The Chaperone

Let me tell you what a chaperone is according to literature.

“The modern rule is that every woman should be her own chaperone.”
-Amy Vanderbilt

“Master of the house
Quick to catch your eye
Never wants a passer-by
To pass him by.
Servant to the poor
Butler to the great
Comforter, philosopher
And lifelong mate!
Everybody’s boon companion
Everybody’s chaperone”
-from Les Misérables

Now let me tell you what I learned a chaperone should really be like; how my sister brought me to a deeper understanding of this important principle of family love.

It happened on a weekend almost a month after my first taste of my sister’s sweet nectar. I was living with my grandparents, who had raised me, working for the summer in preparation for going to college. My sister was on her summer break from college and staying with our father and stepmother on their ranch. At least every other weekend we would visit and I would stay the weekend. Little did I know my sister had plans for us to spend as much time as possible out of the sight of parental displeasure.

When we got to the ranch, my sister was dressed in her cleanest cowboy clothes, pressed jeans, boots, and a frilly blouse. She was supposed to go to a dance contest that night but her date had cancelled. Her idea was to take me instead. She said I could be her chaperone. Our stepmother said it was okay if I, the nerd, didn’t mind. But she said that if we got back after 11:00pm, we’d have to sleep in the camper because the door would be locked.

My poor sister; they would not trust her with a key to the house. I’d had a key to my grandparent’s house since I was in the sixth grade. I told them I was okay with tagging along after my sister so she could go dance. But I was in my ‘at-home’ ragged jeans, sneakers, and a plain white t-shirt. My sister said that it was okay and she had a shirt from school that a guy had given her.

So off we went to go dancing. I tried to tell my sister that I wasn’t a very good dancer. She pulled into an empty parking lot, stopped the car and grabbed my face, where she planted a kiss on my mouth. It wasn’t the type of kiss you’d expect a sister to give her brother. Her tongue seemed determined to replace my own as she pushed it into my mouth and sucked my tongue into her mouth.

When she let go, she told me that I seemed to be able to dance just fine as far as she was concerned.

I was taken back by this turn of events and wondered what she really had in mind for the evening.

The next surprise my sister had for me was our destination. I expected us to go to a cowboy bar for a dance contest. Instead, we pulled into an apartment complex. It was a small building; the type of place where the pool is in the center with all the doors facing the courtyard. We got out, my sister carrying a gym bag, and went to an apartment on the second floor.

A thin blond greeted us at the door and once inside, she kissed my sister like my sister had kissed me. I was a little embarrassed, not just by the sight of them working their mouths against each other and getting glimpses of their tongues, but also by my feelings of jealousy that someone else was kissing my sister.

When they were through bathing each other’s mouth, my sister introduced me, but she didn’t mention that I was her brother. Her friend took my hand and kissed me on the cheek. She was pretty, and she acted as though what she had done was normal. I wondered if she would be more enthusiastic the next time we met.

Then she grabbed her purse and told us she would see us at the party as she went out the door. I looked at my sister, not sure what plans she really had for the night. She grabbed my hand and pulled me after her to a bedroom. Once there she started to explain what was really going on while she unbuttoned her blouse.

I didn’t really hear anything my sister said as her blouse opened and I was treated to a look at her luscious body. She continued to talk as she unhooked her bra and slipped it off her shoulders, revealing her pert breasts with their conical nipples.

Drawn like an iron rod to a magnet, I walked over and cupped her breasts. That quieted her speech. She placed her hand on my face and I looked in her eyes as she drew me to her mouth. We kissed, but for how long I could not tell you. I only know that when we broke the kiss, we were sitting down on the bed and I still held her breasts in my hands.

She pulled my shirt up and I had to let go as she lifted it off my body. But this time when we kissed it was in an embrace and I could feel her hard nipples pushing against my chest. We fell over as she pushed me onto my back and straddled my legs.

She worked my belt and pants open and then pulled them down my legs as she slipped off the edge of the bed. With two quick yanks she had my sneakers across the room followed just as quickly by my socks. Now I was only wearing briefs that did nothing to hide my desire for her.

