Lost Suitcase Adventure

Author's Note: I hope you have fun reading this story. For lack of a better term, the characters are superheroes. They are immune from all diseases and unwanted pregnancies. Please check out my other stories for the same type of entertainment!

LOST SUITCASE ADVENTURE

My name is Jesse and I was flying down to meet my Best Friend Jessica and her husband Tom in Florida. When I was new to my high school she was the one the principal picked to show me around. We hit it off right away. I am a decent looking guy, but she is gorgeous. We were best friends but never boyfriend and girlfriend. There were rumors that I didn't make a move on her because I was playing for the other team. She quickly put those to rest by surprising me and the entire school with a deep tongue kiss in the middle of the gym during a dance. I loved her, but I was never able to make it out of the friend zone. We were both 5' 10" and she always mentioned she was attracted to tall guys. She dated guys on the football and basketball teams, and she always made sure to hook me up with her friends. I'm sure she knew how I felt about her, but we were happy as friends, I made sure not to do anything to ruin that.

Her husband Tom was 6' 6", just her type. I had only met him once before, at their wedding. He was a nice enough guy and wasn't threatened at all by his new wife having a guy as a best friend. They had moved to Florida while they were engaged and I was going to visit for the first time.

Just my luck, I had decided to go down right before a hurricane was about to hit. As we landed, the pilot mentioned we were lucky to have made it because the rain and the wind had just started. Jessica and Tom were waiting for me at baggage claim when my second strike of luck hit. The carousel stopped and my bag was nowhere in sight. I went to the Lost Bag area and filed a claim. They told me they would deliver the bag if they could find it, but it might take a few extra days because of the storm.

We took the short drive to their home. It was pouring and I was a little glad that Tom was driving and not me. When we pulled up they handed me a small umbrella and they had a large golf umbrella for the two of them. They ran to the door, but being tired from the travel and the aggravation of losing my luggage, I walked slowly. This turned out to be the wrong idea, because the wind took control of my umbrella and it flew away. I started to chase after it, but the rain and the wind were too strong. I ran towards their door and I slipped and fell into their flower bed. By the time I got up and walked in the door I was drenched and covered in mud. My only pair of clothes was ruined.

Trying to hold her laughter in, Jessica said, "Oh My God. You look awful."

"Yeah dude, what the hell?!" Tom said, actually laughing.

I was pissed and just said, "Can I have a towel or something?"

"Of course," She said.

Jessica brought me a towel and showed me to my room.

"Why don't you take a shower and I'll find you some clothes," she said.

"Thanks. I'm very tired and I'll probably just go right to sleep afterwards," I said.

"Ok," she said, "We're probably gonna hit the hay too. Thanks for coming down. I'm so happy to see you!" She kissed me on the cheek and walked out of the room.

I got in the shower and began to wash the mud off myself. The warm water felt great and I took a long shower. I dried myself off and walked into my bedroom. To my surprise, instead of a t-shirt and boxers, there was a Black Satin Nightie, Panties, and a note.

"Sorry sweetie, this is all I could find that would fit you. Tom's clothes are huge. Sorry about the Thong, they're still all I wear. See you tomorrow. Love ya." She had kissed it made a mark with her Pink Lipstick.

Jessica was always a joker but this was a little too much. I wrapped my towel around my waist and opened my door. The hallway was pitch black and I could barely make out their closed bedroom door. Now what...they had clearly gone to sleep and I was on my own. I thought about sleeping naked, but quickly decided I didn't want to do that in someone else's house. I picked up Jessica's lingerie and it felt nice. I had always liked the feel of satin, but I never had thoughts of wearing women's underwear.

As I rubbed my fingers on the Thong my mind flashed back to our younger years. Being best friends she didn't mind if I watched her getting dressed. I never saw her naked, but she was always happy to model her lingerie for me and ask if I thought her date would like it. It was look but don't touch, and I was more than happy to just look. Now I was touching. I thought about Jessica wearing the things in my hand and I immediately got hard.

I tried to think of other things to get my erection to go down so I could go to sleep. I sat on the bed and scrolled through my phone to distract myself, but that didn't work. All I could think about was Jessica and her lingerie that she left for me to wear. It's not like anyone would see me dressed like this. I kept a positive thought that my suitcase would arrive in the morning and this would be a one time thing.

