Stuck with My Sister & No Clothes

"Hi, Doug had 2 bail on our long wkend in Maui due 2 biz and we're nonrfndable. Want to spend 3 days in Maui with me and catch up? XO" read the text. I remember it like it was yesterday, a Friday in July 2003 just before noon. My sister Lisa was probably already on her way. I'd never been, and it sounded intriguing. I could use a change, especially since I was just doing a bit of yardwork and housekeeping after graduating from college about a month before at our parents' place in Thousand Oaks. Soon I'd be starting a job in LA and I was bored, so a sendoff was timely. For laughs I looked at stand by opportunities and found some affordable flights -- unbelievable. It started seeming all so real, yet so surreal.

I have to explain -- growing up in Virginia with an older sister like Lisa was a real kick. She was fun, had a ton of friends, didn't condescend to me and most notably was absolutely gorgeous. What really stood out was her body if I may say so. A brunette about 5'4", she had beautiful cheekbones, a winning smile, and a ridiculous, traffic-stopping body, with great hips, a narrow waste and unnecessarily large and protuberant breasts.

When I was 11 and she 14, my hormones started kicking in and I realized that none of the girls around me could hold a candle to the forbidden and ripening fruit living down the hall from me. While I was relatively happy with my social life and was otherwise well adjusted, I did manage to harbor a pretty sick crush on my own sister! For the next four years before she took off for college I looked forward to the summer months so I could get into some proper perving. For some reason our parents installed air conditioners, then discouraged us from using them. The Virginia heat was oppressive and seemingly designed to have us shed as much clothing as we could. During these times she would wear gauzy nighties around the house in the evening and morning. She had a couple that were my favorites, white baby dolls that revealed slightly dark nipples gently waving back and forth as she walked to and from the kitchen. I could even barely make out her thatch below without getting caught, or so I told myself. Instant hardon! Sometimes she wore panties and a tattered UVA t shirt without a bra, which had a similarly stimulating effect on me. I just couldn't tear myself away from staring at her body, particularly when it was silhouetted against brighter light behind and the curves of her breasts were particularly evident.

After 8th grade I was keeping in shape caddying at a local course and knew I had a good body but hers was out of this world -- especially those breasts [I can't bring myself even now to call them tits -- they were too large and well formed for any but the best most luxurious word]. Because I was so entranced by her presence and more than a little bit disturbed by a growing exhibitionist streak I took to wearing as little as I could during the summer mornings and evenings as well. Typically old white briefs with or without a t shirt.

I remembered one hot afternoon in particular after ninth grade when I came home and looked out on our back patio. She was lying on her back in the 95 degree heat on the chaise lounge, sweating copiously in just a white bra and pink panties while taking in the sun. A dark spot about the size of a quarter had formed in the front of her panties. Was it because she knew I was staring at her from my bedroom, or just the inevitable result of too much heat? Probably the latter, but hey that didn't stop me from fantasizing. About a month later [I wanted to the next day, but didn't want to be too obvious] I did the same, laying out on the lounge in just my briefs when I heard the door bang announcing her return from work. I pretended to sleep but my penis was swollen, lying at a 45 degree angle and tucked up against the waistband. Then I heard the screen door to the patio bang and my heart practically jumped out of my chest as she walked closer. She merely shook me by the shoulder and recommended I get out of the hot sun, but I notice that she had to make an effort to avoid staring at my dick. What a sister!

I remembered many times watching TV dressed just so when she would return after midnight from one of her many dates. More than once she would repair to her room without having seen me, and then come downstairs in a nightie and join me in watching the rest of a movie. She was usually half lit and I am sure she noticed my boner tightening the briefs I wore, but she betrayed nothing more than a slight smirk and an occasional compliment for my flat stomach and strong shoulders. The best night of all was when we watched Wild Things together. I noticed she had her hand lying softly between her legs as she sprawled on the couch in her translucent nightie, and would occasionally glance over at me and my obvious erection. I did let her know I thought her body was better than Denise Richard's. Neither one of us dared to stroke ourselves in front of the other though.

