A Surprising Development Ch. 08

Kelly lay with her head on Jackie's chest, slowly twirling her finger around Jackie's nipple. Without lifting her head, she quietly said, "The next we make love, I want you to wear your cowl, you know, your breasts."

"Why, babe?" Jackie asked.

"Because I think you need to. You need to feel the weight of them, the sensation of them when we do," Kelly said. "Just try it." She lifted her head and grinned. "I'll make it worth your while."

***

Next Saturday Morning

Kelly was true to her word. Each night that week the two had sex. Sometimes a quickie or just a blowjob but she made it worth Jackie's while.

And Jackie did as she was told. Every day she wore her cowl all day and for lovemaking at night. She wore the C-cup most of the time but since it needed cleaning every so often she had to wear the D-cup one that Kylie gave her some time back. It got so she didn't care which one she wore and became quite use to the larger breasts. One problem was she didn't have a bra to fit the D's so she had to be discreet when she went to class. By week's end, she didn't give it a second thought.

"Mom," Kelly shouted to Kylie as she entered the apartment. "You're early!"

"There was no traffic," Kylie replied as she gave her daughter a quick hug and kiss on the cheek. She quickly scanned the apartment. "Where's Jackie?"

"She's in the shower. She should be done in a minute or two."

Kylie threw her coat over the back of the chair. "Don't think I'll be needing this today. Spring is here, at least for today."

Jackie came out of bathroom, wrapped in a towel. "Kylie! I'm so glad to see you! Give me a minute to get dressed and I'll be right out."

Kylie got up from her seat and followed her. "Wait a minute, there is something I want to talk with you about."

"Sure, what is it?" Jackie asked.

"Do you tuck? I think it is time you tried it if you don't, Jackie."

Jackie shook her head. "No, I don't and why should I now?"

"Because summer is coming and if you plan on wearing a swim suit, especially a bikini, you better," Kylie said with a smile. "Look I think I have the answer right here." She stood up and removed what appeared to be heavy pieces of cording.

"What's that?" Jackie asked with a little hesitation.

"Drop your towel and we'll try it on." Kylie walked over to her.

She wrapped the cord around Jackie's hips and slipped the other cord, like a thong between her ass cheeks. "Now this might feel a little uncomfortable but it will be ok." She walked around and stood in front of Jackie. The cord widened a bit, having something like a pocket. "It will push your cock down and back. As it does that, it will split yours balls too."

Before Jackie could object, Kylie pulled the cord tight and snapped it to the waistband. "There! How's it feel?"

Jackie squirmed. "I don't know."

Before she could continue, Kelly walked into the room. "Oh my God, Jackie, it looks like you have a puffy pussy!"

"Here," Kylie said handing Jackie a pair of panties, "Put these on."

Jackie slid them up.

"Wow!" Kelly exclaimed, "She has a camel toe!"

Looking down Jackie had to agree. She only had a little bugle and when she turned to look in the mirror, she could see what Kelly was saying.

Kelly handed her a pair of black yoga pants. "Damn sweetie, you look good!" Kelly looked around the room. "Where's your cowl?"

Jackie picked it up off the bed. "All I have is yours, Kylie. And I don't have a bra for it!" she said.

"Don't worry about it," Kylie said as she helped Jackie pull it over her head. "Kelly, get your oversized sweater." She turned to Jackie. "It will be great." She fluffed up her hair. "Your necklace, some earrings and a bracelet, you'll be good to go."

Kylie was right. As the three got into Kylie's car, to everyone it looked like a mom and her two daughters were off for a day of shopping and just having fun.

***

Shopping Together

Kylie had decided that today she would treat the girls to a good old fashion-shopping spree. Everything was going well with her business and she had no money worries. Together with Angie's success as a realtor, she felt she could do this. Kelly wasn't spoiled but never had to want for anything. The good thing was that Kelly never seemed to ask for much. It bothered Kylie a little as she wanted to buy things for her daughter.

Since Jackie came along, Kylie felt that she now had a second daughter. Jackie acted as she was too but like Kelly, she didn't want Kylie spending money on her.

Kylie felt very close to Jackie as she understood the difficult choices Jackie was going through. She wanted to support her in any way she could but she also knew, no matter how close they became, Jackie was not her daughter. She could give advice and guidance but the ultimate decision was up to Jackie. Deep down, Kylie believed that Jackie needed to make that decision sooner rather than later.

The first stop was for shoes.

"Jackie, you have done very well so far," Kylie said as they entered the store, "but you need some summer sandals and most importantly some heels."

