Welcome to College - Becky's Freshman Year
Chapter 1

Copyright© 2016 by LOAnnie2

BDSM Sex Story: Chapter 1 - During a pre-college visit, Becky Freeman was tricked and blackmailed into giving up her virgin ass. Now she's been ordered to report back to him every Friday night of her freshman year. She thinks he likes her, he think's she was a good buttfuck. Nothing in college is as simple as it seems. This is the story of Becky's Freshman Year.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/ft   Blackmail   Coercion   Consensual   Reluctant   Heterosexual   Fiction   School   BDSM   MaleDom   Humiliation   Light Bond   Rough   Anal Sex   Masturbation   Sex Toys   Voyeurism   Public Sex  

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 lovestruck 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.

She took another minute rubbing the oil into herself. Trip was just turning the car onto the loop before Becky considered the vibrator again.

"You're going to want to insert that before you turn it on," Trip said rather casually, the only words he had said since he told her to get herself off.

The brunette girl nodded to him and picked up the toy, squeezing out some of the lube directly onto the toy and rubbing it in with both hands. Once the toy was ready to go she positioned the toy between her thighs. She looked at the cobalt blue toy that contrasted against her white legs with a curiosity. With no further excuse to wait, she brought the toy to the edge of her sex and started to push it in.

Becky let out a deep breath as the blue toy started to open her up. Slowly she started to fuck herself with the still-off toy. The warmth she was feeling from the lube was spreading inside her. She closed her eyes as she started to get more turned on. She didn't know how long she had been just fucking herself with the toy when she started feeling the ears brushing by her clit.

She opened her eyes and looked down. It was now or never as she moved her finger to the button that would turn on the toy and she pressed it, setting it on low. As the phallus hummed to life inside her Becky let out a low moan. The feel of the vibrations inside her and the rabbit ears around her clit was an intense feeling she had never quite experienced before. She held the toy in place just letting it shake her core.

"You should turn on the rotation," Trip said.

Becky's thumb moved over to the other button that controlled the rotation and turned it on low and suddenly stiffened up as it slowly started rotating inside her. A loud moan escaped her lips as she experienced another new sensation. Her eyes were quickly closed again as she let the warmth and vibrations surge through her body.

Trip glanced over at her with a giant smirk on his face. He moved his right hand to put it behind her shoulder. Becky naturally pulled herself just a little off the seat at Trip's hand. As his finger hit the zipper at the back of her dress he couldn't help but be pleased how naturally she's taking to it. As he lowered the zipper he noticed that his pet had apparently pushed the buttons again, turning up the effect of the toy on her pussy.

With the dress unzipped Trip was able to tug at it in such a way that he could free her small breasts from the fabric. Here Becky was in Trip's car, her small breasts exposed, a butt plug sitting firmly in her ass, and a vibrator that she was turning up even more. At this exact moment the only fuck that the formerly innocent Becky could give about being seen like this was the fuck that she was giving the vibrator right now. Even Trip for his part couldn't believe how revved up this plain little freshman girl was getting in his presence.

Becky didn't know how to feel about her situation. The rational side of her brain was screaming at her, trying to get her to regain some sense of composure–to fight this. The pleasure centers of her brain though were on full mutiny and were all for her being swallowed up by the feelings unlike anything that had ever run through her. Subconsciously she didn't realize that the was resisting the pleasure, trying to hold the dam back–she was unintentionally edging herself.

Somewhere in the background, in a far away place Becky's brain registered several horn blasts from a semi truck, but her mind was too far gone to realize that someone must have noticed what was going on under the bright highway lights. Something broke inside of her and she realized that the dam of pleasure she was holding back was bursting–so Becky did the only thing she could do, she jammed the button on the vibrator that turned up the power and let the dam collapse.

Becky's scream of pleasure caught Trip so off guard that the car actually swerved. When he looked over to see Becky pushing herself hard into her seat, her head tilted all the way back. She was breathing sharply and crying out in pleasure through her orgasm. He couldn't help but smile, the orgasming Becky was definitely a sight to behold.

Trip pulled off the freeway and was making the turn to head back to campus the traditional way, the loop nearly complete. He didn't pay attention to the cumming girl until he no longer heard the sounds of the vibrator–Becky had turned it off.

