Lost Suitcase Adventure Pt. 05

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Jesse has a realization and futures are settled.
11.1k words
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Part 5 of the 6 part series

Updated 05/31/2024
Created 01/18/2024
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Author's Note: I was happy with the way Chapter 4 ended and I hadn't thought much about the series since it was published in February. Then the other day I got an interesting comment saying that I had a ton of more material to explore. It's funny I never re-read my own stories after proofing them, mainly because it's hard to get off on your own words. I re-read all 4 chapters and the juices started flowing. Hope this is as enjoyable as the other parts and I haven't gone rusty!

CHAPTER 5

I was on my hands and knees thrusting my hips back as fast as I can. Tom's huge cock is plowing my pussy harder than ever. My pink babydoll is struggling to contain my beautiful DD breasts and my pink g-string isn't doing a good job of holding my clit inside either. As he liked to do, Tom had pulled the string from in between my amazing ass and rested it on my left cheek.

As we continued to fuck doggy style, I glanced over to see a big smile on Jessica's face. My best friend is lying beside us on her king sized martial bed and watching her husband fuck me. She is wearing a matching pink babydoll. When I got matching breasts, she was excited for us to be twins. She wasn't kidding and had bought us a bunch of matching outfits. The only difference right now was that she was 8 months pregnant and her baby bump made a cute impression in her nightie.

It was no surprise that Jessica got pregnant right away. Tom always had huge loads, so when she asked him to try to get her pregnant, his magic sperm did the trick. As her pregnancy progressed, Tom was reluctant to fuck her the way he liked, because he was afraid of hurting her. Their sex life had slowed a bit which is what led to me getting my brains banged in tonight. We had fucked almost daily since I moved in, but he would mix it up between hard and gentle. Nowadays Tom was taking out all his energy on me, not that I minded of course. Jessica was still horny, but was content to have me pleasure her with my tongue.

I was moaning as Tom thrusted in and out. Then I heard a huge slap followed by quick searing pain. Tom had slapped my right cheek so hard that I heard it before I felt it. That's how hard it was that the sound preceded the feeling.

"Ouch Tom!" I yelped.

I looked at Jessica and she was laughing.

"It's not funny!" I yelled at her.

"What's not funny?" Tom asked.

Before I could answer he pulled back and thrusted in really hard, pressing on my prostate.

"The slaaaaaa...Oh My God!" I screamed as my whole body got goosebumps.

He pulled back and thrusted again in the same spot. The pressure of his hips cause my massive boobs to pop free from the top of my nightgown and my rock hard clit escaped from my g-string.

"What was that?" He asked, now giggling as well.

"Holy shit!" I moaned in pleasure.

Suddenly I felt a slap across my left cheek. This one wasn't as loud, but still hurt as much. My boobs were jiggling back and forth while my clit started to leak on the sheets.

I composed myself for a second to get my words out, "Tom, take it easy, Jason is coming in tomorrow!"

That might not have been the best thing to say, because he slapped me again.

"Aww, is my baby worried her boyfriend is gonna see my handprint on her ass?" He said, teasing me.

"He's not my boyfriend!" I said, not sure why I thought that would help.

"Oh really? Then why do you hookup with him every time he comes to visit and talk to him on the phone all the time?" He asked.

In the middle of being fucked hard and spanked I realized something. Holy crap, do I have a boyfriend? I never thought of that before Tom just said it. Sure I had fooled around with Jason every time he came down for business. Now that I think of it, he never seemed to do any work when he was down here. He hung out with his best friend Tom and had sex with me. We kept in touch when he was back home, talking or texting, but that was mostly about sports and current events.

Tom kept fucking me, but eased up for a second as he realized I was having an epiphany. I looked over at Jessica to see her eyes closed and letting out little moans. Her left hand was inside her matching g-string playing with her clit and her right was massaging her breast.

"Jess, do I have a boyfriend?" I asked her.

Jess opened her eyes, but continued to play with herself.

"I thought you knew," she said.

"I guess, I mean, I........" I couldn't finish my sentence because Tom started to pound my prostate again.

"Enough talk about other dudes. It's time to knock up my other girl!" Tom said.

He was right and the pleasure was too fantastic to think about anything but his hard cock destroying my pussy. I slipped back into character, although the moans were completely natural.

"Oh yeah!" I moaned. "Fuck me hard! Give me your babies! Knock me up like my gorgeous best friend!"