Dancing, almost, she wriggled her own pants down her lovely legs, stepping out of them once they were on the floor. I stood back up facing her, each of us in just our underpants. We reached for each other at the same time and laughed at our eagerness.

She surprised me though when she reached into my briefs and took me in her hand. She slipped through my arms and slid down my body, pulling my underwear down with her free hand.

When I felt her warm, wet mouth engulf me I gasped at the pleasure it sent through my body. She made loud slurping sounds with each bob of her head away from me. She cradled my balls with her hand as I looked down through the haze that misted over my eyes. I saw her cheeks draw in as she sucked. Her lips went all the way to the base of my shaft and she swallowed. All this together was my undoing. Before I could warn her I erupted down her throat. My legs lost their feeling from my hips down and I was afraid I was going to collapse on top of her.

Instead, she pushed me back onto the bed again and stood up wriggling out of her panties as she went. My eyes widened at her new look – she had shaven all her pubic hair away except for a small patch trimmed in the shape of a heart. She asked me if I liked it. I told her to get closer and I’d let her know.

My sister told me to crawl up the bed to the top. I always do whatever my sister asks. She followed me; her beautiful naked body had my rapt attention as she crawled over me and positioned her neatly trimmed pussy close to my face. She had cut her pubic hair into a perfectly shaped heart whose point rested the width of two fingers above the hood of her clit. I could see the damp line where her lips met.

I tilted my head and took a deep breath; she’d used vanilla scented cologne that mixed perfectly with her own natural musk. Gently, I pressed my mouth to her and sucked in her right lip. This got a gasp from her as I slid my tongue along the outside. She tasted clean and tart. As I went back the other direction, my upper lip picked-up the moisture she was generating.

When I did the same to her other side, with my tongue in between her lips, I got a whispered yes from her. Now the whole outside of my mouth was damp from her first juices. I took another deep breath. I could smell her on myself and knew I would be able to dream of her fragrance and her flavor for days to come. She asked me not to stop.

Being a quick learner, I continued to taste her, running my mouth and tongue back and forth along the length of her slit and bumping into her emerging clit. Each time I ran into her little nub, she let me know that I was doing exactly what she wanted. Not wanting to ignore any part of her anatomy that needed attention, I started to suck on her little sensitive button with each bump. Her lips deepened in color as they swelled from the pressure and friction I was applying. They seemed to purse in readiness as I lavished them with kisses and licks. The smack of my lips against hers and the wet tendrils that broke across my mouth made my raging hard-on ache for her.

When I decided to concentrate on her hard little clit and scrub it with my tongue, her legs began to shake.

I grasped her butt with both hands, holding her upright and against my mouth so I could continue to enjoy her oozing nectar. My face was getting slick with her juices and I reveled in the responses I was invoking with my attention. I let my hands wander over her body as far as I could reach, from the tips of her toes to her butt and around the front to her nipples, which were hard as little rocks. She held onto each side of my head, trying to keep her balance.

As I continued my ministrations, her inner lips began to blossom and I eagerly sucked on them as well. I found her tight entrance and tried to push my tongue inside, but I made little progress. So I ran my tongue from her little hole to her clit pressing as deeply as I could, my nose plowing the path ahead. Each time I tried to stick my tongue into her she pushed against me as though she was helping. I didn’t want her to miss out on any sensations, so I substituted my middle finger and felt her bounce against my palm with a strangled yelp.

Now she took over the rhythm and grunted as she pushed harder and faster on my finger. All I could do with my mouth was stick my tongue out and flick her clit as she went by. It seemed to be helping because her voice was getting louder with each bounce.

Finally I grabbed her clit in my mouth and pressed down with my lips, then held on as best as I could, lashing her with my tongue and holding her butt hard against me. By now she was yelling yes so loud I was sure that people in the neighboring apartments would hear her and think someone was being hurt. But I held on, I would not let go until she told me to, not until she was satisfied.

