Oral Advocacy Ch. 02: The Roommate

"Thank you, Kate," Derek said as he lay on his back with her beside him propped on her elbow. She gently stroked his chest with her fingertips.

"You're welcome," she said. "And thank you, Derek. I needed that in a way I never realized." She kissed him again and they lay together in the dark for a while before both fell asleep. When she woke up, Derek was still asleep. She saw his morning wood poking up under the sheets but decided to let it go, not sure of what to do the morning after his first time. Derek was awake when she returned and, after he showered, they had breakfast together. Then she drove him back to his dorm. Getting out of the car, he said unsurely, "Well, thanks again. It was nice meeting you and I hope you have a safe drive home."

"Who said anything about going home?" Kate replied. "It's only Saturday. I'll meet you here at 4:00." Derek beamed as Kate drove away, evidently pleased with his good fortune. Kate went for another six-mile run and spent some time in the hotel fitness room, happy to get in a good workout after her weeks spent in trial. After showering and shaving very thoroughly, Kate threw on some tight jeans, a low-cut black top, and black boots. She grabbed some food from the hotel restaurant and watched TV in her room, somewhat discombobulated with no work to do. At 4:00 she drove to Derek's dorm, happy to find him waiting for her outside. By the grin on his face and bulge in his pants, Kate knew he was glad to see her too.

After they entered his dorm room and sat on the couch, Kate turned serious. "Derek, we need to talk," she said sternly as a look of disappointment crossed his face. "Yesterday was great, it really was. But I'm sorry, it can't happen again. Do you understand?"

"I guess so," he said in a confused and deflated tone. "I thought everything went well and I had a great time but..."

Kate stopped him. "That's exactly my point," she said. "You had a great time, but you left me unsatisfied. You can't touch me like that and just leave me hanging."

"Oh," he said. "I'm sorry, it's just that I'd never done that before and..."

"It's okay, it was your first time," she said. "I'm just teasing you. But seriously, I'm crazy horny right now. Have you ever gone down on a woman?"

Derek gulped and shifted uncomfortably. "No, I haven't," he said softly.

"Well, it's time you learn," Kate said. She pulled her shirt over her head and unclasped her bra. Standing up, she shimmied out of her boots and jeans and took her underwear off. She sat back down and pulled Derek toward her, kissing him and letting him suck and fondle her tits until she was wet. Then she pushed his head toward her crotch. Kneeling in front of her as she leaned back on the couch with her legs spread wide, he began to lick her pussy. He started too hard and too fast. Kate guided him with her hands and told him exactly what to do until he got the hang of it.

Derek began to pleasure her exactly how she liked it. As she got close, she thrust her hips forward, smashing her pussy into Derek's face. He backed off slightly and Kate, desperate for release, grabbed his head and pulled it forward. Grinding herself against his tongue, Kate cried out repeatedly as she climaxed intensely. Holding Derek's head against her, she jerked and spasmed as her orgasm continued much longer than she expected.

As soon as it started to subside, Kate released Derek's head. Before he could say anything she stood up and pulled him to his feet. She rapidly undressed him, jerking his pants to his ankles. "All the way off," she said. Fumbling with his shoes and pants, Derek almost fell over as he undressed, Kate waiting impatiently for his cock. As soon as he was naked, she took him to the bed and climbed on top of him.

Easing his cock into her, she began to ride him. Kate loved the feel of her clit rubbing against his shaft as he played with her nipples and squeezed her ass. She orgasmed again, this time letting out soft moans as Derek satisfied her. Kate began to ride him harder, squeezing him with each downward thrust and making sure he got as deep as possible. Moments later, she felt him swell inside her. His muscles tightened and he began to thrust upward. Kate squeezed harder and slammed herself down on his massive erection. This time Derek screamed as he came inside her, his cum leaking back onto himself as she rode him to completion.

Collapsing onto the twin bed next to him, neither of them spoke, the sound of their heavy breathing filling the room. Eventually, Derek just said, "Wow."

"Yeah, that was pretty good, wasn't it," Kate said. She kissed him and, after a while, they both got up and got dressed and went to a restaurant on the outskirts of town, away from campus. About halfway through dinner, Derek asked, "Why are you doing this?"

"I'm hungry," Kate said.

"You know what I mean," he replied. "I don't understand. You're smart, successful, and really pretty. Why are you on a college campus sleeping with guys you barely know?"

