Roommates Pt. 09

If it wasn't for the fact that they were both in their underwear and her in a tank top that might as well have been a bra, their breakfast was fairly normal. They talked about where were the best places to hike outside of the city--he deferred to her as the life-long resident and him the transplant. He felt better about the table hiding the erection that wouldn't go down. He really didn't want to make her feel uncomfortable, but the way that her foot traced up his calf the whole time they were eating made him feel reasonably sure she was okay putting up with his issues.

She bussed the plates to the sink for him, asking if he would make them some sandwiches and snacks for the day while she went to change. He was mid-agreement, as she started out of the kitchen, raising her tank top over her head as she passed him. His "Yes, Cas--" caught in his throat as he saw her bare back and a fleeting profile of her bare breasts as she turned the corner between the kitchen and living room.

"Thanks," she called as she retreated to her room.

A few minutes later, as he was wiping down the counter, he turned to find Casey standing in the doorway. She had on a black sports bra, panties, and a smile. Had she been watching me? he wondered.

"I thought I'd ask if you prefer yoga shorts or pants for the hike. I figured I'd give you the choice, since you made me breakfast."

"Ah," he paused, imagining her in one and then the other. "Shorts? It is going to be warm."

"I'll say," she said as she turned around, letting him get a good look at her ass. Why am I so focused on her breasts when her ass looks like that? And thighs, and... Taylor pressed his hard cock against the counter, moaning from the pressure.

Before long, they were in his car, speeding out of the city, heading up into the foothills to the east. He was wearing a tank top and shorts, but was having trouble concentrating on the road with the ample skin on display in his passenger seat. He gave up trying to hide his erection after a few awkward minutes.

"Can I ask you something personal?" Casey started, after a silence.

"Um, sure."

"Can you tell me about past relationships you've had? Maybe tell me about the longest?"

"Oh!" Taylor was genuinely surprised. "I guess. If you like. Marissa and I met in grad school. We were in different departments but close enough that students from her department would often work with a prof in our department and vice versa. She came to take a class with my advisor and I was in it. We hit it off right away."

"What attracted you to her?"

"Well, she was gorgeous, almost as attractive as... ahem, anyway, she was smart. We had similar tastes in food, music, movies, and books. You know, the usual stuff. She taught dance to kids, so she was in good shape and graceful. She also was insat--... never mind."

"No, no, what were you going to say?"

"She, um, liked sex."

"In general or with you?"

"Both? I am not sure. We had a lot of sex. She didn't say it was out of the ordinary for her to get off twice a day, or three times."

"Every day?"

"Basically. I was twenty-three. It was easy then."

"You mean now, you couldn't..."

"Honestly I do not know. Lately I am fairly certain it wouldn't be a problem."

"So how you've been has been, um, unusual for you?"

"Unusual but not so much that I worry about it."

"So you normally stay hard for entire car rides?"

"Casey!"

"I know, I know, it is just distracting."

"I am trying. Really I am."

"No, I see that, and I really, really appreciate it." Her hand came to rest on his thigh.

"Anyway, no, we had a lot of sex, but we broke up because she graduated before me and got a job across the country. The long-distance was too much for her."

"You would have stayed with her?"

"I think so, at least, it was her call to end it."

"I'm sorry, Taylor."

"Thanks." Her hands squeezed his thigh, perhaps sympathetically, but his cock twitched. "Um, I'm a little sensitive right now, do you mind, uh, I can't believe I'm going to ask you this, not doing that to my thigh?"

She turned towards him now, leaning forward. Even in his peripheral vision he could see down her top. "No."

"No, what?"

"No. I am trying to help you deal with your issue. I have to push you a little or you won't be able to handle more. You'll get used to it." As she spoke, she swayed slightly. He didn't have to be looking to feel pulled in. "Now, pay attention to driving. You just missed our exit."

"Oh shit," he said as he signaled to get over and take the next one to circle back. She did remove her hand, though, and in minutes they were pulling into the trailhead parking lot.

They had been hiking an hour. At first they were walking side by side, sharing stories of hikes and camping trips they had taken as kids with their families and then later as adults with friends. But as the trail began to switch back and forth up the steep face, it narrowed to a single-file width and Taylor fell in behind Casey.

With the incline and the unsteady footing, his eyeline seemed to gravitate towards her yoga-shorts-clad ass. At least that is what he told himself. It wasn't just because he couldn't tear his eyes away. Something rhythmic about her walking--left, right, left, right--was sort of mesmerizing.

"Yes, Casey," he heard himself saying. Wait, what had she asked? He ran back through his mind. Water break?

He snapped out of it as she turned around, hands on her hips. "You're making it hard on yourself, you know," she said, a little rough, but the smile on her face told him she was just teasing.

They drank their water and hiked now, reaching above the treeline to their minor summit by lunch time. He broke out the sandwiches, fruit, and other things he had packed for them to eat. They sat on a stone ledge pushing up from the ground. They talked about the trees and how they differed between here and where he had lived before, a few hours to the interior. He opened the thermos and poured them each a cup of tea, handing her a dark chocolate bar to split. She stood up, setting down her water bottle by her day pack and then planted herself in his lap instead of back on the stone.

