Sister’s Surprise_(0) by Achilles_Heel

A closet cross-dresser is caught and exposed, but gets an even bigger surprise from his sister.

Sister’s Surprise

My parents would never understand. How could they? They raised my to be a good little boy, and that was all they knew. They had no idea about my cross-dressing fantasies. It was a life I kept secret from everybody. And until three days ago, it was secret I kept even from my girlfriend April. A business meeting that ended early also ended our relationship.
I was always small growing up, but that didn’t stop me from being active. In Junior High, I had wrestled and was on the track team. In high school, I joined the swim team, but it was my track career that excelled, breaking a few school records in the high jump (and only a fraction of an inch from a state record). It was during my athletics career, that I met April, a cheerleader, who I thought was the love of my life. We moved in together right after graduation, but soon life together began falling apart. It wasn’t the romantic ideal that we had both envisioned, and soon our life together became unbearable. In a way, I am thankful for her meeting ending early.

That was why I was standing at the door of my sister’s apartment, knocking softly, with boxes of my stuff sitting next to me, containing a total of the life I had left. “April kicked me out”, I said trying hard not to start crying, as the door opened with my sister Jessica standing at the threshold.
“I know”, she replied evenly, a worried look on her face. “She plastered the breakup, along with what you were doing, all over Facebook. You might want to save yourself the trouble and just delete your account”. She smiled weakly at me, as she grabbed a box and hauled it inside. “Jen’s at Tyler’s for the next few weeks for summer vacation, so you can have her room”, she took the box into her daughter’s room.
“You aren’t mad?” I asked, still standing outside the door.
“Of course not”, she replied with some mirth. “We’re family. And besides, growing up, I always thought it was odd that some of my clothes would go missing, and return a few days later. I kinda knew you were closet cross-dresser. But if it made you happy, I wasn’t going to stand in your way, or rat you out”. She seemed to smile at some secret memory, and then she smiled knowingly at me. “Look, there are no judgments here. I love you no matter what. If you want to parade around as Michelle here”, she used the feminine of my name, “then that’s fine by me”.
She help load the rest of my things into her daughter’s pink room without much more conversation, then excused herself to make dinner, and so I could put away some of my things. After she had gone, I stared at the simple brown box April labeled ‘fag’, and that I had crossed out. Inside were a collection of clothes that would take me from Michael to Michelle. I had thought about what Jessica had said about this being a place without judgments.

“I hope you like spaghetti”, Jessica said from the kitchen when she heard my door open. Her back was turned to me, as she scooped the noodles from the pot to a nearby plate. “Oh, and I already hacked into mom and dad’s Facebook and deleted April from their friends, so hopefully, they won’t know about it until you decided to tell them”, she said, adding the red tomato sauce to a pile of noodles on a plate. All strength must have left her hands as she turned to see me, dropping the freshly prepared plate on the floor.
I stood for a while under her shocked gaze. My heart was beating uncontrollably out of my chest. I had decided that for the night at least, I was Michelle. I wore a wrinkled white blouse with nearly exposed shoulders. The straps of my white bra visible as they arched over my shoulders, secretly stuffed with breast forms to give myself some cleavage. I had on a faded pair of hip-hugger levi’s, and some cute yellow socks, no shoes. I also donned a wig, turning my usual short dark hair into long, wavy platinum blonde tresses. Red lipstick coated my pouty lips, my mouth open so I could breathe.
We both stood in silence, the sound of a nearby clock starting to drive me insane as my heart beat at least twenty times per tick-tock. The eons ticked by on that annoying clock, as both of us just stood there. My fears creeping into my mind, suddenly thinking this was a horrible idea. I turned, ready to run back to the room, and return as Michael.
“Wait”, Jessica called after me. “Aren’t you even going to help me clean this up… Michelle”, she said, the name sounding foreign to me, but also so right.
I was unable to form words, my voice fleeing as my heart wanted to. I slowly nodded, as I took a step closer to the kitchen. My knees trembled trying to hold up my own weight.
“When I had read the mean things April has posted about you, I just couldn’t believe them”, Jessica said as I took another shaky step forward. “But now I can see that she was just jealous. Jealous that she will never look half as good as you do right now”.
It was all I could do to smile at her. Growing up, my sister and I were always close. Even though she was three years older, and made some different life choices that had her with a six year old daughter, and a ex-husband at the age of twenty-two. She confided in me that she never regretted any of those decisions. They are what forged her into the strong woman that she was today.
“So,” she said, as she was cleaning spaghetti off of the kitchen floor, “Why is your shirt so wrinkly”, she asked with an amused look.
Finally finding my voice, and feeling much more relaxed, I walked into the kitchen. “Well, when you’re trying to keep a part of your life a secret, even if you do have time for ironing, you still end up throwing the clothes in a pile in a hidden spot when you’re done”, I said. It was actually a concern I had before, but I figured if it was part of my private life, I would just deal with the wrinkly clothes. “I am actually hoping I could do some ironing while I’m staying here”.
“Of course you can, but I have a better idea”, she smiled, the mess on the floor nearly cleaned. “I got some clothes that don’t fit me anymore. You want them? After all, sisters share clothes”.
I was a little taken aback when she called me her sister. I guess, if I were going to live as Michelle, I figured I would be her sister. “That’s sounds great, sis”, I said, trying to change the pitch of my voice to be slightly more feminine.

