Lost Suitcase Adventure Pt. 03

Author's Note: Apparently no one wants this story to end...haha. I was content to be finished with these characters, but you guys got my creative juices flowing. Writing is hard, but once I got started I couldn't stop. The original Chapter 3 I wrote was way too long. I don't like to read stories that are too long, and I assumed others don't either. Chapter 3 quickly became Chapters 3 and 4. Chapter 4 will be published a few days after this one.

Chapter 3 is going to start with Jessica narrating and telling her version of events, including her plan. Then the story will pick up from the end of Chapter 2 from Jesse's perspective. Hope you continue to enjoy these!

Lost Suitcase Adventure 3

JESSICA'S POV -- BACKSTORY

My name is Jessica and I had recently moved to Florida with my then fiancée and now husband, Tom. My best friend from high school is Jesse. I know, a girl and a guy being best friends, can't happen right? It's true though, we hit it off right away and have been close ever since. He was a decent looking guy, and not to toot my own horn, I was told I was the prettiest girl in school. I always knew Jesse wanted to be more than friends, but he was never the take charge guy I wanted. We were the same height and I told him I was attracted to taller guys to test him. All he had to do was grab me and sweep me off my feet, but he was too timid, and never crossed the line.

While I wanted a strong, confident man, I also had a bit of a controlling side. I guess every woman does. I also had a big sense of humor and liked to play jokes, especially by teasing Jesse. I would bring him shopping with me and model clothes in front of him, asking his opinion about how he thought my current love interest would like them. I even took him to Victoria's Secret and modeled lingerie in front of him. I had to hold in my laughter when I could see him getting hard in his pants. I really am a nice person though and if my teasing ever got too mean, I would stop. He never complained and always laughed with me. We had this thing where we would punch each other lightly in the arm and call each other names. I loved him and he loved me, just not in that way.

TWO WEEKS BEFORE THE EVENTS OF CHAPTER ONE

Tom and I had been married for three months. I know this is weird to say after such a short time, but our sex life was getting a little stale. Don't get me wrong, we fucked like bunnies all the time, there was just something missing. One night after our usual session, he rolled off me and sighed. We had both cum, so that wasn't the problem. I was a little frustrated too and not being shy I had to ask.

"What's the matter Babe?" I asked.

"You know I love you, right?" He said.

"Of course, and I love you," I said.

"It just that...we have a great time in bed...I'd just wish we could shake it up a bit," he said.

"What are you thinking?" I asked.

"Do you remember before we were married how we joked about a threesome?" He asked.

"So you still want to fuck another woman?" I asked, a little insulted.

"You would get to play with her too," he said with a big grin on his face.

"Does it have to be a girl? What if I find a hot guy to bring in to our bed?" I asked, wanting to mess with him.

"No way!" He yelled. "I'm not having a Devil's Threeway!"

I started laughing and said, "Ok, let's put a pin in this for now, I'm kinda tired."

"Ok," he said, kissing me, "Love you."

I kissed him back and said, "Love you too."

THE NEXT DAY

I was up all night trying to think of a solution to our problem. Tom had to get up early to go to work. He had a great job at a TV station and I had inherited a nice amount of money from my Grandparents, so I was able to be a stay at home wife. I was eating breakfast when a text from my best friend Jesse came in.

We exchanged a few messages until he mentioned he had some time off coming up. Then it hit me. It was a naughty idea, but I was pretty sure I could pull it off. I knew he would do anything to sleep with me at least once. What if I dressed him up as a girl and let him be our threesome partner? Tom didn't want another guy in our bed, but I had enough control over both of them that I knew I could do it. If either one of them balked or got really upset, I could play it off as a joke like they were both used to from me already. I invited Jesse to come stay with us for a couple days and he was thrilled to come see me.

I got dressed and started working on my plan. I went to Victoria's Secret and bought a bunch of lingerie for Jesse. Then I made a stop at a store where I could buy fake breast inserts and wigs. When Tom got home he saw the bags.

"Ooooh, are you going to put on a fashion show for me tonight?" He asked seductively.

"Actually no, these things aren't for me," I said.

"Really, then who are they for?" He asked.

"Sit down and let me tell you my plan," I said.

"Ok," he said, sitting down on the couch.

"You know my best friend Jesse, right?" I asked.

