Oral Advocacy Ch. 02: The Roommate

Kate smiled broadly as Matt gradually slowed and she felt his erection begin to soften. She loved feeling his cum leak out of her as he withdrew and they both collapsed onto the bed, breathing heavily and completely drained. They lay together for several minutes before Kate propped herself up on her left elbow and rested her right hand on Matt's stomach. She kissed him and said, "That was really great. Thank you."

"You're welcome," he replied. "And thank you too. That was awesome, not having to wear a condom."

"Matt, can I ask you something?" Kate asked. "I know this is kind of awkward, but how many women have you slept with? I'm on birth control but without a condom I could still get..."

"Don't worry," Matt said, cutting her off. "You're only my third and you have nothing to worry about. Trust me."

"Are you serious?" Kate asked. "I mean, I believe you, but how'd you learn to do that if I'm only your third?"

"That's classified," Matt said. "I could tell you, but then I'd have to kill you." Kate looked confused. "It's from Top Gun," he said. "It's a joke. But seriously, I guess I had a great teacher. That's all I can say."

"Okay," Kate said, slightly confused and wondering why he wouldn't say more. But she decided to let it go. They went to sleep, Matt letting Kate sleep in his bed as he took the couch. He really is a nice guy, she thought as she fell asleep.

"Kate?' she heard as she felt someone tapping on her shoulder. "Kate? Time to wake up." She slowly opened her eyes and saw Matt leaning over her. "Sorry to wake you, but I have to leave soon." Kate looked around and saw a clock that said 11:19.

"Oh my God," Kate said. "Did I really sleep past 11:00?"

"Yeah, I let you sleep as long as I could but I have to get going soon," Matt said.

"Oh yeah," Kate said with obvious disappointment. "I forgot I'm sleeping with a baseball stud."

"Not exactly," Matt said as Kate gave him a confused look. "I work for the student paper and cover the team. I go with them on some road trips and this weekend is one of them. Sorry to disappoint."

"No, not at all," Kate said. "I was just confused. Really, you're way better in bed than any athlete, I'm confident of that. But I wish you could stay. Sure you don't have time for one more round?" Kate pulled the sheet down, exposing her firm breasts and flat abs. She kicked the sheet to her ankles and spread her legs, letting Matt admire her tight, shaved pussy and smooth, toned legs.

"Well, I guess I do have a few minutes," Matt said as he quickly got naked. Kate pulled him toward her and put his cock in her mouth. He hardened as she began to suck him, taking it as deeply into her throat as she could. A few moments later, she pulled him into the bed and climbed on top of him. Grabbing his slippery dick, she stroked it as she guided it into her and began to ride him. Matt fondled her breasts as she ground against him, his hard cock rubbing against her clit as he began to thrust upward. Kate continued until she quietly climaxed again. This time she didn't stop, riding Matt harder and taking him deeper until he unloaded inside her once more.

"I hope that lasts you the weekend," Kate said as she climbed off of him.

"You're very talented, Kate Harris," Matt said as he got out of bed and got dressed. "I'm really sorry, but I have to run. Feel free to stay as long as you want. Just shut the door on your way out."

"How long before your roommate gets back?" Kate asked.

"He has class until around 2:00, so he usually gets back a little after that," Matt said.

"Is he really a virgin?" Kate asked as Matt finished packing his bag.

"As far as I know," Matt said. "Why do you ask?"

"He's cute," Kate said.

Seeing the look in her eye, Matt said, "What are you planning to do?"

"Oh, nothing," she replied. "Just fantasizing, that's all."

"Man, you really are horny. Remind me never to become a lawyer," Matt said.

"Or maybe you should. Imagine a whole office filled with Kates," she said, laughing.

"Fair enough," Matt said. "Call me anytime you want to hang out again."

"I will," she said as they hugged. "Have a good trip." After Matt left, she left his door slightly ajar and went for a run. It was a nice day and she hadn't gotten a chance to run lately. She went about six miles, winding through campus and admiring its beauty. Seeing all the young people out and about enjoying their Friday afternoon made Kate nostalgic for her college days. This is much better than sitting in my office, she thought as she returned to Matt's building. She grabbed some food from the food court near the lobby and ate in Matt's room.