Suddenly she stopped moving and I let her swollen clit pop out of my mouth as I looked up at her. I didn’t expect her to smack me in the face with her pussy, but she did, almost hard enough to knock me over. I let go of her in surprise and she fell over backwards, her butt on my chest and bounced several times before going limp. Considering the force that she banged into me with, I was worried that she might be hurt.

I wriggled into a sitting position so I could see her face. She was smiling. Somehow she pushed herself further down the bed, straightening her legs on the way.

She hopped up and grabbed my hand, telling me we had to get washed up and go if we were going to the party. We stumbled into the shower and my sister handed a bar of soap to me. Without any hesitation, I started to rub it all over her. She looked over her shoulder at me in surprise as I reached her breast, then smiled.

We were supposed to hurry with washing so we could go to a party. But rubbing soap all over my sister’s naked body was making us both think the party could wait.

Even though we had just given each other orgasmic delights, her nipples were betraying her continuing desire. She ran her hands over mine as I massaged her breasts and then reached behind her to grab my stiff manhood. I followed her to her butt with the soap, making sure I covered every bit of both sides and the valley that ran between. Her touch was light and teasing, but it was getting me too close to enjoy her body as long as I wanted. I took her hands in mine and moved them back around to her pussy.

Working slowly, I transferred the bar of soap to her hands and then pushed them up and down the open flower of her lips. She tilted her head back and we kissed, moving our tongues in time to the movement of our hands. Pushing back against me, my sister moved her hips up and down, my shaft sliding in the valley between her cheeks. Water pelted over my back and ran down her chest, twin waterfalls leaping over her nipples.

The soap slipped out of her hand and hit the floor with a crash, but we continued our slow dance of lust. Our fingers intertwined and moved between her folds, touching and caressing her most sensitive flesh.

Her legs began to shake and she pulled my hands away.

She told me to stoop down just a little, which of course, I did, eager to find out what new pleasure she had in mind.

Reaching between her legs, she took hold of me and pushed back against my stomach. Then she told me I could stand up again. I was only able to get about half way back to upright position. But the feeling was exquisite.

Her open pussy rested against my shaft and she played with the head using just her fingertips. It was delightful torture. I had to grab her hips to maintain my posture.

As I started to pull back a little, she took most of my length in her grip and started her own movement. She used her soapy slit to scrub my cock and her hands to toy with my balls and shaft.

When she tightened her grip on me I let out a yell of my own, erupting in her hand and pushing her against the wall as I fell forward.

My knees did not want to keep working and I did not want to keep pressing my sister into the shower wall. I slid down to the floor as she laughed. She took a washcloth to clean her hands and then rinsed herself quickly.

Mercy was evidently not on the menu for the night as I was pulled from the shower and told to get dressed. I was weak, but I still would do anything my sister asked. My sister pulled out a slinky black dress and slipped it over her head. It had spaghetti straps and only came down just past her butt. I couldn’t get dressed as fast and had to carry my shoes to the car.

I wondered what was so important about the party. I was looking forward to after the party – figuring that should be enough time for us to recharge our bodies.

My sister drove me to a party in a ritzy neighborhood. I grew up in what I had thought was a big house with my own bedroom and a room where I raised tropical fish. But this place made my home look small. Their huge driveway was filled with cars parked three wide. We still had to park at the curb behind a line of other cars and were still in front of their property.

At the door, a short blond with a pageboy hairstyle met us. She was wearing a little blue shift and no shoes. My sister’s greeting was similar to the one she had given her apartment-lending friend. When she introduced me, I was surprised by the same kind of kiss. We were told we had to take our shoes and socks off, and the guys had to take their shirt off as well. I thought I might enjoy the party after all.

Inside there was a large living room filled with a crowd of people. As we were told, no one had shoes on, dancers or sitters, and none of the guys were wearing shirts. What made me stop and stare was that there were also a number of girls without shirts. Most of them seemed to be dancing, their bare breasts swaying and jiggling while they laughed and talked. There were a few girls sitting on guys laps kissing and fondling. Two girls were necking with each other also.

I’d never even imagined a scene like this. My sister had to pull on me to get my legs in motion.

