A Couple of Wishes Pt. 06

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Ash and Jessy go on a date night and try new things.
12.1k words

Part 6 of the 7 part series

Updated 07/26/2023
Created 05/09/2023
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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 or a body that generally belongs 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 6

Ash was in his male body on all fours in the living room giving Jessy a very sloppy blowjob. He was feeling extremely turned on and his rock-hard dick was swaying between his stomach and thighs as he moved his mouth up and down her shaft. He sucked on it for all he was worth. He thought that he must be getting better at this because it didn't feel nearly as large as it had the last few times. He swirled his tongue around the head and sucked on the precum as it coated his tongue, savoring the taste. He wondered when Jessy might cum, and if he had time to stroke his own dick before she blew her load.

Suddenly he felt something hard but at the same time soft press into his rosebud. He didn't want to stop sucking but it felt like Jessy's dick pressing at his entrance and he decided he wanted to be filled. He pressed backwards with his hips while still sucking her dick. He just couldn't quite make it push into him. He grew frustrated, he didn't want to stop sucking Jessy's dick, but he wanted Jessy to fuck him in the ass. This would be so much easier if his ass self-lubricated like his pussy. He'd be filled by now.

He felt the dick at his hole rub back and forth insistently, a little precum smearing across his rosebud. It still wasn't enough. He sucked for all he was worth trying to hum and get Jessy off faster so he could focus on getting her dick inside him from the opposite end. The hot spongy head kept pressing insistently at his hole. "Unnghh," he moaned through the dick in his mouth, he wanted to be filled already. He started trying to push his hips backwards harder, suddenly it felt painful. He didn't want this anymore, Jessy wasn't two people, she only had one dick.


Ash woke suddenly, sucking on his tongue, his asshole felt like something was trying to force its way in, it hurt.

He shifted forward realizing that Jessy's cock was pressing insistently at his entrance. She was slowly rocking her hips, her cock rubbed between his cheeks and pressed against his rosebud. Ash shook his head to clear the remaining cobwebs. He debated on shifting back into a woman and letting Jessy slide into his vagina but instead he slipped out of bed and walked to the closet, his morning wood pointed out and to the left, bobbing as he walked.

Ash pulled on running shorts, a t-shirt, and his running shoes. His dick pressed against the material of his shorts. He debated on trying running as a woman, but decided he needed the motivation of the extra belly he sported a man. He didn't feel like he needed to lose weight as a woman, he liked his curves, not great motivation for trying to lose a little flab.

Stepping out the front door his erection quickly disappeared in the cool morning air as he started his run.

Thirty minutes later he was back at the house and sweating. He put on the coffee and started some oatmeal. Upstairs, he kicked off his running shoes and stepped into the bathroom. Jessy was standing in front of the mirror, her morning wood sticking out stiff as she moved her hand up and down her shaft.

Ash looked at her dick.

Jessy looked down at her hand slowly stroking her shaft, "This morning wood stuff is hard. Do you let it go down or do you get off?"

Ash looked up at her, "Well this morning I just let it go down and took a run. But most of the time I rub one out."

Jessy looked at him thoughtfully, "Do you want to help with that?"

Ash looked at her, "How did you want help?" Jessy pursed her lips, "Umm, my first thought is your ass, but I was going to save that for tonight after our date."

Ash's hardon from earlier started to return thinking about his dream this morning, "I was going to shower... Maybe we should save my ass for date night sex. Break in one of the rooms we haven't yet." He gave her cock a quick tug, "Hop in the shower and I'll give you a quick blowjob?"

Jessy didn't need to be asked twice. She followed him into the shower for some quick head. Ash quickly got her off, using his hands and mouth. Jessy stepped out first leaving Ash to wash the sweat from his body.

Out of the shower, Ash threw on some boxers and went downstairs to make sure the oatmeal didn't burn. Jessy showed up a few moments later wearing another lace bodysuit in navy blue with a pair of jeans. Ash could see her nipples through the material.

He raised his eyebrows, "Feeling a little daring today? No video meetings?"

Jessy threw him a sultry look. "You know, if you owned this bodysuit, you'd be wearing it too. I really enjoyed wearing the one on Tuesday. I felt secretly sexy all day. It feels like a shame to hide these under other clothing all the time."