"I've worn heels before," Jackie quickly answered.

"Yes," Kelly added, "Mine and only 2 inch ones. You need your own and 3 inch ones."

"Right," Kylie chimed in, "So let's go."

The two girls tried on various styles, nothing over the top. They settled on simple white and pink sandals for each of them. The heels took a little longer.

"They pinch my toes," Jackie complained.

"They might right now till you get use to them," Kylie said, "Now walk over there and back."

As Jackie did, Kylie and Kelly nodded. Jackie was a natural in the heels. No wobble or stumble as she walked and she looked good from behind.

"Ok then," Kylie said putting her credit card back in her pocketbook. "Off to the next stop."

"Jackie, you need more of your own clothes. It's great that you can share with Kelly but you need some things that say who you are," Kylie explained, "So here and the next shop we are going to help you."

They entered a small store and looked around. Kylie guided Jackie towards some blouses while Kelly took them off the rack. She picked out three silky ones, emerald green, a silvery blue, and a deep maroon one. "Which one do you like, sweetie?"

Jackie ran her fingers over the blue one. The texture made her tingle as she imagined it against her skin. "I can't decide."

"Ok then," Kylie said, "Try them all on and we'll see how they look on you."

Jackie did, modeling each one. They all felt exquisite and for the first time since this morning she could feel the cock restraint. She quickly had gotten use to it but now she felt it. The material felt that good.

"I think the blue looks best. It accents your eyes," Kylie said turning to Kelly. "What do you think, Kelly?"

Kelly nodded in agreement.

"Good, now for a skirt." While Jackie was changing Kylie found a skirt for her. It was a black little number than resembled leather but wasn't. "Here, try this one."

Jackie returned still wearing the blouse but now modeling the skirt. It was tight around her hips and ass but not too short to become a problem. What surprised Kylie was the fact that Jackie had hips and a tight ass without padding. She smiled at the thought.

"You look real good, sweetie," Kelly said moving up close to her.

"Thanks, babe," Jackie smiled back.

The final stop made Jackie's heart skip a beat. It was a specialty shop, a small boutique that sold only the finest lingerie. The displays in the window were beautiful and stated 'Direct from Paris.' Jackie hesitated as they approached the door.

Kelly reached out and took Jackie's hand. She smiled as she whispered, "Come on, sweetie, it will be fine."

A young girl greeted them as they entered. "May I help you?" she asked.

"Yes," Kylie replied, "We're looking for a bra and panties set for my daughter." She looked over at Jackie.

Jackie stood, looking at the various item. She vaguely heard Kylie, as she became focus on one item. "Wow!" she said softly as she moved towards it. It was a black bustier with a red ribbon trim. As she moved closer she saw it was made up of crushed velvet and lace with matching

panties and garter straps. It took her breath away and made her heart race. She knew she wanted to feel it against her skin. She turned to the clerk.

"Do you think you have that in my size?" she asked quickly.

The girl who was talking to Kylie now turned to Jackie. "I can look. Any idea to the size you need?"

Jackie wasn't sure but before she could answer, the clerk smiled. "I think I can guess."

"Before you look," Jackie said opening her shopping bag and pulled out the blouse she just bought, "Do you think you might be able to match this color for the ribbon?"

"I'll see," she replied as she gave Jackie a quick glance and she headed to the back.

"Oh Kylie, if it fits I want to buy it!" Jackie said grabbing Kylie's arm. "I'll pay the extra."

The girl returned with two. "I'm afraid that is the closest blue we have. Might be more silvery but I think of these will do." She pointed to the changing room.

"Thank you," Jackie said taking them from her and taking Kelly by the hand. "Come on."

Upon entering the room Jackie quickly stripped down. She stood naked before Kelly, her fake D breasts and "puffy pussy" on display. She took the panties and slid them on. She sighed as the crushed velvet rubbed against her crotch. Looking down she could see her camel toe.

"Here, help me get this on, Kelly."

As Kelly helped, she could see that Jackie was breathing quickly and slightly shaking. "Are you ok, sweetie?"

"Yes," Jackie whispered.

As Kelly finished up, Jackie looked in the mirror. "Oh God!" she said out loud. What she saw in her reflection blew her away. It was exactly what she wanted. No longer was Jack looking at Jackie in the mirror. She turned to Kelly, "Its perfect, babe."

Kylie told Jackie to forget about the price. It was her pleasure. She also bought Jackie a white lace demi-bra and panties set.

"This bra doesn't cover much, Kelly, does it?" Jackie said trying it on.

"Well, sweetie if those were really yours, it might make a difference."

