The Baby Sitter
I know - how cliché! Judging by the adult erotica out there you would think that every babysitter took the job intending to get caught doing something naughty and have sex. It is a common enough fantasy, apparently. I certainly understand the desire for a man to come home and find a sexy and very young woman waiting for him, or perhaps surprised by him. Still, the prevalence of this vignette is astounding and I hesitate to go there, but I am trying to tell these tales as accurately as possible. And so, with the full expectation that I will not be believed, I begin my story.
In high school I lived next to a woman with a younger son, Jeremy. Jeremy was perhaps 8 years old when I was a senior and was a good kid, but he had very few playmates his age in the neighborhood so I wound up entertaining him a fair amount. His mother, Karen, was a petite woman in her late 30's with most of the beauty of her youth still intact. I never did know what she did for a living, but she drove a nice car and kept her expensive home very attractive. She was unmarried and occasionally required the services of a sitter for an evening while she went out. That job usually fell to me.
Babysitting for Jeremy was always fun. We played with his toys, and as an only child of a well off mother he was always buried in cool new toys and video games. It was hard to get him to go to bed on time, but I usually bargained with him for an extra half hour if he promised to go right to bed at 10:30. That usually did the trick since he was tired by then anyway.
He slept like a log, and I was left to fend for myself for a while. Sometimes Karen was early, sometimes late, so I was always afraid to get into anything for fear that she might come home early. I was a nosy brat and wanted desperately to go through the house looking for cool things. Ever since I found a stash of porn at a friend's house when I was 12 I was hooked on searching through adult possessions. A bad habit, I know. Sue me.
One night Karen needed me in a hurry. She had received some last minute invitation to some function or girls night out - I never did ask about her plans. The timing annoyed me. Normally I don't care about last minute things, and I didn't have any serious plans normally, but that night was different. My own parents were out of the house visiting with some friends and I, thinking I would have several hours to myself, had rented a porno. I had planned to curl up with a box of tissues and the remote and do what comes natural to a horny teenager.
I even had the box in my hand when the doorbell rang. I quickly stashed it under a seat cushion and answered the door. There was Karen, dolled up in a short black dress with her short feathery hair looking very fetching, and asking for a "huge, huge favor," as she put it. I agreed to sit for Jeremy and told her I just needed to close up the house first and I would be there in a minute. She left and I put the tape back in my room, annoyed that I would likely be unable to watch it at all now. My parents are light sleepers and always knew when I was staying up late watching the TV, so I couldn't get away with it if they were home. I thought I might go get it later and watch it at Karen's house if the opportunity presented itself, but that seemed risky.
I fed the cats, locked up the house and went next door just as Karen was jumping in her Acura, Jeremy standing in the doorway waving goodbye to her and hello to me. Karen thanked me again and took off.
Jeremy was tired that night. Apparently they had gone to a pool, either the public pool or perhaps they belonged to a club, but he was exhausted. I made him some dinner - always macaroni and cheese and a hot dog - and we watched a little TV until he fell asleep on the couch very early. I picked him up and put him to bed with no trouble. He didn't twitch an eyelid as I carried him upstairs and tucked him in.
As I left his room I noticed another bedroom still had a light on. I explored around the corner and saw the master bedroom door open and the light on. Excitement jumped in me at the chance. It was early, just after 8:30 and Karen said she would be late. The light was already on so I wouldn't have to explain anything if I was caught having turned on the light myself, and Jeremy was in deep slumber. This was my chance.
I went downstairs and turned off the TV so I could hear better in case she drove up, then crept quietly back up the stairs. Jeremy was still fast asleep and I pulled his door almost shut. I went into Karen's bedroom and stood in the door, examining the situation.
It was a large room with a king size bed on the far wall and dressers on the wall to the left. A bathroom door stood on the same wall as the entry door, and sliding closet doors took up much of the remaining wall. A window looked out into the night next to the bed in the corner, with the curtains pulled shut. The room was well kept and neat, so I had to be sure not to disturb anything. I had become an accomplished sneak and learned to survey first and make sure you returned everything the way you found it. As this room was so well kept that would be a problem. The carpet had not been swept in a while so my footprints wouldn't be noticed, especially since this was a "shoes off at the door" kind of house.
I decided to look under the bed first as that was the easiest place to see. I went in and knelt down by the bed and lifted up the bed skirt. Nothing. It was completely clean under there. I saw this as a bad sign. People who kept such clean living spaces usually had clean minds, I figured, or at least were careful enough not to leave anything naughty or incriminating laying around. I was nervous at the though of doing any serious digging, but I figured I had the time. Plus it was exciting!
The nightstand turned out to be a bust, with nothing but some trashy romance novels and women's products like makeup, lotion, tissues, etc. I packed it all back in just as it had been before and wondered about my next snoop. The dresser was a good option, but it gave the highest probability of being seen from outside and I wasn't that desperate yet. The closet was the next best option, but the bathroom was the most secure. Still feeling nervous and exposed I decided on the bathroom, though I didn't expect to find anything there.
Sure enough, the small bathroom was full of makeup, hair care products, skin care, nail care, etc. All the things a woman seems to think she needs to be beautiful. Karen was very good at keeping herself beautiful and I was surprised she had all this stuff in here. You could tell she wore a little makeup, but she never looked cheap or overdone. Her hair was always perfect and her eyes were always slightly highlighted with eyeliner, but otherwise it was hard to detect much makeup. She just glowed naturally, I thought.