"You might want to pull yourself together buttercup, we'll be on campus in three minutes."

Becky was shocked out of her post-orgasm glow by a new sense of panic. She looked down seeing how the dress had slid down, a bit confused as to how that happened. She pulled it back up and reached back as best she could to zip the dress back in place. However she looked down at her drenched pussy and then looked over to Trip. The senior reached back and grabbed another towel and handed it to her.

She took the towel and started drying her pussy, her stomach, and her legs. She had never cum so hard in her life and she started to worry that Trip may not have had her sit on enough towels. She also wrapped the rabbit in the towel and dried it off as best she could before putting in the box. Without thinking about it she lowered the dress, covering herself once she was convinced that things were dry enough to be alright.

"Take that Box with you as we go inside. Consider it a present."

Becky didn't know what to say, so she just blushed. The last minute or so of the car ride to Trip's frat house was rather uneventful. As they parked Trip hit the button that closed the top to his ride. Once it was closed Becky got out of the car onto very shaky legs, the nondescript box in hand that held her new toy, and followed Trip into the frat.

It was a Friday night after all so there were quite a few people hanging out at the frat, and there were a lot of eyes on the girl as she stayed very close to Trip. When she reached the staircase that she knew would lead up to Trip's room two guys stepped between her and Trip.

"You know there's a price to go up?" One of them said to her rather harshly. Instead of responding Becky looked around and found what she was looking for right where she remembered it. She pointed to a picture of her purple panty-clad ass that was taken her first time in the house. The two who stopped her looked a bit surprised for a second and nodded, stepping out of her way all while Trip watched the scene with amusement.

There had been a few changes upstairs. A new sign had affixed Trip's door that told the message she had previously seen inside the room–It was a modified version of the "No Shirt, No Shoes, No Service" sign–it simply read "Ladies, Shirt, Bra, No Service." With the extra no's crossed out and some clever rewriting of the sign. Becky had also noticed that next to each room was now a small locker.

Trip tapped on the sign and looked to the locker. There were a few guys milling about in the hallway and Becky knew exactly what Trip had in mind. Becky's immediate thoughts weren't about the guys who were about to see her naked since she obviously had no pants or panties on. Her thoughts weren't even on the horrible idea that if some guys had the right angle they might be able to see the butt plug. No, at this moment Becky had just hoped that she had cleaned herself up enough that it wouldn't be obvious that not five minutes before her lower half was drenched with her own cum.

Becky reached back and pulled the zipper back down the rest of the way. This time she slid the dress off her shoulders and down her arms, instead letting it fall to the floor. For the moment her only clothing were the necklace, heels, stockings, and of course the butt plug (if you could call that clothing). She awkwardly lowered herself to pick up the dress and put it in the locker, which wasn't unlike the ones you'd find at a pool.

She turned and took the key in her hand, trying to ignore the people who were checking out her naked, butt plugged eighteen-year-old body while Trip opened the door. She quickly got inside and he shut the door hiding her from the rest of the world.

It may have been five months since Becky last found herself in this room, but she was surprised how little seemed to have changed. Trip threw his keys on a desk and glanced to a clock before he looked at her. "Well now, buttercup has had her fun, time for me to have mine."

Becky flushed a little. As much as she hated to admit it he was right. Trip motioned for her to set her box and key down. Once she had done that he spoke again.

"Bend over the bed Becky."

It wasn't a request, it definitely felt like an order to the girl. However it wasn't one she was planning on disobeying and she walked over to Trip's bed, and bent herself over it. Putting her arms out since the bed was a little lower than she expected (heels and all). The naive freshman had a smile on her face as she had her eyes closed and heard Trip behind her.

Soon she heard him approaching and she felt his nimble fingers brush against her pussy. His other hand reached between her cheeks and grabbed the butt plug. Becky took in a quick breath and held it. The hand that brushed against her lips grabbed at the back of her thigh, and his other hand started pulling the plug out. Becky's face cringed as her asshole expanded to allow the plug its exit. Soon she heard a little plop as it came out and felt an odd empty sensation that she didn't expect.

