All characters in this story that engage in any kind of sexual activity are consenting and over the age of 18. If you don't enjoy stories where the characters end up with genitalia that generally belong to the opposite sex and then enjoy using it, this probably isn't for you. All characters are fictional, we just wish this could actually happen.
Day 4
Ash woke before his alarm and slipped out of bed. He padded downstairs, breasts swaying, and his thighs touching each other in his silky pajamas and looked at his pile of new clothes. He needed to put these away. He gathered them up and took them upstairs trying not to wake Jessy. He pulled a few of his older male clothes that he hadn't worn in a few years from the hangers and shelves, and put them in a small pile near the door. He then started putting his new clothes on the shelves and hung up his dresses next to Jessy's. He left his pajamas hanging on the closet door and hopped into the shower to help wake himself and wash his body and condition his hair.
He luxuriated in the warm water streaming down his curves. His skin seemed more sensitive as a woman, and it made showers just that much nicer, even if he couldn't turn the water quite up as hot. He ran his fingers along his curves and started thinking that he'd like to work out more. He needed to get his act together as a man to get rid of the dad bod, but if he wanted to keep this body or trimmer as a woman, he was going to need to do something. Run more often, swim with Jessy, maybe start doing yoga.
Clean and mostly dry, long hair needed more maintenance than he was used to, he went back to the closet. He looked at his new clothes and picked up the bodysuit. It was black, three quarter sleeved, thong bottom, and had plunging V-neck that would show off ample cleavage but not go below his breasts like some bodysuits he had seen some women wearing. He assumed that showing off his breasts, ass, and hips was why Jessy had bought it for him.
He slipped into the bodysuit without a bra or underwear. It hugged his curves, where it didn't show them off, like a second skin. He then pulled on his high waisted jeans the way he'd seen Jessy do it, relieved a little she had chosen some boyfriend cut jeans, and some grey socks. He looked at the effect in the mirror. He felt sexy. Confident, in a way he didn't in men's clothing. Just enough cleavage to tease Jessy and anyone else who might look, but something he could feel confident wearing to anything that didn't require work or formal wear. He quickly pulled back his hair into a short ponytail like Jessy had taught him and went looking for breakfast.
Downstairs he made some soft poached eggs with sautéed tomatoes, and sweet potato hash browns for both Jessy and himself. A pot of coffee brewing while he cooked. He had just finished his breakfast and was looking at his phone wondering if he should order another cute bodysuit he had found when Jessy came downstairs.
She looked at his attire and nodded approvingly. "That looks really good on you, it accentuates your curves really well. I almost want to wear the same thing."
Ash giggled to himself, "You could, but I happen to know you only own lace bodysuits and as far as I know, you've never worn one in public without a blouse on top." He stuck his tongue out at her.
Ash was right, she had a few, all were lacy, two were shaping, but she usually wore them for layering. She felt like Ash had issues a challenge. She ate her breakfast and went upstairs; she picked a white lace bodysuit with a stretcher crotch area to handle her package if it made itself known. She paired it with a knee length heather grey pencil skirt with a slit from knee to mid-thigh in the back. Way overkill for the home office, but she had to dress nicer than Ash.
Walking into their office Ash was already working. He looked over and wolf whistled. "Jessy, wow. Just wow, you look great. How come you've never worn that before?"
"Well before I didn't have to outdress my wife. I have worn this before but it was with the purple turtle neck sweater that you said makes my boobs look so good." Jessy spun for him, walked over and gave him a nice deep kiss and sat in her chair to start the day.
Ash had to really focus to concentrate and get his mind off how good Jessy looked. It took him more than a few tries before he could focus without try to catch a glimpse of her when she leaned back in her chair thinking.
It was 10:28 when Ash got a notification of an email marked URGENT. He looked at his inbox and noticed there was a last-minute invitation asking him to join a meeting with two other teams. He clicked the join button without thinking. One other person was already there. Price squabbles. The Ash didn't notice his camera and mic were on for a moment as he worked on his other screen. It wasn't until he noticed the motion of Prince lean forward to his camera as if trying to get a better view. Ash glanced at the window and realized his video was on. The frame showed a buxom woman in a black three-quarter sleeve top, plenty of cleavage, and her brunette hair pulled back in a ponytail.
Ash quickly turned off the camera a headshot of his male-self popping up. He could see the prince staring at his screen frowning. It looked like he wanted to say something. He opened his mouth to speak just as four more people entered the meeting. Ash watched the prince shut his mouth and lean back frowning. Ash knew prince had seen him dressed as a woman, long hair, and plenty of cleavage. Ash wondered just what the jerk might do now.
The meeting went just fine, Ash had to talk once, he feigned a cough when he started talking to cover his higher voice. The prince had frowned even more. By the end of the meeting Ash wasn't that worried about the prince. The higher ups had moved two projects to Ash's team that had been slated for the prince's team. The prince was scrambling to try and get them back but the folks higher up felt he had enough on his plate already. Ash had no problem with the new projects, they were very similar to several his team had just worked on. He didn't even need to call them to get it started. Just a few quick emails and some calendar notifications for check-ins and they were slotted into the queue.
At noon Jessy came over and sat in his lap. Raising her eyebrows and smiling at him, she suggested a lunch-break make out session. They moved to the sectional and things quickly got heated. Jessy stood up and took off her skirt draping it over the TV next to her underwear that had been there since Saturday. She was left in just the bodysuit and socks. Her hard dick clearly visible through the thin material pressed tight to her stomach.
Jessy straddled Ash and covered his face, neck, and the exposed parts of his breasts with kisses. She opened his pants and pulled them down his legs. Kissing the exposed skin of his hips and then thighs as she went.
Ash's pants finally off Jessy stripped out of her bodysuit her dick sticking out at Ash. Grabbing his hand, she pulled him up from the sectional and removed his bodysuit, pausing to suck on each nipple.
Finally with no clothing between them Jessy pulled in close to Ash, breasts pressing against his, her dick hard against his leg. "So, last night you mentioned you wanted more practice," she breathed heavily, "So how would you feel about a little 69?"
