Helicopter Love: Mom Spies on Son's Sexy Chats (closed for sierrahughes)

[BarryCKretive]

Jeremy was nervous. He’d had a hard time fitting in since he’d started college a few months ago. His social anxiety made it difficult to find new friends. As a result, he spent most of his time holed up in his dorm room studying and frequenting online adult chat rooms. It was almost ridiculous that he had resorted to such a thing given how many young, attractive, and available women seemed to constantly surround him on campus and in class. If only he had the guts to strike up a conversation with any of them.

Jeremy's appearance wasn't the issue. Standing just over 6'1" tall, a bit gangly, with mousy brown hair and deep green eyes. He caught smiles from the occasional pretty girl when crisscrossing campus. He was just so sheepish he kept right on walking in hasty retreat rather than stopping to strike up a conversation.

And so here he sat on a Friday night in front of his laptop, anxious and fidgety. He'd met Maureen online shortly after the semester had started. He saw her profile in a romance chat room and summoned up the courage to type out a simple "hello" in PM.

They'd hit it off from there. Maureen was a few years younger than his mother and every bit the "cougar" he'd hoped to find. Jeremy couldn't admit it to himself at first, but he'd slowly come to realize that his "ideal" woman had a lot of traits in common with his own mother: older, strong, formal, refined, intelligent, buxom, and uncompromising in her high standards for everything. As tough as she had been on him growing up, Jeremy's mother had also taught him what a real woman could be and he found himself drawn to the same archetype as he began to discover his own sexuality.

Maureen fit the mold nicely. She was a single woman in her early forties, successful in her career, and extremely strong-willed. She claimed that she used chat as a diversion from her otherwise busy professional life and didn't have time for dating and relationships. It seemed a bit of a convenient excuse given how much time they spent chatting, but Jeremy certainly didn't mind being the focus of her attention.

And now if she would just sign on. It had been over two days since they last chatted which was unusual for them...

 

[sierrahughes]

Maureen. 42.

Well. Those were the only two things about her that were fake in the chat room. Even the profile picture was real. She had been careful to present a photo only she and her husband would have seen.

As she logged on, she saw what had become almost a daily comfort to her - jeremy96 was already in the chatroom.

"hello"

Came the customary greeting from jeremy96.

hello back

Was the reply from Maureen.

There was a pause. Then she continued.

how was your day? it's friday and you did mention wanting to take a girl out...Abby right? how did that go?

...

Earlier in the day, she had been through a tough board meeting. Letting people go was always difficult and she wished the directors wouldn't do this on a Friday. But then again, there's no good time to do so.

She ran the research and consulting team, and was the only revenue-generating cost centre in the company. So, technically, her team should have been safe. But she found out, ten minutes into the meeting, that a few of her fellow directors had been conspiring to force a cut from her team this time.

She barely managed to fend them off, surprisingly, with support from Michael. He was a hotshot director from the sales team who consistently has brought in the most revenue for the company over the last eleven quarters. So when he threw his weight behind her, the rest backed off. For now.

But she knew there was always a price for everything. Michael asked her out for dinner that very same night. She knew what he had in mind, or at least would try to achieve. She managed to excuse herself this time round, though to some degree of annoyance from Michael.

"Next Friday," she had promised.

...

The reply was coming in soon...

 

[BarryCKretive]

Ah yes... Abby. Vibrant, friendly, outgoing, porcelain skin, long curly red hair... and imaginary.

Well, he'd seen a pretty girl on campus who looked like that. She seemed vibrant. She looked like an Abby - not that Jeremy could summon the courage to introduce himself and ask.

Jeremy fidgeted about how to respond. He really liked Maureen and didn't want to lie to her, but he'd already done so with "Abby". It had started innocently enough. Maureen tended to mother him a bit, needling him for details about his young bachelor college life. Not wanting to appear a total introvert, he'd concocted a blossoming relationship with "Abby."

He knew the more he carried on the charade, the more obvious it would become that he was making things up. Besides, there's plenty of reasonable explanations as to why things didn't work out.

jeremy96: Not so well unfortunately...

 

[sierrahughes]

what happened?

She was about to hit 'enter' when she decided to delete it. Maybe he didn't want her to probe. Or did he?

she probably didn't deserve you...

...was the next response, which she promptly deleted as well. It was truly what she felt. From what she knew about him, he was a sweet boy who would probably treat his lady well. It was her loss. But it sounded way too creepy.

it happens.

She hit the 'enter' key, and stared at it momentarily. What was she thinking?!

i mean...i have an idea...why don't you tell me what sort of girl trouble you've been having and i can give you practical advice?

That was rather more spontaneous, but she smiled to herself, excited about the idea of him opening up to her.

 

[BarryCKretive]

Now he'd done it. His "girl trouble" was that he was afraid of girls; not exactly something he was eager to share. Jeremy didn't want to continue lying to Maureen and if there was anyone he could confide in about his fears of talking to women it was her. After all, she was a woman and she already liked him so what was there to be afraid of?

