Chapter 5: WIPs Motel Pool

Time passed quickly for the unusual couple, and suddenly, it had been a year since they met at the Vista Lodge Motel. While Jack still referred to Chelsea as his niece to most people, there were a few that they trusted who knew the truth. No laws were being broken, but the disparity in their ages usually left people uncomfortable, and Jack didn’t want Chelsea to have issues at school.

Jack and Chelsea’s relationship ended up being stronger than even they thought it could be. They spent many nights laughing, playing, and fooling around. It was nice for Jack to come home to a house that was happy and full of life once again. Chelsea still had her own room but never slept in it. She used it primarily as a place to do schoolwork or relax when Jack was busy.

Chelsea quickly completed her high school education. It turned out she was a very good student and was able to catch up fast enough to graduate at the end of her second term. She made a few friends during her brief time at school, but there was only one that she trusted to disclose the nature of her relationship with Jack.

It was nice for Chelsea to have someone she could openly talk to about such things. She had Jack, but it was nice to have someone else to turn to when she needed advice. Her name was Lucy, and she was a senior, too. They met in English and hit it off after they worked together on an assignment. She was a quiet girl who most people ignored, but Chelsea was able to break her out of her shell by being her usual, friendly self.

As the school year wound down, Chelsea was having difficulty deciding what she wanted to do after high school. That was usually a tough decision for any teen, but in the whirlwind that was the past few years, she never thought about finishing high school, let alone going to college. Jack was patient and offered to let her make her own choice. He was confident they would be fine, romantically, and he was willing to pay for her education. He wasn’t looking for a trophy wife or someone who sat at home all day. He wanted Chelsea to live and be happy herself, not just on his whims.

She was accepted at several schools, including the local Arizona State in Tempe. She was leaning towards staying in town to be with Jack, but he insisted she consider all her options. This was one of the things she loved about Jack. He let her make her own decisions and only wanted the best for her. That was something she hadn’t had in her life, and it was something she had no intention of losing.

A week before graduation, Chelsea came home from school with her friend Lucy. The two were discussing what they wanted to do for the summer before they headed off to college. Lucy had already decided she was going to stay in town. Chelsea also had decided to stay, attend Arizona State, and major in social work. She wanted to be able to help people and teens who were in the situations she had been in.

“Not everyone gets lucky and finds someone like Jack,” she would say. “But maybe I could be a guide to help them through the difficult times.”

Chelsea and Lucy were looking at maps of the ASU campus when Jack got home from work. He was tired but happily greeted the two girls. Chelsea kissed him hello and gave him a big hug, while Lucy said, “Hello, Jack.”

“Hello ladies, what have you been up to?” Jack asked.

“Just looking at the layout of campus and what we want to do there,” Chelsea replied.

“Well, that’s fun! What would you both like to eat if you’d like to stay for supper, that is Lucy?”

“Ok, if you insist. How about pizza?” Lucy suggested.

Pizza was the decision, and after a bit of debate over toppings, two pizzas were ordered for delivery. They all sat outside on the patio talking about future plans and school. Jack enjoyed the banter and youthful enthusiasm the two girls had. He thought back to his time in college and all the fun things he did. The classes, the parties, and the girls. While he knew Chelsea was happy in their relationship, he did feel bad that she might miss out on some of those things. He hoped she’d at least go to a party or two on campus.

After they finished their meal, Jack and Chelsea cleaned up while Lucy looked at the view. It was a nice hot evening, as the sun slowly went down. The sky glowed in shades of yellow, red, and purple. Jack wondered if the girls would like to watch a movie, but Chelsea had a different idea.

“Why don’t we all go for an evening swim?”

“That sounds like a great idea, Chelsea, but did Lucy bring her suit?” inquired Jack.

“Unfortunately, I didn’t,” Lucy said, stifling a grin.

“What am I missing?” Jack wondered out loud.

“Well, we were thinking it might be a nice night to do a little skinny dipping,” Chelsea added before pulling off her shirt.

“Uh ok, well then I’ll leave you two girls alone,” Jack replied, walking away.

“But you’re invited too, Jack,” Lucy said, moving in front of him.

“Don’t you think you’d be a little uncomfortable with that, Lucy?”

“Nope! Last one in is a rotten egg!” she shouted as she pulled her shirt over her head and headed for the pool. In a flash, Jack saw the backsides of two naked teen girls jumping into his pool. He didn’t know what was going on, but he knew Chelsea had something to do with this. He simply sighed, turned around, and started removing clothing.

Jack stood at the edge of the pool in nothing but his tenting boxer shorts looking down at the two naked teens splashing each other with water with the fading sun in the background. He walked briefly to the side of the house and flipped on the pool lights, pulled down his last stitch of clothing, and cannonballed into the water, splashing both of them. He may have been much older, but Chelsea had brought out his youthful, fun side.

The three of them swam around, splashing, playing, and dunking each other under the water. During their play, hands seemed to drift every which way underwater. There were more than a few occasions where Jack felt a hand or other body part rub against his engorged member. Although, he himself had to admit to letting his hands wander over a few pieces of soft girl flesh of both Chelsea and her cute friend.

