A Surprising Development Ch. 04

Chapter 4

Saturday Morning

Kelly sat down with her mom the next morning. They had thrown on their robes and now sat together sipping their tea. "Well, mom," Kelly said, "I think last night went very well, don't you?"

"I hope so," Kylie said with a slight smile, "I hope I didn't go too far."

"What do you mean?"

"It's a pretty big step to take a cock up one's ass for the first time plus finding out their girl friend's mother is more than she could ever begin to believe," Kylie explained. "That's a lot to handle. How do you think Jackie is this morning?"

Kelly took a sip of her tea. "She is taking a shower right now. And from what I could hear through the door, she sounded kind of happy."

At that moment Jackie came bounding into the kitchen. "Good morning!" she said cheerfully. She was dressed in a t-shirt and white cotton panties and it was obvious she had put on her fake "boobs". She gave Kelly a hug and a kiss and then did the same to Kylie. After fixing herself a cup of tea, she sat down at the table. "So what fantastic things do we have planned for today?" she asked.

Kelly looked at her mom and shrugged. "So everything is ok? You're alright?"

"Never better. Of course I'm a little tender, if you know what I mean," Jackie answered.

Kylie reached over and took Jackie's hand. "So about last night, any questions?"

"Questions?" Jackie gave a little laugh, "I have hundreds but you answered a few last night."

"Really?" Kylie asked. "Which ones?"

"Ok then," Jackie began, "It's clear why all of you are so understanding and supportive. Also I understand why it was difficult for you to answer the questions I asked before. So if you don't mind, could you explain all of this to me because I was truly surprised last night. Not upset just surprised."

"I might as well start from the beginning, Jackie," Kylie said and she began her story. She started off as say she was born a boy named Cary. She told Jackie about her four sisters and how they helped her mother raise her. They dressed her up as a little girl and that she got used to wearing panties even before she went to college. With the help and support of Angie and other friends she slowly embraced her feminine side. Soon Cary was gone and Kylie took over. She never looked back.

"But you have breasts and a cock," Jackie said.

"I never transitioned but I had top surgery," Kylie told her.

"You're Kelly's dad, er mom?" Jackie asked, not clearly understanding.

Kylie laughed. "As you discovered last night, everything still works. After Angie and I got married, we decided to have a child. I prayed very hard for a little girl and we were blessed with Kelly. Now I have a question for you?"

"Me?" Jackie sounded surprised.

"Yes," Kylie said seriously, "Now that you know does it changed anything?"

Jackie sat quietly and thought for a moment. Quite a bit had happened in the last twenty-four hours. From wearing breasts to having her ass fucked by Kelly's mom it was a lot to take in. Overall though she understood that she might have come to the realization that Jackie was whom she was. Kylie had shown her that was all right.

"Things have changed a lot, Kylie, Kelly," Jackie said, "Last night opened my eyes to a lot of things." She reached out and took Kylie and Kelly's hands. "I can't wait to see what will happen next. So what are our plans?"

They decided to hit the South Shore today. Traveling from Falmouth to Chatham, they would take their time and hit all the little shops they could find along the way. There was really no plan, just have fun and enjoy themselves.

Jackie was especially more relaxed today than yesterday. Last night certainly appeared to be a game changer for her. She still had questions she needed to ask but most importantly new feelings she needed to address. She remembered Kelly saying that now she was going to be fucked like a woman and instead of being upset over it, she found she welcomed it. She wanted a cock in her ass and who's better than Kylie's? When Kylie showed her hard cock, Jackie knew what she had to do. It was natural and right. She hoped that she could do it again real soon. There was also something she wanted to do.

As they were walking along the streets of Falmouth, checking out the shops, Jackie said to Kelly, "Those two boys we met last night seemed nice."

"Who? Logan and Billy?" Kelly asked. "Why?"

"Yes," Jackie answered, "I don't know, just something you said."

"OMG, Jackie, you want to go out with them, don't you?" Kelly said stopping in the street. "That would be great. I'll call Logan right now."

Kelly called and then turned to Jackie. "It's all set. They will pick us at 6 and we'll go out for a casual dinner. We'll see what happens after that."

"Kelly all I did was ask. I didn't say I wanted to go on a date with them." Jackie said. It was clear she was a little upset.

"Look, it will be fine. I dated Logan for a while in high school. Nothing serious," Kelly explained, "And Billy is just the sweetest guy. He is a senior in high school. Logan is a junior at BC. I'll be there so nothing will happen."

Kylie came out of a store to find her two girls excitedly chatting. "So what's all the excitement, girls?"

