You Look So Pretty

You look so pretty.

Such a simple phrase, yet it almost seemed like mind control when it was used on me. My dear friend Shawna had found out years ago, wanting to play more with my feminine side, that using those four words absolutely melted me into agreement. I tried to fight it, to protest, to summon the courage to finally resist hearing them, but to no avail. One phrase, and I was hers.

At first it had been little things, like getting our nails done together, or styling my hair a certain way. Then Shawna had taught me to do my make-up, mixing up styles depending on if I was going for a more femboy, semi-masculine look, or Rory was out in full force, taking the town by storm. Regardless, she'd slowly drift into my room, guiding me to my little vanity as I felt her hands in my hair, whispering those controlling, subtle words into my ear.

You look so pretty

Outfits, humiliating situations, whatever Shawna found entertaining, I couldn't resist as she gently pushed me again and again into my femininity. Never too far, never into something I'd be far too uncomfortable with, just slightly pushing past my comfort zone, using those four magical words to make me whine, pouting at her as I agreed.

Tonight, I stood in front of the mirror, blushing at the dress Shawna had 'forced' me into. I remember the first time she showed it to me, apparently finding it on sale on a whim, adamantly refusing as I blushed hard seeing it in her arms.

"Oh come on, Rory. It's so cute!" Shawna had said, a slightly amused smirk on her face. "It is so your style."

"NO!" I pouted, refusing to look at her, my face still red. "I can't wear that to Bethany's party!" Shawna placed the dress down over the couch, scooting over to place a hand on my chest, a single finger tilting my head up to look at her.

"Try it on for me, I just want to see you in it." Her eyes gripped me, unable to look away as I whined, stomping my foot at my very persistent friend. But thirty minutes later she led me to our hallway mirror, seeing my complete reflection, the long dirty blonde wig sitting on my head, carefully walking in the heels she had picked out as well to match.

"See?" Shawna said, taking my arm into hers as we both stared at the reflection, squirming at how beautiful I felt. She offered a supportive squeeze, staring into my eyes through the mirror. "You look so pretty, Rory." I whimpered, legs rubbing together as I relented, as we both knew I would.

A week later here I was, staring into that same mirror, unable to tear away from my reflection. It was an older style of dress, not quite mimicking the 1950's fashion I loved dearly, but certainly influenced by it. A beautiful bold red, with white polka dots spread throughout, it even had a little ribbon bow on my breasts, pushed out by some fake ones I had purchased some months ago. With some shapewear around my waist, I was always amazed at how dramatically I could alter my figure, feeling far more feminine despite my broad shoulders holding the straps of my new dress.

White stockings on my feet, which Shawna had demanded I use a garter belt with, feeling the straps on my legs with each step. I wore my best gaff, tucked away safely, although thankfully the dress flared out enough to hide any excitement. Strappy white heels, and silky white gloves completed the outfit, feeling utterly ridiculous yet I couldn't stop myself from running hands all over my body. Shawna exited her room during one of my many self-examinations, grinning to herself.

"There's my beautiful date." I blushed hard, glaring at her as she chuckled.

"I'm not your date, Shawna." I said, pretending I was simply smoothing out the skirt on my dress. But she just laughed all the more, moving to grab my hips.

"Fine, you can just be my wife then, wearing a beautiful dress like that." My blush deepened, looking away as I refused to answer, annoyed at how easily she could silence me with her words. Shawna offered me a final laugh, walking past in her skin tight dress, a beautiful dark purple, hugging her in what seemed impossible ways. Stepping into her own heels, Shawna stood beside me in the mirror, hooking an arm around mine.

"Oh Rory," she said, slowly moving her hand down to entwine in mine, "you look so pretty." I felt my blush grow even further, a large smile on my face as I gripped onto her more tightly, the bundle of nerves I had diminishing just a little hearing that beautiful phrase. Once again, any hesitation I had about leaving the apartment in this beautiful dress was stripped from me, Shawna easily taking control of my feminine side as she always did.

With a knowing smile, she led me out of the door, heading down the street to Bethany's. The party itself was quite tame, although the first ten minutes I was squirming, having so many people gushing over my dress. My feminine self was quite a juxtaposition from my more masculine side, a common trait I'd expert for girls like me, so when I did embrace her it was quite the change for the people in my life.

We chatted, drank, and laughed, Shawna teasing me as I continued to fret and fix the hem of my dress as I sat there. Wearing my pretty, silky gloves, she also took it upon herself to fix me any drinks or food I wanted, forced to sit in place as I was pampered. I couldn't deny the warm excitement that I always got around her, Shawna so easily pushing me further into that submissive nature.

