and surveyed the improvement s I needed to make.
I looked pretty good. My lips were intact and my my eyes were only a little bit of a mess from tears and sweating. Otherwise I was still made up like the whore I'd dressed to emulate just over an hour ago.
I should have been shaken and destroyed, but instead, my loins flexed and my still sort-of hungry cock twitched the same way it always did when I saw the hot gurl in the mirror. I looked myself over and hovered between anger at myself for not being upset and angry at Mr. Carlton and a deeper desire to be proud and feel an accomplishment and a realization that something I hadn't fully acknowledged I wanted had finally happened. I looked myself over and confirmed that I really wasn't messed up physically or superficially. My makeup needed a touch up, but otherwise I was fine.
I took care of the smeared raccoon-eyes with a tissue and some light eye shadow and then repaired my mascara and eye liner. I darkened my shadow out of habit using what I'd learned from Cosmo. In minutes I was repaired and enjoying myself in the mirror. I added more lipstick, my favorite part of makeup application, relishing the smooth spread of the creamy, oily, dark red. That was when I noticed I was excited and my sexual body was betraying my logical mind. My cock pulsed as I moved the lipstick over my tender young lips.
As I began a mental debate in my inner monologue about what my problem was, I bent forward to the mirror adding another coat of lipstick and tried to not have a raging hard cock. I was still fighting on the inside when I heard and felt the floor shift and then heard a pair of knocking raps on the door.
A second later, despite me not answering, the door opened and Mr. Carlton, just below six feet tall and fit, despite his medical problems, stood there deeply analyzing me. Still nude, except for some shiny black cowboy boots, his mature cock was semi hard and close to my left hip, he smiled after a few seconds and pronounced, "Excellent! You are ok. Very good. You make me very happy. Take as long as you need to clean up. Put your makeup back on and dress how ever you want and come back out to the room."
After he left I took another minute and then left the bathroom and went to the bedroom on the opposite side of the top of the stairs. It was called the gurlie-room. I went inside and changed from the simple lingerie to a tight school-girl look, the most complicated and least accessible outfit available. I dawned a tight white top, short plaid skirt, bobby-socks, and swapped out my pumps for the more appropriate Mary-jane shoes. Then, the negative inner voice returned to cursed myself at how stupid the choice was. You idiot, that outfit sends exactly the wrong message to Mr. Carlton, the violator, the liar, and... I self-recriminated and cursed myself deeply as I noticed how my cock was semi-hard but completely on sexual fire.
I undercut the negative feelings and inner voice. I looked at myself in one of the many mirrors in the bedroom and acknowledged how this , my first actual choice ever for my outfit betrayed my logical self and showed my true emotional and subconscious colors. Of all the choices, I selected a school gurl look to present myself with post virginity. Perhaps, nothing was wrong with me at all, and my subconscious was taking over. I might be completely ok.
But I shouldn't be!
Thirty minutes after going into the bathroom and I was back out in the play room and Mr. Carlton. He had just started playing a home made movie. The movie began showing a sunny stretch of beach line at sunset through a hotel window and then panned back toward the room door and I heard Mr. Carlton's voice as he cleared his voice. It dawned on me that the movie starred Mr. Carlton, and was probably going to be a bit...shocking.
The picture panned from the coastline into the hotel suite. In the doorway, stuffing a some cash into a thin black clutch purse was a cute petite possibly adult, possibly younger, transsexual. Her voice gave her away. Her lovely shade of Mexican tan was warm and sexually overwhelming. She had gorgeous almond eyes framed by bleach-blonde hair. She was naturally cute but also wore striking makeup, a fluffy halter top with red bra straps over her shoulder as a fashion flirt, a flowing black cotton miniskirt with warm brown bare legs, and black strappy sandal high-heels. She was cute and looked like what I now understand to be a cheap young street gurl, a young gurlie-boi hooker. The movie was obviously several years old based on Mr. Carlton's younger toned body and richer hair color. In the movie Mr. Carlton asked the gurl to model for him using perfect Spanish. She was giddy and seemed to be having the time of her life. She removed her clothing in a well-practiced playful strip-tease manner. Eventually she worked her top off, showing a cheap cupped bra and a nearly flat chest underneath. The camera moved in closer to reveal the slightest signs of little pointy boi-titties just beginning to grow. Smaller than "a" cups, not much more than swollen nipples, but still, they were tits starting to grow. Mr. Carlton's hands went in front of the camera and tweaked the nipples and caressed the gurlie-boy's warm slightly pointed chest as she moaned in an adolescent gurlie-boi voice. The camera backed away and the gurl went to remove the bra, but Mr. Carlton told her to stop and she smiled and licked her lips with a naughty smile. The camera backed away and a hand gestured for the gurl to continue her striptease.
