Megan’s Descent Pt. 04 by Aenigma
All characters in this story are 18+ This is a work of fantasy/fiction.
This part of the story moves from the Toys & Masturbation Category, into Erotic Couplings, as things have progressively intensified for our main character. I do hope you enjoy this installment. Please note, this story stretches reality a bit.
If this is your first glimpse of the story, I strongly recommend reading the first three parts.
Megan took the latte from Tim, the guy whom she’d developed a crush on. He worked at a quiet coffee shop close to campus and she’d been promising herself that either he’d ask her out, or she’d ask him. He seemed almost harmless, but he was cute with his dark shaggy hair, his thin build, and big, dark eyes. Their first interaction had made it clear he was attracted to Megan and then her girlfriend Ashley had confirmed as much when she explained that he had been sneaking looks at her when she wasn’t looking.
But all that had happened almost two weeks ago, and Megan was different now.
Ashley had been the one that had led her down this path, sharing a porno scene that featured a hugely hung guy fucking a woman with a dick so huge that both college girls could hardly believe would fit or feel good. Ashley had gone a step further and bought them dildos, identical, and large. While it embarrassed Megan, she had become infatuated with that porno scene, and she just had to discover if her body could accommodate such a huge penis.
Her experiment proved successful, and with a mix of pride, and the early tinglings of sluttiness, she had eventually become lovers with Ashley. They had purchased more dildos, and a harness that the girls would take turns wearing, and after numerous sessions, they’d learned to work those big dicks as well as any gifted male could have done, well, theoretically of course.
By now, Megan had gone from the shy rich girl that was interested only in satisfying her parent’s demands for excellent grades, to a very naughty woman who was having quite a lot of sex with her girlfriend Ashley. Ironically, Ashley had yet to take any of their dildos successfully anally, and that had been almost like an aphrodisiac for Megan, the shy young woman that, by both of their accounts had become the bigger slut of the two. Her body had become accustomed to any of their toys, while Ashley.. struggled.
She was back in the coffee shop to get laid.
It’s not that Ashley wasn’t making her cum, that was happening a lot. The two women had quite a few chats about that, what they liked, what they didn’t, what gave them mind-blowing orgasms, and what just got them off. Ashley had paid attention to any details, and she had become the best lover that Megan had ever experienced. Of course, Megan had only ever been with one guy, and the sex with him had been… Less than what she had expected it would be.
So here she was, giving Tim the coffee guy more than he could handle.
Megan’s dark hair framed her soft features and fell along either side of her face, on long curled strands, the majority of her hair was pulled into a ponytail that danced behind her as she spoke. Her makeup, compliments of Ashley bordered on slutty, but both women wanted to send that specific message. Her lips were first outlined and then filled in with a candy-apple gloss, and her eyelashes were long enough to border on scandalous.
Megan had never worn a push-up bra before today but had already made up her mind that she would be wearing them for the rest of her life after seeing the difference the garment made to her very average breasts. Her sequined blouse was cut low enough to give Tim an eyeful if only he’d suck it up, and have the balls to actually look. She wore dark jeans that could have been tighter but hugged her ass nicely and underneath the pink thong hidden between her ass cheeks, that ran along the base of the stainless steel buttplug that Megan found herself wearing more and more frequently now.
Ashley had begged her to buy some ridiculously high heels, but Megan explained that she had no idea how to walk in heels like that and also that she wanted Tim to fuck her, and not have a line of guys form up behind what would have passed for a Stripper walking to the coffee shop.
She was a college girl, not an escort, she’d explained.
“I haven’t seen you in a while,” Tim said, raising one of his brows.
“Oh, have you missed me?” Megan said with her own brow raised.
“You could say that.” he said smiling “Any of our delicious bakery today, my treat,” he said.
“Why haven’t you asked me out, Tim?” Megan asked, unapologetically.
Tim stammered and looked around at the almost empty coffee shop, and scrambled for something to say.
“My girlfriend said you were trying to sneak looks at me when I wasn’t looking, and this is the second time you’ve offered me something on the house. Unless you’re offering every woman that walks in here… I don’t understand.” Megan said and kept her gaze on Tim
“I guess I figured you had a guy.” he finally said.
“Come on, if you thought I had a guy, you wouldn’t be offering me free yummies.” Megan pressed on “I made myself look nice today, just for you.” she added.