Ash agreed, he would have worn it in a heartbeat if it fit him. He had felt sexy and strong wearing his. He walked behind her and squeezed her, cupping a breast with one hand.

"Maybe you should buy me one and then we could match..." He kissed her neck and slid a bowl of oatmeal, sliced peaches, and maple syrup in front of her.

She smiled. "I think we are going to need to go shopping for you again, but you are going to have to build up your wardrobe slowly. We can't afford for you to fill out our closet right away."

Ash gave her another kiss on the cheek and light slap on the ass and went upstairs to dress.

The morning workday went normally. Ash and Jessy barely spoke a word to each other. Emails went out, projects got scheduled, and before they knew it, it was lunch time. Ash looked at his emails so he could clear anything new before he stopped for lunch. An email caught his attention. It was a request for an in-person meeting for Friday at 11 am.

Friday meetings were a little unusual but he responded that he would be there. The meeting invite didn't give an agenda and the attendees were private. Ash wondered what it could be about. He turned around to tell Jessy about going into the office tomorrow when the doorbell rang.

Jessy called over her shoulder, "Would you get that?"

Ash answered the door. It was their next-door neighbor. Ash greeted her. "Hey, Rebecca how is it going?"

Rebecca gave him a look and frowned, looking around suspiciously. "Good, I'm glad it's you who answered the door."

Ash gave her a look of concern, "Is something wrong?"

"It's about your wife," she said shortly, "I think she's cheating on you."

Ash raised his eyebrows.

Rebecca plowed on. "With a woman! I saw the two of them on Monday go to the hot tub. The woman she was with was wearing a red string bikini with shoulder length hair and big," she made a round motion with her hands around her breasts, "You know. Anyway. I'm pretty sure I heard them having sex on your back patio later that night."

She took a deep breath. "And then, last night, I saw them again. Except Jessica walked back across the yard totally naked. I didn't hear them having sex but the woman with the big," she mimed breasts again. "But she was wearing that bikini again and followed her into your house."

Ash took a moment to look at his neighbor with a bemused smile on his face. He gave her a moment to see if she had anything else to say. She looked at him expectantly. Ash looked her in the eyes and asked, "What makes you think she was cheating on me?"

Rebecca huffed a little, "Well that woman, and well it sounded like two women having sex." She made a slightly disgusted face.

Ash grinned at her. "Did you consider that it might be me she was hot tubbing and having sex with?"

Rebecca faltered, "Well umm. No. I. Umm. You don't have..." She mimed large breasts, "And well, I guess it could have been you. I've just never seen you in a bikini before." She seemed to be struggling with the idea that here he was without breasts, but last night he had been a woman. "You usually wear a one-piece suit." She dropped her arms to her sides and sighed. "It did look you last night, I guess on Monday. I was just so sure..." She sighed again, "Now that I think about it. It was you I saw last night. So, I guess it probably was you on Monday too."

Ash gave her smirk and decided to tease her, "Well the swimsuit is new. Monday was the first time I've ever worn a bikini. Did it look ok?"

Rebecca turned a little pink "Umm, well" She rubbed a foot on the door mat. "You looked really good." Her voice got quieter, "I wish I looked that good in a bikini."

She closed her eyes for a moment to collect herself, "Sorry about all this I just, well, I thought, I don't know. You know, strange women in your back yard." She shook her head trying to reconcile Ash the man she'd known for a few years, and Ash the woman in a bikini. "Just try and keep your clothes on next time. I know it's your back yard and all, but." She closed her eyes for a moment. "I really don't want my husband to know you go naked in the hot tub. I don't think..." She shook her head and looked up at him. "Sorry I wasted your time. Have a good day."

Ash smiled at her, "No problem, I'll make sure we use robes next time, so you don't have to see us naked."

Rebecca waved her thanks and Ash watched her walk home.

Back inside Jessy came out of the office. "Who was that?"

Ash grinned. "Oh, just our neighbor." Ash was bating Jessy.

Jessy took the bait. "And... What did she say?"

Ash chuckled, "Oh she was just letting me know that she caught you cheating on me." Ash smirked at her and walked to the kitchen.

Jessy ran around in front of him and stopped him with a hand. "She said what?"

