Brush with the law

Aaron stepped tentatively into the office, unsteady on his four inch heels, and even more unsteady with his new equipment. Nothing had fundamentally changed about him of course, but he felt as if every person he passed could tell he was wearing the prosthetic gaff as if it were on full display or he had a sign on his back letting everyone know he was a man in disguise.

Several times throughout his day he caught Brad staring and he would feel guilty about accepting such lavish gifts from a man he essentially told could never be more than a friend. Not that he had feelings for the sweet man of course, other than guilt. He tried to stay busy, doing a thorough job of filing should help his guilt...even though he was also being paid for doing that.

Lunchtime came around again and Brad saw Erin with her head on her desk, unbeknownst to him she was trying to figure out how she could square things with Brad without leading him on further or having more sex with him. "I've heard of diving into your work but don't you think this is a bit too literal?"

Erin looked up, quickly snatching the paper away that had stuck to her forehead, "Just, uh, I'm sorry I didn't get much sleep last night so I thought I'd take a nap instead of lunch." She smiled nervously.

"A very wise woman once told me never to skip lunch." A slight smile pulled at Erin's lips as she looked up at her boss. "So come along, pond."

"Wait... what? Come where? Who's pond?"

"I'm taking you to lunch."

"That really isn't necessary. I packed a lunch." She raised the half eaten cookie and the small ham sandwich with a single bite taken out as proof.

"It's more for my benefit, remember? We agreed it was the best way to be sure I ate."

Erin rubbed her face, trying to remember if they had actually agreed to doing this, but being as tired as she was she simply accepted it rather than fight the fog in her brain. "Al-alright." She packed away her lunch, finishing the half eaten cookie and grabbing two more for the road before she walked out with Brad. As they were leaving the office Erin's leg buckled for a second but luckily Brad was there to save her from taking a tumble. Of course after that he insisted on walking with one arm wrapped around hers for safety's sake.

As he drove he explained to Erin about a British science fiction show and a delightful redhead named pond that he watched in college which spurred further conversation as they sat at the table about science, both real and theoretical. "And there's this theory of time travel called the bootstrap theory, a man travels back in time to meet Mozart but can't find him anywhere. Panicking he copies out all the music and publishes them himself only to later discover...he was in fact Mozart."

"Okay, but if you go back in time and give yourself a gun, then later go back in time to give your past self a gun where did the gun come from in the first place?"

"Exactly!" Brad smiled excitedly. "There's no cause, only effect. And the gun, or music, is forever trapped in this loop otherwise it will never have existed."

"Unless in the original timeline you buy a gun or sheet music and travel into the past to give yourself these things, you're shunted out of reality or your own history never changed and you simply created a new reality."

Brad smiled brightly, he hadn't had such a discussion with someone since his last days of med school. It didn't matter if they were right or wrong, it was impossible to answer, it was fun to talk about with someone who was as enthusiastic as he was. Erin hadn't realized until it was too late that all throughout their conversation Brad would touch her every chance he could. Erin felt the familiar stiffening as blood went from her brain to her hidden penis until their conversation halted when the waiter came by for their orders. Discreetly she slipped her hand under the table and felt where a bulge should be but found only smoothness. With a relieved smile she continued to inspect her condition under the table. Biting her lip as a finger slipped inside through her panties and touched the hidden head and activated the small twin vibrators. The feeling was nothing like anything before, it was intoxicating and she knew she wanted to get drunk on this feeling as long as possible. Another gentle flick sent a wave of ecstasy straight to her brain.

"Are you okay?"

Aaron snapped his legs shut and pulled his hand away like it had about to be caught in a bear trap, "Um, yeah, no, I mean I'm fine...just hungrier than I thought. I guess." Aaron gulped down his water desperately trying to hide the redness on his face. He wished the world would just swallow him up into oblivion as a strong part of him wanted to do whatever it was he had done, again. The lunch conversation continued but Aaron seemed to be distracted whenever Brad would touch his hand. Once he caught her biting her lip while she lightly ran her thumb over the knuckles of his hand.

Somehow Aaron had managed to survive his lunch ordeal but was continuously on edge throughout the day and constantly stealing glances at Brad and the other women who walked in and out of his view. Finally, with the work day done Aaron rushed home as quickly as the law would allow and sometimes faster than that. He ran into his bathroom and pulled at the prosthetic only to find excruciating pain and the prosthetic itself unmoved from its position. "Holy fuck!" Aaron yelled when the pain hit, and still yet was somehow as horny as ever.

"Mom?!" Sarah knocked on the bathroom door, "Are you okay?!"

"I'm...I'm fine! I just...pulled something."

"Are you sure? Do you want me to call Brad?"

