Feminization, All in Good Fun (2/2)

Kate turned Alex around and guided him into a chair. He felt his garters stretch and tug on the black, thigh high stockings that Kate had dressed him in mere minutes ago. He leaned back, feeling the elaborate set of clasps that held his pink bustier together press against the chair. The gag in his mouth shifted slightly as the buckle in the back caught the top of the chair. This was unreal. He'd been so worried when Kate mentioned that she'd seen some of his porn, but not only was she okay with it, she wanted to try it out. And the feminization stuff, no less! He never would have guessed the evening would play out this way, but he was prepared to see it through to the end.
Kate turned back toward him, a black makeup bag in her hand. “I picked out some makeup for you earlier, dear, I think you're going to like it.” She set the bag down on her vanity, immediately behind Alex. “But, as you might have noticed, you're not the only one who needs to put her face on.”
She was right, Alex noticed. He hadn't seen it before, but Kate wasn't wearing any makeup. She'd put on the black corset and thigh highs, both with red lacing, the black and red thong and 5-inch pumps, but she didn't seem to be wearing cosmetics at all.
“I thought I'd show you how a real girl does her makeup before I did yours, just for reference.” With that, she straddled Alex's legs, leaned forward, pressing her breasts into his face, and grabbed something from the table behind him. When she returned, she sat on his lap, continuing to straddle his legs, and smiled wickedly at him. Then, with the help of her vanity mirror, she applied the foundation she'd just grabbed to her face and neck. When she'd finished, she swapped the compact for one from the black bag and whispered, “your turn,” with another smile.
“It was hard to match things to your skin tone without you there with me at the store, so I decided to go for a less natural look for you,” Kate informed him, as she covered him with foundation. She did her eyeshadow next, creating a smokey effect with black and silver pigments. Though he never got a good look at the powder she was applying to his own eyes, Alex was certain he saw several shades of pink on the palette Kate had been pulling from. Next came liner and mascara. Though Kate was simply able to apply the makeup to herself, she elected to give Alex a set of fake lashes too. With their eyes done, Kate moved on to blush. Again, Alex wasn't quite able to catch what color she was brushing onto his cheeks, but he certainly noticed the effects of the red she used on herself.
“Hmm, this next part is my favorite,” Kate cooed. “But before we get there, we'll need to get this out of the way.” She reached around Alex and unfastened the buckle holding his gag in place, then pulled it slowly from his mouth. “It had to happen sooner or later, I suppose. You'll be needing your mouth later anyway.”
“Sounds fun,” Alex replied, smiling.
“Hmm, no, I don't like the sound of that. Your voice isn't nearly girly enough, it ruins the whole thing. The gag might be out, but if I hear another word out of you, you'll wish I hadn't.”
“How's that?” Alex asked, teasing her.
“I'll clean you up, take the lingerie, and we'll be done for the night. Understand?”
Alex nodded solemnly. Message received, he thought, this time she wants more than to just gag me for a bit.
“Ah, much better,” Kate said, reaching back to the vanity for her final cosmetic. Alex watched as she opened the tube of deep red lipstick and spread it across her lips. He watched it glide left and right, leaving a sexy cream in its wake. Kate pressed her lips together, dabbed them on a tissue to remove the excess, and looked down at Alex. “Ready for yours, honey?”
All he could do was nod.
“Good girl,” she replied, smiling. This time, Alex had no problem seeing what Kate was doing. He watched her pull the plastic away from a brand new tube of pink lipstick, a perfect match to the rest of his outfit. He felt it slide across his lips as he imagined what it must look like. He rolled his lips, pressed them against the tissue she offered, and was surprised to see Kate grab one last tube from the vanity. He watched her pull the brush from the gloss, and parted his lips so she could paint the shimmery clear substance over his lips. It felt wet and tasted like strawberries.
“There we go, sweetie. You're perfect. Just let me get your shoes, and you'll be ready for the real fun.” Kate lifted herself from Alex's lap and crouched next to him. She pulled a black shoe bag from beneath the chair, and removed from it a pair of sexy pink stilettos. The heels were a full 4 inches tall, and each had straps at the ankle and roughly halfway down the shoe itself, both fastened with a little silver buckle. Alex instinctively pointed his toes as Kate slipped the shoes onto his feet and locked him in. Then she stood and helped him to his feet.
