Jessie and Jenny

My name is Jessie, and I'm transsexual. Not the kind you see on Jerry Springer. I'm just a relatively normal, average, nerdy person who just so happened to have been born into the wrong body. This is a story of what happened between myself and my sister. I hope you enjoy it.

~~Jessie <3

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Jenny and I are together for perhaps the last time today. She's here in New York to visit me one final time before my upcoming flight to Europe to be with my boyfriend, Fionn, who I intend to marry. After an enjoyable but otherwise unremarkable evening together in the city, we retire back to my apartment in Brooklyn.

I offer her the choice to sleep on the futon in the living room, but she says "How about right here, like when we were kids?"

I blush a bit and say "Sure."

She jokes, "After all, it's just us girls."

That makes me blush more.

She snuggles up to me, slipping out of most of her clothes. I blush and ask "W-what are you doing?" and she grins.

"I visited the beach at Coney Island early this afternoon. I've got a swimsuit on underneath."

I answer "Oh," trying hard not to sound concerned, but swimsuits are one of my biggest turn-ons-- and it's largely because of her. I smile through my growing blush. "Wow, you've really got a great figure. I'm impressed."

She finally returns my blush. "You've changed quite a bit yourself. You look a lot like mom."

I grin. "Hey! I do -not- look 50."

She laughs. "No, not that, silly."

I, trying to be polite, turn to the corner and sigh. "Night, Jenny."

She, unexpectedly, spoons up behind me and gives me a hug. "Aww, don't you wanna chat? This may be our last chance before you go to Europe." I blush, resisting the urge to wriggle back closer against her warm, soft, swimsuit-clad body. I turn about, facing her, nosetip almost touching nosetip.

"Sure, I'd love to." I return her gentle cuddle, resting a hand chastely on her hip.

"You feel nice," she muses, petting my side absently.

"You do too," I return, smiling. "I've always thought you're so pretty."

She blushes deeper. "Awwww! How sweet." She returns the compliment. "I always thought you were very handsome." She thinks for a moment. "Well... 'pretty', now."

I blush, and admit, "Yeah, I wished there were more girls like you."

She nods. "I wished there were more guys like you. Then you told me you were Jessie instead of James. She suddenly giggles. "Okay, I get it now. Jesse James."

I grin. "Took you long enough."

Then I pause for a moment, becoming suddenly solemn. I realise that, despite myself, I'm growing uncomfortable stiff, and since I'm tucked neatly into my panties, it's becoming painful. I wriggle my hips a little, trying to ease the pain a bit by changing my position. "Yeah.. I guess that did kind of come out of left field a little, didn't it? My change, I mean."

She shrugs. "Not really. I always knew you were different, I just didn't know how different." She rests her hand on my hip, making me blush. "You have really nice hips!"

I grin. "T-thanks."

She starts gently running her hand over my curved hip, tracing my contours. "A part of me wishes you weren't my brother. Well, sister," she muses, petting my side.

"W...why's that?," I ask.

"Because, to be honest, you're really cute, and after what Tommy did... (Tommy was her ex) I wish I knew someone more like you and less like him."

At this point, my blush becomes practically volcanic in its intensity. "I-...I don't know what to say. I kinda wish you weren't my sister either... you're just so beautiful."

She pouts cutely, and gasps "Awww......," then leans in and gives me a slightly un-sisterly kiss on the lips. "Now I'm REALLY sad you're my sibling."

I nuzzle her nose. "Well.... we're both siblings, but what can't two siblings do that any other couple of people can't do?" I carefully phrase this sentence so as to be sufficiently ambiguous to avoid reproach, just in case I'm misinterpreting her with my desire-clouded mind.

She licks her lips softly, thinking. "Well... you know."

I blink. "Nooo," I answer, feigning innocence. "I don't know. Got an example?"

She looks down. "Well, you know... be ... boyfriend and girlfriend.... or, whatever...."

I draw her closer, breathing in softly, considering my next words carefully. "Jenny.... we're both adults." I notice that her breathing is also a bit ragged, her face a bit flush.

"I know... we are." She nestles closer.... "Pretty Jessie."

I return her flush, gently stroking her sides and her lower back through the soft spandex of her one-piece suit.

"Can I tell you a secret?", she whispers.

"Yeah," I whisper back.

Her response makes me blush so heavily that I fear I'm going to faint. "I.... I... I always wanted you."

I softly stammer and murmur, unable for a moment to form words. "J-jenny," I whisper, taking care that each syllable doesn't sound reproachful, so she does not fear for what is going to come out of my mouth next... my voice is soft and strained. "I... always... wanted you too.... There. I said it." My blush does not fade one iota, as I look into her eyes and gently repeat, "I always wanted you...."

Jenny rests her hand down further on my hip, her fingertips almost touching my rear, clad in silk pyjamas. "What did you... what DO you want to do with me?"

