The Weekend with the Babysitter – Part 1

When you are a young teenage boy it gets really hard sometimes to think straight. Certain things you know are wrong become too tempting, and you stop being rational about right and wrong. Such was the dilemma I now faced. I was currently sleeping on one of two couches over at my babysitter Janet’s house. The couches faced each other with a small coffee table in between them. Sleeping on the other couch was one of my best friends, Sarah. We were both 18 years of age and had both developed into our prime sexually speaking. We had not seen each other in three years, but our parents were throwing a party that night so our old babysitter, who was now a senior in college, was having us stay over at her house.

I was well learned in the arts of sex, at least from a practical viewpoint, but had only had my first real kiss a couple of weeks earlier with a summer fling. I understood the basics, and even some secondary options, but had never had a chance to put my knowledge into action. My hormones were raging, and sleeping the same house as Sarah and Janet had started to mess with my mind. What really kicked it off was a TV show we had watched earlier: the show was some b-level story about a guy who could draw tattoos on women and then bring them to life as they slept. Needless to say, that show put some really interesting ideas in my head about what was possible.

We had stayed up until around 11PM and then everybody had turned in for the night. It wasn’t until I got up later that night to use the restroom that I began to think with my other head. As I walked back from the bathroom to the couch I paused and watched Sarah as she slept. In the three years we had not seen each other she had really began to develop into a beautiful girl. She was sleeping on the couch, partially on her right side, with her right leg dangling onto the floor and her left leg bent at the knee but leaning against the back of the couch. She had only worn a loose t-shirt and some loose short shorts to bed that night, and I stared at her exposed leg. I felt my dick begin to get hard, but immediately freaked out when the tip started making its way out of my boxers. I quickly moved my dick so that it would extend vertically through the waist of my boxers, instead of the front slit.

I moved to my couch quickly and quietly so as not to wake Sarah, but the boiling blood in my system refused to cool off. As I lay there on my couch, on top of the blanket, my eyes began to wander again over Sarah’s body. I slowly let my eyes creep up from the sole of her right foot to her calf, then her knee, then her thigh, and then to where her shorts hid the rest. I guess she had decided it was too hot to get under her blanket as I suddenly noticed in the dark that she was sleeping on top of it. My eyes were slowly drawn to her developing breasts. Not knowing how cup sizes worked at the time I didn’t know that she was currently a well-endowed C cup, but that didn’t matter to my brain at the moment. Because she had twisted in her sleep at some point in the night her loose shirt had been bunched up underneath her and was now pulled tight across her chest.

I watched as her covered breasts slowly rose and fell in time with her breathing. At the peak of their rise their outline became even more defined as the shirt was stretched to accommodate Sarah’s bust. Even with what little light there was in the room it was easy to make out the slight bulging outline where her bra covered her breasts. At this point I noticed that I had moved off of the couch and was leaning over the coffee table, craning my neck to get a closer look at her bosom. As my blood began to boil more and more I licked my lips to wet them, and slowly began to shuffle around the coffee table to be closer to Sarah.

When my knees touched the base of the couch she was sleeping on I suddenly became aware of how close I was to her. As I continued to think about what I was doing I began to notice the faint smell of her perfume as it wafted into my nostrils. I closed my eyes and groaned as my lust continued to build. When I opened my eyes I knew what my body wanted to do, even if my mind was still screaming at me not to act on those thoughts. But the time had come and gone for the logical part of my brain to steer me away from what was about to happen. Instead, my other head started to use my brain power to evaluate the situation and determine what the next step should be.

I slowly raised my right arm up over Sarah’s stomach and let it hover directly above her shirt covered abs. Ever so slowly I lowered it until it made contact with her stomach as she took in a deep breath. I let this contact continue four or five more times before once again slowly lowering my open hand onto her stomach. I closed my eyes and focused all of my attention on my senses of touch and smell. I could feel the warmth of her body through the shirt, I could smell the fruity perfume, and I could hear her unlabored breathing. I opened my eyes and with the smallest of movements began to run my hand in a circular motion across her stomach, occasionally let a finger dip into the slight dent in her shirt caused by her belly button. I began to feel her body heat rise and this led me to slightly increase my tempo.

Not satisfied with just her stomach I slowly increased the radius of my rubbing so that the edges of my fingers began to come into contact with her bra, still under her shirt. Inch by inch I rubbed more and more of my hand against her bra and against the base of her breasts. Suddenly she snores real loud, takes a deep breath and goes right on sleeping. Like an elephant running from a mouse I had already bounded back onto my couch before she had settled down, trying my best to seem asleep in case she woke up.

After about ten minutes of watching her closely to see if she was awake, I became confident enough to kneel down next to her again. Worrying that my time for exploration may run out at any minute I become bolder. I realize that feeling a breast through a shirt is all well and good but nothing replaces real skin. I examine how her shirt has bunched up underneath her and slowly begin to worm my fingers under her hip to pull it out. The shirts comes free with little effort and now I am really glad that she wore such a large shirt. With great trepidation I slowly inch the front of her shirt upwards, rolling it as I go.

Inch by delicate inch her stomach is revealed, then the shirt is high enough that I can start to make out her bra. I take measured breaths and extra care to make sure that the shirt movement doesn’t wake her. When enough of the front of the shirt is rolled up to fully expose her breasts I gingerly place the rolled up part just beneath her chin. Once I am sure that it will stay there I allow myself to fully appreciate how nice her breasts really are.

Now, an expert in women’s clothing I am not, but I notice that her bra is one that secures in the front with a little plastic clasp. Scared that fiddling with it may wake her up I decide to run my fingertips across the exposed flesh of her breasts. I run the tips of my fingers up and down both breasts. I then move my fingers to where her nipples would be if the bra was off and start to slowly feel out exactly where they are located. To my surprise they have started to harden and they are easily found.

I run my pointer fingers in small circles around her nipples and I am soon able to see an outline of them through the front of the bra. At this moment I also notice that her breathing has increased its pace just slightly. I slowly lean over her right breast and ever so softly flick her fabric covered nipple with my tongue for a minute before switching to her other breast. My mind is racing a million miles an hour at this point and a loud voice in my head keeps urging me to do more.

Giving into that voice I focus my attention onto the clasp that is holding her bra closed. It seems like a simple enough clasp, just push the plastic spot in the middle to release and then push the plastic tab back in place to close it. It won’t be easy to close her bra in a hurry, but like I said before, my brain wasn’t really thinking logically. I lean back on my knees, take a deep breath and then slowly raise my right hand to the clasp. I move my pointer finger behind the clasp and use my thumb to slowly apply pressure until I hear a click and then the clasp pops open.