"I guess I'm just a friendly gal," Kate said, trying to laugh it off and dodge the question. But Derek persisted and she grew serious. "I know it's crazy, but all my life I've followed the rules. I studied hard, worked hard, did everything I was supposed to. I've always been the good girl, in the top of my class in high school, college, law school, everything. I didn't party in high school--I was too busy studying. Then when I got to college and met a guy I wanted to sleep with, he was a jerk. My first time was totally underwhelming."

"I totally understand," Derek said. Kate started to protest. "No, I'm just kidding. But the high school part does sound familiar."

"You better be kidding," Kate said smiling. "Anyway, all that work and rule following led me to a job that I love, but that leaves no time for anything else. And I guess I just needed a release. When I met Matt, I just needed to get laid so bad. I hadn't realized it. Then when I met you, I don't know, being your first just turned me on more than I expected. Knowing you'll remember me forever and that I could give you a great experience, it was just too much to pass up. I don't know, maybe that's crazy, but it's true."

"No, it's not crazy. It makes sense. I can't say this was how I imagined losing my virginity, but it was great," he said.

"Hopefully your confidence is growing. There are plenty of girls out there who'd be lucky to have you, especially after what I'm going to show you tonight," Kate said.

Derek flushed, obviously turned on but apparently a little apprehensive. "I don't know, I mean, you came on to me and I don't know, I'm just not confident around girls. I don't think any of them are really interested in me."

"You just have to be confident," Kate said. "Look them in the eye, talk to them, listen to them, and be respectful. That's really all there is to it. There have to be some girls here you're interested in. I mean, running around campus I saw tons of beautiful women."

"Well, there is a girl on my dorm floor I kind of have a crush on. She actually lives right across the hall. I've talked to her a few times and we're kind of friends, but I don't know, I just don't think she likes me and it'd be awkward if she turned me down, living so close and all," he said.

"Interesting," Kate said. "You have girls on your floor? That's a new one."

"Yeah, our dorm is coed. Not roommates, but on the floor. The room across from us is a four-person suite of girls," Derek said.

"And who's the one you like?" Kate asked. "Tell me about her."

"Her name is Megan, she's super smart and put together, pre-med, blonde, with a great body just like yours, actually," Derek said.

"Sounds impressive," Kate said, smiling. "Maybe I can help." After they finished eating, Kate drove them back to the dorm and told Derek to go upstairs first. She waited about 10 minutes and then rode the elevator up to Derek's floor but, instead of going to his room, knocked on the door across from his. Moments later, a pretty blonde in shorts and a t-shirt answered.

Feigning surprise, Kate said, "Oh, I'm sorry, I must have the wrong room. I'm looking for Derek?"

"Yeah, he lives across the hall," the woman said.

"Got it," Kate said. "I'm sorry to bother you. It's just that when I came up here with him earlier I wasn't exactly able to focus on what room we were going to, if you know what I mean."

"Uh, not exactly," the woman said.

"Let's just say we were a little preoccupied on the elevator ride up," Kate said. "And definitely in a hurry to get to his room. Anyway, sorry for bothering you."

"No, it's fine," the woman said, sounding intrigued. Kate knew she'd caught her interest. "I'm sorry, I don't think we've met. I'm Megan. Are you Derek's girlfriend?"

"Um, not exactly," Kate said. "But something like that. I'm Kate, it's nice to meet you."

"Sorry, I didn't mean to presume," Megan said. "It's just that I've lived across the hall from him all year and we're kind of friends but he hasn't said anything about you. Do you go to school here?"

"I'm a law student," Kate said. "Third year, I'm graduating next month. Derek and I are just, uh, friends with benefits I think is the term. Anyway, it was nice meeting you. Have a good night." Kate crossed the hall and knocked on Derek's door. As she entered, she noticed Derek give a half-wave and, glancing back, Kate saw Megan was still in her doorway, a slightly confused look on her face.

"What was that about?" Derek asked.

"Just girl talk," Kate said. "Now, I have some things to show you." For the next half hour, Kate showed Derek how to properly kiss a girl. Most guys were too aggressive, trying to shove their tongues down her throat and devour her face. She showed Derek how to kiss her softly and passionately and really take his time. Then she showed him how to fondle and suck her breasts, starting soft and slow and gradually building her arousal.

