Lost Suitcase Adventure Pt. 04

Author's Note: This picks up right where Chapter 3 ends. I'm content with the way it ends, but if there's continued interest I will wrap it up in Chapter 5. If anyone has a suggestion on how they'd like a different ending to go, I'm all ears. Hope you enjoy this installment!

Lost Suitcase Adventure 4

JASON ARRIVES

The day before Jason arrived I got settled into the guest room next to my dressing room. I just brought some essentials. Jason would be staying in a room on the other side of the house, so I would still be able to get ready my normal way.

When Jason got to the house he gave Tom a big bro hug. He kissed Jessica on the cheek and shook my hand. As we had decided, I was introduced as Jessica's best friend from high school, which wasn't a lie. Then they said I was living with them while I decided on my next move in life, which of course was a lie.

Jessica and I dressed more casual than usual around the house. There was no reason to dress sexy in front of Tom's friend. The weather was crappy outside so we stayed in the first day. Jessica and I let the boys catch up while we kept ourselves busy. We heard the TV go on and I heard the sounds of football.

"Why don't you go watch the game with the guys?" Jessica asked.

"I don't know, I wouldn't want to intrude," I said.

"Nonsense. You love football. You still love football, right?" She said.

"Well yeah," I said.

Of course I still loved football. I may have tremendous breasts and have been taking it up the ass steadily for over a year, but my male brain is still in there.

"Go watch with them. See what it feels like to hang out with the guys again," she said.

I walked into the den and asked, "Do you guys mind if I watch with you?"

"Of course," Tom said.

"Wow, beautiful and a football fan!" Jason said.

I blushed.

"Hey Jess, before you sit down do you mind grabbing us some beers?" Tom asked.

I smiled. It was the first time he called me 'Jess'. That name was reserved for Jessica. He usually called me by a pet name, Baby, Babe, Sweetie, or Honey. I was a little impressed that he was able to switch gears for his friend.

I went into the kitchen and grabbed three beers. I popped the caps and walked back into the den, handing one to each of them and sitting down with one of my own. It had been a while since I watched a football game with a beer, so instinct took over and I took a swig from the bottle.

Jason reacted to me drinking directly from the bottle and said, "How is a girl like you not attached? You seem like the perfect woman!"

"Oh I don't know," I said, embarrassed.

"Dude, would you leave her alone. I'm trying to watch the game here!" Tom said.

Jessica ordered pizzas and joined us in the den when they arrived. We all ate as we finished watching the game. It was getting late and we all decided to go to sleep. Jessica and Tom went into the master bedroom, Jason to his guest room, and for the first time in forever I went to my own room.

It was weird sleeping alone. I can't remember the last time I didn't have someone to cuddle with. Not to mention the bed wasn't the most comfortable. In fact I don't think anyone has ever slept on this mattress before. To make things worse there was no TV in here. I tossed and turned for a while before deciding to go into the den and watch TV there. Hopefully that would tire me out and I could come back to bed and fall asleep for the night.

I was wearing a light blue satin nightie and matching panties. Like all of my nightgowns it was a little low cut and just barely covered my ass. These were meant for Jessica and Tom's eyes only. I watched TV for a little bit before I heard footsteps.

Jason walked into the den and said, "Can't sleep either, huh?"

I was flustered, because I didn't expect him to see me dressed this way.

I lied and said, "Yeah, sometimes when I drink too much I can't sleep."

"That's funny, me too!" He said, "Mind if I sit?"

What else could I say but, "Sure."

"What are we watching?" He asked.

"Casino," I said, "It's one of my favorite movies."

"Really? I figured a pretty girl like you would be into rom-coms," he said.

Oops, I thought to myself. This is my first time as a girl being alone with a man that's not Tom and I'm forgetting I'm not a guy anymore. I also noticed it was the third time he complimented my looks.

Not knowing what else to say, "I guess I'm full of surprises," came out of my mouth.

As we watched the movie I noticed that he kept nudging closer. I didn't think much of it, until his hand landed on my thigh. I turned my head to object and as I opened my mouth he kissed me. He slipped his tongue in my mouth as he rubbed my leg. Instinct took over and I began to kiss him back. I was kissing another man besides Tom, and it was his best friend. When that thought hit me I instantly broke the kiss, because I felt like I was cheating on him.

Jason noticed my reluctance and said, "I'm sorry, was that not ok?"

"No, I mean yes, I mean it was nice, but you just caught me off guard," I stuttered.