Tom's put his hands on my hips and now he was controlling all the movements. I couldn't tell if he was thrusting his hips into me or pulling me back and forth on him. He was so strong and I really didn't care. He always felt so good inside of me and I was happy to go along for the ride.

Tom and I were pretty much moaning and grunting, but it was Jessica who let out the loudest scream first. I looked in her direction, a little glassy eyed, and I saw that her fingers had done the trick. She was breathing heavily and I could see her baby bump moving up and down. I'm not sure why, but I thought it made her look even sexier.

"Oh yeah, Baby, I'm gonna cum!" He yelled.

I felt Tom's dick begin to swell and I knew I was about to take a huge load.

"Just another minute, I'm almost there too!" I yelled.

"Sorry Baby, your pussy is too wonderful, I can't wait any longer!" He said.

He pulled me forward, slammed himself deep inside of me, and his dick started to spasm. I yelped and groaned at the same time. Sensing my disappointment, Jessica slid herself over and took my clit inside her mouth. Tom threw his head back and started to bathe my insides.

I wasn't kidding that I was close and thankfully Jessica was there. I wasn't exactly counting because of all of the pleasure, but it think it only took two sucks for me to explode in her mouth. She hadn't blown me as much since she got pregnant, but her mouth always felt amazing. Tom had gotten me 99% of the way home, but she gets credit for being the closer.

I was squirming and panting throughout my orgasm. Tom had started to cum inside me first, and somehow he was still going after I had finished. I was right, it was a huge load and I would definitely have to wear a tampon to bed tonight. When Tom slipped out of me I clenched my cheeks and went to the bathroom to take care of business.

I came back out and Tom and Jessica were lying in their bed. Tom was naked, and Jessica had straightened out her babydoll and panties.

"So what do you think?" Tom asked.

"About what?" I asked, curiously.

"Did I get you pregnant this time?" He asked.

Playing along I said, "I'm not sure. You'll probably have to try again tomorrow!"

"But what about your boyfriend?" Jessica asked, "He'll be here tomorrow."

A light bulb went off in my head. Every time Jason came to visit I only had sex with him and not Tom. How did I not realize this? And why didn't anyone say anything? Did Jason think I was his girlfriend?

"Oh...right...wait, is he really my boyfriend? You two weren't just saying that to fool around?" I asked.

"I guess I just assumed. You two talk all the time, he makes special trips to come see you, and you hook up every time. That sounds like a boyfriend to me," Jessica said.

"But how could I have a boyfriend? How could I be someone's girlfriend? I never thought that could be possible?" I said.

"Have you seen yourself lately?" Tom asked.

"Yeah sweetie, you're smoking hot! Why shouldn't you have a boyfriend and be someone's girlfriend?" Jess said.

"I guess I always thought I'd be like you guys one day, happily married and about to have a family," I said.

"Right, and isn't a boyfriend the first step towards that?" She asked.

"Yeah, but I'm supposed to be the boyfriend!" I said.

Tom chuckled.

"What's so funny?" I asked.

Jessica took my hand and said, "Sweetie, you were never boyfriend material. You are a thousand times better as a woman than you were as a man. You were meant to be a girlfriend, wife, and mother, and nothing else."

"I'm sorry I laughed," Tom said, "I forgot how hard this could be for you sometimes. I just assumed that after everything you've been through that you were 100% woman now. I mean there's a pint of my babies plugged inside of you right now."

"Don't be disgusting," Jessica said to Tom.

"No you're both right," I said, "But wait, girlfriend and wife are simple, but what about the mother part? I know we like to role play, but me getting pregnant isn't really an option."

"One step at a time," Jessica said, "You just realized you have a boyfriend. If it gets to the point where you have a husband, Tom and I will do our best to help you figure out the mother thing."

I kissed Jessica lightly on the lips and said, "Thanks Sweetie! You've been very helpful."

"What about me?" Tom asked.

I leaned over and gave him a big kiss with tongue.

"And thank you for tonight!" I said.

"Honey, you have an early morning, right?" Jessica asked Tom.

"Yeah, going to the office and then picking up Jason, I mean Jesse's boyfriend, from the airport," He said.

"Since you two ruined your side of the bed, why don't you sleep on my side tonight? Jesse and I don't have anything to do but get the house ready for her boyfriend so we can sleep in. I'll sleep in her room tonight so you won't wake me," she said.

Before Jessica got pregnant I had pretty much been sharing their bed. Since she's gotten bigger I would fool around with them in their bed, like tonight, and then go sleep by myself. Lately Jessica has been coming with me. Tom gets very hot when he sleeps and that doesn't mix well with an 8 month pregnant woman. She likes to cuddle against my soft hairless body and I'm happy to help her out.