The gurlie-boi turned away and strutted to the edge of the bed and, still facing away leaned over the hotel bed to give Mr. Carlton her under-skirt view with her red dental-floss-like panties bunched in her ass crack and her little balls drooping outside the panties. She shifted a bit, humping the bed like a male dog on a bitch, and moaned in her voice. The voice was sexy in its own way, but the tone was a flat dry tenor. To me the voice clashed with her otherwise impeccable look. After a few humping motions her already slimy uncut little semi-limp uncut cock fell out of her little panties and popped into view. Her cock was maybe a four or five inches and was shiny and flopped around in all directions.
I had a momentary flash of shock because of her openness and genuine eagerness. She was sexier in a genuine way than any of the porn stars I'd been seeing over the past weeks. I was in awe, but also in a strange way I was reassured that I was not unique in my enthusiasm to be a slutty gurl.
He zoomed in on her cock. It was small and pointed with the foreskin covering the entire cockhead and creating the appearance of a thin funnel made of tight tan skin. The camera followed for almost a minute until the gurl shifted and turned. She pumped back and forth upward and into the air as the camera zoomed out to see her ass-bumping the bed corner like it was a lap-dance. She smiled and abruptly stopped and then lifted her miniskirt over her hips and said in her flat semi-femme tenor, "Jue wohnt to fock me Papi?" She was a dream-cum-true in so many ways. This private porn turned me on, despite the obvious inappropriate aspects.
In the movie and from behind the camera Mr. Carlton said, "You know I do Esmeralda. You know I love that tight little cunt of yours."
In a deep accent, Esmeralda considered a moment and then, her translation complete, she said with a leud smile, "Umm I...lohve jor beeg...umm," Searching for the word she muttered, "Penga, no..." then in a triumphant voice with a huge smile she exclaimed "COCK!"
I smiled at her triumph and thought that she obviously loved what she was doing and was probably worth far more then the twenty or so dollars Mr. Carlton had paid her.
Mr. Carlton chucked a bit and then panned downward to show his ample and totally hard cut daddy-cock.
The movie continued back on her and Mr. Carlton stepping to her. He said something obviously leud in Spanish that I didn't understand and, in a single practiced movement, she wantonly fell to her knees, took his cock in her mouth and eagerly sucked him deeply and enthusiastically. After a few minutes he said something else and, in a likewise practiced and singular movement, the gurl stood, turned and stepped to the window overlooking the beach, bent forward, planted her hands on the large sliding window-door and looked over her shoulder with a gleeful smile.
The camera panned down and showed his shiny raw naked six-inch-or-so cock entering her sex hole. Off screen, she moaned in pained tones that begged him into her. On screen her hips gyrated to let him into her deep and fully. His cock pushed in to the hilt and for a moment everything stopped.
The Gurl's ass froze a moment and off screen her voice went "Ohhhhhhhhh....Ayeeee Pappi...Si..."
Mr. Carlton panned back and now the shot showed her ass with his cock in it, her bra-covered back, her bleach-blonde hair dr****g off her shoulders and the bright mid-day beach. He said to the back of her head, "Now that is a tight pussy."
The gurl smiled over her shoulder as she arched her hips upward beckoning him to fuck her.
Mr. Carlton reached out in a firm manner and set the camera on the bed in a practiced motion and distance that caught the whole fuck scene up to his neck and down to her rich warm thighs. The moans were traded as the fucking began. Now she made moans with utterances of incoherent Spanish phrases. The sounds were deeply sexual and wanton. She was incredible. The gurl was bucking into Mr. Carlton and occasionally reaching under to stroke herself in time with his fuck-thrusts. After only a minute her cock grew and emerged from her foreskin. She stoked herself for more than the few strokes she'd been doing for the first few minutes of the fuck scene and went over the edge. She moaned differently and it was obvious she'd gotten too close to cumming and let go of herself too late. Her head and the fine blonde hair shot back and her hands braced her body at the window as she went into ecstasy.
Mr. Carlton knew her well and knew what was happening. He reached under and grabbed her cock took her over the edge and jacked her orgasm free. She seemed to protest a moment, but then surrendered in the next moment. She moaned deep and loud as she came, first in drops, then a two heavy spurts onto the window. Then he let go, making the orgasm hands-free from that point on. Shot after shot blasted in time with his daddy-cock pumps into her petite body.
In my head I recalled that in some of Mr. Carlton's porn I'd seen, probably the home made dominatrix porn, somebody had called this a ruined orgasm, but it was definitely not ruined in any way for her.
