A femboy biker style look

There’s a definite spring in her step as Riley goes over to her dresser. Eager to start picking out an outfit for you she half hazardously flinging open one of the drawers, as she starts to scrounge around the many folded clothes. Picking up ever piece of fabric that catches her eye, she scrutinizes each bit of dress with a strict appraisal of quality as this can’t be just any old outfit. No, no, no, besides their being the obviousness of Riley needing clothes of her’s that fit you, Riley also feels like she needs to weight which styles she really, really. Who knows when she will get another chance to play dress up with you? With her not knowing if she’s ever going to get a chance like this again, she feels like anything she picks out for you has to be just perfect.

While she does that you start to undress yourself, heart beating enthusiasm as do. Climbing out of the bed you stand back up, stealing glances at the clothing Riley is picking out from her drawers as she searches for a set of the most perfect outfits. First you pull the shirt off over your head, then you tug down your pants, and your underwear. In under a minute your again again naked in nothing but your cute pink chastity case. Not wanting to leave a mess you then fold the clothes neatly, and place them onto the bed. With that done you’ve got a little bit to think about this whole situation. Normally this empty time is where you have some second thoughts about doing something like this.

You don’t though, sure this a little un-surety about what exact is going to happen, but no desire to chicken out of this. You want to follow this through, is if you don’t enjoy this whole crossdressing experience you at least want to try it out! With the trial by fire you’ve experienced with most of the kinks you’ve explore with the girl’s this one seems rather tame. Or maybe the girls have been rubbing off on you, and you’ve just become a bit desensitized to all this overt sexual acts. Being stuck in chastity for a few days also probably helps this fact as well.

“Hmmm okay, how about we start up with this?” Riley asks holding up a black g-string as she seems to have begun to formulate an idea for a outfit.

You dick twitches in your cage as you see the string thin article of clothing as an image of Riley bent over in the skimpy panties flash in your mind.

“I didn’t take you for the kind of girl to wear something so risky.” You swallow, nearly drooling as the Riley pictured in your head now spreads her legs in a overly proactive poise.

“Yeah an old boy friend used to love these, personally they aren’t my type, but I think it will go great with what I have planned.” Riley says turning the panties from front to back to show them off.

“Now come on, come on put them on, I want to see you in them.” Says Riley with a eager smile, as she approaches you, g-sting in her outstretched hand.

“I want to see you in them too...” You whisper under your breath, the Riley in your mind again switching to another sexy position.

“Huh?” Riley cocks her head to the side.

“Nothing, here let me try them on.” You say taking the panties from Riley.

Holding each side with your pointer, and thumbs from each hand you stare at the naughty pair of bottoms. Your cock twitches again with the realization that unlike the boy shorts, these panties are unmistaken feminine. Lewd feminine, like just holding the thing has you feel it exudes an aura of risky female eroticism. Flicking your eyes over to Riley you can see her waiting for you with baited breathe, her tapping a foot with a slight bit of impatience. Not putting it off any longer you decide to dive right into this world of crossdressing, lifting up your leg one at a time you step into the panties one foot at a time. Then you pull the underwear up as shiver running down your spine as you look down at the less then bottoms now hugging your hips.

The g-string feels very minimalist against your body to put it lightly. The skinny part that’s ‘supposed’ to some how cover your rear, ridding up between your ass cheeks. The only modesty it provides for your behind is a small line of fabric which barley covers anything at all. Your front isn’t in as bad shape with their being a enough length of fabric to cover up your crotch well enough. Though with it fitting so snuggly it makes it pretty blatant that your in chastity, as the conforming silk outlines your cage almost to a T. This realization makes you bite your lip as your mind thinks back to being exposed in the lobby. What a humiliating yet undeniably hot experience that was. Makes you wonder what those girls that you ran into before would think of you if they also saw you like this...

“Ahhhhh they look amazing on you, so sexy!” Riley squeals with delight as she races over to you, wrapping her arms around your waist as she squeezes your ass with both hands, nearly lifting you up off your feet in the process.