"She said she saw you on Monday with some woman in a red bikini going to and from the hot tub. She said that later, she heard two women having sex." He let that hang for a moment. Ash's smirk widened to a smile, "She also said last night, she saw you walking naked from the hot tub into the house followed by the same woman as Monday."

Jessy's jaw dropped. She looked hard at Ash, "Well what did you tell her?"

Ash laughed, "I asked her if the woman in the red bikini could have been me. She admitted it could have been, but that she had only seen in me a one piece before." Ash shrugged. "Then I asked how I looked in the bikini, she told me really good." He smiled, "She asked that we not walk naked from the hot tub to the house, something about her husband not knowing and that was it."

Jessy gave him a look that was half horrified and half bemused. "Oh, umm ok, so..." She paused. "So, she accepted that you are a woman who wears bikinis when you stood in front of her as a man? But she didn't recognize you on Monday."

"Apparently. She did see me on Monday before we made the third wish so she wouldn't have recognized me then as a woman."

Jessy turned around and thought about what Ash had said as she walked to the kitchen, Ash followed.

Ash made up some quick sandwiches while Jessy sat at the bar sipping on lemonade, thinking.

Jessy spoke up as he passed her the sandwich. "Do you think that Rebecca remembered you? Well, she didn't know it was you. On Monday, we hadn't made the third wish yet. So. She wouldn't have known it was you as a woman. Last night, she should have known it was you. Bikini or no." She paused and took a bite, chewing thoughtfully, "I wonder if she was confused, remembering the mystery woman, she didn't realize it was you last night. Maybe it caused some sort of dissonance in her memory."

Ash laughed, "Well, If I had seen me, I wouldn't have recognized me. I mean I would have wanted to keep looking, but I wouldn't have recognized me." He sipped his water, "But now we know that other people that didn't see me as a woman before the third wish, see me as me when I'm a woman." He shrugged, "It's kind of nice not having to wonder if I can just go about my normal life no matter how I look."

Jessy finished her sandwich and got up and started to go back to the office.

Ash called to her, "Hey, no "break" for lunchtime?"

She turned around and raised her eyebrow, "Oh? Did you want some of this?" She unbuttoned her pants and slid them down with her thumbs. She stood straight and thrust out her chest. She cupped her breasts through the body suit. "Well... We have a date tonight, and you want to go as a woman. We don't have time to fool around today. You are going to need to finish work early to get us both ready in time for dinner..." She turned around and strutted to the office.

Ash watched her hips sway as she walked through the house, "What a tease," he thought.

Back to work Ash tried to concentrate on not thinking about his half naked wife behind him or how good she looked in the bodysuit. He mostly succeeded and was concentrating on a project when Jessy stood up behind him and wrapped her arms around his chair and cupped his pecs. "Hey babe, wrap it up. You need to go into girl mode. You've never gotten ready for a date before, and I need to help you, and get myself ready."

Ash started to object that he had gotten ready for a date before, when he realized she was right. Usually, he pulled a comb through his hair with a little gel, put on fresh deodorant, and threw on a clean pair of slacks and a nice button up shirt and called it good. Tonight, it was different. He needed to make sure Jessy had time to do his hair and apply his makeup.

Ash wrapped up his work and met Jessy upstairs. She had already taken a shower and freshly shaved her legs. "Ash? What are you waiting for? Girl up and save your legs, be careful, no knicks tonight. I want you to look perfect." Ash tossed his male clothes in the laundry and changed into a woman as he stepped into the shower.

Ash took his time shaving, making sure to not nick himself anywhere. Legs first then his pits. He skipped his lady bits; those were still fine from yesterday. He wondered a little bit if folks would think he was weird having shaved so much when he was back in his male body. It was probably worth any ridicule he might get to make sure he looked the way he wanted as a woman. He shampooed and conditioned his hair and stepped out, Jessy was waiting for him.

She offered him a towel and some scented lotion, "for your legs, then pick out a thong and meet me back here."

Ash dried off and wrapped his hair in the towel and walked to the closet to get a thong. He picked the black pair and slid them up his legs. He looked at himself in the mirror. He looked hot but decided for date nights he needed some sexier underwear, at least a pair in black lace.

Back in the bathroom Jessy was finishing grooming her eyebrows. She motioned Ash to stand in front of her. Ash did as he was asked. Jessy guided him so he was seated on the edge of the counter. Jessy leaned in with a pair of tweezers and started to work on his brows.

