Girls' Night Out Ch. 17

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"Kylie" takes a leap.
12.2k words
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Part 17 of the 21 part series

Updated 06/15/2023
Created 10/26/2022
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Wednesday Night

Kylie was so excited when she arrived home that she decided to reward herself. First she bought some Thai take-out and was going to take a long hot soak in the tub. She thought about how the weekend went as she ate dinner. First they all got along so well. Second they had come to some kind of decision regarding the dress. And finally she had that talk with Chrissie. Kylie couldn't see how that could have gone any better. So overall it was a great weekend and Angie was coming home tomorrow. What could be better?

She leaned back in the tub and immersed her body in the warm scented water. It felt so fucking good. She sipped on her second glass of wine and sighed. Slowly she raised one of her legs out of the water and ran her hands along it. It felt so smooth, like the rest of her body. She never had much body hair to begin with but now using the lotion Angie gave her and the new laser razor there was nothing there. Just rubbing her own body was exciting.

Soaking in warmth, Kylie thought back. She knew that where she was now was where she should be. It was more than his sisters dressing her up. She remembered sitting around waiting for track practice with her then girl friend Michelle. They were stretching, getting loose to run, when Michelle said in all seriousness, "I bet you would make a cute girl." Michelle turned to her friend, Denise, "What do you think?"

Denise looked at her and said, "You know you're right. A little make-up and hair style would do it."

"Stop it," "Kylie" protested.

Michelle smiled. "Just saying, cutie."

"Well don't even think about it cause it is not going to happen, ever!" "Kylie' got up and walked away. How could "she" tell Michelle that at moment "she" was wearing a pair of flowered bikini panties? Just thinking about what Michelle and Denise said made "her" feel excited.

Her thoughts turned to this weekend. Each dress she tried on felt amazing on her. Looking in the mirror at the shop and hearing the girls' comments sent a rush through her. Rose talking about going commando made her heart race, so much so she almost caused a problem! "Could she go commando?" she wondered.

Kylie finished her wine and stepped out onto the fuzzy mat. Starting to dry herself, she stopped and looked in the mirror. She looked herself over from head to toe.

Ravenna had done wonders with her hair. The red was perfect. Not too bright but red enough to catch people's eyes and to make her blue eyes seem brighter. The fact that it was her own hair made it all the better. Ravenna has worked similar magic with the make-up, bringing out the soft look. Now even without make-up, Kylie looked feminine and cute.

She placed her hands under her breasts. They were magnificent. The feeling, the weight, and the look were perfect. The doctor definitely knew her business. She was right too about the sensitivity. Kylie pinched her nipples and resulting sensation made her sigh.

She ran her hands down her sides as she turned around. There had been some definite changes in this area. It was hard to explain why but her hips appeared a little wider and her ass also. Perhaps it was the result of daily riding the stationary bike. That had toned her legs up but was it helping in those areas? She read about butt enhancements but ruled those out. She didn't want any thing to do with that.

The bike had made her legs tighter and she knew that some men had noticed them. It was a little harder in the winter but with yoga pants and tights you could show a little. She realized that wearing heels did a great job showing off her legs and tightening her ass.

Finally there between her legs her cock hung down. It all started there. The feel of satin and silky panties against it always made her hard. Wearing her sister's panties under her clothes in school was a wonderful sensation. When Suzi and mom's friend found out, they didn't make fun of it but in their way encouraged it. There was nothing unusual about Kylie's cock. It was of average size but she swore there was times it grew bigger and harder than it ever did. Angie understood that by Kylie simply wearing sexy lingerie could make it happen. Her hand absent-mindedly went to her cock. Like the rest of her it was smooth and it felt delicious. Slowly it grew in her hand.

"Whoa, slow down, girl," Kylie laughed. "Angie will be home tomorrow." She picked up the wine bottle and swished it around. There was just a little left so she poured in her glass. Finishing it, she headed to the bedroom. "Well, teddy what should we wear tonight," she said picking up the stuffed bear. "Let's see."

"We could wear this," picking out her flannel pj's "Or even this!" grabbing her old football shirt. Her eyes fell on one of new chemise and panties set she bought yesterday. She wore the other one on Tuesday night under her clothes and this one was sitting on top of the dresser. Why she chose it, she couldn't really explain. Perhaps it was from the wine. As she slipped it on, her body shivered from the silky smoothness.

