Michelle and Jessica venture out of the apartment, and into a whole new world
It was not a restful sleep. Haunting questions of my own sexuality plagued my dreams. In one such consuming dream, I was Michael again, bigger, stronger, more masculine than I had ever been before, or could imagine myself being. With this physique, I easily brought woman after woman to my bed. Each succumb to my sexual prowess, each removing their clothes as they fall backwards on an oversized bed, then spreading their toned legs to invite my powerful cock inside of their womanhood. Each one thoroughly defiled, filled with my potent cum, before moving on to the next.
And as my latest sexual conquest, a dark haired teenage girl no older than myself, lay on the bed before me, her slight, petit body became aroused. Her pink nipples hardened beneath my gaze, her chest growing with each deep breath she pulled into her lungs, but not diminished by her exhales. Her legs parted, as I inhaled her scent deeply, and as she welcomed me to her pussy. But in her arousal, she changed. I stared in awe as her clit grew to massive proportions, becoming veined, pulsing with the same sexual power my own cock had. A second look revealed her to be Jessica, my dear sister, made into a man by my dreaming mind. Without words, I was suddenly facing the thick, massive cock of my beloved sister.
As Michael, I turned away, feeling disgusted by her erection. But in the same instant it took to close my eyes and rip my gaze from Jessica’s new body, my hair grew long and wavy, and lightened to the color of straw; my chest grew heavy, giving me the large breasts I had always craved, even to the envy of my sister. But the changes to my body were not yet through, as I felt my own arousal enveloping me. What I felt was a wetness between my legs, a radiating heat coming from between my thighs, and not as a throbbing pulse in my groin. I opened my eyes to look down at my nude form, seeing the wonderful breasts with pert nipples weighing heavy on my chest. My gaze traveled further down, seeing my mound, not shaved smooth as it was last night, but with a small patch of blonde hair, neatly trimmed into a triangle. There was no sign of my cock. My head turned back to my sister as she lay there. Michael was gone, but Michelle was now there. No longer disgusted by the thought of it, I leaned forward, eager to put as much of her beautiful cock into my mouth as I could, desperate to feel the sensation of her powerful orgasm granting me load after load of her pearly cum, rewarding me with the sweet taste that I craved.
My mouth opened wide, wider than I thought it could, to accommodate Jessica’s erection. I felt my lips stretch almost painfully around her. Her hands held tightly to my head, as she pulled my head closer to her pelvis, forcing inch after inch deeper inside of my throat until all of it penetrated me, violating me. She grunted, her marvelous breasts quaking with each thrust she made, as she started to cum. I felt my mouth flood with a sudden force of liquid, as she used my mouth, all while holding my head, stopping my breath, and granting me her cum.
Once her orgasm had subsided, she pulled her cock from my used mouth. I gagged and coughed, massive globs of the thick cum falling from my lips, splattering on her cock and my breasts. “I’m not through wit you yet, Michael”, she said, using my old name, almost as a chance to hurt me emotionally. She quickly stood, and with a spin, had thrown my nubile form to the bed. I bounced slightly on the springs, as Jessica stood between my legs, forcing them open wide. She looked at me with the same fire in her eyes I had experienced before. But her gaze was not locked to my eyes, were our passions seemed to fuel each other, but transfixed on my own womanhood, that being the target of all her lust and desires. Her hands gripped tightly on my knees, pushing my thighs even further apart, my pussy now opened to her and her large cock. She said nothing as her cock angled downward to line up with me, as she leaned forward with her hips…
Even before I was fully aware of my surroundings, my mind was still able to come to a universal truth of life: Alarm clocks are the vilest invention ever created. The annoying, repetitive buzz echoed through the bedroom, seeming louder with each second that past. And as each second past, my dream faded to a distant, inaccessible corner of my mind, leaving me only with a painful erection, and a vague, erotic feeling of what had been.
Jessica’s quick arm shot out to her nightstand, putting an end to the vile noise. I breathed a sigh of relief as the blissful silence returned to the happy bedroom. But the device had done its job, and I was awake. I glanced over at the offending clock. “Did you really set your alarm for 6:30 in the morning on a Saturday?”, I asked more annoyed than curious. I was proud that despite my annoyance, I was able to ask in Michelle’s voice, rather than Michael’s.
“Yeah”, she said groggily, rising slowly from the bed, stretching her arms, and giving her back a little twist. “I told you, we have a lot to do today, love”. She didn’t offer any more explanation, but leaned over to give me a quick kiss, before scooting out of bed, and head into the master bathroom, closing the door behind her.
I could clearly hear the sound of her peeing, which only reminded me of the urgency I had. I too scooted out of bed, and made my way to the spare bathroom. I pulled my hardened clit from the panties I was wearing, and let nature take its course as best I could. My body leaned forward at the hips, desperately trying to aim the stream into the bowl. Once finished, my erection had soften slightly, and I was half a second from tucking myself back into the panties, just has Michael had done a thousand times before while wearing underwear. But I wasn’t Michael anymore, so I had to break myself of those habits. I took a little bit of toilet paper, and made sure my clit was completely dry, especially around the slit, before pulling my panties back up. I also considered that I would just sit down to pee from now on, like girls do, though there would be times when that wouldn’t be a viable option. Some habits were going to be tougher to break than others.
