Lost Suitcase Adventure

She punched me in the arm as is our custom, and said, "Yeah right!"

We agreed to go wash up and meet in her bedroom. I went into the guest bathroom to clean my face. On the vanity was some makeup. I didn't know when she had the chance to put it here, but I didn't mind and touched myself up. She has been enjoying fooling around with Jesse the girl, so why not keep up the charade.

I walked into her bedroom and she was lying in bed completely naked. I can't believe I was finally gonna have sex with Jessica.

"Looks like you're ready," I said.

"Yep, are you ready to make love to your best friend or do you just want to fuck me hard?" She asked.

"How about we start making love slowly and then I'll fuck your brains out!" I said.

"And do you want my ass?" She asked.

I still couldn't believe those words were coming out of her mouth.

"If you're still offering, yes," I said.

"If your dick is as good as your finger, then oh yeah, I'm still offering!"

This time I had to take off my dress so I stepped out of it and tossed it on a chair. Jessica got a first full look at the lingerie she had bought for me in anticipation of my trip. I reached back to unhook my bra and she stopped me.

"No, no, no, bra and panties stay on!" She said. "Now how do you want me?"

"On your back is perfect for starters and then we'll play it by ear," I said.

"You're the boss," she said.

I crawled slowly on the bed until our eyes met. I pecked her on the lips before opening my mouth to give her a deep kiss. We were like two teenagers sucking each other's tongues. As we kissed, I reached down to free myself from my panties. I brushed my hand against her pussy and she was wet again. I lined myself up and slowly entered her. I was finally fucking Jessica! Her pussy was so warm and tight. I've had my share of girls, but only a few seconds in, I knew she was going to be the best. Once I was fully inside of her she broke the kiss.

"How does it feel to finally be inside of your best friend?" She asked.

"Fucking awesome!" I said and then started to repeat our joke, "If I knew it was this good..."

She interrupted, "Yeah, yeah, you would have done it..."

As she was speaking I was slowly pulling out of her and I didn't let her finish her sentence, instead I thrusted back inside of her hard.

"Years Ago!" She screamed. "I wish I let you fuck me years ago!"

I began to kiss her again as I slowly thrusted inside of her. I wanted to enjoy this for as long as possible, so I took my time. I had no idea how long we were making love when she started to moan slowly, "Harder! Harder! Harder!" I was happy fucking her in missionary, but if she wanted it harder I would need to change positions. I pulled out of her to a disappointed groan. I put my hands under her waist and flipped her onto her knees, just like Tom had done to me last night.

Once I had her in doggy, I thought about going right back to work. Then I thought it would be fun to tease her a bit. I put my hands on her cheeks and tapped the left one with my erection. She groaned again in disappointment. I did this over and over until she was thrusting her hips back at me, trying to entice me. Then a flash of red caught my eye. It was coming from her asshole. I looked closer and saw that she had put in a butt plug to get her ready. Wanting to tease her a bit more I grabbed the end and pulled it out a bit before sinking it back in. She let out a huge squeal. I repeated playing with her plug until I finally pulled it out so just the tip was inside of her.

She couldn't take it anymore and she yelled out, "Would you please just fuck me already!"

I couldn't say no to that so I lined up my raging hard boner with her pussy lips and at the same time I pushed the plug back inside her ass. I'd like to think that I filled both holes at the same exact time, but it was probably a few seconds off. I grabbed her waist and began to grant her wish of fucking her harder. I was fucking her deep with full strokes and she was making sounds I had never heard before. This might be the only time I get to fuck her, so I was getting my money's worth. The fact that she was enjoying it so much was the icing on the cake. As fast as I was going I usually would've cum by now, but after how much I came last night, plus the blowjob this morning, I wasn't ready to explode yet. The same couldn't be said for Jessica.

"Oh, Ohh, Ohhh, I'm cumming!" She shouted.

I felt her pussy get even wetter and her body started to shake. I slowed my pace, but continued to fuck her through her orgasm. She was moaning and panting and I was loving that I did this to her.

When she finally relaxed, she asked, "Are you gonna cum yet?"