She kept her hand resting on my leg, on top of my hand, playfully teasing through my hair, that subtle display of control over me. As we said goodbye, walking back hand in hand, there was a nervous energy between us, an unspoken excitement from the evening. Inside the apartment, I could barely breathe as Shawna's intense stare locked onto me, feeling myself suddenly pressed back against the kitchen counter.

Shawna held me in place, staring up at me as I softly whimpered in her arms, gripping my shrunken waist tightly. "You looked so pretty tonight, Rory." I blushed, unable to stop the noises being emitted from my lips, trying to look away as I smiled, but she forced me to look at her with a finger on my chin. The heavy silence in the room was deafening, as I stood trapped from her presence.

"Did you like being pretty for me?" I whined, unable to formulate anything that even resembled words, simply nodding to the dominant woman before me. Shawna smiled, a warm, knowing smile, thoroughly enjoying the effects she was so obviously having over me. With the finger on my chin, she slowly forced me to bend down, far too tall in my heels for her liking, pulling me in for a long, deep kiss. I moaned against her lips, my hands awkwardly at my side, unable to think of anything besides how wonderful she tasted.

Shawna finally broke our kiss, smiling as she held me there, staring into her eyes. With a smirk, she led us both back to her room, my body quivering as I felt her unzip my dress, carefully hanging it up on her door. Her own dress followed suit, watching her intently as I saw that tight dress slowly slip off her body. I blushed standing before her in nothing but my garter, stockings, corset, and gaff, which was working overtime to hide my excitement, Shawna giggling as I was guided to kneeling before her.

Slowly, she removed the rest of her undergarments, her strong body on display before me as I stared in disbelief. Shawna smiled down at me, her hand running through my hair after discarding the wig. Pulled in, I kissed her pussy as she groaned, throwing her head back in relief. I tasted how wet she was, not the only one excited from our evening together, the grip in my hair tightening as I began to lick her.

I listened to her moans, Shawna's legs quivering as I licked and sucked on her clit, lost in the sensation of pleasuring her. I felt her lift a leg over my shoulder to rest on the bed, pulling me even further into her pussy, her body language demanding my obedience. I ignored the straining erection trapped behind my gaff, overcome by the assertiveness of my friend, staring up as I continued to run my tongue through the excited lips of her pussy.

I assumed Shawna must have been close to cumming, as my head was shoved into her pussy, my lips pursed and locked onto her clit. I felt her body shake, legs quiver, silently screaming above me as her pussy danced on my tongue. Riding her orgasm out on my face, having total control over me, I simply stared up in awe, transfixed as I watched her cum hard over and over, head thrown back in ecstasy.

With a final sigh, offering an excitable laugh, Shawna came down from her orgasm, pulling me off her clit as it was far too sensitive to be touched. Playfully, she pushed me against the bed, head resting on her comforter, bending down to offer me another kiss.

"You look so pretty, Rory, with my pussy on your lips." I giggled, blushing hard as Shawna planted a few more tiny kisses on my face, her hand still gripping tightly to my hair. Lifting me up to my feet once more with a finger under my chin, she slowly slid the gaff down my stockings, thoroughly humiliated at how eager my cock was, the tip already glistening, giving away just how much I had enjoyed the past twenty minutes.

Shawna smirked, her hand gently resting on my cock as I moaned, offering the tiniest of strokes as I was pushed to sit on the bed. She climbed onto my lap, rubbing her wet pussy up and down my shaft as I whimpered, barely able to breathe as she stared into my eyes. Leaning in, leaving a trail of kisses on my neck, Shawna moaned into my ear as I was teased.

"Rory, you look so pre-ohhhhhhhh." Shawna was interrupted as she slid onto my cock, feeling her already sensitive pussy stretch around it. I whined in her ear, feeling her so close to my body, her warm breath hot in my ear. Slowly, she moved up and down in my lap, my hands planted on the bed for support, only able to watch as she fucked me.

Already excited from the evening, spending hours dolled up and feeling beautiful, I whimpered as I pressed my forehead to hers, knowing how close I was to cumming. "Shawna..." I could barely speak, my mind's focus gravitating to my cock, ready to burst. She moaned, leaning down to bite my lip, smiling as she sped up in my lap. Staring into my eyes, arms wrapped around my neck, Shawna watched as I was so easily pushed over the edge.

I moaned, gripping the comforter behind me as I came hard, cock pulsing inside of her. Shawna grinned, watching as I succumbed to my orgasm, shaking hard as she continued to slide up and down my sensitive cock. Offering my lips kiss after kiss, she listened intently as I whimpered against her, my eyes rolling back in my head from pleasure.

