A Couple of Wishes Pt. 02

Ash sat in silence for a few minutes, digesting what Jessy had just said. She wanted him to be her wife. Was she starting to view him as a woman? Did he view himself as a woman? Right now, he was a man, he felt like a man. He had a dick and balls like a man. But... He had just asked to buy women's clothing. He was wearing women's underwear like it was a normal thing. Sure, it made sense since he had switched back to a woman during the hike, but he liked wearing it. Not like a crossdresser that gets off on it. But it felt just as natural to wear women's clothing as men's clothing. This was getting complicated.

He hadn't been thinking about the coming week at work and what that would mean for the fantasy. He'd just assumed he'd go to work when he needed to, be a man, and get things done. Part of him also assumed he come back home and be a woman when he got there.

Jessy interrupted his thoughts. "Hey, could you get off the highway at Turtle pike? I think we should stop at the outlets to get most of this stuff, so we don't spend too much." Ash made the turn and sat in silence lost in his thoughts trying for the first time in his life to figure out his gender identity.

They pulled into the parking lot and got out of the car. The stores were busy. Summer had just started, and people seemed eager to get out and apparently buy new clothes. The next hour went by like a whirlwind. Ash felt like the car was starting to fill up with bags. Socks, shoes that hopefully fit, a pair of black flats, strappy sandals, thong sandals, a pair of three inch nude heels, some cute wedges, tops, yoga pants, a pair of high waisted jeans, blouses, some leggings, two sweaters off the sale rack, makeup that he had no idea how to use, Jessy was really enjoying herself. It was like she was a little girl getting to pick out clothes to dress up her dolls.

Ash had asked in the first store how she knew the right size. She had grinned at him, "I've seen you naked enough the last two days to have a pretty good idea of your sizes. You remember the store I worked at the summer after college when we met?"

"I do. The little boutique that you said you made absolutely no money at because you spent everything you made on clothing at the store?" Ash smiled; he had fond memories of that store. Especially his visits to see her after the store closed. More than one makeout session with lots of heavy petting had happened in the overly furnished dressing room.

"Well, the summer there taught me how to guess women's sizes really well. It also taught me how to pick out clothing for different body types. How do you think I shop so fast?"

Ash looked around at the slow-moving shoppers at the racks, most folks were very slow as they looked at clothing, held it up, picked up more. "I guess I thought you didn't like dressing rooms. You have always said they seem so dirty. I figured you'd rather try things on at home."

"I don't and they are, but did you notice I seldom have to return things?"

Ash had honestly not even noticed. He just knew whatever she bought seemed to look great on her and he just enjoyed the view.

He had trusted her choices and helped pick colors and commented on cuts he thought were too low or pants he thought wouldn't flatter his ass. It probably looked like Jessy had lost all of her clothing in an accident and was replacing it all. Ash felt like he looked that way, wearing a sweatshirt and some ladies joggers.

They stopped for a bite to eat at a café, the last time they had eaten had been hours ago back at the lake. Jessy went through her list. "All we have left is the dresses, swimsuits and lingerie. I'm amazed at the sales today, I thought this was going to cost more." Ash had been tracking the costs too. Jessy had gotten a few things for herself, but he hadn't freaked out yet about the price tag. He was also really looking forward to trying all this on. Just that might take hours.

Ash looked up at Jessy, something had been on his mind since they got there. "Jessy, you said you didn't think you'd ever marry a woman. That insinuates that you had considered it and are attracted to women."

Jessy finished the bite of food she was chewing. "Well, I generally prefer men. I like to look at women, they are beautiful, they have curves that men just don't have. I know you've caught me starting at other women's boobs."

"I just thought you were looking at their clothing or comparing assets."

"Well, that's probably true too, but I love breasts. I always have. When I was a little girl, I would get excited to go to the locker room hoping to see all the topless women. Plenty of little girls are obsessed with boobs. Most I think because they can't wait to have a pair of their own. My attraction to breasts is more... sexual." She looked over at him, "I told you that after high school I dated a few women, right?"

"Nope. You never said dated. You said you kissed a few girls in college but never said dated."

