Jessica

I don’t think it would be accurate to say that I was obsessed with Jessica. I think that “preoccupied” is probably a better description, though it was actually her breasts that had me preoccupied. She was very nice, not bad looking and pretty thin but her breasts were phenomenal. She knew it, too; you could tell by the way she dressed to accentuate them, but you could also tell she wasn’t stuck on herself. She seemed very down-to-earth.

We were both working at a big highway project office; she was an administrative assistant at one of the engineering companies and I was an engineer at another. We would run into each other now and again, though I certainly gawked at her more than she was aware of. I was able to successfully hold a conversation with her without dropping my eyes to her chest, though I won’t say it was easy. I just knew that in an office that big, there would be plenty of opportunity to stare at those babies without her knowing about it.

The preoccupation really started during a particularly good week of leering, due to the way she was dressed and the number of viewing opportunities that presented themselves to me. It got to where I was thinking about her tits all the time and I just needed to see more of them. You see, Jessica wore tight shirts, but nothing low-cut or very revealing. The more I thought about it, though, the more I knew I didn’t just want to see her cleavage or even see them in something like a bikini top or bra. I wanted to see them “in the flesh” so to speak. The question was: How?

It is at this point that you will probably think: “Dude, you were totally obsessed and you were totally stalking her!” I’m not going to argue that point because I know that is what it looks like. I will tell you that I didn’t have any fantasies about being with her, I didn’t have any desire to hurt or control her and I wasn’t thinking about anything more than seeing her tits. I wasn’t thinking about kissing her or having sex with her or even touching her tits. I just wanted to see them. What this led to is something that eerily resembles stalking: I went on the Internet, found out where she lived and went to recon her home.

She lived in an apartment over a music store. It was a curious looking building, but one that worked extremely well for my purposes. The apartment was on the second floor, but the second floor wasn’t as big as the first floor so there was a flat roof around three sides of it. Not only that, there was a fire escape on the back side of the building. Based on what I had learned, I formulated a plan that really was my only hope of ever seeing Jessica’s pendulous tits.

I knew what time Jessica generally left work, so I made sure I was at her place and up on the roof in plenty of time. It helped that it was dark out by the time I arrived and I was pleased to note that there weren’t any other buildings close enough for anyone to spot me sneaking around up there. This also meant that essentially the only way to see into Jessica’s windows was from directly outside them. I figured this probably increased the odds that she wouldn’t worry too much about closing her blinds.

I had time to look around a bit before she got there so I checked all of the windows first. There was a window looking into the living room that had a vertical blind that was open but not pulled to the side. The next window was smaller and looked into the kitchen. It had a gauzy drape covering part of it. The next window was even smaller with frosted glass, so I assumed it was the bathroom. I didn’t expect that Jessica would be showering after work, so I wasn’t put off by not being able to see into it.

The last window looked directly in over her bed. It had mini-blinds that were open but not pulled up. This was good because it would help hide me and I fully expected her to change out of her work clothes when she got home. Looking around it appeared the only way I could be spotted up there would be from the inside. I settled near the living room window since I could see that the front door came into that room.

It wasn’t long before Jessica arrived. I peered in cautiously as she entered, tossed her bag on a chair and hung up her coat. I followed as she went into the kitchen where she looked in the refrigerator, pulled something out and put it in the microwave. I watched for the bathroom light to come on after she left the kitchen, but it didn’t and the bedroom one did. I was already getting hard in anticipation, never considering that, though she might change her clothes, she might not necessarily remove her bra. It turned out it was a good thing I didn’t waste my time worrying about that.

On this particular day, she was wearing a long, maroon skirt made of velvet or velour and a skin-tight turtleneck shirt. She opened the closet and kicked her shoes into it, then reached behind her for the zipper to her skirt. Her back was to me at this point as her closet was at the foot of her bed. As she worked the tight skirt over her hips, her shirt covered her ass but I was able to see her long legs as the skirt hit the floor. Then she bent over to pick it up, treating me to a look at her ass and the black thong wedged between her cheeks.

She picked up the skirt and shook it out before turning to lay it on the end of her bed. She was now facing in my direction as she grasped the bottom of her shirt and began to pull it up. I was holding my breath in anticipation when she stopped. She let go of her shirt and reached up with both hands to undo the bun in her hair. She always wore her hair in a professional-looking bun and I was dying to see it cascading over her shoulders. Here was my chance as she shook her hair loose and it fell. Magnificent!

She began pulling her shirt up again, this time by the collar, giving me a nice view of her panties and flat stomach as it rose up. She leaned forward as she pulled it over her head, then whipped her hair back over her shoulders. This gave me my first view of her tits encased in a heavy duty, but still lacy and sexy, bra. I could only stare as she stood before me in bra and panties with her hair down over her shoulders. I pulled my cock out at this point without even daring to blink and began stroking it.

Jessica turned, giving me another great look at her ass, and partly closed her bedroom door, taking some clothes off a hook on the back of it. Setting the clothes on the end of the bed, she reached behind her back and the moment of truth came. Her bra suddenly went slack and she shrugged the straps off her shoulders. The cups slowly slid down to reveal more and more of the objects of my desire. Seeing how big her aureoles and nipples were brought me to the verge of cumming.

I couldn’t believe I was actually seeing them. The aureoles were easily three inches in diameter, her nipples were as big as the tip of my pinkie finger and both were light pink. She dropped the bra onto the bed and before she got her t-shirt on, I was squirting cum on the wall below her window. I continued to watch and stroke as the shirt covered her beauties and she stepped into a pair of sweatpants. When she killed the light and walked from the room, I tucked myself away and followed her.

