Two years ago the most amazing thing happened... I won the lottery. 45 million to be exact. Not nearly that much after taxes, but I won't go into detail on that. Now some (ok maybe most) people would just quit working and live off that. But I've never been able to sit on my ass for long periods of time. So I invested in my dream: opening a resort hotel of my own. And boy, did I have an amitious vision. I wanted it to be the ultimate vacation spot. 750 rooms, 2 four star restaurants, a theme restaurant with a different theme each month, pools, beaches, hiking, a dive shop, a bar, and even a small casino.
Flash forward 2 years, and my resort is fast approaching reality. Money can make things happen quickly. Anyway, I knew this business was risky, so I hatched a plan to test my resort to make sure it lives up to my standards. And if there were any problems, I could fix them before opening.
My 10th high school reunion is coming up. My high school is small and doesn't make a big thing of it, they throw a luncheon every year at homecoming. After a few quick phone calls I have in my hands a faxed copy of the mailing lists from not just my year, but the years surrounding mine as well. So I send out invitations to the ultimate high school reunion, because let's be honest: luncheons are just boring. 3 months later and the day has finally arrived. As my 400 or so guests and their significant others arrive I'm getting nervous. What if it's too much? What if my concept is way off the mark?
I walk out to the podium in the banquet hall where my guests gather to begin my short opening speech. "Well this is a hell of a turnout. I'm glad you all came. I'm sure many of you are thinking that a free weekend getaway to such a spectacular resort is too good to be true. Well, almost. It is free, but I have one request. In your packets that you each received on the way in here there are materials describing all our amenities. Feel free to try anything and everything you want. All of it is on the house this weekend. I only ask that at the end of the weekend, you fill out the survey that you have in your packets. And remember, the only way I can make this place better is with your honesty, so tell me how you feel. Our grand opening is next weekend and I want to make sure this place is ready. Thank you again for coming. There will be a cocktail party and a banquet at 6, and that is the only large scheduled event this weekend. Have a good time." Everyone filed out of the banquet hall and the murmurs sounded very excited. I finally got some reprieve from the tension that had been building.
I designed the weekend so that I would have very little actual hosting to do, the resort should basically run itself and hopefully I would have time to spend with my old friends. So when the cocktail party started, I arrived along with the guests and searched the room for a friendly face. Momentarily, someone tapped my shoulder. I turned around and saw Jessica, a girl from my softball team. We weren't very close, but it was good to see her.
Ok, the truth is that I had wanted her. Badly. And seeing her now, looking 10 times better than she had in school, I wanted her even more. I gave her a hug and we struck up a small conversation, talking about the basics of the past 10 years - where we went to school, what we studied, whether it had any real relevance to our careers, and how the years were just flying by.
"Almost 30." she said, with a sigh.
"Yup. It's amazing how when you're 18, you're not 'almost 20'...but the day you turn 28 you're 'almost 30'" I laughed.
"That's so true. I don't want to be 30."
"You're only as old as you feel. And you look fantastic by the way. The years have not been so kind to some people in this room."
Jessica laughed and blushed, but didn't respond.
"Well, it's been great talking to you. If you'll excuse me, I'm going to go make the rounds and see how everyone's doing. I'll catch up with you later. And if you need me for any reason, ask the front desk." I said as I walked away. I wasn't sure how much more of that tension I could take.
The party was great. Almost everyone was a little buzzed by the time dinner was served...with more wine. Alcohol makes a vacationer happy. I sat at a table with my best friends from high school, everyone I used to hang out with. We were a motley crew of very unusual friends. Most of us were gay all through school, a trait which doesn't make you the most popular person.
"Oh my lord have you seen Heather lately? She got hot!" said Eric.
"Yeah, so is Brian. He was such a dork then. What happened?" chimed in Derek.
"I talked to Jessica for a little bit. As long as I could stand. I left when I was about to ask her up to my room. I figured that might be awkward." I said.
"Oh didn't you hear?" said Greg, "She came out. Her junior year of college she showed up at my brother's graduation with her girlfriend. Then they broke up at his party. Talk about awkward."
