Lost Suitcase Adventure

"How's that Baby?" He asked.

"I feel so...full! You're sooooo Big!" I exclaimed.

"See Sweetie, I told you!" Jessica said.

He pulled back about halfway and thrusted quickly back inside me. I yelled out in pleasure. "Holy shit!"

"Your ass is tighter than a pussy! I take it you're enjoying this?" He asked, already knowing the answer.

"Yesssssss!" I moaned.

"I'm gonna start fucking you now, just tell me if it gets uncomfortable," he said.

Confused I said, "Aren't we already fucking?"

He didn't answer. He pulled back so that just his head was inside of me and thrusted all the way back in. I yelped and realized that now we were fucking. He continued his thrusting and was literally pounding me. His huge dick was busting me open and it felt amazing. As he was going in and out he was brushing against, what I would learn later, is my prostate. Every time he touched it I got a tingle and a little precum leaked out of my dick. I started to breathe heavy and Tom slowed down.

"Feeling good Baby?" He asked.

"Yeah, it's just that I'm getting a little sore from you being on top of me," I said.

"No problem, we can fix that," he said.

He pulled out of me quickly and grabbed me by my hips. He flipped me onto my knees in doggy style position. I locked eyes with Jessica who was still leaning against the headboard and she winked at me. Tom grabbed a hold of my hips and thrusted all the way inside me in one smooth motion. It didn't hurt this time, in fact it felt like he was back where he belonged. He started to pound me again and in this position he was hitting my prostate even better.

As my best friend's husband was fucking me I was staring at her beautiful naked body. She was making cute faces at me and blowing me kisses. She moved her hand down and started to play with her clit. That gave me a naughty idea. I was close enough that I could eat her pussy while I was getting fucked. I put my hands on the bed and tried to inch closer to her. Tom must have thought I was trying to get away and he grabbed my hips and pulled me back towards him. I inched closer and closer to her until I finally had the right angle. I surprised her when my lips touched her soaking wet pussy.

"Ohhhhh," she moaned.

I felt Tom stop for a second and adjust. He must have been looking to see what all the fuss was about. He realized what I was doing and he spanked my left cheek hard.

"So my girls want to have some extra fun," he said.

"Mmmm," Jessica said, "Keep fucking her into my pussy!"

He listened and picked up the pace, fucking me harder than ever. With each thrust I was pushed into her pussy, licking her everywhere I could. When I would get a full lick on her clit, she would yelp out in pleasure. While all of this was going on my dick felt harder than ever and it was dripping on the sheets.

"I'm getting so close to cumming with your dick in my ass!" I yelled.

"Good, because I'm about to bust a huge nut in your ass!" Tom said.

"And I'm about to squirt all over your face!" Jessica screamed.

As much as I would like to say we all came at the same time, nothing is that perfect. Tom's assault on my prostate was too much and I had a massive orgasm, cumming like crazy. My climax had an additional benefit. My asshole squeezed Tom's dick like a vice and it made him explode inside me. Just like when he ejaculated in my mouth, blowing his load in my ass was an experience. His cum was warm and the spasms of his dick gave my entire body goosebumps.

When he finished cumming he pulled out of me. Jessica hadn't cum yet and now that the pounding had stopped I was able to focus solely on her. I had always been good at going down on women and less than a minute later Jessica soaked my face as she had promised.

Once again we all rolled onto our backs and tried to catch our breaths.

Jessica was the first to speak this time and said, "Thanks Sweetie that was unexpected."

"Well your beautiful pussy was staring at me so I had no choice," I said with a smile.

"I don't think I need to ask, but did you enjoy your first fuck?" Tom asked giggling.

"Well, yeah. I don't know if it's something I'd do again, but you certainly made me cum really hard," I said.

"Don't cut yourself short. If it felt so good, why wouldn't you want to do it again? Your ass is amazing, might even be better than Jessica's." He said jokingly.

This time she punched him in the arm and said "Hey!"

"Just kidding sweetheart, you know you're the best!" He said. "So are you two ready for each other?"

"Actually I'm kinda beat," I said.

"Yeah me too," she said.

"Is it ok if we pick this up tomorrow? That's not against the rules, right?" I asked.

"That's fine. You're welcome to fuck my wife tomorrow. I have to go to work, so you two have all day to have some fun," he said.