Kylie felt restless. She was excited over the weekend and what had occurred. Just thinking of what happened with Chrissie made her skin feel alive. She was wishing Angie was here. She tossed under the blanket. The movements made her satiny sleepwear rub over her body. She rolled onto her stomach. Now each movement allowed the material to slide against her. She flipped over on her back.

She carelessly moved her hand over her breast. As she touched her nipple through the cloth, she sighed and moved her legs. It sent a jolt of pleasure through her. She began rubbing both her nipples causing her to squirm on the bed. It felt so good she couldn't stop.

Keeping one hand on her breast, Kylie moved her hand downward. She could feel how hard her cock was as it pressed against the waistband of her panties. Instead of slipping her inside her panties, she wrapped her hand around her cock keeping the satin material in between. She moaned, "Oh fuck!" as she began to move her hand up and down her shaft.

She hadn't done this in a long time but tonight she felt she needed to cum. Each stroke of her hand caused her moan and move about on the bed. The feel of the panties around her cock was exquisite. She started stroking harder and faster.

This was bringing back old memories of when she would steal her sisters' underwear and sneak off to her room. Some days after wearing the panties under her clothes she would come home desperately needing to cum. Now she had that same feeling. Her mind brought back the memory of when Suzi burst in to find her stroking her hard cock with Suzi's panties wrapped around it. Her reaction to seeing it was one more step in acceptance.

Kylie groaned loudly remembering the scene. "Oh God! Yes!" she yelled out as her cock exploded in the satin panties. She kept stroking it, milking every last drop, and hoping the feeling would go on.

She relaxed her grip and let her shrinking cock fall from her hand. Her new panties were soaked from her cum as the wetness spread. Kylie didn't care at that moment. She needed to cum and she did, hard. As she caught her breath she said out loud, "I fucking love this!"

***

Thursday

Kylie sat cross-legged on the bed, her computer on her lap. After last night she was now dressed in her old football shirt. The new chemise and panties were soaking. "Thank God," she thought. "They are machine washable!" She looked at the screen and hit send. She had just purchased three bathing suits. Quite a big step.

The phone rang and Kylie picked it up. "Hi babe, what's up?" she asked. "Everything ok?"

"No! My flight is delayed," Angie began. "Don't know when I'll get home."

"Oh no. At least it is not canceled." Kylie answered back, hoping to sound cheerful.

"You're right. How is everything going, sweetie?"

"Really great, babe," Kylie replied. "Picked out two dresses. I'll show them to you get home. Talked with Chrissie. It went surprisingly well. I just bought three bathing suits. How about you?"

Angie sighed, "It was too long. It could have been done by Tuesday. Learned some things but not much." She paused. "God, do I miss you, sweetie."

"Miss you too, babe," Kylie said. "A lot!"

"Yeah, last night I really wanted you," Angie replied.

Kylie giggled. "Me too. It was hard."

Angie laughed. "Your cock or just the feeling?"

"It was super hard, if you know what I mean," Kylie said.

Angie gave a little groan. "I can guess. My pussy needs your attention, sweetie."

Kylie felt her cock beginning to stir. "If you don't stop right now, I may have to take care of business."

"Is it getting hard?"

Kylie's cock popped from under her shirt. "Yes it is, babe, very hard."

Angie gave a little laugh. "Don't you touch it. I want to remember you that way so when I get home you'll be ready for me."

"Don't you worry, babe, I'll be ready!"

"Look got to run," Angie said quickly. "They just announced something about my flight. I'll call you back if I know more. Love you sweetie."

Kylie put the phone and fell backwards on to the pillows. She looked down to see her cock standing hard and erect. She smiled as she thought, "Just wait, you'll have some fun tonight!"

Kylie jumped and stripped off her shirt. She quickly showered, making sure not to play and got dressed. She knew if she stayed home the feeling would grow and it would be difficult to resist. She put on a pair of soft, silky panties. As she slipped it over her cock the feeling it gave her made her realize this might be a mistake. She got into the car and headed to the gallery.