"That would be nice," Jackie said as she turned away. She then muttered, "Maybe some day." She didn't realize that Kelly heard her. Kelly smiled as she did.

***

Saturday Night

Jackie was so excited about her new purchases that she talked all the way home. Kelly sat in the front seat with a smile and shook her head as she looked over at her mother. Kylie too was smiling.

"So what are we going to do went we get home?" Jackie said leaning forward.

"I think we'll relax, get changed then go out for dinner," Kylie said. "My treat. There is this quaint little French restaurant I've been dying to try."

"So we have to dress nicely?" Jackie asked.

"Yes, Jackie," Kylie laughed. "You can wear your new outfit!"

Jackie fell back into the seat, "Good!"

The three got home and went inside. Jackie asked Kelly to come up stairs. When they entered the bedroom, Jackie shut the door.

"Babe, I'm so excited right now. I can't wait to go out to dinner," Jackie began, "but I need a little help." With that she wiggled off her yoga pants. "I need to untuck before I die!"

Kelly came over and knelt before her. She rubbed her hand on Jackie's crotch. "Having a problem?"

"Yes!" Jackie squirmed, "Now stop it and help me." She was already pulling down her panties.

Kelly gasped. Upclose, it really looked like a puffy pussy. She leaned forward and licked it.

"Oh fuck," Jackie said throwing her head, "Babe, please stop," she whispered.

Deciding she had tortured her enough, she unsnapped the strap. Jackie's cock popped free.

"Oooh!" Jackie moaned, "It feels so good!"

Her cock looked all small and red as it escaped its confinement but in only a few seconds it began to fill and grow larger. Kelly cupped Jackie's balls in her hand and began to massage them. "Poor baby," she said as she kissed the tip. "Buying new clothes really excites you, doesn't it?"

Jackie just nodded her head.

Kelly quickly stood up. "Wait till tonight. I bet you'll look so hot, sweetie!"

Kelly was right although she should have included Kylie and herself in the looking hot category. Jackie wore her new top and black skirt. She undid the blouse enough to show off her cleavage; she was still a D, and the top of her new bustier. She borrowed a choker of pearls from Kelly but included her bobble necklace. Black stocking and her 3-inch heels completed the look.

Kelly wore a similar outfit only her blouse was emerald green and she didn't have that much cleavage to show!

Of the three Kylie was the one that stole the show. Her maroon dress fit her like a glove. It accented her breasts and clung to her hips. Jackie was sure she couldn't be wearing any panties under it. She was definitely a hot MILF tonight.

Jackie didn't tuck tonight. She was so excited about wearing the new clothes out that her cock had become full. It was not erect but it would never be tucked between her legs. Kelly laughed when she saw it.

"Don't get too excited, sweetie, it might ruin the effect."

Jackie laughed too. "I know but I can't help it!"

Kylie announced that tonight they were taking an Uber to and from town. She thought they would eat then walk around Harvard Square for a while. It was a warm spring night so why not. Maybe hit a bar for a few drinks and not risk driving home. Nobody wanted a DUI tonight. The girls thought it was a great idea.

The restaurant was more than Jackie expected. Located in a rather trendy part of Harvard Square, the little French restaurant resembled a part of Paris. There was soft lighting and quiet music. The conversations around the room were carried out in hush overtones. The maitre de greeted them warmly with a tone that was heavy in a French accent.

As they were led to their table, patrons noticed the three women as they passed by. They received nods and smiles as they sat down.

"Wow, Kylie," Jackie said quietly, "This place is amazing."

"Yes, I heard quite a lot about it and always wanted to go here."

The food, the drinks, the atmosphere, and the people were like nothing Jackie ever experienced. It seemed to suck her in like a warm blanket. This entire day was something she would never forget. A total change was occurring to her.

Across the room an older man stood up. With his tailor suit, his manners, and good looks, he caught Jackie's eye. As he moved to the other side of the table and pulled the chair out, a devastating blonde arose. She appeared to be in her late '20's and was dressed in a form fitting black dress. It was long and cut high up her one thigh, which exposed her toned leg. Her long blonde hair accented her face and reached her mid back. Everything about her oozed grace and sexuality. Her movements were sensual and alluring.

Jackie found herself mesmerized at the sight. Unlike any time before where seeing such a beauty would excite her, she found herself feeling jealous of the gorgeous woman. She wanted to look and be like her. Would she ever become that confident? That sure of herself? Such a women?

"Hey, are you alright?" Kelly said, nudging Jackie's arm.

Jackie jolted back to reality. "Yes, yes," she replied quickly, "I'm ok, really ok."

