Playing Dress-Up

Rowan stared in the mirror, trying to comprehend what they were seeing. It was them, alright, despite the outfit. Their thin blonde hair, a little longer than they usually kept it, refused to stay tucked behind their ears.

"This is why I keep it short. It gets in the way when it's long," Rowan complained. Emily walked over with a smirk on her face. She kept encouraging Rowan not to cut their hair because she liked how delicate it made them look and how nice it was to grab.

"Your hair is what you're worried about right now? It looks wonderful, but I hardly would say it's what I'm focusing on," teased Emily. She had a point. Maybe Rowan was focusing on their hair to avoid processing everything else. Rowan had never been sure what, precisely, they were when it came to gender. They'd been born male, and they liked the way they looked - a strong, muscular body and a masculine face. But something about womanhood had always drawn them in. That was why, on a random Tuesday afternoon, Emily had once again dressed Rowan up in her clothes.

Emily always had ideas of just what to pick. It had been a bit rockier the first few times, but now she knew what looked good on Rowan and what Rowan liked, so her choices were always on the mark. She liked to emphasize - really, expose - Rowan's strong back and shoulders, and Rowan didn't mind that at all. They had to admit, they looked good in all the backless, strappy dresses that Emily put on them. Today, Emily had styled them in a brand new dress. Emily claimed she bought it for herself, but it didn't seem her style, so Rowan suspected it was a covert gift for them. It was blue, Rowan's favorite color, in a light shade that matched their eyes. There was, as usual, very little in the back. The fabric draped just above their ass, held up by what felt like a dozen tiny straps that Rowan simply couldn't figure out. This was why Emily was in charge of putting on the dresses.

Other than the dress, Rowan was wearing only white, knee-high tights with lace at the top. The material felt nice on their skin, soft and delicate and sexy. The dress was short enough that Rowan's boxer briefs would've shown underneath it, so they had taken off their underwear and were glad that the dress was loose enough to not completely reveal their erection, which was growing by the second. It wasn't the outfit that turned Rowan on; it was the slow, gentle way that Emily dressed them up and whispered endless compliments in their ear.

"What do you think, beautiful?" Emily was now standing behind Rowan, her hands on either side of their waist. "Do you like it?"

"Yeah," Rowan replied with a smile. Emily nudged them to do a twirl, and they obliged, even though the dress was too short to twirl very much. When they returned to their original position, Emily stood on her tiptoes to nuzzle into Rowan's neck.

"God, you look so gorgeous. So fucking amazing." Emily muttered some other compliments too, but Rowan missed them. Her words were muffled in their neck, and it was hard to focus over the desire surging through their body as Emily kissed and lightly bit them. Rowan couldn't keep a moan from slipping out of their lips, which caused Emily to giggle.

"So sensitive already?"

"I can't help it with you," Rowan replied.

Emily said nothing more, but she slowly ran her hands from Rowan's waist to the hem of the dress. She slid them around to the front, now half on the fabric and half on their thighs. Rowan's eyes closed as their head tilted back and their breathing became heavy. Emily moved her hands under the dress, grazing her fingers along Rowan's inner thighs and kissing along their shoulders.

"Emily," they moaned, wanting so desperately for her to stroke their dick.

"What, Rowan? Use your words." Emily was always such a tease, and she loved being reminded of the power her body and demeanor gave her over Rowan. She was shorter, but only by a few inches, and that didn't matter much when they were both horizontal. Every part of her was soft and pliable, from her chest to her tummy to her ass to her thighs. While she didn't have the body she'd had a few years prior, skinny and a perfect hourglass, she felt her slightly heavier, more mature body suited her just fine, and it still turned heads. Rowan couldn't agree more, and they craved Emily every time they saw her in a low cut top or a tight dress - or even better, in nothing at all.

"Please," Rowan begged, remembering they'd been given instructions. "Please, I wanna fuck you so badly." Emily met Rowan's eyes in the mirror and looked satisfied. She was wearing just a white bralette and denim shorts, embracing the opportunity that early summer gave her to show off her body. Once she heard Rowan beg, she was done holding herself back. Emily spun Rowan around so they were facing her, and she began to kiss them while slowly stroking their dick.

