It was then I noticed the clothes she’d laid out for me on the bed.
“Oh, Bec are you for real?” What can only be described as a ‘naughty schoolgirl’ uniform lay on the bed beside long white socks and white panties and a bra. Black high heels sat on the floor before them. “I can’t wear that, why would you even want me to?”
“You CAN wear it and you will! And ‘why’, is because you need to be schooled in respect Chrissy. Whilst you’re a guest in our house you’ll do as I say. Alright, little broth… little sister?”
I’d never worn women’s clothing before. I wasn’t gay, or for that matter did I think I was bi. I knew I was feminine; I took after my mother more than my father and I often did look at my own body and see female lines and curves. Could I do this? Dress like a girl in front of my sister, I wondered. Right then, before I dropped the towel, the answer came to me. Why not? What would be the harm? If she wanted it, why wouldn’t I want to make her happy? I decided to submit fully. To accept whatever my sister had in mind and possibly open myself to a new understanding of my very nature, to fully experience whatever was to come. Who knows, I might just enjoy it!
Rebecca giggled as I allowed the towel to fall to the floor and she spied my small penis again. To willingly expose myself to my sister’s gaze was a thrilling experience. I reached down and picked up the panties. They were full-backed briefs, silky to the touch, and had a seam of lace around the top. The feeling of stepping into and sliding up my smooth legs a pair of my sister’s panties was wondrous. When I’d finally pulled them up to my crotch, my penis had begun to swell, and it wasn’t lost on my sister.
“Oh, so it does get bigger Chrissy, that’s nice to know,” she exclaimed. I ignored her comment and tucked it into the panties. I had no problem with the bra, made of the matching material it fit me snugly, Rebecca herself not having large breasts. I next slid on the socks and pulled them up to just below my knees. The skirt was a blue pleated tartan and was short enough to leave my panties visible at the rear, I put on the tight white shirt and sat on the bed to place the black heels on my feet. I had some doubt as to whether I could walk in them but when on, I twirled for Rebecca to seek her approval of my new look and found I handled them fine.
I stood before my still-seated sister and awaited her response. She said nothing of my now fully erect cock poking out of the top of the panties, lifting the dress, and I had a horrible feeling she was about to laugh at me and mock my appearance. To the contrary, still without speaking she stood and took me by the hand down the hall to her room. I was seated at her dressing table, and I finally knew what was happening. She began by tying my hair into pigtails, then applying foundation on my face, followed by mascara and eye shadow. Lastly, Bec applied a deep red lipstick to my lips and my transformation was complete. She again took me by the hand, and we stood together before her full-length mirror.
I was a girl. If I’d been shown a photo of myself before this moment, I wouldn’t have recognized myself in it. I turned to Rebecca and almost in tears, I asked if I looked, ok?
“Oh sweety, you look beautiful. I finally have the little sister I’ve always wanted,” she replied and took hold of my other hand. Our bodies facing, merely inches apart. She dressed as what I now saw as a teacher, and me, her student. “But now I have to teach you to really be a girl; are you ready for that Chrissy?”
I nodded in assent and allowed her to lead me back to the chair.
“Show me how a girl sits Chrissy,” Bec asked.
I sat down and crossed my legs, placing my hands on my thighs as ladylike as I thought possible. To my amazement, it displeased her. “Oh no, no, no Chrissy. That’s how a lady like me would sit. You are a dirty little slut! You’ll spread your legs whenever you sit!” Just as I knew she could, her demeanor had changed from saccharine to sour in the blink of an eye. She walked over and forcibly spread my legs, the skirt again riding up over my hard cock.
“Oh, there it is again! My how it’s grown. You like being a girl don’t you Chrissy?” she asked, and it hadn’t been lost on me that she was only calling me ‘Chrissy’ now. “What does ‘it’ want Chrissy, does it want this?” Bec stood back and lifted the front of her skirt. It was only then I noticed she was wearing stay-up, thigh-high stockings. The tops of which came just below her bare, bald pussy. She wore no panties. My sister presented her sex to me, the skirt, the stocking tops, and her hands, all forming the frame around the most beautiful sight I’d ever laid eyes upon. I could see no inner labia, just the perfectly vertical slit of her outer lips. I wanted to kiss it, to lick it, to smell it but dared not act until given license.