The gallery was closed and it was open only Saturday and Sunday since Valentine's Day. Even then there were not many customers who showed up. There was only so much she could do but she found that she would be more than prepared for this year than she was last year. The change from Cary to Kylie re-energized her and caused her to take a hard look at the business. Before it was a pastime, something like a hobby, now it was a true business, a place to work on and make go. Why this happened she had no idea but she didn't care. It was hers and she was going to make it good. It was a major reason she told Ingrid no. She would be giving up what was all hers, to make or break, and she didn't want that.

Kylie tried to keep busy straightening the studio and filing papers but her mind continued to wander. Each step caused the panties to rub up against her cock, sending little shocks through her body. Even the glass bobble between her breasts that hung from her necklace felt good. "Why am I so fucking horny?" she thought. "I just came last night and the sex with Chrissie was great. I feel like I need to cum again. So why now?"

She thought about the three bathing suits she just purchased. The website had many items for cross dressers from breast forms to butt enhancers. There were many choices of clothing too. The best part was a video that explained how to wear a bathing suit and what she could wear under it. Armed with that information she was emboldened to buy.

The first was a one-piece white suit. She stayed away from the racing style with the fear of accenting her shoulders. They weren't broad to begin with but she was taking no chances. The thin straps looked to provide enough support for her breasts and though the front was low enough to show some cleavage it didn't show too much.

The next suit was a two-piece. The top looked to show much more than the one piece, which was ok. Kylie knew she had no problems showing her breasts; even a little side boob was good. The bottom was a traditional bikini so it covered her ass and there was enough material to work with in the front. She picked a coral and blue color pattern, which she liked because of its brightness.

Kylie hesitated on number three but then threw caution to the wind. It was a string bikini with a tiny top and equally tiny bottom. She wasn't sure if she would be even able to wear it much less cover up her cock. She read what the site said and even watched the video. They made it sound so easy. She bought a pair of special liners for it but it seemed to her the only way she could wear it was to tuck. If she had to and it looked all right then that was what she would do. She also realized it depended on what beach they were going to on St. Thomas. That would decide a lot.

Thinking it over, Kylie felt all three were good choices. Each one would require a little risk and daring on her part. The white one should be the easiest to wear and the two piece would mean a little more chancing it. The black one would take a lot on her part but the good thing was that no one was forcing her. She could just say no. Deep down inside she was hoping she had the courage to do it.

Kylie decided that staying at the gallery was not going to do it for her. She had get out and goes some place to take her mind off how she felt. Thinking of bathing suits and tropical beaches was not the right mind set for that. It was after lunch and she didn't really have a breakfast so perhaps food might do it. Then go to the bookstore and browse around.

She went to the local deli and grabbed a salad and water. It was healthy at least. Instead of eating right away, she headed to the bookstore. There might be a cheap paperback she could pick up then go over the canal. She could eat there, read and just relax. It was worth a try.

Kylie smiled and gave a small wave to the woman behind the counter. "Hello Kylie, haven't seen you in a while. Looking for something in particular?" Wendy said smiling back.

"No, Mrs. Duncan, just something to keep my interest for a time."

"Ok, let me know if you need any help." Wendy said returning to what she was doing. Wendy Duncan and her husband had been running the bookstore for quite some time. Kylie found that they had a great selection of books, new and old, and she enjoyed browsing the shop. She also found some great books and education toys that she would buy for Suzi's girls. It was a fantastic local place to shop.

She was sure what she was looking for. Something not too challenging and heavy but something that could be a quick read. Perhaps some kind of bodice buster! She found a section in the paperbacks and picked up the one with the most interesting cover. She laughed to herself. "This one looks trashy enough."

Kylie put the book down on the counter. Wendy picked it up and smiled. "It seems these books fly off our shelves. Good to read on a cold night or hot day on the beach. Will that be all, Kylie?"

"Yes, Mrs. Duncan, for now."

Wendy handed the book back. "Congratulations on your upcoming wedding. I say good for you."

"Thank you, Mrs. Duncan," Kylie replied and she headed out to her car.

As she drove to the canal, Kylie thought about what just occurred. Wendy Duncan was a townie, one that had been here for quite a while. She, like Rose and Mary, and Mr. Edwards set the tone for the community. Kylie was pretty sure they thought Angie and she were lesbians yet it didn't seem to matter. Even Cassie's mom thought it was all right for her daughter to move in with them though Kylie was sure mom was much happier that Cassie was dating Jamie. The point was that Kylie believed she couldn't have chosen a better place to do what she doing. They just seemed to accept her for who she was. Deep down she had a feeling that if they knew her secret, most if not all would shrug it off. Of course, Kylie wasn't 100% sure!