"I think I can go a little longer," I said.

"Wonderful! Can you please cum in my ass?" She pleaded.

Those were words I had never heard before. I pulled myself from her pussy and removed her butt plug. There would be no teasing this time. I put my finger against her asshole and I realized she had lubed up as well. Between her juices on my dick, I should have no problem getting inside. I lined up and she moaned, "Slowly." I was right and slid right in. This was also a new experience for me. No girl had let me fuck her ass before. It was much tighter than her pussy, which if I remember correctly is how Tom described my ass.

I kept feeding her a few inches of my dick before pulling back a little bit. I wanted her to get used to it and loosen up. When our hips met, she let out an "Ahhhhh." I was slowly fucking her ass and she was making those noises again. Then her familiar pleading of "Harder, Harder, Harder," started. I picked up my pace and was fucking her ass as hard as Tom had fucked mine.

"Jessica your ass is gonna make me cum!" I yelled.

"Oh yeah Sweetie! Do It! Do It! Do It! Shoot a huge load in my ass!" She encouraged me.

My dick started to throb and I painted her insides. I didn't count how many times I shot, but it was definitely the most I had ever left inside a woman. We both rolled over onto out backs and lied there for a while without speaking. She leaned over and kissed me on the cheek.

"Thank you so much, that was really great," she said.

"No, thank you. I finally got to live out one of my fantasies. The fact that you enjoyed it so much is the cherry on top. You know I love to make you happy!" I said.

"Well you certainly did!" She said. "And you certainly left a huge load inside of me! I had no idea you had that much cum left!"

"You inspire me to great lengths," I said.

"I think I need to plug up again, I don't want to be leaking either," she said and reached for the butt plug.

She lifted her legs and eased it back into her asshole while letting out a cute squeak.

"Why don't we get cleaned up? Tom should be home soon. That dress you were wearing is fine, but I'd change your lingerie," she said.

I took my dress and went into the guest room. I hopped in the shower quick and washed up. I reapplied some light makeup and picked a white C cup bra with the inserts. For some reason I thought I should have some sort of breasts when Tom saw me. The matching panties were a thong, and when I tried it on it was kinda nice to have that feeling between my cheeks again. I put my dress on and meet Jessica in the kitchen.

Jessica was cooking dinner when Tom got home. He gave her a big kiss on the lips but just said hi to me, which seemed weird. Even though I was still dressed as girl Jesse, was he pretending I wasn't? I guessed maybe it was because we agreed last night was a one time thing. To tell the truth I was a little upset by it, and I wasn't sure why. I just had mind blowing sex with Jessica and I really wasn't attracted to him at all. Why was it bothering me so much that he was basically ignoring me?

Tom changed from his work clothes and we all sat down to dinner. As promised there was no mention of what Jessica and I did this afternoon and there was no talk about what happened between me and Tom last night or this morning. We just talked about his day and if there was anything I wanted to do on my last day there tomorrow. Once we finished, we watched some TV and everyone acted like I wasn't wearing a dress and lingerie. Frankly I missed the attention.

It was getting late and we were startled when the doorbell rang. Tom got up to see who it was.

"Good news Jesse, your suitcase is here!" He said.

While it was a relief that all of my belongings hadn't been lost, I was having fun with my new wardrobe. I had one more night with Jessica and Tom and I decided right there that I wanted to enjoy it. I told them I was going to bring my bag to my room and check it to make sure everything was there.

I brought my suitcase to my room but didn't open it. Instead I went right for my new bag of goodies. I pulled out a white garter belt and stockings. I pulled off my dress and added the accessories to the bra and panty set I was already wearing. I checked my makeup in the mirror and walked into their bedroom. I sat on their bed with my back against the headboard and waited. Not too much later I heard them walking down the hallway. They paused at my room and when they saw I wasn't there, they walked into their bedroom. When they saw me all decked out in lingerie on their bed they both smiled.

I said "I'd like to spend my last night having fun in here with you guys again if that's ok."

Jessica quickly pulled her dress over her head and Tom dropped his shorts and boxers.

THE END