"Yeah, of course, nice guy," he said.

"He's gonna come stay with us for a couple days. I was thinking he could be our extra partner," I said with a smile.

"What?" He said, shocked.

I just kept a big smile on my face and remembered a line from a movie 'Whoever speaks first loses'.

He said, "First of all I told you I'm not doing a Devil's Threesome and second of all you swore to me that he's not gay!"

"He's not, at least not that I know of. I've set him up with plenty of my friends and I know he hooked up with them," I said.

"Then what the hell are you talking about?" He asked, confused.

"Well, we are best friends, but I always had a bit of control over him. I'm thinking I can talk him into dressing up as a girl, a convincing one, and he can play with us," I said.

"But why would he agree to this?" He asked.

"Because he would do anything for the chance to sleep with me," I said.

"So in this scenario I would get my threesome as long as Jesse gets to fuck my wife?" He asked.

"That's my plan," I said.

"No fucking way. I don't want someone fucking my wife, even if he's your best friend," he said.

"Unless?" I asked and paused.

"Unless what? He asked.

"Are we negotiating?" I asked.

"Okay," he said.

"What's the other thing you want that I've been resisting?" I asked.

He thought for a second and said, "You mean? No, really?"

"Yep, if you agree to all of this you can fuck me in the ass!" I said.

"Holy shit!" He said. "So if I agree to a threesome with your cross dressed best friend, I get to finally fuck you in the ass?"

"Yep," I said.

"Can we do it right now?" He asked.

"If that's what you want," I said.

"But what if he doesn't agree to your plan? Then what would I owe you?" He asked.

"Nothing," I said, "I'll take the risk."

He smiled and scooped me off the couch. Our clothes were off in an instant and I was on my knees on our bed. I had bought a couple bottles of lube during my shopping trip and he was more than excited to grab one. I had never had anything up my butt before, so I told him to be gentle.

He started by licking my hole, which surprised me. I actually jumped forward and he laughed, pulling me back towards his tongue. He proceeded to bathe my asshole for the longest time. It felt amazing. I don't know why I resisted ass play this long. Then I heard a cap open and he pressed a finger inside of my ass. If felt weird, but kinda nice. He fingered me with the one before inserting a second. He started to press a third inside me, but he stopped and shoved two fingers from the other hand quickly inside my pussy. The feeling was amazing, and my body started to shake. I was having an orgasm with two fingers inside my ass and two inside my pussy.

"Feeling good Baby?" He asked.

I was out of breath already and moaned, "Yesssss."

"Are you ready to get fucked?" He asked.

Again I moaned, "Yesssss, pleaseee."

He pulled his fingers out and pressed his huge dick against my slightly opened asshole. He grabbed me by the waist and started to slowly push inside me. I'm not gonna lie, it hurt. I was an anal virgin and he was huge. My pussy had become used to his dick, but this was totally different. He sensed my discomfort.

"Babe, why don't you try to rub your clit. Maybe that will help you relax. You're so tight," He said.

"Ok," I said and reached in between my legs.

Just coming down from my first orgasm, my clit was sensitive and the second I touched it I got goosebumps. I started to massage myself and Tom went deeper inside me. Before I knew it his hips touched mine and I had taken all of his huge cock. I kept rubbing my clit and started fingering myself as he held himself inside me.

"Good now Babe," he asked.

I was barely able to speak, "Yeah."

With that he pulled out a little bit and thrusted back inside quickly. The pressure of his dick plus my fingers set me over the edge and I came for the second time. He started fucking me through my orgasm and got a good rhythm going, like I was used to when we fucked the traditional way. Now I focused on trying to meet his thrusts.

"Babe?" He asked, getting out of breath.

"Yeah?" I asked, out of breath too.

"I'm about to cum," he said.

"Mmmm," I said, "Go ahead, do it, cum inside my ass!"

"Really?" He asked.

"Yeah, go for it, blow a huge load up my ass!" I screamed.

Somehow he started fucking me harder and within seconds he screamed and I felt him swell, exploding inside my ass. I was used to him cumming in my pussy, but like everything else in this experience it felt different. Once he was spent he came over and kissed me, thanking me for tonight.