"I hope you don't mind," she said, shifting to find a comfortable position. "The stone was too hard." She continued to shift, probably unable to settle because of his erection pressing back against her.

"Ugh," he moaned a little.

"Are you okay? Am I too heavy?"

"What?" His eyes snapped open. He had clearly been miles away. "No, no, you feel great. I mean, no, it is totally comfort--ab--able," he managed as she rolled her hips.

"Oh, good." She handed him half of the chocolate bar and sat, munching happily, seemingly oblivious to her micro-sifts that were bringing him dangerously close to the edge. His hand rested on her thigh, holding his enamel mug. He moaned a little louder and leaned the side of his face against her back. He was breathing deeply and trying to relax his pelvic floor to forestall cumming right there in his shorts.

She stood up suddenly, turning, putting a hand on each of his knees as she leaned forward. "We should probably head back down." His eyes gravitated right where she intended.

"Yes, Casey," he said without thinking, his breathing ragged.

She fell in behind him as he started out on the return loop of the trail. He was lucky not to know what was going through her head on their way down. Aside from looking at his shoulders and how his muscles flexed beneath the light pack as he navigated the switchbacks, she was wondering when he would snap. Is he just going to let me keep teasing him until he pops? Or will he grab me by my upper arms, push me down on the couch, and slide himself... she let her thoughts wander the whole hour back down the mountain.

Back in the car, driving back to the city, Taylor had been quiet.

"Can I ask you a personal question now?"

"Go ahead. I might not answer, but you can ask."

"Okay, a few days ago you said you had had some boyfriends who felt addicted to you. Can you tell me what happened?"

"Oh, that. Sure. Um, let's see. Let me tell you about Brad. He was a hot shot in the company I was working in. He was very full of himself. To be fair, he was an asset to the company, genuinely treated people with respect, came from a wealthy family, and was really, really good looking. The problem was he knew all this. He had an easy time attracting women. I guess I was young and got taken in by it. Eventually he got around to asking me out and I said 'yes' because, well, I was curious. He took me nice places, had a nice car, a nice apartment, and a nice body. He was a nice guy--sorry, is this too much?"

"No, no, please go on."

"Okay, so we got physical and even though on paper he seemed like this ideal guy, it just wasn't working for me. I couldn't get into it. And he could go a long time."

"Wait, isn't that a good thing?"

"Too much of a good thing. Sometimes I orgasm from penetration, but if it isn't going to happen, it isn't going to happen, so when he would fuck me for an hour, thinking he was some big stud, the whole time, I was thinking, 'when is this over?' So the next day I was sore, and when he wanted another round, I told him I needed another day to recover. And when he wanted to masturbate instead, I asked him to wait until the next day. By the next night, he was really wound up. I could tell how turned on he was. I thought this was more fun than the prospect of another hour drubbing, so I teased him all day at work and then got him excited before bed, but then pretended to fall asleep. I could tell he was masturbating, so I woke up and asked him to stop. He groaned. He told me how turned on he was. I asked him to save it for me. And he did. Two days later I decided it was enough. Are you doing okay, Taylor? You're sweating."

"N-no, I'm fine," he said. His cock was throbbing as he concentrated on the drive. "Please go on."

"Well, that night I could tell he was so turned on that it wouldn't take much. I was hopeful that it would be better than the last time. We made out and I rubbed him through his clothes until he was groaning. Then I asked him to take care of me with his mouth. I wanted to be sure that I got at least something out of this time. He told me he doesn't usually but in this case he didn't mind. He was okay. Clearly not a lot of practice, but he got the job done. He was so proud of himself. He was clearly ready and I teased him some with my hand before I let him enter me. It was only a few minutes before he got this look on his face. 'Oh no,' he was saying. I goaded him a little bit, teasing him and then it was over. When he left my place, I masturbated, thinking about how good I felt. How powerful. But then, as I came down, I was worried I had broken him. But no. He was back two nights later, begging me for more. He eventually learned to use his mouth better than his cock. I realized then what this type of thing can do to a man. Even a mature man. Someone who is in control of himself in most other respects. He just needs to let someone else take over this aspect of their life. Taylor?"

"Yessss."

"Was that story too much?"

"No, it was... ah... illuminating."

"And he was just my first. I've learned a lot about myself since then. And also about how to keep a tight grip on my partners."

Taylor was quiet for the rest of the drive, but she could see the quarter-size wet spot where his cock head pushed at his shorts.

It was mid afternoon. They had both showered. Casey's was satisfying--twice in fact, as she washed the trail dust off her legs and used the shower head to bring herself to two orgasms replaying the car ride conversations and the feeling of his thick cock pressed against her when she sat in his lap. Taylor's was less so. His cock was dripping precum as he washed himself, but he managed to cool himself down enough to tuck into a pair of underwear and pajama bottoms, since they were going to lounge around and read for a bit.

