John--the typical 18 year old nobody, the oldest kid in the senior class, and therefore the oldest virgin, the guy more afraid of girls than of death itself--was crossing into new territory. He was staking out a girl's house.
Or, more accurately, he was stalking, though he couldn't be sure if it could be considered stalking yet if this was his first time doing it. And the target wasn't a girl. It was a 39 year old woman.
And technically, she might have indirectly invited him to do this...but that's a long story. He had Molly's address, and that was the important part.
Molly was a strikingly sexy mail carrier, and John lived on her route. One day she had caught him jerking off to a magazine through the front picture window, and she proceeded to smile and watch him through the dark sunglasses she always wore as he finished.
It marked a significant advancement for John's sex life, or lack thereof. His dick was big, but he lacked the confidence to get far enough with a girl to use this gift. His inexperience with all things sexual only made things worse—he was actually afraid to use his dick because he doubted his ability to use it. And if a guy with such a generous endowment couldn't be good in bed, than he was an even bigger loser than at first glance.
At least that's how John felt. And it was why he was comfortable enough—though barely enough—to jerk off in front of this stranger, this woman, this hot-blooded, big-breasted, wonderfully curvy older woman—because it wasn't going to go any further than that. But when she came back and let him do it again, this time showing him her glorious bare breasts and letting him shoot a load of sperm all over them, John fell hard.
It wasn't love, but lust. And it was quickly becoming an obsession. Years of release that came only from magazines, videos, and the internet via his own hand could do nothing to prepare him for the taste of real sex he was getting increasingly closer to. The normally mild-mannered student was going out of his mind and prepared to do things he never would have considered just two weeks ago.
Tonight was Halloween, and John had come to Molly's house, knowing he could brush his presence off as a coincidence because of the holiday festivities if Molly saw him. Molly had been purposely ambiguous about their unusual relationship, as she neither ended it, nor did she give an indication that it would continue. John was sure she liked having control of how things went, with her being the experienced, responsible adult and all. But when John got a hold of her address, the fuck if he was going to pass up the opportunity to use it.
He staked out the house, but he had no intention of going up to the front door where Molly was handing out candies to kids in costume. He had a much bolder plan. Silently, stealthily, with his sister's digital camera in tow, John snuck into Molly's back yard, identified her bedroom window, and waited.
The night was cold, but John had dressed too warm, and he actually fell asleep. He awoke with a surge of fear, but when he remembered Molly's back yard was protected and private with thick hedges lining the perimeter instead of a plain, chain-link fence, he calmed down. Besides, when he looked at his watch, it was well past the time for the Halloween festivities to have ended. The streets would be empty, and the porch lights would be off. Unless someone was actually back there with him, here, in the dark, he was invisible.
But it wasn't as dark as it used to be. A light came on in Molly's house—the bedroom light. John jumped to his feet and scrambled to the window. The Venetian blinds were down, but not drawn all the way. He could see inside as he got closer, and he discovered two astounding things: One, that Molly was married. Her husband was there with her, laying on the middle of the bed with his clothes on, his forearm over his eyes to shield them from the light. He looked like John's dad did after a long, hard day.
In his lack of experience on the dating scene, John never even thought to look for a wedding band on Molly's finger. He wondered if marriage was the only thing keeping Molly and him at a distance. Maybe she wanted him desperately, but breaking a vow was just a tad too much. John hoped it was true, and he got hard thinking about how she might so badly desire him. Maybe she even thought about him while performing the more physical duties of a wife. But the presence of the husband still frightened John. He nearly left.
It was the second thing he discovered that kept him on track. Molly had always been the mail carrier to John. She always wore a uniform, and while he'd been blessed with the sight of her huge, soft, natural breasts with their long nipples and defined tan lines just days ago, John had yet to see her eyes. But it was night, and Molly was wearing neither her uniform, nor her sunglasses. In fact, in just a pair of white bedtime short-shorts with red trim, knee-high white socks with two red stripes, and a white t-shirt, she was almost wearing nothing at all.
The sight of this beauty wearing so little was almost enough to kill John with over stimulation. She was standing at her closet, putting clothes away, and a generous portion of her perfectly aged ass peeked from under those short-shorts. Molly wore shorts often on her route, so John had seen her legs before, but now they looked longer, stronger, and smoother in the soft bedroom light. When she turned to pick up a new garment to hang or fold, John could see Molly's big breasts--so firm for someone of almost forty, but sagging enough to be undeniably real—stretching out the chest of the t-shirt so far that the bottom on the shirt hung away from and exposed her soft, only slightly swelled tummy.
He put the camera up to the window and turned it on. John stiffening at the whirring noise it made upon startup, but those through the window gave no indication of having heard it. The image of Molly standing there came into the viewfinder.
John almost pushed the button when Molly turned his way. It was a casual movement—he knew he wasn't caught—but the full-on sight her eyes, of which he'd never before seen, caught him off guard. Even looking through the viewfinder of the camera, John could tell Molly had the most beautiful brown eyes, with big, dark lashes, and a very subtle and very unexpected exotic quality to them. Those eyes made her look like a whole new person, and even sexier than before. She looked younger, and her face seemed to shine from the glow the eyes radiated. She wasn't just sexy—she was breathtaking.
She looked back to the closet, but John was still in a trance, and he stayed that way, just watching her, his eyes glazed over, until she moved away from the closet entirely and approached the bed. She was saying something to her husband, and he said something back, but the window itself was closed, and John could only guess what they were saying. He slowly, unconsciously lowered the camera and watched through the glass with his own eyes as Molly crawled onto the foot of the bed on all fours, exaggerating her movements, prowling like a big cat. She was talking the whole time, and it looked like she was drawing out her words.
Still on her hands and knees on the mattress, Molly arched her back, thrusting out her chest so her husband could better see down the neck of her t-shirt, and raising her scantily-covered ass. But the husband kept his arm over his eyes, talking back to Molly casually and as if not in the mood. John couldn't believe it. He was sporting a raging hard-on just watching this, but the dumb ass husband was actually ignoring her!!
Well, he wasn't ignoring her for long. Suddenly the bland expression on what John could see of Molly's husband's face turned into a grin, and the guy laughed, and Molly laughed with him as she bent down toward his crotch. The husband took his arm away from his face and looked down just in time to see Molly lower herself onto her elbows, freeing her hands to undo his belt and pants. To John's amazement, she peeled the material of his khakis away, revealing the fabric of his boxers shorts and a significant bulge beneath.
John could have felt hurt or jealous by this display, but all he wanted was to see more. He knew the very nature of he and Molly's relationship was so weakly supported that watching her with another guy might be the farthest he'd get. Of course, he was also about as horny as he'd ever been in his life. He dared to rub himself through his pants.
Before unleashing the beast that waited beneath her husband's underwear, Molly reached to a nightstand and grabbed an elastic band. She pulled back her long, blonde hair and tied it with the band, holding it in place so it would no longer interfere with what was about to happen. It also gave John an unencumbered view of her face.