My mind paused away from the movie briefly and I felt a sharp wave of embarrassment that, after being fucked and cumming similarly hands free, I personally knew that it was far from a ruined orgasm.
In the movie Mr. Carlton fucked her and urged her on in English, saying, "Yessss, that's a good gurl...cum...cum you little bitch...fuck yes...cum baby." The tranny's cock, flopping up and down, spewing lines of rich semen all over the place. The gurl came hard and moaned over and over.
She paused, on the plateau of ecstasy and catching her breath.
Mr. Carlton denied any reprieve and pushed the skirt up and out of the way in a sharp motion. He gripped her small ass firmly and fucked her hard, deep, and fast. After a minute, she came again, drooling more cum all over the window. Then there was a period of slow smooth fucking that lasted two or three minutes and, again, he grabbed her cock and jacked her into a second orgasm. Her cock was totally limp, but flopped around on all directions throwing cum all over the place.
I was shocked and had to mentally rewind to fully grasp that she'd cum and was cumming again. NONE of the porn movies had shown that.
Could this be me? A dark part deeply hidden inside me woke to ask.
Then, Mr. Carlton leaned into the gurlie-boy's body, curving around it like a hand cupping a softball. He grimaced, no longer trying to hold off his own orgasm, and fucked hard and upward into her. Esmeralda's face showed that she was obviously past the pleasure of the moment and enduring him using her body over the next minute or so. Mr. Carlton, eyes shut in the movie. He was oblivious to Esmeralda and uncaring. He was used her and it was hot. The gurl was his sex doll, just as I'd been. He began some really hard, deep, almost brutal fucking, breathing in and out hard. He was about to cum and he slowed his pace to a controlled rhythmic pumping, like an oil rig. In, out, in, out.
Then, apparently now caught up with the moment and her lover's motions, Esmeralda smiled a wicked smile into the camera and stroked herself as she pumped back into him, shifting form an enduring whore to a wanton slut. She stroked herself smoothly and looked very much into the moment.
Then Mr. Carlton lurched forward powerfully and started to cum. As he came he uttered in a high voice stressed by intense physical activity, "Fuck...yes!...I love little fresh bitches like you...ahhh!" Then he came in her for a while as he pumped her deep sharply over and over for almost a minute. He pulled out. His large meaty daddy cock was glistening and still hard, but flopping around as he stood up. He pulled her back to him, kissed her deeply and then grabbed her bleach blonde hair, that now seemed sleazy in some way, and he pushed her down and made her suck his cock fresh from her ass. She moaned in her deep adolescent and mismatched voice and as she pulled away form his cock and looked up Mr. Carlton's voice said, "Bueno Puta," and his hand appeared in front of the lens and then the movie abruptly stopped.
I was back in Mr. Carlton's upstairs playroom, still standing half way between the stairs and the love seat, captivated and instantly embarrassed at how horny the scene made me.
Mr. Carlton looked at me in one of the ten or fifteen mirrors placed around the room and motioned me to sit on the low couch bed in front of the love seat.
At that point we talked. For like an hour and a half we talked and talked. To this day I do not remember much of the conversation, but I do remember at the end of our long conversation he asked me and then essentially made me suck his cock while I stroked mine and came really hard. Then he made me keep sucking him off until he came.
We talked some more and then he made me do the same thing again. Then, the third time we traded positions and he sucked me and as I approached orgasm I felt him stuff his slick lubed finger up my ass and stroke my prostate. I remember that orgasm to this day. I came more intense than I had ever come before.
Only after he'd violated my ass and made me cum like that did he let me go. I was amazed and ashamed and he knew it.
At that point, my self-loathing dissipating, and my willingness to continue playing on the rise, he sent me home.
I left much earlier than usual, around 1pm. As I undressed and became a boy again I vowed as I left to never go back to his house.
As I left he made me promise I would keep what we'd done a secret. Mr. Carlton explained that letting anyone know would be bad for everyone, but mostly me. He probably wasn't entirely right, but what did I know?
I went home and put the entire event of my first fuck and being dressed like a gurl out of my mind. For a while.
Then, around 11pm that same night I knew that I wanted to go see him the next day.
I did try to see him, but he was gone all day.
The next day, Wednesday, hump day, I saw him through the same windows he's spied on me from and he waved at me to come over. I debated with myself a few minutes and then decided to go back over. I knew what he had in mind and I knew that I consciously didn't want it, but deep in my sex I also knew I did.
I arrived about an hour later than our usual play date start times and I had severe reservations, but an insatiable drive for more.