After she departed for college my own dating life went reasonably well. I was very picky about whom I'd spend time with but while I was never alone too long, I never formed a serious commitment lasting more than a year. During that time the family decamped to California and I welcomed the change of scene.

Lisa had married two years after college an investment banker six years older than she was, and settled in San Francisco. He was a nice guy and seriously well compensated, but probably worked too hard. She worked, not nearly as hard, as a pharma rep -- or "drug dealer" as I kidded her. I am sure with her winning smile and other assets that doctors would pretty much do whatever she said, just to keep gawking at those boobs.

All this background was probably unnecessary, but provides an outline of where my thoughts might head at the notion of spending a weekend at a luxury villa overlooking the Pacific with my older sister who I hadn't seen in ages. Of course, she had no idea. Or maybe she had. I dunno.

I texted back "I'll do my damnedest to get there. Please text hotel number, thanks MUCH" and finished my yardwork. I didn't notice until almost too late that I really had to jam to make the first of the stand by options. I hurriedly stuffed some clothes and a swimsuit into a carry on and headed off to LAX. It was really hot and once I parked, I started sweating profusely running between the many terminals trying to make a flight. United no chance, American stiffed me and finally I boarded a Hawaiian flight about three hours before sundown. I was the last person to board, and they took possession of my luggage and checked it, on account of all the overhead space being full. Typical! All I had on me was my phone, keys and wallet. Hey, at least they didn't charge me.

I arrived several hours later but there was a problem -- somehow my luggage had been mislaid. I cursed myself for failing to put a nametag on the bag in my rush to leave and weighed my options. No shops were open and they promised to call me first thing when it could be found. Sure. So I took a short taxi ride to the hotel. It was gorgeous, with landscaped grounds, a beautiful open reception area with outdoor restaurants next to a large pool with palm trees and a series of villas on either side with views of the crashing surf. The villas appeared to be in the Hawaiian design but with clever plantings and bamboo fencing that separated each. The "butler" asked why I had no luggage and sympathized with my dilemma. He would be sure to follow up the next morning. He also let me know Mrs. -- was waiting in Suite 211, which featured a king bed and a private pool.

I must have looked a sorry sight as we approached the villa. I was haggard and dressed in a sweaty t shirt, shorts, and running shoes. Nonetheless on our knock my sister burst through the door and gave me a nice hug, crushing those breasts against my lower chest.

"It's so good to see you, and you look absolutely great," she lied.

"Thanks for having me over here, it's amazing, and you're amazing too!" I replied.

When she stepped back I saw that I had not been overstating the case. She DID look amazing, at the same weight and body shape that I remembered so well from her senior year in high school. She was dressed in a yellow sundress with a halter top and it was evident she was wearing no bra, about which I expressed no complaints. Her hair was tied in a loose bun and some strands fell around her face, making her look extra cute.

"So tell me, what happened?" I asked.

"Doug called me this morning just after I had boarded that he was stuck in Phoenix for the weekend. Something about closing a financing and a celebration dinner. I'm not mad, after all his work and not mine pays for stuff like this but it's kind of a bummer. I tried a couple girlfriends but they were all tied up even though they'd kill to come here.

"But first things first, you look like you need to relax. Was getting here hard? And where's your bag?"

I told her my story and she laughed it off, putting me at ease. "Well, first take a shower and we'll catch up over room service and a beer, what do you think?"

Nothing could have sounded better. I noted the layout of the place, with a raised platform on which stood a huge bed at the back of the room. It was fronted by a living area featuring stuffed chairs and a couch with a TV on one side and a dining table on the other. To the side of the bed was a stylish and large bathroom featuring a whirlpool about twice the normal size of a tub, and both indoor and outdoor showers. Cool art and craftwork littered the place. Tropical flowers were planted along the sides of the villa and along the sides of the deck out front, in which a small infinity pool about 12 feet square lay. Steps led down to a concrete pathway about 10 feet below, affording guests absolute privacy unless an 11 foot ogre were to trundle by. Magnificent!

