Chapter 1 - The First "Date"

Becky waited nervously in her single dorm room. Typically as a freshman girl she’d be required to share a room with someone, but her new college was renovating the primary freshman dorm, so many students were shifted to older senior dorms that were all singles. Not that she was complaining though, she liked the privacy.

Her boyfriend, or at least that’s how she thought of him would be arriving in a few minutes to pick her up for their first proper date. Sure, it was weird to call someone her boyfriend and to have their first date after their first sexual experience together, but that’s where Becky found herself.

She was an average girl in almost every way. Always quiet in high school, on the nerdy side as well. She wasn’t drop dead gorgeous or anything but she had a definite cuteness about her. In anticipation of seeing Trip again, Becky had spent much of the summer exercising, trying to lose the few little spots of babyfat that had persisted on her slender body. She sat on her bed in khakis and a t-shirt, waiting for her prince to come.

Becky almost launched herself into the air when the knock on her door came. She looked over at her wall and her clock said exactly six. “At least he’s punctual,” she said quietly to herself as she opened the door with a big smile on her face.

It was indeed trip standing before her, his chiseled body dressed in what was clearly a tailored suit. Becky had to make a mental note not to drool as she saw him, but suddenly felt severely underdressed. She looked down a little and noticed he had a garment box in his arms. She just kind of moved out of the way, letting him in without truly being able to speak.

“Just as I thought,” he said to her finally. “Cute and all, but let’s fancy you up a little bit.” He held out the box for her. “Wear everything in here and nothing else, got it?”

“Hi,” she finally managed to squeak out as she kept staring at him. When he handed her the box and listened to the instructions she nodded. She grabbed the box and started making her way for the door.

Trip suddenly pushed her door shut. “It’s alright babe, I’ve seen everything you have to offer, you can change here. It’ll be faster and we can get to dinner sooner as well.”

Becky hesitated for just a moment. He was right on all accounts. Besides, she felt she had to impress him–so something as simple as this would work. Becky wasn’t used to having hot guys like this pay attention to her, so in her mind she resigned herself to the idea that this was the cost of doing business.

She set the box down and opened it, her eyes going wide in delight. She reached inside and pulled out the sparkling emerald green dress. It was even in her size. Matching heels, black stockings, a black choker with an emerald green jewel, and a small velvet bag finished out the box. Her hand instinctively reached for the velvet bag when she heard Trip’s voice.

“Not yet, that’s the last piece.”

She wondered if that’s where the panties were, because she wasn’t seeing them or a bra in the box. But she realized that Trip probably picked out this exact outfit for a specific reason. She sat down on her bed next to the box and untied her shoes. Removing them and her socks she stood back up before reaching down and pulling her shirt up over her head.

Even though she knew she was stripping in front of him she couldn’t stand looking at Trip as she did so, she was still a little embarrassed, so she looked away. Setting her shirt on the bed she undid the button of her khakis, lowered the zipper and pulled the pants down her legs, revealing the pink cotton panties she was going to be wearing for the date.

She took a deep breath and removed her bra. She knew that he was also intentional when he said to wear what was only in the box. Finally Becky reached down, hooking her thumbs into the waistband of her panties and lowering them before stepping out of them. Sure she was showing Trip her tiny ass, but considering he’d been inside it, just showing it again was a small price.

She grabbed the dress once again and decided it would be easiest to pull it over her head. It took her a moment, and she could feel Trip’s eyes all over her naked backside as she did so, but she finally got the dress on, just needing to be zipped up. It only went down to mid-thigh, and if there weren’t panties in the bag Becky knew she’d have to be careful with how she sat tonight. She reached back to zip up the dress but couldn’t quite get it. Trip for his part stepped up and zipped the dress up for her before stepping back.

Becky sat back down on the bed and grabbed the stockings out of the box and put them over her feet before rolling them up her leg. They stopped a few inches short of the dress, and she hoped that was because she was sitting but she had her doubts. Though she did admire the odd contrast between her pale white flesh and the black stockings. She rolled the other stocking up her leg and once she was satisfied they were even she grabbed the heels and put them on.