One interesting thing I saw was a pair of underwear hanging out of the clothes hamper. I'm not a fetishist for dirty underwear, but I was grasping at straws here. I pulled them out and examined them briefly. They were black and skimpy with a narrow thong up the back. They were also very sexy. Perfect, I thought. She at least knows that she is still hot. I gained a little hope.
I replaced the thong and went back into the bedroom where I stood quietly for a minute, listening for danger signs. Nothing. I could hear Jeremy breathing deeply from the other room and nothing from the dark street. The closet beckoned.
I slid the leftmost closet door open and peered in. Long dresses and coats hung from the bar, a shelf of sweaters and boxes above. I moved the long garments aside looking for something else on the floor, but found only shoes. I wasn't prepared to dismantle the carefully perched boxes yet, so I tried the other side of the closet.
This side held the shorter clothes, and below on the floor were more shoes and several boxes. These would be easier to rifle through with minimal disturbance. I examined the scene carefully, then dug in.
Boxes and boxes of shoes, some with the tags still on them, greeted me on my guilty search. A few boxes held other clothing accessories, one held papers that looked official and important, but nothing exciting. I was staring to despair.
Along the side of the closet were a few shelves, recessed back into the wall. More boxes and folded clothes sat here, but on the bottom shelf, behind the shoeboxes, was a different kind of box. A photo box, dark brown and tied with a brown cord, sat like a prize in the dark corner. Karen kept her pictures in regular albums displayed in the living room, so these must be something else. I carefully retrieved it and sat down on the floor, back to the wall, as I prepared to further invade the woman's privacy.
I opened the box and was greeted with a messy pile of photos and letters. I carefully examined each piece and turned it over in the box lid, careful to keep them in order. Many of the pictures were of her ex-husband and were completely common; vacation pictures, family portraits, etc. The letters I ignored unless they had a picture in them, and almost none did.
As I turned over picture after picture I again despaired, as there was nothing even vaguely erotic in here. I had originally been looking for porno, but was now reduced to hoping for shots of a vacation at the beach so I could see Karen in a swimsuit. Again, no such luck.
At the bottom of the pile was a thick manila half-envelope, sealed with a rubber band. I had lost hope and just checked it to be thorough. I removed the rubber band and carefully opened the envelope and was greeted with a small stack of Polaroid shots, and suddenly the evening took a strong turn for the better.
The first was a picture of Karen on a bed, on her knees and wearing a very skimpy see-through nightgown, hands on hips and a lurid, sexy smile on her lovely face. She was younger in this picture, perhaps as much as 10 years, and she looked spectacular. She was a slender woman with small breasts, but they stood high and tight in this picture. My dick nearly sprang to attention in the excitement of this find.
The next picture was in the same room, but less of an outfit. She had removed the negligee and wore only black panties as she lay sideways across the bed, posing for the shot. Still that wonderful mischievous smile graced her red lips and.
The next few pictures were of the same place, but different poses. One, which caught my attention painfully, was of Karen, now completely naked, standing in the middle of the bed and beckoning the photographer to her. It was as if she were looking straight at me, her arm outstretched and inviting me into her fantasy. I was fully erect now and was rubbing myself through my jeans.
The next few pictures were a different place, and started out on the beach with Karen in a bikini. It was either a nude beach or a secluded place, because the top quickly came off and again she was posing for the camera. A few sexy pics later and the venue changed again.
Another room, another sexy lingerie outfit, this time red, but this time she wasn't alone. The first picture had her holding hands with the photographer, and judging by the next picture he was pulling her forward. It showed her kneeling in front of the picture taker with his dick in her mouth!
I damn near messed myself at the sight of lovely Karen with a face full of dick, the wicked grin in full force on her face. Jackpot! It was a little blurry and you couldn't see her very well, but it was obvious. That was my neighbor giving head and it was the hottest thing I had ever seen.
The next few were just as hot and I couldn't contain myself. I unzipped my pants and took out my dick and started jacking off like a wild man. I threw caution to the wind and let my fantasies run wild. In my mind I was the photographer and Karen was going down on me. I kept picking up different pictures and lusting after the images in them. One had her bent over with the photographer's dick inside her from behind. I longed for that to be me and leaned into my masturbation with a will.
"Don't hurt yourself, honey," said Karen from the doorway, arms crossed under her breasts and leaning on the frame.
I jumped right out of my skin. I was busted in every way. I was too stunned to even get up. I just sat there dumbstruck with my face locked in a horrified expression. For a moment I didn't even have the presence of mind to put my dick away, I just sat there holding it like an idiot.
Karen stood there, obviously having been watching me, with a disapproving look on her face. I saw her eyes move over the scene, and when I noticed her looking at my penis I was released from my paralysis and managed to pull up my pants enough to cover myself. Adrenaline flooded me, but it was useless. I could neither flee nor fight and I would just have to take my punishment on this one.
I stood up and zipped up my pants. I stood there trying to curl up and die and waited for her to say something. I figured I needed to start spewing apologies and explanations, but I was still too dumbstruck.
"Do you like going through my personal things?" she asked, her voice low but cold.