My sister consulted the menu and reached for the phone. I closed the door to the shower and shed my stinking clothes. These were not fit for human wear until cleaned, and only barely so after that. I took a cool shower and took extra time soaping my genitals, which responded to my own touch as I reminisced. Afterwards I donned the bathrobe hanging from the closet and went out to find a nice pasta and salad for the two of us, and a bottle of white wine. We spent an hour leisurely catching up and polishing off the bottle. I was hypnotized by her gaze and felt myself getting a bit sleepy.

There was a soft tone announcing someone at the door. We both looked puzzled for a moment and then she laughed.

"I had forgotten I ordered up a massage for Doug and I. Given how everything's been nonrefundable so far, I guess I better not try to cancel this either!" she said.

In strode two demure but attractive young women of Asian Pacific provenance in golf shirts and shorts. The slightly larger one told us that the couples massage was done either on the bed or on the massage tables they had left outside depending on the customers' choice.

"Well I don't want to make this any more work than it already is," she said, adding "why not take care of us on the bed. We're sorry it's so late."

"Oh, it's our, and we hope your, pleasure, ma'am. We hope and your husband enjoy your stay with us."

We looked at each other and laughed again. This sounded like a lot of fun. I noted that my sister failed to correct the masseuse, but said nothing [of course].

"We leave how you want to be massaged up to you. You can be draped or undraped, and can tell us where you want the work done."

"That sounds great," Lisa replied, adding "we think you should just do what you planned to do and what seems right. You're the experts, right? Would that be OK?"

"OK, then I think you should each wrap one of these towels around you and lie on your front on the bed about three feet apart. That way we have room to work. We are going to use very light oils so your bed will remain clean and fresh. We'll move the towel so that your modesty is protected if you want, but we find that many customers prefer to leave that on the mainland." With that we both laughed again, but I was choking inside at the thought of getting a massage right next to my sister from maidens who thought nothing of their customers' nudity!

First the masseuses turned down all the lights except the small bedside lights. My eyes enjoyed the low light and my sister held one of the soft towels to her chest with one hand and pulled the bow on her halter. The dress fell away and I glimpsed a good portion of her right breast as she readjusted the towel. Then she reached up underneath and pulled down a pair of white satin panties, kicking them to the side. This was too much. I held the towel in front of me, wrapped it around my waist under the robe, and made it fast. Then I shucked the robe and climbed on the left side of the bed. My sister followed suit, and the girls started to work by standing next to the bed. First they put a bit of fragrant oil on their hands. I noted approvingly that they weren't simply slopping it all over the place. They were real pros.

The massage started with the upper back, which was very sore due to the outdoor work I had been doing that week. The gal used her elbows and forearms in long sweeping strokes up and down my back to work out the knots. To get extra leverage, she climbed on to the bed and straddled by butt. I was in heaven. I sometimes heard soft sighs from my sister from the ministrations of the other masseuse, who I saw had moved the towel down over her butt and was working on her lower back.

Then my masseuse gently tugged at the towel and I lifted my pelvis in response. I didn't know exactly what to expect but I was sure it would be great. She took the towel and laid on my right cheek and leg, leaving the left exposed. The masseuse then started with my foot and worked her way up my calf and then my thigh. I was getting pretty aroused by her strokes on the inside of my thigh, but my hardened cock was safely tucked upward towards my waist. Then to my surprise she worked her hands into my cheek, pulling it to the side, down and up. This was seriously erotic! Her fingers drifted dangerously close to my most private spot. Then she pushed aside the towel, and poured maybe two drops of oil into my crack and pushed each cheek to the side, making me feel extra vulnerable. I could feel the oil dripping down to my balls.

I had been keeping my eyes closed so as not to disturb my sister but I managed to peek once or twice. She was lying in a similar position with her large breast bulging out -- I could tell because her arms, like mine were at a 90 degree angle from her shoulder. Interestingly, I saw that her breast had a light sheen of oil, so her masseuse had definitely stroked it. If only my hands were permitted this liberty!