"Oh mom," Kelly said with a big smile on her face, "Jackie and I have a date for tonight. We're going out with the Morse boys."

"I see," Kylie said with a tone of disappointment.

"What's the matter, mom? I thought you'd be happy for us. Jackie going out on her first date, with a boy!" Kelly replied.

"I am," Kylie answered, "I just thought that we might just stay home together, you know."

Kelly stepped towards her mom. "I get it. We won't be home late and then..."

"No," Kylie said, now smiling as she took Jackie's hand. "This a big deal and we'll do this right. We'll have some ice cream to celebrate then maybe we can find something special for you to wear tonight!"

They ate their ice cream and then drove to Chatham. "I know a nice jewelry shop there. Jackie, you need your own special piece of jewelry tonight."

Entering the store Kylie knew exactly what she was looking for. She headed for the clerk and asked for the necklaces. The clerk pointed them out and the three girls walked over to the display case. There were numerous necklaces of different types available.

"Jackie, pick out the one you want but if I could make a suggestion," Kylie said pointing out a long silver chain with a glass bobble on the end.

"Why, Kylie, it looks almost like yours," Jackie said leaning over the glass.

"Yes, and I have had this one for a long time. It has always brought me luck."

"Well then that's the one," Jackie said. She turned to the clerk, "How much?"

"We'll take it," Kylie said quickly. She looked at Jackie, "I insist."

***

Saturday Night

The Morse boys were right on time and Jackie and Kelly were ready.

Jackie was very nervous. "I'm not sure I want to do this, Kelly," she said as the boys drove up.

"You said you were ok this afternoon and you were curious to see a date from the other side. It will be fine," Kelly said rubbing Jackie's arm.

Looking down, Jackie said quietly, "Do I look alright?" She was wearing black skinny jeans and a simple white blouse. The blouse was unbuttoned enough to show some cleavage and her new necklace which the glass bobble rested between her breasts. Kylie suggested she add just a touch of padding to her butt to smooth it out.

"You look fine, sweetie," Kelly answered, "Just enough, here and there. So relax, will you?"

Boys took Jackie and Kelly to a small restaurant not too far away. It was more cafeteria style as they ordered their food at the counter and when their number was called it was ready. Being on the other side for the first time Jackie could understand how it felt for the guy when the girl decided on what to eat. Billy told her to get what she wanted and money was no problem. Still, she kept her order small, ordering a fish sandwich and a chocolate frappe. She thanked Billy and he smiled back. "No problem," he said.

It was clear Billy was a little nervous but Jackie did her best to try to make it easy for him. It didn't help that she was nervous also, just thinking of the whole situation. Slowly they began to talk and by the end of the dinner, their conversation was flowing smoothly. Kelly and Logan being good friends made it easier and Jackie was happy to have Kelly along.

"So, Billy," Jackie asked, "Any plans after graduating?"

"I have been asked to play baseball at UConn but I'm not sure," he replied.

Jackie put her sandwich down, "Oh why not?"

"Not sure if I'm that good to play D-1. Might be better to play D-2 ball."

Jackie smiled at him. "Well if UConn thinks you're good enough to talk to, then it seems to me you must be pretty good."

Logan laughed. "See Billy even a girl thinks that." He turned to Jackie. "I've have telling him the same thing since summer. Maybe he'll listen to you. You're much prettier than me!" He laughed again.

Jackie didn't know why she did what she did next. She put her hand on Billy's hand. "You know, sometimes you just have to take a chance and see what happens."

When Billy looked down at her hand, Jackie quickly removed it. Blushing, she said softly, "Sorry."

"I checked the movie theaters and there isn't much playing." Logan said, "Unless you want to go to a club in Plymouth."

"We don't have to go," Kelly said, "What else were you thinking of?"

"We could go back to our house," Logan suggested, "Watch a movie there, and eat popcorn.

Kelly nodded, "What do you think, Jackie?"

"If you're ok with it, so am I," Jackie agreed.

As they got to the house, Billy turned to Jackie. "I'm not big on watching movies especially the kind Logan likes. He's into old movies. Do you like video games?"

Jackie's heart leapt. She loved video games of all types. She was pretty good at them. As she was about to say yes she realized something. She was a girl so how could she be good at video games? Plus what if she was better than Billy? "I don't know. What kind of games?" she answered with some hesitation.

"I have some two people games. We could play together," he replied.

"I don't know if I'll be any good."

Billy smiled. "I'll teach you. It could be fun."