I returned to the bedroom, finding Jessica going through her underwear drawer, her back towards me. “You can keep wearing those panties for today, if you want”, she started, as she pulled a white bra from the drawer, and a blue thong, “But you should probably wear a bra that fits you, and that you’re comfortable wearing”. She pulled off her nightie, then pulled the straps of the bra over her shoulders. Her hands reach behind her with practiced ease, as she grabbed the hooks and secured her bra. She made some minor adjustments, ensuring that her ‘girls’ would be comfortable, and that the straps of the bra rested over her shoulders.
“Why, what are we doing today”, I asked, pulling off my nightie. I had a growing knot in my stomach, suspicious of what she had planned.
She turned her head to look back at me, a sinister smile crossing her face, “just what every teenage girl dreams of…A shopping spree”.
The knot in my stomach hardened into a lump, as tears welled in my eyes. “I can’t”, I muttered softly, not even sure she heard me.
“What’s the matter, Shelly”, she asked, genuine concern in her voice, as she quickly came to my side, ready to hold me.
With her arms to guide me, I sat down on the edge of bed, her resting beside me. “I can’t go out”, I repeated. “Look at me”, I said, looking down with disgust at my flat chest, and panties that had an obvious bulge in them, made more pronounced as I sat. “I may not be Michael any more, but I’m a long ways from being able to be Michelle in public. I have no breasts, my hair isn’t real”, I pulled the blonde wig from my head, hurtling it to the ground. “The only clothes I have are wrinkly from being shoved in a box. And”, I started, my voice suddenly lost in my throat, “I don’t think I could face seeing anyone who knew Michael”. That was the heart of it. I was afraid. If someone I knew were to see Michelle, and figure out that I was once really Michael, I just couldn’t deal with that.
Jessica held me, comforting me, as I both tried not to cry, and as I cried. Her arms never let me go, even as the minutes ticked by. Her whole concern was my happiness, and I could feel that she would have moved heaven and earth if it would bring a smile to my face. Again I felt her love envelop me, as the long minutes stretched into short eternities.
I regained a modicum of my composure, and she used her soft hand to gently lift my chin, to stare at her angelic face. “Michelle, I would never intentionally force you to face that. When the time comes, and Michael’s secret is discovered by the whole world, you can rest assured I will be there at your side”. She used her other hand to gingerly wipe the tears from my cheeks. “If you want to, really want to, we will never leave this apartment again. We will stay together, as sisters and lovers, for the rest of our lives. We will hide Michelle from the entire world.
“But I think at some point, Michelle is going to want to see the world through her new eyes, and revel at all the experiences the world has to offer a girl. From something as subtle as a light breeze wiping at your hair and at your skirt, to the raw sexual empowerment you’ll feel as a man stares at you with unabashed lust. I’m not saying any of that will happen today, but I can promise you it won’t happen until you are able to step outside, and face the world as the powerful young woman we know you’ve become”.
Inwardly, I cursed my sister. She always knew exactly what to say to make me feel better, even in spite of myself. But she wasn’t wrong. I told myself that Michelle was never going to be hidden again. That was who I was now. I was terrified; there was no doubt about that. I swallowed hard, forcing my terror and doubts down with it.
“Why don’t you get dressed”, Jessica started, seeing my apprehensions slowly fade, and my newfound resolve fortifying me for the upcoming day. “When you are dressed, meet me in the bathroom, and I’ll do your makeup”. She leaned over, and placed a gentle kiss on my forehead, then rose, picking up a pair of jeans and shirt as she headed to the bathroom. Before closing the door behind her, she pointed over to her underwear drawer, my breast forms lying on top.
It took another half hour before we were finally ready to leave the house. I was dressed in a pair of jeans, that felt way too tight around the thighs, and that didn’t come up to my waist, resting slightly below. As a result, my panties were also lower, the red waistband only visible at the right angle if someone stood behind me. I also picked out a simple blue blouse, with a thick cotton weave material, enough to conceal my bra and any sign of the breast forms, while at the same time tight enough to allow me a small measure of femininity as it hugged my curves. I had no female shoes that would fit, instead slipping on a pair of running shoes Michael had. A small silver clutch purse, filled with Michael’s wallet and cell phone completed my ensemble. Jessica assured me that I looked fine.
And I learned so much as she applied my makeup. Michael always thought more makeup was more girly, so when Michelle had used makeup before, it was layered on heavily. I must have looked more like a clown than a girl, I reminisced. She added some lipstick to my lips, a softer shade than the fire-engine red I wore the first time she met Michelle. She applied light blush to my cheeks, and carefully added mascara, giving me fuller eyelashes. She even combed my wig a few times before resting it back on my head.
Her own appearance added an extra tightness to the tight jeans I was already wearing. Her jeans were dark blue, boot-cut to show off the snake-skin pattern of the heeled boots she wore. Like mine, they were low-rise, but she had no problem letting everyone see the waistband of her blue thong. She called it a whale-tail, and made sure I understood why, by bending over directly in front of me. She smiled, noticing the obvious effect it had on me. Her top was a deep-vee, showing off every inch of her ample cleavage, while also perfectly concealing her bra. She did her make-up in a fraction of the time it took her to do mine, and then we were out the door.
Even the few steps to the car filled me with dread. What if some of the neighbors had seen Michael come over on Friday night, and now see Michelle leaving Saturday morning? I felt a little better as we got into the car, and headed out.
“We’re going to the Midland Mall”, Jessica said, as she navigated to the freeway. “That’s a good forty-five minutes out of town, and a lot less likely that you’d run into anyone you knew. Plus, I know it has every shop we need”. She placed a comforting hand on my thigh, the same thigh I hadn’t even realized that I was bouncing uncontrollably. “Relax”, she said, risking a quick glance my direction as she drove, and favoring me with a loving smile.
