Oral Advocacy Ch. 04: The Island

It was wonderful tasting him once more, this time in front of Sam. Kate was so turned on she felt the urge to start touching herself as she sucked him. She went slowly, working her way from base to tip and back again over and over. Matt started to moan as his orgasm built. Then she heard Sam start to moan and, out of the corner of her eye, saw that Sam's legs were spread, her hand on her pussy.

A surge of excitement shot through Kate and she felt her own orgasm building. She continued to suck Matt as he stiffened and groaned louder. Sam started to say, "Oh yes, suck it! Suck it!" as Kate deep throated Matt again and again. Hearing Sam excited him further and his cock began to twitch as he thrust into her. Kate kept sucking, taking him as deeply as she could as precum leaked into her mouth and she heard Sam cry out, "Yes! Yes! Suck that cock!"

As she buried her face in Matt's pubes, she heard Sam groan and knew she'd orgasmed. Kate brought her mouth back to the head of Matt's penis and felt it swell just as she moved downward. Hearing Sam orgasm made Matt explode into Kate's mouth with more force than ever before. His cum drenched her tongue and filled her throat as she continued to suck him, his throbbing cock unloading stream after stream inside her.

Kate released his dick and swallowed his load as Sam said breathlessly, "Oh God, that was so hot." Matt's still-hard cock was right in front of Kate's face as he opened his eyes and looked at both of them, a wide smile on his face.

Kate stood up quickly and pulled Matt onto the bed with her. She lay on her back, legs spread and bent at the knees. He knew exactly what to do. He buried his face in her pussy, skipping the foreplay and going straight for her engorged clit. Kate was already on the brink of orgasm and after only a few flicks of Matt's tongue she felt her muscles tighten and her body begin to shudder. She pressed his head against her with her hands and she climaxed intensely, a powerful orgasm rolling over her in waves as she cried out with relief. Matt kept going, making it last for several minutes before it finally subsided.

Kate relaxed her legs, letting her feet dangle over the edge of the bed as Matt rolled onto his side next to her. Sam gazed at them from her chair, obviously aroused and wanting more. "What do you want to see next, Samantha?" Kate asked mischievously.

"I want to watch him fuck you," Sam answered.

Matt was already erect and obviously eager to be inside Kate. She turned over, her head against the mattress and her ass in the air. She felt Matt's hands on her ass, pulling her cheeks apart. Her wet pussy still throbbed from her orgasm as she waited for him to enter her. Feeling his head pressing against her entrance, Kate moaned as Matt made her wait. He reached around and rubbed her nipples between his fingers, his cock still poised at the entrance to her vagina.

As she began to whimper, she felt him slide inside her, gently at first but gradually increasing in intensity with each thrust. Matt pounded her over and over, fucking her as hard as he could as Sam encouraged him. Kate's whole body shook as he fucked her, her tits bouncing and her head sliding back and forth on the bed with each thrust.

When she knew he was close, Kate pulled forward, causing Matt's cock to slip out of her. She rolled onto her back and brought her knees to her chest, exposing her pussy for Matt and Sam. She wanted to see Sam's face as Matt came inside her. Matt quickly entered her again, his torso pressing against Kate's thighs as he drove deeply into her. Kate watched Sam fingering herself as her boyfriend pounded Kate.

Matt came just as she did, again unleashing a massive load inside her. He continued to thrust as he drained his balls, both of them panting and groaning as they climaxed together. When he finished, he rolled over and lay exhausted next to her. Sam sat on the chair, apparently having been denied the second orgasm Kate knew she craved.

"Matt, why don't you go down to the lobby?" Kate said.

"Huh?" he responded. "Why do I need to do that?"

"Go down to the lobby," Kate said firmly. "Samantha and I have some things to discuss." Sam just nodded when Matt looked at her and, with that, he got dressed and left the room. "So cute, isn't he?" Kate said, laughing.

"Yeah," Sam added. "After that, I can see why he's so into you."

"Does that mean we can continue our arrangement, at least until you two leave for Europe?" Kate asked hopefully. "I'll let you watch whenever you want."

Sam hesitated but Kate could tell she wanted to say yes. Sam was staring at Kate, who was lying on her back, her knees in the air and her legs spread. She could feel Matt's cum on her still-wet pussy. "Okay," Sam said finally. "But just until we leave in August."

"Perfect," Kate said. "But there is one more thing I'm going to need."