Then the masseuse took the towel and placed it on my left cheek and leg, so that my right side, facing my sister, was totally exposed. My heart was like a triphammer at first, and I dared to peek at her. She was facing away, but her towel was on her outside leg as well, meaning I had a full view of her amazing body from shoulder to toe! She had tanlines right where you'd like them, across her bra line and hips. The rest of her skin was a nice even tan.

After about ten more minutes working the right side I was seriously relaxed, and at the same time unbelievably aroused. The masseuse gently tapped my left shoulder and I lifted my head towards her. She made a twirling motion so I slowly rotated my left hip over my right while she held the towel up, to protect whatever few shreds of my modesty remained, I guess.

I moved a little closer to the side of the bed so she could stand on the floor and she laid the towel over my knees up to just below my belly button. Then I sneaked a peek at my sister, and saw that she too was being advised to turn over. Her masseuse, with no insight that we were not married, did not take pains to hide her from me and I caught a good glimpse of her shapely breasts and puffy dark pink nipples before the towel was laid upon them. Wow.

Here the masseuses changed up tactics. Mine worked on my upper body for what seemed like ten minutes or so, while Lisa's dealt with each of her uncovered legs in turn. It became more interesting as she picked up each of her knees and gently stretched the limbs, making her towel ride up and expose her hip. Still her thatch was hidden and I dared not peek too hard or too long and risk upsetting this incredible night.

As my masseuse manipulated by stomach muscles, my penis got harder and harder. Luckily my erection tends to stick up rather than out so it was pointed toward my belly button and not the ceiling fan, so it wasn't too embarrassing. For the most part I kept my eyes closed, and let them work silently.

Now I could hear the masseuses changing position, with mine repositioning the towel on my stomach and groin and hers putting it on her groin and legs. Naturally this meant her breasts were entirely uncovered! I couldn't resist but to open my eyes for a moment as if I was awaking, and found her looking right back at my eyes, hers twinkling mischievously! Her breasts, white as snow, were heaving with her breathing and her nipples were clearly erect. Her stomach lay flat and tanned on the bed. I tried to maintain my composure by closing them again but I think my dick kind of jumped right off my stomach under the towel. Did she notice?

Properly chastened I kept my eyes closed and let my mind wander. Wander it did into strange but familiar territory, yet the massage was so good I was in no hurry. Soon the masseuse folded the towel upward, so my thighs were totally exposed. She pushed my legs slightly apart and my foot lodged up against my sister's. She made no attempt to move it away so neither did I. Now the masseuse started on my calf, and made lateral strokes across the leg, alternating with vertical strokes. The towel sort of covered my dick, but I think it was about to come off. Then she mounted the bed and I understood why she moved my legs apart. She knelt between my spread legs and worked the insides and tops of my thighs. Soon only a corner of the towel covered my penis. I couldn't even tell whether my balls were hidden from view. What I could sense was that my cock was weeping precum, as my helmet could feel the slimy mess in which it lay.

As the masseuse's hands rubbed ever closer to my balls, she lightened her touch. I could feel my dick throb up off its sticky resting place and lift an inch or two. As both hands were on my thighs, another slowly pulled the towel away to the left, leaving me entirely naked, right in front of my sister! This I couldn't believe, and yet I kept my eyes closed. Who had moved the towel? The masseuse ran her fingers very lightly back and forth over my balls and in response I could feel them retract into my body, usually the prelude to a massive orgasm. I could tell my cock was pointed straight at my face, and was so hard it wasn't touching my belly. Then the masseuse pressed both hands into my stomach on either side of my cock, stroked upward toward my chest, and then got off the bed. She and her partner were finished. I could hear them both withdraw and the door click shut.

I lay with my eyes closed, feeling incredibly exposed as I knew my sister was right next to me. I turned my head slowly toward her and opened my eyes. She was facing me in a reclined position, looking at my face and also at my cock. The towel was lying loosely across her hips, leaving her breasts uncovered and exposed to my hungry stare. Both had obviously been rubbed well as they had the sheen of the oil. They were so large that they were touching each other. Her beautiful nipples were taut, and I imagine they had been worked well.