“Wooooah down girl!” You laugh trying to squirm away from Riley’s groping paws.

Using your arms you put some space between you and Riley. Though not before she able to get a little nibble on your neck, her leaving tingles on the spot she put her mouth to, and making you blush slightly.

“Heehee sorry I just can’t help it, you totally rock that g-string, its amazing how much it helps shapes up that cute ass of your’s.” Riley says again not able to keep her hands off as she pulls on the side straps of the panties.

“Aaaaaaa sexual harassment!” You laugh as you again push Riley away.

“You know you like it.” Riley smirks in response, putting her hands on her hips and popping her hip to the side in a jaunty poise.

“See your even talking like a sexual harasser!” You says covering your chest, and crotch like a girl would just got peaked on in the shower.

Riley just shakes her head, and grins at you in response. She then turns around and, grabs something else out of the drawer.

“Here catch.” Riley exclaims chucking a pair of jeans at you.

“Oof.” Not able to get your hands up in time the pants hit square in the head, with you catching them as they fall from your face.

You think jeans are kind of a weird choice considering it’s not particularly a feminine thing to wear, but Riley’s the one calling the shots here so you’ll defer to her judgement on this. Moving over you sit down the bed so that you can get the pants on easily. Placing both feet into each pant legs you then stand upwards wiggling around to shimmy the waist band all the way your up hips before buttoning, and zipping yourself up. The pants are a snug fit as they seem to be skinny jeans, and aren’t very lose at all. Examining yourself in the mirror on Riley dresser your surprised that just like the underwear the jeans really help compliment your body shape. The firm, yet painless tightness making your butt stay fixed in round curvatures shape, preventing what little bit of sag your rump did have.

“Awesome, awesome, awesome, now just give me a sec I’ll be right back!” Riley cheers, as she jumps and claps her hands together.

The strawberry blonde then scurries out of the room slamming the door behind her as she leaves. Alone now you cock your head to the side as you’re left wondering just what that girl is cocking up now. She’s really got so much zeal, and energy since the two of you’ve started this cross dressing thing. Rather then her normal relaxed self, Riley’s acting so much more animated. Guess she’s super into this guy dressing as a girl. Then almost to remind you that she’s not the only one, you feel your cock jump. Smirking slightly you look to yourself in the mirror again. Man, maybe it’s just your mind playing tricks on you, even with only the jeans visible you do seem to have an increased girly tinge to your look.

Getting closer to the mirror the the dresser you sway your hips from side to side as you walk close. Part of you thinks you just look silly doing this, yet another voice in the back of your head praises that feminine stride of yours. Putting your hands on the dresser you lean forward as you shift posture to something more subtle, an salutary . Your breathing quickens as you let your left hip thrust outward slightly, while your abdomen leans to the other side so your body like a S shape. The mirror flickers a second, and in your mind you see an absolute minx of a boy in the exact stance as you. It’s you, yet it’s also not you. Your reflection is cuter, sexier, and even though it still clearly a boy, has many aspects of a female. Make on their, face nails done up, hair re-styled. Your feminine doppelgänger then wets his lips with his tongue, and you in turn mimic the motion. Once more your cock throbs as it starts to push against its cage. You guess it make sense girls are hot, girls are cute, so is it so weird to look like a girl?

“I’m BACK!” Riley cries nearly making you jump out of your skin as she kicks open the bed room door.

Whirling around to face her you can see her already placing stuff on the bed, a lot of the stuff seeming to be cosmetic related. Quickly you straighten up hoping that Riley didn’t catch what you were doing as she walked in.

“Now it’s time for make up come here Doug, come here, come here, come here.” Riley repeats again, and again, as she frantically motions for you to come over.

“Alright, alright keep cool.” You wave dismissively as you trot over to Riley.

However the strawberry blonde isn’t feeling to patient right now, grabbing your arm she strings you along to bed as she feels your taking to long.

“Oof hey, I said I was coming...” You complain as Riley forces you to sit down on a towel she’s laid at the edge of the bed.

