She saw Jake in the high school hallway between classes and followed him from a distance, masked by the many other students around them. She always followed him when she could. Jake was usually surrounded by the other socially popular kids, the girls because he was just “too cute”, and the guys because the girls were there. Eileen was not a part of their group. She was the wallflower type, pretty but shy. She would love to talk to Jake, but there was never an opening for her among Jake's entourage. And it was that way all through high school. She rebuffed any other boy who asked her out; she only wanted Jake, and she loved him from afar.

And boy did she love him. She couldn't talk to him at school, and she couldn't call him because she didn't know what to say, even if she had managed to get his cell number, which she hadn't. So she fantasized about being with him. She wrote him notes and letters that he never saw, in which she proclaimed her undying love and willingness to do anything for him. She went to his house after dark and secretly peeked from behind a bush into his bedroom window, watching him walk around or get undressed and ready for bed.

She pretended to be with him every night, hugging her pillow, which she named Jake, and massaging her pussy while pretending he was doing it, working herself to a frenzy as she quietly called out his name. She was totally obsessed with Jake. And for every day at high school, watching for him and following him, she forced herself to believe that one day she'd have him!

After high school, she made sure to be in the same place that Jake was, which ended up being a small town with an expensive private college. He enrolled there, so she moved to the town and found a job at the UPS store. She knew that this time she'd have a chance to see him and date him since he wouldn't have the “cool kids” entourage with him all the time. She would brave up and meet him ... somehow ... and then use sex to snare him for herself. And he'd fall head over heels in love with her, just as she loved him.

Since this was a small town, it was easy to get around on foot, and most everyone walked where they were going. The first time she saw him walking, she followed him and found out that he lived in an apartment in a newer building, but since it was not on the first floor she could not peek through the windows to watch him as she did back home. But every evening she would hang about near his place to watch for Jake, to see if he came out that evening. He usually did, and she would follow him to see the places he went. She was waiting for her chance, hoping to stage a chance meeting on the street.

Eileen got her chance to meet him most unexpectedly one day, when by pure luck he came into the coffee shop where she was having a coffee and a donut. She felt she could not let this opportunity pass, so she worked up the courage to walk to where he was sitting.

“Jake, that is you! I'm Eileen, and we both went to the same high school,” she said.

“Oh yes. I remember seeing you around, Eileen. How are you?”

Jake did remember her, and looking at her now, he saw a pretty girl who he recalled might be a little shy. He hadn't met any girls he liked yet and thought maybe she would be worth a date to see if her ideas on sex might line up with his.

“I'm good. How about you? But how did you end up here?” she asked

“Oh, my parents wanted me to go to this school, so here I am. I guess as long as they're footing the bill, I may as well enjoy it.”

“Are you staying in the dorms?”

“Nah, my folks coughed up the money for an apartment over on Third Street. It's nicer than the dorms. I could show it to you some time.”

“That'd be great,” Eileen exclaimed, maybe a little too enthusiastically. “Say, would you know a good place to eat? Not too expensive. I work at the UPS store and I'm kind of on a budget,” she added.

“Hmmm, well, there is the pub. Oh, and Peter's. It's pretty good and not too expensive. Maybe I could take you there sometime,” he offered. Then he gave her his cell number. “Give me a call when you're free for dinner some night.”

His coffee-to-go was ready and he left. But Eileen had his phone number and an invitation to go out! She was floating above the ground, and her nether region was getting wet just thinking about being with him!

She called Jake later that day, but he said he was busy that evening. She called him again the following day, but he said he was busy again. She convinced herself that she didn't seem too desperate, and called him again on the third day. But Jake was beginning to see a desperate girl who would pester him until he took her out, and that told him that even if she weren't sexually attuned to his kinky side, he would probably be able to persuade her. So he agreed to dinner that evening.

He met her at her apartment, not nearly as nice as his, but that didn't matter. They ate at Peter's and he picked up the tab since he had asked her out, and because his parents were paying for everything while he was at college, including his charge card. After dinner, he invited her to his apartment, which Eileen found was much larger and nicer than hers.

“So, this is my place. Can I get you some beer or wine?” Jake asked.

“Oh, maybe some wine, white if you have it. You have a nice apartment,” she answered.

Eileen was over her head with happiness. Here she was, alone with the guy she'd wanted all through high school! It couldn't get any better.

“Let's sit on the sofa and have our drinks,” he said.