We ended up in the kitchen. I was completely oblivious to anyone my sister might have been introduced me to on the way. Once there though, I was introduced to a girl with long black hair wearing only a matching black thong. I’m sure my sister told me, but I have no idea what her name was. She had the darkest nipples, almost a charcoal grey, and the most perfect all-over tan.

She stepped up to me, took my face in her hands and kissed me, pushing her tongue into my mouth. Without a doubt, I must have turned beet red. She broke away laughing and I looked at my sister for an explanation. My sister just stood there tittering with a couple of beers in her hands. The other girl took one and my sister offered me the other. I shook my head; one of us would need to be sober later when we drove home. There was no need to get me drunk to take advantage of me.

Two other guys came into the kitchen butt naked and talked the pretty girl into going back outside with them. My sister grabbed my hand and we followed them.

Outside there was a pool and a huge motel sized hot tub. There were maybe four or five people around the pool. The trio we followed headed for the bubbling waters of the hot tub. The guys slipped down into the water first and the girl slipped out of her thong. When she turned to get into the tub between them I saw her pussy. It was hairless but still the same color as her nipples. There seemed to be a whole world of new sights opening up to me.

My sister slipped out of her dress, tossing it aside and told me to hurry. I was stunned. Everyone around me was naked, including my sister. I fumbled, getting out of my pants and underpants, afraid that if I took too long one of those guys would try to reach out and grab her and I’d have to hurt them. I nearly jumped into the tub next to the one girl I wasn’t prepared to share.

I needn’t have worried. As soon as my butt hit the seat, my sister slid onto my lap and pulled my hands to her breasts. The three across from us offered boisterous encouragements as my sister reached between our legs and groped around for my cock.

Sitting naked in a hot tub with three other people and my sister sitting on my lap was the last thing I expected to be doing on a Friday night. The smell of beer and chlorine was buffered only by the sweet vanilla fragrance that was all my beautiful sibling was wearing.

Angling her butt against my stomach, she reached for my hard-on, pushing her breasts into my hands. I could feel her nipples between my fingers as I tried to help her keep her balance.

She finally grasped my manhood and stopped wriggling. As soon as she did, she reached a hand back to my head and turned her mouth to mine. I know the others could see our tongues as we tried to match our lips and failed. That did not stop us from trying. Between her tongue flicking across my lips and her hand playing with the tip of my cock, I was in a watery heaven.

When we stopped trying to kiss, I looked across the tub. The girl was succeeding where we had failed. Her mouth was pressed tightly to one guy, their jaws working, while the other was licking a breast. His pink tongue stood out against her dark nipple and his hand was below the bubbling water. Both of her hands were under water too, and by the look of the reactions, she was stroking both of the guys to their immense satisfaction.

This was better than a porn movie. My sister casually played with me as I caressed her breasts and we watched the show being put on in front of us.

The kisser started to stand, pulling the girl up with him until she was sitting on the edge of the tub. The other guy moved with them as she continued to stroke his hard cock. But as she lay back, she pulled him to her mouth and ran her tongue around his swollen head.

The first guy had to break their kiss as she’d lain down, so he slipped down her body, transferring his kissing skills right where she wanted him, between her legs. In moments she had him locked to her pussy, legs crossed behind his head.

The second guy positioned himself with one leg still in the tub and moved her head so it was dangling over the edge. She continued to suck on his cock with him pumping in and out of her mouth. She must have been torturing him because the way he had his face screwed tight he must have been feeling simultaneous pleasure and pain.

The first guy came up for air and reached over and smacked the other guy on the leg. Like it had been rehearsed many times, they swapped positions so fast, they deprived the girl of their stimulation for no more than a second or two. The only difference was the guy at her pussy was pushing his cock into her. For her part, she synchronized her own leg and mouth movement like the act was well practiced.

The guys pulled her off the edge of the tub and into the water. Her legs locked around one and her arms locked around the other, and their hands holding onto her, she floated between their two poles. They were so close to us now; we could reach out and touch them, which is exactly what my sister did.