"Sounds good," I said yawning.

THE NEXT DAY

We had all fallen asleep with Tom on the right side, Jessica in the middle and me on the left. I started to wake up and I was being spooned. I can tell its Tom because of his size and the fact that his morning hardon is pressing against my cheeks. He had thrown my thong across the room and I was so tired after last night that I slept without any panties on. Tom began to stir and I felt him kissing my neck.

"Mmmm Baby, we had so much fun with your friend last night," he said.

Uh oh, he thinks I'm Jessica. Instead of saying something I tried to pull away. He put his hand around my stomach and pulled me back towards him.

"Come on Baby, just a quickie before I have to get up for work. I'm still so horny after last night," he said.

I didn't know what to do. Did I want to be fucked again? Was it ok that Jessica wasn't here? The deal we made was a threesome, now it's just me and him. He started to kiss my neck again and I felt his dick inching closer. I had to say something.

"Tom, it's me. Jessica isn't here," I said.

"That's ok, you'll do," Tom said.

Before I could respond he lifted my butt cheek up and pressed his dick inside of me. After the workout he gave me last night he was able to slide right in.

"Oh yeah! Still so tight!" He said.

"Tom I don't know about this. Should we be doing this while Jessica isn't here?" I asked.

He thrusted deeper inside of me and I gasped.

"What do you think now?" He asked.

"I guess its ok," I said, giving in.

He began to fuck me slowly on my side. In this position I didn't have much leverage to fuck back. He was content to fuck me slowly as he just wanted to get off, and I was enjoying the movements in and out of my ass. I was hard, but I didn't feel close to cumming. He could have been fucking me for five minutes or fifteen minutes, I had no idea. Finally I felt his dick swell and he ejaculated inside me for the second time.

He pulled out and asked, "Was that good for you?"

"It was nice," I said, "I didn't cum, but that's ok."

"No it's not. My girls need to be satisfied. Come take a shower with me and we'll fix that," he said.

I was still not used to being called a girl. But isn't that what I've been for the last day and a half? I'm still wearing lingerie, a wig, and makeup, although my makeup must be totally messed up. I just had my best friend's husband fuck me twice and cum inside me, so I guess girl is the right word. Wait a minute, is he gonna let me fuck him in the shower? Damn these wild thoughts that I'm having. I'm still lying in bed while he had gone into the bathroom.

Tom sticks his head out and said "Water's warm, are you coming?"

I get out of bed and strip down. I started to take off my wig but then I stopped in case he wanted me to keep up the illusion. I got in the shower with him and he was washing himself. I'm too embarrassed to ask how he's gonna help me cum, so I just started washing myself too.

"You know if I knew how much you were going to be into this threesome, I would've had Jessica invite you over much sooner," he said.

"I don't know if I would have agreed if my suitcase hadn't been lost and I ended up in her clothes," I said, "They made me feel so horny."

"Losing your suitcase was just a coincidence. Jessica was convinced she could get you to wear her clothes and fool around with us regardless," he said.

"You guys planned this?" I asked shockingly.

"Yep, that's why she had the wigs, the fake breasts, and everything else you have been enjoying. When you showed up with no clothes it was even easier," he said.

"That sneaky bitch!" I said with a smile.

"You can take it up with her," he said winking, "Now I promised to make you cum."

He spun me around and told me to put my hands on the bench that was built in to the side of the shower. I guess he wasn't going to let me fuck him. He grabbed my hips and thrusted himself inside me. I moaned as he began to fuck me. In this position I had more leverage so I was able to thrust my ass back at him.

"Oh yeah, Girl, get after that cum!" He shouted.

He continued to pound me and I was pushing back at him. My dick was hard again and dripping. I picked one hand off the bench and tried to stroke myself. He grabbed my hand and put it back on the bench.

"No, no, no, you cum from my dick in your ass, not from jerking off!" He said.

I responded by fucking him back as hard as I could. It wasn't long until I was coating the shower tiles with my sperm. Just like last night my orgasm made my ass squeeze his dick and he emptied his third load inside of me. He pulled out of me and I stood up to hear what sounded like applause. I looked to my left and outside the glass shower door was Jessica and she was clapping.

"Looks like you two got started without me!" She said.

"Well you weren't in bed and I was all boned up. I needed a release before I go to work," he said.