JESSE ARRIVES

Tom and I picked up Jesse at the airport. We met him at baggage claim and while he was happy to see me, he was pissed that the airline lost his bag. I couldn't believe my luck. My plan just got a whole lot easier. Jesse filed a claim and they told him with the incoming hurricane it might be a few days before they got his luggage to him. We drove to the house, and when he fell in the mud outside our house, leaving him soaking wet and ruining his only clothes, I had to laugh. I hated that my best friend was having the worst luck of his life, but the irony of everything falling into place was delightful.

I showed him to his room and he said he was going to take a shower. I told him to take his time and I would leave him some clothes that would fit. I didn't want to start with the new clothes yet, because that might spook him. Instead I brought him some of my own, a Black Satin Nightie, Panties. I left him a note that Tom's clothes were too big and this was all I had that would fit him. I kissed the note and walked back to my bedroom. I shut all the hallway lights and closed my bedroom door.

Tom was in bed waiting for me. I got in bed and turned on the TV. I had put cameras in the guest room and bathroom. I felt bad spying on Jesse, but I wanted to see what he would do. He had a surprised look on his face as he read my note and saw that I left him lingerie. We watched him open his door and when he saw the rest of the house was dark he went back inside. He picked up the lingerie and started to rub his fingers on it, feeling the material.

"He does have a cute little body," Tom said.

"Aha, so who's the gay one now?" I said, laughing.

"Yeah right, I'm just saying that I could see him as a girl," he said.

"Told ya, now shush, I want to see what he does next," I said.

Jesse continued to rub my lingerie and we watched him get an erection. He shrugged as if he talked himself into putting the clothes on. He put the nightie on first and then stepped into the thong. He walked into the bathroom and I switched the camera view.

We watched him check himself out in the mirror and Tom and I looked at each other and giggled. His nipples were hard and poking through the satin. He reached down and began to stroke his dick. Then he started to rub his nipples while he jerked off. Tom grabbed my hand and put it on his dick. It was as hard as I've ever felt it, all from watching my best friend jerk off in my lingerie. We watched Jesse cum into the sink. Tom couldn't take it anymore and he basically attacked me, fucking me hard until we fell asleep.

THE NEXT DAY

Tom had to go to work and my plan was in full swing. I got into Jesse's bed in a similar outfit and waited for him to wake up. I started right away with some sexy talk and commented that he was enjoying wearing lingerie. Once he got up we went to my room in search of clothes. He quickly realized that I wasn't kidding that Tom's clothes were way too big. Since all the stores were closed because of the hurricane, I convinced him to have a girl's day with me. He was reluctant at first, but when I bet him I could give him a hardon, he was mine. I stripped naked, and he popped the fastest boner I'd ever seen.

I had him shave his face and then I had him get rid of all the body hair below his eyebrows in the shower. When he came out his dick was still hard. I felt a little bad that I was essentially tricking him. I knew if it got to be too much I would drop it, but he would have to say something to get me to stop. I stared at his dick and noticed how nice it was. I had seen it briefly when he was hooking up with one of my friends, but now it was right in front of my face. I knew I couldn't get him dressed the way I wanted with his dick sticking out, so I helped him out. I dropped to my knees and gave him the best blowjob he's ever had. He's so cute, that he actually tried to stop me, but being the master I am, he didn't resist for long!

Once that problem was solved I got him dressed. I was still using my clothes for now, because I didn't think he wasn't ready for his own things yet. He didn't complain at all and soon he was wearing a pink bra, thong, garter belt, and stockings. Before I put on the stockings I had painted his fingernails and toenails in pink. I let him choose what color wig and he picked blonde.

All decked out in lingerie, I sat him at my makeup table. He briefly objected, but when I told him I had to complete the look he agreed. Once he was all made up I got him into a beautiful black cocktail dress with a flowing skirt. Lastly I gave him a pair of 3" Black Heels.

We spent the day together catching up and he didn't really mention his current wardrobe. He also didn't say anything about what would happen when Tom came home. Jesse didn't know, but I had been texting Tom pictures of him all day. I would comment on how hot 'she' looked and how I was looking forward to tonight. I knew it would be easy to get Jesse to go along, and I wanted to make sure Tom would go along too. I was relieved when he told me he was getting hard thinking about the both of us.

I knew Tom was almost home, but I neglected to tell Jesse. When he came in Jesse panicked. Tom knew exactly what to do. He referred to us as 'my girls' and asked us to stand up so he could see us. He kissed me and then went to kiss Jesse. I wasn't sure what was going to happen, but when Jesse opened his mouth to let Tom's tongue inside I knew we were golden.