I stood up and slipped the nightie over my head. I always had light body hair and the feel of the satin on my skin only made my dick throb. I stepped into the thong and as I pulled it up I realized there was no way to get my hardon inside. The back ran into my crack and tucked in between my cheeks. The new feeling of the satin against my hole gave me a tingle.

I walked back into the bathroom to check out my lingerie. My lingerie...it's weird that I thought of it that way. Frankly, I looked ridiculous, my head with my short hair and a five o'clock shadow, leading down to thin shoulder straps of the gown. It hung just below my bellybutton and I obviously had no breasts to fill it out. The thong fit flat against my crotch with my raging hard dick sticking out of the side. I knew the only way to get it to go down was to rub one out and the thought of jerking off in my best friend's lingerie was exciting.

The feel of the satin on my nipples had made them hard. For a guy, my nipples were highly sensitive. I loved when girls played with them when we would fool around. I reached down with my left hand and began to stroke my dick. I had never felt it this hard. I moved my right hand up to my right nipple and began to rub it. A shiver went up and down my spine. I jerked off while rubbing my nipples. My entire body felt amazing and it wasn't long before I blew my load into the sink.

After a quick rinse and dry with my bath towel, I had shrunk to a size where I could fit comfortably inside my thong. There is was again...My Thong. Other than the small bulge in the front of my panties, from the neck down I didn't look too bad. I was already tired and my quick masturbatory session made me even more tired. I didn't even turn on the TV and went right to sleep.

MORNING

As I started to wake up I rolled on to my back and realized there was someone in bed with me. I was startled and opened my eyes quickly. It was Jessica. She was wearing a similar nightie to mine, except her amazing boobs were sticking up. I noticed her nipples were hard.

"Good morning sleepyhead," she said, "I thought you were never going to wake up."

I started to say, "I had a long day yesterday and..."

Then I remembered I was wearing her lingerie and reached for the sheet to cover myself.

She grabbed my hand and stopped me. "Oh no, I was enjoying the view!" She said, "Looks like my BFF is enjoying herself."

I ignored the fact that she referred to me as a girl and looked down. I was embarrassed to see my morning hardon sticking straight up and there was spot of precum right in the middle. My cheeks turned red.

"I can see that you're wet," she said, "That's ok, I'm a little wet too." And she started to rub the front of her panties.

"Jessica! What are you doing? We're friends and you're married! Tom would kill me if he saw us right now," I said excitedly.

"Gotcha!" She said and started laughing.

I punched her lightly in the arm and jokingly said "Bitch!"

She got out of the bed and said, "Don't worry, Tom had to go to work. Remember he's a producer at our local news station. He's one of the few people that has to work today. Everyone else is stuck in their homes. He wasn't even sure if he'd be home tonight."

"I hope he'll be ok," I said.

"Yeah, I'm not worried, this happens all the time," she said.

My phone buzzed and I said "Oh shit."

"What?" She said.

"It's from the airline. They found my bag but it's in Texas. They said they would get it on the next flight, but they don't know when that will be since all the airports are closed," I said.

"That sucks," she said, "Take a couple minutes to get yourself settled and meet me in my bedroom so we can find you some different clothes. I left you a toothbrush and some toothpaste,"

I walked into the bathroom and took care of business. I was a little reluctant to walk around the house dressed like this, but she had already seen me and Tom wasn't home. When I walked into her bedroom she was already wearing a cute little dress and had all of Tom's dresser drawers open.

"There's gotta be something in here that fits you," she said, "Otherwise there's plenty of my clothes for you!"

"Very funny," I said.

She handed me a pair of boxers and I gave her a look.

"What?" She said.

"Can you at least turn around?" I asked.

"It's not like I haven't seen it before," she said, "If you're bashful you can just pull them up over your panties for now."

I wondered when she had seen me naked and ignored her reference to My Panties, and I just pulled up the boxers. As soon as they reached my waist, they fell back down to my ankles.

"See," she said, "I knew his things were too big for you."

"He's gotta have something smaller, let me try a few more," I said.

"I have a fun idea," she said with a smirk.

"Yeah," I said reluctantly.

"Why don't we have a girl's day? I've always wanted a girl best friend and this is my chance," she said.