Kate then jumped in the shower. The warm water felt great on her smooth skin as she showered and shaved, imagining taking Derek's virginity. She thought about knocking on his door and taking him by surprise, making his fantasies come true. Kate began to get aroused as she imagined Derek inside her and the warm water flowed over her smooth skin. A loud thud jolted her back to reality. This is crazy, she thought. I can't just wait in Matt's apartment and hope some stranger will want to sleep with me. As she turned off the water and began to towel off, Kate was ready to head home.

She wrapped the towel around herself, just barely hiding her ass and tits underneath. As she left the interior bathroom, she stepped into the section of the bathroom with two sinks. Glancing into Matt's room, she saw it was 1:45. Just enough time to get dressed and pack up, she thought. As she crossed the threshold into Matt's room, she heard a noise behind her. Turning around, she saw a man standing in the doorway on the other side of the bathroom.

Kate screamed. "Who are you?" she asked, clutching the towel between her breasts and closing her legs tightly. She quickly recognized Derek from his picture.

"Who am I?" he replied. "Who are you? And what are you doing in my dorm?"

"I'm sorry, you startled me," she said, exhaling loudly. "You must be Matt's roommate. I'm a--a friend of Matt's. I'm sorry to intrude, but I was just leaving. Matt said you wouldn't be back for a while."

"Sorry, class ended early," Derek said with evident confusion. "When I heard the shower I thought it was Matt or...."

"Or who?" Kate asked, wondering who else would be using his shower.

"No one," Derek said. "I didn't know what was going on. Anyway, I'll shut my door. You can use the bathroom." Kate went into Matt's room and got dressed, choosing a gray skirt and button-down white shirt. She brushed her hair, did her makeup, and knocked on Derek's door.

"Sorry again for intruding," Kate said, reaching her hand out. "I'm Kate. It's nice to meet you."

"Nice to meet you too," Derek replied, shaking her hand firmly. "I'm Derek." Kate noticed him glance downward, taking in her body and lingering just a little too long on her breasts. She smiled coyly as his eyes met hers, intrigued by his interest. Maybe I could stick around a while, she thought.

"Well, I'm headed out," Kate said in a disappointed tone. "I was planning to stay all weekend, but Matt apparently has to go on a trip with the baseball team. I guess that leaves me with a long weekend alone. Anyway, it was nice to meet you. Sorry again for surprising you like that. We should have told you I was here."

"No problem," Derek said. "Living in the dorms you get used to people all over the place at all times. How do you know Matt, by the way? You said you're a friend of his?" Kate could tell he was suspicious.

"Uh, I met him a few months ago back home and he invited me up for the weekend," Kate said. "Or at least what I thought would be the weekend. Then he left me hanging with a hotel reservation I have no use for."

"You're welcome to stick around," Derek said. "If you want to, of course."

"Well, I guess I could," Kate said, a little flirtatiously. "Do you have plans? I wouldn't want to intrude."

"I was just going to play some Madden for now and then go out tonight," Derek said. "But that probably doesn't sound too appealing to you, does it?"

"I haven't played Madden in years," Kate said. "Can I join you?"

"You know how to play?" Derek asked.

"What, you think because I'm a girl I don't know how to play Madden?" Kate asked, pretending to be offended. "That's so sexist." Kate had played a decent amount in law school with some of her boyfriend and some of the other guys.

"No, no, I'm just surprised," Derek said. "I'm sorry, I didn't mean to offend you. Of course you can play." He got the game started and they sat on the couch, Kate making sure to hike her skirt up a little as she sat down right next to him, so close they almost touched. He easily won the first three games, Kate not having played in five years.

She could sense Derek's nervousness. Poor guy, she thought. He wants to make a move but doesn't know how. Suddenly, an idea crossed her mind. "Care to make it interesting?" Kate asked as she put her hand on his thigh.

"What do you mean?" Derek said, shifting uncomfortably.

"Well, you'd have to take the worst team and I get the best to make it fair," Kate said as she moved her hand ever so slightly up his thigh. "But for each game you win, I have to remove an article of clothing. And for each game I win, you have to remove one. First one who's naked loses."

"Are you serious?" Derek asked, swallowing hard. Kate just smiled and nodded, moving her hand closer to his crotch so he got the message. "Uh, sure, okay," he said.

"Socks and shoes off before we start, since that's just a waste of time," Kate said, removing her hand. "I assume that leaves you with jeans, boxers, and a shirt. So, to make it even, I need to get down to three articles of clothing." Reaching up under her shirt, she unfastened her bra. "Close your eyes," she said before taking it off and dropping it on Derek's lap. "Now it's even."

