Brittany's Travels Ch. 02

She was once again unsure of that as she pulled the dress on and zipped it up in back. Whether it was her fondness for soccer or a rebellion against her ridiculously feminine name or something else entirely, Brittany had never liked dresses. Even as she had to admit this one flattered her body and flowed gracefully around her calves, Brittany was still not a dress kind of gal.

But you're not Brittany now, you're Erika, she reminded herself. As she admired the attractive reflection in the mirror that wasn't Brittany at all, Brittany resolved to do her best to enjoy her new life.

Winnie made that quite a bit easier with his genuine display of delight when Brittany emerged. "Oh, my darling, you do clean up so well!" he gushed. "I can hardly wait to see your hair finished as well. Angie will be positively thrilled!"

Brittany allowed herself to accept his accolades with an appreciative smile. "Thanks, Winnie," she said. "But tell me, shouldn't a guy like you prefer us less girly?"

"I like my men manly and my women beautiful," he declared. Studying her carefully now from head to toe, he then added, "I only see one more final touch, or two if you prefer. Your eyebrows."

"If you've got to mess with my eyebrows, make it both of them," Brittany said.

Winnie laughed. "No, I meant both eyebrows were the one thing we need to fix. Get back in the chair."

Brittany did as directed. "Okay, I know they're bushy, but we've got to leave something there."

"Of course we will," Winnie said. "But when we're done, they'll be neat and straight instead of wild." He took down a jar of wax and opened it. "I'm afraid this will sting, but it will be over quite quickly and I'm certain you'll like the results."

"No doubt," Brittany allowed. "I've got to admit, Winnie, you've been right about that so far. This woman isn't me, but she's fabulous."

"You've got to stop thinking that way, darling," Winnie said. "Of course she's you. It's a new you, that's all. Now, hold still."

It did indeed sting, on both eyebrows, but Brittany couldn't argue with the results when Winnie spun her chair around to face the mirror. "Lovely," she admitted. "Never imagined I could get those under control."

"I'm glad you're seeing the pleasant side of this like the rest of us are, Brittany."

"Now what was that one other thing you said was up to me?" Brittany was quite afraid she knew the answer; but it was only fair to ask.

"Well, my dear," Winnie said with a grin that was almost shy. "When a woman has bushy, unruly eyebrows, that is usually not the only part of her body that's adorned with too much hair. If you'd like, we could also -"

"No, thank you!" Brittany interrupted. "It hurt more than enough up here, never mind down there! Besides, you know, in prison, that was the one tiny bit of privacy I always had. At least the guards never saw my pussy lips, if they got such a good look at everything else."

"As you wish," Winnie said. "However you want your intimate area to look, keeping in mind that in this job it is likely to be seen a fair bit."

"What?!"

"You are not so naïve as to think there won't be pillow talk on the way to infiltrating the network, are you?"

"Yeah, okay, of course you didn't make me beautiful for nothing," Brittany allowed. "It's just...Winnie, I'm still trying to get all this stuff straight in my mind. It's a big change."

"Big and beautiful," he said, standing behind her to admire her in the mirror with his hands on her shoulders. "Now, the pièce de résistance, let's get those silly curlers out, shall we?"

It was the work of a few minutes for him to remove them, and then to brush and set her hair. When he was done, Brittany was greeted with the sight of herself with a bowlish haircut of darkest brown framing her face. Coupling that with her new clothes, she felt like a middle aged librarian - but a very attractive one. "Winnie," she said, "I've got to admit, you cleaned me up pretty well."

"You'll be irresistible to those losers, I guarantee it."

At that, Brittany decided to act on an idea that had been bubbling up in her mind all morning. She spun the chair around and stood up. "How about you, Winnie? Am I irresistible to you?"

"My dear, haven't you gathered where my interests lie?" But he grinned a bit too broadly as he said it.

"I've gathered where you want me to think they do," Brittany said, stepping towards him at an enticingly slow pace so that he couldn't help but admire his creation at close range. "But I've also gathered what's been happening in those tight pants all morning, most of all when you offered me the Brazilian."

"Nuts. I always tell Angie we ought to go with looser pants for that very reason." The pretentious accent vanished, though he still sounded overeducated and elite to Brittany.

"Does that act ever really work in charming women out of their clothes?" Brittany asked, coming to a stop just inches before him so that her breasts were nearly poking him.

"You'd be surprised at how often it does," he said. "They're not all as perceptive as you are."

"They would be if they hadn't even seen a dick in two years," Brittany said. "If there's one creature comfort Angie hasn't offered me...and that's what I've been craving most of all! I just couldn't really ask her!"

"But you do feel you can ask me?" It was more a statement than a question.

"You said yourself I was beautiful, Winnie, and you made me that way in the first place. Surely you want to fuck your masterpiece?"

"M-more than you can imagine," he said. "But it'd be against all protocol."

"Fuck protocol, and fuck me, Winnie! Angie'll never know."

"Well, she is out on some errands for the morning," Winnie admitted.