Of all the things thus far the heels made her the most nervous, she certainly wasn’t used to wearing anything like these (or this outfit in general), but the rest of the outfit wouldn’t challenge her ability to walk. The black choker was easily put on, she just had to pull her hair back as she did so.

Finally it was time for the velvet bag.

She reached out grabbing it, and was surprised it was as heavy as it was. These were certainly not panties inside, there was something metallic. She opened the bag and dumped the contents out into her right hand and she gasped, dropping the cold metal object onto her bed.

She recognized the strange object, with a bright green jewel on one side and a metallic teardrop on the other side. After her first encounter with Trip she had looked up anal sex back home, and learned way more than she ever wanted to know. But that knowledge now helped her recognize the jeweled butt plug she just dropped.

“Why don’t you go ahead and put that in your mouth, start wetting it,” Trip ordered. He surveyed the small dorm room for a moment. “Then go bend over the chair.”

Becky looked very wide eyed at Trip in response to the order.

“Don’t worry, it’s brand new, notice the golden monogrammed BF behind the jewel.”

Becky picked up the cold metal plug and turned to look at the jewel, indeed it did say BF. Even through her grimacing she managed a small smile. He did think of himself as her boyfriend. Sadly it was lost on the love struck girl that BF was also her own initials. Satisfied for the moment, she brought the plug up to her mouth and took it inside. She swirled her tongue around it, trying to warm it up and wet it up.

She stood up, flattening out the dress as she did and slowly walked over to the chair that was indicated. For as little practice as she had walking in heels, these didn’t seem like they would be too bad, though it did get her wondering how Trip knew her sizes.

“Good, now bend over, grab the far side of the seat from you,” Trip told her once she reached it. As Becky bent herself over, she felt the dress coming up, exposing herself completely to Trip. She grabbed the far end of the seat, finding with her shorter torso it had her arms stretching out completely.

She felt Trip come up behind her. “Spread your legs more,” he ordered and she did so. Becky had no idea how deep she was letting herself get into it with Trip, but she continued to comply. His hand reached forward toward her mouth and grabbed onto the plug. Becky opened her mouth to let the wet plug be pulled out.

Becky was breathing slow and deep as Trip’s hand started rubbing against her pussy. A gasp escaped her lips as a single finger pushed inside her. The ease at which it entered told her what she already knew, Trip had her wet. Much to her disappointment the finger only stayed inside her for a few seconds before it slipped out and started tracing upward to her asshole. She tensed up naturally, but the finger never made any attempt to push in–only to spread a little bit of her juices around.

Only a few more seconds before his finger left and she knew the moment was upon her. With both hands he spread her cheeks and she felt the cold metal pressing against the entrance to her ass. She took in a sharp breath as it started to push in–not nearly as warmed up as she had hoped. Despite the fact that it felt cold she could feel it heating up her rosebud as it expanded. Becky bit her lip and held her breath as the plug kept expanding her until his fingers stopped pushing, and she felt her ass suck the rest of it inside.

Trip stepped back and admired his handiwork. “You can stand back up straight again Becky.”

She let go of the chair but she didn’t immediately stand back up–she was still trying to figure out the sensations she is feeling inside her ass. Finally Becky started to straighten herself out, feeling the plug in her ass make the tiniest shifts as she did so. She reached down pulling the dress down over her ass again and slowly turned around.

“Ready buttercup?”

For all the cringing that Becky was doing she smiled at the sudden nickname–The Princess Bride was one of her favorite movies and stories (truth be told Becky was slightly obsessed with it). She didn’t remember ever mentioning it to Trip, but maybe she did–after all, she didn’t remember most of her initial conversation with him thanks to the alcohol. As weird as she felt, the idea that he remembered after all this time was very sweet to her.

Trip for his part had no clue what was going through Becky’s mind, or that calling her buttercup had any effect on her at all. He was just grinning that this little college freshman now had a buttplug in her ass for this date. He grabbed her hand and pulled her out of the dorm room.

A few minutes later Becky found herself sitting on a towel draped over the leather seats of Trip’s convertible. The freshman found it a bit odd to be sitting on the towel instead of the seats directly but she didn’t know how to question it. Trip closed her door and walked around, getting in his seat, turning on the car and driving it off campus.