Jackie and Billy went down stairs to the game where Billy showed her his games. "How about this one? It's like the old Tour of Duty, only much better. We can play as partners."

He couldn't have made a better choice as far as Jackie was concerned. In high school, she played in a tournament and ended up in third place playing this game. It was going to be easy. Or was it?

Jackie walked around the room as Billy set up the game. She noticed a number of plaques and awards he had earned playing baseball. "Are these all yours?" she asked.

"Yes" he answered quickly.

"I'm quite impressed. You must be very good," Jackie said seating herself beside him.

"I guess so."

"Don't sell yourself short, Billy." Jackie looped her arm around his. "If you don't give yourself a chance, you'll never know if you could. You'll be kicking yourself if you don't try." She looked at him and smiled.

He looked at her and just nodded. "Maybe," he said. He handed Jackie one of the controls. "Here goes." He gave her a brief tutorial and then started playing. Jackie knew just what to do.

"Wow, you're dead already," Billy said with some disbelief in his voice.

"Sorry, I'll try again," Jackie apologized.

She moved slowly and deliberately, thinking out her every move.

"You have to keep up, Jackie!"

"I'm trying, Billy. Don't yell at me!"

Billy put down his controller. "I'm sorry, Jackie. I didn't mean to yell. Look, come over here and we'll do this together."

He slid the ottoman over and sat on it. "Here, you sit in front of me."

Jackie did as she was told.

"Here sit back and hold the controller." Billy handed it to her and then put his arms around her. "Comfortable?"

Jackie nodded. She couldn't believe how it felt. She leaned back and settled in against him. They started playing.

She played dumb and let Billy take charge. She improved slowly until Billy said, "You're ready to play now. I'll get my controller." He started to get up.

"Can't we play seated this way?" Jackie asked. "I might need your help."

So the two played the video seated together on the ottoman. Jackie nestled back into Billy as he kept his arms around her. For Jackie she felt completely relaxed. They laughed at some of her mistakes and she even gave him a hard time if he made one. There were times she slipped down in her seat and Billy put his hands on her waist to pull her up and closer. Each time Jackie felt a little rush of excitement.

"Your hair smells great!" Billy blurted out.

Jackie put her controller down. "Why, thank you."

Billy blushed. "Sorry."

"Don't be sorry," Jackie said turning towards him. "A girl likes to hear such things."

He smiled and then leaned forward. He kissed her, catching Jackie off guard. He then suddenly pulled back. "Oh I'm so sorry, Jackie. I shouldn't have done that." He started to stand up.

The kiss totally surprised Jackie. Her reaction to it did too. It sent a jolt through her body. It was short and she wanted more. She put her hand on his shoulder. "It's alright, Billy. Don't go." She kissed him.

It wasn't a hard kiss but a soft and tender one. She opened her mouth and lightly pushed her tongue into his mouth. She then coaxed his tongue into hers. After a few moments she broke the kiss. "There," she whispered, "Don't be sorry." She kissed him again.

For her first time kissing a boy, Jackie found it strangely exciting. She never in her wildest dreams ever thought of doing it but now it seemed right and natural to do. Her pulse raced a little and her breathing became quicker. She liked it.

"Hey you two," Kelly called from the top of the stairs, "It's awfully quiet down there. It's time to go!"

***

Back at Kelly's House

"Girls!" Kylie yelled from her bedroom, "How was it?"

The two entered the room together. "It went well, Mom."

"Climb in here and tell me all about it," Kylie said as she patted the blanket beside her.

Kelly began to remove her clothing. She looked over at Jackie. "Come on, Jackie, let's go to bed."

Jackie stood still with a confused look on her face.

"Oh come on sweetie," Kelly said jumping into bed naked. "We always sleep together naked. Right Mom?"

Kylie let the blanket down, exposing her naked breasts. "Yes come on girlie, get naked and under these blankets where it warm. I want to hear about my girl's first date."

Jackie crawled in between Kelly and Kylie and began to tell them all about it.

"It was nice to be on the other side for once, to be catered to. Billy was a perfect gentleman," Jackie started.

"Mom they were making out in the basement!" Kelly interrupted, "Tell her."

Jackie gave Kelly a dirty look. "We were playing video games in the basement. We were sitting together on the ottoman and he told me my hair smelled nice. Next thing he kissed me."

Kylie smiled, "How did that feel?"

"I was surprised at first but I have to admit, it felt good."

"Then what did you do?" Kylie asked.

Jackie blushed. "I kissed him back, a real kiss."

"And?"

"It felt right, all warm and tingly. I liked it." Jackie admitted.

