*This is the part two of My Little Sister's Orgy. I recommend you read part one before moving forward.
Let me catch you up real quick...
It had been quite a few years since that fateful weekend. After Cali's little orgy party, her and my relationship was essentially redifined. We spent the rest of our time in that house together finding any opportunity to get each other off. We were pretty good at it, but we did almost get caught by mom and dad once or twice...
I went off to college at NYU. A couple years later, Cali would head off to UNLV. Her friend Jessica (you remember Jessica....) ended up going to school at NYU as well, which gave us plenty of time to reconnect. I was focused on engineering, Cali was in a cheerleading/dance program out in Vegas, and Jessica was a music major. College was a lot of fun, and I met a lot of women. Cali would come out to New York from time to time to visit her best friend Jessica, and of course, come sneak a night with her big brother (which was sometimes hard to hide from the current regular girl I'd be seeing).
With us across the country from each other, my play time with Cali became less and less frequent. When she'd visit, we'd always spend at least a night or two catching up for lost time, but they were always short trips and they didn't happen often.
What did happen often was how much I'd see Jessica. Her and I got really close out in the big apple. So much so that we started dating my junior year. I was really worried at first that Cali would not approve, but she surprised us both by being incredibly ok with it. The only strange part about my relationship with Jessica was that we never really talked much about that night all those years ago. I mean, sure, every once in a while it would come up, and Jessica would poke fun here and there about how close Cali and I were because of the night, but it was never something that was explicitly discussed. I assumed that Cali and her talked about all the other times Cali and I hooked up, but I was always too scared to address it with Jessica once we started getting serious.
There was one very drunken night in college, on a weekend when Cali was visiting, where the three of us hooked up again, but honestly, none of us really remember that night at all...not our finest hour. Cali and Jessica spent the entire next day in Jessica's dorm room puking and asking each other "what the hell did we do last night?" "Did we hook up?" "We didn't fuck James together again, did we?" We all knew what we did, in theory, but none of us had any real memories of it.
During school breaks, when we all gathered back in our home town, Cali, Jessica and I were inseparable. Because the two of them were besties since high school, no one (including our parents) thought it was weird that Cali would tag along for a date night, or seem to be a constant third wheel. I think Jessica loved having me and Cali around. I remember one time we were home, and the three of us were hanging in my room and we were reminiscing on that night. Jessica made a comment about how naughty Cali and I were that night, and I specifically remember wondering just how much Jessica knew about Cali and my ongoing relationship.
All these years, my sexual relationship with Cali had flourished, but as my relationship with Jessica got more and more serious, it became more and more of a secret. Did Jessica know about it? What she ok with it? Would she be? Was I cheating? Cali always reassured me that Jessica was aware, but I never seemed to have the balls to bring it up and actually talk it out with her.
- - - - - - - - - - -
...two years later.
- - - - - - - - - - -
There I stood, a year out of college, working a good job, making good money and living in the city with my, now fiancé, Jessica. She was finishing up her last semester, graduating early. Her graduation ceremony was just a week away, which would soon be followed by a big wedding we had spent the last year planning.
Jessica naturally asked Cali to be her maid of honor. The wedding was set for a month from today and it seemed like everything in our lives were moving in the right direction. What did it mean for me and Cali? Were our wild years behind us? I wasn't sure. We were all growing up fast and life was getting serious. I was about to make Jessica my wife. In a perfect world, I could have both of them forever. But I wasn't ignorant to the fact that that was not a realistic dream.
"One more month!" she squealed in excitement.
"I know! I can't wait!"
"I got you something..." she said.
"Why are you buying gifts??? I didn't buy you anything" I laughed.
"This is a special, 'last hoorah' gift for you." She reached into her purse and pulled out a hotel key. "This is for you."
"I don't get it" I said, looking at her confused. "Are we staying in a hotel tonight?"
"You are!" She looked at me with a devious smile. "I have to head upstate with my mom to make some last minute alterations on my dress this weekend, and so I booked you a night at the Roxy."
"Ok" I said "But why?"
"Well let's just say I'm the greatest future wife ever, and I wanted to give my man one last night of excitement before I become his forever woman!"
"Did you buy me a hooker?" I asked laughingly, shocked at what I was hearing.
She didn't answer. She just winked at me, kissed me and ran off to her room saying "My mom is waiting downstairs. I have to grab my bag and head out!"
She rushed back out and set her bag down next to my feet. She wrapped her arms around my waist and pulled me in close.
"I love you James. Have the time of your life tonight. You deserve it, Mr. Bachelor!"
She kissed me, and off she went.
I sat on the couch and thought about what the hell Jessica was doing. Why would she want me to fuck a hooker? Is this a test? A trap? I did always want to have some sexy night with a stranger in a hotel room. That sounded hot as fuck. I looked down at the room key sitting on the coffee table. I guess it couldn't hurt to just swing by, I told myself.
I grabbed the key, and headed out of the apartment.