The parking lot was cramped, forcing us to a spot a good mile away from the mall’s entrance. I exaggerate of course, but walking any distance when you’re trying hard not to be noticed made the trek seem longer than it should have been. “Try to sway your hips, but just a little”, was a sound piece of advice Jessica gave me as I took my first few steps through the cramped parking lot.
Once inside, the crowds were in a hustle and bustle. Teenage girls flittered from store to store, arm-in-arm with the girl next to them, and with bags adorned with the logo of the shops they had visited. There were teenage boys too, being carefully watched by mall security, as they paced through the main thoroughfare, holding skateboards, looking as if trying to find a secluded spot without witnessed, ready to defy the ‘no skateboarding’ signs posted everywhere. That is, when their attentions weren’t focused on the girls.
“First things first”, Jessica said, standing in front of me, making sure my attention was fully on her. “You know I love you as a blonde, but some old Halloween wig isn’t going to fool anyone for long. We’re going to get you a new wig”. She said, as she led me to the elevator, and pressed down.
The doors to the elevator opened, and we were suddenly face to face with two teen boys within. They made a motion to step out, but seemed to change their mind when they saw us ready to step in, a smile creasing their faces. My heart nearly stopped. I was terrified that they saw right through my disguise. I quickly turned, but Jessica grabbed my hand, giving it a reassuring squeeze, and pulled me into the elevator. The doors closed, and the elevator began slowly down to the basement level. I was sure the teen boys were quietly laughing at the man in drag that was right in front of them.
Jessica and I stepped off the elevator, and made a few quick steps down the long hallway towards the wig store. A snickering came from the elevator as soon as we were out of eyesight. “Man, did you see that blonde”, one of the boys was clearly gloating to the other. “I would have loved to get her on her knees with my cock pumping in an out of her throat”. The elevator doors closed again, the sounds of their hormonal ranting cut short as the doors closed. I had to admit, it was a boost to my confidence.
Jessica giggled, “You know, I sometimes forget that you have the hormones of a teenage boy running through your veins too”. She smiled, as we took a few more steps, and found ourselves in a somewhat secluded area. She stopped, then turned to face me, “tell me, do you have fantasies of a girl on her knees, while your cock pumps in and out of her throat?” It was the first time she had ever referred to my clit as a cock.
I blushed visibly, hearing her talk that way, but at the same time, my clit did respond to the vulgar way she spoke. I stiffened in my tight jeans, wishing I had chosen pants that came up higher, as I had to adjust myself in my pants to be more comfortable, but afraid the tip would be poking out of the top of my waistband. “Jessica!” I scolded her. She knew the effect her words had on me, and had on my clit.
Her grin just widened. “It looks like you’re going to give everybody quite a show as you walk around the mall today. Or, you can follow me into the restroom, and use me like a teenage boy uses a girl”.
I could see the lust on her face, her eyes burning into me, as her cravings overtook her. But it was the look on my face that caused something to snap in her, instantly regretting the proposition. The fire in her eyes faded quickly, as she realized what she just said. She essentially wanted me to be Michael again, to be a vulgar, grunting man, to use her body simply for my own pleasure. “Remember how I said yesterday about what we did? That what we did had nothing to do with you being a girl, but was about me being a woman?”, she reminded me of the words she said, right before taking my clit in her mouth, and sucking me to a powerful orgasm. “I’m so sorry, Michelle. Please forgive me. What I just said was also because I’m a woman. Sometimes I can’t control myself…I didn’t realize…”
“No”, I spoke softly, stopping any further explanation, and holding her face. “You’re right about my hormones, and you can clearly see I’m not in full control either”, I indicated my bulging jeans. With the surge of adrenaline pulsing through me, I found a confidence I hadn’t been expecting. “Let’s go to the restroom”, I started. “There, we’re going to make love just as we did our first time, with our clits rubbing against each other, as sisters, and as lovers”, I spoke quietly. I wanted to grab her, hold her close and kiss her soft lips, pressing our lipstick together. But I was also keenly aware we were in public. As scared as I was that someone may recognize me, I was more afraid that someone may recognize us, as sisters, in the awkward position of an intimate kiss.
I saw her go, walking with a sway in her hips, as I followed behind at a discrete distance, trying hard to keep my erect clit hidden from the eyes of whatever teen boys are looking down from the second floor railing. I hesitated only a moment at the threshold of the ladies room, before pushing the door open and stepping inside. There was no one else in the restroom, my sister poised of the counter, leaning forward while fixing her lipstick, and giving me a clear view of her blue thong’s whale-tail.
She turned her head, smiling at me, but kept her body in the erotic pose a few seconds longer than she needed to. “We’re all alone in here”, she said, putting her lipstick tube back into her purse, as she strolled to the end stall, her hips swaying seductively as she went.
I followed her like a drooling puppy. I admonished myself, knowing I was acting more like a teen boy than a young lady, but at the time, I didn’t care. She was right: We weren’t in control of ourselves, we both had hormones coursing through our young bodies. She closed the door to the stall, locking it, then her arms wrapped around by neck, as her lips pressed hard against mine. Her mouth opened as our tongues playfully darted in and out of each other’s mouth. “We have to be quick, and quiet”, she said, breaking our kiss, and pulling me to the toilet. She spun me around, facing me as she pushed me down to sit on the seat. Her hands wasted no time as she quickly unbuttoned my pants, and slid the zipper down, while her lips still pressed against mine. The head of my clit was clearly visible poking above the waistband, with the shaft outlined against the red satin fabric of my panties. Her hands greedily clawed at the flimsy material, pulling my panties down enough that my clit was free, standing erect. She pulled down my pants enough to ensure they would not interfere with our lovemaking.
