Drunk Aunt is Fun Aunt

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Story of my one night stand in the Caribbean.
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It was 1 am when I was awoken by the villa door slamming shut. I opened my eyes quickly and listened, but the gentle whine of the air conditioning was all I could hear.

"Somebody just got back?" I told myself as I begrudgingly noticed the time.

I had been stuck in all night babysitting my 5 year old cousin while the rest of my family enjoyed the night life of the island.

•••

We were staying in some fancy resort in the Caribbean that my mom picked out. The place was huge and spread out with multiple pools, beaches, and restaurants. We had three bedrooms and three bathrooms spread over 2 floors in our villa which overlooked the ocean. My mom and dad had brought down my uncle and his wife, Kristen. They were both considerably younger, my uncle (my mother's brother) was just 31 and his wife of 6 years was just 28. They were both closer to my age than my parents who were getting close to 50.

We had been on the island for 6 days out of our three week trip. Early on we had decided that one of us should stay back at the hotel every night and babysit to allow everyone else to go out and have a good time.

After a long time at the beach, we had driven back to the hotel. (around 3 o'clock)

They all dropped me and my cousin off and proceeded on into the main town area to enjoy happy hour. (3 P.M.-7 P.M.) on the island. My cousin and I walked through the open air lobby (grabbing a complementary rum punch for myself on the way) and found a golf cart waiting to chauffeur us back to the room which was about a 1/2 mile away down by the beach.

I waved my key-card in front of the door and the lock opened with a systematic click. The rush of cool air hit me hard as I stepped inside the villa. All the lights were off but light shone in through the seams of the curtain shielding the sun streaming in from the balcony. I dropped a few of the beach bags by the door and headed into the kitchen to refresh my drink

About 20 minutes later my cousin was showered and tuckered out from his day of swimming so he headed to the second living room where he had a roll away bed. I knew by nap he meant that he was going to watch the Disney channel of whatever shit kids watch now.

I walked over to my room which was the smallest of all but still had a private balcony and view of the beach, but maybe most importantly a queen size bed and a private bathroom with a big beautiful shower.

I slid open the door to my balcony which was of considerable size. It had both a small couch and a lounge chair. I quickly went back to the kitchen got a snack and my laptop. I sat down on the lounge chair pulled over a table and relaxed. I watched a movie and had a few drinks. Around 6 my cousin came looking for me wanting to go the pool. We walked down and he swam around for a while. I had made sure to pick a seat close to some girls who I made friends with and talked for a while. They were from Connecticut and I got a few of their numbers and told them to call me if they ever came to New York City (where I live) for a "tour." About an hour later, I got a text from my uncle that they were coming back to pick us up for dinner; so I fished my cousin out of the pool. We walked back to the room and by the time we were back he was dry. We changed quickly and called for a golf cart which delivered us to the lobby where the rest of my family was waiting in the car.

My mom was driving as she was the only one who wasn't hammered. My cousin climbed into the way back and I followed. We were in a big SUV with 2 seats in the middle and 3 seats in the way back. My parents sat in the front and my uncle sat on the right side. I climbed in on the left side (People drove on the left side of the road on the island) over my aunt who was probably the drunkest of all. As I shimmied by she grabbed my ass and felt me up pretty good. My aunt and uncle laughed and I blushed.

•••

We went to some Italian place and watched the sunset. We left around 9 and went back to the hotel. My uncle and I brought my cousin back to the room. By the time we were back it was close to 10. Both my cousin and uncle went to bed; the latter took a shower first, but was soon in bed too.

I had another drink and went to bed too. I slipped into the sheets and groped for the clicker. After a few minutes, I settled on a baseball game on ESPN. At 11 I got up to pee and as I returned to bed I heard the door close. I walked into the kitchen to grab a water from the fridge and saw my father coming in. I asked him where they'd been, and he said they had been at the beach bar. He grabbed himself a water too, and stumbled off to bed.

I went to bed soon too, and fell asleep in a few minutes.

•••

At 1 A.M., I awoke to the sound of the villa door slam shut. I looked at the clock and shook my head. I heard hysterical laughing and a bang coming from the hallway, and then an unmistakable "shhhhh!" I rolled my eyes to myself and turned over and fell back asleep.

