Pink and Frills

The deal was, I'd help him dress up like a girl and in exchange we'd do what I wanted this time around. I know, I'm the luckiest girl in the world, having a boy who's into crossdressing. Not forced feminization. It's just that we both like to mess with gender roles a bit, and that in and of itself isn't a matter of or flirtation with power dynamics. A lot of the rest of it is though.

First thing first, we had to pick out the right dress for him. Amazingly, he wears virtually the same size that I do, so I don't have to go and buy clothes separately for him. He picks out the tulip pink dress, not fancy or frilly enough to be a prom dress but nicer than a sundress. Like most of my nicer clothes, the awkward level of formality leaves it with virtually no uses.

"Pink? Think that'll look stereotypical enough on you?" I ask as I take the dress out and toss it onto the bed, landing flat and lifelessly.

"But you know pink's my favorite..." he whines, already pawing through my underwear drawer to find a matching set of a white lacy bra and panties.

"I know. It's adorable."

"Ooh, can I wear these too?" He holds up my pair of white fishnets stockings.

"Wouldn't you rather wear the lace ones?" I ask, taking down the box with his single pair of stiletto shoes.

"Yeah, you're probably right."

He does indeed settle for the other white pair, with lace on the top and no hint of fishnet design. I think they match the lingerie far better than the other pair would. I begin plucking things out of my make-up collection as he undresses, only to be interrupted again almost instantly.

"What about my legs?"

Without looking, I know he forgot to shave them last night. I wouldn't blame him, but he always looks forward to getting dressed up and he always forgets to shave.

"Go shave."

"I was..." I glance over with mild impatience. "Hoping you'd help. I mean, I always nick myself, and I'm too sloppy."

"All the more reason you practice," I retort, expecting him to argue. He just looks at me pleadingly though, so I sigh and follow him into the bathroom.

No matter how many times I see him naked, I never stop loving the sight. He pulls his tee-shirt over his head inelegantly and tosses it onto the floor. He unbuttons and unzips and pulls down his jeans and his boxers in one swift motion, and I resist the urge to grab his hips and go down on him immediately.

He sits on the edge of the tub and turns on the water. I sit near him, but far enough away so as not to be splashed. He catches water in his two hands and uses it to wet the upper regions of his leg too awkward to fit under the faucet without falling into the tub; he then lathers his legs up with shaving cream.

The water off and one leg extended, foot placed on the edge of the tub next to me, I begin to shave his legs for him. It's a slow process, as I'm careful not to nick him, but more rewarding than I'd expected. A job isn't tedious when with stroke you're rewarded with revealing new soft, clean skin.

Attention on the task at hand is harder when I'm gently removing the hair from his inner thighs, my fingers just inches from a certain already well-trimmed region. Even as we're both silent, I can tell he's thinking along the same lines as his cock grows, just a bit.

Once I've finished shaving him, he rinses off and dons his clothing. His make-up is quick and simple, a little mascara, a touch of lipgloss, and a hint of eyeshadow. There's not much I can do with his short hair, so I just tousle it with a bit of gel and, despite his dirty look, add in a thin headband.

"Feel pretty?" I ask, smiling as we both look into the mirror. He couldn't pass for a girl, most likely, but he's still beautiful to me. His lack of natural curves is dulled rather than accentuated by the dress; his mouth is soft and subtly pink.

"Very much so." He grins in return and takes my hand, leading me into the bedroom.

I kiss him passionately, pushing him back towards the bed. He almost stumbles, then pulls himself back in closer to me, his arms around my neck. As I flick my tongue across his lips I can taste his lipstick, the dull flavor of artificiality.

As he clings to me, I keep one arm wrapped around his waist and with the other I stroke his neck, play with his hair. Through the few layers of material I can feel him growing firm.

"Excited so quickly?" I run a hand up his dress and even through his panties, my sudden touch makes him gasp.

"Are you surprised?" he retorts, grabbing onto me more tightly as my fingers slip under the lingerie.