With effort, she pulled her mouth away from mine, as she spun around, her back towards me. I heard her zipper fall, and then saw her slowly lowering her jeans. Again, I marveled at her whale-tail, but only for a brief moment before her thumbs slipped into the waistband of her own panties, and lowered them. I stared in awe at her ass, marveling at its tone and firmness, more evidence of her workout routine. She parted her legs as far as she could considering her pants were around her knees. She reached backwards as she lowered her hips down. She grabbed my clit, sending a surge of sexual energy through me at the touch, while she angled it upwards, guiding me into her body from behind.
She sat down slowly, my clit sliding deeper and deeper inside of her as she impaled herself on my shaft. I reached out to grab her hips, wanting to force myself into her as deep as I could go in only a single thrust, but with shaking arms I controlling those urges, and letting my sister experience every inch on my clit at whatever pace she wanted.
It felt like minutes, maybe hours, before I felt her full weight resting on my lap. From within, I swear she could feel my heartbeat, as my clit pulsed as my heart raced. There was also the experience I was feeling, as her womanhood wrapped around my clit. I could feel her wetness coating me, and her muscles tightening inside of herself, squeezing my clit with the same passion that lovers embrace each other. My own muscled tightened, creating the sensation that I was slipping even deeper inside of her.
My hands slid from her hips, and trailed up the front of her shirt, coming to rest on her breasts. Instinctively, my hands squeezed each firm tit, molesting her as best as I could through her shirt and bra. My fingers ached to play with her sensitive nipples, to hear the sounds of her arousal escape from between her painted lips as I tweaked each nipple between thumb and forefinger. My mind wandered as I imagined her completely naked atop of me, her body mine to play with and do with as I pleased.
With a strength I did not know she possessed, she lifted her hips off of me. The wetness she left at the base of my clit obvious as the cool air in the bathroom caressed me there. I slid slowly out of her, a chill racing up my spine as the exposed flesh of my clit reacted to the cold of being removed from the warmth of her loving pussy.
Jessica pushed back down, causing a feminine moan to escape my lips as my clit penetrated her again, feeling slide deeper than it had before into her. My muscles clenched again, and again I felt as if I slipped further inside. “Shhhh”, she admonished me for moaning. To keep myself silent, my mouth went quickly to the nape of her neck, my lipstick smearing across her porcelain skin, leaving a red trail up to her ear, where I began nibbling at her earlobe
This was the rhythm we repeated, her slowly and methodically bouncing up and down on my lap, as my hands fondled her heavy breasts, and my lips playfully biting at the nape of her neck, and at her earlobes. We were so engrossed with the passion between us, we hadn’t realized the door to the restroom had opened, and someone had entered. At the time, we were blissfully oblivious.
“Oh, Michelle”, Jessica whispered quietly, her voice barely a breath escaping her lips. I felt her pace quicken, as I could tell she was nearing her own climax.
“Oh, Jessica”, I cooed into her ear, also as nothing more than a hot breath on her neck. I was close too, as my body tightened. I resisted the powerful urge to arch my back, fearing it would knock my dear sister off. Instead, my head titled upward, gazing at the blank ceiling, as my hands gripped her chest even tighter. I wanted to scream, as I neared ‘forever’ time, my body tensing. I felt her pussy hold me tightly, tighter than I had felt before, her own ‘forever’ time gripping her as her whole body stopped.
“Michelle!” she silently screamed again with a long held exhalation as her climax overpowered her, her body convulsing on mine.
“Jessica!” my own silent scream joined hers as my ‘forever’ time ended, releasing spurt after spurt of my cum deep inside of her waiting pussy.
A soft knock on the stall door abruptly ended our post-coital bliss, putting a nearly paralyzing fear into both of us, as we quickly untangled our bodies, getting dressed as rapidly as we could. “Midland Mall Security”, a female voice announced herself. “In the future, you ladies should keep your activities at home” the disembodied voice called from the other side of the stall door. “I’m going to let you two go with a warning this time, but you cause another scene, and I’m calling the cops”. Having said her peace, the guard’s footsteps echoed off, the sound of the door opening and closing sealed me and my sister alone again.
We quickly fixed our makeup before leaving the bathroom, and were extremely relieved to see that some burly female security guard was not standing directly outside to remind of us the trouble we would be in if we caused a scene again. “That was amazing”, Jessica whispered in my ear, a mischievous grin plastered on her face. I looked at her, at first to yell at her for how close we had gotten to being caught, but as I saw a streak of my lipstick still not wiped completely away from her neck, I had to admit to myself that it really was amazing. I merely blushed, and she instantly knew that I was thinking the same thing.
“Can I help you girls find something”, the store clerk greeted us warmly, a dumpy woman with a raspy voice, from years of obvious tobacco use. She smiled and seemed pleasant enough.
“We’re looking for a wig for my sister”, Jessica started. “I think she wants a blonde wig, about the same length as the one she has on now, but something less obvious”.
The clerk, Kathy by her nametag, gave a few knowing nods, looking at the wig I had on. “I can always spot the bad ones”, she said, as I suddenly felt a little insulted. “But can you spot the good ones?” she asked, lifting a corner of her own hair up slightly, proving that her full head of hair was as fake as my blonde tresses.
