Bloom Pt. 03

James let himself close his eyes this time as she began working on him, and Kelsey let him. He relaxed into the warmth and intimacy, the sheer femininity of it all. He was rock hard, he knew, and he knew Kelsey did, too, but he managed to hold still for her as she worked. In that moment, there was no sensation better than the feeling of her brush dusting his cheeks, of the lipstick dragging around his mouth. There was a familiarity to it this time, a reminder that he had done this before with her, that here he was safe to be feminine and vulnerable. He relished every time her fingers brushed his skin, nuzzling into them each time, eliciting a small chuckle from Kelsey. When she finally finished and sat back, he groaned aloud at the loss of her touch, his head pulling up from the pillow as if seeking her hands. When he finally opened his eyes, he found her wheeling a full-length mirror out of the closet.

"A pretty outfit deserves to be seen all at once," she said as James sat up. He looked at himself in the mirror, almost unable to believe what he was seeing. Gone was the scruffy, unkempt man, and in his place was a soft, gorgeous woman, staring out from the mirror with shock in her eyes. He leaned forward and began to crawl toward the end of the bed, and couldn't help but notice the way the top of his dress pulled at his chest just right, giving a stunning illusion of cleavage. He reached the end of the bed and climbed off slowly, enjoying seeing the tease of his thong under the short, short skirt, the way his legs looked. He tried to move slowly, sinuously, and was stunned when he pulled it off. He stood in front of the mirror now, admiring the way the skirt flared as if he had curves. He looked for a moment, aghast, before looking over at Kelsey.

She was staring at him, a strange look on her face. If James had to guess it was a mix of pride, lust... and, he realized as he glanced down her body, that feeling he was becoming all too familiar with, that deep longing and sense of loss in the pit of his stomach.

Kelsey had a bulge in her panties, and the moment James saw it, a great many things about his experiences with her suddenly made much, much more sense. The way she knew just how to shave off all the hair, her familiarity with making her underwear fit him, her artwork...

James couldn't help but stare, and Kelsey followed his gaze. Her eyes flew wide open as she realized what he was looking at. "Oh, shit," she said, hands flying to cover her crotch. "Oh, James, I am so sorry. I was going to tell you, but I didn't know how to tell you, and it usually doesn't come untucked, and I've been lying to you the whole time and I'm so, so sorry--"

She cut off as James stepped forward to her, his hands finding hers and pulling them gently away. Looking her directly in the eyes, he slowly fell to his knees until he was right in front of her. Gently, carefully, he slipped his fingers in the waistband of her panties. He heard her gasp as he did, but he wasn't looking up anymore; all his attention was focused right in front of him. He slowly pulled down, watching as the elastic caught on her. He watched her shiver as it pushed on her, until finally the waistband sprang free and fell down.

And there it was. James was face to face with Kelsey's cock. It was small, almost unobtrusive. He saw it twitch now and then, not hard but not completely flaccid either. The moment seemed to stretch on forever; he knew Kelsey wasn't breathing, and he could feel how anxious she was. He could just imagine what she was thinking now: would he do it? Was he disgusted? Would this be the end for them?

In answer, James turned his eyes up to look at her. He saw her, looking anxiously down, and he locked eyes with her. He nodded, so slightly, then opened his mouth and leaned forward. He felt her muscles untense, then suddenly retense as he finally took her in his mouth. She shuddered as he ran his tongue under her shaft. The sensation of her swelling in his mouth was incredible, and he knew he was leaking through his panties and making a mess on the floor. He was enraptured as he felt her grow harder, as he heard her panting. He leaned forward, taking her cock as far as he could, feeling her hitting the back of his throat. He felt Kelsey put her hands on the back of his head, felt her hips thrusting into him. He pulled back, and let her push him back down onto her cock, again and again, glorying in how deeply he could take her, how she felt filling his mouth. He glanced up at her, and was rewarded by seeing her staring down at him, gorgeous mouth open in ecstasy as he finally took her all the way to the base, her cock ramming into the back of his throat..

"Oh, fuck, you pretty little thing, you..." She held her hands on the back of his head, and he obligingly held himself down on her cock as long as he could stand, until finally he had to pull back off of it, coughing. A strand of saliva strung between his lips and her cock, and he saw the lipstick smudges all around her crotch where his mouth had finally met the rest of her body. He looked up at her, a sloppy, excited grin on his face.

She looked down, adoring praise in her eyes. "Are you doing okay? Do you need to take a minute? What you just did, that can be a lot, especially your first time..."

In response, he leaned forward and took her into his mouth again. He went slower this time, sucking on just the tip, then licking up and down the shaft. He relished each of her groans, the way she twined her fingers in his hair and tightened each time he did something she liked. She did this as he finally took her all the way again, locking eyes with her as she looked down at him.

He pulled back, and as he did, he felt his hand brush against a familiar object. Lying on the floor next to him was the dildo he had used last time. He looked at Kelsey, who nodded. He picked it up, locked eyes with Kelsey again, and slowly licked it, from base to tip. He watched Kelsey play with herself while he slowly shoved the fake cock as deep in his mouth as he could. She gasped as she watched him drool around it. He knew he was making a mess, but he wanted it wet for what he did next.