Rowan felt their knees threatening to collapse at the pleasure, and they wrapped their hands in Emily's hair for stability as they moaned into her mouth. Their kisses got sloppier as the pleasure fogged their mind, and their hands began to roam over Emily's body, grabbing onto anything they could find. As the stroking continued, Rowan grew impatient. It felt amazing, but they wanted more, and they wanted it faster. So they began to thrust into Emily's hand, almost involuntarily, driven by a need to feel their dick inside of her. Emily pulled away from the kiss, wearing the look of pride she always did when she made Rowan desperate beyond words.

"You're such a slut," she laughed.

"Only for you," Rowan replied between moans, still fucking her hand and struggling to stay upright.

Emily removed her hand from Rowan's dick, causing them to groan and lurch forward to touch Emily instead. Emily held them back and pushed them onto the bed, stepping out of her shorts and revealing a white lace thong that matched her top and Rowan's tights before crawling into bed on top of her flushed partner. Rowan went to take off the dress, if they could've figured out how, but Emily stopped them.

"I love the way you look in that dress and those tights. Just move it out of the way, but leave it on," Emily instructed. Rowan, always one to be obedient, scrunched the dress up to their waist and then left it alone. Their dick was now fully exposed, but Emily was barely paying attention to that. She was kissing along Rowan's neck and chest, hovering her pelvis above the tip of their dick, and Rowan couldn't take it. Again, Rowan was thrusting, trying to reach Emily and feel the lace of her thong against them. They began to reach their hands towards Emily's hips to bring her pelvis onto them, but Emily caught on quickly and pinned Rowan's hands down above their head.

"So impatient," she whispered in their ear. Still, she gave in to Rowan's desperation. She began to grind on their dick, and Rowan could feel her wetness through her thong. The soft fabric and pressure on their sensitive erection made Rowan moan much louder than before, and Emily kissed them again to muffle the sound.

Rowan groaned, begging again, "I wanna fuck you, please, Emily."

"Then do it, darlin'," she responded, a slight Southern accent slipping out. She released their hands and looked at Rowan expectantly. Rowan immediately grabbed at her thong, taking it off much slower than they might have if they'd had the wherewithal to coordinate their hands at all. Still, it was off eventually, and Emily moaned as Rowan put their hands on her hips, lowering her until they could feel her wetness. Emily began to grind again, this time moaning as her clit glided in circles on Rowan's erection. Rowan didn't think they could get any more desperate than they were a minute ago, but it was building even more now that they were so close to fucking Emily.

Emily must have been able to sense that in Rowan's breathing, in their eyes, and in the way they were grinding back against her. She pulled herself back a bit and lined Rowan's dick up with her entrance.

"Do you want me?" she asked, already knowing the answer.

"Oh my God, yes," Rowan replied, barely able to form the words and certainly unable to keep from speaking much louder than they intended. Emily slid down on their dick, and the two of them moaned in sync as Rowan filled her. She felt amazing, just like she always did, sliding up and down their dick, taking breaks to grind herself on them and moan. Rowan loved when she moaned. Her voice was so sexy, and given how hard she worked to keep an appearance of indifference and maintain her power over them, openly moaning meant she was really overcome by pleasure.

No matter how good it felt, it was never enough for Rowan. They wanted to go deeper, harder, faster - they wanted more. So they used their hold on Emily's waist to flip her over and briefly her off their dick. Rowan fumbled for a moment to put on a condom as Emily touched herself, wetting her fingers in her mouth and biting her lip as she circled her clit. Then Rowan grabbed her face to kiss her, pressing her legs against her chest with their body, and sliding into her dripping wet pussy. She moaned again, and Rowan groaned, forcing themselves to stay focused instead of being overcome by pleasure. Still, they couldn't help it, and they wasted no time speeding up and ramming into Emily as she moaned their name and told them to keep going. It felt so good to make her feel good, and with that on top of the pleasure of being squeezed inside her, Rowan knew they'd orgasm soon. With her always impeccable timing, Emily reached up and put a hand around their throat, pressing on the sides so they could feel the pressure but still mostly breathe.

"That's good baby, you're doing so well. You feel so good."

That was all it took, and Rowan was coming, still thrusting slowly as they spasmed. Their eyes were closed, and they let themselves enjoy just one more moment of bliss inside of Emily before pulling out to clean up. Rowan took a minute to clean up in the bathroom, and as they pulled their dress back down over their crotch, they had to admit they looked good. Leave it to Emily to make them feel like the most beautiful person in the world - second to Emily, of course.