"Not particularly." I caress his shaft while planting more kisses on his waiting mouth. By now, his member is straining against the thin lace, firmly keeping him from outwardly extending to its desired position. He searches for my tongue with his, quite passionately. I'm not certain it's due merely to his desire for even more touch or whether it's colored by his frustration with such close-fitting and possibly mildly itchy underwear. I rather like having him slightly discomforted though, so I make no efforts to free his manhood of its lacy cage.

After the string of kisses grows a bit calmer, my eyes open long enough to spot my harness lying on the dresser. I pull my hands away from him, very much to his disappointment, and begin stripping. He reaches out to me, trying to touch my breasts, but I slap his hand away playfully. Once fully naked, I don the harness and snugly fit in the dildo.

His inquisitive look is answered as I grab his hair and push his head down. He drops onto his knees and begins licking the shaft of my artificial penis. His tongue looks particularly pink and soft against the gently curved blue silicone. My fingertips rest on his shoulders, and I permit him to take his time, licking every inch before finally taking much of it into his mouth. The noises he makes, like little gasps of pleasure muffled by the shaft in his mouth, please me. He looks up at me, eyes full of desire and affection, and I playfully push it a little deeper into his mouth.

When I rest a hand on his head and nod at him, he takes the cue and rises to his feet again.

"You know what I want to do to you," I whisper in his ear, nipping at his earlobe.

"I know," he responds meekly.

"Bend over."

He walks to the bed and complies, hands firmly resting on the sheets, face turned away from me. I lift his dress, throwing the skirt up to reveal the lacy lingerie and stockings fully. I run my hands along the stockings, up past the portion of exposed, smooth thigh, and to the waistband of his panties. In a swift motion I pull them to his feet, and my hands return to rest upon his ass.

I think he lets a silent sigh of relief out when I let go, but I return only moments later with a bottle of lubrication. I squeeze a bit onto the tips of two fingers and then toss it onto the bed near him. He quivers as I return my hand to his ass begin to caress its rosy entrance. To help him relax, I reach around to stroke his member with my other hand. It accomplishes this quite well, and I push the tip of one finger into him. He hardly murmurs, so I slide in a bit further, then pull out a bit. A gasp escapes him and I continue working my hands, both inside of him and on his manhood.

Inserting a second finger into him makes him a bit uncomfortable at first, I can tell by the sharp intake of breath. For a moment I release his shaft to put a hand on his chest, pulling him up to a position much closer to standing so I can kiss the back of his neck reassuringly. Without pause I continue the steady in-out with my fingers, and once he's sufficiently comforted, return my free hand to its former stroking.

When I pull both fingers out of him and reach for the bottle again, he tries to shift away from me nervously. I firmly maintain my grasp on his manhood as I squeeze a bit of lube onto my false one. Once it's properly coated, I move into position and carefully thrust in.

The first push of my hips only gets an inch or two into him, despite the warm-up with my fingers, but it garners a frightened gasp from him. I slowly slide in deeper. He moans and grips the sheets, glancing back at me helplessly. I offer him a reassuring smile- and then force the last inch of the shaft inside him.

We fall into a rhythm with a bit of time. Small noises continue to escape his lips from time to time as I pump his shaft and thrust into his ass in coordinated, steady motions. Minutes pass, but eventually I see the sweet twitch of one leg, accompanied moments afterwards by a fiercer grip on the sheets and heavier breathing.

"Baby, I want you to come," I tell him sweetly. My arm is starting to grow tired, but I only grasp him more firmly.

"I know. I know," he pants, pulling himself a bit closer to the bed. Another gasp from him. Another twitch. He throws his head back for a moment and cries out.

He comes all over the sheets, moaning and clasping the bed. As he pulls himself towards the bed, I finally pull out of him and gently let go of his member. I remove the harness while he gets comfortable, and then cuddle up with him.

"That wasn't so bad now, was it?" I smooth out the folds in his dress as I lovingly kiss his neck.

"Not at all." He puts a finger under my chin and ever-so-gently directs my mouth up to his. It still has a thin layer of lipstick left, and here in my arms, he's even more beautiful than he was before.