They were only a few blocks down the road when Trip finally spoke. “Pull the dress up to your waist buttercup.”

The brunette blinked several times at the unexpected request. “What?”

“I said pull the dress up to your waist, unless you’ve changed your mind about dating me and want to break up?”

Becky’s heart fluttered into overdrive. He DID consider him to be her boyfriend. Sure, Becky was still very nervous about things, but that was the validation she was looking for. She didn’t quite smile, but even as she squirmed around in her seat to pull the dress up, exposing her recently shaven pussy, she was content.

“Mhmm, my buttercup is as pretty as ever,” Trip said. He was a calculating bastard and he knew it. The girl was so naive, so gullible and willing to buy any story. The problem with owning an android phone was how easily it could be broken. Thanks to one of the computer science geeks in the frat (they were inclusive after all), Trip had root access to her phone and emails since their first fateful meeting.

He’d read the emails and text messages where she detailed how she had a college boyfriend. He also smiled at how she didn’t exactly tell people the whole story, at least not text or email wise. Thanks to his phone access he knew of her blog, and was surprised that she detailed his buttfucking of her there–though thankfully she wasn’t smart or stupid enough (he wasn’t really sure which) to detail how that came about. Trip had always had his control over the college sluts around him, but that control was more in small spurts. This would be Trip’s first time controlling a girl as part of a long term project.

The car ride was otherwise uneventful. Becky sat in the convertible with her pussy exposed for Trip and anyone in a semi truck to see (thankfully there were none), and Trip kept stealing bemused glances at his new pet.

When they were about to pull into the restaurant parking lot, Trip told her to pull the dress back down and get ready. The valet didn’t suspect a thing as the two got out of the car and headed inside.

Dinner was uneventful in almost every way possible. Awkward small talk, lots of eating, nothing about the exposure of the car ride or the little metal bulb currently resting in her ass. When it came to dessert, Trip declined for both of them as he said it was already taken care of. This was the only thing that really got Becky’s attention. Soon they were back outside and getting in the car.

A few blocks down the road Trip had Becky once again expose herself, but he also reached into the little space behind his seat and pulled out a wrapped package. Becky took it a little bit surprised, though inside she wondered if this gift was going to be like the one she received earlier.

Unwrapping it Becky found a nondescript long box. Trip nodded and she opened it. Her instinct was right, there was definitely a connection between the two. Inside the long box was a rabbit vibrator, something Becky had seen before online but never in person. A small bottle of warming lubricant was also inside the box. She suddenly understood the presence of the towels.

“We’re going to drive the loop buttercup. I fully intend to have my fun when we get back to campus, but I think it’s only fair you have yours first.” The loop she had learned the day before was what locals called the route that bypassed the college town on the highway. At the speeds they could go it would only be about a fifteen minute extension to their drive.

“So you should take advantage and start to enjoy yourself. We don’t get out of the car until you cum, so hopefully you’re not one of those girls who takes a long time, otherwise it’s going to be awkward sitting in the frat parking lot still trying to get yourself off.”

Becky started to panic for a moment before relaxing. Trip wouldn’t really do that to her she realized (incorrectly of course). She looked down at the toy, the lube, and her own newly bald pussy before taking a deep breath and grabbing the bottle of lubricant out of the box.

She opened the bottle and squirted a small amount onto her right hand. She was trying to be nice about not making too much of a mess for Trip, though with the type of planner that he was she wasn’t so sure that was something she really needed to worry about. Her slick fingers moved down to the soft folds of flesh that were only illuminated by the in-car lighting and of course all the streetlights.

Becky started massaging the while and pink flesh that guarded the core of her being. She felt herself becoming more slick from the combination of the lube and her own natural wetness starting to assert itself. Getting a little more adventurous, she brought the lube bottle close and started to squirt some of the liquid directly onto her sex.

She had started to feel the most basic effects of it when she was spreading it from her fingers to her body, but pouring the warming lube directly onto her pussy made the effects much more pronounced. There was now a profound warmth unlike anything she had ever felt on her pussy or clit before and the sensation was making her feel good.