"Now it's time for the most important lesson," Kate said, pulling down her jeans. She showed Derek how to orally pleasure a woman, from the initial teasing to fingering to gently pleasuring her clit. He learned how to increase pressure as her orgasm built and, finally, how to finish her off. Kate was rewarded with an intense orgasm and screamed extra loud, hoping the neighbors could hear her.

"Now it's your turn," Kate said. "But first, I need to do something. I'll be right back." She grabbed a towel, wrapped it around herself, and went into the hallway. When Megan answered the door, Kate said, "I'm really sorry to bother you. This is so embarrassing. Could I--"

"Could you what?" Megan said after an uncomfortable pause.

Kate lowered her voice to a whisper. "Could I borrow a condom? I mean, not borrow, just, you know, have one?"

"Uh, sure, I guess," Megan said. "Hold on." She went back inside and Kate followed her in, letting the door close behind her. It was a nice dorm room, with a living area surrounded by what appeared to be four bedrooms and two bathrooms. Megan appeared to be the only one home. She returned and handed Kate a condom.

"Thank you so much, you're a lifesaver," Kate said. "I thought he was getting them and he thought I was and we got a little too far into it so thank you. I better get back, thanks again."

"Sounds like you were having a good time over there," Megan said.

"Oh my God, could you hear me?" Kate said sheepishly. Megan nodded. "I'm sorry for being so loud, it's just that, well, Derek brings that out in me. Sorry for disturbing you."

"No, it's fine," Megan said. "I'm just getting ready for finals while all my roommates are out partying. Pre-med's a little different than majoring in communications and criminal justice, you know?"

"I totally understand," Kate said. "But don't forget to have some fun. Speaking of that, do you think I maybe could have another one? I'm not sure one's going to get the job done."

"Uh, yeah, sure," Megan said, disappearing briefly before handing over another condom. Kate thanked her again and returned to Derek's room. They had sex and Kate made him put it on, making sure he knew how to use it. Plus, it made him last longer. Kate orgasmed again as she rode him, again screaming loudly in the hope Megan would hear. They spent the next couple hours in bed, Kate teaching Derek everything she knew about pleasing a woman. They finished with Derek unloading inside her from behind.

Kate went across the hall one more time. It was now almost midnight and Megan was in her pajamas. "I'm so, so sorry," Kate said earnestly. "But do you think I could have one more?"

"I already gave you two," Megan said.

"I know, I know," Kate said. "But he just keeps going and going. Don't worry, I'll pay you back tomorrow," Kate said. "And know, now that I think about it, could you make it two? One for the morning?"

"Sure, whatever," Megan said, returning with two more condoms. "I hope that's enough." As Kate started to leave, Megan added, "I had no idea about you and Derek. He never said anything."

"We always go to my place. I have an apartment off campus. But the landlord's doing some work this weekend so we came here. He probably thinks I'm embarrassed to be hooking up with a sophomore, which is so far from the truth knowing how talented he is. Anyway, I'm sorry to disturb you. To be honest, the twin bed isn't ideal so I don't know if I'll be back. But it is kind of hot doing it in his dorm, you know? Anyway, thanks again," Kate said as she left.

Back in Derek's dorm, he asked her what was going on. "I told you, girl talk. You'll find out soon enough. Now, we need to go another round."

"Kate, I don't know, I'm not sure I can," Derek said.

"Sure, you can," she said, smiling. "I'll help. Trust me, when I want something I don't give up." With that she began sucking his dick, loving the feel of him getting hard inside her mouth. She went at it for a good 15 minutes before she began to ride him again, orgasming again before riding him faster and harder. He thrust upward, straining to finish and working hard for another orgasm. Kate squeezed him as tightly as she could, plunging downward as far as possible until he finally experienced a well-deserved orgasm for the fourth time that day.

In the morning, Kate woke up before Derek and slipped out of his room, taking his key with her. She drove to a nearby store and grabbed a box of condoms and a few other things. Returning to Derek's room, she heard the shower running. Kate quickly undressed and opened the door to the inner bathroom slightly. "Derek?" she called out. "Is that you?"

"Yeah, it's me," he replied. "I thought you left."

"No, just taking care of a couple things," she said as she opened the door fully and stepped inside. "But I do have one more thing to do." Kate opened the shower door and stepped inside.