“I had no idea”, Jessica said, staring in awe. I even had to admit that it looked really good. Jessica and Kathy went around the store, discussing colors, styles, application, and maintenance of wigs. I found myself wandering through the store, until my eye caught one in particular, a gorgeous straw colored blonde wig, wavy hair cascading downward into small curls. I fell in love, as snippets of memories flooded back to me, reminding me of the dream I had last night. I reached over, caressing the hair, feeling just how real it felt. Then I slowly revealed the small tag with its price.
“We should probably be going”, I said, grabbing Jessica’s arm, urging her out of the store.
“Excuse us a moment”, she said to Kathy, leaving the clerk at the counter, as we stepped out of immediate earshot. “What is it?”
“That wig”, I said, pointing to the one that was in my dreams, “is $1200! I have maybe $400 in my account. I thought we were going to pick up a few clothes, definitely new shoes, but I just can’t afford that”.
Again, her ‘I have a secret’ smile crossed her face. “How old are you?” she asked.
“What?” I asked wondering what that had to do with anything. “I’m nineteen”.
“And in nineteen years, has Michelle ever gotten a birthday present from me?” we both knew the answer to that. “That means I have nineteen birthdays worth of presents to make up for, my little sister”, she said, as if it were a plausible explanation to be spending as much as she was planning to. “I told you, I had years of planning for this day”, she quickly dug through her purse, and pulled out a bank statement, holding it out to me. The first thing I noticed was that it also had my name on it. Not Michael, but Michelle. The second thing I noticed was the nearly ten thousand dollar balance. “There’s enough in there for Michelle to start her new life. Clothes, wigs, the boob job if you want it, or the pills if that’s what you want. I opened that account over five years ago, and managed to set aside at least a little bit each month, preparing for this special day”. She removed a thin plastic card from her purse next, handing it to me as well. A gold Visa card, with my name, Michelle, raised across the front.
I couldn’t move. I was speechless as I stared at the card, feeling my eyes starting to water. “Oh no you don’t”, Jessica said, pinching my arm.
“Oww!” I screamed.
“You can get all teary and ruin your makeup once we get home”, she scolded me with a playful smile. I did wrap my arms around her, hugging her tightly, all while struggling to keep my eyes dry.
We went from store to store, racking up a very impressive collection of everything feminine. I had the wig of my dreams, along with expert instructions on how to wear it so that no one could tell. A few new pair of shoes, heels for something formal, and flats for walking around. Michael’s worn sneakers were quickly tossed in a nearby trash bin, now that I was wearing a far more sensible shoe to complete my feminine look. We had several new outfits from various stores; pants, skirts, shirts, tank-tops, a few more revealing outfits I wasn’t going to wear often, but Jessica insist I got.
“Okay, I’m going to run these to the car”, she started, managing to grab hold of every one of the bags.
“Okay”, I said, trying to take some of the bags back to lighten her load, and walk with her.
“Not you, Shelly”, her words pierced me, almost hurting me. “Michelle, you are a strong, independent woman. We’ve been wandering the mall for hours, and no one even suspects, and they’re not going to. But you need to feel that confidence on your own, without me there to constantly reassure you”, she smiled, as I realized she was right. “There are two more things I want to get before we leave the mall. The first is getting your ears pierced. So I want you to go to that jeweler over there”, she pointed to a store across the food court,”and look at all the earrings, and find a pair you like. If you have any sort of problem, just call me, and I’ll come running to you”.
My heart started beating uncontrollably again, as I watched my sister walking away. I turned my head, my body slowly turning too, ready to walk to the jewelers she had pointed out. She was right about how dependant I had gotten over her constant reassurances. Without her at my side, my mind was convinced again that everyone here saw Michael, a gangly teenage boy dressing up as a girl, as if I had lost a Super Bowl bet.
I took about a dozen steps, gaining a little confidence with each, before I had enough willpower to shut out the negative voices in my head as they tried to fill me with doubt. With the next dozen steps, I felt like a confident young woman again.
“Can I help you with something, Miss”? It was a man behind the counter, dressed in a business suit that spoke. I concentrated so intently on taking each step, that I had nearly forgotten I was going somewhere.
“Um, yeah”, I started, making doubly sure I was using Michelle’s voice, “I’m looking to get my ears pierced”.
“We can definitely help you out that”, he said smiling. I was so wrapped up with what I had been thinking, and so worried about what I thought others saw of me, that I didn’t really get to notice what they were actually seeing of me. Stephen, the lone clerk at the jewelry counter, reminded me instantly of what he was actually seeing: A beautiful young girl walking into his store. I saw it in his eyes as my gaze finally lifted to meet his. There was a kind of passion to his look. Nowhere near the intensity I had seen in my sister’s eyes, but it was there, unmistakably primal. He wanted me. Jessica had told me, warned me, about the power I would feel at this moment, and I reveled in it.
“Do you have some earrings in mind”, he asked, his sweet voice rolling through the air like fog along a hillside, lingering and enticing with its held secrets.
“Uh, no, not really”, I admitted. My heart beat wildly in my chest as I uttered my next words, “What do you think would look good on me?” Inwardly, I was shocked at myself. Was I really confident enough in my appearance to actually be flirting with a boy?
Another realization struck me just as hard, nearly stopping my heart: Was I interested in boys? All my life as Michael, I was only interested in girls. And even over the past two day as Michelle emerged, I was with my sister, a girl. Even all the times when Michelle had come out of hiding to play for a few hours, I was more wrapped up in the experience of being a girl to even consider if I wanted to be with boys. This was a new territory for me.