I could hardly eat. Although I knew Jessica was accepting of me like this, this was the first time I had actually been seen as Michelle. Well, not technically, but I’ve written April out of my life now. When April had seen Michelle, I freaked out, and tried to hide. This time I was with Jessica, and although my instinct was to run and hide, I was fighting that urge. I was conflicted, and my stomach was in knots. Hence my loss of appetite.
“Well, I know Michael doesn’t have tits”, Jessica said, breaking the uncomfortable silence with what was bound to be an awkward conversation. “So how come I’m staring at Michelle’s cleavage”.
“Breast forms”, I said, now assured that it was an awkward conversation. “It’s the same as stuffing my bra”. I said, assured I was blushing from head to toe.
“So what size are your breasts”, she started, “with the stuffing?”
“I don’t know”, I said, visibly shrinking. “38C I guess”.
“That’s perfect”, she exclaimed. “I’m 40D now, but I have some 38C bras from before I had Jennifer”, she said. Her voice took a quieter, conspiratorial tone, “and I still sometimes put them on, you know, to make the girls really pop. Hurts like hell, but makes my tits unbelievable”, she winked.
“Jessica”, I said, shocked that she would be some liberal talking to me.
“Oh relax. It’s just a little girl talk between sisters”, she said, smiling, but still staring past my wrinkly shirt to my cleavage. I don’t think I have ever felt so exposed…or excited.