Jesse briefly freaked out about the kiss, but he felt worse that he kissed MY husband instead of the fact that he kissed a guy for the first time. I told him it was ok and he dropped it. Tom went to change and I started in on Jesse. We were going to have that threesome tonight, and I was just about to get him there.

I mentioned how I could see he really enjoyed the kiss with Tom, teasing him that I never knew he liked kissing guys. Then I hit him with the threesome idea. The second I mentioned he would get to fuck me I knew I had him. He agreed so easily that I didn't feel guilty at all. We were all about to have the time of our lives.

We started with handjobs, I jerked Jesse off, and then he jerked Tom off and got his first taste of cum. Then it was time for him to get his first blast of cum in his mouth as he gave his first blowjob. He was reluctant for a second, but once he got going he was a natural cocksucker. To speed things up I sucked his dick while he sucked Tom's. Our threesome was off to a great start.

Then it was time for the main event. Tom had just cum in Jesse's mouth, but he was hard again. He must've been excited as I was. We agreed that Tom would fuck Jesse first. I leaned back against the headboard and had Jesse sit in between my legs. I wanted him to be comfortable, but I also didn't want him to freak out and run away. I wanted a front row seat, because I hadn't seen anyone get fucked before. I started playing with the straps of his nightie and kissing his neck. I told him Tom was gonna make him cum harder than he ever has before, and then he would finally get to fuck me.

Tom pulled off Jesse's thong and Jesse was hard again too. This was a great sign that Jesse was excited and I was happy to be fulfilling my threesome promise to Tom. I thought Tom would dive right it, and start fucking Jesse. He surprised both of us by using his tongue. He ate Jesse's ass like he had eaten mine before he fucked my ass for the first time. I was thrilled he was really getting into it. Jesse was really getting into it too, because once Tom started fingering him, he was begging to be fucked. Maybe my best friend was a little gay after all!

Jesse tensed up as Tom pressed against his hole. I comforted him and gave Tom a suggestive look. Tom knew what I was hinting at and kissed Jessed as he pushed inside of him. Jesse was into it and he put his hand on the back of Tom's head and started making out. It was the hottest thing I had ever seen! My best friend and my husband were swallowing each other's tongues as they were fucking.

Tom fucked Jesse on his back until they decided to change positions into doggy. Jesse was moaning like crazy as Tom pounded him hard. I was just sitting back and enjoying the show. Jesse was staring into my eyes as my husband broke in his ass. I was making cute faces and blowing him kisses. I felt myself getting wet and I started playing with my clit. I don't know how he did it with all that was going on, but Jesse moved forward and licked my pussy. He slid himself closer and was going down on me while he was being fucked. We were all moaning and Tom was basically fucking Jesse into my pussy. It was the most amazing scene ever.

Jesse was the first to cum and I watched him blow a massive load onto the sheets. Trooper that he was, he didn't stop attacking my clit. Tom screamed out and exploded inside Jesse. I'd like to think he felt the same way I did when Tom came in my ass. I was last to cum, but it was worth it. For the first time in my life I squirted, soaking my best friend's face with my juices. After that marathon we were all exhausted and decided to go to sleep. Jesse would have to wait until tomorrow to get his prize.

THE NEXT DAY

I woke up first and saw that the hurricane had passed. I went to the store to stock up our fridge while they slept. When I got home I was treated to a surprise. The bed was empty and I could hear the shower running. I walked into the bathroom to see Jesse bent over the bench in our shower and Tom was pounding his ass again. Not only was Tom plowing him, Jesse was thrusting his hips, fucking him back as hard as he could. I laughed to myself as I realized I've created a monster!

When they were finished all I could think to do was applaud. I found out they had fucked in bed before the shower too, so this was their third time. Tom left for work and I gave Jesse the bag of lingerie. Now he had his own underwear and I told him to get dressed on his own.

When we sat down for breakfast Jesse told me that Tom spilled the beans about my plan. I was thrilled he was ok with it and wasn't mad at me. The three of us had such an awesome time, how could anyone be mad anyway. Jesse assured me he wasn't gay, but maybe a little bi. He also wanted to make sure he could still fuck me and I said of course.