"You're not serious," I said.

"It will be so much fun! I already know how much you enjoyed sleeping in my lingerie, why not try the whole experience! Tom won't be here and we're trapped in the house anyway," she said.

"Jessica, you know I love you, but you're crazy," I said.

"Come on," she said with a cute little grin, "I'll be your best friend!"

She batted her eyelids and gazed at me with her big blue eyes.

"Jessica," I said, starting to cave.

"Sweetie I saw how hard you were in your panties this morning, imagine how good it will feel to be dressed up all day!" She said.

"Your lingerie did feel nice," I said.

"Ok, I'll make you a deal. If I can give you an erection in the next minute, you'll agree to play dress up with me. If not I'll drop it," she said.

"Ok, but you're not allowed to touch me," I said, thinking I outsmarted her.

"Deal," she said.

She proceeded to pull her dress over her head to reveal her amazing body. She hadn't put any underwear on and there wasn't a hair below her eyebrows. I got my first look at my best friend's massive breasts and I was a goner. My dick grew into a massive hardon and was straining my panties so much that I thought they would rip.

"I win," she said with a smile.

"Fine, but this stays between us," I said.

"Deal," she said, "Use Tom's razor to shave your face while I get some things together."

Jessica and Tom had individual sinks outside the entrance to the main bathroom. She directed me to his side while she walked into the bathroom. I lathered up and soon my face was nice and smooth. I heard the shower running and Jessica called me into the bathroom. She had her dress on again and handed me a bottle. The master bedroom shower was huge and it was much nicer than the one in the guest room.

"Ok, hop in the shower and cover your entire body with this. Then wait until I tell you to rinse it off," she said.

I knew exactly what was happening, but I had already agreed to play along with her and just said, "Ok."

I got in the shower and followed her instructions. The lotion she gave me tingled a little and it was a little weird to be standing there waiting for the okay to rinse off. She finally yelled and I watched the little hair that I had go down the drain. I got out of the shower and dried off. I noticed it was a lot quicker to get dry when you have no body hair.

I stepped out of the bathroom with my towel around my waist. Jessica was sitting on the bed with a pile of clothes next to her and a big grin on her face. As I walked towards her I felt a throb in my dick. She pulled my towel off quickly and my erection almost hit her in the face.

"Wow, bigger than I remember!" She said.

Again I was racking my brain to try to figure out when she had seen me naked before. I said, "Thanks."

"Well you can't get dressed like this," she said, "I wonder what we can do about it."

I began to say "Just give it a min-ohhh..."

She totally shocked me and took me into her mouth and began an amazing blowjob. I was breathing heavy and trying to get some words out.

I was finally able to say, "Jessica, what are you doing? We can't."

She pulled off and said, "You don't like it?"

"Of course I do," I said, "It's just that..."

She didn't wait for me to finish and started to suck me again. She took me deep into her throat and it felt awesome. I tried to let her know I was about to cum, but she didn't give me a chance and I unloaded into her mouth. I was still breathing heavy and had my eyes closed. She stood up and gave me a big kiss, similar to the one we had in high school. Except this time I tasted a little bit of myself. I didn't mind because she had made me feel so good.

She broke the kiss and said, "How was that?"

"Fucking awesome!" I said. "You're really good at that!"

"Thanks," she said.

"Why though? Not that I didn't enjoy it, but you're married to a great guy, who would frankly kick my ass," I said.

"I couldn't think of another way to get you ready to get dressed, and we agreed that today stays between us, so why not?" She said with a smile.

"Well I appreciate it," I said as I looked down to see my shrunken dick, "I guess it worked."

"Perfect, let's get you dressed for our girl's day!" She said.

First was the underwear. Of course she picked a pink set. I pulled the thong up my legs and it fit nicely. I still wasn't used to having a string stuck up my ass and I wondered how girls did it all the time. I fumbled with the bra, but Jessica was right there to help me. She fastened it around my chest and I was surprised to see I had the look of boobs that matched her D cups. She explained that she put inserts inside the cups to give me breasts. I wondered why she had inserts to mimic Ds, but went along with it. Next she wrapped this thing around my waist and I realized it was a garter belt.

"I'm wearing stockings? Around the house?" I asked.