Dinner was quick, and Jessica practically dragged me into her room, opening her closet. “What about your other sizes? Do you know your dress size, or female shoe size, or anything else?”
“No”, I admitted. Since dressing up, I basically had to guess sizes, keeping the stuff that fit, tossing everything else, until I discovered my sizes. Discovering my bra and panty size came first, everything else I just had to guess if they’d fit.
“Okay”, she said. She tossed a whole bunch of clothes from her closet onto the bed, and was heading to her dresser drawer, where she keeps her underwear.
“Um, that’s okay”, I said, more than a little embarrassed, “I have plenty of bras and panties.
“Oh, I bet you do”, she said, pulling out a locked box from the rear of the drawer. She pulled off her necklace, a key dangling from the long silver chain, and opened the box, hiding its contents from my view. “Michelle, I want to tell you about my most powerful orgasm”, Jessica started in a somber tone.
“I was just sixteen. I had masturbated several times, reaching mind blowing orgasms. And I had even given Tyler a few hand-jobs, watching his cum oozing out, coating my hand. But I had no idea what levels of ecstasy I could reach.
“You had stayed home sick from school that day, and mom and dad were still at work. I snuck home early, intent on cheering you up. But when I got home, I heard you. It sounded like you were playing. I snuck up the stairs, ready to bust you for faking being sick. I stopped dead in my tracks as the door to my room was wide open. I dared a glance inside, and I saw you, lying on my bed, wearing my clothes. You had your…rather my…pants down around your ankles, my pink Gem t-shirt pulled up to expose one of my black lacy bras. My matching black lace panties was around your waist, but pushed down to your balls, as your magnificent hard cock stood erect, slick with your saliva, your hand pumping up and down your shaft as fast as you could.
“I was captivated by the sight. Even though I could clearly see the little boy jacking off, I envisioned a little girl, exploring herself for the first time. It turned it from a dirty, nasty thing that Tyler made me do to keep him from dumping me, into a thing of beauty. Then you started to cum. Your breaths became labored, as you chest rose and fell trying to catch your breath. Your back arched, as I heard the feminine moans escape your lips. I watched, seeing jet after jet of your pearly semen erupt from your cock, shooting high into the air, and landing on your stomach, your chest, my bra, my panties, my shirt, and on my pants”.
Jessica finally pulled the box out from behind her back, and pulled out two small wads of black cloth, then slowly straightened them out. I nearly fainted as she pulled out the very same bra and panties that I had cum on all those years ago.
“After watching you, I ran to Tyler. I wanted to feel as good as a woman as you had been. I opened my legs to him that day, all while in my mind imagining it was you, my sister, penetrating me, and making me a woman. He had no tenderness as he violated me. I felt his hard cock sliding in and out of my young pussy. His dick throbbing inside of me, his orgasm was herald by grunting and a quickened pace with deeper, more powerful thrusts. I remember trying to arch my back, to feel as you had, but his weight on top of me crushed me. I tried to moan as my own orgasm neared, but he shoved his tongue into my mouth. I had tried to have the experience you had, but Tyler denied me. He even denied me cumming as he slid his spent cock out of me before I was done.
“Just as fast as I ran to him, I fled, returning home, to find you lying in your own bed, sweat dripping from your face as you pretended to sleep. When I got to my room, I smelt my perfume generously sprayed around, thinly disguising the scent of sweat and cum. I found the bra and panties you hid halfway into the laundry hamper, and pulled them out. I stared at them, seeing your dried cum staining them. I don’t know what compelled me, but I slowly undressed, then put them on. I stood, staring at myself in the mirror, my black bra and panties caked with white cum. I finished by dressing in the exact outfit you had just worn. I undid my pants, pushing them down to my ankles, and I lifted my shirt to expose my cum-covered bra. I fell back on my bed, sliding my hand beneath the waistband of my panties. My hand quickly found my clit, still slick with Tyler’s cum, as I rubbed myself to the most powerful orgasm I had ever experienced, all while thinking of my little sister.
“After that, these were yours”, Jessica said, handing me the bra and panties. “I tried wearing them again, but I felt like I had just stolen something from my sister, so I put them away, waiting until Michelle came to me, so that I could give them back to her.
“I have been waiting six years to see you again, Michelle”. Jessica was nearly in tears, as she threw her arms around me. “I love you Michelle”, she whispered in my ear. “I’ve loved you since the first moment I saw you on my bed that day, and for every other time I had snuck home early to see you before you turned back into Michael”.
Her embrace eased, as she leaned back to look me right in the eye. The knot in my stomach returned, feeling the embarrassment of having been caught all those years ago. I could feel myself whither beneath her burning gaze. I was ready to shrink to the size of an ant, and escape the world entirely. That is when she kissed me.
I had no time to hold her off, as her red lips pressed hard against mine, being gently parted by my sister’s invading tongue. Her arms wrapped tighter around my body, one hand holding to the back of my head. I felt powerless in her embrace, but as if being held in the arms of a lover. My eyes closed, knowing I’d be safe in her arms.
My lips relented, as my mouth opened so that her tongue could dance with mine. I had French kissed April a hundred times, but never before had I felt the intensity of this one kiss from my sister. Her tongue invaded my mouth, as I was powerless to stop it.
My mind screamed at me. It was screaming some nonsense about how wrong this was, to be kissing my own sister with a passion I haven’t even shared with an intimate lover. I refused to listen. My mind, heart, and soul, belonged to Jessica now, and my body was hers to do with as she pleased.