“Sorry, sorry, but this is my favorite, part make up is my jam, and your face has such potential not that your not already cute looking you know, like you got a great complexion, your skin practically glows, and your hair has that slickly smooth shine...” Riley apologies though she doesn’t seem too broken up about it as she rambles on, fiddling around with a bottle of cosmetics as she does.

“Here let me see your hand I think cyan would look great on your nails.” Riley orders sitting on the bed next to you, poised with a nail brush covered in cyan nail polish in hand.

You do as she asks, holding out your hand as the weight of the transformation your amount to undergo finally hits you. You tense up as Riley starts to do the first nail, your dull color turning into a vibrate shade of blue, which subtlety reflects the light from the ceiling. However once Riley completes the first the nail she’s stops, and turns her gaze to you.

“You seem nervous you sure you still want to do this?” Riley asks in gentle tone, her face portrays a look of understanding as she speaks like, if you were to call this whole thing off she would do so in a heart beat even if she didn’t want to.

Your heart swells with a warm fuzzy feeling as you see the kindness in Riley’s eyes. She truly has such a tender heart, what a caring person she is.

“No, it just all kind of hit me at once you know, but I think I’ll be fine long as your the one doing it, I really do want to see where this goes.” You speak turning away as you do as a wave of shyness suddenly hits you.

Riley squeezes your hand, hearing you speak of her in such a positive light making her chest swell with pride. She then brings her other hand to your cheek, and gentle turns you mr head to look at her before planting a soft kiss on your lips. She holds the kiss for a few seconds, with her leaving her fore head gently resting against yours as she finally breaks it.

“Hehe you really do know just what to say to make a girl feel good huh Doug.” Riley whispers suppressing a chuckle.

“I-I’m just being honest.” You stutter as your cheeks go red.

“Awww your just so cute when you blush.” Riley laughs, warm smile on her face as she admires the splash of color on your cheeks.

This just makes you blush even harder, which make Riley laugh even more.

“Hehehe don’t worry Doug we can go at your pass if things get to overwhelming we can aways stop remember don’t think this is something you have to power through for my enjoyment, I’m not your dom, and your not my sub right now, we’re just two friends having a good time right now got it?” Riley says by putting what’s happening now in such a plain description it will help your mind calm, and ward
of some of that awkwardness to your feeling.

“R-right!” You nod to Riley putting you hand back into position to she your ready to go.

“Good.” Riley chirps with a warm smile plastered on her face.

She then quickly, and efficiently paints up each one of your finger nails till you have a matching set. Once done with her task, Riley looks over her work with proud satisfaction.

“There, you don’t have to worry about the polish smearing as it’s a fast drying brand, now lets get those toes as well.” Riley then gets down on her hands, and knees leaning down right next to your feet with the nail polish, and brush.

Like before she works quickly to paint your toes. She kicks her legs back, and forth casually as she paints, her even humming a upbeat tone reflective of her cheery mood. Once she’s done your now left with two matching set of cyan nails. Looking at them makes a strange feeling stir with in you, they add such a vibrantness to what is usually a pretty unassuming part of the body. It wiggling both your fingers, and toes you observe how from just a small amount of color you got more of a bright, and playful aura around you.

“There we go, your going to be wearing socks for outfit I have but, it would really bother me to know that your toenails weren’t match your fingers.” Riley admits running a finger over the nail of your big toe, just to really appreciate the shine.

“What do you have planned for me?” Me you ask looking over to the pile of clothes Riley brought in with the cosmetics.

“Well I got a few outfits I want to try out, but you’ll see what they are once you get dressed up.” Riley smiles, not wanting to ruin the surprise to what looks she has for.

“Now I want to work on your face a little, just to add some stuff on I accentuate that natural beauty you already got.” Riley narrows her eyes as she looks at you, she taps a finger to her chin thinking how exactly she should attack this task.

She wants to enhance, and turn your face into something more girly, yet she doesn’t want to completely override your intrinsic features and make you look like a completely different person. You try to stay as still as possible as Riley stares at you,
It suddenly feeling like you’re part of some extravagant art project, and that you shouldn’t move a muscle less you interrupt the artistic process. Watching as the gears in her head turn, Riley then nods to herself as her thinking seems to come to a conclusion of what cosmetics would look best on you.