"Oh, well yeah. I dated a few, lots of kissing, most of it topless. You know, boobs. We never got to the main event though. I fingered a girl once but that's as far as it went. They were complicated, hormonal, they never knew what they wanted. After a while I stopped dating girls. The hardcore lesbian types never appealed to me, so the girls that I was into, I just stopped being into. I never stopped looking at or masturbating to hot girls with great tits that I saw naked in the gym showers." Jessy looked him in the eyes, "I guess I never told you that, maybe I was afraid you wouldn't like that part of me or want to have a threesome. I've never wanted to share you or step outside our marriage. I've felt like you were as close to a soulmate as I was ever going to get. To be honest the last couple years I think I've not had as much sex with you because... well because, I wanted more. I wasn't sure what more was. It's probably why when you said you wanted to have sex with a woman with a dick, I got hooked on it. It was something more. But it got better than that, suddenly you were more. You had the body of a woman, boobs, the soul of a man, and you were already mine."

Ash put his hand on hers and squeezed it. "Jessy, I love you. I accept you and everything you are. I wish you'd told me earlier; I don't know how I would have helped but I would have liked the opportunity to try." He smiled and held her eye contact, "If you want me to be your wife and your husband, I'm in. I've loved the last two days and if I'm honest with myself I think I love being a woman, but it's because of you. You have made me feel special each step of the way. Sure, it helps that we have had a lot of great sex, but it's been more than that. I feel like we are closer than we ever have been. I don't know what it's going to look like when the kids get back, but we have two weeks to figure it out, wife and wife or husband and wife." Jessy had started crying a little. Ash wiped her tears and gave her a kiss.

The kiss was a little longer than most people are really comfortable with in public settings, but people didn't notice or pretended not to care. That moment was all about them. By the time they were done, Jessy had stopped crying, and Ash was a little turned on. Jessy stood up. "Ok we have three things left, swimsuits and lingerie first. Hold on a sec I'll be right back."

Jessy was gone for a few minutes. Ash sat there; he was honest about everything he had said. If only they could just continue their lives with him as both a woman and a man, and Jessy with her enhanced package. I didn't see how that would work, especially with the kids. He was trying to solve that puzzle when Jessy came back. "Let's go, we need to make a pit stop."

Ash grabbed their trash and tossed it, trotting to catch up with Jessy. She led him to the section of stores that was empty. The area was still clean but no one was there. The signs said that the area would be re-opening next year with re-modeled stores and that management had moved these stores to other locations until the renovations were done.

Jessy led him to the women's bathroom. It was still open but vacant. She pulled him in and locked the door. Ash raised an eyebrow and gave her a questioning look. "Strip to your panties please, you can leave you socks on." she commanded.

Ash gave her another questioning look but did as she asked. Almost naked Ash stood there. Jessy at him expectantly. Ash finally asked, "What are we doing?"

"Shhhh, just wait."

Ash started looking around, he'd been in a women's room a few times before, it looked and felt a lot like the men's room, except with all stalls. It smelled less like urine but overall, not much difference. Looking back at Jessy he realized why they were there, he felt his body shifting, his breasts expanding, his shoulders narrow, his hips and ass push out. His hair tickled as it draped down to his shoulders.

This was the first time he'd been standing still for the transformation. It didn't feel weird, just like he was moving from himself to himself, or herself, whatever. He looked down, bulge present, a moment's thought and the bulge was gone, he could just make out the shape of his vulva thought the material. Jessy smiled and pulled a paper tape measure from her purse.

"I'm glad it worked, I wasn't sure it was going to be private enough." She went to work taking his measurements, under his breasts, around his bust, waist, hips. She whipped through them taking measurements on a piece of paper. She pulled out her phone looking up at Ash, "You should get dressed."

Ash dressed, he was still wearing the ruined shirt and it looked a lot better with breasts than without. He decided to take a quick pee before he left entering the stall and quickly went. First pee in a women's room.

When he came out Jessy was also taking a pee break. She yelled through the door. "If you unlock the door and prop it open, I think you'll change back."

Ash tried it and waited, it didn't work, he walked out in the hall, boobs still present. He walked out of the building, yup there they go. He was glad no one was around to see the change, that would have been really hard to explain.