"I'm sorry. I don't know if Tom told you, but my wife died recently. I can't remember the last time I was around a woman as beautiful as you. You're wearing that sexy nightie and I guess I got a little out of control," he said.

"That's ok," I said, standing up, "I'm gonna go back to bed."

"Ok, goodnight," he said.

I got back into my uncomfortable bed and couldn't get the kiss out of my mind. My first thought was that Jason was going to tell Tom and he would be mad at me. Then I thought about how nice the kiss was and I started to question if I wanted more out of my new life than just being with Jessica and Tom. I don't know what time it was when I finally fell asleep.

Since I had a long night I was the last to wake up. I showered and got dressed in another casual dress. When I walked into the kitchen the three of them were eating breakfast.

"I hear my bestie got some action last night!" Jessica said.

"Huh?" I asked, although I knew exactly what she was referring to.

"I heard my boy put the moves on you!" Tom said.

Ok, he clearly wasn't mad, so that was a good thing.

"Oh we were tired and he kissed me, that's all," I said.

"Jeeze, you make it sound like you didn't enjoy it at all," Jason said, jokingly.

"That sounds about right for you!" Jason said, laughing loudly.

"Come on guys, the kiss was nice, I'm just not sure that's what I'm looking for right now," I said.

"I bet I can convince you?" Jason said.

"Oh really," I said, not thinking about what I was saying.

"Let me take you out on a date tonight. It's been a while, but I think it would be good for me to be out with a beautiful woman again," Jason said.

There he goes calling me beautiful again. I was flustered by his offer and looked at Jessica and Tom.

"I think you should go," Jessica said.

"Yeah, why not, you two go have some fun," Tom said.

I was shocked. I expected them to shut this down. Now I'm stuck going on a date with a man.

"Sounds like fun," I said, having no other option.

The weather was nice and the guys went to play golf for the rest of the afternoon. Jessica had been texting with Tom and found out Jason was taking me to a fancy steakhouse and I needed to dress appropriately. Jessica insisted on me going to have my hair, nails, and makeup done. She was making me go all out for my first date with a guy.

We got back home and she picked a short black dress for me. Remember all of my dresses were low cut and this was no exception. She had to top it off by picking a push up bra. My boobs looked tremendous.

"I don't know about all this," I said.

"Why? You look hot!" She said.

"Well yeah, but..." I started to say.

"But what?" She asked.

"What if he's looking to do stuff with me? Isn't this dress sending the wrong signal?" I asked.

"I spoke with Tom and we're ok with you doing anything you want," she said.

"But what if I'm not?" I said.

"You're a big girl, just say no. I'm sure girls have told you no before. Turning men down is one of the perks of being a hot girl!" She said.

"And what about my...?" I asked.

"Your what? Your dick?" She asked.

"Yeah," I said.

"I don't think you're that much of a slut that you're gonna sleep with him on the first date. I can't see him even expecting that. If you want make out with him a little and if he gets frisky, give him a handjob or a blowjob. It's not like you haven't done those things before," she said.

"Gee thanks," I said, not feeling confident about this.

"Come on Sweetie, just relax and have a good time. Don't stress about the sex stuff. A cute guy is taking you to a fancy restaurant. Enjoy being a hot girl. Order the most expensive thing on the menu. Remember this is his first date since his wife passed, he's probably more nervous than you are," she said.

That last part finally calmed me down and I said, "Ok, I'll try to enjoy myself."

"And then the best part will come tomorrow when we can a nice long girl talk about our dates. Tom is taking me out too. I'm gonna want details girlfriend!" She said.

While I was getting ready the guys had come back. We heard a knock at the door.

"Jesse are you ready?" Jason asked through the door.

Jessica opened the door to reveal my outfit to a surprised Jason. I don't know why I did it, but I twirled, letting my flowing skirt spin around and just barely exposing my panties.

"Whoa, looks like the hottest girl in the restaurant will be with me!" He said.

"Definitely!" Jessica said.

Jason reached out his hand and I took it. We held hands as he led me to his rental car. The restaurant was only five minutes away. When the valet opened the door I remembered how to get out like a lady and didn't flash the entire restaurant again. The restaurant was very high end. It was the kind of place I used to take dates too. It was a little weird to be on the opposite end, but a quick cocktail at the bar while we waited for our table calmed my nerves.