She must have seen the desire on my face. “Oh, you do want it don’t you Chrissy? You want your sister’s pussy!” I could tell she was getting off on it. The dirty talking, the exhibitionism. She wanted to fuck as badly as I did but she wanted to build it up for as long as possible and I wouldn’t complain. “You want to lick my pussy little brother?” She’d stuffed up, calling me her brother and not her sister but she went on regardless. “Maybe I SHOULD let you lick my pussy; you have been a good girl up to now.”
She backed away towards the bed and turned, lifting her skirt around her waist, revealing her amazing bottom to me for the first time. “But I don’t think you’re ready for that,” she leaned forward on the bed and still standing, spread her legs. With one hand she clutched her right ass cheek and spread, displaying her anus. “You can lick my ass now Chrissy. If you do a good job, I’ll let you lick my pussy!”
I needed no further prompting. Within seconds I knelt behind my sister, my face level with her butt. She let go of her cheek and I took over, spreading both globes wide, pulling apart her most intimate hole. I spied her pussy beneath her pink anus, dripping with juice. The desire to taste it was overwhelming, but I dared not touch it until allowed. I kissed her sphincter directly, her hole, hot upon my painted lips.
Rebecca sighed at the first contact then groaned when my salivating tongue tried sliding inside her passage. She was still puckered tight so I returned to kissing and licking around her anus, up and down her crack. Again, I tried penetrating her sphincter and found her loosened. My tongue was able to probe deep into her asshole, tasting her feminine earthiness. My mouth hermetically sealed around her anus, my tongue wriggling inside her, I pulled her hips back onto me, burying my face in her ass. “Oh yes Chrissy, lick my ass. Lick your sister’s asshole. Taste my breakfast you little cunt!” The talk spurred me on. I wasn’t sure if it was possible to bring a girl to orgasm anally, but I was trying my best. My jaw tired; my tongue ached, but I would’ve kept going all day if she’d allowed it.
It was Rebecca who put an end to it. Unexpectedly she spun around and dropped to the floor before me. “You passed Chrissy, now I’ll give you something.” Kneeling together she pulled my cock loose of the panties and began stroking me, the head of my dick was already covered in pre-cum and I knew it wouldn’t take much for the real stuff to follow. Rebecca moved in closer and our mouths connected, my face was covered with saliva and the smell of her ass but she showed no sign of revulsion. Our tongues met, entwined. She seemed hungry for the taste of her butt and we kissed with passion. Her saliva dripped from her mouth, she scooped it and smeared it on my cock. The lube sent me over the edge.
Rebecca somehow knew it was about to happen. She leaned back, spreading her legs. Directing the head of my cock towards her cunt she made the last few pulls necessary for me to cum and then it happened. Spurt after spurt of my hot cum sprayed between her legs. The pubic mound taking the most, then her upper thighs and stocking tops. Cum ran down her slit to drop to the floor between us. She milked me until the last ounce had seeped from my cock.
“Did I do good Rebecca?” I meekly asked, seeking her approval.
“It was a very good start, Princess. We’ll have something to eat and drink then continue your training, ok?”
“Yes, Miss,” I said, and this seemed to please her no end. She kissed me again, not sexually or with passion, just a friendly kiss on the forehead and I knew I’d done well.
*
I thought my sister would have been quick to shower again, but she seemed content to just wipe my cum from her pussy and legs with the panties she made me remove, along with the rest of my uniform. Again, I was standing naked before my big sister, awaiting her next move. She removed her clothing as well and my immediate thought was, we were going to fuck. I should’ve known with her it wouldn’t be that simple. Moving to her dresser she removed black lingerie and stockings and handed them to me. “You’ve graduated to women’s clothing now Chrissy. You’ll go to your room and put these on then join me in the kitchen for lunch, ok?” She offered and I nodded and reluctantly left the beautiful sight of my naked sister behind me.
The lingerie she had given me was a tight lace teddy that attached to the thigh-high stockings with suspenders. It contained my erection well and as I admired myself in the mirror, my legs long in the heels, my hair still in pigtails, I firmly believed I could’ve been a trap for any red-blooded man out there.
I did as was told and awaited my sister in the kitchen. She appeared shortly, dressed (surprisingly I thought) in tight brown suit pants and another white shirt. She still had her hair in a bun and the glasses on. I’d expected her to be dressed like me, but she still looked hot; the pants cling tight to her immaculate behind and thighs. And then I noticed it. As she went about making us lunch, I made out the front of her pants for the first time. Namely, what seemed to be down the front of her pants. It lay along her left leg, stretching from her crotch to mid-thigh. The unmistakable outline of a cock. She was wearing a strap-on.
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