I didn't say another word for the rest of dinner, all my attention was on Jessica and how to make her mine.
I spent most of that night at the casino, schooling everyone at Texas Hold 'Em. Afterwards I stumbled up to my room and slept soundly for the night.
The second day passed uneventfully. Well, I was busy, but none of it is relevant to the story I'm telling, so I'll just skip forward to the part that is.
About 9pm, I was sitting in the bar having a drink with some old teammates. We were discussing (surprise) sports. Next thing I knew everyone gets quiet. I looked up and there was Jessica. I invited her to sit, but she just shook her head.
"I'm not feeling very social, but I do need to ask you something."
"Um...can we talk somewhere else?"
I excused myself from the table and we walked out of the bar and headed towards the beach. We walked in silence for a few minutes and when the lights from the resort started to fade she stops. I stopped and started to turn towards her when she reached up and grabbed my head and kissed me hard. We kissed for what seemed like hours, with our tongues sliding together in the most tantalizing way.
"I've wanted to do that for 10 years now...." she said as we broke apart.
"Wow" I said. And I kissed her again. Gentler this time, slowly, making sure I explored every part of her mouth before moving on to her neck and kissing my way down to her collarbone. "Do you want to see where I live here?" I asked.
We walked back and took the elevator up to my penthouse apartment. I keep it simply decorated with a few nice things. I have a flat screen tv and a top of the line entertainment system, a matching couch, loveseat, and recliner in leather, a bar in the living room and a mahogany dining room set. The kitchen is big for an apartment because I love to cook.
Of course Jessica didn't notice any of this, because as soon as we got off the elevator our mouths were attached again as we stumbled through the apartment, only breaking our kisses long enough to shed clothing as we went. By the time we got to my king size bed the only thing between us was our underwear.
I stopped kissing Jessica long enough to take in the full splendor of her nearly nude figure. I ran my hands lightly over her sides and down to her hips, then reached around and felt her ass. Oh what a wonderful ass it was. I kissed her again and ran my nails up her back, giving her goosebumps. I undid her bra and pulled it off, tossing it aside. I pushed her down on the bed and fell on top of her. I let my hands glide up to her perfect tits, gently caressing them and feeling her nipples harden under my palms. I ran my fingers over her nipples, flicking them with each fingertip before taking one in my mouth. At this she sighed audibly.
I took that as my encouragement and gently bit her nipple and held it in my teeth as I flicked my tongue over the tip. I did this until her back arched up and she moaned out loud, then I moved to the other nipple and repeated it. While my mouth was busy with her nipples my hands were moving lower, working down her panties as far as I could reach. I ran my nails up her thigh from her knee to the inside of her hip and heard her moan out loud again. She slowly undulated her hips, telling me she wanted more. Eventually I took my mouth off her chest and sat up. I pulled off her panties and threw them aside.
"I've wanted to to this since high school..." I said as I lowered my mouth to her hot cunt. My tongue on her hot hole made her jump and scream out loud. She was the sexiest thing I'd ever tasted. Somehow I knew she wanted it hard and fast so I worked my tongue inside her and wiggled it a little. I had to keep a tight grip on her hips so I wouldn't lose contact. I worked my way up to her clit and licked little circles around it until her hips were moving so wildly that I couldn't be gentle anymore. I opened my mouth and planted it on her cunt, sucking gently on her clit and making her scream my name out loud.
She bucked wildly and I did my best to stay with her as she moaned and screamed her pleasure and told me how close she was. I kept sucking on her clit and began flicking my tongue back and forth as I was doing it and that was all it took. She shook with her orgasm and screamed and grabbed the back of my head, pressing it harder into her pussy. I shoved my tongue inside her to taste some of her delicious juice. As her shaking subsided I pulled my head away and crawled up to kiss her mouth.
"Oh that was so much better than I ever imagined it could be" she said, and closed her eyes.
"Well at least I lived up to your standards."
"Yeah" she said, eyes still closed.