"Of course, baby. You two have a good sleep and I'll see you tomorrow with Jesse's boyfriend," he said.

"What's all this boyfriend talk?" I asked.

"Just want you to get used to it!" She said.

"Wait, does he think he's my boyfriend?" I asked Tom.

"I don't know. Maybe you need to ask him," Tom said.

"Ok, but don't say anything," I said.

"No problem," Tom said, "I won't interfere. You two need to figure things out."

We all kissed each other goodnight and went to sleep.

I had an interesting night and my dreams were all over the place. It took a while, but now I was exclusively dreaming as a girl. I rarely had sex dreams, but tonight was different. I was on my back getting fucked. We were kissing and saying we loved each other. The problem is that I couldn't make out the man's face or recognize his voice. My eyes were squinting and trying to see who it was. Was it Tom? Was it Jason? Was it someone I haven't met yet? My vision started to get clearer and as I was about to see my mystery lover I was jarred awake. Jessica had been spooning me as she typically did when we slept together and my soon to be nephew kicked me in the back. It's impossible to be mad at a baby, especially one who hasn't been born yet, but I was a little upset he ruined the big reveal.

"Ooooh," Jessica said, feeling the kicks.

"You okay Sweetie?" I asked.

"Yeah, did we wake you?" she asked.

"That's okay, he's probably just anxious to meet his Aunt!" I said.

"Ha, I'll try to tell him to keep it down so we can get some more sleep. Love you," she said.

"Love you too," I said.

I smiled. I was no longer concerned about my mystery lover. Jessica loved me and I loved her. That was good enough for now. The future would figure itself out.

THE NEXT DAY

Jessica and I woke up and cleaned the house in our nighties. We made up the guest room for Jason, even though the expectation was he would be spending the nights in my room as usual.

We showered together as we did a couple times a week. Since she got bigger, she wanted help reaching everything and shaving her legs. When it came to getting dressed she had been a little jealous about my options of clothing. She had bought several maternity dresses that were cute, but she didn't have the sexy options that I did. I told her over and over that she looked beautiful.

In the beginning I dressed casually around Jason, but my wardrobe choices got sexier as time went by. I decided we were going to have the boyfriend/girlfriend talk, so I picked out an extra sexy outfit. I started with a pink bra and panty set. The bra pushed up the girls so they looked more massive than usual. Like all of my underwear, the matching panties were a thong. I don't think I'll ever get used to the wonderful feeling of lace sliding up my smooth legs and resting in between my cheeks. It gives my body a tingle every time. I put on a low cut slinky black dress that hugged all of my curves. It ended just below my ass and depending on how I moved, the pink lace of my bra would peek out around my cleavage. I finished my look with a pair of 3" black heels.

"Damn girl, we're not going clubbing? You know we're just having sandwiches in the kitchen, right? Jessica said.

"You're the one who put 'Boyfriend' in my head. I just want to look good for my man," I said.

"Whoa! Your Man? I'm so happy you're getting into this," she said.

"I've been thinking a lot since last night and I want what you have," I said.

"And you think Jason is The One?" She asked.

"Maybe," I said. "I had a nice dream going last night and right when I was about to find out who The One was, the little guy kicked me and I woke up!"

"Oops," she said, "But that was just a dream. You need to make a decision for real."

"Yeah, baby steps please," I said.

"Speaking of babies, you're welcome to use your nephew to lure a man if Jason isn't good enough," She said.

"Why don't I focus on Jason for now? Our sex life is amazing and I have a lot of fun when I'm with him," I said.

"Do you love him?" She asked.

"I think I do," I said.

"So what's all this Maybe stuff?" She asked. "Lock him up!"

"You think?" I asked, nervously.

"How great would it be for best friends to marry best friends? There's that house down the block for sale. Tom would love to have his best friend close by and that way you and me will always be together," she said.

"You make some good points," I said, "But how do I know if he wants me that way?"

"Um, first off you're insanely hot, you two have a great time together, and if I remember correctly, not only does he fuck you, he also goes down on you and let's you fuck him. I don't know what guy would do that if he wasn't smitten," she said.

"I'm so glad we had this talk," I said, "But now what do I do?"

"Just be your charming self. Guys don't like when you're too pushy. I'll call Tom and tell him to feel Jason out. If things go the way I think they will everything will work out," she said.