“Okay hold still for a second this might tickle a little, oh and close your eyes.” Riley say to you as she picks up a small brush, and case of blush.

You close your eyes like she told you to, and that’s when you feel the brush sweep over your left cheek.

“Hah...” You hold in a laugh as the brush’s touch is quite ticklish to your skin.

Riley seems to pay you no mind though, her focus completely on powdering your face as she’s totally enthralled in her work right now. So you just stay froze like a statute, and bare it. Guess this what they mean when they say beauty is work. With about a minute of padding the brush to your face she then transitions right in the next step, highlighter. For this Riley uses, a different brush that’s long like a pant brush only with small bristles. She’s goes slowly and carefully this time like she is panting a picture on your face. This is delicate work compared to the powdering after all, she can’t just be slap dashing highlighter around. Once she completes that Riley moves on to some mascara. The tool she uses for this job is a tiny brush no bigger then her pinky.

“Okay open your eyes again, and just relax I know your going to want to flinch with this so close to your eyes, but just stay calm I promise I’m not gone touch your eye ball okay?” Says Riley in a low soothing pitch trying her best to lull you into tranquility.

Then patting you reassuringly on the shoulder she slowly starts to bring the brush up to your eye. It takes all your willpower, but somehow you stay still as Riley tidies up your lashes into one smooth shape.

“Now the eyeliner close your eyes again please.” Riley says announcing the next step as she picks up the stencil.

She then outlines just above the top of your upper eyelid, making the line where the end of your lid look thicker. Once both eyes are completed Riley sits back, and smiles basking in the finished product of her work.

“Well tell me what you think?” Riley asks as she hands you a small compact mirror.

First the subtle gleam of lipstick draws your eyes to your lips though not enough to completely overwhelm, or distract from the rest of your face. As next you see your cheeks, the added bit of color, and depth making the skin appear smoother, softer. The highter even makes your face shine a little like, your skin was some valuable metal. All of that culminates in you appearing to give your face a feminine diva aspect to your appearance. Nexts is your eyes which thanks to the conservative amount of eye liner make your eyes really pop, and have them looking a lot bigger, bestowing on you a cute, and innocent look that balances out your diva vibe with an air of nativity. Lastly are your lashes, which after being properly done by Riley give them a shape of a small smoldering flame, the tips tamed into one smooth sharp end at the corner of each eye.

“Woah...” Is the only thing you can say as you bring a hand up to touch your own cheek.

It’s amazing, is that reflection really you? You look up Riley, and she’s grins as she sees that shocked expression on your face.

“See I told you make up was my thing.” Riley giggles as she spins the highlighter brush between her fingers all cool like.

“Yeah I can see that.” Still coming to grips with the changes to your face as you hand the mirror.

“Now then...” Riley stops spinning, taking back the compact mirror she puts it, and the brush down to then pick up a comb.

Riley takes the hair comb, and taps it a few times in her hand.

“Let’s just style up those golden locks of yours eh?” The strawberry blonde smirks as she reaches up her hand, and curls a strand of your blonde hair around her finger.

You gulp, as you’ve always been a bit protective when it came to your hair it’s probably the one thing you really had confidence in appearance wise. It’s partly the reason why you let it grow, you always thought you kind of had that boy band look.

“Just uh be careful okay.” You say giving the comb a skeptical frown.

“Ah come on now, have I steered you wrong so far, come on it’s not like I’m gonna cut it or any thing it’s already the perfect length, I just need to discipline it a bit.”

You sigh, relenting you move your head forward so that Riley can get at your hair with the comb. In only a few minutes she has your more wild, and untamed style surfer dude style of hair into a more feminine look. With her mostly sweeping so that it bunches up neatly a little rather then having it fall all the way in its proper length to give you hair more depth. Now you’ve gone from boy band to tomboy, with your hair re-positioned into something resembling a rough wavy pixie cut that leans to the left. Something that screams, I’m cute, but kind of wild to so watch out! Finally for the finale Riley places a blue hair clip to hold a bang of hair perpendicular to the natural flow of the other strands.