I knew what was going to happen if I delivered myself to him as I walked up the stairs. I put aside questions about sexuality and embraced the rutting desire to experience not only the physical sexual penetration and unique stretching sexual pain-ecstasy but also the surrender and submission to his violation. I was hard and my sexual areas pulsed. Though I was far from OK with it, I put aside my negative thoughts and embraced my lust and desire. I let my need for sex to make sense go. I could figure out my sexuality some other time. In the mean time, I wanted to be his little whore. I went into "my bedroom" and put my things on.
That day I got fucked for my second, third, and forth times and I was his.
Every day the rest of the week, seconds after my mom pulled away from our driveway I was at Mr. Carlton's kitchen door and then upstairs.
The following Monday I went upstairs to find a brand new high-quality Auburn wig with deep red and a few black and reddish highlights over a new sleek black garter belt, new black stockings, a matching shiny black bra, matching sleek shiny panties.
A note placed with care next to them that said, for you, Rebeca.
The misspelled name not withstanding, I soared and almost tore the stockings as I hurried to get them on.
3. How I Started part 3- Gurlie Growth Pains
Seconds after my first fuck Mr. Carlton released my hips and pulled out of my asshole. As he did his cock drew out some of his cum. It slid off his shaft and onto my upper inner thigh and onto the floor. I learned to call this wonderful feeling a cream pie. I could see all of this well in one of the mirrors that was angled upward and gave a full view of his mature cock and my smaller cock and balls. My cock was still dripping. His cum flowed slick and clear down both of my upper thighs and then down to the tops of my stockings where it disappeared into the sheer and shiny fabric.
Mr. Carlton, now backed up and away from me, said nothing at first. He was still orgasmic and stroked himself a bit and then, after looking me over and searching into my eyes for a hint of my state of being, he stepped back and fell onto the love seat with a thin satisfied smile.
I was stunned and probably in shock. I focused and stood as strong as I could, backing away from the short bench a little. I willed myself to not show myself to be a weakling. He seemed to be satisfied by his conquest of me and I resolved to not give him any more satisfaction.
Looking back, I am convinced he was definitely satisfied on some level with his conquest, but he was more likely basking in his favorite post-coital glow - after a tight young virgin gurlie-boi ass.
I turned toward him, expressionless and quiet, feeling humiliated in my gurl's clothes and awkward in my high heels. A drip of sweat trickled down my temple. I looked down and saw my shiny wet cock, still somewhat hard and waving right and left. I caught my breath and waited for him to say something. I was a surrendered person. I was taken...powerless and submissive. A flash of self-recrimination shot through me- "Stupid! What did you expect?!!"
Instead, stood there, a freshly fucked gurlie-boi, and put it aside. I calmly stood awaiting instructions like beaten prisoner.
Mr. Carlton, an older fit man whom I'd know pretty much my entire life as my nice next door neighbor was now also the man who'd just patiently made me his sex toy. He smiled at me more fully and gently said, "Take some time." Then he paused and with his brow furled in a a thoughtful manner he added in an equally thoughtful tone, "This is a big step for you."
He looked away then then back at me considering me a moment and then continued, his tone changed and more commanding and firm. "But, you need to know, you can't leave. I have the doors locked and your clothes are downstairs and locked away. A lot has just happened to you, so we will take it slow now. You take some time in the bathroom and compose yourself. Don't say anything right now. In fact, don't say anything, nothing at all. Not for a while. Not till I tell you its ok. Don't say anything you haven't thought through about five of six times. Nobody knows what just happened and if you think about it you know parts of you really, really liked it. Be honest with yourself, but do not react yet, at least not by saying anything."
He paused again and smiled, and now in a lighter almost playful tone he went on saying, "Just...embrace your feelings and...and, ahhhh, enjoy the moment. Everything is ok. I think that you will know you liked it in a few minutes..."
He closed his eyes and relaxed, ending the moment and silently sending me on my way with the wave of a hand. Then he added, firmly again, "And fix your makeup young lady."
Still stunned, I paused and then a moment later, when it was clear I was at least temporarily dismissed. I stepped away from the bench in my high heels and slowly made my way toward the small bathroom at the top of the stairs. I noticed like never before how the five inch high-heels perked my ass upward by design. I strutted away, despite not being in a perky or strutting mood.
I stepped into to the full bathroom and peered across to the dresser in "my bedroom" and saw that the bottom drawer was in fact open and empty. He'd taken my clothes. Even if I wanted, I wasn't going to escape easily. Skipping a typical look at myself in the mirror I reached out and shut the door, not slamming it in a melancholy manner that matched my defeated attitude. I stepped to the toilet, my heels click-clacking on the floor and sat on the throne and answered a compelling need to go to the toilet.