He was pulling on a T-shirt as he came in into the living room to find Casey sitting the long way on the couch, leaned against the arm rest in her tan tank top and black yoga pants, reading already. She didn't say anything but pulled her legs up, laying them back down on his lap when he sat down.

Taylor had been reading a few minutes when he felt her calves shifting against him. Even the pressure of her legs on his thighs had brought him back to full hardness. As she moved her legs, she slid her left one down his thighs and back up, pushing fabric and his cock upright, trapping it against her right leg, nearer his abdomen. His breath caught in his throat as she squeezed his cock between her calves.

"Are you okay, Taylor? Is this comfortable for you?"

His eyes were closed and he could only nod.

"Okay, you let me know." She would sit still for periods and then slowly rub her legs back and forth, grinding him between them. As soon as he made a sound or indication, she'd stop. A whimper, a groan, or a moan would make the sensations stop, so he tried to keep a neutral expression as she rubbed his cock through the fabric. He was barely pretending to read, his eyes more often closed than not.

But then he felt it. After a particularly long and tight few minutes of pressure, he felt his toes began to tingle. He knew that if she didn't stop, he'd cum.

"Please, Casey," he whispered.

"What was that, Taylor?" She ground harder.

"You have to stop or..."

"Or what, Taylor?"

"I'm going to..."

"What, Taylor? Going to what?"

"I'm going to lose control. You have to stop."

"What makes you think you have control?" she whispered, just audible to him.

"Oh, god, Casey!" He felt the sensations, the tingling at his toes and fingers traveling up his extremities, converging through his groin.

"Oh my god, Taylor, are you going to cum?"

Days of teasing, being edged, wanting, needing, all coming together at once. "Oh fuck!" he managed to croak.

"Oh my god, Taylor, are you going to cum? Are you going to cum right now?"

"I'm--oh god!"

"Are you going to cum all over my legs, on my yoga pants, Taylor? Are you cumming for me?"

He lost it. He felt the hot throb along the length of his cock as pulse after pulse of cum shot out of him. It saturated the thin material covering him. The volume and force made it through, onto her legs, creating a surprisingly large puddle. Taylor sat in a daze, staring as the wetness in his lap widened, marveling in the intensity of the feeling, how long it continued, and the amount he produced. His breathing was still ragged. Had he looked at Casey, he would have seen the absolute wicked delight on her face as she watched him convulse and writhe under her.

After a minute for him to catch his breath, she stood up, semen clinging and running down her calves as she did so. She faced away from him, bending forward as she pulled the tight fabric down her legs. Taylor sat, still stunned on the couch. She set her sodden pants on his lap. "Will you please put those in the wash for me, Taylor?" She was looming over him, but she did not seem angry.

"Yes, Casey," he said, automatically.

"Good boy. We'll talk about how you can atone for this after you make me dinner okay?"

"Yes, Casey." He collected himself and stood up, holding the wet clothing and making his way to his room. Three days worth of cum, he thought. I don't think I've ever been so turned on. I can feel the fog of arousal I had been floating in the last few days lifted, but... I disappointed her. Dammit.

As he stripped out of his pajama pants and drenched underwear, he saw something sitting on his dresser. A letter with his name on it propped against a box he kept his wallet and keys in.

Dear Taylor,

I wanted to give this to you when you are in what is at least a slightly clearer head space. I want you to confirm to me that you consent to what we are doing. I think it would ruin the tension if we talked about it, but we can discuss this if that is something you need. Otherwise, you can leave me a letter on my dresser if there is anything you want me to know but don't feel comfortable telling me. You can also stop anything that is not acceptable in the moment by using the words "edible stopwatch." If you choose to completely end whatever it is we are doing here, you can also simply give me this letter. I will not ask you to move out, although as part of the game we are playing, I will continue to threaten you with that to maintain the power imbalance.

If these terms are acceptable, than please signal your consent by wearing your maroon boxer briefs when you change.

Yours,

Casey

Taylor read the message twice. Without hesitation he pulled open his top drawer and slipped into his maroon underwear, tucking his still half-hard cock into the pouch. He turned and started out of his room before coming back to his desk. He grabbed a piece of paper and wrote quickly on it, folding it in half.

He paused at the threshold of her door--he'd never been in her room--before going in and laying the folded sheet on her dresser. He left, walking into the living room, to find Casey reading on the couch, still in her thong and tank top.

She glanced up and took in his single article of clothing, a smile drawing across her lips. She looked back into her book. "Go make some tea," she said, not looking at him.

"Yes Casey," he said, feeling blood surge to his cock as he did.

As soon as he was in the kitchen, Casey jumped up and silently hurried to her room. She had heard him rustling paper. She saw the sheet laying on her dresser and felt a little nervous. Her fingers trembled a little as she opened up the single page. The white paper held only three words, written in black ink: Break me--please.