The Dorm Roommate

Alice was nervous meeting her roommate for the first time. Roommates were randomly assigned for first years, and she had no idea who she would be paired up with. For the first year, her only option was a shared bedroom. She had only just turned 18 a few months ago, and this would be the first time she'd ever been away from home for more than a few weeks. Now she was taking the leap moving two towns over for college. She was excited to finally have freedom and feel like a real adult.

Walking in and finding her roommate already there and decorating was a great first sign, and everything that followed only seemed to confirm that Alice had lucked out. Madison was sweet, bubbly and friendly. She was a bit shorter than Alice, with shoulder length black hair framing a cute dimpled face. Within the first few minutes they had already connected over liking the same music and tv shows and they found out they even had a class together in the first semester. Alice could admit that she was maybe a bit jealous of her figure, Madison seemed to be one of those skinny girls who still had curves in all the right places. Alice was happy to be lean rather than curvy, it just didn't seem fair some people seemed to get it all.

The room itself seemed fine, if a little small. It was a one room dorm with an attached bathroom. The room had two beds along opposite walls with a cabinet for their belongings. Her only option for the first year had been a shared sleeping area. She'd been intimidated at the idea at first, but now it looked like it could work out.

As they chatted the conversation eventually moved to relationships.

"Do you have a boyfriend?" Madison asked.

"Oh yeah, he's back home." Alice had thought she would be more heartbroken having to go long distance with her boyfriend Jeremy. He'd asked her out to senior prom in the spring and they'd dated over the summer. He was going to the local community college, and she was now several hours drive away. They'd both been on the yearbook committee together, he was a shy quiet guy she'd known for years. If she was being honest however, it was actually somewhat of a relief to get away. In August they'd had sex and Jeremy had become much clingier. He'd tried to see her every day when often she just wanted to see her other friends and her family. When she'd tried to ask for some space, they'd argued. She'd suggested they break up since they were both going away to college and hadn't been dating that long, but he'd cried and convinced her to try long distance for a while.

She brought her mind back to the conversation, "how about you?"

"Oh yeah, I guess I am dating someone," Madison laughed. Alice wasn't quite sure why that was a joke, but she laughed along with her.

The first few days of classes passed in a blur. Alice was realizing quickly that she really didn't know many people on campus. She had few friends who were also in their first year, but none she had any classes with. It was a relief when she got to Psych 101 and saw Madison sitting there waving her over.

They were having lunch between classes a few days later when Madison brought up boys again.

"So... meet any cute guys yet?" Madison asked.

Alice just blushed "oh, I just got here and I uhm...the boyfriend."

"You're too cute! I was only teasing!" Madison laughed.

Again Alice wasn't quite sure what the joke was supposed to be, but laughed along with her.

Alice had never really been one for parties, and she was happy to learn that Madison didn't really go out much herself. On the first Friday night they had a quiet night in their dorm, getting some work done, and streaming random shows. Again Madison steered the topic of conversation towards boys. "My boyfriend is so lame, he got me moved in but says he won't visit for another week!"

Alice was actually experiencing the opposite, her boyfriend was pestering as to when he could visit, but she was putting him off. Still she commiserated, "Aww well that's not too far away, I still feel pretty overwhelmed with school."

"Oh yeah you're right, but a girl has needs you know?" Madison sighed.

Alice was almost ready to turn off her light and head to bed when Madison looked up from her phone and turned to her. "Hey Alice, I'm sorry to ask last minute, but do you mind if I have a friend over for the night?" "Oh", said Alice, momentarily confused. It must be one of Madison's friends who lived off campus, she reasoned, they probably didn't want to pay for a cab after a party. It seemed like Madison was a really good friend if she was willing to do that for a friend. "Oh sure, that's no problem, I was actually going to sleep now anyways." Madison's face lit up, "thanks! I owe you one! I'll make sure we're not too loud." Alice out on her pjs, laid down and turned off the light as Madison quietly slipped out.

Around twenty minutes later Alice heard Madison coming back in with her friend. "Shhh, my roommate's sleeping, it was really nice of her to let you come over." Alice was a little shocked when she heard a deep voice respond, "okay, I gotcha".