“Alright you look great!” Riley exclaims her complementing you, and by proxy her own work.

“Now for the best part!” Riley’s face shows of a an expression of pure excitement, her eyes wild as she grabs the clothes front the pile.

“Here turn around for me.” Riley says grabbing you up on to your feet, she then spins you round so that your backs now to her and begins dressing you.

Before you can register what’s going on she starts to tie something around your chest. Glancing down world you see that she appears to be wrapping a extra long bandana around you. It’s a dark blue with that classic bandana pattern which after Riley knots it up on your left side looks exactly like a tube top bra now. It’s strange how covering something up that isn’t usually covered suddenly brings a sexual nature to part of one’s body. Your normally unassuming boy chest, now feeling like an intimate sexual organ, that needs to be hidden less you shame yourself. Though even with it making you look more ladylike you got to admit it’s kind of cool looking, the idea to use a bandana like a top actually a pretty creative idea. Riley then sticks her fingers down the sides of your pants which makes you shrieks out in surprise. At first you thought that she is trying to feel you up, yet her hand quickly leave you which has you confused, and looking down to realize that Riley has pulled up the straps of your panties to have them teasingly peak out above your jeans, increasing that risky aura surround you. Still a feeling a bit disoriented from that unexpected happening, you suddenly find a black motor bike leather jacket being placed on you by Riley. It clearly being for female despite its tough visage as it doesn’t fall past even the top of your stomach, which has it drawing eyes to your now covered up chest.

The style of the jacket is slick, rather then overly rugged something more akin to what you would see some one riding a crotch rocket on, rather then a chopper. Still you can see the theme of the outfit starting to come together as next is up is another bandana. This time Riley ties it around your head hiding most of your hair under the cloth with just a few stay blonde bangs peaking out. The hair clip Riley put in also causes one heavy strand to stick out on the left side of your face sitting just above your left brow.

“Here now put these on.” Riley then says as she toss you a pair of gloves.

The gloves are black fingerless ridding gloves, something a stereotypical biker, or some sort of action hero from one of your video games would wear.

“These too!” Riley says throwing you a pair of black boots, and plain white socks.

The shoes almost hit you in the face as you just barely got the gloves on before Riley tossed the boots to you. Looking at them you see their a pair of long black lace up boots. They have a modernized look, seeming more sleek then normal work boots. Putting them on after the socks you realizes they are quite right after your lace them up, with them reaching almost half way up your calf in length.

“Okay that’s the last thing, now check yourself out.” Says Riley as she eagerly grabs you by the shoulders, and spins you around to face her dresser with the large mirror.

You find yourself unable to speak as you look at the sight before you. Did all this really happen in a few minutes?

The whole look has so many layered aspects to it. The balance of feminine appearance with your clearly male body, and physique. The biker part of the outfit sitting more on the line of a modern motorist rather then hinting towards some one who sits in a dingy dive bar while smocking, while also keeping the underlying tough factor to the full outfit. The thin straps visible from the panties, and the bandana bra give credence to sexy yet also thoughtful presence when you look at yourself. Like you’re a lewd boy, but there’s also substance underneath your naughty exterior.

“Woah...” Is all you can whisper as you look at yourself

“You look amazing!!!” Riley nearly shouts as she runs up, and gives you a quick hug before then retreating back to get a good look at you.

“Yeah I do huh...” You say looking over to the mirror again as a warm cocky feeling starting to spread over your chest as you do.

Heart beat starting to quicken now, you begin really feeling yourself as you slowly start to move your arms over you body, eyes locked on your reflection. Your appearance never really is something you were to insecure about, but now you feel like you could confidently state you’ve got that mojo. Turning around, to check yourself at every angle in the mirror, the feeling of wanting to show off starts to grow, and grow. Till finally you can’t take it you have to strut your stuff! Striking a poise you turn you back to your reflection, then craning your neck back to the mirror you wipe some imaginary dust off your shoulder, the act of you doing so make you like a badass sexy renegade, well at least in your mind. An Riley’s as well as you can see the Strawberry blonde smile at you while giving you a round of applause at you striking a pose.