Stephen appeared oblivious to whatever internal turmoil I was facing, as he answered my question, “Well, you have such cute ears, so I’m thinking little hearts”, his smiled and voice warmed me, despite myself. “We have some small ones on sale over here in 14 karat gold”, he guided me to the display case.
I’m sure he kept rambling on about how cute I was, or the great deal I would be getting on the earrings, or other such nonsense. I was too wrapped up in my mind to listen or care. I shook it off, not wanting to deal with the new emotions I had dredging up, but being unable to focus on anything else. “We’ll take them”, Jessica’s voice said, startling me from the introspective I was suffering. I hadn’t even notice her return.
My ears hurt, but nothing that I couldn’t deal with, as the little golden hearts dangled from my earlobes. Jessica and I were walking along the fourth floor of the mall, heading slowly to the last secret destination she had planned for the trip.
“Okay, what’s wrong”, she asked as we found a secluded spot, where no one could overhear us. My silence and blank stare made it clear I had something on my mind.
“Am I gay”, I asked her quietly.
Her worried look faded, as her face soften. “Oh Michelle”, she started, comforting me with just her voice, the way only a lover could. “I wish I had the right words for you now, words that would set your mind at ease, and give you back the same confidence I saw before. But it just tears my heart out that I can’t give you an answer. Your sexuality is something you need to decide for yourself. My own journey of discovery led me to a lot of different places, from Tyler, other men, and yes, I’ve experimented with other girls before you. But remember, I will never judge you, no matter what. If you decide you prefer boys, girls, or both, and even if you take another lover and tell me that we will never make love again, you will always have my heart”, she took my trembling hand and placed it on her chest, “forever, my darling sister”.
“I think I’m about to ruin my makeup”, I said, wanting nothing more than to cry at her unconditional love. My arms flew around her, holding her in a tight embrace. I fought with myself not to cry. “And I will never stop making love to you”, I reassured her.
We continued along, my confidence returning ever so slightly, but still plagued with doubts of what Michelle liked sexually. I will never tire of the sensation I have as I make love to a girl, my clit sliding into her, the feelings we seem to share as our bodies become one.
But at the same time, some of what Jessica had done made me feel like I was missing out on a huge chunk of what it was to be a girl. Last night in the bathroom, she sunk to her knees and sucked me off, all while saying that it was something she had to do because she was a woman. And when I met Stephen at the jewelers, I think I felt a fraction of what she was talking about.
We past store after store, Jessica gleefully pulling me along by the arm, leading me closer and closer to our last stop. And as store after store flew by, I began looking ahead to see what was left. Then it became painfully obvious where we were heading: Fredrick’s of Hollywood. “I told you, I already have plenty of underwear”, I said sheepishly.
She held my arm tighter, as if to prevent me from running away as we got closer to the storefront, the windows adorn with peach-skinned mannequins, each wearing something made to excite and entice. “That’s right, sis, you have plenty of underwear”, she said. “But do you have any lingerie? A naughty outfit you reserve just to be seen by your lover, and no one else? Or maybe something to wear when you’re feeling like you deserve a special night, even if it’s with a plastic friend you keep in a nightstand”, she asked, and I caught on to the innuendo immediately. It was weird, but before that moment, I had never really thought about Jessica masturbating. But right then, I couldn’t get the image from my head.
We strolled in, still arm in arm, as she dragged me all over the small store. She pulled me from rack to rack, each filled with a rainbow assortment of transparent panties, bras, camies, baby-dolls, and other clothes, none of which provided enough concealment. “How about this one”, Jessica asked, holding up a see-through bra to my chest. “How about this one”, she asked again, holding something new and just as flimsy up to my waist. She moved through the store like a tornado, grabbing up every dainty piece of flimsy cloth, holding it to my small frame, before discarding it on a nearby shelf. We had spent easily an hour there, before finally finding one that we both liked, a purple silk baby-doll and matching panties. We decided to get the top so that it would fit me without my breast forms. But before she made the purchase, she grabbed an identical set, only in her size, and had the store ring it up as well. “This way, we can look like identical sisters”, she whispered seductively in my ear, as she handed the now well used gold card to the cashier.
The ride home seemed much longer than the ride to the mall. All the while, I kept imagining my sister bringing herself off with a toy. With iron nerves, I decided to ask her something, realizing she had open and honest with me so far. “Can I watch you masturbate”, I asked, the crack in my voice betraying the iron nerves I had seconds ago.
Again a wicked smile creased her face. “Are you saying you never did while we were growing up”, she asked accusingly.
My bones turned to jelly, as I blushed wildly. Yes, growing up, I had spied on my sister as she pleased herself. It was always late at night, when she thought the whole house was asleep. I crept from my bed, and eased down the hall to listen at the door as Jessica climaxed. Then one night, I realized her door was opened just a crack, a narrow beam of light falling on the hallway carpet from her door. It was just enough for me to have an unobstructed view of her on the bed. My mind raced back to that magical night.
I think it was the sound that woke me from the sleep. I must have been eleven or twelve, just barely discovering the joys of masturbation myself, but before I began to fantasize over becoming Michelle. And it was the low moans that I heard that woke me up. Even if my ears didn’t realize it, my dick identified the unmistakable sounds of a woman in pleasure, as my erection grew strained against my briefs.
With stealth, as silent as a ninja, I crept from my own room, my heart beating in my chest, thinking about what to say if I were caught, but nothing coming to mind. Even so, I leaned against the wall near her door, and peered through the crack.