So her friend was a guy. She heard Madison's bed creak, and then again a few more times as they both got in. It wasn't technically allowed to have anyone else in the dorms overnight, but Alice supposed that if he really didn't have a place to stay she shouldn't complain. Still, Alice was surprised Madison was letting a guy share her bed, she wouldn't have thought her roommate would be comfortable with that. She would have said if it was her boyfriend rather than a friend though wouldn't she?

Barely 5 minutes later, she started hearing more noises and the occasional creak. Was Madison making out with this guy? Alice was lying facing away, but slowly turned over and opened her eyes just enough to look across to Madison's bed.

Although the room was dark, the light through the window was enough to illuminate what she saw. She had expected the guy to be one of the college boys from their classes, but this was a man who looked to be at least in his late twenties or early thirties. He was tall, lean and half covered in tattoos. He also had his shorts pulled down with a massive erection. Madison was on her knees facing him, ass up in the air, only wearing a black string thong. It took Alice only a second to realize Madison was giving this man a blowjob. The girl had the man's substantial girth in one hand guiding it into her mouth while she reached back and touched herself with the other. The man reached up and gathered Madison's hair into a pony tail, before forcing her head onto himself a little more.

Rather than pull away or choke, Madison only increased the speed intensity with which she moved up and down on the man's member.

Alice had only given her boyfriend a blowjob one time, he'd finished almost immediately, getting it on her shirt. She'd asked him to reciprocate by going down on her, but he'd declined. She always made excuses to avoid blowjobs after that. As she watched she was shocked at just how much of the man's dick seemed to disappear down Madison's throat.

The man whispered something to Madison and she laid back and spread her legs. The man got to his knees and bent forward, reaching behind her legs and pulling her towards him. In one swift motion he removed her thong. Madison gasped as the man's face buried itself in her crotch, covering her mouth with her hands to keep from moaning out loud.

Alice realized her hand had drifted down to her crotch some time ago and she could feel her own wetness. Was she turned on watching this? Was she jealous? No, she was just a little curious...

Madison continued to writhe around on the bed with the man latched on to her pussy. Alice heard her whisper, "I need you inside me right now."

It seemed the man needed no encouragement, because he immediately laid back on the bed. She looked on as Madison stood up and then squatted down right on the man's member, guiding him into her with both her hands. Alice couldn't believe he would even fit at first. She had measured her boyfriend once just to see and he had been just over 4 inches long, this looked like twice the length and much thicker. Placing her hands on his chest, Madison started lowering herself up and down. She started slowly, but soon she was taking the man's full length, bouncing up and down on him.

Alice was shocked, she didn't think a girl like Madison would do anything like this. At the same time, she had no idea sex could be so intense. Her boyfriend had only ever been on top in missionary, and he never lasted close to this long after they'd started.

When Madison slowed her pace on top, the man reached up with both hands grabbing around her neck and shoulders. Bracing his feet on the bed, he began to thrust upwards into her. Madison buried her face in the man's chest, but her whimpers of pleasure got louder.

After a while of this, they changed positions again. Madison got on her knees and arched her back, pressing her face and chest into the mattress. The man got on his knees behind her and started guiding his dick into her. The second he got the head inside her, Madison slammed herself backwards onto him, taking his full length. He held himself inside her for a long moment before grabbing an ass cheek in each hand. He started thrusting into her, slowly at first, but gradually picking up the pace. The rhythmic slapping of his hips on her ass got louder and louder. Eventually he was pounding into her so hard Alice was sure he would break her. He was pulling her ass back onto him at the same time he thrust forward again and again. He had built up to a speed that Alice was surprised he could maintain. She could see Madison was burying her face in her blanket to keep from screaming, but her moans still sounded like she was very much still enjoying herself. This was proved when after a few minutes of this, the man's pace slowed and he seemed to take a break, breathing heavily. Madison immediately got up to all fours and started forcing herself backwards onto his dick again and again.

Eventually she heard the man mumble something and Madison immediately turned around, got onto her knees, opened her mouth and stuck out her tongue.