With a smile, Shawna slowly pushed me down onto her bed, sliding off my cock as she climbed up my body. Pinning each arm underneath her legs, she lowered her used, sensitive, and freshly fucked pussy onto my lips, watching with those beautiful big eyes as I whined in shock, licking her pussy once more now that it was mixed with hers and my cum. She groaned happily, arching her back while her fingers played with her nipples, licking and swallowing underneath her.

"Oh, Rory," Shawna said, scooting back down my body to kiss me, running a hand through my sweaty hair. "You are so fucking pretty, baby girl." I blushed hard, feeling my cock twitch from her compliment, clearly not finished in being played with. But Shawna just smiled down at me, before settling in beside me, both of us cuddling in our exhaustive states.

"So, are you going to fight me the next time I choose an outfit for you?" Shawna asked, listening to my girlish giggle, our legs entwined as we rested together.

"I mean, probably..." I grinned at the sigh Shawna emitted, rolling her eyes as she offered me another kiss. "But, I'm sure you'll be able to convince me. You always seem to know how."

Shawna smiled, "That's because you're more a fucking girl than I am." We both laughed, certainly not a sentiment I was in any position to argue with. Feeling the nylons on my legs with each movement, I tried to ignore my erection trapped between our bodies, simply holding onto my dear friend in the moment.

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After that night, Shawna demanded more and more from my feminine side, which I was more than happy to indulge. From cute skirts and blouses, taken out for lunches and dinners with her friends, to more casual loungewear around the apartment, now wearing leggings and panties far more than any of my 'boy clothes'. Rarely was I able to walk past our hallway mirror without a quick peek at how great my ass looked in them.

Amusingly, Shawna still had no interest in me whenever I wasn't dolled up as Rory, similar to when we decided to room together. We were friends, nothing more, watching sports or simply co-existing. Yet, when she came home from work, seeing me in the kitchen in one of the many dresses I now owned, a perfect picture of the 1950's housewife, heels clicking along the tiles... she lasted all of ten seconds before I felt her hands under my skirts.

One such night, wearing easily my favourite dress, a beautiful bright pink with black trim complementing the brazen colour, I heard Shawna moan eagerly as her hands slid underneath my petticoats, rubbing and cupping my ass. I blushed, desperately trying to ignore her as I double-checked the oven, my cock once more testing the stitchwork of my gaff. With a smirk, Shawna disappeared to her room, leaving me to cook dinner, a sting on my ass from her parting playful spank.

Finishing and placing everything on a simmer, I turned around and squeaked in surprise, seeing Shawna standing there completely naked, a cock strapped around her. A big cock. I gasped, my face obviously amusing her as she laughed, walking towards me as I blushed, over a head taller than her yet feeling incredibly small in that moment. With one finger, she lowered me to my knees, gently cupping my chin with her hand, cock brushing against my painted lips.

"You look so pretty, Rory," Shawna said, as I softly moaned, her new cock pushing past my lips into my mouth. "My pretty little cocksucker." I whimpered around her cock, staring up as she slowly slid it in and out of me, that intensity and fire returning to her eyes. She continued her teasing show of power, until the dildo was coated with my saliva, my eyes slightly watering from when she tested how far my gag reflex could be pushed.

With a smirk, she helped me back to my feet, soon stepping out of my pretty dress to stand before her, wearing nothing but my nylons and shapewear. My gaff came next, blushing hard at the erection I was sporting, throbbing with excitement from the situation, which Shawna simply laughed at, thoroughly enjoying herself as her cock was placed next to mine. Stroking both of them together, she was more than happy to point out just how much bigger hers was.

Shawna left me with my hands placed on the table, disappearing into her room once more while I listened to the constant and uncontrollable tiny moans escaping my lips. I heard her return, whimpering with excitement as I felt her tease her cock up and down between my asscheeks. I had played with anal toys before, enjoying the experience but not consistently keeping up with it, yet being placed in such a vulnerable position for someone else was a completely new, exciting, and enticing spin on the activity.

Knowing this, Shawna first slipped a gloved finger inside of me, listening to me moan like a little whore as she rubbed lube all around my eager hole. She listened to the effects it was having on me, laughing and teasing as her free hand slapped my ass intermittently, prepping me for her cock. After her finger came something larger, shaking as my ass stretched around it, before it narrowed, being swallowed and fitting snugly between each cheek.

Giving me a final smack, Shawna returned my gaff for me to wear, both washed up for dinner. I glared at her the entire time, unable to take my mind off the plug she'd left inside me, watching that smirk of hers grow through the meal. Afterwards as we cleaned up from dinner, Shawna amused herself with my body, listening to my soft moans as her hands explored me, pinching and rubbing to her heart's content. I felt like I was losing my mind.