Once the three of them were tired of the water, they all climbed out of the pool to dry off. Jack wrapped the towel around his waist out of modesty, but the two girls just let him look at everything they had. As Jack sat down in a chair across from Chelsea and Lucy, he checked Lucy out. She was about 5’10 with raven black hair, an upturned nose, and a thin body. Her breasts were larger than Chelsea’s at a B-cup, and she had a small tuft of pubic hair above her slit. She was quite cute. Previously, Chelsea had told him Lucy was not popular with the boys at school. She had spent most of her time reading alone, until Chelsea came along.

Jack’s mind had wandered while looking at the two girls, when Chelsea got up and walked towards him. She put her arms out for a hug, which Jack graciously accepted, but what he didn’t expect was for her to spin around, sit right on his lap, and grind herself on him.

“Chelsea, honey, what are you doing? You have a guest over.”

“I know. She doesn’t mind, do you, Lucy?” Chelsea asked.

Getting up and walking over, Lucy replied, “Nope, don’t mind at all. I wouldn’t mind watching, to be honest.”

Chelsea reached down between herself and Jack and pulled his hard cock out between her legs. His cock was now sandwiched inside her outer labia as she rubbed herself on it.

“That feels so good, Jack,” Chelsea said. “Does it look good, Lucy?”

“It looks so hot. I wish I could try,” the black-haired girl said.

“You can. Just give me a few more minutes,” Chelsea replied. Jack couldn’t believe what he had just heard.

“Girls, what’s going on? I can tell when I’ve been set up here,” he said with curiosity but also some concern.

Realizing they’d overplayed their hand, Chelsea got off of him and put her arm around her naked friend. Both girls looked at each other and decided to come clean.

“Well, since Lucy and I are going to college next year, we wanted to do something together to signal our adulthood,” Chelsea said.

“To be blunt, Jack, I don’t want to go to college as a virgin. Chelsea offered to help me with that,” Lucy said, blushing in the glow from the pool lights.

“I thought it might be a nice gift for you too, Jack. You took me in almost a year ago, and I wanted to do something special for you,” Chelsea said with a nervous smile.

“Girls, you don’t need to do this. Chelsea, the greatest gift I’ve received was having you in my life, I don’t need anything more special than that. And Lucy, you are a beautiful young woman. Is this really how you want your first time to be?”

Lucy looked down at the ground for a moment or two before looking up and meeting his eyes. “Yes. I want to share it with my friend and her loving partner.” Chelsea and Lucy hugged, and Jack knew this would be an interesting night.

“How long can you stay tonight, Lucy? When do your parents expect you home?” Jack inquired.

“My parents are gone for the night, so I can stay as long as I want. We planned it that way, just in case,” Lucy said with a grin to Chelsea.

“Well, looks like I’ve been outmaneuvered here. Alright, how would you like to do this?” Jack asked, still uncertain but very aroused.

“Let’s go to the bedroom,” replied Chelsea, who took both Jack and Lucy’s hands and headed to the stairs.

When they got to the foot of the bed, Chelsea pulled Jack in for a kiss. Their mouths pushed together, and tongues briefly massaged each other’s. When they separated, Chelsea pushed Lucy towards Jack to get them to kiss. Jack leaned in and kissed the friend of his young girlfriend. It was a surreal experience, but a pleasurable one. He could tell she was inexperienced and guided her to open her mouth a bit more and teased her tongue with his own.

Jack placed his hands around Lucy’s body, holding her close to him. He opened his eyes and looked at Chelsea watching them. She seemed to be ok with this, so he continued. His hands moved up to her chest as he cupped her breasts. They were perky and firm. Lucy let out a moan as she was touched by a man for the first time.

As the two separated for a quick breath, Chelsea moved in to kiss Jack again. Jack alternated between the girls a few times before getting the idea of having them kiss each other. He moved them to face each other, both blushed but soon their lips connected, and they began a tentative but passionate first girl kiss. Jack enjoyed the sight of the two sexy teens making out, but they turned things around on him by quickly pushing him down onto the bed.

Both girls took places on either side of him, looking at the hard steel rod standing up towards the ceiling. Chelsea, the more experienced one, lowered her head and took his cock into her mouth, demonstrating a blowjob to her virgin friend. After a few minutes, bobbing up and down, Chelsea moved to let Lucy try. Jack felt her wrap her hands around the base of his cock and then her soft lips envelop half of his cock in her mouth.

She couldn’t take much more than that, and her teeth scraped him a couple of times, but she tried hard to please him. He was feeling pretty good, but he didn’t want to finish too early, that wouldn’t be a good experience for Lucy. He sat up and got them to stop, removing his cock from her mouth to a groan of disappointment. It was his turn to show Lucy some pleasure and to get her ready if she chose to have her first time tonight.

He lay her down on the bed and looked at her sexy body once again. He couldn’t believe this was something Chelsea was ok with! Looking over at her though, she just smiled, kissed him briefly, and then nodded for him to continue.