Rowan was at once exhausted and packed with adrenaline, creating a fog that left them a bit out of touch with reality. Still, they always pushed through, to the best of their ability, to please Emily. On more than one occasion, Rowan had fallen asleep fingering Emily, pushing themselves to please no matter their exhaustion. Emily enjoyed Rowan being inside of her, and she made that abundantly clear, but it wasn't the kind of pleasure that made her orgasm. That was what part two was for, and Rowan could tell Emily was ready when they walked back in the room and Emily had her upper half propped up on a pillow, smooth legs spread apart to give an invitation.

She smiled at the sight of Rowan entering the room in their dress. "Did you have fun, honey?" she asked with a glimmer in her eye.

"Yes, absolutely," Rowan responded, wishing they were more eloquent. Emily had a way of talking circles around them, especially in these situations, and the fog in their mind was no help. Still, words weren't very important for what was coming next - other than Emily. Rowan made their way over to the bed, treasuring how delicate it made them feel to touch the cold tile with their thin tights.

Rowan decided to return Emily's question, asking her, "did you have fun?" as they climbed into bed and placed themselves between her legs.

"Of course I did! How could I not, when you're involved?"

See, this was exactly the kind of answer Rowan wished they could have thought of. Rowan moved on, leaning their face over Emily's to request a kiss while they lightly glided their fingers over her still wet pussy. Emily complied with the kiss, lifting her head up to meet Rowan's and then yanking their head back by the hair on the nape of their neck.

"Do you wanna please me more?"

Fuck, of course they did. How could they not want to please a woman that looked and talked like that? None of those words came out though, and Rowan just responded with a whine. Emily released their hair, and Rowan wasted no time moving their mouth to her neck and their fingers to her clit. They circled her clit slowly and kissed their way down her body, stopping briefly to lick her nipples and moving away just as she began to writhe in enjoyment. Finally, they reached her pussy, replacing their fingers with their tongue. Emily immediately bucked a bit, but she settled down and moaned quietly as Rowan continued to flick their tongue gently across her clit. After a minute of Rowan slowly moving their tongue faster and Emily's moans growing with the speed, Rowan moved their tongue up and down her slit, passing only lightly over the clit. They could feel Emily growing desperate under them, grinding her clit on their tongue. She tangled her hands in their hair, muttering their name.

The sound of their name in Emily's mouth filled Rowan with so much desire they worried they would burst. They moved their tongue back to her clit, moving back and forth faster now and applying more pressure. With one hand, they reached for her chest, finding her nipple and massaging it between their thumb and forefinger. With the other hand, they used two fingers to find her entrance, the hole that they had just been inside of. They slipped those fingers in with little issue, her pussy dripping wet from arousal, saliva, and the lube of the condom. Emily moaned deeper, writhing despite her obvious attempts to restrain herself.

"Rowan, fuck me!"

Again, the pleasure and desire flooded their body. They picked up the pace with their tongue and inserted another finger. After a couple thrusts with the new finger added, Emily's bucking had gotten to the point that Rowan had to remove their hand from her nipple and press her down by her lower stomach. They began to insert and remove the other hand with more and more speed and pressure. It was exhausting, but what did that matter? All Rowan could process was the moaning growing above them and the legs squeezing around their head, which were occasionally pushed back to the bed when Emily got a burst of self-control. When Emily's moaning grew higher in pitch and there were no longer breaks between her moans, Rowan knew she was about to orgasm, which was only confirmed by the fact that she was no longer controlling her thighs as they pressed into Rowan.

Emily gasped for breath and pushed her pelvis off the bed, but Rowan kept licking and fingering her. They knew she was finishing, but they'd keep pleasing her through the waves of orgasm until she gently pushed their head back as she always did. A few seconds of bucking and whimpering later, Emily pushed on Rowan's head, wearing a smile on her face. Rowan was smiling too, glad to have pleased their girlfriend.

"Thank you," Emily managed to get out before closing her eyes and opening her arms, beckoning Rowan back to her chest. Rowan quickly wiped their face with a tissue before collapsing into Emily's arms, and both of them fell asleep tangled in each other as soon as their skin made contact.