"I'm happy you enjoyed yourselves. Anyway I woke up and saw that our power was back and the hurricane was over. I went to the grocery store while you were sleeping. I thought I would be back before you woke up," she said.

Tom gave himself another quick wash and I stayed in the shower to clean up. He had shot so much cum in me I was sure I would be leaking for weeks. I tried my best and got out. Jessica was waiting for me.

"Last night I thought you said you didn't want to do that again," she said smiling.

"He kinda roped me into doing it in bed and again in the shower," I said.

"He fucked you twice without me?!" She said surprised.

"Well, yeah," I said, reluctantly.

"You little slut!" She said jokingly.

"Hey!" I said, joking back.

"Then you're definitely going to need one of these," she said.

She reached into her drawer and pulled out a tampon.

"You already leaked all over the sheets last night and now he shot two more loads inside of you. I know my Tom is a huge cummer and I don't want you leaking all over the house. Assume the position," she said.

I knew what she meant and I put my hands on the vanity. I felt her push the tampon inside of me. It was definitely smaller than the fingers and the dick that had been inside of me, so it slid in easily. I felt her fiddle and when she was done there was just a string dangling in between my legs.

"There you go, my girl's first tampon," she said giggling.

"Gee thanks," I said.

"Now get yourself dressed and I'll make breakfast. You're welcome to anything in my closet and I left you a bag you might be interested in," she said.

She kissed me on the cheek and left the room. I looked in the mirror to see my makeup smeared all over my face and my wig was wet from the shower and last nights antics. I took some wipes she had and cleaned my face. Then I took off my wig. I looked in the mirror and I looked like me again. The only trace of being a girl was the soreness in my ass and the tampon lodged up there. I still had no desire to be a girl or be with men, but it was ok to fool around with Jessica and Tom. Once I got back home I would go back to being Jesse. I would be chasing skirts and not wearing them.

For now I still had no clothes of my own and was going to spend the day as girl Jesse again. Before getting dressed I applied some light makeup. Nothing crazy like yesterday, just a little on my eyelids and red lipstick this time. The blonde wig was all disheveled so I changed it up and put on the brunette one. I walked into the closet and saw a Victoria's Secret bag. This must be the surprise she was talking about. It was filled with bras and panties. On top there was a note.

"Thought you might like to have some things of your own to take home and remember us by. There are different sizes of bras for you to choose from. XOXO." Again the letter ended with a mark of her lipstick coated lips making an impression on the paper.

When did she have time to buy all this? I though. Oh yeah, this was a setup and she probably had it here for weeks. I was a little excited to have my own things, although I didn't plan on wearing them often. I emptied them on the bed and there were 15 bra and panty sets plus a couple of garter belts and stockings. There were also a second set of breast forms. The bras varied from A to C to D. My guess was I could wear the A with out any inserts. The panties were mostly thongs with some boy shorts mixed in.

I made my choice in underwear from the panties. Because I was still a little sore and had an object lodged in my ass, I didn't feel like having a string ride up there all day. I picked a pair of red boy shorts and those happened to match the A cup bra. I didn't mind that I didn't have to use the inserts. The panties also did a better job of hiding my dick and I liked the way they hugged my butt cheeks. I had a little problem with the bra, but when I got it in place it felt kinda nice pushing up my tiny man boobs. Not wanting to be fancy I picked out a loose fitting white sundress and a pair of white sandals. No reason to put myself through heels again. I checked myself in the mirror and thought I looked pretty good for a man in a dress.

I walked to the kitchen and was greeted with a cat-call whistle as Jessica was putting breakfast on the table. She had made pancakes, which she knew was my favorite. As we ate then questions started.

"Did you like your surprise?" She asked.

"Yeah, I guess. I'm wearing some of it now. I figured that's what you wanted me to do," I said.

"Oh good," she said, "Looks like you went casual and with the smaller bra."

"Yeah I thought I'd try to be a little more comfortable today and I didn't want to wear a thong again after the workout Tom put me through," I said.

Than it was my turn to ask the questions. Tom had already spilled the beans, but I wanted to see how long my Best Friend would continue to mess with me.

"By the way, when did you have time to buy all this stuff? Everything has been closed since I've been here and there's no way you could have known the airline would lose my bag," I said.