I moaned in her arms on the couch once we were finished, lost in that familiar fog of submissiveness, completely underneath Shawna's control. Her cock not once left its place between her legs, stroking it as she teased me, feeling it rub against my stomach as we kissed. Placing a towel on the couch, she sat down on top of it with her legs spread, beckoning me onto her lap. Legs on either side of her, I slid in place as I kissed her, my arms wrapped around her neck.

"Rory," she said between kisses, my gaff thrown across the room, hard cock springing forth between us. "You're going to look so pretty, with my cock in your ass." I whimpered, hearing her dominating tone, my body shaking with excitement. Shawna reached between my legs, freeing the plug from my hole, her cock dripping with lube as I slowly lined it up with my ass. She patiently watched as I took my time, sliding down her big cock, feeling it gradually disappear inside of me.

Before I knew it, I felt myself in her lap, the entire cock sitting comfortable in my ass. A bit bigger than I was used to, but with the lube I was able to handle it, my cock still raging hard as I moaned eagerly, sliding up and down on her much bigger cock. Shawna watched it all eagerly, her hand gently stroking my cock as I began to fuck myself in her lap. Her fingers moved to the tip, teasing me gently as I shook, the mix of pleasures slowly driving me insane.

I sank down hungrily on her cock over and over, amazed at just how wonderful it felt. My legs were tiring, but I didn't dare slow down, feeling that familiar build up inside of me, that tingling sensation trapped in my cock. I moaned, leaning against Shawna for support as I fucked her cock, her encouraging words seeping into my mind.

"That's it sweetie," Shawna said, her hands barely moving on my cock as I whined, slamming her new cock even harder inside of me. "That's it, cum for me. Cum on my cock. My pretty girl." I whimpered, my mind on fire with lust as I shook, the orgasm seeming stretched, always out of reach, far beyond and more powerful than I was used to. My mouth open, unable to even moan properly, just a constant stream of tiny, pathetic noises as I slowly built towards the orgasm I so desperately needed.

With a guttural scream, I finally pushed myself over the edge, legs threatening to give out, quivering on either side of Shawna. I barely felt my cock erupt between us, my g-spot flaring against her cock as I came, the orgasm shattering through my entire body. I rode it as best I could, tears sliding down my face from the intensity of my release.

When I finally came back to my senses, finally able to take a breath, I laughed and cried against my friend, who joined me as she planted a kiss on my forehead. Every movement made me flinch, my ass sensitive with her cock still impaled inside of me.

"Wow, that was fucking hot." I giggled, having to agree with Shawna, who began wiping up all the cum I had shot onto her with a finger, offering it to me to suck on. Over and over I moaned happily as she fed me, finishing by tracing a finger along my cock until it was clean as well.

Shawna moved her hand to my hair, gripping it tightly as I moaned. "Did you enjoy my new cock, Rory?" I moaned, nodding as I shook, feeling it finally slide out of my body. "Good, because you looked so pretty riding it." I blushed, my ass feeling empty without it, leaning against my friend for support.

We both showered and got cleaned up, wearing a cute babydoll as I snuggled up against her on the couch. Exhausted, I quickly fell asleep as she ran a hand through my hair, echoes of being called her good girl floating around in my mind.

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After that night, I was hooked, Shawna no longer even needing her magic phrase to make me bend to her will. Anytime she wished to play with Rory, or steal her for a night out, I was there, wearing whatever beautiful, adorable, scandalous, or humiliating outfit she had chosen for me. Skirts, heels, dresses, leggings, even bathing suits as we lounged around a friend's pool, Shawna enjoyed her full control over my feminine persona.

She was always respectful when I needed a break from being Rory, needing to embrace that more masculine side of myself from time to time. But as she recognised it sated, or seeing myself slowly shifting back, Shawna would always be there, helping me into a cute dress, the words "You look so pretty, Rory" never far from her lips. I had lost count the amount of nights I had sighed happily in her arms, feeling her hands running through my hair.

Rare were the nights where she used my cock, preferring to make me cum with hers. But every once in a while she succumbed to cravings of her own, sliding down in my lap as I moaned, feeling our nylon legs entwined as she fucked me. Regardless of how she did it, the constant theme was how easily she controlled me, dominated me, and kept me docile. I was always her good girl, softly whimpering as she calmly guided me through whatever her plans entailed.

I was a hopeless case, lost staring into her eyes on these nights, knowing I had very little say on what she would be doing with me. All I was left with was the taste of her on my lips, the feeling of the feminine outfit I had been dolled up in, and the lingering effect of her words on my mind.

You look so pretty, Rory.