Jeremy96: Well... The real problem is that I haven't asked her out yet. I don't even think she knows who I am.

Jeremy96: ...

Jeremy96: So yeah... I'm a bit shy when it comes to talking to women. I wanted to sound like a typical college guy who dates women and stuff but...

Jeremy96: I guess I'm still trying to figure it all out. That's part of the reason I came on here... So I can get comfortable talking with women. I don't even know how to introduce myself or what to talk about...

Jeremy sat there and stared at his computer. It was out in the open now. He was a socially awkward virginal dweeb. What would Maureen think of him now? The seconds ticked by at a snail's pace as he watched her prompt for a reply.

Nothing... Jeremy started to worry he'd sabotaged the only female relationship he had going.

Jeremy96: You there?

 

[sierrahughes]

Well this was a pleasant surprise! She had heard about how people were generally a lot more open online, as if the screen of anonymity provided a shield to their actual selves. And she was about a decade too old to have been part of the generation used to going into chatrooms via IRC, ICQ etc.

But she also knew she had to reply fast, and to be really sensitive. Otherwise there was a good chance he would withdraw into his shell, and she would lose her only chance to reach out to him.

Maureen: you do know that's perfectly normal, right?

Maureen: let me share a story with you not many people know about...my husband was a real geek in high school, but when he finally gathered enough courage to talk to a girl, he chose to talk to me...

Maureen: it didn't matter that I was head cheerleader in high school and one of the most popular girls in high school, or that the first encounter with him was really awkward...

Maureen: i remember finding it really cute and sincere, and well...the rest is history...

She didn't continue, because it made her cognisant that he was also no longer around. She had lost him to a really silly car accident almost ten years ago. Since then, she had put all her energy into her career. She thrived, but in the process, she may have lost the connection to her family, and more broadly, socially. She hadn't dated since the day she saw the coffin laid to rest. She couldn't.

 

[BarryCKretive]

Jeremy stated at the screen. He was comforted by Maureen's words. It was silly to be so self conscious with her. There was probably a lot he could learn from her.

Head cheerleader? He liked the sound of that. At least, he liked the thought of head cheerleaders who found geeks to be sexy. He tried to imagine Maureen in a cheerleader outfit. Her profile picture certainly suggested the type of physique that could've been a cheerleader's back in the day.

Maureen had a sexy body and more importantly, seemed very relaxed and comfortable in her own skin. Though she had a similar body type to his mother's, he could tell Maureen was way less conservative and buttoned up. He liked that about her.

Jeremy96: Thanks for that.

Jeremy96: I know it'll work out for me eventually. It's nice to have someone to talk to about these things.

Maybe it was the rubber band effect of the boost of confidence she had given him, but suddenly Jeremy felt more flirtatious than shy.

Jeremy96: Head cheerleader who likes geeks eh? Well I'm a pretty big geek. Think I could ever make it with a hot cheerleader like you?

 

[sierrahughes]

Maureen: haha...

To be honest, she was a little lost for words. She didn't know what to expect after opening up to him like that - she wasn't expecting anything. But for him to come back so quickly, and sort of make a pass at her like this, she didn't quite know how to respond.

But she quickly remembered that any awkwardness may make him withdraw, and she typed the first thing that came to mind.

Maureen: so...you think cheerleaders are hot?

Maureen: and the big geeks i know have big...

She paused, as a completely different word popped into her mind at that very moment. She found herself blushing, and then just as quickly chastising herself for even thinking of that. With him!

Maureen: ...brains. smart boys really...

She was already typing faster than she was thinking. And she could barely stop herself again this time. Twice in as many moments!

Maureen: ...impress me...

Maureen: what do you like about cheerleaders anyway?

She tried to change the subject this time, giving herself a little bit of breathing space. Phew!

 

[BarryCKretive]

Jeremy smiled.

Now it looked like Maureen's responses were coming in a stream of consciousness. Jeremy wondered if he had her a bit flustered. Clearly she hadn't expected him to flirt with her, or was he just bad at it? Either way, she seemed to be playing along or at least humoring him.

What now?

He liked Maureen. Jeremy also felt a strong attraction to her,or at least to his idealized vision of her. All he had to go on was her partially dressed profile picture. He didn't even know what she looked like since her face was obscured in the image.

Yet he knew she was a beautiful, successful, and competent woman who could teach him much in the ways of romance and lovemaking. Her soft spot for geeks explained why she might take interest in a college kid like him.

Maybe she liked him in more than a motherly way or maybe she was simply trying to build his confidence. Either way, she seemed to be inviting him go continue. He thought for a moment and then began typing away.

Jeremy96: Well personally, I don't really have a thing for cheerleaders since they're way out of my league, but I think they're pretty and I enjoy watching their routines.

Jeremy96: But I like the idea of you as a hot cheerleader with a thing for geeks like me.

Jeremy96: I know I'm a little young for you, but I think I could impress you with my size...

Jeremy paused just long enough for Maureen read what he had written so far before quickly continuing

Jeremy96: Brain size I mean...