She started to blush and giggled.

"It's ok, Tom told me," I said.

"That bastard!" She said jokingly. "I was holding out as long as I could."

"Well you know I'm smart and leaving me a bag of lingerie was a dead giveaway anyway," I said.

"So you're ok with what happened last night and our plan to seduce you?" She asked.

"Yeah I had a lot of fun," I said.

"So are you like totally gay now?" She asked.

"No way! Maybe a little bi." I said giggling. "But I still plan on rocking your world after we finish eating, assuming that's still the deal."

"Oh yeah, I'm the only one who didn't get fucked last night!" She said. "And by the way you were amazing with your tongue. If I knew you gave head that well I would've let you go down on me years ago!"

"Oh really," I said and winked. "So best friend of mine, Tom told me a little bit about your plan, but I'd like to hear the whole story from you."

"Sure, here goes. Since we've been together Tom always wanted to have a threesome. I wasn't keen on him having sex with another girl and he didn't want a devil's threesome. We started talking about you and he often mentioned that it was unusual for a girl and a guy to be best friends. We made a deal that if I could convince you to dress up a girl, that we could have our threesome together. I had a feeling you would jump at the chance to finally sleep with me, so I knew it would be easy. Then when your suitcase was lost and you could only fit into my clothes it was like an omen," she said.

"And what if I said no?" I asked.

"Then I would have played it off as a joke and you would have never known the whole story," she said.

"So how do you plan on making it up to me?" I asked suggestively.

"Tom gave us his blessing to do whatever we want so it's up to you. It sounds like you're anxious to fuck me, but I would like to experience your tongue again. You can also fuck me in the ass if you want to," she said.

"Holy shit!" I said, "Really?"

"Of course, we can do anything you want. I am totally faithful to Tom, but he's been working a lot and we haven't had much time to be intimate. He told me today is my one chance to do whatever I want, no questions asked. What better way to do that than with my best friend," she said.

"That's amazing Jessica. I love you so much," I said.

"You know I love you too, and now you finally get to make love to me!" She said.

"Since you enjoyed my tongue so much why don't we start with a 69, I've never done one before and I've been dreaming about another one of your blowjobs," I said.

"Sounds great, let me take off my dress and we'll start on the couch," she said.

"Perfect, I'll take mine off too," I said.

"No, leave it on, and your panties too!" She said.

We walked over to the couch, me fully dressed and Jessica in her purple bra and panties. She pushed me onto my back and jumped on top of me. She kissed me. We made out for a few minutes and then she spun around leaving her thong covered pussy in my face. Her scent was intoxicating and I could see she was wet. She lifted up the skirt of my dress and while leaving my panties on, freed my hard dick.

"Oooh it's so big!" She said, as if she hadn't seen it before.

I took my cue and slid her panties down her legs until they rested on her ankles.

"Whoa, you're so wet already!" I said.

I went right for her engorged clit and as she opened her mouth to moan, she took my dick all the way inside her mouth. This was my first 69 so it took me a second to get going as I wasn't used to the angle. Her expert cocksucking was encouraging me to make her feel good. I used my tongue the same way I did last night, but now I had better access to my hands. I started to finger her pussy and I continued my tongue bath. Then I remembered she said I could fuck her ass if I wanted, so I figured a finger would be ok too. I put one finger in her ass and two in her pussy. It was something I hear the kids call The Shocker. She must have been shocked because she started sucking my dick even faster and then took me inside her throat. The feeling was so intense that I blew my load instantly. I continued to finger both of her holes and focused completely on her clit with my tongue. She had pulled off my dick and she was screaming like I was about to murder her.

"Oh My God! Oh My God! Oh My God!" She screamed, right before having a massive orgasm and covering my face with her juices.

Her whole body was shaking on top of me and I thought for a second she might be having a seizure. When she finally came down from her high I felt her tuck my dick back inside my panties and smooth the front of my dress down. She spun around to face me and started to kiss me again, not caring that her juices were all over my face.

"Fuck, Sweetie! Where did you learn how to do that?! I've never cum so hard in my life, not even with Tom!" She said.

"I just did what I thought would make you feel good. By the way you give the best blowjob I've ever had," I said, and then teasing her back from earlier, "If I knew how good you were at that I would have let you suck my dick years ago!"