I close my eyes for a moment, thinking how to word it. Opening them, I nuzzle noses softly with my sister, and whisper, "I've wanted to make love to you..." I pause. "I've wanted to slowly fill you, to hear you moan... to make you cry out in delight... to please you."

Her blush is almost palpable. "I...I want that..."

I move closer to her, my own hands slowly slipping lower, cupping her girlish rear, not quite as large as my own but perfectly round and soft, through her suit. "I've wanted you so bad..."

My sister nestles closer, her fingertips playing over the tops of my silky panties, just under the waistband of the pyjama bottoms. "Undress me," she asks softly, in a whisper.

"Yes," I answer, thinking of how long I've longed for this moment. "Lie on your back," I whisper, and she complies, lying down on the soft futon. I gingerly stretch the shoulder straps of the maillot, helping her wriggle her arms out through the holes. Then I slowly begin to tug the suit down and off her pretty little body, licking my lips softly as I gaze down at her, whispering, almost worshipfully, "Jenny...."

She gazes up at me, smiling, then grinning. "Jessie...." Her grin softens back into a soft, gentle smile. "Jessie," she repeats, trying out the sound of the word.

"Ohh, Jenny," I gasp, as I catch a glimpse of her soft, round breasts for the first time. They are larger than mine proportionally, yet still of moderate size; round and soft and perfect, standing out well-formed from her trim chest. "Oh, Jenny," I whisper, as I draw the suit further down, watching inch after inch of soft, milky flesh being exposed as I reveal my beautiful little naked sister.

Finally, I slip the suit down below her loins. She is utterly bare, hairless as a baby down there, the soft folds of her womanly cleft peeking out pinkly between soft, trim thighs. "Oh my god, Jenny," I whisper under my breath.

"I epilate.... so I can go swimming without embarrassment," she notes, and I nod.

"It's beautiful... god, YOU'RE beautiful!"

She blushes, cooing softly from my compliment, as I slip the suit down and off my pretty little golden-blonde sister.

I wriggle again, attempting to be discrete as I slip a hand between my thighs, adjusting myself, untucking my rapidly swelling shaft so it is no longer bent painfully back against itself.

"My turn?," I breathe, trembling softly in excitement.

"Let me help," she whispers, reaching down to gently tug down my pyjama bottoms first. "Oh, wow," she moans, a bit distantly, as she sees the sizable bulge in my panties. "BIG sister," she jokes.

"You have no idea," I grin, looking down at her.

"Mmmmm, and the shirt?," she asks.

I nod, and she undoes the buttons of my pyjama top, slipping it off my form, her soft hands incidentally brushing my nipples in the process. "Ohhh...," I gasp at the touch.

"They're more sensitive now?," she asks, and I nod. "Good." She smiles; I do likewise. As she removes my shirt, she giggles a little at my small, perky, developing breasts. "Awwww! Cute!"

I blush. "Thanks," I smile. "Not as gorgeous as you."

She blushes too. "You're adorable, don't put yourself down so much."

I smile.

"Now the last bit," she grins mischeviously, looking down at my panties, hooking one of her slim fingers into the waistband.

I shiver, and nod my assent. "Y-yeah..." I swallow softly.

"You sure about this?," she asks, concerned.

"Yes... oh, god, yes. Please.... please take them off," I whisper, blushing at my own words.

"Mmm, okay," she responds, hooking both thumbs into my panties and tugging them down, revealing my own well-epilated loins. Amazingly, my shaft is harder than it's been in years-- harder than it's been since I went on hormones. Of course, I'm not surprised.

"WOW!," she gasps for a moment. "Oh my god!"

I blush. "I-it's not -that- big."

She blushes as well. "It's perfect."

I gaze into her eyes, smiling like a sphinx. "Enjoy it while you can," I grin, making a joke about my transgendered status.

"I will," she grins back. Her soft hands gently take one of my own. "I want you to feel something," she whispers, drawing my larger hand between her thighs. The heat and wetness are immediately apparent; she's practically soaking wet.

Her voice lowers to a whisper. "Do you know how long I've wanted you?"

I blush, whispering back, "I've wanted you all my life."

She blushes too.... leaning closer, positioning her lips by my ear. "Then take me," she whispers. "Take me, Jessie. Take me."

I move myself atop her, being very careful not to put too much pressure on my delicate little sister, or to hurt her in any way. She's several inches shorter than me, and has an average build, like her father-- not the statuesque shape my mother gave me.

"I -want- you," I whisper, gently guiding the slick, preseed-drooling tip of my almost painfully erect shaft between the parted netherlips of my sister's little treasure. "God, how I want you."

She looks up at me, blushing... and then just repeats her request, almost like a command. "TAKE me..."