Derek easily won the first game. Kate stood in front of him and seductively unbuttoned her shirt, letting it fall to the floor as Derek gaped at her perky tits. He'd obviously expected her to lose the skirt first and throughout the second game couldn't stop looking over at her, allowing Kate to win. He took his jeans off, just as Kate hoped he would. As they started the third game, she could see his cock bulging against his boxers.

Kate lost the third game. Standing in front of Derek, she unfastened her skirt and turned around. She tugged it down past her butt, bending over with her ass right in his face as she slid her skirt to her ankles and stepped out of it. She lingered in front of him for a few seconds, allowing him to enjoy the view of her tight ass in her white panties. "I guess I can't lose any more games," she said as she sat back down, her legs spread slightly so he could enjoy the view. Kate won a close fourth game and Derek's shirt came off. "This one's for the win," she said as they started the fifth game.

Derek managed to keep his focus, refusing to look over at her despite her best efforts to make him peek, and won the final game. "I guess it's time for me to pay up," Kate said. "Promise you won't tell anyone?" Derek nodded his head as Kate stood before him. She slowly put her thumbs inside her panties and lowered them, leaning over and giving Derek a great view of her tits as she did. Stepping out of them, she tossed them onto his lap and said, "You can keep them. Consider it your trophy."

Derek was speechless as he stared at her. Kate could tell he was incredibly nervous. He was also rock hard, which turned Kate on like never before. "You can touch me if you want," she said as she sat down.

"Uh, no it's okay," he said. "I mean, um, yeah, if you want me to. I, just, I mean, sure, but, yeah, I can do that." Kate turned to her right and Derek cupped both of her breasts with his hands, a broad smile crossing his face as he gently rubbed her. Kate's nipples hardened as fondled her and she began to moan lightly, letting him know she liked it.

"Do you want to touch me anywhere else?" she asked flirtatiously. Without waiting for an answer, she guided his right hand to her abdomen, leaned back on the couch, and opened her legs wider. She moved his hand to her pussy and let him rub her for a while, her moans increasing in intensity. Releasing his hand, she suspected he was too inexperienced to get her off and decided to change course.

"Derek, do you want me to suck your cock?" she asked matter of factly. His hand stopped and Kate could sense his nervousness increase. "Have you ever gotten a blowjob before?"

"Uh, well, I, uh," he stammered.

"It's okay," Kate said, pulling him to his feet and wrapping her arms around his shoulders. She kissed him gently and they made out for a few minutes before she moved her hand to his crotch and began stroking him through his boxers. "Just relax and enjoy."

Kate knelt before him and moved her hands up his legs. Derek moaned as she gently rubbed his upper thighs and lower abdomen. She pulled his boxers away from his body with the backs of her hands, lifting them over his erect penis and then down to his ankles. He stepped out of them and Kate nudged his legs apart as she began to lick his shaft. She slowly worked her way up and down before kissing his head and taking it into her mouth.

Derek moaned as slid her mouth down his cock. He was about 6 inches and she was able to take most of him inside her. She quickly felt him begin to stiffen further after only a few minutes. As his muscles tightened and he began to breathe heavily, Kate knew he was close. Increasing her speed slightly, she gently squeezed his balls and took him as deep as she could. Derek cried out loudly as he exploded inside her, his cum drenching her mouth as his cock throbbed. Streams of cum shot into her. It was thicker and saltier than Matt's, Kate noticed as she gulped it down.

Kate sucked him a few more times to make sure she got every drop. Derek pulled back slightly and Kate withdrew, guessing it was too intense for her to continue. She looked up at him and smiled as he opened his eyes, a few drops of cum dribbling down her chin. Standing up, she said, "I hope you enjoyed that."

"That was unbelievable," he said as they slumped onto the couch. They sat in silence for a few minutes.

"Well, I guess I should be going," Kate said. "I have a long drive."

"Already?" Derek said. "You're welcome to stick around." Kate liked the show of confidence.

"Well, I guess I could," she said flirtatiously. "How about this, I'll go to my hotel room for a while and you can meet me for dinner. My treat. How about I pick you up at 6:00?" Derek agreed and Kate left, checking into a nice hotel with a queen-sized bed before picking Derek up at 6:00 and taking him out for dinner. He looked handsome in a pair of gray pants and a button-down long-sleeved blue shirt. Kate wore her red dress, this time with a red thong and pushup bra she knew he wouldn't be able to resist.