I sat and did my business on the toilet, but at first nothing came out. Then I relaxed and a wet fart and a liquid blast shot into the bowl. I took a minute or two for more to happen and then I realized that I didn't really need to go, I just had a weird feeling reminiscent of needing to use the toilet, but it was very different. Like an ache, but also like relief, but at the same time, and yet also like a void that needed filling.
I looked at my cock, saw it was half-hard and touched the head. I was still horny, well my cock was. It wanted to cum. Well sort of. I took my hand away and noted how slick and wet it was. I had cum...and I wanted it again. I'd seen a lot of cum flow from me as he fucked me, but my cock was still horny. Then, my mind emerged beyond the melancholy haze of my post-sex shock. I realized that my mind was also horny. Very horny. The haze lifted nearly completely and I composed myself on the toilet and realized I was done and stood. Now, well composed and sexually excited again, I was surprisingly comfortable in my high heels. I considered briefly how I was far too comfortable in these naughty pumps. Then out of curiosity I looked into the bowl and saw that my fart had only popped free Mr. Calrton's cum load. It was a pale pinkish color that looked like someone who had blown their nose after it was long healed. The cum was not "bloody" it was just pink and thick. My mind delved into a weird detached curiosity instead of revulsion and a my inner voice said, "Huh, that's not too bad at all."
That revelation provoked me to take a personal inventory. Was I hurt on the inside in a very real way? No, I was not. As part of that check I clenched my asshole and felt a dull ache and...something else. An answering and unexpected orgasmic throb passed through me, so I was definitely not on the hurt list. But something was off...or maybe...different. Yes, that was different. Not off, strange and unfamiliar, different; a better or more accurate status. Instead of hurt, I was embarrassed and also excited me in a very wrong way and in a far more different and intense manner than ever before.
Continuing my personal check for damage, I squatted half way down and reached under my cock and balls and stuck a finger up my still-open asshole and found that I had little puckered ass-lips. I later learned to call this ass-cunt-like condition "gaped." I found that I was sensitive, but again, I was not in pain and not really bleeding. There was a huge amount of cum inside me. Perhaps only half had flopped out of me into the toilet. Far more of his semen covered my small fingers. Over and over I searched for damage and found none. I eased my fingers in and out, shallow at first and then deeper, never finding any real blood or pain. This eased my anxiety, but only a bit. I thought that I should hurt, even now, my fingers probing me felt good. I should be grossed out, but I wasn't. When I stood, I looked again and saw the large cum load in the toilet bowl, as if it had been shot there, but it had cum out of me when I farted. A part of me felt an odd accomplishment.
Then another part of me masquerading as "normal and sane" stepped in to halt my fleeting comfort with my new reality as a fucked gurlie-boi. The "normal" part told me I shouldn't feel what happened was an accomplishment, or pleasure...or fucking alright in any way! "What's wrong with you? You're not supposed to like that! You were violated! What the fuck is wrong with you?"
Self recrimination flowed over me and I looked myself in the eyes and felt only a small tinge of mild embarrassment when I should have felt extremely degraded and embarrassed. I didn't feel that way, not really. It wasn't bad or good. I wasn't gay-faggy-boy or straight. The sex was was physical and mental...and emotional. It was stunning and shameful, delicious and awful. Wait, no, was it awful?
As the recriminations flowed I looked at myself in the mirror out of habit and it fell away. I was the same sexy gurl Mr. Carlton had seen also. Red hair, black teddy, stockings, too much makeup, messed up mascara. I smiled a little, my first since he'd done what he'd done to me.
Then, the very last of the self recrimination flowed away and I felt a little proud. I felt I'd earned a moment of satisfaction.
Then, out of habit and completely in line with the grooming process, I did what I was used to at the mirror. Just like the four or five times I did every day I played there, I looked myself over in detail and surveyed the improvement s I needed to make.
I looked pretty good. My lips were intact and my my eyes were only a little bit of a mess from tears and sweating. Otherwise I was still made up like the whore I'd dressed to emulate just over an hour ago.
I should have been shaken and destroyed, but instead, my loins flexed and my still sort-of hungry cock twitched the same way it always did when I saw the hot gurl in the mirror. I looked myself over and hovered between anger at myself for not being upset and angry at Mr. Carlton and a deeper desire to be proud and feel an accomplishment and a realization that something I hadn't fully acknowledged I wanted had finally happened. I looked myself over and confirmed that I really wasn't messed up physically or superficially. My makeup needed a touch up, but otherwise I was fine.