A memory of Brad's sweaty, naked, body as he thrust into Aaron flashes into his mind, "No!" He shouts with every bit of willpower he has left, "I'll be fine…. I'll be fine."

"Okay... just let me know if you need anything." Aaron looks for the adhesive when he is sure Sarah has left. Finding it he reads the warnings and instructions and finds it is a medical adhesive that is designed to be impossible to remove even in water and sweat, once it is set it lasts for a week. Aaron looks at his smooth crotch and swears again quietly before splashing cold water on his face. When that didn't help he took an even colder shower.

After his ice cold shower Aaron returns to the living room in yoga pants and a loose top. "You okay?"

"... yeah." He lied. The cold water had helped quell whatever sudden onslaught of lust he had but now he was left unsatisfied and wanted more than anything to satisfy that hunger. "I could use an ice cream actually."

"Sure. Hey, why don't I go get us some ice cream and since you're hairs already washed and everything we can practice doing your hair for your big date."

Aaron sighed, "Really? Can't you just do it for me before he comes over?"

"I could, but what happens when you guys have a date and I'm at work and at some point I will have a social life myself you know."

"Pfft, you don't need that."

Sarah smirked and rolled her eyes, "I'll get us some ice cream, meanwhile," she took the Aaron's phone and turned it to the hair tutorial she had shown earlier that morning, "you watch this a couple of times then try it yourself and after we can have ice cream."

Aaron sighed, "Fine. For the ice cream."

Fifteen minutes later Sarah returned, after placing the ice cream in the fridge she found her mother struggling with the curling iron and several bobby pins and hair clips dangling from her hair. "Aaagh!" Aaron growled in frustration. "This is impossible!"

"You literally see a woman doing it in the video, mom."

"It's camera tricks or something. Whatever, I can't do it. It's not even that important."

"It is."

"Not doing my hair won't send me to prison, I think we'll be fine."

"It is important! It's an experience all women share at some point. We all try to do our hair, try out new makeup, even the women who don't wear makeup at some point have tried at least once. How often are you watching videos like this?"

"...never."

"Right, and your makeup is very basic."

"...I think it looks fine."

"Yes it's fine but it's basic, do you try any other styles?"

"No."

"Of course not. You're a woman who wears makeup so at some point you'd have tried something different, experimented with your look to see what looks best on you and what you like."

"What if I don't like any of it?"

"Mom. When was your first period."

"What?! Sarah you know I don't-"

"Was it in public? What about your last one? Was it heavy?"

"God Sarah we are not talking about this!"

"We are though! Some women do and you need to be ready for that with some kind of answer that sounds believable. Mom's first period was in sixth grade."

"We don't need to-how do you even know that?!"

"Because mine was in fifth and we talked about it." Aaron remembered Sarah waking up one morning in a near panic, believing that she was dying because she was suddenly bleeding and Erin taking her out for ice cream and explaining what was happening and about to happen with her body. It was one talk he was glad he never had to have. And now here he is about to have it anyway. "She told me all about the first time it happened to her. I was fortunate at least, because apparently grandmother would never talk about such 'dirty things'." Sarah put a hand to her chest and added an affected accent to sound like an older posh woman like her grandmother.

"Fine, fine I get it…" the closest he had in his life to compare it to was his own puberty talk was his father offering to get him a hooker for his birthday which just made him uncomfortable. "Can we just drop the subject for now and...can you help me with my hair?"

"I will to start, but you still need to practice it yourself."

They spent the better part of two hours going over the tutorial, the first few times Sarah did it for him and after had him do it himself, only interjecting when he was getting frustrated or was going about it the wrong way. After the hair training they had dinner and then ice cream which turned into a discussion about their days. Sarah demanded Aaron show her how he walked in heels when he told her how his leg gave out at lunch. "No, no, no! You can't stomp around in them like a horse on amphetamines."

"Hey!"

"For real though, heels aren't like sneakers or boots, they're meant for a much more elegant way of walking. Smoother. More graceful." Aaron rolled his eyes and attempted grace, utterly failing and barely managing to catch himself on the fireplace before he fell completely.

Sarah sighed and used the remaining hours to show her disguised father how to walk gracefully in heels. Each step she was sure to emphasize the sway of her hips.

They repeated this process over the following week, and one remarkable thing Aaron had discovered is doing his hair and focusing on walking gracefully at least provided a distraction from his sexual needs which remained unmet. He knew one way to fix the issue but his male pride refused to masturbate like the woman he wasn't. He was a man who was certainly in control of his faculties and he could wait the, 'five more days', until the glue lost its hold and he could enjoy himself again.