As she ate her lunch, Kylie read her book. It was full of hot scenes of lusty women and dashing men, of ripped bodices and torn shirts, and steamy romps, not only in the bedroom. It was a quick read and she found herself halfway through it by the time she finished her salad. Even though it didn't do much in a way to calm her horniness, it made her think about the corsets she saw in the lingerie shop. Rose had mentioned it and it definitely piqued her curiosity.

Kylie looked down at her phone. "Damn," she said out loud, "How did I miss it?" There was a missed call from Angie. Before she went to the voice mail she saw Angie sent her a text. She opened it. It said she should be landing in Boston at a little after 3. With traffic should be home around 5. Plan supper.

Kylie sighed. "Thank God, she'll be home soon!"

She drove over the local grocery store and picked a roaster chicken and so other items including a bottle of wine for dinner. She knew she didn't need any wine to put herself in the mood and she was pretty sure Angie wouldn't either. As she put her purchases in the car, she looked up. In the same place was the lingerie shop and like the siren's song, it drew her to it.

"What the heck," she said to herself. "Why not?" She slammed the car door and headed over. "Hi Tammy, I'm back," Kylie said as she entered the shop.

"What are you looking for today? Another big date?"

Kylie laughed. "No, not that. The other day went I got fitted for my wedding dress Rose said something about a corset. I'm not really sure exactly what she meant so I'm curious. Perhaps you could help me? I do have my measurements if that is a help?"

"Ok then I'll be right back." Tammy walked over and locked the front door. As she returned she said, "It's been a real slow day and don't want us to be disturbed. I want to do this right. I hope you don't mind."

Kylie shook her head. "It's ok with me as long as you won't get trouble."

"It's no problem. Now let's started."

Tammy explained the difference between corsets and bustiers. She said there was something that was kind of in-between. She guided Kylie into a side room where there were a number of examples.

"Ok we will start with a corset," Tammy said pick out one. It was black with a brocade flower pattern.

"That's very pretty," Kylie said. The thought of trying it on made her feel excited.

"Take off your blouse," Tammy instructed her, "Your bra too, if you want. It's just us two in here."

Kylie looked around, a little embarrassed. "Well ok," she removed both her blouse and bra. The cool air of the shop made her nipples harden.

Tammy looked at Kylie's breasts. She remembered them from the last time. She wanted to reach out and touch them but she resisted. "All right, I'm going to put this around you. There are four grommet clasps in the front and it laces up in the back. The inside has a satin lining but it still might feel odd against your body. Here goes."

Tammy wrapped the corset around Kylie and fastened the clasps. Kylie's breasts rested on the top edge while the bottom edge sat on her pants' belt. "I'm going to tighten the laces in the back. It should be a little tight but I won't overdo it. You need to be comfortable." She started tightening the laces. "Don't inhale! You have to be able to breathe!"

Kylie could feel the corset tightening around her. At first it felt uncomfortable but her body adjusted to the pressure. It felt good to feel it press against her. Maybe a little too good. "Ok, Tammy that's enough!" Kylie said giving a slight moan.

Tammy tied it off in a bow and walk around Kylie. She liked what she saw. The corset gave some real definition to Kylie's hips and ass. She unconsciously bit her lip. "Here look in the mirror."

Kylie turned and looked at herself. "Wow!" she said, "I like the look. I see it has detachable garters too." The narrowing of her waist really gave her a great figure. Her body loved the feeling it gave her.

Tammy went and found the matching bra. "There are two types, full cup and half. I think the half would look better." Kylie slipped it on while Tammy fastened it in the back. Tammy reached around and grabbed Kylie's breasts. "Let's make sure they are all tucked in." As she did she pressed herself against Kylie's back.

"Tammy, what are you doing?" Kylie asked quietly.

All flustered, Tammy jumped back and quickly walked around Kylie. "Sorry, I just." She turned red as she blushed. "Let me get the panties. Thong or bikini? Would you like to try them on?"