"What's that?" Derek said. Kate kissed him and pressed herself against his wet body. His growing erection pressed against her abdomen.

"You need to show me what you learned," she said. "After we get cleaned up, of course." They continued to make out as they showered, alternating between kissing and fondling each other and getting clean. By the end, he was fully aroused. Another reason I love 20-year-olds, Kate thought. As Derek led her into the bed, she said, "Remember what I taught you."

Derek took it slow, kissing her lips and breasts sensually and passionately. He lingered on her breasts for plenty of time, allowing her arousal to build. Then he moved his lips down her abdomen, kissing her gently as he inched his way down. By the time he began kissing her thighs and mons pubis, she could barely stand it. Kate began moving her hips and moaning, desperately needing to feel his tongue on her clit. But Derek denied her, kissing her labia gently and deliberately making her wait for the relief she needed.

Finally, she felt his tongue gently caress her engorged clit. She let out a loud, high-pitched moan and Derek continued to pleasure her. As her muscles tightened and she began to breathe heavily, he suddenly slipped his fingers inside her. Kate squealed and felt herself lose control as he licked and fingered her. She felt him move his other hand just above her clit and press down as he tongued her harder. Kate felt an explosion of pleasure as she climaxed, again crying out loudly but this time not having to embellish.

"You're a fast learner," Kate said as Derek lay next to her, their bodies pressed together in the small bed.

"Yeah, I guess I am," he replied, smiling and obviously proud of himself.

"Now it's your turn," she said, raising up to kneel on the bed. Derek moved to the middle of the bed and Kate knelt between his spread legs. She began to suck his dick, bringing him as deeply into her as she could on each downward thrust and bringing her lips all the way to his head each time she moved upward. She fondled his balls with one hand while propping herself up with the other, letting her long dark hair fall over his hips.

Derek began to tense and said, "I'm not going to last. We should probably switch positions."

"No," Kate said, momentarily switching to stroking him with her hand. "I want you to cum in my mouth." Taking him into her again, Kate felt him grow harder. She could tell he was excited about ejaculating in a woman's mouth for only the second time. She tightened her lips and Derek started grunting and breathing loudly. He began to thrust into her and Kate again stopped, saying, "Just relax and let me do all of the work."

Putting her hands on his thighs, she felt his muscles relax and began to suck him again. Derek lay still as she slightly increased her speed. She knew he was close but not used to having someone else make him cum. She felt his muscles tighten again and his cock swelled. Moments later he let out a loud groan as cum oozed into Kate's mouth. She continued to suck him as his body jerked and his cock pulsed inside her. Derek groaned repeatedly as she slid her mouth up and down his throbbing cock until he put his hand on her shoulder, gesturing for her to stop. Kate slowly slid her mouth off his head, making sure to squeeze the last few drops into her mouth as she did. Raising her head up, she swallowed and said, "Oh, baby, that was great."

Derek just lay on the bed, completely drained and in obvious ecstasy. Eventually he said, "Wow, that was..."

"Delicious?" Kate interrupted.

"I was going to say unbelievable, but sure," he replied.

"I'm glad you liked it," she said. "I love doing that." They lay together in silence for a while before Kate said she had to get going. They got dressed and Kate gathered her things, both happy and a little disappointed Matt hadn't returned yet. As she hugged Derek at the door, she said, "Thanks for a wonderful and very satisfying weekend."

"No, thank you," he said. "For everything."

"You're welcome," she said. "You can be confident know what you're doing. You should ask Megan out. On a real date, not to just hang out. And when she's ready, just do what you did to me and you'll be golden." With that, Kate walked across the hall and knocked on the door. One of Megan's roommates answered and told Kate that Megan was downstairs eating lunch.

Kate found Megan sitting alone at a table in the food court and put the box of condoms into Megan's purse, saying, "Thanks again."

"You're welcome," Megan said. She looked great in a tank top and black yoga pants, her blonde hair in a ponytail. "But I only gave you four, that's a whole box."

"Don't worry about it," Kate said. "Besides, I'm sure you can use them more than me."

"I don't know about that, but thanks," Megan said. As Kate turned to walk away, Megan stopped her. "Hey, can I ask you something?"

"Sure," Kate said.

"Is Derek....available?" Megan asked hesitantly.

"Absolutely," Kate said. "I have finals coming up and then graduation and then I'm moving back home for work. This weekend was kind of our last hurrah."