Kylie hugged her. "My girl's first kiss. I'm so happy for you!"

They snuggled under the blanket, their naked bodies up against each other. Jackie lay between Kelly and Kylie with Kelly spooned up against her back. Kelly kept kissing and nibbling on Jackie, making her squirm. Kylie pressed her body close to her. As she did her cock rubbed up against Jackie's. It felt good and caused Jackie's to begin to get hard. In response, Kylie's began to stiffen.

Jackie's cock wasn't as big as Kylie's. Hers was close to a normal size, only when Kelly put a cock ring on it did it seem to grow bigger and thicker. Kylie's was just a little bigger and thicker even when flaccid. To Jackie, it was very impressive to see it hanging between the legs of such a beautiful woman.

Jackie's hand wandered to Kylie's breasts and began to play with the nipple. Kylie arched her back and moaned. As she did she offered it to Jackie who placed her mouth on it and began to suck it.

"That's it, baby girl, suck mommy's tit," Kylie groaned.

Kelly leaned over Jackie and began kissing her mom. Her hand slid down and grabbed both cocks. Both Jackie and Kylie moaned as the sounds of three women loving each other filled the room.

Jackie removed her mouth from Kylie's breast. "Kylie, make love to me, please." There was a hint of desperation in her voice.

"Yes, girlie," Kylie whispered, "Roll over."

"No, I want to see your face." Jackie said quietly.

Kelly got the lube and covered Kylie's cock with it. She then lubed up Jackie's asshole.

"Ready?" Kylie asked, "I'll be gentle."

Kelly moved next to Jackie and put her arm around her. "Relax, sweetie."

"Hold me, babe," Jackie said looking her in the eyes.

Jackie was prepared this time and after Kylie slipped the head in, she moaned in pleasure. As more of Kylie's cock went in deeper, her moans grew louder. Her cock began to twitch and a stream of pre-cum began to flow from the tip.

Last night was her first time and she wasn't sure what to expect. Still it was amazing. Tonight it was different and so much better. She felt like Kylie was making love to her. She began to match her movements and even wrapped her legs around Kylie's waist. By doing this it made her cock go deeper.

With each stroke, Jackie's cock bobbed up and down with more fluid pouring from it. Kelly reached down and with her lubed hand began stroking it up and down in perfect time with Kylie's movement.

"Oh fuck, Kelly, Oh my God, don't stop! Please!" Jackie groaned loudly.

Kylie looked down into Jackie's face. "That's it baby, cum for mommy."

Tears began to run down Jackie's face. The feeling was growing stronger. "Yes, mommy, fuck me. Oh fuck!"

Kelly began licking Jackie's ear sending shivers through her body. "That's it sweetie, cum for me. You are so fuckin' hot," she whispered breathlessly.

"Oh baby, I'm going to cum and fill your ass," Kylie moaned, "Cum with me."

Kelly's hand rapidly pumped Jackie's cock and Kylie fucked her ass. The feeling became overwhelming. "Oh God," Jackie screamed as her cock sent a stream of cum onto her chest. "I'm cumming!"

Her ass clasped on Kylie's cock. Kylie pushed her cock deep into Jackie's ass, crying out, "Oh fuck, I'm cumming too." She collapsed onto Jackie's chest exhausted yet satisfied.

***

Sunday Morning

"Jackie, you have a visitor," Kylie yelled up to the bedroom, "Its Billy."

"Tell him I'll be down in a minute," Jackie shouted back.

Kylie escorted him to the kitchen. "Do you want anything?" Kylie asked, pouring herself a cup of coffee.

"No thanks," he answered, shifting nervously from foot to foot.

Jackie came bounding into the kitchen. She had dressed quickly throwing on a demin skirt and her college t-shirt. And she remembered to put on her fake breasts! "This is a pleasant surprise. What brings you by?"

Billy stepped close to her. "Could we go someplace and talk," he said softly. "If that's alright with you," he added quickly.

Jackie smiled. "That would be ok. Let me grab a sweater." She turned to Kylie. "Mom, I'm going out with Billy for a few." She kissed her on the cheek. "Love you."

Climbing into Billy's truck, she asked, "Where are we off to?"

"I was going to stop at Dunkin' for a coffee and then go park overlooking the Bay. Do you want anything?"

"Sure a nice hot tea," she answered.

Billy got their drinks and then headed over to the Bay. He parked in the lot and turned off the truck. "I wanted to walk along the beach with you but I think it's too cold for that," Billy stated and then he quickly added, "Unless you want to?"