I lick my lips, take a deep breath, and nod softly. "Yes," I answer, focusing on the moment, on feeling every tender instant of our forbidden, long-desired pairing. I gaze down into her eyes, whispering "Jenny," as I slowly press forward, feeling the bulbous tip of my stiff, purple-pink erection easily parting her slippery, wet, yet TIGHT folds, slipping against the entrance to her vagina.

I enter her soft little sex, moving slowly and lovingly, inch by inch, inside her... inside my beautiful sister, my shaft surrounded by her moist flesh. "Jenny," I whisper again in wonder, that simple name somehow meaning "I love you", and "I need you", and "I've always wanted you," and "God, yes," all at once. "Oh, JENNY!," I whimper, my face betraying the incredible pleasure of my sweet sister's wet, hot little sex about me, as slowly, inch after tortuously wonderful inch, I slip within the object of my sweet desires, filling my sister's sex with my heavy shaft. "Oh... JENNY..."

As my head slips inside her, parting her tight, almost virginal little folds, she lets out a soft, muted gasp.

"N-nnnngh," she sighs, her sweet, hot little sex just as soft and warm as in my dreams, as it slowly envelops my remarkably hard shaft, so long and thick despite being on female hormones for so many years. "J-jessie," she chokes softly, closing her eyes after fixating one last long, haunting glance upon me with her sparkling pools, pleasure and need reflecting upon her irises as upon a mirror. As the tip of my shaft brushes against her g-spot, she trembles, nestling closer, beginning to slowly wrap her sleek thighs about my waist.

I slip deeper, whispering at last the words I've so longed to speak, to admit to her... "I love you.... God, I love you."

She nods softly, letting out a gentle groan. "I love you too!"

I hold her close, like lovers, like mates, my gentle hands cupped over her pretty round rear, which I've admired since childhood. "Jenny," I groan, as my heavy shaft bottoms out within her, my hairless, trim sac nestling against her bare perineum. Slowly, I begin to rock my hips, making love to my darling one in a slow, tender rhythm.

"Oh, ohhhh," she sighs, loving the feeling of her sister's thick shaft inside her tight little slit. "Touch me," she whispers, and I nod, knowing what she wants... reaching down to gently nestle a thumbtip under the hood of her stiff little clit, blushing when I realise how very erect it is. Gingerly, tentatively, I begin to caress her little nubbin, finding a rhythm which makes her moan and whimper in delight... then, I again begin to thrust within her, carefully at first, using my other fingers to keep my hand in place upon her thigh.

"Mmmnnnnnn, Jenny," I whisper.

"Jessie!," she gasps, as if to say "Oh my God!" I moan, thrusting in and out, in and out, still as stiff as the moment I entered her.

"I love you...," I whisper, and slowly thrust in... then out. "I... [*in and out*].... LOVE... [*in and out*].... you.... God, I love you!" A happy tear trickles down my cheek, and I let out a soft sob of joy as I finally express my true feelings to my beautiful, my beloved... Sister making love to sister, naked, unprotected, and unashamed. "Ohhhh," I whimper, shivering a little.

As I grow more adept at pleasuring her, my touches and my thrusts in near-perfect sync, she begins to tremble, evidently approaching climax. I sense this, and mrrrr appreciatively, whispering, "Yes... cum for me... cum for your Jessie." She lets out a helpless little tremulous whimper, unable to form words, the pleasure overwhelming all rational thought. I repeat the words, as if a gentle command or a wish, whispering them softly and gently into her pretty little ear. "CUM for me," stressing that first word, making it a loving sort of command.

"A-ahh," she moans, getting closer.

Again, I repeat... "CUM... for... me...," thrusting in and out, holding off on my own orgasm, the years of female hormones making this much easier.

She manages the words, "Y-you too!," and then cries out in helpless bliss, her sex clasping over and over about my shaft, practically making audible -squish- sounds from being so very wet, as I continue to thrust within my pretty little sister, as she climaxes...

"Ohh," I whisper, letting myself go as she cums about me... "Oh GOD... AH!! A-ahhh! J-jenny! Jenny.... J-enny...," I whine, as my climax overtakes me and I spurt over and over within her, further moistening her already sopping-wet little cunny with slick lubricitive girlcum. "JENNY... ohhh, Jennnnnnnyyy....""

I hold my beautiful sister's naked body close to mine, nestling up with her, the warmth radiating between our naked forms, our joyous coupling complete, sisters united as lovers.

"Now I'm tired," Jenny grins weakly, stifling a yawn.

"Me too," I smile, and kiss her lips. Carefully, I turn us onto our sides, my shaft still inside her. "Goodnight, Jenny," I whisper, kissing her again.

"Mm... goodnight, Jessie," she smiles. "Thank you..."

I held her close, basking in the love and tenderness we shared together. Slowly, I fell asleep, but not before mouthing the words one final time: "I love you........"

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F I N

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Copyright (C) 2006 AnyJessie. Post freely, so long as this attribution is included. I hope you enjoyed the story!