As I rode the subway a few stops, I thought about what type of hooker Jessica had picked out for me. She's a tall, pale skinned, blonde, so maybe she got me a brunette? How about some eastern European model with a terrible accent? Maybe she'd be black? I'd never been with a black woman before. Would she be Asian, with that thick black Asian hair around her pussy? My mind ran wild and before I knew it, I was sitting on the subway with a massive hard on. I adjusted it in my waistband and made sure no one saw me. All clear.
I made my way into the hotel and towards the elevator. I stopped before pushing the button, all of a sudden overcome by a feeling of butterflies in my stomach. Was it guilt? Excitement? I wasn't sure.
"You going up?" a gorgeous young woman asked, creeping up behind me.
I turned to look at her and couldn't help but notice how stunningly beautiful this woman was. Jet black hair and a black cotton pool coverup that hugged her skin tightly, offering very little cover over her erect nipples, getting harder and harder under the hotel A/C. She had on no bikini under it...a fact I was sure of given just how revealing this outfit was. Maybe this was my hooker, I thought? I want to fuck this woman...
"I am" I said, as I pushed the button. She walked into the elevator first. I looked at the room key sleeve, which read 512. I pushed the 5th floor.
"What floor?" I asked her.
"7th, thank you."
Damn, I thought. Not my hooker.
The elevator dinged at the 5th floor and I walked out. I turned back just as the doors closed to snag one more glimpse of that jet black beauty. 512 was just around the corner. What should I do? Knock? Just go inside? Would the hooker be waiting for me, or would she arrive later? I slid the key into the reader and the door clicked open.
As I entered room 512, a familiar scent hit my nostrils. What was that? I couldn't place it. That is, until I walked past the bathroom and into the room. There, on the bed, wrapped delicately in transparent bright white lingerie, was Cali. Her bright orange, curly hair draped over the pillows behind her. Her nipples poking through the smallest amount of white, laced material. Her little red bush poking out the sides of her panties.
"Cali?!" I almost yelled.
"Hey there bachelor boy!" she said in her sexiest voice. "Like what you see?"
"Like it...." I had no words. "I fucking love it sis. What's going on?"
"Jessica asked me to come into town...said she wanted to give me to you as a wedding gift. Some sort of 'last hoorah' for us or something."
What the hell was happening? So Jessica did know all these years but just never said anything. And clearly she was ok with it? I was then immediately struck by that last sentence and realized that maybe she wouldn't be so ok with it from here on out.
"Last hoorah?" I asked her softly. "So...like...the last time?"
"Seems that way" she responded.
This was the first time Cali and I had ever really been confronted with this question. There seemed to be a lot of weight in the air with both of us realizing our relationship would need to realign yet again, back to a more "normal" place. It seemed like this was Jessica's way of letting me know that she would expect this to end after our wedding. It was a sad thought, but, I suppose, not at all a surprise.
"I guess we should have seen that coming" I replied.
"Well I guess we just have to make it one to remember!"
I didn't want to waste another second talking. I ripped my clothes off my body and pounced on top of my little sister. My lips made contact with her neck and I started licking and sucking at it delicately. I then moved down, inch by inch, kiss by kiss, to her breasts. The feeling of shoving my face into her massive rack, feeling it squish into them, never ceased to amaze me. Her pale white skin was so thin that the veins in her breasts could be scene through it. I pulled away the lingerie and put her nipple in my mouth. Her head leaned back as she exhaled a gentle moan.
While playing with her nipples in my mouth, I slid my hand down into her panties, grazing through her orange bush, linking the tip of my middle finger with her already swollen clit.
"Fuck" she slipped out, biting her lower lip.
When I had gotten her nice and wet, and slipped a couple fingers into my little sister, who took in a big deep breath and looked deep into my eyes. She knew what I was about to do to her. I started massaging her g spot with gentle pressure that built up in vigor, bit by bit, until she was riding my hand like it was a saddle. It didn't take long (it never did with Cali) before she flung her head back and contorted her body.
"Ah fuck!" She screamed.
Wave after wave of gushing cum erupted out of my little sister's pussy, making a massive puddle on the hotel comforter.
"James! Fuck!" was about all she could get out as she moaned and tried to find her breath.
I laid beside her as she collected herself.
"You are so fucking hot Cali" I told her. "It's insane to think about how it wasn't that long ago that you came into my room and propositioned me into your little orgy....now look at us!"
"I'm so glad you said yes that day" she said, eyes closed, enjoying her orgasm. "Took our relationship in just the right direction."
"So this is really going to the be the last time huh?" I asked. "Seems like Jess clearly has a feeling about this not progressing post-wedding."
"So what do you say we go crazy tonight and get out of the way all the wild shit we've ever wanted to do to each other."
"Like what?" I asked.
"Let's make a list" she suggested. "Absolutely no judgements."
"Ok" I laughed, getting up to grab a pen and pad off the bedside table. "You go first."
"Ok" she giggled, before letting out this secret. "I want you to give me a golden shower."
"Are you fucking serious?!?" I shouted, eyes bulging out of my head.
"Hey! No judgements!"
"Right, sorry" I said as I wrote it down.
"Your turn."
"I want to fuck you in the ass" I said timidly, not sure what her response would be.