We had a nice time. Following Jessica's suggestion I ordered the Surf and Turf and when Jason asked me what kind of wine I liked, I picked a $300 bottle. He told me about his job and his wife. I was a little surprised he would bring up a previous partner, but because she passed so recently, I understood it was on his mind. I told him about my business, leaving out the specific details about my past. We talked about everything else like current events and sports. He used the term 'perfect woman' again, commenting that I was beautiful, but he could also talk to me like I was his buddy.

When we got back to the house Jessica and Tom were in their room already. The house was mainly dark except for the kitchen where they had left us a bottle of Johnnie Walker Blue. There was a note that said: 'In case you two want a nightcap. See you in the morning.' He gave me a suggestive look and I nodded in agreement. Blue was my favorite. I got two small glasses and put one ice cube in each of them. He was impressed that I knew how to drink high end liquor. He grabbed the bottle and we walked to the couch.

After two glasses my liquid courage was growing. When Jason put his hand on my leg again I remembered that Jessica said that she and Tom were ok with whatever I did tonight. This time I initiated the kiss. I think I surprised him, but he kissed me back and we made out for a few minutes. His hand never moved from my leg and I could see a bulge growing in his pants.

I was feeling good after the wonderful meal and the booze. I wanted to thank him for the night, so I put my hand on the crotch of his pants. This time he was the one who hesitated.

He removed his hand from my thigh and said, "Jess, I think we should slow down."

I was shocked. He was turning me down? I was the one who was worried about him trying to hooking up with me! I shouldn't have been, but I was a little insulted.

For some reason I said, "So you don't think I'm pretty?"

He said, "Are you kidding? I was right when I said you would be the hottest girl in the restaurant. It's just..."

"Just what?" I asked.

He replied, "My wife and I were high school sweethearts and I've never been with anyone else. I like to talk a big game and Tom has been telling me I need to get back out there, but I'm..."

"Nervous?" I said, trying to finish his sentence.

"Yeah," he said.

I rubbed his shoulder and said, "That's ok. We don't have to do anything you don't want to do. But it looks like your dick is thinking otherwise."

What the hell was I saying?! Sure his dick was threatening to burst through his pants because of me, but I didn't want to hook up with him, right? Or did I? Now I was confused. He was giving me an out and I was the one pressing. Maybe I did want to see what it was like to be fucked by another man.

He made the decision for me when he pulled me in for a kiss and started rubbing my leg again. I responded by accepting his tongue in my mouth and massaging his crotch. After some more kissing and rubbing, his hand started to creep inside my dress and he reached the edge of my panties.

I stopped kissing him and came up with the first lie I could think of, "Jason it's kinda my time of the month, so you probably don't want to go any further."

He didn't answer. Instead he continued kissing me and stroking the gusset of my panties. I gasped as he reached lower and touched my dick which was starting to get hard.

He stopped kissing to say, "Don't worry, Tom told me everything."

I was shocked. "He did?!" I said loudly.

He pecked my lips and said "And."

He kissed me again, "I'm."

Another peck, "Cool."

Another, "With!"

One final one, "It," and he was kissing me deeply again while rubbing my crotch.

He had me so worked up all I could say was, "Do you want to go to your room?"

Before I knew it he had scooped me up and he was carrying me to his bedroom. He really was a strong guy. He slowly placed me on the bed and he was on top of me, kissing me like his life depended on it.

When we came up for air he said, "I'd love to see that rocking body of yours if that's ok."

I stood up and said, "Can you unzip me?"

He gladly unzipped me and I spun around. My bra was doing extra work pushing up the twins and I was happy to take it off. My nipples were hard in an instant.

"Those are the most amazing breasts I've ever seen," he said, "My wife's were tiny."

"Just a tip for the future, it's not polite to talk about another woman when there's a half naked one standing in front of you," I said, giggling.

"Right," he said.

I touched the waistband of my thong and said, "I can leave these on if you want."

"No way, I want to see all of you," he said.

I pulled down my panties and my tucked dick started to emerge. I had become an expert at concealing it, but when I get turned on there's no way to keep it at bay.

"You really are a stunner," he said, "You know I've never done this before."

"You're a virgin?" I said jokingly.

"No silly, I mean with a girl like you," he said.

"Well yeah, you told me you've only been with one woman," I said.

"Tell me what to do next," he said.

"Well I'm a little naked here and you're fully clothed so strip!" I said.