Jessica was naked on her small bed. It was the first time I had ever seen a girl naked before, and I was mesmerized. She was lying on her back, the covers tossed from the bed, the overhead light casting the smallest of shadows over her young body, as her breasts were just beginning to grow, and her nipples stood erect from the small chest. Her knees were bent, her feet laying flat against the bed, and her legs were parted. I stared at her pussy. It was totally bald, before she had started growing hair, her mound pronounced, her full lips still hiding her most intimate treasure. I was the body of a young girl.
The strain in my briefs was undeniable now, as my hand reach down to release my hardened cock, taking a firm grip of it. It sent ripples of sexual energy through me as I slowly started to stroke myself, as I had discovered the pleasure of it only a few months ago. However, with my heart racing, I knew this time was going to be something special.
Her hands slid slowly down her body, stopping first as she gripped her small breasts. She played with them, eliciting another moan from her lips as her hands brushed over the sensitive nipples. She covered them entirely with her hands, then spread her fingers to have her nipples protrude through her fingers. Then her fingers would close, tightly pinching her delicate flesh between them, and again another moan escaped her lips.
But her journey did not end at her breasts, as her hand trailed even further along. With her right hand, she cupped her sex, holding it in her palm. Her hand flattened slowly, as she moved it up and down along her prepubescent slit. With building effort, her hand moved quicker. And as I was stroking my little cock while watching her, I tried to keep my strokes in time with hers, as if somehow her strokes and mine were connected, both of us giving each other the pleasure we were feeling.
Her climax was subtle, but unmistakable. Her body stiffened, her back raising from the sheets of the bed, as her hand stopped moving. With a powerful moan, one she kept as quiet as possible, she came, her knees nearly slamming together, as if to hold her hand forever in place, to never give up the sensation she felt.
My own orgasm gripped me as well. As much as I would have loved to say we came at the same time, mine rocked me a few precious seconds after her own. I fell hard against the wall as I came, making a loud thud. My heart stopped a moment afterwards, knowing that there was no way she couldn’t have heard that. Her eyes went wide as she peered at the small crack in the door. I was certain she could see me, and knew without a doubt I was going to be in so much trouble once she told mom and dad. I did the only thing I could think of: I froze, even with my little cock softening in my hand. We stayed like that forever, her staring at me through the door, while I pretended hard to be invisible. I’m sure the pounding in my chest gave me away, as she rose from her bed. She was still naked, and I caught myself admiring her petite, teenage body once more as she walked, her hips swaying with the few steps. My eyes capturing ever moment of the erotic scene, from her budding breasts, covered with a glistening sweat, to the crease between her thighs as she got ever closer to me. I saw her smile, a beautiful, angelic smile meant to comfort any who she deigned to favor with it. I was almost sure she saw me, and was smiling at me, but there was no way to be certain. However, she said nothing as she reached the door, that knowing smile still across her lips, seemingly staring right at me, as I breathed through my mouth to keep as silent as possible. All she did, was close the door securely, and then turn off her light.
The memory flashed though my head in a fraction of a second, reliving it a thousand times over in the time it takes for an eye to blink. “You knew”, I asked, the embarrassment of that night returning to me, somewhat afraid that I could still get in trouble if she told mom and dad.
“Of course, I knew”, Jessica said, a knowing smile on her face, the same smile I remembered from all those years ago, as she favored me with it again. “When you crashed into the hallway, I thought you were going to break down the wall”.
There was a long awkward silence again. “Tell you what”, she broke the quiet with an offer, “when we get back, we change into our new lingerie, and we both masturbate. This time, fully in the light, both of us having a clear view of each other. We can enjoy each other’s body fully”.
Jessica looked absolutely stunning in the lingerie that matched mine. Of course, the clothes were actually designed for a girl, so she filled hers out much better than I ever could. The slight straps of the purple top arched seductively over her soft shoulders. Her firm, D-cup breasts filling in the front of the baby-doll, while still conforming to her frame, giving her cleavage even through the silk material. The ‘M’ over her left breast was clear, as well as her pink nipples, standing erect, as if trying to come through the silk. The lace pattern on the hem of the top complimented the same pattern on the panties, as it drew the eye down to her mound, and between her thighs, where the was barely any material to give her any modesty. She truly looked as if she was dressing for her lover.
The exact same outfit on me looked horrid. I had no breasts to speak of, as the top couldn’t support the breast forms, leaving me woefully inadequate compared to my sister. And try as it might, the lace panties only drew attention to my massive clit, the tip of it protruding nearly four inches over the tiny waistband. The narrow material that crossed in between my thighs only served as a painful reminder that I had once been Michael, biologically a man.
“I don’t think I can do this”, I said, ready to run back into the other room and change, at least into more comfortable panties.
“Please, Michelle, just for a little bit longer, I want to be twins”, she pleaded. I knew right then I was never going to deny her anything if it were in my power.
I sat down on the edge of the bed, and watched as Jessica sat down too. She leaned over from her far side, as we met in the middle share yet another passionate kiss. Her mouth yielded to mine, opening up to me, her breath mingling with mine, and with our tongues playfully slapping each other.
She broke the kiss, leaning back in bed. I followed suit, soon lying beside my sister as she was about to allow me to witness the pleasures a woman could give herself. She moved only slightly, as her hips rose from the bed to push the panties down, but still on her hips, only down enough to expose her pussy once again to my leering gaze. Her hand reached over her head, slipping easily under the pillow, to bring a narrow, six inch vibrator to her lips. Her painted lips spread a red gloss across the silver device, as she worked it in and out of her wet mouth. I saw her saliva glistening off of it each time it was pulled from her puckered mouth.