Jessy came out, "Did you have to come all the way, oh, yeah you did." She said as her hand went to her crotch. "I guess this area really is private."

She led him to a swimsuit store. "Ok we are going to get a nice one piece and a bikini for sunbathing and the hot tub. Find a one-piece swim suit you like and bring them back; you wear a medium."

Ash found two he liked, one sleek green and blue one that looked like a professional swimmer would wear, he wasn't sure about the butt coverage though, it looked a little like a thong. The he grabbed another that was a bit more stylish. A light blue ribbed fabric with cutouts right above the hips, the same high cut over the butt cheeks, they all seemed to have that, padded cups and halter top straps that tied behind the neck. He brought both to Jessy.

Jessy looked up from the two bikinis she was looking at, Ash showed her his choices. "Hmm the blue one would look really good on you." She looked at the other. "Why that one?"

"Umm so I could lap swim?"

"You want to swim laps with me?"

"Yeah, how else am I going to get in shape? I don't want to get fat."

"Babe, you'd be a guy at the pool. Don't get me wrong I think you'd look hot in it but when you leave the house..."

Ash was feeling a little crestfallen. He had forgotten he couldn't wear all the things they'd gotten in public. He paused for a moment before responding timidly. "What if things changed? What if I could stay a woman when we left the house?"

Jessy's eyes twinkled, "Ok, just in case, let's get both, and we will get both of these too." Ash looked at the suits, one was a deep red and looked like it would barely cover anything, ok a lot more than nothing it would be fine at any beach or pool, strings providing the attachment at the hips, back, and neck. The other was black and had that high cut on the butt and looked like the suits that professional female surfers wore.

In lingerie store. Jessy sent him on a mission, "Four thongs, make sure they are seamless, three briefs, and four pairs of whatever else catches your eye, again you're a medium."

Ash felt a little awkward. Some of the women gave him weird looks as he browsed. He hadn't wished back his package after the bathroom so he was walking around with no equipment at all. He wondered if the women would have felt better if they knew that. "They probably would have given me dirty looks anyway if I looked like a woman." he thought to himself, "They only wish they had my curves."

Ash quickly picked out the thongs, basic, solid colors. The briefs were the same, basic, solid colors in some material that felt silky but stretched. The four pairs of whatever he wanted though that was harder, did he want lace? More hipsters, cheekies, boyshorts? Hmmm.

There were a lot of options. In the end he opted for all lace in several bright colors, two boyshorts, and two cheeky panties. Bringing them to Jessy, he dropped them in the offered basket. Jessy had put a body suit in the basket and was looking at bras.

She pointed out two, "You are probably a 36D, you really don't need a push up, just lightly lined. I'd recommend this one for support and this one to lounge around in." Ash picked colors that matched at least one pair of panties and put them in the basket.

Jessy led him to the sports bras. "Ok those bras you picked up yesterday are ok, but they aren't going to provide much support if you go running or are really active. Did you notice how much your boobs moved today on the hike?"

He had, "What do you think I should get?"

She picked out two cute full coverage sports bras, one grey, and one purple. "These are good quality and should support you when you're hiking or running." He motioned for her to toss them in the basket.

"Do you need anything?" Ash asked.

"Nope, I've got plenty from this store, the stuff I really want is much more expensive. But I do have a birthday coming up..." She hinted, "You ready?"

Ash looked around, he kind of wanted some pajamas like Jessy had, the silky fabric with a 3/4 shirt, the short shorts that outlined her breasts and just barely covered her butt. But he held back. "Nope let's go."

As they left the store Ash was stunned, he'd purchased lingerie for Jessy many times before but those had been single sets, or just one bra. The total stunned him. "I didn't realize how much this stuff costs!" he moaned.

Jessy shrugged, "Quality bras and panties aren't cheap, just think about your sports underwear, those are usually $30 a pair. It's not too much different."

Ash was still stunned; they had spent more there than at any other store. "Ok I get it, dresses next?"

"Yup, dresses last."

They ended up going to two stores. The sundress was easy, floral print, scoop neck and wide straps, pockets. It would hug his hips but be easy to walk in, and show plenty of cleavage. The LBD, not so much, that's why they went to two stores.