A few minutes later my Aunt Kristen and my mom opened the door to my room and snuck in. My mom quickly sat down in a chair across the room giggling. I slowly stirred because of the noise and half asleep I rolled on to my back without opening my eyes or noticing the two women in my room.

Suddenly I jerked awake as my aunt jumped on top of me. She was laughing uproariously almost to the point of crying and all wet as if she had just taken a shower. Confused I started swearing at her until I finally pushed her off to the right of me. Quickly she climbed back on top of me straddling my stomach her butt resting on my crotch. I started yelling at her again as my mother turned the light on and I saw that she was wearing just a white fluffy robe courtesy of the hotel. On her head she had towel drying her hair.

My aunt, Kristen, herself was a very good looking woman. She was, as I said before, 28, and had beautifully tanned skin, but only because she had been sunburnt our first day here. She was busty with D cup breasts and wide hips and a full butt. She was a little overweight after she had a child but had recently slimmed down in the past year. Her dirty blonde hair fell to her shoulders and would often have thick curls. Her face was round and full with big lips under her dark brown eyes. She was hot by any man's standards and now she was lying on top of my wearing only a loose fitting robe.

Both my mom and her were laughing so hard I couldn't help but laugh myself. She pulled off the towel from her hair and her beautiful long hair fell down to her left shoulder.

Then she put the towel on her head and said, "I am the angel of peace, here to bring good tidings to you!"

Then she tickled my sides until they burned from my laughing. I struggled to squirm away but she closed her thighs around my stomach hindering me incapable of escaping. All the while her butt rhythmically brushing against my dick which was slowly becoming rock hard. After cursing her out for several minutes she stopped collapsing from her own laughter rolling beside me. My mom had left at some point during my brief torture. Kristen got up to my relief and started out to the kitchen and subsequently to bed...or so I thought.

•••

I began to watch TV and hoped that somebody would return and shut my light off so I wouldn't have to, and I guess you get what you wish for because 5 minutes later, Kristen returned with a bottle of Tequila, a bottle of Margarita mix, and two glasses full of limes and ice. She placed them all on my bedside table and to my joy/surprise her loose robe had come undone bringing the drinks supplies to the room. She had yet to notice her right boob was nearly hanging out of her garment to the point of almost revealing her nipple. She went over to the slider and looked outside towards the beach. The air conditioning was set to a cool 62° and when she turned around, the outlines of her big nipples were clearly visible.

She strolled tipsily over to our new makeshift bar even though she was incredibly drunk all ready. She made me a drink first and it was astonishingly strong, so much so I nearly spit it out. It was nothing for Kristen though who had had so much booze today she probably couldn't tell the difference between vodka and water. She went over to the door and nonchalantly flicked the light off and returned. She rolled into bed next to me getting under the sheets and bumped into my shoulder; I felt that she was still significantly damp. She pawed around under the sheets for the TV remote occasionally feeling up my thigh.

I was only wearing a white NIKE tank top and a pair of very short briefs, so the majority of my skin was exposed. She finally found the clicker after what felt like hours and found HBO or Showtime or whatever premium channel the hotel offered for free. It was 1:30 now and if you know anything about late night HBO you probably could guess what was on. Kristen was already done with her drink after I had just had my second sip and sat down lower in the bed and rested her head on my chest her eyes glued to the TV. The show if you could call it that had just begun, but the real show had not yet begun. I wondered to myself is Kristen really knew what she was doing or if she was this trashed. She grabbed my free hand and led it to her right shoulder, then began to rub my stomach.

A few minutes later she started to squirm trying to get comfortable. I asked what was wrong and she said my T-shirt was uncomfortable. I asked her if she wanted a pillow to be more comfortable. She suddenly sat up and looked straight in my eyes the only light of the TV illuminating her face. She responded no that she needed a person to lay on in a whining voice I would expect from a young child. She grabbed the Margarita from my hand spilling it as she harshly placed it onto the table she pulled me down from my sitting position so I was right next to her lying down. She grabbed the sheets and yanked them away. Then she grabbed my shirt and ripped it over my head before I could even get a word out. I sat back down amused of how angry she had just gotten over a shirt.