"What's that?" Sam asked, clearly intrigued as she stared directly at Kate's vagina. Kate knew Sam wanted her, badly, and was extra-horny after watching her with Matt.

"I want to have a threesome with Matt and..." Kate said.

Sam interrupted her excitedly, "Absolutely!"

"Hold on, let me finish," Kate said. "With Matt and another guy."

"What?" Sam asked, clearly confused and disappointed. "You and two guys?"

"For a long time, I've been fantasizing about having two guys inside me at the same time. It just keeps getting more intense and I have to do it," Kate admitted. "It'd be a one-time thing. And of course, I'll give you what you want--another night together, just the two of us."

"Who would the other guy be?" Sam asked.

Jason flashed into Kate's mind but she quickly ignored the thought. As much as she wanted his 8.5 inch cock to be part of it, there was simply no way that was going to work. "Well, I was thinking Derek," Kate said. "I've already slept with him so he's not some random guy off the street. And of course I'd make it worth your while."

Sam started laughing. "There's no way that's going to happen," she said. "It's fine with me, but he'd never do it without Megan's permission. But good idea, Kate. It's kind of hot now that I think about it."

"Well, we'll just have to see, won't we?" Kate asked. "I'm a very good negotiator, after all. I'm sure it won't be a problem."

"I don't know about that," Sam responded. "I don't know her that well, but she's very strait-laced and she and Derek can't get enough of each other. She has him wrapped around her finger. I don't think she's going to be into this. But if she agrees, I'm on board. And of course you'll have to keep up your end of the bargain."

"Okay, well you can at least get Matt on board." Kate said, excited it may actually be happening and turned on by the idea of another night with Sam. "I can't stop thinking about it. How about I throw in a little bonus for your trouble?"

"What bonus?" Sam asked.

"I'll let you clean me up," Kate said, glancing down at her pussy. Sam just smiled and climbed onto the bed. She began to kiss Kate's thighs and vagina, licking every drop off Matt's cum off of her, making Kate wetten again. Sam's tongue flicked against her clit as Kate spread her legs wide. She felt Sam's hands on her breasts, massaging her nipples as Sam continued going down on her. She knew Sam loved tasting her and Matt at the same time. She soon felt Sam's fingers inside her as her orgasm built. Moments later Kate orgasmed again, this time whimpering softly as Sam relieved her for the third time.

Lifting her head up, Sam looked at Kate expectantly. She rolled over onto her back and spread her legs, clearly hopeful that Kate would return the favor. Instead, Kate said, "Not until Megan and Derek are on board. But I'll tell you what, I'll send Matt up here. I'm sure he's ready for another round and I can tell you need it bad."

Kate got dressed and handed Sam a towel to wear so Matt wouldn't know what was going on. Then she went down to the lobby, where she found him sitting on a couch watching TV. "What were you two doing up there for so long?" he asked, clearly frustrated. "What's going on?"

"We were just talking, woman to woman," Kate said. "Now you need to go upstairs and do your job as a boyfriend."

"Kate, what's going on?" Matt asked.

"I said don't worry about it," Kate said. "Get up there and take care of your girlfriend." She nudged him toward the elevator and, as he got on, added, "And give her 110% this time, okay?" Matt smiled and nodded and got on the elevator. Kate went to the hotel's business center to answer a few work emails and then hung out in the lobby for a while. After about an hour, Matt and Sam returned.

Sam said, "Thank you. Whatever you said to him worked. He was incredible and going down on you first made it that much more intense. That was the best sex I ever had."

"I'm glad to hear it," Kate said. "Is Matt on board?"

"Hell yeah," Matt said.

"Of course he is," Sam said laughing. "He's totally into it."

Kate looked at Matt and could see he was excited about the idea. "I figured as much," Kate said. "I'm really looking forward to it."

"Me too," Matt said. "Derek and I have talked about it before, but we had no idea how to find a woman who'd be interested. Now you just need to get Megan to sign off. As long as she approves Derek will be good to go." They split up for the night and Kate headed to Megan's dorm. She lived in the same room as the year before, only Derek no longer lived across the hall because he and Matt now lived in a house off campus with a few other guys.

It was just after 9:00 p.m. when Kate knocked on the door. Megan answered wearing shorts and a t-shirt, her blonde hair up. She was 5'2," just like Kate, and weighed about the same. Her breasts were smaller, probably 32B, Kate thought, but they were perky and looked great. All in all, she was almost a mirror image of Kate, except blonde and, at 21, ten years younger.