I took care of the smeared raccoon-eyes with a tissue and some light eye shadow and then repaired my mascara and eye liner. I darkened my shadow out of habit using what I'd learned from Cosmo. In minutes I was repaired and enjoying myself in the mirror. I added more lipstick, my favorite part of makeup application, relishing the smooth spread of the creamy, oily, dark red. That was when I noticed I was excited and my sexual body was betraying my logical mind. My cock pulsed as I moved the lipstick over my tender young lips.
As I began a mental debate in my inner monologue about what my problem was, I bent forward to the mirror adding another coat of lipstick and tried to not have a raging hard cock. I was still fighting on the inside when I heard and felt the floor shift and then heard a pair of knocking raps on the door.
A second later, despite me not answering, the door opened and Mr. Carlton, just below six feet tall and fit, despite his medical problems, stood there deeply analyzing me. Still nude, except for some shiny black cowboy boots, his mature cock was semi hard and close to my left hip, he smiled after a few seconds and pronounced, "Excellent! You are ok. Very good. You make me very happy. Take as long as you need to clean up. Put your makeup back on and dress how ever you want and come back out to the room."
After he left I took another minute and then left the bathroom and went to the bedroom on the opposite side of the top of the stairs. It was called the gurlie-room. I went inside and changed from the simple lingerie to a tight school-girl look, the most complicated and least accessible outfit available. I dawned a tight white top, short plaid skirt, bobby-socks, and swapped out my pumps for the more appropriate Mary-jane shoes. Then, the negative inner voice returned to cursed myself at how stupid the choice was. You idiot, that outfit sends exactly the wrong message to Mr. Carlton, the violator, the liar, and... I self-recriminated and cursed myself deeply as I noticed how my cock was semi-hard but completely on sexual fire.
I undercut the negative feelings and inner voice. I looked at myself in one of the many mirrors in the bedroom and acknowledged how this , my first actual choice ever for my outfit betrayed my logical self and showed my true emotional and subconscious colors. Of all the choices, I selected a school gurl look to present myself with post virginity. Perhaps, nothing was wrong with me at all, and my subconscious was taking over. I might be completely ok.
But I shouldn't be!
Thirty minutes after going into the bathroom and I was back out in the play room and Mr. Carlton. He had just started playing a home made movie. The movie began showing a sunny stretch of beach line at sunset through a hotel window and then panned back toward the room door and I heard Mr. Carlton's voice as he cleared his voice. It dawned on me that the movie starred Mr. Carlton, and was probably going to be a bit...shocking.
The picture panned from the coastline into the hotel suite. In the doorway, stuffing a some cash into a thin black clutch purse was a cute petite possibly adult, possibly younger, transsexual. Her voice gave her away. Her lovely shade of Mexican tan was warm and sexually overwhelming. She had gorgeous almond eyes framed by bleach-blonde hair. She was naturally cute but also wore striking makeup, a fluffy halter top with red bra straps over her shoulder as a fashion flirt, a flowing black cotton miniskirt with warm brown bare legs, and black strappy sandal high-heels. She was cute and looked like what I now understand to be a cheap young street gurl, a young gurlie-boi hooker. The movie was obviously several years old based on Mr. Carlton's younger toned body and richer hair color. In the movie Mr. Carlton asked the gurl to model for him using perfect Spanish. She was giddy and seemed to be having the time of her life. She removed her clothing in a well-practiced playful strip-tease manner. Eventually she worked her top off, showing a cheap cupped bra and a nearly flat chest underneath. The camera moved in closer to reveal the slightest signs of little pointy boi-titties just beginning to grow. Smaller than "a" cups, not much more than swollen nipples, but still, they were tits starting to grow. Mr. Carlton's hands went in front of the camera and tweaked the nipples and caressed the gurlie-boy's warm slightly pointed chest as she moaned in an adolescent gurlie-boi voice. The camera backed away and the gurl went to remove the bra, but Mr. Carlton told her to stop and she smiled and licked her lips with a naughty smile. The camera backed away and a hand gestured for the gurl to continue her striptease.
The gurlie-boi turned away and strutted to the edge of the bed and, still facing away leaned over the hotel bed to give Mr. Carlton her under-skirt view with her red dental-floss-like panties bunched in her ass crack and her little balls drooping outside the panties. She shifted a bit, humping the bed like a male dog on a bitch, and moaned in her voice. The voice was sexy in its own way, but the tone was a flat dry tenor. To me the voice clashed with her otherwise impeccable look. After a few humping motions her already slimy uncut little semi-limp uncut cock fell out of her little panties and popped into view. Her cock was maybe a four or five inches and was shiny and flopped around in all directions.
I had a momentary flash of shock because of her openness and genuine eagerness. She was sexier in a genuine way than any of the porn stars I'd been seeing over the past weeks. I was in awe, but also in a strange way I was reassured that I was not unique in my enthusiasm to be a slutty gurl.