He untucked his shirt and after that I think I witnessed the fastest disrobing of all time. He had a nice body and his dick was pointing straight out. He wasn't as stacked as Tom, but he certainly shouldn't be ashamed.

"What do should I do next?" He asked.

"I appreciate that you're being so sweet and asking me what to do, but I've been on the submissive side for so long now, that I'm fine with a man talking control," I said.

"Normally I would start by going down on the girl," he said.

"That's fine with me," I said, giggling.

"Yeah?" He asked, a little surprised.

"Sure, if you want to, be my guest," I said.

I didn't think he would actually do it, but I was wrong. He gently pushed me back onto the bed. I slid myself up so my head was on a pillow. He licked my dick and I sighed in pleasure. A few more licks and he engulfed my head before taking half of me into his mouth. He started to bob up and down. For his first time he was doing a great job. He wasn't as good as Jessica of course, but for my current needs he would do. I was getting close to cumming and I wanted to let him know. He has never sucked cock before and he needed the option.

In between breaths I was able to get out, "Jason, I just want to let you know I'm about to cum."

He looked up at me and smiled, well I think he did. It was hard to tell with my dick almost all the way in his mouth. He didn't hesitate to keep sucking.

I yelled, "Holy shit, I'm cumming!"

He swallowed every drop.

He pulled off and asked, "So how was that?"

"Wonderful," I said and then I had to tease him, "Are you sure you haven't done that before?"

"Nope," he said, "Now if you don't mind I'd love to fuck that amazing ass of yours!"

"I thought you'd never ask!" I said, "How do you want me?"

"I really like kissing you, so why don't you stay the way you are and we can make out while I make sweet love to you!" He said.

"Mmmm, sweet love, sounds nice," I said.

"Do we need anything? Lube?" He asked.

"No, I'm ready, just come up here and fuck me!" I said.

Jason proceeded to kiss every inch of my body, starting at my feet and working his way up. He pecked his way to my lips, stopping to give a smooch to my dick, belly button, and each nipple. When he reached my mouth I lifted up my ass a bit and wrapped my legs around his waist. He reached down and grabbed his dick to place it against my hole. He was smaller than Tom and would have no problem getting inside me. He pressed his head inside of me and didn't stop until his hips touched my cheeks.

"Is that ok Sweetie?" He asked.

"More than ok," I gasped.

Jason proceeded to fuck me, slowly. He wasn't kidding when he said make sweet love. With the exception of our first time, Tom was a little rough, which I loved. It was nice to be taken this way though. He inched ever so slowly in and out of me as we kissed.

Because he was taking his time, this was the longest love making session of my life, as the fucker or the fuckee. I was lying back and enjoying it when I felt Jason's dick start to get bigger.

"Sweetie, I'm about to cum," he yelled.

"Go for it, cum inside me!" I yelled back.

"Yeah?" He asked to make sure.

"Oh yeah, fill me up!" I yelled.

That he did. I was surprised at how much he shot inside me, but then I remembered he hadn't had sex in a long time. When he finished he pulled out and rolled over beside me, panting heavily. I sat back with a smile on my face. When he caught his breath he looked down to see my dick standing straight up. It didn't bother me that he hadn't made me cum from fucking me, because I had just cum from him blowing me. Apparently, it bothered him.

"Oh no, you didn't cum?" He asked all concerned.

"Don't worry about it. Tonight was wonderful," I said.

"No way, my lady deserves to be satisfied!" He said.

Before I could speak he was in between my legs and performing his second blowjob of the night, his second ever. Because I had cum once, it was going to take a while to get me there again, but I wasn't complaining. He took a break to move down to my asshole. It made me gasp when he licked it. I could feel that his load had begun to leak out and he didn't seem to mind. He went back to blowing me and a finger entered the picture. He certainly knew how to please a woman. Between the pressure from his mouth and the finger thrusting in an out of my ass, I blew my load in his mouth again. Like a good boy he swallowed it all again. He crawled up to me and gave me a kiss. We were both exhausted and pretty much passed out for the night.

I woke up to the feeling of being cuddled. I was naked and there was an erection pressing against my cheeks. Jessica wasn't on my left and it took me a minute to realize where I was. The night's events came flashing back, dinner, drinks, kissing, getting blown and getting fucked. I smiled. Then my mind started racing and I got worried. I had such a good thing with Jessica and Tom, and now I had a great night with Jason. Was I happy being with them, or did I want to explore more with Jason, or with other guys? My train of thought was broken when I felt Jason start to stir.