In the end Jessy picked it out, he had no idea what it would look like on him, just that she said he would be stunning. It was getting dark by the time they left. Jessy drove, she was still invigorated, Ash felt wrought out. He hadn't tried anything on, and he was still tired from shopping.

When the garage door closed, they both seemed to hold their breath. They were obviously going to transform but still anticipated it. Jessy felt it first, the pushing sensation and additional tightness in her panties. Ash sat still and tried to feel each thing happening, hair, boobs, vagina, labia, hips, butt, thighs, shoulders. It was weird, it felt so natural to go from one form to another. They got out of the car and brought everything in. Jessy put down most of the bags in the living room and motioned Ash to do the same. "

Let's take a quick shower and then I want a fashion show."

The shower was less than quick, with some solid teasing. They managed to not have sex, but by the time they exited the shower, Jessy was hard, and Ash was wet from more than the shower.

Jessy handed him one of her thongs, "Put this on before you try on the other underwear, that way if they don't fit, we can return them. See you downstairs." She left Ash in the bathroom drying his hair.

Downstairs Jessy had but on a loose shirt, joggers and nothing else. Her nipples stood out thought the thin material of her shirt. She was looking forward to taking it all off again soon. Ash came downstairs wearing only the thong, his hair damp.

Jessy smiled, "Ok time for the fashion show. Lingerie first." Jessy hooked her phone up to the TV so Ash could see each outfit from her perspective.

The panties all fit, he took off Jessy's thong, threw it at her face, and slid into a bright green lacy pair of boyshorts he had purchased. The bras also fit really well, no pinching, good support, no bulge at the top. Jessy had nailed the sizes. The sports bras held his bust comfortably and securely. Jessy laughed when he jumped up and down, his ass jiggling and his boobs shifting but not bouncing around.

Then came the yoga pants, the jeans, Jessy had to help him slide them on but his ass looked great in them, tops, on and on. Everything fit and more importantly really flattered his figure. Soon it was down to the swimsuits. Jessy suggested he also try those on over his panties.

First came the one pieces. They fit well, he was unsure about how much of his ass was exposed, showing off a lot of the green lace of his boyshorts. Jessy assured him that was the style and that they would be fine. The surfer bikini was tight on his chest and flattened his boobs a bit, giving him a little side boob.

Jessy got up and walked around him inspecting, she adjusted a few things, and the side boob went away, giving him nice cleavage and support. The bottoms fit like a glove, and he was pretty sure he could use a diving board without them falling off.

The red string bikini was just that, some triangles but mostly strings. He felt a little exposed but when he saw his image on the TV, he knew why Jessy had picked it. He looked amazing, his underwear ruined the effect it a bit but, damn, he looked so good. It made him feel like a swimsuit model.

The bottoms covered not much but just enough of his butt to make you want to see more. The front dipped low enough he would have to always have to shave pretty much everything to wear it without showing pubic hair. The top had more coverage than he had assumed. The strings pulling the triangles of fabric below his breasts and covering up most of the breast while leaving each side bare. The halter pulled his breasts together creating just a little cleavage.

Jessy had been nursing a semi as Ash changed in and out of the clothes. She knew she had picked things flattering to his figure, but she was getting a bit jealous, he looked great in everything. It hadn't helped that she could see his vulva thought the lace panties each time he took off some pants or bent over, that was a bit distracting. But all that paled to how he looked in that red swimsuit. She debated taking her dick out to masturbate. She watched him turn red when he saw how hard he had made her.

"Is that for me?" He got down on his hands and knees and started to crawl across the floor towards her. "Does me in a bikini make you hard?" She looked at him, damn he made a good-looking woman.

Ash stood up and laughed at her. Teasing her was fun. He stripped out of the swimsuit and looked at the dresses. "I think I'll try those tomorrow; we need to have something to look forward to." he told her. Jessy could only nod. "Speaking of tomorrow, what do we do about tomorrow?" He sat next to her, their hips touching still wearing only the lace boyshorts.

Jessy pulled her eyes from his breasts and looked at him "Tomorrow?"