“You’re beautiful,” Tim said, in a way that Megan processed as having a catch to it.
“You’ve been a perfect Gentleman, I wore this blouse to see if you’d be bold enough to look at my tits while I stood in front of you,” Megan said.
A weird mixture of feelings began to form in her head. Ashley had said that Tim was pretty, ‘too pretty’, and they had gone so far as to wonder if he was gay, but he was obviously shyly attracted to Megan. Ashley had told Megan that there was no way Tim had a big dick, they’d talked at length about that too, Ashley had explained that guys with big dicks are a lot cockier (see what I did there?) and that Tim seemed almost timid, therefore, he had a little dick.
Neither women were interested in little dicks after what they’d done to themselves with the large dildos that they’d acclimated their bodies to at this point. Megan fought off accepting that Tim had a little dick, but he definitely wasn’t acting like a guy that was chasing pussy would. She still thought he was hot but felt like her chances of finally getting a nice fat cock inside her were slipping by the minute.
“Can I take you out sometime?” he asked, steeling himself.
“Give me your phone,” Megan said, and held out her hand.
Tim pulled his phone out of his pocket, handed it to her and she called herself, then handed the phone back to him.
“When?” she asked.
“Any night you’d like, my schedule is kind of open,” he answered.
—
Ironically, they ended up at another coffee shop later that evening. Tim talked a little about himself but listened to her quite a bit more. He was a classic ‘good guy’ and Megan found herself attracted to him even more, in spite of him obviously not having the kind of confidence she had hoped for. What little Tim offered made it clear he hadn’t had as easy a life as Megan, yet there was something about him, and the more they talked, the more that Megan had re-convinced herself to have sex with him. Ashley had been right, Tim was pretty, there was no arguing that having spent as much time sitting across from him as she now had. Megan had dreamt of Tim once, he’d been fucking her with a bigger dick than she had ever expected he’d have at this point, but strangely, he’d been wearing lip gloss at the time.
When he spoke, Megan imagined his lips shining, and tasting like strawberries.
The thoughts conjured words that were made not too subtle references to sex. Megan just wanted to do it, to see what it would be like, and even if it would just be the one time, she’d have slept with another guy, and she couldn’t shake how sexy, in an almost feminine way Tim was. It almost felt like having sex with him, might be similar to having sex with Ashley, except Tim’s dick wouldn’t be detachable.
“Do you have to be back home early, for classes in the morning?” Tim asked, glancing at the clock on the wall of the coffee shop.
“Trying to get rid of me?” Megan answered.
“Hardly, this has been great,” he said with a smile.
“Be honest, why didn’t you ask me out before?” Megan pressed the question once again.
“I just guessed you’d say no,” he said with a shrug of his shoulders.
“So what if I had? Never been turned down by a girl before?” she asked.
“I have, it sucks but whatever, no, I just figured it would be weird, seeing you come in after you blew me off, you know?” he reasoned.
“What if you’d have asked, who knows we might be sleeping together by now,” Megan said with a grin and licked a bit of her upper lip with her tongue.
Tim stared, unable to find something to say in response.
“Don’t you wonder about that? I’ve been wondering,” she said, and realized, finally that at least when it came to sex, her confidence was far greater than Tim’s, and it might not have had anything with him having a small dick, maybe he was just generally introverted, it was clear he wasn’t going out much. She wondered about his lips again.
“Why torture myself?” he blurted out as if she must surely know that he realized he’d never get that far with her.
“Do you live far from here?” Megan asked.
“A block from the place I work, why?” he answered, and his eyes opened a bit more, not yet willing to let himself believe she meant what he hoped she meant.
“Do you live alone?” she continued on.
“I have a roommate, he goes to school here,” he answered and felt a knot rising up in his chest.
“Would it be awkward for you, if we went back to your place?” there, she’d asked. She felt surprised at how easily it had happened. More of Ashley’s influence, no doubt.
“Not awkward no, I keep thinking I’m about to wake up from a dream and be really pissed,” Tim said with a chuckle.
Megan felt that weird tickle and said “Why? We’re just going back there to hang out, maybe watch a movie or something.” she said innocently.
“That sounds great to me,” he said, and stood up, for the first time that night, he held out his hand and surprised Megan.
Was this shy pretty guy finally relaxing a bit? Was he finally gathering up his courage? She let him pull her to her feet, and she held onto his hand, smiling she asked.