With an exasperated breath, she pulled the vibe fully from her mouth, as she drug it down to her thighs, seductively pulling it, and a trail of saliva between her tits, and across her stomach. Her other hand met her at her mound, and twist the black cap at the end of the toy, filling the otherwise quiet of the room with the erotic buzzing sound.
The buzzing became slightly muffled, as she pushed the first few inches of the toy into herself. “Ohhhh”, she exclaimed in a sharp intake of breath as she was penetrated. “Ahhhh”, she moaned again, removing about an inch of the faux cock from her, only to thrust even more inside seconds later. “The real trick”, she started to explain through heaving breathes, “is not the penetration, as much as it is the stimulus on my clit”. Her skilled hands started a stead motion with the silver vibe, holding it upright against her slit, and therefore against her clit, as she slowly pushed the tip in and out of her increasingly slick folds. With her efforts, I could quickly see her imminent climax.
I gazed at her, at her body as she lifted her sweaty back off of the sheets. I watched her heavy breasts rising and falling as she hurried to catch her breath, but never quite doing so. I don’t even think she knew I was in the same room, let alone resting next to her, marveling as she brought herself to an amazing orgasm. As I had seen all those years ago, she froze, holding the vibe securely against herself, perfectly still except for the minute vibrations against her clit. I could see her knees trembling with an overwhelming urge to snap shut together. But Unlike watching her growing up, this time I heard it. “Michelle”, she screamed my name, evidently aware of my presences, and for whom she had put on this performance. “I love you”, she managed to scream while in the throes of her ‘forever’ time. She threw her head back with a powerful force as she climaxed, her whole universe centered on the rapture she felt as she came.
I lay beside her in complete awe as she struggled to come down from her orgasm. I don’t think I have ever seen something as amazing or wholly erotic, sensual, and passionate, as I did just them. My sister struggled to come down from whatever cloud she had just perched. The silver vibe still buzzing away at the entrance of her pussy, still in tender contact with her sensitive clit. She left it there, I guess trying to prolong the sensation, similar to when I saw her thighs clamping down on her hand as a teen. “Wow”, I muttered, watching her body convulse as orgasmic aftershocks rippled through her body.
With effort, she pulled the vibe from body, the silver made to shine as it was coated with her cum. I could tell that she could barely lift the thing, prompting me to reach over, gingerly taking it from her, and turning it off. I held it in my hands, ready to place it beside her, when something overpowered me. It must have been the combination of the erotic display she just performed, and the aroma of her cum as it smeared on her thighs. But for whatever reason, I leaned back in the bed, still beside my beautiful sister in the afterglow of a powerful orgasm, and then put the vibe into my own mouth.
The intoxicating aroma was the first thing to assault my senses, penetrating my mind as easily as the toy penetrated her, all while I was doing nothing to stop it. My tongue then danced over the tip, allowing me the sweet taste of my sister’s cum. It was pure ambrosia. My lips opened wider, pushing more of it into my mouth. I had never felt so full, as the solid toy filled my mouth, touching the back of my mouth, forcing me to overpower my own gag reflexes. I used my tongue to push it out, only to use my hand to force it back in. The two forces played well with each other, as I started fucking my mouth with it. I slowly bobbed my head back and forth too, pretending I was sucking some guy off.
I held the toy in my mouth with my left hand, as my right trailed slowly down my body. Jessica wanted to see me masturbate as well, and I was going to show her how erotic a girl with a clit could be. My right hand pulled my clit free from the small, purple panties, and formed a firm grip around it. “Jessica!” I tried to scream, though I came out as an intelligible slur with the vibrator lodged in my mouth. My hand had years of practice, as I began to stroke my seven inch clit, all for the singular pleasure of my sister, my lover.
It didn’t take long, I’m almost ashamed to admit, before I was moments away from joining my sister on the cloud-perch. My back began to curve, lifting up from the bed, while my ass and shoulders remained firm. My eyes lost all focus, as all I could do was stare blankly at the ceiling above us. I bent my knees, spreading my legs as wide as I could on the bed, all while I continued to stroke my clit. My left hand let go of the vibe, my lips closing around it to keep it in place, as my hand found my nipple, and pinched it hard, eliciting another unintelligible scream from my lips.
With effort, I pushed the vibe from my lips, it falling on my chest, but I didn’t want my next words to be muddled. I wanted my sister to hear clearly what I was going to say as my own climax rocked me. “I love you too, sister!” I screamed, my voice giving out with the last syllable. My hand made a final downward thrust, gripping my clit tightly, just as I came. I have no recollection of the power my orgasm had, only that my cum had come to lie everywhere, and I had no control over my jets of semen as it flew with powerful thrusts out from my clit. Both of our new lingerie became spotted with the white goo, both the baby-doll’s, and the panties. More fell on our exposed flesh, a pool of glossy liquid became nearly invisible, except at the right angle with the light.
Jessica took my hand, my right hand that had just been drenched with my cum, and held it to her lips, kissing it, and sucking at whatever cum she could get. Her tongue eagerly licked every drop from my fingers, before she rest her head on my chest, content. “I love you too, sister”. She mewed, before we both fell to sleep.
I look forward to your responses to this latest installment, as I am working on Chapter 4 (and possibly Chapter 5 as an epilogue). I want to thank everybody that has been so supportive of my first delve into writting, and to assure you that even at the conclusion of this series, I will be looking at creating more.