Finally, it was Friday evening and Aaron was busy cooking dinner for officer Luke and for some reason...he was nervous. He was never the best cook in the world but now he was making dinner for a man who he would be dating. Not out of a desire to actually date the man of course but because he was the lesser of two evils and the least complicated relationship. It was either him or Brad, and dating your boss was never a good idea. Ted was not even an option, he was just too wild and unpredictable, he didn't seem like the relationship type anyway. Not that he wanted a relationship with that horrid man.

Officer Luke was nice and they had fun, if these randomly terrible events hadn't taken place they might have been friends that would share a drink after work. Instead he knows how his cum tasted and how it felt to wake up next to him. He still couldn't get over how he acted that night and was immediately caught by his daughter. He felt the front of his skirt and felt more assured knowing his manhood was safely hidden away, only three more days and he can remove the prosthetic and finally get some relief.

The doorbell rang and Aaron smoothed out the slightly flared dress and approached the door, stopping only to check his makeup in a small mirror by the door before opening it to let Officer Luke see him.

When the door opened Luke smiled and softly said, "Wow." as he took Erin in. She wore a 50's vintage style dress that reminded him of an old movie with Audrey Hepburn he watched with his grandpa. The sleeveless top was solid black, ending just above the waist with a small black ribbon tied around the waist in a bow that fell off on the right side. The skirt began a small flare under the ribbon, a series of white flowers wrapped around the dark blue skirt until it stopped along with the skirt just below her knees. Somehow she looked even more beautiful dressing demurely.

"What? It's not too much is it?" She nervously bunched the side of her skirt in her delicate hands, the maroon painted nails contrasting nicely with the skirt.

"No, you're beautiful." Erin blushed and a small smile came to her face as she stepped back allowing Luke inside.

"Thank you. You look great too...as well." Erin kicked herself for being nervous.

"Hello again Officer Luke." Sarah smiled, placing a plate on the kitchen table.

"Hey yourself stranger," he chuckled, "and I told you you could just call me Luke."

"I'll try to remember that."

"Will you be joining us for dinner?"

"Oh no, I have plans to meet some friends so I'll be getting out of your way in a bit."

Erin's eyes widened behind Luke, "You didn't tell me you had plans, sweetheart."

"It kind of came up at the last moment."

"Ah, Luke. Why don't you make yourself comfortable while I get us something to drink. Sarah, kitchen." Erin grabbed Sarah by the arm and pulled her inside. Luke smirked and took off his bomber jacket, hanging it up on the small hook beside the door.

"You didn't tell me you were leaving!" Aaron whispered.

"Yeah cause I'm gonna stick around and third wheel on my mom's date."

"I don't even know who these people are you're going with, and you can't leave me here alone with him."

"I may be into a lot of things but watching my mom and her boyfriend doing it isn't one of them."

"Sarah!"

"Eyes on the prize mom, with this look you will turn your date into a steady boyfriend. Just remember lots of light touches, laugh at his jokes and plenty of flirting."

"I know how to act on a date, it's just-"

"See, you'll be fine." Sarah kissed Erin's cheek and hurried out of the kitchen. "Office-Luke, it was nice to see you again. I'll get better at that, don't worry." Sarah hugged Luke.

"Not to worry."

Sarah opened the door and called out, "Love you, mom."

"Love you too sweetie." Erin called back as she came out with two glasses of wine.

Luke smiled as he took the offered glass. "Should we toast?"

"Did you have something in mind?" She smiled nervously before placing a hand on his arm.

"I did, actually." He held up his glass, "To a wonderful evening with an enchanting companion." They clinked glasses and each took a sip.

Erin's stiffness soon abated as the night wore on. Their conversation ranged from their day to their childhood. Luke had been a former defensive lineman in highschool and Erin had been a cheerleader. The real Erin had anyway, Aaron was a band geek, typically picked on by the football team and even some of the meaner cheerleaders. "Shame you weren't a quarterback, then we'd be the perfect cliche." Erin laughed nervously, taking another big swallow of wine.

"Yeah, but then I'd have to get a beer gut, shave the top of my head and have a bad combover." He pushed out his stomach in a mock beer gut and Erin laughed again. The one thing she was glad to know is her former bullies lives were nowhere near as interesting as hers.

"Please don't." She giggled, "I rather like the way you look now." She blushed immediately realizing what she had said. And worse...he had meant it. Luke was clean shaven with a strong jawline, nicely coiffed hair and a blue button up shirt that looked to be ironed on to his muscular form. The constant touching between them and the flirting was not helping his situation. 'Just three more days! Just three more.' he told himself.

Luke smiled, "I rather like the way you look right now as well." He ran his thumb over the back of her hand in small circular patterns that sent goosebumps up her arm.