They got settled, sipped their drinks, and talked. Jake heard that Eileen told her parents she was coming to this town to see a friend, and liking it, decided to stay, getting the job at UPS. He told her he wasn't excited about college here, or anywhere, but his parents insisted, and since they were going to pay for everything, he went along. They chatted away, enjoying each other's company, and before long Jake moved closer to her and placed his hand on her leg. She was thrilled!

Pretty soon he leaned in and she was in heaven when he kissed her. She kissed him back, though she wasn't too sure she did it right. But he seemed to like it and kissed her more passionately, and she began to get into it, kissing him back with gusto. Encouraged, Jake slid his hand further up her leg to the hem of her skirt, then slipped a finger under the hem. She noticed his hand and thought she might not have to throw herself at him to get the “snare him with sex” plan in motion. She kissed him more passionately.

Jake decided to play it slow, so he continued to kiss, then took his hand away from her skirt and rested it on her breast, caressing her lightly. She liked the way it felt and wanted more, so she encouraged Jake by kissing him back intensely. Jake continued to fondle her breast, then unbuttoned the top two buttons of her blouse. Eileen wondered what his plan was, and expected it to be pretty great.

Before long, she was helping him take her blouse off. She was getting very turned on, and enjoying all of his attention. She took her bra off to give him full access to her breasts, and he was taking advantage, massaging them with both hands and caressing her nipples, which were now as hard as erasers.

Jake was now pretty sure he could maneuver this girl into bed and decided to try. He put a hand back on her leg, slid it under her skirt and slowly inched it upward as he continued to fondle her breasts with his other hand, watching for her reaction. She simply kissed him with more passion. He slid his hand further and was almost to her panties. She sighed with arousal, and loved that the man she'd desired for years was about to have his way with her.

She wanted to encourage him, so she said, laughing, “I like where you're going with this, you naughty man. I should probably stop you, but I'd rather you continue where you're headed!”

He paused for a moment to say “As pretty as you are, I'd never forgive myself if I didn't at least try.”

They were still kissing when he reached her panties. She could feel his fingers caress over her pussy, with only a bit of thin cloth between them. She began to wiggle a little from the arousal she was feeling.

Being no rookie, he knew when she was past the point of no return. He pressed his fingers against her pussy lips through her panties, and traced her slit from bottom to top, where he pressed slightly against her clitoris. She moaned out loud from the excitement she was feeling, and moved to give him easier access. He had her lift her hips off the sofa and she quickly helped so he could pull her panties off.

With more room and Eileen's cooperation, Jake was hitting his rhythm in diddling her. Up and down her slit he continued, and with the odd finger slipped into her, and she was going crazy with excitement. Soon she was beyond any fantasies she'd imagined with Jake; this was so much better! The moment of truth was now here.

“Shall we go to the bedroom?” he asked.

“Yes, please,” she gasped.

So they went to Jake's room and both undressed. He got a condom from his dresser and put it on before they got on the sheets, and she was surprised when he positioned her on her hands and knees.

“Go ahead and rest on your elbows, put your head down, and spread your legs a bit,” he asked of her, and she quickly did as he asked.

Jake knelt behind her, and she was able to see him by looking between her legs. He brought his penis up to her snatch, patted her a few times with it, to her wild excitement, and then slowly pressed into her. He grabbed her rear to keep her from falling, then pumped in and out. She screamed in ecstasy at the wonderful feel of his dick inside her, despite it being a little painful with this being her first time, though she'd never tell him that. They pushed against each other for their mutual satisfaction until Jake came, jerking and spewing his essence into her. She felt the warmth of his semen, and almost had an orgasm; only her lack of experience kept it from happening.

After their sex, Jake kissed her and said he'd walk her home. They both got dressed and left.

“You were great, Eileen! I loved your energy,” he said as they walked.

“Thank you! You were pretty great too!” she exclaimed.

“One thing, though. I noticed you have a lot of pubic hair. You're too pretty a girl to have all that hair. Do you think you could shave that off before we go out again?”

“You want me to shave my pubic hair?”

“Yes, please. Do it for me,” he asked.

“Okay, I will,” she said.

When they got to her apartment, he kissed her and left after she went in.

Eileen was thrilled at the way the evening went. She loved the sex she had with the man she'd loved for years from afar, and couldn't wait to become even closer to him.

<< To Be Continued >>