“Oh oh oh oh now do something sexy, put your arms above your head, and shift your weight to the right.” Riley motions to you, her eyes full of a viable awe.

“Like this?” You ask interlocking your hands on your neck, and shifting your stance.

“Yeah now give me a flex!” Riley insists getting more, and more hyped up as the show goes on.

“Like this?” You asks curling both your of your arms in the classic body builder pose.

“Yeah, yeah, now do some un expected surprise me!”

Surprise her huh, yeah you can do that. Racking your mind you search your thoughts for an idea till, Ah hah!

“How about this?” You then bend forward towards Riley, and put your pointer finger to your lower lip, pouting you, put on a concerned face, which then slowly morphs into a mischievous expression to with you then blow Riley a kiss.

Riley is left breathless for a second kicking herself that she didn’t ask to take a picture before you did that.

“Now do a ground pose!”

Sliding down on all fours, you take a sitting position, wrapping your arms around your legs, pressing them into your chest as you stare with faux thoughtfulness on your face, as you try to look in deep contemplation. Then you jump to your feet again, giving Riley a wink as you make finger guns, and point at her while playfully sticking out your tongue from the side of your mouth.

“Awesome, you look amazing Doug so stylish, and cute!” Riley clasps her hands together looking like she might just explode from the pure amount of joy.

“Or maybe I should call you some like Diana, all of that feminine energy you got going on, makes it feel almost unbecoming to call you by a boys name.” Riley giggles into her hand.

Your not laughing though. Instead you frown not to keen on that naming. Like your still you, and your still a guy, it’s hard to explain but such a name change felt like a shedding of your identity, which you didn’t like. You’re you, even if you did take on a more feminine life style you’re still the same person who grew up with your mom, and sisters. That person isn’t wrong, they aren’t a inferior stage of your life, and this isn’t the better you. It might be you with a different flavor, but it’s still equal to what you were back then. It might seem like something small to other but to you the shedding of your name just felt like a betray of your life.

“No, please don’t call me that.” You speak in a serious manner that conveys you discomfort pretty seriously.

“Oh I’m sorry I didn’t mean to offend .” Riley’s eyebrows go up, not expecting you to be so opposed to the idea.

“It’s alright, just no girl name changes please.” You say reaffirming your dislike of the idea while telling Riley their no harm done.

Tension then hangs in the air for a minute as the serious tone brought down the mood some what. Quick to bounce back though Riley then happily hops on over to you, and puts her arm around your waist.

“Alright we’ll stick with Doug then.” Riley smiles tha warm friendly smile again.

“Yeah thanks, sorry about that, I mean I do have to thank you, I never would have been able to see my self like this with out you, it’s really kind of well... thrilling.” You speak in a soft tone as you rest your head against Riley’s shoulder as you stare at yourself in the mirror some more.

Heart beating at a sprinting pace as you run a hand from your chest to your stomach down to your thigh as you watch your reflection do the same just to again remind yourself that this is real.

“Hey you don’t have to thank me I’m just glad you like the make over I gave you, and that you allowed me to do it.” Riley chirps, slyly basking in your praise as she looks over you in the mirror with pride despite trying to appear humble.

“No really I want to thank you properly.” You say shifting over to stand in front of Riley as you slip a arm around her waist, and push your body against hers.

Riley raises an eyebrow intrigued, and caught a bit of guard at you being so forward, and taking the initiative like that so suddenly. She isn’t against it how ever. Riley actually finds the idea quite amusing, and wonders what it would be like if you took the lead here. After she was the one whose been domineering so far so she curious to see how you would act in the divers seat for a change. Yet there is one thing first...

“I do have more outfits that I was looking to have you try out, if you have to thank me you think you can wait till we try them all?” Riley asks flicking her eyes over to the pile of clothes on.