Vacation Games

She collapsed onto me and shivered, the last throes of her orgasm tingling away. She kissed my chest, wrapped her arms around me and squeezed tight and let out a sigh. "Are you as nervous as I am right now?" I silently nodded in affirmation, deep in thought, wondering how we got here and if this was a great or terrible idea. She laid her head on my chest a little longer then raised her mouth to mine, kissed me and whispered "I can't wait for me to be yours again later." And with that, she slid off my cock, out of bed and went to turn the shower on.

I laid on the bed with music playing on her phone softly humming in the background. I couldn't believe we were about to go through with it - I was terrified but also excited and still turned on.

It all started months ago. Maybe it was the margaritas that we had on our date or maybe it was just the great sex, but the pillow-talk that night had drifted to raunchy fantasies we hadn't had the balls to act on. It was then I told her about how most girls I've been with have been what you'd call "good girls" and what I really wanted was to have some fun with someone wilder.

"Like what?" she asked.

"I'm nervous even saying this, but I'd love to watch the girl I'm with be a crazy, over-the-top sex-driven nympo...a total slut." As soon as it came out, I began wishing I could have it back, but it was too late now. "I'm not sure why it turns me on...maybe the power of it? I'd like to watch you walk down the street, decide 'I want to suck that guys dick,' shake your cute little ass in his direction for 30 seconds and have him as putty in your hands."

Jessie stared at me, a little apprehensively.

Shit, Mark, why'd you go there? Way too early in the relationship to reveal things like this! I started backtracking, but probably not very well. "Maybe it has something to do with the fact that guys can try to fuck whoever they want, but girls aren't allowed, you mostly just tease because if you did fuck everyone you wanted people would start name-calling - don't you ever see a guy you'd love to jump, but have to think better of it?"

She smiled now. "I mean, I do know that feeling, and you're right, I mostly just convince them to make out with me, so I know I have the power. I just walk away when I'm done."

Maybe I hadn't dug too big of a hole? I knew Jessie had enjoyed her time in college and early adulthood, pushing some boundaries and being wild, but every time I tried to get some stories out of her, she resisted. So I pressed onward, seeing if I could gain any traction.

"Hah, you little tease." I kissed her neck, just above the collarbone. "So you know what I'm talking about, you just played the game a little different. What if we were somewhere where nobody knew you and there were no repercussions, no chance to see any of the people again? Would Bad-Girl Jessie come back out?"

She shot me a glare like I might have stepped into something with that last comment. Gotta stop doing that! But when I thought it was about to get totally shut down, the tone of the conversation changed. "I mean, just like anybody, I see all sorts of sexy people, guys annnnd girls, when we're out. And you know how much I enjoy sex, so yea, I think about getting naked with strangers. If you were comfortable with it, I'd probably take advantage of the chance." She rolled over and looked me in the eye and changing from a matter-of-fact tone to one that was a little bit more sultry, said "so tell me how it would go..."

5 months later, relationship as good as ever, here we were, about to throw a crazy twist on everything. Everything you read online suggests adding people to the bedroom is a recipe for disaster, but I wanted to live out my fantasy and she had latched onto the ideas we talked about, so there was no turning back now - it was almost time to start the games.

She had finished drying off now and slipped a pair of tiny bikini bottoms over her slender legs and round, sexy butt. She looked over her shoulder at me watching her and wiggled her ass a bit. "It's all yours later, love, but you're going to have to share for a while." She came over to the bed and put a hand on my thigh and moved the single sheet off my naked body. She had been generous with her mouth this week, probably because she knew what was coming at the end of it. "Do you have enough in you for one more before I go?" she asked as she bent down and kissed the top of my softened cock.

It was the last day of our vacation in the Caribbean as we had hopped through a few islands on an amazing romantic getaway and then flown back into Miami for a couple of days at the end of the trip. We had spent the first few days exploring South Beach and having some fun, but now the real fun was going to start. At least for one of us.