Chelsea moved up to her friend’s side while Jack moved between Lucy’s legs. She parted them somewhat, revealing her shiny wet virgin pussy to his hungry eyes. Jack lowered his head, parting her legs further using his hands and face until he was inches from her slit. He could smell the sweet aroma of her young, aroused sex.

He could sense her holding her breath and saw Chelsea holding her hand to comfort her. Jack looked once again at her juicy pink interior before dipping his tongue in to have a taste, sliding it from her tight hole up to the top of her clitoris. He felt her legs tighten on his head momentarily but also heard a sharp intake of breath followed by a moan. He figured he hit the right spot. He moved his tongue back down to the bottom and repeated the process, drinking in the sweet and tangy taste of her sex.

After a little while of Jack’s oral activities, he could feel her body tensing up, as she was close to an orgasm. This was the right time to see if she was ready to lose her virginity. He moved up, keeping himself between her soft, creamy legs, until he was face to face with her, kissing her briefly on the lips and letting her taste herself.

“Are you still sure you want to do this?” he asked, looking her into the eyes.

“Oh yes, I want it sooo badly right now!” she replied.

Turning to Chelsea, “Are you sure you want me to do this, Chelsea?” he asked his young girlfriend.

“Yes. I trust you and want you both to enjoy this,” she said, before kissing him, tasting a little bit of her friend too. She was surprised, but she liked how it tasted.

Jack was about to reach down to position himself at Lucy’s entrance when Chelsea beat him to it. She stroked his hard cock a couple of times, sliding it around before finding the correct spot. Jack looked at Lucy for the sign to continue and she kissed him lightly on the lips before nodding.

She was tight, but not as tight as Chelsea was on her first time. Jack slowly pushed inch after inch into the tight teen’s pussy as she moaned at the intrusion. After a minute, he was fully buried inside of her.

“Congrats Lucy, you’re no longer a virgin,” Chelsea said, still holding her hand.

“Thank you for lending me your man, Chelsea. He feels really good inside me,” Lucy said, as she started humping against Jack slightly. Jack got the hint and withdrew himself halfway before shoving it back inside her. Lucy groaned and wrapped her legs around his waist, trying to pull him in more.

Jack began pumping into her tight young snatch, enjoying the sensation of being inside another sexy teen girl. Her pussy was soaking wet as he thrust into her, with Lucy pushing to meet his motions. Chelsea just watched the pair, one hand holding Lucy’s hand, the other was between her legs fingering herself.

Jack moved his mouth down and sucked on one of Lucy’s nipples, exciting her more. Chelsea, seeing this, took the initiative and sucked the other nipple into her mouth too. Jack looked over at his girl, lips attached to another girl’s breast, and wondered how he got so lucky.

Lucy was reaching her apex with all these new sensations running through her body. She was gasping for air and her legs clamped down on Jack’s waist. He knew she was pretty close to cumming. He was getting there too, but he was just holding out to get her there first.

Lucy’s body twitched and suddenly her back arched as she cried out in an intense orgasm. Jack could feel her body tightening around him, milking and squeezing his cock.

“I’m gonna cum, Lucy!” he yelled out.

“Cum in me, Jack!” she replied as the aftershocks rippled through her body.

“Cum in her, Jack. Fill her up,” Chelsea whispered in his ear. That was the final straw, and he shoved in hard before releasing his load deep into her young body. He could feel it filling her before it overflowed and leaked onto the bed. Tired, he pulled out and looked at Lucy’s now defiled pussy, wet with white cum leaking out of it.

He lay down between Lucy and Chelsea, but Chelsea sat up, looking at his cum-covered cock, slick with her friend’s lube. Jack watched as his partially deflating cock was taken into Chelsea’s mouth and sucked on, cleaning all the fluids from it while getting him hard again.

“Do you like what you just tasted?” Jack asked as she removed him from her mouth.

“Kind of, yeah. It was different. Sweet and salty,” Chelsea said. “Do you think you have another load in there for me tonight?”

“I think so. How do you want it?” Jack asked.

“Take me from behind and really pound me. I’m so hot right now!” she said, as she got on all fours. Jack was surprised she didn’t move to a spot on the bed that had more room. She stayed close to Lucy with her head almost between the spent girl’s legs. Jack got behind her, slid himself up and down, and pressed into her tight slit.

Even after a year, Chelsea was still tight as anything as he shoved himself balls deep inside her. The force pushed her head forward, her face nearly touching Lucy’s cream filled pussy. After thrusting into her a few times, he realized that was her intent the whole time. He slowed down to watch as Chelsea tentatively tasted pussy for the first time. Lucy opened her legs wider and inched closer so the other girl could lick her dripping twat.

Jack couldn’t believe what he was watching! Chelsea was eating the creampie from Lucy’s pussy. It was the sexiest thing he’d ever seen. He grabbed Chelsea’s hips and slammed into her hard causing her to moan into the gash at her mouth. Lucy, meanwhile, seemed to be enjoying her friend’s ministrations, putting her hand in Chelsea’s hair and holding her there.