During dinner he told her about school, growing up in Florida, and his friends, including Matt. She told him about being a lawyer and a little bit about her college and law school days. "You're probably wondering how I know Matt and what I'm doing here," she said.

"Definitely," Derek said. "I have no idea what's going on right now."

"Matt didn't say anything about me?" she asked.

"Not a word," he said. Kate told him about the accident, her weekend with Matt, the stress of her job, and her visit to campus. When she finished, Derek sat in stunned silence. Gradually, conversation resumed, with Kate explaining how intense and stressful her job was, leaving so little time for a sex life. Or a social life for that matter.

When the waiter dropped off the check, Kate knew she wanted to go through with it. Waiting for him to walk away, Kate asked in a low voice, "Derek, how is it that you'd never gotten a blowjob before?"

"I don't know," he replied, obviously embarrassed. "I'm just not that good with girls, I guess. I have a bunch of girl friends, but I just have trouble taking that next step, you know? I probably sound like a big loser right now."

"No, you don't. I didn't lose my virginity until I was a sophomore," Kate said truthfully.

"Really?" Derek said. "You're so pretty and smart and confident, I can't believe that."

"Aww, you're really sweet," Kate said. "But it's true."

"Is it that obvious that I'm a virgin?" Matt asked after Kate paid the bill.

"Well, it's not like I can tell from looking at you," Kate replied, laughing. "But last night Matt mentioned it." They got up to leave and walked outside to Kate's car. "Derek, do you want to come back to my hotel with me?"

"I don't know," Derek said. "I mean, Matt's my roommate and one of my best friends."

"It's okay," Kate said. "I want to do this with you." Derek didn't say anything but Kate could tell he wanted her. She moved closer to him and put her hand on his crotch, feeling his hardening cock.

"I assume that's a yes?" she asked. Derek gulped and nodded his head. When they arrived at the hotel, Kate led him to the elevator and into her suite, putting the do not disturb sign out and locking the deadbolt behind them. She led him to the couch and sat next to him. "It's okay if you're nervous. Let's just take it slow and enjoy each other, okay?"

They stood up and she slowly unbuttoned his shirt. Putting her hands on his chest, she could feel his heart pounding. She kissed him deeply, putting her arms around his shoulders as they made out. Derek put his hands on the small of her back as Kate pressed against him, feeling him get hard. She quickly unbuckled his belt and unzipped him, reaching inside his boxers to stroke his shaft.

Kate stepped back and knelt down, pulling Derek's pants to his ankles. He stepped out of his shoes and she pulled his pants and boxers off, again taking him into her mouth and sucking him for a few minutes. Then she stood up and pushed him onto the bed, his massive erection pointed straight at her as he sat on the edge of the bed.

Kate slowly removed her dress, letting him take in the view of her gorgeous body as she stood before him. She slowly undid her bra, his eyes locked on her chest as she slipped it off and freed her tits. Then she turned around and bent over, reaching up and slipping her thong off as he stared at her ass and pussy. As she stepped out of her thong, Derek reached out and felt her tight ass with both hands.

Turning around, she pushed him down onto the bed and climbed on top of him. She put her tits in his face and let him suck and fondle them. Clearly enamored, Derek went at them hard. He has a few things to learn, Kate thought as he devoured them a little too aggressively. But since it was his first time, she didn't interrupt and let him enjoy himself.

After a few minutes, Kate began to lightly stroke Derek's cock. Kate climbed off him and lay on her back, allowing Derek to get on top. He kissed her and began to suck her tits again while his hands wandered all over her legs, ass, and breasts. Kate loved knowing this was his first time and, despite his lack of skill, got turned on from knowing she was about to take his virginity.

As he began to rub against the outside of her pussy, Kate quietly said, "I'm ready." Taking his cock in her hand, she guided it to the opening of her vagina and let him enter her. Derek moaned as he slid inside and began to thrust, gently at first and then a little harder. Kate began to say, "Oh yes, oh yes," increasing in volume as he thrust into her tight, wet pussy. He came quickly, shuddering and groaning loudly as he sprayed his semen into her. Kate hugged him tightly as he thrust a few more times before laying his forehead against her shoulder and pulling her toward him with his hands behind her shoulders as he lay on top of her, his penis still inside her.

As he softened, he withdrew, his cum dripping out of Kate and onto the bed. She lay her head on his chest and wrapped her left arm around his waist, wanting him to enjoy the aftermath of his first time. After a while she raised her head and kissed him.