The man grunted and shot out a rope of cum that splattered across Madison's outstretched tongue and cheek, then another across her chest. Finally she wrapped her lips around the head of his dick and continued to jerk him off with her hands as he grunted again. Alice continued to slowly play with herself as she watched. It wasn't until she looked up at the man's face that she suddenly froze, he was looking straight at her and smiling. How long has he been watching her? Had he seen her watching? Touching herself? Surely it was too dark and she was under her blanket. He might have just realized she was likely awake, which was embarrassing enough! She closed her eyes tight, and before she knew it she had drifted off to sleep.

When she woke up the next morning the man was gone. She expected Alice to be a little awkward with her, but the girl just greeted her with a smile when she saw Alice was awake.

"Hey roomie, sorry if we woke you up at all last night!"

"Oh yeah uh no problem, was that your boyfriend?"

Madison laughed, "No no, that's just a friend."

"Oh wow." Alice said, at a loss for words.

"Ahaha, my boyfriend's fine with it, he knows I need a little something extra sometimes," she said with a wink.

"I really appreciate it! I owe you one. I'm so lucky to have a roommate I can be open with. College is about freedom and experimenting y'know?"

"Your boyfriend's really okay with that?"

"He's the one who suggested it! Sometimes I let him watch," she said with a wink.

"Wait, he suggested it?" Now Alice was confused? Did some guys like that?

Madison ignored her question and asked one of her own with a sly smile, "how about you? Did you enjoy the show?"

Alice felt her face flush red. "Oh I uh, I was sleeping mostly."

"Ahaha well I was trying not to be too loud. Good to know for next time."

Next time? Was Madison planning to do this often? Her thoughts must have shown on her face because Madison went on, "that was okay right? I really don't want to make you uncomfortable if it was too much."

Alice wasn't quite sure how she felt, but she responded reassuringly. She had watched nearly the whole time to be fair.

"Oh uh no it was fine, what I did see was pretty intense."

"Mmmm yeah I know right? Devon is so fucking hot. Knows exactly how to treat a lady."

Alice just blushed in response.

"You're welcome to have a go with him, I'm more than willing to share," Madison teased.

Alice didn't think she could go any more red in the face. "Oh no, I couldn't do that to my boyfriend!"

"Does that mean you would be interested if he wasn't in the picture?" Madison asked slyly.

"I... I don't know. I almost... we almost broke up in the summer."

"Mmmm I think I see. He any good in bed?"

"Ah uhm, well he's the only guy I've even been with... but uh, he's not anything like...I saw last night." Alice was still painfully shy talking about sex.

"Yeah hard for most guys to measure up to that," Madison laughed.

The rest of the week in classes, Alice couldn't get the conversation with Madison out of her head. Was she satisfied with her boyfriend? Maybe Madison had the right idea and college was the time for her to be trying new things. DId she need to find herself as an independent person?

After a few days of going back and forth, she knew what she had to do. The phone conversation breaking up with her boyfriend was awkward, but felt like such a relief afterwards. He had cried and told her he loved her, but she just couldn't say she felt the same. He was a sweet guy, but that's not what she needed right now

That weekend, when Madison let Alice know she would be gone with her own boyfriend for a night, she plucked up her courage again.

"Do you think I could get Devon's number?"

Madison's eyes lit up. "Oh really! For sure! He's going to be psyched, I'll let him know."

Over the next few hours she texted back and forth with Devon. He seemed surprisingly laid back. Asking questions about her move, and how school was going. Once again it fell to her to take the initiative.

So Madison's gone for the night. Are you free to come over? She texted.

He responded in the affirmative and before she knew it, he was outside her building and she was leading him back to her dorm room. This was the first time she'd actually seen him in the light. He was clean shaven with a buzz cut, standing almost a whole foot taller than her. She was nervous, but excited, meeting up with a man almost twice her age. She could admit how turned on she was in anticipation.

Arriving back at her dorm room, Alice was surprised that they didn't immediately just strip down. Instead, they cuddled in her bed for a while just chatting. Eventually he made a move and leaned in for a surprisingly gentle kiss. They started making out fully clothed, but she could feel his large hands running up and down her petite body. One of his hands slipped down the front of her shorts, gripping her sex with three fingers.