I laid down on top of her and she put her arms around me as I let her recover from what was obviously a much needed orgasm. Then, without warning, she rolled me on to my back and ripped off my remaining clothes. Her mouth went for my nipples and her hand went for my cunt at the same time and it was almost too much for me to take. I moaned loudly, and almost screamed as her fingers worked their way up inside me, first one, then two, and finally three fingers pumping in and out of my hot cunt. All the while she was biting and licking my nipples relentlessly. I knew if she kept it up I wouldn't be able to hold out for very long.
Then, almost as suddenly as the onslaught came, she stopped. She looked into my eyes and kissed me. "I know just what you need" she said. And with that, she lowered her head to my cunt and ever so lightly brushed her tongue over my clit. The electricity almost made me scream. She kept licking, barely making contact with my clit, moving with my hips as they bucked involuntarily. Gradually she licked harder and my moans got louder and I felt her hands moving up my thighs. Again I felt her slide three fingers inside me and I almost couldn't take it. She pumped her fingers in and out of my pussy and licked my clit softly. After a few minutes it was too much and the wave of my orgasm crashed over me making me scream incoherently.
As the tide passed she crawled up next to me and kissed me gently.
"That was better than I ever imagined," she said between kisses.
"Oh, and that's just the beginning." And with our 10+ year thirst for each other quenched, we lay down, but neither of us was tired. My fingertips started wandering over her body again, tracing a long and lazy trail down her side, up her back, then over her shoulder to her chest, stopping momentarily to caress her nipples, then continuing their trail over her body.
After a few circuits I could tell she was getting very worked up again. So this time I let my fingertips trace down the outside of her thighs and then back up the inside of her thighs. She opened her legs for me, hooking one leg over me and putting her foot behind me. I brushed my fingers over her pussy lightly and she ground her ass into me. Ever so slowly I pushed one finger inside her, teasing her this time around. With just one finger I went in and out, until her hips matched my rhythm, then I stopped. I removed my finger and moved to her nipples, gently twisting them and flicking them until her moans became audible, then I stopped again. I started running my nails all over her body, and she sighed and ground against me more.
Then she turned around suddenly, pushed me on my back, and straddled me.
"You know my first girlfriend dumped me because of you," she said.
"Oh really. How'd that work?"
"Yeah, apparently I said your name in my sleep a few too many times. And then she caught me masturbating and pretending it was you. She didn't like that. I always got off the best though, when I pretended it was you."
"Show me," I said.
And with that climbed off me and lay down on the bed and began to touch herself. She got three fingers inside herself with no problem and fucked herself slowly, making sure I had a good view. Then she stopped and spread herself open for me, waiting, and I could take no more. I lowered my face to her cunt and licked her clit with fervor. She was dripping wet, and I could tell she did a good job on herself.
"OH....wait....GOD....do you have any toys?"
I stopped licking and leaned over the edge of the bed so I could grab my toy box from underneath. I pulled it up on the bed and told her to pick one. She rummaged through the box of dildos and vibrators and other things for a moment and came up with the most expensive toy in the collection...my harness.
"Fuck me with this...hard."
I put on the harness and wasted no time. I got the dildo inside her with surprising ease and began thrusting deep. Our hips moved in rhythm with each other and we were shaking the whole bed and her screams could probably have been heard by everyone outside through the open window had they not been so drunk. Soon though, she rolled me over again. I was getting the feeling she got off on being in control, so I gave in and let her take control.
She had me on my back and was riding the toy and screaming her pleasure with no cares as to who heard us. I reached up and grabbed her tits and massaged them and twisted her nipples and before long I could tell she was close. A few more grinds and she started shaking. She shook and moaned and collapsed on top of me, my dildo still inside her. We lay there for a few minutes while I let her recover and then I rolled her off me so I could take off the harness. I looked over at her and she was more beautiful than ever. Her body glistened with sweat and her hair was a mess but she was radiant.
When she was fully recovered she went back to the toy box and rummaged a bit more. She came up with handcuffs and a blindfold this time and said "your turn." She pushed me down and put the cuffs on me, looping them around the post of the bed so I couldn't move. Then she put the blindfold on me and I was in darkness.