I was pushed backwards on the bed, her tongue never leaving my mouth, save for the occasional breath. Her lips separated from mine with a smack, and I could still feel her lipstick smeared over my own lips. My tongue jutted outwards, searching in vain for her tongue, and her lips again, not wanting to leave our tender kiss.
I opened my eyes, seeing Jessica straddling my legs, as she pulls her shirt over her head. I envied her chest, the large breasts barely contained in the snug white bra she wore. I wished nothing more than for my own to be as large as hers, to be the envy of women, and the desire of men. She looked down into my eyes, once again burning into my soul, as her hands reached behind her, and the tight bra loosened. With two deft moves, her bra was off her shoulders, held in place by her hands. “I’ve waited a very long time for you, Michelle”, she breathed heavily, and slowly lowered her hands.
My eyes were transfixed on her chest: Two perfect, tanned globes of flesh, a sheen of sweat causing them to glistened under the lights, topped with a tiny areola, and a bubblegum pink nipple. The most shocking, was the small tattoo she had on her left breast, right above her nipple, directly above her heart. It was the single letter ‘M’. “Now that we can be together, I’ll get it finished, so that everyone knows, my heart belongs to Michelle”, she said, before falling forward and our lips locking together again. She devoured me in that kiss, my spirit willingly joining with hers, as her hands fumbled with the zipper and button of my pants.
Again, my mind screamed at me. We were about to take this relationship to a place no brother and sister should. As her hand finally pulled my pants off enough, she broke our kissing, looked downward and smiled. “I guess you’re already wet, hey sister?”, she said, noticing the precum oozing from my rigid cock, the head poking out from the waistband of my pink thong. Hearing her call me her sister again was like a reset in my brain. Michael, her brother, was gone. He would be nothing more than a footnote in the family tree. Michelle, however, had just been born. For too long I had denied who I was. I was Michelle, from that moment, for the rest of my life.
She rolled to the side of the bed, quickly unbuttoning her own pants, and unzipping them. My eyes scanned her body feverishly, as they roamed between her breast as they bounced with the slightest movement, and to her crotch, as she pushed her panties down. I saw the smoothness of her mound, not even a hint of hair, and could smell the heavenly aroma of her sex as it mingled with my own aroma to create a powerful aphrodisiac, assaulting my nose, and overriding anything my mind had tried to say. Jessica, my sister, was about to make me a woman.
Her clothes now tossed haphazardly across the room, she worked on undressing me. She kissed me again, as her arms pulled my shirt off, only breaking the kiss to ensure her efforts didn’t pull off my hair. “I love your breasts, little sis”, she said, looking at my false cleavage. I was worried that she would take off my bra, revealing the flat-chested man my body was. She smiled, her head ducking down, planting kiss after kiss between my breasts.
Her hands grabbed a hold of the waistband of my panties, and with a quick motion, and with me elevating my hips, they were quickly around my ankles. I tried to pull them off my feet, but she held them in place. “Are you ready, little Michelle, to become a woman”, she asked, holding my ‘clit’ upwards, while straddling my legs again.
“Yes”, I screamed through clenched teeth, the anticipation of it all driving me to the verge of ecstasy on its own. “Make this little girl a woman!”
Jessica needed no other encouragement, as she lowered herself on to my seven inch clit. Inch after inch penetrated my own sister, the feeling of her pussy surrounding me. It was a love that only two sisters could ever share. “I want to see you in the throes of ecstasy when you cum, like you were that day six years ago. I want to see my little sister cumming, her back arched, moaning with my name on her lips, and cumming like a torrent inside of me”, she was screaming commands, but I heard none of it. All that mattered was the love we shared, and the beautiful thing happening between us sisters.
With her on top, she had all the control, as I lay there, enjoying the sensation of my first time as a girl. My clit was sliding in and out of her pussy, faster and harder, as her efforts became more primal. Just as bad as she wanted me to cum, to succumb to the orgasm I could feel welling up inside of me, I wanted her to cum. I wanted her to cum in the way only another girl could make her cum. My clit rubbed up against hers, as I quickly felt the unbridled passion culminating. I had no control over my body any longer. My sweaty back lifted off the bed, just as her weight shifted on my hips. My chest rising and falling, trying desperately to keep up with my need for air, as my lips closed, and my breaths became moans of pleasure.
I closed my eyes tight, knowing all too well what was about to happened, but really feeling the experience of it for the first time. As Jessica slammed her body down on my clit, I came, calling her name. Uncontrollable convulsions ripped through me, forcing me to thrust upwards even harder into my sister. “Jessica!”, I screamed as feminine as I could, as I felt each jet of cum penetrating deep inside of her, coating her womb.
Her own orgasm gripped her, squeezing my clit tightly, not letting my precious cum slip from between us, as her moans of pleasure formed my name on her lips. “Oh, Michelle”, she managed, barely conscious as her body convulsed on top of mine.
With my hips thrust upward, I held her there, impaled on my clit, as her body slowly eased, and fell forward, her lips once again touching mine. The air in the room seemed hot, and neither of us could catch our breath as we lie there, still joined, her petite frame pressed firmly against mine, my clit softening, but still within her. We both fought for breath, competing for the same air between our lips. We stayed like that for what seemed another eon, slowly coming to rest.
“Michelle”, she started, “That was the most unbelievable experience I have ever had”. I wanted to say something, anything, but her gentle lips pressed up against mine again, stopping me. Then she rolled on to her back, laying beside me, my clit reluctantly pulled from her pussy. Our hands met, and our fingers interlaces. We fell asleep like that, her head resting beside mine, as sisters. As lovers.

I would very much like to continue this story, but I will base that on the feedback I recieve. 🙂