"Yep," she said, "You'll thank me in a couple minutes. Sit on the bed."

I sat on the bed and I saw she had a small bottle in her hand. She unscrewed the top and I caught the obvious smell of nail polish.

"Really?" I asked.

"Yeah, what's a makeover without a mani/pedi? Except I'm just going to paint your nails," she said.

She grabbed my left foot and went to work. Of course she picked pink nail polish to match my lingerie. She carefully did each toenail before moving onto my fingernails. I could tell she was having a great time.

Once the nail polish had dried, she began to slide black stockings up my legs. The feeling of the nylon on my bare skin was amazing. My body started to get goosebumps and I felt my dick twitch. It was all I could do to stop myself from getting hard again. She told me to stand up and she clipped the stockings to the garter belt.

She could see I had a smile on my face and said, "See, told ya."

"These feel great. I don't know why girls wouldn't want to wear these all the time," I said.

"So my best friend is enjoying herself?" She asked.

"Yeah, this is fun," I said, conceding what she already knew.

"Almost done," she said, "What do you think: Blonde or Brunette?"

"Since you're Brunette, I guess Blonde?" I said.

"That's what I was thinking," she said.

She brought a Blonde wig out of her closet and put it on my head. I had no idea why she had wigs in her closet, but again I didn't ask.

"Almost done, just some makeup and your dress and we can hang out!" She said.

I wanted to object to the makeup, but I had come this far already and I was happy she was having so much fun. She led me over to her makeup table and went to work. I had no idea what she was doing, but after a few minutes I looked pretty good. I had long false eyelashes, cute looking cheeks and bright pink lips. Happy with her work she led me to her closet where I sat a beautiful black cocktail dress with a flowing skirt.

She pulled the dress off the hangar and unzipped the back. "Here, step in," she said, "And I'll zip you up."

"I'm wearing this around the house?" I asked, surprised.

"Yeah, you look so pretty, you might as well wear a pretty dress. Plus if your little friend makes and appearance, the skirt will be able to conceal it," she said.

I stepped into the dress and I have to say, it felt weird. The straps of the dress barely covered my bra straps, but I wasn't used to having bare shoulders. Sure I was wearing stockings, but the lack of material in between my legs was unusual. Speaking of feeling weird, Jessica brought out the last piece of the puzzle, a pair of 3" Black Heels.

"You can't be serious?" I said, "Heels?"

"Sure, we can't have you slipping on my wood floors in your nylons," she said, "Plus a girl needs a good pair of heels."

I put them on and for the first time in my life I was taller than Jessica, because she was wearing sandals with no heel. I stumbled a bit, but quickly got used to them.

"You look great. Too bad you weren't this tall when you were a guy. Maybe we would have hooked up," she said with a wink.

"I still am a guy," I said, punching her lightly in the arm.

"Sure Jesse," she said, "Actually this is perfect, Jesse works for a boy and a girl, so I can call you the same name."

"Whatever you want," I said, "Do you have any food around here? I'm starving!"

I followed Jessica to the kitchen, walking slowly in my heels. I always liked the sound of heels clicking on a wood floor, I just wasn't used to it coming from me. I sat down and forgot to smooth my dress underneath me. My bare ass hit the cold chair and I jumped. Jessica laughed and commented that I had a lot to learn about being a girl.

We had a great day and I almost forgot I was wearing a dress and lingerie. The weather was crappy so we spent most of the time watching TV and catching up. She told me more about Tom and her plans for the future. She also prodded me about my love life and tried to convince me to move to Florida. It was getting late when we were both surprised to hear the Front Door open.

Tom walked in and yelled "Honey I'm Home!"

I froze and my face turned bright red. Tom wasn't supposed to be home. He wasn't supposed to see me like this. Why hadn't he told Jessica he was on his way home? Now what? I was just starting to get along with him. I was totally embarrassed and wondered how I could ever show my face around here again.

Tom walked into the Family Room and said, "Or should I say Honeys I'm home?! I wanted to surprise my wife and her best friend, but it looks like you two surprised me!"

"Tom, we were just messing around since we were trapped in the house and I didn't have any clothes," I said.

"No complaints here," he said, "You look hot Jesse! Is it still Jesse? I guess your name works both ways."

"That's what I said!" Jessica said.