"Mmm, I can taste your cum and my pussy on you," she purred as she licked up my slowly lengthening shaft. Gotta give her credit, she did know how to push my buttons and get me ready to go again, even if she had just ridden me hard less than 10 minutes ago. I started to harden faster, thinking about her sucking her pussy juices and the remnants of my first load off my cock. You could call it a mini-fetish, but I've always enjoyed the dirtiness of oral, both receiving and giving (especially giving), after hot, messy sex. Whether it was simply that it was too "dirty" for most of my early girlfriends to even consider, the submissiveness of it or just that it was a great way to extend the fun while giving my dick a well-needed break, I learned to love after-sex oral. Over the months since our initial dirty pillow-talk, she had learned this and used it to her (and my, I suppose) advantage.

I was mostly hard by now, turned on by her mouth and her words. She swallowed all of me and stuck her tongue out a bit to tap my balls one more time as I grew in her mouth. I grew to fully engorged and her mouth was wrapped around the first 6 inches of my solid 8-inch cock. After a couple big slurps, she looked up at me for approval. I let out a deep breath to signal that I was enjoying it and she dove right back to the task at hand. First licking her way up my shaft, then sucking on my left testicle, followed by a brief suck on my right. But her nervousness was visible - she kept looking up at me, to make sure I was ok. We both knew how dirty the day was about to get; maybe she felt bad about it or maybe she just wanted to make sure I got my enjoyments worth out of it.

Either way, she worked her way up to the top of my cock and buried it deep down her throat once again. She quickly ramped up the intensity, sucking on the head of my cock, then moving past the head, and taking more of me in her mouth. Then she started moving faster, pumping up and down my cock while flicking my head with her tongue every time she came up.

"Baby, that feels amazing, don't stop," I groaned. She kept working me. I looked down at her cute lips and hair in a ponytail, bobbing up and down on my cock.

I couldn't help but think of how my sexy girlfriend was about to become the biggest slut she could, all because of some dirty pillow-talk from months ago. The next time I'd have a chance to get my hands on her, she'd be freshly fucked, covered in cum and, hopefully, still begging for more. As she worked me, my mind drifted to what I had planned out for her and I lost control.

"Oh, shit, baby, I'm going to cum," I managed to get out before unleashing rope after rope of hot cum down her throat. She continued pumping her mouth on me until the last of my spurts was through, and then sucked slowly up my shaft a few more times. She looked up at me, as her lips came off the head of my cock, smiled, and then kissed my hip, then my stomach, then my chest on her way up to my mouth. She kissed me deeply - she had swallowed most of my load but the taste was left on her tongue. She knew I didn't mind, and stuck her tongue deep into my mouth before pulling away.

"12 hours to complete your games?" she confirmed. She already knew the answer. We had talked through the mechanics of it multiple times, but I suppose her wanting to know when I was allowed to have her again wasn't a bad thing.

"Heh, c'mon Jessie, you know this already. You've seen the envelopes and you know most of what's coming. The first one has complete instructions, plus your first task and the following envelopes you can open after you complete the task before it. I hope I made it a challenge for you, but if you have some extra time, you can use your slut-status and do absolutely anything you want to do between noon and midnight, as long as you document it with pictures and video. The only rule is no anal, I want you to save that for me for later."

"Got it," she said with a false bravado. "My ass is yours to fuck later, but the rest of me is anyone's who wants some. Plus, you can have as much fun as you want all day, no rules. Just remember, I want you hard later, so don't have TOO much fun. The envelopes?"

The clock ticket to 11:57am and I muttered "ahh close enough." I climbed out of bed and pulled four sealed envelopes, numbered in order, out of my bag and showed them to her. She quickly drew in her breath as one last indication of her nerves.

I handed her them her, grabbed her ass and pulled her tightly to me, kissed her deeply then looked into eyes and said "See you soon, my sexy little slut!" and pushed her towards the door.