Brittany's panties were damp as a washcloth by the time she coaxed him upstairs a few minutes later. Seeing no point in playing coy at this point, she grabbed at Winnie's pullover with both hands and pulled it out of his pants with a force that even surprised her. He didn't even have time to shut the bedroom door before she had his shirt off and her tongue down his throat and her hungry hands rushing all about his chest.

She felt his arms locked most pleasantly around her, but there was no sign he intended to help her out of her clothes. "Help me off with my dress already...or I mean your dress!" she quipped while undoing his belt buckle.

"It's your dress, Erika," he whispered, as at last he began lifting her skirt up.

Brittany gave up on his belt for the moment and took his face in both of her hands. "This is Brittany, Winnie. It's me you're going to fuck, not this fictional character of yours, all right?!"

"S - sorry."

Brittany released her grip but didn't break her gaze, and he remained frozen with her skirt gathered up in both hands. As the realization washed over her, she began to laugh. "You're afraid of me, aren't you, Winnie? I'm stronger than you and I've been in prison...is that it?"

"Intimidated is a better word than afraid," Winnie said.

Brittany laughed again and raised both arms over her head. "Winnie, undress me. I'm sure I won't be so intimidating when I'm naked."

"You don't know men too well," Winnie quipped, though he did follow her directive.

He stopped to admire the bra he had chosen so wisely, and Brittany took both his hands and placed them on her breasts. "What could be less intimidating, hmmm?" she asked. While he squeezed them gently, she reached back and undid the bra. Once it was out of the way, he continued with even more intense caresses on her bare flesh, much to her delight. "Wonderful, Winnie," she cooed. "I never got enough of this in that place, not even with other women. Can you imagine?"

"No," Winnie admitted.

Brittany was just about to remind him that he hadn't finished undressing her, when he bent down to continue lavishing her breasts with his tongue and moved his hands downward. With a whispering moan of appreciation, Brittany went back to work on his belt just as she felt his fingers slide inside her tights and panties. As she felt him pull them down, she lifted first one leg and then the other as he pulled them all the way off, while she returned the favor with his pants.

With them out of the way, she now saw that his fondness for waxing extended to himself. "Oh, Winnie," she couldn't help chuckling a bit, though she tried not to. "I've never seen that on a man before," she said as she helped herself to a feel about the bare skin around his penis, which was of course standing at rigid attention.

"You like it?" he asked.

"It's a nice surprise." But not nearly as nice as wrapping her fingers tightly around his hardness. "God," she said, giving it a gentle tug that drew a grateful grunt from him. "You don't know how many times I dreamed of this." She sped up her rubbing just enough to work Winnie into a vocal froth, then stopped but kept her grip tighter than ever.

"Brittany!"

"Tell me you're not intimidated anymore!"

He placed his hands on her hips, teasing the edges of her triangle with both thumbs. "I'm not intimidated anymore. I'm really frustrated just now, but not intimidated!"

She slipped her arms around him. "Good answer. Now, let's get in bed."

"Are you sure you're ready?"

Brittany answered not with words, but by placing his right hand between her legs. "Can't you feel how ready I am?"

"That was fast."

"That was waiting two years for this moment. You do not want to make me wait any longer, do you, Winnie?"

"No, ma'am!" He gave her lips an appreciative tease with his fingers, and then leapt onto the bed, which Brittany hadn't made that morning.

He had but a moment for a hungry look at her body before she climbed onto the bed and onto him. She took his cock in both hands, admired it and tickled it gently for a moment, and guided it inside with a triumphant flair. "Free at last!" she declared.

"Oh, that's better!" Winnie said as she marveled at his hairless body rubbing against her full bush as she rocked back and forth. "So frustrating when you stopped - sweet torture!"

"Sweet relief for me!" she replied between moans, as she drank in his wonderful presence clutched within. "Hope it's half as good for you!"

"It is!"

But maybe it wasn't, Brittany began to wonder as she rode him into two orgasms but couldn't yet bring him off. As she caught her breath from the second, she asked, "You one of those guys who has to be on top or what?"

"Harder," Winnie said.

"Didn't have you pegged like that," Brittany exhaled. But harder it was. She bore down harder and faster and slapped into him again and again, surprised it didn't appear to hurt him. It certainly didn't hurt her, as she could feel her most intense buildup yet coming along, and soon they were both groaning loud and hard over the sounds of their bodies slapping together. At last he came, with an outright roar that thrilled Brittany so immensely that she enjoyed her third - the strongest one yet.

"That was quite a finale, Winnie," she said softly, grazing his chest with her fingers as they caught their breath. She sat still, but kept him clutched within her. "I don't think I've ever made a man scream that loud before."

"Thank you..." he was still breathless. "I don't usually come that hard either."

"Had me scared for a minute that they might have heard you downstairs," Brittany joked.

"We did hear him," came a voice from behind.

Brittany whipped around in panic and slid off Winnie's body. Too panicked to cover their naked bodies, she felt her fleeting humiliation vanish in favor of panic as she realized who it was standing at the foot of her bed.

"Angie!" she exclaimed. "Listen, I can explain..."