"Kate, right?" Megan said. "What are you doing here?"

"I was just in town and thought I'd stop by to see how you're doing," Kate said. "Mind if I come in?"

"Um, no, I guess not," Megan said. "I could use a break anyway. I'm so tired of studying."

"On Friday night?" Kate asked as she walked in and sat down on the couch in the common room.

"Yeah, I know, big loser Megan is studying on a Friday night. All my roommates are out at the bars and I'm studying chemistry."

"Chemistry, wow," Kate said. "That was always more than I could handle. You must be pretty smart."

"I guess," Megan said modestly. "I'm a double major in chemistry and biology. I want to go to med school."

"That's impressive. I really admire that," Kate said honestly.

"Thanks," Megan said. "But it doesn't leave any time for socializing. I'm living in the dorms instead of off campus since it's so much quieter here. Unfortunately, I only can go out once a week, so here I am. Third night of the weekend and I'm studying."

"Second night of the weekend?" Kate asked, confused.

"Yeah, everyone starts partying on Wednesday night here. Most of them don't even have Friday classes," Megan said. "I have labs at 8:00 a.m. on Friday, so I mostly miss out on that. Anyway, enough complaining. Did you really just stop by to see me?"

"Well, not exactly," Kate said. "I was in town to visit a friend and thought I'd stop by."

"You mean Matt?" Megan asked. "Derek told me everything. You know, you could have just told him to ask me out."

"Sorry, but I didn't think you'd say yes. He really lacked confidence before my, uh, intervention and I wanted to make sure you were interested. So, I had to come up with a cover story," Kate said, recalling how she'd told Megan that she was Derek's law-student friend with benefits. And how she'd been so loud as Derek fucked her that Megan couldn't help but be intrigued.

"I have to say, asking me for all those condoms and carrying on so loudly certainly got my attention," Megan said. "And I'm glad you did it. Derek's a great guy and the last year has been wonderful. I'm not sure how I'd get through school with his, uh, support."

"You mean without his tongue and his cock?" Kate said quietly.

"Yeah, I guess so," Megan said, laughing.

"About that," Kate said. "I was wondering if I could borrow Derek for a night sometime. I promise I'll return him in one piece."

"What do you mean?" Megan said, turning serious. "You want to sleep with him again?"

"I'll just come right out and say it," Kate said. "For a long time, I've been fantasizing about having sex with two guys at once. I can't get it out of my head. The idea of two cocks inside me at once, I don't know, it just turns me on like crazy. So I was thinking it could be Derek and Matt, just a one-time thing. Totally safe, everyone knows each other, one night only."

Megan didn't respond for a long time. Kate almost started to speak several times, wanting to argue her case like she was in front of a jury. But she stopped herself and let Megan think it over, knowing sometimes it was better to just let things play out.

Finally, after what seemed like an eternity, Megan said, "Just a one-time thing?"

"Absolutely," Kate said.

"And you'll tell me all the details?" Megan said. "Maybe give me some pointers?"

"Uh, yeah, if you want me to," Kate said, surprised that Megan was into it.

"I guess I do kind of owe you. And to be honest, I've always thought about doing that myself," Megan said. "Kind of a fantasy of mine, you know? But I've never had the guts to go through with it. Or the opportunity, for that matter."

"I know what you mean," Kate said. "I'm 31 and I've been completely conventional my whole life. Maybe think of me as a cautionary tale? Sometimes you just have to take that leap."

"Yeah, I guess so," Megan said. "But you're so smart and successful. And so hot, too! Ending up like you wouldn't be so bad, although I'd never be a lawyer. No offense."

"None taken," Kate said. "And thank you. So, you'll tell Derek it's okay with you?"

"Absolutely," Megan said. "He'll be totally into it. He always says I'm the best girlfriend ever, which is true, but this will take it to a whole other level. And who knows, maybe it will open some opportunities for us in the future."

"Awesome," Kate said as she stood to leave. "I'll let you get back to your studying."

"Ah, yes, my studying," Megan said with a sigh. "I wish I could be at a nice resort, with a beach and great food and wine. Someplace warm, where I don't have to think about chemistry or biology or tests or paying for school or years of debt or..."

"That can certainly be arranged," Kate said. "How about the weekend after next?"

"Are you serious?" Megan said. "That'd be thousands of dollars."