Trip's hand released itself from being wrapped around her leg and a pair of fingers plunged inside her pussy, causing Becky to gasp as she had to remember to breathe. The fingers inside her body made her realize for the first time that her pussy felt sore from the orgasm she just had. The fingers were pulled from her pussy after only a moment before they were pressing against her anal ring. The fingers didn't enter her, but they helped spread her juices along the outside.

Becky didn't bother looking back, though she definitely knew what was coming. She wasn't aware that Trip was naked behind her, his cock lubed up and ready and that he considered what he was doing with her own juices a courtesy. Rubbing his fingers on her back to wipe away what else he could of her juices Trip positioned himself behind the bent over girl.

She braced herself for the pressure as she felt the head of Trip's cock against her rosebud, but he pushed forward and much easier than she remembered before (or even earlier this evening) she opened up for him and soon he was imbedded in her ass. Breathing again slowly, Becky got used to the sensation as Trip's cock was quite a bit thicker than the butt plug was–but the sex toy had done its job, it seemed like her ass was much more ready for him this time around.

Trip's cock kept pushing forward into her rectum and through controlled breathing plus the much more ample amounts of lube that he provided this time it was a much less painful experience for her. Soon she felt the dangling of Trip's balls brushing against her still sensitive pussy and she knew he was fully inside her ass. He stayed there for a moment before pulling out again.

Becky could tell a difference from before. Trip wasn't wasting a whole lot of time as he buried himself inside her again, and started to saw in and out of her with ever faster speed. It was just like last time, and what Becky had seen of various porn videos. She had spent a lot of time over the summer watching porn, particularly anal sex videos.

While there were many first time anal videos between couples where the guy was slow and gentle, Becky realized that there was a whole world out there of anal sex videos where guys wanted to see the girls hurt. When the guy was fucking the girls ass with the same if not more ferocity and energy than he would fucking a girl's pussy, it was kind of obvious what the point was.

As Becky contemplated this she felt it was what Trip was doing behind her. Unlike her last experience with Trip, her orgasm came before the anal sex, not during. Having to concentrate on what was going on in her ass made her so much more acutely aware of every feeling of the shaft rubbing against her tightest hole. She hadn't even noticed the grunts she was letting out as Trip hammered her ass.

There was no concept of time for Becky as Trip went to town, though just like that it was over. Trip buried himself to the hilt inside her ass and she felt a spasm as Trip let out a low groan, something guttural. With a loud, pleasured sigh he pulled himself out of her ass. Becky started to straighten herself out when a hand kept her pushed down. Any confusion Becky would have had over this was quickly answered when she once again felt cold steel against her butthole and the plug was once again inserted.

Once Trip stepped away Becky straightened herself out. Both of her lower holes were sore for very different reasons, and with being in heels and stockings it took her a moment to get her balance just right. Trip was toweling himself off and putting his Boxers and pants back on. Becky looked around a bit sheepishly, she wasn't exactly sure what happened now.

Once Trip buttoned his pants he went over to his desk and picked up the vibrator box and the locker key. He smiled at Becky. "This was fun buttercup. Be here at six next Friday."

As Trip opened the door Becky was a little confused. She realized she was being ushered out but it was such an abrupt ending to a nice evening. Was she going to have to get back to her dorm room by herself?

The hallway had a much larger crowd now as she came out and Becky was more acutely aware of it having been dismissed by Trip. Quickly she got the key in the locker, fumbling with it for a moment before she set the box down and was pulling the dress over her head, hiding her nakedness from half the frat. The freshman girl didn't yet know what the walk of shame was, but she certainly felt it as she picked up the box and hightailed it down the stairs.

At the bottom of the stairs she saw the same two guys who were gatekeepers earlier grinning from ear to ear. Before them stood a cute little blonde that Becky figured had to be a fellow freshman standing in a t-shirt and a thong. The blonde girl looked completely freaked out, much like Becky imagined she had the year before (or would have if not for the alcohol). As Becky glanced back the blonde's ass was very red. The same guy who talked to her earlier told her the second door on the left up the stairs.

Becky frowned, that was Trip's room. She glimpsed at a clock and noticed it was 8:30. A part of the brunette was tempted to go back and investigate, but the rational side of her brain was back in control. All Becky wanted to do was get her freshly buttfucked ass back to her dorm so she could clean herself up.

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