Two women were on the TV now and that classic music came on. At almost the same time Kristen stood up and turned the TV off. In the dark she walked over to the blinds and pulled them shut leaving the room in extreme, total darkness. I couldn't see anything even the cliche of not seeing my hand in front of my face. I heard my aunt cross the room and leave. Confused again, I rolled over and tried to fall back asleep wondering about my strange night.

•••

It couldn't have been 5 minutes later when I was awoken by my light coming back on. I sat up as I heard my door slam shut behind me. Slowly my eyes adjusted to the light ready to curse out whoever had woken me up for the ten-thousandth time tonight. As I peered to my door, My Aunt Kristen was standing in front of the door in the same robe as earlier.

"What do yo-you think?" she slurred.

"It's fucking 2 in the morning I'm done playing games!" I said almost yelling.

"Are you sure about that?" she responded seductively as she dropped her robe revealing the sexiest (only) lingerie I had ever seen.

Under her robe she wore full lace lingerie. It had hot pink bra with black see-through-lace covering her stomach. Her panties were black as well but a pink thong rose just above. Below was a black garter holding up matching pink lace stockings. She had obviously put on make up and did her hair too but I had not immediately noticed it. She had put on mascara and pink lipstick the same color as her lingerie. Her hair was curled up at the bottom looking its best.

My jaw had firmly dropped down and she laughed in victory. She walked up to the bed and noticed my obvious dick which had tented in my briefs. She sexily put her leg up on the bed giving me full view of her lingerie clad crotch. At this time I first noticed her pink stiletto heels. She brought her hand down to her crotch and began to rub her clit in a circular motion. I stared at her as she slowly pleasured herself; I was probably drooling. She stopped suddenly and put her foot down and strode back to the door to dim the lights and in doing so I got a sexy spectacle of her voluptuous ass. She turned her head as she dimmed the lights and winked at me and slapped her own ass. I was in a trance or something. I couldn't believe the site of my sexy aunt who I knew almost for my whole life was probably about to take my virginity. She sashayed back toward me and removed the top sheets completely she jump back into bed and straddled me once again.

The only difference this time is was that she forcefully planted herself on my crotch. She kissed me sensually then moved down on to my neck. I stared at the ceiling as my neck was sucked on. The faint light was just enough to see every detail of her body as she gradually made her way down my body. She stopped abruptly and reached for the tequila and some limes. Smiling she squeezed the lime on to my stomach and then poured Tequila over it. She arched her back and moved off of my crotch as she licked me clean staring into my eyes the whole while. She giggled lightly and moved back on to my lap. Kristen stood up straight and reached behind her back and unhooked her bra.

Her breasts fell with gravity almost in slow motion. They were large and round just as I had expected, but unexpectedly her areolae were massive and her nipples were sticking straight out. She spun off of me and yanked me on top of her in one motion. She reached out and grabbed more limes and tequila and handed it to me. Carefully I squeezed the lime onto her stomach, but Kristen quickly grabbed my wrist and moved it to her tits. Understanding now, I took another lime and squeezed it on to the another boob. Then uncorking the tequila I poured it on top. I slid down until my mouth was just at her boobs and she locked her legs around my body. As I sucked on my first tit ever I felt her wetness protruding through her panties and thong. After I was done I rolled back on to my back. Kristen stood up and walked around the bed her boobs bouncing as she walked. She took a shot of Tequila motioning for me to sit up at the same time.

She then climbed back into bed face to face with me and told me to strip her. She laid back down and bent her knees up. I stood on my knees and put my head between her thighs as I attempted to unstrap her sexy stockings. She again reached down to her pussy and began to rub around it getting wetter and wetter all the while. She watched closely as I pulled the stocking off. As I pulled it down her leg sensually she lifted her leg and allowed me to take it completely off. I did the exact same thing with her other leg until I was ready to step up to bat in the big leagues. She repositioned herself in the middle of the bed and I placed my hands on her hips and slipped her panties off. She lifted her butt off to allow me to take them off revealing her pink thong.

"Pull those of with your teeth!" my aunt said giggling at my recent struggle.