"You're not the only one who spent Friday nights studying in college and law school," Kate said. "Listening to all the comments about not having a life, not having fun, never finding a husband, yada, yada, yada. Trust me, I've heard it all. But you know what it gets you? A job that pays more than most people could even dream of." Kate didn't bother to mention that she had nothing to spend it on, given her dwindling number of friends and lack of a spouse. But Megan had Derek, so that wasn't going to be an issue for her.

"So you'll fly me to a resort for a long weekend and take care of the bill?" Megan asked incredulously.

"Absolutely," Kate said. "We can bring Sam too. We'll make it a girls' trip. How about St. Thomas in the Virgin Islands?"

"I'd love that," Megan said wistfully. "But I don't know, Kate, this is crazy. I have school and finals are coming up and..."

"Don't worry about it," Kate said. "I have plenty of money and honestly, Megan, you can take a weekend off. I admire your drive and ambition, I really do. But God knows you and I could use a break once in a while, right? I'll make the arrangements. We'll leave next Thursday as early as we can. I'll call with the details. Just make sure you're packed and ready to go. And ready to have fun, understood?

"Understood," Megan said. "I'm in. I can skip a couple classes, right?" They hugged and Kate returned to her hotel room. The next day, she called Sam and let her know the plans. Everything was working out perfectly, Kate thought just before Matt stopped by and fucked her one more time. After she checked out, she drove home and made the travel arrangements, booking a two-bedroom suite at a resort in St. Thomas and airline tickets for all three. It was pricey, but not terrible given that it was between spring break and the summer. Certainly nothing Kate couldn't handle.

Two Thursdays later Kate woke up early, really excited for the weekend ahead. She hadn't been on a girls trip in forever and needed the vacation as much as Megan did. She knew she'd end up sleeping with Sam, which was fine since she trusted her to keep her end of the bargain. Kate drove to campus, picked up Sam and Megan, and drove another hour to the airport. By late afternoon island time, they were checked in to the suite.

"This is unbelievable," Sam said as they walked in. The suite had two full bedrooms, both with king-sized beds, and a huge living area. The windows looked out over the beach and a lazy river came right to their doorstep, allowing them to swim to the main pool. Kate could tell Megan was even more impressed.

"I've never seen anything like this before," Megan said as she looked out at the light blue water in the distance, the sound of the crashing waves. "I've always heard about places like this, but seeing one up close is on a whole other level. How much did this cost?"

"Don't worry about it," Kate said. "It's my treat." She couldn't help but notice Sam seemed a little more at home, like she was accustomed to finer things. I guess I really don't know much about these two, Kate thought, especially Megan. "Samantha, have you ever been here before?"

"Yeah, to St. Thomas a few times, but not this resort," she replied. "My parents love to travel so I've been all over. But this is the first time I've been here unsupervised."

"How about you, Megan?" Kate asked. "Do you travel a lot?"

"That was the first time I'd been on a plane," Megan said, obviously embarrassed. "I've been to Florida a few times and to Washington, D.C. once. My family doesn't have a ton of money and there are six of us so big vacations were never in the cards."

"In that case let's enjoy this one," Kate said. They all changed into their swimsuits and headed to the beach only a short walk away. Sam's black bikini was tiny, barely hiding her tight, shaved pussy. Her ass looked incredible and her ample breasts practically popped out of the skimpy top. Her skin was flawless and her long, athletic legs and flat abs looked amazing as she walked onto the beach.

Megan looked great too, Kate noticed. She was wearing a red one-piece, apparently not as comfortable flaunting herself as Sam was. But she should be, Kate thought. Megan looked great. Her blonde hair glowed and her cute little ass looked perfect in her swimsuit. Her breasts, while smaller, were still firm and perky. And her face was prettier than Kate had originally thought.

The staff was starting to clean up as they arrived, but they were able to find some lounge chairs and ordered drinks. As they lay in the evening sun, Kate noticed Sam checking her out. She knew she looked good. She was wearing a light blue bikini that left little to the imagination. Her long black hair lay over the front of her shoulders and her smooth legs stretched out before her. All the running and the time in the gym really paid off on days like this, Kate thought.

They ordered several rounds of drinks and took a few dips in the ocean. The water was a little cool, causing Kate's nipples to get hard. Sam noticed and swam over, standing just next to Kate as the water covered her shoulders. She felt Sam's hands on her breasts, her fingers rubbing Kate's nipples through her bikini. "I can't wait for tonight," Sam whispered. Her right hand slid down Kate's abs and inside her bikini bottom.