He zoomed in on her cock. It was small and pointed with the foreskin covering the entire cockhead and creating the appearance of a thin funnel made of tight tan skin. The camera followed for almost a minute until the gurl shifted and turned. She pumped back and forth upward and into the air as the camera zoomed out to see her ass-bumping the bed corner like it was a lap-dance. She smiled and abruptly stopped and then lifted her miniskirt over her hips and said in her flat semi-femme tenor, "Jue wohnt to fock me Papi?" She was a dream-cum-true in so many ways. This private porn turned me on, despite the obvious inappropriate aspects.
In the movie and from behind the camera Mr. Carlton said, "You know I do Esmeralda. You know I love that tight little cunt of yours."
In a deep accent, Esmeralda considered a moment and then, her translation complete, she said with a leud smile, "Umm I...lohve jor beeg...umm," Searching for the word she muttered, "Penga, no..." then in a triumphant voice with a huge smile she exclaimed "COCK!"
I smiled at her triumph and thought that she obviously loved what she was doing and was probably worth far more then the twenty or so dollars Mr. Carlton had paid her.
Mr. Carlton chucked a bit and then panned downward to show his ample and totally hard cut daddy-cock.
The movie continued back on her and Mr. Carlton stepping to her. He said something obviously leud in Spanish that I didn't understand and, in a single practiced movement, she wantonly fell to her knees, took his cock in her mouth and eagerly sucked him deeply and enthusiastically. After a few minutes he said something else and, in a likewise practiced and singular movement, the gurl stood, turned and stepped to the window overlooking the beach, bent forward, planted her hands on the large sliding window-door and looked over her shoulder with a gleeful smile.
The camera panned down and showed his shiny raw naked six-inch-or-so cock entering her sex hole. Off screen, she moaned in pained tones that begged him into her. On screen her hips gyrated to let him into her deep and fully. His cock pushed in to the hilt and for a moment everything stopped.
The Gurl's ass froze a moment and off screen her voice went "Ohhhhhhhhh....Ayeeee Pappi...Si..."
Mr. Carlton panned back and now the shot showed her ass with his cock in it, her bra-covered back, her bleach-blonde hair dr****g off her shoulders and the bright mid-day beach. He said to the back of her head, "Now that is a tight pussy."
The gurl smiled over her shoulder as she arched her hips upward beckoning him to fuck her.
Mr. Carlton reached out in a firm manner and set the camera on the bed in a practiced motion and distance that caught the whole fuck scene up to his neck and down to her rich warm thighs. The moans were traded as the fucking began. Now she made moans with utterances of incoherent Spanish phrases. The sounds were deeply sexual and wanton. She was incredible. The gurl was bucking into Mr. Carlton and occasionally reaching under to stroke herself in time with his fuck-thrusts. After only a minute her cock grew and emerged from her foreskin. She stoked herself for more than the few strokes she'd been doing for the first few minutes of the fuck scene and went over the edge. She moaned differently and it was obvious she'd gotten too close to cumming and let go of herself too late. Her head and the fine blonde hair shot back and her hands braced her body at the window as she went into ecstasy.
Mr. Carlton knew her well and knew what was happening. He reached under and grabbed her cock took her over the edge and jacked her orgasm free. She seemed to protest a moment, but then surrendered in the next moment. She moaned deep and loud as she came, first in drops, then a two heavy spurts onto the window. Then he let go, making the orgasm hands-free from that point on. Shot after shot blasted in time with his daddy-cock pumps into her petite body.
In my head I recalled that in some of Mr. Carlton's porn I'd seen, probably the home made dominatrix porn, somebody had called this a ruined orgasm, but it was definitely not ruined in any way for her.
My mind paused away from the movie briefly and I felt a sharp wave of embarrassment that, after being fucked and cumming similarly hands free, I personally knew that it was far from a ruined orgasm.
In the movie Mr. Carlton fucked her and urged her on in English, saying, "Yessss, that's a good gurl...cum...cum you little bitch...fuck yes...cum baby." The tranny's cock, flopping up and down, spewing lines of rich semen all over the place. The gurl came hard and moaned over and over.
She paused, on the plateau of ecstasy and catching her breath.
Mr. Carlton denied any reprieve and pushed the skirt up and out of the way in a sharp motion. He gripped her small ass firmly and fucked her hard, deep, and fast. After a minute, she came again, drooling more cum all over the window. Then there was a period of slow smooth fucking that lasted two or three minutes and, again, he grabbed her cock and jacked her into a second orgasm. Her cock was totally limp, but flopped around on all directions throwing cum all over the place.