I kissed her on the lips and said, "Love you!"

I went into the kitchen to set up while Jessica called Tom.

"Hey Babe," Tom answered.

"Hi Honey, all good here!" Jessica said.

"Yeah? That's great!" He said.

"Does he have the ring?" She asked.

"I haven't picked him up yet, but last I heard he was shopping for one. I can't see him showing up without one," he said.

"Perfect," she said, "And you're ok with all of this right?"

"What? Hooking our best friends up? Of course. Jason deserves to be happy after all he's been through," he said.

"Agreed, but you're ok losing Jesse? I just want to make sure," she said.

"Yes, didn't we talk about this? You're about to have our son and we're gonna have our family. Sure the crazy sex stuff was fun, but now we're parents," he said.

"Ok, had to check one last time. And all the other stuff we discussed is okay with you too, right?" She asked.

"Jeeze Babe, do you have pregnancy brain or something? Everything we discussed is fine! Now just make sure your BFF is totally in. I can't let Jason have his heart broken again," he said.

"Got it," she said. "Love You!"

"Love You More! See you soon," he said.

Jessica came into the kitchen to find the table set and me sitting down. I had put Sportscenter on the small kitchen TV to catch up last night's scores. I may be a hot babe now, but I still love my sports!

"I spoke to Tom. He's gonna talk to Jason on the way over and everything should be all set. You're sure about this, right?" Jessica asked.

"I did some more thinking in the couple minutes you were on the phone and I've made my mind up. Jason is The One! I want to be with him for the rest of my life! I want everything you said, the house down the block, and if we can figure out a way for me to be a Mom that would be awesome. Ooooh our kids would be Best Friends too!" I said.

Jessica had a huge smile on her face and almost spilled the beans, "I'm so happy all of your dreams are about to come true!"

"Wait, do you know something?" I asked.

Recovering, Jessica said, "No, just that I know how Tom is and he's gonna make sure you two are very happy!"

MEANWHILE AT THE AIRPORT

Jason put his bag in the trunk and got in the passenger seat. The two bros slapped five and Tom started to drive to the house.

"What's up? Why do you have that goofy grin on your face?" Jason asked.

"No reason," Tom said.

"Dude! What's up?" Jason asked.

"Did you get the ring?" Tom asked.

Jason pulled a ring box from his pocket and opened it. The diamond glistened in the sunlight and caught Tom's eye right away. Luckily they were at a red light so Tom could take a good look.

"Holy shit! That's bigger than Jessica's!" Tom said.

"Nice, right?!" Jason asked.

"Yeah, Jesse is gonna love it! Jessica will be jealous for a second, but then happy for her friend," Tom said.

"You're gonna end up having to buy her something, huh?" Jason laughed.

"Probably. Thanks Dick!" Tom said jokingly. "I already got her these huge diamond studs as a Push Present and now I've gotta buy her a bigger ring."

"The things we do for our women," Jason said.

"Have you thought about how you're gonna do it?" Tom asked.

"As quickly as possible! The ring is burning a hole in my pocket. The longer I hold it the more nervous I get," Jason said.

"That's not like you to be nervous," Tom said.

"I know, but remember last time I proposed? I almost threw up," Jason said.

"Haha, that's right. Don't sweat it though. Jesse is real cool and easy going. She'll definitely say Yes. There's nothing to worry about," Tom said.

"That's a relief," Jason said.

"They have lunch set up for us. Let's eat quickly. Then Jessica and I will make ourselves scarce. I'll turn on the cool water features by the pool in the backyard. Take Jesse outside and tell her you're gonna make her the happiest girl in the world! Then Jessica and I will meet you guys with some champagne," Tom said.

"Wow Dude, I didn't know you had that romance in you," Jason said.

"I know right. I wish I did something like that for Jessica. I proposed to her in an Applebee's!" Tom said.

"Yeah I remember. And somehow she still said yes. Maybe you can re-propose when you buy her a bigger diamond ring!" Jason said laughing.

"Remind me to punch you later for that!" Tom said.

"So you upgrade her ring, what's the big deal? It's only a trade off of a few thousand dollars," Jason said.

"Yeah, cause she's not gonna wanna keep both. Are you stupid?" Tom said.

"Haha, like she needs two engagement rings," Jason said.

"I know exactly what she'll say: 'I don't neeed them, I want them.' I wouldn't even ask her to return the original one. Besides it becomes an asset. Better to have a diamond in the safe than money in the bank," Tom said.