As the man and woman exited, they passed by the girls. As they did, the blonde looked directly at Jackie and smiled. The smile and look sent a surge of pleasure through her body.

***

Back at the Apartment

They walked along Harvard Square, stopping in to the numerous stores that were open late. They didn't buy anything but they certainly looked in them, especially at some of high priced clothes. Jackie found the exact same dress the blonde was wearing in the restaurant. She begged Kylie and Kelly to wait while she tried it on. When she did, she looked in the mirror. She knew she didn't look anything like the woman but just seeing herself in the same dress made her feel so good.

"Jesus, Jackie," Kelly said with a whistle, "I can't believe how that fits you! It's amazing."

Kylie walked over and put her hand on the small of Jackie's back. The low cut back allowed her to touch her skin. She lightly caressed it as she said softly, "Makes you wish, doesn't it, sweetie?"

Jackie sighed and nodded, "Yes it does."

It was a good thing Kylie called for the Uber because after window-shopping they hit one of the nearby bars. A few long Island Iced teas were enough to make it obvious not one of them could drive. While in the bar a few guys hit on them but without luck.

"Not tonight, boys," Kylie said, "The three of us have are own plans."

Jackie was surprised to see how many of the guys directed their attention towards Kylie.

"I guess they like older women," she joked.

"More likely get the MILF out of the way and the younger cuties will follow!" Kylie answered with a laugh.

They stumbled into the apartment together. No one was what you call drunk but they were definitely feeling it. Kylie took the girls by the hand. "I think I know a perfect way to end this great day," she said with a wink.

All three laughed and headed to the bedroom.

Kelly and Kylie reached the bedroom first. Stripping off their clothing, they beckoned to Jackie to lie between them. As Jackie started to take off her clothes, Kelly said, "Oh no sweetie, just take off your blouse, skirt, and shoes. Leave the rest on."

Jackie did as she was told and crawl between them.

"You look so fuckin' hot, sweetie," Kelly said as she nibbled on Jackie's neck. Her hand went immediately to Jackie's crotch where she found her cock growing hard beneath the panties. She began to stroke it through the material. "You like that, don't you?"

"Fuck, yes," Jackie sighed.

Kylie slid up the bed and cupping her breasts, and whispered, "Wouldn't you like to suck mommy's tits?" As she did she grabbed one of Jackie's fake breasts and squeezed it. Jackie greedily began to suck on Kylie's breasts.

Kylie softly moaned. "It feels so good, baby. Mommy loves when suck on them."

Kelly pulled Jackie's panties off and let the hard cock spring free. She kissed the tip, tasting the clear drop of pre-cum that formed on it. She placed her mouth over the head and whirled her tongue around it.

"Oh fuck!" Jackie moaned and she sucked harder on Kylie's breasts.

All day dressed as she was, Jackie body was ready to explode. It was like she was sexually aroused all day. She began to rub her fake breasts through the bustier. She imagined they were real and she could feel them.

Kylie whispered in her ear, "Yes, play with your tits, baby. Imagine how good it would feel."

Jackie groaned.

Kylie slid down the bed until she reached Jackie's cock. She motioned to Kelly to move up the bed. As Kelly did, Kylie began to stroke the cock slowly. With her other hand, she positioned two fingers against Jackie's asshole. As she pushed in, she said, "You like your ass fucked, don't you, baby?"

"Yes," Jackie moaned in response.

"You want me to fuck your ass, don't you?"

"Yes," she moaned.

"First, we need to get you ready," Kylie pulled from the nightstand two small metal rings. She placed both in her mouth, making them wet. She wrapped one around the base of Jackie's cock. It closed with a hard metallic click. She quickly did the same around her balls.

"They're too tight!" Jackie grunted.

"Yes, they are tight," Kylie replied with a devilish grin, "Tonight you are going to be fucked, little girl, and you will beg for release." She flipped Jackie onto her stomach. "We will cum before you do. Understand?"

As Kylie positioned herself, Kelly sat in front of Jackie. She pushed Jackie's face into her wet pussy. "Eat me!" she demanded.

Kylie fucked Jackie's ass while she ate Kelly's pussy. They were using Jackie for their own satisfaction tonight. Surprising Jackie didn't care. She was lost in her own sexual haze, tasting Kelly's pussy and feeling Kylie's cock in her ass. Pre-cum poured from her cock onto the bed but she didn't care. It was not just her cock but also her whole body that felt alive. She was aware of how her body was responding. Somehow even her fake breasts bouncing with every movement were adding to the sensations.