Standing in the shoes was easier than Alex had imagined. He got his balance quickly enough, and managed to keep it fairly well. It was walking that was hard. Kate guided him back to the full-length mirror he'd seen himself in earlier, and he had to hold on tight to her arm to keep from falling. “It's all about confidence,” she told him. “You'll get it sooner than you think.”
When he arrived at the mirror, his mouth fell open. As he'd suspected, Kate had stuck with the pink theme. The foundation she'd used made his skin look pale, and the false lashes were incredibly long, giving him an almost doll-like appearance. The pink blush and eye shadow gave some warmth to his face, and made his eyes and cheeks pop, but the things he couldn't take his eyes off of were his lips. They shined and shimmered in the light, and, whenever he opened his mouth, they seemed to part like a curtain rising from the center out, clinging to each other just a half second longer than usual. He loved it.
“I just wish I'd found you a wig,” Kate said. “They're surprisingly hard to come by this time of year, unless you go to a specialty shop. Maybe we'll find you something around halloween.” She wasn't wrong, Alex noted, but he didn't care. He was so blown away by the makeup and lingerie that he couldn't imagine adding more to the ensemble. “It'd be nice to do your nails sometime, too,” Kate continued, seemingly oblivious to Alex's wonder. “Doesn't seem worth it for just an evening though. Maybe we'll find a free weekend sometime soon. Cross that bridge when we come to it though. Now it's time for the fun stuff. Go over to the bed and bend at the waist.”
Alex did as he was told. As he was bending over, Kate cake over to adjust his form, spreading his legs wider, bending his back a little, adjusting his grip on the side of the bed. Once she had him correctly aligned, she retrieved the makeup bag from her vanity and took up a position behind him. “I've actually got one more surprise for you tonight, honey,” she said, as she fiddled with something she'd pulled from the makeup bag. “I figured, since we're getting into one of your fantasies, why not work in one of mine, you know?” With that, she tugged Alex's thong out from between his cheeks, and began to massage his asshole. Alex's knees locked as he barely stopped himself from jumping in surprise. “Oh, don't be scared, I'm sure you'll get a kick out of it,” Kate reassured him. “Besides, you know the safe word, just in case.” As she spoke, she began to spread lube on and around Alex's ass. The cold sensation of the gel against his skin almost made Alex jump again, but he kept his balance. Every now and then he felt Kate slide a finger into him, lubing him up from the inside too. Then he felt the plug. He felt his asshole spread to accommodate the toy, as though welcoming it into his body. He was amazed at how easily it went in. Surely the lube was helping, but between Kate's massage, the clothes and makeup, and the position he was in, he wanted something inside of him, and as soon as that was presented, his body had consumed it eagerly. He felt his ass close around the bottom of the plug as the flared base came to rest against his skin. Then Kate replaced the thong as best she could, and told him to stand up.
“Mmm, I do love the idea of that plug filling you up. Now, girl, on your knees.”
Alex knelt in front of his girlfriend, looking up expectantly at her. He was acutely aware of the toy in his ass as he moved. It felt like every motion he made agitated it just enough to rub him in some new way.
“I bet you're excited to be off your feet, aren't you, doll? Don't worry, you'll be spending the rest of the night on your back and your knees, like a good little girl, so the heels will be more for show. They do look good though, don't they? I bet you're going to love looking at them when you've got your legs in the air later. Mine, on the other hand, do open up some new possibilities.” Kate pulled her thong down, slipped it over her shoes, and tossed it aside as she spoke. Then, stepping forward, she spread her legs just enough to stand directly over Alex, pushing his head back so that it was nearly perpendicular to his neck, her thighs caressing his cheeks and her pussy pressed into his mouth. Alex began eating her out immediately. There was nothing he wanted more than to press his wet, pink lips against hers and flutter his long, sexy lashes up at her as he licked her clit. As he did, he could feel the butt plug shift inside of him, and he clenched his ass around it, appreciating every curve and angle that filled him.
“Oh, yes, that's a good girl,” Kate sighed. “We're going to have some fun together, you and I, aren't we, Alexis?”