I was shocked and had to mentally rewind to fully grasp that she'd cum and was cumming again. NONE of the porn movies had shown that.
Could this be me? A dark part deeply hidden inside me woke to ask.
Then, Mr. Carlton leaned into the gurlie-boy's body, curving around it like a hand cupping a softball. He grimaced, no longer trying to hold off his own orgasm, and fucked hard and upward into her. Esmeralda's face showed that she was obviously past the pleasure of the moment and enduring him using her body over the next minute or so. Mr. Carlton, eyes shut in the movie. He was oblivious to Esmeralda and uncaring. He was used her and it was hot. The gurl was his sex doll, just as I'd been. He began some really hard, deep, almost brutal fucking, breathing in and out hard. He was about to cum and he slowed his pace to a controlled rhythmic pumping, like an oil rig. In, out, in, out.
Then, apparently now caught up with the moment and her lover's motions, Esmeralda smiled a wicked smile into the camera and stroked herself as she pumped back into him, shifting form an enduring whore to a wanton slut. She stroked herself smoothly and looked very much into the moment.
Then Mr. Carlton lurched forward powerfully and started to cum. As he came he uttered in a high voice stressed by intense physical activity, "Fuck...yes!...I love little fresh bitches like you...ahhh!" Then he came in her for a while as he pumped her deep sharply over and over for almost a minute. He pulled out. His large meaty daddy cock was glistening and still hard, but flopping around as he stood up. He pulled her back to him, kissed her deeply and then grabbed her bleach blonde hair, that now seemed sleazy in some way, and he pushed her down and made her suck his cock fresh from her ass. She moaned in her deep adolescent and mismatched voice and as she pulled away form his cock and looked up Mr. Carlton's voice said, "Bueno Puta," and his hand appeared in front of the lens and then the movie abruptly stopped.
I was back in Mr. Carlton's upstairs playroom, still standing half way between the stairs and the love seat, captivated and instantly embarrassed at how horny the scene made me.
Mr. Carlton looked at me in one of the ten or fifteen mirrors placed around the room and motioned me to sit on the low couch bed in front of the love seat.
At that point we talked. For like an hour and a half we talked and talked. To this day I do not remember much of the conversation, but I do remember at the end of our long conversation he asked me and then essentially made me suck his cock while I stroked mine and came really hard. Then he made me keep sucking him off until he came.
We talked some more and then he made me do the same thing again. Then, the third time we traded positions and he sucked me and as I approached orgasm I felt him stuff his slick lubed finger up my ass and stroke my prostate. I remember that orgasm to this day. I came more intense than I had ever come before.
Only after he'd violated my ass and made me cum like that did he let me go. I was amazed and ashamed and he knew it.
At that point, my self-loathing dissipating, and my willingness to continue playing on the rise, he sent me home.
I left much earlier than usual, around 1pm. As I undressed and became a boy again I vowed as I left to never go back to his house.
As I left he made me promise I would keep what we'd done a secret. Mr. Carlton explained that letting anyone know would be bad for everyone, but mostly me. He probably wasn't entirely right, but what did I know?
I went home and put the entire event of my first fuck and being dressed like a gurl out of my mind. For a while.
Then, around 11pm that same night I knew that I wanted to go see him the next day.
I did try to see him, but he was gone all day.
The next day, Wednesday, hump day, I saw him through the same windows he's spied on me from and he waved at me to come over. I debated with myself a few minutes and then decided to go back over. I knew what he had in mind and I knew that I consciously didn't want it, but deep in my sex I also knew I did.
I arrived about an hour later than our usual play date start times and I had severe reservations, but an insatiable drive for more.
I knew what was going to happen if I delivered myself to him as I walked up the stairs. I put aside questions about sexuality and embraced the rutting desire to experience not only the physical sexual penetration and unique stretching sexual pain-ecstasy but also the surrender and submission to his violation. I was hard and my sexual areas pulsed. Though I was far from OK with it, I put aside my negative thoughts and embraced my lust and desire. I let my need for sex to make sense go. I could figure out my sexuality some other time. In the mean time, I wanted to be his little whore. I went into "my bedroom" and put my things on.
That day I got fucked for my second, third, and forth times and I was his.
Every day the rest of the week, seconds after my mom pulled away from our driveway I was at Mr. Carlton's kitchen door and then upstairs.
The following Monday I went upstairs to find a brand new high-quality Auburn wig with deep red and a few black and reddish highlights over a new sleek black garter belt, new black stockings, a matching shiny black bra, matching sleek shiny panties.
A note placed with care next to them that said, for you, Rebeca.
The misspelled name not withstanding, I soared and almost tore the stockings as I hurried to get them on.
3 years ago