"H-how bout a movie?" She stood quickly taking her glass into the living room and pulled Luke along with her.

"If it's anything like the last movie we watched I'm on board."

"No!" She playfully slapped at his arm before picking up the remote and playing a romantic movie.

The movie had lessened the flirting and some of the touching but Luke had started the movie with his arm around her bare shoulder while she drank her wine and eventually ended up around her waist and cuddling when she stretched to put her empty glass on the end table and Luke seized the opportunity. Erin's hands gently rubbed his chest muscles, knowing that she would never have such things and wishing he had done more to bulk up before and maybe none of this would have happened. As she was thinking this she felt Luke's thumb and finger lifting her chin up as he slowly kissed her soft ruby lips. As they parted Luke smiled still gently holding Erin's head. As he waited for some sort of confirmation she wanted to continue Erin's libido had finally had enough. Man or woman it did not care as long it would finally be satisfied!

Erin kissed back hungrily as Luke pulled her onto his lap, her skirt flaring out even more. His passionate kisses soon turned to love bites on her neck. With each bite she wanted it more and more. That small sober part of her fading ever further in the distance as Luke slowly unzipped the back of her dress. "W-wait. Wait." He stopped, "We can't." Luke looked confused for a moment before she continued, "I don't want Sarah to catch us again." Luke smiled and effortlessly lifted her up and carried her into her room with her legs wrapped around his waist. Twice they bumped into a wall as neither of them wanted to stop kissing. Still held up by Luke she pulled herself free of her dress and let it fall to the ground. Luke tossed her onto the bed and she laughed as she bounced. Her deep red bra and matching panties and stockings were on full display for him, along with the red heels she still wore. Silently Luke raised one of her legs and kissed her knee, "Tell me." He said softly before kissing further up her leg. "Tell me what you want."

Aaron swallowed, he had never been great at dirty talk...but he wasn't Aaron right now. He was a sexy woman in bed with a handsome man. "I…." She moaned as he kissed the bottom of her thigh, "I want you."

"What do you want me to do?" He kissed the middle of her thigh and she felt herself quiver, "I want you to….I want you to…" her libido flooded her mind with memories of porn and dirty talk the women there had used, "I want you to fuck me with your big cock." His final kiss landed somewhere between the top of her thigh and her panty line.

"As you wish."

Removing the panties he found Erin's wet and waiting pussy. She didn't know what to expect but it wasn't what happened. Erin felt Luke's tongue slip into her new vagina, an incredible new sensation to be sure. Every touch of what Luke believed to be the clit was like being teased while getting head. The small vibrators reacted with every touch compounding the pleasure even further until, pent up, she came quickly as she grasped Luke's hair. She didn't want it to stop! And the vibrators ensured that it didn't anytime soon when they began to pulse. Usually an orgasm for Aaron was like a firework. One explosion and that was it, but the way the prosthetic was designed it caused a rebounding effect from the little vibrators, sending multiple waves of orgasmic bliss throughout the body. In short Aaron had his first orgasm as a woman. But not the last that night.

Gasping for air Luke stood up and she heard the sound of a belt unbuckling and a zipper being pulled down. Erin sat up, dazed by her own orgasm, and wrapped her lips around the head of his cock. She spent the next few minutes ensuring it was lubed before he picked up both of her legs, threw them over his shoulders, and slowly inserted the head of his penis into her. Still sensitive from her own orgasm she felt another wave of pleasure that nearly caused her to cum again immediately. Grasping the bed sheets as he continued until he was satisfied she could take it before pulling it nearly all the way out and thrusting it back inside. "Oh, Fuck!" Erin moaned. Luke's tenderness changed into full on animalistic lust as he fucked Erin in strange new pleasurable ways. A time later Luke and Erin switched places and Erin sat on his thick cock. Her own lust long since taken over leant forward, being sure to keep his cock inside, kissed him again as she rode him before tearing open his button up shirt and kissing his muscular chest. The small masculine voice had been dragged out back and beaten by her libido would certainly disapprove come the morning but all that mattered to Erin was her pleasure and that this night should never end. It wasn't long before Luke sat up and wrapped his arms around her, kissing her deeply once more and not for the first time, but the first time with new equipment Erin felt a man cum inside of his pussy.

Later, after Luke had slipped out of her, they lay panting while Erin laid on top of him enjoying the sensation her body was getting from skin to skin contact. "I'm sorry I-I forgot about the condom." Luke said slowly catching his breath.

Erin laughed breathlessly, "It's okay, I'm... I'm on birth control." She felt fine in her lie since it wasn't possible for her to get pregnant, no matter how much they had sex. For some reason this thought made Erin smile with hunger once again.