I found her in the kitchen stirring her dinner on the counter, then pouring herself a drink. She took her food and drink to the living room where she settled on the couch to eat and watch TV. I watched her for a little while before deciding it was time to leave. I made my way back to my car and headed for home, but decided even before I got there that I wasn’t quite done yet. Yes, I know that doesn’t sound like someone who is not obsessed and is not a stalker. My thinking was this: I’d seen her tits and that had been my goal, but if I could permanently capture her tits then I wouldn’t have to rely on my memory. I was only going back to videotape her changing her clothes and that would be it.

Back home, I got my video camera all set up and tested it by shooting through a couple of my own windows to see how things would turn out. With a few adjustments, I was able to get a really nice, clear recording. Plus, I realized that I should probably put something around the outside of the lens to cushion it in case I accidentally tapped it against the window. I tested that, too, and determined that I was ready to go. I brought the camera to work the next day and visited Jessica’s roof again after work.

She followed pretty much the same routine as she came in so I didn’t start taping until she was in the bedroom. I had the camera resting in the corner of the window to steady it in case my hands got shaky. Watching on the view screen, I followed Jessica as she moved around the room before finally stopping in front of her closet. She was wearing slacks and a blouse that day, but once again started off by kicking her shoes into the closet. Her back was still to me as she unbuttoned and removed her blouse, but she turned to lay it on the bed and gave me a nice shot of her cleavage as she bent over.

My gaze was alternating back and forth between the view screen, to make sure she stayed in the shot, and the real thing. I could have used my dick as a tripod at this point, it was so stiff. Still facing me, she unfastened her pants and let them slide down her legs. She stepped out of them and bent over to pick them up, giving me another fantastic view of her cleavage. Even if she didn’t take off her bra this time, I still had some satisfactory footage. Again she went to the back of the bedroom door, revealing that her white panties were actually a white thong, and took the clothes hanging there over to the bed.

She set the clothes on the bed and just stood there for a minute, like she was deep in thought about something. This was fine with me as I just kept filming her standing there in her bra and panties. I figured I’d only have another minute or two before she was dressed again and hoped that I’d get to see her breasts again first. When her hands finally came up, I was surprised that they went to the front of her bra rather than the back. She cupped a breast in each hand and lightly massaged them.

At that point, I was just thinking that I was getting some great footage without giving any thought to where this might end up going. She reached behind her back and released her bra, quickly shaking it down her arms. I about hyperventilated as her breasts jiggled before she brought her hands back up to them and started massaging them again. She was running her hands back and forth over her hard nipples, her eyes now closed. I finally caught on to what was happening when she started tugging and pinching her nipples. I could not believe my luck.

I zoomed in enough to frame just her face and tits for a few seconds then back out to make sure I could see her panties as well. A few seconds later, her right hand slid down over her stomach onto the front of her panties where it began to slide up and down. It wasn’t long before that same hand ventured under the waistband and into her panties. Somehow I managed to keep the camera on her despite an overwhelming desire to whip out my cock. Her left hand alternated from one breast to the other, still playing with her nipples a little bit longer before moving down as well.

She pulled her right hand from her panties, yanked them to the side with her left, then went back to stroking herself. I got a quick view of her light brown bush before her hand covered it again. Finally, after a minute or two of this, she grasped both sides of her panties and yanked them down, giving me another quick shot of her bush before it was hidden behind her dangling tits as she bent forward. When she straightened back up, I got a nice long shot of her entire body as she climbed up onto the bed on her knees.

Her bush was a narrow, light-brown strip that was soon covered by her hands again. Her left hand went to the top of her pussy, apparently to stroke her clit, while her right appeared to be plunging a finger or two into her pussy. I don’t know how I stayed conscious through this because I know all of the blood in my body was in my groin. I thought my cock was going to explode out of my pants and blast a hole in her window.

Somehow I managed to keep taping as she played with her pussy, her arms pushing her tits together and up, creating the most incredible cleavage. She started to rock her hips up and down and the look on her face was pricelessly erotic. Her movements got more and more frenetic until she stopped and seemed to convulse a couple of times, her tits jiggling as she did. Finally, she relaxed again and flopped over on her side. I kept the camera running as she lay there naked, catching her breath, her chest heaving.

She rolled onto her back and lay that way for another minute before sitting up. She grabbed the t-shirt and pulled it on, then pulled on the sweatpants as well. The only thing I didn’t get a clear shot of before she was dressed was her bare ass, but I wasn’t complaining. I had a better videotape than I ever dreamed I would have. I finally shut the recorder off when she turned off the light and left the room.

I watched as she turned the microwave back on and got herself a drink, then carried her dinner to the living room and parked herself in front of the TV. I didn’t hang around, knowing that there wasn’t going to be anything better than what I had already captured on video. I climbed down the fire escape and got into my car, rewinding the tape as I drove home. Somehow I managed to get home without speeding or driving erratically and quickly connected the video camera to the back of the TV. Parking myself on the couch, I watched my masterpiece with my pants around my ankles. I was more than pleased with the results of my videotaping and more than satisfied by the time I was done viewing it.

I had seen what I’d set out to see and more and, consequently, had no reason to return to Jessica’s roof. I continued to gawk at her at work, but I now knew what the whole package looked like in the altogether, which made visualizing her naked even easier. I never shared the videotape with anyone, though I did make a few copies so I would never wear out the original. It has always remained my little secret.