He placed the dildo on the floor in front of him, using the suction cup to anchor it to the hardwood. Shuffling forward, he pulled the thing to the side in the back, and lowered himself slowly onto the dildo. He felt the same pressure he'd felt before, and this time he knew to relax into it. He gasped as he was penetrated, thankful he had slicked it up well before trying this. Kelsey was staring wide-eyed, stroking herself furiously. James moved himself all the way down, then back up a little, moaning at how it felt to be so full. He wanted to know what it was like to be filled at both ends.

He looked back at Kelsey, his mouth hanging open. She stepped back up to him, grabbed his hair, and rammed her cock back into his mouth. He bounced on the dildo and sucked on her cock, rocking back and forth between both. He couldn't stop moaning, both mouth and ass full of cock. He couldn't believe how good it felt, how full he was, how bad he had wanted this, and for how long. Here, he let himself go to the moment of bliss.

As he rode and sucked, he remembered what Kelsey had done last time he had seen her, and slowly stroked his hand up her inner thigh until he reached where her legs met, then pushed his fingers up, just like she had done. He was rewarded by a sudden gasp from above, and the tightening of her fingers in his hair. Watching her, he saw her eyes close, and he knew what she was going to say next.

"Oh god, James, I'm going to cum, and if you don't want it in your mouth, you should --" He cut her off by pushing down as far as he could, grabbing at her ass with his free hand for leverage. With her filling him, he felt almost complete for once in his life. She moaned loud and long, her whole body tensing, before James finally felt a hot liquid hit the back of his throat. He held himself there as she came, swallowing every drop. She writhed against him, her whole body wrapped up in her moment of bliss. Finally, she pulled her hands away from his head and withdrew herself. James licked his lips, savoring the taste. He looked at the mess of lipstick all over Kelsey, appreciating the marks of a job well done. Her cock twitched, a few stray drops falling from it, and James briefly felt disappointed he hadn't gotten it all. Well, he'd just have to find time to try again, he reasoned to himself.

Kelsey slowly knelt down, her legs shaking the whole way. She eased herself onto the floor, panting as she leaned back. She let herself recover for a moment before looking over at James, a pleasantly stunned look on her face. She opened and closed her mouth a few times before managing to get out a single, "Wow." She wiped the sweat from her brow. "I haven't been blown like that in a long time. That was your first time?" James nodded. "God damn, cutie, you were incredible! Are you still riding that cock?" In answer, James bobbed up and down on it a few times, moaning with the motion.

Kelsey crawled over to him. He couldn't help but ride the cock as he stared at her beautiful tits. He moaned, finally reaching down to his panties. He was achingly hard, and he had been leaking through them the entire time. He was starting to pull them aside when he felt another pair of hands on his. He dropped his hands and used them to support himself while he rode the dildo. Kelsey deftly pulled his underwear to the side, exposing a cock slick with pre-cum. She leaned down close, looked James in the eyes, and said, "I want you to fuck my face while you fuck yourself, pretty girl."

She took him into her mouth, holding herself completely still. James fervently fucked himself on the dildo, letting the motion move him in and out of Kelsey's mouth. It was incredible. He looked down, seeing the subtle curves from the dress he was wearing, feeling the fullness of the dildo in him, the warmth of Kelsey's mouth...

It was enough. He exploded into her mouth. He spasmed as he came, feeling the dildo move around. Kelsey swallowed every drop she could, but he came so much that she had to pull back, and thick ropes of cum landed on her face. James watched as she was quickly covered. Kelsey laughed in glee at the amount. "Fuck, girl, I didn't expect that! Holy shit! That was just plain impressive!"

James smiled weakly as he slowly pulled himself off the dildo; he hadn't realized how much energy it took to ride. "That was... that was amazing. I didn't know I could ever feel like that. I didn't even know I could do that." He looked at Kelsey, her face covered. "You look incredible."

Kelsey grinned at him. "So do you, babe. Smeared lipstick is a good fucking look for you." She sat up, and grabbed a bandana from the close to wipe off her face. James watched her every move, still satisfied, but now thinking about that deep ache he had been feeling inside.

Kelsey moved to the bed and patted it. "C'mere, pretty. You gotta rest after that; I bet you're exhausted." James nodded, and stood up, his legs wobbling underneath him. He staggered over to the bed and gingerly climbed onto it. Kelsey made room for him, and he lay down with his back to her. She snuggled up close to him, and put her arm around him. He move in, and let himself relax against her. The sweat was evaporating from his skin, and it felt good to have someone close.

Kelsey leaned close and kissed the back of his neck, tenderly. "That was incredible to watch. I've never seen anyone take cock like that their first time. And I was honestly so scared when I realized I'd come untucked. Thank you for being so incredibly cool about it."

James didn't reply. Kelsey waited a moment, then asked, "James? Hon? You okay?"

He took a moment before replying.

"I don't think I'm a man."

Kelsey pulled him close into a tight embrace. "Oh, hon, that's hard to confront. I know. And it's okay. Whoever you are is okay."

James let himself be pulled in, let the exhaustion of the day take him. For the second time, he fell asleep, held by Kelsey in her bed.