"You're really wet," he grinned at her. "Excited?"

She couldn't help but blush. Without responding, she kissed him back and reached out with her own hands into his shorts, feeling his rapidly inflating member. She was shocked how big it grew in her hand. They continued like that for a while, making out while mutually masturbating each other, when Devon rolled her over to her back so he was on top. She could feel her heart jump, this was really happening.

In one smooth motion he pulled off both her shorts and panties. He buried his face in her hairless pussy, starting by just teasing her with his tongue, before slowly building the intensity. Just as she was becoming more and more stimulated, his mouth latched onto her clit and she was wracked by waves of pleasure. She could feel something building as his tongue moved every which way. Devon could apparently feel it too, because he broke off with his mouth and started using his hand again in a firm rhythmic motion. His other hand reached under her shirt, groping her breasts. His pace slowly increased until she couldn't take it any more and was wracked with the shudders of a small orgasm. She tried to cover her mouth with her hands, but could not stop from moaning out. He held her as she shook, pressing firmly against her mound with his hand. The moment her quivering subsided, he sat her up, and pulled off her tank top and bra together. He stood up and stripped himself, his now fully erect cock springing free of his shorts.

"Can you go gentle? You're a lot bigger than my ex." He spread her legs and positioned himself on top of her. "Of course babe," he said, leaning down to kiss her. His dick came forward at the same time, pressing against her waiting snatch. As they kissed she could feel him using his hand to run his dick head back and forth across her pussy lips, teasing her. He continued this until she couldn't take it anymore.

"Fuck me!" she moaned.

"Oh yeah?" He replied with a smile.

"Please fuck me!" She'd lost any sense of apprehension at this point, she needed him inside her now.

Devon slid into her and to her shock she almost came instantly. He was barely halfway in, but the sensation of being filled up was almost too much. It only took a few gentle probing thrusts and she was coming. She cried out in pleasure as she grabbed onto his back and shuddered with the effects of the orgasm. As her quivers and moans subsided, he continued to thrust into her, slowly at first, but building in speed and intensity. She looked down and would have been shocked to see just how much of him was dispersing inside of her if she couldn't already feel herself being stretched. Alice could tell he was still holding back, which she appreciated, but she could feel part of her wanted even more. She wanted to feel his whole length pounding into her. Before she could examine that feeling however, he slowed his pace and looked down at her.

"Do you want to ride me?" He asked.

She got on top, slowly sitting back and letting him slide into her rather than squatting on it as Madison had done. Even controlling the pace like this, the sensation was almost too much. She slowly rocked back and forth on his cock, trying to take more each time. He was reaching up with his hands at the same time, teasing her nipples, running across her collarbone and neck. Alice appreciated that he had listened to her request to be gentle, but now she needed more.

She put on the most innocent and seductive voice she could muster. "Can you fuck me hard now babe? My little teen pussy needs your big dick." Devon's reaction was immediate. He grabbed her ass cheek firmly with each hand and started thrusting up into her from the bottom.

"Hhhnnggg!" The sudden change in rhythm caught her off guard, but not in a bad way. She could already feel another orgasm building. She couldn't hold up her body any more. She collapsed on top of Devon, wrapping her arms around him as he pounded into her. "I'm coming!" She moaned in his ear, and he thrust to the base of his dick inside her, holding himself there as she cried out and quaked on top of him. She only had a few moments to process the sensation of him completely filling her before he was slamming into her again. He used the grip on her ass to slam her on his dick again and again. She had lost all pretense of staying quiet and was all but screaming as he ravaged her. His pace slowed, but she picked up where he left off. She put her feet down on the bed, and began to squat on his dick just as she'd watched Madison. The sensation was intense, but she managed for a while before collapsing back on top of him.

"Can I take you from behind?" He asked, and without responding Alice immediately hopped off and got on all fours, presenting herself to him. He slid into her, again starting gently but before long was pounding away. She was almost starting to regret telling Devon to go harder, but only almost. As she settled into the rhythmic thrusting she could feel something building in him. At the same time he grunted, "I'm gonna come." She let him slide out of her and got on her knees.