Ten minutes later Jessy declared him groomed. She let him look in the mirror. Ash wasn't sure where all the hair she had plucked and come from. His brows looked nicely shaped, still pretty thick but now a bit more sleek.

Jessy pulled out the hair dryer and started drying his hair. After it was almost dry, she stopped and sprayed his hair with some sort of hairspray. Then out came the curling iron. She worked around his head until he had loose curls that just touched his shoulders and framed his face nicely. She hit him again with another blast of hair spray to hold the curls.

Jessy opened the drawer that they had placed his makeup in. She looked at his face critically. "You don't need much makeup; I think we'll focus on your eyes. I'd like to teach you to do this but that will have to wait. I need time to do mine as well." She went to work, the liquid foundation first. Eyeshadow, liner and mascara, a little blush to accent his cheekbones, and a little of the lip-gloss. She turned him towards the mirror.

Ash was amazed. He had been looking at his face as a woman all week and he barely recognized himself. There were still hints of his male features in there but the face that looked back was all woman. She looked like she was going out to impress. He knew Jessy was good at applying makeup but not this good. He felt like she was an artist and he was her canvas.

He turned to Jessy and smiled. "Wow, you're amazing. I look great." She smiled back, "Damn right you do, my wife is going to look hot on her first date night. Now stand up we need to put on your bra."

Ash stood and watched as she removed the backless bra cups from the film and applied first one and then the other and clipped them together. Instant cleavage. Jessy ushered him out of the bathroom.

"I need to get me ready now. Go relax for a little, no touching your hair or makeup."

Ash stood in the bedroom nearly naked. What was he going to do while Jessy got ready? He looked at the clock. Already 5:30, no wonder she wanted to start early. He walked to the closet to get out his dress. Walking with it to the mirror he held it up. On the hanger it didn't look that appealing. No wonder women couldn't figure out what to wear when they did that. The dress looked nothing like what it did when he had it on. He pulled out the nude heels and practiced walking in them. He felt a lot more confident than he had on Sunday when he had first tried them on.

He looked up a couple videos on how to walk in heels, and tried to imitate the women in the videos. He felt like they made his hips sway a lot more than usual, but maybe that was the point. He looked at himself in the mirror. The brunette in heels and lingerie looking back at him was hot. Lots of curves, large breasts with quite a bit of cleavage, eyeshadow that highlighted her light brown eyes, curls framing her cute face. He heard Jessy calling him from the bathroom.

Jessy had somehow done her hair up in a sexy messy bun with a few loose curls that looked amazing. Her eye makeup was just a little sultry, drawing his attention from her deep red lipstick to her eyes. She held up the bottle of nude nail polish. "Hands first feet second." She worked quickly, frowning slightly. "Ash? You need a manicure and a pedicure. Do you ever take care of your nails?" Ash thought his nails as a woman looked much nicer than as a man, "Umm, I trim them and make sure they aren't pointy, does that count?" Jessy sighed and shook her head.

She motioned him aside and painted her own nails a dark purple while Ash dried. "Go grab your dress, and bring it in." Ash did as he was asked, careful to not let his almost dry nails touch the dress. Jessy checked the clock. She helped Ash into his dress, carefully attaching the halter neck so as not to mess up his makeup or hair and then pulled the dress down. She walked around him and nodded after pulling a few wrinkles out. "Grab your heels and meet me downstairs, call the ride share, we need to leave in five."

Ash grabbed his heels and used an app to call the ride share. He grabbed his keys and wallet and waited for Jessy in the front hall.

He stopped at the hall mirror and slipped on his heels. He looked at his reflection and loved what he saw. He would have been too shy to talk to himself if he had seen the woman in the mirror before he got married. He would have thought she was way out of his league, just like he had the first time he met Jessy.

Jessy came down the stairs and spun around, her hands full. "Zip me up please?"

Ash zipped her up, Jessy bent down and slipped into a pair of black slingback platform heels. She stood up and slowly rotated for Ash. She was wearing a black strapless dress that showed just a tiny bit of cleavage but left no doubt she had fantastic breasts. The dress clung to her stomach and curves, ending just a few inches below her ass.