From that point on I'm a little unsure of the exact sequence of events, because, well, I couldn't see. I do know that she got up for a few minutes and the next thing I knew my feet were tied as well. She disappeared for a little bit longer, probably to the kitchen because in a moment or two I felt what had to have been ice on one of my nipples. Then the ice was gone and in its place was her mouth, sucking gently and warming me again. Then the ice was on my other nipple, making me jump and shiver. Then it was her mouth again. She let the ice cube slide down my body to my belly button, and then she ate it.
The next thing I felt was her now very cold tongue working its way inside my pussy. She fucked me with her tongue until the cold faded and she could sense how close I was. She quickly replaced her tongue with her fingers and moved her mouth to my clit and it felt like a jolt of electricity when her tongue made contact. She worked me into a frenzy with her tongue dancing over my clit and her fingers pounding in and out of me until I could stand it no more and gave in to the tidal wave of my orgasm. She stopped and untied me and we lay there in peaceful silence for a few minutes.
Peaceful until my phone rang.
"Someone is looking for you. They asked where you were."
"I'm in my apartment, I'll be down."
5 minutes later I stepped into the hotel lobby. I left Jessica on the verge of sleep in my bedroom. I figured I'd deal with the problem and go back and join her. I hadn't counted on seeing one of my best friends and her older sister. Her sister graduated a year before me, she graduated a year after me. We all played softball together and we were good friends. I was better friends with the younger, but the sexual tension between her sister and me had always been undeniable. Well, in high school everything seemed a lot more complicated than it ever was, so to put it simply, nothing ever came of it.
We chatted for a few minutes when I noticed the time. The bars were closing and people were going to bed. I, on the other hand, had just gotten my second wind from seeing two welcome faces, so I invited them up for drinks, figuring if Jessica was awake we could all talk. Erika, the younger, said she was tired, but Kristen, the older, decided to join me. We didn't say much in the elevator. Something about elevators makes people feel the need to be quiet.
When we got upstairs we cracked open a couple beers and sat in the living room talking. I told her about how the resort came to be and we talked about all the people we'd seen and how we never expected some of them to actually survive in the real world.
We were having a discussion about old crushes and ex girlfriends when Jessica wandered out of the bedroom wearing one of my oversized tshirts. She got a beer and came over and sat down. The look on Kristen's face was priceless.
"So, what's up? Haven't seen you in forever," Jessica said.
"Holy shit" said Kristen, "You're queer too? Wow, that school was just a breeding ground, wasn't it? Holy shit...oh god, did I interrupt when I had the front desk call you? Oh shit...I'm sorry...."
"No, no...you didn't interrupt. We just finished." "Finished?" said Jessica, "If it had been up to me, we'd be going again."
There was an awkward silence, and then Jessica went over to the bar. She came back with a bottle of Southern Comfort and some shot glasses and said, "Hey, let's make it a party."
"Well, I can leave, if you'd rather...." said Kristen.
Jessica grinned a wicked grin and said "no, I think it'll be more fun this way."
Kristen looked at me in shock, and I just shrugged. I had no words for the way this weekend was turning out. The air hummed with sexual tension and we both knew that Jessica was the catalyst fueling the reaction between the three of us. We also knew that at that point, we couldn't do a thing to stop it. Kind of like a crazy roller coaster...some people might wonder why you would want to do such a thing but when it comes down to it, all you can do is strap yourself in and go along for the ride.
"How about a twist on an old softball tradition?" Jessica said as she poured three shots. "Truth or dare....or shot....on your turn you get to pick, and the other two come up with a dare or a question, or you do the shot. If you choose truth or dare and wimp out and decide you'd rather do the shot, you have to do 2."
Kristen quickly figured out what I already knew, which was that there was no saying no to Jessica, even if you wanted to, which in truth we really didn't. There was no denying the tension in the air. At least there was someone in the room willing to do something about it.
"Ok fine, I'll start," Jessica said, "And I pick dare."
"Ok," I said, "I dare you to sit there naked," and Kristen quickly nodded her agreement.
Without a word Jessica stripped off the t-shirt of mine, and it turned out that was all she was wearing. Then, with a grin, she said "your turn."