I instantly put my head right at her crotch where I could feel the heat of her throbbing pussy underneath the thin material. I bit down at the top of the thong and easily ripped it unveiling first her cutely trimmed pubic hair and then her sloppy wet pussy. She shifted her weight onto her left side and moving her left leg bending it at the knee. I had no idea what I was doing which was obvious after a few seconds. She grabbed my head with her right hand and motioned me to her clit which I began to lick rhythmically. She began to moan loudly which I took as meaning I was doing a good job. Soon I realized that maybe I should change things up so I moved hand up making sure not to let my aunt notice. I brought two fingers up and slid them into her welcoming pussy and she almost immediately started to orgasm. Her breathing became frantic and her moaning louder as I slid my fingers in and out. The whole time she was screaming incomprehensible encouragements. Finally she came and her whole body began to convulse and her juice began to spill out of her. As she came down I laid back and watched her as she regained control of herself. She picked her head up from the mattress and smiled bigger than I had ever seen her before.

Now it was my turn as she scrambled up towards my waiting member. She slid my briefs off before I was even close to ready and stuffed my semi hard dick down her mouth and began to pump it systematically. I groaned and tilted my head back in ecstasy. She continued on staring at me with her big brown eyes the whole time. Soon I was close to cumming myself and she could feel it to as she slowed her pace. She released my dick completly and brought up her gigantic tits and began rubbing them against my hard dick. I tried to speak and urge her on but the combination of the sight of her soft tits gliding smoothly up and down my dick and the actual feeling of it left me speechless. Again she brought me so close to orgasm that precut covered her tits and my shaft completely, but again she let go of my dick and backed off.

This time she gave me a couple minutes to cool off before she straddled my crotch and moved my dick in to position. I watched anxiously as her wetness slowly dripped down the inside of her thighs. She watched me laughing as she knew how badly she was teasing me. Just before I was about to beg she led me into her chamber. Honestly I almost came right there but the surprise of it kept me from it. She felt around down there until my dick was just right and then she lowered herself all the way down as if she was just sitting on my lap. Then she brought both of my hands up to her boobs and made sure that I knew not to forget about them. Then she began to ride me. She broke eye contact and looked up to the ceiling closing her eyes actually. I stared right after not wanting to miss a second of it. I massage both boobs as wells as I could as my cock slid in and out of her up and down. Soon she changed the pace and rode me in a circular motion. I told her that I was gonna cum and she immediately quickened the pace back up and her butt and thighs began to make a slapping noise against my legs. I cried out in joy as I shot my seed inside her. She felt the warmness inside her and came down to kiss me never getting off. My dick was still hard so she rode on until she came again screaming and moaning all the while

She got off of me and took a few breaths until she knelt down with her ass to my face and told me it was time for a new position. I was already lubed up from her juices so I began to slowly slide my dick into her ass under her careful instructions. Once I was all the way in I began to quicken the pace. My legs and balls began to slap against her ass and I soon came again. Once we were down and covered in sweat she sucked me off one last time. She carefully and slowly pumped my cock into her mouth until the last ounce of my cum was in her mouth and subsequently swallowed.

She laid her head back for a while and then went and took a final shot of tequila. She walked over to my shower and washed the cum and sweat off of her as I watched voyeuristically. When she was done she once again donned her robe and strode off to her bed with her husband. She made sure to pick up all of her lingerie which was strewn throughout the room and brought our drinks back to the kitchen for cleaning. I sat back and fell asleep laying on my back feeling like the greatest man in the world.

•••

The next morning I woke up at 7:30 and walked without hurry into the kitchen for my morning coffee. I was the second to last to wake as my Aunt Kristen was still asleep. My mom and I joked about how wasted she was and she told the story of Kristen jumping on me which was all in good fun. About and hour later Kristen walked out exhaustedly holding her head up. She filled her mug and downed three Tylenol. She wasn't in a talking mood so later that afternoon I asked her to play cards out on the balcony. The whole time I tried to make small mentions of the previous night, but she said nothing. In fact, she couldn't remember a single thing. At the end of the game she asked why her lingerie was out and I told her I had no idea. Jokingly she said that she probably tried to wake up my uncle and he didn't stir so she handled it herself. I laughed and agreed thinking to myself if her forgetfulness was good or bad for me.

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